[go: up one dir, main page]

WO2000015184A1 - Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables - Google Patents

Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables Download PDF

Info

Publication number
WO2000015184A1
WO2000015184A1 PCT/EP1999/006526 EP9906526W WO0015184A1 WO 2000015184 A1 WO2000015184 A1 WO 2000015184A1 EP 9906526 W EP9906526 W EP 9906526W WO 0015184 A1 WO0015184 A1 WO 0015184A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino
acid
group
salt
hydroxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1999/006526
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
Priority to EP99969020A priority Critical patent/EP1113779A1/fr
Priority to JP2000569769A priority patent/JP2002524484A/ja
Priority to AU59733/99A priority patent/AU5973399A/en
Publication of WO2000015184A1 publication Critical patent/WO2000015184A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61Q5/10—Preparations for permanently dyeing the hair
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4324—Direct dyes in preparations for permanently dyeing the hair

Definitions

  • the invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which stable diazonium salts are used as the coloring component.
  • 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.
  • Special representatives are, for example, p-phenylenediamine, p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2.5 Diaminophenyl) ethanol, 2- (2,5-diaminophenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolon-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • Particularly suitable coupler substances are ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthaiine, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinomino methyl ether, m-phenylenediamine, 2,4 -diaminophenoxyethanol, 1-phenyl-3- methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3- aminophenol, 2-methylresorcinol and 5-methylresorcinol.
  • 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.
  • diazonium salts for dyeing fibers containing keratin is known from the prior art and is described, for example, in the publications CH-PS-630 254, DE 27 39 227, FR-PS-78 05441 and DE-OS-27 57 866.
  • CH-PS-630 254 and DE-OS-39 227 use nitrogen-containing heterocycles as coupling components.
  • the coupling component is an arylamide derivative of acetaldehyde. From DE-OS-27 57 866 naphthyl compounds are known as coupling components.
  • dianzonium salts are used in the presence of suitable coupling components.
  • the dyeing process is carried out in such a way that the keratin-containing fiber to be dyed is first pretreated with the coupling component by removing some of the coupling component Allows time to act on the fiber.
  • the diazonium salt is then applied in a second step.
  • the two-step process is labor-intensive and time-consuming.
  • the object of the present invention is to provide dyes for keratin fibers, in particular human hair, which can be applied to the fiber in a few work steps and which are qualitatively at least equivalent to the usual oxidation hair dyes in terms of color depth, gray coverage and fastness properties, but without necessarily to be dependent on oxidizing agents such as H 2 O 2 .
  • the colorants may have no or only a very low sensitization potential.
  • the stable diazonium salts shown in the formula I can also be used in one-step processes both as direct dyeing agents and in combination with coupling components for dyeing keratin-containing fibers. Colorings with excellent brilliance and depth of color are obtained.
  • the use of oxidizing agents is not necessary, but should not be excluded in principle.
  • the invention relates to a process for dyeing keratin fibers, in particular human hair, in which
  • R 1 , R 2 , R 3 and R 4 independently of one another are a hydrogen atom, a halogen atom, a (C 1 -C 4 ) alkyl group, a (C r C 4 ) alkoxy group, a hydroxy (C 1 -C 4 ) -alkoxy group, a hydroxy group, a sulfo group, a carboxy group, an amino group, which is replaced by a (C, ⁇ ) - alkyl group, hydroxyalkyl group, a C r C 4 acyl group or a optionally substituted benzene group can be substituted or part of a heterocycle, or a (C 1 -C 4 ) acyl group, where two of the radicals can also form a fused-on benzene ring and can be an optionally substituted phenyl group, or together with the N atom one form heterocyclic ring, mean, B) optionally in combination with a compound selected from compounds with primary
  • 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, 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 stable diazonium salts of formula I used according to the invention are preferably selected from the group consisting of 4-diazo-phenylamine sulfate (Variamin blue salt RT), 4-diazo-4'-methoxydiphenylamine chloride (Variamine blue salt B), 4-diazo-3,2'-dimethylazobenzenesulfate (Real garnet salt GBC), 2-methoxy-4-nitrobenzene diazoniumnaphthalene-1, 5-disulfonate, 4-diazo-2,5-dimethoxy-4'-nitroazobenzene chloride-zinc chloride double salt (real black acid K), 2,5-dimethoxy-4- benzoylaminophenyldiazonium chloride (real blue salt RR), 2-methoxy-4-nitrobenzene diazonium 1, 5-naphthalenedisulfonate (real red salt B), 4-chloro-2-nitrobenzene diazonium chloride-zinc chloride, double salt
  • the above-mentioned stable diazonium salts with the formula I are preferably used in the process according to the invention in an amount of 0.03 to 65 mmole, in particular 1 to 40 mmol, based on 100 g of the total colorant. _-.
