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WO2010133640A2 - Composition de coloration comprenant une base d'oxydation para-phénylènediamine secondaire et une base d'oxydation hétérocyclique - Google Patents

Composition de coloration comprenant une base d'oxydation para-phénylènediamine secondaire et une base d'oxydation hétérocyclique Download PDF

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Publication number
WO2010133640A2
WO2010133640A2 PCT/EP2010/056897 EP2010056897W WO2010133640A2 WO 2010133640 A2 WO2010133640 A2 WO 2010133640A2 EP 2010056897 W EP2010056897 W EP 2010056897W WO 2010133640 A2 WO2010133640 A2 WO 2010133640A2
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WIPO (PCT)
Prior art keywords
radical
amino
alkyl
optionally substituted
formula
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PCT/EP2010/056897
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English (en)
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WO2010133640A3 (fr
Inventor
Jean-Baptiste Saunier
Anne-Marie Couroux
Original Assignee
L'oreal
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Priority claimed from FR0953349A external-priority patent/FR2945739B1/fr
Priority claimed from FR0953351A external-priority patent/FR2945741B1/fr
Priority claimed from FR0953350A external-priority patent/FR2945740B1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2010133640A2 publication Critical patent/WO2010133640A2/fr
Publication of WO2010133640A3 publication Critical patent/WO2010133640A3/fr

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    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/38—Percompounds, e.g. peracids
    • 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
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits

Definitions

  • One subject of the invention is a dyeing composition
  • a dyeing composition comprising at least one particular secondary para- phenylenediamine oxidation base and at least one heterocyclic oxidation base selected from pyrazolopyridine, diaminopyrazolinone, diaminopyrazole or their addition salts with an acid or with a base.
  • oxidation bases such as ortho- or para- phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidation bases are colourless or weakly coloured compounds which, in combination with oxidizing products, can give rise, by an oxidative condensation process, to coloured compounds.
  • the "permanent" colouring obtained by virtue of these oxidation dyes furthermore has to satisfy a certain number of requirements.
  • it must be without disadvantage toxicologically, it must make it possible to obtain shades within the desired intensity and it must behave well in the face of external agents, such as light, bad weather, washing, permanent waving, perspiration and rubbing.
  • the dyes must also make it possible to cover white hair and, finally, be as unselective as possible, that is to say make it possible to obtain the smallest possible differences in colouring along the same keratin fibre, which is generally differently sensitized (i.e. damaged) between its tip and its root .
  • the aim of the present invention is to obtain a composition for colouring hair that exhibits enhanced dyeing properties in terms of intensity or chromaticity, and/or selectivity and/or resistance to external agents.
  • composition for dyeing keratin fibres comprising, in a suitable dyeing medium: one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid,
  • heterocyclic oxidation base selected from pyrazolopyridine of formula (II) or (III) ; diamino- N, N-dihydropyrazolone of formula (IV) ; 4, 5-diaminopyrazole of formula (V) or their addition salts with an acid or a base,
  • R' represents an oxygen or nitrogen atom
  • Q represents an oxygen atom or an NH or NH (Ci-C 4 ) alkyl group
  • Y represents a hydroxyl, amino, Ci-C 4 alkyl, (Ci- C 4 ) alkoxy, (Ci-C 4 ) alkylamino or di (Ci-C 4 ) alkylamino radical
  • Zi and Z 2 independently represent: - a simple covalent bond, - a divalent radical chosen from:
  • Zi can also represent a divalent radical -S-, -SO- or -SO2- when R' 1 is a methyl radical,
  • R' 1 and R' 2 independently represent:
  • ring a saturated, unsaturated or aromatic and substituted or unsubstituted 5- to 8-membered ring optionally comprising one or more heteroatoms or groups chosen from N, 0, S, SO 2 or -CO-, it being possible for the ring to be cationic and/or substituted with a cationic radical,
  • Ri 7 , Rig and R 19 being linear or branched Ci-C 5 alkyls which are optionally substituted with one or more hydroxyl groups,
  • R'i when Zi, respectively Z 2 , represents a covalent bond, then R'i, respectively R'2, can also represent:
  • Ci-C ⁇ alkylcarbonyl radical an optionally substituted Ci-C ⁇ alkylcarbonyl radical
  • R' 3, R' 4 and R' 5 which are identical or different, represent: a hydrogen atom, a hydroxyl radical, a Ci-C ⁇ alkoxy radical, a Ci-C ⁇ alkylthio radical, an amino radical, a monoalkylamino radical, a Ci-C ⁇ dialkylamino radical in which the alkyl radicals can form, with the nitrogen atom to which they are attached, a saturated or unsaturated and aromatic or non-aromatic 5- to 8-membered heterocycle which can include one or more heteroatoms or groups chosen from N, O, S, SO2 or CO, it being possible for the heterocycle to be cationic and/or substituted with a cationic radical, an optionally substituted Ci-C ⁇ alkylcarbonyl radical,
