US20050144741A1 - Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer - Google Patents

Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer Download PDF

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Publication number
US20050144741A1
US20050144741A1 US10/869,058 US86905804A US2005144741A1 US 20050144741 A1 US20050144741 A1 US 20050144741A1 US 86905804 A US86905804 A US 86905804A US 2005144741 A1 US2005144741 A1 US 2005144741A1
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radicals
radical
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hydrogen atom
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Gerard Lang
Jean Cotteret
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LOreal SA
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LOreal SA
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Priority to US10/869,058 priority Critical patent/US20050144741A1/en
Publication of US20050144741A1 publication Critical patent/US20050144741A1/en
Priority to US11/339,466 priority patent/US20060117497A1/en
Priority to US11/590,853 priority patent/US7300473B2/en
Abandoned legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00Azo dyes containing onium groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/496Triazoles or their condensed derivatives, e.g. benzotriazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/731Cellulose; Quaternized cellulose derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/737Galactomannans, e.g. guar; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair

Definitions

  • the invention relates to a composition for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising, in a medium which is suitable for dyeing, at least one cationic direct dye of given formula and at least one specific thickening polymer.
  • the invention also relates to the dyeing processes and dyeing devices using the said composition.
  • Two types of dyeing may be distinguished in the haircare sector.
  • the first is semi-permanent or temporary dyeing, or direct dyeing, which uses dyes capable of giving the hair a natural coloration, a more or less pronounced colour change which may withstand shampooing several times. These dyes are also 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 obtain lightening dyeing. Lightening dyeing is carried out by applying a mixture, prepared at the time of use, of a direct dye and an oxidizing agent to the hair, and makes it possible in particular to obtain, by lightening the melanin in the hair, an advantageous effect such as a unified colour in the case of grey hair, or to bring out the colour in the case of naturally pigmented hair.
  • the second is permanent dyeing or oxidation dyeing.
  • oxidation dyes comprising oxidation dye precursors and couplers.
  • Oxidation dye precursors commonly known as “oxidation bases” are compounds which are initially colourless or weakly coloured which develop their dyeing power on the hair in the presence of oxidizing agents added at the time of use, leading to the formation of coloured compounds and dyes.
  • the formation of these coloured 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-modifying 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 fibres, and in particular human keratin fibres such as the hair, containing, in a medium which is suitable for dyeing, (i) at least one cationic direct dye whose structure corresponds to formulae (I) to (IV) defined below, characterized in that it also contains (ii) at least one specific thickening polymer.
  • the cationic direct dye which can be used according to the present invention is a compound chosen from those of formulae (I), (II), (III), (III′) and (IV) below:
  • the C 1 -C 4 alkyl or alkoxy group preferably denotes methyl, ethyl, butyl, methoxy or ethoxy.
  • the cationic direct dyes of formulae (I), (II), (III) and (III′) which 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.
  • Those of formula (IV) which can be used in the dye compositions in accordance with the invention are known compounds and are described, for example, in patent applications FR-2,189,006, FR-2,285,851 and FR-2,140,205 and its Certificates of Addition.
  • the ones most particularly preferred are the compounds corresponding to the structures (I1), (I2), (I14) and (I31).
  • the cationic direct dye(s) used according to the invention preferably represent(s) from 0.001 to 10% by weight approximately relative to the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately relative to this weight.
  • the thickening polymer which can be used according to the present invention is chosen from the group consisting of:
  • nonionic amphiphilic polymers comprising at least one hydrophilic unit and at least one unit containing a fatty chain (ii) 1 , used according to the invention, are preferably chosen from:
  • the anionic amphiphilic polymers (ii) 2 can be chosen from those:
  • One unit of formula (V) which is more particularly preferred according to the present invention is a unit in which R′ denotes H, n is equal to 10 and R denotes a stearyl (C 18 ) radical.
  • Anionic amphiphilic polymers of this type are described and prepared according to an emulsion polymerization process in patent EP-0,216,479 B2.
