EP2007344A1 - Produits éclaircissants et/ou colorants à tolérance cutanée améliorée - Google Patents

Produits éclaircissants et/ou colorants à tolérance cutanée améliorée

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Publication number
EP2007344A1
EP2007344A1 EP07724015A EP07724015A EP2007344A1 EP 2007344 A1 EP2007344 A1 EP 2007344A1 EP 07724015 A EP07724015 A EP 07724015A EP 07724015 A EP07724015 A EP 07724015A EP 2007344 A1 EP2007344 A1 EP 2007344A1
Authority
EP
European Patent Office
Prior art keywords
group
amino
acid
hydroxyethyl
alkyl group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07724015A
Other languages
German (de)
English (en)
Inventor
Horst Höffkes
Elisabeth Poppe
Denise Fuhr
Mustafa Akram
Detlef Hollenberg
Anja Reichert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP2007344A1 publication Critical patent/EP2007344A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61Q5/08—Preparations for bleaching the hair
    • 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 means for dyeing and / or whitening keratinic fibers, i. Agent for use on keratin fibers, in particular human hair, and their use.
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • hair dyeing and / or lightening agents are mixed in solid or pasty form with dilute aqueous hydrogen peroxide solution. This mixture is then applied to the hair and rinsed again after a certain exposure time.
  • the duration of exposure to the hair to achieve complete coloration or lightening is between about 30 and 40 minutes. It is obvious that in the Users of these hair dyes or bleaching agents have a need to reduce this exposure time.
  • coloration and bleaching processes on keratinic fibers usually proceed at alkaline pH values, in particular between 9.0 and 10.5. These pH values are necessary to ensure an opening of the outer cuticle (cuticle) and to allow a penetration of the active species (dye precursors and / or hydrogen peroxide) into the hair.
  • the alkalizing agent used is usually ammonia, which however has the disadvantage of intense odor and possible irritation for the users.
  • aminomethylpropanol or monoethanolamine are used as alternative alkalizing agents to ammonia.
  • they are usually used in admixture with ammonia. But even here, the performance of the ammonia is impaired, especially with regard to the parameters gray covering, whitening performance and color result.
  • the invention relates in a first embodiment to an agent for lightening and / or dyeing keratin fibers, in particular human hair, containing - in each case by weight - a) 0.001 to 5 wt .-% of one or more dye precursors and / or direct dyes; b) 0.1 to 20 wt .-% of at least one imidazole compound according to formula (I) and / or their physiologically acceptable salts wherein
  • R 1 represents a hydrogen atom, an optionally substituted aryl group or a (C 1 -C 6 ) -alkyl group,
  • R 2 represents a hydrogen atom, a carboxaldehyde group, a (C 1 -C 6 ) -alkyl group or a nitro group,
  • R 3 represents a hydrogen atom, a carboxy (C 1 -C 6 ) alkyl group, an amino (Ci-C 6 ) alkyl group, a carboxyl group, a
  • Carboxaldehyde group a (C 1 -C 6 ) -alkyl group, a nitro group, a 2-amino-3-hydroxypropyl group or a group -CH 2 -CH (NH 2 ) -COOH,
  • R 4 represents a hydrogen atom, a carboxaldehyde group or a carboxyl group.
  • Keratin fibers mean furs, wool, feathers and in particular human hair. Although the compositions according to the invention are primarily suitable for dyeing and / or whitening keratin fibers, in principle, there is nothing to prevent their use in other fields as well.
  • compositions according to the invention comprise at least two essential constituents: one or more dye precursors and / or substantive dyes and at least one imidazole compound of the formula (I) and / or their physiologically tolerable salts. These are described below.
  • Dye precursors are understood according to the invention to mean chemical compounds which are not themselves colored, but form a dye only under chemical reaction. This chemical reaction can be triggered, for example, by oxidation of dye precursors.
  • the present invention is not subject to any restrictions.
  • the colorants according to the invention are preferred as dye precursors Developing and / or coupler type oxidation dye precursors, and / or
  • Precursors of natural analog dyes such as indole and indoline derivatives, and mixtures of representatives of these groups.
  • agents according to the invention are preferably provided as colorants. Agents which simultaneously dye and brighten are also referred to as lightening dyes.
  • the agents of the invention are colorants, i. Means for changing the color of keratinic fibers.
  • the so-called oxidation dyes are particularly preferred.
  • the oxidation colorants of the invention contain at least one coupler and at least one developer component. Coupler and developer components are also referred to as oxidation dye precursors.
  • the oxidation colorants according to the invention may also contain substantive dyes as nuances. According to preferred means for dyeing and / or lightening keratinischer fibers are therefore characterized in that they contain at least one oxidation dye precursor of the developer type and / or coupler type.
  • the developer components are usually primary aromatic amines with a further, located in the para or ortho position free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone and 2,4,5,6-tetraaminopyrimidine and its derivatives used.
  • m-phenylenediamine derivatives naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives are generally used.
  • Suitable coupler substances are in particular ⁇ -naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4 -Diaminophenoxyethanol, 2-amino-4- (2-hydroxyethylamino) -anisole (Lehmann's Blue), 1-phenyl-3-methyl-pyrazol-5-one, 2,4-dichloro-3-aminophenol, 1, 3-bis - (2,4-diaminophenoxy) -propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2- Methyl resorcinol, 5-methylresorcinol, 3-amino-6-methoxy-2-methylaminopyridine and 3,5-diamino-2,6-dimeth
  • the colorant further contains 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-amino pyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and its Derivatives used.
  • 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 C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) alkoxy ( C 1 -C 4 ) -alkyl radical, a 4'-aminophenyl radical or a C 1 -C 4 -alkyl radical which is substituted by a nitrogen-containing group, a phenyl or a 4'-aminophenyl radical;
  • G 2 represents a hydrogen atom, a C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) alkoxy (C r to C 4) alkyl radical or a C 1 - to C 4 alkyl radical substituted with a nitrogenous 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 -monohydroxyalkyl radical, 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 fluorine atom
  • G 4 represents a hydrogen atom, a halogen atom or a C 1 - to C 4 -alkyl radical or when G 3 and G 4 are ortho to each other, they may together form a bridging ⁇ , ⁇ -alkylenedioxy group, such as, for example, an ethylenedioxy group.
  • 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.
  • C 1 -C 4 -alkoxy radicals which are preferred according to the invention are, for example, a methoxy or an ethoxy group.
  • 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 especially the amino groups, C 1 - to C 4 monoalkylamino, C 1 - to C 4 dialkylamino, C 1 - to C 4 -Trialkylammonium phenomenon, C 1 - to C 4 - Monohydroxyalkylamino phenomenon, 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, N-bis-
  • Very particular preferred p-phenylenediamine derivatives of the formula (E1) according to the invention are p-phenylenediamine, p-toluenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2- ( ⁇ , ⁇ -dihydroxyethyl) -p-phenylenediamine and N, N bis (.beta.-hydroxyethyl) -p-phenylenediamine.
  • 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 colorants according to the invention, mention may be made in particular of the compounds which correspond to the following formula (E2) and their physiologically tolerated salts:
  • Z 1 and Z 2 independently of one another, are a hydroxyl or NH 2 radical, which is optionally substituted by a C 1 - C 4 alkyl group is substituted to, by a C 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, which is one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, Interrupted or terminated by sulfur or nitrogen atoms and may possibly be substituted by one or more hydroxyl or C 1 - to C 8 -alkoxy radicals, or a direct bond
  • 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, which is one or more nitrogen-containing groups and / or
  • 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 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 bridging Y per molecule and the compounds of the formula (E2) contain at least one amino group which carries at least one hydrogen atom.
  • binuclear 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 ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N, N'-diethyl-N, N ' bis (4'-amino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminoph
  • Very particularly preferred binuclear developer components of the formula (E2) are N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol, Bis (2-hydroxy-5-aminophenyl) methane, 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.
  • p-aminophenol derivatives of the formula (E3) it may be preferred according to the invention to use as the developer component a p-aminophenol derivative or one of its physiologically tolerable salts. Particular preference is given to p-aminophenol derivatives of the formula (E3)
  • G 13 represents a hydrogen atom, a halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) - Alkoxy (C 1 - to C 4 ) -alkyl radical, a C 1 - to C 4 -am inoalkylrest, a hydroxy ⁇ Cr to C 4 ) - alkylamino, a C 1 - to C 4 -hydroxyalkoxy, a C 1 - bis C 1 to C 4 hydroxyalkyl-C 1 -C 4 ) -aminoalkyl or a (C 1 -C 4 -alkylamino) - (C 1 to C 4 ) -alkyl radical, and
  • G 14 represents a hydrogen or halogen atom, a C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a (C 1 - to C 4) - Alkoxy (C r to C 4 ) -alkyl radical, a C 1 - to C 4 -aminoalkyl radical or a C 1 - to C 4 -cyanoalkyl radical, G 15 is hydrogen, C 1 - to C 4 -alkyl, C 1 - to C 4 -monohydroxyalkyl, C 2 - to C 4 -polyhydroxyalkyl, phenyl or benzyl, and
  • G 16 is hydrogen or a halogen atom.
  • Preferred p-aminophenols of the formula (E3) are, in particular, p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 -Amino-3-hydroxymethylphenol, 4-amino-2- ( ⁇ -hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino -2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2 -chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethyl-aminomethyl) -phenol and their physiological
  • Very particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) -phenol and 4-amino 2- (diethylaminomethyl) -phenol.
  • the developer component may be selected from o-aminophenol and its derivatives such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component may be selected from heterocyclic developer components, such as the pyridine, pyrimidine, pyrazole, pyrazole pyrimidine derivatives and their physiologically acceptable salts.
  • Preferred pyridine derivatives are in particular the compounds 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) amino-3-amino-pyridine, 2,3-diamino-6-methoxypyridine, 2- ( ⁇ -methoxyethyl ) amino-3-amino-6-methoxypyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are in particular 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 4,5-diamino-i-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-1-methylpyrazole, 4,5-diamino-1-tert.
  • Triaminopyrazole 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4- ( ⁇ -hydroxyethyl) amino-1-methylpyrazole.
