WO2010133803A1 - Dyeing composition comprising a secondary para-phenylenediamine oxidation base and a specific surfactant - Google Patents

Dyeing composition comprising a secondary para-phenylenediamine oxidation base and a specific surfactant Download PDF

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WO2010133803A1
WO2010133803A1 PCT/FR2010/050964 FR2010050964W WO2010133803A1 WO 2010133803 A1 WO2010133803 A1 WO 2010133803A1 FR 2010050964 W FR2010050964 W FR 2010050964W WO 2010133803 A1 WO2010133803 A1 WO 2010133803A1
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alkyl
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Jean-Baptiste Saunier
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L'oreal
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Priority to FR0953323A priority patent/FR2945732B1/en
Priority to FR0953323 priority
Priority to FR0953329A priority patent/FR2945735B1/en
Priority to FR0953326 priority
Priority to FR0953329 priority
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/411Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair

Abstract

The invention relates to a composition for coloring keratin fibers, comprising, in a suitable dyeing medium: - one or more oxidation bases selected from the compound of formula (I) and the acid addition salts thereof; - one or more surfactants selected from the ones carrying at least one cationic charge, carboxylic ether acids or a salt thereof, and monoglycerol or polyglycerol nonionic surfactants and polyoxyethylene sorbitan esters. The invention also relates to a dyeing method in which said composition is used and in which the aforementioned dyeing composition is applied to the fibers with or without an oxidizing agent. The invention further relates to devices including a plurality of compartments.

Description

DYEING COMPOSITION CONTAINING A BASE OXIDATION PARA- PHENYLENE DIAMINE SECONDARY AND A PARTICULAR SURFACTANT

The invention relates to a dye composition comprising at least one specific secondary para-phenylenediamine oxidation base and at least one particular surfactant. The invention also relates to a process for dyeing keratin fibers, in particular human such as hair, implementing this composition, as well as devices with several compartments suitable. It is known to dye keratinous fibers and in particular human hair, with dye compositions containing oxidation dye precursors, generally called oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds. These oxidation bases are colorless or weakly colored compounds which, combined with oxidizing products, can give rise, by an oxidative coupling process to colored compounds.

It is also known that one can vary the shades obtained with these oxidation bases by combining them with couplers or color modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds. The variety of molecules used in oxidation bases and couplers allows to obtain a rich palette of colors.

The so-called "permanent" coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must have no toxicological drawbacks map, it must allow to obtain shades of the desired intensity and exhibit good resistance to external agents such as light, bad weather, washing, permanent waving, sweating and friction.

The dyes should also allow to cover white hair and, finally be the least selective possible, that is to say, allow to obtain the smallest possible differences in coloration along the same keratin fiber, which is generally differently sensitized (ie damaged) between its tip and its root.

It is already known to use oxidation base of the para-phenylene-type secondary diamine of formula (I) below for coloring keratin fibers, especially hair. In particular, such a basis is disclosed in EP1580184 and EP0055386 documents. This base has disadvantages as to lead to sufficiently intense colors or color and / or too selective. The object of the present invention is to obtain a composition for coloring hair which has improved dyeing properties in terms of intensity or chromaticity and / or selectivity and / or resistance to external agents.

This object is achieved with the present invention which relates to a composition for dyeing keratin fibers 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,

Figure imgf000003_0001
and - one or more surfactants chosen from those bearing at least one cationic charge, of the ether carboxylic acid or a salt thereof, or from nonionic surfactants mono- or polyglycerolated and polyoxyethylenated sorbitan esters.

The invention also relates to a dyeing process using this composition.

It also relates to a multi-compartment device comprising in one of them, the dye composition according to the invention without an oxidizing agent, and in another, a composition comprising one or more oxidizing agents.

According to another variant of the invention, the device comprises a first compartment containing the compound of formula (I) or salt thereof with an acid and optionally one or more oxidation bases of the compound of formula (I) or its salts and optionally one or more couplers; a second compartment containing a composition comprising one or more surfactants as defined above and optionally a third compartment containing a composition comprising one or more oxidizing agents.

The composition of the present invention allows in particular to obtain a dye composition for keratinous fibers which is suitable for oxidation dyeing and in use make it possible to obtain a coloration in varied shades, or intense color, aesthetic, sparingly selective and resistant to the various attacks which hair can suffer such as shampoos, sweat and permanent deformations and light.

It is noteworthy that in what follows, and unless otherwise indicated, the limits of a range of values ​​are included in that range. The compound of formula (I) may be in the form of addition salts chosen in particular from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates. The compound of formula (I) or salts thereof are generally present each in an amount of 0.001 to 10% by weight relative to the total weight of the dyeing composition, preferably between 0.005 and 6% by weight.

The dye composition of the invention may optionally comprise one or more additional oxidation bases conventionally used for dyeing keratinous fibers, different from the compound of formula (I) or salt thereof.

For example, these additional oxidation bases are chosen from para-phenylenediamines different from the compound of formula (I) and its addition salts, bis- alkylenediamines, para-aminophenols, bis-para aminophenols, ortho- aminophenols, heterocyclic bases. Among the para-phenylenediamines, mention may be made by way of example, para-phenylenediamine, para-toluenediamine, p-phenylenediamine 2-chloro, 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-methyl aniline, N, N-bis- (β-hydroxyethyl) para-phenylenediamine, 4-N, N-bis- (β-hydroxyethyl) amino-2- methyl aniline, 4-N, N-bis- (β-hydroxyethyl) amino 2-chloro aniline, 2-β-hydroxyethyl para-phenylenediamine, 2-fluoro para-phenylenediamine, 2-isopropyl para-phenylenediamine, N- (β-hydroxypropyl) para-phenylenediamine, 2-hydroxymethyl para-phenylenediamine, N, N-dimethyl 3-methyl para-phenylenediamine, N, N- (ethyl, β- hydroxyethyl) para-phenylenediamine, N- (β, γ-dihydroxypropyl) para-phenylenediamine, N- (4'-aminophenyl) para-phenylenediamine, N-phenyl para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetylaminoethyloxy para-phenylenediamine, N- (β-methoxyethyl) para-phenylenediamine, 4- aminophénylpyrrolidine, 2-thienyl-para-phenylenediamine, 2-β-hydroxyethylamino 5-amino toluene, 3-hydroxy-1- (4 ' aminophenyl) pyrrolidine, and their addition salts with an acid.

