DE19746250A1 - 2-Alkenyl-1-naphthols use as coupler in oxidation color for hair and other keratin fibers - Google Patents

Abstract

2-Alkenyl-1-naphthols are used as coupler in oxidation hair colors. 2-Alkenyl-1-naphthols of formula (I) are used as coupler in oxidation hair colors; R<1> = optionally substituted 3-9C alkenyl; R<2> = H, Cl, Br, 1-4 C alkyl and/or 1-4 C alkoxy substituents in the 3-, 5-, 6-, 7 or 8-positions. An Independent claim is also included for oxidation colors for coloring keratin fibers, which contain (I) as coupler and a developer component.

Description

The invention relates to the use of substituted α-naphthols for Coloring of keratin fibers and colorants containing these compounds.

For the dyeing of keratin fibers, especially human hair, play the so-called oxidation dyes because of their intense colors and good real properties a preferred role. Contain such colorants Oxidation dye precursors, so-called developer components and Kupp lerkomponenten. The developer components form under the influence of Oxidizing agents or of atmospheric oxygen with each other or under coupling with one or more coupler components, the actual dyes.

Good oxidation dye precursors must first and foremost the following You must fulfill the desired conditions for the oxidative coupling Forming shades in sufficient intensity and authenticity. You must continue have a good Aufziehvermögen on the fiber, in particular at human hair no noticeable differences between strained and freshly grown hair may exist (leveling ability). You should resistant to light, heat and the influence of chemical reducing agents, z. B. against perming fluids. Finally, they should - if as a hair dye  medium used - the scalp is not too much, and before In particular, they should be harmless from a toxicological and dermatological point of view his.

As developer components are usually primary aromatic amines with another, in para or ortho position, free or substi substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic Hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and used its derivatives.

Preferred developer components are p-phenylenediamine, p-toluenediamine, p-aminophenol, 1- (β-hydroxyethyl) -2,5-diaminobenzene, N, N-bis (2-hydroxy ethyl) -p-phenylenediamine, 2- (2,5-diaminophenoxy) -ethanol, 4,5-diamino-1- (2-hy droxyethyl) pyrazole, 1-phenyl-3-carboxyamido-4-amino-pyrazolone-5,4-Ami no-3-methylphenol, 2-hydroxymethyl-4-aminophenol, 2-aminomethyl-4-ami nophenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2-Dimethylamino-4,5,6-triaminopyrimidine, 2-hydroxyethylaminomethyl-4-amino phenol, 1,3-bis [N- (2-hydroxyethyl) -N- (4-aminophenyl) -amino] -2-propanol such as 4,4'-diaminodiphenylamine.

As coupler components are usually m-phenylenediamine derivatives, Naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols ver applies. Particularly suitable coupling agents are 1-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, Resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis- (2,4-diaminophenoxy) -propane, 2-chloro-resorcinol, 4-chloro-resorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-3-hy droxypyridine, 2-methylresorcinol, 5-methylresorcinol, o-aminophenol, 2,5-di methylresorcinol, 2,6-dihydroxypyridine, 2,6-diaminopyridine, 2,6-dihydroxy-  3,4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 3-amino-2-methylamino-6-me thoxypyridine, 2,6-bis- (2-hydroxyethylamino) -toluene, 2,4-diaminophenoxy ethanol and 2-amino-4-hydroxyethylamino-anisole.

With a developer component or a specific coupler / developer Combination usually does not succeed, a naturally acting on the hair To get color nuance. In practice, therefore, usually combinations various developer and / or coupler components used. It exists Therefore, there is always a need for new, improved dye components.

It was therefore the object of the present invention, new coupler Kompo to find the to be placed on oxidation dye precursors An meet requirements to a special degree.

It has now been found that certain substituted α-naphthols the Coupler components meet high requirements. So are most commonly known using these coupler components Developer components brilliant yellow-green to deep blue, in particular get intense reddish shades that are extremely light and washfast are.

A first subject of the present invention therefore relates to the use of substituted α-naphthols of the general formula (I),

in which R ^{1 is} an optionally substituted alkenyl radical having 3 to 9 C atoms and R ^{2 is} a substituent selected from the group consisting of H, Cl, Br, alkyl groups having 1 to 4 carbon atoms and alkoxy groups 1 to 4 carbon atoms, which may be in the 3-, 5-, 6-, 7- or 8-position, as a coupler component in Oxidationshaarstärbemitteln.

