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WO2005117819A1 - Composes de couplage m-phenylene diamine - Google Patents

Composes de couplage m-phenylene diamine Download PDF

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Publication number
WO2005117819A1
WO2005117819A1 PCT/EP2005/004771 EP2005004771W WO2005117819A1 WO 2005117819 A1 WO2005117819 A1 WO 2005117819A1 EP 2005004771 W EP2005004771 W EP 2005004771W WO 2005117819 A1 WO2005117819 A1 WO 2005117819A1
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alkyl
amino
hydrogen
substituted
general formula
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PCT/EP2005/004771
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German (de)
English (en)
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Georg KNÜBEL
Horst Höffkes
Ralph Nemitz
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to EP05740500A priority Critical patent/EP1748822A1/fr
Publication of WO2005117819A1 publication Critical patent/WO2005117819A1/fr

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    • 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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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 present invention relates to agents for dyeing keratin fibers which contain special m-phenylenediamine derivatives, a process for dyeing hair with these agents, and to a part of these m-phenylenediamine derivatives themselves and intermediates which are formed in the preparation of these compounds.
  • oxidation coloring agents play a preferred role because of their intense colors and good fastness properties.
  • colorants contain oxidation dye precursors, so-called developer components and
  • the developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or under coupling with one or more coupler components.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Suitable coupler substances are in particular 1-naphthol, 1, 5-, 2.7- and 1.7- Dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, l-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, l, 3- Bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5- aminophenol.
  • Mono-alkyl-substituted 1,3-phenylenediamines have long been used as a coupler component in oxidative hair colors.
  • 2,4-diaminotoluene has been used in the past for many years, for example as a blue coupler for p-phenylenediamine and p-tolylenediamine.
  • Di-alkyl-substituted 1,3-phenylenediamines have also been used as a coupler component in oxidative hair colors.
  • Good oxidation dye precursors should form the desired color shades in sufficient intensity and fastness in the oxidative coupling. They should also have a good ability to draw onto the fiber, with no noticeable differences between stressed and freshly regrown hair, in particular with human hair (leveling ability). They should be resistant to light, heat, sweat, friction and the influence of chemical reducing agents, e.g. Perm liquids. After all, if they are used as hair dye, they should not stain the scalp too much, and above all they should be harmless from a toxicological and dermatological point of view. Furthermore, the coloring achieved should be easily removed from the hair again by bleaching, if it does not correspond to the individual wishes of the individual and is to be reversed.
  • the invention therefore firstly relates to compositions for dyeing keratin fibers, in particular human hair, containing at least one m-phenylenediamine derivative of the general formula (I) in a cosmetically acceptable carrier as a coupling component
  • R ⁇ R 2, R 3, R 4 are independently H, C ⁇ -6 alkyl, C 2 - 6 hydroxyalkyl, C 2-6 alkoxyalkyl, C 2-6 aminoalkyl, C - ⁇ 0 alkylaminoalkyl, C 3 - ⁇ 2 -dialkylaminoalkyl,
  • R 5 , R 6 independently of one another. 6 alkyl, which is optionally substituted by:
  • R 7 is H, halogen, or C] -6 alkoxy, C ⁇ -6 alkyl, optionally substituted on the aromatic nucleus other than the nearest carbon atom are substituted by:
  • Keratinic fibers are to be understood according to the invention to mean furs, wool, feathers and in particular human hair.
  • the oxidation colorants according to the invention are primarily suitable for dyeing keratin fibers, there is in principle nothing to prevent them from being used in other areas, particularly in color photography.
  • the known acid addition salts can be prepared from them in the usual way.
  • the invention therefore relates both to the compounds present in free form and to their water-soluble, physiologically tolerable salts.
  • such salts are the hydrochlorides, the hydrobromides, the sulfates, the phosphates, the acetates, the propionates, the citrates and the lactates.
  • the hydrochlorides and the sulfates are particularly preferred.
  • Ci- alkyl preferably -C 4 alkyl groups which may be linear or branched, the groups methyl, ethyl, propyl, isopropyl, butyl, pentyl and hexyl.
  • Ethyl and methyl are preferred alkyl groups.
  • a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group can be mentioned as the preferred Ci to C 6 - (mono) hydroxyalkyl group.
  • a 2-hydroxyethyl group is particularly preferred.
  • C 2-6 alkoxyalkyl radicals have a total of 2 to 6 carbon atoms, which are distributed over the alkoxy and the alkyl radical. It can so that there are up to 5 carbon atoms in the alkoxy or alkyl radical. It is preferably a C ⁇ . 3 -alkoxy-C ⁇ .3-alkyl radical, particularly preferably C1. 2 -alkoxy-C 1 . 2 - alkyl group. Both the alkoxy and the alkyl radical can be linear or branched. They are preferably linear.