Among the para-phenylenediamines mentioned above, para-phenylenediamine, para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2-β-hydroxyethyl para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl para-phenylenediamine, 2,6-diethyl para-phenylenediamine, 2,3-dimethyl para-phenylenediamine, N, N-bis- (β-hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, 2-β-acetylaminoethyloxy-para-phenylenediamine, and their addition salts with an acid are particularly preferred.

Among the bisphenylalkylenediamines mention may be made for example, N, N'-bis (β- hydroxyethyl) -N, N'-bis- (4'-aminophenyl) 1, 3-diamino propanol, N , N'-bis- (β-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- ( β-hydroxyethyl) -N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methyl-aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) -N, N ' -bis (4'-amino-3'-methylphenyl) ethylenediamine, 1, 8-bis (2,5-diamino-phenoxy) -3,6-dioxaoctane, and their addition salts with an acid. Among the para-aminophenols that may be mentioned by way of example, para-aminophenol, 4-amino 3-methyl phenol, 4-amino-3-fluorophenol, 4-amino 3-hydroxymethyl phenol, 4- amino-2-methylphenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- (β-hydroxyethyl aminomethyl) phenol, 4- amino 2-fluoro phenol, 1-hydroxy-4-methylamino-benzene, 2-2'- methylenebis-4-aminophenol and their addition salts with an acid.

Among the ortho-aminophenols that may be mentioned by way of example, 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and their addition salts with an acid.

Among the heterocyclic bases include for example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.

Among the pyridine derivatives, there may be mentioned 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-amino pyridine, 2,3-diamino-6-methoxypyridine, 2- (β- methoxyethyl) amino 3-amino-6-methoxypyridine, 3,4-diaminopyridine, and their addition salts with an acid.

Among the pyrimidine derivatives include the compounds described for example in DE 2359399 patents; JP 88-169571; JP 05-63124; EP 0770375 or patent application WO 96/15765 such as 2,4,5, 6-tetra-aminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2 , 4-dihydroxy 5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and the pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2,750,048 and among which there may be mentioned pyrazolo [1, 5-a] pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo [1, 5-a] -pyrimidine-3,7-diamine; pyrazolo [1, 5-a] pyrimidine-3,5-diamine; 2,7-dimethyl pyrazolo [1, 5-a] - pyrimidine-3,5-diamine; 3-aminopyrazolo [1, 5-a] -pyrimidin-7-ol; 3-amino pyrazolo [1, 5- a] -pyrimidin-5-ol; 2- (3-aminopyrazolo [1, 5-a] -pyrimidin-7-ylamino) -ethanol, 2- (7-amino pyrazolo [1, 5-a] -pyrimidin-3-ylamino) - ethanol, 2 - [(3-amino-pyrazolo [1, 5-a] pyrimidin-7-yl) - (2-hydroxy-ethyl) -amino] -ethanol, 2 - [(7-amino-pyrazolo [ 1, 5-a] pyrimidin-3-yl) - (2-hydroxyethyl) -amino] -ethanol, 5,6-dimethyl pyrazolo [1, 5-a] pyrimidine-3,7-diamine, 2,6-dimethyl pyrazolo [1, 5-a] pyrimidine-3,7-diamine, 2, 5, N 7, N 7-tetramethyl pyrazolo- [1, 5-a] pyrimidine-3, 7-diamine, 3-amino-5-methyl-7-imidazolylpropylaminopyrazolo pyrazolo [1, 5- a] pyrimidine and their addition salts with an acid and their tautomeric forms, when a tautomeric equilibrium exists. Among the pyrazole derivatives include the compounds described in patents DE

3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2,733,749 and DE 195 43 988 such as 4,5-diamino-1-methylpyrazole, 4,5-diamino-1- (β- hydroxyethyl) pyrazole, 3,4-diamino pyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4,5-diamino-1, 3-dimethyl pyrazole, 4,5-diamino 3-methyl 1-phenyl pyrazole, 4,5 diamino 1-methyl 3-phenyl pyrazole, 4-amino-1, 3-dimethyl 5-hydrazino pyrazole, 1-benzyl 4,5-diamino 3-methyl pyrazole, 4,5-diamino-3-tert-butyl 1-methyl pyrazole, 4,5-diamino-1-tert-butyl 3-methyl pyrazole, 4,5-diamino-i- (β-hydroxyethyl) 3-methyl pyrazole, 4,5-diamino 1-ethyl 3-methyl pyrazole, 4,5-diamino 1-ethyl 3- (4'-methoxyphenyl) pyrazole, 4,5-diamino 1-ethyl 3-hydroxymethyl pyrazole, 4, 5-diamino 3-hydroxymethyl 1-methyl pyrazole, 4,5-diamino 3-hydroxymethyl 1-isopropyl pyrazole, 4,5-diamino 3-methyl 1-isopropyl pyrazole, 4-amino 5- (2'-aminoethyl ) amino 1, 3-dimethyl pyrazole, 3,4,5-triamino pyrazole, 1-methyl 3,4,5-triamino pyrazole, 3,5-diamino 1-methyl 4-methylamino pyrazole, 3,5-diamino 4- (β-hydroxyethyl) amino-1-methylpyrazole, and their addition salts with an acid. We can also mention the diaminopyrazolinones described in the patent application

FR2886137 and in particular 2,3-diamino-6,7-dihydro-1H, 5H-pyrazol-1-one and its salts.

In general, the addition salts of the oxidation bases and couplers used in the context of the invention are chosen in particular from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates, and the addition salts with a base, such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.

When the composition comprises one or more additional oxidation bases, one (s) -ci represent (s) more preferably from 0.0005 to 12% by weight relative to the total weight of the dyeing composition, preferably from 0.005 to 8 % in weight.

The dye composition according to the invention can also optionally comprise one or more couplers conventionally used for dyeing keratinous fibers. Among these couplers, mention may be made of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene couplers, heterocyclic couplers and their addition salts.

