EP1173143A1 - Procede et colorant pour la coloration de fibres keratiniques - Google Patents

Procede et colorant pour la coloration de fibres keratiniques

Info

Publication number
EP1173143A1
EP1173143A1 EP00917015A EP00917015A EP1173143A1 EP 1173143 A1 EP1173143 A1 EP 1173143A1 EP 00917015 A EP00917015 A EP 00917015A EP 00917015 A EP00917015 A EP 00917015A EP 1173143 A1 EP1173143 A1 EP 1173143A1
Authority
EP
European Patent Office
Prior art keywords
amino
bis
group
aminophenol
methylphenol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00917015A
Other languages
German (de)
English (en)
Inventor
Horst Höffkes
Doris Oberkobusch
Melanie Hitz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1173143A1 publication Critical patent/EP1173143A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols

Definitions

  • the present invention relates to a ner process for the gentler, oxidative dyeing of keratin fibers, in which dyes containing special developer components are applied to the fibers and the oxidation takes place essentially by atmospheric oxygen, and the corresponding dyes.
  • dyeing fibers containing keratin e.g. Wool
  • furs and in particular human hair are generally used either direct dyes or oxidation dyes, which are formed by oxidative coupling of one or more developer components with one another or with one or more coupler components.
  • M-Phenylenediamine derivatives, ⁇ aphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Direct dyes are applied under gentle conditions.
  • their disadvantage is that the dyeings often have insufficient fastness properties.
  • intensive dyes with good fastness properties can be achieved with oxidation dyes, the development of the color usually takes place under the influence of about 2.5-5% by weight of an oxidizing agent, for example H 2 O 2 or H 2 O 2 adducts .
  • an oxidizing agent for example H 2 O 2 or H 2 O 2 adducts .
  • Oxidation colorants with atmospheric oxygen as a very mild oxidizing agent have also already been proposed; in general, however, the oxidations with atmospheric oxygen do not take place completely.
  • EP-B1-0 548 620 for example, it was proposed to limit the hydrogen peroxide content in the oxidation colorants to 1% by weight or less, but at the same time to add special enzymes, peroxidases, to the agent for activation. Colorings with transition metal cations as oxidation catalysts have already been proposed. However, none of these approaches have led to a decisive breakthrough in terms of a competitive market product.
  • the present invention therefore relates to a process for the gentler oxidative dyeing of keratin fibers, in which a colorant which contains at least one developer component of the formula (I) wherein R and R independently of one another represent a Cj to C 4 alkyl group and R represents hydrogen, a halogen atom, a Ci to C 4 alkyl group, a - to C 4 - alkoxy group or a Ci to C 4 hydroxyalkyl group , and is essentially free of conventional chemical oxidizing agents to which fibers are applied and rinsed out again after an exposure time of 10 to 60 minutes.
  • a colorant which contains at least one developer component of the formula (I) wherein R and R independently of one another represent a Cj to C 4 alkyl group and R represents hydrogen, a halogen atom, a Ci to C 4 alkyl group, a - to C 4 - alkoxy group or a Ci to C 4 hydroxyalkyl group , and is essentially free of conventional chemical oxid
  • keratin fibers are to be understood as furs, wool, feathers and in particular human hair.
  • the methods according to the invention are primarily suitable for dyeing keratin fibers, there is in principle nothing to prevent their use in other fields.
  • the exposure time is 20 to 30 minutes.
  • the agents used according to the invention are essentially free of conventional chemical oxidizing agents.
  • Typical chemical oxidizing agents are, for example, persulfates, chlorites and in particular hydrogen peroxide or its adducts with urea, melamine and sodium borate.
  • essentially free of conventional chemical oxidizing agents means that the finished application preparation which is applied to the hair does not contain more than 0.3% by weight of hydrogen peroxide or an amount of another chemical oxidizing agent which is customarily used in its oxidative action. It is irrelevant to the subject matter of the present invention whether the chemical oxidizing agent is packaged separately and is mixed with the coloring agent immediately before use or whether it is formed in situ by constituents of the coloring agent.
  • a method is preferred in which no conventional chemical oxidizing agents other than atmospheric oxygen are involved in the development of the color.
  • the coloring can in principle be carried out with atmospheric oxygen as the only oxidizing agent, in a further preferred embodiment of the present invention, enzymes are used as oxidation catalysts in the dyeing process.