  • Preferred pyrazole-pyrimidine derivatives are, in particular, the derivatives of the pyrazolo [1,5-a] pyrimidine of the following formula (E4) and their tautomeric forms, if a tautomeric equilibrium exists:
  • G 17 , G 18 , G 19 and G 20 independently of one another represent a hydrogen atom, a C 1 - to C 4 -alkyl radical, an aryl radical, a C 1 - to C 4 -hydroxyalkyl radical, a C 2 - to C 4 - a polyhydroxyalkyl (C 1 - to C 4) alkyl alkoxy (Cr to C4), a C 1 - to C 4 - aminoalkyl radical, which may be optionally protected by an acetyl ureide or a sulfonyl residue, a (C 1 - to C ⁇ alkylamino ⁇ d- to C 4 ) alkyl radical, a di - [(Cr to C 4 ) alkyl] - (Cr to C 4 ) aminoalkyl radical, wherein the dialkyl radicals optionally a Form a C 1 -C 4 -hydroxyalkyl or a di- (C 1 -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.
  • oxidation colorants are characterized in that the developer component is selected from 3-methyl-1,4-diaminobenzene, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, 2- (2,5-diaminophenoxy) ethanol , N, N-bis (2'-hydroxyethyl) -1, 4-diaminobenzene, 3-methyl-4-aminophenol and 2-methylamino-4-aminophenol, p-phenylenediamine, 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine , N, N-bis- ( ⁇ -hydroxyethyl) -p-phenylenediamine, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino propan-2-ol, bis (2-hydroxy-5-aminophenyl) methane, N, N, N-bis (2'
  • Preferred agents according to the invention contain as oxidation dye precursor at least one developer component, preferred developer components being selected from p-phenylenediamine, p-toluenediamine, N, N-bis (2-hydroxyethyl) amino-p-phenylenediamine, 1,3-bis- [ 2-hydroxyethyl-4 'aminophenyl) amino] -propan-2-ol, 1, 10-bis (2', 5'-diaminophenyl) -1, 4,7,10-tetraoxadecane, 4-aminophenol, 4- Amino-3-methylphenol, bis (5-amino-2-hydroxyphenyl) methane, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4,5-diamino-1- ( 2-hydroxyethyl) pyrazole.
  • preferred developer components being selected from p-phenylenediamine, p-toluenediamine, N,
  • the colorants of the invention may further contain at least one coupler component.
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used.
  • 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, 1-phenyl 3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2 ' l 4'-diaminophenoxy) -propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2 Chloro-6-methyl-3-aminophenol, 2-amino-3-hydroxypyridine, 2-methylresorcinol, 5-methylresorcinol and 2-methyl-4-chloro-5-aminophenol.
  • Preferred coupler components according to the invention are m-aminophenol and its derivatives, such as, for example, 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- Or-3-aminophenol, o-aminophenol and its derivatives, m-diaminobenzene and its derivatives such as 2,
  • Di- or trihydroxybenzene derivatives such as resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, pyrogallol and 1,2,4-trihydroxybenzene, pyridine derivatives such as 2,6-dihydroxypyridine , 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dihydroxy 4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine and 3,5-diamino-2,6-dimethoxypyridine,
  • Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-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, for example, 6-hydroxybenzomorpholine and 6-aminobenzomorpholine, quinoxaline derivatives such as, for example, 6-methyl-1,2,3,4-tetrahydroquinoxaline, Pyrazole derivatives such as, for example, 1-phenyl-3-methylpyrazol-5-one, indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole, pyrimidine derivatives such as, for example, 4,6-dimethylaminopyrimidine, 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-methyl
  • coupler components according to the invention are 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4-chlororesorcinol , 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol and 2,6-dihydroxy-3,4-dimethylpyridine.
  • indoles and indolines are preferably used as dye precursors 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 as dye precursor at least one indole and / or indoline derivative as a precursor of a natural analog dye.
  • compositions of natural-analogous hair dyes are derivatives of 5,6-dihydroxyindoline of the formula (IIa),
  • R 1 is hydrogen, a C 1 -C 4 -alkyl group or a C 1 -C 4 -hydroxy-alkyl group
  • R 2 is hydrogen or a -COOH group, where the -COOH group may also be present as a salt with a physiologically compatible cation
  • R 3 is hydrogen or a C 1 -C 4 -alkyl group
  • R 4 is hydrogen, a C r C 4 -alkyl group or a group -CO-R 6 , in which R 6 is a C 1 -C 4 -alkyl group, and R 5 is one of the groups mentioned under R 4 , and physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • indoline 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-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially 5, 6-Dihydroxyindolin.
  • R 1 is hydrogen, a C 1 -C 4 alkyl group or a C 1 -C 4 hydroxyalkyl group
  • R 2 is hydrogen or a -COOH group, wherein the -COOH group may also be present as a salt with a physiologically compatible cation,
  • R 3 is hydrogen or a C 1 -C 4 -alkyl group
  • R 4 is hydrogen, a C 1 -C 4 -alkyl group or a group -CO-R 6 , in which R 6 is a C 1 -C 4 -alkyl group, and
  • R 5 is one of the groups mentioned under R 4 , as well as physiologically acceptable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6- dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.
  • N-methyl-5,6-dihydroxyindole N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, and especially the 5,6 -Dihydroxyindol.
  • the indoline and indole derivatives can be used in the colorants used in the process according to 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 indoline derivatives are contained therein usually in amounts of 0.05-10 wt .-%, preferably 0.2-5 wt .-%.
  • the indoline or indole derivative in hair dyes 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.
  • oxidation colorants are characterized in that the coupler component is selected from m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives, preferred agents being resorcinol, 3-amino-2-methylamino-6-methoxypyridine, 3-amino-6-methylphenol, 3-amino-2-hydroxypyridine, 1, 3-bis (2,4-diaminophenoxy) propane, 2,7-dihydroxynaphthalene, 2-methylresorcinol, 5-methyl-resorcinol, 2.5 Dimethyl resorcinol and 4-chlororesorcinol 1-naphthol, 1, 5, 2,7- and 1, 7-dihydroxynaphthalene, 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4- Chlororesorcinol,
  • Preferred agents for dyeing and / or lightening keratinic fibers according to the invention are characterized in that they contain at least one coupler component as the oxidation dye precursor, preferred coupler components being selected from resorcinol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 4- Chlororesorcinol, resorcinol monomethyl ether, 5-aminophenol, 5-amino-2-methylphenol, 5- (2-hydroxyethyl) amino-2-methylphenol, 3-amino-4-chloro-2-methylphenol, 3-amino-2-chloro-6 -methylphenol, 3-amino-2,4-dichlorophenol, 2,4-diaminophenoxyethanol, 2-amino-4- (2 '-hydroxyethyl) amino-anisolsulfat, 1, 3- Bis (2,4-diaminophenoxy) propane, 2-amino-3-hydroxypyridine, 2-methylamino-3-amino-6-me
  • coupler and developer components are used in a particular ratio to each other.
  • oxidation colorants of the present invention containing the coupler component (s) in an amount of 0.01 to 20 wt%, preferably 0.5 to 5 wt%, and the developer component (n) in an amount of 0, are preferable. 01 to 20 wt .-%, preferably from 0.5 to 5 wt .-%, each based on the total oxidation colorant included.
  • the colorants may contain one or more substantive dyes for shade.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols, triphenylmethane dyes, acid dyes, basic dyes, preferably from the group of the international trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 1, 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, Acid Red 92, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Disperse Red 17, 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
  • Phenylamino) azo) benzenesulfonic acid, sodium salt 1 - ((3-aminopropyl) amino) -9, IO-anthracenedione; 3 ', 3 ", 4,5,5', 5", 6,7-Octabromphenolsulfonphtalein; 1 - ((4-Amino-3,5-dimethylpheny1) - (2,6-dichlorophenyl) methylene) -3.5 -dimethyl-4-imino-2,5-cyclohexadiene-phosphoric acid (1: 1) (Basic Blue 77); 3 ', 3 ", 5', 5"-tetrabromo-m-cresolsulfonephthalein; 2,4-dinitro-1-naphthol-7-sulfonic acid disodium salt; 4- [2'-hydroxy-1'-naphthyl) azo] - benzenesulfonic acid sodium salt, 3 '
  • Agents preferred according to the invention for dyeing and / or brightening keratinic fibers are characterized in that they contain at least one substantive dye selected from nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols, preferably from the group known by the international names or trade names Dye 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 Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN 1 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, Acid Black 52, Acid Yellow 87, Basic Orange 31 and Basic Red 51 known compounds as well as 1 , 4-diamino-2-nitro
  • 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 substantive dyes sold under the trademark Arianor are also very particularly preferred cationic substantive dyes according to the invention.
  • 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.
  • oxidation dye precursors or the direct dyes it is not necessary for the oxidation dye precursors or the direct dyes to be in each case homogeneous compounds. Rather, in the hair colorants according to the invention, due to the production process for the individual dyes, in minor amounts, further components may be included, as far as they do not adversely affect the dyeing result or for other reasons, e.g. toxicological, must be excluded.
  • Staining of keratinic fibers can also be accomplished by dyes formed in an oxidatively catalyzed reaction of C, H-acidic compounds with reactive carbonyl compounds.
  • the agent according to the invention therefore contains a combination of component A compounds containing a reactive carbonyl group with component B compounds selected from (a) CH-acidic compounds, (b) compounds having primary or secondary amino group or hydroxy group selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds, (c) amino acids, (d) oligopeptides constructed from 2 to 9 amino acids.
  • component A compounds containing a reactive carbonyl group selected from (a) CH-acidic compounds, (b) compounds having primary or secondary amino group or hydroxy group selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds, (c) amino acids, (d) oligopeptides constructed from 2 to 9 amino acids.
  • Compounds according to the invention having a reactive carbonyl group (also referred to below as reactive carbonyl compounds or component A) have at least one carbonyl group as reactive group which reacts with the compounds of component B to form a chemical bond linking both components. Furthermore, those compounds according to the invention are also included as component A in which the reactive carbonyl group is derivatized or masked in such a way that the reactivity of the carbon atom of the derivatized or masked carbonyl group with respect to component B is always present.
  • These derivatives are preferably condensation compounds of reactive carbonyl compounds with a) amines and derivatives thereof to form imines or oximes as condensation compound b) of alcohols to form acetals or ketals as condensation compound c) of water to form hydrates as addition compound.
  • Component A is preferably selected from the group formed from acetophenone, propiophenone, 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, 2-hydroxypropiophenone, 3-hydroxypropiophenone, 4-hydroxypropiophenone, 2-hydroxybutyrophenone, 3 Hydroxybutyrophenone, 4-hydroxybutyrophenone, 2,4-dihydroxyacetophenone, 2,5-dihydroxyacetophenone, 2,6-dihydroxyacetophenone, 2,3,4-trihydroxyacetophenone, 3,4,5-trihydroxyacetophenone, 2,4,6-dihydroxyacetophenone Trihydroxyacetophenone, 2,4,6-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone diethyl ketal, 4-hydroxy-3-methoxy-acetophenone, 3,5-dimethoxy-4- hydroxyacetophenone, 4-aminoacetophenone, 4-dimethylamino
  • Benzaldehyde, cinnamic aldehyde and naphthaldehyde and their derivatives, in particular having one or more hydroxyl, alkoxy or amino substituents, are very particularly preferably used as the reactive carbonyl compound in the agents according to the invention.