  • anionic amphiphilic polymers cited (ii) 2 (a) it is particularly preferred according to the invention to use the polymers formed from 20 to 60% by weight of acrylic acid and/or methacrylic acid, from 5 to 60% by weight of lower alkyl (meth)acrylates, from 2 to 50% by weight of allyl ether containing a fatty chain of formula (I), and from 0 to 1% by weight of a crosslinking agent which is a well known copolymerizable polyethylenic unsaturated monomer, such as diallyl phthalate, allyl (meth)acrylate, divinylbenzene, (poly)ethylene glycol dimethacrylate and methylenebisacrylamide.
  • a crosslinking agent which is a well known copolymerizable polyethylenic unsaturated monomer, such as diallyl phthalate, allyl (meth)acrylate, divinylbenzene, (poly)ethylene glycol dimethacrylate and methylenebisacryl
  • the ones most particularly preferred are the crosslinked terpolymers of methacrylic acid, of ethyl acrylate, of polyethylene glycol (10 EO) stearyl ether (Steareth-10), in particular those sold by the company Allied Colloids under the names Salcare SC 80 and Salcare SC 90 which are aqueous 30% emulsions of a crosslinked terpolymer of methacrylic acid, of ethyl acrylate and of Steareth-10 allyl ether (40/50/10).
  • anionic amphiphilic polymers (II) 2 can also be chosen from those:
  • (C 10 -C 30 )alkyl esters of unsaturated carboxylic acids in accordance with the invention comprise, for example, lauryl acrylate, stearyl acrylate, decyl acrylate, isodecyl acrylate, dodecyl acrylate and the corresponding methacrylates, lauryl methacrylate, stearyl methacrylate, decyl methacrylate, isodecyl methacrylate and dodecyl methacrylate.
  • Anionic amphiphilic polymers of this type (ii) 2 (b) are described and prepared, for example, according to U.S. Pat. Nos. 3,915,921 and 4,509,949.
  • Anionic amphiphilic polymers (ii) 2 (b) which can be used in the context of the present invention can more particularly denote polymers formed from a mixture of monomers comprising:
  • the said crosslinking agent is a monomer containing a group with at least one other polymerizable group whose unsaturated bonds are not conjugated to each other. Mention may be made in particular of polyallyl ethers such as, in particular, polyallylsucrose and polyallylpentaerythritol.
  • the ones most particularly preferred according to the present invention are the products sold by the company Goodrich under the trade names Pemulen TR1, Pemulen TR2, Carbopol 1382 and even more preferably Pemulen TR1 and the product sold by the company S.E.P.C. under the name Coatex SX.
  • the cationic amphiphilic polymers (i) 3 used according to the invention are preferably chosen from quaternized cellulose derivatives and polyacrylates containing amino side groups.
  • the quaternized cellulose derivatives are, in particular,
  • polyacrylates containing amino side groups (ii) 3 (C), which may or may not be quaternized, contain, for example, hydrophobic groups such as Steareth-20 [polyoxyethylenated (20) stearyl alcohol].
  • the alkyl radicals borne by the above quaternized celluloses or hydroxycelluloses preferably comprise from 8 to 30 carbon atoms.
  • aryl radicals preferably denote phenyl, benzyl, naphthyl or anthryl groups.
  • quaternized alkylhydroxyethyl-celluloses containing C 8 -C 30 fatty chains mention may be made of the products Quatrisoft LM200, Quatrisoft LM-X529-18-A, Quatrisoft LM-X529-18-B (C 12 alkyl) and Quatrisoft LM-X529-8 (C 18 alkyl) sold by the company Amerchol and the products Crodacel QM, Crodacel QL (C 12 alkyl) and Crodacel QS (C 18 alkyl) sold by the company Croda.
  • polyacrylates containing amino side chains mention may be made of the polymers 8781-124B or 9492-103 from the company National Starch.
  • amphiphilic polymers of nonionic type (ii), and of anionic type (ii) 2 described above even more particularly the amphiphilic polymers of class (ii) 1 (a) and (ii) 2 (c) and of class (ii) 2 (a) and (ii) 2 (b).
  • amphiphilic thickening polymers of nonionic, anionic or cationic type used in the compositions of the present invention are preferably present in a proportion of from 0.01 to 10% by weight approximately, in particular in a proportion of from 0.1 to 5% by weight approximately, relative to the total weight of the dye composition applied to the keratin fibres.
  • the medium which is suitable for dyeing (or support) generally comprising water or of a mixture of water and at least one organic solvent to dissolve the compounds which would not be sufficiently water-soluble.
  • organic solvents mention may be made, for example, of C 1 -C 4 lower alkanols such as ethanol and isopropanol; aromatic alcohols such as benzyl alcohol, as well as similar products and mixtures thereof.
  • the solvents can be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
  • the pH of the dye composition in accordance with the invention is generally approximately between 2 and 11 and preferably approximately between 5 and 10. It can be adjusted to the desired value using acidifying or basifying agents usually used for dyeing keratin fibres.
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulphonic acids.
  • basifying agents mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamine and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (VIII) below: in which W is a propylene residue optionally substituted with a hydroxyl group or a C 1 -C 6 alkyl radical; R 33 , R 34 , R 35 and R 36 , which may be identical or different, 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 one or more additional direct dyes which can be chosen, for example, from nitrobenzene dyes, anthraquinone dyes, naphthoquinone dyes, triarylmethane dyes, xanthene dyes and azo dyes which are non-cationic.
