FR2857858A1 - Wash-fast dyeing of keratin fibers, especially human hair, using fused polycyclic aromatic cyclohexane-trione or bis-cyclohexane trione derivative - Google Patents

Abstract

The use of compositions (A) for dyeing keratin fibers, where (A) comprise a dyeing medium containing at least one ninhydrin analog selected from fused polycyclic aromatic cyclohexane-1,2,3-trione derivatives (I) or fused polycyclic bis-cyclohexane-1,2,3-trione derivatives (II), is new. The use of compositions (A) for dyeing keratin fibers is claimed, where (A) comprise a dyeing medium containing at least one fused cyclohexane trione derivative of formulae (I) or (II). [Image] R1 - R6H, halo, alkyl, OH, alkoxy, optionally substituted benzoxy, optionally substituted aryloxy, NH2, mono- or dialkylamino, mono- or di-hydroxyalkylamino, thio, alkylthio, thioalkyl, alkylcarbonyl, CHO, COOH, alkoxycarbonyl, NO2, sulfonato or corresponding protonated groups such as ammonio, imidazolio or pyridinio; or at least 5 membered, monocyclic or fused or non-fused polycyclic aromatic group, optionally containing heteroatom(s) selected from N, O, S and/or P and optionally substituted by one or more of halo, alkyl, OH, alkoxy, NH2, mono- or dialkylamino, mono- or di-hydroxyalkylamino, thio, alkylthio, thioalkyl, alkylcarbonyl, CHO, COOH, alkoxycarbonyl, NO2, sulfonato, trialkylammonio, phenoxy, imidazolyl or pyridinyl; or R1 + R2, R2 + R3, R4 + R5 or R5 + R6OCH2O or a group completing 5- or 6-membered, aromatic or non-aromatic ring, optionally containing heteroatoms and/or substituted as for the aromatic groups R1> - R6>; A : aliphatic or aromatic polycyclic system, optionally containing heteroatoms and/or substituted as for the aromatic groups R1> - R6>; all alkyl moieties have 1-6C. Independent claims are included for: (1) a cosmetic dyeing composition comprising a dyeing medium containing at least one compound (I)/(II) and at least one nonionic, cationic, anionic or amphoteric surfactant and/or polymer; (2) a ready for use cosmetic dyeing composition containing at least one compound (I)/(II) and at least one compound (III) selected from compounds containing a primary or secondary amine function and/or active methylene compounds; (3) a multi-component dyeing agent comprising (A) as first component and a composition (B) containing at least one compound (III), (A) and (B) preferably being contained in separate compartments of a multi-component kit; and (4) a hair dyeing method involving contacting the hair with (A) for a sufficient period, then rinsing and washing the hair.

Description

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Use in hair coloration of cyclic aromatic vicinal trion with condensed rings
The present invention relates to hair dye compositions containing at least one fused-ring polycyclic aromatic vicinal trione, preferably associated with a primary or secondary amine functional compound or an activated methylene compound, a hair dyeing method using such compositions and a multi-component coloring agent for carrying out such a method.

 For a long time, many people have been trying to change the color of their hair and in particular to hide their white hair. To do this, several technologies have been developed.

 It is known to dye human keratin fibers, and in particular the hair, with dye compositions containing oxidation dye precursors, generally known as oxidation bases. These oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, give rise to colored compounds by a process of oxidative condensation.

These dyes are insoluble and are trapped inside the hair fiber.

 It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or color modifiers. The variety of molecules involved in the oxidation bases and couplers allows a rich palette of colors to be obtained.

 The colorations obtained have good toughness to shampoos.

However, the oxidation reaction is carried out using oxidizing products such as hydrogen peroxide in basic medium. These oxidizing agents attack hair keratin make the cosmetic and mechanical properties can degrade sharply in case of repeated staining.

 It is also known to dye human keratinous fibers by a direct dyeing consisting in applying direct dyes to the keratin fibers.

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 which are colored molecules and dyes having an affinity for the fibers. Examples of direct dyes conventionally used are nitro, benzene, anthraquinone, nitropyridine, azo, cationic azo, xanthene, acridine, azine or triarylmethane dyes or natural dyes.

 The colorations thus obtained are, of course, very chromatic and do not cause a chemical degradation of the keratin, but have the disadvantage of being only temporary or semi-permanent, that is to say to fade at better after only 4 to 5 shampoos.

 There is therefore still a need for coloring systems and methods which make it possible to obtain good toughness without involving the use of oxidizing agents capable of degrading the keratinous fibers.

 The Applicant has surprisingly discovered that the use of certain polycyclic aromatic vicinal triones, described in more detail below, makes it possible to color the keratinous fibers, and in particular the hair, with tenacities equivalent to or even greater than those obtained by coloring. oxidation and this in the absence of strong oxidizing agents thus perfectly preserving the keratinous fibers.

