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WO2006050768A1 - Nouveau coupleur m-phénylène diamine - Google Patents

Nouveau coupleur m-phénylène diamine Download PDF

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Publication number
WO2006050768A1
WO2006050768A1 PCT/EP2005/009683 EP2005009683W WO2006050768A1 WO 2006050768 A1 WO2006050768 A1 WO 2006050768A1 EP 2005009683 W EP2005009683 W EP 2005009683W WO 2006050768 A1 WO2006050768 A1 WO 2006050768A1
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Prior art keywords
amino
group
sup
sub
hydroxyethyl
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German (de)
English (en)
Inventor
Georg KNÜBEL
Horst Höffkes
Ralph Nemitz
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication of WO2006050768A1 publication Critical patent/WO2006050768A1/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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Definitions

  • the present invention relates to agents for coloring keratinic fibers containing specific m-phenylenediamine derivatives, a process for dyeing hair with these agents, and the m-phenylenediamine derivatives 3,5-bis - [(2-hydroxyethyl) amino] -anisole.
  • oxidation colorants play a preferential role because of their intense colors and good fastness properties.
  • colorants contain oxidation dye precursors, so-called developer components and coupler components.
  • developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or with coupling with one or more coupler components.
  • developer components are usually primary aromatic amines with another, located in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its Derivatives used.
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used.
  • Suitable coupler substances are, in particular, 1-naphthol, 1,5,7,7,7,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomonomethyl ether, m-phenylenediamine, 1 -Phenyl-3-methyl-pyrazolone-5,2,4-dichloro-3-aminophenol, 1,3-bis (2,4-diamino) phenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol
  • Good oxidation dye precursors are primarily intended to fulfill the following requirements: In the oxidative coupling, they must form the desired color shades in sufficient intensity and authenticity. You must also have a good AufziehFab on the fiber, especially in human hair no significant differences between strained and freshly regrowed hair may exist (leveling ability). They should be resistant to light, heat, sweat, friction and the influence of chemical reducing agents, e.g. Perm liquids. Finally, if applied as a hair dye, they should not stain the scalp too much and above all they should be safe in terms of toxicology and dermatology. Furthermore, the coloring achieved by bleaching should be easily removed from the hair, if it does not meet the individual wishes of each person and should be reversed.
  • the object of the present invention was therefore to develop new coupler components which meet the requirements imposed on oxidation dye precursors, in particular with regard to the toxicological and dermatological properties, and enable dyeings in a broad color spectrum with good fastness properties.
  • a first subject of the present invention are therefore agents for coloring keratinic fibers, in particular human hair, containing in a cosmetically acceptable carrier as coupler component at least one m-phenylenediamine derivative of the formula (I)
  • R 1 is a C 1 to C 2 alkyl group or a C 1 to C 2 monohydroxyalkyl group
  • R 2 , R 3 and R 4 independently of one another represent a hydrogen atom, a methyl or an ethyl group
  • R 5 and R 6 independently of one another represent a branched or unbranched C 2 - to C 6 -
  • keratinic fibers are understood to mean furs, wool, feathers and, in particular, human hair.
  • oxidation dyes according to the invention are primarily suitable for dyeing keratin fibers, in principle there is no obstacle to use in other fields, in particular in color photography.
  • the known acid addition salts can be prepared therefrom in the customary manner. All statements of this document and, accordingly, the scope claimed cover both the compounds present in free form and their water-soluble, physiologically tolerated salts. Examples of 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.
  • the m-phenylenediamine derivatives according to the invention which are present in the colorant are distinguished, in particular, by the fact that intensive, attractive reddish violet shades can be obtained with a number of standard developers, while the coupler component known from WO-A2-93 / 10 744, in combination with corresponding standard developers, is generally blue Color tones results.
  • m-phenylenediamine derivatives are described as coupler components in colorants for coloring keratinic fibers.
  • the aromatic nucleus carries, in addition to the amino substituents, an alkoxy group which may be located in the o- or m-position relative to the two amino groups.
  • the examples describe m-phenylenediamine derivatives whose alkoxy group is in the ortho position to the two amino groups.
