FR2745178A1 - COSMETIC COMPOSITION FOR HAIR COLORING AND METHODS OF PREPARATION - 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

The present invention relates to cosmetic compositions for capillary 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 the dyes and ensuring their stability. A number of solutions exist but often requires the use of surfactants irritating to the skin and / or the eye or containing impurities incompatible with a cosmetic application.

However, in recent years, there is a very important 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.

Non-irritating product investigations converged on amphoteric (ie, having an overall electrical charge of zero) surfactants of the betaine or amphoacetate type, the synthetic 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 thus leads to the release of Na + Cl-, the Cl- anion from monochloroacetic acid, as well as the release of sodium glycolate from the hydrolysis of the starting acid.

The major disadvantages encountered with the surfactants of the above type are the following - detrimental influence on the deposition of dyes on the hair.

- significant increase in the viscosity of the surfactant solution that does not allow
to concentrate the solutions beyond a concentration by weight of about 30% because the
viscosity increases sharply, which prevents the marketing of solutions
concentrated; - deterioration of the cold behavior and emulsifying and stabilizing properties; - problem of compatibility with the other additives of the compositions (agents
thickeners, preservatives, silicone emulsions, fixative resins, agents
conditioners, etc.) It has been unexpectedly found that the performance of the cosmetic compositions which are the subject of the invention can be achieved by a 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, hair coloring is made more effective and more durable.

The present invention relates to cosmetic compositions for hair dyeing comprising: a) from 0.1 to 30% of an amphoteric surfactant derived from an amino acid having an inorganic salt content of at most 1% by weight; b) from 0.01 to 30% of a hair coloring agent, selected from oxidation dyes and direct dyes, and c) a cosmetically acceptable vehicle.

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

The term composition or cosmetic formulation is understood to mean all cosmetic products or preparations such as those described in Annex I ("illustrative list by category of cosmetic products") of European Directive 76/768 / EEC of 27 July 1976 cosmetic.

The coloring agent of any type known from hair dyes may in particular be of anionic, cationic, nonionic or amphoteric nature, or a mixture. Dyestuffs of a nonionic and / or cationic nature will preferably be used.

Among the coloring agents which may be used as constituents of the cosmetic compositions which are the subject of the invention, mention may be made, by way of non-limiting examples, of the class of oxidation dyes: These are the coloring ingredients which will give rise to coloration through an oxidation reaction. The oxidizing agent may be oxygen in the air, oxygenated water, or persulfates of the ammonium persulfate type.

aromatic derivatives containing primary or secondary amine groups such as, for example, N- (2-hydroxyethyl), N-ethyl chloro-p-phenylene diamine; 3,4-methylene dioxyaniline; 4-amino-2-methylphenol, 4-amino-3-hydroxybenzoic acid; 7-amino-4-hydroxy-2-naphthalenesulfonic acid; 4,4'-diaminobenzophenone; bis-1,3- (N- (4-aminophenyl) hydoxyethylamino-2) propan-2-ol, or mixtures thereof.

heterocyclic derivatives such as for example 2-amino-4-methoxy-6-methylpyrimidine, 6-amino-nicotinic acid, 2,6-dihydroxy-3,4-dimethylpyridine, or mixtures thereof.

phenol or polyphenol derivatives such as, for example, pyrocatechol, resorcinol, pyrogallol, phloroglucinol, 1,5-dihydroxy naphthalene, nitro derivatives such as 2-nitro-p-phenylenediamine, 5-chloro-nitro- 3-phenylenediamine, 2-amino-4-nitro-phenol, 4-amino-2-nitro-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-hydroxyethylamino-5-nitro benzene, 4-nitro-3-methylamino-phenoxyethanol, 2-amino-3-methyl-3-nitro benzene, 3-hydroxy-amino 4-nitro benzene, or mixtures thereof.

anthraquinone derivatives, for example those listed by name of the
Color Index as Disperse Violet 4, Disperse Blue I, Acid Violet 43, Disperse Violet 1, Acid Blue 62, or mixtures thereof.

indoamine derivatives, for example N-hydroxyethylamino-2-methoxy-5,2-aminoaniline-4'-benzoquinone-1,4, N- (3-chloro-methylaminophenyl-4 ') -ureido-3-methyl-6-benzoquinone; 1.4 imine.

acridinic dyes, for example acridine orange (basic orange 14), xanthene dyes such as, for example, rhodamine B (basic violet 10), and azotic dyes such as disperse yellow 3, basic red 76, and 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 mixtures thereof.