  • the compounds according to formula (Ca-1) are preferred,
  • R 1 * , R 2 * and R 3 * independently represent a hydrogen atom, a halogen atom, a C ⁇ C 6 alkyl group, a hydroxy group, a CrC ⁇ alkoxy group, a CrC 6 - dialkylamino group, a di (C 2 -C 6 hydroxyalkyl) amino group, a di (C 1 -C 6 -alkoxy-CrC 6 - alkyl) aminoguppe, a CrC 6 -Hydroxyalkyloxy distr, a sulfonyl group, a carboxy group, a sulfonic acid group, a sulfonamido group, a sulfonamide group, a carbamoyl group, a C C 2 -C 6 acyl group or a nitro group,
  • Z ' is a direct bond or a vinylene group
  • R 4 * and R 5 * represent a hydrogen atom or together form, together with the remainder of the molecule, a 5- or 6-membered aromatic or aliphatic ring.
  • the derivatives of the benzaldehydes, naphthaldehydes or cinnamaldehydes of the reactive carbonyl compound according to component C are particularly preferably selected from certain aldehydes.
  • Agents preferred according to the invention are characterized in that they are formulated as hair colorants, based on their weight 0.01 to 20 wt .-%, preferably 0.05 to 15% by weight, particularly preferably 0.1 to 12.5 wt .-% and in particular 0.2 to 10 wt .-% of one or more reactive carbonyl compound (s).
  • CH-acidic compounds are generally considered to carry a bound to an aliphatic carbon atom hydrogen atom, wherein due to electron-withdrawing substituents activation of the corresponding carbon-hydrogen bond is effected.
  • CH-acidic compounds also include enamines which are formed by alkaline treatment of quaternized N-heterocycles with a CH-acidic alkyl group in conjugation with the quaternary nitrogen.
  • the CH-acidic compounds of component B are preferably selected from the group consisting of 1, 2,3,3-tetramethyl-3H-indolium iodide, 1, 2,3,3-tetramethyl-3H-indolium p-toluenesulfonate, 1, 2,3,3-tetramethyl-3H-indolium methanesulfonate, 1,3,3-trimethyl-2-methylenindoline (Fischer's base), 2,3-dimethylbenzothiazolium iodide, 2,3-dimethylbenzothiazolium p-toluenesulfonate, 2,3-dimethyl-naphtho [1,2-d] thiazolium p-toluenesulfonate, 3-ethyl-2-methylnaphtho [1,2-d] thiazolium p-toluenesulfonate, rhodanine, rhodanine-3-acetic acid
  • Suitable compounds having primary or secondary amino group as component B are, for example, primary aromatic amines such as N, N-dimethyl, N, N-diethyl, N- (2-hydroxyethyl) -N-ethyl, N 1 N-bis ( 2-hydroxyethyl) -, N- (2-methoxyethyl), 2,3-, 2,4-, 2,5-dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4 - morpholinoaniline dihydrobromide, 2-, 3-, 4-aminophenol, 2-aminomethyl-4-aminophenoi, 2-hydroxymethyl-4-aminophenoi, o-, p-phenylenediamine, o-toluenediamine, 2,5-diaminotoluene, -phenot , - phenethole, 4-amino-3-methylphenoi, 2- (2,5-dia
  • R 6 is a hydroxyl or an amino group which may be substituted by C 1-4 -alkyl, C 1-4 -hydroxyalkyl or C 1-4 -alkoxy-C 1-4 -alkyl, R 7, R ", R 9, R 1 O and Rl 'is hydrogen, a hydroxy or an amino group represented by a CI-4-alkyl, CI-4-hydroxyalkyl, CI-4-aminoalkyl or CI-4-alkoxy-C1-4-alkyl group Z is a direct bond, a saturated or unsaturated, optionally substituted by hydroxy groups carbon chain having 1 to 4 carbon atoms, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom or a group of the formula III Q- (CH 2 -p-CH 2 -Q ') 1> (III) in which P is a direct bond, a CH 2 or CHOH group, Q and Q' are independently an oxygen atom, an NR 12 group in which
  • the abovementioned compounds can be used both in free form and in the form of their physiologically acceptable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are, for example, 2-, 3-, 4-amino, 2-amino-3-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-diamino, 2-dimethylamino 5-amino, 2-methylamino-3-amino-6-methoxy, 2,3-diamino-6-methoxy, 2,6-dimethoxy-3,5-diamino, 2,4,5 Triamino, 2,6-dihydroxy-3,4-dimethylpyridine, 2,4-dihydroxy-5,6-diamino, 4,5,6-triamino, 4-hydroxy-2,5,6- triamino, 2-hydroxy-4,5,6-trianriino, 2, 4,5,6-tetraamino, 2-methylamino-4,5,6-triamino, 2,4-, 4,5-diamino , 2-Amino-4-methoxy-6-methyl-pyrimidine, 3,5-di
  • indole or indoline derivatives 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.
  • Preferred amino acids are all naturally occurring and synthetic (alpha-amino acids, eg the amino acids obtainable by hydrolysis from vegetable or animal proteins, eg collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein
  • Preferred amino acids are arginine, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), ornithine, lysine and tryptophan, but other amino acids can also be used, such as 6-aminocaproic acid.
  • the oligopeptides may be naturally occurring or synthetic oligopeptides, but also the oligopeptides contained in polypeptide or protein hydrolysates, provided that they have sufficient water solubility for use in the inventive colorants.
  • the oligopeptides contained in polypeptide or protein hydrolysates e.g. Glutathione or the oligopeptides contained in the hydrolysates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein.
  • Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-, 3-, 4-methoxy-, 3- Dimethylamino, 2- (2-hydroxyethyl) -, 3,4-methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, - phenylacetic acid, gallic acid, 2,4,6-trihydroxybenzoic acid, acetophenone, 2-, 4- Chlororesorcinol, 1-naphthol, 1, 5, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2,7-naphthalenesulfonic acid.
  • CH-active compounds there can be exemplified 1, 2,3,3-tetramethyl-3H-indolium iodide, 1,2,3,3-tetramethyl-3H-indolium-p-toluoisulfonate, 1,2,3,3-tetramethyl 3H-indolium methanesulfonate, Fischer's base (1,3,3-trimethyl-2-methylenindoline), 2,3-dimethylbenzothiazolium iodide, 2,3-dimethylbenzothiazolium p-toluenesulfonate, rhodanine, rhodanine-3-acetic acid , 1-ethyl-2-quinaldinium iodide, 1-methyl-2-quinaldinium iodide barbituric acid, thiobarbituric acid, 1,3-dimethylthiobarbituric acid, diethylthiobarbituric acid, oxindole, 3-indoxyla
  • the CH-acidic compounds are preferably selected from the formulas (III) and / or (IV) and / or (V)
  • R 8 and R 9 are independently a linear or cyclic C-rC 6 alkyl group, a C 2 -C 6 alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an aryl-CrC ⁇ -alkyl group, a C r C 6- hydroxyalkyl group, a C 2 -C 6 -polyhydroxyalkyl group, a C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl group, a group R 1 R 11 N- (CH 2 J m -, in which R 1 and R 11 independently of one another represent a hydrogen atom, a Ci-C 4 alkyl group, a CrCi-hydroxyalkyl group or an aryl-Ci-C 6 alkyl group, wherein R 1 and R 11 together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m is a number 2, 3, 4, 5 or 6,
  • R 10 and R 12 independently represent a hydrogen atom or a C 1 -C 6 - alkyl group, wherein at least one of the radicals R 10 and R 12 represents a CrC ß alkyl group,
  • R 11 represents a hydrogen atom, a dC 6 alkyl group, a C r C 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a CrC ⁇ alkoxy group, a C 1 -C 6 - hydroxyalkoxy group, a group R '' R lv N- (CH 2 ) q -, wherein R 1 "and R IV independently represent a hydrogen atom, a CiC 6 alkyl group, a C T C 6 - hydroxyalkyl group or an aryl-CrC ⁇ -alkyl group and q is a number 1, 2, 3, 4, 5 or 6, wherein the radical R 11 together with one of the radicals R 10 or R 12 can form a 5- or 6-membered aromatic ring optionally with a halogen atom, a C r C 6 alkyl group, a CrC ⁇ -hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a Ci-C
  • R 13 and R 14 either form together with the nitrogen atom form a saturated or unsaturated 5- or 6-membered ring, or independently represent a (C 1 - C 6) alkyl group, a (C 2 -C 6) alkenyl group, an aryl group, an aryl- (C 1 -C 6 ) -alkyl group, a (C 2 -C 6 ) -hydroxyalkyl group, a (C 2 -C 6 ) -polyhydroxyalkyl group or a group R'R "N- (CH 2 ) m -, wherein R 1 and R 11 are each independently a hydrogen atom, a (C r C 6 ) alkyl group, a (C r C 6 ) alkenyl group or an aryl-C r C 6 alkyl group, wherein R 1 and R 11 together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m is a number 2, 3, 4, 5 or 6, and
  • R 15 is a hydrogen atom, a (Ci-C 6 ) alkyl group, a (C 2 -C 6 ) alkenyl group, an aryl group, an aryl (C r C 6 ) alkyl group, a (C 2 -C 6 ) Hydroxyalkyl group, a (C 2 -C 6 ) - polyhydroxyalkyl group or a group R '"R' v N- (CH 2 ) n -, where R 1 " and R IV independently of one another represent a hydrogen atom, a C 6) alkyl group, a (C 1 -C 6) - alkenyl group or an aryl-alkyl group -C 6, wherein R can ⁇ v form together with the nitrogen atom form a 5-, 6- or 7-membered ring 1 "and R and n stands for a number 2, 3, 4, 5 or 6
  • Y represents an oxygen atom, a sulfur atom or a group NR V ", wherein R v" stands for a hydrogen atom, an aryl group, a heteroaryl group, a C r C 6 alkyl group or a C r C 6 arylalkyl group,
  • X " is a physiologically acceptable anion
  • Het is an optionally substituted heteroaromatic
  • X 1 represents a direct bond or a carbonyl group.
  • At least one group R 10 or R 12 according to formula III necessarily stands for a C 1 -C 6 -alkyl group.
  • This alkyl group preferably carries at least two hydrogen atoms on its alpha carbon atom.