  • m-phenylenediamine derivatives having an alkoxy group located in the m-position to the two amino groups are generally described, but concrete compounds having such a substitution pattern are not mentioned.
  • the keratinic fiber coloring agents according to the invention preferably contain at least one m-phenylenediamine derivative of the formula (I) in which R 5 and R 6 are identical substituents, more preferably a 2-hydroxyethyl group or a 3-hydroxypropyl group. Particularly preferably, the substituents R 5 and R 6 each represent a 2-hydroxyethyl group.
  • the m-phenylenediamine derivatives of the formula (I) are preferred in which the substituent R 1 is a methyl group.
  • the m-phenylenediamine derivatives of the formula (I) are preferred in which R 2 , R 3 and R 4 are each independently of one another hydrogen or a methyl group. Particularly preferably, R 2 , R 3 and R 4 are hydrogen.
  • the agent according to the invention particularly preferably contains the m-phenylenediamine derivative 3,5-bis - [(2-hydroxyethyl) amino] -anisole.
  • the m-phenylenediamine derivatives of the formula (I) can be prepared by means of conventional organic methods. For example, reference is made at this point to the experimental procedures in the context of the embodiments.
  • the colorants according to the invention may furthermore contain at least one developer component.
  • the developer components are usually primary aromatic amines having a further, in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives ,
  • p-phenylenediamine derivatives of the formula (E1) it may be preferred according to the invention to use as the developer component a p-phenylenediamine derivative or one of its physiologically acceptable salts. Particular preference is given to p-phenylenediamine derivatives of the formula (E1)
  • G 1 represents a hydrogen atom, a d- to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) alkoxy ( C r to C 4) alkyl group a 4'-aminophenyl, or C 1 - to C 4 alkyl radical substituted with a nitrogenous group, a phenyl group or a 4'-aminophenyl radical;
  • G 2 represents a hydrogen atom, a C 1 - to C 4 -alkyl radical, a C r to C 4 -mono-hydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 1 -alkyl ) - C 1 - to C 4 ) -alkyl radical or a C 1 - to C 4 -alkyl radical which is substituted by a nitrogen-containing group;
  • 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 -Monohydroxyalkylrest, a C 2 - to C 4 polyhydroxyalkyl, C 1 - to C 4 -hydroxyalkoxy, C 1 - to C 4 - acetylaminoalkoxy, C 1 - to C 4 - mesylaminoalkoxy or C 1 - to C 4 - carbamoylaminoalkoxy;
  • a halogen atom such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 - to C 4 alkyl radical such as a chlorine, bromine, iodine or fluorine atom
  • a C 1 - to C 4 alkyl radical such as a chlorine, bromine, iodine or flu
  • 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 an ethylenedioxy group.
  • Examples of the C 1 - to C 4 -alkyl radicals mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl are preferred alkyl radicals. According to the invention, preferred C 1 to C 4 alkoxy radicals are, for example, a methoxy or an ethoxy group. Furthermore, as preferred examples of a C 1 - to C 4 -hydroxyalkyl group, a hydroxymethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group may be mentioned. A 2-hydroxyethyl group is particularly preferred.
  • a particularly preferred C 2 to C 4 polyhydroxyalkyl group is the 1, 2-dihydroxyethyl group.
  • halogen atoms are according to the invention F, Cl or Br atoms, Cl atoms are very particularly preferred.
  • the other terms used are derived according to the invention from the definitions given here.
  • nitrogen-containing groups of the formula (E1) are, in particular, the amino groups, C 1 - to C 4 -monoalkylamino groups, C 1 - to C 4 -dialkylamino groups, C 1 - to C 4 -trialkylammonium groups, C 1 - to C 4 -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-N
  • p-phenylenediamine derivatives' of the formula (E1) are p-phenylenediamine, p-toluylenediamine, 2- (beta-hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ß-dihydroxyethyl) -p-phenylenediamine and N, N-bis (.beta.-hydroxyethyl) -p-phenylenediamine.
