FR2919500A1 - Composition, useful for dyeing keratin fibers, preferably human keratin fibers such as hair, comprises cationic cellulose ether, 2,3-diaminopyrazolone derivatives, and second oxidation dyes - Google Patents
Composition, useful for dyeing keratin fibers, preferably human keratin fibers such as hair, comprises cationic cellulose ether, 2,3-diaminopyrazolone derivatives, and second oxidation dyes Download PDFInfo
- Publication number
- FR2919500A1 FR2919500A1 FR0756859A FR0756859A FR2919500A1 FR 2919500 A1 FR2919500 A1 FR 2919500A1 FR 0756859 A FR0756859 A FR 0756859A FR 0756859 A FR0756859 A FR 0756859A FR 2919500 A1 FR2919500 A1 FR 2919500A1
- Authority
- FR
- France
- Prior art keywords
- amino
- para
- composition according
- phenylenediamine
- addition salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 189
- 230000003647 oxidation Effects 0.000 title claims abstract description 66
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 66
- 238000004043 dyeing Methods 0.000 title claims abstract description 61
- 239000000975 dye Substances 0.000 title claims abstract description 56
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 52
- 239000000835 fiber Substances 0.000 title claims abstract description 42
- 210000004209 hair Anatomy 0.000 title claims abstract description 36
- 229920003086 cellulose ether Polymers 0.000 title claims abstract description 31
- 102000011782 Keratins Human genes 0.000 title abstract description 12
- 108010076876 Keratins Proteins 0.000 title abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 112
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- -1 amine compounds Chemical class 0.000 claims abstract description 66
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 239000007800 oxidant agent Substances 0.000 claims abstract description 16
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 claims abstract description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 87
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 239000002585 base Substances 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 125000005518 carboxamido group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 150000002476 indolines Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- KWSVXCAQFTWTEF-UHFFFAOYSA-N 2-(2,5-diaminophenyl)ethanol Chemical compound NC1=CC=C(N)C(CCO)=C1 KWSVXCAQFTWTEF-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000003217 pyrazoles Chemical class 0.000 claims description 8
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000000982 direct dye Substances 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002475 indoles Chemical class 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 150000003222 pyridines Chemical class 0.000 claims description 5
- 239000002562 thickening agent Substances 0.000 claims description 5
- 235000013311 vegetables Nutrition 0.000 claims description 5
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 claims description 4
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 claims description 4
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical class C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical group NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 4
- ZLOJSTQJEWRDGU-UHFFFAOYSA-N 6,7-diamino-2,3-dihydro-1h-pyrazolo[1,2-a]pyrazol-5-one Chemical compound C1CCN2C(N)=C(N)C(=O)N21 ZLOJSTQJEWRDGU-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 108090000854 Oxidoreductases Proteins 0.000 claims description 4
- 102000004316 Oxidoreductases Human genes 0.000 claims description 4
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 4
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 150000005528 benzodioxoles Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 239000002304 perfume Substances 0.000 claims description 4
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical class N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- OQDMCDIRPZVTFZ-UHFFFAOYSA-N 1,3-dihydropyrazol-2-amine Chemical class NN1CC=CN1 OQDMCDIRPZVTFZ-UHFFFAOYSA-N 0.000 claims description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical group NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical class C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims description 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
- LHGQFZQWSOXLEW-UHFFFAOYSA-N 1h-pyrazole-4,5-diamine Chemical class NC=1C=NNC=1N LHGQFZQWSOXLEW-UHFFFAOYSA-N 0.000 claims description 3
- NMEPLWZDUIIAAC-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]pyridazine Chemical class C1=NN=C2C=NNC2=C1 NMEPLWZDUIIAAC-UHFFFAOYSA-N 0.000 claims description 3
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 claims description 3
- KEEQZNSCYCPKOJ-UHFFFAOYSA-N 2,6-diethylbenzene-1,4-diamine Chemical compound CCC1=CC(N)=CC(CC)=C1N KEEQZNSCYCPKOJ-UHFFFAOYSA-N 0.000 claims description 3
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 claims description 3
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 claims description 3
- WNYJRJRHKRZXEO-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)C1=CC(N)=CC=C1N WNYJRJRHKRZXEO-UHFFFAOYSA-N 0.000 claims description 3
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical class C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 claims description 3
- QCCKSFHMARIKSK-UHFFFAOYSA-N 5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline Chemical compound C1CCC2=CC=CC3=C2N1C=C3 QCCKSFHMARIKSK-UHFFFAOYSA-N 0.000 claims description 3
- VHHWHDFVZGPKRT-UHFFFAOYSA-N 5h-pyrazolo[3,4-d][1,3]thiazole Chemical class N1=NC2=NCSC2=C1 VHHWHDFVZGPKRT-UHFFFAOYSA-N 0.000 claims description 3
- UXYHZIYEDDINQH-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=NN=C3C=CC2=C1 UXYHZIYEDDINQH-UHFFFAOYSA-N 0.000 claims description 3
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N alpha-naphthol Natural products C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001907 coumarones Chemical class 0.000 claims description 3
- 150000007857 hydrazones Chemical class 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- CYCBAKHQLAYYHQ-UHFFFAOYSA-N imidazo[4,5-c]pyrazole Chemical class N1=NC2=NC=NC2=C1 CYCBAKHQLAYYHQ-UHFFFAOYSA-N 0.000 claims description 3
- PTFYQSWHBLOXRZ-UHFFFAOYSA-N imidazo[4,5-e]indazole Chemical class C1=CC2=NC=NC2=C2C=NN=C21 PTFYQSWHBLOXRZ-UHFFFAOYSA-N 0.000 claims description 3
- DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical compound C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- 150000003577 thiophenes Chemical class 0.000 claims description 3
- NKNCGBHPGCHYCQ-UHFFFAOYSA-N (2,5-diaminophenyl)methanol Chemical compound NC1=CC=C(N)C(CO)=C1 NKNCGBHPGCHYCQ-UHFFFAOYSA-N 0.000 claims description 2
- WVOAPRDRMLHUMI-UHFFFAOYSA-N (2-methylnaphthalen-1-yl) acetate Chemical compound C1=CC=C2C(OC(=O)C)=C(C)C=CC2=C1 WVOAPRDRMLHUMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- QSXNLJITQBHSMT-UHFFFAOYSA-N 1-(4-aminophenyl)pyrrolidin-3-ol Chemical compound C1=CC(N)=CC=C1N1CC(O)CC1 QSXNLJITQBHSMT-UHFFFAOYSA-N 0.000 claims description 2
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 claims description 2
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 claims description 2
- FCSVCKPGLPKMBG-UHFFFAOYSA-N 2-(2-chloro-3-hydrazinylphenyl)ethanol Chemical compound OCCC=1C(=C(NN)C=CC=1)Cl FCSVCKPGLPKMBG-UHFFFAOYSA-N 0.000 claims description 2
- NWCIKTGBDQPYHS-UHFFFAOYSA-N 2-(2-methoxyethyl)benzene-1,4-diamine Chemical compound COCCC1=CC(N)=CC=C1N NWCIKTGBDQPYHS-UHFFFAOYSA-N 0.000 claims description 2
- XNRMYNWJFOGYTB-UHFFFAOYSA-N 2-(3-hydrazinyl-2-methylphenyl)ethanol Chemical compound OCCC=1C(=C(NN)C=CC1)C XNRMYNWJFOGYTB-UHFFFAOYSA-N 0.000 claims description 2
- DMUXRIHPNREBPF-UHFFFAOYSA-N 2-[2-[2-[2-(2,5-diaminophenoxy)ethoxy]ethoxy]ethoxy]benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(OCCOCCOCCOC=2C(=CC=C(N)C=2)N)=C1 DMUXRIHPNREBPF-UHFFFAOYSA-N 0.000 claims description 2
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 claims description 2
- SWZVJOLLQTWFCW-UHFFFAOYSA-N 2-chlorobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Cl SWZVJOLLQTWFCW-UHFFFAOYSA-N 0.000 claims description 2
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 2
- SRJCJJKWVSSELL-UHFFFAOYSA-N 2-methylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C)=CC=C21 SRJCJJKWVSSELL-UHFFFAOYSA-N 0.000 claims description 2
- UVUGDGRIYQQKIT-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-amine Chemical compound O1CCNC2=CC(N)=CC=C21 UVUGDGRIYQQKIT-UHFFFAOYSA-N 0.000 claims description 2
- HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 claims description 2
- MZQGZBUNWFAKAC-UHFFFAOYSA-N 3-(4-aminoanilino)propan-1-ol Chemical compound NC1=CC=C(NCCCO)C=C1 MZQGZBUNWFAKAC-UHFFFAOYSA-N 0.000 claims description 2
- KUVHMYCSRBIGDS-UHFFFAOYSA-N 3-[(2-hydroxyethylamino)methyl]phenol Chemical compound OCCNCC1=CC=CC(O)=C1 KUVHMYCSRBIGDS-UHFFFAOYSA-N 0.000 claims description 2
- BGGGDHXHMQFBGA-UHFFFAOYSA-N 4-[(2,4-diaminophenoxy)methoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OCOC1=CC=C(N)C=C1N BGGGDHXHMQFBGA-UHFFFAOYSA-N 0.000 claims description 2
- MWKPYVXITDAZLL-UHFFFAOYSA-N 4-[3-(2,4-diaminophenoxy)propoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OCCCOC1=CC=C(N)C=C1N MWKPYVXITDAZLL-UHFFFAOYSA-N 0.000 claims description 2
- PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 claims description 2
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 claims description 2
- MXJQJURZHQZLNN-UHFFFAOYSA-N 4-amino-2-fluorophenol Chemical compound NC1=CC=C(O)C(F)=C1 MXJQJURZHQZLNN-UHFFFAOYSA-N 0.000 claims description 2
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 2
- DHKIYDNMIXSKQP-UHFFFAOYSA-N 4-amino-3-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C=C1CO DHKIYDNMIXSKQP-UHFFFAOYSA-N 0.000 claims description 2
- MNPLTKHJEAFOCA-UHFFFAOYSA-N 4-amino-3-fluorophenol Chemical compound NC1=CC=C(O)C=C1F MNPLTKHJEAFOCA-UHFFFAOYSA-N 0.000 claims description 2
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 claims description 2
- AYAKPRUPZTWPLK-UHFFFAOYSA-N 4-ethoxy-6-methylbenzene-1,3-diamine Chemical compound CCOC1=CC(C)=C(N)C=C1N AYAKPRUPZTWPLK-UHFFFAOYSA-N 0.000 claims description 2
- NQHVJMJEWQQXBS-UHFFFAOYSA-N 4-ethoxybenzene-1,3-diamine Chemical compound CCOC1=CC=C(N)C=C1N NQHVJMJEWQQXBS-UHFFFAOYSA-N 0.000 claims description 2
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 2
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 claims description 2
- HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 claims description 2
- WERSDZKEJFOKJJ-UHFFFAOYSA-N 4-methoxy-5-methylbenzene-1,3-diamine Chemical compound COC1=C(C)C=C(N)C=C1N WERSDZKEJFOKJJ-UHFFFAOYSA-N 0.000 claims description 2
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 claims description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 claims description 2
- UOWYGPTYSRURDP-UHFFFAOYSA-N 4-n,4-n-dipropylbenzene-1,4-diamine Chemical compound CCCN(CCC)C1=CC=C(N)C=C1 UOWYGPTYSRURDP-UHFFFAOYSA-N 0.000 claims description 2
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 claims description 2
- OAQDBKQAJRFJIY-UHFFFAOYSA-N 4-n-[2-(4-amino-n-ethyl-3-methylanilino)ethyl]-4-n-ethyl-2-methylbenzene-1,4-diamine Chemical compound C=1C=C(N)C(C)=CC=1N(CC)CCN(CC)C1=CC=C(N)C(C)=C1 OAQDBKQAJRFJIY-UHFFFAOYSA-N 0.000 claims description 2
- OOPWJBCZQDTTNE-UHFFFAOYSA-N 4-n-[4-(4-aminoanilino)butyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NCCCCNC1=CC=C(N)C=C1 OOPWJBCZQDTTNE-UHFFFAOYSA-N 0.000 claims description 2
- IAHRJSQKTFSDBY-UHFFFAOYSA-N 5-(4-aminoanilino)-3-[(4-aminoanilino)methyl]pentan-1-ol Chemical compound OCCC(CCNC1=CC=C(C=C1)N)CNC1=CC=C(C=C1)N IAHRJSQKTFSDBY-UHFFFAOYSA-N 0.000 claims description 2
- CQPLGGXOAHSQBD-UHFFFAOYSA-N 5-amino-2,4-dimethoxyphenol Chemical compound COC1=CC(OC)=C(O)C=C1N CQPLGGXOAHSQBD-UHFFFAOYSA-N 0.000 claims description 2
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- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- LEGMHPGYPXPXKB-UHFFFAOYSA-N piperidin-2-ol Chemical compound OC1CCCCN1 LEGMHPGYPXPXKB-UHFFFAOYSA-N 0.000 description 1
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- HQRFNKWPPWDXOQ-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3,6-diamine Chemical compound C1=C(N)C=CC2=C(N)C=NN21 HQRFNKWPPWDXOQ-UHFFFAOYSA-N 0.000 description 1
- AMMRTECEGYRILQ-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3,7-diamine Chemical compound NC1=CC=CC2=C(N)C=NN21 AMMRTECEGYRILQ-UHFFFAOYSA-N 0.000 description 1
- PNFZIEOWPDFJBH-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3,7-diamine Chemical compound NC1=CC=NC2=C(N)C=NN21 PNFZIEOWPDFJBH-UHFFFAOYSA-N 0.000 description 1
- CEHRKCVOIOQHDK-UHFFFAOYSA-N pyrazolo[1,5-b]pyridazin-3-amine Chemical compound N1=CC=CC2=C(N)C=NN21 CEHRKCVOIOQHDK-UHFFFAOYSA-N 0.000 description 1
- AYUWHBZBYJYVTO-UHFFFAOYSA-N pyrazolo[5,1-b][1,3]thiazol-3-amine Chemical compound C1=NN2C(N)=CSC2=C1 AYUWHBZBYJYVTO-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical class NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- JCZPOYAMKJFOLA-UHFFFAOYSA-N pyrrolidine-3,4-diol Chemical compound OC1CNCC1O JCZPOYAMKJFOLA-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- MAROONSWSSXHPU-UHFFFAOYSA-N quinoline-2,3-diamine Chemical class C1=CC=C2N=C(N)C(N)=CC2=C1 MAROONSWSSXHPU-UHFFFAOYSA-N 0.000 description 1
- XIZYKAZECQYWGU-UHFFFAOYSA-N quinoline-5,7,8-triamine Chemical compound C1=CC=NC2=C(N)C(N)=CC(N)=C21 XIZYKAZECQYWGU-UHFFFAOYSA-N 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
Description
B07-0709FR FB/ ET OA 07 283B07-0709EN FB / ET OA 07 283
Société Anonyme dite : L'OREALSociété Anonyme known as L'OREAL
Composition de teinture d'oxydation des fibres kératiniques comprenant un ou plusieurs éther(s) de cellulose cationique(s), un ou plusieurs dérivé(s) de diaminopyrazolone, et un ou plusieurs autre(s) colorant(s) d'oxydation, procédé de teinture d'oxydation et utilisation. An oxidation dyeing composition of keratinous fibers comprising one or more cationic cellulose ether (s), one or more diaminopyrazolone derivative (s), and one or more other oxidation dye (s), oxidation dyeing process and use.
Invention de : Marie-Pascale AUDOUSSET Delphine ALLARD Jean-Marc DUMONTIER Composition de teinture d'oxydation des fibres kératiniques comprenant un ou plusieurs éther(s) de cellulose cationique(s), un ou plusieurs dérivé(s) de diaminopyrazolone, et un ou plusieurs autre(s) colorant(s) d'oxydation, procédé de teinture d'oxydation et utilisation. Invention of: Marie-Pascale AUDOUSSET Delphine ALLARD Jean-Marc DUMONTIER Composition for the oxidation dyeing of keratinous fibers comprising one or more cationic cellulose ether (s), one or more derivatives of diaminopyrazolone, and one or more several other oxidation dye (s), oxidation dyeing process and use.
La présente demande a pour objet une composition de teinture d'oxydation des fibres kératiniques, et en particulier des fibres kératiniques humaines telles que les cheveux, comprenant un ou plusieurs éther(s) de cellulose cationique(s), un ou plusieurs dérivé(s) de diaminopyrazolone et/ou un ou plusieurs de leurs sels d'addition à titre de base d'oxydation, et un ou plusieurs second(s) colorant(s) d'oxydation de nature différente du (ou des) premier(s). L'invention a aussi pour objet l'utilisation de cette composition pour la teinture des fibres kératiniques ainsi que le procédé de teinture mettant en oeuvre cette composition. The subject of the present application is an oxidation dyeing composition for keratinous fibers, and in particular human keratinous fibers such as the hair, comprising one or more cationic cellulose ether (s), one or more derivatives (s). ) of diaminopyrazolone and / or one or more of their addition salts as oxidation base, and one or more second oxidation dye (s) of a different nature from the first (s) . The subject of the invention is also the use of this composition for dyeing keratinous fibers as well as the dyeing process using this composition.
Il est connu de teindre les fibres kératiniques et en particulier les cheveux humains avec des compositions tinctoriales contenant des précurseurs de colorant d'oxydation, appelés généralement bases d'oxydation, tels que des ortho- ou para-phénylènediamines, des orthoou para-aminophénols et des composés hétérocycliques. Ces bases d'oxydation sont des composés incolores ou faiblement colorés qui, associés à des produits oxydants, peuvent donner naissance par un processus de condensation oxydative à des composés colorés. On sait également que l'on peut faire varier les nuances obtenues avec ces bases d'oxydation en les associant à des coupleurs ou modificateurs de coloration, ces derniers étant choisis notamment parmi les méta-diamines aromatiques, les méta-aminophénols, les métadiphénols et certains composés hétérocycliques tels que des composés indoliques. La variété des molécules mises en jeu au niveau des bases d'oxydation et des coupleurs, permet l'obtention d'une riche palette de couleurs. It is known to dye keratinous fibers and in particular human hair with dyeing compositions containing oxidation dye precursors, generally known as oxidation bases, such as ortho- or para-phenylenediamines, ortho or para-aminophenols and heterocyclic compounds. These oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, can give rise to colored compounds by a process of oxidative condensation. It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or color modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds. The variety of molecules involved in oxidation bases and couplers, allows to obtain a rich palette of colors.
La coloration dite "permanente" obtenue grâce à ces colorants d'oxydation, doit par ailleurs satisfaire un certain nombre d'exigences. Ainsi, elle doit être sans inconvénient sur le plan toxicologique, elle doit permettre d'obtenir des nuances dans l'intensité souhaitée et présenter une bonne tenue face aux agents extérieurs tels que la lumière, les intempéries, le lavage, les ondulations permanentes, la transpiration et les frottements. Les colorants doivent également permettre de couvrir les cheveux blancs, et être enfin les moins sélectifs possibles, c'est-à-dire permettre d'obtenir des écarts de coloration les plus faibles possibles tout au long d'une même fibre kératinique, qui comporte en général des zones différemment sensibilisées (i.e. abîmées) de sa pointe à sa racine. L'utilisation des éthers de cellulose cationiques dans des compositions de coloration d'oxydation pour fibres kératiniques est connue, notamment, par la demande de brevet WO 2006/099163. Le but de la présente invention est l'obtention de compositions de coloration capillaire stables, notamment sous forme de crèmes, faciles à préparer et à appliquer, ayant de bonnes qualités rhéologiques et conduisant à des colorations peu sélectives et résistantes aux diverses agressions que peuvent subir les fibres kératiniques. De manière surprenante et avantageuse, la Demanderesse a découvert que l'utilisation, en combinaison, d' un ou plusieurs éther(s) de cellulose cationique(s) particulier(s), d'un ou plusieurs dérivé(s) de diaminopyrazolone et/ou un ou plusieurs de ses (ou de leurs) sels d'addition, à titre de première(s) base(s) d'oxydation, et d'un ou plusieurs second(s) colorant(s) d'oxydation de nature différente de la (ou des) première(s) base(s) d'oxydation, permet d'obtenir des compositions de coloration capillaire de très bonne qualité aux propriétés améliorées. Les compositions tinctoriales selon l'invention présentent notamment les propriétés suivantes : • ces compositions tinctoriales peuvent comprendre des colorants sous forme de sels en concentrations élevées sans présenter de problèmes de stabilité, • il est possible d'obtenir des compositions de viscosité correspondant à une crème qui sont stables dans le temps, • ces compositions se distinguent par une facilité de mélange avec la composition oxydante, • ces compositions se distinguent par les qualités rhéologiques des crèmes obtenues (bonne viscosité de crème en mélange), • facilité d'application des compositions après mélange avec la composition oxydante au moment de la mise en oeuvre de la coloration (qualités d'usage sur tête). The so-called "permanent" coloration obtained with these oxidation dyes must also meet a certain number of requirements. Thus, it must be harmless from the toxicological point of view, it must make it possible to obtain shades in the desired intensity and to have good resistance to external agents such as light, bad weather, washing, permanent undulations, sweating and friction. The dyes must also make it possible to cover the white hairs, and finally be the least selective possible, that is to say to make it possible to obtain the lowest possible color differences throughout a single keratinous fiber, which comprises in general, areas that are differently sensitized (ie damaged) from its tip to its root. The use of cationic cellulose ethers in oxidation dyeing compositions for keratinous fibers is known, in particular, from patent application WO 2006/099163. The object of the present invention is to obtain stable hair coloring compositions, in particular in the form of creams, easy to prepare and apply, having good rheological qualities and leading to colorings that are not very selective and resistant to the various aggressions that can undergo keratinous fibers. Surprisingly and advantageously, the Applicant has discovered that the use, in combination, of one or more particular cationic cellulose ether (s), one or more diaminopyrazolone derivative (s) and or one or more of its addition salts (or their salts), as the first base (s) of oxidation, and of one or more second dye (s) of oxidation of different nature of the (or) first (s) base (s) oxidation, allows to obtain hair coloring compositions of very good quality with improved properties. The dyeing compositions according to the invention have, in particular, the following properties: These dyeing compositions may comprise dyestuffs in the form of salts in high concentrations without presenting stability problems, it is possible to obtain viscosity compositions corresponding to a cream. These compositions are distinguished by an ease of mixing with the oxidizing composition, these compositions are distinguished by the rheological qualities of the creams obtained (good viscosity of cream in a mixture), ease of application of the compositions. after mixing with the oxidizing composition at the time of the implementation of the coloration (qualities of use on head).
En outre, les compositions selon l'invention permettent l'obtention de compositions capables de conduire à des colorations aux nuances variées, chromatiques, puissantes, esthétiques, peu sélectives, uniformes sur l'ensemble de la chevelure et résistant bien aux diverses agressions que peuvent subir les fibres. In addition, the compositions according to the invention make it possible to obtain compositions capable of leading to colorations with various shades, chromatic, powerful, aesthetic, not very selective, uniform over the whole of the hair and resistant to the various aggressions that can to undergo the fibers.
Ces compositions sont aussi non-agressives pour le cuir chevelu lors de l'application. La présente invention a pour objet une composition tinctoriale pour fibres kératiniques, et en particulier pour fibres kératiniques humaines telles que les cheveux, comprenant, dans un milieu approprié pour la teinture, un ou plusieurs éther(s) de cellulose cationique(s) particulier(s) décrit(s) ci-dessous, un ou plusieurs dérivé(s) de 2,3-diaminopyrazolone et/ou un ou plusieurs de ses (ou de leurs) sels d'addition (composés A), à titre de bases d'oxydation, et un ou plusieurs second(s) colorant(s) d'oxydation différent(s) du (ou des) composé(s) A. Un autre objet de la présente invention consiste en un procédé de teinture des fibres kératiniques dans lequel la composition cosmétique selon l'invention est mise en oeuvre. Un troisième objet de l'invention concerne l'utilisation de cette composition cosmétique pour la teinture des fibres kératiniques, et en particulier des fibres kératiniques humaines, telles que les cheveux. D'autres caractéristiques, aspects, objets et avantages de la présente invention apparaîtront encore plus clairement à la lecture de la description et des exemples qui suivent. These compositions are also non-aggressive for the scalp during application. The subject of the present invention is a dyeing composition for keratinous fibers, and in particular for human keratinous fibers such as the hair, comprising, in a medium which is suitable for dyeing, one or more particular cationic cellulose ether (s) (s) ( s) described below, one or more derivatives of 2,3-diaminopyrazolone and / or one or more of its (or their) addition salts (compounds A), as bases of oxidation, and one or more second oxidation dye (s) different (s) of (or) compound (s) A. Another object of the present invention is a method of dyeing keratin fibers in which the cosmetic composition according to the invention is used. A third object of the invention relates to the use of this cosmetic composition for dyeing keratinous fibers, and in particular human keratinous fibers, such as the hair. Other features, aspects, objects and advantages of the present invention will become more apparent upon reading the description and the examples which follow.
La composition tinctoriale pour fibres kératiniques, selon l'invention, comprend, dans un milieu approprié pour la teinture : A) un ou plusieurs éther(s) de cellulose cationique(s) comprenant de 4 000 à 10 000 motifs anhydroglucoses, lesdits motifs anhydroglucoses étant substitués par au moins : (i) un substituant de formule [R4R5R6R9N+](X2 ), dans laquelle : R4 et R5 représentent, indépendamment l'un de l'autre, un groupe méthyle ou éthyle, R6 représente un groupe alkyle, linéaire ou ramifié, en C8-C24 ou aralkyle dont la partie alkyle, linéaire ou ramifiée, est en C8-C24, R9 représente un groupe divalent permettant le rattachement au groupement anhydroglucose et choisi parmi -(B)q-CH2-CHOH-CH2- et -CH2CH2-, q désignant 0 ou 1, B désignant un groupe divalent -(CH2CH2O)ä'-, n' un nombre entier allant de 1 à 100, X2 représente un anion ; et (ii) un substituant de formule [R1R2R3R8N+](X1-), dans laquelle : R1, R2, R3 représentent, indépendamment l'un de l'autre, un groupe méthyle ou éthyle, R8 représente un groupe divalent permettant le rattachement au groupement anhydroglucose et choisi parmi -(A)p-CH2-CHOH-CH2- et -CH2CH2-, p désignant 0 ou 1, A désignant un groupe divalent -(CH2CH2O)ä-, n un nombre entier allant de 1 à 100, X1- représente un anion ; B) un ou plusieurs dérivé(s) de 2,3-diaminopyrazolone et/ou un ou plusieurs de ses (ou de leurs) sels d'addition (composé(s) A) ; et C) un ou plusieurs second(s) colorant(s) d'oxydation différent(s) du (ou des) composé(s) A. The dyeing composition for keratin fibers, according to the invention, comprises, in a medium suitable for dyeing: A) one or more cationic cellulose ether (s) comprising from 4,000 to 10,000 anhydroglucose units, said anhydroglucose units; being substituted by at least: (i) a substituent of the formula [R4R5R6R9N +] (X2), wherein: R4 and R5 are, independently of one another, a methyl or ethyl group, R6 is a linear alkyl group or branched, C8-C24 or aralkyl whose linear or branched alkyl part is C8-C24, R9 represents a divalent group allowing attachment to the anhydroglucose group and chosen from - (B) q-CH2-CHOH-CH2- and -CH2CH2-, wherein q is 0 or 1, where B is a divalent group - (CH2CH2O); n 'is an integer from 1 to 100, X2 is an anion; and (ii) a substituent of the formula [R1R2R3R8N +] (X1-), wherein: R1, R2, R3 represent, independently of one another, a methyl or ethyl group, R8 represents a divalent group allowing attachment to the anhydroglucose moiety and selected from - (A) p-CH2-CHOH-CH2- and -CH2CH2-, wherein p is 0 or 1, A is a divalent group - (CH2CH2O) n, n is an integer from 1 to 100, X1- represents an anion; B) one or more derivative (s) of 2,3-diaminopyrazolone and / or one or more of its (or their) addition salts (compound (s) A); and C) one or more second oxidation dye (s) different from the compound (s) A.
De préférence, le substituant (i) de formule [R4RSR6R9N+](X2-) est présent en une moyenne de 0,0003 à 0,08 mole, par mole d'unité anhydroglucose. Les éthers de cellulose cationiques utilisables dans les compositions selon l'invention sont, de préférence, des hydroxyéthyl ou hydroxypropyl celluloses. Les éthers de cellulose cationiques utilisables dans les compositions selon l'invention comprennent, de préférence, plus de 4 500, avantageusement, plus de 5000, et de manière plus préférée, plus de 6000 motifs anhydroglucoses. De préférence, les éthers de cellulose cationiques utilisables dans les compositions selon l'invention comprennent, de préférence, jusqu'à 9000, et de manière préférée, jusqu'à 8000 motifs anhydroglucoses. Ces éthers de cellulose cationiques et leur procédé de préparation sont décrits dans la demande WO 2005/000903. Preferably, the substituent (i) of formula [R4RSR6R9N +] (X2-) is present in an average of 0.0003 to 0.08 mol, per mole of anhydroglucose unit. The cationic cellulose ethers which can be used in the compositions according to the invention are preferably hydroxyethyl or hydroxypropyl celluloses. The cationic cellulose ethers which can be used in the compositions according to the invention preferably comprise more than 4500, advantageously more than 5000, and more preferably more than 6000 anhydroglucose units. Preferably, the cationic cellulose ethers which can be used in the compositions according to the invention preferably comprise up to 9000, and preferably up to 8000 anhydroglucose units. These cationic cellulose ethers and their method of preparation are described in application WO 2005/000903.
Selon une variante préférée, les éthers de cellulose cationiques utilisables dans les compositions selon l'invention sont formés d'au moins un motif (IV) et d'au moins un des motifs (I), (II) ou (III) suivants : (I) /O(CH2CH2O)nH CH2 (CH2CH2O)n.H R1 /O(CH2CH2O)n ùCH2CH ùCH2 + NùR2 I _ CH2 OH R3 X1 (CH2CH2O) n.H H R4 (CH2CH2O)n.ùCH2CHùCH2 NùR5 + OH R6 X2 R1 7Où(CH2CH2O)n ùCH2CHùCH2 + NùR2 CH2 OH R3 X1 H R 1 4 (CH2CH2O)n, CH2CHùCH2 NùR5 + OH R6 (IV) X2 sous réserve que : le nombre total des motifs (I) + (II) + (III) + (IV) soit compris entre 4000 et 10000 ; le rapport [(III) + (IV)] / [(I) + (II) + (III) + (IV)] va de 0,0003 à0,8; le rapport [(II) + (IV)] / [(I) + (II) + (III) + (IV)] va de 0,02 à 0,9 ; les nombres entiers n et n', indépendamment l'un de l'autre, vont de0à5; R1, R2, R3, R4 et R5 représentent, indépendamment l'un de l'autre, un groupe méthyle ou éthyle ; R6 représente un groupement alkyle, linéaire ou ramifié, en C8-C24, de préférence en Cio-Cz4, de manière plus préférée en C12-C24, et mieux encore en C12-C15, ou un groupement aralkyle dont la partie /O(CH2CH2O)nH CH alkyle, linéaire ou ramifiée, est en C8-C24 ; X1- et X2 représentent des anions choisis, de préférence, indépendamment l'un de l'autre, parmi les ions phosphate, nitrate, sulfate et halogénure (Cl-, Br-, F-, I-). According to a preferred variant, the cationic cellulose ethers that can be used in the compositions according to the invention are formed of at least one unit (IV) and at least one of the following units (I), (II) or (III): (I) / O (CH 2 CH 2 O) n H CH 2 (CH 2 CH 2 O) n H R 1 / O (CH 2 CH 2 O) n CH 2 CH ùCH 2 + N 1 R 2 I CH 2 OH R 3 X 1 (CH 2 CH 2 O) n H H R 4 (CH 2 CH 2 O) n CH 2 CH 2 CH 2 N 5 R 5 + OH R 6 X 2 R 1 7 (CH 2 CH 2 O) n CH 2 CH 2 CH 2 + N 1 R 2 CH 2 OH R 3 X 1 HR 1 4 (CH 2 CH 2 O) n, CH 2 CH 2 CH 2 N 5 R 5 + OH R 6 (IV) X 2 provided that: the total number of units (I) + (II) + (III) + ( IV) is between 4000 and 10000; the ratio [(III) + (IV)] / [(I) + (II) + (III) + (IV)] ranges from 0.0003 to 0.8; the ratio [(II) + (IV)] / [(I) + (II) + (III) + (IV)] is from 0.02 to 0.9; the integers n and n ', independently of one another, range from 5 to 5; R1, R2, R3, R4 and R5 represent, independently of one another, a methyl or ethyl group; R6 represents a linear or branched C8-C24, preferably C10-C14, more preferably C12-C24, and more preferably C12-C15, or an aralkyl group whose part / O (CH2CH2O); linear or branched alkyl CH is C8-C24; X 1 and X 2 represent anions chosen, preferably independently of one another, from phosphate, nitrate, sulfate and halide ions (Cl-, Br-, F-, I-).
