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WO2016016441A1 - Composition comprenant un copolymère amps® et un précurseur de colorant d'oxydation et/ou un colorant direct - Google Patents

Composition comprenant un copolymère amps® et un précurseur de colorant d'oxydation et/ou un colorant direct Download PDF

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Publication number
WO2016016441A1
WO2016016441A1 PCT/EP2015/067705 EP2015067705W WO2016016441A1 WO 2016016441 A1 WO2016016441 A1 WO 2016016441A1 EP 2015067705 W EP2015067705 W EP 2015067705W WO 2016016441 A1 WO2016016441 A1 WO 2016016441A1
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composition according
composition
dyes
monomer
chosen
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Aurélie PHELIPOT
Grégory MIALLET
Frédéric Simonet
Nathalie Mougin
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LOreal SA
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LOreal SA
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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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • 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

Definitions

  • the present invention relates to a composition for dyeing keratin fibres comprising at least one copolymer comprising at least one monomer of 2-acrylamido-2- methylpropanesulfonic acid (AMPS®), at least one monomer with a hydrophobic group and at least one ethylenically unsaturated monomer which does not comprise any hydrophobic groups, and at least one oxidation dye precursor and/or one direct dye.
  • AMPS® 2-acrylamido-2- methylpropanesulfonic acid
  • oxidation dyeing In order to dye human keratin fibres durably, dyeing methods have been developed which are referred to as permanent, and are also called oxidation dyeing. These methods employ dyeing compositions containing oxidation dye precursors, also generally known as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds. These oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • oxidation bases also generally known as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidation bases are colourless or weakly coloured compounds which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • oxidation bases can be varied by combining them with couplers or colouring modifiers, the latter being chosen especially from aromatic meta-diaminobenzenes, from meta-aminophenols, from meta- diphenols and from certain heterocyclic compounds such as indole compounds.
  • couplers or colouring modifiers the latter being chosen especially from aromatic meta-diaminobenzenes, from meta-aminophenols, from meta- diphenols and from certain heterocyclic compounds such as indole compounds.
  • couplers or colouring modifiers the variety of molecules used as oxidation bases and couplers allows a wide range of colours to be obtained.
  • the permanent dyeing process thus consists in applying, to the keratin fibres, bases or a mixture of bases and couplers with hydrogen peroxide (H 2 0 2 or aqueous hydrogen peroxide solution), as oxidizing agent, in leaving to spread, and in then rinsing the fibres.
  • hydrogen peroxide H 2 0 2 or aqueous hydrogen peroxide solution
  • the colourings resulting therefrom have the advantage of being permanent, strong and resistant to external agents, in particular to light, bad weather, washing, perspiration and rubbing.
  • the second type of dyeing is "semi-permanent" dyeing or direct dyeing, which consists in applying, to the keratin fibres, direct dyes, which are coloured and colouring molecules that have affinity for the said fibres, in leaving them on for a time, and then in rinsing them off.
  • the direct dyes generally used are chosen from nitrobenzene, anthraquinone, nitropyridine, azo, xanthene, acridine, azine and triarylmethane direct dyes, and natural dyes.
  • compositions containing one or more direct dye(s) are applied to keratin fibres for a time necessary to obtain the desired colouring, and are then rinsed off.
  • the colourings which result therefrom are generally chromatic colourings.
  • amphiphilic polymers comprising at least one ethylenically unsaturated monomer with a sulfonic group, and more particularly the polymers or copolymers of 2-acrylamido-2-methylpropanesulfonic acid which are the subject of patent application FR2818537, has also been discovered for obtaining dyeing solutions which are thickened or in the form of a gel and which are storage-stable.
  • the objective of the present invention is to alleviate the drawbacks of the prior art and thus to propose dyeing compositions which are easy to use, in particular easy to apply and to spread on the hair, and which have good thickening while having good dyeing properties, in particular low selectivity.
  • compositions havin good rinsability which do not require a high amount of water to be rinsed.
  • composition in particular for dyeing keratin fibres, comprising:
  • At least one copolymer comprising at least one monomer of 2- acrylamido-2-methylpropanesulfonic acid (AMPS®), at least one monomer with a hydrophobic group and at least one ethylenically unsaturated monomer which does not comprise any hydrophobic groups, and
  • AMPS® 2- acrylamido-2-methylpropanesulfonic acid
  • At least one oxidation dye precursor and/or one direct dye are at least one oxidation dye precursor and/or one direct dye.
  • composition according to the invention enables the application of the composition to keratin fibres , and also the dyeing properties of the composition, in particular in terms of selectivity, to be significantly improved.
  • the rinsability is also improved, because the amount of water to be used during rinsing is decreased, along with the time required to rinse.
  • composition according to the invention comprises at least one copolymer comprising at least one monomer of 2-acrylamido-2-methylpropanesulfonic acid (AMPS®), at least one monomer with a hydrophobic group and at least one ethylenically unsaturated monomer which does not comprise any hydrophobic groups.
  • AMPS® 2-acrylamido-2-methylpropanesulfonic acid
  • hydrophobic group is understood to be a hydrocarbon-based, branched or unbranched, saturated or unsaturated fatty chain comprising from 6 to 50 carbon atoms.
  • the copolymer(s) may be crosslinked in the presence of a crosslinking agent.
  • crosslinked copolymer is understood to be a non-linear copolymer which is in the form of a three-dimensional network that is insoluble in water but swellable in water, leading to the production of a chemical gel.
  • the crosslinking agent is chosen from polyolefinically unsaturated compounds commonly used for the crosslinking of polymers obtained by radical polymerization.
  • the crosslinking agent is more particularly chosen from ethylene glycol dimethacrylate, tetraallyloxyethane, ethylene glycol diacrylate, diallylurea, triallylamine, trimethylolpropane triacrylate or methylenebisacrylamide, or a mixture of these compounds.
  • the crosslinking agent is trimethylolpropane triacrylate.
