WO1995011002A1 - Ethanediones utilisees pour colorer des fibres contenant de la keratine - Google Patents

Ethanediones utilisees pour colorer des fibres contenant de la keratine Download PDF

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Publication number
WO1995011002A1
WO1995011002A1 PCT/EP1994/003328 EP9403328W WO9511002A1 WO 1995011002 A1 WO1995011002 A1 WO 1995011002A1 EP 9403328 W EP9403328 W EP 9403328W WO 9511002 A1 WO9511002 A1 WO 9511002A1
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WO
WIPO (PCT)
Prior art keywords
amino
brown
alkyl
h2so4
formula
Prior art date
Application number
PCT/EP1994/003328
Other languages
German (de)
English (en)
Inventor
Hinrich Möller
Horst Höffkes
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1995011002A1 publication Critical patent/WO1995011002A1/fr

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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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • 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
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65112—Compounds containing aldehyde or ketone groups
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/027—Material containing basic nitrogen preparing dyes in situ

Definitions

  • the invention relates to the use of ethanediones for dyeing fibers containing keratin and to colorants containing these compounds.
  • dyeing 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 with good fastness properties can be achieved, but the development of the color takes place under the influence of oxidizing agents such as. B. H2O2, 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.
  • Dyeing systems based on the ethanediones described in more detail below have not hitherto been known for dyeing keratin fibers.
  • ethanediones are also outstandingly suitable for dyeing keratin-containing fibers in the absence of oxidizing agents.
  • oxidizing agents should in no way be excluded in principle.
  • keratin fibers e.g. Wool, furs, skins and human hair are considered.
  • the ethanediones 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 ethanedions of formula I
  • Rl and R ⁇ independently of one another for straight-chain or branched alkyl radicals having 1 to 5 carbon atoms, for aryl radicals which are mixed with C 1 -C 4 -alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylamino, C ⁇ - C4-Dialkylamino-,
  • a ino, hydroxy, sulfo, carboxyl groups or halogen atoms can be substituted for furyl, thienyl or pyridyl residues, which are with C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C4-alkylamino-, -C-C4-dialkylamino- groups or halogen atoms can be substituted, or R and R ⁇ together with the two keto groups represent an alicyclic non-quinoid 4-, 5-, 6- optionally substituted with C 1 -C 4 -alkyl, oxo, s
  • 1,2-ethanediones to be used according to the invention are: diacetyl, pentane, hexane, heptane-2,3-dione, hexane-3,4-dione, 4,4-dimethylpentane-2,3-dione , l-phenyl-l, 2-propanedione, l-phenyl-l, 2-butanedione, l- (4-methoxy-, l- (4-chlorophenyl) -l, 2-propanedione, l-phenyl-3 , 3-dimethyl-l, 2-butanedione, octan-4,5-dione, benzil, anisil, salicil, 5,5'-dibromosalicil, 2,2'-furyl, 2,2'-thienyl, 2, 2'-, 4,4'-pyridil, 6,6'-dimethyl-4,4'-pyr
  • the ethanediones of the formula I give shades in the pale yellow to yellow range.
  • the wash resistance of the dyeings is surprisingly high.
  • Particularly brilliant colors in yellow, brown, green and violet Areas with good fastness properties are achieved if the ethanediones of the formula I are used together with compounds having a primary or secondary amino group, with a nitrogen-containing heterocyclic compound or with an aromatic hydroxy compound.
  • Another subject of the invention is therefore agents for dyeing keratin-containing fibers containing at least one ethanedione of the formula I and a compound having a primary or secondary amino group, a nitrogen-containing heterocycle or an aromatic hydroxy compound and a water-containing carrier.
  • 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-, 2-chloro-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3-, 4-aminophenol, o-, m -, p-phenylenediamine, 2,5-diamino-toluene, -phenol, -anisole, -phenethol, 2-chloro-p-phenylenediamine, 4-methylamino-, 3-, 4-dimethylamino-, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro, 4-methylamino, 2-methyl-5-amino, 3-methyl-4-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-, 2,4,5-triamino-, 2,6-dihydroxy-3,4-dimethy1pyridine, 4 , 5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amino-4-methoxy-6-methyl-pyrimidine, 3,5-diamino-pyrazole, -1,2,4-triazole, 3-amino, 3-amino -5-hydroxypyrazo
  • Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methylresorcinol, 3-dimethylaminophenol, resorcinol, 3-methoxyphenol, Catechol, 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, -acetophenone, 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.
  • Particularly suitable compounds with a primary or secondary amino group are amino acids or 01igopeptides composed of 2 to 9 amino acids.
  • Another subject of the invention is therefore agents for dyeing keratin-containing fibers containing at least one ethanedione of the formula I and at least one amino acid or an oligopeptide composed of 2 to 9 amino acids and a water-containing carrier.
  • Suitable amino acids are all naturally occurring and synthetic 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 they have sufficient water solubility for use in the colorants according to the invention.
  • Examples include glutathione or the oligopeptides contained in the hydrolyzates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein.
  • those amino acids or oligopeptides selected from the group consisting of tyrosine, histidine, lysine, phenylalanine, ornithine, DOPA, arginine and tryptophan are particularly suitable for use in the colorants according to the invention.
  • 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 according to the invention can be incorporated into a water-containing cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions such as Sha poos or other preparations that 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, fatty alcohols, fatty acids, fatty acid sorbityl fatty acid, an alkylphenol acid fatty acid, and alkylphenol acid fatty acids, an alkylphenol acid fatty acid, anphenylglycerol fatty acid, anphenylglyceryl fatty acid, anphenylglyceryl fatty acid, anphenylglycerol fatty acid, anphenylglycerol fatty acid, anylphenol fatty acid, and an alkylphenol fatty acid and fatty acid alkanolamides; Thickeners, e.g.
  • natural gums e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums and pectin
  • biosynthetic gums e.g. xanthan
  • 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 and reducing agents to stabilize the ingredients, e.g. As ascorbic acid, finally, dyes for coloring the cosmetic preparations can also be included.
  • 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 ethanediones of formula I as well as the compounds with primary or secondary amino group, e.g. Amino acids or oligopeptides composed of 2 to 9 amino acids, the nitrogen-containing heterocycles or the aromatic hydroxy compounds are contained in an amount of 0.3 to 65, preferably 6 to 20 mmol, in each case based on 100 g of the total colorant.
  • Suitable metal salts are, for example, the formates, carbonates, halides, sulfates, butyrates, variates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of potassium, sodium, lithium, magnesium, Calcium, strontium, barium, manganese, iron, cobalt, copper, zinc; sodium are preferred 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 according to the invention are applied to the hair in the form of the water-containing cosmetic carrier in an amount of 100 g, left there for about 30 minutes and then rinsed out or washed out with a commercially available hair shampoo.
  • the two reactive components can either be applied to the hair at the same time or in succession, irrespective 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 a time 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 separately and together either without water or already in the finished formulation. When stored separately, the reactive components are only intimately mixed with one another immediately before use. In the case of dry storage, a defined amount of warm (50-80 ° C.) water is to be added and a homogeneous mixture is to be produced.
  • warm (50-80 ° C.) water is to be added and a homogeneous mixture is to be produced.
  • a slurry of 10 mmol of an ethanedione of the formula I and 10 mmol of a compound containing an amino group, an aromatic hydroxy compound or a nitrogen-containing heterocycle, 10 mM sodium acetate and a drop of a 20% fatty alkyl ether sulfate solution in 100 ml of water were obtained prepares.
  • 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)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation d'éthanediones pour colorer des fibres contenant de la kératine, notamment des cheveux, ainsi que des colorants qui contiennent ces composés, particulièrement en combinaison avec des amines, des aminoacides et des phénols.
PCT/EP1994/003328 1993-10-19 1994-10-10 Ethanediones utilisees pour colorer des fibres contenant de la keratine WO1995011002A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4335625.7 1993-10-19
DE19934335625 DE4335625A1 (de) 1993-10-19 1993-10-19 Ethandione zum Färben keratinhaltiger Fasern

