EP1858594A1 - Agent de coloration sans ammoniac destine a colorer des fibres contenant de la keratine et comprenant de l'oxygene atmospherique utilise comme agent d'oxydation unique - Google Patents

Agent de coloration sans ammoniac destine a colorer des fibres contenant de la keratine et comprenant de l'oxygene atmospherique utilise comme agent d'oxydation unique

Info

Publication number
EP1858594A1
EP1858594A1 EP06706786A EP06706786A EP1858594A1 EP 1858594 A1 EP1858594 A1 EP 1858594A1 EP 06706786 A EP06706786 A EP 06706786A EP 06706786 A EP06706786 A EP 06706786A EP 1858594 A1 EP1858594 A1 EP 1858594A1
Authority
EP
European Patent Office
Prior art keywords
derivatives
group
composition according
amino
hydrogen
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.)
Ceased
Application number
EP06706786A
Other languages
German (de)
English (en)
Inventor
Sabine Kainz
Horst Höffkes
Marc Krippahl
Claudia Kolonko
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 EP1858594A1 publication Critical patent/EP1858594A1/fr
Ceased legal-status Critical Current

Links

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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/413—Indoanilines; Indophenol; Indoamines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols

Definitions

  • the present invention relates to agents for coloring keratin fibers and their use and a corresponding hair dyeing process.
  • the compositions comprise at least one dye-precursor for a naturally-analogous dye selected from the group of the indole or indoline derivatives, at least one developer-type oxidation dye precursor and at least one coupler-type oxidation dye precursor and are free of (a) ammonia and (b) additional oxidants.
  • Human hair is treated today in a variety of ways with hair cosmetic preparations. These include, for example, the cleansing of hair with shampoos, the care and regeneration with rinses and cures and the bleaching, dyeing and shaping of the hair with dyes, tinting agents, waving agents and styling preparations. In this case, means for changing or nuancing the color of the head hair play a prominent role.
  • dyeing or tinting agents which contain so-called direct drawers as a coloring component. These are dye molecules that attach directly to the hair and do not require an oxidative process to form the paint. These dyes include, for example, the henna already known from antiquity for coloring body and hair. These dyes are usually sensitive to shampooing, so that a much undesirable nuance shift or even a visible "discoloration" can occur.
  • Another way to stain keratin-containing fibers is through the use of stains containing a combination of component A reactive carbonyl compounds, ie compounds having at least one reactive
  • the aforementioned components A and B are generally not themselves dyes, and therefore are not suitable alone for dyeing keratin inconveniencer fibers alone. In combination, they form dyes in a non-oxidative process. However, it is also possible to use corresponding developer and / or coupler-type oxidation dye precursors with or without the use of an oxidizing agent under compounds of component B.
  • oxo staining this staining method (hereinafter called oxo staining) can be readily combined with the oxidative staining system.
  • Components A and B are referred to below as Oxofarbstoffvor area.
  • the oxo dyeing is described, for example, in the publications WO-A1-99 / 18916, WO-A1 -00 / 38638, WO-A1-01/34106 and WO-A1-0 01/47483.
  • oxidation colorants For permanent, intensive colorations with corresponding fastness properties, so-called oxidation colorants are used.
  • Such colorants usually contain oxidation dye precursors, of the so-called developer type
  • Coupler component The developer components form under the influence of oxidants or of atmospheric oxygen with one another or under coupling with one or more Coupler components from the actual dyes.
  • the oxidation stains are characterized by excellent, long lasting staining results.
  • the dyeing is preferably carried out gently with atmospheric oxygen.
  • the dye precursors on indole or indoline base usually used are incorporated for this purpose in a cosmetic carrier, which preferably has a basic pH.
  • the coloration according to this method results in a natural black, brown or blonde coloration of keratin-containing fiber, which, however, especially in the brown and blond area has a slight reddish, bluish or violet color nuance. If additional oxidizing agents are used in the colorants, these color shifts occur negligibly or even not at all.
  • Dyes based on nature-analogous dyes appeal to those consumers who want to gently restore their gray hair to a natural hair color.
  • the aforementioned color shift is undesirable especially for this consumer. Therefore, the coloration with natural dyes is in this respect in need of improvement.
  • hair dyes based on dye precursors of indole or Indoltn type which additionally contain at least one amino acid or an oligopeptide to improve the colorations on grayed hair.
  • the dyeings obtained on blond hair all have an undesirable red or blue cast.
  • From EP-B1-613 366 hair dyes which, in addition to an indoline-type dye precursor, 0.05 to 5 wt.% Of at least one oxidation dye precursor of the developer type and 0.05 to 5 wt.% Of at least one oxidation dye precursor coupler type. It has been found that the indoline derivatives improve the dyeing properties of conventional developer and coupler based oxidation colorants.
  • Document EP-A2-1 254 650 discloses hair colorants which, in addition to indoline derivatives as dye precursor, contain at least one selected organic primary amine as alkalizing agent. When using these colorants, brown to black dyeings should be obtained without a reddish color shift. However, the results obtained with these colorants are still unsatisfactory.
  • a first subject of the invention are therefore agents for the atmospheric oxygen-induced coloring of keratin-containing fibers, in particular human hair, in a cosmetically acceptable carrier
  • the means are free of ammonia and no additional oxidizing agent for the components (a), (b) and (c) is included.
  • keratin-containing fibers are understood to mean furs, wool, feathers and in particular human hair.
  • the colorants according to the invention are primarily suitable for dyeing keratinic fibers, in principle there is no obstacle to their use also in other areas of coloration, as long as the technical problem underlying the invention is solved.
