CH627206A5 - - Google Patents

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Info

Publication number: CH627206A5
Authority: CH; Switzerland
Prior art keywords: amino; formula; acid; sulfonic acid; disulfonic acid
Prior art date: 1978-07-06

Application number

CH738078A

Other languages

German (de)

English (en)

Inventor

Herbert Dr Seiler

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1978-07-06

Filing date

1978-07-06

Publication date

1981-12-31

1978-07-06 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1978-07-06 Priority to CH738078A priority Critical patent/CH627206A5/de

1979-07-04 Priority to CA000331123A priority patent/CA1161034A/en

1979-07-04 Priority to DE19792927102 priority patent/DE2927102A1/de

1979-07-04 Priority to IT49637/79A priority patent/IT1162413B/it

1979-07-04 Priority to CS471579A priority patent/CS208117B2/cs

1979-07-05 Priority to BR7904258A priority patent/BR7904258A/pt

1979-07-05 Priority to FR7917528A priority patent/FR2430442A1/fr

1979-07-05 Priority to ES482256A priority patent/ES482256A1/es

1979-07-05 Priority to BE0/196156A priority patent/BE877517A/fr

1979-07-06 Priority to JP8511279A priority patent/JPS5512187A/ja

1979-07-06 Priority to GB7923613A priority patent/GB2026527B/en

1981-12-31 Publication of CH627206A5 publication Critical patent/CH627206A5/de

1993-05-26 Priority to US08/063,848 priority patent/US5298607A/en

Links

-1 polyazo Polymers 0.000 claims description 84
239000000975 dye Substances 0.000 claims description 72
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
239000000985 reactive dye Substances 0.000 claims description 41
150000001412 amines Chemical class 0.000 claims description 25
VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 25
230000008878 coupling Effects 0.000 claims description 24
238000010168 coupling process Methods 0.000 claims description 24
238000005859 coupling reaction Methods 0.000 claims description 24
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 19
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 19
238000000034 method Methods 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 15
239000000987 azo dye Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 7
150000004056 anthraquinones Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
229910001385 heavy metal Inorganic materials 0.000 claims description 5
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 5
VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
125000004999 nitroaryl group Chemical group 0.000 claims description 4
PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 description 123
239000010949 copper Substances 0.000 description 33
150000003254 radicals Chemical class 0.000 description 21
239000007859 condensation product Substances 0.000 description 17
150000004699 copper complex Chemical class 0.000 description 17
229920000742 Cotton Polymers 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000243 solution Substances 0.000 description 14
MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
239000011651 chromium Substances 0.000 description 10
229910052804 chromium Inorganic materials 0.000 description 9
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 8
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 8
125000000542 sulfonic acid group Chemical group 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
238000009833 condensation Methods 0.000 description 7
229910052802 copper Inorganic materials 0.000 description 7
150000002431 hydrogen Chemical group 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
150000001555 benzenes Chemical class 0.000 description 6
238000004043 dyeing Methods 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
KKAMNIDZQVXDJV-UHFFFAOYSA-N 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)C)=CC=C21 KKAMNIDZQVXDJV-UHFFFAOYSA-N 0.000 description 5
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
150000003457 sulfones Chemical class 0.000 description 5
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 4
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 4
FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 4
HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
229920002678 cellulose Polymers 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
239000004744 fabric Substances 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000002243 precursor Substances 0.000 description 4
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 3
GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 3
HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
241000083869 Polyommatus dorylas Species 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
150000001879 copper Chemical class 0.000 description 3
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
