EP1715836A1 - Procede de coloration de fibres keratiniques - Google Patents

Procede de coloration de fibres keratiniques

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Publication number
EP1715836A1
EP1715836A1 EP04765400A EP04765400A EP1715836A1 EP 1715836 A1 EP1715836 A1 EP 1715836A1 EP 04765400 A EP04765400 A EP 04765400A EP 04765400 A EP04765400 A EP 04765400A EP 1715836 A1 EP1715836 A1 EP 1715836A1
Authority
EP
European Patent Office
Prior art keywords
hydroxy
amino
formyl
methyl
phenylenediamine
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Withdrawn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
EP04765400A
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German (de)
English (en)
Inventor
Martina Seiler
Detlef Hollenberg
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
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Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1715836A1 publication Critical patent/EP1715836A1/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Withdrawn legal-status Critical Current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
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates to a method for dyeing keratin-containing fibers, in particular human hair, in which, after a dyeing step, some of the previously dyed fibers are selectively subjected to an incomplete, oxidative color print for shading. Furthermore, a kit-of-parts, containing a colorant and a color proofing agent, and application aids are the subject of the invention and the use of this kit in the dyeing process according to the invention.
  • oxidation dyes are used for permanent, intensive dyeings with appropriate fastness properties.
  • Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components.
  • the developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or under coupling with one or more coupler components.
  • the oxidation coloring agents are characterized by excellent, long-lasting coloring results. For natural-looking dyeings, however, a mixture of a larger number of oxidation dye precursors usually has to be used; in many cases direct dyes are still used for shading.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Particularly suitable coupler substances are 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene 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 (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6 -methyl-3-aminophenol, 2-methyl resorcinol, 5-methylresorcinol and 2-methyl-4-
  • Coloring agents or tinting agents which contain so-called direct draws as the coloring component are usually used for temporary dyeings. These are dye molecules that attach directly to the hair and do not require an oxidative process to form the color. These dyes include, for example, henna, which is known from antiquity for coloring body and hair. These dyeings are generally significantly more sensitive to shampooing than the oxidative dyeings, so that a much undesired shift in nuances or even a visible "discoloration" occurs much more quickly.
  • Another way to dye keratin-containing fibers is to use dyes that are a combination of components
  • component B compounds selected from (a) CH-acidic compounds, (b) compounds with 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) contain oligopeptides composed of 2 to 9 amino acids.
  • oxo dyeing hereinafter called oxo dyeing
  • the resulting dyeings have color fastnesses on the keratin-containing fibers that are comparable to those of the oxidation dyeing.
  • the range of shades that can be achieved with the gentle oxo dyeing is very wide and the dyeing obtained often has an acceptable brilliance and depth of color.
  • the above-mentioned components A and B hereinafter referred to as oxo dye precursors, are generally not themselves dyes and are therefore not suitable for dyeing keratin fibers on their own. In combination, they form dyes in a non-oxidative process.
  • Corresponding oxidation dye precursors of the developer and / or coupler type with or without the use of an oxidizing agent can, however, also be used among compounds of component B. The oxo dyeing method can thus be easily combined with the oxidative dyeing system.
  • the oxidizing agents contained in the bleaching agents have an oxidative effect on the natural hair dye melanin and possibly on synthetic dyes in the fiber and thereby cause a color change and, ideally, a lightening of the hair color.
  • the basics of bleaching and oxidative dyeing processes are known to the person skilled in the art and are found in relevant monographs, e.g. by K. Schrader, basics and formulations of cosmetics, 2nd edition, 1989, Dr. Alfred Wilsonhig Verlag, Heidelberg, or W. Umbach (ed.), Kosmetik, 2nd edition, 1995, Georg Thieme Verlag, Stuttgart, New York, described in summary.
  • the conventional ready-to-use bleaches for keratin-containing fibers usually contain peroxydisulfate compounds to increase the healing performance and, when used on the fibers, have a pH of greater than pH 9.
  • the result of a lightening process must be distinguished from the result of ultrablonding.
  • the targeted oxidative brightening of keratin-containing fibers treated with colorants is not readily achievable.
  • the oxidative brightening of such color-changed fibers often results in undesirable color shifts to, for example, orange or green tones, which must be avoided at all costs. Only those color effects within the scope of the brightening that are intended to brighten the starting color are desirable.
  • the coloring agent contains a defined minimum number of coloring components and a brightening agent, hereinafter referred to as shading agent, with a defined viscosity is used.
  • a first object of the invention is therefore a process for dyeing keratin fibers, in particular human hair, in which A a dye is applied to the fibers and rinsed off after an exposure time Z1, B the fibers are subsequently dried if necessary, and then C to a part of the previously dyed fibers, a shading agent containing at least one thickener, hydrogen peroxide and at least one alkalizing agent in a cosmetic carrier is applied and rinsed off again after an exposure time Z2, the coloring agent as coloring component (a) containing at least two oxidation dye precursors, at least one oxidation dye precursor must be of the developer type or (b) contains at least two oxo dye precursors, at least one oxo dye precursor being a reactive carbonyl compound.
  • keratin-containing fibers are understood to mean furs, wool, feathers and in particular human hair.
  • colorants of the process according to the invention are primarily suitable for coloring keratin fibers, there is in principle nothing to prevent their use in other areas, in particular in color photography.
  • color pairs result which are formed from an initial coloring and the subsequent shading by the lightening after step C of the process according to the invention.
  • the resulting dyeing of the fiber after step A is defined as the initial dyeing.
  • the lightening results in a lightened color in the shade of the original color.
  • the formation of such color pairs according to the invention can be determined colorimetrically.
  • the colorant of the process according to the invention contains at least one developer component.
  • Primary aromatic amines with a further, in the para or ortho position, free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazole derivatives and 2,4,5,6-tetraaminopyrimidine and the like are usually used as developer components Derivatives used.
  • P-Phenylenediamine derivatives of the formula (E1) are particularly preferred
  • G 1 represents a hydrogen atom, a C to C alkyl radical, a C to C 4 monohydroxyalkyl radical, a C 2 to C polyhydroxyalkyl radical, a (C to C 4 ) alkoxy (C to C 4 ) alkyl radical , a 4'-aminophenyl radical or a C to C 4 - Alkyl radical which is substituted by a nitrogen-containing group, a phenyl or a 4'-aminophenyl radical; G 2 represents a hydrogen atom, a d- to C 4 alkyl radical, a C to C 4 - monohydroxyalkyl radical, a C 2 - to C polyhydroxyalkyl radical, a (C> to C 4) - alkoxy (C -C 4) alkyl radical or a C to C alkyl radical which is substituted by a nitrogen-containing group; G 3 represents a hydrogen atom, a halogen atom, such as a chlorine, bromine, i
  • C to C 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 to C 4 alkoxy radicals preferred according to the invention are, for example, a methoxy or an ethoxy group.
