WO2001005359A2 - Substance destinee a teindre des fibres contenant de la keratine - Google Patents

Substance destinee a teindre des fibres contenant de la keratine Download PDF

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Publication number
WO2001005359A2
WO2001005359A2 PCT/EP2000/006399 EP0006399W WO0105359A2 WO 2001005359 A2 WO2001005359 A2 WO 2001005359A2 EP 0006399 W EP0006399 W EP 0006399W WO 0105359 A2 WO0105359 A2 WO 0105359A2
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amino
group
acid
formyl
methyl
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PCT/EP2000/006399
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German (de)
English (en)
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WO2001005359A3 (fr
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Hinrich Möller
Doris Oberkobusch
Horst Höffkes
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU64324/00A priority Critical patent/AU6432400A/en
Publication of WO2001005359A2 publication Critical patent/WO2001005359A2/fr
Publication of WO2001005359A3 publication Critical patent/WO2001005359A3/fr

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    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the invention relates to an agent for dyeing keratin-containing fibers, in particular human hair, which contains quaternary heterocyclic aldehydes and ketones, and to a method for dyeing keratin-containing fibers, in particular human hair.
  • keratin fibers e.g. B. hair, wool or furs
  • 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
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • Primary aromatic amines with a further free or substituted hydroxyl or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as developer components used.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives are generally used as coupler components.
  • Suitable coupling substances are, in particular, ⁇ -naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol , 2-amino-4- (2-hydroxyethylamino) anisole (Lehmanns Blau), 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-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 3-amino-6-methoxy-2-methylamino-pyridine and 3,5-diamino-2,6-dimethoxypyridine.
  • oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color is usually done under the influence of oxidizing agents such. 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 applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
  • 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.
  • the colorants may have no or only a very low sensitization potential.
  • the invention relates to an agent for dyeing keratin fibers, in particular human hair, containing A) at least one quaternary heterocyclic aldehyde or a ketone with the formula
  • R 1 represents a hydrogen atom, a C ⁇ -C ⁇ alkyl, an aryl or heteroaryl group
  • R 2 , R 3 , R 4 is a hydrogen, halogen atom, a C r C 4 alkyl, C ⁇ C ⁇ alkoxy or is a hydroxyl, nitro, amino group which can be substituted by C 1 -C 4 alkyl groups or CrO t -acyl group, where two of the radicals together can form a fused-on benzene ring
  • R 5 is a C 1 -C 4 alkyl, C r C 4 hydroxyalkyl, C 1 -C 4 carboxyalkyl, C r C 4 sulfoalkyl, an aryl, aralkyl or heteroaryl group or else forms an N-oxide unit together with the nitrogen atom carrying it.
  • Q ,, Q 2 , Q 3 in total represent two carbon atoms and one nitrogen atom, which can also be quaternized
  • X represents a direct bond or an optionally substituted vinylene group
  • Y means halide, benzenesulfonate, p-toluenesulfonate, methanesulfonate, trifluoromethanesulfonate, perchlorate, sulfate, tetrafluoroborate, perchlorate, perfluoroalkanoate, hydrogen sulfate, tetrachlorozincate or oxide of an N-oxide, and B) at least one compound selected from compounds having a primary or secondary amino group or hydroxy group, selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds, and / or CH-active compounds.
  • Keratin-containing fibers are wool, furs, feathers and in particular human hair.
  • the colorants according to the invention can also be used for dyeing other natural fibers, such as, for. As cotton, jute, sisal, linen or silk, modified natural 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 can be used.
  • the compounds having the formula I are preferably selected from 4-formyl-1-methylpyrimidinium, 4-formyl-3-methylpyrimidinium, 2-formyl-1-methylpyrimidinium, 2-formyl-3-methylpyrimidinium, 4- Acetyl-1-methylpyrimidinium-, 4-acetyl-3-methylpyrimidinium-, 2-acetyl-1-methylpyrimidinium-, 2-acetyl-3-methylpyrimidinium-, 5-formyl-1-methylpyrimidinium-, 2,4-dimethoxy -5-formyl-2,4-dimethoxy-1-methylpyrimidinium-, 2,4-dimethoxy-5-formyl-2,4-dimethoxy-3-methylpyrimidinium-, 1,2,4-trimethyl-5-acetylpyrimidi - nium-, 2,3,4-trimethyl-5-acetylpyrimidinium, 2-formyl-1-methylquinoxylinium, 2-formyl, 4-methylquinoxylinium, 2-form
  • the majority of these substances are known from the literature or are commercially available or can be prepared by known synthetic processes, as described, for example, in Organikum, VEB yerr Verlag dermaschineen, Berlin 1981, p. 260.
  • the above-mentioned quaternary heterocyclic aldehydes and ketones with the formula I and the compounds of component B are preferably used in the agents according to the invention in an amount of 0.03 to 65 mmol, in particular 1 to 40 mmol, based on 100 g of the entire colorant. used. They can be used as substantive colorants or in the presence of customary oxidation dye precursors.
  • Coloring agents which contain the quaternary heterocyclic aldehydes and ketones with the formula I in combination with component B as the coloring component result in colorations over a wide range of shades from orange-brown, red-brown to violet-brown.
  • reaction products which are reaction products of quaternary heterocyclic aldehydes and ketones of the formula I with the compounds of component B mentioned, as substantive colorants.
