AU5745499A - Agents for dyeing fibres containing keratin - Google Patents

Description

WO 00/15183 1 PCT/EP99/06525 Agents for Dyeing Fibres Containing Keratin This invention relates to a composition containing 5-arylpenta-2,4 dienyl carbonyl compounds for coloring keratin-containing fibers, more particularly human hair, to the use of 5-arylpenta-2,4-dienyl carbonyl compounds as a coloring component in hair coloring compositions and to a 5 process for coloring keratin-containing fibers, more particularly human hair. In general, keratin-containing fibers, for example hair, wool or pelts, are dyed either with substantive dyes or with oxidation dyes which are formed by oxidative coupling of one or more primary intermediates with one another or with one or more secondary intermediates. Primary and 10 secondary intermediates are also known as oxidation dye precursors. The primary intermediates normally used are primary aromatic amines containing another free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6 15 tetraaminopyrimidine and derivatives thereof. Special representatives are, for example, p-phenylenediamine, p toluylenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N,N-bis-(2 hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)-ethanol, 2-(2,5 diaminophenoxy)-ethanol, 1 -phenyl-3-carboxyamido-4-amino-5-pyrazolone, 20 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl 4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6 diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine. The secondary intermediates used are generally m-phenylene diamine derivatives, naphthols, resorcinol and resorcinol derivatives, 25 pyrazolones and m-aminophenols. Particularly suitable secondary inter mediates are a-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5 amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl WO 00/15183 3 PCT/EP99/06525 In addition, the colorants according to the invention would have very little, if any, sensitizing potential. It has surprisingly been found that the 5-arylpenta-2,4-dienyl carbonyl compounds corresponding to formula (I) below are eminently 5 suitable for coloring keratin-containing fibers, even in the absence of oxidizing agents. They give colors with excellent brilliance and depth of color and lead to a wide variety of shades. In principle, however, oxidizing agents may be present. The present invention relates to a composition for coloring keratin 10 containing fibers, more particularly human hair, containing 5-arylpenta-2,4 dienyl carbonyl compounds corresponding to formula 1: 0 R R1 R3I / \ / R3 (I) 15 in which

R

1 is a hydrogen atom or a C 1 4 alkyl group and

R

2 and R 3 , which may be the same or different, represent a hydrogen atom, a halogen atom, a C 1 4 alkyl group, a C14 alkoxy group, a hydroxy-C1-4 alkoxy group, a hydroxy group, a nitro group, an amino group which may 20 be substituted by C14 alkyl groups or may be part of a heterocycle, or a C1_4 acyl group; two of the substituents together may even form a fused benzene ring, or physiologically compatible salts of such 5-arylpenta-2,4-dienyl carbonyl compounds. 25 In the context of the invention, keratin-containing fibers are understood to include wool, pelts, feathers and, in particular, human hair. In principle, however, the colorants according to the invention may also be used to color other natural fibers such as, for example, cotton, jute, sisal, WO 00/15183 5 PCT/EP99/06525 invention are used together with at least one other component (hereinafter referred to as component B) selected from compounds containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic 5 compounds, amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or CH-active compounds. These are, on the one hand, compounds which on their own color keratin-containing fibers very weakly and only produce brilliant colors in conjunction with the 5-arylpenta-2,4-dienyl carbonyl compounds corresponding to formula I and, 10 on the other hand, compounds which are already used as oxidation dye precursors. The above-mentioned compounds of component B may be used in a quantity of 0.03 to 65 mmol and more particularly 1 to 40 mmol, based on 100 g of the colorant as a whole. 15 In all coloring compositions, several different 5-arylpenta-2,4-dienyl carbonyl compounds corresponding to formula I may also be used together. Similarly, several different compounds of component B may also be used together The embodiment described above also encompasses the use of 20 substances which represent reaction products of 5-arylpenta-2,4-dienyl carbonyl compounds corresponding to formula I with the above-mentioned compounds of component B as substantive colorants. Reaction products such as these may be obtained, for example, by briefly heating the two components in stoichiometric quantities in aqueous alkali metal hydroxides, 25 the reaction products either precipitating from the solution as a solid or being isolated from the solution by concentration through evaporation. The reaction products may also be used in combination with other dyes or dye precursors. Suitable compounds containing a primary or secondary amino group 30 for component B are, for example, primary aromatic amines, such as N,N- WO 00/15183 7 PCT/EP99/06525 radical corresponding to formula 1l: R5 R4 R7 R8 R6 R9 (II) 5 in which R4 is a hydroxy group or an amino group which may be substituted by C 1 .4 alkyl, C 1 .4 hydroxyalkyl, C1.4-alkoxy or C1.