 The polycyclic aromatic vicinal triones mentioned above are preferably used in combination with labile hydrogen compounds, such as primary or secondary amines or activated methylene compounds.

 The colorations thus obtained have good chromaticities and are distinguished in particular by an excellent washing tenacity (several tens of shampoos).

 The invention therefore relates to the use, for hair dyeing, of a composition containing, in a medium suitable for dyeing, at least one compound of formula (I) or (II) or its tautomeric form:

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dans lesquelles R1, R2, R3, R4, R5 et R6 représentent, indépendamment les uns des autres, chacun un atome d'hydrogène, un atome d'halogène, un groupe alkyle en C1-6, hydroxy, alcoxy en Ci~6, benzoxy éventuellement substitué, aryloxy éventuellement substitué, amino,

mono- ou di-(alkyle en Cl-6)-amino, mono- ou di-(hydroxyalkyle en Cl-6)-amino, thio, alkylthio en C1-6, thioalkyle en C1-6, (alkyle en C 1~6)-carbonyle, hydrogénocarbonyle, hydroxycarbonyle, (alcoxy en C1-6)-carbonyle, nitro, sulfonato et tri(alkyle en C1-6)ammonio, ou un groupe aromatique comportant au moins 5 chaînons, monocyclique ou polycyclique à cycles condensés ou non condensés, comportant éventuellement un ou plusieurs hétéroatomes choisis parmi N, 0, S et P, et portant éventuellement un ou plusieurs substituants choisis parmi les atomes d'halogène, les groupes alkyle en C1-6, hydroxy, alcoxy en CI-6' amino, mono- ou di-(alkyle en C1-6)-amino, mono- ou di- (hydroxyalkyle en C1-6)-amino, thio, alkylthio en C1-6, thioalkyle en C1-6, (alkyle en C 1~6)-carbonyle, hydrogénocarbonyle, hydroxycarbonyle, (alcoxy en C1-6)-carbonyle, nitro, sulfonato, tri(alkyle en C1-6)-ammonio, phénoxy, imidazolyle et pyridinyle, ou R1 et R2, R2 et R3, R3 et R4, R4 et R5, ou R5 et R6 forment ensemble, deux par deux, un groupe -O-CH2-O- ou un cycle à 5 ou 6 chaînons, aromatique ou non aromatique, contenant éventuellement un ou plusieurs hétéroatomes choisis parmi N, 0, S et P, et portant éventuellement un ou plusieurs substituants choisis parmi les atomes d'halogène, les groupes alkyle en C , hydroxy, alcoxy en C1-6, amino, mono- ou di-

(alkyle en C1~6)-amino, mono- ou di-(hydroxyalkyle en C1~6)-amino, thio, alkylthio en Ci.6, thioalkyle en C1-6, (alkyle en C i~6)-carbonyle, hydrogénocarbonyle, hydroxycarbonyle, (alcoxy en C1-6)-carbonyle, nitro, sulfonato, tri(alkyle en C1-6)ammonio, imidazolyle et pyridinyle, et

in which R 1, R 2, R 3, R 4, R 5 and R 6 represent, independently of each other, each a hydrogen atom, a halogen atom, a C 1-6 alkyl, hydroxy, C 1-6 alkoxy group, optionally substituted benzoxy, optionally substituted aryloxy, amino,

mono- or di-C 1-6 alkylamino, mono- or di- (C 1-6 hydroxyalkyl) amino, thio, C 1-6 alkylthio, C 1-6 thioalkyl, C 1-6 alkyl; 6) -carbonyl, hydrogen carbonyl, hydroxycarbonyl, (C 1-6 alkoxy) carbonyl, nitro, sulfonato and tri (C 1-6 alkyl) ammonio, or an aromatic group having at least 5 members, monocyclic or polycyclic fused rings or non-condensed, optionally containing one or more heteroatoms selected from N, O, S and P, and optionally bearing one or more substituents selected from halogen atoms, C 1-6 alkyl, hydroxy, C 1-6 alkoxy groups; amino, mono- or di-C 1-6 alkylamino, mono- or di- (C 1-6 hydroxyalkyl) amino, thio, C 1-6 alkylthio, C 1-6 thioalkyl, C 1-6 alkyl 1-6) -carbonyl, hydrogenocarbonyl, hydroxycarbonyl, (C 1-6 alkoxy) -carbonyl, nitro, sulfonato, tri (C 1-6 alkyl) -ammonio, phenoxy, imidazolyl and pyridinyl, or R 1 and R 2, R 2 and R 3 , R3 and R4, R4 and R5, or R5 and R6 formen t together, two-by-two, a -O-CH 2 -O- group or a 5- or 6-membered ring, aromatic or non-aromatic, optionally containing one or more heteroatoms selected from N, O, S and P, and optionally carrying a or more substituents selected from halogen atoms, C 1-6 alkyl, hydroxy, C 1-6 alkoxy, amino, mono- or di-

(C 1-6 alkyl) amino, mono- or di- (C 1-6 hydroxyalkyl) amino, thio, C 1-6 alkylthio, thioC 1-6 alkyl, C 1-6 alkylcarbonyl, hydrogenocarbonyl, hydroxycarbonyl, (C 1-6 alkoxy) carbonyl, nitro, sulfonato, tri (C 1-6 alkyl) ammonio, imidazolyl and pyridinyl, and

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 A represents an aromatic or aliphatic polycyclic system, optionally comprising one or more heteroatoms chosen from N, O, S and P and optionally carrying one or more substituents chosen from substituents of the aromatic groups represented by R 1 to R 6 above.