  • an enzymatic process is the procedure to increase the effect of small amounts of hydrogen peroxide by peroxidases.
  • small amounts of hydrogen peroxide can be formed in situ if appropriate oxidases are used with their substrates. Examples are choline oxidase, glucose oxidase, alcohol oxidase, pyruvate oxidase, oxalate oxidase, cholesterol oxidase, uricase, lactate oxidase, xanthine oxidase, pyranose oxidase, glycerol oxidase and galactose oxidase. In this case too, the effect of the hydrogen peroxide formed can be increased by adding peroxidases.
  • the enzymes - such as laccase - can transfer oxygen directly to suitable dye precursors.
  • the enzyme preparation is expediently mixed with the preparation which contains the dye precursors immediately before use.
  • the application temperatures can range between 15 and 40 ° C.
  • the dyeing process can be accelerated if an aqueous solution of the oxidase system is separately adjusted to the desired pH before mixing with the dye preparation and preincubated for 10-30 minutes at 30-40 ° C, for example in a shaker.
  • the optimal pre-incubation parameters should be chosen depending on the specific activity of the enzyme and the amount of the substrate.
  • the pre-incubation batch is then worked into the coloring cream.
  • the peroxidase is optionally added.
  • the pH of the finished application preparation always depends on their maximum activity. It may be preferred to formulate the enzyme preparation free of antioxidants and / or complexing agents, since these can block the action of the enzymes.
  • the dyeing process is catalyzed by the use of metal cations.
  • Transition metal cations with at least two stable oxidation states are preferred according to the invention. Examples are iron, cobalt, copper, manganese, molybdenum, ruthenium and / or vanadium.
  • the metal cations can be present in the form of salts, complexes or bound to a carrier.
  • metal cations are used in the form of their salts, in principle all physiologically compatible anions can be used as counterions.
  • nitrate, hydroxide, chlorate, sulfate, fluoroacetate, carbonate, perchlorate, complex anions such as hexafluorophosphate, tetrafluoroborate, the halides such as chloride or the anions of carboxylic acids such as formate, acetate, benzoate or citrate are preferred.
  • Suitable ligands in the metal complexes which can be used according to the invention are customary substances of both inorganic and organic nature.
  • the organic ligands in such complexes include, in addition to carboxylates, in particular compounds having primary, secondary and / or tertiary amine and / or alcohol functions, such as pyridine, pyridazine, pyrimidine, pyrazine, imidazole, pyrazole, triazole, 2J'-bispyridylamine , Tris (2-pyridylmethyl) amine, 1,4,7-triazacyclononane, l, 4,7-trimethyl-l, 4,7-triaza-cyclononane, 1,5,9-trimethyl-l, 5,9- triazacyclododecane, (bis - ((1-methylimidazol-2-yl) methyl)) - (2-pyridylmethyl) amine, N, N '- (bis (l-methylimid
  • a complex to be used according to the invention contains further, preferably anionic and among these in particular monodentate or bidentate ligands.
  • these include in particular the halides, such as fluoride, chloride, bromide and iodide, and the (NO 2 ) " group.
  • a (NO 2 ) ' group in the present case a nitro ligand, which is attached to the Metal cation is bound, or a nitrito ligand, which is bound to the metal cation via an oxygen atom.
  • the (NO 2 ) " - Group can also be chelated to a metal cation or it can bridge two metal cations asymmetrically or ⁇ 1 -O.
  • the metal complexes to be used in the activator system according to the invention can also carry other ligands of generally simpler structure, in particular mono- or polyvalent anion ligands. For example, nitrate, acetate, trifluoroacetate, formate, carbonate, citrate, perchlorate and complex anions such as hexafluorophosphate are suitable.
  • the anion ligands are intended to balance the charge between the metal cation and the ligand system.
  • oxo ligands oxo ligands
  • peroxo ligands ligands
  • imino ligands ligands
  • Such ligands in particular can also act as bridges, so that multinuclear complexes are formed.
  • the use of dinuclear or multinuclear complexes in which the metal cations have different oxidation numbers is also possible.
  • anionic counterions which neutralize the cationic metal complex can be present in the metal complex compounds to be used according to the invention.
  • anionic counterions include in particular nitrate, hydroxide, hexafluorophosphate, sulfate, chlorate, perchlorate, the halides such as chloride or the anions of carboxylic acids such as formate, acetate, benzoate or citrate.
