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WO1996022075A1 - Composes diceto pour colorer des fibres contenant de la keratine - Google Patents

Composes diceto pour colorer des fibres contenant de la keratine Download PDF

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Publication number
WO1996022075A1
WO1996022075A1 PCT/EP1996/000056 EP9600056W WO9622075A1 WO 1996022075 A1 WO1996022075 A1 WO 1996022075A1 EP 9600056 W EP9600056 W EP 9600056W WO 9622075 A1 WO9622075 A1 WO 9622075A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
formula
aryl
hydroxy
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.)
Ceased
Application number
PCT/EP1996/000056
Other languages
German (de)
English (en)
Inventor
Hinrich Möller
Horst Höffkes
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 WO1996022075A1 publication Critical patent/WO1996022075A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/32—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using oxidation dyes

Definitions

  • the invention relates to the use of diketo compounds for dyeing fibers containing keratin, in particular human hair.
  • keratin fibers e.g. B. hair, wool or fur
  • 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
  • oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color happens under the influence of oxidizing agents such as. B. H 2 O 2 , which often results in damage to the fiber.
  • Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
  • keratin fibers e.g. Wool, furs, skins and human hair are considered.
  • the diketo compounds described below can also be used for dyeing other natural fibers, e.g. Cotton, jute, sisal, linen or silk, modified natural fibers, e.g. Regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as e.g. Polyamide, polyacrylonitrile, polyurethane and polyester fibers can be used.
  • the invention relates to the use of diketo compounds of the formula I.
  • X represents a saturated or unsaturated alkylene radical having 2 to 4 carbon atoms, optionally by halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl -, C 1 -C 4 alkoxy- (C 1 -C 4 ) alkyl-, formyl-, aryl-, aryl- (C 1 -C 4 ) alkylidene- or formyl- (C 1 -C 4 ) - alkyl radicals can be substituted,
  • R * and R 2 independently of one another for C 1 -C 4 alkyl groups or aryl groups, which are replaced by halogen atoms, hydroxy, C 1-4 alkyl-C 1-4 alkoxy, nitro, bis-C 1-4 alkylamino or carboxy groups can be substituted, or are directly connected to one another so that a cycloaliphatic ring results, as well as the hydrates, semiacetals or semiketals and acetals or ketals of diketo Compounds of formula (I) for dyeing keratin fibers, especially human hair.
  • Examples of the diketo compounds to be used according to the invention are: hexane-2,5-dione, 3-hexene-2,5-dione, 1,2-dibenzoylethylene, 1,2,4-triphenylbutane-1,4-dione , 1,2-dibenzoylethane, 1,2-dibenzoyl-1-chloroethane, 1,1,2,2-tetraacetylethane, cyclohexane-1,4-dione, 5,5-dimethyl-2-phenacylcyclohexane-1,3 -dione, 5-keto-D-fructose, octane-2,5-dione, 1-phenylpentane-1,4-dione, 1,1,4,4-tetraethoxycyclohexane, 4,4-diethoxycyclohexanone, 1,4-cyclohexanedione -monoethylene acetal, 2,6-h
  • 1,2-Dibenzoylethylene, 1,4-cyclohexanedione, acetonylacetone, 1,3-dibenzoylpropane and 1,4-cyclohexanedione monoethylene acetal are preferably used.
  • Suitable compounds with a primary or secondary amino group are, for example, primary aromatic amines such as 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, o-, m-, p-phenylenediamine, 2,5-diaminotoluene, -phenol, -anisole, -phenethol, 2-chloro-p-phenylenediamine, 4-methylamino-, 3-, 4-dimethylamino-, 3,4- Methylene dioxyaniline, 3-amino-2,4-dichloro, 4-methylamino, 2-methyl-5-a
  • Suitable nitrogen-containing heterocycles are e.g. 2-, 3-, 4-amino, 2-amino-3-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-diamino, 2-dimethylamino-5-amino -, 3-amino-2-methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, 3,5-diamino-2,6-dimethoxy-, 2,4,5-triamino-, 2, 6-dihydroxy-3,4-dimethylpyridine, 4,5,6-triamino-, 4-hydroxy-2,5,6-tri- amino-, 2,4,5,6-tetraamino-, 2-methylamino-4 , 5,6-triamino, 2,4-, 4,5-diamino, 2-amino-4-methoxy-6-methyl-pyrimidine, 3,5-diamino-pyrazole, -1,2,4-triazole , 3-amin
  • Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methylresorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucin, hydroxyhydroquinone, 2-, 3-, 4-methoxy, 3-dimethylamino, 2- ( 2-hydroxyethyl) -, 3,4-methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, -phenylacetic acid, gallic acid, 2,4,6-trihydroxybenzoic acid, 2-, 4-methyl-, 2-, 4-chlororesorcinol , 1-, 2-naphthol, 1,5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2,7-naphthalenesulfonic acid.
  • Amino acids or oligopeptides composed of 2 to 9 amino acids are also suitable. All naturally occurring and synthetic amino acids are suitable as amino acids, for example the amino acids accessible by hydrolysis from vegetable or animal proteins, for example collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein. Both acidic and alkaline amino acids can be used. Suitable oligopeptides are all oligopeptides made up of naturally occurring and synthetic amino acids.
  • the oligopeptides can be naturally occurring or synthetic oligopeptides, but also the oligopeptides contained in polypeptide or protein hydrolyzates, provided that they have sufficient water solubility for use in the colorants according to the invention. Examples are e.g. Glutathione or the oligopeptides contained in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein.
  • diketo compounds of the formula I can also be used together in all colorants; Likewise, several different components from the groups of compounds having a primary or secondary amino group, nitrogen-containing heterocycles, aromatic hydroxy compounds or amino acids can also be used together.
  • the use of the isolated reaction products of diketo compounds of the formula I and compounds having a primary or secondary amino group, nitrogen-containing heterocycles, aromatic hydroxy compounds or amino acids as dyes also falls within the scope of the invention.