  • the stable diazonium salts with the formula I are used as the only colorant in the process according to the invention, colorations in the brown range are obtained. Colorings with an even higher brilliance and improved fastness properties (light fastness, wash fastness, fastness to rubbing), especially in the yellow, orange, brown and black range, are achieved if the compounds of the formula I are used together with the compounds referred to as component B. On the one hand, these are compounds which, in their own right, only weakly dye keratin-containing fibers and only produce brilliant colorations together with the diazonium salts of the formula I. On the other hand, there are also compounds that are already used as oxidation dye precursors.
  • the compounds of component B can be used in an amount of 0.03 to 65, in particular 1 to 40, mmol, in each case based on 100 g of the total colorant.
  • Suitable compounds with a primary or secondary amino group as 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-toluenediamine, 2,5-diaminotoluene, -phenol, - phenethol, 4-amino-3-methylphenol, 2- (2,5-diamin
  • R 6 , R 7 , R 8 , R 9 and R 10 represent hydrogen, a hydroxy or an amino group
  • C ⁇ alkyl, C ⁇ hydroxyalkyl, C 1-4 alkoxy, C ⁇ aminoalkyl or C 1-4 alkoxy-C 1-4 - alkyl groups may be substituted, and
  • X for a direct bond, a saturated or unsaturated carbon chain with 1 to 4 carbon atoms optionally substituted by hydroxyl groups, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom, or a group with the formula
  • Y is a direct bond, a CH 2 or CHOH group
  • Hydroxy-C 1-4 -alkyl group means the group 0- (CH 2 ) p -NH or NH- (CH 2 ) p '-O, where p and p' are 2 or 3, and o is a number of 1 to 4, such as 4,4'-diaminostilbene, 4,4'-diaminostilbene-2,2'-disulfonic acid mono- or di-Na salt, 4-amino-4'-dimethylaminostilbene, 4,4 ' -Diaminodiphenylmethane, -sulfide, -sulfoxide, -amin, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, - diphenyl ether, 3,3 ', 4,4'--
  • 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, for example, 2-, 3-, 4-amino, 2-amino-3-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-dimethylpyridine, 2,4-dihydroxy-5,6-diamino-, 4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2nd -Hydroxy-4,5,6-triamino-, 2,4,5,6-tetraami- no-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-
  • Dihydroxyindoline and 4-hydroxyindoline can be used both in free form and in the form of their physiologically tolerable salts, e.g. B. as salts of inorganic acids such as hydrochloric or sulfuric acid.
  • 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-thhydroxybenzoic acid, -acetophenone, 2-, 4-chlororesorcinol, 1-naphthol, 1, 5-, 1, 6-, 1, 7-, 2,3-, 2,6-, 2,7-dihydroxynaphthalene, 2-naphthol-3,6-disulfonic acid Na salt, 6-dimethylamino-4 -hydroxy-2-naphthai
  • 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-tetramethyl - 3H-indolium methanesulfonate, Fischer's base (1,3,3-trimethyl-2-methyleneindoline), 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, diethylthiobarbituric acid, oxindole, 3-in
  • the compounds of component B are particularly preferably selected from the group consisting of N- (2-hydroxyethyl) -N-ethyl-, 2-chloros-p-phenylenediamine, N, N- bis (2-hydroxyethyl) -p-phenylenediamine, 4-aminophenol, p-phenylenediamine, 2- (2,5-diaminophenyl) ethanol, 2,5-diaminotoluene, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro, 2-methyl-5-amino -, 3-methyl-4-amino-, 2-methyl-5- (2-hydroxyethylamino) -, 2-methyl-5-amino-4-chloro, 6-methyl-3-amino-2-chloro, 2-aminomethyl-4-amino, 2-hydroxymethyl-4-amino, 2-amino-4- (2-hydroxyethylamino) -, 3,4-methylenedioxyphenol,
  • Oxidizing agents for example H 2 O 2
  • 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 O 2 .
  • customary direct dyes e.g. from the group of nitrophyne diamines, nitroaminophenols, anthraquinones or indophenols, such as e.g.
  • the substantive dyes are preferably used in an amount of 0.01 to 20% by weight, based on the colorant used.
  • oxidation dye precursors or the optional direct dyes each represent uniform compounds. Rather, in the process according to the invention, due to the production process for the individual dyes, further components can be used in minor amounts are used, provided that they do not adversely affect the color result or must be excluded for other reasons, e.g. toxicological
  • the method according to the invention already gives intense colorations at physiologically acceptable temperatures of below 45 ° C. It is therefore particularly suitable for coloring human hair.
  • the individual components are usually incorporated into a water-containing cosmetic carrier.
  • Suitable water-containing cosmetic carriers are e.g. B creams, emulsions, gels or also surfactant-containing foaming solutions such as shampoos or other preparations that are suitable for use on the keratin-containing fibers. If necessary, it is also possible to incorporate the components into anhydrous carriers
  • 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, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group about 10 to 22 carbon atoms.
  • anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group about 10 to 22 carbon atoms
  • glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups can be contained in the molecule.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium and Mono-, di- and t ⁇ alkanoiammonium salts with 2 or 3 carbon atoms in the alkanol group,
  • Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) x -CH 2 -COOH, in which R is a linear one