  • the AMPS® copolymer(s) are crosslinked by a crosslinking agent, preferably trimethylolpropane triacrylate.
  • the 2-acrylamido-2-methylpropanesulfonic acid monomer(s) of the copolymer contained in the composition in accordance with the invention are in free form or are partially or completely neutralized by an inorganic base (sodium hydroxide, potassium hydroxide or aqueous ammonia) or an organic base, such as mono-, di- or triethanolamine, an aminomethylpropanediol, N-methylglucamine, basic amino acids, such as arginine and lysine, and the mixture of these compounds.
  • an inorganic base sodium hydroxide, potassium hydroxide or aqueous ammonia
  • organic base such as mono-, di- or triethanolamine, an aminomethylpropanediol, N-methylglucamine, basic amino acids, such as arginine and lysine, and the mixture of these compounds.
  • AMPS® monomers preferably correspond to the following general formula (1 ):
  • X + denotes a cationic counterion, in particular an alkali metal or alkaline-earth metal, or an ammonium, preferably ammonium, or a mixture of cations
  • Ri denotes a hydrogen atom or a linear or branched Ci-C 6 alkyl radical such as methyl, and Ri preferably denotes a hydrogen atom.
  • the 2-acrylamido-2-methylpropanesulfonic acid monomer(s) according to the invention are partially or completely salified in the form of the ammonium salt.
  • the 2-acrylamido-2-methylpropanesulfonic acid monomer(s) according to the invention are completely salified, preferably in the form of the ammonium salt.
  • the AMPS® copolymer(s) comprise at least one monomer with a hydrophobic group which is preferably an ethylenically unsaturated monomer comprising at least one fatty hydrocarbon-based chain comprising from 6 to 50 carbon atoms, preferably from 6 to 22 and more particularly from 12 to 18 carbon atoms.
  • the monomer wih a hydrophobic group is preferably chosen from the acrylates or acrylamides of formula (2):
  • R-i denotes a hydrogen atom or a linear or branched Ci-C 6 alkyl radical, preferably methyl
  • Y denotes O or NH
  • R 2 denotes a hydrocarbon-based radical comprising from 6 to 50 carbon atoms and more preferably from 6 to 22 carbon atoms and even more preferably from 12 to 18 carbon atoms
  • x denotes a number ranging from 0 to 100.
  • Y denotes an oxygen atom.
  • Ri group represents a methyl
  • x represents an integer between 3 and 25, and x is preferably equal to 4.
  • the R 2 group represents an alkyl radical comprising from 12 to 18 carbon atoms.
  • Y denotes an oxygen atom
  • the Ri group represents a methyl
  • the R 2 group represents an alkyl radical comprising from 12 to 18 carbon atoms
  • x represents an integer between 3 and 25, and x is preferably equal to 4.
  • the hydrophobic monomer of formula (2) is tetraethoxylated (4EO) lauryl methacrylate, corresponding to the compound of formula (2) in which the Y group denotes O, the R 2 group represents and alkyl radical comprising 12 carbon atoms and x is equal to 4.
  • the monomer with a hydrophobic group is tetraethoxylated lauryl methacrylate.
  • the AMPS® copolymer may comprise at least one monomer of formula (2) in which x is equal to 0, with Y representing an oxygen atom, the Ri group representing a methyl, and the R 2 group representing an alkyl radical comprising from 12 to 18 carbon atoms.
  • the monomer with a hydrophobic group is preferably lauryl methacrylate.
  • the AMPS® copolymer comprises at least one monomer of formula (2) in which x is equal to 0, with Y preferably denoting an oxygen atom, the Ri group representing a methyl, and the R 2 group representing an alkyl radical comprising from 12 to 18 carbon atoms, and at least one monomer of formula (2) in which Y denotes an oxygen atom, the Ri group represents a methyl, the R 2 group represents an alkyl radical comprising from 12 to 18 carbon atoms, and x represents an integer between 3 and 25, and x is preferably equal to 4.
  • the AMPS® copolymer comprises, as monomers with a hydrophobic group, lauryl methacrylate and tetraethoxylated lauryl methacrylate.
  • the AMPS® copolymer(s) also comprise at least one ethylenically unsaturated monomer, which does not comprise any hydrophobic groups, preferably corresponding to the following general formula (3):
  • R-i denotes a hydrogen atom or a linear or branched Ci-C 4 alkyl radical
  • Ri preferably denotes a hydrogen atom
  • R 2 denotes a linear or branched C C 4 alkyl radical
  • R 3 denotes a linear or branched C C 4 alkyl radical
  • R 2 and R 3 preferably denote a methyl.
  • the ethylenically unsaturated monomer which does not comprise any hydrophobic groups is chosen from (meth)acrylamides such as acrylamide, (meth)acrylic acids and the esters ((meth)acrylates) thereof, such as 2-hydroxyethyl acrylate, vinylpyrrolidones, N-(Ci-C 4 )alkylacrylamides, and N,N-di(Ci-
  • C 4 )alkylacrylamides such as N,N-dimethylacrylamide.
  • the ethylenically unsaturated monomer which does not comprise any hydrophobic groups is N,N-dimethylacrylamide.
  • the AMPS® copolymer is chosen from the copolymers of 2- acrylamido-2-methylpropanesulfonic acid, preferably completely salified, of N,N- dimethylacrylamide, of tetraethoxylated lauryl methacrylate and of lauryl methacrylate, preferably crosslinked, such as for example the copolymer sold under the name Sepimax zen by Seppic, with I NCI name Polyacrylate crosspolymer-6.
  • the AMPS® copolymer(s) described above may be present in concentrations ranging from 0.01 % to 30 % by weight, more preferably from 0.1 % to 10 % by weight and even more preferably from 0.5% to 2 % by weight, relative to the total weight of the composition.
  • Oxidation dye precursors and/or direct dyes are characterized by:
  • composition according to the invention comprises at least one oxidation dye precursor and/or one direct dye.
