FR2945744A1 - Composition, useful for dyeing keratin material, preferably hair, comprises oxidation bases having 2((2-(4-amino-phenylamino)-ethyl)-(2-hydroxy-ethyl)-amino)-ethanol and methyl-quinoline-4-carbaldehyde - Google Patents

Abstract

Composition comprises one or more oxidation bases comprising 2-[[2-(4-amino -phenylamino)-ethyl]-(2-hydroxy-ethyl)-amino]-ethanol (I) or its addition salt with an acid; and one or more 1-methyl-quinoline-4-carbaldehyde compound (II), in a medium. Composition comprises one or more oxidation bases comprising 2-[[2-(4-amino-phenylamino)-ethyl]-(2-hydroxy-ethyl)-amino]-ethanol (I) or its addition salt with an acid; and one or more 1-methyl-quinoline-4-carbaldehyde compound of formula (II), in a medium. [Image].

Description

The subject of the invention is a dye composition comprising at least one particular para-phenylenediamine secondary oxidation base and a sodium salt of at least one alkali metal salt. The invention also relates to a dyeing composition comprising at least one secondary para-phenylenediamine oxidation base. 4-formyl-1-méthylquinolium. The subject of the invention is also the use of this composition for dyeing keratinous fibers as well as the dyeing process using this composition.

It is known to dye keratinous fibers and in particular human hair with dye compositions containing oxidation dye precursors, generally known as 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, when combined with oxidizing products, can give rise to colored compounds by a process of oxidative condensation. It is also known that the shades obtained with these oxidation bases can be varied 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 than indolic compounds. The variety of molecules involved in oxidation bases and couplers, allows to obtain a rich palette of colors. The so-called "permanent" coloration obtained with these oxidation dyes must also meet a certain number of requirements. Thus, it must be harmless from the toxicological point of view, it must make it possible to obtain shades in the desired intensity and to have good resistance to external agents such as light, bad weather, washing, permanent undulations, sweating and friction.

The dyes must also make it possible to cover the white hair, and finally be the least selective possible, that is to say, to obtain the lowest possible color differences throughout the same keratin fiber, which is in general differently sensitized (ie damaged) between its point and its root.

It is already known to use oxidation bases of the para-phenylene diamine secondary type of formula (I) below for dyeing keratinous fibers, especially the hair. In particular, such a base is disclosed in EP1580184 and EP0055386. This base has the drawbacks of leading to insufficiently intense or chromatic and / or too selective staining. Furthermore, it is known to use, in the field of dyeing keratin fibers, dyeing compositions using a salt of 4-formyl-1-methylquinolium, but the shades obtained are often selective and not very tenacious, particularly to light. The object of the present invention is to obtain a composition for hair dyeing which has improved dyeing properties in terms of intensity or chromaticity, and / or selectivity and / or resistance to external agents such as light .

This object is achieved with the present invention which relates to a dyeing composition of keratinous fibers comprising, in a suitable dyeing medium, one or more oxidation bases selected from compounds of formula (I) or its salts. addition with an acid, OH HO and -one or more compounds of formula (II) CHO N X-1 CH 3 (II)

X- denoting an anion for ensuring the electrical neutrality of the compound of formula (II).

The invention also relates to a dyeing process using this composition. Another subject of the invention is the use of the composition of the present invention for dyeing keratinous fibers, in particular human keratinous fibers such as the hair. The composition of the present invention makes it possible in particular to obtain a keratinous fiber coloring composition which is suitable for use in oxidation dyeing and makes it possible to obtain a coloring with various shades, intense or chromatic, aesthetic, not very selective and resistant. well to the various aggressions that can undergo the hair such as the shampoos, the sweat and the permanent deformations and in particular the light .. It should be noted that in what will follow, and unless another indication, the terminals of a domain of values are included in this area.

The compound of formula (I) may be in the form of addition salts chosen in particular from acid addition salts such as hydrochlorides, hydrobromides, sulphates, citrates, succincts, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates. The compound of formula (I) or its salts are generally present each in an amount of between 0.001 to 10% by weight of the total weight of the dye composition, preferably between 0.005 and 6%. The compound of formula (II) is used in salt form preferably chosen from hydrochloride, hydrobromide, sulphate, citrate, succinate, tartrate, lactate, tosylate, benzenesulfonate, phosphate and acetate. .

