WO1997030684A1 - Cosmetic hair dyeing composition and methods for preparing same - Google Patents

Abstract

A composition including (a) 0.1-30 % of at least one amino acid-derived amphoteric surfactant with an inorganic salt content of at most 1 wt % relative to said surfactant, (b) 0.01-30 wt % of a hair treatment agent selected from oxidation dyes and direct dyes, and (c) a cosmetically acceptable carrier. The methods for making said composition comprise preparing a carboxylic or sulphonic amino acid-derived surfactant with an inorganic salt content of at most 1 %, and mixing same with the other components.

Description

 Cosmetic composition for hair coloring and preparation procedures.

The present invention relates to cosmetic compositions for hair use comprising surfactants derived from amino acids and dyes. In the field of hair compositions intended to permanently or temporarily modify the coloring of the hair, a major difficulty consists in optimizing the deposition of dyes and ensuring their stability. A number of solutions exist but often require the use of surfactants which are irritating to the skin and / or the eye or which contain impurities which are incompatible with a cosmetic application.

However, in recent years, there has been a very great need for surfactants which are both effective and which are not irritating to the skin or the eyes and which can be used without particular precautions with maximum safety.

Research into non-irritant products has converged on amphoteric surfactants (that is to say having an overall electrical charge of zero) of the betaine or amphoacetate type, the synthesis methods of which are generally based on a carboxylation reaction of a fatty amine, for example an alkylamidoethylethanolamine or an alkylimidazoline, on monochloroacetic acid or its sodium salt. This synthesis therefore leads to the release of Na ⁺ CI ^" , the Cl ~ anton from monochloroacetic acid, as well as to the release of sodium glycolate from the hydrolysis of the starting acid.

The major drawbacks encountered with surfactants of the above type are as follows:

- harmful influence on the deposition of dyes on the hair. - Significant increase in the viscosity of the surfactant solution which does not allow the solutions to be concentrated beyond a concentration by weight of around 30% because the viscosity increases suddenly, which prevents the marketing of concentrated solutions;

- deterioration of the cold resistance and of the emulsifying and stabilizing properties; - problem of compatibility with the other additives in the compositions (thickening agents, preservatives, silicone emulsions, fixing resins, conditioning agents, etc.),

It has been unexpectedly found that the performance of the cosmetic compositions which are the subject of the invention can be achieved by careful control of the contents of inorganic salts (in particular NaCl) in the amphoteric surfactants constituting them: by limiting this content to a value of less than 1%, not necessarily zero, the coloring of the hair is made more effective and more durable. The subject of the present invention is cosmetic compositions for hair coloring comprising:

a) from 0.1 to 30% of an amphoteric surfactant derived from amino acid having an inorganic salt content of at most 1% by weight; b) from 0.01 to 30% of a hair coloring agent, chosen from oxidation dyes and direct dyes, and c) a cosmetically acceptable vehicle.

The compositions which are the subject of the invention can be formulated in a large number of types of products, such as foams, styling gels, shampoos, conditioners, rinsing formulas, sun protection lotions and ultraviolet radiation, and many other compositions of the same type, in particular any formulation used for styling or for facilitating combing of the hair.

By the term composition or cosmetic formulation means all products or cosmetic preparations as those described in Annex I ( "illustrative list by category of cosmetic products") of the European Directive ^No. 76/768 / EEC of 27 July 1976 called cosmetic directive.

The coloring agent of any type known among the hair dyes may be in particular of an anionic, cationic, nonionic, amphoteric nature, or a mixture. Preferably coloring agents of nonionic and / or cationic nature will be used. Among the coloring agents capable of being used as constituents of the cosmetic compositions forming the subject of the invention, there may be mentioned by way of nonlimiting examples:

- among the class of dyes by oxidation:

These are the coloring ingredients that will give rise to coloring via an oxidation reaction. The oxidizing agent can be air oxygen, hydrogen peroxide, or ammonium persulfate persulfates.

- the aromatic derivatives containing primary or secondary amine groups such as for example N- (hydroxyethyl-2), N-ethyl chloro p-phenylene diamine; 3,4-methylene dioxyanilin; 4-amino-2-methylphenol, 4-amino-3-benzoic acid; 7-amino-4 hydroxy-naphthalene-2 sulfonic acid; diamino-4,4 'benzophenone; bis-1, 3- (N- (4-amino phenyl) hydroxyethylamino-2) propan-2-ol, or mixtures thereof. - heterocytic derivatives such as for example 2-amino-4-methoxy-6-methylpyrimidine, 6-amino nicotinic acid, 2,6-dihydroxy-3,4-dimethyl-3,4-pyridine, or mixtures thereof.

- phenol or polyphenol derivatives such as for example pyrocatechol, resorcinol, pyrogallol, phloroglucinol, dihydroxy-1,5 naphthalene

- nitro derivatives such as nitro-2 p-phenylene diamine, chloro-5 nitro-3 o- phenylene diamine, amino-2 nitro-4 phenol, amino-4 nitro-2 phenol

- among the class of direct dyes: - nitro derivatives containing an aromatic group such as for example 3-amino-4-hydroxy nitrobenzene, 3,4-diamino nitrobenzene, 2-amino N-hydroxyethyl amino-5 nitro benzene , 4-nitro-3-methylamino phenoxyethanol, 2-amino-3-methyl-nitro benzene, 3-hydroxy-4-amino nitro benzene, or mixtures thereof.