 In a preferred embodiment of the present invention, A is selected to form by condensation with the two C6-trione rings a delocalized electron system.

 The halogen atoms include the chlorine, bromine, fluorine and iodine atoms.

 The compounds of formulas (I) and (II) include, of course, also the acid addition salts and the corresponding base addition salts.

The polycyclic aromatic vicinal triones of formula (I) and (II) above are used in the present invention in a cosmetically acceptable medium generally containing a large fraction of water. When dissolved in such an aqueous medium, these compounds are in hydration equilibrium with the gemini diol form (or carbonyl hydrate) corresponding to the following formulas (Ib) and (IIa):

When, in the present application, triones of formula (I) and (II) are concerned, they therefore always include not only the

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 formula (I) and (II) but also the corresponding hydrated forms of formula (Ibis) and (IIbis).

où les substituants R1 à R4 ont les définitions indiquées ci-dessus pour R1 à R6. In a preferred embodiment of the compounds of formula (II) of the present invention, A represents a naphthalene ring forming by condensation with the two adjacent C6 rings a pyrene-1,2,3,6,7,8-hexone of formula (III):

where the substituents R1 to R4 have the definitions given above for R1 to R6.

dans laquelle les substituants R1 à R8 ont la signification indiquée ci-dessus pour les substituants R1 à R6de la formule (I). In another preferred embodiment of the compounds of formula (Et) of the present invention, A represents a perylene ring forming, by condensation with the two adjacent C6 rings, a dibenzo- [cd, lm] perylene-1,2, 3,8,9,10-hexone of formula (IV)

wherein the substituents R1 to R8 have the meaning indicated above for the substituents R1 to R6 of the formula (I).

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Preferred examples of cyclic polycyclic aromatic vicinal triones with fused rings which can be used in accordance with the present invention for coloring hair fibers are as follows:

1ri-phénaléne-1,G,-trlone

1RI-phenalen-1, G, -trlone

4,9-dihydroxy-lH-phénalène-l,2,3-trione

4,9-dihydroxy-lH-phenalene-l, 2,3-trione

4,9-diméthoxy-1H-phénalène-1,2,3-trione

4,9-dimethoxy-1H-phenalene-1,2,3-trione

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5-nitro-lH-phénalène-l,2,3-trione

5-nitro-lH-phenalene-l, 2,3-trione

1,2,3,6,7,8-pyrenehexone @

5,6,12,13-tétrachloro-dibenzo [cd,lm]pérylène-1,2,3,8,9,10-hexone

5,6,12,13-tétraphénoxy-dibenzo[cd,lm]pérylène-l,2,3,8,9,10-hexone

5,6,12,13-tetrachloro-dibenzo [cd, lm] perylene-1,2,3,8,9,10-hexone

5,6,12,13-tetraphenoxy-dibenz [cd, lm] perylene-l, 2,3,8,9,10-hexon

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The polycyclic aromatic vicinal triones of formula (I) and (II) used in the present invention are known. The synthesis of the exemplified compounds (a) to (g) is described for example in the two following publications: # 1H-phenalene-1,2,3-trione: G. Errera Gazz. Chim. Ital. 431,583 (1913) # 1,2,3,6,7,8-pyrenehexone: R. Gleiter, R. Kraemer, H. Irngartinger, C.

Bissinger, J. Org. Chem. 57, 252 (1992).

 According to the present invention, the polycyclic aromatic vicinal triones of formula (I) and (II) described above can be used alone for coloring hair fibers. Indeed, these compounds are capable of generating molecules stained with the amine functions of keratin (color reaction). Compounds of formula (I) and / or (II) may also be used together with at least one labile hydrogen compound selected from those having a primary or secondary amine function and those having an activated methylene function. It is of course also possible to use a mixture of such labile hydrogen compounds.

 The primary amine or secondary amine compounds are preferably aromatic amines.