In the composition of the present invention, the compound or compounds of formula (II) generally represent an amount of between 0.01 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.05 and 5% . The dye composition according to the invention may contain one or more couplers conventionally used for dyeing keratinous fibers.

Among these couplers, there may be mentioned meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers, heterocyclic couplers and their addition salts. By way of example of a coupler, mention may be made of 2-methyl-5-aminophenol, 5-N- (13-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-dihydroxy benzene, 1,3-dihydroxy-2-methyl benzene, 4- chloro 1,3-dihydroxybenzene, 2,4-diamino 1- (13-hydroxyethyloxy) benzene, 2-amino-4- (R-hydroxyethylamino) -1-methoxybenzene, 1,3-diamino benzene, 1,3 bis (2,4-diaminophenoxy) propane, 3-ureido aniline, 3-ureido-1-dimethylamino benzene, sesamol, 1-13-hydroxyethylamino-3,4-methylenedioxybenzene, 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-hydroxy-pyridine, 6-hydroxybenzomorpholine 3,5-diamino-2,6-dimethoxypyridine, 2,6-dihydroxy-3-4-dimethylpyridine, 3-amino-2 - methylamino-6-methoxypyridine, 1-N- (R-hydroxyethyl) amino-3,4-methylene dioxybenzene, 2,6-bis- (R-hydroxyethylamino) toluene, 3-methyl-1-phenyl-5- pyrazolone and their addition salts with an acid.

In the composition of the present invention, the coupler or couplers, if they are present, generally represent an amount of between 0.001 and 10% by weight of the total weight of the dyeing composition, preferably between 0.005 and 6%. 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 its salts. By way of example, these additional oxidation bases are chosen from para-phenylenediamines, different from the oxidation bases of formula (I), bis-phenylalkylenediamines, para-aminophenols, bis-para-aminophenols, ortho aminophenols, heterocyclic bases and their addition salts. Among the para-phenylenediamines, there may be mentioned, for example, para-phenylenediamine, para-toluenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine and 2,6-dimethyl-para-phenylenediamine. 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N, N-dimethyl-para-phenylenediamine, N, N-diethyl-para-phenylenediamine, N, N-dipropyl para-phenylenediamine 4-amino N, N-diethyl-3-methylaniline, N, N-bis- (13-hydroxyethyl) para-phenylenediamine, 4-N, N-bis (13-hydroxyethyl) amino-2-methylaniline , 4-N, N-bis - ((3-hydroxyethyl) amino 2-chloroaniline, the

2-13-hydroxyethyl para-phenylenediamine, 2-fluoro para-phenylenediamine, 2-isopropyl para-phenylenediamine, N- (13-hydroxypropyl) para-phenylenediamine, 2-hydroxymethyl para-phenylenediamine, N, N-dimethyl 3 methyl para-phenylenediamine, N, N- (ethyl, 13-hydroxyethyl) para-phenylenediamine, N - ((3-yl-dihydroxypropyl) para-phenylenediamine, N- (4'-aminophenyl) para-phenylenediamine, N-phenyl para-phenylenediamine, 2-13-hydroxyethyloxy para-phenylenediamine, 2-13-acetylaminoethyloxy-para-phenylenediamine, N- (13-methoxyethyl) para-phenylenediamine, 4-aminophenylpyrrolidine, 2- thienyl para-phenylenediamine, 2- (3-hydroxyethylamino-5-amino-toluene, 3-hydroxy-1- (4'-aminophenyl) pyrrolidine and their addition salts with an acid.From the para-phenylenediamines mentioned above, the paraphenylenediamine, para-toluenediamine, 2-isopropyl para-phenylenediamine, 2-13-hydroxyethyl-para-phenyl ylenediamine, 2- [3-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N, N-bis- ([3-hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, 2- [3-acetylaminoethyloxy para-phenylenediamine, and their acid addition salts are particularly preferred.