  • R' an -O-CO-R, -CO-O-R, NR-CO-R' or -CO-NRR' radical with R and R' as defined above, - a halogen, an -NHSO 3 H radical, an optionally substituted Ci-C 4 alkyl radical, a saturated, unsaturated or aromatic and optionally substituted carbon ring, - it being possible for R' 3, R' 4 and R' 5 to form, in pairs, a ring which is or is not partially saturated, • X represents an ion or group of ions which makes it possible to provide the electronegativity of the derivative of formula (II), with the condition that at least one of the groups R' 1 and R' 2 represents a cationic radical ;
  • R ' , R " , R '" and R which are identical or different, represent: a linear or branched, C1-C10, preferably Ci-C ⁇ alkyl radical optionally substituted with one or more radicals chosen from the group constituted by an ORi 5 radical, an NRi 6 Ri7 radical, a carboxyl radical, a sulphonic radical, a CONRi 6 Ri7 carboxamido radical, an SO2NR6R7 sulphonamido radical, a heteroaryl or an aryl optionally substituted with one or more (Ci-C 4 ) alkyl, hydroxyl, C1-C2 alkoxy, amino or (di) (C1-C2) alkylamino groups; an aryl radical optionally substituted with one or more (C1-C4) alkyl, hydroxyl, C1-C2 alkoxy, amino or (di) (C1-C2) alkylamino radicals; a 5- or 6-membered
  • R "' and R may also represent a hydrogen atom
  • Ri5, R16 and Ri 7 which are identical or different, represent: a hydrogen atom; - a linear or branched Ci-C 4 alkyl radical optionally substituted with one or more radicals chosen from a hydroxyl radical, C1-C2 alkoxy radical, CONR 8 R 9 carboxamido radical, SO2R8 sulphonyl radical, or an aryl radical optionally substituted with a (Ci-C 4 ) alkyl, hydroxyl, C1-C2 alkoxy, amino or (di) (C1-C2) alkylamino radical; an aryl radical optionally substituted with a (Ci-C 4 ) alkyl, hydroxyl, C1-C2 alkoxy, amino or (di) (C1-C2) alkylamino radical;
  • R16 and Ri7 which are identical or different, may also represent a CONRi 8 Ri 9 carboxamido radical or an SO2R18 sulphonyl radical;
  • R18 and Ri 9 which are identical or different, represent a hydrogen atom; a linear or branched Ci-C 4 alkyl radical optionally substituted with one or more hydroxyl or C1-C2 alkoxy radicals;
  • R ' and R " on the one hand, and R “' and R on the other hand, may form with the nitrogen atom(s) to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle, optionally substituted with one or more radicals chosen from the group constituted by halogen atoms, amino, (di) (Ci-C 4 ) alkylamino, hydroxyl, carboxyl, carboxamido or (C1-C2) alkoxy radicals, or Ci-C 4 alkyl radicals optionally substituted with one or more hydroxyl, amino, (di) alkylamino, alkoxy, carboxyl or sulphonyl radicals;
  • R"' and R may also form, together with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle, the carbon atoms of which may be replaced with an optionally substituted oxygen or nitrogen atom ;
  • X represents un oxygen atom, or a group NH
  • Y represents a hydrogen atom or a Ci-C 4 alkyl radical
  • Z represents a methyl radical when n is 0, r Z reprssents a Ci-C 4 alkyle radical, a group OR or NR' 'R' ' ' when n is 1 or higher, R' ' et R' ' ', identical or the same being a hydrogen atom, a Ci- C 4 alkyl radical; or R 5 forms with the nitrogen atom of NR 3 R 4 in position 5 a heterocyclic group having at least 4 members, at least one of R21, R22, R23 et R24 being a hydrogen atom.
  • Another subject of the invention is a dyeing method using this composition.
  • composition of the present invention for dyeing keratin fibres, in particular human keratin fibres such as the hair.
  • the invention also relates to multicompartment devices comprising compositions employing one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more heterocyclic oxidation bases chosen from the oxidation bases of formula (II) , (III) (IV) and (V) or their addition salts with an acid or with a base.
  • the composition of the present invention makes it possible, in particular, to obtain a composition for colouring keratin fibres that is suitable for use in oxidation dyeing and that makes it possible to obtain a colouring with varied, intense or chromatic, attractive and not very selective shades which is highly resistant to the various attacks to which the hair may be subjected such as shampoos, sweat, permanent deformations and light. It should be noted that in what follows, and unless otherwise indicated, the limits of a range of values are included in this range.
  • the compounds of formula (I), (II), (III) (IV) or (V) may be in the form of addition salts especially chosen from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates .
  • an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates .
  • the compounds of formula (I), (II), (III) (IV) or (V) are each generally present in an amount of between 0.001% and 10% by weight approximately and preferably between 0.005% and 6% by weight relative to the total weight of the dyeing composition .
