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US20030177591A1 - Method of dyeing keratin-containing fibers - Google Patents

Method of dyeing keratin-containing fibers Download PDF

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Publication number
US20030177591A1
US20030177591A1 US10/398,825 US39882503A US2003177591A1 US 20030177591 A1 US20030177591 A1 US 20030177591A1 US 39882503 A US39882503 A US 39882503A US 2003177591 A1 US2003177591 A1 US 2003177591A1
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alkyl
phenyl
substituted
hydrogen
formula
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Peter Mockli
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Priority to US11/235,912 priority Critical patent/US7189268B2/en
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    • 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
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • 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
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/16—1,3-Diazoles or hydrogenated 1,3-diazoles ; (Benz)imidazolium

Definitions

  • the present invention relates to a method of dyeing keratin-containing fibres, especially human hair, using cationic imidazole azo dyes.
  • Cationic imidazole azo dyes and the use thereof for dyeing hair are already known, for example, from WO 95/01772 and EP-A-714 954.
  • Such dyes are especially suitable for dyeing undamaged hair, since they are capable of penetrating into the hair shaft relatively easily on account of their low molecular weight. They also exhibit good fastness to washing on undamaged hair, but are washed out of severely damaged (bleached) hair relatively easily.
  • the present invention accordingly relates to a method of dyeing keratin-containing fibres, which comprises using a dye of formula
  • R 1 and R 2 are each independently of the other hydrogen, C 1 -C 4 alkyl, halogen or nitro,
  • R 3 and R 4 are each independently of the other unsubstituted C 1 -C 4 alkyl or C 1 -C 4 alkyl substituted by OH, C 1 -C 4 alkoxy, halogen, CN or by phenyl,
  • X 1 and X 2 are each independently of the other hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen,
  • R 5 is hydrogen or C 1 -C 4 alkyl
  • R 6 is C 5 -C 12 alkyl or C 5 -C 8 cycloalkyl each unsubstituted or substituted by OH, C 1 -C 4 alkoxy, halogen, CN or phenyl, or R 6 is C 1 -C 4 alkyl substituted by phenyl or by C 5 -C 8 cycloalkyl, or wherein R 5 and R 6 together with the nitrogen atom linking them form a piperazine ring, which is substituted, at the nitrogen atom that is not bonded to the phenyl group, by C 1 -C 8 -alkyl or phenyl, or which is quaternised at that nitrogen atom by two such groups, the C 1 -C 8 -alkyl radicals and phenyl mentioned as substituents of the nitrogen atom of the piperazine ring being unsubstituted or substituted by OH, C 1 -C 4 alkoxy, halogen, CN or phenyl,
  • alkyl radicals are to be understood generally as straight-chain or branched alkyl radicals, for example methyl, ethyl, n- and iso-propyl and n-, sec- and tert-butyl.
  • alkyl radicals and also the cycloalkyl groups may be mono- or poly-substituted, for example by hydroxy, carboxy, halogen, cyano or C 1 -C 4 alkoxy.
  • the alkoxy radicals may contain from 1 to 12 carbon atoms, preferably from 1 to 4 carbon atoms. They are, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentyloxy or n-hexyloxy.
  • the alkoxy groups too, may be substituted, for example by the radicals mentioned as possible substituents for the alkyl groups, especially by hydroxy or C 1 -C 4 alkoxy.
  • Suitable anions X ⁇ include both inorganic and organic anions, for example halide, such as chloride, bromide or iodide, sulfate, hydrogen sulfate, methyl sulfate, boron tetrafluoride, aminosulfonate, perchlorate, carbonate, bicarbonate, phosphate, nitrate, benzenesulfonate, formate, acetate, propionate, lactate, and complex anions, such as the anion of a zinc chloride double salt.
  • halide such as chloride, bromide or iodide
  • sulfate hydrogen sulfate, methyl sulfate, boron tetrafluoride
  • aminosulfonate perchlorate
  • carbonate bicarbonate
  • phosphate nitrate
  • benzenesulfonate formate
  • acetate propionate
  • lactate complex anions
  • the anion is generally predetermined by the preparation process.
  • chlorides, hydrogen sulfates, sulfates, methosulfates, phosphates, formates, lactates or acetates are present.
  • Halogen is to be understood as fluorine, bromine or iodine or, especially, chlorine.
  • Each of R 1 and R 2 is preferably methyl and especially hydrogen.
  • Each of R 3 and R 4 is preferably ethyl, hydroxyethyl or especially methyl.
  • Each of X 1 and X 2 is preferably methoxy, methyl, chlorine or especially hydrogen.
  • R 5 is preferably hydrogen, methyl or ethyl, especially hydrogen or methyl.
  • R 5 is hydrogen.
