WO2000038631A1 - Agents permettant de colorer les fibres de keratine - Google Patents

Agents permettant de colorer les fibres de keratine Download PDF

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Publication number
WO2000038631A1
WO2000038631A1 PCT/EP1999/009906 EP9909906W WO0038631A1 WO 2000038631 A1 WO2000038631 A1 WO 2000038631A1 EP 9909906 W EP9909906 W EP 9909906W WO 0038631 A1 WO0038631 A1 WO 0038631A1
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WIPO (PCT)
Prior art keywords
group
lll
iii
naphthyl
halogen
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PCT/EP1999/009906
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German (de)
English (en)
Inventor
Hinrich Möller
Bernd Meinigke
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU30385/00A priority Critical patent/AU3038500A/en
Publication of WO2000038631A1 publication Critical patent/WO2000038631A1/fr

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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
    • A61K8/46—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
    • 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 an agent for dyeing keratin-containing fibers, in particular human hair, which contains certain naphthyl-azo compounds, the use of these compounds as a coloring component in hair dye compositions and a process for dyeing keratin-containing fibers, in particular human hair.
  • 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 hydroxyl or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as developer components.
  • the coupler components naphtha are usually in ⁇ m-phenylenediamine, thole, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives used.
  • coupler substances are ⁇ -naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4 -Diaminophenoxyethanol, 2-amino-4- (2-hydroxyethylamino) anisole
  • the object of the present invention is to provide colorants for keratin fibers, in particular for human hair, which are qualitatively at least equivalent to the usual oxidation hair colorants in terms of color depth, gray coverage and fastness properties, but without necessarily relying on oxidizing agents such as e.g. B. H 2 0 2 to be instructed.
  • the colorants may have no or only a very low sensitization potential.
  • the invention relates to an agent for dyeing keratin fibers, in particular human hair, containing naphthyl azo compounds of the formula I,
  • R 1 represents hydrogen, halogen, a sulfo group, nitro group, an arylazo group,
  • R 2 represents a phenyl group or naphthyl group which can be substituted by halogen, hydroxyl, amino, sulfo, carboxy, nitro or C 1 -C 4 alkoxy groups,
  • M for hydrogen, an alkali or 1/2 alkaline earth metal, 1/3 Al (III), 1/2 Zn (II), 1/4 Ti (IV), 1/4 Zr (IV), 1/3 Cr ( lll), 1/2 Co (ll), 1/2 Fe (ll), 1/3 Mo (lll) or 1/6 Mo (VI), 1/3 W (lll) or 1/6 W ( VI) or ammonium.
  • Keratin-containing fibers are wool, furs, feathers and in particular human hair.
  • the colorants according to the invention can also be used for dyeing other natural fibers, such as, As cotton, jute, sisal, linen or silk, modified natural fibers, such as. B. regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibers such as. B. polyamide, polyacrylonitrile, polyurethane and polyester fibers can be used.
  • the compounds having the formula I are preferably selected from the group of the following azo compounds: Chromotrop 2R, Chromotrop 2B, eriochrome blue SE, pontacyl violet ABSN, pontacyl violet 4R, sodium salt of 2- (4-sulfophenylazo) chromotropic acid, sodium salt of 2- (2-pyridylazo ) - chromotropic acid.
  • the above-mentioned azo compounds having the formula I are usually present in the agents according to the invention in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total colorant. They can be used as substantive colorants or in the presence of other components.
  • Colorants which contain the azo compound having the formula I alone are preferably used for colorations in the range from red, red-violet, blue-violet and red-brown.
  • azo compounds with the formula I are used in combination with metal seeds of the 2nd and 3rd main group of the periodic table and / or salts of the transition metals.
  • the compounds having the formula I and the metal salts are preferably used in a molar ratio of 0.5: 1 to 2: 1 in this embodiment.
  • the metal salts which are preferably used are preferably selected from the chlorides, sulfates, acetates, lactates and nitrates of Ca, Mg, Al (III), Zn (II), Ti (IV), Zr (IV), Cr (III), Co ( ll), Fe (ll), Mo (III, VI), Wllll, VI).
  • Oxidizing agents e.g. B. H 2 0 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 0 2 .
  • the colorants according to the invention contain, in addition to the compounds contained according to the invention, customary oxidation dye precursors, in particular selected from the compounds mentioned above, and / or substantive dyes, for example, to further modify the color shades.
  • customary oxidation dye precursors in particular selected from the compounds mentioned above, and / or substantive dyes, for example, to further modify the color shades.
  • B. from the group of nitrophenylenediamines, nitroamino phenols, anthraquinones or indophenols, such as. B.
  • HC Yellow 2 under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, 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 as well as picramic acid 2-amino-6-chloro-4-nitrophenol, 4-amino-2-nitrodiphenylamine -2'-carboxylic acid, 6-nitro-1, 2,3,4-tetrahydroquinoxaline, 4-N-ethyl-1, 4-bis (2'-hydroxyethylamino) -2-nitrobenzene hydrochloride and 1-methyl-3- nitro-4- (2'-hydroxyethyl) aminobenzene.