  • Support materials which can be used according to the invention are, for example, zeolites, layered silicates or sol / gel systems.
  • Zeolites are aluminosilicates made from three-dimensionally cross-linked aluminate and silicate tetrahedral building blocks. All zeolites have a one- or multi-dimensional channel and pore system.
  • the preferred carrier materials include the zeolites of the A, K, L, P-L, O, T, X, Y and ⁇ type and mixtures thereof.
  • the metal compounds according to the invention can both be present on the surface of the zeolite and also be located within the pores or enclosed within the pores. The charge balance can also be carried out at least in part by the zeolite.
  • Layered silicates which can be used according to the invention are also aluminosilicates, but they are not have the typical zeolite pore structure. Layered silicates rather form platelet-like structures in the suspended state, on the surface of which the metal compounds can accumulate.
  • Examples of layered silicates according to the invention are, in addition to bentonite, as a conventional mixture of montmorillonite and kaolinite, the product of extremely swellable hectorite sold by Henkel under the trade name Dehydril HT.
  • Sol / gel systems according to the invention are amorphous, glass-like substances which are composed of interpenetrating inorganic (silicate) and optionally organic (polymer-analogous) networks.
  • Sol / gel systems can be synthesized both on the basis of silicon dioxide and on the basis of titanium dioxide.
  • the compounds containing metal cations can be made up both in a common preparation with the dye precursors and separately.
  • the metal cation-containing compounds are preferably dissolved or suspended separately in a suitable solvent, for example in water, ethanol or acetone, and, if appropriate, stirred with the oxidizing agent preparation immediately before dyeing the hair.
  • This preparation is then mixed with a preparation containing the dye precursors.
  • the resulting ready-to-use hair color preparation should preferably have a pH in the range from 6 to 10. A pH of 6.5 to 8 is particularly preferred.
  • the application temperatures can be in a range between 15 and 40 ° C.
  • the present invention furthermore relates to hair colorants for use in the process according to the invention.
  • Essential components of these agents are developer components of the formula (I).
  • Examples of the C 1 -C 4 -alkyl groups mentioned as substituents in the compounds according to the invention are the groups methyl, ethyl, propyl, isopropyl and butyl. Ethyl and methyl groups are preferred alkyl groups.
  • Developer components of the formula (I) in which the radical R is hydrogen are preferred according to the invention.
  • a very particularly preferred developer component is 4-amino-2 - ((diethylamino) methyl) phenol.
  • the method according to the invention using 4-Amino-2 - ((diethylamino) methyl) phenol as developer component enables coloring in a wide range of shades and with high light and shampoo fastness.
  • the colorants can also contain further developer components.
  • Preferred developer components according to the invention are p-phenylenediamine, p-toluenediamine, p-aminophenol, o-aminophenol, 1 - (2'-hydroxyethyl) -2,5-diaminobenzene, N, N-bis (2-hydroxyethyl) -p -phenylene diamine, 2- (2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolone-5, 4-amino-3-methylphenol, 2,4,5,6 -Tetraamino-pyrimidine, 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-hydroxyethyla
  • developer components are p-phenylenediamine, p-toluenediamine, p-aminophenol, l- (2'-hydroxyethyl) -2,5-diaminobenzene, 4-amino-3-methylphenol, 2,4,5, 6-tetraaminopyrimidine, 2 -Hydroxy-4,5,6-triaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 4,5-diamino-1 - (2-hydroxyethyl) pyrazole, 2-aminomethyl-4-aminophenol , N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, bis- (2-hydroxy-5-aminophenyl) methane, lJ0-bis- (2,5-diaminophenyl) -l, 4,7,10 -tetraoxadecane and o-aminophenol.
  • the agents according to the invention can also contain one or more coupler components.
  • Coupler substances are often aromatic or heterocyclic ring systems which have two reactive groups in the meta position.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used as coupler components.