  • oxidation dye precursors mention may be made of oxidation bases, optionally combined with one or more couplers.
  • the oxidation bases may be chosen from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and the addition salts thereof.
  • the oxidation base(s) of the invention are chosen from para- phenylenediamines and heterocyclic bases.
  • para-phenylenediamines examples that may be mentioned include para-phenylenediamine, para-tolylenediamine, 2-chloro-para- phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para- phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para- phenylenediamine, ⁇ , ⁇ -dimethyl-para-phenylenediamine, N,N-diethyl-para- phenylenediamine, ⁇ , ⁇ -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( -hydroxy
  • para-phenylenediamine para-tolylenediamine, 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, 2- -acetylaminoethyloxy-para-phenylenediamine and 2- methoxymethyl-para-phenylenediamine, and the addition salts thereof with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines examples that may be mentioned include N,N'-bis( -hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1 ,3-diaminopropanol, ⁇ , ⁇ '- 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 1 ,8-bis(2,5-diaminophenoxy)-3
  • para-aminophenols examples that may be mentioned include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3- chlorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2- hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2- aminomethylphenol, 4-amino-2-( -hydroxyethyl-aminomethyl)phenol and 4-amino-2- fluorophenol, and the addition salts thereof with an acid.
  • ortho-aminophenols examples that may be mentioned include
  • heterocyclic bases mention may be made in particular 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, for instance 2,5- diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the addition salts thereof.
  • Other pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[1 ,5-a]pyridine oxidation bases or the addition salts thereof, described, for example, in patent application FR 2 801 308.
  • Examples that may be mentioned include pyrazolo[1 ,5-a]pyrid-3-ylamine, 2- acetylaminopyrazolo[1 ,5-a]pyrid-3-ylamine, 2-(morpholin-4-yl)pyrazolo[1 ,5-a]pyrid-3- ylamine, 3-aminopyrazolo[1 ,5-a]pyridine-2-carboxylic acid, 2-methoxypyrazolo[1 ,5- a]pyrid-3-ylamine, (3-aminopyrazolo[1 ,5-a]pyrid-7-yl)methanol, 2-(3-aminopyrazolo[1 ,5- a]pyrid-5-yl)ethanol, 2-(3-aminopyrazolo[1 ,5-a]pyrid-7-yl)ethanol, (3-aminopyrazolo[1 ,5- a]pyrid-2-yl)
  • oxidation bases according to the invention are chosen from 3-aminopyrazolo[1 ,5-a]pyridines preferably substituted in position 2 with:
  • a cationic or non-cationic 5- to 7-membered heterocycloalkyl group comprising from 1 to 3 heteroatoms, which is optionally substituted with one or more (CrC 6 )alkyl groups such as di(Ci-C 4 )alkylpiperazinium;
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2359399, JP 88169571 , JP 05-63124 and 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, 2,5,6-triaminopyrimidine and the addition salts thereof, and the tautomeric forms thereof, when a tautomeric equilibrium exists.
  • the heterocyclic oxidation bases of the invention are chosen from 4,5-diaminopyrazoles such as 4,5-diamino-1-(P- hydroxyethyl)pyrazole. 4,5-Diamino-1-( -methoxyethyl)pyrazole may also be used.
  • the oxidation base(s) present in the composition of the invention are generally present in an amount ranging from 0.001 % to 10% by weight approximately of the total weight of the dyeing composition, and preferably ranging from 0.005% to 5% by weight relative to the total weight of the dyeing composition.
  • the additional couplers that are conventionally used for the dyeing of keratin fibres are chosen from the meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof.
  • Examples that may be mentioned include 1 ,3-dihydroxybenzene, 1 ,3- dihydroxy-2-methylbenzene, 4-chloro-1 ,3-dihydroxybenzene, 1 -hydroxy-3- aminobenzene, 2-methyl-1 ,3-dihydroxybenzene, 5-amino-6-chloro-2-methylphenol, 2- methyl-5-aminophenol, 2-methyl-5-hydroxyethylaminophenol, 2,4-diamino-1 -( ⁇ - hydroxyethyloxy)benzene, 2-amino-4-( -hydroxyethylamino)-1 -methoxybenzene, 1 ,3- diaminobenzene, 1 ,3-bis(2,4-diaminophenoxy)propane, 3-ureidoaniline, 3-ureido-1 - dimethylaminobenzene, sesamol, thymol, 1 ⁇ -hydroxyethylamino-3,4- methylenedioxybenzen
  • addition salts of the oxidation bases and couplers that may be used in the context of the invention are especially chosen from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the coupler(s) are generally present in a total amount ranging from 0.001 % to 10% by weight approximately of the total weight of the composition, and preferably ranging from 0.005% to 5% by weight relative to the total weight of the composition.
  • the direct dye(s) according to the invention may be chosen from synthetic direct dyes and natural direct dyes or mixtures thereof.
  • a direct dye is understood to be any dye which does not require the presence of a chemical oxidizing agent other than air for colouring.
  • a synthetic direct dye is understood to be any direct dye that does not exist in the natural state, including dyes obtained semi-synthetically.
  • Suitable synthetic direct dyes include azo, methine, carbonyl, azine, xanthene, nitro(hetero)aryl, tri(hetero)arylmethane, (metallo)porphyrin and phthalocyanine direct dyes, alone or as mixtures.
  • azo direct dyes examples include the following dyes, described in Colour Index International, 3rd edition:
  • the methine dyes are derived from methine, azomethine, hydrazono, mono- and diarylmethane, indoamine (or diphenylamine), indophenol, indoaniline and (hemi)cyanine compounds, such as styryl, streptocyanine, carbocyanine, azacarbocyanine, diazacarbocyanine and tetraazacarbocyanine, such as tetraazapentamethine, dyes, and optical and geometric isomers thereof.