- anthraquinone derivatives such as, for example, those listed by name in the Color Index such as Disperse violet 4, Disperse blue 1, Acid violet 43, Disperse violet 1, Acid blue 62, or mixtures thereof.

- the indoamine derivatives horn for example N-hydroxyethylamino-2-methoxy-5,2 'aminoaniline-4' benzoquinone-1, 4, N- (chloro-3 'methylaminophenyl-4') ureido-3 methyl-6 benzoquinone- 1, 4 imine. - acridinic dyes such as for example acridine orange (basic orange 14)

- xanthene dyes such as rhodamine B (basic violet 10)

- Azo dyes such as Disperse Yellow 3, Basic Red 76, Acid Red 35, Disperse Black 5, or mixtures thereof.

- triarylmethane dyes such as for example basic green 1, basic violet 14, basic blue 26 or their mixtures.

- azine dyes such as basic red 2.

In the present application, the term “amino acid” means, in the manner well known to those skilled in the art, a compound carrying at least one amine function and one acid function such as those present in amino acids and natural acids, in particular carboxylic acid, sulfonic, phosphonic functions.

Surfactants derived from amino carboxylic acid or amino sulfonic acid which can be used according to the invention are amphoteric surfactants comprising: - at least one ammonium function or one amino function capable of being protonated, and

- at least one carboxylic or sulfonic acid function, respectively. These surfactants can in particular be betaine or sulfobetaine surfactants, including amidoalkylbetaines and amidoalkyl sulfobetaines, or also amphoacetate surfactants or also called amphodiacetates.

Among the betaine type surfactants, there may be mentioned for example:

betaines of formula 1:

Ri R ₂ R3 NR ₄ C (0) 0 ^" (1) the sulfo-betaines of formula 2:

Rl R ₂ R3NR ₄ S0 ₃ - (2) amidoalkylbetaines of formula 3: RιC (0) - NH R ₄ N (R ₂ R3) R ₅ C (0) 0- (3) and amidoalkylsulfo-betaines of formula 4 :

R ₁ C (0) - NH R ₄ N (R ₂ R3) R5 Sθ3- (4) formulas in which the radical Ri represents an alkyl or alkenyl radical having from 10 to 24 carbon atoms, the radicals R ₂ , and R3 , identical or different, represent an alkyl radical having from 1 to 4 carbon atoms, and the radicals R4 and R5, identical or different, represent an alkylene radical having from 1 to 4 carbon atoms.

The betaines of formula (1) can be obtained in particular by carboxylation of the amine of formula R1R2R3N by the halocarboxylic acid of formula Hal-RijCOOH or one of its salts whereas the sulfobetaines of formula (2) can be obtained in particular by sulfonation of the amine of formula R1R2R3N by the halosulfonic acid of formula Hal-R4 ~ Sθ3H or one of its salts, in the presence of an alkaline agent. These reactions are accompanied by the release of the corresponding alkali halide salt.

The amidoalkylbetaines or sulfobetaines are obtained analogously from the corresponding amidoalkylamine.

Among the surfactants of amphoacetate type, there may be mentioned more particularly

the alkylamphoacetates corresponding to the general formula (5):

RiCpj - NH - Rs -N - Ry - OH (5) CH ₂ C (O) OM in which Ri has the above meaning and most often represents coconut and lauryl chains, Rg and R7 which are identical or different, represent an alkylene radical having 2 to 6 carbon atoms, and M represents a hydrogen or metal atom alkaline, or an ammonium ion.

The present invention relates more particularly to cosmetic compositions comprising amphoteric surfactants such as alkylamphoacetates, and more particularly the amidoamine derivatives listed in the dictionary "Cosmetics Toiletries Fragrance Association" Edition 1994 under the names of alkylamphoacetate or alkylamphodiacetate and corresponding to the formula :

RiC (O) - NH - CH ₂ CH ₂ -N - CH ₂ CH ₂ - OH

CH ₂ C (0) 0 Na and their counterparts more generally corresponding to formula (5)

RιC (0) - NH - R ₆ -N - R ₇ - OH (5)

CH ₂ C (O) OM

formulas in which Ri, Rg, R7 and M have the above meanings.

A generally used method for preparing alkylamphoacetates is the reaction of an alkylimidazoline of formula (6).

in which Rj, RQ and R7 have the meanings given above, or of one of its open-cycle derivatives with a monohaloacetic acid, preferably chloroacetic acid or one of its salts in the presence of an alkaline agent (see in particular US-A 2,528,378 and US-A 2,773,068).

Preferably the pH of the reaction mixture is adjusted so that it does not exceed 10 during the reaction (see European patent application EP-A-0 647 469).

The alkali is preferably sodium hydroxide and the pH is preferably maintained between 8.5 and 9.5, the reaction temperature is preferably between 75 and 85 ^° C. For the purposes of the present invention, the various surfactants derived from carboxylic or sulfonic amino acids described above must have a low content of inorganic salts, in particular of alkali halides which can come from their synthesis, namely at most 1% by weight . Absolute purity with regard to inorganic salts is not necessary and very good properties are observed for contents of 0.05 to 1% by weight.