  • C 5 -C 12 Alkyl radicals R 6 are preferably corresponding unsubstituted alkyl radicals, especially C 5 -C 8 alkyl radicals and preferably C 6 -C 8 alkyl radicals.
  • C 5 -C 8 Cycloalkyl radicals R 6 are preferably corresponding unsubstituted cycloalkyl radicals, especially cyclohexyl radicals.
  • R 6 is preferably phenyl-substituted or cyclohexyl-substituted C 1 -C 4 alkyl, especially phenyl-substituted C 1 -C 4 alkyl.
  • R 6 is especially preferably C 5 -C 8 alkyl
  • R 5 and R 6 together with the nitrogen atom linking them form a piperazine ring which is substituted, at the nitrogen atom that is not bonded to the phenyl group, by C 1 -C 4 alkyl or phenyl.
  • Especially preferred dyes used according to the invention are those of formula
  • X 1 and X 2 are each independently of the other hydrogen, methyl or methoxy,
  • R 5 is hydrogen
  • R 6 is benzyl, C 6 -C 8 alkyl or cyclohexyl
  • R 5 and R 6 together with the nitrogen atom linking them form a piperazine ring, which is substituted, at the nitrogen atom that is not bonded to the phenyl ring, by C 1 -C 4 alkyl or phenyl, and
  • X ⁇ is an anion
  • R 1 and R 2 are each independently of the other hydrogen, C 1 -C 4 alkyl, halogen or nitro,
  • R 3 and R 4 are each independently of the other unsubstituted C 1 -C 4 alkyl or C 1 -C 4 alkyl substituted by OH, C 1 -C 4 alkoxy, halogen, CN or by phenyl,
  • X 1 and X 2 are each independently of the other hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen,
  • R 5 is hydrogen or C 1 -C 4 alkyl
  • R 6 ′ is C 5 -C 8 alkyl; C 5 -C 8 cycloalkyl or phenyl-substituted C 1 -C 4 alkyl;
  • R 5 and R 6 together with the nitrogen atom linking them form a piperazine ring, which is substituted, at the nitrogen atom that is not bonded to the phenyl group, by C 1 -C 4 -alkyl or phenyl, and
  • X ⁇ is an anion
  • R 6 ′ is especially preferably C 5 -C 8 alkyl, phenyl-substituted C 1 -C 8 alkyl or C 5 -C 8 cycloalkyl.
  • the invention relates also to the compounds of formula (3).
  • the dyes of formula (1) can be prepared according to methods known per se (see e.g. EP-A-714 954).
  • the dyes of formula (1) can be obtained, for example, by reacting a compound of formula
  • substituents have the definitions and preferred meanings indicated above.
  • compounds of formula (4) those compounds which, instead of the methoxy group indicated, contain halogen, e.g. chlorine, or C 2 -C 4 alkoxy.
  • the compounds of formulae (4) and (5) are known or can be prepared in a manner known per se.
  • the compounds of formula (4) can be obtained by diazotising 4-alkoxyanilines, coupling the product with an imidazole and then carrying out alkylation and quaternisation.
  • the reaction of a compound of formula (4) with an amine of formula (5) can be carried out, for example, at a temperature of about from 40 to 100° C., preferably from 40 to 70° C., optionally under pressure and/or in an inert gas atmosphere, and in an inert solvent, e.g. in water or especially aliphatic alcohols, e.g. C 1 -C 8 alcohols, such as methanol, ethanol or especially isopropanol. It is also possible to carry out the reaction in aprotic polar solvents, such as dimethylformamide or dimethyl sulfoxide. In the case of amines that are liquid under the reaction conditions, it is possible, if desired, to dispense with a solvent.
  • the invention relates also to compositions for dyeing keratin-containing material that comprise such dyes.
  • the compounds of formula (1) are present in the compositions according to the invention preferably in an amount of from 0.001% to 5%, especially from 0.01% to 1%, based on the total dyeing composition.
  • the dyes of formula (1) according to the invention produce colour shades in the range from yellowish-red to bluish-red, and the fastness properties are excellent. Attention is drawn to the property thereof that enables hair that has already been dyed a dark colour still to be distinctly altered in shade.
  • the dyes are distinguished by a good storage stability also at alkaline pH values, e.g. pH 9.5.
  • dyes of formula (1) in admixture with one or more further cationic dyes, for example in mixtures comprising a dye of formula (1) and at least one of the dyes described in WO 95/01772.
  • one, two, three or even more dyes from WO 95/01772 may be used.
  • dyes there may be mentioned as examples of such dyes the yellow dye according to Example 1, the red dye according to Example 4 and the orange dye according to Example 46 of WO 95/01772.
  • dye mixtures comprising a dye of formula (1) and the yellow dye according to Example 1 and/or the red dye according to Example 4 and/or the orange dye according to Example 46 of WO 95/01772.