Selon une variante particulière, les éthers de cellulose cationiques utilisables dans les compositions selon l'invention, sont formés d'au moins un motif (IV) et d'au moins un des motifs (I), (II) ou (III) ci-dessus dans le(s)quel(s) R6 est un groupement dodécyle linéaire. According to a particular variant, the cationic cellulose ethers that can be used in the compositions according to the invention are formed of at least one unit (IV) and at least one of the units (I), (II) or (III) ci above in which R6 is a linear dodecyl group.
Parmi les éthers de cellulose cationiques utilisables dans les compositions de l'invention, on peut citer les polymères de type SOFTCAT SL-5, SL-30, SL-60 et SL-100 (INCI : Polyquaternium-67) commercialisés par la société Amerchol. Les éthers de cellulose cationiques particulièrement préférés sont les polymères de type SL-60 et SL-100. La composition selon l'invention peut comprendre un ou plusieurs éther(s) de cellulose cationique(s) tel(s) que défini(s) précédemment. La concentration en éther(s) de cellulose cationique(s) des compositions selon l'invention va de préférence de 0,01 à 10 % en poids, en particulier de 0,05 à 3 % en poids, et de manière plus préférée de 0,1 à 1 % en poids, par rapport au poids total de la composition. Par "dérivé(s) de 2,3-diaminopyrazolone" ou "composé(s) A", on entend un (ou des) composé(s) comportant dans sa (ou leur) structure moléculaire la sous-structure suivante : Le (ou les) dérivé(s) de 2,3-diaminopyrazolone selon l'invention répond(ent), de préférence, à la formule générale (V) suivante : Among the cationic cellulose ethers that may be used in the compositions of the invention, mention may be made of the polymers of the SOFTCAT SL-5, SL-30, SL-60 and SL-100 (INCI: Polyquaternium-67) type marketed by Amerchol. . Particularly preferred cationic cellulose ethers are SL-60 and SL-100 polymers. The composition according to the invention may comprise one or more cationic cellulose ether (s) as defined previously. The concentration of cationic cellulose ether (s) of the compositions according to the invention is preferably from 0.01 to 10% by weight, in particular from 0.05 to 3% by weight, and more preferably from 0.1 to 1% by weight, relative to the total weight of the composition. By "derivative (s) of 2,3-diaminopyrazolone" or "compound (s) A" is meant a compound (or compounds) comprising in its (or their) molecular structure the following substructure: or the 2,3-diaminopyrazolone derivative (s) according to the invention preferably corresponds to the following general formula (V):
O /NH2O / NH2
R i NR3R4 R2 (V) dans laquelle : ^ R1, R2, R3 et R4, identiques ou différents, représentent, indépendamment l'un de l'autre : - un atome d'hydrogène ; - un groupe alkyle en C1-C1o, de préférence en C1-C6, linéaire ou ramifié, éventuellement substitué par un ou plusieurs groupes choisis parmi les groupes OR5, NR6R7, carboxy, les groupes sulfoniques, carboxamido CONR6R7, sulfonamido SO2NR6R7, les hétérocycles aliphatiques tel que la pipéridine, les aryles éventuellement substitués par un ou plusieurs groupe(s) choisi(s) parmi les groupes alkyle en C1-C4, hydroxy, alcoxy en C1-C2, amino et (di)alkyl(C1-C2)amino ; - un groupe aryle éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes alkyle en C1-C4, hydroxy, alcoxy en C1-C2, amino et (di)alkyl(C1-C2)amino ; - un groupe hétéroaryle à 5 ou 6 chaînons, éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes alkyle en C1-C4 et alcoxy en C1-C2 ; ^ R5, R6 et R7, identiques ou différents, représentent : - un atome d'hydrogène ; - un groupe alkyle en C1-C4, de préférence en C1-C2, linéaire ou ramifié, éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes hydroxy, alcoxy en C1-C2, carboxamido CONR8R9, sulfonyle S02R8, aryle éventuellement substitué par un groupe alkyle en C1-C4, hydroxy, alcoxy en C1-C2, amino, (di)alkyl(C1-C2)amino ; - un groupe aryle éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes alkyle en C1-C4, hydroxy, alcoxy en C1-C2, amino, (di)alkyl(C1-C2)amino ; - un groupe carboxamido CONR8R9; - un groupe sulfonyle S02R8; ^ R8 et R9, identiques ou différents, représentent un atome d'hydrogène ; un groupe alkyle en C1-C4, linéaire ou ramifié, éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes hydroxy et alcoxy en C1C2 ; ^ R1 et R2 d'une part, et R3 et R4 d'autre part, peuvent également former ensemble avec le (ou les) atome(s) d'azote au(x)quel(s) ils sont rattachés un hétérocycle, saturé ou insaturé, comportant de 5 à 7 chaînons, éventuellement substitué ou N-substitué par un ou plusieurs groupe(s) choisi(s) parmi les atomes d'halogène, les groupes amino, (di)alkyl(C1-C4)amino, (di)hydroxyalkyl(C1-C2)amino, hydroxy, carboxy, carboxamido, (di)alkyl(C1-C2)carboxamido, alcoxy en C1-C2 et les groupes alkyle en C1-C4 éventuellement substitués par un ou plusieurs groupes choisis parmi les groupes hydroxy, amino, (di)alkylamino, alcoxy, carboxy et sulfonyle ; lesdits hétérocycles formés par R1 et R2 d'une part, et R3 et R4 d'autre part, avec le (ou les) atome(s) d'azote au(x)quel(s) ils sont rattachés, pouvant être identiques ou différents, et les chaînons formant lesdits hétérocycles pouvant être, de préférence, choisis parmi des atomes de carbone, d'azote et d'oxygène. Selon un mode de réalisation particulier, R1 et R2, identiques ou différents, sont choisis, indépendamment l'un de l'autre, parmi : - un groupe alkyle en C1-C6 éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes hydroxy, alcoxy en C1-C2, amino et (di)alkyl(C1-C2)amino ; et - un groupe phényle, méthoxyphényle, éthoxyphényle, ou benzyle. In which: R1, R2, R3 and R4, which may be identical or different, represent, independently of one another: a hydrogen atom; a linear or branched C1-C10, preferably C1-C6, alkyl group optionally substituted with one or more groups chosen from OR5, NR6R7, carboxy groups, sulphonic groups, carboxamido CONR6R7, sulphonamido SO2NR6R7, aliphatic heterocycles; such as piperidine, aryls optionally substituted with one or more groups selected from C 1 -C 4 alkyl, hydroxy, C 1 -C 2 alkoxy, amino and (di) C 1 -C 2 alkyl amino groups; ; an aryl group optionally substituted by one or more groups chosen from among the C 1 -C 4 alkyl, hydroxy, C 1 -C 2 alkoxy, amino and (di) C 1 -C 2 alkyl amino groups; a 5- or 6-membered heteroaryl group, optionally substituted by one or more group (s) chosen from C1-C4 alkyl and C1-C2 alkoxy groups; R5, R6 and R7, which may be identical or different, represent: a hydrogen atom; - a C1-C4 alkyl group, preferably C1-C2, linear or branched, optionally substituted by one or more group (s) chosen from hydroxyl groups, C1-C2 alkoxy, carboxamido CONR8R9, sulfonyl SO2R8 aryl optionally substituted with C 1 -C 4 alkyl, hydroxy, C 1 -C 2 alkoxy, amino, (di) (C 1 -C 2) alkylamino; an aryl group optionally substituted with one or more groups chosen from C1-C4alkyl, hydroxy, C1-C2alkoxy, amino, (di) (C1-C2) alkylamino; a carboxamido group CONR8R9; a sulfonyl group SO2R8; R8 and R9, identical or different, represent a hydrogen atom; a linear or branched C1-C4 alkyl group optionally substituted by one or more groups selected from hydroxy and C1-C2 alkoxy groups; R1 and R2 on the one hand, and R3 and R4 on the other hand, can also form together with the nitrogen atom (s) to which they are attached a saturated heterocycle or unsaturated, having from 5 to 7 members, optionally substituted or N-substituted with one or more groups selected from halogen atoms, amino groups, (di) (C 1 -C 4) alkylamino, (di) hydroxy (C 1 -C 2) alkylamino, hydroxy, carboxy, carboxamido, (C 1 -C) alkyl (C 1 -C 2) carboxamido, C 1 -C 2 alkoxy and C 1 -C 4 alkyl groups optionally substituted by one or more groups selected from hydroxy, amino, (di) alkylamino, alkoxy, carboxy and sulfonyl groups; said heterocycles formed by R1 and R2 on the one hand, and R3 and R4 on the other hand, with the nitrogen atom (s) to which they are attached, which may be identical or different, and the links forming said heterocycles may be preferably selected from carbon, nitrogen and oxygen. According to a particular embodiment, R1 and R2, which are identical or different, are chosen, independently of one another, from: - a C1-C6 alkyl group optionally substituted by one or more selected group (s) ) among hydroxy, C1-C2 alkoxy, amino and (di) C1-C2 alkylamino groups; and a phenyl, methoxyphenyl, ethoxyphenyl or benzyl group.
De préférence, R1 et R2, identiques ou différents, sont choisis, indépendamment l'un de l'autre, parmi les groupes méthyle, éthyle, 2-hydroxyéthyle, 3-hydroxypropyle, 2-hydroxypropyle et phényle. Selon un autre mode de réalisation, R1 et R2 forment ensemble avec les atomes d'azote auxquels ils sont rattachés un cycle à 5 ou 6 chaînons, saturé ou insaturé, éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les atomes d'halogène, les groupes amino, (di)alkyl(C1-C4)amino, (di)hydroxyalkyl(C1-C2)amino, hydroxy, carboxy, carboxamido, (di)alkyl(C1-C2)carboxamido, alcoxy en C1-C2, les groupes alkyle en C1-C4 éventuellement substitués par un ou plusieurs groupe(s) choisi(s) parmi les groupes hydroxy, amino, (di)alkylamino, alcoxy, carboxy et sulfonyle. De préférence, R1 et R2 forment ensemble avec les atomes d'azote auxquels ils sont rattachés un cycle pyrazolidine ou pyridazolidine, éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes alkyle en C1_C4, hydroxy, alcoxy en C1-C2, carboxy, carboxamido, amino et (di)alkyl(C1-C2)amino. De préférence, R1 et R2 forment ensemble avec les atomes d'azote auxquels ils sont rattachés un cycle pyrazolidine ou pyridazolidine, éventuellement substitué par un ou plusieurs groupes choisis parmi les groupes alkyle en C1_C4, hydroxy, alcoxy en C1-C2, carboxy, carboxamido, amino et (di)alkyl(C1-C2)amino. De manière encore plus avantageuse, R1 et R2 forment ensemble avec les atomes d'azote auxquels ils sont rattachés, un cycle pyrazolidine, 25 pyridazoline ou pyridazolidine. En ce qui concerne R3 et R4, ces derniers, identiques ou différents, sont plus particulièrement choisis parmi un atome d'hydrogène ; un groupe alkyle en C1-C6, linéaire ou ramifié, éventuellement substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes hydroxy, alcoxy en C1-C2, 30 amino, (di)alkyl(C1-C2)amino et les hétérocycles aliphatiques tel que la pipéridine ; un groupe phényle éventuellement substitué par un ou plusieurs groupes choisis parmi les groupes hydroxy, amino et alcoxy en C1-C2. Preferably, R1 and R2, which are identical or different, are chosen, independently of one another, from methyl, ethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl and phenyl groups. According to another embodiment, R1 and R2 together with the nitrogen atoms to which they are attached form a saturated or unsaturated 5- or 6-membered ring, optionally substituted with one or more groups selected from among the halogen atoms, amino groups, (di) (C 1 -C 4) alkylamino, (di) hydroxyalkyl (C 1 -C 2) amino, hydroxy, carboxy, carboxamido, (di) (C 1 -C 2) alkylcarboxamido, alkoxy C1-C2, C1-C4 alkyl groups optionally substituted with one or more groups selected from hydroxy, amino, (di) alkylamino, alkoxy, carboxy and sulfonyl groups. Preferably, R1 and R2 together with the nitrogen atoms to which they are attached form a pyrazolidine or pyridazolidine ring, optionally substituted by one or more group (s) chosen from C1-C4 alkyl, hydroxy, C1-alkoxy groups. -C 2, carboxy, carboxamido, amino and (di) (C 1 -C 2) alkylamino. Preferably, R 1 and R 2 together with the nitrogen atoms to which they are attached form a pyrazolidine or pyridazolidine ring, optionally substituted by one or more groups selected from C 1 -C 4 alkyl, hydroxy, C 1 -C 2 alkoxy, carboxy, carboxamido groups. amino and (di) (C1-C2) alkylamino. Even more advantageously, R 1 and R 2 together with the nitrogen atoms to which they are attached form a pyrazolidine, pyridazoline or pyridazolidine ring. As regards R3 and R4, the latter, which are identical or different, are more particularly chosen from a hydrogen atom; a linear or branched C1-C6 alkyl group optionally substituted with one or more groups chosen from hydroxyl, C1-C2 alkoxy, amino, (di) C1-C2 alkylamino groups; and aliphatic heterocycles such as piperidine; a phenyl group optionally substituted with one or more groups selected from hydroxy, amino and C1-C2 alkoxy groups.
De préférence, R3 et R4, identiques ou différents, sont choisis parmi un atome d'hydrogène, un groupe méthyle, éthyle, isopropyle, 2-hydroxyéthyle, 3-hydroxypropyle, 2-hydroxypropyle et 2-carboxyéthyle , 2-diméthylaminoéthyle, pyrrolidin-1-yle, 3-hydroxypyrrolidin-1-yle, 4-pipéridin-1-yle, 4-méthylpipéridin-1-yle, et 3-diméthylaminopipéridin-1-yle. Selon un mode de réalisation particulier, les groupes R3 et R4 représentent un atome d'hydrogène. Selon un autre mode de réalisation, R3 et R4 forment ensemble avec l'atome d'azote auquel ils sont rattachés, un cycle comportant de 5 à 7 chaînons choisi parmi les hétérocycles pyrrolidine, pipéridine, homopipéridine, pipérazine et homopipérazine ; ledit cycle pouvant être substitué ou N-substitué par un ou plusieurs groupe(s) choisi(s) parmi les groupes hydroxy, amino, (di)alkyl(C1-C2)amino, (di)hydroxyalkyl(C1-C2)- amino, carboxy, carboxamido, (di)alkyl(C1-C2)carboxamido et alkyle en C1-C4 éventuellement substitué(s) par un ou plusieurs groupe(s) choisi(s) parmi les groupes hydroxy, amino et (di)alkylamino en C1-C2. Plus particulièrement, R3 et R4 forment ensemble avec l'atome d'azote auquel ils sont rattachés un cycle comportant de 5 à 7 chaînons choisi parmi la pyrrolidine, le 2,5-diméthylpyrrolidine, l'acide pyrrolidine-2-carboxylique, l'acide 3-hydroxypyrrolidine-2-carboxylique, l'acide 4-hydroxypyrrolidine-2-carboxylique, la 2,4-dicarboxypyrrolidine, la 3-hydroxy-2-hydroxyméthylpyrrolidine, la 2-carboxamidopyrrolidine, la 3-hydroxy-2-carboxamidopyrrolidine, la 2-(diéthylcarboxamido)pyrrolidine, la 2-hydroxyméthylpyrrolidine, la 3,4-dihydroxy-2-hydroxyméthylpyrrolidine, la 3-hydroxypyrrolidine, la 3,4-dihydroxypyrrolidine, la 3-aminopyrrolidine, la 3-méthylaminopyrrolidine, la 3-diméthylaminopyrrolidine, la 4-amino-3-hydroxypyrrolidine, la 3-hydroxy-4-(2-hydroxyéthyl)aminopyrrolidine, la pipéridine, la 2,6-diméthylpipéridine, la 2-carboxypipéridine, la 2-carboxamidopipéridine, la 2-hydroxyméthylpipéridine, la 3-hydroxy-2-hydroxyméthylpipéridine, la 2-hydroxypipéridine, la 3-hydroxypipéridine, la 4-hydroxypipéridine, la 3-hydroxyméthylpipéridine, la homopipéridine, la 2-carboxyhomopipéridine, la 2-carboxamidohomopipéridine, l'homopipérazine, le N-méthylhomopipérazine et le N-(2-hydroxyéthyl)homopipérazine. De préférence, R3 et R4 forment ensemble avec l'atome d'azote auquel ils sont rattachés un cycle comportant de 5 à 7 chaînons choisi parmi la pyrrolidine, la 3-hydroxypyrrolidine, la 3-aminopyrrolidine, la 3-diméthylaminopyrrolidine, l'acide pyrrolidine-2-carboxylique, l'acide 3-hydroxypyrrolidine-2-carboxylique, la pipéridine, l' hydroxypipéridine, l'homopipéridine, le 1,4-diazépane, la N-méthylhomopipérazine et la N-13-hydroxyéthylhomopipérazine. Conformément à un mode de réalisation encore plus préféré de l'invention, R3 et R4 forment ensemble avec l'atome d'azote auquel ils sont rattachés un cycle à 5 chaînons tel que la pyrrolidine, la 3-hydroxypyrrolidine, la 3-aminopyrrolidine ou la 3-diméthylaminopyrrolidine. Preferably, R 3 and R 4, which may be identical or different, are chosen from a hydrogen atom, a methyl, ethyl, isopropyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl and 2-carboxyethyl, 2-dimethylaminoethyl, pyrrolidine, 1-yl, 3-hydroxypyrrolidin-1-yl, 4-piperidin-1-yl, 4-methylpiperidin-1-yl, and 3-dimethylaminopiperidin-1-yl. According to a particular embodiment, the groups R 3 and R 4 represent a hydrogen atom. According to another embodiment, R3 and R4 together with the nitrogen atom to which they are attached form a 5- to 7-membered ring chosen from pyrrolidine, piperidine, homopiperidine, piperazine and homopiperazine heterocycles; said ring may be substituted or N-substituted with one or more groups selected from hydroxy, amino, (di) (C1-C2) alkylamino, (di) hydroxyalkyl (C1-C2) amino , carboxy, carboxamido, (di) alkyl (C1-C2) carboxamido and C1-C4 alkyl optionally substituted with one or more groups selected from hydroxy, amino and (di) alkylamino groups. C1-C2. More particularly, R3 and R4 together with the nitrogen atom to which they are attached form a 5- to 7-membered ring selected from pyrrolidine, 2,5-dimethylpyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, 4-hydroxypyrrolidine-2-carboxylic acid, 2,4-dicarboxypyrrolidine, 3-hydroxy-2-hydroxymethylpyrrolidine, 2-carboxamidopyrrolidine, 3-hydroxy-2-carboxamidopyrrolidine, 2- (diethylcarboxamido) pyrrolidine, 2-hydroxymethylpyrrolidine, 3,4-dihydroxy-2-hydroxymethylpyrrolidine, 3-hydroxypyrrolidine, 3,4-dihydroxypyrrolidine, 3-aminopyrrolidine, 3-methylaminopyrrolidine, 3-dimethylaminopyrrolidine , 4-amino-3-hydroxypyrrolidine, 3-hydroxy-4- (2-hydroxyethyl) aminopyrrolidine, piperidine, 2,6-dimethylpiperidine, 2-carboxypiperidine, 2-carboxamidopiperidine, 2-hydroxymethylpiperidine, 3-hydroxy-2-hydroxymethylpiperidine, 2-hydroxypiperidine, 3-hydroxypiperidine, 4-hydroxypiperidine, 3-hydroxymethylpiperidine, homopiperidine, 2-carboxyhomopiperidine, 2-carboxamidohomopiperidine, homopiperazine, N-methylhomopiperazine and N- (2-hydroxyethyl) homopiperazine. Preferably, R 3 and R 4 together with the nitrogen atom to which they are attached form a 5- to 7-membered ring selected from pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine, 3-dimethylaminopyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, piperidine, hydroxypiperidine, homopiperidine, 1,4-diazepane, N-methylhomopiperazine and N-13-hydroxyethylhomopiperazine. According to an even more preferred embodiment of the invention, R 3 and R 4 together with the nitrogen atom to which they are attached form a 5-membered ring such as pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine or 3-dimethylaminopyrrolidine.
Les composés de formule (V) peuvent être éventuellement salifiés par des acides minéraux forts tels que par exemple HC1, HBr, HI, H2SO4, H3PO4, ou des acides organiques tels que, par exemple, l'acide acétique, lactique, tartrique, citrique, succinique, benzènesulfonique, para-toluènesulfonique, formique, ou méthanesulfonique. The compounds of formula (V) may optionally be salified with strong mineral acids such as, for example, HCl, HBr, HI, H 2 SO 4, H 3 PO 4, or organic acids such as, for example, acetic, lactic, tartaric or citric acid. succinic, benzenesulfonic, para-toluenesulfonic, formic, or methanesulfonic.