In the context of the present application, preference is given to α-naphthols in which R ^{1 is} a propenyl radical of the formula (II)

in which R ^{3 is} in turn hydrogen or a C ₁ - to C ₄ -alkyl group. Particular preference is given to those α-naphthols in which R ^{3 is} hydrogen. The substituent R ² is particularly preferably hydrogen in the α-naphthols according to the invention. Such compounds are already known from J. Med. Chem. 39, 2788, (1996).

Another object of the present invention relates Oxidationsfär agent for dyeing keratin fibers containing coupler components and Ent Wicklerkomponenten in a hydrous carrier, acting as a coupler component contain one of the aforementioned substituted α-naphthols.

Keratin fibers in the context of the present application are furs, wool, To understand feathers and especially human hair. Although the Oxidation dye of the invention primarily for dyeing Keratin fibers are suitable, is in principle a use also on others Areas, especially in color photography.

The oxidation colorants of the invention may one or more Ent Wicklerkomponenten and, if desired, in addition to the invention Coupler components contain even more coupler components. In terms of the other developer and coupler components is at the beginning of the  Description of listed substances, the preferred further Represent dye components. Particularly preferred developer components are 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 1- (β-hydroxyethyl) -2,5-diaminobenzene, p-phenylenediamine, p-toluenediamine, p-aminophenol, 3-methyl-p-aminophenol, 2-aminomethyl-p-aminophenol and 2-hydroxymethyl-p-aminophenol. As coupler components are according to the invention in particular 1-naphthol, 2,7-dihydroxynaphthalene, 2,6-dihydroxy-3,4-di methylpyridine, 2,4-diaminophenoxyethanol, 1,3-bis (2,4-diaminophenoxy) -pro pan, 2-amino-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine and 2,6-bis (2-hydroxyethylamino) -toluene. These further developer and coupler components are commonly used in free form. at However, substances with amino groups may be preferred, in salt form, especially in the form of the hydrochlorides and sulfates use.

The hair colorants of the invention contain both the developer components and the coupler components preferably in an amount of 0.005 to 20 wt .-%, preferably 0, 1 to 5 wt .-%, each based on the total An oxidation. This developer components and Kupp lerkomponenten generally used in about molar amounts to each other. Although the molar use has proved to be useful, so is a certain excess of individual oxidation dye precursors not disadvantageous, so that developer components and coupler components in a molar ratio from 1: 0.5 to 1: 2 may be included.

In a preferred embodiment, hair dye according to the invention contain means for further modifying the color shades in addition to the oxidation color stoffvorprodukten additionally customary substantive dyes, eg. B. from the Grup pe of nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols, such as under international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Disperse  Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 known compounds and 4-amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-1,2,3,4-tetrahydro quinoxaline, hydroxyethyl-2-nitro-toluidine, picric acid, 2-amino-6-chloro-4-ni trophenol and 4-N-ethyl-1,4-bis (2'-hydroxyethylamino) -2-nitrobenzene-hydro chloride in an amount of 0.01 to 20 wt .-%, based on the total Oxida tionshaarfärbemittel. 4-Amino-2-nitro-diphenylamine-2'-carboxylic acid, 6-Ni tro-1,2,3,4-tetrahydroquinoxaline and HC Red BN are particularly useful in the invention preferred substantive dyes.

Furthermore, the preparations according to the invention can also be used in nature occurring dyes such as henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, Include bluewood, madder root, catechu, sedre and alcano root.

It is not necessary that the oxidation dye precursors or fa culturally contained direct dyes in each case uniform compounds represent. Rather, in the hair colorants according to the invention, conditional by the manufacturing process for the individual dyes, in subordinate Quantities still contain other components, as far as these are not the Dyeing result adversely affect or other reasons, eg. B. toxicological, must be excluded.