  • the dyeing compositions according to the invention comprise, in addition to the dyes of formula (1) according to the invention, customary direct dyes, for example from the group of the nitroanilines, nitrophenylenediamines, nitroaminophenols, anthraquinones, indophenols, phenazines, phenothiazines, methines or the compounds known as Arianors, such as, for example, the compounds known by the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 6, Basic Yellow 57, Basic Yellow 9, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, Basic Red 2, Basic Violet 14, Basic Blue 3, Basic Blue 6, Basic Blue 7, Basic Blue 9, Basic Blue 12, Basic Blue 26, HC Blue 2, HC Blue 7, HC Blue 12, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 und Basic Brown 17, and also picramic acid, 2-
  • cationised nitroaniline and anthraquinone dyes for example those described in the following patent specifications: U.S. Pat. No. 5,298,029, especially In column 2, line 33 to column 5, line 38; U.S. Pat. No. 5,360,930, especially in column 2, line 38 to column 5, line 49; U.S. Pat. No. 5,169,403, especially in column 2, line 30 to column 5, line 38; U.S. Pat. No. 5,256,823, especially in column 4, line 23 to column 5, line 15; U.S. Pat. No. 5,135,543, especially in column 4, line 24 to column 5, line 16;
  • cationic azo dyes e.g. according to GB-A-2 319 776, as well as the oxazine dyes described in DE-A-299 12 327 and mixtures thereof with the other direct dyes mentioned therein, are likewise very suitable for combination.
  • compositions of the invention according to this embodiment contain the dyes preferably in an amount of from 0.01 to 5% by weight, based on the total dyeing composition.
  • the dyeing compositions according to the invention may also comprise naturally occurring dyes, such as, for example, henna red, henna neutral, henna black, camomile blossom, sandalwood, black tea, Rhamnus frangula bark, sage, campeche wood, madder root, catechu, sedre and alkanet root.
  • Naturally occurring dyes such as, for example, henna red, henna neutral, henna black, camomile blossom, sandalwood, black tea, Rhamnus frangula bark, sage, campeche wood, madder root, catechu, sedre and alkanet root.
  • oxidation dye precursors where present, or for the dyes each to be single compounds, but rather there may in addition be present in the dyeing compositions according to the invention, in lesser amounts, further components predetermined by the preparation processes for the individual dyes, provided such components do not have an adverse effect on the dyeing result or do not need to be excluded for other reasons, for example on toxicological grounds.
  • the dyes of formula (1) according to the invention may also readily be used in combination with other dyes and/or adjuvants used in the colouring of hair, for example with
  • oxidising agents in the form of permanent-wave fixing solution as described in DE-A-19 713 698, especially page 4, lines 52 to 55, or EP-A-1 062 940, especially page 6, lines 41 to 47, (and in the equivalent WO 99/40895),
  • oxidation dyeing compositions as described in EP-A-850 636, especially page 5, line 41 to page 7, line 52, EP-A-850 637, especially page 6, line 50 to page 8, line 44, EP-A-850 638, especially page 7, line 20 to page 9, line 26, and EP-A-852 135, especially page 4, line 54 to page 6, line 53,
  • oxidation dyeing compositions with cationic couplers as described in WO 99/48856, especially page 9, line 16 to page 13, line 8, and WO 99/48875, especially page 11, line 20 to page 12, line 13,
  • oxidation dyes in the presence of oxidoreductase enzyme as described in WO 99/17730, especially page 4, line 11 to page 13, line 28, and WO 99/36034, especially pages 3 to 15,
  • thickening polymers as described in EP-A-970 684, especially page 48, line 16 to page 51, line 4,
  • sugar-containing polymers as described in EP-A-970 687, especially page 28, line 17 to page 29, line 23,
  • anionic surfactants as described in WO 00/10518, especially page 45, line 11 to page 48, line 3,
  • non-ionic surfactants as described in WO 00/10519, especially page 45, line 11 to page 50, line 12, or
  • silicones as described in WO 00/12057, especially page 45, line 9 to page 55, line 2.
  • the dyeing compositions according to the invention produce intense dyeings even at physiologically tolerable temperatures of less than 45° C. They are accordingly suitable especially for dyeing human hair.
  • the dyeing compositions can usually be incorporated into an aqueous cosmetic carrier.
  • Suitable aqueous cosmetic carriers include, for example, creams, emulsions, gels and also surfactant-containing foaming solutions, e.g. shampoos or other preparations, that are suitable for use on keratin-containing fibres. Such forms of use are described in detail in Research Disclosure 42448 (August 1999).
  • the dyeing compositions according to the invention are also excellently suitable for the dyeing method described in DE-A-3 829 870 using a dyeing comb or a dyeing brush.
  • the dyeing compositions according to the invention may furthermore comprise any active ingredient, additive or adjuvant known for such preparations.
