WO2006103036A1 - Agents servant a colorer des fibres keratiniques - Google Patents

Agents servant a colorer des fibres keratiniques Download PDF

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Publication number
WO2006103036A1
WO2006103036A1 PCT/EP2006/002757 EP2006002757W WO2006103036A1 WO 2006103036 A1 WO2006103036 A1 WO 2006103036A1 EP 2006002757 W EP2006002757 W EP 2006002757W WO 2006103036 A1 WO2006103036 A1 WO 2006103036A1
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group
alkyl group
hydroxy
alkyl
amino
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PCT/EP2006/002757
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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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Publication of WO2006103036A1 publication Critical patent/WO2006103036A1/fr

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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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • A61K8/4933—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
    • 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

Definitions

  • the invention relates to agents for the oxidative dyeing of keratin-containing fibers, in particular human hair, containing specific N-heterocyclic compounds, the use of these compounds for dyeing keratin-containing fibers, and a corresponding method 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 free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives 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 coupling agents are, in particular, ⁇ -naphthol, 1,5,7,7-di- or 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomonomethyl 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-methylaminopyridine and 3,5-diamino-2,6-dimethoxypyridine.
  • p-phenylenediamine and its derivatives can cause allergic reactions in some people, the so-called para-allergic. 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 subject of the invention are agents for dyeing keratin-containing fibers, in particular human hair, which contain in a cosmetic carrier at least one compound according to formula I and / or their physiologically acceptable salts,
  • R 1 and R 2 are independently a hydrogen atom, a halogen atom, a linear or branched Ci-C 6 alkyl group, a cyano group, a hydroxy group, a -C 6 monohydroxyalkyl, a C 2 -C 6 - polyhydroxyalkyl group, a Ci-C 6 alkoxy group, a hydroxy (C r C6) - alkoxy group, a group R 1 R 11 N- (CH 2) P, wherein R 1 and R 11 are independently a hydrogen atom, a Ci- Ce-alkyl group, a C r C 6 -Hydroxyalkyl distr or an aryl-C r 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 is an oxygen atom or a sulfur atom
  • Cyano group a hydroxy group, a C r C 6 monohydroxyalkyl group, a
  • R ⁇ v are independent of each other is a hydrogen atom, a Ci-C 6 alkyl group, a C r C 6 hydroxyalkyl group or an aryl-C r C 6 alkyl group and m is an integer from 0 to 6, or a group NR 7 , wherein R 7 represents a linear or cyclic C r C 6 alkyl group, a C 2 -C 6 - alkenyl group, an optionally substituted aryl group, an aryl (Ci-C 6) - alkyl group, a -C 6 monohydroxyalkyl, a C 2 - C 6 - Polyhydroxyalkyl distr, a CrC 6 alkoxy (CrC 6 ) alkyl group, a group R v R vl N- (CH 2 ) q -, wherein R v and R v ⁇ independently represent a hydrogen atom, a C r C 6 alkyl group, a C r C 6 -hydroxyalky
  • substituents R 1 and R 2 form an aromatic, optionally substituted six-membered ring (Benzannelmaschine) together with the remainder of the molecule.
  • This six-membered ring is again preferably substituted by two radicals R 8 and R 9 , which 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 r C 6 - Monohydroxyalkyl group, a C 2 -C 6 -
  • Polyhydroxyalkyl group a Ci-C 6 alkoxy, a hydroxy (CrC 6 ) alkoxy group, a group R vll R vn ⁇ N- (CH 2 ) r -, wherein R v "and R v ⁇ " independently represent a hydrogen atom , a CrC alkyl 6 alkyl group, a C r C 6 hydroxyalkyl group, or an aryl-C r C 6, and r is a whole number from 0 to. 6
  • the compounds of the formulas I are preferably selected from at least one of the compounds according to formulas (II) and / or (III) and / or their physiologically tolerable salts
  • R 7 represents a linear or cyclic C r C 6 alkyl group, a C 2 -C 6 alkenyl group, an optionally substituted aryl group, an aryl (d-Ce) alkyl group, a C r C 6 monohydroxyalkyl group, a C 2 -C 6 - polyhydroxyalkyl group, a C 1 -C 6 alkoxy (CrC 6) alkyl group, a group R v R vl N- q (CH 2) -, in which R V and R VI are each independently a Hydrogen atom, a C r C 6 alkyl group, a CrC 6 -hydroxyalkyl group or an aryl (C r C 6 ) alkyl group, wherein R v and R v ⁇ together with the nitrogen atom, an optionally substituted, 5-, 6- or 7 -membered ring, and q is an integer from 2 to 6.
  • R 8 and R 9 independently represent a hydrogen atom, a halogen atom, a linear or branched Ci-C 6 alkyl group, a cyano group, a hydroxy group, a Ci-C 6 monohydroxyalkyl, a C 2 -C 6 - polyhydroxyalkyl , a C r C 6 alkoxy group, a hydroxy (dC 6 ) alkoxy group, a group R v "R vlll N- (CH 2 ) r-, wherein R v " and R v ⁇ "independently represent a hydrogen atom , a C r C 6 alkyl group, a C r C 6 hydroxyalkyl group or an arylCroC 6 alkyl group, and r is an integer of 0 to 6.
  • the compounds according to formula I are selected from the group formed from 2-aminoindolin-3-one, 2-amino-1-methylindolin-3-one, 2-aminoindan-1, 3-dione and the physiologically acceptable Salts of these compounds.
  • the compounds according to the invention are present as physiologically acceptable salts, they are preferably formed by reacting the compounds of the formula I with organic or inorganic acids.