The surfactants with a low content of inorganic salts constituting hair cosmetic compositions which are the subject of the invention can be obtained according to various purification methods well known to those skilled in the art, such as for example purification by dialysis or by electrodialysis of solutions. aqueous surfactants as described in French patent application N * 95 04 014 filed by the Applicant on April 5, 1995, the precipitation of inorganic salts, in particular by a third solvent, or liquid liquid extraction, or alternatively by methods of synthesis not leading to the formation of inorganic salts. For example, an alkylamphoacetate suitable for the invention can be obtained directly by reaction of an aminoalkylalkanolamine of formula (7):

R ₁ C (O) NH R ₆ NH R ₇ - OH (7) in which Ri, Rβ and R ₇ have the meaning indicated above with formaldehyde and a cyanide of formula (8):

XCN (8) in which X represents a hydrogen atom or an alkali metal, in particular lithium, sodium or potassium, provided that if X is a hydrogen atom, the nitrile obtained is hydrolyzed with an alkaline agent. Such cyanide process is described in British Patent Application ^No. 94.23573 filed November 22, 1994. The alkali agent is preferably sodium hydroxide.

Preferably, Rg and R7 are identical and represent an ethylene radical in formula (7).

The preferred methods of preparation of surfactants suitable for the cosmetic compositions which are the subject of the invention are the electrodialysis of aqueous solutions of surfactants or the cyanide process.

In general, the surfactants derived from amino acids having an inorganic salt content of at most 1% by weight, used in the hair cosmetic compositions which are the subject of the invention are present in an amount corresponding to approximately

0.1-30%, advantageously 0.5-30% by weight relative to the total weight of the formulation, preferably 2 to 10%. The quantities can be adjusted to obtain the best level of performance.

The compositions which are the subject of the invention relate above all to the hair area with the aim of permanently or temporarily modifying the external appearance of the hair but may be used for the purpose of modifying the coloring of any other part of the hair system. and in particular the eyelashes, eyebrows, and hair. The pH of the compositions which are the subject of the invention can advantageously be between 3 and 11, preferably between 5 and 10.

It is adjusted by alkaline agents such as monoethanolamine, diethanolamine, triethanolamine, ammonia, ammonium carbonates, potassium or sodium, sodium hydroxide, 2-Pamino-2 nπethyl-2 propanol -1, or with acidifying agents such as phosphoric, hydrochloric, tartaric, acetic, lactic or citric acids. The compositions which are the subject of the invention can be applied to natural, permanent, colored or bleached hair. The hair may also have undergone a lightening treatment, either with an ammonia hydrogen peroxide solution or containing alkaline agents such as the aliphatic or hydroxyaliphatic amines, or with an ammoniacal solution of alkali peroxides or persalts, such as sodium peroxide, potassium peroxide, sodium perborate, sodium percarbonate, or any other oxidizing agent known to those skilled in the art.

The cosmetic compositions which are the subject of the invention comprise a vehicle, or a mixture of several vehicles, which are compatible with a hair application. These vehicles can be present in particular at concentrations of between 0.5% and 99.5%, preferably between 5 and 99.5%. The term "compatible with a hair application" here means that the vehicle does not damage or exert negative effects on the appearance of the hair or does not create irritation of the skin and / or the eye and / or the scalp. The vehicles compatible with the applications described in this invention include, for example, those used in sprays, foams, tonics, gels, shampoos, or rinsing lotions. The choice of the appropriate vehicle will depend on the nature of the constituents in particular of the resin, and according to whether the formulated product is supposed to be left on the surface where it was applied (for example sprays, foams, tonic lotion, or gels) or rinsed after use (e.g. shampoo, conditioner, rinse lotions).

The vehicles which can be used include a large number of products usually used in cosmetic compositions for the hair. The vehicles may include a solvent to dissolve or disperse the ingredients used, such as as water, Cf -Cg alcohols, and their mixtures, in particular water and methanol, ethanol, isopropanol, and their mixtures.

Vehicles can also contain a wide variety of other compounds such as ketones such as acetone, hydrocarbons (such as isobutane, hexane, decene), halogenated hydrocarbons (such as freons), linalool, esters (such as ethyl acetate, dibutyl phthalate), and volatile silicones (in particular siloxanes such as phenyl pentamethyl siloxane, methoxypropyl heptamethyl cyclotetrasiloxane, chloropropyl pentamethyl disiloxane. hydroxypropyl pentamethyl disiloxane, octamethyl cyclotetrasiloxane, decamethyl cyclopenta siloxane, cyclodimethicone, and dimethicone), and mixtures thereof.

When these hair cosmetic compositions are in the form of sprays, tonic lotions, gels, or foams, the preferred solvents include water, ethanol, volatile silicone derivatives, and mixtures thereof. The solvents used in these mixtures can be miscible or immiscible with each other.

Foams and aerosol sprays can also use any propellant capable of generating the products in the form of foam (in the case of foam) or in the form of fine, uniform sprays. By way of examples, mention may be made of trichlorofluoromethane, dichlorodifluoromethane, difluoroethane, dimethyl ether, propane, n-butanβ, or isobutane.

These vehicles can take many forms. For example, vehicles in the form of emulsions include water in oil, oil in water, and oil in water in silicone emulsions. These emulsions cover a wide viscosity range, from 0.1 to 200 Pa.s. These emulsions can also be delivered in the form of sprays using either a mechanical pump type device, or in the form of an aerosol pressurized by the use of a propellant gas. These vehicles can also be delivered in the form of foam. Mention may be made, for example, of anhydrous liquid solvents, such as oils, alcohols and silicones, homogeneous aqueous mixtures such as hydroalcoholic mixtures, and the rheologically modified versions of these two systems, for example when the viscosity of the system has been increased by the addition of gums, resins, polymers, or salts).

