DE19842070A1 - Composition for dyeing of keratin containing fibers, e.g. hair, comprising a 5-arylpenta-2,4-dienylcarbonyl compound or salt - Google Patents

Abstract

Hair dye composition comprising a 5-arylpenta-2,4-dienylcarbonyl compound or salt of formula (I). Agent for dyeing keratin-containing fibers, especially human hair, containing as coloring component at least one 5-arylpenta-2,4-dienylcarbonyl compound of formula (I) or a physiologically acceptable salt of this: R<1> = H or 1-4C alkyl R<2> and R<3> (same or different) = H, halo, 1-4 C alkyl, 1-4C alkoxy, hydroxy-(1-4C)-alkoxy, hydroxy, nitro, amino group which is optionally substituted by 1-4C alkyl groups or which may be a constituent of a heterocycle, or a 1-4 C acyl group; or the two residues may together form a condensed-on benzene ring

Description

The invention relates to an agent for dyeing keratin fibers, in particular human hair containing 5-arylpenta-2,4-dienylcarbonyl compounds Formation of 5-arylpenta-2,4-dienylcarbonyl compounds as a coloring component in hair dye averaging and a process for dyeing keratin fibers, especially human hair.

For dyeing keratin fibers, e.g. B. hair, wool or furs come in all mean either direct dyes or oxidation dyes by oxidative Coupling one or more developer components with each other or with one or several coupler components are created for use. Coupler and developer compo nenten are also referred to as oxidation dye precursors.

Primary aromatic amines with a wide range are usually used as developer components ren, in the para or ortho position free or substituted hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used.

Special representatives are, for example, p-phenylenediamine, p-toluenediamine, 2,4,5,6-tetra aminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-diamino phenyl) ethanol, 2- (2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazo lon-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-amino phenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-tri amino-4-hydroxypyrimidine.

Usually m-phenylenediamine derivatives, naphthols, resor are used as coupler components cin and resorcinol derivatives, pyrazolones and m-aminophenols are used. As a coupler substance zen are particularly suitable for α-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2- methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-  diaminophenoxyethanol, 1-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1,3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-amino phenol, 2-methylresorcinol and 5-methylresorcinol.

With regard to other conventional dye components, it is expressly mentioned "Dermatology", edited by Ch. Culnan, H. Maibach, published by Marcel Dekker Inc., New York, Basel, 1986, vol. 7, Ch. Zviak, The Science of Hair Care, chap. 7, pages 248-250 (Direct dyes), and Chap. 8, pages 264-267 (oxidation dyes), and the "European inventory of cosmetic raw materials", 1996, published by the European Commission, available in diskette form from the Federal Association of German Industrial and Trading company for pharmaceuticals, health products and personal care products, Mannheim, Referred.

With oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color is generally done under the influence of oxidizing agents such as. B. H ₂ O ₂ , which in some cases can damage the fiber. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes have a sensitizing effect on people with sensitive skin. Direct dyes are appli ed under gentler conditions, but their disadvantage is that the dyeings often have insufficient fastness properties.

The use of the 5-arylpenta-2,4-dienylcarbonyl compounds described in more detail below for dyeing keratin fibers is not yet known.

The object of the present invention is to provide colorants for keratin fibers, in particular human hair, which are qualitatively at least equivalent in terms of color depth, gray coverage and fastness properties to the usual oxidation hair colorants, but without necessarily relying on oxidizing agents such as e.g. B. H ₂ O _{2 to be} instructed. In addition, the colorants may have no or only a very low sensitization potential.

Surprisingly, it has now been found that the 5-arylpenta- 2,4-dienylcarbonyl compounds also evolve in the absence of oxidizing agents excellent for dyeing keratin fibers. They also produce colorations  outstanding brilliance and depth of color and lead to diverse color nuances. The use of oxi However, agents should not be excluded in principle.

The invention relates to an agent for dyeing keratin-containing fibers, in particular human hair, containing 5-arylpenta-2,4-dienylcarbonyl compounds having the formula I or their physiologically tolerable salts,

in which R ^{1 represents} a hydrogen atom or a C ₁ -C ₄ alkyl group and
R ² and R ^{3 may be the} same or different and represent a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, hydroxy-C ₁ -C ₄ alkoxy group, a hydroxy group, nitro group , Amino group which is substituted by C ₁ -C ₄ alkyl groups or can be part of a heterocycle, or a C ₁ -C ₄ acyl group, where two of the radicals together can form a fused benzene ring.

Among keratin fibers are wool, furs, feathers and especially human hair to understand. In principle, however, the colorants according to the invention can also be used for dyeing other natural fibers, such as. B. cotton, jute, sisal, linen or silk, modified nature fibers such as B. regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as B. polyamide, polyacrylonitrile, polyurethane and polyester fibers be used.

The compounds with the formula I can be used as cis and also as trans isomers become. The compounds of the formula I are preferably selected from the group following 5-arylpenta-2,4-dienylcarbonyl compounds: 4-dimethylaminophenylpenta-2,4-die nal, 4-diethylaminophenylpenta-2,4-dienal, 4-methoxyphenylpenta-2,4-dienal, 3,4-dimethoxy phenylpenta-2,4-dienal, 2,4-dimethoxyphenylpenta-2,4-dienal, 4-piperidinophenylpenta-2,4- dienal, 4-morpholinophenylpenta-2,4-dienal, 4-pyrrolidinophenylpenta-2,4-dienal or 4-dime thylaminophenylhexa-2,4-dien-2-one, 4-diethylaminophenylhexa-2,4-dien-2-one, 4-methoxyphe nylhexa-2,4-dien-2-one, 3,4-dimethoxyphenylhexa-2,4-dien-2-one, 2,4-dimethoxyphenylhexa-  2,4-dien-2-one, 4-piperidinophenylhexa-2,4-dien-2-one, 4-morpholinophenylhexa-2,4-dien-2-one and 4-dimethylamino-1-naphthyl-penta-2,4-dienal.