  • azo, azomethine, methine or tetraazapentamethine direct dyes that may be used according to the invention, mention may be made of the cationic dyes described in patent applications WO 95/15144, WO 95/01772 and EP 714954; FR 2189006, FR 2285851 , FR 2140205, EP 1378544, EP 1674073.
  • indoamine dyes that may be used according to the invention, mention may be made of the following compounds:
  • X " representing an anion preferably chosen from chloride, iodide, methyl sulfate, ethyl sulfate, acetate and perchlorate.
  • the synthetic direct dyes of the carbonyl family examples include dyes chosen from quinone, acridone, benzoquinone, anthraquinone, naphthoquinone, benzanthrone, anthranthrone, pyranthrone, pyrazolanthrone, pyrimidinoanthrone, flavanthrone, idanthrone, flavone, (iso)violanthrone, isoindolinone, benzimidazolone, isoquinolinone, anthrapyridone, pyrazoloquinazolone, perinone, quinacridone, quinophthalone, indigoid, thioindigo, naphthalimide, anthrapyrimidine, diketopyrrolopyrrole and coumarin dyes.
  • the synthetic direct dyes of the azine family mention may be made especially of azine, fluorindine, acridine, (di)oxazine and (di)thiazine dyes.
  • azine dyes examples include the following compounds:
  • the synthetic direct dyes of the xanthene family mention may be made especially of xanthene, thioxanthene and pyronine dyes.
  • nitro(hetero)aryl synthetic direct dyes are more particularly nitrobenzene or nitropyridine direct dyes.
  • nitrobenzene direct dyes that may be used according to the invention, mention may be made in a nonlimiting manner of the following compounds:
  • triarylmethane dyes that may be used according to the invention, mention may be made of the following compounds:
  • cationic or non-cationic compounds optionally comprising one or more metals or metal ions, such as, for example, alkali metals and alkaline-earth metals, zinc and silicon.
  • nitrobenzene dyes examples include nitrobenzene dyes; azo, methine, azomethine, hydrazono or styryl direct dyes; azacarbocyanines such as tetraazacarbocyanines (tetraazapentamethines); quinone direct dyes, and in particular anthraquinone, naphthoquinone or benzoquinone direct dyes; azine direct dyes; xanthene direct dyes; triarylmethane direct dyes; indoamine direct dyes, indigoid direct dyes, phthalocyanine direct dyes and porphyrin direct dyes, alone or as mixtures.
  • nitrobenzene dyes examples include nitrobenzene dyes; azo, methine, azomethine, hydrazono or styryl direct dyes; azacarbocyanines such as tetraazacarbocyanines (tetraazapentameth
  • the dye(s) are chosen from (poly)azo dyes such as (di)azo dyes; hydrazono dyes; (poly)methine dyes such as styryl dyes; anthraquinone dyes or naphthalimide dyes.
  • these dyes are (poly)cationic.
  • the dyes are chosen from cationic dyes known as "basic dyes".
  • Het + represents a cationic heteroaryl group, preferably bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, optionally substituted with one or more (Ci-C 8 ) alkyl groups such as methyl;
  • Ar + represents an aryl group, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferentially ammonium, particularly tri(CrC 8 alkyl)ammonium such as trimethylammonium;
  • - Ar represents an aryl group, especially phenyl, which is optionally substituted, preferably with one or more electron-donating groups such as i) optionally substituted Ci-C 8 alkyl, ii) optionally substituted Ci-C 8 alkoxy, iii) (di)(Ci-C 8 alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group, iv) aryl(Ci-C 8 alkyl)amino, or v) optionally substituted N-(Ci-C 8 alkyl)-N-aryl(Ci-C 8 alkyl)amino, or alternatively Ar represents a julolidine group; - Ar' is an optionally substituted divalent (hetero)arylene group such as phenylene, particularly para-phenylene, or naphthalene, which are optionally substituted, preferably with one or more Ci-C 8 alkyl, hydroxyl or CrC 8
  • - Ar is an optionally substituted (hetero)aryl group such as phenyl or pyrazolyl, which are optionally substituted, preferably with one or more Ci-C 8 alkyl, hydroxyl, (di)(CrC 8 alkyl)amino, Ci-C 8 alkoxy or phenyl groups;
  • R a and R b which are identical or different, represent a hydrogen atom or a Ci-C 8 alkyl group, which is optionally substituted, preferably with a hydroxyl group;
  • R a and R b represent a hydrogen atom or a CrC 4 alkyl group, which is optionally substituted with a hydroxyl group;
  • - Q " represents an organic or inorganic anionic counterion, such as a halide or an alkyl sulfate.
  • dyes may be chosen from the cationic dyes referred to as "basic dyes".
  • the dyes of formulae (I), ( ⁇ ) and (II) described in patent applications WO 95/15144, WO 95/01772 and EP 714954 are more particularly preferred.
  • the direct dyes are chosen from the following compounds:
  • R 1 represents a C C 4 alkyl group such as methyl
  • R 2 and R 3 which are identical or different, represent a hydrogen atom or a Ci-C 4 alkyl group such as methyl;
  • R 4 represents a hydrogen atom or an electron-donating group such as optionally substituted Ci-C 8 alkyl, optionally substituted Ci-C 8 alkoxy, or (di)(Ci-C 8 alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group; particularly, R 4 is a hydrogen atom;
  • - Z represents a CH group or a nitrogen atom, preferably CH;
  • Q " is as defined previously, and represents in particular a halide such as a chloride, or an alkyl sulfate such as methyl sulfate or mesityl.
  • natural dyes is understood to be any dye or dye precursor that is naturally occurring and that is produced either by extraction (and possible purification) from a plant or animal matrix, optionally in the presence of natural compounds such as ash or ammonia, or by chemical synthesis.
  • Natural dyes that may be mentioned include lawsone, henna, curcumin, chlorophyllin, alizarin, kermesic acid, purpurin, purpurogallin, indigo, Tyrian purple, sorghum, carminic acid, catechin, epicatechin, juglone, bixin, betanin, quercetin, chromene dyes and chroman dyes, including haematein and brazilein, and laccaic acids.
