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WO1995011001A1 - 1,3-propanediones utilisees pour la teinture de fibres keratiniques - Google Patents

1,3-propanediones utilisees pour la teinture de fibres keratiniques Download PDF

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Publication number
WO1995011001A1
WO1995011001A1 PCT/EP1994/003327 EP9403327W WO9511001A1 WO 1995011001 A1 WO1995011001 A1 WO 1995011001A1 EP 9403327 W EP9403327 W EP 9403327W WO 9511001 A1 WO9511001 A1 WO 9511001A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
formula
mmol
propanedione
acid
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/EP1994/003327
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 WO1995011001A1 publication Critical patent/WO1995011001A1/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
    • 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
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/4973—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 1,3-propanediones for dyeing keratin-containing fibers and to colorants containing these compounds.
  • 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 1,3-propanediones described in more detail below have not hitherto been known for dyeing fibers containing keratin.
  • 1,3-propanediones are outstandingly suitable for dyeing keratin-containing fibers even 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 1,3-propanediones 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 are used.
  • the invention relates to the use of 1,3-propanediones of the formula I.
  • R 1 , R ⁇ and R3 independently of one another hydrogen atoms, C1-C4-alkyl, C2-C4-hydroxyalkyl, C ⁇ -C4-carboxyalkyl, Cj-C4-0xoalkyl-, furyl, thienyl, pyridyl or with C ⁇ -C4_Ai
  • ⁇ yi f is Q-C4-alkoxy, C - C4-alkylamino, amino, hydroxy, nitro, carboxy, sulfo or halogen-substituted phenyl, benzyl or benzoyl groups, and R 1 and R3 together can also form a saturated or unsaturated, optionally containing an O atom, optionally substituted with C 1 -C 4 -alkyl, phenyl, hydroxyl or oxo groups, on the 5, 6 or 7 ring an aromatic ring system is condensed and its acetals or ketals for dyeing kerat
  • 1,3-propanediones to be used according to the invention are: acetylacetone, 3-methyl-2,4-pentanedione, 2,4-dioxopentanoic acid, malondialdehyde (as tetrabutylammonium salt), 1,1,3,3-tetramethoxy, 1,1,3,3-tetraethoxypropane, 2,4-hexanedione, 3,5-heptanedione, 2,4-0ctanedione, 2,4-nonanedione, 2,6-dimethyl-3,5-heptanedione, 2, 4,6-heptane trione, 1-, 3-phenyl-acetylacetone, 1,3-diphenyl-acetylacetone, dibenzoylmethane, dianisoylmethane, benzoylacetone, di-benzoylacetone, 3-0xo-3-phenylpropionaldehyde, di-
  • the 1,3-propanediones of the formula I can also be present in the form of with monohydric C j-C4 alcohols formed acetals.
  • the substances are generally available in the chemical trade or can be prepared by the synthesis methods described in "Weygand Hilgetag, Organochemical Experimental Art, 1970, pages 289, 949, 994, 1001".
  • the 1,3-propanediones of the formula I give shades in the pale yellow to yellow range.
  • the washability of the dyeings is surprising high. Particularly brilliant colors in the yellow, brown, green and violet range with good fastness properties (light fastness, wash fastness, fastness to rubbing) are achieved if the 1,3-propanediones of the formula I together with compounds having a primary or secondary amino group, be used with a nitrogen-containing heterocyclic compound or an aromatic hydroxy compound.
  • a further subject of the invention are therefore agents for dyeing keratin-containing fibers containing at least one 1,3-propanedione of the formula I and a compound with 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, 3rd -Amino-2,4-dichloro-, 4-methylamino-, 2-methyl-5-amino-,
  • Suitable nitrogen-containing heterocycles are, for example, 2-, 3-, 4-amino, 2-amino-3-hydroxy, 2,6-diarnino, 2,5-diamino, 2,3-diamino, 2-di- methylamino-5-amino-, 3-amino-2-methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,4,5-triamino-, 2,6-dihydroxy-3, 4-dimethylpyridine, 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-hydroxypyrazole, 2-,
  • Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methylresorcinol, 3-dimethylaminophenol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, 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-dihydroxynaphtha1in, 6-di eth 1 amino-4-hydroxy-2 -naphthalenesulfonic acid, 3,6
  • Particularly suitable compounds with a primary or secondary amino group are amino acids or oligopeptides composed of 2 to 9 amino acids.
  • a further subject of the invention is therefore agents for dyeing keratin-containing fibers containing at least one 1,3-propanedione 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.
  • 1,3-propanediones of the formula I can also be used together in all of the colorants according to the invention; Likewise, several different components from the groups of compounds having a primary or secondary amino group, nitrogen-containing heterocycles or aromatic hydroxy compounds can also be used together.
  • 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 Shampoos 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 alkola ide; Thickeners, e.g.
  • natural gums e.g. B. gum arabic, karaya-gum i, guar-gu mi, locust bean gum, linseed engu ⁇ nen and pectin
  • biosynthetic gums e.g. xanthan gum and dextrans
  • methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose clays such as. B. bentonite or fully synthetic hydrocolloids, such as polyvinyl alcohol or polyvinylpyrrolidone, 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 oil Reducing agents to stabilize the ingredients, e.g. As ascorbic acid, finally, dyes for coloring the cosmetic preparations can also be included.
  • clays such as. B. bentonite or fully synthetic hydrocolloids, such as polyvinyl alcohol or polyvinylpyrrolidone
  • 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
  • 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 1,3-propanediones of formula I as well as the compounds with primary or secondary amino group, e.g. Amino acids or oligopeptides made up of 2 to 9 amino acids, or the nitrogen-containing heterocycles, are in each case in an amount of 0.3 to 65, preferably 6 to 20 mmol, in each case based on 100 g of the total colorant , contain.
  • 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, Calciu s, strontiums, bariums, 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 total 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 (1,3-propanedione of formula I and amino group-containing compound, nitrogen-containing heterocycle or aromatic hydroxy compound) can either be applied to the hair simultaneously 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 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 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.
  • a slurry of 10 mmol of a 1,3-propanedione of the formula I, 10 mmol of a compound containing amino groups, an aromatic hydroxyl compound or a nitrogen-containing heterocycle, 10 mmol of sodium acetate and a drop of a 20% texapon- Prepare N25 solution in 100 ml of water. Salts were optionally added in an amount of 10 mmol each. 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 de 1,3-propanediones pour teindre des fibres kératiniques, notamment des cheveux humains, ainsi que des colorants contenant ces composés, notamment associés à des amines et des acides aminés.
PCT/EP1994/003327 1993-10-19 1994-10-10 1,3-propanediones utilisees pour la teinture de fibres keratiniques Ceased WO1995011001A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934335627 DE4335627A1 (de) 1993-10-19 1993-10-19 1,3-Propandione zum Färben keratinhaltiger Fasern
DEP4335627.3 1993-10-19