  • the counterion of these salts is preferably selected from the group of the anions halide, benzenesulfonate, p-toluenesulfonate, C 1 -C 4 -alkanesulfonate, trifluoromethanesulfonate, perchlorate, 0.5 sulfate, (C r C 4 ) -alkyl sulfate, hydrogensulfate, tetrafluoroborate, hexafluorophosphate and tetrachlorozincate selected.
  • Examples of linear and branched C 1 -C 6 -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.
  • C 1 -C 6 -alkoxy radicals which are 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,
  • Methoxy hexy Ig group are examples of inventive C 1 -C 6 -Akoxy-CrC 6 - alkyl groups.
  • a preferred hydroxyCrC 6 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 arylCrC 6 -alkyl groups are benzyl and 2-phenylethyl.
  • 2-dimethylaminoethyl, piperidinomethyl, pyrrolidinomethyl, morpholinomethyl are preferred radicals of the group R'R "N- (CH 2 ) n-, where the diethylaminomethyl,
  • Piperidinomethyl, 2-dimethylaminoethyl, dimethylamino and the amino group are particularly preferred.
  • a preferred C- M carboxyalkyl group is the 3-carboxypropyl group.
  • the groups 1-carboxypropylene and 1-carboxyethylene are preferred carboxy (C r )
  • 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 hydroxyalkyl 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 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) and (RP2),
  • R 7 is defined as described 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 C 1 -C 6 - monohydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a C r C 6 alkoxy group, a hydroxy (C r C 6 ) alkoxy group, a group R vll R VIII N- (CH 2 ) r-, wherein R v "and R vl" are independently a hydrogen atom, a CrC 6 alkyl group, a CrC alkyl 6 hydroxyalkyl group, or an aryl-C r C 6, and r is a whole number from 0 to. 6
  • 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.
  • these reactive carbonyl compounds are aldehydes or ketones.
  • the reactive carbonyl compounds are preferably selected from compounds according to formula VII,
  • 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, diphen
  • R 9a is a hydrogen atom, a C r 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 CrC 6 alkyl, C 1 -C 6 -AIkOXy-, Ci-C 6 aminoalkyl, C 1 -C 6 - Hydroxyalkyl group, a C t -C 6 alkoxyC r C 6 alkyloxy group, a C 2 -C 6 acyl group, an acetyl, carboxyl, carboxylato, carbamoyl, sulfo, sulfato, sulfonamide, suifonamido , C 2 -C 6 alkenyl, an aryl, an arylC r C 6 alkyl group, a hydroxy, a nitro, a pyrrolidine, a morpholino, a piperidino, an amino or Ammonio or a 1-imidazole (in) io group, where the last three groups with one or more Ci-C 6 alky
  • Z is a direct bond, a carbonyl, a carboxy (C 1 -C 4 ) -alkylene, an optionally substituted C 2 -C 6 -alkenylene, C 4 -C 6 -alkadienylene, furylene, thienylene, Arylene, vinylenarylene, vinylenfururylene, vinylenthienylene group, wherein Z together with the -YR 9a group can also form an optionally substituted 5-, 6- or 7-membered ring,
  • Y is a group which is selected from carbonyl, a group according to formula VI.1 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 r C 6 alkyl group, a Ci-C 6 hydroxyalkyl group, a C 2 - C 6 -Polyhydroxya kyl distr, a CrC 6! - Alkoxy-C 1 -C 6 -alkyl group
  • R 14 and R 15 independently of one another represent a C 1 -C 6 -alkyl group, an aryl group or form together with the structural element OC-0 of the formula IX 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, 2,3,4-trihydroxyacetophenone, 3,4,5-trihydroxyacetophenone, 2,4,6-trihydroxyacetophenone, 2,4,6- Trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone diethyl ketal, 4-hydroxy-3-methoxy-acetophenone, 3,5-dimethoxy-4-hydroxyacetophenone, A-aminoacetophenone, 4-dimethylaminoaceto
  • 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-methoxy- benzaldehyde, 2-hydroxy-4-methoxybenzaldehyde, 2-ethoxy-4-hydroxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde,
  • Benzaldehyde, cinnamic aldehyde and naphthaldehyde and their derivatives, in particular with one or more of these, are very particularly preferred in the agents according to the invention a plurality of hydroxy, alkoxy and amino substituents used as the reactive carbonyl compound.
  • the compounds according to formula X are preferred,
  • R 16, R 17 and R 18 independently represent a hydrogen atom, a halogen atom, a C r C 6 alkyl group, a hydroxy group, a C 1 -C 6 - alkoxy group, an amino group, a C r C 6 dialkylamino group, a di (C 2 -C 6 - hydroxyalkyl) amino group, a di (Ci-C 6 -alkoxy-CrC 6 alkyl) aminoguppe, a C 1 - C 6 -Hydroxyalkyloxy distr, a sulfonyl group, a carboxyl group, a sulfonic acid group, a sulfonamido group , a sulfonamide group, a carbamoyl group, a C 2 -C 6 acyl group, an acetyl group or a nitro group,
  • Z ' is a direct bond or a vinylene group
  • 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-dimethylbenzaldehyde, 4-hydroxy-2,6-dimethylbenzaldehyde, 4-hydroxy-3,5-dimethoxybenzaldehyde, 4-hydroxybenzaldehyde 3,5-dimethylbenz
  • G 1 is a hydrogen 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 ) -
  • G 2 is a hydrogen 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 ) -
  • 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
  • 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 ⁇ , ⁇ -alkylenedioxy 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-diethyl-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-N
  • p-phenylenediamine derivatives of the formula (E1) are p-phenylenediamine, p-toluenediamine, 2- (ß-hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ß-dihydroxyethyl) -p-pheny! Endiamin and N , N-bis (.beta.-hydroxyethyl) -p-phenylenediamine.