Among the bis-phenylalkylenediamines, mention may be made, by way of example, of N, N'-bis- ((3-hydroxyethyl) N, N'-bis (4'-aminophenyl) -1,3-diamino propanol, the N, N'-bis - ([3-hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis; - (13-hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methylaminophenyl) tetramethylenediamine, N, N'-bis (ethyl) N, N'-bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1,8-bis (2,5-diamino phenoxy) -3,6-dioxaoctane, and their addition salts with an acid. Among para-aminophenols, para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluoro phenol, 4-amino-3-hydroxymethylphenol, 4-amino-2 are exemplified. methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (13-hydroxyethylaminomethyl) phenol, 4-amino-2 -fluorine o phenol, 1-hydroxy-4-methylamino-benzene, 2-2'-methylenebis-4-amino phenol and their addition salts with an acid. Among the ortho-aminophenols, mention may be made, for example, of 2-amino phenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and their addition salts with an acid. Among the heterocyclic bases that may be mentioned by way of example are pyridine derivatives, pyrimidine derivatives and pyrazole derivatives. Among the pyridine derivatives, mention may be made of the compounds described for example in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino-3-amino pyridine, 2,3-diamino-6-methoxy-pyridine, 2 - ((3-methoxyethyl) amino-3-amino-6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid Among the pyrimidine derivatives the compounds described for example in DE 2359399, JP 88-169571, JP 05-63124, EP 0770375 or WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4- hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2750048 and among which mention may be made of 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-amino pyrazolo [1,5-a] pyrimidin-7-ol; 3-amino pyrazolo [1,5-a] pyrimidin-5-ol; 2- (3-amino pyrazolo [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-hydroxyethyl) 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-imidazolylpropylamino pyrazolo [1,5-a] pyrimidine and their acid addition salts and their tautomeric forms, when tautomeric equilibrium exists. Among the pyrazole derivatives, mention may be made of the compounds described in DE 3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 as the 4.5 1-methyl pyrazole, 4,5-diamino-1- (13-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-phenylpyrazole, 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 1- (13-hydroxyethyl) 3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 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-meth 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- (13-hydroxyethyl) amino-1-methyl pyrazole, and their addition salts with an acid. There may also be mentioned diaminopyrazolinones described in 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 that can be used in the context of the invention are chosen especially from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates and addition salts with a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines. The dye composition in accordance with the invention may also contain one or more direct dyes that may be chosen in particular from nitro dyes of the benzene series, azo direct dyes and methine direct dyes. These direct dyes may be nonionic, anionic or cationic in nature. The medium suitable for dyeing, also known as a dyeing medium, generally comprises water or a mixture of water and one or more solvents such as, for example, lower C 1 -C 4 alkanols, 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 can 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 approximately.

The dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic polymers, cationic, nonionic, amphoteric, zwitterionic or their mixtures, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents. The adjuvants above are generally present in an amount for each of them between 0.01 and 20% by weight relative to the weight of the composition. Of course, one skilled in the art will take care to choose this or these optional additional compounds such that the advantageous properties intrinsically attached to the oxidation dyeing composition according to the invention are not, or not substantially impaired by the addition or additions envisaged. The pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used for dyeing keratin fibers or else using conventional buffer systems. Among the acidifying agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids. Among the alkalinizing agents that may be mentioned, by way of example, are ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium or potassium hydroxides and following formula (III): ## STR2 ## wherein W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical; Ra, Rb, Rd and Rd, which may be identical or different, represent a hydrogen atom, a C1-C4 alkyl radical or a C1-C4 hydroxyalkyl radical. 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 suitable for dyeing keratinous fibers, and especially human hair. It can result from mixing at the time of use of several compositions. In a particular variant it results from the mixture of two compositions, one containing one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and optionally one or more couplers and the other containing the compound or compounds of formula (II). The composition of the invention may be applied to the hair in the presence of an oxidizing agent which allows the coloration of the keratinous fibers. The oxidizing agents conventionally used for the oxidation dyeing of keratinous fibers are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and oxidase enzymes. among which there may be mentioned peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred. The process of the present invention is a process in which the composition according to the present invention as defined above is applied to the fibers for a time sufficient to develop the desired coloration. The color can be revealed at acidic, neutral or alkaline pH.

