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WO1995031959A1 - Derives d'acide 2-oxyacetique utilises pour colorer des fibres contenant de la keratine - Google Patents

Derives d'acide 2-oxyacetique utilises pour colorer des fibres contenant de la keratine Download PDF

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Publication number
WO1995031959A1
WO1995031959A1 PCT/EP1995/001764 EP9501764W WO9531959A1 WO 1995031959 A1 WO1995031959 A1 WO 1995031959A1 EP 9501764 W EP9501764 W EP 9501764W WO 9531959 A1 WO9531959 A1 WO 9531959A1
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WO
WIPO (PCT)
Prior art keywords
group
amino
groups
alkyl
formula
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/EP1995/001764
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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 WO1995031959A1 publication Critical patent/WO1995031959A1/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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C07C309/61—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups

Definitions

  • the invention relates to the use of 2-0xoacetic acid derivatives for dyeing keratin fibers and dyes 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 happens under the influence of oxidizing agents such as. B. H2Ü2 ! 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 2-0xoacetic acid derivatives described in more detail below have so far not been known for dyeing keratin-containing fibers.
  • 2-0xoacetic acid derivatives 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.
  • wool, furs, skins and human hair can be considered as fibers containing keratin.
  • the 2-0xoacetic acid derivatives described in more detail below can in principle also be used for dyeing other natural fibers, such as cotton, jute, sisal, linen or silk, modified natural fibers, such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers , such as polyamide, polyacrylonitrile, -, polyurethane and polyester fibers can be used.
  • the invention relates to the use of 2-0xoacetic acid derivatives of the formula I.
  • R 1 and R ⁇ independently of one another for hydrogen, halogen atoms, C 1 -C 4 -alkyl groups, Ci-C / j-alkanoyl groups, Ci-Cj-alkoxy groups, nitro, hydroxyl, sulfo, carboxyl or NR 4 R ⁇ -Groups, where R 4 and R ⁇ independently of one another are hydrogen or Cj-C / j-alkyl groups, and R3 is hydrogen, a Ci-Cz ⁇ -alkyl group, an aryl group, a hydroxy group, one optionally with Ci-C / j-alkyl or aryl substituted amino group, a an arenoyl group, a C3-Cs-alkenyl group, a mono- or dihydroxy-C2-Cö-alkyl group, an amino-C ⁇ -C4-alkyl group, a sulfo-C ⁇ -C4-alkyl group, a carboxy-Cj
  • R ⁇ and R? independently of one another, hydrogen, halogen atoms, hydroxyl groups, amino groups substituted with C ⁇ -C4-alkyl or aryl, C ⁇ ⁇ C4-alkyl groups, C ⁇ -C4-alkoxy groups, carboxy groups, sulfo groups mean, R 8 for hydrogen, a C ⁇ -C4 alkyl group or a _2-C6-hydroxyalkyl group and n stands for 0, 1 or 2, and their alkali, alkaline earth or ammonium salts for dyeing keratin-containing fibers.
  • Preferred uses are 2-0xoacetic acid derivatives of the formula I in which R is a hydrogen atom or a sulfo group and R ⁇ and R ⁇ are hydrogen.
  • Examples of the 2-0xoacetic acid derivatives to be used according to the invention are: 2- (2-aminophenyl) -, 2- (2-amino-5-methylphenyl) -, 2- (2-amino-5-chlorophenyl) -, 2- (2-amino-5-nitrophenyl) -, 2- (2-amino-5-methoxyphenyl) -, 2- (2-hydroxylaminophenyl) -, 2- (2- (2-hydroxylethylamino) - phenyl) -, 2- (2-benzylaminophenyl) -, 2- (2- (2-sulfoethylamino) -phenyl) -, 2- (2- (3-sulfopropylamino) -phenyl) -, 2- (2- Allylaminophenyl) -, 2- (2-carboxymethylaminophenyl) -, 2- (2-amino-5-bromophenyl) -, 2-
  • 2-0xoacetic acid derivatives of the formula I are new substances. For this reason, 2-0xoacetic acid derivatives of the formula I mel 1 I claimed, in which R ⁇ stands for hydrogen and R * represents a sulfo group located in the 5-position. A manufacturing method is given in the example section.
  • the 2-0xoacetic acid derivatives of the formula I give shades in the pale yellow to yellow range.
  • the wash resistance of the dyeings is surprisingly high.
  • Particularly brilliant colorations in the yellow, brown, green, violet and black range with good fastness properties are achieved if the 2-0xoacetic acid derivatives of the formula I together with compounds having a primary or secondary amino group a nitrogen-containing heterocyclic compound or an aromatic hydroxy compound can be used.
  • these are compounds which, on their own, also only weakly dye hair and only give brilliant dyeings together with the 2-0xoacetic acid derivatives of the formula I.
  • Another subject of the invention is therefore agents for dyeing keratin-containing fibers containing at least one 2-0xoacetic acid derivative 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-phenylene diamine, 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- Methylenedioxyan lin, 3-amino-2,4-dichloro-, 4-methylamino-, 2-methyl-5-amino-, 3-methyl-4-a
  • Suitable nitrogen-containing heterocycles are, for example, 2-, 3-, 4-amino, 2-amino-3-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-diamino, 2-dimethyl amino-5-amino-, 3-amino * -2-methylamino-6-methoxy-, 2,3-diamino-6-methoxy-, S ⁇ -diamino- ⁇ . ⁇ -dimethoxy-, 2,4,5- Triamino-, 2,6-dihydroxy-3,4-dimethyl-pyridine, 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-triazo
  • Suitable aromatic hydroxy compounds are e.g. 2-, 4-, 5-methylresorcinol, 3-dimethylaminophenol, 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-tri-hydroxybenzoic acid, -acetophenone, 2-, 4th -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-
  • Particularly suitable compounds with a primary or secondary amino group are amino acids or oligopeptides composed of 2 to 9 amino acids.
  • Another subject of the invention is therefore agents for dyeing keratin-containing fibers containing at least one 2-0xoacetic acid derivative 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.
  • All naturally occurring and synthetic amino acids are suitable as amino acids, e.g. which are obtained by hydrolysis from vegetable or animal proteins, e.g. Collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein accessible amino acids. Both acidic and alkaline amino acids can be used.
  • Suitable oligopeptides are all oligopeptides composed 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 are e.g. Glutathione or the oligopeptides contained in the hydrolysates of collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein.
  • amino acids or oligopeptides that are selected from are particularly suitable for use in the colorants according to the invention the group tyrosine, histidine, lysine, phenylalanine, ornithine, DOPA, arginine and tryptophan.
  • 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 on fatty alcohols, on fatty acids, on alkyl phenols, fatty acid sorbides, on fatty acid sorbides, on fatty acids, on alkyl phenols, Thickeners, e.g. B.
  • 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
  • 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. B. gum arabic, karaya gum, guar gumrni, locust bean gum, linseed gums and pectin, biosynthetic gums, eg xanthan gum i and dextrans, synthetic gums, e.g. B. agar and algin, starch fractions and derivatives such as amylose, amylopectin and dextrins, modified cellulose molecules, for. 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 as well as reducing agents for stabilizing the ingredients, e.g. B. 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 2-0xoacetic acid derivatives of the formula I and the compounds having a 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 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 entire colorant, contain.
  • 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; sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate are preferred, which in the given case are present in an amount of 0.3 to 65, preferably 6 to 20 mmol , based on 100 g of the total colorant, are contained.
  • 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 (2-0xoacetic acid derivative of the formula I and amino group-containing compound, nitrogen-containing heterocycle or the aromatic hydroxy compound) can either be applied to the hair simultaneously or in succession, it being irrelevant 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 anhydrous or already in the finished formulation. When stored separately, the reactive components are only intimately mixed with one another immediately before use. With dry storage, a defined amount of warm (50 - 80 ° C) water must be added and a homogeneous mixture created.