  • alkyl used for the alkyl radicals and for the groups comprising an alkyl part means a linear or branched carbon chain comprising from 1 to 4 carbon atoms which is unsubstituted or substituted with one or more heterocycles or by one or more phenyl groups or by one or more groups chosen from halogen atoms, such as chlorine, bromine, iodine and fluorine; or hydroxyl, alkoxy, amino, carbonyl, carboxamido, sulphonyl, -CO2H, -SO3H, -PO3H2, - PO4H2, -NHSO3H, sulphonamide, mono (C1-C4) alkylamino or tri (Ci- C 4 ) alkylammonium radicals, or else by a di (Ci-C 4 ) alkylamino radical in which the two alky
  • alkoxy used for alkoxy radicals and for the groups comprising an alkoxy part means a linear or branched O-carbon chain comprising from 1 to 4 carbon atoms which is unsubstituted or substituted with one or more groups chosen from heterocycles; halogen atoms, such as chlorine, bromine, iodine and fluorine; or hydroxyl, amino, carbonyl, carboxamido, sulphonyl, -CO2H, -SO 3 H, -PO 3 H 2 , -PO 4 H 2 , -NHSO 3 H, sulphonamido, mono (Ci- C 4 ) alkylamino or tri (Ci-C 4 ) alkylammonium radicals, or else by a di (Ci-C 4 ) alkylamino radical in which the two alkyl groups can form, together with the nitrogen atom of said di (Ci-C 4 ) alkylamino group
  • heterocycle is understood to mean a 5-, 6-, 7- or 8-membered aromatic or non- aromatic ring comprising from 1 to 3 heteroatoms chosen from nitrogen, sulphur and oxygen atoms. These heterocycles can be fused to other heterocycles or to a phenyl group.
  • these heterocycles can be quaternized by a (Ci-C 4 ) alkyl radical .
  • phenyl is understood to mean a phenyl radical which is unsubstituted or substituted with one or more cyano, carbonyl, carboxamido, sulphonyl, -CO 2 H, -SO 3 H, -PO 3 H 2 , -PO 4 H 2 , hydroxyl, amino, mono (Ci-C 4 ) alkylamino or di (Ci-C 4 ) alkylamino radicals, in which, in the case of the last radical, the two alkyl groups may form, together with the nitrogen atom of said di (Ci-C 4 ) alkylamino group to which they are bonded, a ring which can be interrupted by one or more nitrogen, oxygen or sulphur atoms.
  • -NHSO3H radical an amino radical; a (Ci-C 4 ) alkylamino radical; a di (Ci-C 4 ) alkylamino radical in which the two alkyl groups can, jointly with the nitrogen atom to which they are bonded, form a ring which can be interrupted by one or more nitrogen, oxygen or sulphur atoms; a heterocycle as defined above; a sulphonamide radical; a carbonyl radical; a (Ci-C 4 ) alkoxy- carbonyl radical; a carboxamido radical; or a group of formula:
  • R'" represents an oxygen or nitrogen atom
  • Q represents an oxygen atom or an NH or NH (Ci-C 4 ) alkyl group
  • Y represents a hydroxyl, amino, Ci-C 4 alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) alkylamino or di (Ci-C 4 ) alkylamino radical.
  • cationic ring or "cationic heterocycle” is understood to mean a ring comprising one or more quaternary ammonium groups .
  • Ri 7 Ri 8 Ri 9 type of the trimethylammonium, triethylammonium, dimethyIethy1ammonium, diethylmethylammonium, diisopropylmethylammonium, diethylpropylammonium, ( ⁇ -hydroxy- ethyl) diethylammonium, di ( ⁇ -hydroxyethyl) methylammonium or tri ( ⁇ -hydroxyethyl) ammonium radicals .
  • the compounds of formula (III) can optionally be salified with strong inorganic acids, such as, for example, HCl, HBr, HI, H 2 SO 4 or H 3 PO 4 , or organic acids, such as, for example, acetic acid, lactic acid, tartaric acid, citric acid, succinic acid, benzenesulphonic acid, para-toluenesulphonic acid, formic acid or methanesulphonic acid.
  • strong inorganic acids such as, for example, HCl, HBr, HI, H 2 SO 4 or H 3 PO 4
  • organic acids such as, for example, acetic acid, lactic acid, tartaric acid, citric acid, succinic acid, benzenesulphonic acid, para-toluenesulphonic acid, formic acid or methanesulphonic acid.
  • anionic groups such as -CO 2 H, -SO3H, -POsH 2 or
  • the compounds of formula (II) or (III) can be salified by alkali metal or alkaline earth metal hydroxides, such as sodium hydroxide or potassium hydroxide, by aqueous ammonia or by organic amines.
  • solvates for example a hydrate or a solvate of a linear or branched alcohol, such as ethanol or isopropanol.
  • derivative of formula (III) is understood to mean all mesomeric or isomeric forms .
  • R' i or R' 2 denote a heterocycle
  • this heterocycle is preferably a cationic heterocycle or a heterocycle substituted with a cationic radical.
  • Mention may be made, by way of example, of imidazoles substituted with a quaternary ammonium radical or imidazoliums, piperazines substituted with a quaternary ammonium radical or piperaziniums, pyrrolidines substituted with a quaternary ammonium radical or pyrrolidiniums, or diazepanes substituted with a quaternary ammonium radical or diazepaniums .
  • R' i or R' 2 represent an -N + Ri 7 Ri 8 Ri 9 group, Ri 7 , Rig and Rig being linear or branched Ci-C 5 alkyls which are optionally substituted with one or more hydroxyl groups, such as trialkylammonium, tri (hydroxyalkyl) ammonium, (hydroxylalkyl) dialkylammonium or di (hydroxyalkyl) alkylammonium.
  • hydroxyl groups such as trialkylammonium, tri (hydroxyalkyl) ammonium, (hydroxylalkyl) dialkylammonium or di (hydroxyalkyl) alkylammonium.