150000002790 naphthalenes Chemical class 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
239000004627 regenerated cellulose Substances 0.000 description 3
YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
ZDFCTUISEBJBEQ-UHFFFAOYSA-N 3-amino-4-hydroxynaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=C(O)C(N)=CC(S(O)(=O)=O)=C21 ZDFCTUISEBJBEQ-UHFFFAOYSA-N 0.000 description 2
VNWVMZDJPMCAKD-UHFFFAOYSA-N 3-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1O VNWVMZDJPMCAKD-UHFFFAOYSA-N 0.000 description 2
DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 2
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
ZTTJTIAKGUQOMO-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[2-methoxy-5-methyl-4-[(2-sulfophenyl)diazenyl]phenyl]diazenyl]naphthalene-2,7-disulfonic acid Chemical compound COc1cc(N=Nc2ccccc2S(O)(=O)=O)c(C)cc1N=Nc1c(O)c2c(N)cc(cc2cc1S(O)(=O)=O)S(O)(=O)=O ZTTJTIAKGUQOMO-UHFFFAOYSA-N 0.000 description 2
HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 2
DXQHKRLJFRUIKF-UHFFFAOYSA-N 7-(ethylamino)-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NCC)=CC=C21 DXQHKRLJFRUIKF-UHFFFAOYSA-N 0.000 description 2
CUJGROXHJQNORR-UHFFFAOYSA-N 7-amino-6-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(O)C(N)=CC2=C1S(O)(=O)=O CUJGROXHJQNORR-UHFFFAOYSA-N 0.000 description 2
CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 2
CYJJLCDCWVZEDZ-UHFFFAOYSA-N 8-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(N)=CC=CC2=C1 CYJJLCDCWVZEDZ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000000732 arylene group Chemical group 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000003599 detergent Substances 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
ICIDZHMCYAIUIJ-UHFFFAOYSA-N dinaphthalen-1-yldiazene Chemical compound C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ICIDZHMCYAIUIJ-UHFFFAOYSA-N 0.000 description 2
FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000463 material Substances 0.000 description 2
238000001465 metallisation Methods 0.000 description 2
PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 2
YYHJPNVCYHVPJK-UHFFFAOYSA-N naphthalen-1-yl-(2-phenylnaphthalen-1-yl)diazene Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1N=NC1=CC=CC2=CC=CC=C12 YYHJPNVCYHVPJK-UHFFFAOYSA-N 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000001005 nitro dye Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000021286 stilbenes Nutrition 0.000 description 2
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CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000001769 aryl amino group Chemical group 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
229950011260 betanaphthol Drugs 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000004700 cobalt complex Chemical class 0.000 description 1
MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000010985 leather Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
BIYQLXLSSLKTNE-UHFFFAOYSA-N n-(3-aminophenyl)-2-hydroxyacetamide Chemical compound NC1=CC=CC(NC(=O)CO)=C1 BIYQLXLSSLKTNE-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000009980 pad dyeing Methods 0.000 description 1
QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical group Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000010979 ruby Substances 0.000 description 1
229910001750 ruby Inorganic materials 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CH738078A 1978-07-06 1978-07-06 CH627206A5 (ja)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
CH738078A CH627206A5 (ja)	1978-07-06	1978-07-06
CA000331123A CA1161034A (en)	1978-07-06	1979-07-04	Reactive dyes, processes for their manufacture and use thereof
DE19792927102 DE2927102A1 (de)	1978-07-06	1979-07-04	Reaktivfarbstoffe, deren herstellung und verwendung
IT49637/79A IT1162413B (it)	1978-07-06	1979-07-04	Coloranti reattivi e procedimento per la loro produzione ed applicazione
CS471579A CS208117B2 (en)	1978-07-06	1979-07-04	Method of making the reactive dyes
BR7904258A BR7904258A (pt)	1978-07-06	1979-07-05	Corantes reativos, sua preparacao e seu emprego
FR7917528A FR2430442A1 (fr)	1978-07-06	1979-07-05	Colorants reactifs, leur procede de preparation et leur utilisation
ES482256A ES482256A1 (es)	1978-07-06	1979-07-05	Procedimiento para la preparacion de colorantes reactivos.
BE0/196156A BE877517A (fr)	1978-07-06	1979-07-05	Colorants reactifs, leur procede de preparation et leur utilisation
JP8511279A JPS5512187A (en)	1978-07-06	1979-07-06	Reactive dye* prepatation and application thereof
GB7923613A GB2026527B (en)	1978-07-06	1979-07-06	Reactive dyes processes for their manufacture and use thereof
US08/063,848 US5298607A (en)	1978-07-06	1993-05-26	Reactive dyes containing fluorotriazine and vinylsulfonyl radicals