  • Coupler components preferred according to the invention are: m-aminophenol and its derivatives such as 5-amino-2-methylphenol, 5-
  • Diaminophenoxyethanol 1,3-bis- (2,4-diaminophenoxy) propane, 1-methoxy-2-amino-
  • Resorcinol monomethyl ether 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol,
  • Pyridine derivatives such as 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine,
  • Naphthalene derivatives such as 1-naphthol, 2-methyl-1-naphthol, 2-
  • Morpholine derivatives such as 6-hydroxybenzomorpholine and 6-aminobenzomorpholine,
  • Pyrazole derivatives such as, for example, l-phenyl-3-methylpyrazol-5-one,
  • Indole derivatives such as 4-hydroxyindole, 6-hydroxyindole and 7-
  • Methylenedioxybenzene derivatives such as 3,4-methylenedioxyphenol, 1-
  • Coupler components in the sense of the invention 2,4-diaminophenoxyethanol, 1,3-bis (2,4-diamino-phenoxy) propane, 2-methylamino-3-amino-6-methoxypyridine, 1-naphthol, 6-methyl -l, 2,3,4-tetrahydroquinoxaline, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 2-amino-3-hydroxypyridine , Resorcinol, 4-chlororesorcinol, 2,4-dichloro-3-aminophenol, 1,5-dihydroxynaphthalene, 1, 7-dihydroxynaphthalene, 2,7-dihydroxy-naphthalene, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 2 - Amino-5-chloro-3-hydroxypyridine, 3,5-diamino-2,6-dimethoxypyridine
  • the developer and coupler components are usually used in free form.
  • substances with amino groups however, it can be preferred to use them in salt form, in particular in the form of the hydrochlorides and sulfates.
  • the colorants according to the invention preferably contain both the developer components and the coupler components in an amount of 0.005 to 20% by weight, preferably as 0.1 to 5 wt .-%, each based on the entire oxidizing colorant.
  • Developer components and coupler components are generally used in approximately molar amounts to one another. If molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1 : 2, may be included.
  • the colorants according to the invention contain, in addition to the oxidation dye precursors, customary direct dyes for further modification of the color shades.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, 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-l, 2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitro-toluidine, picramic acid, 2-amino-6-chloro-4-nitrophenol 4-ethylamino-3-nitrobenzoic acid and 2-chloro 6-ethylamino-1-hydroxy-4-nitrobenzene.
  • the agents according to the invention in accordance with this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20% by weight, based on the total colorant.
  • the colorants according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • dye components contained in the colorants according to the invention can also be indoles and indolines, and also their physiologically tolerable salts.
  • Preferred examples are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihy- hydroxy indole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 5,6-
  • Dihydroxyindole-2-carboxylic acid, 6-aminoindole and 4-aminoindole are also preferred. Also preferred are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 5 , 6-dihydroxyindoline-2-carboxylic acid, 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • oxidation dye precursors or the substantive dyes each represent uniform compounds. Rather, in the colorants according to the invention, due to the production processes for the individual dyes, further components may also be present in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. toxicological, must be excluded.
  • the hair colorants furthermore contain at least one dye of the reactive carbonyl compound type, selected from the group of aromatic, heteroaromatic or unsaturated aldehydes or ketones, dialdehydes or diketones or acetals, semi-aminals or imine derivatives of such reactive carbonyl compounds.
  • Suitable compounds of the aromatic aldehyde type are e.g. described in the German patent applications DE 196 30 274 AI and DE 196 30 275 AI. Suitable compounds are e.g. the 2-hydroxybenzaldehyde, the 4-hydroxy-3-methoxy-benzaldehyde (vanillin) and the 4-hydroxy-3-methoxy-cinnamaldehyde (coniferyl aldehyde).
  • Suitable compounds of the heteroaromatic aldehyde type are described, for example, in German Offenlegungsschrift DE 197 17 280 AI.
  • Particularly suitable dyes are, for example, trans- ⁇ - (2-furyl) acrolein, l-methylindole-3-aldehyde, 2- (1,3,3-trimethyl-2-indolinylidene) acetaldehyde or antipyrin-4-aldehyde.
  • German patent application DE 197 45 356J Special products of this type with a pyridinium group are described in German patent application DE 197 45 356J, for example the very suitable 4-formyl-1-methylpyridinium benzenesulfonate and 4-formyl-1-methylquinolinium methanesulfonate or methyl sulfate .
  • Suitable dyes of the unsaturated aldehyde type are described, for example, in German Offenlegungsschrift DE 197 17 224 AI.
  • Dialdehydes and diketones and their derivatives which are suitable as dyes according to the invention are e.g. alicyclic and cyclic 1,2- and 1,3-dicarbonyl compounds, such as isatin, ninhydrin, alloxan, isobarbituric acid, p- and o-quinones, 1,3-indanediones and their derivatives.