Ils peuvent aussi être sous forme de solvates, par exemple, un hydrate, ou un solvate d'alcool linéaire ou ramifié, tel que l' éthanol ou l'isopropanol. A titre d'exemples de dérivés de formule (V), on peut citer les composés présentés ci-dessous ou leurs sels d'addition : 4,5-diamino-1,2-diméthyl-1,2-dihydropyrazol-3-one ; 4-amino-5-méthylamino-1,2-diméthyl-1,2-dihydropyrazol-3-one ; 4-amino-5-diméthylamino-1,2-diméthyl-1,2-dihydropyrazol-3-one ; 4-amino-5-(2-hydroxyéthyl)amino-1,2-diméthyl-1,2-dihydropyrazol-3-one ; 4-amino-5-(pyrrolidin-1-yl)-1,2-diméthyl-1,2-dihydropyrazol-3-one ; 4-amino-5-(pipéridin-1-yl)-1,2-diméthyl-1,2-dihydropyrazol-3-one ; 4,5-diamino-1,2-di-(2-hydroxyéthyl)-1,2-dihydropyrazol-3-one ; 4-amino-5 -méthylamino-1,2-di-(2-hydroxyéthyl)-1,2-dihydropyrazol-3 - one 4-amino-5-diméthylamino-1,2-di-(2-hydroxyéthyl)-1,2-dihydropyrazol-3- one 4-amino-5-(2-hydroxyéthyl)amino-1,2-di-(2-hydroxyéthyl)-1, 2-dihydropyrazol-3-one ; 4-amino-5-(pyrrolidin-l-yl)-1,2-di-(2-hydroxyéthyl)-1, 2-dihydropyrazol-3-one 4-amino-5 -(pipéridin-1-yl)-1,2-di-(2-hydroxyéthyl)-1,2-dihydropyrazol-3 - one ; 4,5-diamino-1,2-diéthyl-1,2-dihydropyrazol-3-one ; 4,5-diamino-1,2-phényl-1,2-dihydropyrazol-3-one ; 4,5-diamino-1-éthyl-2-méthyl-1,2-dihydropyrazol-3-one ; 4,5-diamino-2-éthyl-1-méthyl-1,2-dihydropyrazol-3-one ; 4,5-diamino-1-phényl-2-méthyl-1,2-dihydropyrazol-3-one 4,5-diamino-2-phényl-1-méthyl-1,2-dihydropyrazol-3-one 4,5-diamino-1-(2-hydroxyéthyl)-2-méthyl-1,2-dihydropyrazol-3-one ; 4,5-diamino-2-(2-hydroxyéthyl)-1-méthyl-1,2-dihydropyrazol-3-one ; 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l-one ; 2-amino-3-méthylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l-one ; 2-amino-3-diméthylamino-6,7-dihydro-1 H,5H-pyrazolo [ 1,2-a]pyrazol- l -one 2-amino-3-éthylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l-one ; 2-amino-3-isopropylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l- one ; 2-amino-3-(2-hydroxyéthyl)amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a] -pyrazol-1-one ; 2-amino-3-(2-hydroxypropyl)amino-6,7-dihydro-1 H,5H-pyrazolo [ 1,2-a]-pyrazol-1-one ; 2-amino-3-bis(2-hydroxyéthyl)amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a] -pyrazol-1-one; 2-amino-3-(pyrrolidin-l-yl)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-lone 2-amino-3-(3-hydroxy-pyrrolidin-l-yl)-6,7-dihydro-1H,5H-pyrazolo[1,2-a] -pyrazol-l-one ; 2-amino-3-(pipéridin-l-yl)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l- one 2,3-diamino-6-hydroxy-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l-one ; 2,3-diamino-6-méthyl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l-one ; 2,3-diamino-6,6-diméthyl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l- one ; 2,3-diamino-5,6,7,8-tétrahydro-1H,6H-pyridazino[1,2-a]pyrazol-l-one ; 2,3-diamino-5,8-dihydro-1H,6H-pyridazino[1,2-a]pyrazol-l-one ; 4-amino-5-diméthylamino-1,2-diéthyl-1,2-dihydropyrazol-3-one ; 4-amino-1,2-diéthyl-5-éthylamino-1,2-dihydropyrazol-3-one ; 4- amino -1,2-diéthyl-5-isopropylamino-1,2-dihydropyrazol-3-one , 4- amino -1,2-diéthyl-5-(2-hydroxyéthylamino)-1,2-dihydropyrazol-3-one ; 4-amino-5 -(2-diméthylamino éthylamino)-1,2-diéthyl-1,2-dihydropyrazol-3 - one 4-amino-5-[bis(2-hydroxyéthyl)amino]-1,2-diéthyl-1,2-dihydropyrazol-3one ; 4-amino-1,2-diéthyl-5-(3-imidazol-1-yl-propylamino)-1, 2-dihydropyrazol-3-one ; 4-amino-1.2-diéthyl-5-(3-hydroxypyrrolidin-l-yl)-1,2-dihydropyrazol-3- one 4-amino-5-pyrrolidin-l-yl-1,2-diéthyl-1,2-dihydropyrazol-3- one 4-amino-5 -(3 -diméthylaminopyrrolidin- l -yl)-1,2-diéthyl-1,2-dihydropyrazol-3-one ; 4-amino-1,2-diéthyl-5-(4-méthylpipérazin-1-yl)pyrazolidin-3-one ; dont certains sont figurés ci-dessous pour illustrer les noms par des structures chimiques : O~ NH2 H3cùN~N NHZ 4,5-diamino-1,2-diméthyl-1,2CH3 dihydropyrazol-3-one O~ NH2 4,5-diamino-1,2-diéthyl-1,2-dihydro- % pyrazol-3-one c2H5 N NHz C2H5 O, NHZ 4,5-diamino-1,2-diphényl-1,2- Ph~N~N NH2 dihYdroPYrazol-3-one Ph O ~ NH2 4,5-diamino-1-éthyl-2-méthyl-1,2-H3C'N,N NH2 dihydropyrazol-3-one C2H5 O~ NH2 4,5-diamino-1-phényl-2-méthyl-1,2- H3C'N NH2 dihydropyrazol-3-one Ph O\ NH2 4-amino-5-(pyrrolidin-1-yl)-1,2-diéthyl- C2H5 N \ 1,2-dihydropyrazol-3-one C2H5 O~ \ NH2 4-amino-5-(3-diméthylaminopyrrolidin- ÇH3 1-yl)-1,2-diéthyl-1,2-dihydropyrazol-3-one C2H5 N•N N. CH3 C2H5 O, NH2 2,3-diamino-6,7-dihydro-lH,5H-pyrazolo \/v [1,2-a]pyrazol-l-one /NI NH2 O NH2 2-amino-3-méthylamino-6,7-dihydro- N 1H,5H-pyrazolo[1,2-a]pyrazol-l-one AH O~ NH2 2-amino-3-éthylamino-6,7-dihydro-lH,5H- N pyrazolo[1,2-a]pyrazol-1-one O~ 2 2-amino-3-(2-hydroxyéthyl)amino-6,7- N NH dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-l- OH one O, NH2 2-amino-3-(2-hydroxypropyl)amino-6,7- \/v dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-l- N' ~NH one OH O~ NH2 2-amino-3-bis(2-hydroxyéthyl)amino-6,7- OH dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-l- ~~ one ~N N OH O\ /NH2 2-amino-3-isopropylamino-6,7-dihydro- N'NH 1H,5H-pyrazolo[1,2-a]pyrazol-1-one Ç N O~ NH2 2-amino-3-(pyrrolidin-1-yl)-6,7-dihydro- N 1H,5H-pyrazolo[1,2-a]pyrazol-1-one ~ O NH2 2-amino-3-(3-hydroxypyrrolidin-l-yl)-6,7- N, OH dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-1- N N one / O~ NH2 2,3-diamino-6-hydroxy-6,7-dihydro-lH,5H- N pyrazolo[1,2-a]pyrazol-1-one \N NH2 / HO O0 ~ NH2 2,3-diamino-6-méthyl-6,7-dihydro-lH,5H- N,N NH2 pyrazolo[1,2-a]pyrazol-1-one O0 ~ NH2 2,3-diamino-6,6-diméthyl-6,7-dihydro- N'N NH2 1H,5H-pyrazolo[1,2-a]pyrazol-1-one O0 ~ NH2 2,3-diamino-5,6,7,8-tétrahydro-lH,6H- NH2 pyridazino[1,2-a]pyrazol-1-one N NN O0 ~ NH2 2,3-diamino-5,8-dihydro-lH,6H- N~N NH2 pyridazino[1,2-a]pyrazol-1-one O%~ NH2 4,5-diamino-1-(2-hydroxyéthyl)-2-méthyl- H cùN, ~NH 1,2-dihydropyrazol-3-one s N z OH /NH2 4,5-diamino-2-(2-hydroxyéthyl)-l-méthyl- \ 1,2-dihydropyrazol-3-one N NH2 HO CH3 Parmi ces composés, les dérivés de 2,3-diaminopyrazolone de formule (V) particulièrement préférés sont les suivants : 2,3-diamino-6,7-dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-l-one ; 2-amino-3-éthylamino-6,7-dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-lone ; 2-amino-3-isopropylamino-6,7-dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-1-one ; 2-amino-3-(pyrrolidin-l-yl)-6,7-dihydro-lH,5H-pyrazolo[1,2-a] -pyrazol-1-one ; 4,5-diamino-1,2-diméthyl-1,2-dihydropyrazol-3-one ; 4,5-diamino-1,2-diéthyl-1,2-dihydropyrazol-3-one ; 4,5-diamino-1,2-di-(2-hydroxyéthyl)-1,2-dihydropyrazol-3-one ; 2-amino-3-(2-hydroxyéthyl)amino-6,7-dihydro-lH,5H-pyrazolo[1,2-a] -pyrazol-1-one ; 2-amino-3-diméthylamino-6,7-dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-1-one ; 2,3-diamino-5,6,7,8-tétrahydro-lH,6H-pyridazino[1,2-a]pyrazol-l-one 4-amino-1,2-diéthyl-5-pyrrolidin-l-yl-1,2-dihydropyrazol-3-one ; 4-amino5 -(3 -diméthylamino-pyrrolidin- l -yl)-1,2-diéthyl-1,2-dihydropyrazol-3one ; 2,3-diamino-6-hydroxy-6,7-dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-lone. On préfère encore plus particulièrement la 2,3-diamino-6,7-dihydro-lH,5H-pyrazolo[1,2-a]pyrazol-l-one et ses sels, tel que le sel de diméthane sulfonate de 2,3-diamino-6,7-dihydro-lH,5H-pyrazolo-[1,2-a]pyrazol-1-one, de formule : 2 (CH3SO3H) La (ou les) base(s) d'oxydation choisie(s) parmi les dérivés de la 2,3-diaminopyrazolone et leurs sels d'addition (composés A) est (ou sont) en général présente(s) chacune en quantité allant de 0,001 à 1 % en poids du poids total de la composition tinctoriale, de préférence de 0, 005 à 6 % en poids de ce poids. They can also be in the form of solvates, for example a hydrate, or a linear or branched alcohol solvate, such as ethanol or isopropanol. By way of examples of derivatives of formula (V), mention may be made of the compounds presented below or their addition salts: 4,5-diamino-1,2-dimethyl-1,2-dihydropyrazol-3-one ; 4-amino-5-methylamino-1,2-dimethyl-1,2-dihydropyrazol-3-one; 4-amino-5-dimethylamino-1,2-dimethyl-1,2-dihydropyrazol-3-one; 4-amino-5- (2-hydroxyethyl) amino-1,2-dimethyl-1,2-dihydropyrazol-3-one; 4-amino-5- (pyrrolidin-1-yl) -1,2-dimethyl-1,2-dihydropyrazol-3-one; 4-amino-5- (piperidin-1-yl) -1,2-dimethyl-1,2-dihydropyrazol-3-one; 4,5-diamino-1,2-di- (2-hydroxyethyl) -1,2-dihydropyrazol-3-one; 4-amino-5-methylamino-1,2-di- (2-hydroxyethyl) -1,2-dihydropyrazol-3-one 4-amino-5-dimethylamino-1,2-di- (2-hydroxyethyl) -1 2-dihydropyrazol-3-one 4-amino-5- (2-hydroxyethyl) amino-1,2-di- (2-hydroxyethyl) -1,2-dihydropyrazol-3-one; 4-amino-5- (pyrrolidin-1-yl) -1,2-di- (2-hydroxyethyl) -1,2-dihydropyrazol-3-one 4-amino-5 - (piperidin-1-yl) -1 2-di- (2-hydroxyethyl) -1,2-dihydropyrazol-3-one; 4,5-diamino-1,2-diethyl-1,2-dihydropyrazol-3-one; 4,5-diamino-1,2-phenyl-1,2-dihydropyrazol-3-one; 4,5-diamino-1-ethyl-2-methyl-1,2-dihydropyrazol-3-one; 4,5-diamino-2-ethyl-1-methyl-1,2-dihydropyrazol-3-one; 4,5-diamino-1-phenyl-2-methyl-1,2-dihydropyrazol-3-one 4,5-diamino-2-phenyl-1-methyl-1,2-dihydropyrazol-3-one 4,5- diamino-1- (2-hydroxyethyl) -2-methyl-1,2-dihydropyrazol-3-one; 4,5-diamino-2- (2-hydroxyethyl) -1-methyl-1,2-dihydropyrazol-3-one; 2,3-diamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3-methylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-Amino-3-dimethylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one 2-amino-3-ethylamino-6,7-dihydro-1H, 5H- pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3-isopropylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3- (2-hydroxyethyl) amino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3- (2-hydroxypropyl) amino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3-bis (2-hydroxyethyl) amino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-Amino-3- (pyrrolidin-1-yl) -6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-l-2-amino-3- (3-hydroxy-pyrrolidin) -1- yl) -6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3- (piperidin-1-yl) -6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one 2,3-diamino-6-hydroxy-6,7 dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2,3-diamino-6-methyl-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2,3-diamino-6,6-dimethyl-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2,3-diamino-5,6,7,8-tetrahydro-1H, 6H-pyridazino [1,2-a] pyrazol-1-one; 2,3-diamino-5,8-dihydro-1H, 6H-pyridazino [1,2-a] pyrazol-1-one; 4-amino-5-dimethylamino-1,2-diethyl-1,2-dihydropyrazol-3-one; 4-amino-1,2-diethyl-5-ethylamino-1,2-dihydropyrazol-3-one; 4-amino-1,2-diethyl-5-isopropylamino-1,2-dihydropyrazol-3-one, 4-amino-1,2-diethyl-5- (2-hydroxyethylamino) -1,2-dihydropyrazol-3- one; 4-Amino-5- (2-dimethylaminoethylamino) -1,2-diethyl-1,2-dihydropyrazol-3-one 4-amino-5- [bis (2-hydroxyethyl) amino] -1,2-diethyl- 1,2-dihydropyrazol-3one; 4-amino-1,2-diethyl-5- (3-imidazol-1-yl-propylamino) -1,2-dihydropyrazol-3-one; 4-Amino-1,2-diethyl-5- (3-hydroxypyrrolidin-1-yl) -1,2-dihydropyrazol-3-one 4-amino-5-pyrrolidin-1-yl-1,2-1,2-diethyl dihydropyrazol-3-one 4-amino-5- (3-dimethylaminopyrrolidin-1-yl) -1,2-diethyl-1,2-dihydropyrazol-3-one; 4-amino-1,2-diethyl-5- (4-methylpiperazin-1-yl) pyrazolidin-3-one; some of which are shown below to illustrate the names by chemical structures: O ~ NH2 H3cuNNNHZ 4,5-diamino-1,2-dimethyl-1,2CH3 dihydropyrazol-3-one O ~ NH2 4,5- diamino-1,2-diethyl-1,2-dihydro-pyrazol-3-one c2H5 N NHz C2H5 O, NH4 4,5-diamino-1,2-diphenyl-1,2-phN-N NH2 dihydro-pyrazole -3-one Ph 2 O-NH 2 4,5-diamino-1-ethyl-2-methyl-1,2-H 3 CN, N NH 2 dihydropyrazol-3-one C 2 H 5 O -NH 2 4,5-diamino-1-phenyl 2-methyl-1,2-H3C'N NH 2 dihydropyrazol-3-one Ph 2 NH 2 4-amino-5- (pyrrolidin-1-yl) -1,2-diethyl-C 2 H 5 N 1,2-dihydropyrazol -3-one C2H5 O-NH2 4-amino-5- (3-dimethylaminopyrrolidin-C H) -1-yl) -1,2-diethyl-1,2-dihydropyrazol-3-one C 2 H 5 N • N N CH 3 C 2 H 5 O , NH 2 2,3-diamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one / NH 2 NH 2 2-amino-3-methylamino-6.7 1H, 5H-pyrazolo [1,2-a] pyrazol-1-one O-NH 2 -amino-3-ethylamino-6,7-dihydro-1H, 5H-N pyrazolo [1,2-a] pyrazol-1-one a] pyrazol-1-one O-2-amino-3- (2-hydroxyethyl) amino-6,7-N NH dihydro-1H, 5H-pyrazolo [1,2- a] pyrazol-1-OH one O, NH 2 2-amino-3- (2-hydroxypropyl) amino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-N 2-amino-3-bis (2-hydroxyethyl) amino-6,7-OH dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one ~ NN 1H-NH-2-amino-3-isopropylamino-6,7-dihydro-N'NH 1H, 5H-pyrazolo [1,2-a] pyrazol-1-one N NO 2 -NH 2 -amino-3 ( pyrrolidin-1-yl) -6,7-dihydro-N, 1H, 5H-pyrazolo [1,2-a] pyrazol-1-one-O-NH 2 -amino-3- (3-hydroxypyrrolidin-1-yl) - 6,7-N, OH dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-NN-one / O-NH 2 2,3-diamino-6-hydroxy-6,7-dihydro-1H, 5H N pyrazolo [1,2-a] pyrazol-1-one N NH 2 / HO 2 O 2 NH 2 2,3-diamino-6-methyl-6,7-dihydro-1H, 5H-N, N NH 2 pyrazolo [1] , 2-a] pyrazol-1-one O0-NH2 2,3-diamino-6,6-dimethyl-6,7-dihydro-N'N NH2 1H, 5H-pyrazolo [1,2-a] pyrazol-1 O 2 -NH 2 2,3-diamino-5,6,7,8-tetrahydro-1H, 6H-NH 2 pyridazino [1,2-a] pyrazol-1-one N N N OO 2 NH 2 2,3-diamino 5,8-Dihydro-1H, 6H-N-N-NH 2 pyridazino [1,2-a] pyrazol-1-one O% -NH 2 4,5-diamino-1- (2-hydroxyethyl) -2-methyl-HNH 4 -NH-1,2-dihydropyrazol-3-one N-OH / NH 2 4,5-diamino-2- (2-hydroxyethyl) -1-methyl-1,2-dihydropyrazol-3-one N NH 2 HO Among these compounds, the 2,3-diaminopyrazolone derivatives of formula (V) that are particularly preferred are the following: 2,3-diamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol l-one; 2-amino-3-ethylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3-isopropylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3- (pyrrolidin-1-yl) -6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 4,5-diamino-1,2-dimethyl-1,2-dihydropyrazol-3-one; 4,5-diamino-1,2-diethyl-1,2-dihydropyrazol-3-one; 4,5-diamino-1,2-di- (2-hydroxyethyl) -1,2-dihydropyrazol-3-one; 2-amino-3- (2-hydroxyethyl) amino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2-amino-3-dimethylamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one; 2,3-Diamino-5,6,7,8-tetrahydro-1H, 6H-pyridazino [1,2-a] pyrazol-1-one 4-amino-1,2-diethyl-5-pyrrolidin-1-yl -1,2-dihydropyrazol-3-one; 4-amino-5- (3-dimethylamino-pyrrolidin-1-yl) -1,2-diethyl-1,2-dihydropyrazol-3-one; 2,3-diamino-6-hydroxy-6,7-dihydro-lH, 5H-pyrazolo [1,2-a] pyrazol-lone. Even more preferred is 2,3-diamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one and its salts, such as 2,3-dimethanesulfonate salt. -diamino-6,7-dihydro-1H, 5H-pyrazolo [1,2-a] pyrazol-1-one, of formula: ## STR4 ## The chosen oxidation base (s) (s) ) among the 2,3-diaminopyrazolone derivatives and their addition salts (compounds A) is (are) generally present (each) in an amount ranging from 0.001 to 1% by weight of the total weight of the dyeing composition preferably from 0.005 to 6% by weight of this weight.
Le (ou les) second(s) colorant(s) d'oxydation différent(s) du (ou des) composé(s) A, peut (ou peuvent) être choisi(s) parmi les colorants d'oxydation benzéniques, hétérocycliques et naphtaléniques. A titre d'exemples de colorants d'oxydation utilisables, on peut citer les bases benzéniques cationiques ou non, les bases hétérocycliques, les coupleurs benzéniques, les coupleurs hétérocycliques, les coupleurs naphtaléniques, et leurs sels d'addition. Dans un mode de réalisation particulier, lescompositions selon l'invention comprennent une ou plusieurs base(s) d'oxydation dérivée(s) de 2,3-diaminopyrazolone de formule (V), une ou plusieurs seconde(s) base(s) d'oxydation différente(s) de la base (ou des bases) d'oxydation 2,3-diaminopyrazolone(s) de formule (V), et un ou plusieurs coupleur(s) d'oxydation, notamment des coupleurs benzéniques tels que les méta-aminophénols et leurs sels d'addition. Selon un mode de réalisation, la (ou les) seconde(s) base(s) d'oxydation est (ou sont) choisie(s) parmi les bases d'oxydation benzéniques qui peuvent être cationiques ou non-cationiques. A titre de bases d'oxydation benzéniques non cationiques utilisables, on peut citer les para-phénylènediamines, les bis- phénylalkylènediamines, les para-aminophénols, les ortho-aminophénols, et leurs sels d'addition. Parmi les para-phénylènediamines de ce type, on peut citer à titre d'exemple, la para-phénylènediamine, la para-toluylènediamine, la 2-chloro-para-phénylénediamine, la 2,3-diméthylpara-phénylénediamine, la 2,6-diméthyl-para-phénylènediamine, la 2,6-diéthyl-paraphénylènediamine, la 2,5-diméthyl-para-phénylénediamine, la N,N-diméthyl-para-phénylènediamine, la N,N-diéthyl-para-phénylènediamine, la N,N-dipropyl-para-phénylènediamine, la 4-amino-N,N-diéthyl-3-méthyl-aniline, la N,N-bis-((3-hydroxyéthyl)-para-phénylénediamine, la 4-N,N-bis-((3-hydroxyéthyl)amino-2-méthyl- aniline, la 4-N,N-bis-((3-hydroxyéthyl)amino-2-chloroaniline, la 2-(3-hydroxyéthyl-para-phénylénediamine, la 2-fluoro para-phénylènediamine, la 2-isopropyl-para-phénylènediamine, la N-((3-hydroxy- propyl)-para-phénylènediamine, la 2-hydroxyméthyl-para-phénylène- diamine, la N,N-diméthyl-3-méthyl-para-phénylénediamine, la N,N-(éthyl,(3-hydroxyéthyl)-para-phénylénediamine, la N-((3,y-dihydroxypropyl)-para-phénylénediamine, la N-(4'-aminophényl)-para-phénylènediamine, la N-phényl-para-phénylènediamine, la 2-(3-hydroxyéthyloxy-para-phénylénediamine, la 2-(3-acétylamino-éthyloxy-para-phénylénediamine, la N-((3-méthoxyéthyl)-paraphénylénediamine, la 4-aminophénylpyrrolidine, la 2-thiényl-paraphénylènediamine, le 2-(3-hydroxyéthylamino-5-aminotoluène, la 3-hydroxy-1-(4'-aminophényl)pyrrolidine, et leurs sels d'addition. The second (or more) different oxidation dye (s) of the compound (s) A, may (or may) be chosen from benzene, heterocyclic oxidation dyes. and naphthalenic. As examples of oxidation dyes that can be used, mention may be made of cationic or non-cationic benzene bases, heterocyclic bases, benzene couplers, heterocyclic couplers, naphthalenic couplers, and their addition salts. In a particular embodiment, the compositions according to the invention comprise one or more base (s) of oxidation derived from 2,3-diaminopyrazolone of formula (V), one or more second base (s) different oxidation (s) of the base (or bases) of oxidation 2,3-diaminopyrazolone (s) of formula (V), and one or more coupler (s) oxidation, including benzene couplers such as meta-aminophenols and their addition salts. According to one embodiment, the second base (s) of oxidation is (or are) chosen from among the benzene oxidation bases which may be cationic or non-cationic. Non-cationic benzene oxidation bases which may be used include para-phenylenediamines, bisphenylalkylenediamines, para-aminophenols and ortho-aminophenols, and their addition salts. Among the para-phenylenediamines of this type, para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethylpara-phenylenediamine, 2.6 may be mentioned by way of example. dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N, N-dimethyl-para-phenylenediamine, N, N-diethyl-para-phenylenediamine, N, N-dipropyl-para-phenylenediamine, 4-amino-N, N-diethyl-3-methyl-aniline, N, N-bis - ((3-hydroxyethyl) -para-phenylenediamine, 4-N, N-bis - ((3-hydroxyethyl) amino-2-methylaniline, 4-N, N-bis - ((3-hydroxyethyl) amino-2-chloroaniline, 2- (3-hydroxyethyl-para-phenylenediamine) , 2-fluoro para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N - ((3-hydroxypropyl) -para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N, N- dimethyl-3-methyl-para-phenylenediamine, N, N- (ethyl, (3-hydroxyethyl) -para-phenylenediamine e, N - ((3, y-dihydroxypropyl) -para-phenylenediamine, N- (4'-aminophenyl) -para-phenylenediamine, N-phenyl-para-phenylenediamine, 2- (3-hydroxyethyloxy-para) phenylenediamine, 2- (3-acetylamino-ethyloxy-para-phenylenediamine, N - ((3-methoxyethyl) -paraphenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl-para-phenylenediamine, 2- (3-hydroxyethylamino) -5- amino-toluene, 3-hydroxy-1- (4'-aminophenyl) pyrrolidine, and their addition salts.
Parmi les para-phénylènediamines citées ci-dessus, la para-phénylènediamine, la para-toluylènediamine, la 2-isopropyl-para-phénylènediamine, la 2-(3-hydroxyéthyl-para-phénylénediamine, la 2-(3-hydroxyéthyloxy-para-phénylénediamine, la 2,6-diméthyl-paraphénylénediamine, la 2,6-diéthyl-para-phénylénediamine, la 2,3-diméthyl-para-phénylénediamine, la N,N-bis-((3-hydroxyéthyl)-para-phénylènediamine, la 2-chloro para-phénylènediamine, la 2-(3-acétylaminoéthyloxy-para-phénylénediamine, et leurs sels d'addition sont particulièrement préférés. Parmi les bis-phénylalkylènediamines non cationiques, on peut citer à titre d'exemple, le N,N'-bis-((3-hydroxyéthyl)-N,N'-bis-(4'aminophényl)-1,3-diaminopropanol, la N,N'-bis-((3-hydroxyéthyl)-N,N'-bis-(4'-aminophényl)éthylènediamine, la N,N'-bis-(4-aminophényl)- tétraméthylènediamine, la N,N'-bis-((3-hydroxyéthyl)-N,N'-bis-(4- aminophényl)tétraméthylènediamine, la N,N'-bis-(4-méthylamino- phényl)tétraméthylènediamine, la N,N'-bis(éthyl)-N,N'-bis-(4'-amino, 3'-méthylphényl)éthylènediamine, le 1,8-bis-(2,5-diaminophénoxy)-3,6-dioxaoctane, et leurs sels d'addition. Parmi les para-aminophénols non-cationiques, on peut citer à titre d'exemple, le para-aminophénol, le 4-amino-3-méthylphénol, le amino-2-méthoxyméthylphénol, le 4-amino-2-aminométhylphénol, le 4-amino-2-((3-hydroxyéthylaminométhyl)phénol, le 4-amino-2-fluorophénol, et leurs sels d'addition. Parmi les ortho-aminophénols non-cationiques, on peut citer à titre d'exemple, le 2-aminophénol, le 2-amino-5-méthylphénol, le 2-amino-6-méthylphénol, le 5-acétamido-2-aminophénol, et leurs sels d'addition. A titre de bases d'oxydation benzéniques cationiques utilisables dans les compositions selon l'invention, on peut citer les para- phénylènediamines telles que notamment décrites dans les demandes de brevets FR-A-2 766 177 et FR-A-2 766 178, les para-aminophénols tels que décrits par exemple dans les demandes de brevet FR-A-2 766 177 et FR-A-2 766 178, les ortho-phénylènediamines telles que décrites par exemple dans les demandes de brevet FR-A-2 782 718, FR-A-2 782 716 et FR-A-2 782 719, des ortho-aminophénols ou des bases doubles cationiques telles que des dérivés de type 4-amino-3-fluorophénol, le 4-amino-3-hydroxyméthylphénol, le 4- amino-2-méthylphénol, le 4-amino-2-hydroxyméthylphénol, le 4-bis(aminophényl)alkylènediamine décrites dans les demandes de brevet FR-A-2 766 179, portant au moins un atome d'azote quaternaire. De préférence, les bases d'oxydation benzéniques cationiques utilisables dans les compositions selon l'invention sont des para- phénylènediamines cationiques. De manière avantageuse, une variante consiste à mettre en oeuvre des bases d'oxydation cationiques de structure paraphénylènediamine, dont au moins une des fonctions amine est une amine tertiaire, porteur d'un noyau pyrrolidinique, la molécule possédant au moins un atome d'azote quaternisé. De telles bases sont, par exemple, décrites dans le document EP-A-1 348 695. Par "base hétérocyclique" ou "base d'oxydation hétérocyclique", on entend, au sens de la présente invention, toute base d'oxydation comportant au moins un groupe hétérocyclique, différent d'un groupe pyrrolidinyle dont l'atome d'azote est substitué par un groupement para-aminophényle et possédant au moins un atome d'azote quaternisé. A titre de bases d'oxydation hétérocycliques utilisables dans les compositions selon l'invention, on peut citer les pyridines, les pyrimidines, les pyrazoles, les pyrazolopyrimidines condensées, les pyrazolotriazoles, les pyrazolotétrazoles, les pyrazolopyridazines, les pyrazolothiazoles, les pyrazoloimidazoles, les pyrazolobenzimidazoles, les pyrazoloquinolines, les aminopyrolidines, les aminopyrazolines, les mono- ou diaminotétraquinoléines, les diamino- ou triamino- quinoléines, les aminoindazoles, les diaminouraciles, les aminoindolénines, les hydrazones, la julolidine ou la lilolidine, ainsi que leurs dérivés et leurs sels d'addition. Parmi les dérivés pyridiniques, on peut citer les composés décrits par exemple dans les brevets GB-A-1 026 978 et GB-A-1 153 196, comme la 2,5-diaminopyridine, la 2-(4-méthoxy- phényl)amino-3-aminopyridine, la 2,3-diamino-6-méthoxypyridine, la 2-((3-méthoxyéthyl)amino-3-amino-6-méthoxypyridine, la 3,4-diaminopyridine, et leurs sels d'addition. D'autres bases d'oxydation pyridiniques utilisables dans la présente invention sont les 3-aminopyrazolo[1,5-a]pyridines ou leurs sels d'addition, décrits, par exemple, dans la demande de brevet FR-A-2 801 308. A titre d'exemple, on peut citer la pyrazolo[1,5-a]- pyridin-3-ylamine ; la 2-acétylaminopyrazolo[1,5-a]pyridin-3-ylamine la 2-morpholin-4-yl-pyrazolo[1,5-a]pyridin-3-ylamine ; l'acide 3-aminopyrazolo[1,5-a]pyridin-2-carboxylique ; la 2-méthoxypyrazolo-[1,5-a]pyridine-3-ylamino ; le (3-aminopyrazolo[1,5-a]pyridine-7- yl)méthanol ; le 2-(3-aminopyrazolo[1,5-a]pyridine-5-yl)éthanol ; le 2-(3-aminopyrazolo-[1,5-a]-pyridine-7-yl)éthanol ; le (3-amino-pyrazolo[1,5-a]pyridine-2-yl)méthanol ; la 3,6-diaminopyrazolo-[1,5-a]pyridine ; la 3,4-diaminopyrazolo[1,5-a]pyridine ; la pyrazolo-[1,5-a]pyridine-3,7-diamine ; la 7-morpholin-4-yl-pyrazolo[1,5-a]-pyridin-3-ylamine ; la pyrazolo[1,5-a]pyridine-3,5-diamine ; la 5-morpholin-4-yl-pyrazolo[1,5-a]pyridin-3-ylamine ; le 2-[(3-aminopyrazolo[1,5-a]pyridin-5-yl)-(2-hydroxyéthyl)amino]éthanol ; le 2-[(3-aminopyrazolo[1,5-a]pyridin-7-yl)-(2-hydroxyéthyl)amino]éthanol ; la 3-aminopyrazolo[1,5-a]pyridine-5-ol ; 3-aminopyrazolo[1,5-a]pyridine- 401 la 3-aminopyrazolo[1,5-a]pyridine-6-ol ; la 3-aminopyrazolo[1,5-a]pyridine-7-ol, ainsi que leurs sels d'addition. Parmi les dérivés pyrimidiniques, on peut citer les composés décrits par exemple dans les brevets DE-A-2359399 ; JP 88-169571 JP 05-63124 ; EP-A-0770375 ou demande de brevet WO 96/15765 comme la 2,4,5,6-tétra-aminopyrimidine, la 4-hydroxy-2,5,6-triaminopyrimidine, la 2-hydroxy-4,5,6-triaminopyrimidine, la 2,4-dihydroxy-5,6-diaminopyrimidine, la 2,5,6-triaminopyrimidine, et les dérivés pyrazolopyrimidiniques tels ceux mentionnés dans la demande de brevet FR-A-2 750 048 et parmi lesquels on peut citer la pyrazolo-[1,5-a]pyrimidine-3,7-diamine ; la 2,5-diméthylpyrazolo[1,5-a]-pyrimidine-3,7-diamine ; la pyrazolo[1,5-a]pyrimidine-3,5-diamine la 2,7-diméthylpyrazolo[1,5-a]pyrimidine-3,5-diamine ; le 3-amino-pyrazolo[1,5-a]pyrimidin-7-ol ; le 3-aminopyrazolo[1,5-a]pyrimidin-5-ol ; le 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)éthanol, le 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)éthanol, le 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyéthyl)amino]- éthanol, le 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)(2-hydroxy- éthyl)amino] éthanol, la 5,6-diméthylpyrazolo[1,5-a]pyrimidine- 3,7-diamine, la 2,6-diméthylpyrazolo[1,5-a]pyrimidine-3,7-diamine, la 2, 5, N7, N7-tétraméthylpyrazolo[1,5-a]pyrimidine-3,7-diamine, la 3-amino-5-méthyl-7-imidazolylpropylaminopyrazolo[1,5-a]pyrimidine, leurs sels d'addition, et leurs formes tautomères lorsqu'il existe un équilibre tautomérique. Parmi les dérivés pyrazoliques, on peut citer les composés décrits dans les brevets DE-A-38 43 892, DE-A-41 33 957 et demandes de brevet WO 94/08969, WO 94/08970, FR-A-2 733 749 et DE-A-195 43 988 comme le 4,5-diamino-1-méthylpyrazole, le 4,5-diamino-1-(3-hydroxyéthyl)pyrazole, le 3,4-diaminopyrazole, le 4,5-diamino- 1-(4'-chlorobenzyl)pyrazole, le 4,5-diamino-1,3-diméthyl-pyrazole, le 4,5-diamino-3-méthyl-1-phénylpyrazole, le 4,5-diamino-1-méthyl-3-phénylpyrazole, le 4-amino-1,3-diméthyl-5-hydrazino- pyrazole, le 1-benzyl-4,5-diamino-3-méthylpyrazole, le 4,5-diamino-3-tert-butyl-1-méthylpyrazole, le 4,5-diamino-1-tert-butyl-3-méthyl-pyrazole, le 4,5-diamino-1-(3-hydroxyéthyl)-3-méthylpyrazole, le 4,5-diamino-1-éthyl-3-méthylpyrazole, le 4,5-diamino-1-éthyl-3-(4'-méthoxyphényl)pyrazole, le 4,5-diamino-1-éthyl-3-hydroxyméthylpyrazole, le 4,5-diamino-3-hydroxyméthyl-1-méthylpyrazole, le 4,5-diamino-3-hydroxyméthyl-1-isopropylpyrazole, le 4,5-diamino-3-méthyl-1-isopropylpyrazole, le 4-amino-5-(2'-aminoéthyl)amino-1,3-diméthylpyrazole, le 3,4,5-triaminopyrazole, le 1-méthyl-3,4,5-triaminopyrazole, le 3,5-diamino-1-méthyl-4-méthylaminopyrazole, le 3,5-diamino-4-(3-hydroxyéthyl)amino-1-méthylpyrazole, et leurs sels d'addition. A titre de pyrazolotriazoles, on peut citer les composés 3-amino-4-méthyl-6-méthylthio-2-phénylpyrazolo[3,2-c]-s-triazole, 3-amino-2,4,6-triméthylpyrazolo[3,2-c]-s-triazole, 3-amino-4,6-diméthylpyrazolo[3,2-c]-s-triazole. De tels composés sont décrits dans le document US 5,457,200. On peut aussi citer les composés 7-amino-2,6-diméthylpyrazolo[1,5-b]-1,2,4-triazole, 7-amino-3,6-diméthylpyrazolo-[3,2-c]-1,2,4-triazole, 7-amino-3-méthylpyrazolo[3,2-c]-1,2,4-triazole, 7-amino-3-méthyl-6-carboxypyrazolo[3,2-c]-1,2,4-triazole, 7-amino-2-méthylpyrazolo[1,5-b]-1,2,4-triazole, 7-amino-2-phénylpyrazolo-[1,5-b]-1,2,4-triazole, 7-amino-2-méthyl-6-carboxypyrazolo[1,5-b]-1,2,4-triazole. Ces composés sont décrits dans la demande de brevet EP-A-923 929. Among the para-phenylenediamines mentioned above, para-phenylenediamine, para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2- (3-hydroxyethyl-para-phenylenediamine, 2- (3-hydroxyethyloxy-para) phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N, N-bis- ((3-hydroxyethyl) -para- phenylenediamine, 2-chloro-para-phenylenediamine, 2- (3-acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof are particularly preferred.) Among the non-cationic bisphenylalkylenediamines, mention may be made, by way of example, of N, N'-bis - ((3-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) -1,3-diaminopropanol, N, N'-bis - ((3-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis - ((3-hydroxyethyl) -N, N'-bis - (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methylaminophenyl) t tramethylenediamine, N, N'-bis (ethyl) -N, N'-bis (4'-amino, 3'-methylphenyl) ethylenediamine, 1,8-bis (2,5-diaminophenoxy) -3, 6-dioxaoctane, and their addition salts. Among the non-cationic para-aminophenols, para-aminophenol, 4-amino-3-methylphenol, amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, amino-2 - ((3-hydroxyethylaminomethyl) phenol, 4-amino-2-fluorophenol, and their addition salts Among the non-cationic ortho-aminophenols, there may be mentioned, by way of example, the 2- aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and their addition salts, as cationic benzene oxidation bases which can be used in the compositions according to the invention may be cited para-phenylenediamines such as in particular described in patent applications FR-A-2,766,177 and FR-A-2,766,178, para-aminophenols as described for example in patent applications FR-A-2 766 177 and FR-A-2 766 178, ortho-phenylenediamines as described for example in patent applications FR-A-2 782 718, FR-A-2 782 716 and FR-A-2 782 719, ortho-aminophenols or cationic double bases such as 4-amino-3-fluorophenol derivatives, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol , 4-amino-2-hydroxymethylphenol, 4-bis (aminophenyl) alkylenediamine described in patent applications FR-A-2 766 179, bearing at least one quaternary nitrogen atom. Preferably, the cationic benzene oxidation bases that can be used in the compositions according to the invention are cationic para-phenylenediamines. Advantageously, one variant consists in using cationic oxidation bases of paraphenylenediamine structure, at least one of the amine functions of which is a tertiary amine carrying a pyrrolidine ring, the molecule having at least one nitrogen atom. quaternized. Such bases are, for example, described in document EP-A-1 348 695. By "heterocyclic base" or "heterocyclic oxidation base" is meant, within the meaning of the present invention, any oxidation base comprising at least one heterocyclic group, other than a pyrrolidinyl group, the nitrogen atom of which is substituted by a para-aminophenyl group and having at least one quaternized nitrogen atom. As heterocyclic oxidation bases that can be used in the compositions according to the invention, mention may be made of pyridines, pyrimidines, pyrazoles, condensed pyrazolopyrimidines, pyrazolotriazoles, pyrazolotetrazoles, pyrazolopyridazines, pyrazolothiazoles, pyrazoloimidazoles and pyrazolobenzimidazoles. pyrazoloquinolines, aminopyrrolidines, aminopyrazolines, mono- or diaminotetraquinolines, diamino or triaminoquinolines, aminoindazoles, diaminouracils, aminoindolenines, hydrazones, julolidine or lilolidine, and their derivatives and salts thereof. 'addition. Among the pyridine derivatives, mention may be made of the compounds described for example in patents GB-A-1 026 978 and GB-A-1 153 196, such as 2,5-diaminopyridine, 2- (4-methoxyphenyl) amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2 - ((3-methoxyethyl) amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and their addition salts. Other pyridinic oxidation bases that may be used in the present invention are 3-aminopyrazolo [1,5-a] pyridines or their addition salts, described, for example, in patent application FR-A-2 801 308. By way of example, mention may be made of pyrazolo [1,5-a] pyridin-3-ylamine, 2-acetylaminopyrazolo [1,5-a] pyridin-3-ylamine and 2-morpholin-4-yl. pyrazolo [1,5-a] pyridin-3-ylamine, 3-aminopyrazolo [1,5-a] pyridin-2-carboxylic acid, 2-methoxypyrazolo [1,5-a] pyridine-3- (3-aminopyrazolo [1,5-a] pyridin-7-yl) methanol, 2- (3-aminopyrazolo [1,5-a] pyridin-5-yl) ethanol; aminopyrazolo- [1,5-a] pyridin-7-yl ethanol; (3-amino-pyrazolo [1,5-a] pyridin-2-yl) methanol; 3,6-diaminopyrazolo [1,5-a] pyridine; 3,4-diaminopyrazolo [1,5-a] pyridine; pyrazolo [1,5-a] pyridine-3,7-diamine; 7-morpholin-4-yl-pyrazolo [1,5-a] pyridin-3-ylamine; pyrazolo [1,5-a] pyridine-3,5-diamine; 5-morpholin-4-yl-pyrazolo [1,5-a] pyridin-3-ylamine; 2 - [(3-aminopyrazolo [1,5-a] pyridin-5-yl) - (2-hydroxyethyl) amino] ethanol; 2 - [(3-aminopyrazolo [1,5-a] pyridin-7-yl) - (2-hydroxyethyl) amino] ethanol; 3-aminopyrazolo [1,5-a] pyridin-5-ol; 3-aminopyrazolo [1,5-a] pyridine-3-aminopyrazolo [1,5-a] pyridin-6-ol; 3-aminopyrazolo [1,5-a] pyridin-7-ol, as well as their addition salts. Among the pyrimidine derivatives, mention may be made of the compounds described, for example, in DE-A-2359399; JP 88-169571 JP 05-63124; EP-A-0770375 or patent application WO 96/15765 such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6 triminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in the patent application FR-A-2 750 048 and among which mention may be made pyrazolo [1,5-a] pyrimidine-3,7-diamine; 2,5-dimethylpyrazolo [1,5-a] pyrimidine-3,7-diamine; pyrazolo [1,5-a] pyrimidine-3,5-diamine 2,7-dimethylpyrazolo [1,5-a] pyrimidine-3,5-diamine; 3-amino-pyrazolo [1,5-a] pyrimidin-7-ol; 3-aminopyrazolo [1,5-a] pyrimidin-5-ol; 2- (3-aminopyrazolo [1,5-a] pyrimidin-7-ylamino) ethanol, 2- (7-aminopyrazolo [1,5-a] pyrimidin-3-ylamino) ethanol, 2 - [(3 aminopyrazolo [1,5-a] pyrimidin-7-yl) (2-hydroxyethyl) amino] ethanol, 2 - [(7-aminopyrazolo [1,5-a] pyrimidin-3-yl) (2-hydroxy) ethyl) amino] ethanol, 5,6-dimethylpyrazolo [1,5-a] pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo [1,5-a] pyrimidine-3,7-diamine, 2,5-N7-N7-tetramethylpyrazolo [1,5-a] pyrimidine-3,7-diamine, 3-amino-5-methyl-7-imidazolylpropylaminopyrazolo [1,5-a] pyrimidine, their addition salts , and their tautomeric forms when there is a tautomeric equilibrium. Among the pyrazole derivatives, mention may be made of the compounds described in DE-A-38 43 892, DE-A-41 33 957 and patent applications WO 94/08969, WO 94/08970 and FR-A-2 733 749. and DE-A-195 43 988 such as 4,5-diamino-1-methylpyrazole, 4,5-diamino-1- (3-hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-4,5-diamino-1- 1- (4'-Chlorobenzyl) pyrazole, 4,5-diamino-1,3-dimethyl-pyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl 3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl- 1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methyl-pyrazole, 4,5-diamino-1- (3-hydroxyethyl) -3-methylpyrazole, 4,5-diamino-1 3-methyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3- (4'-methoxyphenyl) pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diaminoethyl 3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3-methyl-1 isopropylpyrazole, 4-amino-5- (2'-aminoethyl) amino-1,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole, 3,5 1-diamino-1-methyl-4-methylaminopyrazole, 3,5-diamino-4- (3-hydroxyethyl) amino-1-methylpyrazole, and their addition salts. As pyrazolotriazoles, mention may be made of the compounds 3-amino-4-methyl-6-methylthio-2-phenylpyrazolo [3,2-c] -s-triazole, 3-amino-2,4,6-trimethylpyrazolo [3 , 2-c] -s-triazole, 3-amino-4,6-dimethylpyrazolo [3,2-c] -s-triazole. Such compounds are described in US 5,457,200. Mention may also be made of 7-amino-2,6-dimethylpyrazolo [1,5-b] -1,2,4-triazole, 7-amino-3,6-dimethylpyrazolo [3,2-c] -1 compounds. 2,4-triazole, 7-amino-3-methylpyrazolo [3,2-c] -1,2,4-triazole, 7-amino-3-methyl-6-carboxypyrazolo [3,2-c] -1 2,4-triazole, 7-amino-2-methylpyrazolo [1,5-b] -1,2,4-triazole, 7-amino-2-phenylpyrazolo [1,5-b] -1,2, 4-triazole, 7-amino-2-methyl-6-carboxypyrazolo [1,5-b] -1,2,4-triazole. These compounds are described in patent application EP-A-923,929.