  • the dye composition in accordance 1: with the invention contains, in addition to the cationic direct dye(s) (i), one or more oxidation bases chosen from the oxidation bases conventionally used for oxidation dyeing and among which mention may be made in particular of para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
  • the oxidation base(s) preferably represent(s) from 0.0005 to 12% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately relative to this weight.
  • the dye composition in accordance with the invention can also contain, in addition to the cationic direct dye (i) and the thickening polymer (ii) as well as the oxidation bases, one or more couplers so as to modify the shades obtained or to enrich them with glints, by using the cationic direct dye(s) (i) and the oxidation base(s).
  • the couplers which can be used in the dye composition in accordance with the invention can be chosen from the couplers used conventionally in oxidation dyeing and among which mention may be made in particular of meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers.
  • the coupler(s) When it is (they are) present, the coupler(s) preferably represent(s) from 0.0001 to 10% by weight approximately relative to the total weight of the dye composition, and even more preferably from 0.005 to 5% by weight approximately relative to this weight.
  • 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 any other form which is suitable for dyeing keratin fibres, and in particular human hair. It can be obtained by mixing, at the time of use, a composition, which may be pulverulent, containing the cationic direct dye(s) with a composition containing the specific thickening polymer.
  • the dye composition in accordance with the invention also comprises at least one oxidizing agent chosen, 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. It is particularly preferred to use hydrogen peroxide or enzymes.
  • Another subject of the invention is a process for dyeing keratin fibres, and in particular human keratin fibres such as the hair, using the dye composition as defined above.
  • At least one dye composition as defined above is applied to the fibres, for a period which is sufficient to develop the desired coloration, after which the fibres are rinsed, optionally washed with shampoo, rinsed again and dried.
  • the time required to develop the coloration on the keratin fibres is generally between 3 and 60 minutes and even more specifically between 5 and 40 minutes.
  • At least one dye composition as defined above is applied to the fibres, for a period which is sufficient to develop the desired coloration, without final rinsing.
  • the dyeing process comprises a first step which consists in separately storing, on the one hand, a composition (A1) comprising, in a medium which is 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) comprising, in a medium which is suitable for dyeing, at least one oxidizing agent, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibres, the composition (A1) or the composition (B1) containing the thickening polymer (ii) as defined above.
  • the dyeing process comprises a first step which consists in separately storing, on the one hand, a composition (A2) comprising, in a medium which is suitable for dyeing, at least one cationic direct dye (i) as defined above, and, on the other hand, a composition (B2) comprising, in a medium which is suitable for dyeing, at least one oxidizing agent, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibres, the composition (A2) or the composition (B2) containing the thickening polymer as defined above.
  • a composition (A2) comprising, in a medium which is suitable for dyeing, at least one cationic direct dye (i) as defined above
  • a composition (B2) comprising, in a medium which is suitable for dyeing, at least one oxidizing agent, and then in mixing them together at the time of use, after which this mixture is applied to the keratin fibres, the composition (A2) or the composition (B2) containing the thickening polymer
  • Another subject of the invention is a multi-compartment dyeing device or dyeing “kit” or any other multi-compartment packaging system, a first compartment of which comprises the composition (A1) or (A2) as defined above and a second compartment of which comprises the composition (B1) or (B2) as defined above.
  • These devices can be equipped with means for dispensing the desired mixture onto the hair, such as the devices described in patent FR 2,586,913 in the name of the Applicant.
  • Example 1 Example 2
  • Example 3 Cationic direct dye of 0.2 formula (I1)
  • Diurethane (HMD) of oxy- 1.0 AM* ethylenated (66 EO) and oxy- propylenated (14 PO) C 16 -C 18 alcohols, sold under the name Dapral T212 by the company
  • compositions were each applied for 30 minutes to locks of natural grey hair containing 90% white hairs.
  • the locks of hair were then rinsed, washed with a standard shampoo and then dried.
US10/869,058 1998-07-09 2004-06-17 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer Abandoned US20050144741A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US10/869,058 US20050144741A1 (en) 1998-07-09 2004-06-17 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer
US11/339,466 US20060117497A1 (en) 1998-07-09 2006-01-26 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer
US11/590,853 US7300473B2 (en) 1998-07-09 2006-11-01 Composition for dyeing keratin fibers with a cationic direct dye and a thickening polymer