 Examples of such aromatic amines are N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine and N- (2-hydroxyethyl) -N-ethyl-p-phenylenediamine. N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, N- (2-methoxyethyl) -p-phenylenediamine, 2,3-, 2,4- or 2,5-dichloro-p-phenylene diamine, 2-chloro-p-phenylenediamine, 2,5dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3- or 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, ortho-phenylenediamine, p-phenylenediamine, ortho-toluenediamine, 2,5-diaminotoluene, 2,5-diaminophenol, 2,5-diaminophenethol, 4-amino-3-methylphenol, 2- (2,5-diaminophenyl) -ethanol, 2,4-diaminophenoxyethanol, 2- (2,5-diaminophenoxy) -

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dans laquelle
R9 représente un groupe hydroxy ou amino éventuellement substitués par un groupe alkyle en Ci-4, hydroxyalkyle en CI-4 ou (alcoxy en Ci.4)-(alkyle en Cl-4),
R10, R11, R12, R13 et R14 représentent chacun indépendamment un atome d'hydrogène, un groupe hydroxy ou un groupe amino, éventuellement substitués par ethanol, 4-methylaminoaniline, 3-amino-4- (2'-hydroxyethyloxy) aniline, 3,4-methylenediaminoaniline, 3,4-methylenedioxyaniline, 3-amino-2,4-dichlorophenol, 4- methylaminophenol, 2-methyl-5-aminophenol, 3-methyl-4-aminophenol, 2-methyl-5- (2-hydroxyethylamino) phenol, 6-methyl-3-amino-2-chlorophenol, 2- methyl-5-amino-4-chlorophenol, 3,4-methylenedioxyphenol,
5- (2-hydroxyethylamino) -4-methoxy-2-methylphenol, 4-amino-2-hydroxymethylphenol, 1,3-diamino-2,4-dimethoxybenzene, 2-, 3-, 4-aminobenzoic acid , 2-amino-, 3-amino or 4-aminophenylacetic acid, 2,3- acid,
2,4-, 2,5-, 3,4- or 3,5-diaminobenzoic acid, 4-amino- or 5-amino-salicylic acid, 3-amino-4-hydroxybenzoic acid, -amino-3-hydroxybenzoic acid
2-amino-, 3-amino or 4-aminobenzenesulfonic acid, 3-amino-4-hydroxybenzenesulfonic acid, 4-amino-3-hydroxynaphthalene-1-sulfonic acid, 6-amino-7-hydroxynaphthalene acid, 2-sulfonic acid, 7-amino-4-hydroxynaphthalene-2-sulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid, 3-amino-2-naphthoic acid, 3- aminophthalic acid, 5-aminoisophthalic acid, 1,3,5-triaminobenzene, 1,2,4-triaminobenzene, 1,2,4,5-tetraaminobenzene, 2,4,5-triaminophenol, pentaaminobenzene, hexaaminobenzene, 2,4,6-triaminoresorcinol, 4,5-diaminopyrochatecol, 4,6-diaminopyrogallol, 3,5-diamino-4-hydroxypyrochatecol, and aromatic anilines and aromatic phenols with another aromatic residue corresponding to formula (II)

in which
R9 is hydroxy or amino optionally substituted with C1-4alkyl, C1-4alkylalkyl or (C1-4alkoxy) - (C1-4alkyl),
R10, R11, R12, R13 and R14 each independently represent a hydrogen atom, a hydroxy group or an amino group, optionally substituted with

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C 1-4 alkyl, C 1-4 hydroxyalkyl or (C 1-4 alkoxy) - (C 1-4 alkyl), or a carboxylic or sulfonic acid group,
Z represents a direct bond, a saturated or unsaturated, optionally hydroxylated, C1-C4 hydrocarbon chain, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group of formula Q- (CH2-P- Where P represents a direct bond or a group -CH2- or -CHOH-, Q and Q 'represent, independently of one another, an oxygen atom, a group NR15 where R15 represents a hydrogen atom, a C1-4 alkyl or C1-4 hydroxyalkyl group, or a 0- (CH2) pNH or NH- (CH2) p'-0 group where p and p 'are 2 or 3 and o is a number between 1 and 4.

 The nonaromatic primary or secondary amines are, for example, 2-aminoethanol, 2-methoxyethylamine, 2-ethoxyethylamine, 2- (2-aminoethoxy) ethanol, 2- or 3-aminopropanol, 2,3-dihydroxypropylamine, 4-hydroxypropylamine, 2-aminopropane-1,3-diol, 2-amino-2-methylpropanol, 2-amino-2-methylpropane-1,3-diol, 2-amino-2-hydroxymethylpropane-1,3 diol, tetrahydropentylamine, pentahydroxyhexylamines such as glucamine, Dglucosamine, D-galactosamine, 1,2-diaminoethane, 1,2- or 1,3-diaminopropane, 1,3-diamino-2-propanol, 2- (2-Aminoethylamino) ethylamine, 2- (2-aminoethylamino) ethanol, 3- (2-aminoethylamino) propylamine and 3- (2-aminoethylamino) propanol.