  • reaction products can e.g. B. can be obtained by briefly heating the two components in stoichiometric amounts in an aqueous neutral to weakly alkaline medium, where they either precipitate out of the solution as a solid or are isolated therefrom by evaporation of the solution.
  • the reaction products can also be used in combination with other dyes or dye precursors.
  • 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- (2-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, - phenethole, 4-amino- 3-methylphenol, 2- (2,5-diaminophenyl
  • Triaminophenol pentaaminobenzene, hexaaminobenzene, 2,4,6-triaminoresorcinol, 4,5-
  • Diaminobrenzcatechin 4,6-Diaminopyrogallol, 3,5-Diamino-4-hydroxybrenzcatechin, aromatic nitrites, anilines, especially anilines containing nitro groups, such as 4-nitroaniline,
  • R 7 , R 8 , R 9 , R 10 and R 11 represent hydrogen, a hydroxy or an amino group through
  • C ⁇ alkyl, C 1-4 hydroxyalkyl, C ⁇ alkoxy, C 1-4 aminoalkyl or C 1-4 alkoxyC 1-4 alkyl groups may be substituted, and
  • Q for 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 having the formula
  • Y is a direct bond, a CH 2 or CHOH group
  • Z and Z independently of one another for an oxygen atom, an NR 2 group in which R 12 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 is a number from 1 to 4, such as 4,4'-diaminostilbene and its hydrochloride, 4,4 '-Diaminostilbene-2,2'-disulfonic acid mono- or -di-Na salt, 4-amino-4'-dimethylaminostilbene and its hydrochlorind, 4,4'-diaminodiphenylmethane, -sulfide, -sulfoxide, -amine, 4, 4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, diphenyl ether, S.S
  • 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 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-methylamino-3-amino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,6-dimethoxy-3,5-diamine-, 2,4,5-triamino-, 2,6-dihydroxy-3,4-dimethylpyridine, 2,4-dihydroxy-5,6-diamino, 4,5,6-triamino, 4-hydroxy-2,5,6-triamino, 2-hydroxy -4,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2- Amino-4-methoxy-6
  • Suitable aromatic hydroxy compounds are e.g. B. 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucin, hydroxy hydroquinone, 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, -acetophenone, 2-, 4-chlororesorcinol, 1-naphthol, 1, 5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2,7- naphthalene sulfonic acid.
  • CH-active compounds which may be mentioned are 1, 2,3,3-tetramethyl-3H-indolium iodide, 1, 2,3,3-tetramethyl-3H-indolium-p-toluenesulfonate, 1, 2,3,3-tetramethyl - 3H-indolium methanesulfonate, Fischer's base (1,3,3-trimethyl-2-methyleneindoline), 2,3-dimethyl-benzothiazolium iodide, 2,3-dimethyl-benzothiazolium-p-toluenesulfonate, rhodanine, rhodanine-3-acetic acid , 1-methyl-2-quinaldinium iodide, 1-ethyl-2-quinaldinium iodide, 1, 4-dimethylquinolinium iodide, barbituric acid, thiobarbituric acid, 1, 3-dimethylthiobarbituric acid, 1, 3-diethyl
  • 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, 2-amino-4- (2-hydroxyethylamino) anisole, 2- (2,4-diaminophenoxy) ethanol, 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-diethy
  • Oxidizing agents e.g. B. H 2 O 2
  • Oxidizing agents are generally used in an amount of 0.01 to 6% by weight, based on the application solution.
  • a preferred oxidizing agent for human hair is H 2 O 2 .
  • the colorants according to the invention contain, in addition to the compounds according to the invention, customary direct dyes, for example, for further modification of the color shades.
  • customary direct dyes for example, for further modification of the color shades.
  • B. from the group of nitro-phenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as. B.
  • HC Yellow 2 under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 known compounds as well as 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 1-methyl- 3-nitro-4- (2'-hydroxyethyl) aminobenzene.
  • 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.
  • preparations 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.
  • oxidation dye precursors or the optional direct dyes each represent uniform compounds. Rather, in the colorants according to the invention, due to the production process for the individual dyes, still in minor amounts Other components may be included, provided they do not adversely affect the coloring result or for other reasons, e.g. B. toxicological, must be excluded.
  • the colorants according to the invention produce intensive colorations even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants can usually be incorporated into a water-containing cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. B. creams, emulsions, gels or surfactant-containing foaming solutions such.
  • the colorants according to the invention can contain all active ingredients, additives and auxiliaries known in such preparations.
  • 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 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.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • 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,
  • Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear one
  • Alkyl group with 10 to 22 carbon 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 alkane sulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, alpha-sulfofatty acid methyl ester 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 C atoms and x 0 or 1 to 12,
  • 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 to fatty alcohols with 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid , Isostearic acid and palmitic acid.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO 0 - or -SOs ⁇ 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 coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyl 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 cocoacylaminoethylhydroxyethylcarboxymethyl giycinat.
  • a preferred zwitterionic surfactant is the fatty acid
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 1-4 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, coconut acylaminoethylaminopropionate and C 12 . 18 - acyl sarcosine.