Examples of coupler include 2-methyl-5-aminophenol, 5-N- (β- hydroxyethyl) amino-2-methylphenol, 6-chloro-2-methyl-5-aminophenol, 3 -amino phenol, 2,4-dichloro-3-aminophenol, 5-amino-4-chloro-o-cresol, 1, 3-dihydroxybenzene, 1, 3-dihydroxy-2-methylbenzene, 4- chloro 1, 3-dihydroxybenzene, 2,4-diamino i- (β-hydroxyethyloxy) benzene, 2-amino 4- (β-hydroxyethylamino) 1-methoxybenzene, 1, 3-diaminobenzene, 1, 3 -bis- (2,4-diaminophenoxy) propane, 3-ureido aniline, 3-ureido-1-dimethylamino benzene, sesamol, 1-β-hydroxyethylamino-3,4-methylenedioxybenzene, the α-naphthol, 2 methyl-1-naphthol, 1, 5-dihydroxy naphthalene, 2,7-Naphthalenediol, 1-acetoxy-2-Methylnaphthalene, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy N-methyl indole, 2-amino-3-hydroxypyridine, 6-hydroxy-benzomorpholine 3,5-diamino-2,6-dimethoxypyridine, 2,6-dihydroxy-3-4- dimethyl pyridine, the e 3-amino-2-methylamino-6-methoxypyridine, 1-N- (β- hydroxyethyl) amino-3,4-methylenedioxybenzene, 2,6-bis (β-hydroxyethylamino) toluene, 3-methyl -1-phenyl-5-pyrazolone and the addition salts thereof with an acid.

In the composition of the present invention, the coupler, when present, generally represent a quantity of between 0.001 and 10% by weight relative to the total weight of the dyeing composition, preferably between 0.005 and 6% by weight. The dye composition according to the invention may further contain one or more direct dyes which may be chosen from nitro dyes of the benzene series, azo direct dyes, methine direct dyes. These direct dyes may be of nonionic, anionic or cationic in nature.

In the composition of the present invention, the direct dye, if present, generally represent a quantity of between 0.001 and 20% by weight relative to the total weight of the dyeing composition, preferably between 0.01 and 10% by weight.

As indicated above, the dye composition according to the invention may comprise one or more surfactants containing at least one cationic charge. More particularly, these surfactants are selected from compounds comprising at least one cationic charge and at least one alkyl or alkenyl chain, C 12 -C 30 optionally bearing at least one ester or amide function.

And surfactants used in the composition according to the invention may comprise a cationic charge and no anionic charge, or include both a cationic and an anionic charge. In the latter case, the surfactants are amphoteric or zwitterionic species.

Examples of suitable cationic surfactants there may be mentioned: (i) quaternary ammonium salts of formula (II):

Figure imgf000007_0001
in which

X 'is an anion chosen for example from the group of halides (chloride, bromide or iodide) or alkyl (C 2 -C 6), more particularly methyl sulphate, phosphates, alkyl or alkylaryl sulphonates, anions derived acid organic such as acetate or lactate, and

(1) the radicals R to R 3, identical or different, represent an aliphatic radical, linear or branched -C 4, or an aryl or alkylaryl radical, the alkyl radical optionally bearing an alkoxy group, alkylamide, R 4 denotes an alkyl radical, linear or branched Ci -C 3 O 6, preferably C 4 - C 22; or

(2) Ri and R 2, identical or different, represent an aliphatic radical, linear or branched -C 4, or a radical as aryl and alkylaryl, the alkyl radical optionally bearing an alkoxy group, alkylamide or hydroxyalkyl , -C 4;

R 3 and R 4, identical or different, denote an alkyl or alkenyl radical, linear or branched -C 2 -C 30, said radical optionally comprising at least one ester or amide function;

Advantageously, the cationic surfactant according to option (1) above is a salt (e.g. chloride) of behenyl trimethyl ammonium and depending on the option (2) a salt (e.g. chloride) of stearamidopropyl dimethyl (myristyl acetate) ammonium chloride sold under the name "Ceraphyl 70" by the company Van Dyk.

(Ii) quaternary ammonium salts of imidazolinium of formula (III):

Figure imgf000008_0001
in which

R 5 represents an alkenyl or alkyl radical 2 -C 30,

R 6 represents a hydrogen atom, an alkyl radical or a -C 4 alkenyl or alkyl radical 2 -C 30,

R 7 represents an alkyl radical -C 4, R 8 represents a hydrogen atom, an alkyl radical -C 4,

X is an anion X selected from the group including halides, phosphates, acetates, lactates, alkylsulphates, alkylsulphonates or alkylarylsulphonates.

Preferably, R 5 and R 6 denote a mixture of alkenyl or alkyl radicals comprising from 12 to 21 carbon atoms for example derivatives of fatty acids of tallow, R 7 denotes methyl, R 3 denotes hydrogen. Such a product is e.g. Quaternium- 27 (CTFA 1997) or Quaternium-83 (CTFA 1997) sold under the names "Rewoquat" W75, W90, W75PG, W75HPG by Witco; (Iii) the quaternary diammonium salts of formula (IV):

2X

Figure imgf000008_0002
(IV) wherein

R 9 denotes an alkyl radical or alkenyl, C12-C30,

R 10, Rn, R 12, R 1 3 and R 14, identical or different are selected from hydrogen or an alkyl radical in C 4 and X is an anion chosen in particular from the group of halides, acetates, phosphates, nitrates and methyl.

Such quaternary diammonium salts comprise propane tallow diammonium dichloride.