 The compounds with an activated methylene function are chosen, for example, from the following: 1,2,3,3-tetramethyl-3H-indolium iodide, 1,2,3,3-tetramethyl-3H-indolium p-toluenesulphonate 1,2,3,3-tetramethyl-3Hindolium methanesulfonate, 1,3,3-trimethyl-2-methylene-indoline, 2,3-dimethylbenzothiazolium iodide, 2,3-dimethyl-p-toluenesulfonate, benzothiazolium, rhodanine, rhodanine-3-acetic acid, i-ethyl-2-quinaldinium iodide, 1-methyl-2-quinaldinium iodide, barbituric acid, thiobarbituric acid, acid

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 1,3-dimethylthiobarbituric acid, diethylthiobarbituric acid, oxindole, 3-indoxyl acetate, coumarone and 1-methyl-3-phenyl-2-pyrazolinone.

 These primary and secondary amines and these activated methylene compounds as well as other labile hydrogen compounds are also described in DE 43 17 855, DE 197 17 222, DE 198 45 481 and DE 197 45 355 where are used for the staining of keratinous fibers in combination with ninhydrin derivatives.

 When the polycyclic aromatic vicinal triones of formula (I) and (II) are used in combination with a primary or secondary amine or with an activated methylene compound, it is necessary to keep these different reagents separately to avoid a premature color reaction. The contacting of the reagents is then done immediately before application to the hair, by extemporaneous mixing of two compositions respectively containing the vicinal triones of formula (I) and (II) and the compounds with labile hydrogen.

 The invention therefore also relates to a multi-component hair coloring agent comprising # as a first component, a composition (a) containing at least one polycyclic aromatic vicinal trione of formula (I) or (II), and # as a second component, a composition (b) containing at least one primary or secondary amine functional compound or at least one activated methylene compound, as described above.

 This multi-component hair coloring agent is preferably in the form of a multi-compartment kit, with at least a first compartment containing the first component (composition (a)) and at least a second compartment containing the second component (composition (b)).

 The invention also relates to a dye cosmetic composition containing at least one polycyclic aromatic vicinal trione of formula (I) or (II) and at least one cosmetic active ingredient.

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 The cosmetic active principles present in the cosmetic compositions of the present invention are chosen, for example, from vitamins, saccharides, oligosaccharides, hydrolysed or non-modified polysaccharides, modified or otherwise, amino acids, oligopeptides, peptides and hydrolysed proteins. or not, modified or not, amino polyacids, enzymes, branched or unbranched fatty acids and alcohols, animal, vegetable or mineral waxes, ceramides and pseudo-ceramides, hydroxylated organic acids, UV filters, agents antioxidants and anti-free radical agents, chelating agents, anti-dandruff agents, seborrhea regulating agents, soothing agents, cationic, anionic, nonionic or amphoteric surfactants, cationic, anionic, neutral or amphoteric polymers, organomodified silicones, mineral, vegetable or animal oils, polyisobutene and poly (α-olefins), fatty esters, anionic polymers in dissolved or dispersed form, nonionic polymers in dissolved or dispersed form, reducing agents, solvents, hair dyes such as direct dyes or oxidation dye precursors (bases and / or couplers) different from the primary or secondary amine compounds claimed, the oxidizing agents such as hydrogen peroxide optionally combined with persalts, the pigments and their mixtures.

 The cosmetic active ingredient is preferably present in an amount of from 0.001 to 50% by weight, in particular from 0.01 to 20% by weight, and most preferably from 0.1 to 10% by weight, based on the total weight of the cosmetic composition.

 In a preferred embodiment of the cosmetic dye composition according to the invention, the cosmetic active ingredient is a surfactant and / or a polymeric agent (polymer), these agents may be of a nonionic, cationic, anionic or amphoteric nature.

 It follows from the above that the hair dyeing compositions used in the present invention are storage stable when they contain, as sole coloring reagents, polycyclic aromatic vicinal triones.

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 of formula (I) or (II), but they must be prepared immediately before use, when they contain both polycyclic aromatic vicinal triones of formula (I) or (II) and compounds with labile hydrogen such that primary and secondary amines or activated methylene compounds.

 These ready-to-use coloring compositions, whether stable in storage or prepared immediately before use, preferably have a pH of between 2 and 12, and in particular between 3 and 11.

 Their polycyclic aromatic vicinal trion content of formula (I) or (II) is preferably between 0.0001% and 30% by weight.

 The compounds with labile hydrogen used in combination with the triones of formula (I) or (II) are preferably present in a proportion of 0.0001% to 30% based on the total weight of the composition.

 The present invention further relates to a hair dyeing method comprising applying to the hair a hair dye composition ready for use as described above. This composition is left in contact with the hair fibers for a time sufficient to obtain the desired color. This exposure time is generally between 5 minutes and 1 hour, and in particular between 15 and 30 minutes. The color reaction between the polycyclic aromatic vicinal triones and the amine functions of keratin or the labile hydrogen compounds that may be present may be accelerated by heating the impregnated hair with the coloring composition. The heating temperature preferably does not exceed 80.degree. C., and in particular is less than or equal to 60.degree.