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR9808835 1998-07-09
FR9808835A FR2780883B1 (fr) 1998-07-09 1998-07-09 Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un polymere epaississant
US35057999A 1999-07-08 1999-07-08
US10/869,058 US20050144741A1 (en) 1998-07-09 2004-06-17 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer

Related Parent Applications (1)

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US35057999A Continuation 1998-07-09 1999-07-08

Related Child Applications (1)

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US11/339,466 Continuation US20060117497A1 (en) 1998-07-09 2006-01-26 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer

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US20050144741A1 true US20050144741A1 (en) 2005-07-07

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US10/869,058 Abandoned US20050144741A1 (en) 1998-07-09 2004-06-17 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer
US11/339,466 Abandoned US20060117497A1 (en) 1998-07-09 2006-01-26 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer
US11/590,853 Expired - Lifetime US7300473B2 (en) 1998-07-09 2006-11-01 Composition for dyeing keratin fibers with a cationic direct dye and a thickening polymer

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US11/339,466 Abandoned US20060117497A1 (en) 1998-07-09 2006-01-26 Composition for dyeing keratin fibres with a cationic direct dye and a thickening polymer
US11/590,853 Expired - Lifetime US7300473B2 (en) 1998-07-09 2006-11-01 Composition for dyeing keratin fibers with a cationic direct dye and a thickening polymer

Country Status (20)

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US (3) US20050144741A1 (xx)
EP (1) EP0970684B1 (xx)
JP (2) JP2000086472A (xx)
KR (1) KR100355642B1 (xx)
CN (1) CN1310689C (xx)
AR (1) AR019892A1 (xx)
AT (1) ATE297181T1 (xx)
AU (1) AU719497B2 (xx)
BR (1) BR9903212B1 (xx)
CA (1) CA2277353A1 (xx)
DE (1) DE69925674T2 (xx)
DK (1) DK0970684T3 (xx)
ES (1) ES2244157T3 (xx)
FR (1) FR2780883B1 (xx)
HU (1) HU221345B1 (xx)
MX (1) MX231692B (xx)
PL (1) PL204183B1 (xx)
PT (1) PT970684E (xx)
RU (1) RU2180833C2 (xx)
ZA (1) ZA994102B (xx)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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
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
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
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
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
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
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
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
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
US20060075582A1 (en) * 2004-09-13 2006-04-13 Alain Lagrange Composition comprising at least one substituted carbocyanin derivative, process for treating keratin fibers using it, device therefor and use thereof
US7419511B2 (en) 2004-09-13 2008-09-02 L'oreal, S.A. Compositions comprising at least one substituted carbocyanin derivative, processes for treating keratin fibers using them, device therefor and uses thereof
US7427301B2 (en) 2004-09-13 2008-09-23 L'ORéAL S.A. Composition comprising at least one substituted carbocyanin derivative, process for treating keratin fibers using it, device therefor and use thereof
US20060090269A1 (en) * 2004-09-13 2006-05-04 Alain Lagrange Compositions comprising at least one substituted carbocyanin derivative, processes for treating keratin fibers using them, device therefor and uses thereof
US20090300857A1 (en) * 2005-08-30 2009-12-10 Ciba Corporation Dyes containing a thiol group
US7771490B2 (en) 2005-08-30 2010-08-10 Ciba Corporation Dyes containing a thiol group
US7481847B2 (en) 2006-03-28 2009-01-27 L'oreal S.A. Dye composition comprising at least one cationic hydrazone direct dye, dyeing process, and multi-compartment devices
US20070234487A1 (en) * 2006-03-28 2007-10-11 Alain Lagrange Dye composition comprising at least one cationic hydrazone direct dye, dyeing process, and multi-compartment devices

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FR2780883A1 (fr) 2000-01-14
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PT970684E (pt) 2005-09-30
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US7300473B2 (en) 2007-11-27
EP0970684B1 (fr) 2005-06-08
HU221345B1 (en) 2002-09-28
AR019892A1 (es) 2002-03-20
DK0970684T3 (da) 2005-07-18
CN1310689C (zh) 2007-04-18
US20060117497A1 (en) 2006-06-08
PL204183B1 (pl) 2009-12-31
DE69925674T2 (de) 2006-03-30
BR9903212A (pt) 2000-05-30
JP2000086472A (ja) 2000-03-28
HUP9902330A2 (hu) 2000-03-28
DE69925674D1 (de) 2005-07-14
HUP9902330A3 (en) 2000-11-28
ATE297181T1 (de) 2005-06-15
HU9902330D0 (en) 1999-09-28
FR2780883B1 (fr) 2001-04-06
ES2244157T3 (es) 2005-12-01
CA2277353A1 (fr) 2000-01-09
EP0970684A1 (fr) 2000-01-12
JP2004339236A (ja) 2004-12-02
AU3796699A (en) 2000-03-09
RU2180833C2 (ru) 2002-03-27
ZA994102B (en) 2000-01-25
AU719497B2 (en) 2000-05-11
KR100355642B1 (ko) 2002-10-09
US20070039107A1 (en) 2007-02-22
MX231692B (en) 2005-10-28

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