WO2006102987A1 - Agents pour colorer des fibres keratiniques - Google Patents

Agents pour colorer des fibres keratiniques Download PDF

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Publication number
WO2006102987A1
WO2006102987A1 PCT/EP2006/002307 EP2006002307W WO2006102987A1 WO 2006102987 A1 WO2006102987 A1 WO 2006102987A1 EP 2006002307 W EP2006002307 W EP 2006002307W WO 2006102987 A1 WO2006102987 A1 WO 2006102987A1
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group
alkyl group
hydroxy
alkyl
hydrogen atom
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PCT/EP2006/002307
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German (de)
English (en)
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Hinrich Möller
Horst Höffkes
Doris Oberkobusch
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Henkel Kommanditgesellschaft Auf Aktien
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the invention relates to compositions for the oxidative dyeing of keratin-containing fibers, in particular human hair, containing specific cationic, heterocyclic compounds, the use of these compounds for dyeing keratin-containing fibers, and to a corresponding process for dyeing keratin-containing fibers, in particular human hair.
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • the developer components are usually primary aromatic amines having a further, in the para or ortho position free or substituted hydroxy or amino group, Djaminopyridinderivate, heterocyclic hydrazones, 4-Aminopyra- zolonderivate and 2,4,5,6-tetraaminopyrimidine and its derivatives used.
  • m-phenylenediamine derivatives naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine are generally used. used derivatives.
  • Suitable coupler substances are in particular ⁇ -naphthol, 1, 5, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol , 2-amino-4- (2-hydroxyethylamino) -anisole (Lehmann's Blue), 1-phenyl-3-methyl-pyrazol-5-one, 2,4-dichloro-3-aminophenol, 1, 3-bis - (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 3-amino-6-methoxy-2 -methylamino-pyridine and 3,5-diamino-2,6-dimeth
  • p-phenylenediamine and its derivatives can be found in some persons, the so-called; Parallergic, cause allergic reactions. It is therefore always an object to provide colorants, in particular for the coloring of keratin-containing fibers such as hair, which do not have an allergenic effect. Consequently, it is desirable to develop oxidative dyes which are not derived from p-phenylenediamine yet possess excellent dyeing properties.
  • a ', first object of the invention are means for dyeing keratin fibers, in particular human hair, which contain in a cosmetic carrier at least one compound according to formula I,
  • R 1 represents a linear or cyclic C r C 6 alkyl group, a C 2 -C 6 alkenyl group, an optionally substituted aryl group, an Ai ⁇ yI (C 1 -C 6 ) alkyl group, a Ci-C 6 -monohydroxyalkyl group, a 'C 2 -C 6 polyhydroxyalkyl group, a C 1 -C 6 alkoxy (C 1 -C 6 ) alkyl group, a group R 1 R 11 N- (CH 2 ) m -, wherein R 1 and R 11 are independently a hydrogen atom, a C r C 6 alkyl group, a -C 6 hydroxyalkyl group, or an aryl (C r C6) - alkyl group, wherein R 1 and R 11 a together with the nitrogen atom, optionally substituted, 5-, 6- or 7-membered ring, and m is an integer from 2 to 6,
  • R 2 and R 3 independently of one another represent a hydrogen atom, a halogen atom, a linear or branched C 1 -C 6 -alkyl group, a cyano group, a hydroxy group, a C 1 -C 6 -monohydroxyalkyl group, a C 2 -C 6 -hydroxyalkyl group, a C 1 -C 6 -hydroxyalkyl group C 6 alkoxy, a hydroxy (dC 6 ) - alkoxy group, a group R 111 R 1 V (CHz) n -, wherein R 1 "and R IV independently represent a hydrogen atom, a Ci-C 6 alkyl group , a C 1 -C 6 -hydroxyalkyl group or an alkyl-C 1 -C 6 -alkyl group and n is an integer from 0 to 6, or together with the residual molecule form an aromatic, optionally substituted six-membered ring, X represents an oxygen atom, a sulfur
  • A is a CR 7b H group in which R 7b is a hydrogen atom or a (C 1 -C 4 ) -alkyl group,
  • the substituent -A-NH 2 of the formula I preferably binds at the ortho position to the iminium nitrogen atom of the heterocycle.
  • a bond to the ortho position means, according to the invention, a bond to the CH group directly adjacent to the iminium nitrogen atom of the heterocycle.
  • the group -A-NH 2 is in conjugation via a double bond system to the iminium nitrogen atom.
  • a in formula (I) is a CH 2 group.
  • substituents R 2 and R 3 form an aromatic, optionally substituted six-membered ring (Benzannelmaschine) together with the remainder of the molecule.
  • This six-membered ring is in turn preferably with two radicals R 8 and R 9 substituted which are independently atom for a hydrogen atom, a halogen atom, a linear or branched d-C ⁇ alkyl group, a cyano group, a hydroxy group, a C r C 6 monohydroxyalkyl , a C 2 -C 6 -
  • the formula I preferably represents compounds of the formulas II, III, IV, V, VI and VIl,
  • the compounds are according to.