  • binuclear developer components which can be used in the dyeing compositions according to the invention, mention may be made in particular of the compounds corresponding to the following formula (E2) and their physiologically tolerated salts:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 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 which is optionally part of a bridging ring system, the bridge Y is an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring, of one or more nitrogen-containing groups and / or one or more heteroatoms such Oxygen, sulfur or nitrogen atoms may be interrupted or terminated and may be substituted by one or more hydroxyl or C r to C 8 alkoxy, 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 -hydroxyalkyl 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 the formula (E2) contain only one bridge Y per molecule and the compounds of the formula (E2) contain at least one amino group which carries at least one hydrogen atom.
  • Preferred binuclear developer component of the formula (E2) are in particular: N 1 N'-bis (.beta.-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-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N, N'-diethyl- N, N'-bis (4'-arnino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminophenyl)
  • binuclear developer components of the formula (E2) are N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, bis - (2-hydroxy-5-aminophenyl) -methane, 1, 3-bis (2,5-diaminophenoxy) -propan-2-ol, N, N'-bis (4'-aminophenyl) -1 , 4-diazacycloheptane and 1, 10-bis- (2 ', 5'-diaminophenyl) -1, 4,7,10-tetraoxadecan or one of its physiologically acceptable salts.
  • Bis (2-hydroxy-5-aminophenyl) methane is a most preferred dinuclear developing agent of formula (E2).
  • p-aminophenol derivatives of the formula (E3) it may be preferred according to the invention to use as the developer component a p-amino phenol 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 (C 1 - to C 4 ) - AIkOXy- (C 1 - to C 4 ) -alkyl radical, a C 1 - to C 4 -Aminoalkylrest, a hydroxy (C r to C 4 ) - alkylamino, a C 1 - to C 4 -hydroxyalkoxy, a C 1 - to C 4 -hydroxyalkyl- (C 1 -C 4 ) -aminoalkyl radical or a (di-C 1 - to C 4 -alkylamino) - (C 1 -C 4 ) -alkyl radical, and
  • G 14 represents a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a d- to C 4 monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) - -alkoxy - (C 1 - to C 4) alkyl group a C 1 - to C 4 -aminoalkyl radical or a Ci to C4 - cyanoalkyl,
  • G 15 is hydrogen, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
  • G 16 is hydrogen or a halogen atom.
  • Preferred p-aminophenols of the formula (E3) are, in particular, p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 -Amino-3-hydroxymethylphenol, 4-amino-2- ( ⁇ -hydroxyethoxy) -phenol, A-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- (diethyl-aminomethyl) -phenol and their physiologically
  • Particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) -phenol and A-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 be selected from 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-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 Patent Publication JP 02019576 A2 or in Laid-Open Specification 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-butyl
  • Preferred pyrazole-pyrimidine derivatives are, in particular, the derivatives of the pyrazolo [1,5-a pyrimidine of the following formula (E4) and its tautomeric forms, provided that a tautomeric equilibrium exists: in which:
  • G, G, G and G are independently a Wasserst off atom, a C 1 - to C 4 -alkyl radical, an aryl radical, a C 1 - to C 4 -hydroxyalkyl group, a C 2 - to C 4 - polyhydroxyalkyl a (C 1 - to C 4) alkoxy (Cr to C4) alkyl group a C 1 - to C 4 - aminoalkyl radical, which may be optionally protected by an acetyl ureide or a sulfonyl residue, a ( C 1 -, alkyl to C 4) alkylamino (Cr to C4) a DH (C 1 - to C 4) alkyl] - (C r to C 4 aminoalkyl), wherein the dialkyl residues optionally a Carbon cycle or a heterocycle with 5 or 6 chain members, a C 1 - to C 4 -hydroxyalkyl or a di- (Cr to C 4 )
  • the pyrazolo [1, 5-a] -pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization from an aminopyrazole or from hydrazine.
  • the dyeing agents according to the invention contain at least one further coupler component.
  • further coupler components which can be used are m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives.
  • 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomonomethyl ether m-phenylenediamine, 1-naphthol, 1-naphthol, 1-naphthol, 1-naphthol are particularly suitable.
  • Coupler components according to the invention are m-aminophenol and its derivatives such as, for example, 5-amino-2-methylphenol, N-
  • Di- or trihydroxybenzene derivatives such as, for example, 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, for example, 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1, 7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 2,3-dihydroxynaphthalene, 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 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyrimidine , 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.