  • Further preferred examples of a C r to C 4 -hydroxyalkyl group are a H yd roxym ethyl, a 2-hydroxyethyl, a 3-hydroxypropyl or a 4-hydroxybutyl group. A 2-hydroxyethyl group is particularly preferred.
  • a particularly preferred C 2 - to C 4 polyhydroxyalkyl group containing 1, 2- dihydroxyethyl is.
  • halogen atoms according to the invention are F, Cl or Br atoms, Cl atoms are very particularly preferred.
  • the other terms used are derived from the definitions given here.
  • nitrogen-containing groups of the formula (E1) are in particular the amino groups, C to C 4 monoalkylamino groups, C to C 4 dialkylamino groups, C to C 4 trialkylammonium groups, C to C monohydroxyalkylamino groups, imidazolinium and ammonium.
  • Particularly preferred p-phenylenediamines of the formula (E1) are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p- phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p- phenylenediamine, N, N-dipropyl-p-phenylenediamine, 4-amino-3-methyl- (N, N-diethyl) -aniline, N, N-bis- (ß-hydroxyethyl) -p-phenylenediamine, 4-N, N-bis (ß-hydroxyethyl) amino-2-methylaniline, 4-N, N-bis
  • p-phenylenediamine derivatives of the formula (E1) which are particularly preferred 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, one can name in particular the compounds which correspond to the following formula (E2) and their physiologically tolerable salts:
  • Z 1 and Z 2 independently of one another represent a hydroxy or NH 2 radical, which is optionally substituted by a C to C 4 alkyl radical, by a C to C 4 hydroxyalkyl radical and / or by a bridging Y or the part, if appropriate of a bridging ring system
  • the bridging Y stands for an alkylene group with 1 to 14 carbon atoms, such as, for example, a linear or branched alkylene chain or an alkylene ring which is composed of one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms can be interrupted or terminated and possibly substituted by one or more hydroxy or d to C 8 alkoxy radicals, or a direct bond
  • G 5 and G 6 independently of one another represent a hydrogen or halogen atom, a C r to C 4 alkyl, a C to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a
  • Preferred dinuclear developer components of the formula (E2) are in particular: N, N'-bis (ß-hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1, 3-diamino-propan-2-ol, N, N'-bis (ß-hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylene diamine, N, N'-bis - (ß-hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylene diamine, N, N'-bis (4-methylaminophenyl) tetramethylene diamine, N, N'-diethyl-N, N ' bis (4'-amino-3 , methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminophenyl) methane, 1,
  • Very particularly preferred dinuclear 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-tetraoxadecane or one of their physiologically acceptable salts.
  • P-Aminophenol derivatives of the formula (E3) are particularly preferred
  • G 1 represents a hydrogen atom, a halogen atom, a C r to C 4 alkyl radical, a d to C 4 monohydroxyalkyl radical, a C 2 to C 4 polyhydroxyalkyl radical, a (C r to C) alkoxy (C to C 4 ) -alkyl radical, a C to C -aminoalkyl radical, a hydroxy- (C to C 4 ) -a) alkylamino radical, a C to C 4 -hydroxyalkoxy radical, ad- to C -hydroxyalkyl- (C r to C 4 ) -aminoalkyl or a (di-C to C 4 -alkylamino) - (d- to C 4 ) -alkyl, and G 14 represents a hydrogen or halogen atom, a C to C 4 -alkyl radical, a C to C monohydroxyalkyl, a C 2 to C polyhydroxyalkyl radical, a
  • 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- (D-hydroxyethoxy) phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino -2-aminomethylphenol, 4-amino-2- (ß-hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ß-dihydroxyethyl) -phenol, 4-amino-2-fluorophenol, 4-amino-2 -chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethylaminomethyl) phenol and their physiologically tolerable salts
  • Very particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol and 4-amino- 2- (diethylaminomethyl) -phenol.
  • the developer component can be selected from o-aminophenol and its derivatives, such as, for example, 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.
  • the developer component can be selected from heterocyclic developer components, such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • heterocyclic developer components such as, for example, the pyridine, pyrimidine, pyrazole, pyrazole-pyrimidine derivatives and their physiologically tolerable salts.
  • Preferred pyridine derivatives are, in particular, the compounds described in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4'-methoxyphenyl) amino-3-aminopyridine, 2,3-diamino-6-methoxy-pyridine, 2- (ß-
  • Methoxyethyl amino-3-amino-6-methoxy-pyridine and 3,4-diamino-pyridine.
  • Preferred pyrimidine derivatives are, in particular, the compounds which are described in German patent DE 2 359 399, Japanese laid-open patent publication JP 02019576 A2 or in laid-open publication WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy- 2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6- triaminopyrimidine.
  • Preferred pyrazole derivatives are in particular the compounds described in the patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740 931 and DE 195 43 988, such as 4.5 -Diamino-1-methylpyrazole, 4,5- diamino-1 - (ß-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-
  • Triaminopyrazole 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole and 3,5-diamino-4- ( ⁇ -hydroxyethyl) amino-1-methylpyrazole.
  • Preferred pyrazolo-pyrimidine derivatives are, in particular, the derivatives of pyrazolo [1, 5-a] pyrimidine of the following formula (E4) and its tautomeric forms, provided there is a tautomeric equilibrium:
  • G 17 , G 18 , G 19 and G 20 independently represent a hydrogen atom, ad- to C 4 -alkyl radical, an aryl radical, a C to C -hydroxyalkyl radical, a C 2 - to C 4 - Polyhydroxyalkyl radical is a (C to C 4 ) alkoxy (C to C) alkyl radical, a C to C 4 aminoalkyl radical which can optionally be protected by an acetyl-ureide or a sulfonyl radical, a (d to C 4 ) -Alky!