  • C2- 6 -aminoalkyl, preferably C 2-4 -aminoalkyl, C 2- ⁇ 0 -Alkylaminoalkylreste, C 2-6 -Alkylaminoalkylreste and preferably C 3 i 2 - dialkylaminoalkyl, preferably C 3-9 -Dialkylaminoalkylreste may each be linear or branched Have alkyl radicals. Each individual alkyl group preferably has 1 to 3 carbon atoms. The alkyl radicals present in the respective groups are preferably defined as above for the pure alkyl radicals.
  • radicals are optionally substituted, depending on the number of carbon atoms in the alkyl or alkoxy radical, there may preferably be 1 to 3, particularly preferably 1 or 2, in particular one substituent.
  • R 5 , R 6 , R 7 and X may have substituents, some of which may in turn be substituted by -OH. Preferably only one of these further OH substituents is present.
  • C -4 alkyl and C M alkoxy radicals are in turn linear or branched, preferably linear, and particularly preferably ethyl or methyl. If one of the radicals R 1 to R 7 and X contains a hydroxyl group bonded to an alkylene radical, the hydroxyl group is preferably terminal and the alkylene radical is linear.
  • a hydroxyethyl radical is therefore preferably a 2-hydroxyethyl radical. If the rest of R 7 is a C ⁇ . 6 -alkoxy or Ci- 6 -alkyl radical, this may be substituted, but not on the C atom which is closest to the aromatic nucleus to which the radical R 7 is attached.
  • Halogen is generally F, Br, CI or I, preferably CI or Br.
  • An m-phenylenediamine derivative of the general formula (I) particularly preferably has a maximum of four OH groups, preferably a maximum of two OH groups.
  • the m-phenylenediamine derivative of the general formula (I) preferably contains a maximum of four nitrogen atoms, particularly preferably two nitrogen atoms.
  • the m-phenylenediamine derivative of the general formula (I) contains a maximum of a further four oxygen atoms, preferably a maximum of a further two oxygen atoms.
  • R 1 , R 2 , R 3 , R 4 are independently hydrogen, C -4 alkyl or C 2-4 hydroxyalkyl.
  • R 1 and R 3 are particularly preferably hydrogen and R 2 and R 4 are hydrogen or C 2-4 -hydroxyalkyl.
  • R 5 and R 6 independently of one another are C 4 - alkyl.
  • X is preferably hydrogen.
  • R 7 is preferably hydrogen or C alkyl.
  • R 1 , R 2 , R 3 , R 4 , X are hydrogen and R 5 , R 6 is methyl.
  • R 7 particularly preferably denotes hydrogen or methyl.
  • R 1 , R 3 , X, R 7 are hydrogen, R 5 , R 6 is methyl and R 2 , R 4 -CH 2 -CH 2 OH.
  • the agent according to the invention can contain one or more, for example at least two different m-phenylenediamine derivatives, e.g. of the general formula (I).
  • the m-phenylenediamine derivatives of the formula (I) can be prepared using conventional organic methods. As an example, reference is made to the experimental procedures in the context of the exemplary embodiments.
  • the agents for dyeing keratin fibers according to the invention preferably contain the at least one m-phenylenediamine derivative of the general formula (I) in an amount of 0.001 to 15% by weight, particularly preferably 0.05 to 5% by weight, based on the finished agent .
  • the agent for dyeing keratin fibers can be selected from any suitable agents which are particularly suitable for dyeing human hair.
  • an otherwise customary carrier of agents for coloring human hair is used as the cosmetically acceptable carrier.
  • the colorants according to the invention can, apart from the m-phenylenediamine derivatives of the general formula (I), be composed according to known colorants or contain the usual ingredients for them. Examples of other suitable ingredients preferred according to the invention are given below.
  • Agents according to the invention can have the following ingredients in the amounts indicated.
  • Suitable colorant compositions are described, for example, in DE-U 1-299 11 819, DE-A-101 25 451, DE-Ul-201 11 036 and the specialist book Cosmetics, ed. W. Umbach, 2nd ed. 1995, G. Thieme Verlag Stuttgart, New York.
  • the colorants according to the invention can also contain at least one developer component.