  • R' 3, R' 4 and R' 5 radicals can independently be a hydrogen atom or an optionally substituted Ci-C 4 alkyl radical. Mention may be made, by way of example, of the methyl, ethyl, hydroxyethyl, aminoethyl, propyl or butyl radicals. According to a specific embodiment, R' 3/ R' and R' 5 independently represent a hydrogen atom or a Ci-C 4 alkyl radical.
  • R' 4 and R' 5 together form a partially saturated or unsaturated 5- or 8-membered ring, in particular a cyclopentene or cyclohexene, which is optionally substituted.
  • the compound of formula (III) corresponds to the following formula (III') :
  • ⁇ l represents covalent bond, an -NR' 6 (CH 2 ) q ⁇ radical or an - O(CH 2 ) P - radical and R' i is a cationic radical.
  • Ci-C ⁇ alkyl radical optionally substituted with a hydroxyl, (C1-C2) alkoxy, amino or (di) (C1-C2) alkylamino radical;
  • radicals R and R which may be identical or different, are chosen from methyl, ethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl and phenyl radicals.
  • radicals R ' and R " form, together with the nitrogen atoms to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6- membered ring.
  • the radicals R ' and R " form, together with the nitrogen atoms to which they are attached, a pyrazolidine or pyridazolidine ring, optionally substituted with one or more C1-C4 alkyl, hydroxyl, (C1-C2) alkoxy, carboxyl, carboxamido, amino or (di) (C1-C2) alkylamino radicals.
  • the radicals R and R form, together with the nitrogen atoms to which they are attached, a pyrazolidine or pyridazolidine ring.
  • the radicals R "' and R which may be identical or different, they are more particularly chosen from a hydrogen atom; a linear or branched Ci-C ⁇ alkyl radical optionally substituted with one or more hydroxyl, (C1-C2) alkoxy, amino or (di) (C1-C2) alkylamino radicals; a phenyl radical optionally substituted with one or more hydroxyl, amino or (C1-C2) alkoxy radicals .
  • the radicals R and R' which may be identical or different, are chosen from a hydrogen atom and a methyl, ethyl, isopropyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl or 2-carboxyethyl radical.
  • the radicals R and R represent a hydrogen atom.
  • the radicals R "' and R form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, piperidine, homopiperidine, piperazine and homopiperazine heterocycles; said rings possibly being substituted with one or more hydroxyl, amino, (di) (C1-C2) alkylamino, carboxyl, carboxamido or C1-C4 alkyl radicals optionally substituted with one or more hydroxyl, amino or C1-C2 (di) alkylamino radicals.
  • radicals R "' and R form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, 2, 5-dimethylpyrrolidine, pyrrolidine-2-carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, 4-hydroxypyrrolidine-2-carboxylic acid,
  • the radicals R "' and R form, together with the nitrogen atom to which they are attached, a 5- or 7-membered ring chosen from pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine, 3-dimethylaminopyrrolidine, pyrrolidine-2- carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, piperidine, hydroxypiperidine, homopiperidine, diazepane, N-methylhomopiperazine and N- ⁇ -hydroxyethylhomopiperazine .
  • a 5- or 7-membered ring chosen from pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine, 3-dimethylaminopyrrolidine, pyrrolidine-2- carboxylic acid, 3-hydroxypyrrolidine-2-carboxylic acid, piperidine, hydroxypiperidine, homopiperidine, diazepane, N-methylhomopiperazine and N- ⁇ -hydroxyethylhomopiperazine .
  • the radicals R "' and R form, together with the nitrogen atom to which they are attached, a 5-membered ring such as pyrrolidine, 3-hydroxypyrrolidine, 3-aminopyrrolidine or 3-dimethylaminopyrrolidine .
  • the diamino-N, N-dihydropyrazolone derivatives of formula (IV), or the addition salts thereof, which are particularly preferred are the following: 2, 3-diamino-6, 7-dihydro-lH, 5H-pyrazolo[l,2-a] pyrazol-1-one ; ⁇
  • the compound of formula (II) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the following compounds are particularly useful in the present invention 4, 5-diamino-l- methylpyrazole, 4, 5-diamino-l- (2-hydroxyethyl) -pyrazole, 4,5- diamino-1- (4 ' -chlorobenzyl) -pyrazole, 4, 5-diamino-l, 3- dimethyl-pyrazole, 4, 5-diamino-3-methyl-l-phenyl-pyrazole, 4, 5-diamino-l-methyl-3-phenylpyrazole, 4-amino-l, 3-dimethyl- 5-hydrazino-pyrazole, l-benzyl-4, 5-diamino-3-methylpyrazole, 4, 5-diamino-3-tert-butyl-l-methylpyrazole, 4, 5-diamino-l- tert-butyl-3-methyl-pyrazole, 4, 5-diamino-l- ( ⁇ -hydroxyethyl) - 3-methylpyrazole,
  • the diaminopyrazole (V) is such that R26 is a hydrogen atom.
  • R21, R22, R23, R24 represent a hydrogen atom or a C1-C4 alkyl radical and R25 is a alkyl, hydroxyalkyl or alkoxyalkyl radical.
  • Prefered compounds of formula (V) are 4, 5-diamino-l- (2- hydroxyethyl) -lH-pyrazole and the corresponding salt such as 4, 5-diamino-l- (2-hydroxyethyl) -lH-pyrazole sulfate having the following formula :
  • the dyeing composition according to the invention may contain and preferably does contain one or more couplers conventionally used for dyeing keratin fibres.