4 -alkoxy-C 1 .4-alkyl groups,

R

4 , R 6 , R 7 , R 8 and R 9 represent hydrogen, a hydroxy group or an amino group which may be substituted by C 1 .4 alkyl, C 1

.

4 hydroxyalkyl, C 1

.

4 alkoxy, C1.4 aminoalkyl or C1.4-alkoxy-Cl.

4 -alkyl groups and 10 X is a direct bond, a saturated or unsaturated, optionally hydroxy substituted carbon chain containing 1 to 4 carbon atoms, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom or a group corresponding to formula Ill: 15

Z-(CH

2

-Y-CH

2 -Z')o (1ll) in which Y is a direct bond, a CH 2 or CHOH group, Z and Z' independently of one another represent an oxygen atom, an NR 1 0 20 group, where R 10 is hydrogen, a C 1 .4 alkyl or a hydroxy-C 1

.

4 -alkyl group, the group O-(CH 2 )p-NH or NH-(CH 2 )p.-O, where p and p' = 2 or 3, and o is a number of 1 to 4, such as for example 4,4'-diaminostilbene, 4,4'-diaminostilbene-2,2'-disul fonic acid monosodium or disodium salt, 4-amino-4'-dimethylaminostilbene, 25 4,4'-diaminodiphenyl methane, -sulfide, -sulfoxide, -amine, 4,4' diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, -diphenyl ether, 3,3',4,4'-tetraaminodiphenyl, 3,3'4,4'-tetraaminobenzo- WO 00/15183 9 PCT/EP99/06525 resorcinol, 1-naphthol, 1,5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethyl amino-4-hydroxy-2-naphthalene sulfonic acid, 3,6-dihydroxy-2,7-naphtha lene sulfonic acid. Examples of CH-active compounds are 1,2,3,3-tetramethyl-3H 5 indolium iodide, 1, 2

,

3

,

3 -tetraamethyl-3H-indolium-p-toluene sulfonate, 1,2,3,3-tetramethyl-3H-indolium methane sulfonate, Fischer's base (1,3,3 trimethyl-2-methylindoline), 2,3-dimethylbenzothiazolium iodide, 2,3 dimethylbenzothiazolium-p-toluene sulfonate, rhodanine, rhodanine-3 acetic acid, 1-ethyl-2-quinaldinium iodide, 1-methyl-2-quinaldinium iodide, 10 barbituric acid, thiobarbituric acid, 1,3-dimethyl thiobarbituric acid, diethyl thiobarbituric acid, oxindole, 3-indoxyl acetate, coumaranone and 1-methyl 3-phenyl-2-pyrazolinone. Suitable amino acids are any naturally occurring and synthetic amino acids, for example the amino acids obtainable by hydrolysis from 15 vegetable or animal proteins, for example collagen, keratin, casein, elastin, soya protein, wheat gluten or almond protein. Both acidic and alkaline amino acids may be used. Preferred amino acids are arginine, histidine, tyrosine, phenyl alanine, DOPA (dihydroxyphenyl alanine), ornithine, lysine and tryptophane. 20 The oligopeptides may be naturally occurring or synthetic oligo peptides and the oligopeptides present in polypeptide or protein hydrolyzates providing they are sufficiently soluble in water for use in the colorants according to the invention. Examples of such polypeptides are glutathione and the oligopeptides present in the hydrolyzates of collagen, 25 keratin, casein, elastin, soya protein, wheat gluten or almond protein. These oligopeptides are preferably used together with compounds containing a primary or secondary amino group or with aromatic hydroxy compounds. In a particularly preferred embodiment, the compounds of 30 component B are selected from the group consisting of N-(2-hydroxyethyl)- WO 00/15183 11 PCT/EP99/06525 Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 and also picramic acid, 2-amino-6-chloro-4-nitrophenol, 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 5 1 -methyl- 3 -nitro-4-(2'-hydroxyethyl)-aminobenzene. The compositions according to the invention in this embodiment contain the substantive dyes in a quantity of, preferably, 0.01 to 20% by weight, based on the colorant as a whole. The oxidation dye precursors or the substantive dyes present, if any, 10 do not have to be single compounds. Instead, the hair colorants according to the invention - due to the processes used for producing the individual dyes - may contain small quantities of other components providing they do not adversely affect the coloring result or have to be ruled out for other reasons, for example toxicological reasons. 15 The colorants according to the invention produce intensive colors even at physiologically compatible temperatures of <450C. Accordingly, they are particularly suitable for coloring human hair. For application to human hair, the colorants are normally incorporated in a water-containing cosmetic carrier. Suitable water-containing cosmetic carriers are, for 20 example, creams, emulsions, gels or even surfactant-containing foaming solutions, for example shampoos or other formulations suitable for application to the keratin-containing fibers. If necessary, the colorants may even be incorporated in water-free carriers. The colorants according to the invention may also contain any of the 25 known active substances, additives and auxiliaries typical of such formulations. In many cases, the colorants contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle. In many cases, however, it has been found to be of advantage to select the surfactants from anionic, zwitterionic or 30 nonionic surfactants.