 After obtaining the desired coloration, the hair is rinsed and washed.

 When labile hydrogen compounds such as primary or secondary amines or activated methylene compounds are used, the reagents involved in the color reaction can also be applied in two stages, ie two compositions can be successively applied. different

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 containing respectively at least one polycyclic aromatic vicinal trione of formula (I) or (II) and at least one compound having a primary or secondary amine function or an activated methylene function.

 The present invention therefore also relates to a two-step hair dyeing process comprising applying to the hair one after the other, in any order, a composition (a) and a composition ( b) as defined above for the multicomponent coloring agent.

 This separate application of the two reactive compositions has the advantage of avoiding the manipulation of colored compositions and thus reduces the risk of staining of materials such as clothing.

 The Applicant has found that satisfactory capillary stains are also obtained when an intermediate rinsing step is inserted between the application of the first composition and the application of the second composition.

 In a manner analogous to that described above, the hair impregnated with composition (a) and / or (b) may be heated, preferably to a temperature of 80 ° C., and in particular to a temperature not exceeding 60 C, such heating to accelerate the color reaction and shorten the exposure time.

Example
The following composition is prepared: 1H-phenalene-1,2,3-trione (compound of formula (a)) 10 -2 moles
Ethanol 50 g
NaOH qsp pH 7
Distilled water qs 100 g

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This composition is applied to two strands of natural hair and permed with 90% of white hair, 1 g each. The bath ratio is 5, the exposure time is 30 minutes and the temperature is 60 C. At the end of the exposure time, the locks are rinsed and then washed with a standard shampoo.

The intensity of coloration is evaluated by colorimetry according to the system
CIELAB using a Minolta CM3600d colorimeter (illuminant D65, viewing angle: 10, specular component included).

The CIELAB notation system defines a color space in which each color is defined by 3 parameters (L *, a * and b *): - the parameter L * reflects the clarity of the color, the value of L * being equal to
0 for black and 1 for absolute white. The higher the L * value, the less intense the color.

 the parameter a * corresponds to the axis of the green-red antagonistic pair and the parameter b * to the axis of the blue-yellow antagonistic pair.

AE reflète la variation globale de la couleur. Sa valeur est d'autant plus grande que la variation de couleur est importante.

The table below shows the parameters L *, a * and b * of strands of natural hair and hair permed before and after the rise of the color, as well as AE defined by the following equation:

AE reflects the overall variation of color. Its value is all the greater as the color variation is important.

<Tb>
<Tb>

Hair <SEP> L * <SEP> a * <SEP> b * <SEP> AE <SEP> Color
<tb> natural <SEP> Before <SEP> staining <SEP> 60,84 <SEP> 0,03 <SEP> 11,63- <SEP> natural <SEP> After <SEP> staining <SEP> 25,71- 2.45 <SEP> 6.54 <SEP> 35.58 <SEP> Matte
<tb> permuted <SEP> Before <SEP> staining <SEP> 61.78 <SEP> 0.33 <SEP> 12.74- <SEP> permuted <SEP> After <SEP> staining <SEP> 18.93- 0.14 <SEP> 2.33 <SE> 44.11 <SEP> mat
<Tb>

Claims (17)

 mono- or di-C 1-6 alkylamino, mono- or di- (C 1-6 hydroxyalkyl) amino, thio, C 1-6 alkylthio, C 1-6 thioalkyl, C 1-6 alkyl; 6) -carbonyl, hydrogen carbonyl, hydroxycarbonyl, (C 1-6 alkoxy) carbonyl, nitro, sulfonato and tri (C 1-6 alkyl) ammonio, or an aromatic group having at least 5 members, monocyclic or polycyclic fused rings or non-condensed, optionally containing one or more heteroatoms selected from N, O, S and P, and optionally bearing one or more substituents selected from halogen atoms, C 1-6 alkyl, hydroxy, C 1-6 alkoxy, amino, mono- or di-C 1-6 alkylamino, mono- or di- (C 1-6 hydroxyalkyl) amino, thio, C 1-6 alkylthio, C 1-6 thioalkyl, C 1-6 alkyl (6) -carbonyl, hydrogenocarbonyl, hydroxycarbonyl, (C 1-6 alkoxy) -carbonyl, nitro, sulfonato, tri (C 1-6 alkyl) -ammonio, phenoxy, imidazolyl and pyridinyl, or R 1 and R 2, R 2 and R 3 , R3 and R4, R4 and R5, or R5 and R6 formen t together, two-by-two, a -O-CH 2 -O- or a 5- or 6-membered aromatic or non-aromatic ring, optionally containing one or more heteroatoms selected from N, O, S and P, and

 wherein R 1, R 2, R 3, R 4, R 5 and R 6 independently of one another are each hydrogen, halogen, C 1-6 alkyl, hydroxy, C 1-6 alkoxy; optionally substituted benzoxy, optionally substituted aryloxy, amino,