  • indoline derivatives of the feature (a) of the agent according to the invention preference is given to compounds of the formula (Ia) and / or their physiologically tolerable salts with an organic or inorganic acid in the agents according to the invention,
  • R 1 is hydrogen, a C r 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 r C 4 alkyl group, and
  • R 5 is one of the groups mentioned under R 4 .
  • 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-butyl-5,6 - dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid and 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • N-methyl-5,6-dihydroxyindoline N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and especially 5, 6-Dihydroxyindolin.
  • Derivatives of the 5,6-dihydroxyindole of the formula (Ib) or their physiologically tolerable salts with an organic or inorganic acid are also suitable as precursors of naturally-analogous hair dyes according to feature (a) of the composition according to the invention.
  • 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, where the -COOH group may also be present as a salt with a physiologically compatible cation,
  • R 3 is hydrogen or a C r C 4 -alkyl group
  • R 4 represents hydrogen, -C 4 alkyl group or a group -CO-R 6 in which R 6 represents a C r C 4 alkyl group
  • R 5 is one of the groups mentioned under R 4 ,
  • 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.
  • indoline and indole derivatives can be used in the colorants of the invention both as free bases and in the form of their physiologically acceptable salts with inorganic or organic acids, for.
  • hydrochlorides sulfates and hydrobromides are used.
  • the precursors of naturally-analogous dyes are preferably present in the compositions according to the invention in an amount of from 0.01 to 10% by weight, in particular from 0.1 to 5% by weight, based in each case on the weight of the ready-to-use colorant.
  • the oxidation dye precursors of the developer type of the feature (b) of the agents according to the invention are preferably present in an amount of 0.01 to 5 wt .-%, in particular from 0.1 to 3 wt .-%, each based on the weight of the ready dye.
  • the developer components according to the invention may be selected from the group which is formed from p-phenylenediamine derivatives, binuclear developer components, p-aminophenol and its derivatives, pyrimidine derivatives, pyrazole derivatives and pyrazolopyrimidine derivatives and the physiologically acceptable salts of these compounds.
  • preferred developer components are mentioned according to the invention.
  • 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 - to C 4 ) -alkyl radical, a 4'-aminophenyl radical or a C 1 - 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 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 - to C 4 ) -alkyl radical or a C 1 - to C 4 -alkyl radical which is substituted by a nitrogen-containing group;
  • G 3 represents a hydrogen atom, a halogen atom such as a chlorine, bromine, iodine or fluorine atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -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 ,
  • 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 dyeing compositions according to the invention, mention may be made in particular of the compounds corresponding to the following formula (E2) and their physiologically tolerated salts: in which:
  • Z 1 and Z 2 independently of one another represent a hydroxyl or NH 2 radical which is optionally substituted by a C 1 - to C 4 -alkyl radical, by a C 1 - to C 4 -hydroxyalkyl radical and / or by a bridge Y.
  • 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 , Sulfur or nitrogen atoms may be interrupted or terminated and may possibly be substituted by one or more hydroxyl or C 1 - 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 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -hydroxyalkyl radical, a C 1 - to C 4 -aminoalkyl radical or a direct compound for bridging Y,
  • G 7 , G 8 , G 9 , G 10 , G 11 and G 12 independently of one another represent a hydrogen atom, a direct bond to the bridge Y or a C 1 - to C 4 -alkyl radical, with the proviso that the compounds of the Formula (E2) contain only one bridge Y per molecule.
  • Preferred binuclear developer component of the formula (E2) are in particular: N, N l-bis (.beta.-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) -1,3-diamino-propan-2-ol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) - tetramethylenediamine, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetrannethylenediamine, N, N '-Diethyl- N.N'-bis - ⁇ ' - amino-S'-methylphenyO-ethylenediamine, bis (2-hydroxy-5-amin
  • 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-tetraoxadecane or one of their physiologically acceptable salts.
  • p-aminophenol or a p-aminophenol derivative or one of the physiologically tolerated salts of the abovementioned compounds 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 r to C 4 ) alkyl, a C 1 - to C 4 -Aminoalkylrest, a hydroxy (C r to C 4 ) alkylamino, a C 1 - to C 4 -hydroxyalkoxy, a C 1 - C 4 hydroxyalkyl aminoalkyl (C r to C 4), or (di-C 1 - to C 4 -alkylamino) - alkyl group (Cr to C4), and
  • G 14 is a hydrogen or halogen atom, a C 1 - to C 4 -alkyl radical, a C 1 - to C 4 -monohydroxyalkyl radical, a C 2 - to C 4 -polyhydroxyalkyl radical, a (C 1 - to C 4 ) - Alkoxy (C r to C 4 ) -alkyl radical, a C 1 - to C 4 -aminoalkyl radical or a C r to C 4 -cyanoalkyl radical, G 15 is hydrogen, C 1 - to C 4 alkyl, C 1 - to C 4 - monohydroxyalkyl radical, a C 2 - to C 4 polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
  • G 16 is hydrogen or a halogen atom.
  • Preferred p-aminophenols of the formula (E3) are, in particular, p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4 -Amino-3-hydroxymethylphenol, 4-amino-2 ⁇ ( ⁇ -hydroxyethoxy) -phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino 2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol, 4-amino-2- ( ⁇ , ⁇ -dihydroxyethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2 chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethylaminomethyl) phenol and their physiologically acceptable 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 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, pyrazolopyrimidine derivatives and their physiologically acceptable salts.
  • Preferred pyridine derivatives are, in particular, the compounds described in the patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2- (4-methoxyphenyl) -amino-3-amino-pyridine, 2,3-diamino-6-methoxy-pyridine, 2- ( ⁇ -