WO 00/15183 13 PCT/EP99/06525 030, - sulfated hydroxyalkyl polyethylene and/or hydroxyalkylene propylene glycol ethers according to DE-A-37 23 354, - sulfonates of unsaturated fatty acids containing 12 to 24 carbon atoms 5 and 1 to 6 double bonds according to DE-A-39 26 344, - esters of tartaric acid and citric acid with alcohols in the form of addition products of around 2 to 15 molecules of ethylene oxide and/or propylene oxide with fatty alcohols containing 8 to 22 carbon atoms. Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether 10 sulfates and ether carboxylic acids containing 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, more particularly, unsaturated CB- 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid. 15 In the context of the invention, zwitterionic surfactants are surface active compounds which contain at least one quaternary ammonium group and at least one -COO) or -SO3) group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl am 20 monium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylaminopropyl dimethyl ammonium glycinate, and 2 alkyl-3-carboxymethyl-3-hydroxyethy imidazolines containing 8 to 18 car bon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. A preferred zwitterionic surfactant is the fatty acid 25 amide derivative known by the CTFA name of Cocamidopropyl Betaine. Ampholytic surfactants are surface-active compounds which, in addition to a C818 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 which are capable of forming inner salts. Examples of suitable ampholytic surfactants 30 are N-alkyl glycines, N-alkyl propionic acids, N-alkyl aminobutyric acids, N- WO 00/15183 15 PCT/EP99/06525 quaternized protein hydrolyzates. Also suitable for use in accordance with the invention are cationic silicone oils such as, for example, the commercially available products Q2 7224 (manufacturer: Dow Corning; a stabilized trimethyl silyl amodimethi 5 cone), Dow Corning 929 Emulsion (containing a hydroxylamino-modified silicone which is also known as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil@-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethyl siloxanes, quaternium-80). 10 Alkyl amidoamines, particularly fatty acid amidoamines, such as the stearyl amidopropyl dimethyl amine obtainable as Tego Amid@S 18, are distinguished not only by their favorable conditioning effect, but also and in particular by their ready biodegradability. Quaternary ester compounds, so-called "esterquats", such as the 15 the methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketed under the trade name of Stepantex@, are also readily biodegradable. One example of a quaternary sugar derivative suitable for use as a cationic surfactant is the commercially available product Glucquat@100 20 (CTFA name: Lauryl Methyl Gluceth-10 Hydroxypropyl Dimonium Chloride). The compounds containing alkyl groups used as surfactants may be single compounds. In general, however, these compounds are produced from native vegetable or animal raw materials so that mixtures with 25 different alkyl chain lengths dependent upon the particular raw material are obtained. The surfactants representing addition products of ethylene and/or propylene oxide with fatty alcohols or derivatives of these addition products may be both products with a "normal" homolog distribution and products 30 with a narrow homolog distribution. Products with a "normal" homolog WO 00/15183 17 PCT/EP99/06525 carboxymethyl cellulose, starch fractions and derivatives, such as amylose, amylopectin and dextrins, clays such as, for example, bentonite or fully synthetic hydrocolloids such as, for example, polyvinyl alcohol, 5 - structurants, such as glucose and maleic acid, - hair-conditioning compounds, such as phospholipids, for example soya lecithin, egg lecithin and kephalins, and also silicone oils, - protein hydrolyzates, more particularly elastin, collagen, keratin, milk protein, soya protein and wheat protein hydrolyzates, condensation 10 products thereof with fatty acids and quaternized protein hydrolyzates, - perfume oils, dimethyl isosorbide and cyclodextrins, - solubilizers, such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, - antidandruff agents, such as Piroctone Olamine and Zinc Omadine, 15 - other substances for adjusting the pH value, - active substances, such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and salts thereof, plant extracts and vitamins, - cholesterol, 20 - UV filters, - consistency factors, such as sugar esters, polyol esters or polyol alkyl ethers, - fats and waxes, such as spermaceti, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, 25 - fatty acid alkanolamides, - complexing agents, such as EDTA, NTA and phosphonic acids, - swelling and penetration agents, such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, tannins, 30 pyrrole, WO 00/15183 19 PCT/EP99/06525 in which

R

1 is a hydrogen atom or a C1.4 alkyl group and

R

2 and R 3 , which may be the same or different, represent a hydrogen atom, a halogen atom, a C 1

.