 1. Use for the hair coloration of a composition containing, in a medium suitable for dyeing, at least one compound of formula (I) or (II): <Desc / Clms Page number 17>  optionally bearing one or more substituents selected from halogen atoms, C 1-6 alkyl, hydroxy, C 1-6 alkoxy, amino, mono- or di-C 1-6 alkylamino, mono- or di- (C1-6 hydroxyalkyl) amino, thio, C1-6 alkylthio, C1-6thioalkyl, (C1 -6 alkyl) -carbonyl, hydrogenocarbonyl, hydroxycarbonyl, C1-6 alkoxycarbonyl nitro, sulfonato, tri (C 1-6 alkyl) aminio, imidazolyl and pyridinyl, and A represents an aromatic or aliphatic polycyclic system, optionally comprising one or more heteroatoms selected from N, O, S and P and optionally bearing one or more substituents selected from substituents of the aromatic groups represented by R 1 to R 6 above.  2. Use according to claim 1, characterized in that A represents a naphthalene nucleus which forms, by condensation with the two adjacent C6 rings, a 1,2,3,6,7,8-hexene-pyrene of formula ( III)

 in which the substituents R1 to R4 have the meaning given in claim 1.  3. Use according to claim 1, characterized in that A represents a perylene ring forming, by condensation with the two adjacent C6 rings, a dibenzo- [cd, lm] perylene-1,2,3,8,9, 10-hexone of formula (IV): <Desc / Clms Page number 18>  (IV) wherein the substituents R1 to R8 have the meaning given in claim 1 for the substituents R1 to R6 of the formula (I).

 4. Use according to one of claims 1 to 3, characterized in that the composition further comprises at least one compound having a primary or secondary amine function or at least one activated methylene compound or a mixture thereof .  5. Use according to Claim 4, characterized in that the compound comprising a primary or secondary amine function is an aromatic amine chosen from N, N-dimethyl-p-phenylenediamine and N, N-diethyl-p-phenylenediamine, N - (2-hydroxyethyl) -N-ethyl-p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, N- (2-methoxyethyl) -p-phenylenediamine, 2 3-, 2,4- or 2,5-dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3- or 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, orthophenylenediamine, p-phenylenediamine, ortho-toluenediamine, 2,5-diaminotoluene, 2,5-diaminophenol, 2,5-diaminophenethol, 4-amino-3-methylphenol, 2- (2,5-diaminophenyl) ethanol, 2,4-diaminophenoxyethanol, 2- (2,5-diaminophenoxy) ethanol, 4- methylaminoaniline, 3-amino-4- (2-hydroxyethyloxy) aniline, 3,4-methylenediaminoaniline, 3,4-methylenedioxyaniline, 3-amino-2,4-dichlorophenol, 4-methylaminophenol, 2-methyl-5-aminophenol, 3-methyl-4-aminophenol, 2-methyl- 5- (2hydroxyethylamino) phenol, 6-methyl-3-amino-2-chlorophenol, 2-methyl-5-amino-4-chlorophenol, 3,4-methylenedioxyphenol, 5- (2-hydroxyethylamino) -4-methoxy-2 methylphenol, 4-amino-2-hydroxymethylphenol, 1,3-diamino-2,4-dimethoxybenzene, 2-, 3-, 4-aminobenzoic acid, 2-amino-, 3-amino acid or 4-aminophenylacetic acid, 2,3-, 2,4-, 2,5-, 3,4- or 3,5-diaminobenzoic acid, <Desc / Clms Page number 19> Z represents a direct bond, a saturated or unsaturated, optionally hydroxylated, C 4 'hydrocarbon-based chain, a carbonyl, sulphonyl or imino group, an oxygen or sulfur atom, or a group of formula Q- (CH 2 -P); Where P represents a direct bond or a group -CH2- or -CHOH-, Q and Q 'represent, independently of one another, an oxygen atom, a group NR15 where R15 represents a hydrogen atom, a C 1-4 alkyl or C 1-4 hydroxyalkyl group, or an O- (CH 2) pNH or NH- (CH 2) p -O group where p and p 'are 2 or 3 and o is a number between 1 and 4 or an aliphatic amine selected from 2-aminoethanol, 2-methoxyethylamine, 2-ethoxyethylamine, 2- (2-aminoethoxy) ethanol, 2- or 3-aminopropanol, 2,3 dihydroxypropylamine, 4-hydroxypropylamine, 2-aminopropane-1,3-diol,  C1-4alkyl, C1-4alkylalkyl or (C1-4alkoxy) -C1-4alkyl) or a carboxylic or sulfonic acid group,

R10, R11, R12, R13 and R14 each independently represent a hydrogen atom, a hydroxy group or an amino group, optionally substituted with  C1-C4alkyl-C1-4alkyl or (C1-4alkoxy) -C1-4alkyl,