  • Particularly preferred further 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.
  • the hair colorants according to the invention contain both the developer components and the coupler components preferably in an amount of 0.005 to 20 wt .-%, preferably 0.1 to 5 wt .-%, in each case based on the total oxidation colorant.
  • developer components and coupler components are generally used in approximately molar amounts to each other.
  • a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components are in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1: 2, may be included.
  • the colorants may contain at least one precursor of a naturally-analogous dye.
  • indoles and indolines which have at least one hydroxyl or amino group, preferably as a substituent on the six-membered ring.
  • These groups may carry further substituents, e.g. Example in the form of etherification or esterification of the hydroxy group or alkylation of the amino group.
  • the colorants contain at least one indole and / or indoline derivative.
  • Particularly suitable precursors of natural-analogous hair dyes are derivatives of 5,6-dihydroxyindoline of the formula (IIa),
  • a 1 is hydrogen, a C r C 4 -alkyl group or a C r C 4 -hydroxy-alkyl group,
  • - A 2 is hydrogen or a -COOH group, wherein the -COOH group also as
  • a 3 is hydrogen or a C 1 -C 4 -alkyl group
  • a 4 and A 5 are each independently hydrogen, a C r C 4 alkyl group or a group -CO-A 6 , in which A 6 is a C r C 4 alkyl group, as well as physiologically acceptable salts of these compounds an organic or inorganic acid.
  • Preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxy-indoline, 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 (IIb) are also suitable as precursors of naturally-analogous hair dyes.
  • radicals A 1 , A 2 , A 3 , A 4 and A 5 have the meanings given above, and physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • 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.
  • hydrochlorides sulfates and hydrobromides are used.
  • the indole or Indoün derivatives are contained in these usually in amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-%.
  • 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, ornithine, lysine, serine and histidine, in particular arginine.
  • the colorants according to the invention may contain one or more substantive dyes for shade.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those under the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, Disperse 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 ( ⁇ -hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- ( ⁇ -hydroxyethyl) -aminophenol, 2- (2 ' Hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxyethyl) amino-4-methyl-2-
  • agents according to the invention may 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) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic substantive dyes of group (c).
  • the cationic direct dyes which are driven ver ⁇ under the trademark Arianor ® are, according to the invention also very particularly preferred cationic direct dyes.
  • the agents according to the invention according to this embodiment preferably contain the substantive dyes in an amount of from 0.01 to 20% by weight, based on the total colorant.
  • preparations of the invention may also naturally occurring dyes such as henna red, henna neutral, henna black, chamomile, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • the oxidation dye precursors or the direct dyes are in each case homogeneous compounds. Rather, in the inventive hair dye, 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, e.g. Toxi ⁇ ecological, must be excluded.
  • the colorants according to the invention may furthermore contain all active ingredients, 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 surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such. Legs 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 so ⁇ as the mono-, di- and Trialkanolammoniumsalze with 2 or 3 C-atoms in the Alkanolgrup- Pe, linear fatty acids with 10 bis 22 carbon atoms (soaps),
  • 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 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.
  • Nonionic surfactants contain as hydrophilic group z.
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula RO- (Z) x . These connections are identified by the following parameters.
  • the alkyl radical R ' contains from 6 to 22 carbon atoms and may be both linear and branched. Preference is given to primary linear and methyl branched in 2-Ste! Ment 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 When so-called "oxo-alcohols" are used 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 one particular alkyl radical R '. Usually, however, these compounds are produced starting from natural fats and oils or mineral oils. In this case, the alkyl radicals R 'are mixtures corresponding to the starting compounds or corresponding to the particular work-up of these compounds.
  • R ' 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- 6 alkyl groups or consisting 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 Used oligosaccharides 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 particularly preferred are alkyl glycosides in which x is 1: 1 to 1, 4.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • this substance class as a further constituent of the preparations according to the invention in the event that an effect of a perfume oil on the hair going beyond 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 H or -SO 3 H 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 cocoacylaminopropyl- dimethylammonium glycinate, and 2-alkyl-3-carboxamethyl-3-hydroxyethylimidazolines having in each case 8 to 18 C atoms in the alkyl or acyl group, and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
  • ampholytic surfactants are to be understood as meaning those 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-alkyl Propionic 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, acylaminoethylaminopropionat the coconut and the C 12-i 8 acyl sarcosine.