  • P-Phenylenediamine derivatives of the formula (E1) are particularly preferred
  • G 1 represents a hydrogen atom, a Ci to C 4 alkyl radical, a Ci to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C r to C 4) - alkoxy (d- to C 4 ) -alkyl, a 4'-aminophenyl or a Ci- to C -alkyl radical which is substituted by a nitrogen-containing group, a phenyl or a 4'-aminophenyl radical;
  • G 2 represents a hydrogen atom, a Ci to C 4 alkyl radical, a Ci to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (Ci to C 4) - alkoxy (C ⁇ - to C 4 ) alkyl radical or a C 1 -C 4 -alkyl radical which is substituted by a nitrogen-containing group;
  • G 3 represents a hydrogen atom,
  • Examples of the Cr to C alkyl radicals mentioned as substituents in the compounds are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals.
  • Preferred Cr to C 4 alkoxy radicals are, for example, a methoxy or an ethoxy group.
  • preferred examples of a C 1 -C 4 -hydroxyalkyl group are a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group.
  • a 2-hydroxy ethyl group is particularly preferred.
  • a particularly preferred C 2 - to C 4 - polyhydroxyalkyl group is 1, 2-dihydroxyethyl.
  • halogen atoms are F, CI or Br atoms, Cl atoms are very particularly preferred.
  • the other terms used are derived from the definitions given here.
  • nitrogen-containing groups of the formula (E1) are in particular the amino groups, Cr to C monoalkylamino groups, Cr to C 4 dialkylamino groups, Cr to C 4 trialkylammonium groups, Cr to C monohydroxyalkylamino groups, imidazolinium and ammonium.
  • 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-
  • P-Phenylenediamine derivatives of the formula (E1) which are very particularly preferably used according to the invention are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p-phenylenediamine and N-bis (ß-hydroxyethyl) -p-phenylenediamine.
  • developer component compounds 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 coloring compositions according to the invention, one can name in particular the compounds which correspond to the following formula (E2) and their physiologically tolerable salts:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 radical which is optionally substituted by a C ⁇ - to C 4 -alkyl radical, by a Cr to C 4 - hydroxyalkyl radical and / or by a bridging Y.
  • 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 are interrupted or terminated by one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms can and may be substituted by one or more hydroxyl or Cr to C 8 alkoxy radicals, or a direct bond
  • G 5 and G 6 independently of one another represent a hydrogen or halogen atom, a Cr to C 4 alkyl radical, a Cr to C 4 monohydroxyalkyl, a C 2 to C 4 polyhydroxyalkyl, a Cr to C 4 aminoalkyl or a direct connection to the bridging Y
  • G 7 , G 8 , G 9 , G 10 , G 11 and G 12 are independent from each other for a hydrogen atom, a direct bond to the bridging Y or a Cr to C 4 alkyl radical
  • Preferred dinuclear developer components 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 (ß-hydroxyethyl) -N, N'-bis (4 , -aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylene diamine, N, N'-bis - (ß-hydroxyethyl) -N, N'-bis- (4-aminophenyl) tetramethylene diamine, N, N'-bis (4-methyl-aminophenyl) tetramethylene diamine, N, N'-diethyl-N, N ' -bis- (4'-amino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminophen
  • Very particularly preferred dinuclear developer components of the formula (E2) are N, N'-bis (ß-hydroxyethyl) -N, N'-bis (4'-aminophenyl) -l, 3-diamino-propan-2-ol, Bis (2-hydroxy-5-aminophenyl) methane, 1,3-bis (2,5-diaminophenoxy) propan-2-ol, N, N'-bis (4'-aminophenyl) -l, 4-diazacycloheptane and l, 10-bis- (2 ', 5'-diaminophenyl) -l, 4,7,10-tetraoxadecane or one of their physiologically tolerable salts.
  • P-Aminophenol derivatives of the formula (E3) are particularly preferred
  • G 13 represents a hydrogen atom, a halogen atom, a Cr to C alkyl radical, a Cr to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a (Cr to C 4 ) alkoxy (Cr to C 4 ) -alkyl radical, a C to C 4 -aminoalkyl radical, a hydroxy- (Cr to C 4 ) -alkylamino radical, a Cr to C 4 -hydroxyalkoxy radical, a Cr to C -hydroxyalkyl- (C ⁇ -to C 4 ) -aminoalkyl radical or a (di-Cr to C 4 alkylamino) - (Cr to C 4 ) alkyl radical, and G 14 represents a hydrogen or halogen atom, a Cr to C 4 alkyl radical, a Cr to C 4 monohydroxyalkyl radical, one C2 to C 4 polyhydroxyalkyl, a (Cr to flu
  • 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- (ß-hydroxyethoxy) phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino -2-aminomethylphenol, 4-amino-2- (ß-hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ß-dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2 -chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (die
  • 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 can also be selected from o-aminophenol and its derivatives, such as, for example, 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component can be selected from heterocyclic developer components, such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • heterocyclic developer components such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • Preferred pyridine derivatives are, in particular, the compounds described in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) amino-3-aminopyridine , 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 patent publication JP 02019576 A2 or in laid-open publication 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-triaminopyrirnidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6- triaminopyrimidine.