These substances are known from the literature or are commercially available.

The above 5-arylpenta-2,4-dienylcarbonyl compounds having the formula I. are preferably in the agents according to the invention in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total colorant turns. They can be used as direct dyes or in the presence of oxidation dyes precursors are used.

Coloring agents that have the 5-arylpenta-2,4-dienylcarbonyl compounds as the coloring component of formula I alone, are preferably used for dyeing in the brown area. Colorings with an even higher brilliance and improved fastness properties (light fastness, Fastness to washing, fastness to rubbing), especially in the yellow, orange, violet, brown and black colors rich are achieved if the compounds of formula I used according to the invention together with at least one other component (in the following component B ge named), selected from compounds with primary or secondary amino group or Hydroxy group selected from primary or secondary aliphatic or aromatic Amines, nitrogen-containing heterocyclic compounds, amino acids, from 2 to 9 amino acidic oligopeptides and aromatic hydroxy compounds, and / or CH active connections. On the one hand, these are connections that are al Linen keratin fibers only weakly and only together with the 5-arylpenta-2,4- dienylcarbonyl compounds of formula I give brilliant colorations. On the other hand are but also compounds that are already used as oxidation dye precursors the.

The above-mentioned compounds of component B can be used in an amount of in each case 0.03 to 65, in particular 1 to 40 mmol, in each case based on 100 g of the total Colorant can be used.

Several different 5-arylpenta-2,4-dienylcarbonylver can also be used in all colorants bonds of formula I are used together; Likewise, several ver different compounds of component B are used together.  

The embodiment described above also includes the use of sol Chen substances, the reaction products of 5-arylpenta-2,4-dienylcarbonyl compounds of Represent formula I with the compounds of component B mentioned, as direct Colorants. Such reaction products can e.g. B. by briefly heating the two Components are obtained in stoichiometric amounts in aqueous alkali metal hydroxides, whereby they either precipitate out of the solution as a solid or by evaporating the solution be isolated from it. The reaction products can also be used in combination with other colors substances or dye precursors are used.

Suitable compounds with primary or secondary amino group as component B are e.g. B. primary aromatic amines such as N, N-dimethyl, N, N-diethyl, N- (2-hydroxyethyl) -N-ethyl, N, N-bis (2-hydroxyethyl) -, N- (2nd -Methoxyethyl-), 2,3-, 2,4-, 2,5-dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3- , 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o-, p-phenylenediamine, o-toluenediamine, 2,5-diaminotoluene, -phenol, -phenethol, 4-amino-3 -methylphenol, 2- (2,5-diaminophenyl) ethanol, 2,4-diaminophenoxyethanol, 2- (2,5-diaminophenoxy) ethanol, 4-methylamine, 3-amino-4- (2'-hydroxyethyloxy ) -, 3,4-methylenediamino-, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro-, 4-methylamino-, 2-methyl-5-amino-, 3-methyl-4-amino-, 2-methyl-5- (2-hydroxyethylamino) -, 6-methyl-3-amino-2-chloro, 2-methyl-5-amino-4-chloro, 3,4-methylenedioxy-, 5- ( 2-hydroxyethylamino) -4-methoxy-2-methyl-, 4-amino-2-hydroxymethylphenol, 1,3-diamino-2,4-dimethoxybenzene, 2-, 3-, 4-aminobenzoic acid, -phenylacetic acid, 2,3 -, 2.4-, 2.5-, 3.4- , 3,5-diaminobenzoic acid, 4-, 5-aminosalicylic acid, 3-amino-4-hydroxy-, 4-amino-3-hydroxybenzoic acid, 2-, 3-, 4-aminobenzenesulfonic acid, 3-amino-4-hydroxybenzenesulfonic acid, 4-amino-3-hydroxynaphthalene-1-sulfonic acid, 6-amino-7-hydroxynaphthalene-2-sulfonic acid, 7-amino-4-hydroxynaphthalene-2-sulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid , 3-amino-2-naphthoic acid, 3-aminophthalic acid, 5-aminoisophthalic acid, 1,3,5-, 1,2,4-triaminobenzene, 1,2,4,5-tetraaminobenzene, 2,4,5-triaminophenol, Pentaaminobenzene, hexaaminobenzene, 2,4,6-triaminoresorcinol, 4,5-diamino-catechol, 4,6-diaminopyrogallol, 3,5-diamino-4-hy droxybrenzcatechin, aromatic nitriles, anilines, in particular anilines containing nitro groups, such as 4-nitroaniline , 4-nitro-1,3-phenylenediamine, 2-nitro-4-amino-1- (2-hydroxyethylamino) benzene, 2-nitro-1-amino-4- [bis- (2-hydroxyethyl) amino] -benzene, 4-amino-2-nitrodiphenylamine-2'-car bonic acid, 2-amino-6-chloro-4-nitrophenol, 1-amino-5-chloro-4- (2-hydroxyethylamino) -2-nitro ben zol, aromatic anilines or phenols with a further aromatic radical, as shown in formula II

in the R ⁴ for a hydroxy or an amino group which can be substituted by C _1-4 -alkyl-, C _1-4 -hydroxyalkyl-, C _1-4 -alkoxy- or C _1-4 -alkoxy-C _1-4 - alkyl groups may be substituted, R ⁴ , R ⁶ , R ⁷ , R ⁸ and R ^{9 represents} hydrogen, a hydroxyl or an amino group which is substituted by C _1-4 -alkyl-, C _1-4 -hydroxyalkyl, C _{1 -4} alkoxy, C _1-4 aminoalkyl or C _1-4 alkoxyC _1-4 alkyl groups may be substituted, and
X for a direct bond, a saturated or unsaturated carbon chain, optionally substituted by hydroxyl groups, having 1 to 4 carbon atoms, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the formula III