  • G 17 , G 18 and G 19 independently represent a hydrogen atom, a hydroxy group, a (C r C 6 ) alkoxy group or an amino group and
  • G 20 represents a hydroxy group or a group -NG 21 G 22 , wherein G 21 and
  • G 22 independently of one another represent a hydrogen atom, a (C 1 -C 6 ) -alkyl group, a (C 1 -C 6 ) -hydroxyalkyl group, with the proviso that at most two of the groups G 17 , G 18 , G 19 and G 20 represent a hydroxy group and at most two of the radicals G 17 , G 18 and G 19 are a hydrogen atom.
  • Particularly preferred pyrimidine derivatives are, in particular, the compounds described in German patent DE 2 359 399, Japanese laid-open specification JP 02019576 A2 or in published patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy -2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6 -Triaminopyrimidin.
  • Preferred pyrazole derivatives are selected according to the invention from compounds of the formula (E5),
  • G 23 , G 24 , G 25 independently of one another represent a hydrogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 monohydroxyalkyl group, a C 2 to C 6 polyhydroxyalkyl group, an optionally substituted aryl group or an optionally substituted aryl-C 1 to C 6 alkyl group and
  • G 26 represents a hydrogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 -
  • Monohydroxyalkyl group or a C 2 to C 6 polyhydroxyalkyl group is provided.
  • Particularly preferred pyrazole derivatives are, in particular, the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, EP-740 931 and DE 195 43 988, such as 4, 5-diamino-1-methylpyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4.5 Diamino-1, 3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazino-pyrazole , 1-Benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-
  • Preferred pyrazolopyrimidine derivatives are, in particular, the derivatives of the pyrazolo [1,5-a] pyrimidine of the following formula (E6) and its tautomeric forms, provided that a tautomeric equilibrium exists:
  • G 27, G 28, G 29 and G 30 are independently a hydrogen atom, a C 1 - to C 4 -alkyl radical, an aryl radical, a Ci to C 4 -hydroxyalkyl group, a C 4 polyhydroxyalkyl radical Gabis a ( C 1 - to C ⁇ -Akoxy- (C 1 - to C 4 ) -alkyl radical, a C 1 - to C 4 -Aminoalkylrest, which may be protected by an acetyl-ureide or a sulfonyl radical, a (C 1 - to C 4) alkylamino (C r to C, alkyl group a Di 4) - [(C r to C 4) alkyl] - (C r to C 4) aminoalkyl, wherein the dialkyl residues optionally form a carbon cycle or a heterocycle with 5 or 6 chain members, a C 1 - to C 4 -hydroxyalkyl or a di- (
  • the pyrazolo [1, 5-a] -pyrimidines of the above formula (E6) can be prepared as described in the literature by cyclization starting from an aminopyrazole or from hydrazine.
  • the coupler components used are generally m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives.
  • Suitable coupler substances are, in particular, 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-chloro-resorcinol, 4-chloro-resorcinol , 2-chloro-6-methyl-3-aminophenol, 2-amino-3
  • Coupler components (c) which are preferred according to the invention are selected from at least one member of the group of compounds which is formed from m-aminophenol and its derivatives, such as preferably 5-amino-2-methylphenol, IM-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,
  • m-phenylenediamine and its derivatives such as preferably 2,4-diaminophenoxyethanol, 1,3-bis (2, 1 , 4'-diaminophenoxy) -propane, 2-amino-1-methoxy-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 , 2 - ( ⁇ 3 - [(2-hydroxyethyl) amino] -2-methoxy-5-methylphenyl ⁇ amino) ethanol, 3-amino-4- (2-methoxyethoxy) -5-methylphenylamine, 2 - ( ⁇ 3- [(2-hydroxyethyl) amino] -4-methoxy-5-methylphenyl ⁇ amino) ethanol and 2 -
  • Di- or trihydroxybenzene derivatives such as preferably resorcinol and derivatives (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 preferably 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 preferably mono- or Dihydroxynaphthalinderivate, 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, 1, 3-dihydroxynaphthalene and 2,3-dihydroxynaphthalene,
  • 1-naphthol 2-methyl-1-naphthol
  • 2-hydroxymethyl-1-naphthol 2-hydroxymethyl-1-naphthol
  • 2-hydroxyethyl-1-naphthol 2-hydroxyethyl-1-naphthol
  • 1,5-dihydroxynaphthalene 1, 6-dihydroxynaphthalene , 1, 7-d
  • Morpholine derivatives such as preferably 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
  • Quinoxaline derivatives such as preferably 6-methyl-1,2,3,4-tetrahydroquinoxaline,
  • Methylenedioxybenzene derivatives such as preferably 1-hydroxy-3,4-methylenedioxybenzene, 1-amino-3,4-methylenedioxybenzene and 1- (2'-hydroxyethyl) amino-3,4-methylenedioxybenzene.
  • the dye precursors of naturally-occurring dyes of the indole or indoline type with at least one of the following combinations of developer and coupler components according to Table 1: Table 1: preferred combinations of developer and coupler components
  • the respective developer or coupler components according to Table 1 are preferably selected from their preferred individual representatives and / or their physiologically acceptable salts mentioned above in the context of the respective classes of compounds. It is very particularly preferred that the agents according to the invention comprise at least one of the following feature combinations for the features (b) and (c): Particularly preferred combinations according to K1 from Table 1 are: p-toluenediamine and resorcinol 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and resorcinol p-toluenediamine and 2-methylresorcinol 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and 2-methylresorcinol p-toluenediamine and 4-chlororesorcinol 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and 4-chlororesorcinol
  • K2 from Table 1 Particularly preferred combinations according to K2 from Table 1 are: 4,5-diamino-1- (2-hydroxyethyl) pyrazole and resorcinol 4,5-diamino-1- (2-hydroxyethyl) pyrazole and 2-methylresorcinol 4,5-diamino- 1- (2-hydroxyethyl) pyrazole and 4-chlororesorcinol
  • Particularly preferred combinations according to K3 from Table 1 are: 2,4,5,6-tetraaminopyrimidine and resorcinol 2,4,5,6-tetraaminopyrimidine and 2-methylresorcinol 2,4,5,6-tetraaminopyrimidine and 4-chlororesorcinol 4-hydroxy -2,5,6-triaminopyrimidine and resorcinol 4-hydroxy-2,5,6-triaminopyrimidine and 2-methylresorcinol 4-hydroxy-2,5,6-triaminopyrimidine and 4-chlororesorcinol 2,4,5,6-tetraaminopyrimidine, 2-methylresorcinol and 1, 5-dihydroxynaphthalene