- Azine dyes such as basic red 2.

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

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

These surfactants may be in particular betaine or sulfobetaine surfactants, including amidoalkylbetaines and amidoalkyl sulfobetaines, or alternatively amphoacetate surfactants or amphodiacetates.

Among the surfactants of betaine type, mention will be made, for example
betaines of formula 1
R1 R2 R3 NR4 C (O) O- (1)
sulfobetaines of formula 2:
R1R2R3NR4SO3- (2)
amidoalkyl betaines of formula 3:
R1C (O) -NH R4N (R2R3) R5C (O) O- (3)
and the amidoalkylsulfobetaines of formula 4:
R1C (O) -NH R4N (R2R3) R5SO3- (4) in which the radical R1 represents an alkyl or alkenyl radical having from 10 to 24 carbon atoms, the radicals R2, and R3, which are identical or different, represent a alkyl radical having 1 to 4 carbon atoms, and the radicals R4 and R5, identical or different, represent an alkylene radical having 1 to 4 carbon atoms.

The betaines of formula (i) can be obtained in particular by carboxylation of the amine of formula R1 R2R3N with the halocarboxylic acid of formula Hal-R4COOH or a salt thereof, whereas the sulphobetaines of formula (2) can be obtained in particular by sulfonation of the amine of formula R 1 R 2 R 3 N by the halosulfonic acid of formula
Hal-R4-SO3H or a salt thereof in the presence of an alkaline agent. These reactions are accompanied by the release of the corresponding alkaline halide salt.

The amidoalkyl betaines or sulfobetaines are obtained analogously from the corresponding amidoalkylamine.

dans laquelle R1 a la signification ci-dessus et représente le plus souvent des chaînes coco et lauryle, R6 et R7 identiques ou différents, représentent un radical alkylène ayant 2 à 6 atomes de carbone, et M représente un atome d'hydrogène ou de métal alcalin, ou un ion ammonium.Among the surfactants of the amphoacetate type, mention will be made more particularly of alkylamphoacetates corresponding to the general formula (5):

in which R 1 has the above meaning and most often represents coco and lauryl chains, R 6 and R 7, which are identical or different, represent an alkylene radical having 2 to 6 carbon atoms, and M represents a hydrogen or metal atom. alkali, or an ammonium ion.

et leurs homologues répondant plus généralement à la formule (5)

formules dans lesquelles R1, R6 , R7 et M ont les significations ci-dessus.The present invention more specifically relates to cosmetic compositions comprising amphoteric surfactants such as alkylamphoacetates, and more particularly the amidoamine derivatives listed in the Cosmetics dictionary.
Toiletries Fragrance Association "1994 edition under the names alkylamphoacetate or alkylamphodiacetate and having the formula:

and their counterparts more generally responding to formula (5)

formulas in which R1, R6, R7 and M have the meanings above.

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

in which R 1, R 6 and R 7 have the meanings given above, or of one of its open-ring 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 set to 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 temperature of the reaction being preferably between 75 and 85in.

For the purposes of the present invention, the various surfactants derived from carboxylic or sulphonic amino acids described above must have a low content of inorganic salts, in particular alkali halides which may derive from their synthesis, namely at most 1% by weight. . Absolute purity with respect to the 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 cosmetic hair compositions which are the subject of the invention may be obtained according to various purification methods well known to those skilled in the art, such as, for example, the purification by dialysis or electrodialysis of solutions. aqueous surfactants as described in the French patent application N95 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 according to synthetic methods 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):
In which R1, R8 and R7 have the meaning indicated above with formaldehyde and a cyanide of formula (8): ## STR2 ##
XCN (8) wherein X represents a hydrogen atom or an alkali metal, especially lithium, sodium or potassium, provided that if X is a hydrogen atom, the nitrile obtained is hydrolyzed with an alkaline agent.