The cosmetic compositions which are the subject of the invention may contain conditioning agents. Among the conditioning agents which can be used in the context of this invention, there are conditioning agents of animal origin, such as animal protein hydrolysates and their salts, such as the dimethyl- or trimethyl ammonium stearate salts of collagen, silk, keratin hydrolysates; cationic copolymer conditioning agents of synthetic origin, better known under the name polyquaternium, such as the copolymer of N, N'-bis ((dimethylamino) -3 propyl) urea and oxy-1, 1 ¹ bis (chloro-2 ) ethane or polyquaternium-2, the copolymer of diallyldimethyl ammonium chloride and acrylamide or polyquaternium-7; cationic derivatives of polysaccharides, such as cocodimonium hydroxyethylcellulose, guar hydroxypropyl trimonium chloride, hydroxypropyl guar chloride hydroxypropyl trimonium (JAGUAR C13S, JAGUAR C162 marketed by RHONE-POULENC), poly (oxyethanediyl-1,2 ether) ) 2-hydroxy-3-trimethylammonium chloride propyl cellulose or polyquaternium-10; silicones and silicone derivatives such as amodimethicone, cyclomethicone, ketyl dimethicone copolyol, cyclomethicone, dimethicone copofyol, trimethylsilyl amodimethicone, polyquaternium-80; cationic type surfactants such as distearyl dimethyl ammonium chloride. The conditioning agents used as constituents of the hair cosmetic compositions which are the subject of the invention are preferably chosen from conditioning agents of synthetic origin, in particular polyquaterniums -2, -7, and -10, and cationic derivatives of polysaccharides. , such as cocodimonium hydroxyethylcellulose, guar hydroxypropyl trimonium chloride, hydroxypropyl guar hydroxypropyl trimonium chloride.

It will be preferred to use the cationic derivatives of polysaccharides, and in particular the guar derivatives such as guar chloride hydroxypropyl trimonium and hydroxypropyl guar chloride hydroxypropyl trimonium.

The performance of the cosmetic compositions which are the subject of the invention can also be improved by the use of plasticizing agents. The plasticizing agent may advantageously represent from 0.1 to 20% by weight of the formulation, preferably from 1 to 15%. Among the particularly useful plasticizing agents, there may be mentioned adipates, phthalates, isophthalates, azelates , stearates, copolyois silicones, glycols, castor oil, or mixtures thereof.

The hair cosmetic compositions which are the subject of the invention may also contain fixative resins which are advantageously present at concentrations of 0.01 to 10% by weight relative to the total weight of the formulation, preferably from 0.5 to 5 %.

The fixing resins capable of being used according to the invention are preferably chosen from the following resins: acrylate / acrylamide, polyvinylmethyl copolymers ether / maleic anhydride, vinyl acetate / crotonic acid, octylacrylamide / butylaminoethyl acrylate / methacrylate, polyvinylpyrrolidone (PVP), polyvinylpyrrolidone copolymers, in particular polyvinylpyrrolidone and methyl methacrylate copolymers, and polyvinyl acetate copolymers vinyl (VA), polyvinyl alcohol, copolymers of polyvinyl alcohol and crotonic acid, copolymers of polyvinyl alcohol and maleic anhydride, polystyrene sodium sulfonate; a polyvinylpyrrolidone / ethyl methacrylate / methacrylic acid terpolymer, poly (methylvinyl ether / maleic acid) monomethyl ether; polycondensates of ethylene glycol / ethylene glycol terephthalate, polycondensates of diester, terephthalic acid / sulfoisophthalic acid / glycol, and their mixtures, poly (vinyl acetate) grafted on polyoxyalkylene trunks such as poly (acetate of vinyl) grafted onto polyoxyethylene trunks (EP-A-219 048), polyester copolymers based on ethylene terephthalate and / or propylene terephthalate, and polyoxyethylene terephthalate units, with a ratio of the number of ethylene terephthalate units and / or propylene terephthalate in the number of polyoxyethylene terephthalate units of the order of 1/10 to 10/1, preferably of the order of 1/1 to 9/1, the polyoxyethylene terephthalates having polyoxyethylene units having a weight molecular on the order of 300 to 5000, preferably on the order of 600 to 5000 (US-A-3,959,230, US-A-3,893,929, US-A-4,116,896, US-A-4,702,857 , US-A-4,770,666); polyester sulfone oligomers obtained by sulfonation of an oligomer derived from ethoxylated allyl alcohol, dimethyl terephthalate and 1,2-propylene diol, having from 1 to 4 sulfone groups (US Pat. No. 4,968,451); polyester copolymers based on propylene terephthalate and polyoxyethylene terephthalate units and terminated by ethyl or methyl units (US-A-4711 730) or polyester oligomers terminated by alkylpolyethoxy groups (US-A-4 702 857) or groups anionic sulfopolyethoxy (US-A-4,721,580); sulfoaroyles (US-A-4,877,896); the polyester-polyurethanes obtained by reaction of a polyester with a molecular mass of 300-4000 in number obtained from adipic acid and / or terephthalic acid and / or sulfoisophthalic acid and a diol of mass less than 300. on a prepolymer with terminal isocyanate groups obtained from a polyoxyethylene glycol with a molecular weight of 600-4000 and a diisocyanate (FR-A-2 334 698); polyester sulfone oligomers obtained by condensation of isophthalic acid. dimethyl sulfosuccinate and diethylene glycol (FR-A-2 236 926); polyester sulfones obtained by condensation of dimethyl terephthalate / isophthalic acid / sodium dimethyl sulfonate isophthalate / ethylene glycol (EP-A-540 374); or their mixtures.