Publications (1)

Publication Number Publication Date
WO1995011002A1 true WO1995011002A1 (fr) 1995-04-27

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ID=6500494

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Application Number Title Priority Date Filing Date
PCT/EP1994/003328 WO1995011002A1 (fr) 1993-10-19 1994-10-10 Ethanediones utilisees pour colorer des fibres contenant de la keratine

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WO (1) WO1995011002A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4434494A1 (de) * 1994-09-27 1996-03-28 Henkel Kgaa 2-Hydroxy-1-ethanon-Derivate zum Färben keratinhaltiger Fasern
DE19653292C1 (de) * 1996-12-20 1998-04-09 Wella Ag Mittel und Verfahren zum Färben von Keratinfasern
DE19717222A1 (de) * 1997-04-24 1998-10-29 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
FR2763241B1 (fr) 1997-05-13 1999-07-02 Oreal Composition de teinture des fibres keratiniques comprenant une pyrazolin-4,5-dione et une amine primaire aromatique
US6228130B1 (en) 1998-11-03 2001-05-08 Bristol-Myers Squibb Company Primary intermediate in oxidative hair dyeing
US7374580B2 (en) 2004-06-14 2008-05-20 L'oreal S.A. Dyeing compositions comprising A 1,2-indandione derivative
FR2871375B1 (fr) * 2004-06-14 2007-07-13 Oreal Compositions tinctoriales comprenant un derive de 1,2-indanedione
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 (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2466492A1 (en) * 1979-10-03 1981-04-10 Elf Aquitaine Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid
GB2181750A (en) * 1985-10-16 1987-04-29 Oreal Dyeing keratinous fibres
EP0359465A2 (fr) * 1988-09-12 1990-03-21 Bristol-Myers Squibb Company Système colorant
WO1993019725A1 (fr) * 1992-04-06 1993-10-14 Henkel Kommanditgesellschaft Auf Aktien Agents pour la coloration des fibres keratiniques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2466492A1 (en) * 1979-10-03 1981-04-10 Elf Aquitaine Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid
GB2181750A (en) * 1985-10-16 1987-04-29 Oreal Dyeing keratinous fibres
EP0359465A2 (fr) * 1988-09-12 1990-03-21 Bristol-Myers Squibb Company Système colorant
WO1993019725A1 (fr) * 1992-04-06 1993-10-14 Henkel Kommanditgesellschaft Auf Aktien Agents pour la coloration des fibres keratiniques

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Publication number Publication date
DE4335625A1 (de) 1995-04-20

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