  • the cationic surfactants used are in particular those of the type of the quaternary ammonium compounds, the esterquats and the amidoamines.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg.
  • alkyltrimethylammonium chlorides dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg.
  • cetyltrimethylammonium chloride stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethyl ammonium chloride, Lauryldimethylbenzylammoniumchlorid and Tricetylmethylam- moniumchlorid, as well as under the INCI names Quaternium-27 and Quaternium-83 known Imidazoiium compounds.
  • 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 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 trade names Stepantex® ®, ® and Dehyquart® Armocare® ®.
  • 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 is that available under the name Tegoamid ® S 18 commercially stearamidopropyl dimethylamine.
  • cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning, a stabilized trimethyl isilylamodimethicone), Dow Corning 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 (Her ⁇ manufacturers: Th. Goldschmidt; diquaternary Poiydimethylsiloxane, 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 plant 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 which are obtained as catalysts in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alkoxides.
  • Limited homolog distributions are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or -aikoholates are used as catalysts. The use of products with narrow homolog distribution is preferred.
  • the colorants according to the invention may contain further active ingredients, auxiliaries and additives, for example nonionic polymers such as vinylpyrrolidone / inylacrylate 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, diethyl sulfate quaternized dimethylamino-ethylmethane acrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium-methochloride
  • nonionic polymers such as vinylpyrrolidone / inylacrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / inyla
  • Copolymers and quaternized polyvinyl alcohol quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate-hydroxypropyl methacrylate copolymers, anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers , Vinyl pyrrolidone / vinyl acrylate copolymers,
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. Methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as e.g. Bentonite or fully synthetic hydrocolloids such as e.g. Polyvinyl alcohol, structurants such as maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins,
  • 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,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, fiber-structure-improving agents, especially mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl-1-alkylamidoethyl-2 -alkylimidazolinium methosulfate defoamers such as silicones, dyes for staining the agent,
  • Antidandruff active ingredients such as Piroctone Olamine, zinc Omadine and Climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines,
  • Substances for adjusting the pH such as, for example, customary acids, especially edible acids and bases, active substances such as allantoin, pyrrolidonecarboxylic acids and their salts, and bisabolol, Vitamins, provitamins and vitamin precursors, in particular those of groups A, B 3 , B 5 , B 6 , C, E, F and H,
  • Plant extracts such as extracts of green tea, oak bark, stinging nettle, witch hazel, hops, chamomile, burdock root, horsetail, hawthorn, lime blossom, almond, aloe vera, spruce needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime, wheat, kiwi , Melon, orange, grapefruit, sage, rosemary, birch, mallow, meadowfoam, quenelle, yarrow, thyme, melissa, toadstool, coltsfoot, marshmallow, meristem, ginseng and ginger root,
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as spermaceti, beeswax, montan wax and paraffins,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate,
  • the agents according to the invention preferably contain the dye precursors in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing 3 to 70% by weight of a C 1 -C 4 -alkoxy, in particular ethanol or isopropanol.
  • the compositions according to the invention may additionally contain further organic solvents, for example methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • the actual oxidative coloring of the fibers can be done basically with atmospheric oxygen.
  • a chemical oxidizing agent is used, especially if, in addition to the coloring, a lightening effect on human hair is desired.
  • Suitable oxidizing agents are persulfates, chlorites and in particular hydrogen peroxide or its storage products of urea, melamine and sodium borate.
  • the dyeing center! may also be applied to the hair together with a catalyst which inhibits the oxidation of the dye precursors, e.g. by atmospheric oxygen, activated.
  • catalysts are e.g. 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+ . Particularly suitable are Zn 2+ , Cu 2+ and Mn 2+ .
  • the metal ions can in principle 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 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, 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.
  • Pyruvate oxidase and pyruvic acid or its 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.