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH738078A CH627206A5 (ja)	1978-07-06	1978-07-06

Publications (1)

Publication Number	Publication Date
CH627206A5 true CH627206A5 (ja)	1981-12-31

Family

ID=4324232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH738078A CH627206A5 (ja)	1978-07-06	1978-07-06

Country Status (10)

Country	Link
JP (1)	JPS5512187A (ja)
BE (1)	BE877517A (ja)
BR (1)	BR7904258A (ja)
CA (1)	CA1161034A (ja)
CH (1)	CH627206A5 (ja)
CS (1)	CS208117B2 (ja)
DE (1)	DE2927102A1 (ja)
ES (1)	ES482256A1 (ja)
FR (1)	FR2430442A1 (ja)
GB (1)	GB2026527B (ja)

Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2842640A1 (de) *	1978-09-29	1980-04-10	Bayer Ag	Reaktivfarbstoffe
DE2901547A1 (de) *	1979-01-16	1980-07-24	Bayer Ag	Reaktivfarbstoffe
JPS5848672B2 (ja) *	1979-07-06	1983-10-29	住友化学工業株式会社	セルロ−ズ系繊維の染色法
JPS56118976A (en) *	1980-02-20	1981-09-18	Sumitomo Chemical Co	Dyeing of cellulosic fiber
JPS6018358B2 (ja) *	1980-03-04	1985-05-09	住友化学工業株式会社	セルロ−ズ系繊維材料の染色方法
DE3011447A1 (de) *	1980-03-25	1981-10-01	Hoechst Ag, 6000 Frankfurt	Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
DE3019960A1 (de) *	1980-05-24	1981-12-03	Hoechst Ag, 6000 Frankfurt	Verfahren zum faerben und bedrucken von hydroxy- und/oder carbonamidgruppen enthaltenden fasermaterialien
US4663440A (en) *	1980-06-04	1987-05-05	Sumitomo Chemical Company, Limited	Bisazo brown reactive dye
JPS5742986A (en) *	1980-08-29	1982-03-10	Nippon Kayaku Kk	Dyeing of natural or synthetic fiber by using reactive monoazo compound
US4937326A (en) *	1980-11-26	1990-06-26	Sumitomo Chemical Company, Limited	Reactive scarlet dyes having both monochlorotriazinyl and vinylsulfone type reactive groups linked via N-alkylated amino
DE3165870D1 (en) *	1980-11-26	1984-10-11	Sumitomo Chemical Co	Reactive monoazo scarlet dyes
JPS57183478A (en) *	1981-05-06	1982-11-11	Sumitomo Chemical Co	Dyeing of cellulosic fiber
JPS5792054A (en) *	1980-11-28	1982-06-08	Nippon Kayaku Co Ltd	Copper-containing reactive dye
JPS57161174A (en) *	1981-03-24	1982-10-04	Sumitomo Chemical Co	Dyeing of cellulosic fiber
DE3116296A1 (de) *	1981-04-24	1982-11-11	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von kupferkomplexazofarbstoffen
US4841031A (en) *	1981-05-06	1989-06-20	Sumitomo Chemical Company, Limited	Reactive dye having both monochlorotriazinyl and vinylsulfone type reactive groups
DE3118402A1 (de) *	1981-05-09	1982-12-09	Hoechst Ag, 6000 Frankfurt	Azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
JPS5815559A (ja) *	1981-07-21	1983-01-28	Sumitomo Chem Co Ltd	二官能型反応性化合物
DE3141908A1 (de) *	1981-10-22	1983-05-05	Hoechst Ag, 6230 Frankfurt	Wasserloesliche pyridon-azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
DE3142035A1 (de) *	1981-10-23	1983-05-05	Hoechst Ag, 6230 Frankfurt	Wasserloesliche monoazo-pyridonverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
DE3274256D1 (en) *	1981-11-25	1987-01-02	Sumitomo Chemical Co	Reactive dye
JPS5891767A (ja) *	1981-11-25	1983-05-31	Sumitomo Chem Co Ltd	モノアゾ化合物およびそれを用いるセルロ−ス繊維の染色方法
EP0085025B1 (de) *	1982-01-21	1986-10-15	Ciba-Geigy Ag	Reaktivfarbstoffe, deren Herstellung und Verwendung
DE3373110D1 (en) *	1982-01-29	1987-09-24	Ciba Geigy Ag	Reactive dyes, their preparation and their use
DE3217812A1 (de) *	1982-05-12	1983-11-17	Hoechst Ag, 6230 Frankfurt	Monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
JPS5915451A (ja) *	1982-07-19	1984-01-26	Sumitomo Chem Co Ltd	金属ホルマザン化合物、その製造法およびそれを用いる繊維材料の染色方法
DE3229799A1 (de) *	1982-08-11	1984-02-23	Hoechst Ag, 6230 Frankfurt	Wasserloesliche kupferkomplex-disazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
US4510030A (en) *	1982-12-21	1985-04-09	Nippon Light Metal Company Limited	Method for cathodic protection of aluminum material
