US20030019053A9 - Dye composition for keratin fibres, with a cationic direct dye and a substantive polymer - Google Patents

Dye composition for keratin fibres, with a cationic direct dye and a substantive polymer Download PDF

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Publication number
US20030019053A9
US20030019053A9 US09/287,176 US28717699A US2003019053A9 US 20030019053 A9 US20030019053 A9 US 20030019053A9 US 28717699 A US28717699 A US 28717699A US 2003019053 A9 US2003019053 A9 US 2003019053A9
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composition
composition according
keratin fibers
dye
cationic
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US20020046432A1 (en
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Christine Rondeau
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LOreal SA
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LOreal SA
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Assigned to L'OREAL S.A. reassignment L'OREAL S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RONDEAU, CHRISTINE
Publication of US20020046432A1 publication Critical patent/US20020046432A1/en
Publication of US20030019053A9 publication Critical patent/US20030019053A9/en
Priority to US10/761,213 priority Critical patent/US20040148711A1/en
Priority to US11/727,834 priority patent/US7485157B2/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • 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
    • 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
    • A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
    • 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
    • A61K8/4966—Triazines or their condensed derivatives
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4322—Direct dyes in preparations for temporarily coloring the hair further containing an oxidizing agent

Definitions

  • the invention relates to a dye composition for keratin fibers, especially human keratin fibers, such as the hair, this composition comprising, in a medium suitable for dyeing, at least one cationic direct dye of the below given formulae and at least one specific cationic or amphoteric substantive polymer.
  • the invention also relates to the dyeing processes and devices using this composition.
  • the first type of dyeing is semi-permanent or temporary dyeing, also known as direct dyeing, which uses dyes capable of giving the hair's natural coloration a more or less pronounced color change that may be resistant to several shampoo-washes.
  • These dyes are known as direct dyes; they can be used with or without an oxidizing agent. In the presence of an oxidizing agent, the aim is to effect a lightening dyeing.
  • the lightening dyeing is carried out by applying the mixture, prepared at the time of use, of a direct dye and of an oxidizing agent to the hair, and obtains, by lightening the melanin in the hair, an advantageous effect, such as unifying the color in the case of grey hair, or bringing out the color in the case of naturally pigmented hair.
  • the second type of dyeing is permanent dyeing or oxidation dyeing.
  • This type of dyeing is carried out with so-called “oxidation” dyes comprising oxidation dye precursors and couplers.
  • Oxidation dye precursors commonly referred to as “oxidation bases,” are compounds that are initially colorless or only weakly colored, and that develop their dyeing power on the hair in the presence of oxidizing agents added at the time of use, leading to the formation of colored compounds and dyes.
  • the formation of these colored compounds and dyes results either from an oxidative condensation of the “oxidation bases” with themselves, or from an oxidative condensation of the “oxidation bases” with coloration modifier compounds, commonly known as “couplers,” which are generally present in the dye compositions used in oxidation dyeing.
  • a first subject of the present invention is thus a composition for dyeing keratin fibers, and especially human keratin fibers, such as the hair, which composition comprises, in a medium suitable for dyeing, (i) at least one cationic direct dye whose structure corresponds to the following formulae, and (ii) at least one specific cationic or amphoteric substantive polymer.
  • the cationic direct dye which can be used according to the present invention is a compound selected from those of formulae (I), (II), (III) and (III′) below:
  • D represents a nitrogen atom or a —CH group
  • R 1 and R 2 are identical or different and represent a hydrogen atom, a C 1 -C 4 alkyl radical which is unsubstituted or substituted with a —CN, —OH or —NH 2 radical, or R 1 and R 2 form, with a carbon atom of the benzene ring, an optionally oxygenated or nitrogenous heterocycle which is unsubstituted or substituted with one or more C 1 -C 4 alkyl radicals, or R 1 and R 2 may each be a 4′-aminophenyl radical;
  • R 3 and R′ 3 are identical or different and represent a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine and fluorine, a cyano group, a C 1 -C 4 alkyl radical, or a C 1 -C 4 alkoxy or acetyloxy radical;
  • X ⁇ represents an anion preferably selected from chloride, methyl sulphate and acetate
  • A represents a group selected from structures A1 to A19 below:
  • R 4 represents a C 1 -C 4 alkyl radical which is unsubstituted or substituted with a hydroxyl radical and R 5 represents a C 1 -C 4 alkoxy radical, with the proviso that when D represents —CH, and A represents A 4 or A 13 and R 3 is other than an alkoxy radical, then R 1 and R 2 do not simultaneously represent a hydrogen atom;
  • R 6 represents a hydrogen atom or a C 1 -C 4 alkyl radical
  • R 7 represents a hydrogen atom, an alkyl radical which is unsubstituted or substituted with a —CN radical or with an amino group, a 4′-aminophenyl radical, or forms, with R 6 , an optionally oxygenated and/or nitrogenous heterocycle which is unsubstituted or substituted with a C 1 -C 4 alkyl radical;
  • R 8 and R 9 are identical or different and represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine or fluorine, a C 1 -C 4 alkyl or C 1 -C 4 alkoxy radical or a —CN radical;
  • X ⁇ represents an anion, preferably selected from chloride, methyl sulphate and acetate
  • B represents a group selected from structures B1 to B6 below:
  • R 10 represents a C 1 -C 4 alkyl radical
  • R 11 and R 12 are identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical
  • R 13 represents a hydrogen atom, a C 1 -C 4 alkoxy radical, a halogen atom, such as bromine, chlorine, iodine or fluorine, or an amino radical;
  • R 14 represents a hydrogen atom, a C 1 -C 4 alkyl radical, or forms, with a carbon atom of the benzene ring, a heterocycle which is optionally oxygenated and/or substituted with one or more C 1 -C 4 alkyl groups;
  • R 15 represents a hydrogen atom or a halogen atom such as bromine, chlorine, iodine or fluorine;
  • R 16 and R 17 are identical or different and represent a hydrogen atom or a C 1 -C 4 alkyl radical
  • D 1 and D 2 are identical or different and represent a nitrogen atom or a —CH group
  • X ⁇ represents an anion, preferably selected from chloride, methyl sulphate and acetate
  • E represents a group selected from structures E1 to E8 below:
  • R′ represents a C 1 -C 4 alkyl radical
  • E can also represent a group of structure E9 below:
  • R′ represents a C 1 -C 4 alkyl radical.
  • cationic direct dyes of formulae (I), (II), (III) and (III′) that can be used in the dye compositions in accordance with the invention are known compounds and are described, for example, in patent applications WO 95/01772, WO 95/15144 and EP-A-0,714,954.
  • the preferred cationic direct dyes of formula (I) that can be used in the dye compositions in accordance with the invention include the compounds corresponding to structures (I1) to (I55) below:
  • those most preferred compounds include those corresponding to structures (I1), (I2), (I14) and (I31).
  • the preferred cationic direct dyes of formula (II) that can be used in the dye compositions in accordance with the invention, include the compounds corresponding to structures (II1) to (II12) below:
  • the preferred cationic direct dyes of formula (III) that can be used in the dye compositions in accordance with the invention, include the compounds corresponding to structures (III1) to (III18) below:
  • the preferred cationic direct dyes of formula (III′) that can be used in the dye compositions in accordance with the invention, include the compounds corresponding to structures (II′1) to (III′3) below:
  • the at least one cationic direct dye used according to the invention preferably is present in amount ranging from about 0.001 to about 10% by weight relative to the total weight of the dye composition, and even more preferably from about 0.005 to about 5% by weight relative to this weight.
  • the cationic or amphoteric substantive polymer that can be used according to the present invention is selected from:
  • polyquaternary ammonium polymers selected from:
  • D can be zero or can represent a group —(CH 2 ), —CO— in which r represents a number equal to 4 or 7;
  • Preferred cationic cellulosic derivatives include quaternized cellulose ether derivatives such as those described in European patent application EP-A-0,189,935, and in particular the polymer sold under the name “Quatrisoft LM 200” by the company Union Carbide. These polymers are also defined in the CTFA dictionary (5th edition, 1993) as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a lauryldimethylammonium group, and are listed therein under the name “Polyquaternium 24”.
  • Preferred substantive polymers of the methacryloyloxyethyltrimethylammonium halide homopolymer and copolymer type include the products that are referred to in the CTFA dictionary (5th Edition, 1993) as (1) “Polyquaternium 37”, (2) “Polyquaternium 32” and (3) “Polyquaternium 35”, and which correspond (1) to crosslinked poly(methacryloyloxyethyltri-methylammonium chloride) homopolymer, as a 50% dispersion in mineral oil, sold under the name Salcare SC95 by the company Allied Colloids, (2) to the crosslinked copolymer of acrylamide and of methacryloyloxyethyltrimethylammonium chloride (20/80 by weight), as a 50% dispersion in mineral oil, sold under the name Salcare SC92 by the company Allied Colloids, and (3) to the methosulphate of the copolymer of methacryloyloxyethyltrimethylammonium
  • the preferred substantive polymers of the copolymer of dimethyldiallylammonium halide and of (meth)acrylic acid type that can be used according to the invention, include the copolymers of diallyldimethylammonium chloride and of acrylic acid, such as the one in proportions (80/20 by weight) sold under the name Merquat 280 by the company Calgon.