(Iv) quaternary ammonium salts containing at least one ester function of formula (V):

(G r H 2r O) z O

R 17 - C - (OC n H 2n) y N - (C H 2p O) χ - R 16 X

RI5 (V) wherein:

• R 5 is selected from alkyl, -C 6 hydroxyalkyl, -C 6 dihydroxyalkyl, C 2 -C 6; • R 1 6 is selected from the radical R 19 -CO-, an alkyl radical or R 2 o alkenyl

C 1 -C 22 linear or branched, a hydrogen atom,

• R 18 is selected from the radical R 21 -CO-, R 22 alkyl or alkenyl, C 1 -C 6 linear or branched, a hydrogen atom,

• R 17, R 19 and R 21, identical or different, are chosen from alkyl or alkenyl, C 12 -C 22, linear or branched;

• n, p and r, which are identical or different, are integers ranging from 2 to 6;

• there is an integer from 1 to 10;

• x and z, which are identical or different, are integers ranging from 0 to 10;

• X is a simple or complex anion, organic or inorganic. more particularly the ammonium salts of formula (V) wherein:

• R 15 denotes a methyl or ethyl radical,

• x and y are equal to 1;

• z is equal to 0 or 1;

• n, p and r are equal to 2; R 16 is selected from the radical R 19 -CO-, methyl, ethyl, alkyl or alkenyl, C 14 -C 22 - the hydrogen atom;

• R 17, R 19 and R 21, identical or different, are chosen from alkyl or alkenyl, C 7 -C 21 linear or branched, saturated or unsaturated;

• R 18 is selected from the radical R 21 -CO-, the hydrogen atom. Such compounds are for example marketed under the names

DEHYQUART by Cognis, Stepanquat® by the company Stepan, Noxamium by CECA Rewoquat WE 18 by Rewo-Witco. According to a particularly advantageous embodiment of the invention, the composition comprises, as surfactant (s) cation (s), one or more cationic surfactants of formula (II), and preferably one or more cationic surfactants of formula (II) corresponding to the option (1). Examples of surfactant (s) amphoteric (s) or zwitterionic surfactant (s) include the compounds derived from secondary or tertiary aliphatic amines in which the aliphatic group is a linear or branched chain containing 8 to 22 , and preferably 10 to 24, carbon atoms and containing at least one anionic group such as, for example, a carboxylate, sulfonate, sulfate, phosphate or phosphonate. There may be mentioned in particular (C 8 _ 2 o) alkylbetaines, sulphobetaines, (C 8

2 o) amido (C 6-8) alkyl betaines or (C 8 _ 2 o) amido (C 6 _ 8) sulphobetaines.

Among the amine derivatives include the products sold under the name Miranol ®, as described in US patents 2,528,378 and US 2,781,354 and classified in the CTFA dictionary, 3rd edition, 1982, under the names names Amphocarboxyglycinate-glycinate and respective structures of Amphocarboxypropionate (a) and (b):

R a -CONHCH 2 CH 2 -N (R b) (R c) (CH 2 COO ") (a) wherein:

R 3 represents an alkyl group derived from an acid R 3 -COOH present in hydrolysed coconut oil or a heptyl, nonyl or undecyl radical, R b represents a beta-hydroxyethyl group, and

R c represents a carboxymethyl group; and

R a '-CONHCH 2 CH 2 -N (B) (B') (b) in which: B represents -CH 2 CH 2 OX ',

B 'is - (CH 2) z -Y \ with z = 1 or 2,

X 'represents the -CH 2 CH 2 -COOH group or a hydrogen atom, Y' represents -COOH or the -CH 2 -CHOH-SO 3 H,

R 3 'represents an alkyl group of an acid R a' -COOH present in coconut oil or in hydrolysed linseed oil, alkyl, in particular Ci 7 and its iso form, a group -C 7 unsaturated.

These compounds are classified in the CTFA dictionary, 5th edition, 1993, under the names disodium cocoamphodiacetate, disodium lauroamphodiacetate caprylamphodiacetate disodium capryloamphodiacetate, disodium cocoamphodipropionate, disodium lauroamphodipropionate, disodium caprylamphodipropionate disodium capryloamphodipropionate, disodium lauroamphodipropionique acid, cocoamphodipropionic acid. Examples include the cocoamphodiacetate sold by Rhodia under the trade name Miranol ® C2M concentrate.

Preferably, the surfactant carrying at least one cationic charge are chosen from behenyltrimethylammonium chloride, methosulfate behenyl trimethyl ammonium methosulfate methyl alkyl imidazolinium alkylamidoethyl (QUATERNIUM-

87) ammonium chloride, cetyl trimethyl ammonium, and a mixture of cocamido propyl betaine and cetyl betaine (MIRASPEC TAM 40 / M - Rhodia), or mixtures thereof.

Preferably the surfactant carrying at least one cationic charge of the invention are cationic. As indicated above, the dye composition according to the invention may also comprise one or more ether carboxylic acid or a salt thereof.

Ether carboxylic acids or their salts are selected from alkyl- or alkenyl- acids (C 6 -C 24) ether carboxylic acids and their salts, polyoxyalkylenated (C 6 - C 24) aryl ether carboxylic acids and salts thereof, polyoxyalkylenated (C 6 -C 24) alkylamido ether carboxylic acids and salts thereof, especially those having from 2 to 50 alkylene oxide, in particular ethylene, such as the compounds provided by the company KAO under the names Akypo.

One can also use mixtures of these surfactants.

The salts are in particular chosen from alkaline salts, especially sodium, ammonium salts, amine salts, amino alcohol salts such as triethanolamine or monoethanolamine, and magnesium salts.

The surfactants of the polyoxyalkylenated ether carboxylic acid type are those having Formula (N '): R 1 - (OC 2 H 4) ^ - OCH 2 COOA in which:

Ri represents a radical or a mixture of alkyl or alkenyl linear or branched C 8 -C 22, an alkyl (C 8 -C 9) alkylphenyl, a radical R 2 CONH-CH 2 -CH 2 - with R 2 denoting a linear alkyl or branched alkenyl or Cn-C 2 - I, and n is an integer or decimal number (average value) which may vary from 2 to 24 and preferably 2 to 10,

A denotes H, ammonium, Na, K, Li, Mg or a monoethanolamine or triethanolamine rest. One can also use mixtures of compounds of formula (N '), in particular mixtures in which the R groups | are different.

More particularly, the radical Ri is an alkyl group comprising from 8 to 18 carbon atoms and the aryl group denotes preferably phenyl.