JPS59122549A (ja) *	1982-12-28	1984-07-16	Sumitomo Chem Co Ltd	新規なモノアゾ化合物
JPS59152958A (ja) *	1983-02-17	1984-08-31	Sumitomo Chem Co Ltd	フタロシアニン化合物およびそれを用いて染色または捺染する方法
JPS59157154A (ja) *	1983-02-25	1984-09-06	Sumitomo Chem Co Ltd	モノアゾ化合物およびそれを用いる染色または捺染方法
JPS59174649A (ja) *	1983-03-24	1984-10-03	Sumitomo Chem Co Ltd	モノアゾ化合物およびそれを用いる染色または捺染法
US4631341A (en) *	1983-05-23	1986-12-23	Sumitomo Chemical Company, Limited	Anthraquinone compound having both monohalogenotriazinyl and vinylsulfone type fiber reactive groups
JPS59217766A (ja) *	1983-05-25	1984-12-07	Sumitomo Chem Co Ltd	アントラキノン化合物およびそれを用いる捺染または染色法
US4592818A (en) *	1983-09-12	1986-06-03	Outboard Marine Corporation	Cathodic protection system
JPS6071782A (ja) *	1983-09-27	1985-04-23	住友化学工業株式会社	セルロ−ズ系繊維のチ−ズ染色法
JPS60229957A (ja) *	1984-04-27	1985-11-15	Mitsubishi Chem Ind Ltd	反応性染料
CH663215A5 (de) *	1984-04-09	1987-11-30	Mitsubishi Chem Ind	Reaktive azofarbstoffe.
JPS612762A (ja) *	1984-06-14	1986-01-08	Sumitomo Chem Co Ltd	ジスアゾ化合物およびそれを用いる染色または捺染法
JPS61123670A (ja) *	1984-11-20	1986-06-11	Sumitomo Chem Co Ltd	モノアゾ化合物およびそれを用いて染色または捺染する方法
JPS61171769A (ja) *	1985-01-24	1986-08-02	Sumitomo Chem Co Ltd	モノアゾ化合物およびそれを用いて染色または捺染する方法
JPS60215061A (ja) *	1985-03-26	1985-10-28	Sumitomo Chem Co Ltd	繊維反応性モノアゾ化合物
JPH0670188B2 (ja) *	1985-05-28	1994-09-07	三菱化成株式会社	ジスアゾ系染料
JPH0649838B2 (ja) *	1985-05-30	1994-06-29	住友化学工業株式会社	モノアゾ化合物およびそれを用いる染色または捺染方法
DE3624136A1 (de) *	1985-09-30	1987-04-09	Hoechst Ag	Wasserloesliche azoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe
JPH0689264B2 (ja) *	1985-10-09	1994-11-09	三菱化成株式会社	反応染料
DE3603101A1 (de) *	1986-02-01	1987-08-06	Hoechst Ag	Wasserloesliche disazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
JPS6248768A (ja) *	1986-06-05	1987-03-03	Sumitomo Chem Co Ltd	繊維反応性トリフエノジオキサジン化合物
JPH0788478B2 (ja) *	1986-12-24	1995-09-27	住友化学工業株式会社	モノアゾ化合物及びそれを用いる染色又は捺染方法
US4876334A (en) *	1987-02-06	1989-10-24	Ciba-Geigy Corporation	Triazinyl reactive dyes in which the triazinyl is furter substituted with a reactive radical
DE3705789A1 (de) *	1987-02-24	1988-09-01	Hoechst Ag	Kupferkomplex-formazan-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe
EP0302006B1 (de) *	1987-07-03	1992-02-05	Ciba-Geigy Ag	Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
US4925928A (en) *	1988-06-23	1990-05-15	Ciba-Geigy Corporation	Reactive dyes containing vinylsulfonylalkylamino bound to a bis-(triazinylamino)-benzene group
ES2071076T3 (es) *	1989-07-24	1995-06-16	Ciba Geigy Ag	Colorantes formazano reactivos con las fibras, procedimiento para su obtencion y uso de los mismos.
EP0501252B1 (de) *	1991-02-27	1996-04-10	Bayer Ag	Bifunktionelle Reaktivfarbstoffe
GB2270923B (en) *	1992-09-24	1995-11-08	Sandoz Ltd	Fibre-reactive monoazo copper complexes
DE4333777A1 (de) *	1993-10-04	1995-04-06	Bayer Ag	Polyfunktionelle Azoreaktivfarbstoffe
KR0135648B1 (ko) *	1995-04-08	1998-04-22	성낙관	2환성 금속착염포르마잔유도체, 그 유도체의 제조방법, 그 유도체를 함유하는 조성물 및 그 유도체를 이용한 염색방법
DE19922825A1 (de) *	1999-05-19	2000-11-23	Dystar Textilfarben Gmbh & Co	Neue fluortriazinhaltige brillantgelbe Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von hydroxy- und amidgruppenhaltigen Materialien
DE102004017977A1 (de) *	2004-04-14	2005-11-10	Dystar Textilfarben Gmbh & Co. Deutschland Kg	Mischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und Verwendung
DE102005025010A1 (de)	2005-05-30	2006-12-07	Dystar Textilfarben Gmbh & Co Deutschland Kg	Reaktivfarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung
EP3294812A1 (en) *	2015-05-12	2018-03-21	Huntsman Advanced Materials (Switzerland) GmbH	Mixtures of reactive dyes and their use for the dyeing or printing of textile fibre materials