  • Nonionic surfactants contain z as a hydrophilic group.
  • B. a Potyol distr, a Polyalkylenglykoletheroli or a combination of Polyol- and Polyglykol- etheroli. 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, for.
  • 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), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ® -Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiioxane, Quatemium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
  • esterquats such as those sold under the trademark Stepantex ® methylhydroxyalkyldialkoyloxyalkylammonium.
  • a suitable cationic surfactant quaternary sugar derivative is the 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 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 narrow homolog distribution can be used.
  • "normal” homolog distribution Mixtures of homologs understood that are obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alkoxides as catalysts.
  • 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.
  • nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallydiallyl ammonium - ammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone-
  • Imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyl-trimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert.-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyacrylic acids, for example, anionic polymers such as anionic polymers, such as anionic polymers , Vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert.-butylacrylamide terpolymers
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic cum, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amyiopectin 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 phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils
  • 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, 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,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, 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 as well as antioxidants.
  • the constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; z.
  • emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
  • Suitable metal salts are e.g. B. formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkali metals, such as potassium, sodium trium or lithium, alkaline earth metals, such as magnesium, calcium, strontium or barium, or of aluminum, manganese, iron, cobalt, copper or zinc, where 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 present in an amount of 0.03 to 65, in particular 1 to 40, mmol based on 100 g of the total color
  • the pH of the ready-to-use coloring preparations is usually between 3 and 11, preferably between 5 and 10.
  • Yet another object of the present invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which a colorant containing
  • R 1 represents a hydrogen atom, a C 1 -C 4 alkyl, an aryl or heteroaryl group
  • R 2 , R 3 , R 4 is a hydrogen, halogen atom, a C r C 4 alkyl, C r C 4 alkoxy or C r C 4 hydroxyalkoxy group, a hydroxyl, nitro, amino group which is formed by CrC -Alkyl groups can be substituted, or C r C 4 -acyl group, where two of the radicals together can form a fused-on benzene ring
  • R 5 is a C r C 4 alkyl, C r C 4 hydroxyalkyl, dC-carboxyalkyl, dC ⁇ sulfoalkyl, an aryl, aralkyl or heteroaryl group or together with the nitrogen atom carrying them an N -Oxide unit forms means Q 1f Q 2 , Q 3 in total represent two carbon atoms and one nitrogen atom, which can also be quaternized
  • Y means halide, benzenesulfonate, p-toluenesulfonate, methanesulfonate, trifluoromethanesulfonate, perchlorate, sulfate, tetrafluoroborate, perchlorate, perfluoroalkanoate, hydrogen sulfate, tetrachlorozincate or oxide of an N-oxide, and B) at least one compound having a primary or secondary amine Hydroxy group, selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, aromatic hydroxy compounds, and / or at least one CH-active compound, and also conventional cosmetic ingredients, applied to the keratin-containing fibers, for some time, usually about 30 minutes , leave on the fiber and then rinsed out or washed out with a shampoo.
  • a primary or secondary amine Hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, aromatic
  • the quaternary heterocyclic aldehydes and ketones of the formula I and the compounds of component B can either be applied to the hair simultaneously or else in succession, it being irrelevant which of the two components is applied first.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. There may be an interval of up to 30 minutes between the application of the first and the second component. Pretreatment of the fibers with the saline solution is also possible.
  • the quaternary heterocyclic aldehydes and ketones of the formula I and the compounds of component B can either be stored separately or together, either in a liquid to pasty preparation (aqueous or anhydrous) or as a dry powder. If the components are stored together in a liquid preparation, this should be largely anhydrous to reduce a reaction of the components. When stored separately, the reactive components are only intimately mixed with one another immediately before use. In dry storage, a defined amount of warm (30 to 80 ° C) water is usually added before use and a homogeneous mixture is produced. Examples
  • a slurry of 5 mmol of an aromatic nitroso compound with the formula I, if appropriate 5 mmol of an oxidation dye precursor of component B and 5 mmol of sodium acetate and a drop of a 20% strength fatty alkyl ether sulfate solution in 50 ml of water at 50 ° C. were prepared. The slurries were mixed together after cooling to 30 ° C and adjusted to pH 6 with dilute NaOH or hydrochloric acid.
  • a strand of 90% gray, untreated human hair was introduced into this dye mixture at 30 ° C. for 30 minutes.
  • the tress was then rinsed with lukewarm water for 30 seconds, dried with warm air and then combed out.