In addition, cationic resins can also be used. These cationic resins consist in whole or in part of cationic monomers such as for example dimethylaminoethyl methacrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethyl ammonium chloride, or mixtures thereof. Preferably, the fixing resins which are the subject of the invention will be of the polyvinylpyrrolidone (PVP) type, polyvinylpyrrolidone and methyl methacrylate copolymers, polyvinylpyrrolidone and vinyl acetate (VA) copolymer, polycondensates of ethylene terephthalate. glycol / ethylene glycol, diester polycondensates, terephthalic acid / anhydride / sulfoisophthalic / glycol, and mixtures thereof. These fixative resins are preferably dispersed or dissolved in the chosen vehicle.

These hair cosmetic compositions can also comprise surfactants which serve to disperse, emulsify, dissolve and stabilize various compounds used for their emollient or humectant properties. The surfactants can be used in these compositions at concentrations advantageously varying from 0.05 to 50% by weight of the preparation. There are thus anionic, nonionic, cationic, zwitterionic or amphoteric surfactants or mixtures of these surfactants.

Mention will in particular be made of surfactants such as

. alkyl esters sulfonates of formula R-CH (Sθ3M) -COOR '. where R represents a Cg-C2o alkyl radical. preferably in C-jo-Cig, R 'an alkyl radical in C- | -Cg, preferably in C1-C3 and M an alkali cation (in particular sodium, potassium, lithium), a substituted or unsubstituted ammonium (in particular methyl -, dimethyl-, trimethyl-, tetramethylammonium, or dimethylpiperidinium) or derivative of an alkanolamine (in particular monoethanolamine, diethanolamine or triethanolamine). Mention may very particularly be made of methyl ester sulfonates whose radical R is C- _j 4-C1 g;

. the alkyl sulfates of formula ROSO3M, where R represents a C10-C24 alkyl or hydroxyalkyl radical. preferably in C12-C20 and very particularly in C-) 2-Ci8. M representing a hydrogen atom or a cation of the same definition as above, as well as their ethoxylated (OE) and / or propoxylated (OP) derivatives, having on average from 0.5 to 6 units, preferably from 0, 5 to 3 OE and / or OP motifs;

. alkylamide sulfates of formula RCONHROSO3M where R represents a C2-C22 alkyl radical. preferably in Cg-C2o. R 'a C2-C3 alkyl radical, M representing a hydrogen atom or a cation of the same definition as above, as well as their ethoxylated (OE) and / or propoxylated (OP) derivatives, having an average of 0, 5 to 60 OE and / or OP patterns;

. the salts of C3-C24 saturated or unsaturated fatty acids. preferably C-14-C20. 'Alkylbenzenesulfonates ^are C9-C20. primary or secondary alkyl sulfonates ^c 8 ~ ^c 22- ^{, es} alkylglycerol sulfonates, the sulfonated polycarboxylic acids described in GB-A-1 082 179, paraffin sulfonates, N-acyl N-alkyltaurates, alkylphosphates, alkylisethionates, alkylsuccinamates, alkylsulfosuccinates, monoesters or diesters of sulfosuccinates, N-acyl sarcosinates, alkyl glycoside sulfates, polyethoxycarboxylates, the cation of which is an alkali metal (especially sodium, potassium, lithium), a substituted or unsubstituted ammonium (especially methyl-, dimethyl- , trimethyl-, tetramethylammonium or dimethylpiperidinium) or derived from an alkanolamine (in particular monoethanolamine, diethanolamine or triethanolamine);

- non-ionic surfactants, such as for example

. polyoxyalkylenated alkylphenols (in particular polyoxyethylenated, polyoxypropylenated, polyoxybutylenated) in which the alkyl substituent is Cg-C- | 2 and containing from 5 to 25 oxyalkylene units; by way of example, mention may be made of the Triton X-45, X-114, X-100 or X-102 sold by Rohm & Haas Cy. ; . glucosamides, glucamides;

. glycerolamides derived from N-alkylamines (US-A-5,223,179 and FR-A-1,585,966). polyoxyalkylenated Cg-C22 aliphatic alcohols containing from 1 to 25 oxyalkylene units (in particular oxyethylene, oxypropylene); by way of example, mention may be made of TERGITOL 15-S-9, TERGITOL 24-L-6 NMW sold by Union Carbide Corp., NEODOL 45-9, NEODOL 23-65, NEODOL 45-7, NEODOL 45-4 marketed by Shell Chemical Cy. KYRO EOB marketed by The Procter & Gamble Cy. . the products resulting from the condensation of ethylene oxide with a hydrophobic compound resulting from the condensation of propylene oxide with propylene glycol, such as the Pluronic sold by BASF;

. amine oxides such as C10-C18 dimethylamine alkyl oxides, Cg-C22 ethyl dihydroxy ethylamine alkoxy oxides;

. the alkylpolyglycosides described in US-A-4565 647 and their polyoxyalkylenated derivatives; . fatty acid amides in Cg-C2o. ethoxylated fatty acids

. ethoxylated amides, amines, amidoamines

- cationic surfactants, for example. alkyldimethyiammonium halides

- amphoteric and zwitterionic surfactants, containing not more than 1% of inorganic salts, for example .the condensation products of fatty acids and protein hydrolysates, alkylamphopropionates or -dipropionates, which are used to reduce the irritation caused by other surfactants, mainly anionic surfactants.