Polyoxyalkylenated ether carboxylic acids or their salts are preferably chosen from those of formula (N ') in which R denotes a radical or a mixture of alkyl radicals (Ci2-Ci 4), cocoyl, oleyl; a nonylphenyl or octylphenyl radical, A denotes a hydrogen or sodium atom, and n varies from 2 to 20 and preferably 2 to 10.

More preferably used are compounds of formula (N ') in which R denotes an alkyl radical (C 2 -C 4), A denotes a hydrogen or sodium atom, and n is from 2 to 10.

Among the commercial products can be used preferably the products sold by the company Chem Y under the names:

AKYPO® NP 70 (R = nonylphenyl, n = 7, A = H) AKYPO® NP 40 (R = nonylphenyl, n = 4, A = H) AKYPO® OP 40 (R = octylphenyl, n = 4, A = H )

AKYPO® OP 80 (R = octylphenyl, n = 8, A = H) AKYPO® OP 190 (R = octylphenyl, n = 19, A = H) AKYPO® RLM 38 (R = alkyl (C 12 -C 14), n = 3.8, A = H) AKYPO® RLM 38 NV (R = alkyl (C 12 -C 14), n = 4, A = Na) AKYPO® RLM 45 (R = alkyl (C 12 -C 14) , n = 4.5, A = H)

AKYPO® RLM 45 NV (R = alkyl (C 12 -C 14), n = 4.5, A = Na) AKYPO® RLM 100 (R = alkyl (C 12 -C 14), n = 10, A = H ) AKYPO® RLM 100 NV (R = alkyl (C 12 -C 14), n = 10, A = Na) AKYPO® RLM 130 (R = alkyl (C 12 -C 14), n = 13, A = H) AKYPO® RLM 160 NV (R = alkyl (C 12 -C 14), n = 16, A = Na) or by Sandoz under the names: Sandopan DTC-Acid (R = (C 1 3), n = 6, A = H) SANDOPAN DTC (R = (C 1 3), n = 6, A = Na) Sandopan LS 24 (R = alkyl (C 12 -C 14), n = 12, A = Na) Sandopan JA 36 (R = alkyl (C- | 3), n = 18, A = H), and more particularly the products sold under the following names: AKYPO® RLM 45 AKYPO® RLM 100 AKYPO® RLM 38. the composition according to the invention may also comprise one or more nonionic surfactants selected from nonionic surfactants mono- or polyglycerolated and polyoxyethylenated sorbitan esters.

In particular, nonionic surfactants mono- or polyglycerolated are selected from the group consisting of mono- fatty alcohols or polyglycerolated. By fatty alcohol, more particularly denotes aliphatic alcohols having a saturated alkyl chain or an alkenyl chain comprising at least one introduction (-C = C-) and preferably 1 to 3 unsaturated bonds, these chains being linear or branched and comprising 8 to 40 carbon atoms, more preferably from 10 to 30 carbon atoms. The alkyl or alkenyl chain may optionally be substituted with an additional hydroxy group. More specifically, the fatty alcohols are preferably of formula R-OH, with R designating a linear alkyl or alkenyl radical or branched, optionally substituted by one hydroxy group and having from 8 to 40 carbon atoms, more preferably from 10 to 30 carbon carbon.

According to an advantageous embodiment of the invention, the surfactant not correspond to formula (IM ') below:

Figure imgf000013_0001
wherein: R represents an alkyl or alkenyl radical having 1 to 3 unsaturated bonds (-C = C-), linear or branched, containing from 8 to 40 carbon atoms and preferably 10 to 30 carbon atoms; m is a number (average value) ranging from 1 to 30 preferably from 1 to 15 and even more preferably from 1 5 to 10. Preferably, the fatty alcohol mono- or polyglycerolated of formula (IM ') are selected from fatty alcohols -C 2 -C 24 comprising from 1 to 10 moles of glycerol, more particularly from oleyl alcohol containing 2 mol of glycerol, oleyl 4 mol of glycerol alcohol, lauryl alcohol 1 5 mol of glycerol.

The one or more polyoxyethylene sorbitan esters of the invention are polyoxyethylene esters of fatty alcohols and sorbitol anhydride. Preferably, these esters are monoesters. These esters in particular include a number of moles of ethylene oxide less than or equal to 30, preferably between 2 and 30, more preferably between 2 and 10, preferably between 2 and 6. Preferably they have the following structure (IV)

Figure imgf000013_0002
w, x, y, z denoting respectively a number between 0 and 20 and such that w + x + y + z is less than or equal to 30, preferably between 2 and 30, more preferably between 2 and 10, preferably between 2 and 6 (mean values). R denotes an alkyl or alkenyl radical, linear or branched comprising from 8 to 30 carbon atoms and optionally substituted by hydroxy. According to one embodiment even more preferred of the invention, the one or more polyoxyethylene sorbitan esters are such that the number of moles of ethylene oxide ranges from 2 to 5 (inclusive).

Examples of polyoxyethylene sorbitan esters of the invention, there may be mentioned sorbitan monolaurate oxyethylenated with 4 EO or polysorbate 21, sorbitan monostearate oxyethylenated with 4 EO or polysorbate 61, mono-oleate sorbitan oxyethylenated with 5 EO or polysorbate 81. These sorbitan esters are for example marketed by Uniqema under the name Tween 21, Tween 61 or Tween 81.

The composition according to the invention has a content of surfactant (s) as described above ranging from 0.01 to 20% by weight based on the weight of the dye composition, and preferably from 0.05 to 10% by weight.

It should be noted that in the particular case of surfactants of the acid type (s) ether carboxylic acid (s), their content may range from 0.01 to 30% by weight based on the weight of the dye composition, and preferably from 0.1 to 15% by weight. The medium suitable for dyeing, also called dye carrier generally comprises water or a mixture of water and one or more solvents such as lower alkanols -C 4, such as ethanol and isopropanol, polyols such as propylene glycol, dipropylene glycol or glycerol, and polyol ethers such as dipropylene glycol monomethyl ether. The solvent or solvents are generally present in proportions which may be between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 3 and 30% by weight.