  • Particularly preferred alkyl groups are the methyl, ethyl, propyl, n-butyl, iso-butyl, n-pentyl, neo-pentyl, n-hexyl.
  • R 10 and R 12 are each independently hydrogen or a methyl group, wherein at least one group R 10 or R 12 is a methyl group.
  • Y according to formula III is an oxygen or a sulfur atom, more preferably an oxygen atom.
  • the radical R 8 according to formula III is preferably selected from a (C 1 -C 6 ) -alkyl group (particularly preferably a methyl group), a C 2 -C 6 -alkenyl group (in particular an allyl group), a hydroxy- (C 2 - to C 6 ) alkyl group, especially a 2-hydroxyethyl group, or an optionally substituted benzyl group.
  • R 11 according to formula III is preferably a hydrogen atom.
  • the radicals R 9 , R 10 and R 12 is a methyl group
  • the radical R 11 is a hydrogen atom
  • Y is an oxygen or sulfur atom
  • the radical R 8 is selected from a (CrC 6 ) - Alkyl group (particularly preferably a methyl group), a C 2 -C 6 alkenyl group (in particular an allyl group), a hydroxy (C 2 - to C 6 ) - alkyl group, in particular a 2-hydroxyethyl group, or an optionally substituted benzyl group.
  • the compounds according to formula III are selected from one or more
  • X " in formula (III) and in the above lists preferably represents halide, benzenesulfonate, p-toluenesulfonate, C 1 -C 4 -alkanesulfonate, trifluoromethanesulfonate, perchlorate, 0.5 sulfate, hydrogensulfate, tetrafluoroborate, hexafluorophosphate or tetrachlorozincate , Bromide, iodide, hydrogen sulfate or p-toluenesulfonate used as X ' .
  • the radical Het according to formula (IV) preferably represents the molecule fragment of the formula (VI),
  • R 16 and R 17 independently represent a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, a linear or cyclic C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, an optionally substituted aryl group, a cyanomethyl group, a Cyanomethylcarbonyl group, an optionally substituted heteroaryl group, an arylCrC ⁇ -alkyl group, a C 1 -C 6 -hydroxyalkyl group, a C 2 -C 6 -polyhydroxyalkyl group, a C r C 6 -alkoxy group, a C r C 6 -alkoxycarbonyl group, a C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl group, a CrC ⁇ -sulfoalkyl group, a CrC ⁇ -carboxyalkyl group, a group R VIII R lx N- (CH 2
  • X 2 and X 3 independently represent a nitrogen atom or a group CR 15 , wherein R 15 represents a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, a linear or cyclic C r C 6 alkyl group, a C 2 -C 6 alkenyl group, an optionally substituted aryl group, a cyanomethyl group, a cyanomethylcarbonyl group, an optionally substituted heteroaryl group, an arylC r C 6 alkyl group, a C r C 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a C 1 - C 6 alkoxy, a Ci-C 6 alkoxycarbonyl, a Ci-Ce-alkoxy-C ⁇ C ⁇ -alkyl group, a Ci-C 6 -Sulfoalkyl distr, a Ci-C 6 -Carboxyalkyl distr and a group R X R
  • the radical Het according to formula (V) is particularly preferably derived from the heteroaromatics furan, thiophene, pyrrole, isoxazole, isothiazole, imidazole, oxazole, thiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1, 2,3-triazine, 1, 2 , 4-triazine, 1, 3,5-triazine, benzopyrrole, benzofuran, benzothiophene, benzimidazole, benzoxazole, indazole, benzoisoxazole, benzoisothiazole, indole, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, acridine, benzoquinoline, benzoisoquinoline, benzothiazole , Phenazine, benzocinnoline, benzoquinazoline, benzoquinox
  • the compounds according to formula (IV) are selected from the group consisting of 2- (2-furoyl) -acetonitrile, 2- (5-bromo-2-furoyl) -acetonitrile, 2- (5-methyl-2-trifluoromethyl- 3-furoyl) - acetonitrile, 3- (2,5-dimethyl-3-furyl) -3-oxopropanitrile, 2- (2-thenoyl) -acetonitrile, 2- (3-thenoyl) -acetonitrile, 2- (5-fluoro-2-thenoyl ) -acetonitrile, 2- (5-chloro-2-thenoyl) -acetonitrile, 2- (5-bromo-2-thenoyl) -acetonitrile, 2- (5-methyl-2-thenoyl) -acetonitrile, 2- (2 , 5-dimethylpyrrol-3-oyl) -acetonitrile, 2-
  • Agents preferred according to the invention are characterized in that they are formulated as hair colorants, based on their weight 0.01 to 20 wt .-%, preferably 0.05 to 15% by weight, particularly preferably 0.1 to 12.5 wt .-% and in particular 0.2 to 10 wt .-% of one or more CH-acidic compound (s) included.
  • the agents according to the invention contain at least one imidazole compound according to formula (I) and / or their physiologically acceptable salts.
  • the imidazole compound (s) of formula (I) is / are used within narrower ranges.
  • agents according to the invention are preferred which contain at least one imidazole compound of the formula (I) and / or their physiologically tolerable salts in amounts of from 0.5 to 15% by weight, preferably from 2.5 to 12.5% by weight, especially preferably from 3 to 10 wt .-% and in particular from 4 to 8 wt .-%.
  • the imidazole compounds according to formula I are selected from at least one member of a group which is formed from histamine, D-histidine, L-histidine, DL-histidine, D-histidinol, L-histidinol, DL-histidinol, imidazole, imidazole 4-acetic acid, imidazole-4-carboxylic acid, imidazole-4,5-dicarboxylic acid, imidazole-2-carboxaldehyde, imidazole-4-carboxaldehyde, imidazole-5-carboxaldehyde, 2-nitroimidazole, 4-nitroimidazole, 4-methylimidazole-5 carboxaldehyde, N-methylimidazole-2-carboxaldehyde, 4-methylimidazole, 2-methylimidazole, N-methylimidazole, N- (4-aminophenyl) -imidazole, and the physiologically acceptable salts
  • Imidazole is particularly preferably used according to the invention. Accordingly, preferred agents according to the invention are characterized in that the imidazole compound according to formula (I) and / or its physiologically tolerable salts is / are selected from histamine, D-histidine, L-histidine, DL-histidine, D-histidinol, L-histidinol, DL-histidinol, imidazole, imidazole-4 acetic acid, imidazole-4-carboxylic acid, imidazole-4,5-dicarboxylic acid, imidazole-2-carboxaldehyde, imidazole-4-carboxaldehyde, imidazole-5-carboxaldehyde, 2-nitroimidazole, 4-nitroimidazole, 4-methylimidazole-5-carboxaldehyde, N-methylimidazole-2-carboxaldehyde, 4-methylimidazole, 2-methylimidazole, N
  • the agents according to the invention optionally contain ammonia (calculated as 100% NH 3 ), the amount of which is limited to a maximum of 2% by weight, based on the total agent or, in the case of multi-component agents, of the ready-to-use mixture.
  • Preferred agents or application mixtures according to the invention contain not more than 1, 8% by weight of ammonia, more preferably not more than 1, 5 wt .-% ammonia, even more preferably not more than 1, 25 wt .-% ammonia, more preferably at most 1, 0 wt. -% ammonia and in particular at most 0.5 wt .-% ammonia.
  • the agents are ammonia-free.
  • compositions according to the invention can also be prepared directly before use from two or more separately packaged preparations. This is particularly useful for the separation of incompatible ingredients to avoid premature reaction.
  • a common way is therefore to mix an agent A according to the invention with an oxidizing agent preparation B directly before use to form an application mixture.
  • Another object of the present invention is therefore an agent for dyeing and / or whitening keratinic fibers, in particular human hair, which immediately before application to the hair from a flowable preparation A, an oxidizing agent preparation B containing at least one oxidizing agent selected from hydrogen peroxide and whose addition compounds are obtained on solid carriers and a preparation C, which are mixed together to a dyeing and / or Aufhellansatz, wherein the composition A and / or C is a composition of the invention, or the composition A oxidation dye precursor (s) and the composition C contains imidazole (s) (or vice versa).
  • the mixture of formulations A, B and C prior to use results in an application mixture containing oxidation dye precursor (s) and imidazole (s).
  • preferred application mixtures satisfy the first embodiment of the present invention, ie particularly preferred means of the second embodiment are so made up and / or are mixed together in a ratio such that the use mixture contains said amounts of oxidation dye precursor (s) and imidazole (s).
  • An oxidizer formulation B contains at least one oxidizer selected from hydrogen peroxide and its attachment compounds to solid supports.
  • hydrogen peroxide itself is preferably used.
  • the hydrogen peroxide is used as a solution or in the form of a solid addition compound of hydrogen peroxide to inorganic or organic compounds, such as sodium perborate, sodium percarbonate, magnesium percarbonate, sodium percarbamide, polyvinylpyrrolidone n H 2 O 2 (n is a positive integer greater than 0), urea peroxide and melamine peroxide used.
  • aqueous hydrogen peroxide solutions are aqueous hydrogen peroxide solutions.
  • concentration of a hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; preferably 6 to 12 percent solutions in water are used.
  • the oxidizing agent preparation B - based on their weight - 0.5 to 10 wt .-%, preferably 0.75 to 9.0 wt .-%, particularly preferably 1 to 8.0 wt .-%, more preferably 1, 25 to 7.0 wt .-% and in particular 1, 5 to 6.0 wt .-% hydrogen peroxide (calculated as 100% H 2 O 2 ) contains.
  • the oxidizer formulation B is preferably an aqueous, flowable oxidizer formulation. Accordingly, preferred agents for dyeing and / or lightening keratinic fibers according to the invention are characterized in that the flowable oxidizing agent preparation B - based on their weight - 40 to 90 wt .-%, preferably 50 to 85 wt .-%, particularly preferably 55 to 80 wt .-%, more preferably 60 to 77.5 wt .-% and in particular 65 to 75 wt .-% water.
  • agents according to the invention which are 0.5 to 15 wt.%, Preferably 1 to 12.5 wt.%, Particularly preferably 2.5 to 10 wt.% And in particular 3 to 6 wt .-% hydrogen peroxide (calculated as 100% H 2 O 2 ) included.
  • the flowable oxidizing agent preparation B an emulsifier or a surfactant is added, wherein surface-active substances depending on the field of application as surfactants or as Emulsifiers are selected and selected from anionic, cationic, zwitterionic, ampholytic and nonionic surfactants and emulsifiers. These substances are described in detail below.