A titre de pyrazolotétrazoles, on peut citer les composés 7-amino-6-méthylpyrazolo[1,5-e]tétrazole, 7-amino-6-phénylpyrazolo-[1,5-e]tétrazole, 7-amino-6-carboxypyrazolo[1,5-e]tétrazole décrits dans la demande de brevet EP-A-923 929. A titre de pyrazolopyridazine, on peut citer la 3-aminopyrazolo-[1,5-b]pyridazine. De tels composés sont décrits dans le document US 5,457,200. A titre de pyrazolothiazoles, on peut citer les composés 3-amino-2-méthylpyrazolo[3,2-b]thiazole, 3-aminopyrazolo[3,2-b]-thiazole, 3-amino-2,5-diméthyl-6-phénylpyrazolo[3,2-b]thiazole. De tels composés sont décrits dans le document US 5,427,200. As pyrazolotetrazoles, mention may be made of the compounds 7-amino-6-methylpyrazolo [1,5-e] tetrazole, 7-amino-6-phenylpyrazolo [1,5-e] tetrazole, 7-amino-6-carboxypyrazolo [1,5-e] tetrazole described in patent application EP-A-923,929. As pyrazolopyridazine, mention may be made of 3-aminopyrazolo [1,5-b] pyridazine. Such compounds are described in US 5,457,200. As pyrazolothiazoles, mention may be made of the compounds 3-amino-2-methylpyrazolo [3,2-b] thiazole, 3-aminopyrazolo [3,2-b] thiazole, 3-amino-2,5-dimethyl-6 -phénylpyrazolo [3,2-b] thiazole. Such compounds are described in US 5,427,200.
A titre de pyrazoloimidazoles, on peut citer les composés 3-amino-4-benzylpyrazolo[1,5-a]imidazole, 3-amino-2,4-diméthylpyrazolo[1,5-a] imidazole, 3-amino-4-méthylpyrazolo[1,5-a]imidazole. De tels composés sont décrits dans le document US 5,457,200. On peut aussi citer les composés 7-amino-6-méthylpyrazolo[1,5-a]imidazole, 7-aminopyrazolo[1,5-a]imidazole, 7-amino-2-méthylpyrazolo[1,5-a]-imidazole, 7-amino-2-phénylpyrazolo[1,5-a]imidazole décrits dans la demande de brevet EP-A-923 929. A titre de pyrazolobenzimidazoles, on peut citer les composés 7-amino-6-méthylpyrazolo[1,5-a]benzimidazole, 6,7-diaminopyrazolo- [1,5-a]benzimidazole, 6,7-diamino-2-méthylpyrazolo[1,5-a]- benzimidazole, 6,7-diamino-2-phénylpyrazolo[1,5-a]benzimidazole décrits, par exemple, dans la demande de brevet EP-A-923 929. A titre de pyrazoloquinolines, on peut citer les composés 3-amino-2-phénylpyrazolo[1,5-a]quinoline. De tels composés sont décrits dans le document US 5,457,200. A titre d'aminopyrazolines, on peut citer les composés 1-(4'-aminophényl)-3-aminopyrazoline, 1-(4'-hydroxyphényl)-3-aminopyrazoline. De tels composés sont décrits dans le document FR-A-2 018 056. As pyrazoloimidazoles, mention may be made of the compounds 3-amino-4-benzylpyrazolo [1,5-a] imidazole, 3-amino-2,4-dimethylpyrazolo [1,5-a] imidazole, 3-amino-4- methyl-pyrazolo [1,5-a] imidazole. Such compounds are described in US 5,457,200. Mention may also be made of 7-amino-6-methylpyrazolo [1,5-a] imidazole, 7-aminopyrazolo [1,5-a] imidazole, 7-amino-2-methylpyrazolo [1,5-a] imidazole compounds. , 7-amino-2-phenylpyrazolo [1,5-a] imidazole described in patent application EP-A-923,929. Pyrazolobenzimidazoles include 7-amino-6-methylpyrazolo [1,5-compounds]. a] benzimidazole, 6,7-diaminopyrazolo [1,5-a] benzimidazole, 6,7-diamino-2-methylpyrazolo [1,5-a] benzimidazole, 6,7-diamino-2-phenylpyrazolo [1] , 5-a] benzimidazole described, for example, in the patent application EP-A-923,929. As pyrazoloquinolines, mention may be made of the 3-amino-2-phenylpyrazolo [1,5-a] quinoline compounds. Such compounds are described in US 5,457,200. As aminopyrazolines, mention may be made of the compounds 1- (4'-aminophenyl) -3-aminopyrazoline, 1- (4'-hydroxyphenyl) -3-aminopyrazoline. Such compounds are described in FR-A-2 018 056.
A titre de mono- ou diaminotétrahydroquinoléines, on peut citer les composés 5-amino-1,2,3,4-tétrahydroquinoléine, 5-amino-7-chloro-8-pipéridino-1,2,3,4-tétrahydroquinoléine, 5-amino-7-chloro-8-morpholino-1,2,3,4-tétrahydroquinoléine, 5,7-diamino-6-méthyl-8-hydroxy-1,2,3,4-tétrahydroquinoléine, 5-amino-8-méthoxy-1,2,3,4-tétrahydroquinoléine, 5-amino-7-chloro-8-diméthylamino-1,2,3,4-tétra-hydroquinoléine. De tels composés sont décrits dans le document DE-A-24 41 895. A titre de diaminoquinoléines, on peut citer les composés 5,7-diamino-6-méthyl-8-hydroxyquinoléine et 5,7-diamino-2-méthyl-8-hydroxyquinoléine. De tels composés sont décrits dans le document DE-A-24 41 598. A titre de triaminoquinoléines, on peut citer 5,7-diamino-8-méthylaminoquinoléine, 5,7-diamino-8-diméthylaminoquinoléine, 5,7-diamino-8-morpholinoquinoléine, 5,7-diamino-8-béta-hydroxyéthyl- aminoquinoléine, 5,7,8-triaminoquinoléine. De tels composés sont décrits dans le document DE-A-24 41 599. A titre d'aminoindazoles, on peut citer 4,7-diamino-5-méthylindazole, 4,7-diamino-5,6-diméthylindazole, 6,7-diamino- indazole, 6-hydroxy-7-aminoindazole, 1-éthyl-6-hydroxy-7-amino- indazole, 6-aminoindazole, 5,6-diaminoindazole. De tels composés sont décrits dans le document FR-A-2 315 906, DE-A-14 92 166. A titre de diaminouraciles, on peut citer les composés 5,6-diaminouracile, 5,6-diamino-2-thiouracile, 5,6-diamino-3-méthyluracile, 5-amino-3-méthyl-6-méthylaminouracile, 5-amino-3-méthyl-6- béta-hydroxyéthylaminouracile, 5-amino-3-méthyl-6-benzylamino- uracile, 5-amino-3-méthyl-6-phénylaminouracile, 5,6-diamino-1- phényluracile, 5,6-diamino-1,3-diméthyluracile, 5-amino-1,3-diméthyl-6-méthylaminouracile, 5-amino-1,3-diméthyl-6-béta-hydroxyméthyl-aminouracile, 5-amino-1,3-diméthyl-6-benzylaminouracile, 5-amino-1,3-diméthyl-6-phénylaminouracile, 5-amino-1,3-diméthyl-6-diméthylaminouracile. De tels composés sont décrits dans le document DE-A-25 33 629. A titre d'aminoindolénines, on peut citer les composés 2-méthyl-5-aminoindolénine, 1-béta-hydroxyéthyl-2-méthyl-5-amino- indolénine. De tels composés sont décrits dans le document FR-A-1 602 547. A titre d'hydrazones, on peut citer les composés N-méthylpyridone-4-hydrazone, N-méthylthiazolonehydrazone, N- méthylthiazolone-2-hydrazone, N,N-diméthylbenzimidazolone- hydrazone, N-méthylpyridone-2-hydrazone, N-méthylbenzothiazolone- 2-hydrazone, 1,2-diméthylindazolone-3-hydrazone, 1,2,6-triméthyl- pyridone-4-hydrazone, 1-méthylquinolone-2-hydrazone, 1,2,6- triméthyl-3-nitropyridone-4-hydrazone, 1,2,6-triméthyl-3-amino-pyridone-4-hydrazone, N-méthylcyclohexénothiazolonehydrazone, 1,2,5-triméthylpyrazolone-3-hydrazone, 1,2-diméthylindazolone-3-hydrazone, 1,2-diméthyl-5-chloroindazolone-3-hydrazone, 1-méthyl-2-éthyl-5-nitroindazolone-3-hydrazone, N-méthylquinolone-4-hydrazone, N-méthylbenzothiazolone-2-oméga-benzènesulfonylhydrazone. De tels composés sont décrits dans le document FR-A-1 602 547. A titre de dérivés de julolidine ou de lilolidine, on peut citer les composés 9-aminojulolidine, 9-amino-8-méthyljulolidine, 9-amino-8,10-diméthyljulolidine, 8-aminolilolidine. De tels composés sont décrits dans le document DE-A-24 41 597. De préférence, les bases d'oxydation hétérocycliques utiles pour la présente invention sont choisies parmi les pyridines, les pyrimidines, les pyrazoles et les pyrazolopyrimidines. Encore plus préférentiellement, elles sont choisies parmi les 4,5-diaminopyrazoles. De manière particulièrement préférée, les bases d'oxydation benzéniques ou hétérocycliques utilisées dans les compositions selon l'invention sont choisies parmi les para-phénylènediamines cationiques ou non, les para-aminophénols cationiques ou non, les dérivés pyrazoliques, ainsi que leurs sels d'addition. Encore plus préférentiellement, les bases d'oxydation utilisées dans les compositions selon l'invention sont choisies par les dérivés pyrazoliques et leurs sels d'addition. A titre de coupleurs benzéniques utilisables dans les compositions selon l'invention, on peut citer les méta-aminophénols, les méta-phénylènediamines, les méta-diphénols, ainsi que leurs sels d'addition. As mono- or diaminotetrahydroquinolines, mention may be made of 5-amino-1,2,3,4-tetrahydroquinoline, 5-amino-7-chloro-8-piperidino-1,2,3,4-tetrahydroquinoline compounds. amino-7-chloro-8-morpholino-1,2,3,4-tetrahydroquinoline, 5,7-diamino-6-methyl-8-hydroxy-1,2,3,4-tetrahydroquinoline, 5-amino-8 -methoxy-1,2,3,4-tetrahydroquinoline, 5-amino-7-chloro-8-dimethylamino-1,2,3,4-tetrahydroquinoline. Such compounds are described in DE-A-24 41 895. As diaminoquinolines, mention may be made of the compounds 5,7-diamino-6-methyl-8-hydroxyquinoline and 5,7-diamino-2-methyl- 8-hydroxyquinoline. Such compounds are described in DE-A-24 41 598. As triaminoquinolines, mention may be made of 5,7-diamino-8-methylaminoquinoline, 5,7-diamino-8-dimethylaminoquinoline, 5,7-diamino- 8-morpholinoquinoline, 5,7-diamino-8-beta-hydroxyethyl-aminoquinoline, 5,7,8-triaminoquinoline. Such compounds are described in DE-A-24 41 599. As aminoindazoles, mention may be made of 4,7-diamino-5-methylindazole, 4,7-diamino-5,6-dimethylindazole, -diaminoindazole, 6-hydroxy-7-aminoindazole, 1-ethyl-6-hydroxy-7-aminoindazole, 6-aminoindazole, 5,6-diaminoindazole. Such compounds are described in document FR-A-2 315 906, DE-A-14 92 166. By way of diaminouraciles, mention may be made of the compounds 5,6-diaminouracil, 5,6-diamino-2-thiouracil, 5,6-diamino-3-methyluracil, 5-amino-3-methyl-6-methylaminouracil, 5-amino-3-methyl-6-beta-hydroxyethylaminouracil, 5-amino-3-methyl-6-benzylaminuracil, 5-amino-3-methyl-6-phenylaminouracil, 5,6-diamino-1-phenyluracil, 5,6-diamino-1,3-dimethyluracil, 5-amino-1,3-dimethyl-6-methylaminouracil, 5- amino-1,3-dimethyl-6-beta-hydroxymethyl-aminouracil, 5-amino-1,3-dimethyl-6-benzylaminouracil, 5-amino-1,3-dimethyl-6-phenylaminouracil, 5-amino-1, 3-dimethyl-6-diméthylaminouracile. Such compounds are described in DE-A-25 33 629. As aminoindolenines, mention may be made of the compounds 2-methyl-5-aminoindolenine, 1-beta-hydroxyethyl-2-methyl-5-aminoindolenine . Such compounds are described in document FR-A-1 602 547. As hydrazones, mention may be made of the compounds N-methylpyridone-4-hydrazone, N-methylthiazolonehydrazone, N-methylthiazolone-2-hydrazone, N, N dimethylbenzimidazolone hydrazone, N-methylpyridone-2-hydrazone, N-methylbenzothiazolone-2-hydrazone, 1,2-dimethylindazolone-3-hydrazone, 1,2,6-trimethylpyridone-4-hydrazone, 1-methylquinolone-2 -hydrazone, 1,2,6-trimethyl-3-nitropyridone-4-hydrazone, 1,2,6-trimethyl-3-amino-pyridone-4-hydrazone, N-methylcyclohexenothiazolonehydrazone, 1,2,5-trimethylpyrazolone-3 -hydrazone, 1,2-dimethylindazolone-3-hydrazone, 1,2-dimethyl-5-chloroindazolone-3-hydrazone, 1-methyl-2-ethyl-5-nitroindazolone-3-hydrazone, N-methylquinolone-4-hydrazone N-methylbenzothiazolone-2-omega-benzenesulfonylhydrazone. Such compounds are described in document FR-A-1 602 547. As derivatives of julolidine or of lilolidine, mention may be made of the compounds 9-aminojulolidine, 9-amino-8-methyljulolidine, 9-amino-8,10 dimethyljulolidine, 8-aminolilolidine. Such compounds are described in DE-A-24 41 597. Preferably, the heterocyclic oxidation bases useful for the present invention are selected from pyridines, pyrimidines, pyrazoles and pyrazolopyrimidines. Even more preferentially, they are chosen from 4,5-diaminopyrazoles. In a particularly preferred manner, the benzene or heterocyclic oxidation bases used in the compositions according to the invention are chosen from cationic or non-cationic para-phenylenediamines, cationic or non-cationic para-aminophenols, and pyrazole derivatives, as well as their salts. addition. Even more preferably, the oxidation bases used in the compositions according to the invention are chosen by the pyrazole derivatives and their addition salts. As benzene couplers that may be used in the compositions according to the invention, mention may be made of meta-aminophenols, meta-phenylenediamines and meta-diphenols, as well as their addition salts.
Les méta-aminophénols, pouvant être utilisés, à titre de coupleurs benzéniques, dans les compositions tinctoriales conformes à l'invention, sont, de préférence, choisis parmi les composés de formule (VI) suivante : OH N H R7 R8 (VI) dans laquelle : R7 représente un atome d'hydrogène, un groupe alkyle en C1-C4, monohydroxyalkyle en C1-C4 ou polyhydroxyalkyle en C2-C4 ; R8 représente un atome d'hydrogène, un groupe alkyle en C1-C4, alcoxyle en C1-C4 ou un atome d'halogène choisi parmi le chlore, le brome ou le fluor ; R9 représente un atome d'hydrogène, un groupe alkyle en C1-C4, alcoxyle en C1-C4, monohydroxyalkyle en C1-C4, polyhydroxyalkyle en C2-C4, monohydroxyalcoxyle en C1-C4 ou polyhydroxyalcoxyle en C2-C4 et parmi leurs sels d'addition. Parmi les méta-aminophénols de formule (VI) ci-dessus, on peut, plus particulièrement, citer le méta-aminophénol, le 5-amino-2-méthoxyphénol, le 5-amino-2-((3-hydroxyéthyloxy)phénol, le 5-amino-2-méthylphénol, le 5-N-((3-hydroxyéthyl)amino-2-méthylphénol, le 5-N-((3-hydroxyéthyl)amino-4-méthoxy-2-méthylphénol, le 5-amino-4-méthoxy-2-méthylphénol, le 5-amino-4-chloro-2-méthylphénol, le 5- amino-2,4-diméthoxyphénol, le 5-(y-hydroxypropylamino)-2-méthylphénol, et leurs sels d'addition. Les méta-phénylènediamines, pouvant être utilisées à titre de coupleurs benzéniques dans la composition tinctoriale conforme à l'invention sont, de préférence, choisies parmi les composés de formule (VII) suivante : NHR10 RI1 (VII) dans laquelle : R10 représente un atome d'hydrogène, un groupe alkyle en C1-C4, monohydroxyalkyle en C1-C4 ou polyhydroxyalkyle en C2-C4 ; R11 et R12, identiques ou différents, représentent un atome d'hydrogène, un groupe alkyle en C1-C4, monohydroxyalcoxyle en C1-C4 ou polyhydroxyalcoxyle en C2-C4 ; R13 représente un atome d'hydrogène, un groupe alcoxyle en C1-C4, aminoalcoxyle en C1-C4, monohydroxyalcoxyle en C1-C4, polyhydroxyalcoxyle en C2-C4 ou un groupe 2,4- diaminophénoxyalcoxyle ; et parmi leurs sels d'addition. Parmi les méta-phénylènediamines de formule (VII) ci-dessus, on peut, plus particulièrement citer le 2,4-diaminobenzène, le 3,5-diamino-1-éthyl-2-méthoxybenzène, le 3,5-diamino-2-méthoxy-1-méthylbenzène, le 2,4-diamino-1-éthoxybenzène, le 1,3-bis-(2,4-diaminophénoxy)propane, le bis-(2,4-diaminophénoxy)méthane, le 1-((3-aminoéthyloxy)-2,4-diaminobenzéne, le 2-amino-1-(3-hydroxyéthyloxy)-4-méthylaminobenzène, le 2,4-diamino-1-éthoxy-5-méthylbenzène, le 2,4-diamino-5-(3-hydroxyéthyloxy)-l-méthylbenzène, le 2,4-diamino-1-(3,y-dihydroxy-propyloxy)benzène, le 2,4-diamino-1-((3-hydroxyéthyloxy)benzène, le 2-amino-4-N-((3-hydroxyéthyl)-amino-1-méthoxybenzène, et leurs sels d'addition. Les méta-diphénols, pouvant être utilisés, à titre de coupleurs benzéniques dans les compositions tinctoriales conformes à l'invention, sont, de préférence, choisis parmi les composés de formule (VIII) suivante OH dans laquelle : R14 et R15, identiques ou différents, représentent un atome d'hydrogène, un groupe alkyle en C1-C4 ou un atome d'halogène choisi parmi le chlore, le brome ou le fluor ; et parmi leurs sels d'addition. Parmi les méta-diphénols de formule (VIII) ci-dessus, on peut, plus particulièrement, citer le 1,3-dihydroxybenzène, le 2-méthyl-1,3-dihydroxybenzène, le 4-chloro-1,3-dihydroxybenzène, le 2-chloro-1,3- dihydroxybenzène, et leurs sels d'addition. A titre de coupleurs hétérocycliques utilisables dans les compositions selon l'invention, on peut citer les coupleurs hétérocycliques azolés, les coupleurs pyridiniques, les thiophènes, les indolines, les indoles, les benzofuranes, les 8-amino-6- méthoxyquinoléines, les 4-hydroxyquinolones, les benzodioxoles, les hydroxybenzamides, le sésamol et ses dérivés, les benzomorpholines, ainsi que leurs sels d'addition. Les coupleurs hétérocycliques azolés utilisés dans les compositions selon l'invention peuvent être, en particulier, choisis parmi les carbazoles, les hydroxyindazoles, les benzoxazoles, les pyrazoloazoles et les pyrazolotriazoles, les pyrroloazoles, les imidazoloazoles, les thiazoloazoles, les pyrrolo oxazoles, les hydroxypyrazolo pyrimidines, les isoxazolones, les indazolones et les benzimidazoles. The meta-aminophenols which may be used as benzene couplers in the dyeing compositions in accordance with the invention are preferably chosen from compounds of the following formula (VI): ## STR2 ## in which R7 represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 monohydroxyalkyl group or a C2-C4 polyhydroxyalkyl group; R8 represents a hydrogen atom, a C1-C4 alkyl, C1-C4 alkoxyl or a halogen selected from chlorine, bromine or fluorine; R9 represents a hydrogen atom, a C1-C4 alkyl, C1-C4 alkoxyl, C1-C4 monohydroxyalkyl, C2-C4 polyhydroxyalkyl, C1-C4 monohydroxyalkoxyl or C2-C4 polyhydroxyalkoxyl and among their salts; 'addition. Among the meta-aminophenols of formula (VI) above, it is more particularly possible to mention meta-aminophenol, 5-amino-2-methoxyphenol, 5-amino-2 - ((3-hydroxyethyloxy) phenol, 5-amino-2-methylphenol, 5-N - ((3-hydroxyethyl) amino-2-methylphenol, 5-N - ((3-hydroxyethyl) amino-4-methoxy-2-methylphenol, 5- amino-4-methoxy-2-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-2,4-dimethoxyphenol, 5- (y-hydroxypropylamino) -2-methylphenol, and their salts The meta-phenylenediamines, which can be used as benzene couplers in the dyeing composition according to the invention, are preferably chosen from the following compounds of formula (VII): NHR10 RI1 (VII) in which: R10 represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 monohydroxyalkyl group or a C2-C4 polyhydroxyalkyl group; R11 and R12, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl group; C 1 -C 4 monohydroxyalkoxyl or C 2 -C 4 polyhydroxyalkoxy; R13 represents a hydrogen atom, a C1-C4 alkoxyl group, a C1-C4 aminoalkoxyl, a C1-C4 monohydroxyalkoxyl, a C2-C4 polyhydroxyalkoxyl or a 2,4-diaminophenoxyalkoxyl group; and among their addition salts. Among the meta-phenylenediamines of formula (VII) above, mention may more particularly be made of 2,4-diaminobenzene, 3,5-diamino-1-ethyl-2-methoxybenzene, 3,5-diamino-2 methoxy-1-methylbenzene, 2,4-diamino-1-ethoxybenzene, 1,3-bis- (2,4-diaminophenoxy) propane, bis- (2,4-diaminophenoxy) methane, (2-aminoethyloxy) -2,4-diaminobenzene, 2-amino-1- (3-hydroxyethyloxy) -4-methylaminobenzene, 2,4-diamino-1-ethoxy-5-methylbenzene, 2,4-diamino 5- (3-hydroxyethyloxy) -1-methylbenzene, 2,4-diamino-1- (3-yl-dihydroxypropyloxy) benzene, 2,4-diamino-1 - ((3-hydroxyethyloxy) benzene, 2-amino-4-N - ((3-hydroxyethyl) amino-1-methoxybenzene, and their addition salts.) The meta-diphenols, which can be used as benzene couplers in the dye compositions according to the present invention. the invention are preferably chosen from compounds of the following formula (VIII) OH in which: R14 and R15, which are identical or different, have a hydrogen atom, a C1-C4 alkyl group or a halogen atom selected from chlorine, bromine or fluorine; and among their addition salts. Among the meta-diphenols of formula (VIII) above, 1,3-dihydroxybenzene, 2-methyl-1,3-dihydroxybenzene and 4-chloro-1,3-dihydroxybenzene may be mentioned more particularly. 2-chloro-1,3-dihydroxybenzene, and their addition salts. As heterocyclic couplers that can be used in the compositions according to the invention, mention may be made of azole heterocyclic couplers, pyridine couplers, thiophenes, indolines, indoles, benzofurans, 8-amino-6-methoxyquinolines, and the like. hydroxyquinolones, benzodioxoles, hydroxybenzamides, sesamol and its derivatives, benzomorpholines, as well as their addition salts. The azole heterocyclic couplers used in the compositions according to the invention may be, in particular, chosen from carbazoles, hydroxyindazoles, benzoxazoles, pyrazoloazoles and pyrazolotriazoles, pyrroloazoles, imidazoloazoles, thiazoloazoles, pyrrolooxazoles and hydroxypyrazoles. pyrimidines, isoxazolones, indazolones and benzimidazoles.