  • Formula I selected from salts with counterion An ' the group consisting of 2-aminomethyl-1,3,3-trimethylindolium, 2- (1-aminoethyl) -1,3,3-trimethylindolinium, 2-aminomethyl-3-methylbenzothiazolium, 2 - Aminomethyl-3-methylbenzoxazolium, 2-aminomethyl-1, 3-dimethyl-benzimidazolinium, 2-aminomethyl-1-methyl-quinolinium and 4-aminomethyl-1-methyl-quinolinium.
  • the compounds according to the invention are preferably formed by reaction of the compounds of the formula I with organic or inorganic acids.
  • the salts are preferably physiologically compatible.
  • the anion An ' is preferably selected from the group of the anions halide, benzenesulfonate, p- Toluene sulfonate, C r C 4 alkanesulfonate, trifluoromethanesulfonate, perchlorate, 0.5 sulfate, (C 1 - C 4 ) alkyl sulfate, hydrogen sulfate, tetrafluoroborate, hexafluorophosphate and Tetrachlorozinkat selected.
  • C 1 -C 8 -alkyl radicals are the groups methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl and tert-butyl, n-pentyl and n-hexyl.
  • Examples of corresponding cyclic alkyl groups are cyclopentyl and cyclohexyl.
  • Examples of preferred C 2 -C 6 -alkenyl radicals are vinyl and allyl.
  • CrC 6 -alkoxy radicals preferred according to the invention are, for example, a methoxy or an ethoxy group.
  • Examples of a C 2 -C 6 -polyhydroxyalkyl group are the 2,3-dihydroxypropyl group,
  • Methoxyhexyl distrin are examples of inventive C 1 -C 6 -Akoxy-C 1 -C 6 - alkyl groups.
  • a preferred hydroxy-d-Ce-alkoxy group is the 2-hydroxyethoxy group.
  • Preferred aryl groups are phenyl, naphthyl and biphenyl.
  • halogen atoms are F, Cl, Br or I atoms, with Cl and Br atoms being very particularly preferred.
  • Preferred arylC r C 6 alkyl groups are benzyl and 2-phenylethyl.
  • Dimethylaminoethyl, diethylaminomethyl, dimethylaminomethyl, 2-methylaminoethyl, 2-dimethyl-aminoethyl, piperidinomethyl, pyrrolidinomethyl, morpholinomethyl are preferred radicals of the group R'R "N- (CH 2 ) ⁇ -, with the diethylaminomethyl, piperidinomethyl, 2-dimethylaminoethyl, dimethylamino and amino groups being particularly preferred.
  • a preferred C 1-4 carboxyalkyl group is the 3-carboxypropyl group.
  • the groups 1-carboxypropylene and 1-carboxyethylene are preferred carboxy (C r C 4 ) ' alkylene groups.
  • the compounds according to the invention can be prepared by methods known from the literature, e.g. according to N. Gamon et al., Liebigs Ann. Chem., 1980, 2072-2094.
  • Keratin fibers are wool, furs, feathers and especially human hair to understand.
  • the colorants of the invention can in principle but also for dyeing other natural fibers such.
  • As regenerated cellulose, nitro, alkyl or Hydr ⁇ xyalkyl- or acetyl cellulose can be used.
  • reaction products of the above-described oxidative coupling of the compounds according to formula I are colored and can be used according to the invention as cationic substantive dyes in colorants for keratin-containing fibers.
  • Preferred reaction products as an ingredient of colorants for keratin-containing fibers, in particular human hair, are selected from compounds of the formulas (RP1) to (RP6),
  • R 1 , R 2 , R 3 , R 4 , A and An "are as defined under formula (I) and R 8 and R 9 are independently a hydrogen atom, a halogen atom, a linear or branched C r C 6 alkyl group, a cyano group, a hydroxy group, a d-Ce monohydroxy acyl group, a C 2 -C 6 polyhydroxyalkyl group, a C 1 -C 6 alkoxy group, a hydroxy (C r C 6 ) alkoxy group, a group R v "R nll N- (CH 2 ) r, wherein R v " and R v ⁇ "independently of one another represent a hydrogen atom, a Ci-Ce-alkyl group, a Ci-C 6 -Hydroxyalkyl distr or an aryl-CrC 6 - alkyl group and r is an integer of 0 to 6. 10
  • reaction products are preferably present in an amount of 0.01-10% by weight, preferably 0.1-3% by weight, based in each case on the ready-to-use colorant.
  • the reaction products can be used both in the presence of the compounds of formula (I) and in the absence of the compounds of formula (I) in the colorants application.