  • the direct dyes are chosen from ionic or nonionic species, preferably cationic or nonionic species.
  • the direct dye(s) may represent from 0.0001 % to 10% by weight, preferably from 0.005% to 5% by weight relative to the total weight of the dyeing composition.
  • the composition according to the invention comprises at least one chemical oxidizing agent.
  • chemical oxidizing agent is understood to be an oxidizing agent other than atmospheric oxygen.
  • the chemical oxidizing agent(s) are chosen, for example, from hydrogen peroxide, urea peroxide, alkali metal bromates, peroxygenated salts, such as for example persulfates or perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates.
  • the oxidizing agent is hydrogen peroxide.
  • the oxidizing agent(s) generally represent from 0.1 % to 50% by weight, preferably from 0.5% to 20% by weight and better still from 1 % to 15% by weight relative to the total weight of the dyeing composition. According to one embodiment, the dyeing composition according to the invention does not comprise an oxidizing agent.
  • the dyeing composition according to the invention does not comprise an oxidizing agent, the oxidizing agent being provided by an oxidizing composition.
  • the composition according to the invention comprises at least one basifying agent.
  • the basifying agent(s) may be inorganic, organic or hybrid.
  • the inorganic basifying agent(s) are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium carbonate or bicarbonate, potassium carbonate or bicarbonate, sodium hydroxide or potassium hydroxide, or mixtures thereof.
  • the organic basifying agent(s) are preferably chosen from organic amines with a pKb at 25°C of less than 12, preferably less than 10 and even more advantageously less than 6. It should be noted that it is the pKb corresponding to the highest basicity function .
  • the organic amines do not comprise any alkyl or alkenyl fatty chain comprising more than ten carbon atoms.
  • the organic basifying agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (la) below:
  • formula (la) W is a divalent Ci-C 6 alkylene radical optionally substituted with one or more hydroxyl groups or a Ci-C 6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as O, or NR U ;
  • R x , R y , R z , R t and R u which are identical or different, represent a hydrogen atom or a Ci-C 6 alkyl, Ci-C 6 hydroxyalkyl or CrC 6 aminoalkyl radical.
  • Examples of amines of formula (la) that are mentioned include 1 ,3- diaminopropane, 1 ,3-diamino-2-propanol, spermine and spermidine.
  • alkanolamine is understood to be an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C C 8 alkyl groups bearing one or more hydroxyl radicals.
  • Organic amines chosen from alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising one to three identical or different C1-C4 hydroxyalkyl radicals are in particular suitable for performing the invention.
  • MAA monoethanolamine
  • diethanolamine triethanolamine
  • monoisopropanolamine diisopropanolamine
  • N-dimethylaminoethanolamine 2-amino-2-methyl-1 -propanol
  • triisopropanolamine 2-amino-2-methyl-1 ,3-propanediol
  • 3-amino-1 ,2-propanediol 3- dimethylamino-1 ,2-propanediol and tris(hydroxymethylamino)methane.
  • amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function more particularly chosen from carboxylic acid, sulfonic acid, phosphonic acid and phosphoric acid functions.
  • the amino acids may be in neutral or ionic form.
  • amino acids that may be used in the present invention, mention may be made in particular of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
  • the amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in a ureido function.
  • Such basic amino acids are preferably chosen from those corresponding to formula (lib) below, and also the salts thereof:
  • R represents a group chosen from:
  • the compounds corresponding to formula (lib) are histidine, lysine, arginine, ornithine and citrulline.
  • the organic amine may also be chosen from organic amines of heterocyclic type. Besides histidine that has already been mentioned in the amino acids, mention may in particular be made of pyridine, piperidine, imidazole, triazole, tetrazole and benzimidazole.
  • the organic amine may also be chosen from amino acid dipeptides.
  • amino acid dipeptides that may be used in the present invention, mention may be made especially of carnosine, anserine and balenine.
  • the organic amine may also be chosen from compounds comprising a guanidine function.
  • amines of this type that may be used in the present invention, besides arginine, which has already been mentioned as an amino acid, mention may be made especially of creatine, creatinine, 1 ,1 -dimethylguanidine, 1 ,1 -diethylguanidine, glycocyamine, metformin, agmatine, N-amidinoalanine, 3-guanidinopropionic acid, 4- guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-1 -sulfonic acid.
  • Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid.
  • Guanidine carbonate or monoethanolamine hydrochloride may be used in particular.
  • the basifying agent(s) present in the composition according to the invention are chosen from alkanolamines, and amino acids in neutral or ionic form, in particular basic amino acids, and preferably corresponding to those of formula (lib).
  • the basifying agent(s) are chosen from alkanolamines, and in particular monoethanolamine (MEA), and basic amino acids in neutral or ionic form.
  • MEA monoethanolamine
  • the basifying agent is monoethanolamine.
  • the composition according to the invention has a content of basifying agent(s) ranging from 0.01 % to 30% by weight and preferably from 0.1 % to 20% by weight relative to the weight of the dyeing composition.
  • the composition according to the invention comprises aqueous ammonia, or a salt thereof, then the amount by weight of basifying agent(s) other than the aqueous ammonia is greater than that of the aqueous ammonia (expressed as NH 3 ).
  • composition according to the invention may also comprise a solvent such as water or a mixture of water and one or more organic solvents or a mixture of organic solvents.
  • a solvent such as water or a mixture of water and one or more organic solvents or a mixture of organic solvents.
  • organic solvent is understood to be an organic substance that is capable of dissolving or dispersing another substance without chemically modifying it.
  • organic solvents examples include Ci-C 4 lower alkanols, such as ethanol and isopropanol; polyols and polyol ethers such as 2- butoxyethanol, propylene glycol, hexylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, hexylene glycol, and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol.