  • this further peroxo compound is in principle not limited to conventional peroxo compounds known to those skilled in the art, for example ammonium peroxydisulfate, potassium peroxodisulfate, sodium peroxydisulfate, ammonium persulfate, potassium persulfate, sodium persulfate, percarbonates such as magnesium percarbonate Peroxides such as barium peroxide and perborates, urea peroxide and melamine peroxide are among these peroxo compounds which may also be used in combination.
  • Partoxysulfates, in particular combinations of at least two peroxide sulphates, are preferred according to the invention and / or lightening keratinic fibers which additionally comprise from 0.01 to 2% by weight of at least one solid peroxo compound selected from ammonium, alkali containing imetalic and alkaline earth metal persulfates and peroxydisulfates, preferred agents containing peroxydisulfates, which are preferably selected from sodium peroxydis
  • the flowable oxidizer composition B additionally contains at least one peroxy compound, which is preferably selected from ammonium and alkali metal persulfates and peroxydisulfates, preferred agents containing at least 2 different peroxydisulfates.
  • compositions according to the invention may comprise at least one compound of amino acids and / or oligopeptides, these in each case having at least two amino groups and at least one -COOH or -SO H group and having their 2,5-
  • % solution in water in each case has a pH greater than 9.0.
  • Preferred alkalizing agents are aminocarboxylic acids, in particular ⁇ -aminocarboxylic acids and omega-aminocarboxylic acids.
  • ⁇ -aminocarboxylic acids lysine and especially arginine are again particularly preferred.
  • Said amino acids can preferably be added to the agents according to the invention in free form. In a number of cases, however, it is also possible to use the amino acids in Use salt form. Preferred salts are then the compounds with hydrohalic acids, in particular the hydrochlorides and hydrobromides.
  • amino acids can also be used in the form of oligopeptides and protein hydrolysates if it is ensured that the required amounts of the amino acids used according to the invention are contained therein.
  • reference is made to the disclosure of DE-OS 22 15 303, to which reference is expressly made.
  • a particularly preferred alkalizing agent is arginine, especially in free form but also used as carbonate or hydrochloride.
  • Agents preferred according to the invention are characterized in that they additionally contain from 0.05 to 5% by weight, preferably from 0.1 to 2.5% by weight, particularly preferably from 0.15 to 1% by weight and in particular 0.2 to 0.5 wt .-% amino acid (s), preferably (one) amino acid (s) from the group glycine and / or alanine and / or VaNn and / or lysine and / or leucine and / or threonine.
  • amino acid (s) preferably (one) amino acid (s) from the group glycine and / or alanine and / or VaNn and / or lysine and / or leucine and / or threonine.
  • the anhydrous compositions of the present invention may additionally contain at least one other bleaching enhancer other than the inorganic persalts.
  • bleach amplifiers it is possible to use compounds which, under perhydrolysis conditions, give aliphatic peroxycarboxylic acids having preferably 1 to 10 C atoms, in particular 2 to 4 C atoms, and / or optionally substituted perbenzoic acid.
  • Suitable substances are those which carry O- and / or N-acyl groups of the stated C atom number and / or optionally substituted benzoyl groups.
  • polyacylated alkylene diamines in particular tetraacetylethylenediamine (TAED), acylated triazine derivatives, in particular 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-triazine (DADHT), acylated glycolurils, especially tetraacetylglycoluril (TAGU), N-acylimides, in particular N-nonanoylsuccinimide (NOSI), acylated phenolsulfonates, in particular n-nonanoyl or isononanoyloxybenzenesulfonate (n- or iso-NOBS), carboxylic anhydrides, in particular phthalic anhydride, acylated polyhydric alcohols, in particular triacetin, ethylene glycol diacetate and 2,5- diacetoxy-2,5-dihydrofuran.
  • TAED tetraacetylethylened
  • anhydrous compositions according to the invention may additionally contain as bleaching boosters at least one optionally hydrated SiO 2 compound.
  • the optionally hydrated SiO 2 compounds in amounts of 0.05 wt .-% to 15 wt .-%, especially preferably in amounts of 0.15 wt .-% to 10 wt .-% and most preferably in amounts of 0.2 wt .-% to 5 wt .-%, each based on the anhydrous composition according to the invention to use.
  • the present invention is in principle subject to no restrictions. Preference is given to silicic acids, their oligomers and polymers and their salts. Preferred salts are the alkali salts, especially the potassium and sodium salts. The sodium salts are very particularly preferred.
  • the optionally hydrated SiO 2 compounds can be present in various forms.
  • the SiO 2 compounds are preferably used in the form of silica gels (silica gel) or particularly preferably as water glass. These SiO 2 compounds may be partially present in aqueous solution.
  • water glasses which are formed from a silicate of the formula (SiO 2 ) n (Na 2 O) m (K 2 O) p , where n is a positive rational number and m and p are each independently one positive rational number or for O 1 with the provisos that at least one of the parameters m or p is different from 0 and the ratio between n and the sum of m and p is between 1: 4 and 4: 1.
  • the water glasses in small amounts may contain other additives, such as phosphates or magnesium salts.
  • particularly preferred water glasses are sold among others by Henkel under the names Ferrosil® ® 119, soda water glass 40/42, Portil ® A, Portil ® AW and Portil ® W and by Akzo under the name Britesil® ® C20.
  • Agents preferred according to the invention are characterized in that they additionally contain 0.05 to 15% by weight, more preferably 0.15 to 10% by weight and in particular 0.2 to 5% by weight of at least one optionally hydrated SiO 2 compound
  • Preferred agents include water glasses formed from a silicate of the formula (SiO 2 ) n (Na 2 O) m (K 2 O) p , where n is a positive rational number and m and p are independently one positive rational number or 0, with the provisos that at least one of the parameters m or p is different from 0 and the ratio between n and the sum of m and p is between 1: 4 and 4: 1.
  • compositions which are preferred according to the invention additionally comprise 0.1 to 25% by weight, preferably 0.5 to 20% by weight, particularly preferably 1 to 15% by weight and in particular 1.5 to 10% by weight of at least one substance from the groups of
  • Monoalkyl carbonates (carbonic acid monoesters) and / or
  • Carbonic acid monoamides and / or
  • Particularly suitable carbonates are ammonium, alkali metal and alkaline earth metal carbonates and bicarbonates.
  • sodium bicarbonate, sodium carbonate are particularly preferred.
  • compositions according to the invention may preferably also contain at least one carbonic acid monoester and / or at least one carbonic acid monoamide. These substances are described in detail below.
  • Agents preferred according to the invention are characterized in that they contain at least one carbonic acid monoester of the formula (VII)
  • R represents a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical, or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle.
  • R preferably represents a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, sulfonic acid groups or halogens as substituents.
  • Further preferred radicals R are phenyl and benzyl radicals and further substituted representatives. More preferably, R is a C 1-6 alkyl group.
  • CrC ⁇ -alkyl groups are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • Particularly preferred agents according to the invention are characterized in that the radical R in formula (VII) is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, tert-butyl as well as hydroxymethyl and hydroxyethyl radicals.
  • compositions according to the invention may contain carbonic acid monoamides.
  • preferred agents according to the invention are characterized in that they contain at least one carbonic acid monoamide of the formula (VIII)
  • R is a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical, or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle.
  • R preferably represents a substituted or unsubstituted, straight-chain or branched alkyl, alkenyl or alkynyl radical, preference being given to hydroxy, amino, nitro, sulfonic acid groups or halogens as substituents.
  • Further preferred radicals R are phenyl and benzyl radicals and further substituted representatives. More preferably R is a Ci. 6- alkyl group.
  • CrC 6 -alkyl groups are the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl.
  • radical R in formula (VIII) is selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, tert-butyl as well as hydroxymethyl and hydroxyethyl radicals.
  • the acidic H atom of the carbonic acid monoester or monoamide may also be in neutralized form, i. salts of carbonic acid monoesters or carbonic acid monoamides can also be used according to the invention.
  • agents according to the invention are preferred which contain the carbonic acid monoester or the carbonic acid monoamide in completely or partially neutralized form, preferably in the form of its alkali metal, ammonium, alkaline earth metal or aluminum salt and in particular in the form of its sodium salt.
  • compositions according to the invention contain one or more carbonic acid monoesters and / or one or more carbonic acid monoamides
  • these agents according to the invention preferably, the one or more carbonic acid monoesters and / or carbonic acid monoamides in amounts of 0.1 to 20 wt.%, Preferably from 0.5 to 18 wt.%, Particularly preferably from 2 to 15 wt.% And especially from 5 to 12 % By weight, based in each case on the total agent.
  • compositions according to the invention may preferably also contain at least one silyl carbonate and / or at least one silyl carbamate. These substances are described in detail below.
  • Agents preferred according to the invention are characterized in that they contain at least one silyl carbonate of the formula (IX)
  • radicals R 1 , R 2 and R 3 independently of one another represent a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or a trialkylsilyl group, preferably a trimethylsilyl group or a substituted or unsubstituted Aryl group or a substituted or unsubstituted heterocycle or a halogen, a substituted or unsubstituted hydroxy, oxo, amino, imino groups and the radical R 4 is a chemical bond to the Si atom or to one of the radicals R 1 , R 2 or R 3 , a hydrogen atom, a saturated or unsaturated, straight-chain, branched, or cyclic, substituted or unsubstituted hydrocarbon radical, or a substituted or unsubstituted silyl or alumyl group or a substituted or unsubstituted aryl group or a substituted
  • Preferred radicals R 1 , R 2 and R 3 in the abovementioned formula (IX) are substituted or unsubstituted, straight-chain or branched alkyl radicals.
  • the alkyl radicals having 1 to 5 carbon atoms and the hydroxyalkyl radicals are preferred, so that preferred agents according to the invention are characterized in that the radicals R 1 , R 2 and R 3 in formula (IX) are selected from methyl, ethyl, n Propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, hydroxymethyl and hydroxyethyl radicals.
  • Preferred radicals R 4 in the abovementioned formula (IX) are hydrogen, substituted or unsubstituted, straight-chain or branched alkyl radicals and trialkylsilyl radicals. Among them, preferred are hydrogen, methyl, ethyl, tert-butyl and trimethylsilyl radicals.
  • agents according to the invention are preferred which comprise at least one silyl carbonate in completely or partially neutralized form, preferably in the form of its alkali metal, ammonium, alkaline earth metal or aluminum salt and in particular in the form of its sodium salt.
  • compositions of the invention may contain silyl carbamates.