  • the use of the dye precursors according to formula (I) in the colorants offers advantages in terms of the color fastness of the obtained dyeings. Furthermore, there is the option to use these reactive dye precursors together with other reactants in the compositions of the invention. It may therefore be advantageous to use at least one compound of the formula (I) together with at least one reactive carbonyl compound and / or with at least one oxidation dye precursor of the developer and / or coupler type.
  • Reactive carbonyl compounds according to the invention have at least one carbonyl group as reactive group which reacts with the compound of formula I under condensation to form a Schiff base. Furthermore, according to the invention, those compounds which can be used as reactive carbonyl components in which the reactive carbonyl group is derivatized such that the reactivity of the carbon atom of the derivatized carbonyl group with respect to the compounds of the formula I are always present.
  • These derivatives are preferably addition compounds a) of amines and their derivatives to form imines or oximes as addition compound b) of alcohols to form acetals or ketals as addition compound c) when component B is derived from aldehydes, of water to form hydrates as addition compound to the carbon atom of the carbonyl group of the reactive carbonyl compound, these derivatives are preferably not themselves colored. 11
  • these reactive carbonyl compounds are aldehydes or ketones.
  • the reactive carbonyl compounds are preferably selected from compounds according to formula VII 1
  • AR is benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, carbazole, pyrrole, pyrazole, furan, thiophene, 1,2,3-triazine, 1, 3,5-triazine, quinoline, isoquinoline, indole, indoline, Indolizine, indan, imidazole, 1,2,4-triazole, 1, 2,3-triazole, tetrazole, benzimidazole, 1, 3-thiazole, benzothiazole, indazole, benzoxazole, quinoxaline, quinazoline, quinolizine, cinnoline, acridine, julolidine, Acenaphthene, fluorene, biphenyl, diphenylmethane, benzophenone, diphenyl ether, azobenzene, chromone, coumarin, diphenyl
  • R 9a represents a hydrogen atom, a C 1 -C 6 -alkyl, C 2 -C 6 -acyl, C 2 -C 6 -alkenyl, C 1 -C 4 perfluoroalkyl, an optionally substituted aryl or heteroaryl group .
  • R 10, R 11 and R 12 independently represent a hydrogen atom, a halogen atom, a C r C 6 alkyl, C r C 6 alkoxy, Ci-C 6 aminoalkyl, C 1 -C 6 - hydroxyalkyl group, a Ci-Ce-alkoxy-CrCe-alkyloxy, a C 2 -C 6 acyl group, an acetyl, carboxyl, carboxylato, carbamoyl, sulfo, sulfato, sulfonamide, sulfonamido, C 2 -C 6 alkenyl, an aryl, an aryl-C r C 6 alkyl group, a hydroxy, a nitro, a pyrrolidino, a morpholino, a piperidino, an amino or ammonio or a 1-imidazol (in) iooli, wherein the last three groups having one or more C r C 6 alky
  • Z is a direct bond, a carbonyl, a carboxy (C r C 4 ) alkylene, an optionally substituted C 2 -C 6 alkenylene, C 4 -C 6 alkadienylene, furylene, thienylene -, Arylen-, Vinylenarylen-, Vinylenfurfurylen-, Vinylenthienylenoli, where Z together with the -YR 9a group can also form an optionally substituted 5-, 6- or 7-ring,
  • Y is a group which is selected from carbonyl, a group according to formula VIII and a group according to formula IX,
  • R 13 represents a hydrogen atom, a hydroxy group, a C 1 -C 4 - alkoxy group, a -C 6 alkyl group, a -C 6 hydroxyalkyl group, a C 2 - C 6 -polyhydroxyalkyl group, a CRCE-alkoxy-alkyl group CRCE .
  • R 14 and R 1S independently of one another represent a C 1 -C 6 -alkyl group, an aryl group or together with the structural element OC-0 of the formula IX form a 5- or 6-membered ring.
  • the reactive carbonyl compound is more preferably selected from the group consisting of acetophenone, propiophenone, 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, 2-hydroxypropiophenone, 3-hydroxypropiophenone, 4-hydroxypropiophenone, 2-hydroxybutyrophenone, 3-hydroxybutyrophenone, 4- Hydroxybutyrophenone, 2,4-dihydroxyacetophenone, 2,5-dihydroxyacetophenone, 2,6-dihydroxyacetophenone,.