R9 represents a hydroxy or amino group optionally substituted with a  in which

 4-amino- or 5-amino-salicylic acid, 3-amino-4-hydroxybenzoic acid, 4-amino-3-hydroxybenzoic acid, 2-amino-, 3-amino or 4-aminobenzene sulfonic acid, 3-amino-4-hydroxybenzenesulfonic acid, 4-amino-3-hydroxynaphthalene-1-sulfonic acid, 6-amino-7-hydroxynaphthalenesulfonic acid, 7-amino-4-hydroxynaphthalene-2-ene sulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid, 3-amino-2-naphthoic acid, 3-aminophthalic acid, 5-aminoisophthalic acid, 1,3,5-triaminobenzene, 1,2,4triaminobenzene, 1,2,4,5-tetraaminobenzene, 2,4,5-triaminophenol, pentaminobenzene, hexaaminobenzene, 2,4,6-triaminoresorcinol, 4,5-diaminopyrochatecol, 4, 6-diaminopyrogallol, 3,5-diamino-4-hydroxypyrochatecol, and aromatic anilines and aromatic phenols having another aromatic residue, corresponding to formula (II) <Desc / Clms Page number 20> 2-propanol, 2- (2-aminoethylamino) ethylamine, 2- (2-aminoethylamino) ethanol, 3- (2-aminoethylamino) -propylamine, 3- (2-aminoethylamino) propanol. 2-amino-2-methylpropanol, 2-amino-2-methylpropane-1,3-diol, 2-amino-2-hydroxymethylpropane-1,3-diol, tetrahydropentylamine, pentahydroxyhexylamines such as glucamine, -glucosamine, D-galactosamine, 1,2-diaminoethane, 1,2- or 1,3-diaminopropane, 1,3-diamino-  6. Use according to claim 4, characterized in that the activated methylene compound is selected from the group consisting of 1,2,3,3-tetramethyl-3H-indolium iodide, 1,2,3,3-p-toluenesulphonate. 3-tetramethyl-3H-indolium, 1,2,3,3-tetramethyl-3H-indolium methanesulfonate, 1,3,3-trimethyl-2-ethylene-indoline, 2,3-dimethylbenzothiazolium iodide, 2,3-dimethylbenzothiazolium toluenesulfonate, rhodanine, rhodanine-acetic acid, 1-ethyl-2-quinaluminium iodide, 1-methyl-2-quinaldinium iodide, barbituric acid, thiobarbituric acid, 1,3-dimethylthiobarbituric acid, diethylthiobarbitic acid, oxindole, 3-indoxyl acetate, coumarone and 1-methyl-3-phenyl-2-pyrazinone.  7. Use according to any one of the preceding claims, characterized in that the composition has a pH of between 2 and 12, preferably between 3 and 11.  8. Use according to any one of the preceding claims, characterized in that the concentration of the polycyclic aromatic vicinal trion (s) of formula (I) or (II) is between 0.0001% and 30%, relative to the total weight of the composition.  9. Dyeing cosmetic composition containing at least one polycyclic aromatic vicinal trione of formula (I) or (II) as defined in claim 1, and at least one surfactant and / or a polymeric agent of a nonionic, cationic nature, anionic or amphoteric.  10. A ready-to-use dye cosmetic composition containing at least one polycyclic aromatic vicinal trione of formula (I) or (II) as defined in claim 1 and at least one compound having a primary or secondary amine function or at least one minus an activated methylene compound or a mixture thereof.  11. Multi-component hair coloring agent comprising <Desc / Clms Page number 21>  # as a first component, a composition (a) containing at least one polycyclic aromatic vicinal trione of formula (I) or (II) as defined in claim 1, and # as a second component, a composition (b) containing at least one compound having a primary or secondary amine function or at least one activated methylene compound as defined in claims 4 to 7 or a mixture thereof.  12. hair dyeing agent according to claim 11, characterized in that it is in the form of a multi-compartment kit, with at least a first compartment containing the composition (a) and at least a second compartment containing the composition (b).  13. Hair dyeing method comprising applying to the hair, a hair dye composition according to one of claims 9 and 10, a sufficient exposure time to allow obtaining the desired color, and then rinsing and washing the hair.  14. Hair dyeing process according to claim 13, characterized in that it comprises heating the hair impregnated with hair dyeing composition to a temperature of 80 C, preferably 60 C.  A hair dyeing process comprising applying to the hair one after the other, in any order, a composition (a) and a composition (b) as defined in claim 11.  16. Hair dyeing method according to claim 15, characterized in that an intermediate rinsing step is inserted between the application of the first composition and the application of the second composition.  17. A hair dyeing method according to any one of claims 15 or 16, comprising heating hair impregnated with the composition (a) and / or (b) to a temperature of 80 C, preferably 60 C.