4 alkyl group, a C1.4 alkoxy group, a hydroxy-C 1 4 5 alkoxy group, a hydroxy group, a nitro group, an amino group which may be substituted by C 1

-

4 alkyl groups or may be part of a heterocycle, or a C1-4 acyl group; two of the substituents together may even form a fused benzene ring, or physiologically compatible salts of such 5-arylpenta-2,4-dienyl carbonyl 10 compounds as a coloring component in oxidation hair colorants. The present invention also relates to a process for coloring keratin containing fibers, more particularly human hair, in which a colorant containing A) 5-arylpenta-2,4-dienyl carbonyl compounds corresponding to formula 15 1: 0 R R3 R1 in which

R

1 is a hydrogen atom or a C1.4 alkyl group and 20 R 2 and R 3 , which may be the same or different, represent a hydrogen atom, a halogen atom, a C1.4 alkyl group, a C14 alkoxy group, a hydroxy-C 1 --alkoxy group, a hydroxy group, a nitro group, an amino group which may be substituted by C1.4 alkyl groups or may be part of a heterocycle, or a C1_4 acyl group; two of the substituents together 25 may even form a fused benzene ring, or physiologically compatible salts of such 5-arylpenta-2,4-dienyl carbonyl compounds, B) at least one compound containing a primary or secondary amino group WO 00/15183 21 PCT/EP99/06525 precursor, 10 mmol of sodium acetate and one drop of a 20% fatty alkyl ether sulfate solution in 100 ml of water was prepared. The suspension was briefly heated to around 800C and, after cooling, was filtered and then adjusted to pH 6. 5 A tress of 90% grey, non-pretreated human hair was placed in this coloring solution for 30 minutes at 300C. The tress was then rinsed for 30 seconds with luke-warm water, dried with warm air and then combed out. The particular shades and depths of color are shown in Table 1 below. 10 The depth of color was evaluated on the following scale: very faint, if any, color (+) : weak intensity + : medium intensity +(+) :medium to strong intensity ++ : strong intensity ++(+) :strong to very strong intensity ++ : very strong intensity

Claims (9)

1. A composition for coloring keratin-containing fibers, more particularly human hair, characterized in that it contains as a coloring component at least one 5-arylpenta-2,4-dienyl carbonyl compound 5 corresponding to formula I: 0 RR R3 R1 in which R 1 is a hydrogen atom or a C 1 . 4 alkyl group and 10 R 2 and R 3 , which may be the same or different, represent a hydrogen atom, a halogen atom, a C 1 . 4 alkyl group, a C 1 .4 alkoxy group, a hydroxy-C 1 . 4 alkoxy group, a hydroxy group, a nitro group, an amino group which may be substituted by C1.4 alkyl groups or may be part of a heterocycle, or a C 1 - 4 acyl group; two of the substituents together may even form a fused 15 benzene ring, or physiologically compatible salts of such 5-arylpenta-2,4-dienyl carbonyl compounds.

2. A composition as claimed in claim 1, characterized in that 4 dimethylaminophenyl penta-2,4-dienal,

4-diethylaminophenyl penta-2,4 20 dienal, 4-methoxyphenyl penta-2,4-dienal, 3,4-dimethoxyphenyl penta-2,4 dienal, 2,4-dimethoxyphenyl penta-2,4-dienal, 4-piperidinophenyl penta 2,4-dienal, 4-morpholinophenyl penta-2,4-dienal, 4-pyrrolidinophenyl penta 2,4-dienal or 4-dimethylaminophenyl hexa-2,4-dien-2-one, 4 diethylaminophenyl hexa-2,4-dien-2-one, 4-methoxyphenyl hexa-2,4-dien 25 2-one, 3,4-dimethoxyphenyl hexa-2,4-dien-2-one, 2,4-dimethoxyphenyl hexa-2,4-dien-2-one, 4-piperidinophenyl hexa-2,4-dien-2-one, 4 morpholinophenyl hexa-2,4-dien-2-one and 4-dimethylamino-1-naphthyl penta-2,4-dienal are used as the compounds of formula 1. WO 00/15183 25 PCT/EP99/06525 aminophthalic acid, 5-aminoisophthalic acid, 1,3,5-, 1,2,4-triaminobenzene, 1,2,4,5-tetraaminobenzene tetrahydrochloride, 2,4,5-triaminophenol trihydrochloride, pentaaminobenzene pentahydrochloride, hexaamino benzene hexahydrochloride, 2 ,4,6-triaminoresorcinol trihydrochloride, 4,5 5 diaminopyrocatechol sulfate, 4,6-diaminopyrogallol dihydrochloride, 3,5 diamino-4-hydroxypyrocatechol sulfate, aromatic nitriles, anilines, more particularly 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-nitro 10 diphenylamine-2'-carboxylic acid, 2 -amino-6-chloro-4-nitrophenol, 1-amino