  • acetonaphthone chromone, chromone-2-carboxylic acid, flavone, 3-hydroxyflavone, 3,5,7-trihydroxyflavone, 4 ', 5,7-trihydroxyflavone, 5,6,7-trihydroxyflavone, quercetin, 1-indanone, 9- Ruorenone, 3-hydroxyfluorenone, anthrone, 1, 8-dihydroxyanthrone, vanillin, coniferylaldehyde, 2-methoxybenzaldehyde, 3-methoxybenzaldehyde, A-
  • Ethoxybenzaldehyde 4-hydroxy-2,3-dimethoxybenzaldehyde, 4-hydroxy-2,5-dimethoxybenzaldehyde, 4-hydroxy-2,6-dimethoxybenzaldehyde, 4-hydroxy-2-methylbenzaldehyde, 4- Hydroxy-3-methylbenzaldehyde, 4-hydroxy-2,3-dimethylbenzaldehyde, 4-hydroxy-2,5-dimethylbenzaldehyde, 4-hydroxy-2,6-dimethylbenzaldehyde, 4-hydroxy-3, 5-dimethoxybenzaldehyde, 4-hydroxy-3,5-dimethylbenzaldehyde, 3,5-diethoxy-4-hydroxybenzaldehyde, 2,6-diethoxy-4-hydroxybenzaldehyde, 3-hydroxy-4-methoxybenzaldehyde, 2-hydroxy-4-methoxybenzaldehyde, 2-ethoxy-4-hydroxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde,.
  • Benzaldehyde, cinnamic aldehyde and naphthaldehyde and their derivatives, in particular having one or more hydroxyl, alkoxy and amino substituents, are very particularly preferably used as the reactive carbonyl compound in the agents according to the invention.
  • the compounds according to formula X are preferred,
  • R 16 , R 17 and R 18 are each independently hydrogen, halogen, C r C 6 alkyl, hydroxy, C 1 -C 6 alkoxy, amino, C r C 6 dialkylamino , a di (C 2 -C 6 -hydroxyalkyl) amino group, a di (C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl) amino group, a C 1 - 17
  • R 19 and R 20 represent a hydrogen atom or together form, together with the remainder of the molecule, a 5- or 6-membered aromatic or aliphatic ring.
  • Very particularly preferred compounds of the reactive carbonyl compounds are selected from the group consisting of vanillin, coniferyl aldehyde, 2-methoxybenzaldehyde, 3-methoxybenzaldehyde, 4-methoxybenzaldehyde, 2-ethoxybenzaldehyde, 3-ethoxybenzaldehyde, 4-ethoxybenzaldehyde, 4-hydroxy-2,3- dimethoxybenzaldehyde, 4-hydroxy-2,5-dimethoxybenzaldehyde, 4-hydroxy-2,6-dimethoxybenzaldehyde, 4-hydroxy-2-methylbenzaldehyde, 4-hydroxy-3-methylbenzaldehyde, 4- Hydroxy-2,3-dimethylbenzaldehyde, 4-hydroxy-2,5-direthylbenzaldehyde, 4-hydroxy-2,6-dimethylbenzaldehyde, 4-hydroxy-3,5-dimethoxybenzaldehyde, 4-hydroxybenzaldehyde 3,5-dimethyl
  • G 1 represents a hydrogen atom, a C 1 - to C 4 -alkyl radical, a d- to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) - AIkOXy- ( C 1 - to C 4 ) -alkyl radical, a 4'-aminophenyl radical or a C 1 - to C 4 - alkyl radical which is substituted by a nitrogen-containing group, a phenyl or a 4'-aminophenyl radical;
  • G 2 represents a hydrogen atom, a C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) - 19
  • G 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 Polyhydroxyalkyl radical, a C 1 - to C 4 -hydroxyalkoxy radical, a C 1 - to C 4 -acetylaminoalkoxy radical, a C 1 - to C 4 -mesylaminoalkoxy radical or a C 1 -
  • G 4 represents a hydrogen atom, a halogen atom or a C 1 - to C 4 -alkyl radical or, when G 3 and G 4 are ortho to each other, they may together form a bridging ⁇ , ⁇ r-alkylenedioxo group, such as, for example, an ethylenedioxy group.
  • Particularly preferred p-phenylenediamines of the formula (E1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2 , 6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, 'N, N-ethyl-p-phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4-amino-3-methyl- (N, N-diethyl) -aniline, N, N-bis- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) -amino 2-methylaniline, 4-
  • Very particularly preferred p-phenylenediamine derivatives of the formula (E1) according to the invention are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p-phenylenediamine and N, N bis (.beta.-hydroxyethyl) -p-phenylenediamine.
  • binuclear developer components which can be used in the dyeing compositions according to the invention, mention may be made in particular of the compounds corresponding to the following formula (E2) and their physiologically tolerated salts:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 -ReSt, which is optionally substituted by a C 1 - to C 4 -alkyl radical, by a C 1 - to C 4 -
  • the bridge Y is an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, of one or more nitrogen-containing groups and / or one or more
  • Heteroatoms such as oxygen, sulfur or nitrogen atoms may be interrupted or terminated and possibly by one or more hydroxyl or C 1 -
  • C 8 alkoxy may be substituted, or a direct bond
  • G 5 and G 6 independently of one another represent a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -
  • G 7 , G 8 , G 9 , G 10 , G 11 and G 12 are each independently
  • Hydrogen atom a direct bond to the bridging Y or a C 1 - to C 4 -
  • Preferred dinuclear developing agents of the formula (E2) are in particular: N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) -1,3-diamino-propan-2-ol, N , N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis ( .beta.-hydroxyethyl) -N, N'-bis (4-aminophenyl) - tetramethylenediamine, N, N'-bis (4-methyl-aminophenyl) tetramethylenediamine, N 1 N'-diethyl-N, N'-bis - (4-amino-3-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminophenyl)
  • Very particularly preferred binuclear developer components of the formula (E2) are N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, Bis (2-hydroxy-5-aminophenyl) methane, N, N'-bis (4-aminophenyl) -1, 4-diazacycloheptane and 1, 10-bis- (2,5-diaminophenyl) -1, 4 , 7,10-tetraoxadecane or one of its physiologically acceptable salts.