Such a cyanide process is described in British Patent Application No. 94.23573 filed November 22, 1994. The alkaline agent is preferably sodium hydroxide.

Preferably, R6 and R7 are identical and represent an ethylene radical in formula (7).

The preferred methods of preparation of the surfactants which are 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 amino acid-derived surfactants having an inorganic salt content of not more than 1% by weight, used in the hair cosmetic compositions forming the subject of the invention, are present in an amount corresponding to about 0.degree. , 1-30%, advantageously 0.5-30% by weight relative to the total weight of the formulation, preferably from 2 to 10%. The quantities can be adjusted to obtain the best level of performance.

The compositions forming the subject of the invention relate above all to the hair field in order to modify permanently or temporarily 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 eyelashes, eyebrows, and hairs.

The pH of the compositions forming the subject of the invention may advantageously be between 3 and 11, preferably between 5 and 10.

 It is adjusted by alkaline agents such as monoethanolamine, diethanolamine, triethanolamine, ammonia, ammonium, potassium or sodium carbonates, sodium hydroxide, 2-amino-2-methylpropanol -1, or with acidifying agents such as phosphoric acid, hydrochloric acid, tartaric acid, acetic acid, lactic acid or citric acid.

The compositions forming the subject of the invention can be applied to natural, permed, colored or bleached hair. The hair may also have been subjected to a lightening treatment, either with a solution of ammoniacal oxygenated water or containing alkaline agents such as aliphatic or hydroxyaliphatic amines, or with an ammoniacal solution of peroxides or alkaline 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 forming the subject of the invention comprise a vehicle, or a mixture of several vehicles, which are compatible with a capillary application. These vehicles may 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" means here that the vehicle does not damage or exert any negative effects on the appearance of the hair or does not cause irritation of the skin and / or the eye and / or the scalp.

Vehicles compatible with the applications described in this invention include, for example, those used in sprays, foams, tonics, gels, shampoos, or rinse lotions. The choice of the appropriate vehicle will depend on the nature of the constituents, particularly the resin, and whether the formulated product is intended to be left on the surface where it has been applied (eg sprays, foams, toner, or gels) or rinsed after use (eg shampoo, conditioner, rinse lotions).

The vehicles that may be used include a large number of products commonly used in hair cosmetic compositions. The vehicles may comprise a solvent for solubilizing or dispersing the ingredients used, such as water, C1-C6 alcohols, and mixtures thereof, in particular water and methanol,
Ethanol, isopropanol, and mixtures thereof.

The vehicles may 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, decamethylcyclopenta siloxane, cyclodimethicone, and dimethicone), and mixtures thereof.

When these cosmetic hair 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 may 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 foams) or in the form of fine, uniform sprays. By way of examples, mention may be made of trichlorofluoromethane, dichlorodifluoromethane, difluoroethane, dimethyl ether, propane, n-butane, or isobutane.

These vehicles can take a lot of forms. For example, vehicles in the form of emulsions include water-in-oil, oil-in-water, and oil-in-silicone emulsions. These emulsions cover a wide range of viscosity, from 0.1 to 200 Pa.s. These emulsions can also be delivered in the form of sprays using either a device of mechanical pump type, or in the form of aerosol pressurized by the use of a propellant gas. These vehicles can also be delivered in the form of foam. Examples which may be mentioned are anhydrous liquid solvents, such as oils, alcohols and silicones, homogeneous aqueous mixtures such as hydroalcoholic mixtures, and 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 that can be used in the context of this invention, there are the conditioning agents of animal origin, such as hydrolysates of animal proteins and their salts, such as the dimethyl or trimethyl ammonium stearate salts of collagen hydrolysates, silk, keratin; 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 of oxy-1,1 'bis (chloro-2) ethane or polyquaternium-2, the copolymer of diallyldimethylammonium chloride and acrylamide or polyquaternium-7; cationic derivatives of polysaccharides, such as cocodimonium hydroxyethylcellulose, guar hydroxypropyltrimonium chloride, hydroxypropyl guar hydroxypropyltrimonium chloride (Jaguar C13S, Jaguar C162 sold by RHONE-POULENC), poly (oxyethanediyl-1,2) ether, ) 2-hydroxy-trimethylammonium-3-propyl cellulose or polyquaternium-10 chloride; silicones and silicone derivatives such as amodimethicone, cyclomethicone, copolyol cetyl dimethicone, cyclomethicone, dimethicone copolyol, trimethylsilyl amodimethicone, polyquaternium-80; cationic surfactants such as distearyl dimethyl ammonium chloride.