Z- (CH ₂ -Y-CH ₂ -Z ') _o (III)

in which Y is a direct bond, a CH ₂ or CHOH group,
Z and Z 'independently of one another for an oxygen atom, an NR ¹⁰ group in which R ^{10 is} hydrogen, a C _1-4 alkyl or a hydroxyC _1-4 alkyl group, the group O- (CH ₂ ) _p -NH or NH- (CH ₂ ) _p '-O, where p and p' are 2 or 3, and
o means a number from 1 to 4,
such as 4,4'-diaminostilbene, 4,4'-diaminostilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene, 4,4'-diaminodiphenylmethane, sulfide, sulfoxide, amine. 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, -diphenyl ether, 3,3 ', 4,4'-tetraaminodiphenyl, 3,3', 4,4'-tetraamino-benzophenone, 1,3 - bis (2,4-diaminophen oxy) propane, 1,8-bis (2,5-diaminophenoxy) -3,6-dioxaoctane, 1,3-bis (4-aminophenylamino) per pan, -2 -propanol, 1,3-bis- [N- (4-aminophenyl) -2-hydroxyethylamino] -2-propanol, N, N-bis- [2- (4-aminophenoxy) ethyl] methylamine, N-phenyl -1,4-phenylenediamine.

The aforementioned compounds can be used both in free form and in the form of their physio logically compatible salts, in particular as salts of inorganic acids, such as salt or Sulfuric acid.  

Suitable nitrogen-containing heterocyclic compounds are e.g. B. 2-, 3-, 4-amino-, 2-amino- 3-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-diamino, 2-dimethylamino-5-amino, 2-methyl mino-3-amino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,6-dimethoxy-3,5-diamino-, 2,4,5-triami no-, 2,6-dihydroxy-3,4-dimethylpyridine, 2,4-dihydroxy-5,6-diamino-, 4,5,6-triamino-, 4-hydro xy-2,5,6-triamino-, 2-hydroxy-4,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triami no-, 2,4-, 4,5-diamino, 2-amino-4-methoxy-6-methyl-pyrimidine, 3,5-diaminopyrazole, -1,2,4-tri azole, 3-amino, 3-amino-5-hydroxypyrazole, 2-, 3-, 8-aminoquinoline, 4-aminoquinine, 2-, 6- Aminonicotinic acid, 5-aminoisoquinoline, 5-, 6-aminoindazole, 5-, 7-aminobenzimidazole, -benzo thiazole, 2,5-dihydroxy-4-morpholinoaniline and indole and indoline derivatives, such as 4-, 5-, 6-, 7- Aminoindole, 5,6-dihydroxyindole, 5,6-dihydroxyindoline and 4-hydroxyindoline. The aforementioned Compounds can be used both in free form and in the form of their physiologically acceptable Salts, e.g. B. as salts of inorganic acids, such as hydrochloric or sulfuric acid, who used the.

Suitable aromatic hydroxy compounds are e.g. B. 2-, 4-, 5-methylresorcinol, 2,5-dimethyl resorcin, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucin, Hydroxyhydroquinone, 2-, 3-, 4-methoxy, 3-dimethylamino, 2- (2-hydroxyethyl) -, 3,4-methylene dioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, -phenylacetic acid, gallic acid, 2,4,6-trihy droxybenzoic acid, acetophenone, 2-, 4-chlororesorcinol, 1-naphthol, 1,5-, 2,3-, 2,7-dihydroxy naphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2,7-naphtha linsulfonic acid.

1,2,3,3-Tetramethyl-3H-in can be mentioned as examples of CH-active compounds dolium iodide, 1,2,3,3-tetramethyl-3H-indolium-p-toluenesulfonate, 1,2,3,3-tetramethyl-3H-indo lium methanesulfonate, Fischer's base (1,3,3-trimethyl-2-methylene indoline), 2,3-dimethyl benzothiazolium iodide, 2,3-dimethyl-benzothiazolium-p-toluenesulfonate, rhodanine, rhodanine-3 acetic acid, 1-ethyl-2-quinaldinium iodide, 1-methyl-2-quinaldinium iodide barbituric acid, thiobar bituric acid, 1,3-dimethylthiobarbituric acid, diethylthiobarbituric acid, oxindole, 3-indoxy acetate, Coumaranone and 1-methyl-3-phenyl-2-pyrazolinone.

All naturally occurring and synthetic α-ami are preferred as amino acids no acids in question, e.g. B. by hydrolysis of vegetable or animal proteins, e.g. B. Collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein, available chen amino acids. Both acidic and alkaline amino acids be used. Preferred amino acids are arginine, histidine, tyrosine, phenylalanine,  DOPA (dihydroxyphenylalanine), ornithine, lysine and tryptophan. But also other amino acids ren, such as B. 6-aminocaproic acid can be used.