One can also advantageously add to these hair compositions metal sequestering agents, more particularly those sequestering calcium such as citrate ions or emollient agents such as silicones or oils or fatty substances used for this purpose in the cosmetic industry (in particular oils mineral, fatty acid esters, triglycerides).

It is also advantageous to incorporate into the hair cosmetic compositions forming the subject of the invention humectants. Mention may be made of glycerol, sorbitol, urea, collagen, gelatin, aloe vera, hyaluronic acid. It is also possible to envisage emollients which are generally chosen from alkylmonoglycerides, alky Id iglycerides, triglycerides such as oils extracted from plants and plants (in particular palm, copra, cottonseed, soybean, sunflower oils , olive, grapeseed, sesame, peanut, castor oil ...) or oils of animal origin (especially tallow, fish oils ....), derivatives of these oils such as hydrogenated oils, lanolin derivatives, mineral oils or paraffinic oils, perhydrosqualane, squaiene, diols like 1-2-propanediol, 1-3 -buta nediol, cetyl alcohol, stearyl alcohol , oleic alcohol, polyethylene glycols or polypropylene glycols, fatty esters such as isopropyl palmitate, ethyl-2-hexyl cocoate, myristyl myristate, lactic acid esters, stearic acid, l behenic acid, isostearic acid, sili oils cones grouping cyclic polydimethylsiloxanes, hydroxylated polydimethylsiloxanes,-ω, polydimethylsiloxanes < ^χ -ω trimethylsilylated, polyorganosiloxanes such as polyalkylmethylsiloxanes, polymethylphenylsiloxanes, ies polydiphenylsilones silicone silicones, SILBIONE 70646 oil sold by the company RHONE-POULENC or DC 190 sold by DOW CORNING) or mixed silicone derivatives including different types of derivatization (such as mixed polyalkylmethylsiloxane-silicone copolyether copolymers).

To further reduce irritation or aggression on the scalp, it is also possible to add water-soluble or water-dispersible polymers such as collagen or certain non-allergenic derivatives of animal or vegetable proteins (wheat protein hydrolisates for example), natural hydrocolloids ( such as guar, carob, tara gum) or from fermentation processes such as xanthan gum and derivatives of these polycarbohydrates such as modified celluloses (for example hydroxyethylcellulose, carboxymethylcellulose), guar or carob derivatives such as their nonionic derivatives (for example hydroxypropylguar), anionic derivatives (carboxymethylguar) or mixed nonionic / anionic derivatives such as carboxy-hydroxypropyl-guars. To the basic constituents, it is optionally possible to add in combination powders or mineral particles such as calcium carbonate, mineral oxides in powder form or in colloidal form (particles of smaller size or of the order of one micrometer, sometimes of a few tens of nanometers) such as titanium dioxide, silica, aluminum salts, kaolin, talc, clays and their derivatives. Preservatives such as the methyl, ethyl, propyl and butyl esters of p-hydroxybenzoic acid, sodium benzoate, the product sold under the brand name GERMABEN or any chemical agent preventing bacterial proliferation or molds and traditionally used compositions cosmetics can advantageously be introduced into the compositions of the invention, in particular up to 0.01 to 3% by weight. The amount of these products is generally adjusted to avoid any proliferation of bacteria, molds or yeasts in cosmetic compositions. As an alternative to these chemical agents, it is sometimes possible to use agents modifying the activity of water and greatly increasing the osmotic pressure such as carbohydrates or salts. To protect the hair from the aggressions of the sun and UV rays, we can add to these formulations sun filters which are either chemical compounds strongly absorbing UV radiation like the compounds authorized in the European directive N * 76/768 / EEC, its annexes and subsequent amendments to this directive, or titanium dioxide or cerium oxides in the form of powder or colloidal particles. These powders can optionally be surface treated to increase the effectiveness of their anti-UV action, to facilitate their incorporation into cosmetic formulations or to inhibit surface photoreactivity.

To these ingredients, it is generally possible to add, in order to increase the pleasure during the use of the composition by the consumer, one or more perfumes, coloring agents for the composition among which the products described in Annex IV may be mentioned ("list of coloring agents allowed for use in cosmetic products ") of the European Directive ^No. 76/768 / EEC of 27 July 1976, known as cosmetics directive ,, and / or opacifiers such as pigments. Bactericidal or fungicidal agents can also be incorporated into the composition in order to improve the disinfection of the scalp such as, for example, triclosan. Finally, the composition may also contain viscous or gelling polymers, such as crosslinked polyacrylates - in particular the CARBOPOL brand products marketed by GOODRICH -, cellulose derivatives such as hydroxypropylcellulose, carboxymethylcellulose, guars and their derivatives, carob , tara or cassia gum, xanthan gum, alginates, carrageenans, chitin derivatives such as chitosan, etc. used alone or in combination, or the same compounds, generally in the form of water-soluble polymers modified by hydrophobic groups covalently linked to the polymer backbone as described in patent WO 92/16187 and / or water to bring the total of the constituents of the formulation to 100%.