  • the dyeing compositions in many cases comprise at least one surfactant, there being suitable in principle anionic and also zwitterionic, ampholytic, non-ionic and cationic surfactants. In many cases, however, it has proved advantageous to select the surfactants from anionic, zwitterionic and non-ionic surfactants.
  • Anionic surfactants suitable for use in the preparations according to the invention include any anionic surface-active substance that is suitable for use on the human body. Such a substance is characterised by an anionic group that imparts water solubility, for example a carboxylate, sulfate, sulfonate or phosphate group, and a lipophilic alkyl group having approximately from 10 to 22 carbon atoms.
  • an anionic group that imparts water solubility for example a carboxylate, sulfate, sulfonate or phosphate group, and a lipophilic alkyl group having approximately from 10 to 22 carbon atoms.
  • glycol or polyglycol ether groups, ester, ether and amide groups and also hydroxy groups may be present in the molecule.
  • suitable anionic surfactants each in the form of sodium, potassium or ammonium salts or mono-, di- or tri-alkanolammonium salts having 2 or 3 carbon atoms in the alkanol group:
  • acyl sarcosides having from 10 to 18 carbon atoms in the acyl group
  • acyl taurides having from 10 to 18 carbon atoms in the acyl group
  • acyl isothionates having from 10 to 18 carbon atoms in the acyl group
  • sulfosuccinic acid mono- and di-alkyl esters having from 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid monoalkylpolyoxyethyl esters having from 8 to 18 carbon atoms in the alkyl group and from 1 to 6 oxyethyl groups,
  • alkyl sulfates and alkyl polyglycol ether sulfates of formula R′—O(CH 2 —CH 2 —O) x′ —SO 3 H, in which R′ is a preferably linear alkyl group having from 10 to 18 carbon atoms and x′ 0 or from 1 to 12,
  • esters of tartaric acid and citric acid with alcohols that are addition products of approximately from 2 to 15 molecules of ethylene oxide and/or propylene oxide with fatty alcohols having from 8 to 22 carbon atoms.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having from 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and also especially salts of saturated and especially unsaturated C 8 -C 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • zwitterionic surfactants denotes surface-active compounds that carry at least one quaternary ammonium group and at least one —COO ( ⁇ ) or —SO 3 ( ⁇ ) group in the molecule.
  • Zwitterionic surfactants that are especially suitable are the so-called betaines, such as the N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, for example cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines having from 8 to 18 carbon atoms in the alkyl or acyl group and also cocoacylaminoethylhydroxyethylcarboxymethyl glycinate.
  • a preferred zwitterionic surfactant is the fatty acid
  • Ampholytic surfactants are to be understood as meaning surface-active compounds that, in addition to a C 8 -C 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.
  • ampholytic surfactants include N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl-glycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each having approximately from 8 to 18 carbon atoms in the alkyl group.
  • Ampholytic surfactants to which special preference is given are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C 18 acylsarcosine.
  • Non-ionic surfactants contain as the hydrophilic group, for example, a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups.
  • Such compounds are, for example:
  • ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethyl-ammonium chlorides and trialkylmethylammonium chlorides, for example cetyltrimethyl-ammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride.
  • Further cationic surfactants that can be used in accordance with the invention are quaternised protein hydrolysates.
  • cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilised trimethylsilylamodimethicone), Dow Corning 929 emulsion (comprising a hydroxylamino-modified silicone, which is also referred to as amodimethicone), SM-2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and also Abil®-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; diquaternary polydimethylsiloxanes, quaternium-80).
  • Alkylamidoamines especially fatty acid amidoamines, such as the stearylamidopropyl-dimethylamine obtainable under the name Tego Amid® 18, are distinguished not only by a good conditioning action but also especially by their good biodegradability.
  • Quaternary ester compounds so-called “esterquats”, such as the methyl hydroxyalkyl-dialkoyloxyalkylammonium methosulfates marketed under the trade mark Stepantex®, are also very readily biodegradable.
  • quaternary sugar derivative that can be used as cationic surfactant is the commercial product Glucquat®100, according to CTFA nomenclature a “lauryl methyl gluceth-10 hydroxypropyl dimonium chloride”.
  • the alkyl-group-containing compounds used as surfactants may be single substances, but the use as starting materials of natural raw materials of vegetable or animal origin is generally preferred in the preparation of such substances, with the result that the substance mixtures obtained have different alkyl chain lengths according to the particular starting material used.
  • the surfactants that are addition products of ethylene oxide and/or propylene oxide with fatty alcohols or derivatives of such addition products may either be products having a “normal” homologue distribution or products having a restricted homologue distribution.
  • “Normal” homologue distribution is to be understood as meaning mixtures of homologues obtained in the reaction of fatty alcohol and alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts.
  • Restricted homologue distributions are obtained when, for example, hydrotalcites, alkali metal salts of ether carboxylic acids, alkali metal oxides, hydroxides or alcoholates are used as catalysts.