  • couplers conventionally used for dyeing keratin fibres.
  • couplers mention may especially be made of meta- phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers, heterocyclic couplers, and the addition salts thereof.
  • couplers examples include 2-methyl- 5-aminophenol, 5-N- ( ⁇ -hydroxyethyl) amino-2-methylphenol, 6-chloro-2-methyl-5-aminophenol, 3-aminophenol, 2, 4-dichloro-3- aminophenol, 5-amino-4-chloro-o-cresol, 1, 3-dihydroxybenzene, 1, 3-dihydroxy-2-methylbenzene, 4-chloro-l, 3-dihydroxybenzene, 2, 4-diamino-l- ( ⁇ -hydroxyethyloxy) benzene, 2-amino-4- ( ⁇ - hydroxyethylamino) -1-methoxybenzene, 1, 3-diaminobenzene, 1,3- bis (2, 4-diaminophenoxy) propane, 3-ureidoaniline, 3-ureido-l- dimethylaminobenzene, sesamol, l- ⁇ -hydroxyethylamino-3, 4- methylenedioxybenzene, ⁇
  • the coupler (s) is (are) each generally present in an amount of between 0.001% and 10% by weight approximately and preferably between 0.005% and 6% by weight relative to the total weight of the dyeing composition .
  • the dyeing composition of the invention may optionally comprise one or more additional oxidation bases conventionally used for dyeing keratin fibres other than the compounds of formula (I), (II) (III) (IV) and (V) or the salts thereof.
  • these additional oxidation bases are chosen from para-phenylenediamines other than the compound of formula (I) or the salts thereof, bis (phenyl) alkylenediamines, para-aminophenols, bis-para-aminophenols, ortho-aminophenols and heterocyclic bases other than the oxidation bases of formula (II) (III), (IV) and (V) and the addition salts thereof .
  • para-phenylenediamines mention may be made, for example, of para-phenylenediamine, para-toluenediamine, 2- chloro-para-phenylenediamine, 2, 3-dimethyl-para- phenylenediamine, 2, 6-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-methylaniline, N, N- bis ( ⁇ -hydroxyethyl) -para-phenylenediamine, 4-N,N-bis( ⁇ - hydroxyethyl) amino-2-methylaniline, 4-N,N-bis ( ⁇ - hydroxyethyl)
  • para-phenylenediamine para-toluenediamine, 2-isopropyl-para- phenylenediamine, 2- ⁇ -hydroxyethyl-para-phenylenediamine, 2- ⁇ - hydroxyethyloxy-para-phenylenediamine, 2, 6-dimethyl-para- phenylenediamine, 2, 6-diethyl-para-phenylenediamine, 2,3- dimethyl-para-phenylenediamine, N,N-bis ( ⁇ -hydroxyethyl) -para- phenylenediamine, 2-chloro-para-phenylenediamine and 2- ⁇ -acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof with an acid are particularly preferred.
  • the bis (phenyl) alkylenediamines mention may be made, for example, of N, N'-bis ( ⁇ -hydroxyethyl) -N, N' -bis (4'- aminophenyl) -1, 3-diaminopropanol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'- bis (4'-aminophenyl) ethylenediamine, N,N'-bis(4- aminophenyl) tetramethylenediamine, N, N' -bis ( ⁇ -hydroxyethyl) - N, N' -bis (4-aminophenyl) tetramethylenediamine, N, N' -bis (4- methylaminophenyl) tetramethylenediamine, N, N' -bis (ethyl) -N, N' - bis (4'-amino-3'-methylphenyl) ethylenediamine and l,8-bis(2,5
  • para-aminophenol examples include para-aminophenol, 4-amino-3-methylphenol, 4-amino- 3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2- methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2- methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino- 2- ( ⁇ -hydroxyethylaminomethyl) phenol, 4-amino-2-fluorophenol, 1- hydroxy-4-methylaminobenzene and 2, 2' -methylenebis (4-amino- phenol) and the addition salts thereof with an acid.
  • para-aminophenol 4-amino-3-methylphenol, 4-amino- 3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2- methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2- methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino- 2- ( ⁇ -hydroxye
  • ortho-aminophenols mention may be made, for example, of 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6- methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid.
  • heterocyclic bases mention may be made, for example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2, 5-diaminopyridine, 2- (4- methoxyphenyl) amino-3-aminopyridine, 2, 3-diamino-6- methoxypyridine, 2- ( ⁇ -methoxyethyl) amino-3-amino-6- methoxypyridine and 3, 4-diaminopyridine, and the addition salts thereof with an acid.
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2359399, JP 88-169571; JP 05-63124; EP 0 770 375 or patent application WO 96/15765, such as 2, 4, 5, 6-tetraaminopyrimidine, 4-hydroxy- 2, 5, 6-triaminopyrimidine, 2-hydroxy-4, 5, 6-triaminopyrimidine, 2 , 4-dihydroxy-5, 6-diaminopyrimidine and 2, 5, 6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of 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-dimethylpyrazol
  • addition salts of the additional oxidation bases and of the couplers that may be used in the context of the invention are chosen especially from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates, and the addition salts with a base, such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, amines or alkanolamines .
  • an acid such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates
  • a base such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, amines or alkanolamines .