The conditioning agents used as constituents of the hair cosmetic compositions that are the subject of the invention are preferably chosen from conditioning agents of synthetic origin, in particular the polyquaterniums -2, -7, and -10, and the cationic derivatives of polysaccharides. such as cocodimonium hydroxyethylcellulose, hydroxypropyl trimonium guar chloride, hydroxypropyl guar hydroxypropyltrimonium chloride.

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

The performance of the cosmetic compositions which are the subject of the invention can also be improved by the use of plasticizing agents. The plasticizer may advantageously represent from 0.1 to 20% by weight of the formulation, preferably from 1 to 15%. Among the plasticizers which are particularly useful, mention may be made of adipates, phthalates, isophthalates and azelates. , stearates, silicone copolyols, glycols,
Castor oil, or mixtures thereof.

The hair cosmetic compositions which are the subject of the invention may also contain fixing 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% by weight. %.

The fixing resins that may be used according to the invention are preferably chosen from the following resins: acrylate / acrylamide copolymers, polyvinylmethyl ether / maleic anhydride, vinyl acetate / crotonic acid, octylacrylamide / acrylate / butylaminoethyl methacrylate, polyvinylpyrrolidone (PVP), copolymers of polyvinylpyrrolidone, especially copolymers of polyvinylpyrrolidone and methyl methacrylate. copolymers of polyvinylpyrrolidone and vinyl acetate (VA), polyvinyl alcohol, copolymers of polyvinyl alcohol and crotonic acid, copolymers of polyvinyl alcohol and maleic anhydride, sodium polystyrene sulfonate; a polyvinylpyrrolidone / ethyl methacrylate / methacrylic acid terpolymer, poly (methylvinyl ether / maleic acid) monomethyl ether; polycondensates of ethylene glycol terephthalate / ethylene glycol, polycondensates of diester, terephthalic acid / anhydride / sulfoisophthalic / glycol, and mixtures thereof, polyvinyl acetate grafted onto polyoxyalkylene trunks such as poly (acetate vinyl) grafted on polyoxyethylene trunks (EP-A-219 048), polyester copolymers based on ethylene terephthalate units and / or propylene terephthalate. and polyoxyethylene terephthalate, with a ratio of the number of units of ethylene terephthalate and / or propylene terephthalate to 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 molecular weight of the order of 300 to 5000, preferably of 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); sulfonated polyester oligomers obtained by sulfonation of an oligomer derived from ethoxylated allyl alcohol, dimethyl terephthalate and 1,2-propylene diol having from 1 to 4 sulfonated groups (US-A-4,968,451); polyester copolymers based on propylene terephthalate and polyoxyethylene terephthalate units and terminated with ethyl or methyl units (US-A-4,711,730) or polyester oligomers terminated by alkylpolyethoxy groups (US-A-4,702,857) or sulfopolyethoxy anionic groups (US-A-4,721,580); sulfoaroyles (US-A-4,877,896); polyesterpolyurethanes obtained by reacting a polyester with a number-average molecular mass of 300-4000 obtained from adipic acid and / or terephthalic acid and / or sulfoisophthalic acid and a diol having a mass of less than 300, on a prepolymer with terminal isocyanate groups obtained from a polyoxyethylene glycol with a molecular mass of 600-4000 and a diisocyanate (FR-A-2 334 698); sulphonated polyester oligomers obtained by condensation of isophthalic acid, dimethyl sulphosuccinate and diethylene glycol (FR-A-2,236,926); sulfonated polyesters obtained by condensation of dimethyl terephthalate / isophthalic acid / sodium dimethylsulfonate isophthalate / ethylene glycol (EP-A-540 374); or their mixtures.