  • the use of products having restricted homologue distribution may be preferred.
  • non-ionic polymers for example vinylpyrrolidone/vinyl acrylate copolymers, polyvinyl-pyrrolidone and vinylpyrrolidone/vinyl acetate copolymers and polysiloxanes,
  • cationic polymers such as quaternised cellulose ethers, polysiloxanes having quaternary groups, dimethyldiallylammonium chloride polymers, copolymers of dimethyldiallylammonium chloride and acrylic acid, as available commercially under the name Merquat® 280 and the use of which in hair dyeing is described, for example, in DE-A-4 421 031, especially page 2, lines 20 to 49, or EP-A-953 334, especially page 27, line 17 to page 30, line 11, acrylamide/dimethyldiallylammonium chloride copolymers, diethyl-sulfate-quaternised dimethylaminoethyl methacrylate/vinylpyrrolidone copolymers, vinylpyrrolidone/imidazolinium methochloride copolymers,
  • zwitterionic and amphoteric polymers such as, for example, acrylamidopropyl-trimethyl-ammonium chloride/acrylate copolymers and octylacrylamide/methyl methacrylate/tert-butylaminoethyl methacrylate/2-hydroxypropyl methacrylate copolymers,
  • anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate/crotonic acid copolymers, vinylpyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobornyl acrylate copolymers, methyl vinyl ether/maleic anhydride copolymers and acrylic acid/ethyl acrylate/N-tert-butyl acrylamide terpolymers,
  • thickeners such as agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean flour, linseed gums, dextrans, cellulose derivatives, e.g. methyl cellulose, hydroxyalkyl cellulose, hydroxyethyl ethylcellulose and carboxymethyl cellulose, starch fractions and derivatives, such as amylose, amylopectin and dextrins, clays, e.g. bentonite or fully synthetic hydrocolloids such as, for example, polyvinyl alcohol,
  • structuring agents such as glucose and maleic acid
  • hair-conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin, and cephalins, silicone oils, and also conditioning compounds, for example such as those described in DE-A-19 729 080, especially page 2, lines 20 to 49, EP-A-834 303, especially page 2, line 18 to page 3, line 2, or EP-A-312 343, especially page 2, line 59 to page 3, line 11,
  • protein hydrolysates especially elastin, collagen, keratin, milk protein, soya protein and wheat protein hydrolysates, condensation products thereof with fatty acids and also quaternised protein hydrolysates, and phospholipids, like ceramide,
  • perfume oils dimethyl isosorbitol and cyclodextrins
  • solubilisers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
  • anti-dandruff active ingredients such as piroctones, olamines and zinc Omadine
  • active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidonecarboxylic acids and salts thereof, plant extracts and vitamins,
  • consistency regulators such as sugar esters, polyol esters or polyol alkyl ethers
  • fats and waxes such as spermaceti, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
  • complexing agents such as EDTA, NTA and phosphonic acids
  • swelling and penetration substances such as polyols and polyol ethers, as listed extensively, for example, in EP-A-962 219, especially page 27, lines 18 to 38, for example glycerol, propylene glycol, propylene glycol monoethyl ether, butyl glycol, benzyl alcohol, carbonates, hydrogen carbonates, guanidines, ureas and also primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole,
  • polyols and polyol ethers as listed extensively, for example, in EP-A-962 219, especially page 27, lines 18 to 38, for example glycerol, propylene glycol, propylene glycol monoethyl ether, butyl glycol, benzyl alcohol, carbonates, hydrogen carbonates, guanidines, ureas and also primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole,
  • opacifiers such as latex
  • pearlising agents such as ethylene glycol mono- and di-stearate
  • propellants such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air, and also
  • the constituents of the aqueous carrier are used in the preparation of the dyeing compositions according to the invention in the amounts customary for that purpose; for example emulsifiers are used in concentrations of from 0.5 to 30% by weight and thickeners in concentrations of from 0.1 to 25% by weight of the total dyeing composition.
  • the pH value of the ready-to-use dyeing preparations is usually from 2 to 11, preferably from 5 to 10.
  • the dyeing compositions are usually applied to the hair in an amount of from 50 to 100 g in the form of a mixture with the aqueous cosmetic carrier, left on the hair for approximately 30 minutes and then rinsed off or washed off with a commercially available hair shampoo.
  • the compounds used according to the invention and, where used, the oxidation dye precursors may be applied to the keratin-containing fibres either simultaneously or in succession, the order in which they are applied being unimportant.
  • the compounds used according to the invention and, where used, the oxidation dye precursors of the compositions according to the invention may be stored separately or together, either in a liquid to paste-like preparation (aqueous or non-aqueous) or in the form of a dry powder.
  • a liquid preparation aqueous or non-aqueous
  • the preparation should be substantially anhydrous in order to reduce reaction of the components.