  • pyrazolo [1, 5-a] pyrimidines of the formula (E4) above one can mention in particular: pyrazolo [1, 5-a] pyrimidine-3,7-diamine; 2,5-dimethyl-pyrazolo [1,5-a] pyrimidine-3,7-diamine; Pyrazolo [1,5-a] pyrimidine-3,5-diamine; 2,7-dimethylpyrazolo [1,5-a] pyrimidine-3,5-diamine; 3-aminopyrazolo [1,5-a] pyrimidin-7-ol; 3-aminopyrazolo [1,5-a] pyrimidin-5-ol; 2- (3-aminopyrazolo [1,5-a] pyrimidin-7-ylamino) ethanol; 2- (7-aminopyrazolo [1,5-a] pyrimidin-3-ylamino) ethanol; 2 - [(3-Arninopyrazol
  • pyrazolo [1, 5-a] pyrimidines of the above formula (E4) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.
  • indoles and indolines which have at least one hydroxyl or amino group, preferably as a substituent on the six-membered ring, are preferably used as precursors of nature-analogous dyes. These groups can carry further substituents, e.g. B. in the form of etherification or esterification of the hydroxy group or an alkylation of the amino group. These indoles or indolines can be used as developer components in oxidation hair colors.
  • Derivatives of 5,6-dihydroxyindoline of the formula (Ia) are particularly suitable as precursors of natural hair dyes,
  • R stands for hydrogen, a CC 4 alkyl group or a dd-hydroxyalkyl group
  • R 2 stands for hydrogen or a -COOH group, where the -COOH group can also be present as a salt with a physiologically compatible cation
  • R 3 represents hydrogen or a CC alkyl group
  • - R 4 represents hydrogen, a CC 4 alkyl group or a group -CO-R 6 , in which R 6 represents a CC 4 alkyl group
  • R 5 represents one of the groups mentioned under R 4 , and physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6 dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid and 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially the 5 6-Dihydroxyindolin.
  • R 1 stands for hydrogen, a CC 4 alkyl group or a CC 4 hydroxyalkyl group
  • R 2 stands for hydrogen or a -COOH group, where the -COOH group can also be present as a salt with a physiologically compatible cation
  • R 3 represents hydrogen or a C r C alkyl group
  • R 4 stands for hydrogen, a CC 4 alkyl group or a group -CO-R 6 , in which R 6 stands for a CC 4 alkyl group, and R 5 stands for one of the groups mentioned under R 4 , as well as physiologically tolerable salts of these compounds with an organic or inorganic acid.
  • Particularly preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5, 6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 6-hydroxyindole, 6-aminoindole and 4-aminoindole.
  • N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole and in particular 5.6 are to be emphasized -Dihydroxyindol.
  • the indoline and indole derivatives can be used in the colorants used in the process according to the invention both as free bases and in the form of their physiologically tolerable salts with inorganic or organic acids, for.
  • the indole or indoline derivatives are usually contained in these in amounts of 0.05-10% by weight, preferably 0.2-5% by weight.
  • the indoline or indole derivative in hair colorants in combination with at least one amino acid or an oligopeptide.
  • the amino acid is advantageously an ⁇ -amino acid; very particularly preferred ⁇ -amino acids are arginine, omithin, lysine, serine and histidine, in particular arginine.
  • the colorants of the process according to the invention contain at least one coupler component.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives and heterocyclic compounds are generally used as coupler components.
  • Coupler components preferred according to the invention are m-aminophenol and its derivatives such as 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2,6-dimethyl 3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2'-hydroxyethyl) amino- 2-methylphenol, 3- (diethylamino) phenol, N-cyclopentyl-3-aminophenol, 1, 3-dihydroxy-5- (methylamino) benzene, 3-ethylamino-4-methylphenol and 2,4-dichloro-3- aminophenol,
  • o-aminophenol and its derivatives m-diaminobenzene and its derivatives such as, for example, 2,4-diaminophenoxyethanol, 1, 3-bis (2 ', 4'-diaminophenoxy) propane, 1-methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 1, 3-bis (2 ', 4'-diaminophenyl) propane, 2,6-bis (2'-hydroxyethylamino) -1-methylbenzene and 1-amino-3-bis - (2'-hydroxyethyl) aminobenzene,
  • o-diamino benzene and its derivatives such as 3,4-diamino benzoic acid and 2,3-diamino-1-methylbenzene, di- or trihydroxybenzene derivatives such as resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2 -Chlorresorcin, 4-Chlorresorcin, Pyrogallol and 1, 2,4-Trihydroxybenzol,
  • 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-d
  • Coupler components which are particularly preferred according to the invention are 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, m-phenylenediamine, 1-phenyl-3 -methyl-pyrazol-5-one, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2-chloro -6-methyl-3-aminophenol, 3-amino-2-methylamino-6-methoxypyridine, 2-amino-3-hydroxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2-methylresorcinol, 5-methylresorcinol, 2 -Methyl-4-chloro-5-aminophenol and the physiological
  • At least one compound selected from m-aminophenol or its derivatives as a coupler At least one compound selected from m-aminophenol or its derivatives as a coupler.
  • At least one heterocyclic developer selected from pyrazole derivatives and pyrimidine derivatives
  • At least one compound selected from m-aminophenol or its derivatives as a coupler At least one compound selected from m-aminophenol or its derivatives as a coupler.
  • At least one compound selected from m-aminophenol or its derivatives as a coupler At least one compound selected from m-aminophenol or its derivatives as a coupler.
  • the aforementioned preferred oxidation dye precursors are used as preferred developers or couplers in the combinations mentioned above.
  • the colorants of the process according to the invention preferably contain both the developer components and the coupler components in an amount of 0.005 to 10% by weight, preferably 0.1 to 5% by weight, based in each case on the total oxidation colorant.
  • Developer components and coupler components are generally used in approximately molar amounts to one another. If molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1: 2 , can be included.
  • the colorants of the process according to the invention can contain one or more substantive dyes.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds and 1 , 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1, 4-bis (ß-hydroxyethyl)
  • the colorants may also contain a cationic substantive dye.
  • a cationic triphenylmethane dyes such as, for example, Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14,
  • aromatic systems which are substituted by a quaternary nitrogen group, such as, for example, Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
  • substantive dyes which contain a heterocycle which has at least one quaternary nitrogen atom, as described, for example, in EP-A2-998 908, to which at this point explicit reference is made to claims 6 to 11.
  • Preferred cationic direct dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic direct dyes of group (c).
  • the cationic direct dyes which are sold under the trademark Arianor ® are, according to the invention also very particularly preferred cationic direct dyes.