  • the pH values given in this specification are the pH values at 25 ° C.
  • the use of the hair dyeing agent in a weakly alkaline medium is particularly preferred.
  • the application temperatures can be in a range between 15 and 40 0 C.
  • the hair dye is removed by rinsing of the hair to be dyed.
  • the Nach ⁇ wash with a shampoo is omitted if a strong surfactant-containing carrier, such as a dyeing shampoo was used.
  • the preparation with the dye precursors may also be applied to the hair without prior mixing with the oxidation component.
  • the oxidation component is then applied, if appropriate after an intermediate rinse.
  • the corresponding agent is adjusted to a pH of about 4 to 7.
  • an air oxidation is initially desired, wherein the applied agent preferably has a pH of 7 to 10.
  • the use of acidified Peroxidisulfat- solutions may be preferred as the oxidizing agent.
  • a second subject matter of the present application is the use of the inventive m-phenylenediamine derivatives for dyeing keratinic fibers.
  • a third object of the present invention is a process for coloring keratinic fibers, in which a hair colorant according to the invention is applied to the fibers and rinsed off again after a contact time.
  • a fourth subject of the present invention is the m-phenylenediamine derivative 3,5-bis [(2-hydroxyethyl) amino] -anisole.
  • the invention furthermore relates to the first intermediate of the synthesis of the inventive m-phenylenediamine, 2-chloroethyl-3 - ⁇ [(2-chloroethoxy) carbonyl] amino ⁇ -5-methoxyphenylcarbamate.
  • the invention additionally relates to the second intermediate of the synthesis of the inventive m-phenylenediamine, 3- [3-methoxy-5- (2-oxo-1,3-oxazolidin-3-yl) phenyl] - 1, 3 oxazolidin-2-one.
  • the cream base used had the following composition:
  • Ci 6 -i 8 fatty alcohol (INCI name: Cetearyl alcohol) (Cognis)
  • N-dimethyl-N- (C 8-18 -cocoamidopropyl) ammonium acetobetaine about 30% active ingredient, INCI name: Aqua (Water), Cocamidopropyl Betaine) (Cognis)
  • the dissolved dye precursors were incorporated successively into the hot cream. It was then made up to 97 g with distilled water and adjusted to a pH of 9.5 with ammonia. After filling with distilled water to 100 g, the mixture was stirred cold ( ⁇ 30 0 C), resulting in a homogeneous cream.

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Abstract

L'invention concerne des agents pour colorer des fibres de kératine, notamment des cheveux humains, ces agents contenant comme éléments de couplage, dans un support cosmétiquement acceptable, au moins un dérivé de m-phénylène diamine de formule (I), dans laquelle R<SUP>1</SUP> signifie un groupe alkyle C<SUB>1</SUB>- à C<SUB>2 </SUB>ou un groupe monohydroxyalkyle C<SUB>1</SUB>- à C<SUB>2</SUB>, R<SUP>2</SUP>, R<SUP>3</SUP> et R<SUP>4</SUP> désignent indépendamment l'un de l'autre un atome hydrogène, un groupe méthyle ou un groupe éthyle, et R<SUP>5</SUP> et R<SUP>6</SUP> représentent indépendamment l'un de l'autre un groupe hydroxyalkyle C<SUB>2</SUB>- à C<SUB>3</SUB>ramifié ou non. Les éléments de couplage de l'invention permettent, notamment au moyen de p-toluylène diamine, de 4-aminophénol, de 4-amino-3-méthylphénol, de 4,5-diamino-1-(2-hydroxyéthyle)pyrazol, de 1-(2-hydroxyéthyle)-2,5-diaminobenzène, de 2,4,5,6-tétraaminopyrimidine et de bis-(2-hydroxy-5-aminophényle)méthane, de réaliser des colorations de haute intensité, présentant une bonne voire très bonne résistance dans la gamme chromatique rouge et violette.
