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EP0998256A1 - Utilisation de di- et d'oligoacylaromatiques pour colorer des fibres a base de keratine - Google Patents

Utilisation de di- et d'oligoacylaromatiques pour colorer des fibres a base de keratine

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Publication number
EP0998256A1
EP0998256A1 EP98936419A EP98936419A EP0998256A1 EP 0998256 A1 EP0998256 A1 EP 0998256A1 EP 98936419 A EP98936419 A EP 98936419A EP 98936419 A EP98936419 A EP 98936419A EP 0998256 A1 EP0998256 A1 EP 0998256A1
Authority
EP
European Patent Office
Prior art keywords
amino
group
acid
hydroxy
compounds
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.)
Withdrawn
Application number
EP98936419A
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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
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Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0998256A1 publication Critical patent/EP0998256A1/fr
Withdrawn legal-status Critical Current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

Definitions

  • the invention relates to the use of di- and oligoacylaromatics for dyeing keratin-containing fibers, in particular human hair, and to an agent for dyeing keratin-containing fibers, which contains di- and oligoacylaromatics, and a method for dyeing keratin-containing fibers.
  • 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
  • Coupler and developer components are also referred to as oxidation dye precursors.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and their derivatives are usually used as developer components.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Particularly suitable coupler substances are 1-naphthol, pyrogallol, 1, 5-, 2,7- and 1,7-dihydroxynaphthalene, o-aminophenol, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine , 1-phenyl-3-methyl-pyrazolone-5, 2,4-dichloro-3-aminophenol, 1,3-bis (2,4-diaminophenoxy) propane, 4-chlororesorcinol, 2-chloro-6-methyl -3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2,6-
  • oxidation dyes With oxidation dyes it is possible to achieve intensive dyeings with good fastness properties, but the development of the color generally takes place under the influence of oxidizing agents such as H 2 O 2 , which in some cases can damage the fibers. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes have a sensitizing effect on people with sensitive skin. Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
  • US Pat. No. 3,158,542 describes systems for dyeing keratin-containing fibers which describe 1,2-diacetylbenzenes or 1,2-diacetylcycloaliphatics in combination with amines, such as amino acids and aliphatic and aromatic amines.
  • amines such as amino acids and aliphatic and aromatic amines.
  • these systems described have the disadvantage that the variety of color tones is very limited and that 1,2-diacetylated aromatics stain the scalp very strongly when used in humans.
  • the object of the present invention is to provide colorants for keratin fibers, in particular human hair, which are at least equivalent in quality to conventional oxidation hair colorants in terms of color depth, gray coverage and fastness properties, but without necessarily being dependent on oxidizing agents such as H 2 O 2 .
  • Another object of the present invention is to provide colorants with which a wide variety of color shades can be obtained. Staining of the skin areas should be avoided if possible.
  • the colorants may have no or only a very low sensitization potential.
  • the present invention accordingly relates to the use of di- and oligoacyl aromatics of the following formula (1)
  • R 1 and R 2 each independently represent a lower (C -C 4 ) alkyl group, an aryl or heteroaryl group
  • R 3 , R 4 and R 5 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 4 alkoxy group or a hydroxy (C 1 -C 4 ) alkoxy group, a hydroxy group, nitro group, amino group or C r C 4 acyl group, with the proviso that 1, 2-diacetylbenzenes are excluded, in Presence of at least one compound with primary or secondary amino group or hydroxy group, selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides and aromatic hydroxy compounds made up of 2 to 9 amino acids, and / or at least one CH-active compound , for dyeing keratin fibers.
  • Keratin-containing fibers are wool, furs, feathers and in particular human hair.
  • the colorants according to the invention can also be used to dye 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.
  • the present invention also includes the use of substances which represent reaction products of the individual components with one another.
  • Another object of the present invention is an agent for dyeing keratin fibers, in particular human hair, which contains
  • a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides and aromatic hydroxy compounds composed of 2 to 9 amino acids, and / or at least one CH- active connection.
  • Suitable compounds with the formula (1) which can be used as component A are 1, 3-diacetylbenzene, 1, 4-diacetylbenzene, 1, 3,5-triacetylbenzene, 2-benzoyl-acetophenone, 2- (4-methoxybenzoyl ) -acetophenone, 2- (2-furoyl) -acetophenone, 2- (2-pyridoyl) -acetophenone and 2- (3-pyridoyl) -acetophenone and mixtures thereof, 1, 4-diacetylbenzene, 2- (2-furoyl ) -acetephenon and 2- (3-pyridoyl) -acetephenon are preferred.
  • Suitable compounds with a primary or secondary amino group of component B are, for example, primary aromatic amines such as N, N-dimethyl, N, N-diethyl, N- (2-hydroxyethyl) -N-ethyl, N, N-bis - (2-hydroxyethyl) -, N- (2-methoxyethyl-), 2,3-, 2,4-, 2,5-dichloro-p-phenylenediamine, 2-chloro-p-phenylenediamine, 2,5-dihydroxy -4-morpholinoaniline dihydrobromide, 2-, 3-, 4-aminophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o-, p-phenylenediamine, o-, m-toluenediamine , 2,5-diaminotoluene, phenol, phenethol, 4-amino-3-methylphenol, 2- (2,5-diamin
  • R 6 represents a hydroxy or an amino group which can be substituted by C 1-4 alkyl, C 1-4 hydroxy alkyl or C ⁇ alkoxy-C ⁇ alkyl
  • R 7 , R 8 , R 9 , R 0 and R 11 for hydrogen, a hydroxyl or an amino group which is substituted by a C 1-4 alkyl, C M hydroxyalkyl, C 1-4 aminoalkyl or C ⁇ alkoxy-C ⁇ - alkyl group can be substituted, represent a carbon or sulfonic acid group