In addition, cationic resins can also be used. These cationic resins consist entirely or partly of cationic monomers such as, for example, dimethylaminoethyl methacrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethylammonium chloride, or mixtures thereof.

Preferably, the fixing resins which are the subject of the invention will be of the polyvinylpyrrolidone (PVP) type, copolymers of polyvinylpyrrolidone and methyl methacrylate, copolymer of polyvinylpyrrolidone and of vinyl acetate (VA), polycondensates of ethylene terephthalate glycol / ethylene glycol, diester polycondensates, terephthalic acid / anhydride / sulfoisophthalic acid / g lycol, and mixtures thereof.

These fixative resins are preferably dispersed or solubilized in the chosen vehicle.

These cosmetic hair compositions may also comprise surfactants which serve to disperse, emulsify, solubilize, 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. Anionic and nonionic surfactants are thus found. cationic, zwitterionic or amphoteric compounds or mixtures of these surfactants.

In particular, surfactants such as. alkyl ester sulfonates of formula R-CH (SO 3 M) -COOR ', where R represents a C 8 -C 20 alkyl radical, preferably a C 10 -C 16 alkyl radical, R' a C 1 -C 6 alkyl radical, preferably a C 1 -C 3 alkyl radical, and M an alkaline cation (especially sodium, potassium, lithium), a substituted or unsubstituted ammonium (in particular methyl-dimethyl-, trimethyl-, tetramethylammonium, or dimethylpiperidinium) or derived from an alkanolamine (in particular monoethanolamine, diethanolamine or triethanolamine). Mention may especially be made of methyl ester sulfonates whose radical R is C14-C16; alkylsulfates of formula ROsO3M, where R represents a C10-C24, preferably C12-C20, and especially C12-C18, alkyl or hydroxyalkyl radical, M representing a hydrogen atom or a cation of the same definition as above; as well as their ethoxylated (EO) and / or propoxylated (PO) derivatives, having on average from 0.5 to 6 units, preferably from 0.5 to 3 EO and / or OP units; . alkylamide sulphates of formula RCONHR'OSO3M where R represents an alkyl radical
C2-C22, preferably C6-C20, R 'a C2-C3 alkyl radical, M representing a hydrogen atom or a cation of the same definition as above, and their ethoxylated derivatives (EO) and / or propoxylated (PO), with an average of 0.5 to 60 EO and / or
OP; . saturated or unsaturated C8-C24, preferably C14-C20 fatty acid salts, C8-C20 alkylbenzenesulfonates, primary or secondary alkylsulfonates,
C8-C22, alkylglycerol sulphonates, sulphonated polycarboxylic acids disclosed in GB-A-1 082 179, paraffin sulfonates, N-acyl N-alkyltaurates, alkylphosphates, alkylisethionates, alkylsuccinamates, alkylsulfosuccinates, monoesters or diesters sulfosuccinates, N-acyl sarcosinates, sulphates of alkylg lycosides, 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 derivative of an alkanolamine (especially monoethanolamine, diethanolamine or triethanolamine) - nonionic surfactants, such as for example. polyoxyalkylenated alkylphenols (especially polyoxyethylenated, polyoxypropylenated, polyoxybutylenated) whose alkyl substituent is C 6 -C 12 and containing from 5 to
.the condensation products of fatty acids and protein hydrolysates, alkylampho
propionates or -dipropionates, which are used to reduce the irritation caused by
other surfactants, mainly anionic surfactants.

It is also advantageous to add to these hair compositions agents
sequestering metals, especially those sequestering calcium such as
citrate ions or emollient agents such as silicones or oils or fats
used in this respect in the cosmetics industry (in particular mineral oils, fatty acid esters, triglycerides, ....).