  • Such dyes are found e.g. in the German patent application DE 43 35 627 AI.
  • Suitable compounds are e.g. the malonic dialdehyde, preferably in the form of its dimethyl acetal, the 2-nitro-1,3-indanedione or the 2-acetyl-1J-cyclohexanedione.
  • the diketones suitable according to the invention also include cyclic dicarbonyl compounds such as e.g. the isatin and its derivatives, e.g. are described in German Offenlegungsschrift DE 44 09 143 AI.
  • cyclic dicarbonyl compounds such as e.g. the isatin and its derivatives, e.g. are described in German Offenlegungsschrift DE 44 09 143 AI.
  • Another suitable cyclic dicarbonyl compound is e.g. also dehydro-ascorbic acid, the suitability of which as a hair dye is known from German patent application DE 197 45 354.6.
  • the acetals, imine derivatives and semi-aminals of the reactive carbonyl compounds mentioned are also suitable. Such compounds are obtained by reaction of the carboxyl group with primary alcohols or amines and optionally elimination of water.
  • Suitable imine derivatives of glutacondialdehyde are, for example, the mono-N-methylaniline derivative of glutaconaldehyde (5-N-methylanilinopentadienal) or the N- (5-anilino-2,4-pentadien-l-ylidene) anilinium chloride.
  • Another suitable vinylogous cyanine dye is 7-dimethylamino-2,4,6-heptatrienylidene-dimethylammonium perchlorate.
  • Such connections are known as hair color medium components known for example from German published patent application DE 197 17 223 AI.
  • Suitable amino acids are e.g. the naturally occurring and synthetic amino acids, e.g. Arginine, histidine, phenylalanine, dihydroxyphenylalanine, ornithine, lysine.
  • Suitable peptides are above all oligo- and polypeptides which have sufficient water solubility in the preparations according to the invention for keratin reduction. Examples are e.g. Glutathione or the oligopeptides contained in the hydrolysates of collagen, keratin, elastin, casein, plant proteins such as soy protein, wheat gluten or almond protein.
  • Suitable aromatic amines and aminophenols are N, N-dimethyl-, N, N-diethyl-, N- (2-hydroxyethyl) -N-ethyl-, N, N-bis- (2-hydroxyethyl) -, N- (2 -Methoxyethyl-), 2-chloro, 2,3-, 2,4- and 2,5-dichloro-p-phenylenediarnine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3- and 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o- and p-phenylenediamine, o- and m-toluenediamine, 2,5-diamino-phenol, -toluene and -phenethol, 4- Amino-3-methylphenol, 2- (2,5-diaminophenyl) ethanol, 2,4-diaminophen
  • R represents a hydroxy or an amino group which may be substituted by C 1-4 alkyl, C ⁇ -hydroxyalkyl or C -alkoxy-C -alkyl
  • R, R, R, R and R represent hydrogen, a hydroxy - or an amino group which is formed by C 4 alkyl, C 4 hydroxyalkyl, or C -alkoxy-C -alkyl group can be a carbon or sulfonic acid group
  • X represents a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms optionally substituted by hydroxyl groups, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the formula (III)
  • Y is a direct bond, a CH 2 or CHOH group
  • Z and Z 'independently of one another are an oxygen atom, an NR 10 group, in which R 10
  • Hydrogen, a C 4 alkyl or hydroxy C 4 alkyl group means the group
  • the abovementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable phenols are e.g. 2-, 3- or 4-methoxy-, 3-dimethylamino-, 2- (2-hydroxyethyl) - and 3,4-methylenedioxyphenol, resorcinol and 2-, 4- and 5-methylresorcinol, 2- and 4-chlororesorcinol, 2,5-dimethylresorcinol, pyrocatechol, hydroquinone, pyrogallol, phloroglucin, hydroxyhydroquinone, 2,4- or 3,4-dihydroxybenzoic or phenylacetic acid, gallic acid, 2,4, 6-trihydroxybenzoic acid or 2,4,5-trihydroxyacetophenone, 1-naphthol, 1,5-, 2,3- and 2,7-dihydroxy-naphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid or the 3,6-dihydroxy-2,7-naphthalenedisulfonic acid.