  • the colorants can contain the substantive dyes in an amount of 0.1 to 5% by weight, based on the total colorant.
  • the colorants of the process according to the invention can also contain naturally occurring dyes, such as those contained in henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root ,
  • the colorants used in the process according to the invention contain no substantive dyes.
  • the oxidation dye precursors or the substantive dyes each represent uniform compounds. Rather, in the hair colorants according to the invention, due to the production process for the individual dyes, further components may be present in minor amounts, provided that these do not adversely affect the coloring result or must be excluded for other reasons, for example toxicological ones.
  • the dyes which can be used in the colorant of the process according to the invention reference is also expressly made to the monograph Ch. Zviak, The Science of Hair Care, chapter 7 (pages 248-250; direct dyes) and chapter 8, pages 264-267; Oxidation dye precursors), published as Volume 7 of the "Dermatology" series (ed.,: Ch., Culnan and H.
  • the colorant of the process according to the invention can be used as a coloring component, at least one combination, preferably a three combination, selected from the
  • B compounds selected from (a) CH-acidic compounds, (b) compounds with 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) from 2 up to 9 amino acids constructed oligopeptides, wherein at least one representative of this combination must be a compound with a reactive carbonyl group according to component A.
  • Compounds according to the invention with a reactive carbonyl group have at least one carbonyl group as a reactive group which reacts with the compounds of component B to form a chemical bond linking the two components.
  • Compounds A in which the reactive carbonyl group is derivatized or masked such that the reactivity of the carbon atom of the derivatized or masked carbonyl group with respect to component B is always present are also included as component A according to the invention.
  • These derivatives are preferably condensation compounds of ' reactive carbonyl compounds with a) amines and their derivatives with the formation of imines or oximes as the condensation compound b) alcohols with the formation of acetals or ketals as the condensation compound c) water with the formation of hydrates as the condensation compound of aldehydes.
  • Component A is preferably selected from the group formed from acetophenone, propiophenone, 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, 2-hydroxypropiophenone, 3-hydroxypropiophenone, 4-hydroxyproprophenone, 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-trihydroxyacetophe- non, 2,4,6-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone, 3,4,5-trimethoxyacetophenone diethyl ketal, 4-hydroxy-3-methoxyacetophenone, 3,5-dimethoxy-4-hydroxyacetophenone, 4-aminoacetophenone, 4-dimethylaminoacetophenone, 4-morpholinoace
  • Ethoxybenzaldehyde 4-hydroxy-2,3-dimethoxy-benzaldehyde, 4-hydroxy-2,5-dimethoxy-benzaldehyde, 4-hydroxy-2,6-dimethoxy-benzaldehyde, 4-hydroxy-2-methyl-benzaldehyde, 4- Hydroxy-3-methyl-benzaldehyde, 4-hydroxy-2,3-dimethyl-benzaldehyde, 4-hydroxy-2,5-dimethyl-benzaldehyde, 4-hydroxy-2,6-dimethyl-benzaldehyde, 4-hydroxy-3, 5-dimethoxy-benzaldehyde, 4-hydroxy-3,5-dimethyl-benzaldehyde, 3,5-diethoxy-4-hydroxy-benzaldehyde, 2,6-diethoxy-4-hydroxy-benzaldehyde, 3-hydroxy-4-methoxy benzaldehyde, 2-hydroxy-4-methoxy-benzaldehyde, 2-ethoxy-4-hydroxy-benzaldehyde, 3-
  • Formylmethylene-1, 3,3-trimethylindoline Fischer's aldehyde or tribase aldehyde
  • 2-indolaldehyde, 3-indolaldehyde 1-methylindole-3-aldehyde, 2-methylindol-3-aldehyde, 1 - acetylindol-3-aldehyde, 3 -Acetylindol, 1-methyl-3-acetylindole, 2- (1 ', 3, 3'-trimethyl-2-indoli- nyliden) acetaldehyde, 1-methylpyrrole-2-aldehyde, 1-methyl-2-acetylpyrrole, 4-pyridine aldehyde, 2-pyridine aldehyde, 3-pyridine aldehyde, 4-acetylpyridine, 2-acetylpyridine, 3-acetylpyridine, pyridoxal, quinoline-3-aldehyde, quinoline-4-alde
  • CH-acidic compounds which carry a hydrogen atom bonded to an aliphatic carbon atom are generally regarded as CH-acidic, activation of the corresponding carbon-hydrogen bond being effected on account of electron-withdrawing substituents.
  • CH-acidic compounds also include enamines which are formed by alkaline treatment of quaternized N-heterocycles with a CH-acidic alkyl group conjugated to 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-methyleneindoline (Fischer's base), 2,3-dimethyl-benzothiazolium iodide, 2,3-dimethyl-benzothiazolium-p- toluenesulfonate, 2,3-dimethyl-naphtho [1,2-d] thiazolium-p-toluenesulfonate, 3-ethyl-2-methyl-naphtho [1, 2-d] thiazolium-p-toluenesulfonate, rhodanine, rhodanine-3-
  • Trimethylquinoxalinium iodide 3-ethyl-2-methyl-benzoxazolium-p-toluenesulfonate, 3-ethyl-2-methyl-benzothiazolium-p-toluenesulfonate, 1-ethyl-4-methyl-quinolinium-p-toluenesulfonate, 1 - ethyl-2- methylquinolinium p-toluenesulfonate, and 1, 2,3-trimethylquinoxalinium p-toluenesulfonate.