It is also possible to advantageously incorporate the humectant agents with the hair cosmetic compositions which are the subject of the invention. There may be mentioned glycerol, sorbitol,
Urea, collagen, gelatin, aloe vera, hyaluronic acid. Emollients which are generally chosen from alkylmonoglycerides, alkyldiglycerides and triglycerides, such as oils extracted from plants and plants (especially palm, coconut, cottonseed, soybean, sunflower, olive, grapeseed, sesame, peanut, castor ...) 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, squalene, diols such as -2-propanediol, 1,3-butanediol,
Cetyl alcohol, stearyl alcohol, oleic alcohol, polyethylene glycols or polypropylene glycols, fatty esters such as isopropyl palmitate, 2-ethylhexyl cocoate, myristyl myristate, esters of lactic acid , Stearic acid, behenic acid, isostearic acid, silicone oils comprising cyclic polydimethylsiloxanes, polydimethylsiloxanes-e, hydroxylated, polydimethylsiloxanes, trimethylsilylated, polyorganosiloxanes such as polyalkylmethylsiloxanes, polymethylphenylsiloxanes, polydiphenylsiloxanes, derivatives thereof. amino silicones.

silicone waxes, silicone copolyethers (such as SILBIONE 70646 oil marketed by RHONE-POULENC or DC 190 marketed by DOW)
CORNING) or mixed silicone derivatives including various types of derivatization (such as mixed polyalkylmethylsiloxane-silicone copolyether copolymers).

To further reduce the irritation or aggression of 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 (hydrolisates of wheat proteins for example), natural hydrocolloids ( such as guar gum, carob, tara, etc.) 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 as their nonionic derivatives (for example hydroxypropylguar), anionic derivatives (carboxymethylguar) or mixed nonionic / anionic derivatives such as carboxy-hydroxypropyl guars.

The basic constituents may optionally be added in combination with powders or mineral particles such as calcium carbonate, mineral oxides in the form of powder or in colloidal form (particles of smaller size or of the order of one micrometer, sometimes of some 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 trademark GERMABEN or any chemical agent avoiding bacterial proliferation or molds and traditionally used in the compositions Cosmetics may advantageously be introduced into the compositions of the invention, especially up to 0.01 to 3% by weight. The amount of these products is generally adjusted to prevent any proliferation of bacteria, molds or yeasts in the cosmetic compositions.

As an alternative to these chemical agents, it is sometimes possible to use agents that modify the activity of water and strongly increase the osmotic pressure, such as carbohydrates or salts.

To protect the hair from sun and UV rays, we can add to these formulations sunscreens which are either chemical compounds strongly absorbing UV radiation such as the compounds authorized in the European directive N 76/768 / CEE, its annexes and subsequent amendments to this Directive, or titanium dioxide or cerium oxides in the form of powder or colloidal particles. These powders may 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 to increase the approval during the use of the composition by the consumer, one or more perfumes, coloring agents of the composition among which may be mentioned the products described in Annex IV ("lisp of the european directive n 76/768 / EEC of 27 July 1976, known as the "cosmetic directive". and / or opacifying agents such as pigments. It is also possible to incorporate in the composition bactericidal or fungicidal agents in order to improve the disinfection of the scalp, for example triclosan. Finally, the composition may also contain viscosifying or gelling polymers, such as crosslinked polyacrylates -particularly CARBOPOL brand products sold 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 .... used alone or in combination, or the same compounds, generally in the form of hydrosoluble polymers modified by hydrophobic groups covalently bonded to the polymer backbone as described in 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, especially in amounts of the order of 0.1-7% by weight, to control the hardness of calcium and magnesium, agents such as water-soluble salts of polycarboxylic acids with a molecular mass of about 2,000 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 especially polyacrylates with a molecular weight of about 2,000 to 10,000 (US-A-3,308,067), copolymers of arylic acid and maleic anhydride with a molecular weight of from 5,000 to 75,000 (EP
A-66 915) polyethylene glycols of molecular weight of the order of 1000 to 50 000.

The subject of the invention is also a method for manufacturing a composition as described above, characterized in that it comprises the steps of: a) purifying an amino acid-derived surfactant having an inorganic salt content greater than 1 % by weight, by a separation technique suitable for obtaining 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 method which is the subject of the invention is characterized in that it comprises the steps of: a) preparing a surfactant of formula (5) by reacting an aminoalkylalkanolamine of formula (7)
Wherein R 1, R 6 and R 7 have the above meanings, with a cyanide of formula (8)
XCN (8) wherein 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 a salt content inorganic compounds 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 low inorganic salt content
A pilot electrodialyzer of the TS-2-10P type marketed by the Company is used.
Eurodia. This electrodialyzer has a total effective membrane surface of 2000 cm 2 and comprises 10 cells with 2 compartments of 200 cm 2 of useful unit area.