  • 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, chamomile flowers, sandalwood, black tea, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • 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. B. creams, emulsions, gels or surfactant-containing foaming solutions such.
  • B. shampoos or others Preparations that are suitable for use on 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 ingredients, 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 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.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts with 2 or 3 carbon atoms in the alkanol group,
  • 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, acyiisethionates 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 alkane sulfonates with 12 to 18 carbon atoms, linear alpha olefin sulfonates with 12 to 18 carbon atoms, methyl
  • 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 surface-active compounds that contain at least one quaternary ammonium group and at least one -COO () - or -S0 3 () 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-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
  • 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 -S0 3 H group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylamino-butyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylamino acetic acids each about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-coconut alkyl aminopropionate, coconut acylaminoethyl aminopropionate and C 12 . 18 - 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
  • Addition products of ethylene oxide with sorbitan fatty acid esters Addition products of ethylene oxide with fatty acid alkanolamides.
  • 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 Tr.alkylmethylammoniumchlor.de, z. B.
  • 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 polydimethylsiloxane, Quaternium-80).
  • alkylamidoamines especially fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, are notable for their good biodegradability.
  • esterquats such as those sold under the trademark Stepantex ® methylhydroxyalkyldialkoyloxyalkylammonium.
  • a suitable cationic surfactant quaternary sugar derivative is the commercial product Glucquat ® 100, according to 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 homologues which are obtained as catalysts when fatty alcohol and alkylene oxide are reacted 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 can be 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, dimethyldiallyl polymers -Dimethyldiallylammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate,
  • Thickeners such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. As methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as. B. bentonite or fully synthetic hydrocolloids such. B.
  • polyvinyl alcohol such as glucose and maleic acid
  • hair conditioning compounds such as phospholipids, for example soy lecithin, egg lecithin and cephalins, and silicone oils
  • protein hydrolysates especially elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, the Condensation products with fatty acids as well as 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 whale, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters, fatty acid alkanolamides,
  • Complexing agents such as EDTA, NTA and phosphonic acids, 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.
  • the constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; z.
  • 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. B. formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of NH 4 ⁇ potassium, sodium or lithium, with sodium acetate, lithium bromide, 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.
  • the pH of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.
  • the present invention further relates to the use of naphthyl azo compounds of the formula I,
  • R represents hydrogen, halogen, a sulfo group, nitro group, an arylazo group,
  • R 2 represents a phenyl group or naphthyl group which can be substituted by halogen, hydroxyl, amino, sulfo, carboxy, nitro or CC 4 alkoxy groups,
  • M for hydrogen, an alkali or 1/2 alkaline earth metal, 1/3 Al (III), 1/2 Zn (II), 1/4 Ti (IV), 1/4 Zr (IV), 1/3 Cr ( lll), 1/2 Co (ll), 1/2 Fe (ll), 1/3 Mo (lll) or 1/6 Mo (VI), 1/3 W (lll) or 1/6 W ( VI) or ammonium stands as a coloring component in hair dyes.
  • Yet another object of the present invention relates to a process for dyeing keratin-containing fibers, in particular human hair, in which a colorant containing naphthyl azo compounds of the formula I
  • R 1 represents hydrogen, halogen, a sulfo group, nitro group, an arylazo group
  • R 2 represents a phenyl group or naphthyl group which can be substituted by halogen, hydroxyl, amino, sulfo, carboxy, nitro or C ⁇ C ⁇ alkoxy groups
  • the naphthyl azo compounds of the formula I and the further components can either be applied to the hair at the same time or else in succession, it being irrelevant which of the components is applied first. There may be an interval of up to 30 minutes between the application of the individual components. Pretreatment of the fibers with a salt solution is also possible.
  • 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:
  • the strands of hair were first immersed in the 1% metal salt solution at 30 ° C. for 10 minutes and blotted with absorbent paper. The tresses were then immersed in a solution containing the remaining constituents.