  • p-aminophenol derivatives of the formula (E3) 22 it may be preferred according to the invention to use as the developer component in the compositions according to the invention a p-aminophenol derivative or one of its physiologically tolerable salts. Particular preference is given to p-aminophenol derivatives of the formula (E3) 22
  • G 13 represents a hydrogen atom, a halogen atom, a C 1 - to C 4 -alkyl radical, a Cr to C 4 monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a
  • G 14 represents a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a
  • G 15 is hydrogen, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -
  • Monohydroxyalkyl radical a C 2 to C 4 polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
  • G 16 is hydrogen or a halogen atom.
  • Preferred p-aminophenols of the formula (E3) are, in particular, p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 -Amino-3-hydroxymethylphenol, 4-amino-2- ( ⁇ -hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino 2-aminomethylphenol, 4-amino-2- ( ⁇ , -hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino 2-chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethylaminomethyl) -phenol and their physiologically acceptable salts
  • Very particularly preferred compounds of formula (E3) are p-aminophenol, A- amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ß-dihydroxyethyl) - and 4- Iphenol amino-2- (diethylaminomethyl) -phenol.
  • the developer component may be selected from o-aminophenol and its' derivatives, such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component may preferably be selected from heterocyclic developer components such as the pyridine ⁇ , pyrimidine, pyrazole, pyrazol-Pyrimidiri' derivatives and their physiologically acceptable salts.
  • Preferred pyridine derivatives are, in particular, the compounds described in the 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- ( ⁇ -
  • Methoxyethyl amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are, in particular, the compounds described in German patent DE 2 359 399, Japanese laid-open specification JP 02019576 A2 or in published patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6- triaminopyrimidine.
  • Preferred pyrazole derivatives are, in particular, the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740 931 and DE 195 43 988, such as 4,5 Diamino-1-methylpyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) -pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1- (4'-chlorobenzyl) -pyrazole, 4,5- Diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-Benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-but
  • Coupler components are preferably selected from m-aminophenol and its derivatives such as 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2 , 6-dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2- Hydroxyethyl) -amino-2-methylphenol, 3- (diethylamino) -phenol, N-cyclopentyl-3-aminophenol, 1,3-dihydroxy-5- (methylamino) -benzene, 3-ethylamino-4-methylphenol and 2,4 dichloro-3-aminophenol,
  • m-aminophenol and its derivatives such as 5-amino-2-methylphenol, N-cyclopentyl
  • o-aminophenol and its derivatives m-diaminobenzene and its derivatives such as 2,4-diaminophenoxyethanol, 1, 3-bis (2,4-diaminophenoxy) -propane, 1-methoxy-2-amino-4- (2 -hydroxyethylamino) benzene, 1, 3-bis (2,4-diaminophenyl) -propane, 2,6-bis (2-hydroxyethylamino) -1-methylbenzene and 1-amino-3-bis (2-hydroxyethyl) - aminobenzene,
  • o-diaminobenzene and its derivatives such as 3,4-diaminobenzoic acid and 2,3-diamino-1-methylbenzene,
  • Di- or trihydroxybenzene derivatives such as resorcinol, Resorcinmonometh 'yl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1, 2,4-trihydroxybenzene, pyridine derivatives such as 2,6 Dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6 Dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine, naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl
  • Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine
  • quinoxaline derivatives such as 6-methyl-1,2,3,4-tetrahydroquinoxaline
  • Pyrazole derivatives such as 1-phenyl-3-methylpyrazol-5-one, 1 indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole,
  • Pyrimidine derivatives such as 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-
  • Methylenedioxybenzene derivatives such as 1-hydroxy-3,4-methylenedioxybenzene
  • coupler components according to the invention are 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 3-aminopheol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4-chlororesorcinol , 2-chloro-6-methyl-3-aminophenol, 2-methyl resorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol and 2,6-dihydroxy-3,4-dimethylpyridine.
  • Indoles and indolines which have at least one hydroxyl or amino group, preferably as a substituent on the six-membered ring, can furthermore be used as precursors of naturally-analogous dyes in the compositions according to the invention.