  • the reactive components are intimately mixed with one another only immediately before use. In the case of dry storage, before use a defined amount of hot (from 50 to 80° C.) water is usually added and a homogeneous mixture prepared.
  • a strongly alkaline 10% solution of a non-ionic surfactant (Plantaren 2000, Henkel) is adjusted to pH 9.5 using citric acid. 0.1% of the dye of formula
  • [0152] is dissolved therein and a strand of human hair, bleached white, is treated with the dye solution at room temperature. After only a short period of time, the strand has been dyed a red shade, which is still very intense even after shampooing ten times. The dye also has a strong affinity for undamaged hair. In that case, too, the fastness to washing is very good.
  • a surfactant base consisting of 10% cocoamphoglycinate and 90% water is applied for 20 minutes to a strand each of bleached and unbleached white human hair (“Italian white virgin” IMHAIR Ltd.), rinsed and shampooed once. Very intense, vibrant scarlet dyeings of identical shade are obtained on both qualities of hair. Surprisingly, both the colour strength and fastness to washing are excellent and very similar for both qualities of hair, which speaks for the good levelling ability of this product.
  • Example 4 illustrates a method for “lightening” dyeings, as described also in WO 97/20545.
  • the solution is combined with the same weight of a 6% hydrogen peroxide solution and the mixture is immediately applied to a strand of dark-blonde natural European hair. After 5 minutes, the strand of hair is rinsed and dried.
  • a dye formulation is prepared from
  • [0181] is slurried in 40 g 2-propanol at room temperature. The temperature is then raised to 45-50° C. and 40 g of N-phenylpiperazine is added. The mixture is stirred for 30 hours. Then the reaction mass is diluted with 140 g of methyl-ethyl-ketone, cooled to room temperature, when crystallization occurs. The crystal suspension is separated by filtration, washed twice with 20 g methyl-ethyl-ketone and dried in a vacuum dryer to get 63 g of a dark powder.

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  • Plural Heterocyclic Compounds (AREA)
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US10/398,825 2000-10-12 2001-10-10 Method of dyeing keratin-containing fibers Abandoned US20030177591A1 (en)

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US20040143913A1 (en) * 2001-07-11 2004-07-29 Moeckli Peter Method of coloring hair using cationic dyes
US20040187231A1 (en) * 2003-03-18 2004-09-30 Eliu Victor Paul Cationic dimeric dyes
US20040244127A1 (en) * 2001-09-24 2004-12-09 Jean-Marie Adam Cationic reactive dyes
US20040244125A1 (en) * 2001-10-10 2004-12-09 Peter Mockli Method of dyeing keratin-containing fibres
US20040250355A1 (en) * 2001-10-15 2004-12-16 Jean-Marie Adam Method of colouring keratin-containing fibres using diazonium salts
US20050125913A1 (en) * 2003-12-11 2005-06-16 Saroja Narasimhan Method and compositions for coloring hair
FR2872035A1 (fr) * 2004-06-23 2005-12-30 Oreal Utilisation de composes polycationiques en teinture des fibres keratiniques
US20060037151A1 (en) * 2004-06-23 2006-02-23 L'oreal Use of polycationic compounds in the dyeing of keratinous fibres
EP1648402A1 (fr) * 2003-06-16 2006-04-26 L'oreal Composition tinctoriale eclaircissante comprenant au moins un colorant direct cationique a chromophores mixtes
US20070124872A1 (en) * 2003-12-19 2007-06-07 Eliu Victor P Method of coloring with capped diazotized compound and coupling component
US20070214580A1 (en) * 2004-04-02 2007-09-20 Eliu Victor P Cationic Imidazolazo Dyes Containing A 2,5-Diaminophenyl
US20090255063A1 (en) * 2006-07-18 2009-10-15 Sophie Marquais-Bienewald Polymeric hair dyes
US9839592B2 (en) 2015-03-19 2017-12-12 Noxell Corporation Fluorescent compounds for treating hair
US9839593B2 (en) 2015-03-19 2017-12-12 Noxell Corporation Method of coloring hair with direct dye compounds
US9844501B2 (en) 2015-03-19 2017-12-19 Noxell Corporation Compositions for dyeing hair with cationic direct dyes
US9849072B2 (en) 2015-03-19 2017-12-26 Noxell Corporation Method of coloring hair with direct dye compounds