  • the preferred substantive polymers of the polyquaternary ammonium type which can be used according to the invention include:
  • D can be zero or can represent a group —(CH 2 ) r —CO—, further wherein r represents a number equal to 4 or 7, and wherein the molecular mass of said polymers is preferably less than 100,000, and even more preferably less than or equal to 50,000.
  • Such polymers are sold, for a example, by the company Miranol under the names “Mirapol A15”, “Mirapol AD1”, “Mirapol AZ1” and “Mirapol 175”.
  • PVP vinylpyrrolidone polymers
  • the concentration of substantive polymer (ii) in the dye composition according to the invention can range from about 0.01 to about 10% relative to the total weight of the dye composition, and preferably from 0.1 to 5%.
  • the medium suitable for dyeing generally comprises water or a mixture of water and at least one organic solvent, which can dissolve the compounds that would not be sufficiently soluble in the water.
  • organic solvents include, for example, C 1 -C 4 lower alkanols, such as ethanol and isopropanol; aromatic alcohols such as benzyl alcohol or phenoxyethanol, as well as similar products and mixtures thereof.
  • the solvents can be present in preferred proportions ranging from about 1 to about 40% by weight relative to the total weight of the dye composition, and even more preferably from about 5 to about 30% by weight.
  • the pH of the dye composition in accordance with the invention generally ranges from about 2 to about 11 and preferably from about 5 to about 10.
  • the pH can be adjusted to the desired value using acidifying or basifying agents typically used in the dyeing of keratin fibers.
  • acidifying agents include inorganic or organic acids, such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids, such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
  • basifying agents include aqueous ammonia, alkaline carbonates, alkanolamines, such as mono-, di- and triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (VII) below:
  • W is a propylene residue optionally substituted with a hydroxyl group or a C 1 -C 6 alkyl radical
  • R 18 R 19 , R 20 and R 21 are identical or different and represent a hydrogen atom or a C 1 -C 6 alkyl or C 1 -C 6 hydroxyalkyl radical.
  • the dye composition in accordance with the invention can contain at least one additional direct dye that can be selected, for example, from nitrobenzene dyes, anthraquinone dyes, naphthoquinone dyes, triarylmethane dyes, xanthine dyes and azo dyes which are non-cationic.
  • the dye composition in accordance with the invention contains, in addition to the at least one cationic direct dye (i), at least one oxidation base selected from the oxidation bases conventionally used for oxidation dyeing, for example, para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
  • at least one oxidation base selected from the oxidation bases conventionally used for oxidation dyeing, for example, para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
  • the at least one oxidation base is preferably present in an amount ranging from about 0.0005 to about 12% by weight relative to the total weight of the dye composition, and even more preferably from about 0.005 to about 6% by weight relative to the total weight of the dye composition.
  • the dye composition in accordance with the invention can also contain, in addition to the at least one cationic direct dye (i), the at least one substantive polymer (ii), and the at least one oxidation base, at least one coupler so as to modify the shades obtained or to enrich them with glints, by using the at least one cationic direct dye (i) and the at least one oxidation base.
  • the at least one coupler that can be used in the dye composition in accordance with the invention can be selected from the couplers conventionally used in oxidation dyeing, for example, meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers.
  • the at least one coupler is preferably present in an amount ranging from about 0.0001 to about 10% by weight relative to the total weight of the dye composition, and even more preferably from about 0.005 to about 5% by weight relative to the total weight of the dye composition.
  • the dye composition in accordance with the invention can also contain various adjuvants conventionally used in compositions for dyeing the hair, such as antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, surfactants, film-forming agents, ceramides, preserving agents, screening agents and opacifiers.
  • adjuvants conventionally used in compositions for dyeing the hair such as antioxidants, penetrating agents, sequestering agents, fragrances, buffers, dispersing agents, surfactants, film-forming agents, ceramides, preserving agents, screening agents and opacifiers.
  • the dye composition according to the invention can be in various forms, such as in the form of liquids, shampoos, creams or gels or in any other form which is suitable for dyeing keratin fibers, and, especially, human hair.
  • the presentation in shampoo form is particularly preferred.
  • the dye composition in accordance with the invention also contains at least one oxidizing agent selected, for example, from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, such as perborates and persulphates, and enzymes, such as peroxidases, lactases and two-electron oxidoreductases.