  • Preferred primary or secondary aromatic amines of component B are selected from N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine, N- (2-hydroxyethyl) -N-ethyl-p-phenylenediamine, N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, N- (2-methoxyethyl) -p-phenylenediamine, 2,3-dichloro-p-phenylenediamine, 2,4-dichloro-p-phenylenediamine, 2,5- Dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl 4-aminophenol, o-phenylenediamine,
  • R 7 for a hydroxy or an amino group, which is substituted by C -4 alkyl, C 1-4 hydroxyalkyl, C 1-4 alkoxy or C 1-4 alkoxy-C 1-4 alkyl groups can be stands
  • R 8 , R 9 , R 10 , R 11 and R 12 independently of one another for a hydrogen atom, a hydroxyl or an amino group, which can be substituted by dC 4 -alkyl-, CC -hydroxyalkyl, C r C 4 -alkoxy-, dC - Aminoalkyl or CC 4 alkoxy-dC 4 alkyl groups can be substituted, and
  • 4,4'-diaminostilbene and its hydrochloride 4,4'-diaminostilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochloride, 4, 4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfoxide, 4,4'-diaminodiphenylamine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, 4,4 ' -Diaminodiphenylether, S.S ' ⁇ ' - Tetraamino-diphenyl, 3,3 ', 4,4'-Tetraamino-benzophenone, 1, 3-bis- (2,4-diaminophenoxy) -propane, 1,
  • the abovementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are e.g. B. 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-amino-3-hydroxy-pyridine, 2,6-diamino-pyridine, 2,5-diamino-pyridine, 2- (aminoethylamino) -5-aminopyridine, 2,3-diamino-pyridine, 2-dimethylamino-5-amino-pyridine, 2-methylamino-3-amino-6-methoxy-pyridine, 2,3-diamino-6-methoxy-pyridine, 2,6- Dimethoxy-3,5-diamino-pyridine, 2,4,5-triamino-pyridine, 2,6-dihydroxy-3,4-dimethylpyridine, N- [2- (2,4-diaminophenyl) aminoethyl] -N - (5-amino-2-pyridyl) amine, N- [2- (4
  • the hydroxypyrimidines disclosed in DE-U1-299 08 573 can also be used as heterocyclic compounds.
  • the aforementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, e.g. B. as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable aromatic hydroxy compounds are e.g. B. 2-methylresorcinol, 4-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 3- Dimethylaminophenol, 2- (2-hydroxyethyl) phenol, 3,4-methylenedioxyphenol, 2,4-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 2,4-dihydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid, gallic acid, 2 , 4,6-trihydroxybenzoic acid, 2,4,6-trihydroxyacetophenone, 2-chlororesorcinol, 4-chlororesorcinol, 1-naphthol, 1,5-dihydroxynaphthalene,
  • the compounds of component A and the compounds of component B are preferably used in the agents according to the invention in each case in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total colorant.
  • the molar ratio of the compound of component A and the compound of component B can be in the range from 0.5 to 2.0, preference being given to using equimolar amounts.
  • the actual colorant is produced by mixing components A and B immediately before use by mixing.
  • Oxidative dyeing of the fibers can generally be carried out with atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a lightening effect of the natural pigments of the human hair is desired.
  • oxidation dye precursors is therefore not a mandatory requirement for the use of oxidizing agents in the colorants of the process according to the invention.
  • oxidizing agents are hydrogen peroxide or its adducts with urea, melamine and sodium borate. If the dye precursors and the oxidizing agent are stored separately, the actual colorant is produced by mixing immediately before use.
  • the oxidation coloring agent can also be applied to the hair together with a catalyst which oxidizes the dye precursors, e.g. activated by atmospheric oxygen.
  • a catalyst which oxidizes the dye precursors, e.g. activated by atmospheric oxygen.
  • Such 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+ .
  • Zn 2+ , Cu 2+ and Mn 2+ are particularly suitable.
  • the metal ions can be used in the form of any physiologically acceptable salt or in the form of a complex compound.
  • Preferred salts are the acetates, sulfates, halides, lactates and tartrates.
  • Suitable enzymes are, for example, peroxidases, which can significantly increase the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the help of atmospheric oxygen, such as, for example, the laccases, or in Generate small amounts of hydrogen peroxide in situ and thus activate the oxidation of the dye precursors biocatalytically.
  • Particularly suitable catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the substrates specific therefor, for example pyranose oxidase and for example D-glucose or galactose, glucose oxidase and D-glucose, glycerol oxidase and glycerol , Pyruvate oxidase and pyruvic acid or its salts, - alcohol oxidase and alcohol (MeOH, EtOH), lactate oxidase and lactic acid and their salts, - tyrosinase oxidase and tyrosine, uricase and uric acid or their salts, choline oxidase and choline, Amino acid oxidase and amino acids.
  • 2-electron oxidoreductases in combination with the substrates specific therefor, for example pyranose oxidase and for example D
  • the actual coloring agent is expediently prepared immediately before use by mixing the preparation of the oxidizing agent with the preparation containing the compounds of the formula I and, if appropriate, dye precursors.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 12. It is particularly preferred to use the hair dye in a weakly alkaline environment. Application temperatures can range between 15 and 40 ° C. After an exposure time of 5 to 45 minutes, the hair dye is rinsed off from the hair to be colored. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a coloring shampoo was used.
  • an agent according to the invention can be applied to the hair, if appropriate 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 necessary after an intermediate rinse. After a further exposure time of 10 to 20 minutes, rinsing is carried out and, if desired, re-shampooed.
  • the corresponding agent is adjusted to a pH of about 4 to 7.
  • air oxidation is initially aimed for, the agent applied preferably having a pH of 7 to 10. In the subsequent accelerated postoxidation, the use of acidified peroxidisulfate solutions as the oxidizing agent can be preferred.
  • the agents of the process according to the invention preferably contain the ingredients according to the invention in a suitable aqueous, alcoholic or aqueous-alcoholic cosmetic carrier.
  • a suitable aqueous, alcoholic or aqueous-alcoholic cosmetic carrier are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions, such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • surfactant-containing foaming solutions such as shampoos, foam aerosols or other preparations which are suitable for use on the hair.
  • aqueous-alcoholic solutions are understood to mean aqueous solutions containing 3 to 70% by weight of a dC 4 alcohol, in particular ethanol or isopropanol.
  • the agents according to the invention can additionally contain further organic solvents, such as, for example, methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. All water-soluble organic solvents are preferred.
  • the colorants and the shading agents of the process according to the invention can furthermore contain all active ingredients, additives and auxiliaries known for such preparations.
  • the colorants and / or the shading agents contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle. In many cases, however, it has proven to be advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic Group such as B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • anionic Group such as B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups can be contained in the molecule.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearin acid and palmitic acid.
  • Non-ionic surfactants contain z.
  • Such compounds are, for example, adducts of 2 to 30 mol of ethylene oxide and / or 0 to 5 mol of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols with 8 to 15 C atoms in the alkyl group, C 12 -C 22 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol, C 8 -C 22 alkyl mono- and oligoglycosides and their ethoxylated analogues, and adducts of 5 to 60 moles of ethylene oxide with castor oil and hardened castor oil.
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula R 1 0- (Z) ⁇ . These connections are characterized by the following parameters.