The cosmetic compositions which are the subject of the invention may also contain polymeric dispersing agents, in particular in an amount of the order of 0.1-7% by weight. To control the hardness of calcium and magnesium, agents such as. the water-soluble salts of polycarboxylic acids with a molecular mass of the order of 2000 to 100,000, obtained by polymerization or copolymerization of ethylenically unsaturated carboxylic acids such as acrylic acid, maleic acid or anhydride, fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, methylenemalonic acid, and in particular polyacrylates with a molecular weight of the order of 2,000 to 10,000 (US-A-3,308,067). copolymers of arylic acid and maleic anhydride with a molecular mass of the order of 5,000 to 75,000 (EP-A-66,915). polyethylene glycols of molecular mass of the order of 1000 to 50,000.

The subject of the invention is also a method of manufacturing a composition as described above, characterized in that it comprises the steps consisting in: a) purifying a surfactant derived from amino acid having an inorganic salt content greater than 1 % by weight, by a suitable separation technique to obtain a surfactant having a content of said salts of at most 1% by weight, and b) mixing the surfactant thus obtained with the coloring agent and the vehicle, and optionally the other ingredients.

Another process which is the subject of the invention is characterized in that it comprises the steps consisting in: a) preparing a surfactant of formula (5) by reaction of an aminoalkylalkanolamine of formula (7)

R-) C (O) NH Rg NH R ₇ -OH (7),

in which R- _j , Rg and R7 have the above meanings, with a cyanide of formula (8) XCN (8) in which X represents a hydrogen or alkali metal atom, followed by an alkaline hydrolysis of the nitrile formed in the case where X is a hydrogen atom, and

b) mixing the surfactant having an inorganic salt content of at most 1% by weight thus obtained, with the coloring agent and the vehicle, and optionally the other ingredients.

The following examples illustrate the invention.

REFERENCE EXAMPLE: Preparation of cocoamphomonoacetate with a low content of inorganic salts

A TS-2-10P type pilot electrodialyser sold by the company Eurodia is used. This electrodialyzer has a total useful membrane surface of 2000 cm? and comprises 10 cells with 2 compartments of 200 cm ² of useful unit area.

The anionic and cationic membranes used are membranes sold by the company Eurodia or Tokoyama Soda, the references of which are Neosepta AM1 and Neosepta CMX respectively.

2 liters of cocoamphomonoacetate solution at 26% by weight are electrodialysis. This starting material was prepared by reaction of cocoimidazoline with chloroacetic acid in accordance with Example 3 of European patent application EP-A-0 647 469, the pH being adjusted to 7 by addition of HCl.

The operation is carried out at ambient temperature with a current density of 18.4 mA / cm ² . The initial NaCl content is 8.5% relative to the total weight of the solution. The viscosity of the initial solution is 44 mPa.s.

The electrodialysis is stopped after 8 hours.

The final sodium chloride content is dosed and a value of 0.6% is found, the sodium glycolate is also dosed and it is observed that it goes from a content of 1.2% to 0.6% . The final viscosity is 71 mPa.s. The cocoamphomonoacetate concentration goes from 26% to 33%.

The irritant potential was assessed by the Eytex method on the product itself and in formulation. EXAMPLE 1: PREPARATION OF A COLORING SHAMPOO

Three coloring shampoos of the following compositions were prepared.

% in weight

A B C (according to the invention) (comparison)

- Lauryl Ether Sodium Sulfate

Empicol ESB 3M 7 10 7

- Product of the reference example (30%) 3 -

- Miranol C2M (30%) - - 3

(cocoamphoacetate containing 11% NaCl inorganic salts)

- Coloring solution * 31, 43 31, 43 31, 43

- Curator q.s q.s. q.s.

- Distilled water qs 100 qs 100 qs K the pH being adjusted to 6.5 with citric acid.

The coloring solution corresponding to a copper reflection, proposed by Sté Les Colorants

Wacker, has the following composition:

% wt

Covariane Purple W 5121 1.2 Covariane yellow W 1125 1, 9

Covarian red W 3121 1, 4

Solvarian 95.5

(the dyes being completely dissolved in the solvarian)

The tests are carried out on degraded Indian hair ref NWI R hair from ia Sté HTS (Germany) - wick of 5g. For each test, a series of 3 wicks was produced.

The wicks are wetted without washing them and are wrung between two fingers. Using a disposable pipette, apply 3 ml of coloring shampoo from root to tip. It is then distributed over the entire hair, massaging lightly and lathering. Leave to act for 60 minutes so that the coloring develops completely. Add a little warm water 35-37 ° C and massage lightly. Finally, rinse thoroughly with lukewarm water until the rinsing water is completely clear. Results:

The measurement of the color of the locks was carried out visually and by measurement with a Coloπmeter Lab using a LUCI QC V1.0 device Dr Bruno Lange GmbH after treatment and after 5 successive washes with a 10% solution of lauryl ether sodium sulfate.

For the visual evaluation, the intensity of the color of the locks is compared with a starting discolored lock of hair having a very light ash blonde coloring. Right after the treatment, we see that

- locks treated with shampoo A have an intense pink coloring.

- the locks treated with shampoo B have a blond coloring,

- the locks treated with shampoo C have a pinkish blonde coloring.

The colors classified in decreasing order of intensity are A> C »B» ash blonde reference.