  • at least one oxidizing agent selected, for example, from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, such as perborates and persulphates, and enzymes, such as peroxidases, lactases and two-electron oxidoreductases.
  • the use of hydrogen peroxide or of enzymes is particularly preferred.
  • Another subject of the invention is a method for dyeing keratin fibers, especially human keratin fibers, such as the hair, using the dye composition as defined above.
  • At least one dye composition as defined above is applied to the keratin fibers, for a period of time sufficient to develop the desired coloration, after which the fibers are rinsed, optionally washed with shampoo, rinsed again and dried.
  • the time required to develop the coloration on the keratin fibers generally ranges from 3 to 60 minutes, and more preferably ranges from 5 to 40 minutes.
  • At least one dye composition as defined above is applied to the keratin fibers, for a period which is sufficient to develop the desired coloration, without final rinsing.
  • the dyeing process when the dye composition in accordance with the invention contains at least one oxidation base and at least one oxidizing agent, the dyeing process includes a first step which comprises separately storing, on the one hand, a composition (A1) comprising, in a medium suitable for dyeing, at least one cationic direct dye (i) as defined above and at least one oxidation base, and, on the other hand, a composition (B1) containing, in a medium suitable for dyeing, at least one oxidizing agent, followed by mixing them together at the time of use, before applying this mixture to the keratin fibers, the composition (A1) or the composition (B1) containing the cationic or amphoteric substantive polymer (ii) as defined above.
  • the dyeing process includes a first step which comprises separately storing, on the one hand, a composition (A2) comprising, in a medium suitable for dyeing, at least one cationic direct dye (i) as defined above, and, on the other hand, a composition (B2) containing, in a medium suitable for dyeing, at least one oxidizing agent, followed by mixing them together at the time of use, before applying this mixture to the keratin fibers, the composition (A2) or the composition (B2) containing the cationic or amphoteric substantive polymer as defined above.
  • a composition (A2) comprising, in a medium suitable for dyeing, at least one cationic direct dye (i) as defined above
  • a composition (B2) containing, in a medium suitable for dyeing, at least one oxidizing agent followed by mixing them together at the time of use, before applying this mixture to the keratin fibers, the composition (A2) or the composition (B2) containing the cationic or amphoteric substantive polymer as defined above.
  • Another subject of the invention is a multi-compartment dyeing device or “kit” or any other multi-compartment packaging system, a first compartment of which contains composition (A1) or (A2) as defined above and a second compartment of which contains composition (B1) or (B2) as defined above.
  • These devices can be equipped with a means for applying the desired mixture to the hair, such as the devices described in French Patent No. FR-2,586,913 in the name of L'Oréal.
  • Cationic direct dye of formula I(2) 0.125 g para-Aminophenol 0.120 g 5-N- ⁇ -Hydroxyethylamino-2-methylPhenol 0.125 g
  • Substantive polymer copolymer of 1.0 g A.M.* diallyldimethylammonium chloride and of acrylic acid (80/20 by weight), sold under the name Merquat 280 by the company Calgon Oleyl alcohol polyglycerolated with 2 mol of glycerol 4.0 g Oleyl alcohol polyglycerolated with 4 mol of glycerol, 5.69 g A.M.* containing 78% active material (A.M.) Oleic acid 3.0 g Oleylamine containing 2 mol of ethylene oxide, sold 7.0 g under the trade name Ethomeen O12 by the company Akzo Diethylaminopropyl laurylaminosuccinamate, sodium 3.0 g A.M.* salt,
  • Oleyl alcohol 5.0 g Oleic acid diethanolamide 12.0 g Propylene glycol 3.5 g Dipropylene glycol 0.5 g Propylene glycol monomethyl ether 9.0 g Ethanol 7.0 g Sodium metabisulphite as an aqueous solution 0.455 g A.M.* containing 35% A.M. Ammonium acetate 0.8 g Antioxidant, sequestering agent qs Fragrance, preserving agent qs Aqueous ammonia containing 20% NH 3 10.0 g
  • this composition was mixed with an equal amount of an aqueous 20-volume hydrogen peroxide solution (6% by weight).
  • the dye composition below was prepared: Cationic direct dye of formula I(14) 0.09 g Substantive polymer of polyquaternary ammonium 1.0 g A.M.* type of formula (IV) Nonylphenol containing 9 mol of ethylene oxide 8.0 g 2-Amino-2-methylpropanol qs pH 9 Demineralized water qsp 100 g
US09/287,176 1998-04-06 1999-04-06 Dye composition for keratin fibres, with a cationic direct dye and a substantive polymer Abandoned US20030019053A9 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/761,213 US20040148711A1 (en) 1998-04-06 2004-01-22 Dye composition for keratin fibers, with a cationic direct dye and a substantive polymer
US11/727,834 US7485157B2 (en) 1998-04-06 2007-03-28 Dye composition for keratin fibers, with a cationic direct dye and a substantive polymer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9804234 1998-04-06
FR9804234A FR2776923B1 (fr) 1998-04-06 1998-04-06 Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un polymere substantif