  • the alkyl radical R 1 contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear and methyl-branched aliphatic radicals in the 2-position are preferred. Examples of such alkyl radicals are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. 1-Octyl, 1-decyl, 1-lauryl, 1-myristyl are particularly preferred. When using so-called "oxo alcohols" as starting materials, compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • the alkyl polyglycosides which can be used according to the invention can contain, for example, only a certain alkyl radical R. Usually, however, these compounds are made from natural fats and oils or mineral oils. In this case, the alkyl radicals R are mixtures corresponding to the starting compounds or corresponding to the respective working up of these compounds.
  • R 1 consists essentially of C 8 and C 10 alkyl groups, essentially from C 2 and C 14 alkyl groups, essentially from C 8 to C 16 alkyl groups or essentially from 2 - Up to Ci6 alkyl groups.
  • Any mono- or oligosaccharides can be used as the sugar building block Z.
  • Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used. Examples of such sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar components are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain on average 1.1 to 5 sugar units. Alkyl polyglycosides with x values of 1.1 to 1.6 are preferred. Alkyl glycosides in which x is 1.1 to 1.4 are very particularly preferred.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • the person skilled in the art will preferably resort to this substance class as a further ingredient of the preparations according to the invention.
  • alkoxylated homologs of the alkyl polyglycosides mentioned can also be used according to the invention. These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • zwitterionic surfactants can be used, in particular as co-surfactants.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COO (" > - or -SOa ⁇ group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N, N dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline, each with 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the INCI name Cocamidopropyl Betaine.
  • Ampholytic surfactants are also particularly suitable as co-surfactants.
  • Ampholytic surfactants are understood to mean those surface-active compounds which in addition to a C 8 -C 18 alkyl or acyl group, the molecule contains at least one free amino group and at least one -COOH or -S0 3 H group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkyl aminopropionate, cocoacylaminoethyl aminopropionate and C 12 . ⁇ 8 acyl sarcosine.
  • the cationic surfactants used are, in particular, those of the quaternary ammonium compound, esterquat and amidoamine type.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, and the compounds known under the INCI names Quaternium-27 and Quaternium-83 compounds imidazolium.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Ester quats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines.
  • Such products are sold, for example, under the trademarks Stepantex ® , Dehyquart ® and Armocare ® .
  • alkylamidoamines are usually produced by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • a compound from this group of substances which is particularly suitable according to the invention is that commercially available stearamidopropyldimethylamine under the name Tegoamid ® S 18.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® - Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quatemium-80).
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to INCI nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride”.
  • the compounds with alkyl groups used as surfactant can each be uniform substances. However, it is generally preferred to use native vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts from the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • the colorants and the shading agents of the process according to the invention can contain further active ingredients, auxiliaries and additives, such as, for example, nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes, cationic polymers such as quaternized cellulose ethers, polysiloxanes , Dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallyl-ammonium chloride copolymers, dimethylamino-ethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone-imidazolinium-methochloride copolymers and quaternized polyvinyl alcohol -methyl-amidopolymer-acrylate, for example, tamperidonylammony
  • Cholesterol, consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax and paraffins, fatty acid alkanolamides, complexing agents such as EDTA, NTA, ß-alanine diacetic acid and phosphonic acids, swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogenates , Guanidines, ureas and primary, secondary and tertiary phosphates, opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers pearlescent agents such as ethylene glycol mono- and distearate as well as PEG-3 distearate, pigments, stabilizing agents for hydrogen peroxide and other oxidizing agents, blowing agents such as propane-butane mixtures, N 2 0, dimethyl ether,
  • the application temperatures of the colorant can be in a range between 15 and 40 ° C.
  • an exposure time Z1 preferably 2 to 60 minutes, particularly preferably 5 to 45 minutes, the hair dye is rinsed out removed from the hair to be dyed. Washing with a shampoo is not necessary if a carrier with a high surfactant content, such as a coloring shampoo, has been used.
  • step C of the method according to the invention directly after step A or step B.
  • the period defined as a direct connection in the sense of the invention is a maximum of 90 minutes.
  • the preferred time interval between the completion of step A of the process according to the invention and the beginning of the execution of step C should not be longer than 60 minutes, particularly preferably not longer than 45 minutes, very particularly preferably not longer than 20 minutes.
  • a sharper contrast transition between the dyed and the oxidatively lightened hair areas is brought about if the hair is dried between step A and C and the shading agent is applied to the dry hair.
  • the shading agent is applied to part of the keratin-containing fibers previously dyed in step A.
  • the selected fiber bundles are preferably selected as uniformly as possible over the area of the entire head hair area.
  • the selected fiber bundles are either completely or partially treated with the shading agent. With a full treatment, highlights with light color effects are obtained. In the case of a partial treatment, for example, the fiber tips or other selected areas of the fiber bundle can be selectively nuanced.
  • the shading agent can be applied to the selected strand of fibers by hand using suitable protective gloves.
  • the shading agent is preferably applied to the hair areas intended for shading with an applicator, such as a brush, a brush or an applicette.
  • An applicette is understood to be a broad brush with a tip at the end of the handle, which allows and simplifies the division of fiber bundles or strands from the total amount of fibers.
  • a round brush has a handle and a bristle head.
  • the bristles of the bristle head are arranged in the form of a cylinder in the form of a cylinder around a central body of the bristle head, the sum of the attached bristles with one bristle end describing a substantially cylindrical outer surface, while the other end is attached to the body of the bristle head.
  • the body of the bristle head is in turn positioned at one end of the round brush style or is part of an end portion of the style.
  • the round brush used in the method according to the invention preferably has bristles with a length of at most 2 cm and has a diameter of the cylindrical bristle head of at most 2.5 cm.
  • the cylinder of the bristle head has a maximum length of 4 cm.
  • a mascara brush is ideal for applying the shading agent.
  • a particularly preferred possibility of achieving an improved uniform application of the shading agent for applying the color effects in the form of highlights in the form of highlights over the head hair area while maintaining sharp contrasts is offered by the use of a hood with a hole pattern evenly distributed over the surface of the hood, possibly only drawn.
  • the preferably dry fibers are therefore covered with such a hood after step B.
  • the shading agent according to step C is distributed to the selected hair areas with the hands, as with a shampoo or with a brush.
  • the shading agent is rinsed off and the hood is removed.