  • developer component compounds in the compositions according to the invention which contain at least two aromatic nuclei which are substituted by amino and / or hydroxyl groups.
  • 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 radical which is optionally substituted by a C 1 - to C 4 -alkyl radical, by a C 1 - to C 4 -hydroxyalkyl radical and / or by a bridge Y. or the where appropriate, is part of a bridging ring system;
  • the bridge Y represents an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, which may be 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 -
  • Polyhydroxyalkyl radical a C 1 - to C 4 -aminoalkyl radical or a direct compound for bridging Y,
  • G 7 , G 8 , G 9 , G 10 , G 11 and G 12 independently of one another represent a hydrogen atom, a direct bond to the bridge Y or a C 1 to C 4 alkyl radical, with the provisos that
  • the compounds of formula (E2) contain at least one amino group which carries at least one hydrogen atom.
  • 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 ( ⁇ -hydroxyethyl) -N, N'-bis (4-arninophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N 1 N 1 -diethyl-N, N'-bis - (4-amino-3-methylphenyl) -ethylenediamine, bis (2-hydroxy-5-aminophenyl) -methane
  • Very particularly preferred binuclear developer components of the formula (E2) are N, N'-bis (.beta.-hydroxyethyl) -N, N l 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 their physiologically acceptable salts.
  • p-aminophenol derivatives of the formula (E3) 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)
  • G 13 represents a hydrogen atom, a halogen 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
  • G 14 represents a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a
  • C r to C 4 monohydroxyalkyl radical a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) alkoxy alkyl (C r to C 4) a C 1 - to C 4 aminoalkyl, or a C 1 to C 4 cyanoalkyl radical,
  • G 15 is hydrogen, a C r 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-fluorophenol, 4-amino-2 chlorophenol, 4-amino-2,6-
  • Very particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol and 4-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, pyrazole pyrimidine 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-buty
  • the coupler components optionally additionally present in the agents according to the invention 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, o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as 2,4-dichloro-3 aminophenol, o-a
  • Diaminophenoxyethanol 1, 3-bis (2,4-diaminophenoxy) -propane, 1-methoxy-2-amino
  • Di- or trihydroxybenzene derivatives such as resorcinol, resorcinol monomethyl 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- Hydr
  • 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
  • indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole
  • pyrimidine derivatives such as For example, 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyhmidine, 2-amino-4-hydroxy 6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine, or
  • Methylenedioxybenzene derivatives such as 1-hydroxy-3,4-methylenedioxybenzene, 1-amino-3,4-methylenedioxybenzene and 1- (2-hydroxyethyl) amino-3,4-methylenedioxybenzene.
  • coupler components according to the invention are 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4-chlororesorcinol , 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 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 can carry further substituents, for. 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, a C r C 4 -alkyl group or a C r C 4 -hydroxy-alkyl group,
  • 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 group, and
  • G 25 is 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.
  • derivatives of the 5,6-dihydroxyindole of the formula Xb are also suitable as precursors of naturally-analogous hair dyes.
  • G 27 is hydrogen, a C r C 4 -alkyl group or a C r 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 an alkyl group 4 C r C,
  • G 30 is hydrogen, a C r C 4 alkyl group or a group -CO-G 32 in which G 32 is a C r C 4 alkyl group, and
  • G 31 is one of the groups mentioned under G 30 , as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • 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-5,6-dihydroxyindole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, and especially the 5,6 -Dihydroxyindol.
  • 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 usually in these Amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-% included.
  • 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 Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds as well as 1 , 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis (.beta.-hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- (.beta.-hydroxyethyl) -aminophenol, 2 (2-hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxye
  • 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:
  • 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.
  • compositions according to the invention according to this embodiment contain the substantive dyes preferably in an amount of 0.01 to 20 wt .-%, preferably from 0.01 to 10 wt .-%, each based on the total colorant.
  • preparations of the invention may also naturally occurring dyes, such as those contained in henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkanel.