After a residence time of about 3 to 50 minutes, preferably about 5 to 30 minutes, the keratinous fibers are rinsed, washed with shampoo, rinsed again and then dried. The oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing hair and as defined above. The invention also relates to a multi-compartment device or "kit" of dyeing in which a first compartment contains the dye composition of the present invention defined above and a second compartment contains one or more oxidizing agents. Another device consists of a first compartment containing a composition comprising one or more oxidation bases selected from the compound of formula (I) or its addition salts with an acid and optionally one or more couplers, a second compartment containing a composition comprising the compound (s) of formula (II) and a third compartment containing one or more oxidizing agents. These devices may be equipped with means for delivering the desired mixture onto the hair, such as the devices described in patent FR-2 586 913 in the name of the applicant.

From these devices, it is possible to dye the keratinous fibers from a process which comprises mixing a dye composition comprising one or more compounds of formula (I), and one or more compounds of formula (II) , and optionally one or more different couplers of the compounds of formula (II) with one or more oxidizing agents, and the application of the mixture obtained on the keratinous fibers for a time sufficient to develop the desired coloration. The examples which follow serve to illustrate the invention without, however, being limiting in nature.

EXAMPLES

EXAMPLES OF DYEING EXAMPLE 1 The following compositions are prepared: Composition Composition 1 2 2 - [{2 - [(4-Aminophenyl) amino] ethyl} (2 -0 -0.01 mol hydroxyethyl) amino] ethanol trihydrochloride 4-Formyl-1-methylquinolinium 4- 0.01 mol Methylbenzenesulphonate Sulfite of sodium 0.1 g 0.1 g Sodium lauryl ether sulphate oxyethylenated (2.2OE) 1.0g 1.0g at 30% in aqueous solution Ethanol 5.0 g 5.0 g Ammonia at 20% NH3 4.0 g 4.0 g Demineralized water qs 100 g 100 g Application mode

Compositions 1 and 2 are mixed weight for weight. The mixture obtained is applied to gray hair with 90% of white hair at a rate of 10 g per 1 g of hair. After 30 minutes of laying, the hair was then rinsed, washed with standard shampoo and dried.

Results Capillary staining was evaluated visually. We obtain a coloration of brown hair with purple reflection. 10

Claims (13)

REVENDICATIONS1. Coloring composition of keratinous fibers comprising, in a medium suitable for dyeing keratinous fibers: one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, H HO and one or more compounds (II) of formula CHO N X-1 CH3 (II) X- denoting an anion making it possible to ensure the electrical neutrality of the compound of formula (II). 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 of the total weight of the dye composition. 3. Composition according to any one of the preceding claims, characterized in that X- denotes a chloride, bromide, sulfate, citrate, succinate, tartrate, lactate, tosylate, benzene sulphonate, phosphate or acetate anion. 4. Composition according to any one of the preceding claims, characterized in that the compound or compounds of formula (II) generally represent an amount of between 0.01 and 10% by weight of the total weight of the dye composition, preferably between 0.05 and 5%. 5. Composition according to any one of the preceding claims, characterized in that it contains one or more couplers. 6. Composition according to the preceding claim, characterized in that the coupler or couplers are selected from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers, heterocyclic couplers and their addition salts. 7. Composition according to any one of claims 5 or 6, characterized in that the coupler or couplers represent an amount of between 0.001 and 10% by weight of the total weight of the dye composition, preferably between 0.005 and 6%. 8. Composition according to any one of the preceding claims, characterized in that it contains one or more oxidizing agents. 9. Composition according to the preceding claim, characterized in that the oxidizing agent is selected from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes and preferably the hydrogen peroxide. 10. A process for dyeing keratinous fibers, wherein the composition as defined in any one of claims 1 to 9 is applied to the keratinous fibers for a time sufficient to develop the desired coloration. 11. The method of claim 10 in the presence of an oxidizing agent selected from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes and preferably the peroxide of hydrogen. 12. Multi-compartment device in which a first compartment contains a dye composition as defined in any one of claims 1 to 9 and a second compartment contains one or more oxidizing agents. 13. Multi-compartment device in which a first compartment contains a dye composition comprising one or more oxidation bases selected from the compound of formula (I) or one of its salts with an acid and optionally one or more couplers other than compounds of formula (II) as described in any one of claims 1 to 7, a second compartment containing a composition comprising one or more compounds of formula (II) as described in any one of claims 1 to 4 and a third compartment containing one or more oxidizing agents.