  • the hood is preferably made of at least one film, which preferably consists of polyethylene or polyvinyl chloride. If the hood consists of a film layer, it is possible to pre-punch or draw the hole pattern. In the case of a merely pre-drawn grid, the film has no holes and must be pierced at the selected pre-drawn point and the strand of hair must then be pulled through the hole that is created in the process. It is preferred according to the invention to manufacture the hood from two layers of film lying one above the other. This Foil trays are preferably made of polyethylene or polyvinyl chloride. The film inside the hood preferably has no prefabricated holes. Furthermore, the outer film carries the preferably pre-punched hole pattern.
  • the holes of the hole pattern or their drawing preferably have a diameter of 0.1 to 0.75 mm.
  • the holes, which may only be drawn, are preferably arranged such that they lie on the imaginary lines of a grid.
  • the grid preferably consists of squares. All, possibly only pre-drawn, holes are evenly spaced along the grid lines, which is preferably 0.5 to 2 cm.
  • the hood preferably has the shape of a boat or a helmet.
  • the shape of the helmet is particularly preferred.
  • a hood as shown in FIGS. 1 to 4 is very particularly preferred.
  • This hood consists primarily of two side parts (1) and (2) as well as a middle part (3) and a screen part (4). These parts are preferably connected to one another at their contact points by a welded and / or sewn seam (8) and (9).
  • the seams and the outer edges of parts (1), (2), (3) and (4) are edged with a hem.
  • the hem preferably consists of the material of the outer film.
  • the parts (1), (2) and (3) of the hood consist of 2 superimposed foils.
  • the outer film has a pre-punched hole pattern, the inner film has no holes.
  • Both superimposed foils are connected on the one hand by the connecting seam of the parts (1), (2) and (3), and on the other hand by the hem.
  • the hood when pulled over the head, covers the back of the head and has an opening for the face at the front (see FIG. 2, the "front view”).
  • the screen part (4) is attached to the upper part of the field of view.
  • the edge of the screen part and the outer edge of the parts (1), (2) and (3) are bordered by a hem as previously described.
  • the hem is extended at the lower part of the field of vision beyond the edge of the hood and forms bands (5) and (6) on the right and left, with which the hood can be attached to the head by knotting the bands under the chin.
  • the elastic band (7) which is incorporated along the lower edge of the central part (3).
  • the elastic band ensures a tight fit of the hood.
  • the hood adapts to different head sizes with the help of the elastic band.
  • the contact time Z2 is preferably 5 to 60 minutes, particularly preferably 20 to 45 minutes.
  • the fiber bundles which have been divided off and treated with the shading agent are wrapped in a foil, preferably in aluminum foil, and are left in this foil for the duration of the exposure time Z2.
  • This embodiment can preferably be used with shorter exposure times of up to 30 minutes.
  • the shading agents of the process according to the invention contain hydrogen peroxide.
  • the hydrogen peroxide is used as a solution or in the form of a solid addition compound of hydrogen peroxide onto inorganic or organic compounds, such as sodium perborate, sodium percarbonate,
  • the shading agents preferably contain hydrogen peroxide in an amount of 0.5 to 6.0% by weight, based on the weight of the shading agent.
  • the shading agents of the process according to the invention preferably contain additional peroxo compounds. These are to be understood as those peroxo compounds which are neither hydrogen peroxide itself nor addition products of hydrogen peroxide with other components.
  • the selection of the peroxo compounds additionally contained in the agents according to the invention is in principle not subject to any restrictions; Typical peroxo compounds known to the person skilled in the art are, for example, ammonium peroxydisulfate, potassium peroxydisulfate, sodium peroxydisulfate, ammonium persulfate, potassium persulfate, sodium persulfate, potassium peroxydiphosphate and peroxides such as magnesium and barium peroxide.
  • the inorganic compounds are preferred according to the invention.
  • the peroxydisulfates, in particular ammonium peroxydisulfate are particularly preferred.
  • the peroxo compounds are contained in the shading agents used according to the invention preferably in amounts of 1 to 40% by weight, in particular in amounts of 2 to 30% by weight.
  • the pH of the shading agents used according to the invention is preferably in a pH range from pH 2.5 to 12.0, particularly preferably from pH 8.5 to 11.0.
  • the shading agents of the process according to the invention contain, as a preferred alkalizing agent, at least one compound selected from ammonium, alkali metal and alkaline earth metal hydroxides, carbonates, bicarbonates, hydroxycarbonates and carbamides, and also alkali phosphates.
  • the shading agent can additionally contain at least one SiO 2 compound, which can optionally be hydrated. It can be preferred according to the invention that the optionally hydrated SiO 2 compounds in amounts of 0.05% by weight to 15% by weight, particularly preferably in amounts of 0.15% by weight to 10% by weight and entirely particularly preferably in amounts of 0.2% by weight to 5% by weight, based in each case on the entire shading agent.
  • the quantities given each reflect the content of the Si0 2 compounds (without their water content) in the compositions.
  • the present invention is in principle not subject to any restrictions.
  • Silicic acids, their oligomers and polymers and their salts are preferred.
  • Preferred salts are the alkali salts, especially the potassium and sodium salts.
  • the sodium salts are very particularly preferred.
  • the optionally hydrated Si0 2 compounds can be in various forms.
  • the Si0 2 compounds are preferably used in the form of silica gels (silica gel) or particularly preferably as water glass. These Si0 2 compounds can partly be present in aqueous solution.
  • water glasses which are formed from a silicate of the formula (Si0 2 ) n (Na 2 ⁇ ) m (K 2 0) p , where n stands for a positive rational number and m and p independently of one another positive rational number or for 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.
  • the water glasses can also contain small amounts of other additives, such as phosphates or magnesium salts.
  • Water glasses which are particularly preferred according to the invention are marketed, inter alia, by Henkel under the names Ferrosil ® 119, sodium water glass 40/42, Portil ® A, Portil ® AW, Portil ® N and Portil ® W and by Akzo under the name Britesil ® C20 ,
  • the shading agent has a preferred viscosity of 5,000 to 100,000 mPas, particularly preferably 30,000 to 80,000 mPas (Brookfield rotary viscometer, 25 ° C., spindle # 4, 20 rpm).
  • the viscosity is adjusted by the thickener contained in the shading agent.
  • Polymers can increase the viscosity of aqueous and non-aqueous phases in cosmetic preparations. In aqueous phases, their viscosity-increasing function is based on their solubility in water or their hydrophilic nature. They are used in both surfactant and emulsion systems.