PCT/EP2005/009683 2004-11-15 2005-09-09 Nouveau coupleur m-phénylène diamine Ceased WO2006050768A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1847526A1 (fr) * 2006-04-18 2007-10-24 DyStar Textilfarben GmbH &amp; Co. Deutschland KG Composés de couplage et compositions pour la teinture des cheveux les contenant
RU2377969C2 (ru) * 2006-06-20 2010-01-10 Л`Ореаль КОМПОЗИЦИЯ ДЛЯ ОКРАСКИ КЕРАТИНОВЫХ ВОЛОКОН, ВКЛЮЧАЮЩАЯ 2,3-ДИАМИНО-6,7-ДИГИДРО-1Н,5Н-ПИРАЗОЛО[1,2-a]ПИРАЗОЛ-1-ОН, п-ФЕНИЛЕНДИАМИН ИЛИ п-ТОЛУИЛЕНДИАМИН И ЗАМЕЩЕННЫЙ м-АМИНОФЕНОЛ
US8481299B2 (en) 2009-03-04 2013-07-09 L'oreal Use of probiotic microorganisms to limit skin irritation
US10238897B2 (en) 2007-09-04 2019-03-26 L'oreal Use of a lysate of bifidobacterium species for treating sensitive skin
US11154731B2 (en) 2007-09-04 2021-10-26 L'oreal Cosmetic use of Bifidobacterium species lysate for the treatment of dryness

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ES2748836T3 (es) * 2012-03-30 2020-03-18 Oreal Composición compuesta por (2,5-diaminofenil) etanol, un tensioactivo alquilpoliglucósido no iónico, un éster de sorbitán oxietilenado o un alcohol graso polialcoxilado o poliglicerolado en un medio rico en sustancias grasas, proceso de teñido y dispositivo correspondiente
FR2988593B1 (fr) * 2012-03-30 2016-07-15 Oreal Composition de coloration mettant en œuvre le (2,5-diaminophenyl)ethanol, un alcool gras polyalkoxyle ou polyglycerole dans un milieu riche en corps gras, le procede de coloration et le dispositif

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DE10260834A1 (de) * 2002-12-23 2004-07-01 Henkel Kgaa Neue Kupplerkomponenten
DE10260820A1 (de) * 2002-12-23 2004-07-01 Henkel Kgaa Neue Kupplerkomponenten
EP1496046A1 (fr) * 2003-07-08 2005-01-12 Henkel Kommanditgesellschaft auf Aktien Nouvel agent copulant

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Publication number Priority date Publication date Assignee Title
DE10260834A1 (de) * 2002-12-23 2004-07-01 Henkel Kgaa Neue Kupplerkomponenten
DE10260820A1 (de) * 2002-12-23 2004-07-01 Henkel Kgaa Neue Kupplerkomponenten
EP1496046A1 (fr) * 2003-07-08 2005-01-12 Henkel Kommanditgesellschaft auf Aktien Nouvel agent copulant

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1847526A1 (fr) * 2006-04-18 2007-10-24 DyStar Textilfarben GmbH &amp; Co. Deutschland KG Composés de couplage et compositions pour la teinture des cheveux les contenant
WO2007118818A1 (fr) * 2006-04-18 2007-10-25 Dystar Textilfarben Gmbh & Co Deutschland Kg Copulants et compositions de coloration capillaire les contenant
RU2377969C2 (ru) * 2006-06-20 2010-01-10 Л`Ореаль КОМПОЗИЦИЯ ДЛЯ ОКРАСКИ КЕРАТИНОВЫХ ВОЛОКОН, ВКЛЮЧАЮЩАЯ 2,3-ДИАМИНО-6,7-ДИГИДРО-1Н,5Н-ПИРАЗОЛО[1,2-a]ПИРАЗОЛ-1-ОН, п-ФЕНИЛЕНДИАМИН ИЛИ п-ТОЛУИЛЕНДИАМИН И ЗАМЕЩЕННЫЙ м-АМИНОФЕНОЛ
US10238897B2 (en) 2007-09-04 2019-03-26 L'oreal Use of a lysate of bifidobacterium species for treating sensitive skin
US11154731B2 (en) 2007-09-04 2021-10-26 L'oreal Cosmetic use of Bifidobacterium species lysate for the treatment of dryness
US8481299B2 (en) 2009-03-04 2013-07-09 L'oreal Use of probiotic microorganisms to limit skin irritation

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