5-chloro-4-(2-hydroxyethylamino)-2-nitrobenzene, aromatic anilines and phenols containing another aromatic radical, such as 4,4'-diaminostilbene dihydrochloride, 4,4'-diaminostilbene-2,2'-disulfonic acid sodium salt, 4,4' diaminodiphenyl methane, -sulfide, -sulfoxide, -amine, 4,4' 15 diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, -diphenyl ether, 3,3',4,4'-tetraaminodiphenyl tetrahydrochloride, 3,3'4,4' tetraaminobenzophenone, 1, 3 -bis-(2,4-diaminophenoxy)-propane tetra hydrochloride, 1,8-bis-( 2 ,5-diaminophenoxy)-3,6-dioxaoctane tetrahydro chloride, 1, 3 -bis-(4-aminophenylamino)-propane, -2-propanol, 1,3-bis-[N 20 ( 4 -aminophenyl)-2-hydroxyethylamino]-2-propanol, N,N-bis-[2-(4-amino phenoxy)-ethyl]-methylamine trihydrochloride; 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-diamino-, 2-dimethylamino-5-amino-, 3-amino-2 25 methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, 3,5-diamino-2,6 dimethoxy-, 2,4,5-triamino-, 2,6-dihydroxy-3,4-dimethyl pyridine, 4,5,6-tri amino-, 2-hydroxy-4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2,4,5,6-tetra amino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amino-4 methoxy-6-methyl pyrimidine, 2,3,4-trimethyl pyrrole, 2,4-dimethyl-3-ethyl 30 pyrrole, 3,5-diaminopyrazole, -1,2,4-triazole, 3-amino-, 3-amino-5- WO 00/15183 27 PCT/EP99/06525 hydroxyethylamino)-, 2-methyl-5-amino-4-chloro-,

6-methyl-3-amino-2 chloro-, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 3,4-methylenedioxyphenol, 3,4-diaminobenzoic acid, 2,5-diamino-, 2 dimethylamino-5-amino-, 3 -amino-2-methylamino-6-methoxy-, 2,3-diamino 5 6-methoxy-, 3,5-diamino-2,6-dimethoxy-, 2,6-dihydroxy-3,4-dimethyl pyridine, 2-hydroxy-4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2,4,5,6 tetraamino-, 2 -methylamino-4,5,6-triaminopyrimidine, 3,5-diaminopyrazole, 3 -amino-5-hydroxypyrazole, 5,6-dihydroxyindole and 5,6-dihydroxyindoline and physiologically compatible salts thereof formed with preferably 10 inorganic acids.

7. A composition as claimed in any of claims 1 to 6, characterized in that it contains substantive dyes from the group of nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols, preferably in a quantity of 0.01 to 20% by weight, based on the colorant as a whole. 15 8. A composition as claimed in any of claims 1 to 7, characterized in that ammonium or metal salts from the group of formates, carbonates, halides, sulfates, butyrates, valerates, caproates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkaline earth metals, such as potassium, sodium or 20 lithium, alkaline earth metals, such as magnesium, calcium, strontium or barium, or of aluminium, manganese, iron, cobalt, copper or zinc are added.

9. A composition as claimed in any of claims 1 to 8, characterized in that it contains oxidizing agents, more particularly H 2 0 2 , in a quantity of 25 0.01 to 6% by weight, based on the solution applied.

10. A composition as claimed in any of claims 1 to 9, characterized in that it contains anionic, zwitterionic or nonionic surfactants.

11. The use of 5-arylpenta-2,4-dienyl carbonyl compounds corresponding to formula 1: 30 WO 00/15183 29 PCT/EP99/06525 or physiologically compatible salts of such 5-arylpenta-2,4-dienyl carbonyl compounds, B) at least one compound containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or 5 aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound and typical cosmetic ingredients is applied to the keratin-containing fibers, left thereon for a while, normally for about 30 minutes, and then rinsed out 10 again or washed out with a shampoo.