  • the dyeing composition in accordance with the invention may also contain one or more direct dyes which may, in particular, be chosen from nitrobenzene dyes, azo direct dyes or methine direct dyes. These direct dyes may be of nonionic, anionic or cationic nature.
  • the medium suitable for dyeing also known as dyeing vehicle, generally comprises water or a mixture of water and of one or more solvents such as, for example, Ci-C 4 lower alkanols, for instance ethanol and isopropanol, polyols such as propylene glycol, dipropylene glycol or glycerol, and polyol ethers such as dipropylene glycol monomethyl ether.
  • the solvent (s) is (are) in general present in proportions which may be between 1% and 40% by weight approximately, and more preferably between 3% and 30% by weight approximately, relative to the total weight of the dyeing composition.
  • the dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickening agents and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents such as, for example, volatile or non-volatile, modified or unmodified silicones, film-forming agents, ceramides, preservatives or opacifying agents .
  • adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic,
  • the above adjuvants are generally present in an amount, for each of them, of between 0.01% and 20% by weight relative to the weight of the composition.
  • the pH of the dyeing composition in accordance with the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It may be adjusted to the desired value by using acidifying or basifying agents commonly used in the dyeing of keratin fibres or else by means of conventional buffering systems.
  • acidifying agents mention may be made, by way of example, of inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid or sulphonic acids.
  • basifying agents mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and also derivatives thereof, sodium or potassium hydroxides and compounds of formula (A) below:
  • R a , R b , R c and R d which are identical or different, represent a hydrogen atom, a Ci-C 4 alkyl radical or a Ci-C 4 hydroxyalkyl radical.
  • composition according to the invention may comprise one or more oxidizing agents.
  • the oxidizing agents are those conventionally used for the oxidation dyeing of keratin fibres, which are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, peracids and oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
  • composition with or without oxidizing agent according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibres, and especially human hair. It may result from the mixing of several compositions at the time of use.
  • compositions one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, optionally one or more additional oxidation bases other than the compounds of formula (I) or of formulae (II) (III) (IV) (V) or salts thereof, and optionally one or more couplers, a second composition comprising the oxidation base(s) of formula (II) (III) (IV) (V) or salts thereof and optionally a third composition comprising one or more oxidizing agents as described previously.
  • compositions one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, the oxidation base(s) of formula (II) (III) (IV) (V) or salts thereof, optionally one or more additional oxidation bases other than the compounds of formula (I) or of formula (II) (III) (IV) (V) or salts thereof, and optionally one or more couplers, another composition comprising one or more oxidizing agents as described previously.
  • the composition of the invention is therefore applied to the hair for colouring keratin fibres either as is, or in the presence of one or more oxidizing agents for colouring keratin fibres .
  • the method of the present invention is a method in which, applied to the fibres, is the composition without oxidizing agent according to the present invention as defined previously, either alone or in the presence of an oxidizing agent for a sufficient time to develop the desired colouring.
  • the colour may be developed at acid, neutral or alkaline pH and the oxidizing agent may be added to the composition of the invention only at the time of use or it may be used starting from an oxidizing composition containing it, applied simultaneously with or sequentially to the composition of the invention.
  • the composition without oxidizing agent according to the present invention is mixed, preferably at the time of use, with a composition containing, in a medium suitable for dyeing, one or more oxidizing agents.
  • the mixture obtained is then applied to the keratin fibres. After a leave-in time of 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, the keratin fibres are rinsed, washed with shampoo, rinsed again, then dried.
  • the oxidizing agents are those indicated previously.
  • the oxidizing composition may also contain various additives conventionally used in compositions for dyeing hair and as defined previously.
  • the pH of the oxidizing composition containing the oxidizing agent is such that after mixing with the dyeing composition, the pH of the resulting composition applied to the keratin fibres preferably varies between 3 and 12 approximately, and more preferably still between 5 and 11. It may be adjusted to the desired value by means of acidifying or basifying agents customarily used in the dyeing of keratin fibres and as defined previously.
  • Another subject of the invention is a dyeing kit or multicompartment device in which a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above comprising one or more oxidation bases chosen from the compounds of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from the compounds of formula (II) (III) (IV) (V) or their addition salts with an acid or a base and a second compartment contains one or more oxidizing agents.
  • a second device is constituted by a first compartment containing a composition comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, optionally one or more additional oxidation bases other than those of formula (I), (II) (III)
  • a third device may optionally comprise the two compartments from the second device plus a third compartment containing a composition that comprises one or more oxidizing agents.
  • composition was diluted extemporaneously with 1 times its weight of 20-volume aqueous hydrogen peroxide solution, the pH of which is 3.
  • each of the extemporaneous mixtures thus produced was applied to grey hair containing 90% white hair in an amount of 10 g per 1 g of hair. After leaving in for 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • composition C3 was prepared :
  • composition was diluted extemporaneously with 1 times its weight of 20-volume aqueous hydrogen peroxide solution, the pH of which is 3.
  • the extemporaneous mixture thus produced was applied at ambient temperature to grey hair containing 90% white hair in an amount of 10 g per 1 g of hair. After leaving in for 30 minutes, the hair was then rinsed, washed with a standard shampoo and dried.
  • composition C4 was prepared :
  • composition was diluted extemporaneously with 1 times its weight of 20-volume aqueous hydrogen peroxide solution, the pH of which is 3.