  • Alkyl group with 10 to 22 carbon atoms and x 0 or 1 to 16,
  • Sulfosuccinic acid mono- and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid mono-alkyl polyoxyethyl esters with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkane sulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, alpha-sulfofatty acid methyl ester of fatty acids with 12 to 18 carbon atoms, alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) x -SO 3 H, in which R is a preferably linear alkyl group with 10 to 18 C atoms and x 0 or 1 to 12,
  • Esters of tartaric acid and citric acid with alcohols the addition products of about 2 to 15 molecules of ethylene oxide and / or propylene oxide to 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 those surface-active compounds which carry at least one quaternary ammonium group and at least one -COO H or -SO ⁇ 'group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyl dimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyl dimethylammonium glycinate, and 2-alkyl -3-carboxymethyl-3-hydroxyethyl-imidazoiine each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under the CT
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a C 8 . 18 alkyl or acyl group in the molecule contain at least one free amino group and at least one -COOH or -SO 3 H group 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 18C Atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C 12 _ ⁇ 8 acyl sarcosine.
  • Nonionic surfactants contain z as a hydrophilic group.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • Examples of the cationic surfactants which can be used in the processes according to the invention are, in particular, quaternary ammonium compounds.
  • Ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g. B. cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethyl ammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • 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) and Abil®-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, Quaternium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid®S 18, are characterized in particular by their good biodegradability.
  • esterquats such as those sold under the trademark Stepantex ® methylhydroxyalkyldialkoyloxyalkylammonium.
  • 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 narrow homolog distribution can be used.
  • "normal” homolog division are understood to mean mixtures of homologs which are obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides -
  • hydroxides or alcoholates can be used as catalysts.
  • the use of products with a narrow homolog distribution can be preferred.
  • auxiliaries and additives are, for example, nonionic polymers such as, for example, vinylpyrrolidone-acrylate copolymers,
  • Imidazolinium methochloride copolymers and quaternized polyvinyl alcohol, zwitterionic and amphoteric polymers such as, for example, acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert.-butylaminoethyl methacrylate ⁇ hydroxydyl methacrylate copolymers, for example polyacrylic acids, polyacrylic polymers, anionic polymers, anionic polymers, anionic polymers, anionic polymers, Vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone / vinyl acrylate
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans,
  • Cellulose derivatives e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and
  • Dextrins clays such as e.g. B. bentonite or fully synthetic hydrocolloids such as e.g.
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin,
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol 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,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as whale, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether,
  • Pearlescent agents such as ethylene glycol mono- and distearate
  • Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, C0 2 and air as well
  • constituents of the water-containing carrier are used in the usual amounts for the preparation of the agents used in the process according to the invention, 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, for example, formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, Propionates, phosphates and phosphonates of alkali 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 are 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 used.
  • the pH of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.
  • the components and customary cosmetic ingredients are usually applied to the fibers containing keratin, left on the fiber for some time, usually about 30 minutes, and then rinsed out or washed out with a shampoo.
  • the stable diazonium salts of the formula I and the compounds of component B are applied to the hair in one process step, i.e. the components are applied together or in succession, but without the fiber being present in one of the components.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. Pretreatment of the fibers with the saline solution is not excluded.
  • the stable diazonium salts of the formula I and the compounds of component B are preferably stored separately, 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. Examples
  • a slurry of 10 mmoles of a stable diazonium salt of Formula I, 10 mmoles of an oxidation dye precursor, 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 tress was then rinsed with lukewarm water for 30 seconds, dried with warm air and then combed out.
  • the color depth was rated on the following scale:

Landscapes

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

Abstract

L'invention concerne un procédé de coloration de fibres contenant de la kératine, notamment de cheveux humains. Ce procédé consiste à appliquer sur les fibres en une seule opération A) au moins un sel de diazonium stable de la formule (I) où R<1>, R<2>, R<3> et R<4>, indépendamment les uns des autres, représentent un atome d'hydrogène, un atome d'halogène, un groupe alkyle (C1-C4), un groupe alcoxy (C1-C4), un groupe hydroxy-(C1-C4)-alcoxy, un groupe hydroxy, un groupe sulfo, un groupe carboxy, un groupe amino qui peut être substitué par un groupe alkyle (C1-C4), un groupe hydroxyalkyle, un groupe acyle C1-C4 ou un groupe benzène éventuellement substitué ou pouvant faire partie intégrante d'un hétérocycle, ou un groupe acyle (C1-C4), deux des restes pouvant former un noyau benzène fusionné, et peut être un groupe phényle éventuellement substitué ou former avec l'atome N un noyau hétérocyclique, ou bien les sels physiologiquement compatibles de ce sel de diazonium; B) éventuellement en association avec un composé sélectionné parmi des composés contenant un groupe amino primaire ou secondaire sélectionné parmi des amines aromatiques primaires ou secondaires, des composés hétérocycliques azotés et/ou des composés hydroxy aromatiques et/ou des composés actifs CH.
PCT/EP1999/006526 1998-09-15 1999-09-04 Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables Ceased WO2000015184A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99969020A EP1113779A1 (fr) 1998-09-15 1999-09-04 Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables
JP2000569769A JP2002524484A (ja) 1998-09-15 1999-09-04 安定なジアゾニウム塩を用いてケラチン含有繊維を染色する方法
AU59733/99A AU5973399A (en) 1998-09-15 1999-09-04 Method for dyeing fibres containing keratin using stable diazonium salts

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998142071 DE19842071A1 (de) 1998-09-15 1998-09-15 Verfahren zum Färben von keratinhaltigen Fasern unter Verwendung von stabilen Diazoniumsalzen
DE19842071.4 1998-09-15