  • acrylamide copolymer acrylamide / sodium acrylate copolymer, acrylamide / sodium acryloyldimethyltaurate copolymer, acrylate / acetoacetoxyethyl methacrylate copolymer, acrylate / beheneth-25 methacrylate copolymer, Acrylates / C 10-30 Alkyl Acrylate Crosspolymer, Acrylates / Ceteth-20 Itaconate Copolymer, Acrylates / Ceteth-20 Methacrylate Copolymer, Acrylates / Laureth-25 Methacrylate Copolymer, Acrylates / Palmeth-25 Acrylate Copolymer, Acrylates / Palmeth-25 Itaconate Copolymer, Acrylates / Steareth-50 Acrylate Copolymer, Acrylates / Steareth-20 Itaconate Copolymer, Acrylates / Steareth-50 Acrylate Copolymer, Acrylates / Steareth
  • Acryloyldimethyltaurate ⁇ / P copolymer ammonium alginate, ammonium polyacryloyldimethyl taurate, amylopectin, ascorbyl methylsilanol pectinate, Astragalus Gummifer Gu, Attapulgite, Avena Sativa (Oat) Kernel Flour, Bentonite, Butoxy Chitosan, Caesalpinia Spinosa Gum, Calcium Alginate, Calcium Carboxymethyl Cellulose, Calcium Carrageenan, Calcium Potassium Carbomer, Calcium Starch Octenylsuccinate, C20-40 Alkyl Stearate, Carbomer, Carboxybutyl Chitosan, Carboxymethyl Chitin, Carboxymethyl Chitosan, Carboxymethylethyl Carboxymymethyl Carboxymethyldroxan , Cellulose Acetate Propionate Carboxylate, Cellulose Gum, Ceratonia Siliqua Gum, Cetyl
  • a second subject of the present application is a kit containing
  • (b) contains at least two oxo dye precursors, at least one oxo dye precursor must be a reactive carbonyl compound.
  • the shading agent resulting from mixing the contents of containers C2a and C2b has a viscosity of 5000 to 100000 mPas (Brookfield rotational viscometer, 25 ° C, spindle # 4, 20 rpm).
  • the colorant and the shading agent as a mixture of C2a and C2b have the preferred features as described in the first subject of the invention.
  • the applicators mentioned in the first subject of the invention serve as applicators.
  • the hood has the preferred features as already described in the first subject of the invention.
  • the colorant is preferably present in two containers C1a and C1b in the kit. If it is an oxidative coloring agent, container C1a contains the so-called coloring cream, which contains the dye precursors, and a container containing hydrogen peroxide is stored in container 1b. If it is an oxo dye, the compounds of component A can be stored separately in container C1a and the compounds of component B in container C1b.
  • a third object of the invention is the use of the kit according to the second object of the invention in a method of the first object of the invention.
  • Ci6-C ⁇ 8 fatty alcohol (INCI name: Cetearyl Alcohol) (Cognis)
  • Aculyn ® 33 (INCI name: Acrylates Copolymer) (Rohm & Haas)
  • Turpinal ® SL 1-hydroxyethane-1, 1-diphosphonic acid (INCI name: Etidronic Acid, Aqua (Water)) (Solutia)
  • Eumulgin ® B2 cetylstearyl alcohol with approx. 20 EO units (INCI name: Ceteareth-20)
  • Aerosil ® 200 silicon dioxide (INCI name: silica) (Degussa)
  • a coloring cream according to Table 2 is produced:
  • compositions are produced in accordance with Tables 3 and 4:
  • a coloring cream according to Table 2 was mixed with the oxidizing agent preparation according to Table 5 in a weight ratio of 1: 1.
  • 1 g of the shading agent is applied to a fiber bundle consisting of approx.
  • One third of the hair fibers from the previously colored strand of hair Apply the mascara brush evenly over the entire area of the fiber bundle, leave it on the hair for 10 minutes at 32 ° C and then rinse off.
  • the lock of hair was dried and the color result of the nuanced hair was assessed.
  • the hair was given a blonde color with light blonde hues in the nuanced area.
  • a hair colorant was prepared in which the color cream from Table 2 was mixed with the oxidizing agent preparation according to Table 5 in a weight ratio of 1: 1.
  • This hair dye was applied to the entire head hair of a test person with light blond hair and rinsed off again after a contact time of 30 minutes (step A of the method according to the invention).
  • the hair was dried (step B of the process according to the invention) and was given a uniformly blonde color.
  • the head hair is covered with a hood with a perforated grid, and individual strands of hair are pulled through the holes in the hood, evenly distributed over the entire surface of the hood, using a crochet hook.
  • the strands of hair drawn through are combed.
  • the shading agent is prepared from 25.0 g of the shading powder according to Table 3 and 50 ml of the composition according to Table 4 by mixing and applied to the strands of hair with a brush. After an exposure time of 30 minutes, the shading agent is rinsed off and the hood is removed from the head (step C according to the invention).
  • the hair is washed with a commercially available shampoo and then dried.
  • Hair with a blonde base tone and light blonde highlights is obtained both in the top coat and in the hair areas below.
  • the highlights are even nuanced from the hairline to the tips and form a sharp contrast to the non-nuanced hair.

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Abstract

La présente invention concerne un procédé de coloration de fibres kératiniques, notamment de cheveux humains. Selon ledit procédé, certaines fibres colorées au préalable, sont soumises de façon sélective, directement après une étape de coloration, à une décoloration oxydative incomplète pour le nuançage. On obtient ainsi des reflets colorés uniformes possédant exclusivement la nuance éclaircie de la coloration mise en oeuvre dans le cadre du procédé selon l'invention.
EP04765400A 2003-11-21 2004-09-18 Procede de coloration de fibres keratiniques Withdrawn EP1715836A1 (fr)

Applications Claiming Priority (2)

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DE10354812A DE10354812A1 (de) 2003-11-21 2003-11-21 Verfahren zur Färbung keratinhaltiger Fasern
PCT/EP2004/010510 WO2005051336A1 (fr) 2003-11-21 2004-09-18 Procede de coloration de fibres keratiniques

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EP (1) EP1715836A1 (fr)
CN (1) CN1882307A (fr)
AU (1) AU2004292736A1 (fr)
DE (1) DE10354812A1 (fr)
WO (1) WO2005051336A1 (fr)

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US20060265818A1 (en) 2006-11-30
US7413579B2 (en) 2008-08-19

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