WO1999025314A1 - Utilisation de phenothiazines alkylees pour la coloration de fibres keratiniques - Google Patents

Utilisation de phenothiazines alkylees pour la coloration de fibres keratiniques Download PDF

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Publication number
WO1999025314A1
WO1999025314A1 PCT/EP1998/007162 EP9807162W WO9925314A1 WO 1999025314 A1 WO1999025314 A1 WO 1999025314A1 EP 9807162 W EP9807162 W EP 9807162W WO 9925314 A1 WO9925314 A1 WO 9925314A1
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group
compounds
alkyl group
hydrogen atom
independently
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PCT/EP1998/007162
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German (de)
English (en)
Inventor
Bernd Meinigke
Hinrich Möller
David Rose
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 AU12339/99A priority Critical patent/AU1233999A/en
Publication of WO1999025314A1 publication Critical patent/WO1999025314A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B21/00—Thiazine dyes

Definitions

  • the invention relates to the use of alkylated phenothiazines for dyeing keratin-containing fibers, in particular human hair, an agent for dyeing keratin-containing fibers which contains alkylated phenothiazines, 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.
  • the direct dyes form the color directly on the fiber due to their own color.
  • the color on the fiber fades over time or is washed out during washing. Compared to the oxidation dyes, the intensity of the coloring and the fastness properties are lower.
  • Oxidation dye precursors sometimes have a sensitizing effect on people with sensitive skin. Direct dyes are applied under gentler conditions. They are often used in combination with oxidation dyes to obtain certain color shades.
  • the published patent application DE 33 05 305 A1 describes a process for dyeing hair with basic dyes, in which the hair is changed in such a way that more than 75% of the cystine bonds of the peptide chain of the keratin of the hair are converted into S-sulfocysteine groups, the larger one Part of the peptide chains Molecular weight between about 1100 and about 7500. Methylene blue, for example, is used as the basic colorant.
  • the keratin-containing fibers first have to be pretreated in a complex manner in order to obtain a coloration. The authenticity properties of the copies obtained by this process are unsatisfactory.
  • the object of the present invention is to provide colorants for keratin-containing fibers, in particular human hair, which can be used as direct colorants and which are at least equivalent in quality to conventional oxidation hair colorants in terms of color depth, gray coverage and fastness properties.
  • 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.
  • alkylated phenothiazines used according to the invention are outstandingly suitable as substantive substances for dyeing keratin-containing fibers. They result in colors with excellent brilliance and depth of color and lead to a wide range of shades.
  • oxidizing agents is not necessary, but it should not be excluded in principle.
  • the present invention accordingly relates to the use of alkylated phenothiazines of the following formula I.
  • R 1 and R 2 are each independently an NH 2 , NHR 8 or NR 8 R 9 group, in which R 8 and R 9 represent a (C 1 -C 4 -alkyl group, R 3 to R 6 are each independently a hydrogen atom or a (C, -C 4 ) alkyl group,
  • R 7 is a hydrogen atom, a halogen atom or a nitro group and X represents the anion of a mineral acid or organic acid, with the proviso that if R 1 and R 2 are both an NR 8 R 9 group, then at least one of the radicals R 3 to R 6 is a (C r C 4 ) alkyl group for dyeing keratin fibers.
  • the present invention therefore furthermore relates to an agent for dyeing keratin-containing fibers, in particular human hair, which contains (A) one or more alkylated phenothiazines of the following formula I.
  • R 1 and R 2 are each independently an NH 2 , NHR 8 or NR 8 R 9 group in which R 8 and R 9 represent a (C r C 4 ) alkyl group, R 3 to R 6 each are independently a hydrogen atom or a (CC 4 ) alkyl group,
  • R 7 is a hydrogen atom, a halogen atom or a nitro group and X represents the anion of a mineral acid or organic acid, with the proviso that if R 1 and R 2 are both an NR 8 R 9 group, then at least one of the radicals R 3 to R 6 is a (C 1 -C 4 ) alkyl group,
  • condensation dye precursors from the group of reactive carbonyl compounds and compounds with primary or secondary amino group or hydroxy group selected from primary or secondary aromatic amines, nitrogen-containing heterocyclic compounds and aromatic hydroxy compounds.
  • 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.
  • Suitable compounds with the formula I which can be used as component A are Azur A, Azur B, Azur C, 1, 9-dimethylmethylene blue, toluidine blue, Neu methylene blue N, thionine, methylene green and methylene green-zinc chloride double salt.
  • the compounds of the formula I are preferably present in the compositions according to the invention in an amount of 0.03 to 65, in particular 1 to 40 mmol, based on 100 g of the total colorant.
  • oxidation dye precursors or condensation dye precursors mentioned as components B and C are well known in the field of hair colorants. Condensation dye precursors are described, for example, in German patent application 197 17 224.5.
  • Preferred developer components according to the invention are p-phenylenediamine, p-toluylenediamine, p-aminophenol, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, N, N-bis- (2-hydroxyethyl) -p-phenylenediamine , 2- (2,5-diaminophenoxy) -ethanol, 1 -pheny!
  • Coupler components preferred according to the invention are 1-naphthol, pyrogallol, 1, 5-, 2,7- and 1,7-dihydroxynaphthalene, o-aminophenol, 5-amino-2-methylphenol, m-amino- phenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazolon-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-dihydroxypyridine, 2,6-diaminopyridine, 2-amino-3-hydroxypyridine, 2, 6-dihydroxy-3,4-diaminopyridine, 3-amino-2-methylamino-6-meth
  • developer components and coupler components are usually used in approximately molar amounts to one another. If the molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components can preferably be present in the colorant in a molar ratio of 1: 0.5 to 1: 2. The total amount of
  • Oxidation dye precursors are generally at most 20% by weight, based on the total agent.
  • oxidation dye precursors it is not necessary for the oxidation dye precursors to be uniform compounds. Rather, in the hair 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.