  • These groups may carry further substituents, e.g. Example in the form of etherification or esterification of the hydroxy group or alkylation of the amino group.
  • Particularly suitable precursors of naturally-analogous hair dyes are derivatives of the 5,6-dihydroxyindoline of the formula Xa,
  • - G 21 is hydrogen, hydroxy-alkyl group, a C 1 -C 4 -AIkYlQrUpPe or a C r C 4,
  • G 22 is hydrogen or a -COOH group, where the -COOH group may also be in the form of a salt with a physiologically compatible cation,
  • G 23 is hydrogen or a C 1 -C 4 -alkyl group
  • G 24 is hydrogen, a C 1 -C 4 alkyl group or a group -CO-G 26 in which
  • G 26 is a C 1 -C 4 -alkyl radical
  • G 25 represents one of the groups mentioned under G 24 , as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6 dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid and 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially 5, 6-Dihydroxyindolin.
  • G 27 is hydrogen, a Ci-C 4 alkyl group or a C 1 -C 4 hydroxyalkyl group,
  • G 28 is hydrogen or a -COOH group, where the -COOH group may also be present as a salt with a physiologically compatible cation,
  • G 29 is hydrogen or a C 1 -C 4 -alkyl group
  • G 30 is hydrogen, a C 1 -C 4 alkyl group or a group -CO-G 32 in which
  • G 32 is a C 1 -C 4 -alkyl group
  • G 31 stands for one of the groups mentioned under G 30 , as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • indole Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5, 6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5 , 6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.
  • N-methyl-5 ⁇ -dihydroxy-indole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, and in particular the 5,6-dihydroxyindole ,
  • the indoline and indole derivatives can be used in the colorants of the invention both as free bases and in the form of their physiologically acceptable salts with inorganic or organic acids, for.
  • the hydrochlorides the sulfates and hydrobromides, are used.
  • the indole or indoline derivatives are contained therein usually in amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-%.
  • the colorants according to the invention for further modifying the color shades in addition to the compounds according to the invention additionally contain conventional substantive dyes, such as nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those having the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, Disperse 28
  • agents according to the invention may preferably contain a cationic substantive dye. Particularly preferred are
  • aromatic systems substituted with a quaternary nitrogen group such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
  • Preferred cationic substantive dyes of group (c) are in particular the following compounds: 29
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) are very particularly preferred cationic substantive dyes of group (c).
  • the cationic direct dyes, which are sold under the trademark Arianor ® are, according to the invention particularly preferred substantive dyes. 31
  • compositions according to this embodiment contain the Djrekt istden dyes preferably in an amount of 0.01 to 20 wt .-%, preferably from 0.01 to 10 wt .-%, each based on the total colorant.
  • compositions according to the invention may additionally contain color enhancers.
  • the color enhancers are preferably selected from the group consisting of piperidine, piperidine-2-carboxylic acid, piperidine-3-carboxylic acid, piperidine-4-carboxylic acid, pyridine, 2-hydroxypyridine, 3-hydroxypyridine, 4-hydroxypyridine, imidazole, 1-methylimidazole, Arginine, histidine, pyrrolidine, proline, pyrrolidone, pyrrolidone-5-carboxylic acid, pyrazole, 1, 2,4-triazole, piperazidine, their derivatives and their physiologically acceptable salts.
  • the color intensifiers mentioned above can be used in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, in each case based on 100 g of the total colorant.
  • the agent according to the invention already gives intensive dyeings under air oxidation. It can therefore be dispensed with the presence of additional oxidizing agents. However, it may u. U. be desirable, the inventive compositions to achieve the nuances that are lighter than the keratin-containing fiber to be dyed, hydrogen peroxide or Add 32 other oxidizing agents. Oxidizing agents are generally used in an amount of 0.01 to 6 wt .-%, based on the application solution. A preferred oxidizing agent for human hair is H 2 O 2 .
  • Oxidation catalysts are, for example, metal salts, metal chelate complexes or metal oxides, which allow a slight change between two oxidation states of the metal ions. Examples are salts, chelate complexes or oxides of iron, ruthenium, manganese and copper.
  • oxidation catalysts are enzymes especially in the presence of classical developer systems of the p-phenylenediamine or p-aminophenol type. Suitable enzymes are e.g. Peroxidases that can significantly increase the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as, for example, the laccases, or generate small amounts of hydrogen peroxide in situ and thus biocatalytically activate the oxidation of the dye precursors. Particularly suitable catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the specific substrates, e.g.
  • Lactate oxidase and lactic acid and their salts Lactate oxidase and lactic acid and their salts
  • the colorants according to the invention give intensive dyeings even at physiologically compatible temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants can usually be incorporated into an aqueous cosmetic carrier.
  • Suitable hydrous cosmetic carriers are for.
  • As creams, emulsions, gels or surfactant-containing foaming solutions such.