  • Suitable nitrogen-containing heterocyclic compounds are, for example, 2-, 3-, 4- amino-, 2-amino-3-hydroxy-, 2,6-diamino-, 2,5-diamino-, 2,3-diamino-, 2-dimethylamino -5-amino-, 2-methylamino-3-amino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,6-dimethoxy-3,5-diamino-, 2,4,5-triamino - and 2,6-dihydroxy-3,4-dimethylpyridine, 2,4-dihydroxy-5,6-diamino, 4,5,6-triamino, 4-hydroxy-2,5,6-triamino-, 2nd -Hydroxy-4,5,6-triamino-, 2,4,5, 6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino- and 2-
  • the aforementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, e.g. B. as salts of inorganic acids such as hydrochloric or sulfuric acid.
  • These dyeing systems can be further enhanced by suitable nitrogen-containing heterocycles such as piperidine, piperidine-2-, -3- or -4-carboxylic acid, pyridine, 2-, 3- or 4-hydroxypyridine, imidazole, 1-methylimidazole, histidine, pyrrolidine , Pyrrolidone, pyrrolidone-5-carboxylic acid, pyrazole, 1,2,4-triazole, piperazine and their physiologically tolerable salts.
  • suitable nitrogen-containing heterocycles such as piperidine, piperidine-2-, -3- or -4-carboxylic acid, pyridine, 2-, 3- or 4-hydroxypyridine, imidazole, 1-methylimidazole, histidine, pyrrolidine , Pyrrolidone,
  • the oxidation dye precursors can be incorporated into a suitable water-containing carrier.
  • suitable water-containing carrier are for the purpose of coloring hair e.g. Creams, emulsions, gels or also foaming solutions containing surfactants, e.g. Shampoos, aerosols or other preparations that are suitable for use on the hair.
  • the colorants according to the invention can furthermore contain all active substances, additives and auxiliaries known for such preparations.
  • the colorants contain at least one surfactant, and in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic Alkyl group with about 10 to 22 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic Alkyl group with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • 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 with 10 to 22 C atoms and x 0 or 1 to 16, acyl sarcosides with 10 to 18 C- Atoms in the acyl group, acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group,
  • Sulfosuccinic acid mono- 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) ⁇ -SO-H, in which R is a preferably linear alkyl group with 10 to 18 C atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 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 ⁇ group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines each with 8 to 18 carbon atoms in the alkyl or acyl group and cocosacylaminoethylhydroxyethylcarboxymethylglycineate
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the LNCI name cocamidopropyl betaine.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8 -C 8 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 .
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-coconut alkylaminopropionate, cocoacylaminoethyl aminopropionate and C] 2 cosin - ⁇ 8 -Acylsar-.
  • 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
  • Examples of the cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone) will), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
  • Quaternary ester compounds so-called “esterquats”, such as the methyl-hydroxyalkyl-dialkoyloxyalkyl-ammonium methosulfates sold under the trademark Stepantex and the products sold under the trademark De-hyquart ® such as Dehyquart ® AU-46 are also very readily biodegradable.
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to INCI nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride".
  • the compounds with alkyl groups used as surfactants can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologues which are obtained as catalysts when converting fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • the hair treatment compositions according to the invention can preferably also contain a conditioning active ingredient selected from the group formed by cationic surfactants, cationic polymers, alkylamidoamines, paraffin oils, vegetable oils and synthetic oils.
  • Cationic polymers can be preferred as conditioning agents. These are usually polymers that contain a quaternary nitrogen atom, for example in the form of an ammonium group.
  • Preferred cationic polymers are, for example, quaternized cellulose derivatives, such as are available under the names of Celquat ® and Polymer JR ® commercially.
  • the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ® 400 are preferred quaternized cellulose derivatives.
  • Merquat ® 100 poly (dimethyldiallylammonium chloride)
  • Mer- quat ® 550 dimethyldiallylammonium chloride-acrylamide copolymer
  • Merquat ® 280 dimethyldiallylammonium chloride-acrylic acid copolymer
  • Polyquaternium 27 known polymers with quaternary nitrogen atoms in the main polymer chain.
  • Cationic polymers of the first four groups are particularly preferred; polyquaternium-2, polyquaternium-10 and polyquaternium-22 are very particularly preferred.
  • conditioning agents are silicone oils, in particular dialkyl and alkylarylsiloxanes, such as dimethylpolysiloxane and methylphenylpolysiloxane, and their alkoxylated and quaternized analogs.