A titre de carbazoles utilisés dans les compositions de l'invention, on peut citer le 1,3,6,8-tétraaminocarbazole, le 1,3,6,8-tétraamino-9-n-propylcarbazole, le 1,3,6,8-tétraamino-9-13-hydroxyéthylcarbazole, le 1,3,6,8-tétraamino-9-(2'-N,N-diméthylaminoéthyl)-carbazole, et leurs sels d'addition. Ces composés sont décrits dans la demande DE-A-27 15 680. On peut aussi citer, à titre de carbazoles, le 3-aminocarbazole décrit dans la demande DE-A-277 496. A titre d'hydroxyindazoles utilisés, de manière préférée, dans les compositions selon l'invention, on peut citer les monohydroxyindazoles suivants : la 4-hydroxyindazole, la 5-hydroxyindazole, la 6-hydroxyindazole, la 7-hydroxyindazole, la 7-hydroxy-1-méthylindazole, la 4-hydroxy-6-méthylindazole, la 7-hydroxy-6-méthylindazole, la 7-hydroxy-4,6-diméthylindazole, la 6-hydroxy-7-bromoindazole, la 6-hydroxy-7-chloroindazole et la 6-hydroxy-5,7-dichloroindazole. Ces hydroxyindazoles sont décrits dans la demande de brevet DE-A-26 23 564. As carbazoles used in the compositions of the invention, mention may be made of 1,3,6,8-tetraaminocarbazole, 1,3,6,8-tetraamino-9-n-propylcarbazole, 1,3,6,8-tetraaminocarbazole and 1,3,6,8-tetraamino-9-n-propylcarbazole. 8-tetraamino-9-13-hydroxyethylcarbazole, 1,3,6,8-tetraamino-9- (2'-N, N-dimethylaminoethyl) -carbazole, and their addition salts. These compounds are described in application DE-A-27 15 680. It is also possible to mention, as carbazoles, the 3-aminocarbazole described in application DE-A-277 496. As hydroxyindazoles used, preferably in the compositions according to the invention, mention may be made of the following monohydroxyindazoles: 4-hydroxyindazole, 5-hydroxyindazole, 6-hydroxyindazole, 7-hydroxyindazole, 7-hydroxy-1-methylindazole, 4-hydroxy- 6-methylindazole, 7-hydroxy-6-methylindazole, 7-hydroxy-4,6-dimethylindazole, 6-hydroxy-7-bromoindazole, 6-hydroxy-7-chloroindazole and 6-hydroxy-5,7 -dichloroindazole. These hydroxyindazoles are described in patent application DE-A-26 23 564.
A titre de benzoxazoles utilisés dans les compositions selon l'invention, on peut citer les diaminobenzoxazoles suivants : la 5,7-diaminobenzoxazole, la 5,7-diamino-2-méthylbenzoxazole, la 5,7-diamino-2-éthylbenzoxazole, la 5,7-diamino-2-butylbenzoxazole, la 5-diméthylamino-7-aminobenzoxazole, la 5-amino-7-diéthylaminobenzoxazole et la 4,6-diaminobenzoxazole. Ces benzoxazoles sont décrits dans la demande de brevet DE-A-27 19 424. A titre de pyrazoloazoles utilisés dans les compositions selon l'invention, on peut citer les pyrazolo[1,5-b]-1,2,4-triazoles, les pyrazolo[3,2-c]-1,2,4-triazoles, les pyrazolotétrazoles, les pyrazolo[1,5-a]imidazoles, les pyrazolo[1,5-e]pyrazoles et les pyrazolo[1,5-e]-1,2,3-triazoles. De manière préférée, les pyrazolo[1,5-b]-1,2,4-triazoles sont choisis parmi les 2-méthylpyrazolo[1,5-b]-1,2,4-triazole, 2-éthylpyrazolo[1,5-b]-1,2,4-triazole, 2-isopropylpyrazolo[1,5-b]-,2,4-triazole, 2-phénylpyrazolo[1,5-b]-,2,4-triazole, 2,6-diméthylpyrazolo-[1,5-b]-1,2,4-triazole, 6-méthyl-2-éthylpyrazolo-[1,5-b]-1,2,4-triazole, 6-méthyl-2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, 6-méthyl-2-phénylpyrazolo[1,5-b]-1,2,4-triazole, 6-carboxy-2-méthylpyrazolo-[1,5-b]-1,2,4-triazole, 6-carboxy-2-éthylpyrazolo[1,5-b]-1,2,4-triazole, 6-carboxy-2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, 6-carboxy-2-phénylpyrazolo[1,5-b]-1,2,4-triazole, 6-phényl-2-méthylpyrazolo-[1,5-b]-1,2,4-triazole, 6-phényl-2-éthylpyrazolo[1,5-b]-1,2,4-triazole, 6-phényl-2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, 6-phényl-2-phényl-pyrazolo[1,5-b]-1,2,4-triazole, 6-amino-2-méthylpyrazolo[1,5-b]-1,2,4-triazole, 6-amino-2-éthylpyrazolo[1,5-b]-1,2,4-triazole, 6-amino-2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, 6-amino-2-phénylpyrazolo-[1,5-b]-1,2,4-triazole, 6-éthylthio-2-méthylpyrazolo[1,5-b]-1,2,4-triazole, 6-éthylthio-2-éthylpyrazolo[1,5-b]-1,2,4-triazole, 6-éthylthio-2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, 6-éthylthio-2-phényl-pyrazolo[1,5-b]-1,2,4-triazole, 6-éthoxy-2-méthylpyrazolo[1,5-b]-1,2,4-triazole, 6-éthoxy-2-éthylpyrazolo[1,5-b]-1,2,4-triazole, 6-éthoxy-2-isopropylpyrazolo[1,5-b]-1,2,4-triazole, 6-éthoxy-2-phénylpyrazolo[1,5-b]-1,2,4-triazole, 6-méthyl-2-(2'-aminoéthyl)-pyrazolo[1,5-b]-1,2,4-triazole, 6-carboxy-2-(2'-aminoéthyl)pyrazolo-[1,5-b]-1,2,4-triazole, 6-phényl-2-(2'-aminoéthyl)pyrazolo[1,5-b]-1,2,4-triazole, 6-éthylthio-2-(2'-aminoéthyl)pyrazolo[1,5-b]-1,2,4-triazole, 2-(2'-aminoéthyl)pyrazolo[1,5-b]-1,2,4-triazole, 2-(2'-hydroxyéthyl)pyrazolo[1,5-b]-1,2,4-triazole, 6-méthyl-2-(2'-hydroxy-éthyl)pyrazolo[1,5-b]-1,2,4-triazole, 6-éthylthio-2-(2'-hydroxyéthyl)-pyrazolo[1,5-b]-1,2,4-triazole, 6-carboxy-2-(2'-hydroxyéthyl)pyrazolo-[1,5-b]-1,2,4-triazole, 6-phényl-2-(2'-hydroxyéthyl)pyrazolo[1,5-b]-1,2,4-triazole, 7-chloro-2,6-diméthylpyrazolo[1,5-b]-1,2,4-triazole, 7-bromo-2,6-diméthylpyrazolo[1,5-b]-1,2,4-triazole, et leurs sels d'addition. As benzoxazoles used in the compositions according to the invention, mention may be made of the following diaminobenzoxazoles: 5,7-diaminobenzoxazole, 5,7-diamino-2-methylbenzoxazole, 5,7-diamino-2-ethylbenzoxazole, 5,7-diamino-2-butylbenzoxazole, 5-dimethylamino-7-aminobenzoxazole, 5-amino-7-diethylaminobenzoxazole and 4,6-diaminobenzoxazole. These benzoxazoles are described in the patent application DE-A-27 19 424. As pyrazoloazoles used in the compositions according to the invention, mention may be made of pyrazolo [1,5-b] -1,2,4-triazoles , pyrazolo [3,2-c] 1,2,4-triazoles, pyrazolotetrazoles, pyrazolo [1,5-a] imidazoles, pyrazolo [1,5-e] pyrazoles and pyrazolo [1,5] -e] -1,2,3-triazoles. Preferably, the pyrazolo [1,5-b] -1,2,4-triazoles are chosen from 2-methylpyrazolo [1,5-b] -1,2,4-triazole, 2-ethylpyrazolo [1, 5-b] -1,2,4-triazole, 2-isopropylpyrazolo [1,5-b] -, 2,4-triazole, 2-phenylpyrazolo [1,5-b] -, 2,4-triazole, 2 6-dimethylpyrazolo [1,5-b] -1,2,4-triazole, 6-methyl-2-ethylpyrazolo [1,5-b] -1,2,4-triazole, 6-methyl-2 isopropylpyrazolo [1,5-b] -1,2,4-triazole, 6-methyl-2-phenylpyrazolo [1,5-b] -1,2,4-triazole, 6-carboxy-2-methylpyrazolo [ 1,5-b] -1,2,4-triazole, 6-carboxy-2-ethylpyrazolo [1,5-b] -1,2,4-triazole, 6-carboxy-2-isopropylpyrazolo [1,5- b] -1,2,4-triazole, 6-carboxy-2-phenylpyrazolo [1,5-b] -1,2,4-triazole, 6-phenyl-2-methylpyrazolo [1,5-b] - 1,2,4-triazole, 6-phenyl-2-ethylpyrazolo [1,5-b] -1,2,4-triazole, 6-phenyl-2-isopropylpyrazolo [1,5-b] -1,2, 4-triazole, 6-phenyl-2-phenyl-pyrazolo [1,5-b] -1,2,4-triazole, 6-amino-2-methylpyrazolo [1,5-b] -1,2,4- triazole, 6-amino-2-ethylpyrazolo [1,5-b] -1,2,4-triazole, 6-amino-2-isopropylpyrazolo [1,5-b] -1,2,4-t riazole, 6-amino-2-phenylpyrazolo [1,5-b] -1,2,4-triazole, 6-ethylthio-2-methylpyrazolo [1,5-b] -1,2,4-triazole, 6 1-ethylthio-2-ethylpyrazolo [1,5-b] -1,2,4-triazole, 6-ethylthio-2-isopropylpyrazolo [1,5-b] -1,2,4-triazole, 6-ethylthio-2 phenyl-pyrazolo [1,5-b] -1,2,4-triazole, 6-ethoxy-2-methylpyrazolo [1,5-b] -1,2,4-triazole, 6-ethoxy-2-ethylpyrazolo [1,5-b] -1,2,4-triazole, 6-ethoxy-2-isopropylpyrazolo [1,5-b] -1,2,4-triazole, 6-ethoxy-2-phenylpyrazolo [1.5] b) -1,2,4-triazole, 6-methyl-2- (2'-aminoethyl) -pyrazolo [1,5-b] -1,2,4-triazole, 6-carboxy-2- 1-aminoethyl) pyrazolo [1,5-b] -1,2,4-triazole, 6-phenyl-2- (2'-aminoethyl) pyrazolo [1,5-b] -1,2,4-triazole 6-ethylthio-2- (2'-aminoethyl) pyrazolo [1,5-b] -1,2,4-triazole, 2- (2'-aminoethyl) pyrazolo [1,5-b] -1,2 , 4-triazole, 2- (2'-hydroxyethyl) pyrazolo [1,5-b] -1,2,4-triazole, 6-methyl-2- (2'-hydroxy-ethyl) pyrazolo [1.5- b] -1,2,4-triazole, 6-ethylthio-2- (2'-hydroxyethyl) -pyrazolo [1,5-b] -1,2,4-triazole, 6-carboxy-2- (2 ') hydroxyethyl) pyrazolo [1, 5-b] -1,2,4-triazole, 6-phenyl-2- (2'-hydroxyethyl) pyrazolo [1,5-b] -1,2,4-triazole, 7-chloro-2,6- dimethylpyrazolo [1,5-b] -1,2,4-triazole, 7-bromo-2,6-dimethylpyrazolo [1,5-b] -1,2,4-triazole, and their addition salts.
De manière préférée, les pyrazolo[3,2-c]-1,2,4-triazoles sont choisis parmi les 3-méthylpyrazolo[3,2-c]-1,2,4-triazole, 3-méthylsulfinyl-6-phénylpyrazolo[3,2-c]-1,2,4-triazole, 3-éthyl-pyrazolo[3,2-c]-1,2,4-triazole, 3-isopropylpyrazolo[3,2-c]-1,2,4-triazole, 3-phénylpyrazolo[3,2-c]-1,2,4-triazole, 3-(2'aminoéthyl)-pyrazolo[3,2-c]-1,2,4-triazole, 3-(2'-hydroxyéthyl)pyrazolo[3,2-c]-1,2,4-triazole, 6-méthyl-3-éthylpyrazolo[3,2-c]-1,2,4-triazole, 3,6-diméthylpyrazolo[3,2-c]-1,2,4-triazole, 6-méthyl-3-isopropylpyrazolo-[3,2-c]-1,2,4-triazole, 6-méthyl-3-phénylpyrazolo[3,2-c]-1,2,4-triazole, 6-méthyl-3-(2'amino éthyl)pyrazolo[3,2-c]-1,2,4-triazole, 6-méthyl-3-(2'-hydroxyéthyl)pyrazolo[3,2-c]-1,2,4-triazole, 6-méthyl-3-méthyl-thiopyrazolo[3,2-c]-1,2,4-triazole, 6-phényl-3-méthylpyrazolo[3,2-c]-1,2,4-triazole, 6-phényl-3-éthylpyrazolo[3,2-c]-1,2,4-triazole, 6-isopropyl-3-éthylpyrazolo[3,2-c]-1,2,4-triazole, 6-phényl-3-isopropylpyrazolo[3,2-c]-1,2,4-triazole, 6phényl-3-phénylpyrazolo-[3,2-c]-1,2,4-triazole, 6-phényl-3-(2'aminoéthyl)pyrazolo[3,2-c]-1,2,4-triazole, 6-phényl-3-(2'-hydroxyéthyl)pyrazolo-[3,2-c]-1,2,4-triazole, 6-phényl-3-méthylthiopyrazolo[3,2-c]-1,2,4-triazole, 6-éthylthio-3-méthylpyrazolo[3,2-c]-1,2,4-triazole, 6-éthylthio-3-éthylpyrazolo[3,2-c]-1,2,4-triazole, 6-éthylthio-3-isopropylpyrazolo[3,2-c]-1,2,4-triazole, 6-éthylthio-3-phénylpyrazolo[3,2-c]-1,2,4-triazole, 6-éthylthio-3(2'amino éthyl)pyrazolo[3,2-c]-1,2,4-triazole, 6-éthylthio-3-(2'-hydroxy-éthyl)pyrazolo[3,2-c]-1,2,4-triazole, 6-trifluorométhyl-3-méthylthiopyrazolo[3,2-c]-1,2,4-triazole, 6-trifluorométhylpyrazolo[3,2-c]-1,2,4-triazole, 6-carboxy-3-méthylpyrazolo[3,2-c]-1,2,4-triazole, 6-carboxy-3-éthylpyrazolo[3,2-c]-1,2,4-triazole, 6-carboxy-3-isopropylpyrazolo-[3,2-c]-1,2,4-triazole, 6-carboxy-3-phénylpyrazolo[3,2-c]-1,2,4- triazole, 6-carboxy-3-(2'aminoéthyl)pyrazolo[3,2-c]-1,2,4-triazole, 6-carboxy-3-(2'-hydroxyéthyl)pyrazolo[3,2-c]-1,2,4-triazole, 7-chloro-3,6-diméthylpyrazolo[3,2-c]-1,2,4-triazole, 7-méthoxycarbonyl-3,6-diméthylpyrazolo[3,2-c]-1,2,4-triazole, et leurs sels d'addition. Preferably, the pyrazolo [3,2-c] -1,2,4-triazoles are chosen from 3-methylpyrazolo [3,2-c] -1,2,4-triazole, 3-methylsulfinyl-6- phenylpyrazolo [3,2-c] -1,2,4-triazole, 3-ethyl-pyrazolo [3,2-c] -1,2,4-triazole, 3-isopropylpyrazolo [3,2-c] -1 2,4-triazole, 3-phenylpyrazolo [3,2-c] -1,2,4-triazole, 3- (2'aminoethyl) -pyrazolo [3,2-c] -1,2,4-triazole 3- (2'-hydroxyethyl) pyrazolo [3,2-c] -1,2,4-triazole, 6-methyl-3-ethylpyrazolo [3,2-c] -1,2,4-triazole, 3 6-dimethylpyrazolo [3,2-c] -1,2,4-triazole, 6-methyl-3-isopropylpyrazolo [3,2-c] -1,2,4-triazole, 6-methyl-3- phenylpyrazolo [3,2-c] -1,2,4-triazole, 6-methyl-3- (2'aminoethyl) pyrazolo [3,2-c] -1,2,4-triazole, 6-methyl- 3- (2'-hydroxyethyl) pyrazolo [3,2-c] -1,2,4-triazole, 6-methyl-3-methyl-thiopyrazolo [3,2-c] -1,2,4-triazole, 6-phenyl-3-methylpyrazolo [3,2-c] -1,2,4-triazole, 6-phenyl-3-ethylpyrazolo [3,2-c] -1,2,4-triazole, 6-isopropyl- 3-ethylpyrazolo [3,2-c] -1,2,4-triazole, 6-phenyl-3-isopropylpyrazolo [3,2-c] -1,2,4-triazole, 6ph nyl-3-phenylpyrazolo [3,2-c] -1,2,4-triazole, 6-phenyl-3- (2'aminoethyl) pyrazolo [3,2-c] -1,2,4-triazole, 6-phenyl-3- (2'-hydroxyethyl) pyrazolo [3,2-c] -1,2,4-triazole, 6-phenyl-3-methylthiopyrazolo [3,2-c] -1,2,4 -triazole, 6-ethylthio-3-methylpyrazolo [3,2-c] -1,2,4-triazole, 6-ethylthio-3-ethylpyrazolo [3,2-c] -1,2,4-triazole, 6 3-ethylthio-3-isopropylpyrazolo [3,2-c] -1,2,4-triazole, 6-ethylthio-3-phenylpyrazolo [3,2-c] -1,2,4-triazole, 6-ethylthio-3 (2-aminoethyl) pyrazolo [3,2-c] -1,2,4-triazole, 6-ethylthio-3- (2'-hydroxy-ethyl) pyrazolo [3,2-c] -1,2, 4-triazole, 6-trifluoromethyl-3-methylthiopyrazolo [3,2-c] -1,2,4-triazole, 6-trifluoromethylpyrazolo [3,2-c] -1,2,4-triazole, 6-carboxy- 3-methylpyrazolo [3,2-c] -1,2,4-triazole, 6-carboxy-3-ethylpyrazolo [3,2-c] -1,2,4-triazole, 6-carboxy-3-isopropylpyrazolo [3,2-c] -1,2,4-triazole, 6-carboxy-3-phenylpyrazolo [3,2-c] -1,2,4-triazole, 6-carboxy-3- (2'-aminoethyl) pyrazolo [3,2-c] -1,2,4-triazole, 6-carboxy-3- (2'-hydroxyethyl) pyrazolo [3,2-c] -1,2,4- triazole, 7-chloro-3,6-dimethylpyrazolo [3,2-c] -1,2,4-triazole, 7-methoxycarbonyl-3,6-dimethylpyrazolo [3,2-c] -1,2,4- triazole, and their addition salts.
De manière préférée, les pyrazolotétrazoles sont choisis parmi les pyrazolo[5,1-e]tétrazole, 6-méthylpyrazolo[5,1-e]tétrazole, 6-phénypyrazolo[5, 1-e]tétrazole, 6-carboxypyrazolo[5,1-e]tétrazole, 7-chloro-6-méthylpyrazolo[5,1-e]tétrazole, et leurs sels d'addition. De manière préférée, les pyrazolo[1,5-a]imidazoles sont choisis parmi les pyrazolo[1,5-a]imidazole, 2-méthylpyrazolo[1,5-a]imidazole, 2-phénylpyrazolo[1,5-a]imidazole, pyrazolo[1,5-a]benzimidazole,6-méthylpyrazolo[1,5-a]imidazole, 2,6-diméthylpyrazolo[1,5-a]- imidazole, 6-méthyl-2-phénylpyrazolo[1,5-a]imidazole, 6-méthylpyrazolo[1,5-a]benzimidazole, 6-phénylpyrazolo[1,5-a]- imidazole, 6-phényl-2-méthylpyrazolo[1,5-a]imidazole, 2,6-diphénylpyrazolo[1,5-a]imidazole, 6-phénylpyrazolo[1,5-a]benzimidazole, 6-carboxypyrazolo[1,5-a]imidazole, 6carboxy-2-méthylpyrazolo[1,5-a]imidazole, 6-carboxy-2-phénylpyrazolo[1,5-a]-imidazole, 6-carboxypyrazolo[1,5-a]benzimidazole, 6-éthoxypyrazolo-[1,5-a]imidazole, 6-éthoxy-2-méthylpyrazolo[1,5-a]imidazole, 6-éthoxy-2-phénylpyrazolo[1,5-a]imidazole, 6-trifluorométhylpyrazolo-[1,5-a]benzimidazole, 6-aminopyrazolo[1,5-a]imidazole, 6-amino-2-méthylpyrazolo[1,5-a]imidazole, 6-amino-2-phénylpyrazolo[1,5-a]-imidazole, 6-aminopyrazolo[1,5-a]benzimidazole, 6-éthylthiopyrazolo-[1,5-a]imidazole, 6-éthylthio-2-méthylpyrazolo[1,5-a]imidazole, 6-éthylthio-2-phénylpyrazolo[1,5-a]imidazole, 7-chloro-6-méthyl-pyrazolo[1,5-a]imidazole, 7-chloro-6-méthylpyrazolo[1,5-a]- benzimidazole, et leurs sels d'addition. De manière préférée, les pyrazolo[5,1-e]pyrazoles sont choisis parmi le 8-amino-4-méthylpyrazolo[5,1-e]pyrazole, le 8-amino-5-chloro-4-méthylpyrazolo[5,1-e]pyrazole, et leurs sels d'addition. De manière préférée, les pyrazolo[5,1-e]-1,2,3-triazoles sont choisis parmi les 5-méthylpyrazolo[5,1-e]-1,2,3-triazole, 5-méthyl-6-chloropyrazolo[5,1-e]-1,2,3-triazole, 5-phénylpyrazolo[5,1-e]-1,2,3- triazole, et leurs sels d'addition. In a preferred manner, the pyrazolotetrazoles are chosen from pyrazolo [5,1-e] tetrazole, 6-methylpyrazolo [5,1-e] tetrazole, 6-phenypyrazolo [5,1-e] tetrazole, 6-carboxypyrazolo [5, 1-e] tetrazole, 7-chloro-6-methylpyrazolo [5,1-e] tetrazole, and their addition salts. Preferably, the pyrazolo [1,5-a] imidazoles are chosen from pyrazolo [1,5-a] imidazole, 2-methylpyrazolo [1,5-a] imidazole, 2-phenylpyrazolo [1,5-a] imidazole, pyrazolo [1,5-a] benzimidazole, 6-methylpyrazolo [1,5-a] imidazole, 2,6-dimethylpyrazolo [1,5-a] imidazole, 6-methyl-2-phenylpyrazolo [1.5] -a] imidazole, 6-methylpyrazolo [1,5-a] benzimidazole, 6-phenylpyrazolo [1,5-a] imidazole, 6-phenyl-2-methylpyrazolo [1,5-a] imidazole, 2,6- diphenylpyrazolo [1,5-a] imidazole, 6-phenylpyrazolo [1,5-a] benzimidazole, 6-carboxypyrazolo [1,5-a] imidazole, 6carboxy-2-methylpyrazolo [1,5-a] imidazole, 6- carboxy-2-phenylpyrazolo [1,5-a] imidazole, 6-carboxypyrazolo [1,5-a] benzimidazole, 6-ethoxypyrazolo [1,5-a] imidazole, 6-ethoxy-2-methylpyrazolo [1, 5-a] imidazole, 6-ethoxy-2-phenylpyrazolo [1,5-a] imidazole, 6-trifluoromethylpyrazolo [1,5-a] benzimidazole, 6-aminopyrazolo [1,5-a] imidazole, 6-amino -2-methylpyrazolo [1,5-a] imidazole, 6-amino-2-phenylpyrazolo [1,5-a] imidazole, 6-aminopyrazolo [1, 5-a] benzimidazole, 6-ethylthiopyrazolo [1,5-a] imidazole, 6-ethylthio-2-methylpyrazolo [1,5-a] imidazole, 6-ethylthio-2-phenylpyrazolo [1,5-a] imidazole 7-chloro-6-methyl-pyrazolo [1,5-a] imidazole, 7-chloro-6-methylpyrazolo [1,5-a] benzimidazole, and their addition salts. Preferably, the pyrazolo [5,1-e] pyrazoles are chosen from 8-amino-4-methylpyrazolo [5,1-e] pyrazole, 8-amino-5-chloro-4-methylpyrazolo [5.1 pyrazole, and their addition salts. Preferably, the pyrazolo [5,1-e] -1,2,3-triazoles are chosen from 5-methylpyrazolo [5,1-e] -1,2,3-triazole, 5-methyl-6- chloropyrazolo [5,1-e] -1,2,3-triazole, 5-phenylpyrazolo [5,1-e] -1,2,3-triazole, and their addition salts.
Ces pyrazoloazoles sont décrits dans la demande de brevet WO 97/35551. A titre de pyrroloazoles utilisés dans les compositions selon l'invention, on peut citer les pyrrolo[1,2-b]-1,2,4-triazoles, pyrrolo[2,1-c]-1,2,4-triazoles, pyrrolo[1,2-c]imidazoles, pyrrolo-[1,2-e]tétrazoles, pyrrolo[1,2-a]pyrroles, pyrrolo[1,2-a]imidazoles, pyrrolo[1,2-c]-1,2,3-triazoles, et leurs sels d'addition. De manière préférée, les pyrrolo[1,2-b]-1,2,4-triazoles sont choisis parmi les 3,4-dicyano-8-méthylpyrrolo[1,2-b]-1,2,4-triazole, 3,4-dicyano-8-phénylpyrrolo[1,2-b]-1,2,4-triazole, 3,4-dicyano-8-tertbutylpyrrolo[1,2-b]-1,2,4-triazole, 5-chloro-3,4-dicyano-8-méthylpyrrolo[1,2-b]-1,2,4-triazole ainsi que les 5-cyano-4-éthoxycarbonyl-8- méthylpyrrolo[1,2-b] 1,2,4-triazole, 5-cyano-4-carboxy-8-méthyl- pyrrolo[1,2-b]-1,2,4-triazole, 4,5-dicyano-8-méthylpyrrolo[1,2-b]- 1,2,4-triazole, 5-cyano-8-méthyl-4-phénylpyrrolo[1,2-b]-1,2,4-triazole, 4,8-diméthylpyrrolo[1,2-b]-1,2,4-triazole, 4,5-di(éthoxycarbonyl)-8-méthylpyrrolo[1,2-b]-1,2,4-triazole, 3-chloro-5-cyano-4-éthoxy-carbonyl-8-méthylpyrrolo[1,2-b]-1,2,4-triazole, 5-cyano-4-éthoxy-carbonyl-8-phénylpyrrolo[1,2-b]-1,2,4-triazole, 5-cyano-4-carboxy-8-phénylpyrrolo[1,2-b]-1,2,4-triazole, 4,5-dicyano-8-phénylpyrrolo-[1,2-b]-1,2,4-triazole, 4,5-di(éthoxycarbonyl)-8-phénylpyrrolo[1,2-b]-1,2,4-triazole, 3-chloro-5-cyano-4-éthoxycarbonyl-8-phénypyrrolo-[1,2-b]-1,2,4-triazole, 4-cyano-5-carboxy-8-(2-nitro-5-hydroxyphényl)-pyrrolo[1,2-b]-1,2, 4-triazole, et leurs sels d'addition. These pyrazoloazoles are described in patent application WO 97/35551. As pyrroloazoles used in the compositions according to the invention, there may be mentioned pyrrolo [1,2-b] -1,2,4-triazoles, pyrrolo [2,1-c] -1,2,4-triazoles pyrrolo [1,2-c] imidazoles, pyrrolo [1,2-e] tetrazoles, pyrrolo [1,2-a] pyrroles, pyrrolo [1,2-a] imidazoles, pyrrolo [1,2-c] 1,2,3-triazoles, and their addition salts. Preferably, the pyrrolo [1,2-b] -1,2,4-triazoles are chosen from 3,4-dicyano-8-methylpyrrolo [1,2-b] -1,2,4-triazole, 3,4-dicyano-8-phenylpyrrolo [1,2-b] -1,2,4-triazole, 3,4-dicyano-8-tertbutylpyrrolo [1,2-b] -1,2,4-triazole, 5-chloro-3,4-dicyano-8-methylpyrrolo [1,2-b] -1,2,4-triazole and also 5-cyano-4-ethoxycarbonyl-8-methylpyrrolo [1,2-b] 1 , 2,4-triazole, 5-cyano-4-carboxy-8-methylpyrrolo [1,2-b] -1,2,4-triazole, 4,5-dicyano-8-methylpyrrolo [1,2- b] - 1,2,4-triazole, 5-cyano-8-methyl-4-phenylpyrrolo [1,2-b] -1,2,4-triazole, 4,8-dimethylpyrrolo [1,2-b] 1,2,4-triazole, 4,5-di (ethoxycarbonyl) -8-methylpyrrolo [1,2-b] -1,2,4-triazole, 3-chloro-5-cyano-4-ethoxy-carbonyl 8-methylpyrrolo [1,2-b] -1,2,4-triazole, 5-cyano-4-ethoxycarbonyl-8-phenylpyrrolo [1,2-b] -1,2,4-triazole, -cyano-4-carboxy-8-phenylpyrrolo [1,2-b] -1,2,4-triazole, 4,5-dicyano-8-phenylpyrrolo [1,2-b] -1,2,4- triazole, 4,5-di (ethoxycarbonyl) -8-phenylpyrrolo [1,2-b] -1,2,4-triazole, 3-chloro-5-cyano-4-ene thoxycarbonyl-8-phenypyrrolo [1,2-b] -1,2,4-triazole, 4-cyano-5-carboxy-8- (2-nitro-5-hydroxyphenyl) -pyrrolo [1,2-b] -1,2,4-triazole, and their addition salts.
De manière préférée, les pyrrolo[2,1-c]-1,2,4-triazoles sont choisis parmi les 5,6-dicyano-3-méthylpyrrolo[2,1-c]-1,2,4-triazole, 7-chloro-5,6-dicyano-3-méthylpyrrolo[2,1-c]-1,2,4-triazole, ainsi que les 6,7-dicyano-3-méthylpyrrolo[2,1-c]-1,2,4-triazole, 5-chloro-6,7 dicyano-3-méthylpyrrolo[2,1-c]-1,2,4-triazole, 6,7-di(éthoxycarbonyl)-3-méthylpyrrolo[2,1-c]-1,2,4-triazole, 7-cyano-3-méthyl-6-phényl-pyrrolo[2,1-c]-1,2,4-triazole, 7-cyano-3-méthyl-6-tertbutylpyrrolo-[2,1-c]-1,2,4-triazole, et leurs sels d'addition. De manière préférée, les pyrrolo[1,2-c]imidazoles sont choisis parmi les 6,8-dicyano-5-éthoxycarbonylpyrrolo[1,2-c]imidazole, 4-chloro-6,8-dicyano-5-éthoxycarbonylpyrrolo[1,2-c]imidazole, et leurs sels d'addition. Preferably, the pyrrolo [2,1-c] -1,2,4-triazoles are chosen from 5,6-dicyano-3-methylpyrrolo [2,1-c] -1,2,4-triazole, 7-chloro-5,6-dicyano-3-methylpyrrolo [2,1-c] -1,2,4-triazole, as well as 6,7-dicyano-3-methylpyrrolo [2,1-c] -1 2,4-triazole, 5-chloro-6,7-dicyano-3-methylpyrrolo [2,1-c] -1,2,4-triazole, 6,7-di (ethoxycarbonyl) -3-methylpyrrolo [2], 1-c] -1,2,4-triazole, 7-cyano-3-methyl-6-phenylpyrrolo [2,1-c] -1,2,4-triazole, 7-cyano-3-methyl- 6-tert-butylpyrrolo [2,1-c] -1,2,4-triazole, and their addition salts. Preferably, the pyrrolo [1,2-c] imidazoles are chosen from 6,8-dicyano-5-ethoxycarbonylpyrrolo [1,2-c] imidazole, 4-chloro-6,8-dicyano-5-ethoxycarbonylpyrrolo [ 1,2-c] imidazole, and their addition salts.