The dye composition according to the invention may also contain various adjuvants used conventionally in compositions for dyeing the hair, such as anionic, nonionic, or mixtures thereof, anionic, cationic, nonionic, amphoteric, zwitterionic or mixtures thereof, thickening agents, inorganic or organic, and associative thickeners anionic, cationic, nonionic and amphoteric surfactants, antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, conditioning agents such as for example, volatile or nonvolatile silicones, modified or unmodified, film formers, ceramides, preservatives, opacifying agents.

The above adjuvants are generally present in an amount for each of them of between 0.01 and 20% by weight based on the weight of the composition. Of course, those skilled in the art will take care to select this or these optional additional compounds such that the advantageous properties intrinsically attached to the oxidation dyeing composition in accordance with the invention are not, or not substantially, impaired by the envisaged addition. The pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between approximately 1 to 1 5. It can be adjusted to the desired value using acidifying or basifying agents usually used for dyeing keratinous fibers or alternatively using conventional buffer systems. Among the acidifying agents, mention may be made, by way of example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, and sulphonic acids.

Among the basifying agents, mention may, for example, ammonia, alkali metal carbonates, alkali metal silicates and metasilicates, alkanolamines such as mono-, di- and triethanolamine and also derivatives thereof, sodium hydroxide, potassium or magnesium, alkali metal salts of carboxylate and pyrrolidine compounds of formula (VI) below: a X

NWN

Rc Rd (VI) in which W is a propylene residue optionally substituted with a hydroxyl group or an alkyl radical -C 4; R 3, R b, R c and R d, identical or different, represent a hydrogen atom, an alkyl radical or C 4 -C 4 hydroxyalkyl. The composition according to the invention may comprise one or more oxidizing agents. The oxidizing agents conventionally used for the oxidation dyeing of keratin fibers are for example hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, peracids and oxidase enzymes among which may be mentioned peroxidases, oxidoreductases with 2 electrons such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred. The dye composition according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form appropriate for carrying out dyeing of keratinous fibers, and especially human hair. It may result from mixing at the time of the use of several compositions. In a first particular variant it results from the mixing of at least two compositions, one comprising one or more oxidation bases chosen from the compounds of formula (I) or their addition salts with an acid, optionally one or more additional oxidation base different from the compound of formula (I) or salt thereof, and optionally one or more couplers, a second composition comprising the surfactant as previously described and optionally a third composition comprising one or more oxidizing agents such as described above in a second particular variant it results from the mixing of two compositions, one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, or surfactants such as described above, optionally one or more additional oxidation base different from the compound of formula (I) or salt thereof, and optionally one or more couplers, another composition comprising one or more oxidizing agents as described above.

The composition of the invention is therefore applied to the hair for coloring keratin fibers, either as such or in the presence of one or more oxidizing agents, for coloring keratin fibers.

The method of the present invention is a method comprising applying to the fibers the composition according to the present invention as defined above, either alone or in the presence of one or more oxidizing agents.

Color can be revealed at acidic, neutral or alkaline Moreover, the oxidizing agents, if present, can be added to the composition of the present disclosure at the time of use or alternatively may be put in work from an oxidizing composition (s) containing, applied simultaneously or sequentially to the composition of the invention.

In one embodiment of particular and preferred embodiment of the invention, the composition of the present invention free of agent (s) oxidant (s) is mixed, preferably at the time of use, with a composition comprising in a medium is suitable for dyeing, one or more oxidizing agents. The mixture obtained is then applied to the keratin fibers.

The oxidizing agents are those indicated above. Whether with or without oxidizing agents, the pause time of the composition or compositions ranges from 3 to 50 minutes approximately, preferably 5 to about 30 minutes.

The temperature during application is typically between room temperature (15-25 ° C) and 80 0 C, preferably between room temperature and 60 0 C.

At the end of this dwell time, the keratin fibers are rinsed with water, optionally washed with shampoo, rinsed with water again and then dried.

The oxidizing composition may also contain various adjuvants used conventionally in compositions for dyeing the hair and as defined above.

The pH of the oxidizing composition containing the oxidizing agent is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratinous fibers preferably varies between 3 and 12 approximately, and even more preferably between 5 and 1 1. It can be adjusted to the desired value using acidifying or basifying agents usually used for dyeing keratin fibers and as defined above. Composition ready for use with or without oxidizing agent, which is finally applied to the keratin fibers may be in various forms, such as in the form of liquids, creams or gels or in any other form appropriate for carrying a dyeing keratinous fibers, and especially human hair. The invention also relates to a multi-compartment device or "kit" in which a first compartment contains the dye composition of the present invention defined above free of oxidizing agent and a second compartment contains a composition comprising one or one oxidizing agent.

A second device consists of 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 different additional oxidation bases compound of formula (I) or salt thereof and optionally one or more couplers and a second compartment containing a composition comprising the surfactant as described above. A third device may include the two compartments of the second device plus a third compartment containing a composition comprising one or more oxidizing agents.

These devices can be equipped with a means for applying to the hair the desired product, such as the devices described in patent FR-2 586 913. The examples which follow serve to illustrate the invention without being limiting in nature .

example 1

We are re com osition the following uantities ex rhymed in ram:

Figure imgf000017_0001

MA: expressed as active material Application Mode

The composition was diluted extemporaneously with 1, 5 times its weight of hydrogen peroxide at 20 volumes.

The mixture was applied to natural gray hair containing 90% white to 10 g per 1 g of hair for 30 minutes.

The hair was then rinsed, washed with a standard shampoo and dried.

Results

The ca Illaire coloration was evaluated visually.

Figure imgf000018_0001

example 2

the following composition was prepared (amounts expressed in grams unless otherwise indicated:

Figure imgf000018_0002

MA: expressed as active material Application Mode

The composition was diluted extemporaneously with 1, 5 times its weight of hydrogen peroxide at 20 volumes.

The mixture was applied to natural gray hair containing 90% white at 10 g per 1 g of hair for 30 minutes at room temperature.

The hair was then rinsed, washed with a standard shampoo and dried.

Results

The ca Illaire coloration was evaluated visually.