The oligopeptides can be naturally occurring or synthetic oligopeptides, however the oligopeptides contained in polypeptide or protein hydrolyzates, if they are about sufficient water for use in the colorants of the invention dispose of solubility. As examples are e.g. B. Glutathione and those in the hydrolysates of Kolla gene containing keratin, casein, elastin, soy protein, wheat gluten or almond protein to call gopeptides. Preference is given to agents which contain the compounds having the formula I. together with compounds with primary or secondary amino group or with aromatic Contain hydroxy compounds.

The compounds of component B are particularly preferably selected from the Group consisting of N- (2-hydroxyethyl) -N-ethyl-, 2-chloro-p-phenylenediamine, N, N-bis (2- Hydroxyethyl) -p-phenylenediamine, 4-aminophenol, p-phenylenediamine, 2- (2,5-diaminophenyl) - ethanol, 2,5-diaminotoluene, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro-, 2-methyl-5-amino-, 3-methyl-4-amino, 2-methyl-5- (2-hydroxyethylamino) -, 2-methyl-5-amino-4-chloro, 6-methyl-3- amino-2-chloro, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 3,4-methyl lendioxyphenol, 3,4-diaminobenzoic acid, 2,5-diamino-, 2-dimethylamino-5-amino-, 3-amino- 2-methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, 3,5-diamino-2,6-dimethoxy-, 2,6-dihy doxy-3,4-dimethylpyridine, 2-hydroxy-4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2,4,5,6-tetra amino, 2-methylamino-4,5,6-triamino-pyrimidine, 3,5-diaminopyrazole, 3-amino-5-hydroxypyra zol, 5,6-dihydroxyindole and 5,6-dihydroxyindoline and their preferably inorganic Acids formed physiologically acceptable salts.

On the presence of oxidizing agents, e.g. B. H ₂ O ₂ , can be omitted. However, it can It may be desirable to add hydrogen peroxide or other oxidizing agents to the agents according to the invention to achieve the shades that are lighter than the keratin-containing fiber to be colored. Oxidizing agents are generally used in an amount of 0.01 to 6% by weight, based on the application solution. An oxidant preferred for human hair is H ₂ O ₂ .

In a preferred embodiment, the colorants according to the invention contain white teren modification of the color shades in addition to the compounds contained according to the invention additionally conventional direct dyes, e.g. B. from the group of nitrophenylenediamines, Nitroaminophenols, anthraquinones or indophenols, such as. B. the international one  Designations 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 picramic acid 2-amino-6-chloro-4-nitro phenol, 4-amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, 4- N-ethyl-1,4-bis (2'-hydroxyethylamino) -2-nitrobenzene hydrochloride and 1-methyl-3-nitro-4- (2'- hydroxyethyl) aminobenzene. The inventive agents according to this embodiment contain the substantive dyes preferably in an amount of 0.01 to 20% by weight, based on the entire colorant.

It is not necessary that the oxidation dye precursors or those optionally contain direct dyes each represent uniform compounds. Rather, in the colorants of the invention, due to the manufacturing process for the individual NEN dyes, in minor amounts, other components may be included, so far these do not adversely affect the coloring result or for other reasons, e.g. B. Toxicity logical, must be excluded.

The colorants according to the invention already result at a physiologically compatible temperature temperatures of less than 45 ° C intense coloring. They are therefore particularly suitable for dyeing of human hair. The dye can be used on human hair agents are usually incorporated into a water-containing cosmetic carrier. Ge Suitable water-containing cosmetic carriers are e.g. B. creams, emulsions, gels or surfactant-containing foaming solutions such as B. shampoos or other preparations for the application on the keratin fibers are suitable. If necessary, it is too possible to incorporate the colorants in anhydrous carriers.

Furthermore, the colorants according to the invention can all be known in such preparations contain active ingredients, additives and auxiliary substances. In many cases, the colorants contain at least Mostly a surfactant, in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases it has turned out to be Proven partially, the surfactants from anionic, zwitterionic or nonionic surfactants to select.

Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carb oxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms. In addition, the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups. 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 carbon 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 carbon atoms and x = 0 or 1 to 16,
• Acyl sarcosides with 10 to 18 carbon atoms in the acyl group,
• Acyl taurides with 10 to 18 carbon atoms in the acyl group,
• Acyl isethionates with 10 to 18 carbon atoms in the acyl group,
• - Monosulfonic succinate and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl esters with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups,
• Linear alkanesulfonates with 12 to 18 carbon atoms,
• Linear alpha-olefin sulfonates with 12 to 18 carbon atoms,
• - Alpha-sulfofatty acid methyl esters of fatty acids with 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 a preferably linear alkyl group with 10 to 18 carbon atoms and x = 0 or 1 to 12,
• Mixtures of surface-active hydroxysulfonates according to DE-A-37 25 030,
• - Sulphated hydroxyalkyl polyethylene and / or hydroxyalkylene propylene glycol ether according to DE-A-37 23 354,
• - Sulfonates of unsaturated fatty acids with 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 to 15 molecules of ethylene oxide and / or propylene oxide on fatty alcohols with 8 to 22 Represent carbon atoms.

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

Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one -COO ^(-) - or -SO ₃ ^(-) 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-dimethylammonium glycinate, for example the cocoacylaminopropyl-dimethylammonium glycinate, and 2-alkyl -3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate. A preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine.