  • X represents a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms, optionally substituted by hydroxy groups, a carbonyl, sulfonyl or Imino group, an oxygen or sulfur atom, or a group with the formula III
  • Y is a direct bond, a CH 2 or CHOH group, Z and Z 'independently for an oxygen atom, an NR 12 group, wherein R 12 is hydrogen, a C 1-4 alkyl, or hydroxy-C 1-4 alkyl group, the group
  • the abovementioned compounds can be used both in free form and in the form of their physiologically tolerable salts, in particular as salts of inorganic acids, such as hydrochloric or sulfuric acid.
  • Suitable nitrogen-containing heterocyclic compounds are e.g. 2-, 3-, 4-amino, 2-amino-3-hydroxy, 3-amino-2-hydroxy, 2,6-diamino, 2,5-diamino, 2,3-diamino, 2-dimethylamino-5-amino-, 2-methylamino-3-amino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,6-dimethoxy-3,5-diamino-, 2,4, 5-triamino, 2,6-dihydroxy-3,4-dimethylpyhdine, 2,4-dihydroxy-5,6-diamino, 4,5,6-triamino, 4-hydroxy-2,5,6-triamino -, 2-Hydroxy-4,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-dia
  • amino acids are suitable as amino acids, for example those obtained by hydrolysis from vegetable or animal proteins, for example Collagen, keratin, casein, elastin, soy protein, wheat gluten or almond protein, accessible amino acids. Both acidic and alkaline amino acids can be used.
  • Preferred amino acids are arginine, histidine, tyrosine, phenylalanine, DOPA (dihydroxyphenylalanine), ornithine, lysine and tryptophan.
  • 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.
  • Use together with compounds having a primary or secondary amino group or with aromatic hydroxy compounds is preferred.
  • Suitable aromatic hydroxy compounds are e.g. 2-, 4-, 5-methylresorcinol, 2,5-dimethylresorcinol, 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, -acetophenone, 2-, 4-chlororesorcinol , 1-naphthol, 1, 5-, 2,3-, 2,7-dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalenesulfonic acid, 3,6-dihydroxy-2,7-naphthalenesulfonic acid.
  • CH-active compounds which may be mentioned are 1, 2,3,3-tetramethyl-3H-indolium iodide, 1, 2,3,3-tetramethyl-3H-indolium-p-toluenesulfonate, 1, 2,3,3-tetrams - 3-H-indolium methanesulfonate, Fischer's base (1, 3,3-trimethyl-2-methylene indoline), 2,3-dimethyl-benzothiazolium iodide, 2,3-dimethyl-benzothiazolium p-toluenesulfonate, rhodanine, rhodanine -3-acetic acid, 1-ethyl-2-quinaldinium iodide, 1-methyl-2-quinaldinium iodide, barbituric acid, thiobarbituric acid, 1, 3-dimethylthiobarbituric acid, diethylthio-barbituric acid, oxindole,
  • coloring substances can also be used together in all coloring agents;
  • components from the groups of compounds with primary or secondary amino group, of nitrogen-containing heterocycles, aromatic hydroxy compounds or amino acids can be used together, provided that they do not impair the reinforcing effect of the added substances desired according to the invention.
  • oxidizing agents for example H 2 0 2
  • H 2 0 2 oxidizing agents
  • Oxidizing agents are generally used in an amount of 0.01 to 6% by weight, based on the application solution.
  • a preferred oxidizing agent for human hair is H 2 0 2 .
  • the colorants according to the invention result in a wide range of color shades in the range from yellow-orange to brown-black; the fastness properties are excellent, the sensitization potential is very low.
  • the colorants according to the invention contain, in addition to the compounds contained according to the invention, customary direct dyes, e.g. from the group of nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 known compounds and 4-amino-2-nitrodiphenylamine-2 ' -carboxylic acid, 6-nitro-1, 2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitro-toluidine, picramic acid, 2-amino-6-chloro-4-nitrophenol, 4-ethylamino-3-nitrobenzoic acid and 2-chloro-6-ethylamino-1-hydroxy-4-nitrobenzene.
  • the agents according to the invention in accordance with this embodiment preferably contain the substantive dyes in an amount of 0.01 to 20% by weight, based on the total colorant.
  • preparations according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, Millennium blossom, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • naturally occurring dyes such as, for example, henna red, henna neutral, henna black, Millennium blossom, sandalwood, black tea, sapwood, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • Further dye components contained in the colorants according to the invention can also be indoles and indolines, and also their physiologically tolerable salts.
  • Preferred examples are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 6 -Hydroxyindole, 6-aminoindole and 4-aminoindole.
  • oxidation dye precursors or the optional direct dyes each represent uniform compounds. Rather, in the colorants according to the invention, due to the production processes for the individual dyes, further components may also be present in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. toxicological, must be excluded.
  • the colorants according to the invention produce intensive colorations even at physiologically tolerable temperatures of below 45 ° C. They are therefore particularly suitable for dyeing human hair.
  • the colorants can usually be incorporated into a water-containing cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions such as Shampoos or other preparations that are suitable for use on the keratin fibers. If necessary, it is also possible to incorporate the colorants into anhydrous carriers.
  • the colorants according to the invention can contain all active substances, additives and auxiliaries known in such preparations.
  • the colorants contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants being suitable in principle. In many In some cases, however, it has proven advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Suitable anionic surfactants in preparations according to the invention are all anionic surface-active substances suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • anionic group such as. B. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group with about 10 to 22 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • anionic surfactants are, in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanol ammonium salts with 2 or 3 carbon atoms in the alkanol group, linear fatty acids with 10 to 22 carbon atoms (Soap),