  • Preferred pyrazole derivatives are in particular the compounds described in the 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-l-methylpyrazole, 4,5-diamino-1 - (ß-hydroxyethyl) -pyrazole, 3,4-diaminopyrazole, 4,5-diamino-l - (4 1 - chlorobenzyl) -pyrazole, 4,5- Diamino-l, 3-dimethylpyrazole, 4,5-diamino-3-methyl-l-phenylpyrazole, 4,5-diamino-l-methyl-3-phenylpyrazole, 4-amino-l, 3-dimethyl-5-hydrazinopyrazole, l-benzyl-4,5-diamino-3-methylpyrazole, 4,5-di
  • Preferred pyrazole-pyrimidine derivatives are in particular the derivatives of pyrazole- [1,5-a] -pyrimidine of the following formula (E4) and its tautomeric forms, provided that there is a tautomeric equilibrium:
  • G 17 , G 18 , G 19 and G 20 independently represent a hydrogen atom, a Cr to C alkyl radical, an aryl radical, a Cr to C hydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical a ( Cr to C 4 ) alkoxy- (Cr to C 4 ) - alkyl radical, a Cr to C 4 -aminoalkyl radical, which can optionally be protected by an acetyl-ureide or a sulfonyl radical, a (Cr to C) alkylamino - (Cj to C) alkyl radical, a di - [(Cr to C) alkyl] - (Cr to C 4 ) - aminoalkyl radical, the dialkyl radicals optionally forming a carbon cycle or a heterocycle with 5 or 6 chain links, a C ⁇ - to C 4 - Hydroxyalkyl or a di (Cr to C 4 ) - [hydroxyal
  • pyrazole- [1,5-a] -pyrimidines of the above formula (E4) one can mention in particular: pyrazole- [1,5-a] -pyrimidine-3,7-diamine; 2,5-dimethylpyrazole- [1,5-a] pyrimidine-3,7-diamine; Pyrazole- [1,5-a] pyrimidine-3,5-diamine; 2,7-dimethylpyrazole- [1,5-a] pyrimidine-3,5-diamine; 3-aminopyrazole [l, 5-a] - ⁇ yrimidin-7-ol; 3-aminopyrazole- [1,5-a] pyrimidin-5-ol; 2- (3-aminopyrazole- [1,5-a] pyrimidin-7-ylamino) ethanol; 2- (7-aminopyrazole [l, 5-a] pyrimidine-3-ylamino) ethanol; 2 - [(3-aminopyrazo
  • the pyrazole [1,5-a] pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.
  • the colorants according to the invention contain at least one further coupler component.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used as coupler components.
  • Suitable coupler substances are, in particular, 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomino methyl ether, m-phenylenediamine, l-phenyl -3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2 ', 4'-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2 -Chlor-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylre
  • 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
  • Coupler components which are particularly preferred 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, 2,6-dihydroxy-3,4-dimethylpyridine, 2 - ⁇ ( ⁇ 3- [2- Hydroxyethyl) amino] -2-methoxy-5-methylphenyl ⁇ amino) ethanol, 2- ( ⁇ 3 - [2-hydroxyethyl) amino] -4-methoxy-5-methylpheny 1 ⁇ amino) ethanol and 2 - [( 3-morpholin-4-ylphenyl) amino] ethanol.
  • coupler / developer combinations have proven to be particularly suitable according to the invention: p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, 1 - (2-hydroxyethyl) -2,5-diaminobenzene, 1 - (2-hydroxyethyl) -4,5-diaminopyrazole and bis- (2-hydroxy-5 -aminophenyl) methane in each case in combination with the compounds from the examples, in particular with 2- ( ⁇ 3 - [(2-hydroxyethyl) amino] -4,5-dimethylphenyl ⁇ amino) ethanol.
  • the colorants can contain at least one precursor of a nature-analog dye.
  • These groups can carry further substituents, e.g. B. in the form of etherification or esterification of the hydroxy group or an alkylation of the amino group.
  • the colorants contain at least one indole and / or indoline derivative.