Ampholytic surfactants are surface-active compounds which, in addition to a C _8-18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO ₃ H group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkyl amidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkyl aminoacetic acid each with about 8 up to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C _12-18 acylsarcosine.

Nonionic surfactants contain z as a hydrophilic group. B. a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group. Such connections are, for example

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

Examples of the cationi which can be used in the hair treatment compositions according to the invention In particular, surfactants are quaternary ammonium compounds. Ammo are preferred  nium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and Trialkylmethylammoniumchloride, e.g. B. Cetyltrimethylammonium chloride, stearyltrimethylam monium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldi methylbenzylammonium chloride and tricetylmethylammonium chloride. More fiction The quaternized protein hydrolyzates represent usable cationic surfactants. Also suitable according to the invention are cationic silicone oils such as those in the Commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethyl sifylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino modified Silicon, which is also called Amodimethicone), SM-2059 (Manufacturer: General Elec tric), SLM-55067 (manufacturer: Wacker) and Abil®-Quat 3270 and 3272 (manufacturer: Th. Gold schmidt; diquaternary polydimethylsiloxanes, Quaternium-80).

Alkylamidoamines, especially fatty acid amidoamines such as that under the name Tego Amid®S 18 available stearylamidopropyldimethylamine are characterized by a good con ditioning effect especially due to its good biodegradability.

Quaternary ester compounds are also very readily biodegradable "Esterquats", such as the methylhydroxyalkyl sold under the trademark Stepantex® dialkoyloxyalkylammonium methosulfates.

This is an example of a quaternary sugar derivative that can be used as a cationic surfactant Commercial product Glucquat®100, according to CTFA nomenclature a "Lauryl Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride ".

The compounds with alkyl groups used as surfactants can each be a act uniform substances. However, it is usually preferred in the manufacture of these Substances from native vegetable or animal raw materials, so that one sub punch mixtures with different alkyl chain lengths depending on the respective raw material receives.

In the case of surfactants, the addition products of ethylene and / or propylene oxide with fatty alcohol hole or derivatives of these investment products, both products with a "normal" homolog distribution as well as those with a narrow homolog distribution be used. Under "normal" homolog distribution, mixtures of Homologues understood that one under the implementation of fatty alcohol and alkylene oxide  Use of alkali metals, alkali metal hydroxides or alkali metal alcoholates as kata lysators receives. On the other hand, narrow homolog distributions are obtained if at for example hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates can be used as catalysts. The use of pro Products with a narrow homolog distribution can be preferred.

Other active ingredients, auxiliaries and additives are, for example

• - Nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers, poly vinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes,
• - cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary Groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammoni umchloride copolymers, dimethylaminoethyl methacrylate quaternized with diethyl sulfate Vinyl pyrrolidone copolymers, vinyl pyrrolidone imidazolinium methochloride copolymers and quaternized polyvinyl alcohol,
• - zwitterionic and amphoteric polymers such as acrylamidopropyl trimethyl ammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert-butyla minoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers,
• Anionic polymers such as polyacrylic acids, crosslinked polyacrylic acids, Vinyl acetate / crotonic acid copolymers, vinylpyrrolidone-vinyl acrylate copolymers, vinyllace tat / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride co polymers and acrylic acid / ethyl acrylate / N-tert-butylacrylamide terpolymers,
• Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, Karaya gum, locust bean gum, linseed gums, dextrans, cellulose deri vate, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch Fractions and derivatives such as amylose, amylopectin and dextrins, clays such. B. bentonite or fully synthetic hydrocolloids such. B. polyvinyl alcohol,
• Structurants such as glucose and maleic acid,
• Hair-conditioning compounds such as phosphofipids, for example soy lecithin, Egg lecithin and cephaline, as well as silicone oils,
• Protein hydrolyzates, in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and qua ternized protein hydrolyzates,
• - perfume oils, dimethyl isosorbide and cyclodextrins,
• - Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and Diethylene glycol,
• - anti-dandruff agents such as Piroctone Olamine and Zink Omadine,  
• - other substances for adjusting the pH value,
• - Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their Salts, plant extracts and vitamins,
• - cholesterol,
• - light stabilizers,
• - consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
• - Fats and waxes such as walrus, beeswax, montan wax, paraffins, fatty alcohols and Fatty acid esters,
• - fatty acid alkanolamides,
• Complexing agents such as EDTA, NTA and phosphonic acids,
• Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, Hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phos phate, imidazole, tannins, pyrrole,
• Opacifiers such as latex,
• - pearlescent agents such as ethylene glycol mono- and distearate,
• - blowing agents such as propane-butane mixtures, N ₂ O, dimethyl ether, CO ₂ and air and
• - antioxidants.

The constituents of the water-containing carrier are used to produce the inventive Colorants used in amounts customary for this purpose; e.g. B. are emulsifiers in Concentrations from 0.5 to 30 wt .-% and thickeners in concentrations from 0.1 to 25 wt .-% of the total colorant used.

For the coloring result it can be advantageous to add ammonium or metal salts to the coloring agents to admit. Suitable metal salts are e.g. B. formates, carbonates, halides, sulfates, Bu tyrates, valemates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propio nates, phosphates and phosphonates of alkali metals, such as potassium, sodium or lithium, earth alkali metals, such as magnesium, calcium, strontium or barium, or of aluminum, Man gan, iron, cobalt, copper or zinc, with sodium acetate, lithium bromide, calcium bromide, Calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate are preferred. These salts are preferably in an amount from 0.03 to 65, in particular from 1 to 40, mmol based on 100 g of the total dye means included.