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Abstract

Substance destinée à teindre des fibres contenant de la kératine, en particulier des cheveux humains, qui contient (A) au moins un aldéhyde hétérocyclique quarternaire ou une cétone de formule (I) dans laquelle R1 représente un atome d'hydrogène, un groupe alkyle C¿1?-C4, un groupe aryle ou un groupe hétéroaryle, R?2, R3, R4¿ représentent un atome d'hydrogène, un atome d'halogène, un groupe alkyle C¿1?-C4, un groupe alcoxy C1-C4 ou un groupe hydroxyalcoxy C1-C4, un groupe hydroxy, nitro ou amino qui peut être substitué par des groupes alkyle C1-C4, ou un groupe acyle C1-C4, deux restes pris ensemble pouvant également former un anneau benzol condensé, R?5¿ représente un groupe alkyle C¿1?-C4, un groupe hydroxyalkyle C1-C4, un groupe carboxyalkyle C1-C4, un groupe sulfoalkyle C1-C4, un groupe aryle, aralkyle ou hétéroaryle ou également, avec l'atome d'azote le portant, une unité N-oxyde, Q1, Q2, Q3 représentent au total deux atomes de carbone et un atome d'azote qui peut également être quaternisé, X représente une liaison directe ou un groupe vinylène éventuellement substitué, Y représente halogénure, benzolsulfonate, p-toluolsulfonate, méthanesulfonate, trifluorométhanesulfonate, perchlorate, sulfate, tétrafluoroborate, perfluoroalcanoate, sulfate d'hydrogène, tétrachlorozincate ou oxyde d'un N-oxyde, et (B) au moins une liaison choisie parmi des liaisons dotées d'un groupe amino ou hydroxy primaire ou secondaire, choisi parmi des amines aromatiques primaires ou secondaires, des liaisons hétérocycliques azotées et des liaisons hydroxy aromatiques et/ou des liaisons à activité CH.
PCT/EP2000/006399 1999-07-15 2000-07-06 Substance destinee a teindre des fibres contenant de la keratine WO2001005359A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU64324/00A AU6432400A (en) 1999-07-15 2000-07-06 Agent for coloring keratin fibers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999133187 DE19933187A1 (de) 1999-07-15 1999-07-15 Mittel zum Färben von keratinhaltigen Fasern
DE19933187.1 1999-07-15