  • the colorants produce intensive colorations even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants can be incorporated into a water-containing or even into an anhydrous cosmetic carrier.
  • suitable anhydrous carriers are paraffin oil perliquidium or silicone oils of suitable viscosity. If necessary, anhydrous emulsifiers can be added to the oils.
  • Suitable water-containing cosmetic carriers are, for example, creams, emulsions, gels or also surfactant-containing foaming solutions such as shampoos or other preparations which are suitable for use on the hair.
  • the water-containing cosmetic carrier usually contains wetting and emulsifying agents, such as anionic, nonionic or ampholytic surfactants, for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on alkyl phenols, fatty acid sorbides, on fatty acid sorbides, on alkyl phenols, Thickeners, e.g. B.
  • anionic, nonionic or ampholytic surfactants for example fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on alkyl phenols, fatty acid sorbides, on
  • fatty alcohols fatty acids, paraffin oils, fatty acid esters and other fat components in emulsified form
  • water-soluble polymeric thickeners such as natural gums, e.g. Gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin, biosynthetic gums, for example xanthan gum and dextrans, synthetic gums, e.g. B. agar agar and algin, starch fractions and derivatives such as amylose, amylopectin and dextrins, modified cellulose molecules, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, clays such as. B.
  • hair care additives such as water-soluble cationic polymers, anionic polymers, nonionic polymers, amphoteric or zwitterionic polymers, pantothenic acid, vitamins, plant extracts or cholesterol, pH-adjusting agents, complexing agents and perfume oils Stabilization of the ingredients, e.g. B. ascorbic acid, finally can also contain dyes for coloring the cosmetic preparations.
  • solubilizers such as ethylene, 1,3-propylene, 1,2-propylene, 1,2-butylene glycol, glycerol, ethanol, tert. Butanol, 2-propanol or phenethol in amounts of 2-50% may be useful.
  • the diketo compounds of the formula I and the compounds having a primary or secondary amino group, the amino acids or oligopeptides composed of 2 to 9 amino acids, the nitrogen-containing heterocycles or the aromatic hydroxy compounds are in each case in an amount of 0.3 to 65, preferably 6 up to 20 mmol, based in each case on 100 g of the total colorant.
  • Suitable metal salts are e.g. the formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of potassium, sodium, lithium, magnesium, calcium, strontiums, bariums, manganese , Iron, cobalt, copper, zinc; preferred are sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate, which in the given case in an amount of 0.3 to 65, preferably 6 to 20 mmol, based on 100 g of the entire colorant are included.
  • the pH of the ready-to-use coloring preparations is between 2 and 11, preferably between 5 and 9.
  • the colorants are in an aqueous or also an anhydrous cosmetic carrier in an amount of 50- 100 g applied to the hair, left there for about 30 minutes and then rinsed out or washed out with a commercially available hair shampoo.
  • the water-free carrier it is applied to damp hair.
  • the two reactive components can either be applied to the hair at the same time or else one after the other, regardless of which of the two components is applied first; the ammonium or metal salts can be added to the first or 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 hair with the saline solution is also possible.
  • the two reactive components can be stored together, for example as a dry powder or in an anhydrous liquid formulation.
  • a dry powder or in an anhydrous liquid formulation With dry storage, a defined amount of warm (50 - 80 ° C) water must be added and a homogeneous mixture created.
  • an anhydrous formulation When using an anhydrous formulation, the hair must be moistened beforehand in order to achieve a sufficient coloring effect.
  • the reactive components are only intimately mixed with one another immediately before use.
  • Aqueous formulations are preferably used here.
  • one of the reactive components can also be present as a powder or in an anhydrous liquid formulation. Examples
  • a slurry of 10 mmoles of a diketo compound of formula I and 10 mmoles of a reactant, 10 mmoles of sodium acetate and a drop of a 20% fatty alkyl ether sulfate solution in 100 ml of water was prepared.
  • the slurry was heated to boiling temperature and filtered after cooling, the pH was then adjusted to 6.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation de composés dicéto de la formule (I) pour colorer des fibres contenant de la kératine, notamment pour des cheveux naturels. Dans cette formule, X désigne un reste alkylène saturé ou insaturé ayant entre 2 et 4 atomes de C, qui peut éventuellement être substitué par des restes halogène, des restes hydroxy, des restes alcoxy C1-C4, des restes alkyle C1-C4, des restes hydroxyalkyle C1-C4, des restes alcoxy C1-C4-alkyle (C1-C4), des restes formyle, des restes aryle, des restes aryle-alkyle (C1-C4) ou des restes formyle-alkyle (C1-C4), et R1 et R2 désignent indépendamment l'un de l'autre des groupes alkyle C¿1?-C4 ou des groupes aryle pouvant être substitués par des atomes d'halogène, des groupes hydroxy, des groupes alkyle C1-C4-alcoxy C1-C4, des groupes nitro, des groupes alkylamino-bis-C1-C4 ou des groupes carboxy, ou sont mutuellement liés, de manière à former un composé cycloaliphatique. L'invention concerne également des hydrates, des semi-acétals ou des semi-cétals ou des cétals des composés dicéto de la formule (I) pour colorer des fibres contenant de la kératine, notamment des cheveux naturels.
PCT/EP1996/000056 1995-01-18 1996-01-09 Composes diceto pour colorer des fibres contenant de la keratine Ceased WO1996022075A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19501304.2 1995-01-18
DE1995101304 DE19501304A1 (de) 1995-01-18 1995-01-18 Diketo-Verbindungen zum Färben keratinhaltiger Fasern