The pH value of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.  

Another object of the present invention relates to the use of 5-arylpenta-2,4-dienylcarbonyl compounds having the formula I or their physiologically tolerable salts

in which R ^{1 represents} a hydrogen atom or a C ₁ -C ₄ alkyl group and
R ² and R ^{3 may be the} same or different and represent a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, hydroxy-C ₁ -C ₄ alkoxy group, a hydroxy group, nitro group , Amino group which is substituted by C ₁ -C ₄ alkyl groups or can be part of a heterocycle, or are a C ₁ -C ₄ acyl group, it also being possible for two of the radicals together to form a fused-on benzene ring,
as a coloring component in oxidation hair dyes.

Yet another object of the present invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which a colorant,

• A) at least one 5-arylpenta-2,4-dienylcarbonyl compound having the formula I or its physiologically tolerable salts
  in which R ^{1 represents} a hydrogen atom or a C ₁ -C ₄ alkyl group and
  R ² and R ^{3 may be the} same or different and represent a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, hydroxy-C ₁ -C ₄ alkoxy group, a hydroxyl group, nitro group , Amino group which may be substituted by C ₁ -C ₄ -alkyl groups or may be part of a heterocycle, or a C ₁ -C ₄ -acyl group, it also being possible for two of the radicals together to form a condensed benzene ring,
• B) at least one compound with primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic ami NEN, nitrogen-containing heterocyclic compounds, amino acids, from 2 to 9 amino acidic oligopeptides and aromatic hydroxy compounds, and / or at least one CH-active compound,

and common cosmetic ingredients applied to the keratin fibers, some Leave time, usually about 30 minutes, on the fiber and then remove it again rinses or is washed out with a shampoo.

The 5-arylpenta-2,4-dienylcarbonyl compounds of the formula I and the compounds of the com component B can either be applied to the hair simultaneously or else one after the other, it doesn't matter which of the two components is applied first becomes. The optionally contained ammonium or metal salts can be the first or be added to the second component. Between applying the first and the second component can be up to 30 minutes apart. Pretreatment too the fibers with the saline solution is possible.

The 5-arylpenta-2,4-dienylcarbonyl compounds of the formula I and the compounds of the com Component B can either be stored separately or together, either in one liquid to pasty preparation (aqueous or anhydrous) or as a dry powder. Who If the components are stored together in a liquid preparation, this should be used for Reduction of a reaction of the components to be largely anhydrous. At the separate The reactive components are only stored immediately before use other intimately mixed. Dry storage is usually done before use a defined amount of warm (50 to 80 ° C) water added and a homogeneous Mi manufactured.  

Examples Preparation of a coloring solution

A slurry of 10 mmoles of a 5-arylpenta-2,4-dienylcarbonate compound became of the formula I, 10 mmol of an oxidation dye precursor, 10 mmol of sodium acetate and prepares a drop of a 20% fatty alkyl ether sulfate solution in 100 ml of water. The on Slurry was briefly heated to approx. 80 ° C and filtered after cooling, the pH was then set to 6.

A streak of 90% was not grayed in this dyeing solution at 30 ° C. for 30 minutes, not pretreated human hair introduced. The streak was then lukewarm for 30 seconds Rinsed water, dried with warm air and then combed out.

The respective color shades and color depths are shown in Table 1 below ben.

The color depth was rated on the following scale:
-: no or very pale color
(+): weak intensity
+: medium intensity
+ (+): medium to strong intensity
++: strong intensity
++ (+): strong to very strong intensity
+++: very strong intensity

Colorings with 5- (4-N, N-dimethylaminophenyl) -penta-2,4-dien-1-al

Table 1

Claims (12)