  • Agents preferred according to the invention are characterized in that they contain a silyl carbamate of the formula (X)
  • radicals R 1 , R 2 and R 3 independently of one another represent a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or for a trialkylsilyl group, preferably a trimethylsilyl group or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocycle or a halogen, a substituted or unsubstituted hydroxy, oxo, amino groups and the radicals R 4 and R 5 independently of one another for a chemical bond to the Si atom or to a the radicals R 1 , R 2 or R 3 , a hydrogen atom, a saturated or unsaturated, straight-chain, branched or cyclic, substituted or unsubstituted hydrocarbon radical or a substituted or unsubstituted SiIyI or alumino group or a substituted or unsubstituted
  • Preferred radicals R 1 , R 2 and R 3 in the abovementioned formula (X) are substituted or unsubstituted, straight-chain or branched alkyl radicals.
  • the alkyl groups are 1 to 5 carbon atoms and the hydroxyalkyl radicals are preferred, so that preferred agents according to the invention are characterized in that the radicals R 1 , R 2 and R 3 in formula (X) are selected from methyl, ethyl, n-propyl, iso-propyl , n-butyl, iso-butyl, terf-butyl, hydroxymethyl and hydroxyethyl radicals.
  • Preferred radicals R 4 and R 5 in the abovementioned formula (X) are hydrogen, substituted or unsubstituted, straight-chain or branched alkyl radicals and trialkylsilyl radicals. Among them, preferred are hydrogen, methyl, ethyl, tert-butyl and trimethylsilyl radicals.
  • compositions according to the invention contain one or more silyl carbonates and / or one or more silyl carbamates
  • agents according to the invention are preferred which contain the silyl carbonate (s) and / or silyl carbamate (s) in amounts of from 0.1 to 25% by weight .%, Preferably from 0.5 to 20 wt.%, Particularly preferably from 1 to 15 wt.% And in particular from 1, 5 to 10 wt.%, Each based on the total agent.
  • the agents according to the invention preferably have a pH of from 5.0 to 9.0, preferably from 5.5 to 8.0, particularly preferably from 6.0 to 7.7, more preferably from 6.2 to 7.2 and especially from 6.5 to 6.8.
  • the dyeing and / or lightening agents according to the invention may additionally comprise at least one cyanate of the formula M + [OCN] ' in the M + for K + , Na + , Li + or NH 4 + or Y 2 Ca 2+ , Y 2 Mg 2+ or Y 2 Zn 2+ and / or at least one compound of the formula H 2 NC (O) -L, in which L is a group displaceable by the anion ⁇ OOH group.
  • preferred agents according to the invention additionally contain
  • cyanates potassium cyanate, KOCN, and / or sodium cyanate, NaOCN, and / or lithium cyanate, LiOCN, and / or ammonium cyanate, NH 4 OCN, and / or calcium cyanate, Ca (OCN) 2 , and / or magnesium cyanate, Mg (OCN ) 2 , and / or zinc cyanate, Zn (OCN) 2 .
  • Agents preferred according to the invention are characterized in that they contain 0.075 to 4% by weight, preferably 0.1 to 2.5% by weight and in particular 0.2 to 1% by weight of sodium cyanate and / or potassium cyanate and / or ammonium cyanate with sodium cyanate being particularly preferred.
  • H 2 NC (O) -L in which L is selected from -S-CH 2 -COOH, -S- (CH 2 ) 3 SO 3 H, -S- (CH 2 ) 2 -NH 2l -OCH 3 , -O- (C 6 H 4 ) -SO 3 M, -Q + , -NH-OH, -O-C (O) -R 1 , -O-C (O) -H, -O-CH ( OH) 2 , -SO 3 M, -PH (O) OH, -P (O) (OH) 2 , - (NH-glucosamine) n , -NH-C (O) -NH 2 , -NH-NH 2 , -NH-CN, -P (OH) (O) -C (O) NH 2 , -SCN, -OCN, -SC (NH) NH 2 ,
  • M is -H, Na, K, NH 4
  • Q is selected from quaternary ammonium radicals, heteroaryl radicals or nonaromatic heterocycles formed from tertiary amines and R 1 is --H, -CH 3 , -CH 2 CH 3 , - ( CH 2 J 2 CH 3 , -CH (CH 3 ) 2 or another alkyl group.
  • Particularly preferred agents according to the invention contain from 0.075 to 4% by weight, preferably from 0.1 to 3.5% by weight and in particular from 0.2 to 3% by weight of at least one of the compounds listed below:
  • the dyeing and / or brightening agents according to the invention contain nonionic surfactants.
  • Such surfactants having an HLB of 5.0 and greater are preferred.
  • HLB value For the definition of the HLB value, explicit reference is made to the statements in Hugo Janistyn, Handbuch der Kosmetika und Riechstoffe, III. Volume: The personal care products, 2nd edition, Dr. med. Alfred Hüthig Verlag Heidelberg, 1973, pages 68-78 and Hugo Janistyn, Paperback of modern perfumery and cosmetics, 4th edition, Scientific Publishing Company m.b.H. Stuttgart, 1974, pages 466-474, as well as the original works cited therein.
  • non-ionic surface-active substances are substances that are commercially available as solids or liquids in pure form because of their ease of processing.
  • the definition of purity in this context does not refer to chemically pure compounds. Rather, especially when it comes to natural-based products, mixtures of different homologs can be used, for example, with different alkyl chain lengths, such as those obtained with products based on natural fats and oils. Even with alkoxylated products, mixtures of different degrees of alkoxylation are usually present.
  • purity in this context refers rather to the fact that the chosen substances should preferably be free from solvents, stabilizers and other impurities.
  • Preferred nonionic surfactants are:
  • - alkoxylated fatty alcohols having 8 to 22, in particular 10 to 16, carbon atoms in the fatty alkyl group and 1 to 30, in particular 1 to 15, ethylene oxide and / or
  • Preferred fatty alkyl groups are, for example, lauryl, myristyl, cetyl, but also stearyl, isostearyl and oleyl groups.
  • Particularly preferred compounds of this class are, for example, lauryl alcohol with 2 to 4 ethylene oxide units, oleyl and Cetyl alcohol having in each case 5 to 10 ethylene oxide units, cetyl and stearyl alcohol and mixtures thereof with 10 to 30 ethylene oxide units and the commercial product Aethoxal ® B (Henkel), a lauryl alcohol with 5 ethylene oxide and 3 propylene oxide units.
  • alkoxylated fatty alcohols it is also possible to use so-called "end-capped” compounds according to the invention
  • the alkoxy group has no OH group at the end but is "closed” in the form of an ether, in particular a C 1 -C 4 -alkyl ether.
  • An example of such a compound is the commercially available product ® Dehypon LT 054, a Ci-2 -i ⁇ Fettalkoholol + 4.5 ethylene oxide-butyl ether.
  • - alkoxylated fatty acids having 8 to 22, in particular 10 to 16, carbon atoms in the fatty acid group and 1 to 30, in particular 1 to 15, ethylene oxide and / or propylene oxide units.
  • Preferred fatty acids are, for example, lauric, myristic, palmitic, stearic, isostearic and oleic acids.
  • - alkoxylated, preferably propoxylated and especially ethoxylated, mono-, di- and triglycerides examples are glycerol monolaurate + 20 ethylene oxide and glycerol monostearate + 20 ethylene oxide.
  • Polyglycerol esters and alkoxylated polyglycerol esters are for example poly (3) glycerol diisostearate (commercial product: Lameform ® TGI (Henkel)) and poly (2) glycerinpolyhydroxy- stearate (commercial product: Dehymuls ® PGPH (Henkel)).
  • Sorbitan fatty acid esters and alkoxylated sorbitan fatty acid esters such as sorbitan monolaurate and sorbitan monolaurate + 20 ethylene oxide (EO).
  • Alkylphenols and Alkylphenolalkoxylate having 6 to 21, in particular 6 to 15, carbon atoms in the alkyl chain and 0 to 30 ethylene oxide and / or propylene oxide units.
  • Preferred representatives of this class are, for example, nonylphenol + 4 EO, nonylphenol + 9 EO, octylphenol + 3 EO and octylphenol + 8 EO.
  • nonionic surfactants are the alkoxylated fatty alcohols, the alkoxylated fatty acids and the alkylphenols and alkylphenol alkoxylates.
  • Agents according to the invention which contain non-ionic surface-active substances in amounts of 1 to 5% by weight have proved to be particularly advantageous.
  • the dyeing and / or brightening agents according to the invention may contain all known in such preparations active ingredients, additives and excipients.
  • the agents contain at least one surfactant, wherein in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • anionic surfactants may be very particularly preferred.
  • Preferred anionic surfactants are alkyl sulfates, alkyl ether carboxylic acid salts having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, such as C 2 H 25 - (C 2 H 4 O) 6 -CH 2 - COONa, and especially salts of saturated and especially unsaturated C8-C22 carboxylic acids such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • anionic surfactants should preferably be present in solid, in particular powder form. Very particular preference is given to solid soaps, especially sodium stearate, at room temperature. These are preferably present in amounts of from 5 to 20% by weight, in particular from 10 to 15% by weight.
  • Suitable nonionic surfactants are in particular C 8 -C 22 -alkyl mono- and oligoglycosides and their ethoxylated analogs.
  • the nonethoxylated compounds have been found to be particularly suitable.
  • cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride,
  • Tricetylmethylammonium chloride Tricetylmethylammonium chloride.
  • Further cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • Alkylamidoamines in particular fatty acid amidoamines, such as the stearylamidopropyldimethylamine obtainable under the name Tego Amid® S 18, are distinguished not only by a good conditioning action but also by their good biodegradability. Also very good biodegradability are quaternary Ester für styrene, so-called "esterquats", such as the Distearoylethylhydroxyethylammoniummethosulfat available in a blend with Cetearylalkohle under the name Dehyquart® ® F 75 miles.
  • esterquats such as the Distearoylethylhydroxyethylammoniummethosulfat available in a blend with Cetearylalkohle under the name Dehyquart® ® F 75 miles.
  • the compounds containing alkyl groups used as surfactants may each be uniform substances. However, it is usually preferred to start from the production of these substances from native plant or animal raw materials, so as to obtain substance mixtures with different, depending on the particular raw material alkyl chain lengths.
  • nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers
  • anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids and
  • Vinyl acetate / crotonic acid copolymers provided that they are stable as solids or preferably in
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic,
  • Structurants such as glucose, maleic acid and lactic acid, hair conditioning compounds such as phospholipids, for example soya lecithin, egg
  • 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,
  • Dyes for coloring the preparations Active substances such as panthenol, pantothenic acid, allantoin, pyrrolidonecarboxylic acids and their salts,
  • Fats and waxes such as spermaceti, beeswax, montan wax, paraffins,
  • Swelling and penetration substances such as carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • compositions according to the invention may contain at least one ammonium compound from the group of ammonium chloride, ammonium carbonate, ammonium bicarbonate, ammonium sulfate and / or ammonium carbamate in an amount of from 0.5 to 10, preferably from 1 to 5,% by weight, based on the total composition of the composition ,
  • dyeing and / or brightening agents according to the invention may contain further active ingredients, auxiliaries and
  • Additives such as nonionic polymers such as vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallyl-ammonium chloride copolymers, with Diethyl sulfate quaternized dimethylamino-ethyl methacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacryl
  • methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such.