  • the agents according to the invention for the oxidative dyeing of keratinic fibers preferably comprise at least one derivative of the general formula (I) in an amount of from 0.01 to 10% by weight, more preferably from 0.1 to 3% by weight, based on the finished composition Medium. , , , , ; ⁇ . , • ⁇ ;
  • the agent for coloring keratinous fibers can be selected from any suitable agents that are particularly suitable for dyeing human hair.
  • a cosmetically acceptable carrier used is in particular an otherwise customary carrier of agents for dyeing human hair.
  • the colorants according to the invention may be composed according to known colorants or contain the usual ingredients for them.
  • compositions of the invention preferably contain the dye precursors in a suitable aqueous, alcoholic or aqueous-alcoholic.
  • Carrier for the purpose of hair coloring such carriers are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, Schaumaerqsole or other preparations which are suitable for use on the hair. But it is also conceivable to integrate the dye precursors in a powdered or tablet-shaped formulation. 34
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alcohol, in particular ethanol or isopropanol.
  • the compositions of the invention may additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1, 2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • Suitable colorant compositions are described, for example, in DE-U1-299 11 819, DE-A-101 25 451, DE-U1-201 11 036, Kosmetik, ed. W. Umbach, 2nd ed. 1995, G. Thieme Verlag Stuttgart , New York.
  • the colorants of the invention may contain all known in such preparations.
  • the colorants contain at least one surfactant, whereby in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing ,, anionic group such. As a carboxylate, sulfate, sulfonate or phosphate group un, d is a lipophilic alkyl group having about 10 to 22 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule.
  • Acylsarcosides having 10 to 18 C atoms in the acyl group, acyl taurides having 10 to 18 C atoms in the acyl group, acyl isethionates having 10 to 18 C atoms in the acyl group, sulfosuccinic acid mono- and dialkyl esters having 8 to 18 C atoms in the acyl group Alkyl group and sulfosuccinic acid mono-alkylpolyoxyethyl esters having 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkane sulfonates having 12 to 18 carbon atoms, linear alpha-olefin sulfonates having 12 to 18 carbon atoms, alpha sulfo fatty acid methyl esters of fatty acids with 12 to 18 C atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 C atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid , Isostearic acid and palmitic acid.
  • Nonionic surfactants contain as hydrophilic group z.
  • a polyol group for example, a polyalkylene glycol ether or a combination of polyol and Polyglykolether- group.
  • Such compounds are, for example
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula R 1 O- (Z) x . These connections are identified by the following parameters.
  • the alkyl radical R 1 contains 6 to 22 carbon atoms and may be both linear and branched. Preference is given to primary linear and 2-methyl-branched aliphatic 37
  • alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, tr-cetyl and 1-stearyl Particular preference is given to 1-octyl, 1-decyl, 1-lauryl, 1 -Myristyl Use of so-called "oxo-alcohols" as starting materials outweighs compounds with an odd number of carbon atoms in the alkyl chain.
  • the alkyl polyglycosides which can be used according to the invention can contain, for example, only one particular alkyl radical R 1 .
  • these compounds are prepared starting from natural fats and oils or mineral oils.
  • the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the particular work-up of these compounds.
  • C 10 alkyl groups mainly of C 2 - - and C - ⁇ - alkyl groups essentially of C 8 - to Ci6 alkyl groups or Ci essentially of alkyl polyglycosides are those in which R 1 consists essentially of C 8 are particularly preferred 2 - to Ci 6 alkyl groups.
  • sugar building block Z it is possible to use any desired mono- or oligosaccharides.
  • sugars with 5 or 6 carbon atoms and the corresponding oligosaccharides are used.
  • Such sugars are, for example, glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, altrose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar building blocks are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain on average from 1.1 to 5 sugar units. Alkyl polyglycosides having x values of 1.1 to 1.6 are preferred. Very particular preference is given to alkyl glycosides in which x is 1.1 to 1.4.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • this substance class as a further constituent of the preparations according to the invention in the event that an effect of the perfume oil on the hair which exceeds the duration of the hair treatment is desired.
  • alkoxylated homologs of said alkyl polyglycosides can also be used according to the invention. These homologs may contain on average up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • zwitterionic surfactants can be used, in particular as cosurfactants.
  • Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one -COO 9 or -SO 3 ("J) group in the molecule.
  • N-dimethylammonium glycinates for example cocoalkyl dimethylammonium glycinate
  • N-acylaminopropyl N N-dimethylammonium glycinates, for example cocoacylaminopropyldimethylammonium glycinate
  • 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazolines each having A preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI name cocamidopropyl betaine.
  • ampholytic surfactants are also particularly suitable as co-surfactants.
  • am- pholytica surfactants are surface-active compounds which, apart from a C 8 -C 8 alkyl or acyl group in the molecule at least one free amino group and at least one -COOH or -SO 3 H group and to form internal Salts are capable.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkyl aminopropionate, the Kokosacyiaminoethylaminopropionat and the C 2-18 acyl sarcosine.