1. Agent for dyeing keratin-containing fibers, in particular human hair, containing at least one 5-arylpenta-2,4-dienylcarbonyl compound having the formula I or its physiologically tolerable salts as the coloring component
in which R ^{1 represents} a hydrogen atom or a C ₁ -C ₄ alkyl group and
R ² and R ^{3 can be the} same or different and represent a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, hydroxy-C ₁ -C ₄ alkoxy group, a hydroxy group, nitro group, Amino group which can be substituted by C ₁ -C ₄ alkyl groups or can be part of a heterocycle, or a C ₁ -C ₄ acyl group, it also being possible for two of the radicals together to form a fused-on benzene ring. 2. Composition according to claim 1, characterized in that as compounds with the Formula I 4-dimethylaminophenylpenta-2,4-dienal, 4-diethylaminophenylpenta-2,4-di enal, 4-methoxyphenylpenta-2,4-dienal, 3,4-dimethoxyphenylpenta-2,4-dienal, 2,4-di methoxyphenylpenta-2,4-dienal, 4-piperidinophenylpenta-2,4-dienal, 4-morpholinophe nylpenta-2,4-dienal, 4-pyrrolidinophenylpenta-2,4-dienal or 4-dimethylaminophenyl hexa-2,4-dien-2-one, 4-diethylaminophenylhexa-2,4-dien-2-one, 4-methoxyphenylhexa- 2,4-dien-2-one, 3,4-dimethoxyphenylhexa-2,4-dien-2-one, 2,4-dimethoxyphenylhexa-2,4- dien-2-one, 4-piperidinophenylhexa-2,4-dien-2-one, 4-morpholinophenylhexa-2,4-dien-2- on and 4-dimethylamino-1-naphthyl-penta-2,4-dienal can be used. 3. Agent according to one of claims 1 to 2, characterized in that the 5-aryl penta-2,4-dienylcarbonyl compounds having the formula I in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total dye means are included. 4. Agent according to one of claims 1 to 3, characterized in that it is additionally at least one compound with primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic  Amines, nitrogen-containing heterocyclic compounds, amino acids, from 2 to 9 Amino acid-based oligopeptides and aromatic hydroxy compounds, and / or contains at least one CH-active compound. 5. Means according to claim 4, characterized in that the further connection is selected from
primary or secondary amines from the group consisting of N- (2-hydroxyethyl) -N-ethyl-, N- (2-methoxyethyl-), 2,3-, 2,4-, 2,5-dichloro-p -phenylene diamine, 2-chloro-p phenylene diamine, N, N-bis (2-hydroxyethyl) -p-phenylene diamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3-, 4-aminophenol, o -, m-, p-Phenylenediamine, 2,4-Diami nophenoxyethanol, 2- (2,5-Diaminophenyl) -ethanol, 2,5-Diaminotoluol, -phenol, -phenethol, 4-Methylamino-, 3-Amino-4 - (2'-Hydroxyethyloxy) -, 3,4-methylenediamino, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro, 4-methylamino, 2-methyl-5-amino, 3-methyl -4-amino-, 2-methyl-5- (2-hydroxyethylamino) -, 2-methyl-5-amino-4-chloro, 6-methyl-3-amino-2-chloro, 5- (2- Hydroxyethylamino) -4-methoxy-2-methyl-, 4-amino-2-aminomethyl-phenol, 4-amino-2-hydroxymethylphenol, 1,3-diamino-2,4-dimethoxy benzene, 2-, 3-, 4 -Aminobenzoic acid, -phenylacetic acid, 2,3-, 2,4-, 2,5-, 3,4-, 3,5-diaminobenzoic acid, 4-, 5-aminosalicylic acid, 3-amino-4-hydroxy-, 4 -Amino-3-hydroxy benzoic acid e, 2-, 3-, 4-aminobenzenesulfonic acid, 3-amino-4-hydroxybenzenesulfonic acid, 4-amino-3-hydroxynaphthalene-sulfonic acid, 6-amino-7-hydroxynaphthalene-2-sulfonic acid, 7-amino-4-hydroxynaphthalene -2-sulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid, 3-amino-2-naphthoic acid, 3-aminophthalic acid, 5-aminoisophthalic acid, 1,3,5-, 1,2,4-triaminobenzene , 1,2,4,5-tetraaminobenzene tetrahydrochloride, 2,4,5-triami nophenol trihydrochloride, pentaaminobenzene pentahydrochloride, hexaaminobenzene hexahydrochloride, 2,4,6-triaminoresorcinol trihydrochloride, 4,5-diaminobenzate catechol sulfate, 4, 6-diaminopyrogallol dihydrochloride, 3,5-diamino-4-hydroxycatechol sulphate, aromatic nitriles, anilines, in particular anilines containing nitro groups, such as 4-nitro aniline, 4-nitro-1,3-phenylenediamine, 2-nitro 4-amino-1- (2-hydroxyethylamino) benzene, 2-nitro-1-amino-4- [bis- (2-hydroxyethyl) amino] benzene, 4-amino-2-nitrodiphenylamine-2'-carboxylic acid , 2-amino-6-chloro-4-nitrophenol, 1-amino-5-chloro-4- (2-hydroxyethylam ino) - 2-nitrobenzene, aromatic anilines or phenols with a further aromatic radical such as 4,4'-diaminostilbene dihydrochloride, 4,4'-diaminostilbene-2,2'-disulfonic acid, Na salt, 4,4'- Diaminodiphenylmethane, sulfide, sulfoxide, amine, 4,4'-diaminodiphenylamine-2-sulphonic acid, 4,4'-diaminobenzophenone, diphenyl ether, 3,3 ', 4,4'-tetraaminodiphenyl tetrahydrochloride, 3,3' , 4,4'-tetraamino-benzophenone, 1,3-bis (2,4-diaminophenoxy) propane tetrahydrochloride, 1,8-bis (2,5-diaminophenoxy) -3,6-dioxaoctane tetrahydrochloride , 1,3-bis- (4-aminophenylamino) propane, -2-propanol, 1,3-bis- [N- (4-aminophenyl) -2-hydroxyethylamino] -2-propanol, N, N-bis- [2- (4-aminophenvxy) ethyl] methylamine-trihy drochloride,