The anionic and cationic membranes used are membranes marketed by Eurodia or Tokoyama Soda whose references are respectively
Neosepta AM1 and Neosepta CMX.

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

The reaction is carried out at ambient temperature with a current density of 18.4 mA / cm 2. The initial NaCl content is 8.5% based on 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 content of sodium chloride is determined and a value of 0.6% is found, the sodium glycolate is also measured and it is found that it passes from a content of 1.2% to 0.6% . The final viscosity is 71 mPa.s. The concentration of cocoamphomonoacetate increases from 26% to 33%.

The irritant potential was evaluated 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.

ABC
(according
the invention) (comparative) - Lauryl Ether Sodium Sulfate
Empicol ESB 3M 7 10 7 - Reference example product (30%) 3 - Miranol C2M (30%) - - 3 (cocoamphoacetate containing 11% of inorganic NaCl salts) - Coloring solution * 31,43 31,43 31 , 43 - Conservative qs qsqs

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

The coloring solution corresponding to a coppery reflection, proposed by the company Les Dyes
Wacker, has the following composition:% odes
Covariane Purple W 5121 1,2
Yellow Covariane W 1125 1.9
Covariane red W 3121 1,4
Solvariane 95.5 (the dyes being totally dissolved in the solvarian)
The tests are performed on Indian hair degraded ref NWI R hair of the company HTS (Germany) - wick of 5g. For each test, a series of 3 wicks was performed.

The wicks are wetted without washing and squeezed between two fingers. Using a disposable pipette, apply 3 ml of shampoo dye from the root to the tip. Then spread over the entire hair by massaging slightly and lather. Allowed to act for 60 min so that the coloring develops completely. A little warm water (35-370 ° C) is added and the mixture is massed slightly. Finally rinse thoroughly with lukewarm water until the rinse water is completely clear.

Results:
The measurement of the color of the locks was carried out visually and by measurement with the Lab colorimeter using a LUCI QC V1.0 apparatus 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 faded lock of hair having a very light ashy blond coloring. Just after the treatment, it is found that - the locks treated with the shampoo A have an intense pink color, - the locks treated with the shampoo B have a blond coloring, - the locks treated with the shampoo C have a rosy blond coloring.

The colorations in descending order of intensity are A>C>>B>> reference
ash blond.

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

<tb> Hair <SEP> treated <SEP> reference <SEP> A <SEP> B <SEP> C
<tb> Just <SEP> after <SEP> processing <SEP>
<tb> L: <SEP> degree <SEP> of <SEP> white <SEP> 55,53t1 <SEP>, 40 <SEP> 36,21 <SEP> +0,99 <SEP> 35,67 + 0, 98 <SEP> 36.66 <SE> s 0.61 <SEP>
<tb> a <SEP>: <SEP> intensity <SEP> of <SEP> red <SEP> 2.27 + 0.18 <SEP> 11.43 + 0.36 <SEP> 9.64t0.43 <SEP > i0,65t0,57 <SEP>
<tb> b <SEP>: <SEP> intensity <SEP> yellow <SEP> 15.42 # 0.50 <SEP><SEP> 11.1 <SEP> 8t0.41 <SEP> i <SEP> 3.55t0, 43 <SEP> 12.39+ <SEP> 0.29
<tb> aDrès <SEP> 5 <SEP> Washes
<tb> L <SEP>: <SEP> degree <SEP> of <SEP> white <SEP> 41.34 <SEP> + <SEP> 1.07 <SEP> 43.52 # 1.25 <SEP><SEP> 42.28 + 1.06 <SEP>
<tb> a <SEP>: <SEP> intensity <SEP> of <SEP> red <SEP> 9.93+ <SEP> 0.55 <SEP> 7.71 <SEP> + <SEP> 0.62 <SEP> 8.97t0.70
<tb> b <SEP>: <SEP> intensity <SEP> of <SEP> yellow <SEP> 12.67 + 0.41 <SEP> 15.18t0.33 <SEP> 13.73t0.53 <SEP>
<Tb>
The hair treated with shampoo A has a lesser degree of whiteness and a greater intensity of red compared to others.
Thus, the surfactant low in inorganic salts improves the fixing of the dye and increases the persistence of the dye on the hair.