  • Ether carboxylic acids of the formula R-0- (CH 2 -CH 2 0) x -CH 2 -COOH, in which R is a linear alkyl group with 10 to 22 C atoms and x 0 or 1 to 16, acyl sarcosides with 10 to 18 C atoms in the acyl group, acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group, sulfosuccinic acid and dialkyl esters with 8 to 18 C atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl ester with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, methyl al
  • esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and in particular salts of saturated and in particular unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one - COO (' »- or
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyl dimethylammonium glycinate, and 2 -Alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ -18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -S0 3 H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 . 18 acyl sarcosine.
  • Nonionic surfactants contain z as a hydrophilic group.
  • Examples of the cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, for.
  • the quaternized protein hydrolyzates are further cationic surfactants which can be used according to the invention.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) as well as Abil®-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxane, quaterium-80).
  • alkylamidoamines in particular fatty acid amidoamines such as stearylamidopropyldimethylamine, available under the name Tego Amid®S 18, stand out a good conditioning effect especially due to its good biodegradability.
  • quaternary sugar derivative that can be used as a cationic surfactant is the commercial product Glucquat®100, according to the CTFA nomenclature a "lauryl methyl gluceth-10 hydroxypropyl dimonium chloride".
  • the compounds with alkyl groups used as surfactants can each be uniform substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with different alkyl chain lengths depending on the respective raw material are obtained.
  • both products with a "normal” homolog distribution and those with a narrowed homolog distribution can be used.
  • “Normal” homolog distribution is understood to mean mixtures of homologs which are obtained as catalysts from the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • Cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, and vinylpyrrolidone-methidolidolidol imidolidolinolidol imidolidol imidoxinolidol imidonyl chloride imidazole amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chlor
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose de vate, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxy methyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such as e.g. Polyvinyl alcohol,
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils,
  • Protein hydrolyzates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolyzates, their condensation products with fatty acids and quaternized protein hydrolyzates, perfume oils, dimethyl isosorbide and cyclodextrins,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol,
  • Anti-dandruff agents such as piroctone olamine and zinc omadine, other substances for adjusting the pH value,
  • Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins, cholesterol, Light stabilizers,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, fatty acid aeanolamides,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole, opacifiers such as latex,
  • Pearlescent agents such as ethylene glycol mono- and distearate
  • Blowing agents such as propane-butane mixtures, N 2 0, dimethyl ether, C0 2 and air and antioxidants.
  • constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; e.g. emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
  • Suitable metal salts are e.g. Formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkaline earth metals, such as potassium, sodium or lithium, alkaline earth metals, such as magnesium, calcium, strontium or Barium, or of aluminum, manganese, iron, cobalt, copper or zinc, with sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate being preferred.
  • These salts are preferably present in an amount of 0.03 to 65, in particular 1 to 40 mmol, based on 100 g of the total colorant.
  • the pH of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.
  • the colorants are generally 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 with a commercially available one Washed out hair shampoo.
  • the compounds of components A and B can either be applied to the hair simultaneously or in succession, it being irrelevant which of the two components is applied first.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. There may be an interval of up to 30 minutes between the application of the first and the second component. Pretreatment of the fibers with the saline solution is also possible.
  • Components A and B of the agents according to the invention can either be stored separately or together, either in a liquid to pasty preparation (aqueous or anhydrous) or as a dry powder. If the components are stored together in a liquid preparation, this should be largely anhydrous to reduce a reaction of the components. When stored separately, the reactive components are only intimately mixed with one another immediately before use. In dry storage, a defined amount of warm (50 to 80 ° C) water is usually added before use and a homogeneous mixture is produced.
  • a slurry of 10 mmoles of a coloring component, 10 mmoles of an amine, 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 briefly heated to about 80 ° C and filtered after cooling, the pH was then adjusted to 6.
  • a strand of 90% gray, untreated human hair was placed in this coloring solution at 30 ° C. for 30 minutes.
  • the colored streak was then rinsed for 30 seconds with lukewarm water, dried in a warm (30-40 ° C.) air stream and then combed out. Then the colorations are assessed visually in daylight.
  • the color depth was rated on the following scale:

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Abstract

L'invention concerne l'utilisation, pour colorer des fibres à base de kératine, de di- et d'oligoacylaromatiques de la formule (1) suivante dans laquelle R<1> et R<2> désignent chacun indépendamment l'un de l'autre un groupe alkyle (C1-C4) inférieur, un groupe aryle ou hétéroaryle, R<3>, R<4> et R<5> désignent chacun indépendamment les uns des autres un atome d'hydrogène, un atome d'halogène, un groupe alkyle C1-C4, un groupe alcoxy C1-C4 ou un groupe hydroxy-alcoxy (C1-C4), un groupe hydroxy, un groupe nitro, un groupe amino ou un groupe acyle C1-C4, sous réserve que les 1,2-diacétylbenzènes soient exclus, en présence d'un composé à groupe amino primaire ou secondaire ou à groupe hydroxy, sélectionné dans le groupe comprenant des amines aliphatiques ou aromatiques primaires ou secondaires, des composés hétérocycliques contenant de l'azote, des aminoacides, des oligopeptides composés de 2 à 9 aminoacides et des composés hydroxy aromatiques, et/ou au moins un composé à activité CH.
EP98936419A 1997-07-22 1998-07-13 Utilisation de di- et d'oligoacylaromatiques pour colorer des fibres a base de keratine Withdrawn EP0998256A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1997131400 DE19731400A1 (de) 1997-07-22 1997-07-22 Verwendung von Di- und Oligoacylaromaten zum Färben von keratinhaltigen Fasern
DE19731400 1997-07-22
PCT/EP1998/004332 WO1999004754A1 (fr) 1997-07-22 1998-07-13 Utilisation de di- et d'oligoacylaromatiques pour colorer des fibres a base de keratine

Publications (1)

Publication Number Publication Date
EP0998256A1 true EP0998256A1 (fr) 2000-05-10

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ID=7836486

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98936419A Withdrawn EP0998256A1 (fr) 1997-07-22 1998-07-13 Utilisation de di- et d'oligoacylaromatiques pour colorer des fibres a base de keratine

Country Status (5)

Country Link
EP (1) EP0998256A1 (fr)
JP (1) JP2001510782A (fr)
AU (1) AU8542198A (fr)
DE (1) DE19731400A1 (fr)
WO (1) WO1999004754A1 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5628799A (en) * 1991-09-26 1997-05-13 Clairol Incorporated Hair dying methods and kits which contain a dopa species, reactive direct dye, and a ferricyanide oxidant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9904754A1 *

Also Published As

Publication number Publication date
JP2001510782A (ja) 2001-08-07
DE19731400A1 (de) 1999-01-28
AU8542198A (en) 1999-02-16
WO1999004754A1 (fr) 1999-02-04

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