With regard to hair colorants and tinting agents according to the invention applicable dyes is further expressly to the monograph Ch. Zviak, The Science of Hair Care, chapter 7, pages 248-250 (direct Dyes), as well as chapter 8, pages 264-267; (Oxidation dye precursors), appeared as volume 7 of the series "Dermatology" (ed .: Ch. Culnan and H. Maibach), publishing house Marcel Dekker Inc., New York, Basel, 1986, as well as the "European Inventory of Cosmetic Raw Materials", published by the European Community, available in disk form from the Federal Association  German industrial and trading company for pharmaceuticals, health food and personal care product e.V., Mannheim.

To prepare the colorants of the invention, the oxidation color fabric precursors incorporated into a suitable aqueous carrier. To the Hair coloring purposes are such carrier z. As creams, emulsions, gels or surfactant-containing foaming solutions, eg. As shampoos, foam aerosols or other preparations suitable for use on the hair.

Furthermore, the colorants of the invention may all be used in such formulations tions known active ingredients, additives and excipients. In many cases ent keep the colorants at least one surfactant, wherein in principle both anionic as well as zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, it has proved to be advantageous, the Surfactants from anionic, zwitterionic or nonionic surfactants select.

Suitable anionic surfactants in preparations according to the invention are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. Example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 10 to 22 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule. Examples of suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 C atoms in the alkanol group,

• - linear fatty acids with 10 to 22 carbon atoms (soaps),
• Ether carboxylic acids of the formula RO- (CH ₂ -CH ₂ O) _x -CH ₂ -COOH, in which R is a linear alkyl group having 10 to 22 C atoms and x = 0 or 1 to 16,
• Acylsarcosides having 10 to 18 C atoms in the acyl group,
• Acyltaurides having 10 to 18 C atoms in the acyl group,
• Acyl isethionates having 10 to 18 C atoms in the acyl group,
• - Sulfobernsteinsäuremono- and -dialkylester having 8 to 18 carbon atoms in the Alkyl group and sulfosuccinic acid mono-alkylpolyoxyethylester with 8 bis 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups,
• linear alkanesulfonates having 12 to 18 C atoms,
• - linear alpha-olefin sulfonates having 12 to 18 C atoms,
• - alpha-sulfob fatty acid methyl esters of fatty acids containing 12 to 18 carbon atoms,
• Alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH ₂ -CH ₂ O) _x -SO ₃ H, in which R is preferably a linear alkyl group having 10 to 18 C atoms and x = 0 or 1 to 12,
• Mixtures of surface-active hydroxysulfonates according to DE-A-37 25 030,
• - Sulfated hydroxyalkylpolyethylene and / or hydroxyalkylenepropylene glycol ether according to DE-A-37 23 354,
• - Sulfonates of unsaturated fatty acids having 12 to 24 carbon atoms and 1 to 6 Double bonds according to DE-A-39 26 344,
• - esters of tartaric acid and citric acid with alcohols, the addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide Represent fatty alcohols having 8 to 22 carbon atoms.

Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule and in particular salts of saturated and in particular unsaturated C ₈ -C ₂₂ carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid ,

Zwitterionic surfactants are those surface-active compounds be distinguished, which carry at least one quaternary Aminoniumgruppe and minde least one -COO ^(-) - or -SO ₃ ^(-) group in the molecule. Particularly suitable zwitterionic ionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethyl ammonium glycinates, for example the cocoalkyl dimethylammoniumgly cinate, N-acyl-aminopropyl-N, N-dimethylammoniumglycinate, for example Kokosacylaminopropyl-dimethylammoniumglycinat, and 2-Alkyl-3-carboxy-methyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the Kokosacylaminoethylhydroxyethylcarboxymethyl glycinate. A preferred zwitterionic surfactant is the fatty acid amide derivative known by the CTFA name Cocamidopropyl Betaine.

Ampholytic surfactants are understood as meaning those surface-active compounds which, apart from a C _8-18 -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 are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-al kylamidopropylglycine, N-alkyltaurines, N-alkylsarcosines, 2-Alkylaminopropi onsäuren and Alkylaminoessigsäuren each having about 8 to 18 C atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-coco alkylaminopropionate, cocoacylaminoethylaminopropionate and C _12-18 acylsarcosine.