  • Derivatives of 5,6-dihydroxyindoline of the formula (Ha) are particularly suitable as precursors of nature-analogous hair dyes,
  • R 1 stands for hydrogen, a C 1 -C 4 -alkyl group or a C] -C 4 -hydroxy-alkyl group
  • - R 2 stands for hydrogen or a -COOH group
  • the -COOH group can also be present as a salt with a physiologically compatible cation
  • R stands for hydrogen or a C 4 alkyl group
  • R 4 stands for hydrogen, a C 4 alkyl group or a group -CO-R 6 , in which R 6 stands for a C 4 alkyl group
  • R 5 represents one of the groups mentioned under R 4 , as well as physiologically tolerable 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 that 5,6-Dihydroxyindolin.
  • R 1 stands for hydrogen, a CrC 4 alkyl group or a C 1 -C 4 hydroxyalkyl group
  • R 2 stands for hydrogen or a -COOH group
  • the -COOH group also as a salt with a physiologically acceptable cation may be present
  • R represents hydrogen or a C 1 -C 4 alkyl group
  • R 4 represents hydrogen, a C 1 -C 4 alkyl group or a group -CO-R 6 , in which R 6 represents a C ⁇ - C 4 alkyl group
  • R 5 stands for one of the groups mentioned under R 4 , and physiologically tolerable 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 in particular 5.6 are to be emphasized -Dihydroxyindol.
  • the indoline and indole derivatives can be used in the colorants according to the invention both as free bases and in the form of their physiologically tolerable salts with inorganic or organic acids, for.
  • the indole or indoline derivatives are usually contained in these in amounts of 0.05-10% by weight, preferably 0.2-5% by weight.
  • the indoline or indole derivative in colorants in combination with at least one amino acid or an oligopeptide.
  • the amino acid is advantageously an ⁇ -amino acid; very particularly preferred ⁇ -amino acids are arginine, omithin, lysine, serine and histidine, in particular arginine.
  • the colorants according to the invention can contain one or more direct dyes for shading.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred direct dyes are those with the international names 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 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 and 1 , 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis ( ⁇ -hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- ( ⁇ -hydroxyethyl) aminophenol, 2 - (2'-Hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxyethyl) arnin
  • the agents according to the invention can also contain a cationic direct dye.
  • a cationic direct dye such as, for example, Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14,
  • aromatic systems which are substituted with a quaternary nitrogen group, such as, for example, Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
  • substantive dyes which contain a heterocycle which has at least one quaternary nitrogen atom, as described, for example, in EP-A2-998 908, to which at this point explicit reference is made to claims 6 to 11.
  • Preferred cationic direct dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic direct dyes of group (c).
  • the cationic direct dyes which are sold under the brand Arianor® ® are, according to the invention also very particularly preferred cationic direct dyes.
  • the agents according to the invention in accordance with this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20% by weight, based on the total colorant.
  • preparations according to the invention can also contain naturally occurring dyes, such as those contained in henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • naturally occurring dyes such as those contained in henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • the oxidation dye precursors or the substantive dyes each represent uniform compounds. Rather, in the hair colorants according to the invention, due to the production process for the individual dyes, further components may be present in minor amounts, provided that these do not adversely affect the coloring result or must be excluded for other reasons, for example toxicological ones.
  • the dyes which can be used in the hair dyeing and toning agents according to the invention reference is also expressly made to the monograph Ch. Zviak, The Science of Hair Care, chapter 7 (pages 248-250; direct dyes) and chapter 8, pages 264-267; Oxidation dye precursors), published as Volume 7 of the "Dermatology" series (ed .: Ch., Culnan and H.
  • the colorants according to the invention can furthermore contain all active substances, additives and auxiliaries known for such preparations.
  • the colorants contain at least one surfactant, with both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups can be contained in the molecule.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon 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.
  • Non-ionic surfactants contain z.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such compounds are, for example, adducts of 2 to 30 mol of ethylene oxide and / or 0 to 5 mol of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols with 8 to 15 C atoms in the alkyl group, Ci2-C22 fatty acid mono- and diesters of addition products of 1 to 30 mol ethylene oxide with glycerol, C8-C22 alkyl mono- and oligoglycosides and ethoxylated analogs thereof and addition products of 5 to 60 mol ethylene oxide onto castor oil and hydrogenated castor oil.
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula R * O- (Z) ⁇ . These connections are characterized by the following parameters.
  • the alkyl radical R 1 contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and methyl-branched aliphatic radicals in the 2-position are preferred. Examples of such alkyl radicals are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred. When using so-called "oxo alcohols" as starting materials, 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 a certain alkyl radical R 1 .
  • these compounds are made from natural fats and oils or mineral oils.