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Abstract

L'invention concerne des agents permettant de colorer les fibres de kératine, notamment les cheveux, qui contiennent un composé naphtyl-azo de formule (I), dans laquelle R1 représente hydrogène, halogène ou un groupe sulfo, nitro ou arylazo; R2 représente un groupe phényle ou naphtyle pouvant être substitué par un halogène ou par des groupes hydroxy, amino, sulfo, carboxy, nitro ou alcoxy C¿1?-C4; M représente hydrogène, un métal alcalin ou un 1/2 métal alcalino-terreux, 1/3 Al(III), 1/2 Zn(II), 1/4 Ti(IV), 1/4 Zr(IV), 1/3 Cr(III), 1/2 Co(II), 1/2 Fe(II), 1/3 Mo(III) ou 1/6 Mo(VI), 1/3 W(III) ou 1/6 W(VI) ou ammonium.
PCT/EP1999/009906 1998-12-23 1999-12-14 Agents permettant de colorer les fibres de keratine WO2000038631A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30385/00A AU3038500A (en) 1998-12-23 1999-12-14 Agent for dying keratin fibers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998159721 DE19859721A1 (de) 1998-12-23 1998-12-23 Mittel zum Färben von keratinhaltigen Fasern
DE19859721.5 1998-12-23

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WO2000038631A1 true WO2000038631A1 (fr) 2000-07-06

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WO (1) WO2000038631A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012066028A3 (fr) * 2010-11-18 2012-07-26 L'oreal Colorants directs anioniques ayant un contre-ion tétraalkylammonium, composition colorante les contenant, et procédé de coloration de fibres kératiniques en partant de ces colorants
JP2015517558A (ja) * 2012-05-24 2015-06-22 ロレアル アンモニウム又はホスホニウム対イオンを担持するアニオン性染料又は光沢剤、これらを含む染料組成物、及びこれらの染料を使用してケラチン繊維を染色する方法
WO2016198643A1 (fr) * 2015-06-12 2016-12-15 L'oreal Procédé de coloration des cheveux en plusieurs étapes employant au moins un sel de titane et un colorant synthétique direct
WO2016198666A1 (fr) 2015-06-12 2016-12-15 L'oreal Procédé de teinture des cheveux, exempt d'agent oxydant chimique, au moyen d'un sel de titane et un colorant

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Publication number Priority date Publication date Assignee Title
GB0911493D0 (en) 2009-07-02 2009-08-12 Univ Leeds Catalysed dye systems
FR3014682B1 (fr) 2013-12-13 2015-12-18 Oreal Procede de coloration capillaire mettant en œuvre au moins un orthodiphenol, un derive du titane et un acide carboxylique
FR3014681B1 (fr) * 2013-12-13 2015-12-18 Oreal Procede de coloration capillaire mettant en œuvre au moins un orthodiphenol, un sel organique de titane et d'acide carboxylique
FR3029409B1 (fr) 2014-12-08 2016-12-09 Oreal Procede de coloration capillaire mettant en œuvre au moins un colorant, un sel organique de titane, et un polysaccharide non cellulosique
FR3029406B1 (fr) 2014-12-08 2016-12-09 Oreal Procede de coloration capillaire mettant en œuvre au moins un colorant, un sel de titane, et un polymere epaississant anionique
FR3029407B1 (fr) 2014-12-08 2016-12-09 Oreal Procede de coloration capillaire mettant en œuvre au moins un colorant direct et/ou naturel, un sel de titane, un polysaccharide cellulosique et eventuellement un solvant organique particulier
FR3029405B1 (fr) 2014-12-08 2019-08-02 L'oreal Procede de coloration capillaire mettant en œuvre au moins un colorant, un sel de titane, et un silicate insoluble