The results of the colorimeter measurement are collated in the following table:

Treated hair reference A B C

Just for treatment

L: degree of white 55.53 + 1.40 36.21 ± 0.99 35.67 ± 0.98 36.66 ± 0.61 a: intensity of red 2.27 ± 0.18 11.43 ± 0.36 9.64 ± 0.43 10.65 ± 0.57 b: yellow intensity 15.42 ± 0.50 11, 18 + 0.41 13.55 ± 0.43 12.39 ± 0.29 aorès 5 Lavaαes

L: degree of white 41, 34 ± 1.07 43.52 ± 1.25 42.28 ± 1.06 a: intensity of red 9.93+ 0.55 7.71 ± 0.62 8.97 ± 0.70 b: intensity of yellow 12 .67 ± 0.41 15.18 ± 0.33 13.73 ± 0.53

The hair treated with shampoo A has a lesser degree of white and a greater intensity of red compared to the others. Thus, the surfactant poor in inorganic salts improves the fixing of the dye and increases the remanence of the dye on the hair.

Claims

1. Cosmetic composition for hair coloring, comprising a) from 0.1 to 30% of at least one amphoteric surfactant derived from amino acid and having an inorganic salt content of at most 1% by weight relative to said surfactant; b) from 0.01 to 30% of a hair coloring agent chosen from oxidation dyes and direct dyes, and c) a cosmetically acceptable vehicle.

2. Composition according to claim 1, in which the amphoteric surfactant is derived from carboxylic or sulfonic amino acid and is chosen from betaine, sulfobetaine, amidoalkylbetaine, amidoalkylsulfobetaine and amphoacetate surfactants.

3. Composition according to claim 2, in which the surfactant derived from amino carboxylic or sulfonic acid is chosen from:

- the betaines of formula 1, + R1 R2 R3NR4 C (O) O ^" (1) _ the sulfo-betaines of formula 2: Ri R2 R3NR4 SO3- (2)

_ the amidoalkylbetaines of formula 3: RιC (0) - NH R2 N (R3 R4) R5 C (O) 0 "(3)

_ the amidoalkylsulfo-betaines of formula 4:

RlC (O) - NH R2 N (R3 R4) R5 Sθ3 ^_ (4) - the alkylamphoacetates of formula (5): RιC (0) - NH - Rg - N - R7 - OH (5)

CH2 C (0) 0 M

formulas in which the radical R- _| represents an alkyl or alkenyl radical having from 10 to 24 carbon atoms, the radicals R2 and R3, identical or different, represent an alkyl radical having from 1 to 4 carbon atoms, the radicals R4 and R5 identical or different represent an alkylene radical having from 1 to 4 carbon atoms, the radicals Rg and R7 which are identical or different, represent an alkylene radical having 2 to 6 carbon atoms and M represents a hydrogen or alkali metal atom or an ammonium group.

4. Composition according to any one of the preceding claims, in which the surfactant has an inorganic salt content of 0.05 to 1% by weight.

5. Composition according to any one of the preceding claims, in which the surfactant having said content of inorganic salts is obtained by a dialysis process, in particular by electrodialysis, of precipitation of inorganic salts or of liquid-liquid extraction.

6. Composition according to one of claims 1 to 4, in which the amino acid-derived surfactant is an alkylamphoacetate of formula (5) obtained by reaction of an aminoalkylalkanolamine of formula (7)

R- _| C (0) NH R ₆ NH R ₇ -OH (7),

in which R- | , Rg and R7 have the previous meanings, with a cyanide of formula

(8)

XCN (8) in which X represents a hydrogen or alkali metal atom, followed by an alkaline hydrolysis of the nitrile formed in the case where X is a hydrogen atom.

7. Composition according to any one of the preceding claims, comprising from 2 to 10% of surfactant derived from amino acid having said content of inorganic salts.

8. Composition according to any one of the preceding claims, in which the coloring agent is of nonionic or cationic nature.

9. Composition according to any one of the preceding claims, comprising from 0.5 to 99.5% by weight of the said vehicle.

10. Composition according to any one of the preceding claims, characterized in that the vehicle is chosen from water, alcohols, hydrocarbons, halogenated hydrocarbons, esters, ketones, volatile silicones and mixtures of at any two of these products.

11. Composition according to any one of the preceding claims, further comprising a conditioning agent, or a fixing resin.

12. Composition according to any one of the preceding claims, further comprising at least one agent from anionic, cationic, nonionic or amphoteric surfactants; sequestering, humectant or emollient agents; protective agents for the skin or scalp such as water-soluble or water-dispersible polymers, non-allergenic derivatives of animal or vegetable proteins, hydrocolloids and their derivatives.

13. A method of manufacturing a composition according to any one of claims 1 to 12, characterized in that it comprises the steps consisting in; a) purifying an amino acid-derived surfactant having an inorganic salt content greater than 1% by weight, by a suitable separation technique to obtain a surfactant having a said salt content of at most 1% by weight, and b ) mix the surfactant thus obtained with the coloring agent and the vehicle, and optionally the other ingredients.

14. A method of manufacturing a composition according to any one of claims 1 to 12, characterized in that it comprises the steps consisting in: a) preparing a surfactant of formula (5) by reaction of an aminoalkylalkanolamine of formula (7)

R- _| C (0) NH R ₆ NH R ₇ -OH (7).

in which R- _j , Rg and R7 have the above meanings, with a cyanide of formula (8) XCN (8) in which X represents a hydrogen or alkali metal atom, followed by an alkaline hydrolysis of the nitrile formed in the case where X is a hydrogen atom, and

b) mixing the surfactant having an inorganic salt content of at most 1% by weight thus obtained, with the coloring agent and the vehicle, and optionally the other ingredients.