De manière préférée, les pyrrolo[1,2-e]tétrazoles sont choisis parmi les 6,7-dicyanopyrrolo[1,2-e]tétrazole, 6-cyano-7-éthoxycarbonylpyrrolo[1,2-e]tétrazole, 5-chloro-6,7-dicyanopyrrolo-[1,2-e]tétrazole, et leurs sels d'addition. Preferably, the pyrrolo [1,2-e] tetrazoles are chosen from 6,7-dicyanopyrrolo [1,2-e] tetrazole, 6-cyano-7-ethoxycarbonylpyrrolo [1,2-e] tetrazole, 5- chloro-6,7-dicyanopyrrolo [1,2-e] tetrazole, and their addition salts.
De manière préférée, les pyrrolo[1,2-a]imidazoles sont choisis parmi les 2,3,7-tricyano-6-méthylpyrrolo[1,2-a]imidazole, 2,3,7-tricyano-6-trifluorométhylpyrrolo[1,2-a]imidazole, 2,3,7-tricyano-6-tertbutylpyrrolo[1,2-a]imidazole, 2,3,7-tricyano-6-phénylpyrrolo-[1,2-a]imidazole, 2,3,7-tricyano-6-éthoxycarbonylpyrrolo[1,2-a]-imidazole, 5-chloro-2,3,7-tricyano-6-tertbutylpyrrolo[1,2-a]imidazole, 5-chloro-2,3,7-tricyano-6-phénylpyrrolo[1,2-a]imidazole, 7-cyano-6-éthoxycarbonylpyrrolo[1,2-a]benzimidazole, 7-cyano-6-phénylpyrrolo-[1,2-a]benzimidazole, 7-amido-6-éthoxycarbonypyrrolo[1,2-a]-benzimidazole, et leurs sels d'addition. Preferably, the pyrrolo [1,2-a] imidazoles are chosen from 2,3,7-tricyano-6-methylpyrrolo [1,2-a] imidazole, 2,3,7-tricyano-6-trifluoromethylpyrrolo [ 1,2-a] imidazole, 2,3,7-tricyano-6-tert-butylpyrrolo [1,2-a] imidazole, 2,3,7-tricyano-6-phenylpyrrolo [1,2-a] imidazole, 2 , 3,7-tricyano-6-ethoxycarbonylpyrrolo [1,2-a] imidazole, 5-chloro-2,3,7-tricyano-6-tertbutylpyrrolo [1,2-a] imidazole, 5-chloro-2, 3,7-Tricyano-6-phenylpyrrolo [1,2-a] imidazole, 7-cyano-6-ethoxycarbonylpyrrolo [1,2-a] benzimidazole, 7-cyano-6-phenylpyrrolo [1,2-a] benzimidazole 7-Amido-6-ethoxycarbonypyrrolo [1,2-a] benzimidazole, and their addition salts.
De manière préférée, les pyrrolo[1,2-c]-1,2,3-triazoles sont choisis parmi les 5,6,8-tricyanopyrrolo[1,2-c]-1,2,3-triazole, 5,8-dicyano-6-éthoxycarbonylpyrrolo[1,2-c]-1,2,3-triazole, 4-chloro-5,8-dicyano-6-éthoxycarbonylpyrrolo[1,2-c]-1,2,3-triazole, et leurs sels d'addition. Preferably, the pyrrolo [1,2-c] -1,2,3-triazoles are chosen from 5,6,8-tricyanopyrrolo [1,2-c] -1,2,3-triazole, 5, 8-dicyano-6-ethoxycarbonylpyrrolo [1,2-c] -1,2,3-triazole, 4-chloro-5,8-dicyano-6-ethoxycarbonylpyrrolo [1,2-c] -1,2,3- triazole, and their addition salts.
Ces pyrroloazoles sont décrits dans la demande de brevet WO 97/35554. A titre d'imidazoloazoles utilisés dans les compositions selon l'invention, on peut citer les imidazolo[3,2-a] imidazoles, imidazolo[1,2-b]-1,2,4-triazoles et les imidazolo[2,1-c]-1,2,4-triazoles, et leurs sels d'addition. De manière préférée, les imidazolo[3,2-a] imidazoles sont choisis parmi les 7,8-dicyano-imidazolo[3,2-a]imidazole, 7,8-dicyano- 4-méthylimidazolo[3,2-a]imidazole, 7,8-dicyano-4-éthyl-imidazolo- [3,2-a]imidazole, 7,8-dicyano-4-isopropylimidazolo[3,2-a]imidazole, 7,8-dicyano-4-phénylimidazolo[3,2-a]imidazole, 5-chloro-7,8-dicyano-4-méthylimidazolo[3,2-a]imidazole, 7,8-dicyano-4-trifluorométhyl-imidazolo[3,2-a]imidazole, et leurs sels d'addition. De manière préférée, les imidazolo[1,2-b]-1,2,4-triazoles sont choisis parmi les imidazolo[1,2-b]-1,2,4-triazole, 6-méthylimidazolo-[1,2-b]-1,2,4-triazole, 6-isopropylimidazolo[1,2-b]-1,2,4-triazole, 6-phénylimidazolo[1,2-b]-1,2,4-triazole, 2,6-diméthylimidazolo[1,2-b]-1,2,4-triazole, 6-isopropyl-2-méthylimidazolo[1,2-b]-1,2,4-triazole, 2-méthyl-6-phénylimidazolo[1,2-b]-1,2,4-triazole, 6-méthyl-2-phénylimidazolo[1,2-b]-1,2,4-triazole, 6-isopropyl-2-phénylimidazolo[1,2-b]-1,2,4-triazole, 7-chloro-2,6-diméthylimidazolo[1,2-b]-1,2,4-triazole, 7-chloro-2-phényl-6-tertbutylimidazolo[1,2-b]-1,2,4-triazole, 6-trifluorométhylimidazolo[1,2-b]-1,2,4-triazole, et leurs sels d'addition. De manière préférée, les imidazolo[2,1-c]-1,2,4-triazoles sont choisis parmi les imidazolo[2,1-c]-1,2,4-triazole, 5-méthyl-imidazolo[2,1-c]-1,2,4-triazole, 5,8-diméthylimidazolo[2,1-c]-1,2,4-triazole, 5-méthyl-8-phénylimidazolo[2,1-c]-1,2,4-triazole, 8-phényl-imidazolo[2,1-c]-1,2,4-triazole, 6-chloro-5,8-diméthylimidazolo-[2,1-c]-1,2,4-triazole, et leurs sels d'addition. De manière préférée, les imidazolo[2,1-c]-1,2,4-triazoles sont choisis parmi les imidazolo[2,1-c]-1,2,4-triazole, 5-méthyl-imidazolo[2,1-c]-1,2,4-triazole, 5,8-diméthylimidazolo[2,1-c]-1,2,4-triazole, 5-méthyl-8-phénylimidazolo[2,1-c]-1,2,4-triazole, 8-phénylimidazolo[2, 1-c]-1,2,4-triazole, 6-chloro-5,8-diméthylimidazolo-[2,1-c]-1,2,4-triazole, et leurs sels d'addition. Ces imidazoloazoles sont décrits dans la demande de brevet WO 97/35552. Les thiazoloazoles sont décrits dans la demande de brevet FR-A2 752 524. A titre de pyrrolooxazoles utilisés dans les compositions selon l'invention, on peut citer les composés décrits, de manière générale, dans les demandes de brevet FR-A-2 752 522, et leurs sels d'addition. A titre d' hydroxypyrazolopyrimidines utilisées dans les compositions selon l'invention, on peut citer les hydroxypyrazolo-[1,5-a]pyrimidines et plus particulièrement les 2-hydroxy-5-méthyl-7-éthylpyrazolo[1,5-a]pyrimidine, 2-hydroxy-5,6,7-triméthylpyrazolo- [1,5-a]pyrimidine, 2-hydroxy-5,7-diméthyl-6-éthylpyrazolo[1,5-a]- pyrimidine, 2-hydroxy-7-méthylpyrazolo[1,5-a]pyrimidine, 2-hydroxy-5-méthyl-7-carboxypyrazolo[1,5-a]pyrimidine, 2,7-dihydroxy-5,6-diméthylpyrazolo[1,5-a]pyrimidine et leurs sels d'addition. Ces hydroxypyrazolopyrimidines sont décrites dans la demande de brevet DE-A-40 29 324. 37 A titre d'isoxazolones utilisées dans les compositions selon l'invention, on peut citer les 4-carboxy-13,y-benzoisoxazolone, 1-acétyl-4-carboxy-(3,y-benzoisoxazolone, 6-carboxy-(3,y-benzoisoxazolone, 1-acétyl-6-carboxy-(3,y-benzoisoxazolone, (3,y-benzoisoxazolone, 1-acétyl-(3,y-benzoisoxazolone, 4-méthyl-(3,y-benzoisoxazolone, 1-acétyl-4-((3-hydroxyéthylamino)carbonyl-(3,y-benzoisoxazolone, 3-phénylisoxazol-5-one, 2-acétyl-3-phénylisoxazol-5-one, 3,4-diphénylisoxazol-5-one, 3-méthylisoxazol-5-one, 3,4-tétraméthylèneisoxazol-5-one, et leurs sels d'addition. 15 méthyl-5-chloroindazolone, 1-méthyl-6-chloroindazolone, 1-éthyl-5chloroindazolone, 1-éthyl-6-bromo-indazolone, 5-aminoindazolone, 6-diméthylaminoindazolone, 5-diéthylaminoindazolone, 1-méthyl-5-diméthylaminoindazolone 5-dibutylaminoindazolone, 1-éthyl-5-dipropylaminoindazolone, et leurs sels d'addition. Ces indazolones sont décrites dans la demande de brevet 25 DE-A-26 32 390. A titre de benzimidazoles utilisés dans les compositions selon l'invention, on peut citer le 4,7-dihydroxybenzimidazole, la 4,7-dihydroxy-1-méthylbenzimidazole, le 4,7-dihydroxy-2-méthyl-benzimidazole, le 4,7-dihydroxy-1-éthylbenzimidazole, le 4,7dihydroxy-1-propylbenzimidazole, 4,7-dihydroxy-1-butyl- benzimidazole, le 4,7-dihydroxy-2-éthylbenzimidazole, le 4,7-dihydroxy-2-butylbenzimidazole, le 4,7-dihydroxy-1,2-diméthylbenzimidazole, le 4,7-diméthoxybenzimidazole, le 4,7-diméthoxy-1-méthylbenzimidazole, le 4,7-diméthoxy-1-éthylbenzimidazole, le 4,7diméthoxy-2-méthylbenzimidazole, le 4,7-diméthoxy-2- Ces isoxazolones sont décrites dans la demande de brevet FR-A-2 040 260. A titre d'indazolones utilisées dans les compositions selon l'invention, on peut citer les indazolone, 5-chloroindazolone, 6- chloroindazolone, 1-éthylindazolone, 5-diméthylaminoindazolone, 1- méthylindazolone, 1-isopropylindazolone, 1-butylindazolone, 3- chloroindazolone, 4-chloroindazolone, 5-méthylindazolone, 6- méthylindazolone, 5-éthylindazolone, 6-propylindazolone, 5- butylindazolone, 1,5-diméthylindazolone, 1,6-diméthylindazolone, 1- éthylbenzimidazole, le 5,6-dihydroxybenzimidazole, le 5,6-dihydroxy-1-méthylbenzimidazole, le 5,6-dihydroxy-1-éthylbenzimidazole, le 5,6-dihydroxy-1-butylbenzimidazole, le 5,6-dihydroxy-2-méthy- benzimidazole, le 5,6-dihydroxy-2-butylbenzimidazole, le 5,6-dihydroxy-2-phénylbenzimidazole, le 5,6-diméthoxybenzimidazole, le 5,6-diméthoxy-1-méthylbenzimidazole, le 5,6 diméthoxy-1-éthylbenzimidazole, le 5,6-diméthoxy-1-propylbenzimidazole, le 5,6-diméthoxy-2-méthylbenzimidazole, le 5,6-diméthoxy-2butylbenzimidazole, le 5,6-diméthoxy-2-phénylbenzimidazole, le 5,6-diméthoxy-1,2-diméthylbenzimidazole, le 4-hydroxy-7-méthoxybenzimidazole, le 5-hydroxy-6-méthoxybenzimidazole, le 4-hydroxy-7-méthoxy-1-méthylbenzimidazole, le 5-hydroxy-6-méthoxy-1,2-diméthylbenzimidazole. Ces benzimidazoles sont décrits dans la demande de brevet DE-A-28 12 678. These pyrroloazoles are described in the patent application WO 97/35554. As imidazoloazoles used in the compositions according to the invention, mention may be made of imidazolo [3,2-a] imidazoles, imidazolo [1,2-b] -1,2,4-triazoles and imidazolo [2, 1-c] -1,2,4-triazoles, and their addition salts. Preferably, the imidazolo [3,2-a] imidazoles are chosen from 7,8-dicyanoimidazolo [3,2-a] imidazole, 7,8-dicyano-4-methylimidazolo [3,2-a] imidazole, 7,8-dicyano-4-ethylimidazolo [3,2-a] imidazole, 7,8-dicyano-4-isopropylimidazolo [3,2-a] imidazole, 7,8-dicyano-4-phenylimidazole [3,2-a] imidazole, 5-chloro-7,8-dicyano-4-methylimidazolo [3,2-a] imidazole, 7,8-dicyano-4-trifluoromethylimidazolo [3,2-a] imidazole , and their addition salts. Preferably, the imidazolo [1,2-b] -1,2,4-triazoles are chosen from imidazolo [1,2-b] -1,2,4-triazole, 6-methylimidazolo- [1,2] b) -1,2,4-triazole, 6-isopropylimidazolo [1,2-b] -1,2,4-triazole, 6-phenylimidazolo [1,2-b] -1,2,4-triazole, 2,6-dimethylimidazolo [1,2-b] -1,2,4-triazole, 6-isopropyl-2-methylimidazolo [1,2-b] -1,2,4-triazole, 2-methyl-6- phenylimidazolo [1,2-b] -1,2,4-triazole, 6-methyl-2-phenylimidazolo [1,2-b] -1,2,4-triazole, 6-isopropyl-2-phenylimidazolo [1, 2-b] -1,2,4-triazole, 7-chloro-2,6-dimethylimidazolo [1,2-b] -1,2,4-triazole, 7-chloro-2-phenyl-6-tertbutylimidazolo [ 1,2-b] -1,2,4-triazole, 6-trifluoromethylimidazolo [1,2-b] -1,2,4-triazole, and their addition salts. Preferably, the imidazolo [2,1-c] -1,2,4-triazoles are chosen from imidazolo [2,1-c] -1,2,4-triazole, 5-methyl-imidazolo [2, 1-c] -1,2,4-triazole, 5,8-dimethylimidazolo [2,1-c] -1,2,4-triazole, 5-methyl-8-phenylimidazolo [2,1-c] -1 2,4-triazole, 8-phenylimidazolo [2,1-c] -1,2,4-triazole, 6-chloro-5,8-dimethylimidazolo [2,1-c] -1,2, 4-triazole, and their addition salts. Preferably, the imidazolo [2,1-c] -1,2,4-triazoles are chosen from imidazolo [2,1-c] -1,2,4-triazole, 5-methyl-imidazolo [2, 1-c] -1,2,4-triazole, 5,8-dimethylimidazolo [2,1-c] -1,2,4-triazole, 5-methyl-8-phenylimidazolo [2,1-c] -1 2,4-triazole, 8-phenylimidazolo [2,1-c] -1,2,4-triazole, 6-chloro-5,8-dimethylimidazolo [2,1-c] -1,2,4- triazole, and their addition salts. These imidazoloazoles are described in patent application WO 97/35552. The thiazoloazoles are described in the patent application FR-A-2,752,524. As pyrrolooxazoles used in the compositions according to the invention, mention may be made of the compounds described, in a general manner, in patent applications FR-A-2,752. 522, and their addition salts. As hydroxypyrazolopyrimidines used in the compositions according to the invention, mention may be made of hydroxypyrazolo [1,5-a] pyrimidines and more particularly 2-hydroxy-5-methyl-7-ethylpyrazolo [1,5-a] pyrimidine, 2-hydroxy-5,6,7-trimethylpyrazolo [1,5-a] pyrimidine, 2-hydroxy-5,7-dimethyl-6-ethylpyrazolo [1,5-a] pyrimidine, 2-hydroxy- 7-methylpyrazolo [1,5-a] pyrimidine, 2-hydroxy-5-methyl-7-carboxypyrazolo [1,5-a] pyrimidine, 2,7-dihydroxy-5,6-dimethylpyrazolo [1,5-a] pyrimidine and their addition salts. These hydroxypyrazolopyrimidines are described in the patent application DE-A-40 29 324. As isoxazolones used in the compositions according to the invention, mention may be made of 4-carboxy-13, -benzoisoxazolone, 1-acetyl- 4-carboxy- (3-yl) benzoisoxazolone, 6-carboxy- (3-yl) benzoisoxazolone, 1-acetyl-6-carboxy- (3-yl) benzoisoxazolone, (3-yl) benzoisoxazolone, 1-acetyl-3 N-benzoisoxazolone, 4-methyl- (3-yl) benzoisoxazolone, 1-acetyl-4 - ((3-hydroxyethylamino) carbonyl- (3-yl) benzoisoxazolone, 3-phenylisoxazol-5-one, 2-acetyl-3 phenylisoxazol-5-one, 3,4-diphenylisoxazol-5-one, 3-methylisoxazol-5-one, 3,4-tetramethyleneisoxazol-5-one, and their addition salts, methyl-5-chloroindazolone, 1 -methyl-6-chloroindazolone, 1-ethyl-5chloroindazolone, 1-ethyl-6-bromoindazolone, 5-aminoindazolone, 6-dimethylaminoindazolone, 5-diethylaminoindazolone, 1-methyl-5-dimethylaminoindazolone 5-dibutylaminoindazolone, 1-ethyl- 5-dipropylaminoindazolone, and their addition salts These indazolone The benzimidazoles used in the compositions according to the invention include 4,7-dihydroxybenzimidazole, 4,7-dihydroxy-1-methylbenzimidazole, and the like, which are described in German Offenlegungsschrift No. 2,632,390. , 4,7-dihydroxy-2-methyl-benzimidazole, 4,7-dihydroxy-1-ethylbenzimidazole, 4,7dihydroxy-1-propylbenzimidazole, 4,7-dihydroxy-1-butylbenzimidazole, 4,7 2-dihydroxy-2-ethylbenzimidazole, 4,7-dihydroxy-2-butylbenzimidazole, 4,7-dihydroxy-1,2-dimethylbenzimidazole, 4,7-dimethoxybenzimidazole, 4,7-dimethoxy-1-methylbenzimidazole, 4,7-Dimethoxy-1-ethylbenzimidazole, 4,7-dimethoxy-2-methylbenzimidazole, 4,7-dimethoxy-2 These isoxazolones are described in patent application FR-A-2,040,260. As indazolones used in the compositions according to the invention include indazolone, 5-chloroindazolone, 6-chloroindazolone, 1-ethylindazolone, 5-dimethylaminoindazolone, 1-methylindazolone, 1-isopropylindazolone, 1-b utylindazolone, 3-chloroindazolone, 4-chloroindazolone, 5-methylindazolone, 6-methylindazolone, 5-ethylindazolone, 6-propylindazolone, 5-butylindazolone, 1,5-dimethylindazolone, 1,6-dimethylindazolone, 1-ethylbenzimidazole, 5,6-methylindazolone dihydroxybenzimidazole, 5,6-dihydroxy-1-methylbenzimidazole, 5,6-dihydroxy-1-ethylbenzimidazole, 5,6-dihydroxy-1-butylbenzimidazole, 5,6-dihydroxy-2-methylbenzimidazole, 5,6-dihydroxy-2-butylbenzimidazole, 5,6-dihydroxy-2-phenylbenzimidazole, 5,6-dimethoxybenzimidazole, 5,6-dimethoxy-1-methylbenzimidazole, 5,6-dimethoxy-1-ethylbenzimidazole, 5,6-dimethoxy-1-propylbenzimidazole, 5,6-dimethoxy-2-methylbenzimidazole, 5,6-dimethoxy-2-butylbenzimidazole, 5,6-dimethoxy-2-phenylbenzimidazole, 5,6-dimethoxy-1, 2-dimethylbenzimidazole, 4-hydroxy-7-methoxybenzimidazole, 5-hydroxy-6-methoxybenzimidazole, 4-hydroxy-7-methoxy-1-methylbenzimidazole, 5-hydroxy-6-methoxy-1,2-dimethylbenzimide imidazol. These benzimidazoles are described in patent application DE-A-28 12 678.
A titre de benzimidazoles utilisés dans les compositions selon l'invention, on peut encore citer les co-cyanoacétylbenzimidazoles, décrits de manière générale dans la demande DE-A-24 46 632, et en particulier le 5-amino-l-méthyl-2-(co-cyanoacétyl)benzimidazole, ainsi que leurs sels d'addition. As benzimidazoles used in the compositions according to the invention, mention may also be made of co-cyanoacetylbenzimidazoles, generally described in application DE-A-24 46 632, and in particular 5-amino-1-methyl-2 - (co-cyanoacetyl) benzimidazole, as well as their addition salts.
A titre de coupleurs pyridiniques utilisés dans les compositions selon l'invention, on peut citer la 2-amino-3-hydroxypyridine, les 2,3-diaminopyridines, les 3-amino-5-hydroxypyridines, et leurs sels d'addition. A titre de 2,3-diaminopyridines utilisées dans les compositions selon l'invention, on peut citer les 6-méthoxy-3-amino-2-phényl- aminopyridine, 6-méthoxy-3-amino-2-(4'-hydroxyphényl)pyridine, 6-méthoxy-3-amino-2-(2'-méthoxyphényl)aminopyridine, 6-méthoxy-3-amino-2-(2'-hydroxyphényl)aminopyridine, 6-méthoxy-3-amino-2-diéthylaminopyridine, 6-méthoxy-3-amino-2-diméthylaminopyridine, le 6-méthoxy-3-amino-2-(méthyl, 2'-hydroxyéthyl)aminopyridine, 6-méthoxy-3-amino-2-(n-butyl, 2'-hydroxyéthyl)pyridine, 6-méthoxy-3-amino-2-bis-(2'-hydroxyéthyl)aminopyridine, 6-méthoxy-3-amino-2-(2',3'-dihydroxypropyl)aminopyridine, 6-méthoxy-3-amino-2-(1',1'-diméthyl-2'-hydroxyéthyl)aminopyridine, 6-méthoxy-3-amino-2-(l'-hydroxyméthyl-2'-hydroxyéthyl)aminopyridine, 6-méthoxy-3-amino-2-(l'-méthyl-2'-hydroxyéthyl)aminopyridine, 6-méthoxy-3-amino-2-(3'-diméthylaminopropyl)aminopyridine, 6-méthoxy-3-amino-2-bis-(méthoxyéthyl)aminopyridine, 6-méthoxy-3-amino-2-bis-(2'-propényl)-aminopyridine, 6-méthoxy-3-amino-2-pyrrolidinylpyridine, 6-méthoxy-3-amino-2-(3'-acétamidopyrrolidinyl)pyridine, 6-méthoxy-3-amino-2-(2',5'-diméthylpyrrolidinyl)pyridine, 6-méthoxy-3-amino-2-(2'-diméthylaminoéthyl)aminopyridine, 6-méthoxy-3-amino-2-morpholino-pyridine, 6-méthoxy-3-amino-2-(2'-méthylpyrrolidinyl)pyridine, 6-méthoxy-3-amino-2-pipérazinylpyridine, 6-méthoxy-3-amino-2-pyridinylpyridine, 6-méthoxy-3-amino-2-pyrrolidinylpyridine, 6-méthoxy-3-amino-2-(2'-méthylpyridinyl)pyridine, 6-méthoxy-3-amino-2-(2'-hydro xyéthylpyridinyl)pyridine, 6-méthoxy-3-amino-2-(2'-pyrrolidinyléthyl)aminopyridine, 6-méthoxy-3-amino-2-(3'-imidazolin-ylpropyl)aminopyridine, 6-méthoxy-3-amino-2-(3'(3"-méthyl-imidazolium)propyl)aminopyridine, 6-(2'-trifluoroéthoxy)-5-trifluoro-méthyl-2,3-diaminopyridine, 6-phénoxy-5-trifluorométhyl-2,3-diaminopyridine, la 6-méthoxy-2,3-diaminopyridine, et leurs sels d'addition. As pyridine couplers used in the compositions according to the invention, there may be mentioned 2-amino-3-hydroxypyridine, 2,3-diaminopyridines, 3-amino-5-hydroxypyridines, and their addition salts. As 2,3-diaminopyridines used in the compositions according to the invention, mention may be made of 6-methoxy-3-amino-2-phenylaminopyridine, 6-methoxy-3-amino-2- (4'-hydroxyphenyl) ) pyridine, 6-methoxy-3-amino-2- (2'-methoxyphenyl) aminopyridine, 6-methoxy-3-amino-2- (2'-hydroxyphenyl) aminopyridine, 6-methoxy-3-amino-2-diethylaminopyridine 6-methoxy-3-amino-2-dimethylaminopyridine, 6-methoxy-3-amino-2- (methyl, 2'-hydroxyethyl) aminopyridine, 6-methoxy-3-amino-2- (n-butyl) -2- hydroxyethyl) pyridine, 6-methoxy-3-amino-2-bis (2'-hydroxyethyl) aminopyridine, 6-methoxy-3-amino-2- (2 ', 3'-dihydroxypropyl) aminopyridine, 6-methoxy 3-amino-2- (1 ', 1'-dimethyl-2'-hydroxyethyl) aminopyridine, 6-methoxy-3-amino-2- (1'-hydroxymethyl-2'-hydroxyethyl) aminopyridine, 6-methoxy- 3-amino-2- (1'-methyl-2'-hydroxyethyl) aminopyridine, 6-methoxy-3-amino-2- (3'-dimethylaminopropyl) aminopyridine, 6-methoxy-3-amino-2-bis- ( methoxyethyl) aminopyridine, 6-methoxy-3-amino-2-bis- (2'-propenyl) ) -aminopyridine, 6-methoxy-3-amino-2-pyrrolidinylpyridine, 6-methoxy-3-amino-2- (3'-acetamidopyrrolidinyl) pyridine, 6-methoxy-3-amino-2- (2 ', 5') dimethylpyrrolidinyl) pyridine, 6-methoxy-3-amino-2- (2'-dimethylaminoethyl) aminopyridine, 6-methoxy-3-amino-2-morpholino-pyridine, 6-methoxy-3-amino-2- (2 ') methylpyrrolidinyl) pyridine, 6-methoxy-3-amino-2-piperazinylpyridine, 6-methoxy-3-amino-2-pyridinylpyridine, 6-methoxy-3-amino-2-pyrrolidinylpyridine, 6-methoxy-3-amino-2 (2'-Methylpyridinyl) pyridine, 6-methoxy-3-amino-2- (2'-hydroxyethyl) pyridinyl) pyridine, 6-methoxy-3-amino-2- (2'-pyrrolidinylethyl) aminopyridine, 6-methoxy- 3-amino-2- (3'-imidazolinylpropyl) aminopyridine, 6-methoxy-3-amino-2- (3 '(3'-methylimidazolium) propyl) aminopyridine, 6- (2'-trifluoroethoxy) - 5-trifluoromethyl-2,3-diaminopyridine, 6-phenoxy-5-trifluoromethyl-2,3-diaminopyridine, 6-methoxy-2,3-diaminopyridine, and their addition salts.
De préférence, parmi ces derniers composés, le coupleur pyridinique est choisi parmi les composés 6-méthoxy-3-amino-2- hydro xyéthylaminopyridine, 6-méthoxy-3-amino-2-(2',3'-dihydroxy- propyl)aminopyridine, 6-méthoxy-3-amino-2-(l'-méthyl-2'-hydroxy- éthyl)aminopyridine, 6-méthoxy-3-amino-2-pyrrolidinylpyridine, 6-méthoxy-3-amino-2-(2'-méthylpyrrolidinyl)pyridine, 6-méthoxy-3-amino-2-(2'-méthylpyridinyl)pyridine, 6-méthoxy-3-amino-2-(2'-hydroxyéthylpyridinyl)pyridine, la 6-méthoxy-2,3-diaminopyridine, et leurs sels d'addition. Ces coupleurs peuvent être peuvent être préparés selon des méthodes connues et décrites dans la littérature. On pourra se reporter à titre d'exemples à la demande de brevet DE-A-32 33 540. A titre de 3-amino-5-hydroxypyridines utilisées dans les compositions selon l'invention, on peut citer la 3-amino-5-hydroxy-2,6-diméthoxypyridine, la 3-amino-5-hydroxy-2,6-di-(2'-hydroxyéthyloxy)- pyridine, et leurs sels d'addition. Ces 3-amino-5-hydroxypyridines sont décrites dans la demande de brevet DE-A-34 42 128. Preferably, among these latter compounds, the pyridinic coupler is chosen from the compounds 6-methoxy-3-amino-2-hydroxyethylaminopyridine, 6-methoxy-3-amino-2- (2 ', 3'-dihydroxypropyl) aminopyridine, 6-methoxy-3-amino-2- (1'-methyl-2'-hydroxyethyl) aminopyridine, 6-methoxy-3-amino-2-pyrrolidinylpyridine, 6-methoxy-3-amino-2- ( 2'-methylpyrrolidinyl) pyridine, 6-methoxy-3-amino-2- (2'-methylpyridinyl) pyridine, 6-methoxy-3-amino-2- (2'-hydroxyethylpyridinyl) pyridine, 6-methoxy-2, 3-diaminopyridine, and their addition salts. These couplers can be can be prepared according to known methods described in the literature. Reference may be made, by way of example, to the patent application DE-A-32 33 540. As 3-amino-5-hydroxypyridines used in the compositions according to the invention, mention may be made of 3-amino-5 hydroxy-2,6-dimethoxypyridine, 3-amino-5-hydroxy-2,6-di- (2'-hydroxyethyloxy) pyridine, and their addition salts. These 3-amino-5-hydroxypyridines are described in patent application DE-A-34 42 128.
A titre de coupleurs pyridiniques, on utilisera, de préférence, la 2-amino-3-hydroxypyridine et ses sels d'addition. A titre de thiophènes utilisés dans les compositions selon l'invention, on peut citer les co-cyanoacétylthiophènes, décrits de manière générale dans la demande DE-A-24 46 632, et en particulier le 5-amino-2-(co-cyanoacétyl)thiophène, ainsi que leurs sels d'addition. A titre d'indolines utilisées dans les compositions selon l'invention, on peut citer les 5-aminoindolines, les 6-aminoindolines, les 7-aminoindolines, la 4-hydroxyindoline, la 5-hydroxyindoline, la 6-hydroxyindoline, la 5,6-dihydroxyindoline, les 5,6-diaminoindoline et 5,7-diaminoindoline, la 5-amino-6-nitroindoline, la 5-bromo-7-nitroindoline, la 6-nitroindoline, et leurs sels d'addition, et notamment, leurs chlorhydrates. Ces indolines sont décrites dans le brevet US 4,013,404. As pyridine couplers, use will preferably be made of 2-amino-3-hydroxypyridine and its addition salts. As thiophenes used in the compositions according to the invention, mention may be made of the co-cyanoacetylthiophenes, generally described in application DE-A-24 46 632, and in particular 5-amino-2- (co-cyanoacetyl) thiophene, as well as their addition salts. As indolines used in the compositions according to the invention, mention may be made of 5-aminoindolines, 6-aminoindolines, 7-aminoindolines, 4-hydroxyindoline, 5-hydroxyindoline, 6-hydroxyindoline, 5, 6-dihydroxyindoline, 5,6-diaminoindoline and 5,7-diaminoindoline, 5-amino-6-nitroindoline, 5-bromo-7-nitroindoline, 6-nitroindoline, and their addition salts, and especially their hydrochlorides. These indolines are described in US Pat. No. 4,013,404.