  • oxidation dye precursors present in the agents according to the invention or the substantive dyes optionally contained in each case represent uniform compounds. Rather, in the colorants according to the invention, due to the production process for the individual dyes, in minor amounts, other components may be included, as far as they do not adversely affect the dyeing result or for other reasons, eg. As toxicological, must be excluded.
  • 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. Consequently, the presence of additional oxidizing agents can be dispensed with. However, it may u. It may be desirable to add hydrogen peroxide or other oxidizing agents to the compositions of the present invention for achieving the hues that are brighter than the keratin-containing fiber to be dyed. Oxidizing agents are usually used in an amount of 0.01 to 6 wt .-%, based on the application solution. An oxidizing agent preferred for human hair is H 2 O 2 .
  • Oxidationsmittei or the oxidizing agent combination can be used according to the invention in conjunction with oxidation catalysts in the hair dye for use.
  • 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.
  • compositions according to the invention for the oxidative dyeing of keratinic fibers preferably contain at least one derivative of the general formula (I) in an amount of 0.01 to 10% by weight, particularly preferably 0.1 to 3% by weight, based on the finished composition ,
  • 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 can be composed according to known colorants or contain the usual ingredients for these.
  • the agents according to the invention preferably contain the dye precursors in one suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • surfactant-containing foaming solutions such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • Aqueous-alcoholic solutions of the present invention are aqueous solutions containing, to understand 3 to 70 wt .-% of a C r C 4 -alcohol, in particular ethanol or isopropanol in a sense.
  • 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, wherein 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. Example, a carboxylate, sulfate, sulfonate or phosphate group and 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.
  • anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as mono-, di- and trialkanolammonium salts with 2 or 3 C atoms in the alkanol group, linear fatty acids having 10 to 22 C atoms (Soap),
  • 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 methyl-branched in the 2-position aliphatic radicals.
  • Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. Particularly preferred are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl.
  • oxo-alcohols compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • 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.
  • R 1 consists essentially of C 8 and C 10 alkyl groups, essentially of C 12 and C 14 alkyl groups, essentially of C 8 to C 16 alkyl groups or essentially of C 12 - to C 16 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, in addition to their surfactant effect, the fixation to improve 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 those surface-active compounds which carry in the molecule at least one quaternary ammonium group and at least one -COO W or -SC ⁇ group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinates, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example the cocoacylaminopropyldimethylammoniumglycinate, and 2-alkyl-3-carboxy-methyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl-hydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
  • ampholytic surfactants are understood as meaning surface-active compounds which, in addition to a C 8 -C 18 -alkyl or acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and for the formation of 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-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12-18 acylsarcosine.
  • the cationic surfactants used may in particular be those of the quaternary ammonium compounds, esterquats and amidoamines type become.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.
  • 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 (manufacturer: Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing hydroxylamino-modified silicone which is also known as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® - Quat 3270 and 3272 (manufacturer: Th Goldschmidt; diquatemäre polydimethylsiloxanes, quaternium. -80).
  • 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 / inylacetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallyl ammonium chloride copolymers, dimethylaminoethyl quaternized with diethyl sulfate methacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride / acrylate copolymers and oct
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabicum, karaya gum, locust bean gum, linseed gums, dextrans, celulose derivatives, eg. 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 hydrocolioids such. For example, polyvinyl alcohol,
  • Structureants such as glucose and maleic acid, hair conditioning compounds such as phospholipids, 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,
  • 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, with 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.
  • the dyeing creams according to Table 1 and the developer emulsion according to Table 2 were prepared by a known method.
  • Each dyeing cream was mixed with the developer emulsion in a ratio of 1: 1 and dyed for each mixture on a natural white strand of hair (from Kerling) for 30 minutes at 32 ° C.
  • the weight ratio of the application mixture to the hair was 4 to 1.