Publications (1)

Publication Number Publication Date
WO1996022075A1 true WO1996022075A1 (fr) 1996-07-25

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ID=7751710

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/000056 Ceased WO1996022075A1 (fr) 1995-01-18 1996-01-09 Composes diceto pour colorer des fibres contenant de la keratine

Country Status (2)

Country Link
DE (1) DE19501304A1 (fr)
WO (1) WO1996022075A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19717224A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Verwendung von ungesättigten Aldehyden zum Färben von keratinhaltigen Fasern
DE19717222A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
FR2768733B1 (fr) * 1997-09-19 1999-10-29 Oreal Nouveaux composes 4,4-dihydroxypyrazolin-5-ones ; leurs procedes de preparation et utilisations cosmetiques
FR2937540B1 (fr) * 2008-10-27 2016-02-26 Oreal Utilisation d'un compose organique multicetone pour proteger la couleur vis-a-vis du lavage de fibres keratiniques teintes artificiellement ; procede de coloration

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0020274A1 (fr) * 1979-05-31 1980-12-10 Pierre Fabre S.A. Nouveau colorant naturel en particulier à usage capillaire et préparations cosmétiques le contenant
DE4335627A1 (de) * 1993-10-19 1995-04-20 Henkel Kgaa 1,3-Propandione zum Färben keratinhaltiger Fasern

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0020274A1 (fr) * 1979-05-31 1980-12-10 Pierre Fabre S.A. Nouveau colorant naturel en particulier à usage capillaire et préparations cosmétiques le contenant
DE4335627A1 (de) * 1993-10-19 1995-04-20 Henkel Kgaa 1,3-Propandione zum Färben keratinhaltiger Fasern

Also Published As

Publication number Publication date
DE19501304A1 (de) 1996-07-25

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