Parmi les 5,7-diaminoindolines, on peut citer : la 5,7-diamino-1-méthylindoline, la 5,7-diamino-2-méthylindoline, la 5,7-diamino-3-méthylindoline, la 5,7-diamino-2,2-diméthylindoline, la 5,7-diamino-2,3-diméthylindoline, la 5,7-diamino-2-méthyl-3-éthylindoline, la 5,7- diamino-1-éthyl-2-méthyl-2-éthylindoline, la 5,7-diamino-6-méthylindoline, la 5,7-diamino-1,6-diméthylindoline, la 5-diméthylamino-7-amino-l-butylindoline, la 5-diéthylamino-7-amino-2,2-dipropylindoline, la 5-amino-7-diméthylamino-2-méthyl-3-butylindoline, 5-amino-7-dibutylamino-3,3-diéthylaminoindoline, la 5,7-bis-diméthylaminoindoline, et leurs sels d'addition. Ces indolines sont décrites dans la demande de brevet DE-A-27 16 671. On peut également citer les indolines suivantes et leurs sels : la 6-aminoindoline, la 6-hydroxyindoline, la 1-éthyl -6-aminoindoline, la 1-N-éthyl-4-hydroxyindoline. Ces indolines sont décrites dans la demande de brevet DE-A-19 16 139. Among the 5,7-diaminoindolines, mention may be made of: 5,7-diamino-1-methylindoline, 5,7-diamino-2-methylindoline, 5,7-diamino-3-methylindoline, 5,7-diamino-1-methylindoline and diamino-2,2-dimethylindoline, 5,7-diamino-2,3-dimethylindoline, 5,7-diamino-2-methyl-3-ethylindoline, 5,7-diamino-1-ethyl-2-methyl -2-ethylindoline, 5,7-diamino-6-methylindoline, 5,7-diamino-1,6-dimethylindoline, 5-dimethylamino-7-amino-1-butylindoline, 5-diethylamino-7-amino 2,2-dipropylindoline, 5-amino-7-dimethylamino-2-methyl-3-butylindoline, 5-amino-7-dibutylamino-3,3-diethylaminoindoline, 5,7-bis-dimethylaminoindoline, and their salts addition. These indolines are described in the patent application DE-A-27 16 671. Mention may also be made of the following indolines and their salts: 6-aminoindoline, 6-hydroxyindoline, 1-ethyl-6-aminoindoline, 1- N-ethyl-4-hydroxyindoline. These indolines are described in patent application DE-A-19 16 139.
Parmi les 5,6-dihydroxyindolines, on peut citer : la 5,6-dihydroxyindoline, la N-méthyl-5,6-dihydroxyindoline, la N-éthyl-5,6-dihydroxyindoline, la N-propyl-5,6-dihydroxyindoline, la N-butyl-5,6-dihydroxyindoline et la 2-carboxy-5,6-dihydroxyindoline, et leurs sels d'addition. Ces indolines sont décrites dans la demande de brevet WO 01/93818. Among the 5,6-dihydroxyindolines, mention may be made of: 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6- dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and 2-carboxy-5,6-dihydroxyindoline, and their addition salts. These indolines are described in the patent application WO 01/93818.
A titre d'indoles utilisés dans les compositions selon l'invention, on peut citer le 6-hydroxyindole et ses dérivés, le 5,6-dihydroxyindole et ses dérivés, le 4-hydroxyindole et ses dérivés, ainsi que leurs sels d'addition. De préférence, le coupleur indolique est le 6- hydroxyindole. A titre de benzofuranes utilisés dans les compositions selon l'invention, on peut citer les hydroxybenzofuranes, les diaminobenzofuranes et les co-cyanoacétylbenzofuranes, et leurs sels d'addition. As indoles used in the compositions according to the invention, mention may be made of 6-hydroxyindole and its derivatives, 5,6-dihydroxyindole and its derivatives, 4-hydroxyindole and its derivatives, as well as their addition salts. . Preferably, the indole coupler is 6-hydroxyindole. As benzofurans used in the compositions according to the invention, mention may be made of hydroxybenzofurans, diaminobenzofurans and co-cyanoacetylbenzofurans, and their addition salts.
De manière préférée, les hydroxybenzofuranes utilisés sont les 2-méthyl-6-hydroxybenzofurane, 3-méthyl-6-hydroxybenzofurane, 2,4-diméthyl-6-hydroxybenzofurane, 3-n-propyl-6-hydroxybenzofurane, 2-éthyl-5-hydroxybenzofurane, 2-méthyl-5-hydroxybenzofurane, 3-méthyl-5-hydroxybenzofurane, le 3-isobutyl-5-hydroxybenzofurane, 3-éthyl-5-hydroxybenzofurane, 2,6-diméthyl-5-hydroxybenzofurane, 3,6-diméthyl-5-hydroxybenzofurane, 6,7-diméthyl-5-hydroxybenzofurane, 3-n-propyl-5-hydroxybenzofurane, 3-méthyl-4-n-propyl-5-hydroxy-benzofurane, 2-hexyl-5-hydroxybenzofurane, 2-n-propyl-5-hydroxy-benzofurane, 4-tertiobutyl-5-hydroxybenzofurane, 6-tertiobutyl-5-hydroxybenzofurane, 4-méthyl-5-hydroxybenzofurane, 3-méthyl-5-n-propyl-4-hydroxybenzofurane, 2-éthyl-4-hydroxybenzofurane, 2-méthyl-6-pentyl-4-hydroxybenzofurane, 6-pentyl-4-hydroxybenzofurane, 3,5-diméthyl-4-hydroxybenzofurane, 3,7-diméthyl-4-hydroxybenzofurane, 2,6-di-tertiobutyl-4-hydroxybenzofurane, 2-méthyl-4- hydroxybenzofurane, 3-méthyl-4-hydroxybenzofurane, 2-méthyl-7-éthyl-4-hydroxybenzofurane, 2,7-diméthyl-4-hydroxybenzofurane, 2-isopropyl-4-hydroxybenzofurane, 3-éthyl-4-hydroxybenzofurane, 3-méthyl-7-tertiobutyl-4-hydroxybenzofurane, 3-méthyl-5-tertiobutyl-4-hydroxybenzofurane, 2,6-diméthyl-4-hydroxybenzofurane, 3-isopropyl- 4-hydroxybenzofurane, 3-n-propyl-4-hydroxybenzofurane, 3-méthyl-7-n-propyl-4-hydroxybenzofurane, 3-méthyl-6-n-propyl-7-hydroxybenzofurane, 3-méthyl-7-hydroxybenzofurane, 2-éthyl-4-méthyl-7-hydroxybenzofurane, 2-éthyl-5-méthyl-7-hydroxybenzofurane, et leurs sels d'addition. Ces hydroxybenzofuranes sont décrits dans la demande de brevet EP-A-O 506 549. In a preferred manner, the hydroxybenzofurans used are 2-methyl-6-hydroxybenzofuran, 3-methyl-6-hydroxybenzofuran, 2,4-dimethyl-6-hydroxybenzofuran, 3-n-propyl-6-hydroxybenzofuran, 2-ethyl-5 1-hydroxybenzofuran, 2-methyl-5-hydroxybenzofuran, 3-methyl-5-hydroxybenzofuran, 3-isobutyl-5-hydroxybenzofuran, 3-ethyl-5-hydroxybenzofuran, 2,6-dimethyl-5-hydroxybenzofuran, dimethyl-5-hydroxybenzofuran, 6,7-dimethyl-5-hydroxybenzofuran, 3-n-propyl-5-hydroxybenzofuran, 3-methyl-4-n-propyl-5-hydroxybenzofuran, 2-hexyl-5-hydroxybenzofuran, 2-n-propyl-5-hydroxy-benzofuran, 4-tert-butyl-5-hydroxybenzofuran, 6-tert-butyl-5-hydroxybenzofuran, 4-methyl-5-hydroxybenzofuran, 3-methyl-5-n-propyl-4-hydroxybenzofuran, 2-ethyl-4-hydroxybenzofuran, 2-methyl-6-pentyl-4-hydroxybenzofuran, 6-pentyl-4-hydroxybenzofuran, 3,5-dimethyl-4-hydroxybenzofuran, 3,7-dimethyl-4-hydroxybenzofuran, 2, 6-di-tert-butyl-4-hydroxybenzofuran, 2-methyl-4-hydroxybenzoate furan, 3-methyl-4-hydroxybenzofuran, 2-methyl-7-ethyl-4-hydroxybenzofuran, 2,7-dimethyl-4-hydroxybenzofuran, 2-isopropyl-4-hydroxybenzofuran, 3-ethyl-4-hydroxybenzofuran, 3- methyl-7-tert-butyl-4-hydroxybenzofuran, 3-methyl-5-tert-butyl-4-hydroxybenzofuran, 2,6-dimethyl-4-hydroxybenzofuran, 3-isopropyl-4-hydroxybenzofuran, 3-n-propyl-4-hydroxybenzofuran, 3-methyl-7-n-propyl-4-hydroxybenzofuran, 3-methyl-6-n-propyl-7-hydroxybenzofuran, 3-methyl-7-hydroxybenzofuran, 2-ethyl-4-methyl-7-hydroxybenzofuran, 2- ethyl-5-methyl-7-hydroxybenzofuran, and their addition salts. These hydroxybenzofurans are described in patent application EP-A-0 506 549.
De manière préférée, les diaminobenzofuranes utilisés sont les 5,7-diaminobenzofurane, 5,7-diamino-2-méthylbenzofurane, 5,7-diamino-2-éthylbenzofurane, 5-diméthylamino-7-aminobenzofurane, 4,6-diaminobenzofurane, et leurs sels d'addition. Ces diaminobenzofuranes sont décrits dans la demande de brevet DE-A-27 19 424. De manière préférée, les co-cyanoacétylbenzofuranes utilisés sont les co-cyanoacétylbenzofuranes décrits de manière générale dans la demande DE-A-24 46 632, et en particulier le 5-amino-2-(co-cyano-acétyl)benzofurane, ainsi que leurs sels d'addition. A titre de 8-amino-6-méthoxyquinoléines utilisées dans les compositions selon l'invention, on peut citer les 8-amino-6-méthoxyquinoléine, 8-amino-5-bromo-6-méthoxyquinoléine, 8-amino-5-chloro-6-méthoxyquinoléine, 8-amino-5,7-dibromo-6-méthoxy- quinoléine, 8-amino-5-méthyl-6-méthoxyquinoléine, 8-amino-5,7-diméthyl-6-méthoxyquinoléine, 8-amino-5-éthyl-6-méthoxyquinoléine, 8-amino-5-butyl-6-méthoxyquinoléine, 8-amino-5-phényl-6-méthoxy-quinoléine, 8-amino-2-phényl-6-méthoxyquinoléine, 8-amino-2-benzyloxy-6-méthoxyquinoléine, 8-amino-4-diméthylamino-6-méthoxy-quinoléine, 8,4-diamino-6-méthoxyquinoléine, 8-amino-4-chloro-6-méthoxyquinoléine, et leurs sels d'addition. Ces 8-amino-6-méthoxyquinoléines sont décrites dans la demande de brevet DE-A-26 26 141. A titre de 4-hydroxyquinolones utilisées dans les compositions selon l'invention, on peut citer les 7-diméthylamino-4-hydroxy-2- quinolone, 6-méthyl-4-hydroxy-2-quinolone, 6-diméthylamino-4- hydroxy-2-quinolone, 6-méthoxy-4-hydroxy-2-quinolone, 8-chloro-4- hydroxy-2-quinolone, 1-méthyl-7-diméthylamino-4-hydroxy-2-quinolone, 1-méthyl-4-hydroxy-2-quinolone, 1-méthyl-8-chloro-4-hydroxy-2-quinolone, 1,6-diméthyl-4-hydroxy-2-quinolone, 1-méthyl-6-diméthylamino-4-hydroxy-2-quinolone, 6-(2-hydroxyéthyl)-4-hydroxy-2-quinolone, 1-isopropyl-4-hydroxy-2-quinolone, 1-méthyl-7-isopropyl-4-hydroxy-2-quinolone, 1-n-butyl-8-bromo-4-hydroxy-2-quinolone, et leurs sels d'addition. Ces 4-hydroxyquinolones sont décrites dans la demande de brevet DE-A-23 34 738. In a preferred manner, the diaminobenzofurans used are 5,7-diaminobenzofuran, 5,7-diamino-2-methylbenzofuran, 5,7-diamino-2-ethylbenzofuran, 5-dimethylamino-7-aminobenzofuran, 4,6-diaminobenzofuran, and their addition salts. These diaminobenzofurans are described in patent application DE-A-27 19 424. Preferably, the co-cyanoacetylbenzofurans used are the co-cyanoacetylbenzofurans described generally in application DE-A-24 46 632, and in particular the 5-amino-2- (co-cyanoacetyl) benzofuran, as well as their addition salts. As 8-amino-6-methoxyquinolines used in the compositions according to the invention, mention may be made of 8-amino-6-methoxyquinoline, 8-amino-5-bromo-6-methoxyquinoline and 8-amino-5-chloro. 6-methoxyquinoline, 8-amino-5,7-dibromo-6-methoxyquinoline, 8-amino-5-methyl-6-methoxyquinoline, 8-amino-5,7-dimethyl-6-methoxyquinoline, 8-amino 5-ethyl-6-methoxyquinoline, 8-amino-5-butyl-6-methoxyquinoline, 8-amino-5-phenyl-6-methoxy-quinoline, 8-amino-2-phenyl-6-methoxyquinoline, 8-amino 2-Benzyloxy-6-methoxyquinoline, 8-amino-4-dimethylamino-6-methoxy-quinoline, 8,4-diamino-6-methoxyquinoline, 8-amino-4-chloro-6-methoxyquinoline, and their salts thereof addition. These 8-amino-6-methoxyquinolines are described in the patent application DE-A-26 26 141. As 4-hydroxyquinolones used in the compositions according to the invention, mention may be made of 7-dimethylamino-4-hydroxy-4-hydroxyethylolines. 2- Quinolone, 6-methyl-4-hydroxy-2-quinolone, 6-dimethylamino-4-hydroxy-2-quinolone, 6-methoxy-4-hydroxy-2-quinolone, 8-chloro-4-hydroxy-2- quinolone, 1-methyl-7-dimethylamino-4-hydroxy-2-quinolone, 1-methyl-4-hydroxy-2-quinolone, 1-methyl-8-chloro-4-hydroxy-2-quinolone, 1,6- dimethyl-4-hydroxy-2-quinolone, 1-methyl-6-dimethylamino-4-hydroxy-2-quinolone, 6- (2-hydroxyethyl) -4-hydroxy-2-quinolone, 1-isopropyl-4-hydroxy- 2-quinolone, 1-methyl-7-isopropyl-4-hydroxy-2-quinolone, 1-n-butyl-8-bromo-4-hydroxy-2-quinolone, and their addition salts. These 4-hydroxyquinolones are described in patent application DE-A-23 34 738.
A titre de benzodioxoles utilisés dans les compositions selon l'invention, on peut citer les composés décrits, de manière générale, dans les demandes de brevet DE-A-197 18 534 et DE-A-28 13 076. De manière préférée, les benzodioxoles utilisés sont les 5- amino-1,3-benzodioxole, 5-hydroxy-1,3-benzodioxole, 5-amino-2- méthyl-1,3-benzodioxole, 5-hydroxy-2,2-diméthyl-1,3-benzodioxole, 5-hydroxy-2-éthyl-1,3-benzodioxole, 5-hydroxy-2-butyl-1,3-benzo- dioxole, 5-hydroxy-2-phényl-1,3-benzodioxole, 5,6-dihydroxy-1,3- benzodioxole, 4,7-dihydroxy-1,3-benzodioxole, 4,7-diamino-2-méthyl- 1,3-benzodioxole, 5,6-diamino-2,2-diphényl-1,3-benzodioxole, 4,5,7-triamino-1,3-benzodioxole, 5-hydroxy-7-méthyl-2,2-diéthyl-1,3-benzodioxole, et leurs sels d'addition avec un acide, décrits dans la demande de brevet DE-A-28 13 076. A titre d'hydroxybenzamides utilisés dans les compositions selon l'invention, on peut citer les 2,4-dihydroxybenzamides et en particulier les N-phényl-2,4-dihydroxybenzamide, N-(2'-méthoxy-phényl)-2,4-dihydroxybenzamide, N-(3'-méthoxyphényl)-2,4-dihydroxybenzamide, N-(4'-méthoxyphényl)-2,4-dihydroxybenzamide, N-(4'-carboxyphényl)-2,4-dihydroxybenzamide, N-(2'-pyridyl)-2,4-dihydroxybenzamide, N-(3'-pyridyl)-2,4-dihydroxybenzamide, N-(2',5'-diméthoxyphényl)-2,4-dihydroxybenzamide, N-(3',5'-diméthoxyphényl)-2,4-dihydroxybenzamide, N-(2'-méthoxy-5'-aminophényl)-2,4- dihydroxybenzamide, N-(4'-(N,N-diméthylamino)phényl)-2,4- dihydroxybenzamide, N-(4'-hydroxyphényl)-2,4-dihydroxybenzamide, N-méthyl-2,4-dihydroxybenzamide, N-benzyl-2,4-dihydroxybenzamide, le 2,4-dihydroxybenzamide non substitué, et leurs sels d'addition avec un acide. Ces hydroxybenzamides sont décrits dans la demande de brevet DE-A-38 22 449. A titre de dérivés de sésamol utilisés dans les compositions selon l'invention, on peut citer outre le sésamol, le 1-N-f3-hydroxyéthylamino-3,4-méthylènedioxybenzène. A titre de benzomorpholines utilisées dans les compositions selon l'invention, on peut citer la 6-hydroxybenzomorpholine et la 6-aminobenzomorpholine, et leurs sels d'addition avec un acide. 44 A titre de coupleur(s) naphtalénique(s) utilisable(s) dans les compositions selon l'invention, on peut citer les naphtalènes substitués de formule (IX) suivante, et leurs sels d'addition : OR5 dans laquelle : R5 représente un atome d'hydrogène ou un groupement ùCO-R dans lequel R représente un groupe alkyle en C1-C4 ; R6 représente un atome d'hydrogène, un groupe hydroxyle, un groupe alkyle en C1-C4 ou un groupe ùSO3H ; R7 représente un atome d'hydrogène, ou un groupe hydroxyle ; étant entendu qu'au moins un des groupes R5 à R7 est différent d'un atome d'hydrogène. Parmi les naphtalènes substitués de formule (IX), utilisables de manière préférée dans les compositions tinctoriales conformes à l'invention, on peut notamment citer -l'alpha-naphtol, - le 1,7-dihydroxynaphtalène, - le 2,7-dihydroxynaphtalène, - le 2,5-dihydroxynaphtalène, - le 2,3-dihydroxynaphtalène, - le 1-acétoxy-2-méthylnaphtalène, - le 1-hydroxy-2-méthylnaphtalène, - l'acide 1-hydroxy-4-naphtalène sulfonique, et leurs sels d'addition avec un acide ou une base. De manière particulièrement préférée, les coupleurs d'oxydation utilisés dans les compositions selon l'invention sont choisis parmi les méta-aminophénols, les méta-phénylènediamines, les méta-diphénols, les indolines et les indoles, ainsi que leurs sels d'addition. As benzodioxoles used in the compositions according to the invention, mention may be made of the compounds described, in general, in the patent applications DE-A-197 18 534 and DE-A-28 13 076. Preferably, the benzodioxoles used are 5-amino-1,3-benzodioxole, 5-hydroxy-1,3-benzodioxole, 5-amino-2-methyl-1,3-benzodioxole, 5-hydroxy-2,2-dimethyl-1, 3-benzodioxole, 5-hydroxy-2-ethyl-1,3-benzodioxole, 5-hydroxy-2-butyl-1,3-benzodioxole, 5-hydroxy-2-phenyl-1,3-benzodioxole, 5, 6-dihydroxy-1,3-benzodioxole, 4,7-dihydroxy-1,3-benzodioxole, 4,7-diamino-2-methyl-1,3-benzodioxole, 5,6-diamino-2,2-diphenyl- 1,3-benzodioxole, 4,5,7-triamino-1,3-benzodioxole, 5-hydroxy-7-methyl-2,2-diethyl-1,3-benzodioxole, and their addition salts with an acid, described in the patent application DE-A-28 13 076. As hydroxybenzamides used in the compositions according to the invention, mention may be made of 2,4-dihydroxybenzamides and in particular N-phenyl-2,4-dihydrox N- (2'-methoxy-phenyl) -2,4-dihydroxybenzamide, N- (3'-methoxyphenyl) -2,4-dihydroxybenzamide, N- (4'-methoxyphenyl) -2,4-dihydroxybenzamide, N, N- (2'-methoxyphenyl) -2,4-dihydroxybenzamide - (4'-carboxyphenyl) -2,4-dihydroxybenzamide, N- (2'-pyridyl) -2,4-dihydroxybenzamide, N- (3'-pyridyl) -2,4-dihydroxybenzamide, N- (2 '), 5'-dimethoxyphenyl) -2,4-dihydroxybenzamide, N- (3 ', 5'-dimethoxyphenyl) -2,4-dihydroxybenzamide, N- (2'-methoxy-5'-aminophenyl) -2,4-dihydroxybenzamide, N- (4 '- (N, N-dimethylamino) phenyl) -2,4-dihydroxybenzamide, N- (4'-hydroxyphenyl) -2,4-dihydroxybenzamide, N-methyl-2,4-dihydroxybenzamide, N-benzyl 2,4-dihydroxybenzamide, unsubstituted 2,4-dihydroxybenzamide, and their addition salts with an acid. These hydroxybenzamides are described in the patent application DE-A-38 22 449. As sesamol derivatives used in the compositions according to the invention, there may be mentioned besides sesamol, 1-N-f3-hydroxyethylamino-3, 4-methylenedioxybenzene. As benzomorpholines used in the compositions according to the invention, mention may be made of 6-hydroxybenzomorpholine and 6-aminobenzomorpholine, and their addition salts with an acid. As naphthalenic coupler (s) usable in the compositions according to the invention, mention may be made of the substituted naphthalenes of formula (IX) below, and their addition salts: OR5 in which: R5 represents a hydrogen atom or a group -CO-R wherein R represents a C1-C4 alkyl group; R6 represents a hydrogen atom, a hydroxyl group, a C1-C4 alkyl group or an ùSO3H group; R7 represents a hydrogen atom, or a hydroxyl group; it being understood that at least one of the groups R5 to R7 is different from a hydrogen atom. Among the substituted naphthalenes of formula (IX) which may be used in the dyeing compositions in particular in the invention, mention may be made especially of alpha-naphthol, 1,7-dihydroxynaphthalene and 2,7-dihydroxynaphthalene. 2,5-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 1-acetoxy-2-methylnaphthalene, 1-hydroxy-2-methylnaphthalene, 1-hydroxy-4-naphthalene sulfonic acid, and their addition salts with an acid or a base. In a particularly preferred manner, the oxidation couplers used in the compositions according to the invention are chosen from meta-aminophenols, meta-phenylenediamines, meta-diphenols, indolines and indoles, as well as their addition salts.
De préférence, le (ou les) colorant(s) d'oxydation de l'invention est (ou sont) choisi(s) parmi les colorants d'oxydation benzéniques ou hétérocycliques. Les bases d'oxydation et coupleurs d'oxydation peuvent être présents dans les compositions de l'invention, sous forme de sels d'addition avec un acide ou de sels d'addition avec une base. Les sels d'addition avec un acide utilisables dans le cadre de l'invention sont, notamment, choisis parmi les chlorhydrates, les bromhydrates, les sulfates, les citrates, les succinates, les tartrates, les lactates, les acétates, les alkylsulfates et les alkylsulfonates. Lorsque les bases d'oxydation ou les coupleurs d'oxydation contiennent une ou plusieurs fonctions acide carboxylique ou sulfonique, les sels d'addition avec une base sont envisageables. Les sels d'addition avec une base utilisables dans le cadre des compositions tinctoriales de l'invention sont, notamment, ceux obtenus avec la soude, la potasse, l'ammoniaque ou les amines. La concentration en second(s) colorant(s) d'oxydation, différent(s) des composés A des compositions selon l'invention, va de préférence de 0,005 à 15 % en poids, en particulier de 0,01 à 10 % en poids, et de manière plus préférée de 0,5 à 5 % en poids, par rapport au poids total de la composition. La composition tinctoriale conforme à l'invention peut, en outre, contenir un ou plusieurs colorant(s) direct(s) pouvant notamment être choisi(s) parmi les colorants nitrés benzéniques, les colorants directs azoïques, les colorants directs méthiniques et leurs sels d'addition. Ces colorants directs peuvent être de nature non ionique, anionique ou cationique. Le milieu utilisé dans les compositions selon la présente invention est un milieu aqueux ou un milieu contenant de l'eau et au moins un solvant organique. Le (ou les) solvant(s) organique(s) utilisé(s) dans les compositions selon la présente invention peut (ou peuvent) être choisi(s) parmi les alcools monohydroxylés et les polyols. A titre d'alcools monohydroxylés utilisables, on peut citer les alcools inférieurs en C1-C4 comme l'éthanol, l'isopropanol, le tertiobutanol, le n-butanol, et leurs mélanges. De préférence, l'alcool utilisé est l'éthanol. À titre de polyols utilisables, on peut citer le propylèneglycol, les polyéthylèneglycols, les éthers de polyols comme le 2-butoxyéthanol, le monométhyléther de propylèneglycol, le monoéthyléther et le monométhyléther du diéthylèneglycol, ainsi que les alcools aromatiques comme l'alcool benzylique ou le phénoxyéthanol, et leurs mélanges. La concentration en solvant(s) organique(s) dans les compositions selon la présente invention est comprise de préférence entre 0 et 30 %, et de manière plus préférée entre 0 et 20 % en poids par rapport au poids total de la composition. La composition tinctoriale conforme à l'invention peut également contenir un ou plusieurs adjuvants utilisés classiquement dans les compositions pour la teinture des cheveux, tels que les agents tensioactifs anioniques, cationiques, non-ioniques, amphotères, zwittérioniques ou leurs mélanges ; les polymères non-ioniques, amphotères, zwittérioniques, anioniques, cationiques additionnels - autres que les éthers de cellulose cationiques selon l'invention -, ou leurs mélanges ; les agents de pénétration ; les agents séquestrants ; les parfums ; les tampons ; les agents dispersants ; les agents conditionneurs tels que par exemple des silicones volatiles ou non volatiles, modifiées ou non modifiées ; les agents filmogènes ; les céramides ; les agents conservateurs ; les agents opacifiants ; les vitamines ; les acides aminés ; les oligopeptides ; les peptides ; les protéines hydrolysées ou non, modifiées ou non ; les enzymes ; les acideset alcools gras ramifiés ou non ; les cires animales, végétales ou minérales ; les acides organiques hydroxylés ; les filtres UV ; les agents anti-oxydants et les agents anti-radicaux libres ; les agents antipelliculaires ; les agents régulateurs de séborrhée ; les agents apaisants ; les huiles minérales, végétales ou animales ; les polyisobutènes et poly(a-oléfines) ; ; les pigments ; les acides, bases, plastifiants, charges minérales, nacres, paillettes ; les agents antistatiques et les agents réducteurs. Le (ou les) adjuvant(s) ci-dessus est (ou sont), en général, présent(s) en quantité comprise, pour chacun d'eux, de préférence entre 0,01 et 40 % en poids, et de manière plus préférée entre 0,1 et 25 % en poids par rapport au poids de la composition. Les compositions selon la présente demande peuvent également contenir, en tant qu'adjuvant cosmétique additionnel, au moins un agent épaississant encore appelé "agent d'ajustement de la rhéologie". L'agent (ou les agents) d'ajustement de la rhéologie peut (ou peuvent) être choisi(s) parmi les agents épaississants minéraux ou organiques, et en particulier les épaississants associatifs polymériques, les alcools gras additionnels ù autres que les tensioactifs glycérolés selon l'invention ù (alcool oléïque), les dérivés cellulosiques additionnels ù autre que les éthers de cellulose cationiques selon l'invention -(hydroxyéthylcellulose, hydroxypropylcellulose, carboxyméthyl-cellulose) et les gommes d'origine microbienne (gomme de xanthane, gomme de scléroglucane). Preferably, the oxidation dye (s) of the invention is (or are) chosen from benzene or heterocyclic oxidation dyes. The oxidation bases and oxidation couplers may be present in the compositions of the invention, in the form of acid addition salts or addition salts with a base. The addition salts with an acid that can be used in the context of the invention are, in particular, chosen from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, acetates, alkyl sulphates and alkylsulfonates. When the oxidation bases or oxidation couplers contain one or more carboxylic acid or sulphonic acid functions, the addition salts with a base are conceivable. The addition salts with a base which can be used in the context of the dyeing compositions of the invention are, in particular, those obtained with soda, potassium hydroxide, ammonia or amines. The concentration of second oxidation dye (s), different from the compounds A of the compositions according to the invention, is preferably from 0.005 to 15% by weight, in particular from 0.01 to 10% by weight. weight, and more preferably from 0.5 to 5% by weight, relative to the total weight of the composition. The dyeing composition in accordance with the invention may, in addition, contain one or more direct dye (s) which may be chosen in particular from nitrobenzene dyes, azo direct dyes, methine direct dyes and their salts. addition. These direct dyes may be nonionic, anionic or cationic in nature. The medium used in the compositions according to the present invention is an aqueous medium or a medium containing water and at least one organic solvent. The organic solvent (s) used in the compositions according to the present invention may be chosen from monohydric alcohols and polyols. As monohydroxy alcohols which may be used, mention may be made of C 1 -C 4 lower alcohols, such as ethanol, isopropanol, tert-butanol and n-butanol, and mixtures thereof. Preferably, the alcohol used is ethanol. Suitable polyols that may be mentioned include propylene glycol, polyethylene glycols, polyol ethers such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or polyethylene glycol. phenoxyethanol, and mixtures thereof. The concentration of organic solvent (s) in the compositions according to the present invention is preferably between 0 and 30%, and more preferably between 0 and 20% by weight relative to the total weight of the composition. The dye composition in accordance with the invention may also contain one or more adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof; additional nonionic, amphoteric, zwitterionic, anionic, cationic polymers - other than the cationic cellulose ethers according to the invention - or their mixtures; penetrating agents; sequestering agents; the perfumes ; tampons; dispersants; conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified; film-forming agents; ceramides; preservatives; opacifying agents; vitamins; amino acids; oligopeptides; peptides; hydrolysed or unmodified proteins, modified or not; enzymes; branched and unbranched acids and fatty alcohols; animal, vegetable or mineral waxes; hydroxylated organic acids; UV filters; antioxidants and anti-free radical agents; antidandruff agents; regulating agents of seborrhea; soothing agents; mineral, vegetable or animal oils; polyisobutenes and poly (α-olefins); ; pigments; acids, bases, plasticizers, mineral fillers, nacres, flakes; antistatic agents and reducing agents. The adjuvant (s) above is (or is) generally present in an amount of, for each of them, preferably between 0.01 and 40% by weight, and preferably more preferably between 0.1 and 25% by weight relative to the weight of the composition. The compositions according to the present application may also contain, as additional cosmetic adjuvant, at least one thickening agent also called "rheology adjusting agent". The rheology adjusting agent (or agents) may (or may be) chosen from mineral or organic thickeners, and in particular polymeric associative thickeners, additional fatty alcohols other than glycerolated surfactants. According to the invention (oleic alcohol), the additional cellulosic derivatives other than the cationic cellulose ethers according to the invention - (hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose) and the gums of microbial origin (xanthan gum, gum of scleroglucan).