  • Particularly preferred combinations according to K5 from Table 1 are: p-aminophenol and 2,4-diaminophenoxyethanol p-aminophenol and 2-amino-1-methoxy-4- (2-hydroxyethylamino) benzene p-aminophenol and 2,6-bis ( 2'-hydroxyethylamino) -1-methylbenzene 4-amino-3-methylphenol and 2,4-diaminophenoxyethanol 4-Amino-3-methylphenol and 2-amino-1-methoxy-4- (2-hydroxyethylamino) -benzene 4-Amino-3-methylphenol and 2,6-bis (2'-hydroxyethylamino) -1-methylbenzene
  • K7 from Table 1 Particularly preferred combinations according to K7 from Table 1 are: p-toluenediamine and 2-amino-3-hydroxypyridine 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and 2-amino-3-hydroxypyridine p-toluenediamine and 2,6-dihydroxy- 3,4-dimethylpyridine 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine and 2,6-dihydroxy-3,4-dimethylpyridine 2- ( ⁇ -hydroxyethyl) -p-phenylenediamine, 2-amino-3-hydroxypyridine and 2- methylresorcinol
  • Particularly preferred combinations according to K8 from Table 1 are: bis (2-hydroxy-5-aminophenyl) methane and 2-amino-3-hydroxypyridine bis (2-hydroxy-5-aminophenyl) methane and 3-amino-2 -methylamino-6-methoxypyridine Bis- (2-hydroxy-5-aminophenyl) -methane and 2,6-dihydroxy-3,4-dimethylpyridine Bis- (2-hydroxy-5-aminophenyl) -methane and 3,5-diamino -2,6-dimethoxy
  • Particularly preferred combinations according to K9 from Table 1 are: p-aminophenol and 2-amino-3-hydroxypyridine 4-amino-3-methylphenol and 2-amino-3-hydroxypyridine p-aminophenol and 3-amino-2-methylamino-6 methoxypyridine 4-amino-3-methylphenol and 3-amino-2-methylamino-6-methoxypyridine p-aminophenol and 2,6-dihydroxy-3,4-dimethylpyridine 4-amino-3-methylphenol and 2,6-dihydroxy-3 , 4-dimethylpyridine p-aminophenol and 3,5-diamino-2,6-dimethoxypyridine 4-amino-3-methylphenol and 3,5-diamino-2,6-dimethoxypyridine
  • resorcinol and its derivatives as coupler component, in particular 2-methylresorcinol, in addition to further improving the technical effect as a further coupler component at least one naphthalene, in particular at least one of the above representatives, more preferably 1, 5-dihydroxynaphthalene to use in the inventive compositions.
  • physiologically tolerated salts of the corresponding enumerated compounds can also be used.
  • the coupler-type oxidation dye precursors of feature (c) of the compositions according to the invention are preferably present in an amount of from 0.01 to 5% by weight, in particular from 0.1 to 3% by weight, based in each case on the weight of the ready-to-use colorant.
  • the dye precursors of naturally-analogous dyes (a) and the developer components (b) are preferably in a molar ratio of 10 to 1 to 1 to 2, more preferably in a molar ratio of 8 to 1 to 2 to 1, most preferably in a molar ratio of 6 to 1 to 3 to 1 in the inventive compositions.
  • the coupler components (c) and the developer components (b) are preferably in a molar ratio of 8 to 1 to 1 to 2, more preferably in a molar ratio of 6 to 1 to 2 to 1, most preferably in a molar ratio of 2.5 to 1 to 4.5 to 1 in the inventive compositions.
  • the dye precursors of naturally-analogous dyes (a) and the coupler components (c) are preferably in a molar ratio of 2: 1 to 1: 2, more preferably in a molar ratio of 1.5 to 1 to 1: 1.5, most preferably in one Molar ratio of 1, 5 to 1 to 1 to 1 in the inventive compositions.
  • the ready-to-use hair dye preparation according to the invention should preferably have a pH in the range from 6 to 12. Particularly preferred is the use of the hair dye in an alkaline environment.
  • the alkalizing agents (d) usable in the present invention are preferably selected from the group consisting of basic amino acids, alkali hydroxides, alkanolamines, alkali carbonates, alkali hydrogencarbonates, alkali metal metasilicates, alkali phosphates and alkali hydrogen phosphates.
  • the alkali metal ions used are preferably lithium, sodium, potassium, in particular sodium or potassium.
  • the basic amino acids which can be used as alkalizing agents according to the invention are preferably selected from the group formed from L-arginine, D-arginine, D, L-arginine, L-histidine, D-histidine, D, L-histidine, L-lysine, D-lysine, D, L-lysine, more preferably L-arginine, D-arginine, D, L-arginine used as an alkalizing agent according to the invention.
  • the alkali metal hydroxides which can be used as the alkalizing agent according to the invention are preferably selected from the group formed from sodium hydroxide and potassium hydroxide.
  • alkanolamines which can be used as alkalizing agents according to the invention are preferably selected from primary amines having a C 2 -C 6 -alkyl basic body which carries at least one hydroxyl group.
  • Particularly preferred alkanolamines are selected from the group formed from 2-aminoethan-1-ol (monoethanolamine), 3-aminopropan-1-ol, 4-aminobutan-1-ol, 5-aminopentan-1-ol, 1 -Aminopropan-2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol , 1-amino-2-methylpropan-2-ol, 3-aminopropane-1, 2-diol, 2-amino-2-methylpropane-1,3-diol.
  • Alkanolamines are examples of al
  • a cosmetically acceptable carrier is understood in particular to be an otherwise customary carrier of agents for coloring human hair.
  • the colorants according to the invention may be composed with regard to the features essential to the invention according to known colorants or contain them for these conventional ingredients. Examples of further suitable and inventively preferred ingredients are given below.
  • the agents according to the invention preferably contain the components according to the invention 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.
  • a suitable aqueous, alcoholic or aqueous-alcoholic carrier for the purpose of hair coloring
  • 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.
  • the dye precursors in a powdered or tablet-shaped formulation.
  • aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing 3 to 70% by weight of a C 1 -C 4 -alkoxy, in particular ethanol or isopropanol.
  • the compositions of the invention may additionally contain other organic solvents, such as methoxybutanol, benzyl alcohol, ethyl diglycol or 1, 2-propylene glycol. Preference is given to all water-soluble organic solvents.