  • the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the respective working up of these compounds.
  • R 1 consists essentially of Cg and Cio-alkyl groups, essentially from C] 2 - and C ⁇ 4 -alkyl groups, essentially from C 8 - to Ci 6 -alkyl groups or essentially from C ⁇ - to C ⁇ 6 alkyl groups.
  • Any mono- or oligosaccharides can be used as the sugar building block Z.
  • sugar with 5 or 6 carbon atoms and the corresponding Oligosaccharides used.
  • examples of such sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar components are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain on average 1.1 to 5 sugar units. Alkyl polyglycosides with x values from 1.1 to 1.6 are preferred. Alkyl glycosides in which x is 1.1 to 1.4 are very particularly preferred.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • the person skilled in the art will preferably resort to this substance class as a further ingredient of the preparations according to the invention.
  • alkoxylated homologs of the alkyl polyglycosides mentioned can also be used according to the invention. These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • zwitterionic surfactants can be used, in particular as co-surfactants.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COO ⁇ or -SOs ⁇ group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and also the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI name Cocamidopropyl Betaine.
  • pholytic surfactants are understood to mean those surface-active compounds which addition to a C-C ⁇ g - alkyl or acyl group, contain at least one free amino group and contain at least one -COOH or -SO3H group and are capable of forming inner salts.
  • 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 with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are the N-coconut alkylaminopropionate, the coconut acylaminoethylaminopropionate and the C 2- i 8 acyl sarcosine.
  • cationic surfactants in particular can be those of the quaternary ammonium compound, esterquat and amidoamine type.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names quatemium-27 and quatemium-83.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Ester quats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred ester quats 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 sold, for example, under the brands Stepantex ® , Dehyquart ® and Armocare ® .
  • the alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An invented According to the invention, a particularly suitable compound from this group of substances is stearamidopropyldimethylamine, which is commercially available under the Tegoamid ® S 18 brand.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Coming; a stabilized trimethylsilylamodimethicone), Dow Coming 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM- 2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® - Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxane, 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 with alkyl groups used as surfactant can 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 with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts when converting fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates as catalysts be used. The use of products with a narrow homolog distribution can be preferred.
  • the colorants according to the invention can contain further active ingredients, auxiliaries and additives, such as, for example, nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternized cellulose ethers , Dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallyl-ammonium chloride copolymers, dimethylamino-ethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinylalphamido-methylethyl alcohol, zamperidyl chloride, for example, amino
  • methyl cellulose As methyl cellulose, hydroxyalkyl cellulose and carboxy methyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such.
  • B. bentonite or fully synthetic hydrocolloids such as polyvinyl alcohol, structurants such as maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, protein hydrolyzates, in particular elastin, collagen, keratin, milk protein, soy protein and Wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins, Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, active substances which improve fiber structure, in particular mono-, di- and oligosacchari
  • Quaternized amines such as methyl l-alkylamidoethyl-2-alkylimidazolinium methosulfate defoamers such as silicones, dyes for coloring the agent, anti-dandruff agents such as piroctone olamines, zinc omadines and climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines to adjust the pH, such as customary acids, especially edible acids and bases, active ingredients such as AUantoin, pyrrolidonecarboxylic acids and their salts, and bisabolol, vitamins, provitamins and vitamin precursors, especially those from groups A, B 3 , B 5 , B 6 , C , E, F and H, plant extracts such as the extracts from green tea, oak bark, nettle, witch hazel, hops, chamomile, burdock root, horsetail, white doe, linden flowers, almond,
  • Cholesterol consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax and paraffins, fatty acid alkanolamides, complexing agents such as EDTA, NTA, ⁇ -alanine diacetic acid and phosphonic acids, swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonate , Ureas and primary, secondary and tertiary phosphates,
  • Opacifiers such as latex, styrene PVP and styrene / acrylamide copolymers pearlescent agents such as ethylene glycol mono- and distearate and PEG-3 distearate, pigments, stabilizing agents for hydrogen peroxide and other oxidizing agents, - Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air, antioxidants, contain.
  • the agents according to the invention preferably contain the dye precursors in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier are, for example, creams, emulsions, gels or also 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 are to be understood as meaning aqueous solutions containing 3 to 70% by weight of a C 1 -C 4 alcohol, in particular ethanol or isopropanol.
  • the agents according to the invention can additionally contain further organic solvents, such as, for example, methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. All water-soluble organic solvents are preferred.
  • the actual oxidative coloring of the fibers can basically be done with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a lightening effect on human hair is desired.