Figure imgf000019_0001

example 3

the following composition was prepared (amounts expressed in grams unless otherwise indicated:

Figure imgf000019_0002
MA: expressed as active ingredient

Application method

The composition was diluted extemporaneously with 1, 5 times its weight of 25 volume hydrogen peroxide and having a pH of 3.

The mixture thus produced was applied to natural gray hair containing 90% white hairs, at a rate of 10 g per 1 g of hair for 30 minutes.

The hair was then rinsed, washed with a standard shampoo and dried.

Results

The hair coloration was evaluated visually.

Pitch Reflection

Composition 1 Light Golden Brown

example 4

the following composition was prepared (amounts expressed in grams unless otherwise indicated:

Figure imgf000020_0001
Application method

The composition was diluted extemporaneously with 1, 5 times its weight of hydrogen peroxide at 20 volumes and whose pH is 3.

The mixture thus produced was applied to natural gray hair containing 90% white hairs, at a rate of 10 g per 1 g of hair for 30 minutes.

The hair was then rinsed, washed with a standard shampoo and dried.

Result

The ca Illaire coloration was evaluated visually.

Figure imgf000021_0001

Claims

1. Composition of coloring keratin fibers comprising, in a medium appropriate for dyeing keratinous fibers: - one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid,
Figure imgf000022_0001
and
- one or more surfactants chosen from those bearing at least one cationic charge, of the ether carboxylic acid or a salt thereof, or from nonionic surfactants mono- or polyglycerolated and polyoxyethylenated sorbitan esters.
2. Composition according to the preceding claim, characterized in that the content of compound of formula (I) is between 0.001 to 10% by weight relative to the total weight of the dyeing composition.
3. Composition according to any one of the preceding claims, characterized in that the surfactant carrying at least one cationic charge are selected from: (i) quaternary ammonium salts of formula (II):
Figure imgf000022_0002
in which
X 'is an anion chosen for example from the group of halides (chloride, bromide or iodide) or alkyl (C 2 -C 6), more particularly methyl sulphate, phosphates, alkyl or alkylaryl sulphonates, anions derived acid organic such as acetate or lactate, and
(1) the radicals R to R 3, identical or different, represent an aliphatic radical, linear or branched -C 4, or an aryl or alkylaryl radical, the alkyl radical optionally bearing an alkoxy group, alkylamide, R 4 denotes an alkyl radical, linear or branched Ci 6 -C 30, preferably C 4 -
(2) Ri and R 2, identical or different, represent an aliphatic radical, linear or branched -C 4, or a radical as aryl and alkylaryl, the alkyl radical optionally bearing an alkoxy group, alkylamide or hydroxyalkyl , -C 4;
R 3 and R 4, identical or different, denote an alkyl or alkenyl radical, linear or branched C 12 -C 30, said radical optionally comprising at least one ester or amide function; (Ii) quaternary ammonium salts of imidazolinium of formula (III):
Figure imgf000023_0001
in which
R 5 represents an alkenyl or alkyl radical C12-C30,
R 6 represents a hydrogen atom, an alkyl radical or a -C 4 alkenyl or alkyl radical C12-C30,
R 7 represents an alkyl radical -C 4, R 8 represents a hydrogen atom, an alkyl radical -C 4,
X is an anion X selected from the group including halides, phosphates, acetates, lactates, alkylsulphates, alkylsulphonates or alkylarylsulphonates. (Iii) the quaternary diammonium salts of formula (IV):
Figure imgf000023_0002
in which
R 9 denotes an alkyl radical or alkenyl, C12-C30,
R 10, Rn, R 2, R 1 3 and R 14, identical or different are selected from hydrogen or an alkyl radical -C 4, and
X is an anion chosen in particular from the group of halides, acetates, phosphates, nitrates and methyl sulfates;
(Iv) quaternary ammonium salts containing at least one ester function of formula (V):
(C n H 2n O) z
R 17 - C - (OC n H 2n) y N - (C p H 2p O) x - R 16
R '(V) wherein:
• R 5 is selected from alkyl, dC 6 hydroxyalkyl dC 6 dihydroxyalkyl, C 2 -C 6;
• R 6 is selected from the radical R 19 -CO-, a radical R 2 o alkyl or alkenyl, linear Ci-C 22 or branched, a hydrogen atom, • Ris is selected from the radical R 21 -CO-, R 22 alkyl or alkenyl radical -C 6 linear or branched, a hydrogen atom,
• R 17, R 19 and R 21, identical or different, are chosen from alkyl or alkenyl, C 12 -C 22, linear or branched; • n, p and r, which are identical or different, are integers ranging from 2 to 6;
• there is an integer from 1 to 10;
• x and z, which are identical or different, are integers ranging from 0 to 10;
• X is a simple or complex anion, organic or inorganic.
4. Composition according to the preceding claim, characterized in that the surfactant carrying at least one cationic charge are selected from cationic surfactants of formula (II), and preferably one or more cationic surfactants of formula (II) corresponding to option (1).
5. Composition according to the preceding claim, characterized in that the surfactant carrying at least one cationic charge are chosen from amphoteric or zwitterionic surfactants include: aliphatic secondary or tertiary amino derivatives, in which the aliphatic group is a linear or branched chain containing 8 to 22 carbon atoms and comprising at least one anionic group such as, for example, a carboxylate, sulfonate, sulfate, phosphate or phosphonate, - alkyl betaines, sulphobetaines, alkylamidoalkyl (C 6 -C 8) betaines, alkylamidoalkyl (C 6 -C 8) sulphobetaines.
6. Composition according to any one of the preceding claims, characterized in that the or ether carboxylic acids are chosen from alkyl or alkenyl acids (C 6 -C 24) ether carboxylic acids, polyoxyalkylenated (C 6 - C 24) aryl ether carboxylic acids and their salts, polyoxyalkylenated (C 6 -C 24) alkylamido ether carboxylic acids and salts thereof, and mixtures thereof.
7. Composition according to any one of the preceding claims, characterized in that the ether carboxylic acids or correspond to the formula (N '): R 1 - (OC 2 H 4) ^ - OCH 2 COOA in which:
R 1 represents a radical or a mixture of linear alkyl or alkenyl radicals or branched C 8 -C 22, an alkyl (C 8 -C 9) alkylphenyl, a radical R 2 CONH-CH 2 -CH 2 - with R 2 denoting a linear alkyl or alkenyl or branched C 11 -C 21, n is an integer or decimal ranging from 2 to 24 a denotes H, ammonium, Na, K, Li, Mg or a monoethanolamine or triethanolamine rest.
8. Composition according to the preceding claims, characterized in that the ether carboxylic acids or correspond to the formula (N ') wherein R 1 denotes a radical or a mixture of alkyl groups (C 12 -C 14 alkyl), cocoyl, oleyl ; a nonylphenyl or octylphenyl radical; A denotes a hydrogen or sodium atom; n ranges from 2 to 20.
9. Composition according to any one of the preceding claims, characterized in that the nonionic surfactants mono- or polyglycerolated correspond to the
Figure imgf000025_0001
in which :
R represents an alkyl or alkenyl radical having 1 to 3 unsaturated bonds (-C = C-), linear or branched, containing from 8 to 40 carbon atoms; m represents a number from 1 to 30.
10. Composition according to Claim 3, characterized in that the mono fatty alcohols or polyglycerolated of formula (IM ') are chosen from fatty alcohols -C 2 -C 24 comprising from 1 to 10 moles of glycerol, more particularly from oleic alcohol containing 2 mol of glycerol, oleyl alcohol containing 4 mol of glycerol, lauryl alcohol with 1 5 moles of glycerol.
11. Composition according to any one of the preceding claims, characterized in that the polyoxyethylene sorbitan esters have the structure (IV)
Figure imgf000025_0002
w, x, y, z respectively denoting a number from O to 20, such that w + x + y + z is less than or equal to 30, preferably between 2 and 30,
R denotes an alkyl or alkenyl radical, linear or branched comprising from 8 to 30 carbon atoms and optionally substituted by hydroxy.
12. Composition according to any one of the preceding claims, characterized in that the or sorbitan esters comprise a number of moles of ethylene oxide of between 2 and 10, preferably between 2 and 6 (average values).
13. Composition according to any one of the preceding claims, characterized in that the one or more polyoxyethylene sorbitan esters are chosen from sorbitan monolaurate oxyethylenated with 4 EO, the sorbitan monostearate oxyethylenated with 4 EO, sorbitan monooleate sorbitan oxyethylenated with 5 EO.
14. Composition according to any one of the preceding claims, characterized in that the content of surfactant (s) represents from 0.01 to 20% by weight based on the weight of the dye composition, and preferably from 0.05 to 10% by weight.
15. A composition according to any preceding claim, characterized in that it comprises one or more couplers.
16. A composition according to any preceding claim, characterized in that it contains one or more additional oxidation base different from the compound of formula (I) or salts thereof, in particular chosen from ortho- or para-phenylenediamines , double bases, ortho- or para-aminophenols, and heterocyclic bases, and the addition salts of these compounds with an acid.
17. A composition according to any preceding claim, characterized in that it contains one or more oxidizing agents, in particular selected from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts , peracids and oxidase enzymes, and preferably hydrogen peroxide.
18. Process for dyeing keratin fibers, characterized in that a composition as defined in any one of claims 1 to 16 is applied to the keratin fibers without an oxidizing agent.
19. Process for dyeing keratin fibers, characterized in that a composition as defined in any one of claims 1 to 16 is applied to the keratin fibers in the presence of one or more oxidizing agents.
20. Multi-compartment device in which a first compartment contains a dye composition as defined in any one of claims 1 to 16 and a second compartment containing a composition comprising one or more oxidizing agents.
21. Multi-compartment device in which a first compartment comprises one or more oxidation bases chosen from the compound of formula (I) or a salt thereof with an acid as claimed in claim 1 and optionally one or more bases of different oxidizing the compound of formula (I) or salt thereof and optionally one or more couplers; a second compartment contains a composition comprising one or more surfactants as described in any one of claims 1 and 3 to 13, and optionally a third compartment containing a composition comprising one or more oxidizing agents.
PCT/FR2010/050964 2009-05-19 2010-05-19 Dyeing composition comprising a secondary para-phenylenediamine oxidation base and a specific surfactant WO2010133803A1 (en)