  • the colorants according to the invention may contain one or more substantive dyes for shading.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred substantive dyes are those of the HC Yellow 2, HC Yellow 4, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange 1, Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds as well as 1, 4-diamino-2 ⁇ nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis ( ⁇ -hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- ( ⁇ -hydroxyethyl) aminophenol, 2- (2'-hydroxyethyl) amino-4,6-dinitrophenol, 1- (2'-hydroxyethyl) amino-4-methyl-2-nitrobenzene, 1-amino-4
  • agents according to the invention may contain a cationic substantive dye. Particularly preferred are
  • Preferred cationic substantive dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic substantive dyes of group (c).
  • the cationic direct dyes which are sold under the brand Arianor® ® are, according to the invention also very particularly preferred cationic direct dyes.
  • the agents according to the invention according to this embodiment preferably contain the substantive dyes in an amount of from 0.01 to 20% by weight, based on the total colorant.
  • preparations of the invention may also naturally occurring dyes such as henna red, henna neutral, henna black, chamomile, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • the compounds A or 2 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, 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.
  • the colorants of the invention may further contain all known for such preparations active ingredients, additives and excipients.
  • the colorants contain at least one surfactant, with both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle.
  • anionic surfactants in preparations according to the invention are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such.
  • Example a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 10 to 22 carbon atoms.
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule.
  • esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 C atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid , Isostearic acid and palmitic acid.
  • Nonionic surfactants contain as hydrophilic group z.
  • Such compounds are, for example
  • Preferred nonionic surfactants are alkyl polyglycosides of the general formula R 1 O- (Z) x . These connections are identified by the following parameters.
  • the alkyl radical R 1 contains 6 to 22 carbon atoms and may be both linear and branched. Preference is given to primary linear and methyl-branched in the 2-position aliphatic radicals.
  • Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. Particularly preferred are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl.
  • oxo-alcohols compounds with an odd number of carbon atoms in the alkyl chain predominate.
  • alkyl polyglycosides which can be used according to the invention can contain, for example, only one particular alkyl radical R 1 .
  • these compounds are prepared starting from natural fats and oils or mineral oils. In this case are present as alkyl radicals R mixtures according to the starting compounds or according to the respective workup of these compounds.
  • R 1 consists essentially of C 8 - and C-io-alkyl groups essentially of C 12 - and C - ⁇ - alkyl groups essentially of C 8 - to C 6 -alkyl or substantially from C 12 - to Ci 6 alkyl groups.
  • sugar building block Z it is possible to use any desired mono- or oligosaccharides.
  • sugars with 5 or 6 carbon atoms and the corresponding oligosaccharides are used.
  • Such sugars are, for example, glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, altrose, mannose, gulose, isose, talose and sucrose.
  • Preferred sugar building blocks are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain on average from 1.1 to 5 sugar units. Alkyl polyglycosides having x values of 1.1 to 1.6 are preferred. Very particular preference is given to alkyl glycosides in which x is 1: 1 to 1, 4.
  • the alkyl glycosides can also serve to improve the fixation of fragrance components on the hair.
  • this substance class as a further constituent of the preparations according to the invention in the event that an effect of the perfume oil on the hair which exceeds the duration of the hair treatment is desired.
  • alkoxylated homologs of said alkyl polyglycosides can also be used according to the invention. These homologs may contain on average up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • zwitterionic surfactants can be used, in particular as cosurfactants.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO H or -SO 3 H group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium-glycinate, for example, the cocoalkyl dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammoniumglycinate, for example Kokosacylaminopropyl-dime- thylammoniumglycinat, and 2-alkyl 3-carboxymethyl-3-hydroxyethyl-imidazolines having in each case 8 to 18 carbon atoms in the alkyl or acyl group, and the Kokosacylaminoethyl- hydroxyethylcarboxymethylglycinat.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
  • ampholytic surfactants are understood to mean those surface-active compounds which, apart from a C 8 -C 18 -alkyl or acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and which are capable of forming internal salts are.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12-18 acylsarcosine.
  • the cationic surfactants used may in particular be those of the quaternary ammonium compounds, esterquats and amidoamines type.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Esterquats are known substances which have at least one ester function and at least one quaternary ammonium group as structural element. hold.
  • Preferred esterquats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are marketed under the brands Stepantex® ®, ® and Dehyquart® Armocare® ®.
  • the alkylamidoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group of substances that available under the brand Tegoamid ® S 18 commercially stearamidopropyl dimethylamine is.
  • cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • cationic silicone oils such as, 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, quaternium-80).
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to INCI nomenclature a "lauryl methyl GIu- Ceth-10 hydroxypropyl dimonium chloride".
  • the compounds used as surfactant with alkyl groups may each be uniform substances. However, it is generally preferred to use native vegetable or animal raw materials in the production of these substances, so that substance mixtures having different alkyl chain lengths depending on the respective raw material are obtained.