  • Bentonite or fully synthetic hydrocolloids such as e.g. polyvinyl alcohol,
  • Structural agents 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
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, fiber structure-improving agents, in particular mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl-1-alkylamidoethyl -2-alkylimidazolinium methosulfate
  • Anti-dandruff agents such as Piroctone Olamine, Zinc Omadine and Climbazole,
  • Light stabilizers in particular derivatized benzophenones, cinnamic acid derivatives and
  • Active ingredients 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 ,
  • Plant extracts such as extracts of green tea, oak bark, stinging nettle, witch hazel,
  • Spruce needle horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime,
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as spermaceti, beeswax, montan wax and paraffins,
  • fatty acid fatty acid
  • Complexing agents such as EDTA 1 NTA, ⁇ -alaninediacetic acid and phosphonic acids, swelling and penetrating agents such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates, opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate, pigments,
  • Stabilizers for hydrogen peroxide and other oxidizing agents blowing agents such as propane-butane mixtures, N 2 O 1 dimethyl ether, CO 2 and air, antioxidants
  • compositions according to the invention may contain the ingredients in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier for the purpose of hair coloring such carriers are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as shampoos, 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.
  • pul-shaped or tablet-shaped formulation which is preferred for dyeing and / or brightening agents.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C 1 -C 4 -alkoxyethane, 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.
  • Preferred agents according to the invention are characterized in that they additionally contain a nonaqueous solvent, particularly preferred compositions according to the invention the solvent in a concentration of 0.1 to 30 weight percent, preferably in a concentration of 1 to 20 weight percent, most preferably in a concentration of 2 - 10 weight percent, each based on the agent included.
  • the solvent is selected from ethanol, n-propanol, isoropanol, n-butanol, propylene glycol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, phenoxyethanol and benzyl alcohol and mixtures thereof.
  • the pH of the compositions according to the invention can be adjusted within a wide range by suitable ingredients such as acidifying agent or alkalizing agent.
  • Oxidative dyeing of the fibers can in principle be carried out with atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent is used, especially if, in addition to the coloring, a lightening effect on human hair is desired. This lightening effect may be desired regardless of the staining method.
  • the presence of oxidation dye precursors is therefore not a mandatory requirement for the use of oxidizing agents in the compositions of the invention.
  • Suitable oxidizing agents are persulfates, chlorites and in particular hydrogen peroxide or its addition products of urea, melamine and sodium borate.
  • the oxidation colorant can also be applied to the hair together with a catalyst which promotes 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 include peroxidases, which can significantly enhance the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as, for example, the laccases, or generate small amounts of hydrogen peroxide in situ and thus biocatalytically activate the oxidation of the dye precursors.
  • catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the specific substrates, for example pyranose oxidase and, for example, D-glucose or galactose, Glucose oxidase and D-glucose, glycerol oxidase and glycerin,
  • Pyruvate oxidase and pyruvic acid or its salts - alcohol oxidase and alcohol (MeOH, EtOH), lactate oxidase and lactic acid and its salts, tyrosinase oxidase and tyrosine, uricase and uric acid or their salts, choline oxidase and choline, amino acid oxidase and amino acids.
  • the actual colorant is conveniently prepared immediately prior to use by mixing the preparation of the oxidizing agent with the preparation containing the compounds of formula I and optionally dye precursors.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range of 6 to 12. Particularly preferred is the use of the hair dye in a weakly alkaline medium.
  • 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 washing with a shampoo is omitted if a strong surfactant-containing carrier, such as a dyeing shampoo was used.
  • an agent according to the invention may optionally be applied to the hair with additional dye precursors but also without prior mixing with the oxidation component. After an exposure time of 20 to 30 minutes, the oxidation component is then applied, if appropriate after an intermediate rinse. After a further exposure time of 10 to 20 minutes, the product is then rinsed and, if desired, shampooed again.
  • 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 peroxydisulfate solutions may be preferred as the oxidizing agent.
  • compositions of the invention are mixed immediately before application with a hydrogen peroxide solution.
  • concentration of this hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; As a rule, 6-12% solutions in water are used.
  • the proportions of dyeing and / or lightening agent and hydrogen peroxide solution are usually in the range 1: 1 to 1: 2, with an excess of hydrogen peroxide solution is particularly selected when no too pronounced Blondier Stil is desired.
  • compositions according to the invention may contain further ingredients.
  • use of certain metal ions or complexes may be preferred to obtain intense colorations.
  • Agents according to the invention which additionally contain Cu, Fe, Mn, Ru ions or complexes of these ions are preferred here.
  • Preferred agents according to the invention additionally contain Cu, Fe, Mn, Co, Ce, V, Ru ions or complexes of these ions, with particularly preferred agents being 0.0001 to 2.5% by weight, preferably 0.001 to 1 wt .-% of at least one compound from the group copper chloride (CuCl 2 ), copper sulfate (CuSO 4 ), iron (II) sulfate, manganese (II) sulfate, manganese (II) chloride, cobalt (II) chloride, cerium sulfate, cerium chloride , Vanadium sulfate, manganese dioxide (MnO 2 ).
  • CuCl 2 copper chloride
  • CuSO 4 copper sulfate
  • iron (II) sulfate iron
  • manganese (II) sulfate manganese (II) chloride
  • cobalt (II) chloride cerium sulfate, cerium chloride , Vanadium
  • Complex images are substances that can complex metal ions.
  • Preferred complexing agents are so-called chelating agents, ie substances which form cyclic compounds with metal ions, a single ligand occupying more than one coordination site on a central atom, i. H. at least "bidentate".
  • chelating agents ie substances which form cyclic compounds with metal ions, a single ligand occupying more than one coordination site on a central atom, i. H. at least "bidentate”.
  • normally stretched compounds are closed by complex formation via an ion into rings.
  • the number of bound ligands depends on the coordination number of the central ion.
  • Customary and preferred chelate complex images in the context of the present invention are, for example, polyoxycarboxylic acids, polyamines, ethylenediaminetetraacetic acid (EDTA), nitrilotriacetic acid (NTA) and hydroxyethanediphosphonic acids or their alkali metal salts.
  • complex-forming polymers ie polymers which carry functional groups either in the main chain itself or laterally to it, which can act as ligands and react with suitable metal atoms usually with the formation of chelate complexes, can be used according to the invention.
  • the polymer-bound ligands of the resulting metal complexes can originate from only one macromolecule or belong to different polymer chains.
  • Complexing groups (ligands) of conventional complexing polymers are iminodiacetic acid, hydroxyquinoline, thiourea, guanidine, dithiocarbamate, hydroxamic acid, amidoxime, aminophosphoric acid, (cyclic) polyamino, mercapto, 1,3-dicarbonyl - And crown ether residues with z. T. very specific. Activities towards ions of different metals.
  • Base polymers of many also commercially important complex-forming polymers are polystyrene, polyacrylates, polyacrylonitriles, polyvinyl alcohols, polyvinylpyridines and polyethyleneimines. Natural polymers such as cellulose, starch or chitin are also complex-forming polymers. In addition, these can be provided by polymer-analogous transformations with other ligand functionalities.
  • Hydroxyl groups is at least 5,
  • polycarboxylic acids a) are understood as meaning carboxylic acids, including monocarboxylic acids, in which the sum of carboxyl and the hydroxyl groups contained in the molecule is at least 5.
  • Complexing agents from the group of nitrogen-containing polycarboxylic acids, in particular EDTA are preferred.
  • these complexing agents are at least partially present as anions. It is irrelevant whether they are introduced in the form of acids or in the form of salts.
  • alkali metal, ammonium or alkylammonium salts, in particular sodium salts are preferred.
  • polymeric aminodicarboxylic acids their salts or their precursors.
  • polyaspartic acids or their salts and derivatives which, in addition to cobuilder properties, also have a bleach-stabilizing action.
  • polyacetals which can be obtained by reacting dialdehydes with polyolcarboxylic acids which have 5 to 7 C atoms and at least 3 hydroxyl groups.
  • Preferred polyacetals are obtained from dialdehydes such as glyoxal, glutaraldehyde, terephthalaldehyde and mixtures thereof and from polyol carboxylic acids such as gluconic acid and / or glucoheptonic acid.
  • phosphonates are, in particular, hydroxyalkane or aminoalkanephosphonates.
  • hydroxyalkane phosphonates 1-hydroxyethane-1,1-diphosphonate (HEDP) is of particular importance. It is preferably used as the sodium salt, the disodium salt neutral and the tetrasodium salt alkaline (pH 9).
  • Preferred aminoalkane phosphonates are ethylenediamine tetramethylene phosphonate (EDTMP), diethylene triamine pentamethylene phosphonate (DTPMP) and their higher homologs. They are preferably in the form of neutral sodium salts, eg. B.
  • the complexing agent used here is preferably HEDP from the class of phosphonates.
  • the aminoalkanephosphonates also have a pronounced heavy metal binding capacity. Accordingly, in particular if the agents also contain bleach, it may be preferable to use aminoalkanephosphonates, in particular DTPMP, or to use mixtures of the phosphonates mentioned. These substances will be described below.
  • phosphonates preferably hydroxyalkane or aminoalkane phosphonates and in particular 1-hydroxyethane-1,1-diphosphonate (HEDP) or its di- or tetrasodium salt and / or ethylenediamine tetramethylene phosphonate (EDTMP) or its hexasodium salt and / or diethylene triamine pentamethylene phosphonate (DTPMP ) or its hepta- or octasodium salt.
  • HEDP 1-hydroxyethane-1,1-diphosphonate
  • ETMP ethylenediamine tetramethylene phosphonate
  • DTPMP diethylene triamine pentamethylene phosphonate
  • Particularly preferred agents according to the invention contain one or more substances from the group
  • NTA nitrilotriacetic acid
  • EDDG ethylenediamine-N-N'-diglutaric acid
  • cyclodextrins preferred agents being phosphonates, preferably hydroxyalkane or aminoalkane phosphonates and in particular 1-hydroxyethane-1,1-diphosphonate (HEDP) or its di- or tetrasodium salt and / or ethylenediamine tetramethylene phosphonate (EDTMP) or its hexasodium salt and or diethylenetriaminepentamethylenephosphonate (DTPMP) or its hepta- or octasodium salt.