Claims (14)

 A cosmetic composition for hair dyeing, comprising a) from 0.1 to 30% of at least one amino acid derived amphoteric surfactant and having an inorganic salt content of at most 1% by weight with respect to said surfactant; b) from 0.01 to 30% of a hair dye agent selected from oxidation dyes and direct dyes, and  (c) a cosmetically acceptable vehicle.  2. Composition according to claim 1, wherein the amphoteric surfactant is derived from amino carboxylic or sulfonic acid and is selected from the surfactants betaine, sulfobetaine, amidoalkylbétaine, amidoalkylsulfobétaine and amphoacétate.  3. Composition according to Claim 2, in which the surfactant derived from amino carboxylic or sulphonic acid is chosen from: betaines of formula 1,  R1 R2R3NR4C (O) O- (1)  sulfobetaines of formula 2:  +  RiR2R3NR4SO3- (2)  amidoalkyl betaines of formula 3:  + R1C (O) -NH R2N (R3Rq) RgC (O) O- (3)  amidoalkylsulfobetaines of formula 4:  + R1C (O) -NH R2 N (R3 R4) R SO3- (4) - the alkylamphoacetates of formula (5):

 formulas in which the radical R 1 represents an alkyl or alkenyl radical having from 10 to 24 carbon atoms, the radicals R 2 and R 3, which are identical or different, represent an alkyl radical having from 1 to 4 carbon atoms, the radicals R 4 and R 5, identical or different represent an alkylene radical having 1 to 4 carbon atoms, the radicals R6 and R7, which may be identical or different, represent an alkylene radical having 2 to 6 carbon atoms and M represents a hydrogen or an alkali metal atom or an ammonium group.  4. A composition according to any one of the preceding claims wherein the surfactant has an inorganic salt content of 0.05 to 1% by weight.  5. Composition according to any one of the preceding claims wherein the surfactant having said content of inorganic salts is obtained by a dialysis process, in particular by electrodialysis, precipitation of inorganic salts or liquid-liquid extraction.  6. Composition according to one of claims 1 to 4, wherein the amino acid derivative surfactant is an alkylamphoacetate of formula (5) obtained by reaction of an aminoalkylalkanolamine of formula (7) Wherein R 1, R 6 and R 7 have the above meanings, with a cyanide of formula (8) XCN (8) wherein 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.  A composition according to any one of the preceding claims, comprising from 2 to 10% of an amino acid derivative surfactant 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 said vehicle.  10. Composition according to any one of the preceding claims, characterized in that the vehicle is selected from water, alcohols, hydrocarbons, halogenated hydrocarbons, esters, ketones, volatile silicones and mixtures of at least two of these products.  11. Composition according to any one of the preceding claims further comprising a conditioning agent, or a fixative resin.  12. Composition according to any one of the preceding claims, further comprising at least one of anionic, cationic, nonionic or amphoteric surfactants; sequestering, humectant or emollient agents; protective agents for the skin or the 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 of: a) purifying an amino acid derivative surfactant having an inorganic salt content greater than 1 % in weight. by a separation technique suitable for obtaining a surfactant having a salt content of at most 1% by weight. and b) mixing the surfactant thus obtained with the coloring agent and the carrier, and optionally the other ingredients.  14. A method of manufacturing a composition according to any one of claims 1 to 2. characterized in that it comprises the steps of: a) preparing a surfactant of formula (5) by reaction of an aminoalkylalkanolamine of formula (7) Wherein R 1, R 6 and R 7 have the above meanings, with a cyanide of formula (8) XCN (8) wherein 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 a salt content inorganic compounds of at most 1% by weight thus obtained, with the coloring agent and the vehicle, and optionally the other ingredients.