  • the surfactants which are adducts of ethylene oxide and / or propylene oxide with fatty alcohols or derivatives of these addition products
  • both products with a "normal” homolog distribution and those with a narrow homolog distribution can be used.
  • "normal" homolog distribution are meant mixtures of homologs which are obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alkoxides as catalysts.
  • Narrowed homolog distributions are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts.
  • the use of products with narrow homolog distribution may be preferred.
  • colorants according to the invention further active ingredients, auxiliaries and additives, such as
  • nonionic polymers for example 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, diethyl sulfate-quaternized dimethylaminoethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol,
  • zwitterionic and amphoteric polymers for example acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate hydroxypropyl methacrylate copolymers, anionic polymers, for example polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers , Vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert.
  • anionic polymers for example polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers , Vinylpyrrolidone / vinyl acrylate copo
  • Butyl acrylamide terpolymers, amphiphilic polymers such as, for example, the polymers according to the INCI name: designations acrylates / beheneth-25 methacrylate copolymer, acrylates / C 10-30 alkyl acrylate crosspolymer, acrylates / ceteth-20 itaconates 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-20 Methacrylate Copolymer, Acrylates / Stearyl Methacrylate Copolymer, Acrylates A / inyl Isodecanoate Crosspolymer,
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabicum, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. For example, 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 wheat protein hydrolysates, their condensation products with fatty acids and quaternized protein hydrolysates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, fiber-structure-improving agents, especially mono-, di- and oligosaccharides such as glucose, galactose, fructose, fructose and lactose, quaternized amines such as methyl-1-alkylamidoethyl 2-alkylimidazolinium methosulfate defoamers such as silicones, dyes for staining the agent,
  • Antidandruff active ingredients such as Piroctone Olamine, zinc Omadine and Climbazole, light stabilizers, in particular derivatized benzophenones, cinnamic acid derivatives and triazines,
  • Substances for adjusting the pH such as, for example, customary acids, in particular edible acids and bases, active substances such as allantoin, pyrrolidonecarboxylic acids and their salts, and also bisabolol, Vitamins, provitamins and vitamin precursors, in particular those of the groups A 1 B 3 , B 5 , B 6 , C, E, F and H,
  • Plant extracts such as extracts of green tea, oak bark, stinging nettle, witch hazel, hops, chamomile, burdock root, horsetail, hawthorn, lime blossom, almond, aloe vera, spruce needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime, wheat, kiwi , Melon, orange, grapefruit, sage, rosemary, birch, mallow, meadowfoam, quenelle, yarrow, thyme, lemon balm, toadstool, coltsfoot, marshmallow, meristem, ginseng and ginger root ,.
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as spermaceti, beeswax, montan wax and paraffins, fatty acid alkanolamides,
  • - swelling and penetrating substances 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,
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air,
  • the colorant can also be applied to the hair together with an oxidation activator, which activates the oxidation of the dye precursors by the atmospheric oxygen.
  • the oxidation activators are preferably selected from the group formed from carbonates, Hydrogen carbonates, carbamates, carboxylic acid esters or their salts, aldehydes, especially aliphatic aldehydes, 1, 3-dihydroxyacetone, imidazole and its derivatives, alkali metal and Ammoniumperoxidisulfaten, metal ions, iodides, quinones and enzymes.
  • the oxidative dyeing is formed by atmospheric oxygen, it may be advantageous according to the invention to use metal ions as the oxidation activator.
  • 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.
  • the activators are preferably present in amounts of 0.01 to 5 wt.%, Based on the weight of the total colorant, in the inventive compositions.
  • 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.
  • a second subject matter of the present invention is a process for coloring keratinic fibers, in which a hair colorant according to the invention is applied to the fibers and rinsed off again after a contact time.
  • inventive colorant formulations E1 to E6 were prepared by a production process known to the person skilled in the art. The following raw materials were used:
  • Ci6-Ci 8 fatty alcohol (INCI name: Cetearyl alcohol) (Cognis Germany) Lorol® ® techn.
  • C 2 -C 18 fatty alcohol (INCI name: coconut alcohol) (Cognis Germany)
  • Each natural hair strand was dyed.
  • the hair each received an intense, permanent natural color without red, blue or purple stitch.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des agents permettant une coloration induite par l'oxygène atmosphérique de fibres contenant de la kératine, comprenant au moins précurseur de coloration pour un colorant de type naturel, sélectionné parmi le groupe des dérivés d'indole ou d'indoline, au moins un produit semi-fini de coloration par oxydation de type solvant ainsi qu'au moins un produit semi-fini d'oxydation de type agent de couplage, exempts d'ammoniac et d'autres agents d'oxydation. Les colorations ainsi obtenues présentent une couleur intense, tiennent longtemps et ne présentent pas de teinte rouge, bleue, ou violette.
EP06706786A 2005-03-18 2006-02-09 Agent de coloration sans ammoniac destine a colorer des fibres contenant de la keratine et comprenant de l'oxygene atmospherique utilise comme agent d'oxydation unique Ceased EP1858594A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005013067A DE102005013067A1 (de) 2005-03-18 2005-03-18 Ammoniakfreies Oxidationsfärbemittel zur Färbung keratinhaltiger Fasern mit Luftsauerstoff als einzigem Oxidationsmittel
PCT/EP2006/001151 WO2006097167A1 (fr) 2005-03-18 2006-02-09 Agent de coloration sans ammoniac destine a colorer des fibres contenant de la keratine et comprenant de l'oxygene atmospherique utilise comme agent d'oxydation unique