US9855202B2 (en) 2015-03-19 2018-01-02 Noxell Corporation Compositions for dyeing hair with cationic direct dyes
US9872823B2 (en) 2015-03-19 2018-01-23 Noxell Corporation Method for improving fastness properties of fluorescent compounds on hair
US9913791B2 (en) 2015-03-19 2018-03-13 Noxell Corporation Method for improving acid perspiration resistance of fluorescent compounds on hair
US9918919B1 (en) 2016-09-16 2018-03-20 Noxell Corporation Method of coloring hair with washfast yellow imidazolium direct dye compounds
US9943472B2 (en) 2015-03-19 2018-04-17 Noxell Corporation Acid perspiration resistant fluorescent compounds for treating hair
US9982138B2 (en) 2016-09-13 2018-05-29 Noxell Corporation Hair color compositions comprising stable violet-blue to blue imidazolium dyes
US10034823B2 (en) 2016-09-16 2018-07-31 Noxell Corporation Method of coloring hair with washfast blue imidazolium direct dye compounds

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FR2825624B1 (fr) 2001-06-12 2005-06-03 Oreal Composition de teinture des fibres keratiniques humaines avec des colorants directs et des composes dicationiques
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EP1631715B1 (fr) * 2003-06-11 2012-01-04 Basf Se Formulations d'agents de blanchiment optique stables au stockage
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US7201779B2 (en) 2003-06-16 2007-04-10 L'oreal S.A. Dye composition comprising at least one direct dye containing mixed chromophores
US7438728B2 (en) 2004-12-15 2008-10-21 L'oreal S.A. Dissymmetrical diazo compounds comprising 2-pyridinium group and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device
FR2879196B1 (fr) * 2004-12-15 2007-03-02 Oreal Composes diaz0iques symetriques a groupements 2-imidazolium et bras de liaison non cationique, compositions les comprenant, procede de coloration et dispositif
US7396368B2 (en) 2004-12-15 2008-07-08 L'oreal S.A. Symmetrical diazo compounds comprising 4-pyridinium groups and a cationic or non-cationic linker, compositions comprising them, method for coloring, and device
US7247713B2 (en) 2004-12-15 2007-07-24 L'oreal, S.A. Symmetrical diazo compounds containing 2-pyridinium groups and cationic or non-cationic linker, compositions comprising them, method of coloring, and device
US7288639B2 (en) 2004-12-15 2007-10-30 L'oreal S.A. Dyssymmetrical diazo compounds having at least one 4-pyridinium unit and a cationic or non-cationic linker, compositions comprising them, method of coloring, and device
FR2889954B1 (fr) 2005-08-26 2007-10-19 Oreal Colorants mixtes cationiques comprenant un chromophore anthraquinone et leur utilisation en colorant capillaire
JP2009507944A (ja) 2005-08-30 2009-02-26 チバ ホールディング インコーポレーテッド チオール基を含む染料
EP2029674B1 (fr) 2006-06-13 2013-05-22 Basf Se Colorants tricationiques
KR100851614B1 (ko) * 2007-02-28 2008-08-12 로레알 줄롤리딘 유닛을 가지는 양이온성 아조 염료, 그를포함하는 염색용 조성물, 및 염색 방법
KR101614167B1 (ko) * 2008-01-17 2016-04-20 바스프 에스이 중합체성 모발 염료
MX2011005938A (es) * 2008-12-05 2011-06-27 Unilever Nv Coloracion de fibras queratinosas usando un pretratamiento comprendiendo una sal de hierro y un revelador de color comprendiendo tanino hidrolizable.
TW201116595A (en) 2009-07-15 2011-05-16 Basf Se Polymeric hair dyes
CN103068930B (zh) 2010-08-17 2015-09-30 巴斯夫欧洲公司 二硫化物或硫醇聚合物染发剂
GB201201536D0 (en) * 2012-01-30 2012-03-14 Sheedy Paul D Method and apparatus for communicating messages to individuals
KR102244166B1 (ko) 2013-09-02 2021-04-26 로레알 양이온성 스티릴 디술파이드 염료를 사용하는 케라틴 섬유 염색 방법, 및 상기 염료를 포함하는 조성물

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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040143913A1 (en) * 2001-07-11 2004-07-29 Moeckli Peter Method of coloring hair using cationic dyes
US7078498B2 (en) 2001-07-11 2006-07-18 Cibe Specialty Chemicals Corporation Method of coloring hair using cationic dyes
US20040244127A1 (en) * 2001-09-24 2004-12-09 Jean-Marie Adam Cationic reactive dyes
US6949630B2 (en) 2001-09-24 2005-09-27 Ciba Specialty Chemicals Corporation Cationic reactive dyes
US7354572B2 (en) 2001-10-10 2008-04-08 Ciba Specialty Chemicals Corp. Method of dyeing keratin-containing fibres