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WO2001005359A2 true WO2001005359A2 (fr) 2001-01-25
WO2001005359A3 WO2001005359A3 (fr) 2001-04-26

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AU (1) AU6432400A (fr)
DE (1) DE19933187A1 (fr)
WO (1) WO2001005359A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001010379A2 (fr) * 1999-08-06 2001-02-15 Henkel Kommanditgesellschaft Auf Aktien Agent servant a colorer des fibres keratiniques
EP1433785A1 (fr) * 2002-12-23 2004-06-30 Henkel Kommanditgesellschaft auf Aktien Produits pour la teinture des fibres kératiniques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2830194B1 (fr) * 2001-09-28 2003-12-19 Oreal Composition contenant un derive de pyrazine et utilisation pour la teinture directe ou d'oxydation et/ou l'eclaircissement optique des fibres keratiniques

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1134729A (en) * 1966-11-08 1968-11-27 Research Corp Quinoxaline-di-n-oxides
WO1995001772A1 (fr) * 1993-07-05 1995-01-19 Ciba-Geigy Ag Procede de teinture de fibres keratiniques
EP0873744A2 (fr) * 1997-04-24 1998-10-28 Henkel Kommanditgesellschaft auf Aktien Utilisation de composés carbonyles hétérocycliques pour teindre les fibres kératiniques
DE19745356A1 (de) * 1997-10-14 1999-04-15 Henkel Kgaa Verwendung von Oniumaldehyden und -ketonen zum Färben von keratinhaltigen Fasern
DE19746137A1 (de) * 1997-10-18 1999-04-22 Henkel Kgaa Verwendung von Phenaziniumsalzen zum Färben von keratinhaltigen Fasern
DE19859750A1 (de) * 1998-12-23 2000-06-29 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
FR2787707A1 (fr) * 1998-12-23 2000-06-30 Oreal Procede de teinture mettant en oeuvre un derive cationique et un compose choisi parmi un aldehyde, une cetone, une quinone et un derive de la di-imino-isoindoline ou de la 3-amino-isoindolone

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1134729A (en) * 1966-11-08 1968-11-27 Research Corp Quinoxaline-di-n-oxides
WO1995001772A1 (fr) * 1993-07-05 1995-01-19 Ciba-Geigy Ag Procede de teinture de fibres keratiniques
EP0873744A2 (fr) * 1997-04-24 1998-10-28 Henkel Kommanditgesellschaft auf Aktien Utilisation de composés carbonyles hétérocycliques pour teindre les fibres kératiniques
DE19745356A1 (de) * 1997-10-14 1999-04-15 Henkel Kgaa Verwendung von Oniumaldehyden und -ketonen zum Färben von keratinhaltigen Fasern
DE19746137A1 (de) * 1997-10-18 1999-04-22 Henkel Kgaa Verwendung von Phenaziniumsalzen zum Färben von keratinhaltigen Fasern
DE19859750A1 (de) * 1998-12-23 2000-06-29 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
FR2787707A1 (fr) * 1998-12-23 2000-06-30 Oreal Procede de teinture mettant en oeuvre un derive cationique et un compose choisi parmi un aldehyde, une cetone, une quinone et un derive de la di-imino-isoindoline ou de la 3-amino-isoindolone

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001010379A2 (fr) * 1999-08-06 2001-02-15 Henkel Kommanditgesellschaft Auf Aktien Agent servant a colorer des fibres keratiniques
WO2001010379A3 (fr) * 1999-08-06 2001-11-15 Henkel Kgaa Agent servant a colorer des fibres keratiniques
US6755872B1 (en) 1999-08-06 2004-06-29 Henkel Kommanditgesellschaft Auf Aktien Dyeing agent for keratinous fibers
EP1433785A1 (fr) * 2002-12-23 2004-06-30 Henkel Kommanditgesellschaft auf Aktien Produits pour la teinture des fibres kératiniques

Also Published As

Publication number Publication date
DE19933187A1 (de) 2001-01-18
AU6432400A (en) 2001-02-05
WO2001005359A3 (fr) 2001-04-26

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