Publications (1)

Publication Number Publication Date
EP1858594A1 true EP1858594A1 (fr) 2007-11-28

Family

ID=36218373

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06706786A Ceased EP1858594A1 (fr) 2005-03-18 2006-02-09 Agent de coloration sans ammoniac destine a colorer des fibres contenant de la keratine et comprenant de l'oxygene atmospherique utilise comme agent d'oxydation unique

Country Status (7)

Country Link
US (1) US20080104774A1 (fr)
EP (1) EP1858594A1 (fr)
CN (1) CN101141998A (fr)
AU (1) AU2006224851A1 (fr)
DE (1) DE102005013067A1 (fr)
RU (1) RU2007138375A (fr)
WO (1) WO2006097167A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007039330A1 (de) * 2007-08-20 2009-02-26 Henkel Ag & Co. Kgaa Haarbehandlungsmittel
FR2951373B1 (fr) * 2009-10-16 2012-04-13 Oreal Composition comprenant au moins un derive de 1,8-dihyroxy-naphtalene et au moins un agent alcalinisant different de l'ammoniaque, procede de coloration des fibres keratiniques a partir de la composition
FR3022454B1 (fr) * 2014-06-20 2017-10-06 Oreal Procede de coloration des fibres keratiniques comprenant l'application d'un colorant auto-oxydable et d'une base d'oxydation (hetero)cyclique particuliere en l'absence d'oxydant
FR3022455B1 (fr) * 2014-06-20 2017-09-01 Oreal Procede de coloration des fibres keratiniques comprenant l'application d'une base d'oxydation (hetero)cyclique particuliere en l'absence d'oxydant et en milieu riche en corps gras
ITUA20161586A1 (it) * 2016-03-11 2017-09-11 Beauty & Business S P A Composizione per colorare la fibra cheratinica