Publications (1)

Publication Number Publication Date
WO2000015184A1 true WO2000015184A1 (fr) 2000-03-23

Family

ID=7880938

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/006526 Ceased WO2000015184A1 (fr) 1998-09-15 1999-09-04 Procede de coloration de fibres contenant de la keratine a l'aide de sels de diazonium stables

Country Status (5)

Country Link
EP (1) EP1113779A1 (fr)
JP (1) JP2002524484A (fr)
AU (1) AU5973399A (fr)
DE (1) DE19842071A1 (fr)
WO (1) WO2000015184A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003030841A1 (fr) * 2001-10-04 2003-04-17 Henkel Kommanditgesellschaft Auf Aktien Procede de coloration de fibres keratiniques
WO2003032939A1 (fr) * 2001-10-15 2003-04-24 Ciba Specialty Chemicals Holding Inc. Procede destine a colorer des fibres contenant de la keratine au moyen de sels diazoiques
US6790239B1 (en) 1999-10-23 2004-09-14 Henkel Kommanditgesellschaft Auf Aktien Agent for coloring keratin containing fibers
US7223295B2 (en) 2003-05-15 2007-05-29 Ciba Specialty Chemicals Corporation Method of coloring porous material
FR3076212A1 (fr) * 2017-12-29 2019-07-05 L'oreal Procede de soin/reparation des fibres keratiniques mettant en œuvre un compose diazonium et un apport energetique

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19949033A1 (de) * 1999-10-12 2001-04-19 Henkel Kgaa Haarfärbeverfahren
DE10020732B4 (de) * 2000-04-27 2006-09-21 Kpss-Kao Professional Salon Services Gmbh 1,2,4,5-Tetraaminobenzol enthaltendes Haarfärbemittel
AU2003206919A1 (en) * 2002-02-25 2003-09-09 Ciba Specialty Chemicals Holding Inc. Method of colouring keratin-containing fibres
BR0314007A (pt) 2002-09-02 2005-07-19 Ciba Sc Holding Ag Método de colorir material poroso
FR2920778B1 (fr) 2007-09-11 2009-10-30 Oreal Composes quinoliniums azoiques a motif disulfure/thiol, compositions les comprenant, procede de coloration de fibres keratiniques et dispositif.
FR2921382B1 (fr) 2007-09-21 2009-10-30 Oreal Colorant derive de phenyl-pyridol[1,2-a]indolium thiol-disulfure, composition tinctoriale comprenant ce colorant, procede d'eclaircissement des matieres keratiniques a partir de ce colorant
FR2921258A1 (fr) * 2007-09-24 2009-03-27 Oreal Composition tinctoriale comprenant au moins un precurseur incolore disulfures/thiol, proced de coloration a partir de la composition
FR2925311B1 (fr) 2007-12-21 2009-12-18 Oreal Procede d'eclaircissement de fibres keratiniques humaines mettant en oeuvre une composition anhydre et une amine organique particuliere et dispositif approprie
FR2940067B1 (fr) 2008-12-19 2011-02-25 Oreal Composition oxydante pour le traitement des fibres keratiniques comprenant un polymere cationique, un amide gras et un agent-oxygene
FR2940055B1 (fr) 2008-12-19 2015-03-27 Oreal Composition de teinture d'oxydation des fibres keratiniques comprenant le para-aminophenol, du dipropyleneglycol, et un precurseur de colorant additionnel.
FR2954159B1 (fr) 2009-12-22 2012-02-10 Oreal Agent de coloration et/ou de decoloration des fibres keratiniques comprenant une composition comprenant un agent alcalinisant et une composition anhydre comprenant un oxydant, l'une ou l'autre des compositions pouvant contenir un corps gras
FR2954127B1 (fr) 2009-12-22 2015-10-30 Oreal Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties, comprenant un corps gras et un agent sequestrant.