nitrogen-containing heterocyclic compounds selected from the group consisting of 2-, 3-, 4-amino, 2-amino-3-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-dia mino-, 2-dimethylamino-5-amino-, 3-amino-2-methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, 3,5-diamino-2,6-dimethoxy-, 2nd , 4,5-triamino, 2,6-dihydroxy-3,4-dimethylpyridine, 4,5,6-triamino, 2-hydroxy-4,5,6-triamino, 4-hydroxy-2,5 , 6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amino-4-methoxy- 6-methyl-pyrimidine, 2,3,4-trimethylpyrrole, 2,4-dimethyl-3-ethyl-pyrrole, 3,5-diaminopyrazole, -1,2,4-triazole, 3-amino, 3-amino -5-hydroxypyrazole, 2-, 3-, 8-aminoquinoline, 4-aminoquinoline, 2-, 6-aminonicotinic acid, 5-aminoisoquinoline, 5-, 6-aminoindazole, 5-, 7- aminobenzimidazole, -benzothiazole, 2,5-dihydroxy-4-morpholinoaniline and indole and indoline derivatives, such as 4-, 5-, 6-, 7-aminoindole, 4-, 5-, 6-, 7-hydroxyindole, 5,6-dihydroxyindole, 5 , 6-dihydroxyindoline and 4-hydroxyindoline, and each s from the physiologically tolerable salts of these compounds formed with preferably inorganic acids,
aromatic hydroxy compounds selected from the group consisting of 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-, 3-, 4-methoxy -, 3-dimethylamino, 2- (2-hydroxyethyl) -, 3,4-methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, phenylacetic acid, gallic acid, 2,4,6-trihydroxybenzoic acid, acetophe non, 2-, 4-chiorresorcinol, 1-naphthol, 1,5-, 2,3-, 2,7-dihydroxynaphthaün, 6-dimethyia mino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2, 7-naphthalenesulfonic acid, and
CH-active compounds selected from the group consisting of 1,2,3,3-tetra methyl-3H-indolinium iodide, 1,2,3,5-tetramethylindolinium p-toluenesulfonate, 1,2,3,5-Te tramethylindolinium methanesulfonate, 2,3-dimethylbenzothiazolium iodide, 2,3-dimethylbenzothiazolium-p-toluenesulfonate, rhodanine, rhodanine-3-acetic acid, 1-ethyl (methyl) -2-quinaldinium iodide, barbituric acid, thiobarbituric acid, 1,3-dimethyl (ethyl ) thiobarbituric acid, oxindole, coumaranone and 1-methyl-3-phenyl-2-pyrazolinone. 6. Composition according to claim 5, characterized in that the further connection is selected from the group consisting of N- (2-hydroxyethyl) -N-ethyl-, 2-chloro-p-phe nylenediamine, N, N-bis (2-hydroxyethyl) p-phenylenediamine, 4-aminophenol, p-phenylene diamine, 2- (2,5-diaminophenyl) ethanol, 2,5-diaminotoluene, 3,4-methylenedioxyaniline, 3-  Amino-2,4-dichloro, 2-methyl-5-amino, 3-methyl-4-amino, 2-methyl-5- (2-hydroxyethyl amino) -, 2-methyl-5-amino-4-chloro, 6-methyl-3-amino-2-chloro, 2-aminomethyl-4-ami nophenol, 2-hydroxymethyl-4-aminophenol 3,4-methylenedioxyphenol, 3,4-diaminobes zoic acid, 2,5-diamino, 2-dimethylamino-5-amino, 3-amino-2-methylamino-6-meth oxy, 2,3-diamino-6-methoxy, 3,5-diamino-2,6-dimethoxy, 2,6-dihydroxy-3,4-dime thylpyridine, 2-hydroxy-4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-pyrimidine, 3,5-diaminopyrazole, 3-amino-5-hydroxypyra zol, 5,6-dihydroxyindole and 5,6-dihydroxyindoline and in each case from the preferred physiologically acceptable salts of these ver bonds. 7. Composition according to one of claims 1 to 6, characterized in that it draws directly dyes from the group of nitrophenylenediamines, nitroaminophenols, An thrachinones or indophenols preferably in an amount of 0.01 to 20% by weight, based on the entire colorant. 8. Agent according to one of claims 1 to 7, characterized in that ammonium or metal salts selected from the group of formates, carbonates, halides, Sulfates, butyrates, valemates, capronates, acetates, lactates, glycolates, tartrates, citrates, Gluconates, propionates, phosphates and phosphonates of alkali metals, such as potassium, Sodium or lithium, alkaline earth metals such as magnesium, calcium, strontium or Ba rium, or of aluminum, manganese, iron, cobalt, copper or zinc, who add the. 9. Composition according to one of claims 1 to 8, characterized in that it contains oxidizing agents, in particular H ₂ O ₂ , in an amount of 0.01 to 6% by weight, based on the application solution. 10. Agent according to one of claims 1 to 9, characterized in that it is anioni contains, zwitterionic or nonionic surfactants. 11. Use of 5-arylpenta-2,4-dienylcarbonyl compounds with the formula I or their physiologically tolerable salts
in which R ^{1 represents} a hydrogen atom or a C ₁ -C ₄ alkyl group
R ² and R ^{3 can be the} same or different and represent a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, hydroxy-C ₁ -C ₄ alkoxy group, a hydroxy group, nitro group, Amino group which can be substituted by C ₁ -C ₄ alkyl groups or can be part of a heterocycle, or a C ₁ -C ₄ acyl group, where two of the radicals together can form a fused-on benzene ring,
as a coloring component in oxidation hair dyes. 12. A process for dyeing keratin-containing fibers, in particular human hair, in which a colorant

• A) at least one 5-arylpenta-2,4-dienylcarbonyl compound having the formula I or its physiologically tolerable salts
  in which R ^{1 represents} a hydrogen atom or a C ₁ -C ₄ alkyl group and
  R ² and R ^{3 can be the} same or different and represent a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, hydroxy-C ₁ -C ₄ alkoxy group, a hydroxy group, nitro group, Amino group which can be substituted by C ₁ -C ₄ alkyl groups or can be part of a heterocycle, or a C ₁ -C ₄ acyl group, where two of the radicals can together form a fused-on benzene ring,
• B) at least one compound with a primary or secondary amino group or hydroxy group, selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides and aromatic hydroxy compounds composed of 2 to 9 amino acids, and / or at least one CH-active Compound, as well as usual cosmetic ingredients applied to the keratin fibers, left on the fiber for some time, usually about 30 minutes, and then rinsed out or washed out with a shampoo.