  • Ci-C 4 lower alkanols such as ethanol and isopropanol
  • polyols and polyol ethers such as 2- butoxyethanol, propylene glycol, hexylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, hexylene glycol, and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol.
  • the organic solvents or water may be present in proportions preferably of between 1 % and 90% by weight approximately, and even more preferably between 50% and 85% by weight approximately, relative to the total weight of the dyeing composition.
  • the dyeing composition according to the invention is aqueous.
  • aqueous composition according to the present application is understood to be a composition comprising at least 5% of water.
  • An aqueous composition preferably comprises more than 10% by weight of water, more preferably more than 20% by weight of water, even better still at least 30% of water, or even at least 40% of water.
  • the composition according to the invention comprises water in an amount ranging from 50% to 90% relative to the total weight of the composition, better still from 75% to 85% by weight, relative to the total weight of the composition.
  • composition according to the invention may also contain various adjuvants conventionally used in hair treatment compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof other than the AMPS ® copolymers used in the compositions according to the invention, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners other than the copolymers according to the invention, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance volatile or non-volatile, modified or unmodified silicones, film- forming agents, ceramides, preserving agents, opacifiers and fatty substances.
  • adjuvants conventionally used in hair treatment compositions such as anionic, cationic, nonionic, amphoteric or zwitterio
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 40% by weight relative to the weight of the dyeing composition, and preferably between 0.1 % and 20% by weight relative to the weight of the dyeing composition.
  • the composition according to the invention comprises at least one modified or non modified starch .
  • the botanical origin of the starch molecules used in the present invention may be cereals or tubers.
  • the starches are chosen, for example, from corn starch, rice starch, cassava starch, barley starch, potato starch, wheat starch, sorghum starch and pea starch.
  • the starches may be chemically or physically modified especially by one or more of the following reactions: pregelatinization, oxidation, crosslinking, esterification, etherification, amidation, heat treatments.
  • Ci-C 6 acyl acetyl
  • Ci-C 6 hydroxyalkyl hydroxyethyl or hydroxypropyl
  • carboxymethyl or octenylsuccinic especially Ci-C 6 acyl (acetyl), Ci-C 6 hydroxyalkyl (hydroxyethyl or hydroxypropyl), carboxymethyl or octenylsuccinic.
  • Monostarch phosphates (of the type Am-0-PO-(OX) 2 ), distarch phosphates (of the type Am-O-PO-(OX)-O-Am) or even tristarch phosphates (of the type Am-0-PO-(0-Am) 2 ) or mixtures thereof (Am meaning starch) may especially be obtained by crosslinking with phosphorus compounds.
  • X especially denotes alkali metals (for example sodium or potassium), alkaline-earth metals (for example calcium or magnesium), ammonium salts, amine salts, for instance those of monoethanolamine, diethanolamine, triethanolamine, 3-amino-1 ,2- propanediol, or ammonium salts derived from basic amino acids such as lysine, arginine, sarcosine, ornithine or citrulline.
  • alkali metals for example sodium or potassium
  • alkaline-earth metals for example calcium or magnesium
  • ammonium salts for instance those of monoethanolamine, diethanolamine, triethanolamine, 3-amino-1 ,2- propanediol, or ammonium salts derived from basic amino acids such as lysine, arginine, sarcosine, ornithine or citrulline.
  • the phosphorus compounds may be, for example, sodium tripolyphosphate, sodium orthophosphate, phosphorus oxychloride or sodium trimetaphosphate.
  • Distarch phosphates or compounds rich in distarch phosphate will preferentially be used, for instance the products sold under the references Prejel VA-70-T AGGL (gelatinized hydroxypropyl cassava distarch phosphate), Prejel TK1 (gelatinized cassava distarch phosphate) and Prejel 200 (gelatinized acetyl cassava distarch phosphate) by the company Avebe, or Structure Zea from National Starch (gelatinized corn distarch phosphate).
  • Amphoteric starches may also be used according to the invention; these amphoteric starches containing one or more anionic groups and one or more cationic groups.
  • the anionic and cationic groups can be bonded to the same reactive site of the starch molecule or to different reactive sites; preferably they are bonded to the same reactive site.
  • the anionic groups may be of carboxylic, phosphate or sulfate type, preferably carboxylic.
  • the cationic groups may be of primary, secondary, tertiary or quaternary amine type.
  • amphoteric starches are selected in particular from the compounds of the formulae:
  • St-O represents a starch molecule
  • R identical or different, represents a hydrogen atom or a methyl radical
  • R' identical or different, represents a hydrogen atom, a methyl radical or a -COOH group
  • n is an integer 2 or 3
  • M denotes a hydrogen atom, an alkali metal or an alkaline-earth metal such as Na, K, Li, NH 4 , a quaternary ammonium or an organic amine, and R" represents a hydrogen atom or an alkyl radical having from 1 to 18 carbon atoms.
  • starches of formula (I) or (II) Use is made in particular of the starches of formula (I) or (II). More particularly use is made of starches modified with 2-chloroethylaminodipropionic acid, i.e., the starches of formula (I) or (II) in which R, R', R" and M represent a hydrogen atom and n is 2.
  • Starchs may be chosen from modified starchs esterified in aqueous medium by a C1 -C6 acyl functional group, an acetyl functional group, a C1 -C6 hydroxyalkyl group such as hydroxyethyl, hydroxypropyl, a carboxyalkyi functional group such as carboxymethyl, an octenylsuccinic functional group.
  • Preferred starchs that can be used in the composition according to the invention are chosen from modified starchs, preferably chosen from potato starch, such as O-carboxymethylated potato starchs.
  • O-carboxymethyl starch denotes a starch that has been modified by substitution, in free hydroxyl groups, of a hydrogen with a carboxymethyl group -CH 2 COOH. It may be present as is, or in the form of a salt, for example an alkali metal salt.
  • O-Carboxylmethyl starches may be prepared, for example, by reacting a starch with monochloroacetic acid, or an alkali metal salt of monochloroacetic acid (for example the sodium salt).