  • the extemporaneous mixture thus produced was applied at ambient temperature to grey hair containing 90% white hair in an amount of 10 g per 1 g of hair. After leaving in for 30 minutes, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually. A chestnut colouring of the hair with red highlights was obtained.

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Abstract

L'invention concerne une composition pour colorer des fibres de kératine qui comprend, dans un milieu de coloration approprié : une ou plusieurs bases d'oxydation sélectionnées parmi un composé de formule (I) ou ses sels d'addition avec un acide, et une ou plusieurs bases d'oxydation hétérocycliques sélectionnées parmi pyrazolopyridine de formule (II) ou (III); diamino-N, N-dihydropyrazolone de formule (IV); 4,5- diaminopyrazole de formule (V) ou leurs sels d'addition avec un acide ou une base. La composition de la présente invention permet en particulier d'obtenir une coloration avec des teintes variées, intenses et/ou chromatiques, attrayantes et faiblement sélectives, et qui présente une haute résistance aux diverses attaques auxquelles les cheveux peuvent être soumis.
PCT/EP2010/056897 2009-05-19 2010-05-19 Composition de coloration comprenant une base d'oxydation para-phénylènediamine secondaire et une base d'oxydation hétérocyclique WO2010133640A2 (fr)

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
FR0953350 2009-05-19
FR0953349A FR2945739B1 (fr) 2009-05-19 2009-05-19 Composition tinctoriale comprenant une base d'oxydation para-phenylene diamine secondaire et une base d'oxydation aminopyrazolopyridine
FR0953351A FR2945741B1 (fr) 2009-05-19 2009-05-19 Composition tinctoriale comprenant une base d'oxydation para-phenylene diamine secondaire et une base diaminopyrazolinone
FR0953351 2009-05-19
FR0953349 2009-05-19
FR0953350A FR2945740B1 (fr) 2009-05-19 2009-05-19 Composition tinctoriale comprenant une base d'oxydation para-phenylene diamine secondaire et une base d'oxydation diaminopyrazole
US18407009P 2009-06-04 2009-06-04
US18407809P 2009-06-04 2009-06-04
US61/184,070 2009-06-04
US61/184,078 2009-06-04
US18441909P 2009-06-05 2009-06-05
US61/184,419 2009-06-05

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EP2651386A2 (fr) * 2010-12-17 2013-10-23 L'Oréal Composition de coloration comprenant au moins quatre précurseurs de colorants incluant au moins une base d'oxydation et au moins un coupleur
US20130312203A1 (en) * 2010-12-17 2013-11-28 L'oreal Dyeing composition comprising a fatty substance, a pyrazolopyridine oxidation base and a coupler
US8663341B2 (en) 2012-06-25 2014-03-04 The Procter & Gamble Company Hair colorant compositions comprising 2-Methoxymethy1-1,4-diaminobenzene, methods, and kits comprising the compositions
US20140259454A1 (en) * 2010-12-17 2014-09-18 L'oreal Dye composition comprising a heterocyclic oxidation base and a 4-aminoindole coupler
US9012691B2 (en) 2012-10-26 2015-04-21 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US20150202125A1 (en) * 2012-08-02 2015-07-23 L'oreal Dye composition comprising nonionic guar gum or a nonionic derivative thereof, process and device for the same
WO2015173322A1 (fr) * 2014-05-16 2015-11-19 L'oreal Composition comprenant un coupleur phénolique particulier et une base d'oxydation
US9309185B2 (en) 2012-10-26 2016-04-12 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9539192B2 (en) 2014-04-02 2017-01-10 Noxell Corporation Hair colouring compositions, kits, method, and use thereof
US9587116B2 (en) 2014-11-04 2017-03-07 Noxell Corporation Azo direct dyes and method for dyeing hair using these dyes
US9688609B2 (en) 2014-11-04 2017-06-27 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine
US9695109B2 (en) 2014-11-04 2017-07-04 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
US9758469B2 (en) 2014-11-04 2017-09-12 Noxell Corporation Process for the preparation of 2-substituted-1,4-benzenediamines and salts thereof
US9827185B2 (en) 2012-08-02 2017-11-28 L'oreal Dyeing composition comprising at least one fatty substance, at least one oxidizing agent and at least one non-ionic, anionic and amphoteric surfactant
US9993409B2 (en) 2014-05-16 2018-06-12 L'oreal Composition for dyeing keratin fibres, comprising an oxidation base and a particular heteroaryl coupler
CN108472235A (zh) * 2015-12-21 2018-08-31 莱雅公司 用于染发的包含杂环氧化显色碱和2-氨基-5-乙基苯酚成色剂的组合物
US10201483B2 (en) 2012-08-02 2019-02-12 L'oreal Dye composition in cream form comprising at least one oil and little or no solid fatty alcohol, dyeing process and suitable device
US10226411B2 (en) 2012-08-02 2019-03-12 L'oreal Dyeing composition comprising a fatty substance, a non-ionic guar gum, an amphoteric surfactant and a non-ionic or anionic surfactant, and an oxidizing agent, dyeing process and suitable device
US11213471B2 (en) 2015-12-21 2022-01-04 L'oreal Composition for dyeing the hair, comprising an oxidation base, a 2-amino-5-ethylphenol coupler and a fatty substance