Nonionic surfactants contain as hydrophilic group z. Example, a polyol group, a polyalkylene glycol ether or a combination of polyol and Po lyglykolethergruppe. Such compounds are, for example

• - Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 mol Propylene oxide to linear fatty alcohols having 8 to 22 carbon atoms, to fatty acids with 12 to 22 C-atoms and at alkylphenols with 8 to 15 C-atoms in the alkyl group,
• C _12-22 fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol,
• C _{8-22 alkyl} mono- and oligoglycosides and their ethoxylated analogs,
• - Addition products of 5 to 60 moles of ethylene oxide with castor oil and ge hardened castor oil,
• - Addition products of ethylene oxide to sorbitan fatty acid esters
• - Addition products of ethylene oxide to fatty acid alkanolamides.

Examples of those used in the hair treatment compositions according to the invention Baren cationic surfactants are in particular quaternary ammonium compounds. Preference is given to aminonium halides, such as alkyltrimethylammonium chlorides, Dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distea ryldimethylammonium chloride, lauryldimethylammonium chloride, lauryldi methylbenzylammonium chloride, methyl-1-alkylamidoethyl-2-alkyl-imidazolini um-methosulphate and tricetylmethylammonium chloride. Further according to the invention useful cationic surfactants are the quaternized protein hydrolysates represents.

Also suitable according to the invention are cationic silicone oils, such as, for example See the commercially available products Q2-7224 (manufacturer: Dow Corning; stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxyl-amino-modified silicone, also called Amodime thicone), SM-2059 (manufacturer: General Electric), SLM-55067 (Manufacturer: Wacker) and Abil® Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, quaternium-80).

Alkylamidoamines, in particular fatty acid amidoamines such as the name Tego Amid®S 18 available Stearylamidopropyldimethylamine draw in addition to a good conditioning effect, especially by their good biodegradability.  

Also very good biodegradable are quaternary ester compounds, soge called "esterquats" such as those sold under the trademark Stepantex® Methyl-hydroxyalkyldialkoyloxyalkyl methosulfates.

An example of a quaternary sugar that can be used as a cationic surfactant Derivat represents the commercial product Glucqua®100, according to CTFA nomenclature a "Lauryl Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride".

The compounds with alkyl groups used as surfactants may each be because they are about uniform substances. However, it is usually preferred in the production of these substances from native plant or animal Raw materials so that mixtures of substances with different, receives from the respective raw material dependent alkyl chain lengths.

For the surfactants, the adducts of ethylene and / or propylene oxide to fatty alcohols or derivatives of these addition products can represent Both products with a "normal" homolog distribution and those with a narrow homolog distribution can be used. Under "normal" Homolog distribution is understood to mean mixtures of homologs which in the reaction of fatty alcohol and alkylene oxide using Alkali metals, alkali metal hydroxides or alkali metal alcoholates as Catalysts receives. Narrow homolog distributions are opposed obtained, for example, when hydrotalcites, alkaline earth metal salts of Ethercarboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates as Kata lysatoren be used. The use of products with restricted Homolog distribution may be preferred.

Further customary constituents of the preparations according to the invention can be:

• - Anionic, zwitterionic, amphoteric and nonionic polymers such as For example, vinyl acetate / crotonic acid copolymers, polydimethylsiloxanes,  Vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / iso bornyl-acrylate copolymers, methyl vinyl ether / maleic anhydride copoly mers and their esters, uncrosslinked polyols crosslinked with polyols acids, acrylamidopropyl trimethyl ammonium chloride / acrylate copolymers, Octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-Hy hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolid on / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethylmeth acrylate / vinylcaprolactam terpolymers and optionally derivatized Cellulose ethers.
• - Symmetrical and asymmetrical, linear and branched dialkyl ethers with a total of between 12 and 36 C atoms, in particular 12 to 24 C atoms, for example, di-n-octyl ether, di-n-decyl ether, di-n-nonyl ether, di-n-un decyl ether and di-n-dodecyl ether, n-hexyl n-octyl ether, n-octyl-n-de cyl ether, n-decyl-n-undecyl ether, n-undecyl-n-dodecyl ether and n-hexyl-n-Un decyl ether and di-tert-butyl ether, di-iso-pentyl ether, di-3-ethyl decyl ether, tert-butyl n-octyl ether, iso-pentyl n-octyl ether and 2-methyl pentyl-n-octyl ether,
• Defoamers like silicones,
• Thickeners such as agar-agar, guar gum, alginates, xanthan gum, Gum arabic, karaya gurumi, locust bean gum, linseed gum men, dextrans, gelatin, pectins, cellulose derivatives, eg. Methylcellulose, Hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and Derivatives such as amylose, amylopectin and dextrins, clays such. B. bentonite or fully synthetic hydrocolloids such as. B. polyvinyl alcohol as well polyacrylamides
• - structurants such as maleic acid, mono-, di- and oligosaccharides,
• - perfume oils, dimethylisosorbide and cyclodextrins,
• Solubilizers, such as ethanol, isopropanol, ethylene glycol, propylene glycol, Glycerine and diethylene glycol,
• Dyes for staining the agent,  
• Antidandruff active ingredients such as Piroctone Olamine, Zinc Omadine and climbazol,
• - other substances for adjusting the pH,
• animal and vegetable protein hydrolysates, in particular elastin, Collagen, keratin, milk protein, soy protein, almond protein and Wheat protein hydrolysates, and their fatty acid condensation products and quaternized derivatives,
• - Vitamins and vitamin precursors, such as panthenol, its derivatives and biotin,
• - plant and honey extracts, in particular extracts of oak bark, Stinging nettle, witch hazel, hops, chamomile, burdock root, horsetail, Lime blossom, almond, aloe vera, coconut, mango, apricot, lime, Wheat, kiwi, melon, orange, grapefruit, sage, rosemary, birch, Meadowfoam, Quendel, Yarrow, Hauhechel, Meristem, Ginseng and ginger root,
• - Other active ingredients such as ceramides, allantoin, pyrrolidonecarboxylic acids, and bisabolol,
• - sunscreen,
• 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 penetration substances such as glycerol, propylene glycol monoethyl ether, Carbonates, bicarbonates, guanidines, ureas and primary, secondary tertiary and tertiary phosphates,
• Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers,
• - Pearlescing agents such as ethylene glycol mono- and distearate as well PEG-3 distearate,
• - Complexing agents such as EDTA, NTA, β-alaninediacetic acid and phosphone acids,
• - Reducing agents and stabilizers such. B. thioglycolic acid and their Derivatives, thiolactic acid, cysteamine, thiomalic acid, α-mercap toethanesulfonic acid and ascorbic acid, sulfites and dithionites,  
• - Propellants such as propane-butane mixtures, N ₂ O, dimethyl ether, CO ₂ , N ₂ and air and
• - antioxidants.

Regarding other components as well as quantity ranges for the individual Ingredients is based on the handbooks known to the expert, for. B.K. Schrader, bases and formulations of cosmetics, 2nd edition, Hüthig book Verlag, Heidelberg, 1989, referenced.

The constituents of the water-containing carrier are used to prepare the inventions Colorants according to the invention are used in quantities customary for this purpose; z. B. are emulsifiers in concentrations of 0.5 to 30 wt .-% and Thickener in concentrations of 0.1 to 25 wt .-% of the total Dye used.

The oxidative development of the staining can basically be done with atmospheric oxygen respectively. Preferably, however, a chemical oxidant is used, especially if, in addition to the coloring, a whitening effect on human hair is desired. The oxidizing agents are persulfates, chlorites and ins particular hydrogen peroxide or its addition products to urea, Melamine and potassium and sodium borate in question. Furthermore, it is possible to To perform oxidation with the aid of enzymes. The enzymes can be used for Transfer of atmospheric oxygen to the developer component or to To enhance the effect of small amounts of existing oxidizing agent serve. An example of an enzymatic process represents the procedure that Effect of small amounts (eg 1% by weight and less, based on the total Means) to amplify hydrogen peroxide by peroxidases.

Conveniently, the preparation of the oxidizing agent immediately before the hair color with the preparation of the oxidation dye precursors mixed. The resulting ready-to-use hair dye preparation should be ready before zugt a pH in the range of 6 to 10 have. Particularly preferred  the use of hair dyes in a mildly alkaline environment. The Application temperatures can range between 15 and 40 ° C lie. After a contact time of about 30 minutes, the hair dye by rinsing away from the hair to be dyed. The rinsing with egg A shampoo is omitted if a strong surfactant-containing carrier, eg. B. a Dyeing shampoo, was used.

The following examples are intended to explain the subject matter of the invention in more detail.