Publications (1)

Publication Number Publication Date
WO1995011001A1 true WO1995011001A1 (fr) 1995-04-27

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PCT/EP1994/003327 Ceased WO1995011001A1 (fr) 1993-10-19 1994-10-10 1,3-propanediones utilisees pour la teinture de fibres keratiniques

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DE (1) DE4335627A1 (fr)
WO (1) WO1995011001A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1010419A3 (fr) * 1998-12-15 2001-04-25 Wella Aktiengesellschaft Agent contenant de l'indanedione et des amines aromatiques pour la teinture des fibres
EP1609458A1 (fr) 2004-06-14 2005-12-28 L'oreal Compositions tinctoriales comprenant un dérivé de 1,3-indanedione
EP1609457A1 (fr) 2004-06-14 2005-12-28 L'oreal Compositions tinctoriales comprenant un derive de 1.2-indanedione
US7179304B2 (en) 2003-07-25 2007-02-20 L'oreal S.A. Process for dyeing keratin fibers with at least one polycyclic aromatic vicinal trione
US7367993B2 (en) 2004-06-14 2008-05-06 L'oreal S.A. Dyeing compositions comprising at least one 1,3-indandione derivative
US7374580B2 (en) 2004-06-14 2008-05-20 L'oreal S.A. Dyeing compositions comprising A 1,2-indandione derivative

Families Citing this family (17)