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Publication number	Priority date	Publication date	Assignee	Title
GB901434A (en) *	1959-03-04	1962-07-18	Ici Ltd	Azo dyestuffs
CH407373A (de) *	1960-10-28	1966-02-15	Ciba Geigy	Verfahren zur Herstellung neuer Farbstoffe
DE1265698C2 (de) *	1961-05-06	1968-11-07	Hoechst Ag	Verfahren zur Erzeugung von nassechten Faerbungen und Drucken
GB1093656A (en) *	1965-03-23	1967-12-06	Ici Ltd	New water-soluble reactive metal-complex azo dyestuffs, their preparation and use
DE1644208C3 (de) *	1967-04-19	1978-06-01	Bayer Ag, 5090 Leverkusen	Reaktivfarbstoffe
IT1121683B (it) *	1975-11-06	1986-04-10	Ciba Geigy Ag	Coloranti reattivi per fibre de procedimento per la loro produzione ed applicazione
CA1097621A (en) *	1976-07-12	1981-03-17	Herbert Seiler	Fibre-reactive azo dyestuffs, their manufacture and use

1978
- 1978-07-06 CH CH738078A patent/CH627206A5/de not_active IP Right Cessation
1979
- 1979-07-04 CA CA000331123A patent/CA1161034A/en not_active Expired
- 1979-07-04 DE DE19792927102 patent/DE2927102A1/de active Granted
- 1979-07-04 CS CS471579A patent/CS208117B2/cs unknown
- 1979-07-05 BE BE0/196156A patent/BE877517A/fr not_active IP Right Cessation
- 1979-07-05 FR FR7917528A patent/FR2430442A1/fr active Granted
- 1979-07-05 ES ES482256A patent/ES482256A1/es not_active Expired
- 1979-07-05 BR BR7904258A patent/BR7904258A/pt not_active IP Right Cessation
- 1979-07-06 JP JP8511279A patent/JPS5512187A/ja active Granted
- 1979-07-06 GB GB7923613A patent/GB2026527B/en not_active Expired