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US10/761,213 Continuation US20040148711A1 (en) 1998-04-06 2004-01-22 Dye composition for keratin fibers, with a cationic direct dye and a substantive polymer

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US20020046432A1 US20020046432A1 (en) 2002-04-25
US20030019053A9 true US20030019053A9 (en) 2003-01-30

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US09/287,176 Abandoned US20030019053A9 (en) 1998-04-06 1999-04-06 Dye composition for keratin fibres, with a cationic direct dye and a substantive polymer
US10/761,213 Abandoned US20040148711A1 (en) 1998-04-06 2004-01-22 Dye composition for keratin fibers, with a cationic direct dye and a substantive polymer
US11/727,834 Expired - Fee Related US7485157B2 (en) 1998-04-06 2007-03-28 Dye composition for keratin fibers, with a cationic direct dye and a substantive polymer

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US11/727,834 Expired - Fee Related US7485157B2 (en) 1998-04-06 2007-03-28 Dye composition for keratin fibers, with a cationic direct dye and a substantive polymer

Country Status (21)

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US (3) US20030019053A9 (fr)
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US20040258641A1 (en) * 2003-04-01 2004-12-23 Gregory Plos Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor
US20040256598A1 (en) * 2003-04-01 2004-12-23 Gregory Plos Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor
US20050005371A1 (en) * 2003-04-01 2005-01-13 Chrystel Pourille-Grethen Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor
US20050008594A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Composiiton for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof
US20050005368A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye
US20050008593A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof
US20050031562A1 (en) * 2003-04-01 2005-02-10 Luc Gourlaouen Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof
US20050028301A1 (en) * 2001-09-28 2005-02-10 Florent Pastore Dyeing composition with a brightening effect for human kerationous fibres
US20050076457A1 (en) * 2003-04-01 2005-04-14 Gregory Plos Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof
US20050098763A1 (en) * 2003-04-01 2005-05-12 Gregory Plos Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof
US20060010617A1 (en) * 2002-12-24 2006-01-19 Luc Gourlaouen Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener
US20070130701A1 (en) * 2004-02-03 2007-06-14 Mitsubishi Pencil Co., Ltd. Hair color
US20090288674A1 (en) * 2003-04-01 2009-11-26 L'oreal S.A. Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing

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US20040200009A1 (en) * 2001-06-11 2004-10-14 Laurent Vidal Dyeing composition for keratinous fibers comprising a particular dicationic diazo dye
US7407516B2 (en) 2001-06-11 2008-08-05 L'oreal, S.A. Dyeing composition for keratinous fibers comprising a dicationic diazo dye
US20050028301A1 (en) * 2001-09-28 2005-02-10 Florent Pastore Dyeing composition with a brightening effect for human kerationous fibres
US20060010617A1 (en) * 2002-12-24 2006-01-19 Luc Gourlaouen Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener
US20050008594A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Composiiton for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof
US20050005368A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye
US20050008593A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof
US20050031562A1 (en) * 2003-04-01 2005-02-10 Luc Gourlaouen Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof
US20050005371A1 (en) * 2003-04-01 2005-01-13 Chrystel Pourille-Grethen Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor
US20050076457A1 (en) * 2003-04-01 2005-04-14 Gregory Plos Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof
US20050098763A1 (en) * 2003-04-01 2005-05-12 Gregory Plos Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof
US20040256598A1 (en) * 2003-04-01 2004-12-23 Gregory Plos Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor
US20040258641A1 (en) * 2003-04-01 2004-12-23 Gregory Plos Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor
US20090288674A1 (en) * 2003-04-01 2009-11-26 L'oreal S.A. Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing
US7736631B2 (en) 2003-04-01 2010-06-15 L'oreal S.A. Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing
US20070130701A1 (en) * 2004-02-03 2007-06-14 Mitsubishi Pencil Co., Ltd. Hair color
US7503939B2 (en) 2004-02-03 2009-03-17 Mitsubishi Pencil Co., Ltd. Hair color

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US20040148711A1 (en) 2004-08-05
DE69921225D1 (de) 2004-11-25
US20080078036A1 (en) 2008-04-03
JPH11343218A (ja) 1999-12-14
PT953334E (pt) 2005-03-31
DK0953334T3 (da) 2004-11-08
DE69921225T2 (de) 2005-11-17
PL392259A1 (pl) 2010-11-22
EP0953334A3 (fr) 2000-03-08
ES2232091T3 (es) 2005-05-16
CA2266053A1 (fr) 1999-10-06
EP0953334A2 (fr) 1999-11-03
AU2254099A (en) 1999-10-14
PL392260A1 (pl) 2010-11-22
CZ114599A3 (cs) 1999-10-13
HUP9900867A2 (hu) 1999-12-28
ZA992429B (en) 1999-10-08
PL332363A1 (en) 1999-10-11
AU722097B2 (en) 2000-07-20
US7485157B2 (en) 2009-02-03
BR9901590B1 (pt) 2013-11-05
CN1233466A (zh) 1999-11-03
JP4563947B2 (ja) 2010-10-20
AR017729A1 (es) 2001-09-12
EP0953334B1 (fr) 2004-10-20
US20020046432A1 (en) 2002-04-25
HU9900867D0 (en) 1999-05-28
CN1289055C (zh) 2006-12-13
MX231224B (es) 2005-10-10
MX9903129A (es) 2000-04-30
KR19990082966A (ko) 1999-11-25
BR9901590A (pt) 2000-05-30
JP2006169262A (ja) 2006-06-29
ATE279903T1 (de) 2004-11-15
FR2776923B1 (fr) 2003-01-10
HUP9900867A3 (en) 2000-06-28
RU2160087C1 (ru) 2000-12-10
CA2266053C (fr) 2010-06-08
FR2776923A1 (fr) 1999-10-08
JP3899204B2 (ja) 2007-03-28

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