Citations (1)

* 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

Patent Citations (1)

* 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

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6790239B1 (en) 1999-10-23 2004-09-14 Henkel Kommanditgesellschaft Auf Aktien Agent for coloring keratin containing fibers
WO2003030841A1 (fr) * 2001-10-04 2003-04-17 Henkel Kommanditgesellschaft Auf Aktien Procede de coloration de fibres keratiniques
WO2003032939A1 (fr) * 2001-10-15 2003-04-24 Ciba Specialty Chemicals Holding Inc. Procede destine a colorer des fibres contenant de la keratine au moyen de sels diazoiques
US7192453B2 (en) 2001-10-15 2007-03-20 Ciba Specialty Chemicals Corporation Method of coloring keratin-containing fibres using diazonium salts
US7223295B2 (en) 2003-05-15 2007-05-29 Ciba Specialty Chemicals Corporation Method of coloring porous material
FR3076212A1 (fr) * 2017-12-29 2019-07-05 L'oreal Procede de soin/reparation des fibres keratiniques mettant en œuvre un compose diazonium et un apport energetique

Also Published As

Publication number Publication date
DE19842071A1 (de) 2000-03-16
EP1113779A1 (fr) 2001-07-11
JP2002524484A (ja) 2002-08-06
AU5973399A (en) 2000-04-03

Similar Documents

Publication Publication Date Title
EP1194117A2 (fr) Substance destinee a la teinture de fibres keratiniques
WO2000038636A1 (fr) Agent permettant de colorer les fibres de keratine
EP1037586A1 (fr) Utilisation d&#39;aldehydes et de cetones d&#39;onium pour colorer des fibres a base de keratine
WO2000076466A1 (fr) Derives de xanthene pour teindre des fibres contenant de la keratine
EP0977546A1 (fr) Utilisation d&#39;aldehydes insatures pour colorer des fibres a base de keratine
EP1113779A1 (fr) Procede de coloration de fibres contenant de la keratine a l&#39;aide de sels de diazonium stables
WO2000038632A1 (fr) Procede permettant de colorer les fibres de keratine au moyen de derives de l&#39;acide 2-oxocarboxylique associes a des nucleophiles
EP1028694A1 (fr) Utilisation d&#39;indanones pour colorer des fibres a base de keratine
WO1998047472A1 (fr) Utilisation d&#39;isatines 1-substituees pour la coloration de fibres keratiniques
EP1139988B1 (fr) Agents permettant de colorer les fibres de keratine
EP0873746A2 (fr) Agent de teinture pour les fibres kératiniques
EP0873743A2 (fr) Utilisation de benzylidene-cétones pour teindre les fibres kératiniques
EP1028695A1 (fr) Agent de coloration pour fibres a base de keratine, a teneur en acide dehydroascorbique
EP1139990B1 (fr) Agent permettant de colorer les fibres de keratine
EP1194116B1 (fr) Agent de coloration de fibres contenant de la keratine
WO1999019558A2 (fr) Utilisation de derives de malonaldehyde pour colorer des fibres contenant de la keratine
EP1112055A1 (fr) Produit de coloration de fibres contenant de la keratine
EP1198457B1 (fr) Azafluorenones quaternarises et leur utilisation dans des agents pour colorer des fibres a base de keratine
WO2001005359A2 (fr) Substance destinee a teindre des fibres contenant de la keratine
WO2001003661A1 (fr) Agent de coloration de fibres contenant de la keratine et comprenant au moins un compose aromatique nitroso
WO2001030312A1 (fr) Agent pour colorer des fibres a base de keratine
EP0998256A1 (fr) Utilisation de di- et d&#39;oligoacylaromatiques pour colorer des fibres a base de keratine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 1999969020

Country of ref document: EP

ENP Entry into the national phase

Ref country code: JP

Ref document number: 2000 569769

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 59733/99

Country of ref document: AU

WWP Wipo information: published in national office

Ref document number: 1999969020

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1999969020

Country of ref document: EP