  • an O-carboxymethyl starch in the form of an alkali metal salt, and more preferably in the form of a sodium salt, is used.
  • the O-carboxylmethyl starch is prepared from starch derived from potato.
  • the O-carboxymethyl starch may also be totally or partially crosslinked. Preferably, it is partially crosslinked.
  • the crosslinking of the starch may be performed, for example, by heating the starch, or by reacting it with crosslinking agents such as phosphates or glycerol.
  • the O-carboxymethyl starch is a partially crosslinked sodium salt of O-carboxymethyl potato starch.
  • a partially crosslinked sodium salt of O-carboxymethyl potato starch is sold, for example, under the name Primojel by the company Avebe.
  • Preferred starchs are chosen from crosslinked sodium carboxymethyl potato starch.
  • the modified or non modified starch or starches may be present in an amount ranging from 2 to 20% by weight relative to the total weight of the dyeing composition, more preferably this amount ranges from 2 to 10% by weight relative to the total weight of the composition, and more preferably still from 2 to 6% by weight.
  • Another subject of the invention is a method for dyeing human keratin fibres, in particular the hair, comprising the application, to the keratin fibres, of the composition according to the invention, alone or in the presence of a chemical oxidizing agent, as described above.
  • the method uses a chemical oxidizing agent
  • the latter may be provided by an oxidizing composition.
  • the oxidizing composition is preferably aqueous.
  • composition A The dyeing composition (composition A) and the oxidizing composition (composition B) are preferably mixed in a weight ratio (A)/(B) ranging from 0.2 to 10 and preferably ranging from 0.5 to 2.
  • the dyeing composition according to the invention is mixed with an oxidizing composition comprising an oxidizing agent as described above.
  • the mixture obtained is subsequently applied to the keratin fibres and left on for approximately 3 to 50 minutes, preferably approximately 5 to 30 minutes, then a rinsing and shampooing step may follow, then another rinsing, and finally drying.
  • the dyeing composition and the oxidizing composition described may be applied one after the other, in any order, with or without intermediate rinsing.
  • the keratin fibres may be dried at a temperature ranging from 50 to 80°C or left to dry in the open air.
  • the keratin fibres may be dried by means of a hairdryer, a drying hood or a straightening iron so as to carry out a hair shaping step.
  • Multi-compartment device
  • a subject of the invention is a two-compartment device for dyeing keratin fibres.
  • a first compartment contains the dyeing composition (A) according to the invention and a second compartment contains the oxidizing composition (B) as described above.
  • compositions are prepared (unless otherwise mentioned, the amounts are expressed in g% active material).
  • TMPTA triacrylate
  • composition according to the invention A and the comparative composition B are mixed with one and a half times their weight of 20 volume oxidizing agent (6 g% hydrogen peroxide).
  • Each mixture obtained is applied to locks of hair containing 90% natural grey (NG) hair and locks of hair containing 90% permanent-waved grey (PG) hair, in a proportion of 15 g of mixture per 1 g of hair.
  • NG natural grey
  • PG permanent-waved grey
  • the viscosity is measured by means of a Rheomat RM 180 rheometer (shear rate 200 s "1 , 25°C, measurement at 30 s, spindle 3).
  • the dyeing compositions are easy to apply and to spread on the hair.
  • composition A according to the invention has a higher viscosity than comparative composition B.
  • composition A according to the invention is easy to use, that is to say easy to apply and to spread on the hair.
  • the hair colouring is evaluated using a Minolta 2600D spectrocolorimeter (illuminant D65, angle 10°, specular component included) in the CIEL * a * b * system.
  • L * represents the intensity. Chromaticity is measured by the values a * and b * , a * representing the red/green axis and b * the yellow/blue axis.
  • L * , a * and b * represent the values measured on dyed natural hair and L0 * , aO * and bO * represent the values measured on permanent-waved dyed hair.
  • Composition A NG 20.77 2.88 4.00 0.57 (invention) PG 20.69 2.32 3.94
  • composition A according to the invention leads to a lower ⁇ value than composition B, and therefore the colouring obtained with composition A is less selective than the comparative composition B.
  • compositions are prepared (unless otherwise mentioned, the amounts are expressed in g% active material).
  • composition A' according to the invention
  • Cetylstearylic alcohol (C16/C18 50/50) 1 1 ,5
  • composition is applied to locks of hair containing 90% natural grey (NG) in a proportion of 10 g of mixture per 1 g of hair.
  • NG natural grey
  • the locks are left 30 minutes at room temperature.
  • the lock is placed a first time vertically under tap water at 35°C (2 litres/min) for 5 seconds (1 st cycle) : an evaluation of the rinsabilty is done according to the ranking defined hereafter.
  • the lock is placed a second time vertically under tap water at 35°C (2 litres/min) for 5 seconds and followed by a slight wriging between two finger out the water (2 nd cycle) : an evaluation of the rinsabilty is done again .
  • This last operation is repeated 3 times, with an evaluation of rinsability after each cycle .
  • the scores obtained after each cycle are added in order to obtain a final score.
  • composition A' 0,50 1 ,25 2,25 3,25 3,75 1 1 ,00 (invention)
  • composition B' 0,00 0,50 1 ,00 1 ,50 2,00 5,00 (comparative)
  • composition A' according to the invention presents a much better rinsability compared to composition B' that represents a conventional hair dyeing composition on the market.
  • composition A' allows to decrease the rinsing time and the amount of water used for rinsing, compared to comparative composition.
  • compositions are prepared (unless otherwise mentioned, the amounts are expressed in g% active material).
  • composition A' according to the invention as above described
  • composition according to the invention A' and the comparative composition B' are mixed with one and a half times their weight of oxidizing composition.
  • Each mixture obtained is applied to locks of hair containing 90% natural grey (NG) hair, in a proportion of 10 g of mixture per 1 g of hair. After a leave-on time of 30 minutes at room temperature, the hair is rinsed with water, washed with a standard shampoo and then dried.