  • the cationic surfactants used may in particular be those of the quaternary ammonium compounds, esterquats and amidoamines type.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular 39
  • Yeast chlorides and bromides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylchloronium chloride, as well as the imidazolium compounds known under the INCI names Quatemium-27 and Qüaternium- ⁇ S.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred esterquats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are marketed under the brands Stepantex® ®, ® and Dehyquart® Armocare® ®.
  • the alkylamidoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group of substances that available under the brand Tegoamid ® S 18 commercially stearamidopropyl dimethylamine is.
  • cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • cationic silicone oils such as the commercially available products Q2-7224 (manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicones), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® - Quat 3270 and 3272 (manufacturer: Th Goldschmidt; diquatemäre polydimethylsiloxanes. 40 quaternium-80).
  • Q2-7224 manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone
  • Dow Corning 929 emulsion containing a hydroxylamino-modified silicone, also referred to as amodimethicones
  • SM -2059 manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to INCI nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride”.
  • the compounds used as surfactant with alkyl groups may each be uniform substances. However, it is generally preferred to use native vegetable or animal raw materials in the production of these substances, so that substance mixtures having different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrow homolog distribution can be used.
  • normal homolog distribution are meant mixtures of homologs obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts. Narrowed homolog distributions, on the other hand, are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts.
  • the use of products with narrow homolog distribution may be preferred.
  • auxiliaries and additives are, for example, nonionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallyl ammonium chloride copolymers, diethyl sulfate-quaternized dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, 41
  • nonionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copo
  • zwitterionic and amphoteric polymers such as acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methylmethacrylate / tert-butylaminoethylmethacrylamide hydroxypropyl methacrylate copolymers, anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, Vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert-butyl acrylamide terpolymers, ⁇
  • Thickening agents such as agar-agar, guar gum, alginates, xanthan gum, gum arabicum, karaya gum, locust bean gum, linseed gums, dextrans, celulose derivatives, e.g. For example, methyl cellulose, hydroxyalkyl cellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. As bentonite or fully synthetic hydrocolloids such.
  • Structurants such as glucose and maleic acid
  • hair-conditioning compounds such as PhosRholipide, for example soya lecithin, egg lecithin and cephalins, and silicone oils'
  • Protein hydrolysates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, their condensation products with fatty acids and quaternized protein hydrolysates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
  • Anti-dandruff agents such as Piroctone Olamine and Zinc Omadine, other pH adjusters,
  • Active substances such as panthenol, pantothenic acid, allantoin, pyrrolidonecarboxylic acids and their salts, plant extracts and vitamins, cholesterol, light stabilizers,
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as spermaceti, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, fatty acid alkanolamides, 42
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole, opacifiers such as latex,
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air and antioxidants.
  • Suitable metal salts are, for. As formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkali metals such as potassium, sodium or lithium, alkaline earth metals such as magnesium, calcium, Strontium or barium, or of aluminum, manganese, iron, cobalt, copper or zinc, sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate being preferred. These salts are preferably contained in an amount of 0.03 to 65 mmol, especially 1 to 40 mmol, based on 100 g of the total colorant.
  • the pH of the ready-to-use dyeing preparations is usually between 2 and 11, preferably between 5 and 10.
  • Non-pretreated human hair was inserted into the freshly prepared staining solution at 3O 0 C for 30 minutes graying a strand of 90%, is introduced.
  • the tress was then rinsed for 30 seconds with lukewarm water, dried with warm air (30 0 C to 40 0 C) and then combed out.

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Abstract

L'invention concerne des agents servant à colorer par oxydation des fibres kératiniques, notamment des cheveux humains, et contenant comme précurseur de colorant d'oxydation des composés de formule (I), les groupes R1, R2, R3, X, A et An- étant définis dans la revendication 1. Ces précurseurs de colorant conviennent à la coloration avec oxydation par l'air ou en présence d'autres agents oxydants, comme le peroxyde d'hydrogène. L'invention concerne également l'utilisation des dérivés selon la formule (I) pour colorer des fibres kératiniques, ainsi qu'un procédé correspondant pour colorer des fibres kératiniques, notamment des cheveux humains.
PCT/EP2006/002307 2005-04-01 2006-03-14 Agents pour colorer des fibres keratiniques WO2006102987A1 (fr)

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Citations (3)

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US20040187225A1 (en) * 2001-04-02 2004-09-30 Laurent Vidal Novel dyeing composition for dyeing keratinous fibres comprising a particular dicationic diazo dye
US20040244124A1 (en) * 2001-06-12 2004-12-09 Gregory Plos Dyeing composition for human keratinous fibres with oxidation dyes and dicationic compounds
WO2005012437A1 (fr) * 2003-07-24 2005-02-10 Ciba Specialty Chemicals Holding Inc. Colorants directs cationiques

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