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Abstract

L'invention concerne des agents servant à colorer des fibres kératiniques, en particulier des cheveux humains, par oxydation. Ces agents comprennent, en tant que précurseur de colorant d'oxydation, des composés de formule (I) dans laquelle les groupes R1, R2, X, et Y sont tels que définis dans la première revendication. Ces précurseurs de colorant d'oxydation sont conçus pour une coloration par oxydation à l'air, ou en présence d'agents d'oxydation supplémentaires, tels que le peroxyde d'hydrogène. La présente invention concerne en outre des dérivés de formule (I) servant à colorer des fibres kératiniques, ainsi qu'un procédé correspondant pour colorer des fibres kératiniques, en particulier des cheveux humains.
PCT/EP2006/002757 2005-04-01 2006-03-25 Agents servant a colorer des fibres keratiniques WO2006103036A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4335623A1 (de) * 1993-10-19 1995-04-20 Henkel Kgaa Indolinon-Derivate zum Färben keratinhaltiger Fasern
EP1010419A2 (fr) * 1998-12-15 2000-06-21 Wella Aktiengesellschaft Agent contenant de l'indanedione et des amines aromatiques pour la teinture des fibres
EP1609458A1 (fr) * 2004-06-14 2005-12-28 L'oreal Compositions tinctoriales comprenant un dérivé de 1,3-indanedione

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4335623A1 (de) * 1993-10-19 1995-04-20 Henkel Kgaa Indolinon-Derivate zum Färben keratinhaltiger Fasern
EP1010419A2 (fr) * 1998-12-15 2000-06-21 Wella Aktiengesellschaft Agent contenant de l'indanedione et des amines aromatiques pour la teinture des fibres
EP1609458A1 (fr) * 2004-06-14 2005-12-28 L'oreal Compositions tinctoriales comprenant un dérivé de 1,3-indanedione

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
FOX, JAY B., JR. ET AL: "Ruhemann's purple from ninhydrin, ascorbate, and nitrite", BIOORGANIC CHEMISTRY , 12(3), 235-41 CODEN: BOCMBM; ISSN: 0045-2068, 1984, XP009068089 *
GAMON N ET AL: "DARSTELLUNG UND EIGENSCHAFTEN VON BETA-PHOSPHA-TRINETHINCYANIN- FARBSTOFFEN MIT INDOLIN-ENDGRUPPEN SYNTHESIS AND PROPERTIES OF BETA-PHOSPHATRIMETHINECYANINE DYES WITHINDOLINE END GROUPS", LIEBIGS ANNALEN DER CHEMIE, VERLAG CHEMIE GMBH. WEINHEIM, DE, vol. 12, 1980, pages 2072 - 2094, XP001038529, ISSN: 0170-2041 *

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