Examples colorations

A cream base of the following composition was first prepared [all statements are in g], unless stated otherwise:

tallow 17.0 Lorol®techn. ¹ 4.0 Texapon®N 28 ² 40.0 Dehyton®K ³ 25.0 Eumulgin®B 2 ⁴ 1.5 distilled water 12.5 ¹ C _12-18 fatty alcohol (HENKEL) @ ² sodium lauryl ether sulfate (about 28% by weight of active substance; CTFA name: sodium laureth sulfate) (HENKEL) @ ³ fatty acid amide derivative having a betaine structure of the formula R-CONH (CH ₂ ) ₃ N⁺ (CH ₃ ) ₂ CH ₂ COO⁻ (about 30% by weight of active substance, CTFA name cocoamidopropyl betaine) (HENKEL) @ ⁴ cetylstearyl alcohol with approx. 20 mol EO (CTFA name: Ceteareth-20) (HENKEL)

On the basis of this cream, the following hair dye cream emulsion was then prepared:

cream base 50.0 developer component 7.5 mmol Kupplerkomponente 7.5 mmol Na ₂ SO ₃ (inhibitor) 1.0 (NH ₄ ) ₂ SO ₄ 1.0 conc. ammonia solution ad pH 10 water ad 100

The ingredients were mixed together in order. After adding the Oxidation dye precursors and the inhibitor was first with kon centered ammonia solution adjusted the pH of the emulsion to 10, then was made up to 100 g with water.

The oxidative development of the dyeing was with 3 wt .-% hydrogen per oxide solution carried out as an oxidation solution. To this was added 100 g of the emulsion with 50 g of hydrogen peroxide solution (3 wt .-% strength) and mixed.

The staining cream was standardized to about 5 cm long strands, 90% applied gray, but not particularly pre-treated human hair and leave it at 32 ° C for 30 minutes. After completion of the dyeing process was rinsed the hair, washed with a conventional shampoo and on then dried.

For the finishes, the following coupler and developer components were used:

• - Coupler component
  2-allyl-1-naphthol (K1)
• - developer components
  p-toluenediamine (E1)
  2,4,5,6-tetraaminopyrimidine (E2)
  p-aminophenol (E3)
  1- (β-hydroxyethyl) -2,5-diaminobenzene (E4)
  3-methyl-4-aminophenol (E5)
  2- (2,5-diaminophenoxy) ethanol (E6).

The following colors were found:

Claims (8)

1. Use of substituted α-naphthols of the formula (I)
in which R ^{1 is} an optionally substituted alkenyl radical having 3 to 9 C atoms and R ^{2 is} a substituent selected from the group formed by H, Cl, Br, alkyl groups having 1 to 4 carbon atoms and / or Alkoxy groups having 1 to 4 carbon atoms, which may be in 3, 5, 6, 7 or 8 position,
as a coupler component in Oxidationshaarstärbemitteln. 2. Use according to claim 1, characterized in that R ^{1 is} a propenyl radical of the formula (II)
in which R ^{3 is} in turn hydrogen or a C ₁ - to C ₄ -alkyl group. 3. Use according to claims 1 and 2, characterized in that R ^{3 is} hydrogen. 4. Use according to claims 1 to 3, characterized in that R ^{2 is} hydrogen. 5. oxidation dye for dyeing keratin fibers containing Kupplerkom components and developer components in a hydrous carrier, characterized in that it is a coupler component α-naphthol derivative according to any one of claims 1 to 4. 6. oxidation colorant according to claim 5, characterized in that Developer components in an amount of 0.005 to 20 wt .-%, preferably Wise 0.1 to 5 wt .-%, and coupler components in an amount of 0.01 to 20 wt .-%, preferably 0.5 to 5 wt .-%, each based on the entire oxidation colorants are included. 7. oxidation dye according to claim 5 or 6, characterized in that at least one developer component selected from 2,4,5,6-tetra aminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 1- (β-hydroxy ethyl) -2,5-diaminobenzene, p-phenylenediamine, p-toluenediamine, p-aminophenol, 3-methyl-p-aminophenol and 2-aminomethyl-p-aminophenol. 8. oxidation dye according to one of claims 5 to 7, characterized gekenn that at least one substantive dye continue to contain is.