  • HEDP 1-hydroxyethane-1,1-diphosphonate
  • ETMP ethylenediamine tetramethylene phosphonate
  • DTPMP diethylenetriaminepentamethylenephosphonate
  • Preferred agents according to the invention are formulated with little or no water. Particularly preferred agents according to the invention are characterized in that they contain less than 5% by weight, preferably less than 2% by weight, more preferably less than 1% by weight and in particular less than 0.5% by weight of water, preferred agents being anhydrous.
  • the water content of the agent can be determined, for example, by means of titration according to Karl Fischer.
  • a second object of the present invention is a process for whitening keratin fibers, in particular human hairs, characterized in that, if desired, a pre-treatment agent M1 is applied to the fiber, then an agent M2 is applied to the fiber, wherein, if desired, the agent M2 before the Application of a further agent M3 is added, this agent M2 is rinsed from the fiber after a time of 5-30 minutes and after treatment optionally a post-treatment agent M4 applied to the fiber and rinsed after a contact time of a few minutes, wherein at least one the agent M1, M2 or M3 is an agent according to the invention.
  • the agents according to the invention can accordingly be formulated as single-component agents (dyeing and whitening agents M2 or aftertreatment agents M4), as two-component agents (M2 + M3) or as three-component agents (M2 + M3 + M4) and used accordingly. Separation into multicomponent systems is particularly suitable where incompatibilities of the ingredients are to be expected or feared; the agent to be used In such systems the consumer is prepared by mixing the component just prior to use.
  • a dyeing and whitening process in which the whitening cream and the oxidizing agent are initially separate is preferred.
  • a further subject of the present invention is therefore a process for dyeing and lightening human hair, in which an aqueous-based composition containing hydrogen peroxide is mixed with an agent according to the invention to form a homogeneous composition and applied to the hair.
  • the aqueous composition contains from 1 to 20% by weight, preferably from 2 to 10% by weight and in particular from 3 to 6% by weight of hydrogen peroxide, calculated as 100% H 2 O 2 .
  • aqueous-based composition comprising hydrogen peroxide is mixed with an agent according to the invention in a weight ratio of 1: 5 to 10: 1, preferably 1: 2 to 5: 1 and in particular 1: 2 to 2: 1 mixed into a homogeneous composition, and this is applied to the hair.
  • a further subject matter of the present invention is therefore a process for dyeing and lightening human hair which comprises an aqueous-based composition containing hydrogen peroxide with a further agent containing preferably at least one alkalinity donor and / or substantive hair dye and / or at least one oxidation dye precursor, and a composition according to the invention mixed to a homogeneous composition, and this is applied to the hair.
  • Another object of the present invention is the use of at least one imidazole compound according to formula (I) and / or their physiologically acceptable salts wherein
  • R 1 represents a hydrogen atom, an optionally substituted aryl group or a (C r C 6 ) alkyl group,
  • R 2 represents a hydrogen atom, a carboxaldehyde group, a (C 1 -C 6 ) -alkyl group or a nitro group,
  • R 3 represents a hydrogen atom, a carboxy-fCrC ⁇ alkyl group, an amino (Ci-C 6 ) alkyl group, a carboxyl group, a
  • Carboxaldehyde group a (C r C 6 ) alkyl group, a nitro group, a 2-amino-3-hydroxypropyl group or a group -CH 2 -CH (NH 2 ) -COOH 1
  • R 4 represents a hydrogen atom, a carboxaldehyde group or a
  • Carboxyl group in combination with one or more dye precursors and / or substantive dyes in agents for dyeing and / or lightening keratinic fibers.
  • the use of the mixtures is the achievement of certain advantageous
  • the mutated mutandis applies to the preferred agents.
  • the concentrations of developers and couplers were in each case 1 mMoI / 100 g of drug solution, the concentrations of direct drawers 0.1 and 0.2%.
  • the concentrations of hydrogen peroxide were 6.0%, the concentrations of imidazole and (for the comparative experiments) of ammonium peroxydisulfate 4.0% (see tables).
  • the solutions were additionally stabilized with 1.5% turpinal (60% solution of hydroxyethanediphosphonic acid) and 0.1% dipicolinic acid.
  • the dE values are only of limited use.
  • the data are stable in coloration against the combination of hydrogen peroxide / imidazole and in view of a lightening of the basic hair color by this combination in the presence of the dyes - in each case in comparison to the data with hydrogen peroxide - interpret as follows:
  • the hair becomes both lighter, redder and more yellowish as compared to bleaching with hydrogen peroxide. If one now assumes that the Euronatur hair is not significantly changed by the influence of the oxidizing agent white, then one can in difference formation of the data for L, a and b for the lightening with the combination of imidazole / hydrogen peroxide in comparison to the lightening with hydrogen peroxide and calculate the influence of the imidazole on the dye stability by calculating the dE values.
  • the dark-blond hair should be brightened at the same time, it is possible to estimate by double difference formation of the data (ddL, dda, ddb) whether in addition to dye formation there is still a lightening and a color shift characteristic of further lightening beyond that of hydrogen peroxide. However, it is assumed that the dye formation on the dark blond hair is done in the same way as on the natural white hair.
  • the following table summarizes the data for dL, da and db for the tints on natural blond and dark blond hair for the respective dye combinations.
  • the differences on natural blond hair show the influence of imidazole on color formation, the differences on dark blond hair the differences in dye formation and lightening. Forming the "double" differences of these values (ddL, dda, and ddb), the difference in dye formation drops out, and it can be estimated whether imidazole provides additional brightening beyond the influence of hydrogen peroxide on the dark blond hair.
  • Strands of dark blond hair (code: Kerling 7/0) weighing about 0.5 g were doused in beakers containing 15 times the amount of active substance solution and bleached at 32 ° C. for 30 minutes.
  • the concentrations of hydrogen peroxide in the drug solutions was 6.0 wt .-%, the concentrations in the drug solutions of imidazole-2-carboxaldehyde was 5.0 wt .-% and Mergital CS 50 10 wt .-%.
  • Turpinal SL 50% solution of hydroxyethanediphosphonic acid
  • dipicolinic acid 0.1% by weight
  • Plantacare 1200 UP 2.00 2.00 2.00
  • Strands of dark blond hair (code: Kerling 7/0) weighing about 0.5 g were doused in beakers containing 15 times the amount of colorant and dyed at 32 ° C. for 30 minutes.
  • the strands were dyed with the imidazole-containing colorants according to the invention were given a more uniform and intense coloration.

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Abstract

Produits à performance accrue et à effet irritant réduit destinés à l'éclaircissement et/ou la coloration de fibres kératiniques, en particulier des fibres kératiniques humaines. Ces produits contiennent - respectivement par rapport à leur poids - 0,001 à 5 % en poids d'au moins un précurseur de colorant et/ou de colorants directs et 0,1 à 20 % en poids d'au moins un composé imidazole conforme à la formule (I) et/ou leurs sels physiologiquement tolérables. Dans la formule (I), R<SUB>1</SUB> représente un atome d'hydrogène, un groupe aryle éventuellement substitué ou un groupe (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyle, R<SUB>2</SUB> représente un atome d'hydrogène, un groupe carboxaldéhyde, un groupe (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyle ou un groupe nitro, R<SUB>3</SUB> représente un atome d'hydrogène, un groupe carboxy-(C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyle, un groupe amino (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyle, un groupe carboxyle, un groupe carboxaldéhyde, un groupe (C<SUB>1</SUB>-C<SUB>6</SUB>)-alkyle, un groupe nitro, un groupe 2-alino-3-hydroxypropyle ou un groupe CH<SUB>2</SUB>-CH(NH<SUB>2</SUB>)-COOH, R<SUB>4</SUB> représente un atome d'hydrogène, un groupe carboxaldéhyde ou un groupe carboxyle.
EP07724015A 2006-04-13 2007-04-05 Produits éclaircissants et/ou colorants à tolérance cutanée améliorée Withdrawn EP2007344A1 (fr)

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DE200610017901 DE102006017901A1 (de) 2006-04-13 2006-04-13 Aufhell- und/oder Färbemittel mit verbesserter Hautverträglichkeit
PCT/EP2007/003074 WO2007118616A1 (fr) 2006-04-13 2007-04-05 Produits éclaircissants et/ou colorants à tolérance cutanée améliorée

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DE102006034957A1 (de) * 2006-07-28 2008-01-31 Henkel Kgaa Wasserstoffperoxid-Aktivierung mit Betainen und/oder Aminoxiden
ITUA20161586A1 (it) * 2016-03-11 2017-09-11 Beauty & Business S P A Composizione per colorare la fibra cheratinica
FR3060340B1 (fr) * 2016-12-20 2020-05-01 L'oreal Composition de coloration capillaire comprenant un colorant d’oxydation, un agent oxydant, un compose heterocyclique azote, et un derive polyphosphore
FR3060316B1 (fr) * 2016-12-20 2020-05-01 L'oreal Composition d’eclaircissement capillaire comprenant un agent oxydant, un compose heterocyclique azote et un derive polyphosphore
CN107049841A (zh) * 2017-06-20 2017-08-18 广州市花安堂生物科技有限公司 一种永久型染发组合物
DE102018221959A1 (de) * 2018-12-17 2020-06-18 Henkel Ag & Co. Kgaa Oxidationsfärbemittel in Rotnuancen mit verbesserter Echtheit und verbesserter Homogenität
FR3090358B1 (fr) * 2018-12-21 2020-12-18 Oreal Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel hétérocyclique insaturé et composition les comprenant
FR3090349B1 (fr) * 2018-12-21 2020-12-18 Oreal Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel hétérocyclique saturé et composition les comprenant
FR3090345B1 (fr) 2018-12-21 2021-06-25 Oreal Procédé de coloration des matières kératiniques mettant en œuvre un colorant direct et un sel ammonium aliphatique et composition les comprenant
FR3111552B1 (fr) * 2020-06-23 2024-04-05 Oreal Composition pour la décoloration et la coloration simultanées des fibres kératiniques comprenant un sel hétérocyclique particulier et procédé mettant en œuvre cette composition

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DE3929333A1 (de) * 1989-09-04 1991-03-07 Henkel Kgaa Egalisierende oxidationshaarfaerbemittel
MX9705954A (es) * 1995-02-03 1998-02-28 Cosmederm Technologies Formulaciones y metodos para reducir irritacion de la piel.
DE10025672A1 (de) * 2000-05-24 2001-11-29 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
DE102004028599A1 (de) * 2004-06-12 2005-12-29 Henkel Kgaa Milde Bleichmittel mit erhöhter Aufhellleistung

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