* 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
DE19501304A1 (de) * 1995-01-18 1996-07-25 Henkel Kgaa Diketo-Verbindungen zum Färben keratinhaltiger Fasern
DE19501302A1 (de) * 1995-01-18 1996-07-25 Henkel Kgaa Diketo-Verbindungen zum Färben keratinhaltiger Fasern II
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
DE19745355A1 (de) * 1997-10-14 1999-04-15 Henkel Kgaa Verwendung von Indanonen zum Färben von keratinhaltigen Fasern
DE19745292A1 (de) * 1997-10-14 1999-04-15 Henkel Kgaa Verwendung von Malonaldehydderivaten zum Färben von keratinhaltigen Fasern
DE19857848A1 (de) * 1998-12-15 2000-06-21 Wella Ag Mittel zum Färben von Fasern mit einem Gehalt an 1,3-Indandionen
DE10029933A1 (de) * 2000-06-17 2001-12-20 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
DE10045856A1 (de) 2000-09-14 2002-03-28 Henkel Kgaa Haarfärbemittel mit Indigoderivaten
GB0108615D0 (en) * 2001-04-05 2001-05-23 Procter & Gamble Hair colouring compositions and their use
FR2857857A1 (fr) * 2003-07-25 2005-01-28 Oreal Utilisation en coloration capillaire de derives de ninhydrine a substituants aryle ou aryloxy
US7179306B2 (en) 2003-07-25 2007-02-20 L'oreal S.A. Process for dying keratin fibers comprising at least one aryl or aryloxy substitutent-based ninhydrin derivative
FR2857870B1 (fr) * 2003-07-25 2005-10-14 Oreal Utilisation en coloration de derives de ninhydrine a substituants aryle ou aryloxy
FR2857869B1 (fr) * 2003-07-25 2006-03-17 Oreal Utilisation en coloration capilllaire de triones vicinales aromatiques polycycliques a cycles condenses
FR2857858A1 (fr) * 2003-07-25 2005-01-28 Oreal Utilisation en coloration capillaire de triones vicinales aromatiques polycycliques a cycles condenses
FR2929112B1 (fr) * 2008-03-31 2010-07-30 Oreal Composition de teinture comprenant au moins un derive de cyclanone et au moins un alcoxysilane

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3009833A1 (de) * 1980-03-14 1981-10-01 Henkel Kgaa Verbessertes haarfaerbeverfahren mittels azo-entwicklungsfarbstoffen
JPS6136208A (ja) * 1984-07-26 1986-02-20 Shiseido Co Ltd 染毛料
WO1993019725A1 (fr) * 1992-04-06 1993-10-14 Henkel Kommanditgesellschaft Auf Aktien Agents pour la coloration des fibres keratiniques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3009833A1 (de) * 1980-03-14 1981-10-01 Henkel Kgaa Verbessertes haarfaerbeverfahren mittels azo-entwicklungsfarbstoffen
JPS6136208A (ja) * 1984-07-26 1986-02-20 Shiseido Co Ltd 染毛料
WO1993019725A1 (fr) * 1992-04-06 1993-10-14 Henkel Kommanditgesellschaft Auf Aktien Agents pour la coloration des fibres keratiniques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 10, no. 194 (C - 358) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1010419A3 (fr) * 1998-12-15 2001-04-25 Wella Aktiengesellschaft Agent contenant de l'indanedione et des amines aromatiques pour la teinture des fibres
US7179304B2 (en) 2003-07-25 2007-02-20 L'oreal S.A. Process for dyeing keratin fibers with at least one polycyclic aromatic vicinal trione
EP1609458A1 (fr) 2004-06-14 2005-12-28 L'oreal Compositions tinctoriales comprenant un dérivé de 1,3-indanedione
EP1609457A1 (fr) 2004-06-14 2005-12-28 L'oreal Compositions tinctoriales comprenant un derive de 1.2-indanedione
US7367993B2 (en) 2004-06-14 2008-05-06 L'oreal S.A. Dyeing compositions comprising at least one 1,3-indandione derivative
US7374580B2 (en) 2004-06-14 2008-05-20 L'oreal S.A. Dyeing compositions comprising A 1,2-indandione derivative

Also Published As

Publication number Publication date
DE4335627A1 (de) 1995-04-20

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