US20040244125A1 (en) * 2001-10-10 2004-12-09 Peter Mockli Method of dyeing keratin-containing fibres
US7192453B2 (en) 2001-10-15 2007-03-20 Ciba Specialty Chemicals Corporation Method of coloring keratin-containing fibres using diazonium salts
US20040250355A1 (en) * 2001-10-15 2004-12-16 Jean-Marie Adam Method of colouring keratin-containing fibres using diazonium salts
US7166710B2 (en) 2003-03-18 2007-01-23 Ciba Specialty Chemicals Corporation Cationic dimeric dyes
US20040187231A1 (en) * 2003-03-18 2004-09-30 Eliu Victor Paul Cationic dimeric dyes
EP1648402A1 (fr) * 2003-06-16 2006-04-26 L'oreal Composition tinctoriale eclaircissante comprenant au moins un colorant direct cationique a chromophores mixtes
US7494514B2 (en) 2003-12-11 2009-02-24 Revlon Consumer Products Corporation Method and compositions for coloring hair
US20050125913A1 (en) * 2003-12-11 2005-06-16 Saroja Narasimhan Method and compositions for coloring hair
US20070124872A1 (en) * 2003-12-19 2007-06-07 Eliu Victor P Method of coloring with capped diazotized compound and coupling component
US7482438B2 (en) 2004-04-02 2009-01-27 Ciba Specialty Chemicals Corp. Cationic imidazolazo dyes containing a 2,5-diaminophenyl moiety
US20070214580A1 (en) * 2004-04-02 2007-09-20 Eliu Victor P Cationic Imidazolazo Dyes Containing A 2,5-Diaminophenyl
US7326259B2 (en) 2004-06-23 2008-02-05 L'oreal S.A. Use of polycationic compounds in the dyeing of keratinous fibres
US20060037151A1 (en) * 2004-06-23 2006-02-23 L'oreal Use of polycationic compounds in the dyeing of keratinous fibres
EP1618865A1 (fr) * 2004-06-23 2006-01-25 L'oreal Utilisation de composés polycationiques en teinture des fibres kératiniques
FR2872035A1 (fr) * 2004-06-23 2005-12-30 Oreal Utilisation de composes polycationiques en teinture des fibres keratiniques
US20090255063A1 (en) * 2006-07-18 2009-10-15 Sophie Marquais-Bienewald Polymeric hair dyes
US7731761B2 (en) 2006-07-18 2010-06-08 Ciba Corporation Polymeric hair dyes
US9849072B2 (en) 2015-03-19 2017-12-26 Noxell Corporation Method of coloring hair with direct dye compounds
US9839593B2 (en) 2015-03-19 2017-12-12 Noxell Corporation Method of coloring hair with direct dye compounds
US9844501B2 (en) 2015-03-19 2017-12-19 Noxell Corporation Compositions for dyeing hair with cationic direct dyes
US9839592B2 (en) 2015-03-19 2017-12-12 Noxell Corporation Fluorescent compounds for treating hair
US9855202B2 (en) 2015-03-19 2018-01-02 Noxell Corporation Compositions for dyeing hair with cationic direct dyes
US9872823B2 (en) 2015-03-19 2018-01-23 Noxell Corporation Method for improving fastness properties of fluorescent compounds on hair
US9913791B2 (en) 2015-03-19 2018-03-13 Noxell Corporation Method for improving acid perspiration resistance of fluorescent compounds on hair
US9943472B2 (en) 2015-03-19 2018-04-17 Noxell Corporation Acid perspiration resistant fluorescent compounds for treating hair
US9982138B2 (en) 2016-09-13 2018-05-29 Noxell Corporation Hair color compositions comprising stable violet-blue to blue imidazolium dyes
US9918919B1 (en) 2016-09-16 2018-03-20 Noxell Corporation Method of coloring hair with washfast yellow imidazolium direct dye compounds
US10034823B2 (en) 2016-09-16 2018-07-31 Noxell Corporation Method of coloring hair with washfast blue imidazolium direct dye compounds

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WO2002031056A1 (fr) 2002-04-18
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US20040049020A1 (en) 2004-03-11
KR20030036914A (ko) 2003-05-09
WO2002030374A1 (fr) 2002-04-18
EP1324741A1 (fr) 2003-07-09
DE60122545D1 (de) 2006-10-05
BR0114585A (pt) 2003-08-26
EP1325085A1 (fr) 2003-07-09
DE60122545T2 (de) 2007-10-04
EP1324741B1 (fr) 2006-08-23
US20060026776A1 (en) 2006-02-09
MXPA03002559A (es) 2003-06-30
JP2004511609A (ja) 2004-04-15
MX239064B (es) 2006-07-31
JP2004510799A (ja) 2004-04-08
KR100832255B1 (ko) 2008-05-28
KR100843113B1 (ko) 2008-07-02
KR20030041163A (ko) 2003-05-23
ES2269481T3 (es) 2007-04-01
AU2002215936A1 (en) 2002-04-22
BR0114586A (pt) 2003-08-26
AU2002215016A1 (en) 2002-04-22
US7189268B2 (en) 2007-03-13
US6762287B2 (en) 2004-07-13
ATE337049T1 (de) 2006-09-15

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