L'agent (ou les agents) d'ajustement de la rhéologie préféré(s) est (ou sont) choisi(s) parmi les alcools gras, les éthers de celluloses non ioniques et les gommes d'origine microbienne. La concentration en agent(s) épaississant(s) est comprise de préférence entre 0,01 et 20 % en poids, et de manière plus préférée entre 1 et 10 % en poids, par rapport au poids total de la composition. Bien entendu, l'homme de l'art veillera à choisir ce (ou ces) éventuel(s) composé(s) complémentaire(s) de manière telle que les propriétés avantageuses attachées intrinsèquement à la composition de teinture d'oxydation conforme à l'invention ne soient pas, ou substantiellement pas, altérées par la (ou les) adjonction(s) envisagée(s). Le pH de la composition tinctoriale conforme à l'invention va généralement de 3 à 12 environ, et de préférence de 5 à 11 environ. I1 peut être ajusté à la valeur désirée au moyen d'agent(s) acidifiant(s) ou alcalinisant(s), habituellement utilisés en teinture des fibres kératiniques ou bien encore à l'aide de système(s) tampon(s) classique(s). Parmi les agents acidifiants, on peut citer, à titre d'exemple, les acides minéraux ou organiques comme l'acide chlorhydrique, l'acide orthophosphorique, l'acide sulfurique, les acides sulfoniques et les acides carboxyliques comme l'acide acétique, l'acide tartrique, l'acide citrique et l'acide lactique. The preferred rheology adjusting agent (s) is / are selected from fatty alcohols, nonionic cellulose ethers and microbial gums. The concentration of thickening agent (s) is preferably between 0.01 and 20% by weight, and more preferably between 1 and 10% by weight, relative to the total weight of the composition. Of course, those skilled in the art will take care to choose this (or these) optional compound (s) in such a way that the advantageous properties intrinsically attached to the oxidation dyeing composition according to the invention. are not, or not substantially, impaired by the proposed addition (s). The pH of the dyeing composition according to the invention is generally from 3 to 12 approximately, and preferably from 5 to 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agent (s), usually used for dyeing keratin fibers or else using conventional buffer system (s). (s). Among the acidifying agents, mention may be made, for example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, sulphonic acids and carboxylic acids such as acetic acid. tartaric acid, citric acid and lactic acid.
Parmi les agents alcalinisants on peut citer, à titre d'exemple, l'ammoniaque, les carbonates alcalins, les alcanolamines telles que les Among the alkalinizing agents that may be mentioned, for example, ammonia, alkaline carbonates, alkanolamines such as
mono-, di- et triéthanolamines ainsi que leurs dérivés, les hydroxydes de sodium ou de potassium et les composés de formule (X) suivante : Rai Rb NùWùN / \ Rd Rd (X) mono-, di- and triethanolamines and derivatives thereof, sodium or potassium hydroxides and compounds of the following formula (X): Rai Rb NùWùN / Rd Rd (X)
dans laquelle :in which :
W est un reste propylène éventuellement substitué par un groupe hydroxyle ou un groupe alkyle en C1-C4 ; W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl group;
Ra, Rb, Rc et Rd, identiques ou différents, représentent un atome d'hydrogène, un groupe alkyle en C1-C4 ou hydroxyalkyle en C1-C4. Ra, Rb, Rc and Rd, which may be identical or different, represent a hydrogen atom, a C1-C4 alkyl group or a C1-C4 hydroxyalkyl group.
La composition tinctoriale selon l'invention peut se présenter sous des formes diverses, telles que sous forme de crèmes, de gels, ou sous toute autre forme appropriée pour réaliser une teinture des fibres kératiniques, et notamment des cheveux humains. The dye composition according to the invention may be in various forms, such as in the form of creams, gels, or in any other form suitable for dyeing keratin fibers, and especially human hair.
Le procédé de teinture des fibres kératiniques de la présente The process for dyeing keratinous fibers of the present invention
invention est un procédé dans lequel on applique sur les fibres la composition selon la présente invention telle que définie précédemment, de préférence en présence d'au moins un agent oxydant pendant un temps suffisant pour développer la couleur désirée. La couleur peut être révélée à pH acide, neutre ou alcalin et l'agent (ou les The invention is a process in which the composition according to the present invention as defined above is applied to the fibers, preferably in the presence of at least one oxidizing agent for a time sufficient to develop the desired color. The color can be revealed at acidic, neutral or alkaline pH and the agent (or
agents) oxydant(s) peut (ou peuvent) être ajouté(s) à la composition de l'invention juste au moment de l'emploi ou il(s) peut (ou peuvent) être mis en oeuvre à partir d'une composition oxydante le(s) contenant, appliquée simultanément ou séquentiellement à la composition de l'invention. agents) can be added to the composition of the invention just at the time of use or they can (or can) be used from a oxidizing the (s) containing, applied simultaneously or sequentially to the composition of the invention.
Selon un mode de réalisation particulier, la composition selon la présente invention est une composition prête à l'emploi, mélangée, de préférence au moment de l'emploi, à une composition contenant, dans un milieu approprié pour la teinture, au moins un agent oxydant, cet agent (ou ces agents) oxydant(s) étant présent(s) en une quantité suffisante pour développer une coloration. Le mélange obtenu est ensuite appliqué sur les fibres kératiniques. Après un temps de pause de 3 à 50 minutes environ, de préférence, 5 à 30 minutes environ, les fibres kératiniques sont rincées, lavées au shampooing, rincées à nouveau, puis séchées. Les agents oxydants classiquement utilisés pour la teinture d'oxydation des fibres kératiniques sont, par exemple, le peroxyde d'hydrogène, le peroxyde d'urée, les bromates de métaux alcalins, les persels tels que les perborates et persulfates, les peracides et les enzymes oxydases parmi lesquelles on peut citer les peroxydases, les oxydo-réductases à 2 électrons telles que les uricases et les oxygénases à 4 électrons comme les laccases, ces oxydoréductases étant éventuellement associées à leurs cofacteurs habituels tels que l'acide urique pour les uricases. L'agent oxydant préféré est le peroxyde d'hydrogène. La composition oxydante peut également renfermer divers adjuvants utilisés classiquement dans les compositions pour la teinture des cheveux, tels que définis précédemment. Le pH de la composition oxydante renfermant l'agent oxydant est tel qu'après mélange avec la composition tinctoriale, le pH de la composition résultante appliquée sur les fibres kératiniques varie, de préférence, de 3 à 12 environ, et préférentiellement, de 5 à 10. I1 peut être ajusté à la valeur désirée au moyen d'agent(s) acidifiant(s) ou alcalinisant(s) habituellement utilisé(s) en teinture des fibres kératiniques, tel(s) que défini(s) précédemment. La composition prête à l'emploi qui est finalement appliquée sur les fibres kératiniques, peut se présenter sous des formes diverses, telles que sous forme de crèmes, de gels ou sous toute autre forme appropriée pour réaliser une teinture des fibres kératiniques, et notamment des fibres kératiniques humaines tels que les cheveux. L'invention a aussi pour objet un dispositif à plusieurs compartiments ou "kit" de teinture comprenant au moins un premier compartiment contenant la composition tinctoriale définie ci-dessus et au moins un deuxième compartiment contenant une composition oxydante. Ce dispositif peut être équipé d'un moyen permettant de délivrer sur les cheveux le mélange souhaité, tel que les dispositifs décrits dans la demande de brevet FR-A2 586 913. Les exemples qui suivent servent à illustrer l'invention sans toutefois présenter un caractère limitatif. EXEMPLES According to a particular embodiment, the composition according to the present invention is a ready-to-use composition, mixed, preferably at the time of use, with a composition containing, in a medium suitable for dyeing, at least one agent. oxidizing agent, wherein the oxidizing agent (s) is present in an amount sufficient to develop a color. The mixture obtained is then applied to the keratinous fibers. After a pause of about 3 to 50 minutes, preferably about 5 to 30 minutes, the keratinous fibers are rinsed, washed with shampoo, rinsed again and then dried. The oxidizing agents conventionally used for the oxidation dyeing of keratinous fibers are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids, and the like. oxidase enzymes among which include peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases, these oxidoreductases being optionally associated with their usual cofactors such as uric acid for uricases. The preferred oxidizing agent is hydrogen peroxide. The oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing hair, as defined above. The pH of the oxidizing composition containing the oxidizing agent is such that, after mixing with the dye composition, the pH of the resulting composition applied to the keratinous fibers preferably varies from 3 to 12 approximately, and preferably from 5 to 10. It can be adjusted to the desired value by means of acidifying agent (s) or alkalinizing agent (s) usually used in dyeing keratinous fibers, as defined previously (s). The ready-to-use composition which is finally applied to the keratinous fibers may be in various forms, such as in the form of creams, gels or in any other form suitable for dyeing keratinous fibers, and especially human keratin fibers such as hair. The invention also relates to a multi-compartment device or "kit" of dyeing comprising at least a first compartment containing the dye composition defined above and at least a second compartment containing an oxidizing composition. This device may be equipped with means for delivering the desired mixture onto the hair, such as the devices described in the patent application FR-A2 586 913. The following examples serve to illustrate the invention without, however, presenting a character limiting. EXAMPLES
Les compositions suivantes ont été réalisées. Pour certains produits, notamment des produits commerciaux, ces données sont 10 également exprimées en grammes de matière active (M.A.). Composition 1 Composition 2 1-méthyl-2-hydroxy-4-béta- 0,27 g 0,22 g hydroxyéthylaminobenzène 1-méthyl-2-hydroxy-4- 1,12 g 0,9 g aminobenzéne 1,4-diaminobenzène 0,36 g 0,128 g 1-hydroxy-4-aminobenzène 0,09 g 0,16 g 2,3-diamino-6,7-dihydro-1,8 g 1,68 g lH,5H-pyrazolo[1,2-a]- pyrazol-1-one, 2 CH3SO3H Ether de cellulose cationique 0,3 g 0,3 g (Softcat SL-100 vendu par Amerchol) Mélange d'alcools linéaires 3 g 3 g en C18-C24, à plus de 95 % en poids d'alcools (Cis/C20/C22/C24 dans des proportions respectives de 7/58/30/6) (Nafol 2022 EN vendu par Sasol) Solution aqueuse à 60 % en 2 g 5 g poids de chlorure (soit 1,2 g M.A.) (soit 3,0 g M.A.) d'hexadiméthrine (Mexomère PO vendu par Chimex) 5 Solution aqueuse à 40 % en 4 g 4 g poids polyquaternium-6 (soit 1,6 g M.A.) (soit 1,6 g M.A.) (Merquat 100 vendu par Ondéo) Polymère carboxyvinylique (Carbopol 980 vendu par 0,4 g 0,4 g Noveon) Acide oléique 3 g 3 g Alcool oléique polyglycérolé 1,5 g 1,5 g (2 moles) Alcool stéarylique 5,5 g 5,5 g oxyéthyléné à 2 moles d'oxyéthylène Alcool stéarylique 3,3 g 3,3 g oxyéthyléné à 21 moles d'oxyéthylène Monoéthanolamide d'acide 5 g 5 g laurique Alcool laurique à 1,5 moles 2 g 2 g de glycérol (INCI : glyceryl lauryl ether) Monoéthanolamine pure 1 g 1 g Solution aqueuse d'ammoniac ll g ll g à 20 % en poids Acide érythorbique 0,5 g 0,5 g Acide éthylène diamine 0,2 g 0,2 g tétracétique (EDTA) Sulfite de sodium 0,5 g 0,5 g TiO2 (anatase, non traité) 0,3 g 0,3 g Parfum 0,5 g 0,5 g Eau déminéralisée q.s.p. 100 g 100 g Protocole d'application The following compositions were made. For some products, especially commercial products, these data are also expressed in grams of active ingredient (MA). Composition 1 Composition 2 1-methyl-2-hydroxy-4-beta- 0.27 g 0.22 g hydroxyethylaminobenzene 1-methyl-2-hydroxy-4- 1,12 g 0.9 g aminobenzene 1,4-diaminobenzene 0 , 36 g 0.128 g 1-hydroxy-4-aminobenzene 0.09 g 0.16 g 2,3-diamino-6,7-dihydro-1,8 g 1,68 g 1 H, 5H-pyrazolo [1,2- a] - pyrazol-1-one, 2 CH3SO3H Cationic cellulose ether 0.3 g 0.3 g (Softcat SL-100 sold by Amerchol) Mixture of linear alcohols 3 g 3 g in C18-C24, more than 95 % by weight of alcohols (Cis / C20 / C22 / C24 in respective proportions of 7/58/30/6) (Nafol 2022 EN sold by Sasol) 60% aqueous solution in 2 g of 5 g of chloride (either 1.2 g MA) (ie 3.0 g MA) of hexadimethrine (Mexomère PO sold by Chimex). A 40% aqueous solution in 4 g 4 g polyquaternium-6 weight (ie 1.6 g MA) (ie 1 g). , 6 g MA) (Merquat 100 sold by Ondéo) Carboxyvinyl polymer (Carbopol 980 sold by 0.4 g 0.4 g Noveon) Oleic acid 3 g 3 g Oleic alcohol polyglycerol 1.5 g 1.5 g (2 moles) Stearyl alcohol 5.5 g 5.5 g oxyethylenated with 2 moles of oxyethylene Stearyl alcohol 3.3 g 3.3 g oxyethylenated with 21 moles of oxyethylene Monoethanolamide of acid 5 g 5 g lauric alcohol lauric alcohol 1.5 mol 2 g 2 g glycerol (INCI: glyceryl lauryl ether) pure monoethanolamine 1 g 1 g aqueous ammonia solution ll g ll g at 20% by weight erythorbic acid 0.5 g 0.5 g ethylene diamine 0.2 g 0 , 2 g tetracetic (EDTA) Sodium sulphite 0.5 g 0.5 g TiO2 (anatase, untreated) 0.3 g 0.3 g Perfume 0.5 g 0.5 g Demineralized water qs 100 g 100 g Application Protocol
Chaque composition est diluée extemporanément, avec une fois et demie son poids d'oxydant commercialisé sous l'appellation "Oxydant crème n 1" de 1'OREAL PROFESSIONNEL (pH voisin de 3) à 20 volumes d'eau oxygénée (6 % en poids d'H2O2). Le mélange ainsi réalisé, présentant une bonne viscosité, est appliqué facilement sur des cheveux gris, à 90 % de cheveux blancs, à raison de 10 g pour 1 g de cheveux, pendant 20 minutes pour l'exemple 1 et 30 minutes pour l'exemple 2. Les cheveux sont ensuite facilement rincés, lavés avec un shampooing standard et séchés. Each composition is diluted extemporaneously, with one and a half times its weight of oxidizing agent sold under the name "Cream Oxidizer No. 1" of the PROFESSIONAL ORAL (pH of about 3) to 20 volumes of hydrogen peroxide (6% by weight H2O2). The mixture thus produced, having a good viscosity, is easily applied to gray hair, to 90% of white hair, at the rate of 10 g per 1 g of hair, for 20 minutes for example 1 and 30 minutes for the hair. Example 2. The hair is then easily rinsed, washed with standard shampoo and dried.
La coloration capillaire est évaluée de manière visuelle. Les résultats obtenus sur les cheveux naturels gris, à 90 % de cheveux blancs, après traitement, sont les suivants : Nuance Composition 1 Rouge intense Composition 2 Cuivré intense Ces colorations possèdent de bonnes propriétés notamment en termes de sélectivité et de ténacité. Elles possèdent aussi une bonne 20 intensité. Les compositions obtenues sont stables dans le temps. Capillary staining is evaluated visually. The results obtained on the natural gray hair, with 90% of white hair, after treatment, are as follows: Nuance Composition 1 Intense red Composition 2 Intense copper These colorations have good properties in particular in terms of selectivity and toughness. They also have good intensity. The compositions obtained are stable over time.
Les compositions suivantes ont également été réalisées : Composition 3 Composition 4 1-hydroxy-3-aminobenzène 0,35 g 5-amino-6-chloro-o-crésol 0,5 g 0,8 g 1-méthyl-2-hydroxy-4- 0,2 g aminobenzéne 1,3-dihydroxybenzène 0,25 g 2,3-diamino-6,7-dihydro- 3 g 1,9 g 1H,5H- 52 pyrazolo[1,2-a]pyrazol-1-one, 2 CH3SO3H Ether de cellulose cationique 0,6 g 0,6 g (Softcat SL-100 vendu par Amerchol) Solution aqueuse à 60 % en 2 g 2 g poids de chlorure (soit 1,2 g M.A.) (soit 1,2 g M.A.) d'hexadiméthrine (Mexomere PO vendu par Chimex) Solution aqueuse à 40 % en 2 g 2 g poids de polyquaternium-6 (Merquat 100 vendu par (soit 0, 8 g M.A.) (soit 0,8 g M.A.) Ondéo) Céto/stéaryl sulfate de sodium (C16/C1g en proportions 50/50) 1,5 g 1,5 g (Lanette E vendu par Cognis) Alcool laurique oxyéthyléné 3 g 3 g à 12 moles d'oxyéthylène Amide d'acides de colza 4 g 4 g oxyéthyléné à 4 moles d'oxyéthylène (Amidet N vendu par Kao) Monoéthanolamide d'acide 4 g 4 g alkyl (C13/C15, 70 : 30, à 50 % de linéaires) éther carboxylique à 2 moles d'oxyéthylène (Amidet A 15 vendu par Kao) Alcool oléocétylique 2 g 2 g oxyéthyléné à 30 moles d'oxyéthylène Alcool laurique oxyéthyléné 8 g 8 g à 2,5 moles d'oxyéthylène Glycérol 3 g 3 g Solution aqueuse 10,5 g 10,5 g d'ammoniac à 20 % en poids (soit à 2,1 g M.A.) (soit à 2,1 g M.A.) Acide érythorbique 0,4 g 0,4 g Sulfite de sodium 0,1 g 0,1 g Acide éthylène diamine 0,2 g 0,2 g tétracétique (EDTA) Parfum 0,5 g 0,5 g Eau déminéralisée q.s.p. 100 g 100 g Protocole d'application The following compositions were also carried out: Composition 3 Composition 4 1-hydroxy-3-aminobenzene 0.35 g 5-amino-6-chloro-o-cresol 0.5 g 0.8 g 1-methyl-2-hydroxy- 4- 0,2 g aminobenzene 1,3-dihydroxybenzene 0.25 g 2,3-diamino-6,7-dihydro-3 g 1,9 g 1H, 5H-52 pyrazolo [1,2-a] pyrazol-1 -one, 2 CH3SO3H Cationic cellulose ether 0.6 g 0.6 g (Softcat SL-100 sold by Amerchol) 60% aqueous solution in 2 g 2 g chloride (1.2 g MA) (ie 1 2 g MA) of hexadimethrine (Mexomere PO sold by Chimex) 40% aqueous solution in 2 g 2 g of polyquaternium-6 (Merquat 100 sold by (ie 0.8 g MA) (ie 0.8 g MA Sodium keto / stearyl sulfate (C16 / C1g in proportions 50/50) 1.5 g 1.5 g (Lanette E sold by Cognis) Oxyethylenated lauric alcohol 3 g 3 g to 12 moles of oxyethylene Amide d. rapeseed acids 4 g 4 g oxyethylenated with 4 moles of oxyethylene (Amidet N sold by Kao) Monoethanolamide acid 4 g 4 g alkyl (C13 / C15, 70: 30, 5 0% of linear) 2-moles of carboxylic ether of oxyethylene (Amidet A sold by Kao) Oleocetyl alcohol 2 g 2 g oxyethylenated with 30 moles of oxyethylene Oxy-ethylenated lauric alcohol 8 g 8 g with 2.5 moles of oxyethylene Glycerol 3 g 3 g aqueous solution 10.5 g 10.5 g ammonia 20% by weight (ie 2.1 g MA) (ie 2.1 g MA) erythorbic acid 0.4 g 0.4 g Sodium sulphite 0.1 g 0.1 g Ethylene diamine 0.2 g 0.2 g Tetraacetic acid (EDTA) Perfume 0.5 g 0.5 g Demineralized water qs 100 g 100 g Application Protocol
Chaque composition est diluée extemporanément, avec une fois et demie son poids d'oxydant commercialisé sous l'appellation "Oxydant crème n 1" de 1'OREAL PROFESSIONNEL (pH voisin de 3) à 20 volumes d'eau oxygénée (6 % en poids d'H2O2). Le mélange ainsi réalisé, présentant une bonne viscosité, est appliqué facilement sur des cheveux gris, à 90 % de cheveux blancs, à raison de 10 g pour 1 g de cheveux, pendant 20 minutes pour l'exemple 1 et 30 minutes pour l'exemple 2. Les cheveux sont ensuite rincés facilement, lavés avec un shampooing standard et séchés. Each composition is diluted extemporaneously, with one and a half times its weight of oxidizing agent sold under the name "Cream Oxidizer No. 1" of the PROFESSIONAL ORAL (pH of about 3) to 20 volumes of hydrogen peroxide (6% by weight H2O2). The mixture thus produced, having a good viscosity, is easily applied to gray hair, to 90% of white hair, at the rate of 10 g per 1 g of hair, for 20 minutes for example 1 and 30 minutes for the hair. Example 2. The hair is then rinsed easily, washed with a standard shampoo and dried.
La coloration capillaire est évaluée de manière visuelle. Les résultats obtenus sur les cheveux naturels gris, à 90 % de cheveux blancs, après traitement, sont les suivants : Nuance Composition 3 Cuivré très intense Composition 4 Cuivré rouge Ces colorations possèdent de bonnes propriétés notamment en 20 termes de sélectivité et de ténacité. Elles possèdent aussi une bonne intensité. Les compositions obtenues sont stables dans le temps. Capillary staining is evaluated visually. The results obtained on the natural gray hair, with 90% of white hair, after treatment, are as follows: Nuance Composition 3 Copper very intense Composition 4 Copper red These colors have good properties in particular in terms of selectivity and toughness. They also have good intensity. The compositions obtained are stable over time.
Les compositions suivantes ont, en outre, été réalisées : Composition 5 Composition 6 1-méthyl-2-hydroxy-4-béta- - 0,2 g hydroxyéthylaminobenzène 1-hydroxy-3-aminobenzène 0,35 g 1,3-dihydroxybenzène 0,25 g 5-amino-6-chloro-o-cresol 0,5 g 0,8 g 2,3-diamino-6,7-dihydro- 3 g 1,9 g lH,5H-pyrazolo[1,2-a]- pyrazol-1-one, 2 CH3SO3H Ether de cellulose cationique 0,2 g 0,2 g (Softcat SL-100 vendu par Amerchol) Solution aqueuse à 60 % en 0,5 g 0,5 g poids de chlorure (soit 0,3 g M.A.) (soit 0,3 g M.A.) d'hexadiméthrine (Mexomere PO vendu par Chimex) Solution aqueuse à 40 % en 3 g 3 g poids de polyquaternium-6 (Merquat 100 vendu par Ondéo) Monoéthanolamide d'acides 18 g 18 g de coprah (Monamid CMA vendu par Uniquema) Mélange d'esters cétyliques 0, 8 g 0, 8 g (35 % en poids), glycérides de végétaux hydrogénés (30 % en poids), ozokérite (20 % en poids), acide stéarylique (10 % en poids) et alcool cétéarylique (5 % en poids) (Strahl and Pitsch SP 446P vendu par Strahl and Pitsch) N-oleyl dihydrosphingosine 0,01 g 0,01 g (Mexanyl GZ vendu par Chimex) Glycérol 3 g 3 g Cire liquide de Jojoba 0,2 g 0,2 g (Pur jojoba oil vendu par Jojoba Israël) Chlorure d'hydroxyéthyl behenamidopropyl 3 g 3 g dimonium Amine oléique 3 g 3 g oxyéthylénée à 2 moles d'oxyéthylène Monoéthanolamide de 6 g 6 g l'acide laurique Acide dilinoléique 5 g 5 g Disodium amphodiacétate 3g 3g de farine de germe de blé à (soit 0,75 g M.A.) (soit 0,75 g M.A.) 25 % en poids dans l'eau (Mackam 2W vendu par Mac Intyre) Acide L-ascorbique 0,5 g 0,5 g Monoéthanolamine pure 1,21 g 1,21 g Sulfite de sodium 0,5 g 0,5 g Acide éthylène diamine 0,2 g 0,2 g tétracétique (EDTA), sel disodique, 2 H2O Solution aqueuse 14,25 g 14,25 g d'ammoniac à 20 % en (soit 2,85 g M.A.) (soit 2,85 g M.A.) poids Parfum 0,5 g 0,5 g Eau déminéralisée q.s.p. 100 g 100 g Protocole d'application The following compositions were furthermore carried out: Composition 5 Composition 6 1-methyl-2-hydroxy-4-beta-0.2 g hydroxyethylaminobenzene 1-hydroxy-3-aminobenzene 0.35 g 1,3-dihydroxybenzene 0 25 g 5-amino-6-chloro-o-cresol 0.5 g 0.8 g 2,3-diamino-6,7-dihydro-3 g 1,9 g 1H, 5H-pyrazolo [1,2-d] a] - pyrazol-1-one, 2 CH3SO3H Cationic cellulose ether 0.2 g 0.2 g (Softcat SL-100 sold by Amerchol) 60% aqueous solution in 0.5 g 0.5 g weight of chloride ( 0.3 g MA) (ie 0.3 g MA) of hexadimethrine (Mexomere PO sold by Chimex) 40% aqueous solution in 3 g 3 g of polyquaternium-6 (Merquat 100 sold by Ondéo) Monoethanolamide 18 g 18 g of coconut (Monamid CMA sold by Uniquema) Cetyl ester mixture 0.8 g 0.8 g (35% by weight), hydrogenated vegetable glycerides (30% by weight), ozokerite (20% by weight) weight), stearyl acid (10% by weight) and cetearyl alcohol (5% by weight) (Strahl and Pitsch SP 446P sold by Strahl and P itsch) N-oleyl dihydrosphingosine 0.01 g 0.01 g (Mexanyl GZ sold by Chimex) Glycerol 3 g 3 g Liquid Jojoba wax 0.2 g 0.2 g (Pure jojoba oil sold by Jojoba Israel) Chloride hydroxyethyl behenamidopropyl 3 g 3 g dimonium oleic amine 3 g 3 g oxyethylenated with 2 moles of oxyethylene Monoethanolamide of 6 g 6 g lauric acid dilinoleic acid 5 g 5 g Disodium amphodiacetate 3g 3g of wheat germ meal at (ie 0 75 g MA) (ie 0.75 g MA) 25% by weight in water (Mackam 2W sold by Mac Intyre) L-ascorbic acid 0.5 g 0.5 g Pure monoethanolamine 1.21 g 1.21 Sodium sulfite 0.5 g 0.5 g Ethylene diamine 0.2 g 0.2 g Tetraacetic acid (EDTA), disodium salt, 2 H2O Aqueous solution 14.25 g 14.25 g ammonia 20% (2.85 g MA) (2.85 g MA) Weight Fragrance 0.5 g 0.5 g Demineralized water qs 100 g 100 g Application Protocol
Chaque composition est diluée extemporanément, avec un poids égal d'oxydant commercialisé sous l'appellation "Oxydant crème n 1" de 1'OREAL PROFESSIONNEL (pH voisin de 3) à 20 volumes d'eau oxygénée. Le mélange ainsi réalisé, présentant une bonne viscosité, est appliqué facilement sur des cheveux gris, à 90 % de cheveux blancs, à raison de 10 g pour 1 g de cheveux, pendant 30 minutes. Les cheveux sont ensuite rincés facilement, lavés avec un shampooing standard et séchés. Each composition is diluted extemporaneously, with an equal weight of oxidant marketed under the name "Cream Oxidant No. 1" of the PROFESSIONAL ORAL (pH of about 3) to 20 volumes of hydrogen peroxide. The mixture thus produced, having a good viscosity, is easily applied to gray hair, with 90% of white hair, at a rate of 10 g per 1 g of hair, for 30 minutes. The hair is then rinsed easily, washed with standard shampoo and dried.
La coloration capillaire est évaluée de manière visuelle. Les résultats obtenus sur les cheveux naturels gris, à 90 % de cheveux blancs, après traitement, sont les suivants : Nuance Composition 5 Cuivré très intense Composition 6 Cuivré rouge Ces colorations possèdent de bonnes propriétés notamment en termes de sélectivité et de ténacité. Elles possèdent aussi une bonne intensité. Les compositions obtenues sont stables dans le temps. 5715 Capillary staining is evaluated visually. The results obtained on the natural gray hair, with 90% of white hair, after treatment, are as follows: Nuance Composition 5 Copper very intense Composition 6 Copper red These colors have good properties in particular in terms of selectivity and toughness. They also have good intensity. The compositions obtained are stable over time. 5715
Claims (40)
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FR0756859A FR2919500B1 (en) | 2007-07-31 | 2007-07-31 | KERATIN FIBER OXIDATION DYE COMPOSITION COMPRISING ONE OR MORE CATIONIC CELLULOSE ETHER (S), ONE OR MORE DIAMINOPYRAZOLONE DERIVATIVES, AND ONE OR MORE OTHER OXIDATION COLOR (S). |
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FR3008615A1 (en) * | 2013-07-19 | 2015-01-23 | Oreal | COLORING COMPOSITION COMPRISING A PARTICULAR AMPHOTERE ACTIVE TENSIO AND A SUGAR-BASED THICKENING POLYMER |
EP2560606B1 (en) | 2010-04-19 | 2017-08-23 | Kao Germany GmbH | Colouring composition |
CN111454787A (en) * | 2015-10-13 | 2020-07-28 | 美利肯公司 | Novel whitening agents for cellulosic substrates |
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CN103938298B (en) * | 2013-01-18 | 2016-01-20 | 孙剑锋 | Inhale the preparation method of color fibre and suction look non-weaving cloth |
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Cited By (5)
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EP2560606B1 (en) | 2010-04-19 | 2017-08-23 | Kao Germany GmbH | Colouring composition |
FR3008613A1 (en) * | 2013-07-19 | 2015-01-23 | Oreal | COLORING COMPOSITION COMPRISING PARTICULAR AMPHOTER ACTIVE TENSIO AND OXYETHYLENE AMIDE SURFACTANT |
FR3008615A1 (en) * | 2013-07-19 | 2015-01-23 | Oreal | COLORING COMPOSITION COMPRISING A PARTICULAR AMPHOTERE ACTIVE TENSIO AND A SUGAR-BASED THICKENING POLYMER |
CN111454787A (en) * | 2015-10-13 | 2020-07-28 | 美利肯公司 | Novel whitening agents for cellulosic substrates |
CN111454787B (en) * | 2015-10-13 | 2022-11-01 | 美利肯公司 | Novel whitening agents for cellulosic substrates |
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