Also Published As

Publication number	Publication date
JPS5512187A (en)	1980-01-28
GB2026527B (en)	1982-09-22
DE2927102C2 (ja)	1989-11-16
BR7904258A (pt)	1980-04-08
DE2927102A1 (de)	1980-01-17
GB2026527A (en)	1980-02-06
ES482256A1 (es)	1980-08-16
FR2430442B1 (ja)	1983-11-10
FR2430442A1 (fr)	1980-02-01
JPS6248709B2 (ja)	1987-10-15
BE877517A (fr)	1980-01-07
CA1161034A (en)	1984-01-24
CS208117B2 (en)	1981-08-31

Publication	Publication Date	Title
DE2927102C2 (ja)	1989-11-16
DE1644208C3 (de)	1978-06-01	Reaktivfarbstoffe
DE2556640C2 (de)	1983-10-27	Reaktivfarbstoffe, deren Herstellung und Verwendung
DE2614550C3 (de)	1981-06-25	Neue Reaktivfarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von Cellulose sowie natürlichen und synthetischen Polyamidsubstraten
DE2611550C2 (de)	1987-03-26	Faserreaktive Farbstoffe, deren Herstellung und Verwendung
CH660016A5 (de)	1987-03-13	Reaktivfarbstoffe und deren herstellung.
DE1644204B2 (de)	1977-09-22	Reaktivfarbstoffe und deren verwendung
DE2650555A1 (de)	1977-05-18	Faserreaktive farbstoffe, deren herstellung und verwendung
DE1644203B2 (de)	1977-11-17	Reaktivfarbstoffe
DE2838540C2 (de)	1982-12-02	Reaktivfarbstoffe, deren Herstellung und Verwendung
DE2653199A1 (de)	1977-06-02	Faserreaktive farbstoffe, deren herstellung und verwendung
US5298607A (en)	1994-03-29	Reactive dyes containing fluorotriazine and vinylsulfonyl radicals
EP0085654B1 (de)	1987-08-19	Reaktivfarbstoffe, deren Herstellung und Verwendung
DE2331518A1 (de)	1974-01-10	Neue farbstoffe, deren herstellung und verwendung
DE3107265A1 (de)	1982-09-09	Reaktivfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben oder bedrucken von fasermaterialien
CH635859A5 (de)	1983-04-29	Azofarbstoffe sowie deren herstellung.
US4614818A (en)	1986-09-30	Process for the preparation of amino-fluoro-s-triazine dyes by reaction of cyanuric fluoride with an amino dye and an amide in one operation
DE1544505C3 (de)	1977-04-14	Reaktivfarbstoffe und Verfahren zu deren Herstellung und Anwendung
DE1644206C3 (de)	1978-06-01	Wasserlösliche Reaktivfarbstoffe, deren Herstellung und Verwendung zum Färben von Cellulosematerialien, Wolle, Seide, Polyamid- und Polyurethanfasern
DE2102217C3 (de)	1978-02-02	Reaktivfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE1544499C3 (de)	1977-08-18	Reaktivfarbstoffe
DE1261257B (de)	1968-02-15	Verfahren zur Herstellung von Farbstoffen
DE1544505B2 (de)	1976-08-26	Reaktivfarbstoffe und verfahren zu deren herstellung und anwendung
CH624137A5 (en)	1981-07-15	Process for the preparation of fibre-reactive dyes
CH615450A5 (en)	1980-01-31	Process for preparing fibre-reactive dyes

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Date	Code	Title	Description
1996-10-31	PUE	Assignment	Owner name: CIBA-GEIGY AG TRANSFER- CIBA SC HOLDING AG
1997-05-15	PFA	Name/firm changed	Owner name: CIBA SC HOLDING AG TRANSFER- CIBA SPECIALTY CHEMIC
1998-08-14	PL	Patent ceased