  • silicones examples include the products sold by Dow Coming under the names DC 190, DC 200, DC 344, DC 345 and DC 1401 as well as the commercial products Q2-7224 (manufacturer: Dow Coming; a stabilized trimethylsilylamodimethicone), Dow Coming® 929 emulsion (containing a hydroxyl-amino-modified silicone, which is also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt ; diquaternary polydimethylsiloxanes, Quaternium-80).
  • Paraffin oils, synthetically produced oligomeric alkenes and vegetable oils such as jojoba oil, sunflower oil, orange oil, almond oil, wheat germ oil and peach seed oil can also be used as conditioning agents.
  • suitable hair conditioner compounds are phospholipids, for example soy lecithin, egg lecithin and cephalins.
  • nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride / acrylate-copolyamide methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers
  • anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobomyyl acrylate copolymers and acrylic acid copolymers / Ethyl
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such as e.g. Polyvinyl alcohol,
  • Structurants such as glucose and maleic acid
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized 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 zinc 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,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as whale, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary
  • 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 as well
  • constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; e.g. emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0J to 25% by weight of the total colorant.
  • the coloring solution was applied to locks of hair (Kerling natural white). After a contact time of 30 minutes at 32 ° C., the strands of hair were rinsed, dried and the resulting dye result was determined visually according to the pocket dictionary of colors (2nd edition, Musterschmidt-Verlag Switzerland-Göttingen, 1975).

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Abstract

L'invention concerne un procédé permettant une coloration d'oxydation, moins agressive, de fibres kératiniques. Ce procédé consiste à appliquer sur les fibres un colorant pratiquement exempt d'agent d'oxydation chimique usuel, puis à l'éliminer par rinçage après un temps d'imprégnation compris entre 10 et 60 minutes. Ce colorant contient au moins un composant développeur de formule (I), dans laquelle R<1> et R<2> représentent indépendamment l'un de l'autre un groupe alkyle C1-C4 et R<3> représente hydrogène, un atome d'halogène, un groupe alkyle C1-C4, un groupe alcoxy C1-C4 ou un groupe hydroxyalkyle C1-C4. Ce procédé permet d'obtenir des colorations nuancées présentant une stabilité élevée à la lumière et au shampooing.
EP00917015A 1999-04-09 2000-03-30 Procede et colorant pour la coloration de fibres keratiniques Withdrawn EP1173143A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19916032 1999-04-09
DE1999116032 DE19916032A1 (de) 1999-04-09 1999-04-09 Verfahren zum Färben keratinischer Fasern und Färbemittel
PCT/EP2000/002805 WO2000061090A1 (fr) 1999-04-09 2000-03-30 Procede et colorant pour la coloration de fibres keratiniques

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EP1173143A1 true EP1173143A1 (fr) 2002-01-23

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DE19936442A1 (de) * 1999-08-03 2001-02-08 Henkel Kgaa Neue Entwickler-Kuppler-Kombinationen
DE10156667A1 (de) * 2001-11-17 2003-05-28 Henkel Kgaa Oxidationsfärbemittel auf der Basis zweikerniger Entwicklerkomponenten
DE102005005875A1 (de) * 2005-02-09 2006-08-24 Wella Ag 3-Amino-2-aminmethyl-phenol-Derivate und diese Verbindungen enthaltende Färbemittel

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DE3543345A1 (de) * 1985-12-07 1987-06-11 Wella Ag Oxidationshaarfaerbemittel auf der basis von 4-amino-2-aminomethyl-phenolen
ATE121288T1 (de) * 1991-12-20 1995-05-15 Goldwell Ag Verfahren zum oxidativen färben von menschlichen haaren und mittel zur durchführung dieses verfahrens.
DE4429343A1 (de) * 1994-08-18 1996-02-22 Henkel Kgaa Haarfärbemittel
DE19704831C1 (de) * 1997-02-08 1998-04-09 Goldwell Gmbh Haarfärbemittel
DE19735866C1 (de) * 1997-08-19 1998-10-15 Goldwell Gmbh Haarfärbemittel
FR2769211B1 (fr) * 1997-10-03 1999-12-24 Oreal Composition de teinture des fibres keratiniques et procede de teinture mettant en oeuvre cette composition

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Title
See references of WO0061090A1 *

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WO2000061090A1 (fr) 2000-10-19
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