  • NG natural grey
  • the hair colouring is evaluated using a Minolta 2600D spectrocolorimeter
  • L * represents the intensity : the lower the value of L * , the more intense the color is.
  • Chromaticity is measured by the values a * and b * , a * representing the red/green axis and b * the yellow/blue axis.
  • composition according to the invention allows to obtain a lower L * value, thus a more intense coloration, than comparative composition.

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Abstract

La présente invention concerne une composition, en particulier pour la coloration des fibres de kératines, comprenant : a) au moins un copolymère comprenant au moins un monomère d'acide 2-acrylamido-2-méthylpropanesulfonique (AMPS ®), au moins un monomère avec un groupe hydrophobe et au moins un monomère éthylénique insaturé qui ne comprend aucun groupe hydrophobe, et b) au moins un précurseur de colorant d'oxydation et/ou un colorant direct.
PCT/EP2015/067705 2014-08-01 2015-07-31 Composition comprenant un copolymère amps® et un précurseur de colorant d'oxydation et/ou un colorant direct Ceased WO2016016441A1 (fr)

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FR1457476A FR3024357B1 (fr) 2014-08-01 2014-08-01 Composition comprenant un copolymere d'amps® et un precurseur de colorant d'oxydation et/ou un colorant direct

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
EP3485943A1 (fr) * 2017-11-17 2019-05-22 Kao Germany GmbH Composition modifiant la couleur des cheveux
CN114286712A (zh) * 2019-06-28 2022-04-05 莱雅公司 用于将角蛋白纤维染色的组合物
WO2024199790A1 (fr) * 2023-03-29 2024-10-03 Henkel Ag & Co. Kgaa Produit de nettoyage des cheveux pour le nettoyage et la décoloration des cheveux colorés

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GB1153196A (en) 1965-07-07 1969-05-29 Schwarzkopf Verwaltung G M B H Method of Dyeing Hair
FR2140205A1 (fr) 1971-06-04 1973-01-12 Oreal
FR2189006A1 (fr) 1972-06-19 1974-01-25 Oreal
DE2359399A1 (de) 1973-11-29 1975-06-12 Henkel & Cie Gmbh Haarfaerbemittel
FR2285851A1 (fr) 1974-09-27 1976-04-23 Oreal Derives de l'amino-3 pyridine et compositions tinctoriales les contenant
US4017460A (en) 1975-12-10 1977-04-12 National Starch And Chemical Corporation Novel starch ethers
DE3843892A1 (de) 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
JPH0563124A (ja) 1991-09-03 1993-03-12 Mitsubishi Electric Corp 混成集積回路装置
DE4133957A1 (de) 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
WO1994008970A1 (fr) 1992-10-16 1994-04-28 Wella Aktiengesellschaft Colorants d'oxydation pour cheveux, renfermant des derives du 4,5-diaminopyrazole, nouveaux derives du 4,5-diaminopyrazole et leur procede de fabrication
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WO1995015144A1 (fr) 1993-11-30 1995-06-08 Ciba-Geigy Ag Colorants cationiques pour fibres keratiniques
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WO1996015765A1 (fr) 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Colorants d'oxydation
FR2733749A1 (fr) 1995-05-05 1996-11-08 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
EP0770375A1 (fr) 1995-10-21 1997-05-02 GOLDWELL GmbH Composition pour la teinture des cheveux
DE19543988A1 (de) 1995-11-25 1997-05-28 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate
FR2818537A1 (fr) 2000-12-22 2002-06-28 Oreal Composition de teinture d'oxydation pour fibres keratiniques a base de polymeres amphiphiles d'au moins un monomere a insaturation ethylenique a groupement sulfonique en comportant une partie hydrophobe
FR2818544A1 (fr) * 2000-12-22 2002-06-28 Oreal Composition de teinture directe pour fibres keratiniques a base de polymeres amphiphiles d'au moins un monomere a insaturation ethylenique a groupement sulfonique et comportant une partie hydrophobe
EP1378544A2 (fr) 2002-07-05 2004-01-07 L'oreal Composés tétraazapentaméthiniques et leur application pour la teinture des fibres kératiniques
FR2848109A1 (fr) * 2002-12-09 2004-06-11 Oreal Compositions oxydantes contenant un melange de polymeres dont au moins un copolymere a base d'acide acrylique ou d'acrylate d'alkyle eventuellement hydroxyle et d'acide 2-acrylamido-2-methylpropane sulfonique
EP1600150A1 (fr) * 2004-05-28 2005-11-30 L'oreal Composition pour le traitement de matières kératiniques comprenant un composé polycarboxylique particulier et un polymère épaississant et procédés la mettant en oeuvre
EP1674073A1 (fr) 2004-12-23 2006-06-28 L'oreal Utilisation de porphyrine ou phtalocyanine particuliere pour la coloration de matieres keratiniques humaines, compositions les comprenant, procede de coloration et composes
WO2010084055A2 (fr) * 2009-01-22 2010-07-29 Unilever Plc Composition colorante pour cheveux
US20140086854A1 (en) * 2011-03-08 2014-03-27 Clariant Finance (Bvi) Limited Polymers Based On Sulfonic Acids, Amides And Special Cross-Linking Agents
JP2013047205A (ja) * 2011-07-28 2013-03-07 Seiwa Kasei Co Ltd 毛髪処理剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3485943A1 (fr) * 2017-11-17 2019-05-22 Kao Germany GmbH Composition modifiant la couleur des cheveux
CN114286712A (zh) * 2019-06-28 2022-04-05 莱雅公司 用于将角蛋白纤维染色的组合物
WO2024199790A1 (fr) * 2023-03-29 2024-10-03 Henkel Ag & Co. Kgaa Produit de nettoyage des cheveux pour le nettoyage et la décoloration des cheveux colorés

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FR3024357A1 (fr) 2016-02-05

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