  • Persulfates, chlorites and in particular hydrogen peroxide or their adducts with urea, melamine and sodium borate are suitable as oxidizing agents.
  • the oxidation coloring agent can also be applied to the hair together with a catalyst which activates the oxidation of the dye precursors, for example by atmospheric oxygen.
  • catalysts are, for example, metal ions, iodides, quinones or certain enzymes.
  • Suitable metal ions are, for example, Zn 2+ , Cu 2+ , Fe 2+ , Fe 3+ , Mn 2+ , Mn 4+ , Li + , Mg 2+ , Ca 2+ and Al 3+ .
  • Zn 2+ , Cu 2+ and Mn 2+ are particularly suitable.
  • the metal ions can be used in the form of any physiologically acceptable salt or in the form of a complex compound.
  • Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
  • Suitable enzymes are e.g. Peroxidases, which can significantly increase the effects of small amounts of hydrogen peroxide. Furthermore, such enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the help of atmospheric oxygen, such as for example the laccases, or generate small amounts of hydrogen peroxide in situ and in this way activate the oxidation of the dye precursors biocatalytically.
  • Particularly suitable catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the substrates specific for this, e.g. Pyranose oxidase and e.g.
  • D-glucose or galactose glucose oxidase and D-glucose, glycerol oxidase and glycerol, pyruvate oxidase and pyruvic acid or their salts, alcohol oxidase and alcohol (MeOH, EtOH), lactate oxidase and lactic acid and their salts, tyrosinase -Oxidase and tyrosine, uricase and uric acid or their salts, choline oxidase and choline, amino acid oxidase and amino acids.
  • the actual hair dye is expediently prepared immediately before use by mixing the preparation of the oxidizing agent with the preparation containing the dye precursors.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 12. It is particularly preferred to use the hair dye in a weakly alkaline environment. Application temperatures can range between 15 and 40 ° C. After an exposure time of generally 5 to 45 minutes, the hair dye is removed from the hair to be colored by rinsing. The washing up with a shampoo is not necessary if a carrier with a high surfactant content, e.g. a coloring shampoo, has been used.
  • the preparation with the dye precursors can also be applied to the hair without prior mixing with the oxidation component.
  • the oxidation component is then applied, if necessary after an intermediate rinse.
  • the skin is rinsed and, if necessary, re-shampooed.
  • the corresponding agent is adjusted to a pH of about 4 to 7.
  • air oxidation is initially aimed for, the agent applied preferably having a pH of 7 to 10.
  • the use of acidified peroxidisulfate solutions as the oxidizing agent can be preferred.
  • a second subject of the present application is the use of the m-phenylenediamine derivatives according to the invention for dyeing keratin fibers.
  • a third object of the present invention is a process for dyeing keratin fibers, in which a hair dye according to the invention is applied to the fibers and rinsed off again after an exposure time.
  • a fourth object of the present invention is an m-phenylenediamine derivative of the general formula (I) with the meaning R 1 , R 3 , hydrogen, R 7 hydrogen or methyl, X hydrogen or methoxy, R 5 , R 6 methyl and R 2 , R 4 -CH 2 -CH 2 OH.
  • a fifth object of the invention are the intermediates 4-methoxy-5,6-dimethyl-1,3-diaminobenzene, 2-chloroethyl 5 - ⁇ [(2-chloroethoxy) carbonyl] amino ⁇ -2-methoxy-3,4-dimethylphenylcarbamate , 3- [2-methoxy-3,4-dimethyl-5- (2-oxo-1,3-oxazolidin-3-yl) phenyl] -1, 3-oxazolidin-2-one, 2-chloroethyl-3- ⁇ [(2-chloroethoxy) carbonyl] amino ⁇ -4,5-dimethylphenyl carbamate and 3- [2,3-dimethyl-5- (2-oxo-l, 3-oxazolidin-3-yl) phenyl] -l , 3-oxazolidin-2-one.
  • the invention is illustrated by the examples below.
  • the cream base used had the following composition:
  • Ci ö -is fatty alcohol (INCI name: Cetearyl alcohol) (Cognis) Ci 2 -i 8 fatty alcohol (INCI name: Coconut alcohol) (Cognis) lauryl ether sulfate, sodium salt (approx. 27.5% active substance; INCI name : Sodium Laureth Sulfate) (Cognis) N, N-dimethyl-N- (C 8- 18 -kokosamidopropy l) ammoniumacetobetain (ca. 30% active substance; INCI name: Aqua (Water), Cocamidopropyl Betaine) (Cognis) cetyl stearyl alcohol with approx. 20 EO units (INCI name: Ceteareth-20) (Cognis)
  • the dissolved dye precursors were worked into the hot cream one after the other.