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62215986A (ja) * 1986-03-18 1987-09-22 Toshiba Corp 定着装置
DE3725030A1 (de) * 1987-07-29 1989-02-09 Henkel Kgaa Oberflaechenaktive hydroxysulfonate
DE3843892A1 (de) * 1988-12-24 1990-06-28 Wella Ag Oxidationshaarfaerbemittel mit einem gehalt an diaminopyrazolderivaten und neue diaminopyrazolderivate
DE3926344A1 (de) * 1989-08-09 1991-02-28 Henkel Kgaa Verfahren zur herstellung von hellfarbigen oelsaeuresulfonaten
DE4016177A1 (de) * 1990-05-19 1991-11-21 Henkel Kgaa Oxidationsfaerbemittel fuer keratinfasern
FR2671722B1 (fr) * 1991-01-21 1993-04-16 Oreal Utilisation de derives indoliques a titre de coupleurs dans la teinture des fibres keratiniques.
DE4133957A1 (de) * 1991-10-14 1993-04-15 Wella Ag Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
US5518506A (en) * 1992-04-09 1996-05-21 L'oreal Process for dyeing keratinous fibres with an alkaline composition containing para-aminophenols substituted in position 2 in combination with 6- or 7-hydroxindole
DE4234887A1 (de) * 1992-10-16 1994-04-21 Wella Ag Oxidationshaarfärbemittel mit einem Gehalt an 4,5-Diaminopyrazolderivaten sowie neue 4,5-Diaminopyrazolderivate und Verfahren zu ihrer Herstellung
DE4440957A1 (de) * 1994-11-17 1996-05-23 Henkel Kgaa Oxidationsfärbemittel
FR2733749B1 (fr) * 1995-05-05 1997-06-13 Oreal Compositions pour la teinture des fibres keratiniques contenant des diamino pyrazoles, procede de teinture, nouveaux diamino pyrazoles et leur procede de preparation
DE19745356A1 (de) * 1997-10-14 1999-04-15 Henkel Kgaa Verwendung von Oniumaldehyden und -ketonen zum Färben von keratinhaltigen Fasern
DE19827000A1 (de) * 1998-06-23 1999-12-30 Henkel Kgaa Färbemittel
WO1999066890A1 (fr) * 1998-06-23 1999-12-29 Henkel Kommanditgesellschaft Auf Aktien Colorant pour colorer des fibres keratiniques
FR2787708B1 (fr) * 1998-12-23 2002-09-13 Oreal Procede de teinture mettant en oeuvre un compose a methylene actif et un compose choisi parmi un aldehyde, une cetone, une quinone et un derive de la di-imino-isoindoline ou de la 3-amino-isoindolone
US6702863B1 (en) * 1999-06-22 2004-03-09 Lion Corporation Hairdye composition
DE19951134A1 (de) * 1999-10-23 2001-04-26 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
DE50113473D1 (de) * 2000-06-06 2008-02-21 Henkel Kgaa Verfahren zur oxidativen färbung keratinischer fasern
DE60221179T2 (de) * 2001-04-23 2008-03-20 Kao Corp. Haarfärbemittel
DE10240758A1 (de) * 2002-08-30 2004-03-11 Henkel Kgaa Neue Farbstoffkombination
DE10260834A1 (de) * 2002-12-23 2004-07-01 Henkel Kgaa Neue Kupplerkomponenten
DE10260835A1 (de) * 2002-12-23 2004-07-01 Henkel Kgaa Neue Färbemittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006097167A1 *

Also Published As

Publication number Publication date
AU2006224851A1 (en) 2006-09-21
DE102005013067A1 (de) 2006-10-19
RU2007138375A (ru) 2009-04-27
CN101141998A (zh) 2008-03-12
WO2006097167A1 (fr) 2006-09-21
US20080104774A1 (en) 2008-05-08

Similar Documents

Publication Publication Date Title
DE102005062830A1 (de) Oxidationsfärbemittel zur Färbung keratinhaltiger Fasern
DE102005055270A1 (de) Neuer Farbstoffvorproduktkombinationen
EP2152226A2 (fr) Colorants d'oxydation destinés à colorer des fibres kératiniques au moyen d'oxygène atmosphérique comme unique agent d'oxydation
EP1787632A1 (fr) Combinations nouvelles des colorants de base
EP1795179A1 (fr) Association de précurseurs de colorants comprenant un dérivé de diaminopyrazole, un derivé de m-aminophénol et un derivé de pyrimidine
EP1797863A1 (fr) Association de précurseurs de colorants comprenant un dérivé de diaminopyrazole, un derivé de m-aminophénol et un derivé de m-phénylène diamine
DE102005055340A1 (de) Neue Farbstoffvorproduktkombinationen
EP1324742B1 (fr) Colorants d'oxydation contenant 2-chloro-4-aminophenol
EP1696871B1 (fr) Colorant d'oxydation en tube
DE10260835A1 (de) Neue Färbemittel
WO2006097167A1 (fr) Agent de coloration sans ammoniac destine a colorer des fibres contenant de la keratine et comprenant de l'oxygene atmospherique utilise comme agent d'oxydation unique
EP2037871A1 (fr) Colorants d'oxydation pour la coloration de fibres kératiniques avec l'oxygène de l'air comme unique agent oxydant
EP1453477B1 (fr) Combinaison revelateurs-coupleur contenant du 2,4-dichloro-3-aminophenol
DE10103657A1 (de) Neue Kupplerkomponente für Oxidationsmittel
DE102005055496A1 (de) Azofarbstoffe zum Färben keratinhaltiger Fasern
EP1286647B1 (fr) Procede de coloration par oxydation de fibres de keratine
EP1787685B1 (fr) Combinaisons de précurseurs de coloration
DE102005062645A1 (de) Neue Kupplerkomponenten
DE102004036688A1 (de) Kationische Azoverbindungen als direktziehende Farbstoffe zur Färbung keratinischer Fasern
EP1453476B1 (fr) Nouveaux colorants d'oxydation contenant du 2,4-dichloro-3-aminophenol
WO2002026200A1 (fr) Colorant d'oxydation contenant du 2-amino-5-methylphenol
EP1731196A1 (fr) Procédé en plusieurs étapes pour la coloration de fibres kératiniques
EP1301163B1 (fr) Colorants d'oxydation capillaires renfermant comme coupleur au moins un 2,4-diaminophenylether disubstitue
DE102004053653A1 (de) Oxidationsfärbemittel ohne Entwicklerkomponente
DE10242748A1 (de) Haarbehandlungsmittel

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20070619

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

17Q First examination report despatched

Effective date: 20080114

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: HENKEL AG & CO. KGAA

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

18R Application refused

Effective date: 20090926