  • coloring substances with the formula I and different compounds from components B and C can also be used together in all coloring agents.
  • This embodiment also includes the use of such substances, the reaction products of the individual components, namely the phenothiazines and the oxidation dye precursors
  • the compounds of components B and C can each be present in the agents according to the invention in an amount of 0.03 to 65, in particular 1 to 40 mmol, based on 100 g of the total colorant.
  • the colorants according to the invention result in a wide range of color shades in the range from yellow to yellow-brown, orange, brown-orange, medium brown, dark brown, violet, dark violet to blue-black and 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 the nitrophenylenediamines, nitroaminophenols, anthraquinones, indophenols or the compounds known as Arianors, such as e.g.
  • HC Yellow 2 under the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yeliow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HCBIue 2, Disperse Blue 3, Basic Blue 99 , HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16, Basic Brown 17, Picramic acid and 2-amino-6-chloro-4-nitrophenol known compounds as well as 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.
  • the colorants 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, sapwood, 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, sapwood, 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. 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 water-free 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 trium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts
  • Ether carboxylic acids of the formula RO- (CH 2 -CH 2 O) 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,
  • Mono and dialkyl sulfosuccinic acid with 8 to 18 carbon atoms in the alkyl group and mono alkyl polyoxyethyl sulfosuccinate 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 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 -SO ⁇ group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyl-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 cocoacylaminoethyl-hydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known under
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8-18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts.
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltauhne, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 C. 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.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group.
  • Such connections are, for example
  • 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 are preferred,
  • Dialkyldimethylmonium chlorides and trialkylmethylammonium chlorides e.g. 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 polydimethylsiloxanes, Quatemium-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.
  • 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 usually preferred in the manufacture of these substances from native vegetable or animal raw materials to go out, so that substance mixtures with different, depending on the respective raw material alkyl chain lengths 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.
  • auxiliaries and additives are, for example, 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, dimethyldiallylammonyl dimethyldiallyl - methyldiallylammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone-
  • nonionic polymers such as, for example, vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers and polysiloxanes
  • cationic polymers such as
  • 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 / 2-hydroxypropyl methacrylate copolymers, polyacrylic acids, for example, anionic polymers, such as anionic polymers , Vinyl acetate / crotonic acid copolymers, vinyl pyrrolidone ⁇ / inylacrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert-butylacrylamide terpolymers,
  • Thickening agents such as agar agar, guar gum, alginates, xanthan gum, gum arabic cum, karaya gum, locust bean gum, linseed gums, dextrans, cellulose loose derivatives, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. B. bentonite or fully synthetic hydrocolloids such as polyvinyl alcohol,
  • Structurants such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example soy lecithin,
  • Protein hydrolyzates especially elastin, collagen, keratin, milk protein,
  • 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,
  • 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, CO 2 and air as well
  • the constituents of the water-containing carrier are used to produce the colorants according to the invention in amounts customary for this purpose; for example Emulsifiers in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant used.
  • Suitable metal salts are, for example, formates, carbonates, halides, sulfates, butyrates, valerates, capronates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates from 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, preference being given to sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc sulfate, ZnCl 2 double salts, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate are. These salts are preferably present in an amount of 0.03 to 65, in particular 1 to 40 mmol, based on 100
  • the pH of the ready-to-use coloring preparations is usually between 2 and 11, preferably between 5 and 9.
  • the compounds of the formula I used according to the invention are generally used in the presence of a water-containing cosmetic carrier in an amount of 0.03 to 65, in particular 1 to 40 mmol, in each case based on 100 g of the entire colorant, applied to the hair, left there for about 30 minutes and then rinsed out or washed out with a commercially available hair shampoo. Further optional colorants, if used, can be applied in the same amount as the compounds of formula I used according to the invention.
  • the compounds with the formula I and further colorants can either be applied to the hair simultaneously or else in succession, it being irrelevant which of the components is applied first.
  • the optionally contained ammonium or metal salts can be added to the first or the second component. Between the application of the first and the second Components can be up to 30 minutes apart. Pretreatment of the fibers with the saline solution is also possible.
  • the compounds with the formula I and further colorants 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 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. The colorations were then assessed visually in daylight.
  • the color depth was rated on the following scale:

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Abstract

L'invention concerne l'utilisation de phénothiazines alkylées de la formule (I) pour la coloration de fibres kératiniques. Dans cette formule (I), R1 et R2 représentent indépendamment l'un de l'autre un groupe NH¿2?-, NHR?8- ou NR8R9, R8 et R9¿ représentant un groupe alkyle (C¿1?-C4); R?3 à R6¿ représentent respectivement et indépendamment l'un de l'autre un atome d'hydrogène ou un groupe alkyle (C¿1?-C4); R?7¿ représente un atome d'hydrogène, un atome d'halogène ou un groupe nitro et X représente l'anion d'un acide minéral ou d'un acide organique. Si R1 et R2 représentent ensemble un groupe NR8R9, au moins un des restes R3 à R6 est un groupe alkyle (C¿1?-C4).
PCT/EP1998/007162 1997-11-13 1998-11-10 Utilisation de phenothiazines alkylees pour la coloration de fibres keratiniques WO1999025314A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU12339/99A AU1233999A (en) 1997-11-13 1998-11-10 Use of alkylated phenothiazines for dyeing keratinous fibres

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19750303.9 1997-11-13
DE1997150303 DE19750303A1 (de) 1997-11-13 1997-11-13 Verwendung von alkylierten Phenothiazinen zum Färben von keratinhaltigen Fasern

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WO1999025314A1 true WO1999025314A1 (fr) 1999-05-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7371744B2 (en) 2001-05-30 2008-05-13 Photopharmica Limited Biologically active methylene blue derivatives

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2308936C2 (ru) 2001-03-19 2007-10-27 Л`Аван Гард Инк. Композиция для одновременного осветления и окрашивания волос, содержащая устойчивые к обесцвечиванию кислотные и основные красители
DE10260881A1 (de) * 2002-12-23 2004-07-08 Henkel Kgaa Mittel zum Färben von keratinhaltigen Fasern
FR2889946B1 (fr) * 2005-09-01 2012-08-17 Oreal Compositions tinctoriales comprenant au moins un compose de type leuco protege, procede de coloration les mettant en oeuvre
CN101325986B (zh) 2005-10-06 2012-12-26 西巴特殊化学制品控股公司 *嗪二硫化物染料
FR3060994B1 (fr) * 2016-12-22 2020-10-02 Oreal Procede de coloration des fibres keratiniques mettant en oeuvre au moins un colorant azinium particulier et au moins un colorant fluorescent

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4066746A (en) * 1968-05-01 1978-01-03 Lever Brothers Company Reducing the drying time of hair with fluorine-containing vinyl polymers
DE3305305A1 (de) * 1982-02-17 1983-08-25 L'Oreal, 75008 Paris Polymerisat auf keratin-basis, verfahren zu seiner herstellung und mittel, das dieses polymerisat enthaelt
DE4302013C1 (de) * 1993-01-26 1994-06-01 Uwe Dr Fiedeldei Verfahren zur Herstellung reiner Phenothiazinfarbstoffe

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4066746A (en) * 1968-05-01 1978-01-03 Lever Brothers Company Reducing the drying time of hair with fluorine-containing vinyl polymers
DE3305305A1 (de) * 1982-02-17 1983-08-25 L'Oreal, 75008 Paris Polymerisat auf keratin-basis, verfahren zu seiner herstellung und mittel, das dieses polymerisat enthaelt
DE4302013C1 (de) * 1993-01-26 1994-06-01 Uwe Dr Fiedeldei Verfahren zur Herstellung reiner Phenothiazinfarbstoffe

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7371744B2 (en) 2001-05-30 2008-05-13 Photopharmica Limited Biologically active methylene blue derivatives
US7732439B2 (en) 2001-05-30 2010-06-08 Photopharmica Limited Biologically active methylene blue derivatives
US7855197B2 (en) 2001-05-30 2010-12-21 Photopharmica Limited Biologically active methylene blue derivatives
US7915254B2 (en) 2001-05-30 2011-03-29 Photopharmica Limited Biologically active methylene blue derivatives
US8188074B2 (en) 2001-05-30 2012-05-29 Photopharmica Limited Biologically active methylene blue derivatives

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AU1233999A (en) 1999-06-07

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