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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)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation de dérivés d'acide 2-oxyacétique pour colorer des fibres contenant de la kératine, notamment des cheveux naturels, ainsi que des colorants contenant ces composés, notamment en combinaison avec des amines, des acides aminés et des phénols.
PCT/EP1995/001764 1994-05-19 1995-05-10 Derives d'acide 2-oxyacetique utilises pour colorer des fibres contenant de la keratine Ceased WO1995031959A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944417546 DE4417546A1 (de) 1994-05-19 1994-05-19 2-Oxoessigsäurederivate zum Färben keratinhaltiger Fasern
DEP4417546.9 1994-05-19

Publications (1)

Publication Number Publication Date
WO1995031959A1 true WO1995031959A1 (fr) 1995-11-30

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Application Number Title Priority Date Filing Date
PCT/EP1995/001764 Ceased WO1995031959A1 (fr) 1994-05-19 1995-05-10 Derives d'acide 2-oxyacetique utilises pour colorer des fibres contenant de la keratine

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DE (1) DE4417546A1 (fr)
WO (1) WO1995031959A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19859722A1 (de) * 1998-12-23 2000-06-29 Henkel Kgaa Verfahren zum Färben von keratinhaltigen Fasern unter Verwendung von 2-Oxocarbonsäurederivaten in Kombination mit Nucleophilen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0039455A1 (fr) * 1980-05-02 1981-11-11 Henkel Kommanditgesellschaft auf Aktien Coupleurs pour compositions tinctoriales pour cheveux, leur préparation et compositions tinctoriales les contenant
US4452603A (en) * 1980-07-17 1984-06-05 Wella Aktiengesellschaft Process for dyeing hair and composition therefor
EP0400330A1 (fr) * 1989-05-27 1990-12-05 Wella Aktiengesellschaft Colorants d'oxydation pour cheveux

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0039455A1 (fr) * 1980-05-02 1981-11-11 Henkel Kommanditgesellschaft auf Aktien Coupleurs pour compositions tinctoriales pour cheveux, leur préparation et compositions tinctoriales les contenant
US4452603A (en) * 1980-07-17 1984-06-05 Wella Aktiengesellschaft Process for dyeing hair and composition therefor
EP0400330A1 (fr) * 1989-05-27 1990-12-05 Wella Aktiengesellschaft Colorants d'oxydation pour cheveux

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
STUENZI, HANS, AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 34, no. 2, 1981, CANBERRA, pages 365 - 371 *

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