US11324682B2 (en) 2015-12-21 2022-05-10 L'oreal Composition for dyeing the hair, comprising an oxidation base of para-phenylenediamine type and a 2-amino-5-ethylphenol coupler

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US9125834B2 (en) * 2010-12-17 2015-09-08 L'oreal Dye composition comprising a heterocyclic oxidation base and a 4-aminoindole coupler
US9220671B2 (en) * 2010-12-17 2015-12-29 L'oreal Dye composition comprising at least four dye precursors including at least one oxidation base and at least one coupler
US20140007358A1 (en) * 2010-12-17 2014-01-09 L'oreal Dye composition comprising at least four dye precursors including at least one oxidation base and at least one coupler
US20130312203A1 (en) * 2010-12-17 2013-11-28 L'oreal Dyeing composition comprising a fatty substance, a pyrazolopyridine oxidation base and a coupler
EP2651386A2 (fr) * 2010-12-17 2013-10-23 L'Oréal Composition de coloration comprenant au moins quatre précurseurs de colorants incluant au moins une base d'oxydation et au moins un coupleur
US20140259454A1 (en) * 2010-12-17 2014-09-18 L'oreal Dye composition comprising a heterocyclic oxidation base and a 4-aminoindole coupler
US9370477B2 (en) * 2010-12-17 2016-06-21 L'oreal Dyeing composition comprising a fatty substance, a pyrazolopyridine oxidation base and a coupler
US8663341B2 (en) 2012-06-25 2014-03-04 The Procter & Gamble Company Hair colorant compositions comprising 2-Methoxymethy1-1,4-diaminobenzene, methods, and kits comprising the compositions
US8702814B2 (en) 2012-06-25 2014-04-22 The Procter & Gamble Company Hair colorant compositions comprising 2-methoxymethyl-1,4-diaminobenzene and 2,6-diaminopyridine, methods, and kits comprising the compositions
US8709100B2 (en) 2012-06-25 2014-04-29 The Procter & Gamble Company Hair colorant compositions comprising 2-methoxymethyl-1,4-diaminobenzene and 5-amino-4-chloro-o-cresol, methods, and kits comprising the compositions
US20150202125A1 (en) * 2012-08-02 2015-07-23 L'oreal Dye composition comprising nonionic guar gum or a nonionic derivative thereof, process and device for the same
US10201483B2 (en) 2012-08-02 2019-02-12 L'oreal Dye composition in cream form comprising at least one oil and little or no solid fatty alcohol, dyeing process and suitable device
US10226411B2 (en) 2012-08-02 2019-03-12 L'oreal Dyeing composition comprising a fatty substance, a non-ionic guar gum, an amphoteric surfactant and a non-ionic or anionic surfactant, and an oxidizing agent, dyeing process and suitable device
US10137063B2 (en) * 2012-08-02 2018-11-27 L'oreal Dye composition comprising nonionic guar gum or a nonionic derivative thereof, process and device for the same
US9827185B2 (en) 2012-08-02 2017-11-28 L'oreal Dyeing composition comprising at least one fatty substance, at least one oxidizing agent and at least one non-ionic, anionic and amphoteric surfactant
US9012691B2 (en) 2012-10-26 2015-04-21 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9309185B2 (en) 2012-10-26 2016-04-12 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9539192B2 (en) 2014-04-02 2017-01-10 Noxell Corporation Hair colouring compositions, kits, method, and use thereof
US9993409B2 (en) 2014-05-16 2018-06-12 L'oreal Composition for dyeing keratin fibres, comprising an oxidation base and a particular heteroaryl coupler
WO2015173322A1 (fr) * 2014-05-16 2015-11-19 L'oreal Composition comprenant un coupleur phénolique particulier et une base d'oxydation
FR3020943A1 (fr) * 2014-05-16 2015-11-20 Oreal Composition comprenant un coupleur phenolique particulier, et une base d'oxydation
US9758469B2 (en) 2014-11-04 2017-09-12 Noxell Corporation Process for the preparation of 2-substituted-1,4-benzenediamines and salts thereof
US9587116B2 (en) 2014-11-04 2017-03-07 Noxell Corporation Azo direct dyes and method for dyeing hair using these dyes
US9695109B2 (en) 2014-11-04 2017-07-04 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
US9688609B2 (en) 2014-11-04 2017-06-27 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine
CN108472235A (zh) * 2015-12-21 2018-08-31 莱雅公司 用于染发的包含杂环氧化显色碱和2-氨基-5-乙基苯酚成色剂的组合物
US20180369104A1 (en) * 2015-12-21 2018-12-27 L'oreal Composition for dyeing the hair, comprising a heterocyclic oxidation base and a 2-amino-5-ethylphenol coupler
US11213471B2 (en) 2015-12-21 2022-01-04 L'oreal Composition for dyeing the hair, comprising an oxidation base, a 2-amino-5-ethylphenol coupler and a fatty substance
US11324682B2 (en) 2015-12-21 2022-05-10 L'oreal Composition for dyeing the hair, comprising an oxidation base of para-phenylenediamine type and a 2-amino-5-ethylphenol coupler
US11730688B2 (en) * 2015-12-21 2023-08-22 L'oreal Composition for dyeing the hair, comprising a heterocyclic oxidation base and a 2-amino-5-ethylphenol coupler

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