  • the mixture was then made up to 97 g with distilled water and filled with Ammonia adjusted a pH of 9.5. After filling up to 100 g with distilled water, the mixture was stirred cold ( ⁇ 30 ° C.), a homogeneous cream being formed.
  • a strand of hair (80% gray; 330 mg to 370 mg in weight) was added to each of the mixtures thus obtained.
  • the mixtures and the strands of hair were then each placed on a watch glass and the strands of hair were well embedded in the coloring creams. After 30 minutes ( ⁇ 1 minute) of exposure at room temperature, the strands of hair were removed and washed with an aqueous Texapon EVR solution 9 until the excess color was removed.
  • the strands of hair were air-dried and their shade was determined and noted under the daylight lamp (color testing device HE240A) (Taschenlexikon der Weg Arthur, A.

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Abstract

La présente invention concerne un agent pour colorer des fibres de kératine, en particulier des cheveux humains, contenant, dans un support acceptable d'un point de vue cosmétique, en tant que composé de couplage, au moins un déviré de m-phénylène diamine de formule générale (I) dans laquelle R1, R2, R3, R4 représentent indépendamment H, alkyle en C1-6, hydroxyalkyle en C2-6, alcoxyalkyle en C2-6, aminoalkyle en C2-6, alkylaminoalkyle en C2-10, dialkylaminoalkyle en C3-12; R5, R6 représentent indépendamment alkyle en C1-6 éventuellement substitué par -OH, alcoxy en C1-4 éventuellement substitué par OH, -NH2, -NHR, -NR2 où R représente indépendamment alkyle en C1-4 éventuellement substitué par OH; R7 représente H, halogène ou alcoxy en C1-6, alkyle en C1-6, qui sont éventuellement substitués, excepté au niveau de l'atome de C adjacent au noyau aromatique, par -OH, alcoxy en C1-4 éventuellement substitué par OH, -NH2, -NHR, -NR2 où R représente indépendamment alkyle en C1-4 éventuellement substitué par OH; X représente H, halogène, alcoxy en C1-6 qui est éventuellement substitué par -OH ou alcoxy en C1-4; ou des sels de celui-ci.
PCT/EP2005/004771 2004-05-28 2005-05-03 Composes de couplage m-phenylene diamine WO2005117819A1 (fr)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2009084695A1 (fr) 2007-12-28 2009-07-09 Carna Biosciences Inc. Dérivé de 2-aminoquinazoline

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EP0819425A1 (fr) * 1996-07-19 1998-01-21 L'oreal Composition de teinture d'oxydation des fibres kératiniques et procédé de teinture mettant en oeuvre cette composition
EP1002518A1 (fr) * 1998-11-20 2000-05-24 L'oreal Composition de teinture d'oxydation des fibres keratiniques et procédé de teinture mettant en oeuvre cette composition
WO2004058204A1 (fr) * 2002-12-23 2004-07-15 Henkel Kommanditgesellschaft Auf Aktien Nouveaux constituants de copulation
EP1496046A1 (fr) * 2003-07-08 2005-01-12 Henkel Kommanditgesellschaft auf Aktien Nouvel agent copulant

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EP0819425A1 (fr) * 1996-07-19 1998-01-21 L'oreal Composition de teinture d'oxydation des fibres kératiniques et procédé de teinture mettant en oeuvre cette composition
EP1002518A1 (fr) * 1998-11-20 2000-05-24 L'oreal Composition de teinture d'oxydation des fibres keratiniques et procédé de teinture mettant en oeuvre cette composition
WO2004058204A1 (fr) * 2002-12-23 2004-07-15 Henkel Kommanditgesellschaft Auf Aktien Nouveaux constituants de copulation
WO2004058205A1 (fr) * 2002-12-23 2004-07-15 Henkel Kommanditgesellschaft Auf Aktien Nouveaux composants coupleurs
EP1496046A1 (fr) * 2003-07-08 2005-01-12 Henkel Kommanditgesellschaft auf Aktien Nouvel agent copulant

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MANN, FREDERICK G. ET AL: "Synthetic antimalarials. XVIII. 3-(Dialkylaminoalkylamino) diphenylamines", JOURNAL OF THE CHEMICAL SOCIETY, ABSTRACTS 910-14 CODEN: JCSAAZ; ISSN: 0590-9791, 1947, XP009052071 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009084695A1 (fr) 2007-12-28 2009-07-09 Carna Biosciences Inc. Dérivé de 2-aminoquinazoline

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