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FR1164505A (fr) * 1954-01-12 1958-10-10 Oreal Nouvelle teinture pour cheveux
GB1009796A (en) * 1963-04-24 1965-11-10 Partipharm A G Method of dyeing hair
DE1212683B (de) * 1963-09-04 1966-03-17 Therachemie Chem Therapeut Mittel zum Faerben von Haaren
EP0659398A1 (fr) * 1993-12-22 1995-06-28 L'oreal Procédé de coloration directe des fibres kératiniques humaines à l'aide de colorants sulfoniques et de vapeur d'eau

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FR1164505A (fr) * 1954-01-12 1958-10-10 Oreal Nouvelle teinture pour cheveux
GB1009796A (en) * 1963-04-24 1965-11-10 Partipharm A G Method of dyeing hair
DE1212683B (de) * 1963-09-04 1966-03-17 Therachemie Chem Therapeut Mittel zum Faerben von Haaren
EP0659398A1 (fr) * 1993-12-22 1995-06-28 L'oreal Procédé de coloration directe des fibres kératiniques humaines à l'aide de colorants sulfoniques et de vapeur d'eau

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KANAZAWA ET AL.: "Adsorption of dye onto silk and wool proteins", FUKUSHIMA DAIGAKU KYOIKUGAKUBU RONSHU, RIKA HOKOKU, vol. 59, 1996, pages 7 - 11, XP000901841 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012066028A3 (fr) * 2010-11-18 2012-07-26 L'oreal Colorants directs anioniques ayant un contre-ion tétraalkylammonium, composition colorante les contenant, et procédé de coloration de fibres kératiniques en partant de ces colorants
US9968534B2 (en) 2010-11-18 2018-05-15 L'oreal Anionic direct dye having a tetraalkylammonium counterion, dyeing composition comprising them and method for dyeing keratinous fibres starting from these dyes
JP2015517558A (ja) * 2012-05-24 2015-06-22 ロレアル アンモニウム又はホスホニウム対イオンを担持するアニオン性染料又は光沢剤、これらを含む染料組成物、及びこれらの染料を使用してケラチン繊維を染色する方法
WO2016198643A1 (fr) * 2015-06-12 2016-12-15 L'oreal Procédé de coloration des cheveux en plusieurs étapes employant au moins un sel de titane et un colorant synthétique direct
WO2016198666A1 (fr) 2015-06-12 2016-12-15 L'oreal Procédé de teinture des cheveux, exempt d'agent oxydant chimique, au moyen d'un sel de titane et un colorant
FR3037240A1 (fr) * 2015-06-12 2016-12-16 Oreal Procede de coloration capillaire en plusieurs etapes mettant en œuvre au moins un sel de titane et un colorant direct synthetique
FR3037238A1 (fr) * 2015-06-12 2016-12-16 Oreal Procede de coloration capillaire, exempt d'oxydant chimique, mettant en œuvre un sel de titane, et un colorant particulier
CN107949366A (zh) * 2015-06-12 2018-04-20 莱雅公司 使用至少一种钛盐和合成直接染料的多步骤染发方法
JP2018521032A (ja) * 2015-06-12 2018-08-02 ロレアル 少なくとも１つのチタン塩及び合成直接染料を使用する多工程染毛方法
US10716744B2 (en) 2015-06-12 2020-07-21 L'oreal Multi-step hair dyeing process using at least one titanium salt and a synthetic direct dye

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DE19859721A1 (de) 2000-06-29

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