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FR0953323A FR2945732B1 (en) 2009-05-19 2009-05-19 Dye composition comprising a secondary diamine para-phenylene oxidation base and a surfactant has cationic charge.
FR0953323 2009-05-19
FR0953329A FR2945735B1 (en) 2009-05-19 2009-05-19 Dye composition comprising a para-phenylene diamine secondary oxidation base and a nonionic surfactant particular
FR0953326 2009-05-19
FR0953329 2009-05-19
FR0953326A FR2945733B1 (en) 2009-05-19 2009-05-19 Dye composition comprising a secondary diamine para-phenylene oxidation base and a carboxylic acid ether.

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US8802071B2 (en) 2011-06-24 2014-08-12 L'oreal Compositions containing a fatty quaternary amine, a nonionic surfactant, and a carboxylate compound for lifting color and/or imparting shine onto keratinous substrates
US8802069B2 (en) 2011-06-24 2014-08-12 L'oreal Compositions containing a phospholipid, a nonionic surfactant, and a carboxylate compound for lifting color and/or imparting shine onto keratinous substrates
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
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US9688609B2 (en) 2014-11-04 2017-06-27 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine
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WO2012175690A3 (en) * 2011-06-24 2013-10-31 L'oreal Compositions containing an amine or a phospholipid, a nonionic surfactant, and a carboxylate compound for lifting color and/or imparting shine onto keratinous substrates
US8802071B2 (en) 2011-06-24 2014-08-12 L'oreal Compositions containing a fatty quaternary amine, a nonionic surfactant, and a carboxylate compound for lifting color and/or imparting shine onto keratinous substrates
US8802069B2 (en) 2011-06-24 2014-08-12 L'oreal Compositions containing a phospholipid, a nonionic surfactant, and a carboxylate compound for lifting color and/or imparting shine onto keratinous substrates
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
US9309185B2 (en) 2012-10-26 2016-04-12 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9012691B2 (en) 2012-10-26 2015-04-21 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

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