WO2011141462A1 - Composition de coloration capillaire comprenant des colorants chromanes et/ou chromènes - Google Patents

Composition de coloration capillaire comprenant des colorants chromanes et/ou chromènes Download PDF

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Publication number
WO2011141462A1
WO2011141462A1 PCT/EP2011/057517 EP2011057517W WO2011141462A1 WO 2011141462 A1 WO2011141462 A1 WO 2011141462A1 EP 2011057517 W EP2011057517 W EP 2011057517W WO 2011141462 A1 WO2011141462 A1 WO 2011141462A1
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zinc
composition
salts
dyes
chosen
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PCT/EP2011/057517
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English (en)
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Boris Lalleman
Alain Lagrange
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L'oreal
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Publication of WO2011141462A1 publication Critical patent/WO2011141462A1/fr

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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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • the subj ect of the invention is a composition for dyeing keratin fibres comprising one or more dyes chosen from chromene dyes, chromane dyes and mixtures thereof, one or more zinc salts, benzoic acid and/or one or more salts thereof, and one or more specific compounds.
  • the invention also relates to a process using said composition and to the use of said composition.
  • oxidation bases such as ortho- or para-phenylenediamines, ortho- or para-aminopheno ls and heterocyclic compounds.
  • oxidation bases are generally combined with couplers .
  • couplers are colourless or weakly co loured compounds which, when combined with oxidizing products, can give rise to coloured compounds via a process of oxidative condensation.
  • This type o f oxidizing dyeing makes it possible to obtain permanent colourings, but it causes a degradation of the keratin fibres owing to the use o f oxidizing agents.
  • dye keratin fibres and in particular human hair
  • dye compositions containing direct dyes Conventional dyes which are used are in particular dyes of nitrobenzene, arthraquinone, nitropyridine, azo, xanthene, acridine, azine or triarylmethane type or natural dyes. These dyes are coloured or colouring mo lecules which have a certain affinity for keratin fibres.
  • compositions containing one or more direct dyes are applied to the keratin fibres for a period o f time necessary to obtain the desired co louration, and are then rinsed out.
  • the resulting colourations are particularly chromatic co lourations which are, however, temporary or semi-permanent since the nature of the interactions that bind the direct dyes to the keratin fibre, and their desorption from the surface and/or from the core of the fibre, are responsible for their poor dyeing power and their poor fastness with respect to washing or perspiration.
  • composition for dyeing keratin fibres, and in particular the hair comprising :
  • composition containing no chemical oxidizing agent other than the oxygen in the air containing no chemical oxidizing agent other than the oxygen in the air
  • a subj ect of the invention is also a process for dyeing keratin fibres, such as human keratin fibres, and in particular the hair, comprising the application, to said fibres, of said composition in one or more steps .
  • the invention finally relates to the use of said composition and to a kit comprising said composition.
  • composition according to the invention should not comprise any chemical oxidizing agent other than the oxygen in the air.
  • chemical oxidizing agent denotes hydrogen peroxide, urea peroxide, alkali metal bromates, and persalts such as perborates and persulphates .
  • the dyes used in the composition according to the invention are dyes chosen from chromene dyes and chromane dyes .
  • chromene or chromane dye is intended to mean dyes which comprise, in their structure, at least one bicyclic compound of formula (A) below:
  • the dyes of formula (A) are chosen from the dyes having the fo llowing formulae :
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 which may be identical or different, represent, independently of one another, a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group, an optionally substituted alkoxy group or an optionally substituted acyloxy group,
  • Ri2, Ri3, Ri6, Ri and R 2 o which may be identical or different, represent, independently of one another, a hydrogen atom or a C 1 -C4 alkyl radical,
  • Ri4, Ri5, Ri7 and Ris which may be identical or different, represent, independently of one another, a hydrogen atom, a hydroxyl radical or a C1-C4 alkoxy radical,
  • dyes of formula (I) as defined above, they can be in two tautomeric forms denoted (la) and (lb):
  • alkyl radicals cited in the previous definitions of the substituents are linear or branched, saturated, generally C 1 -C 20 , particularly C1-C10, preferably Ci-C 6 , hydrocarbon-based radicals, such as methyl, ethyl, propyl, butyl, pentyl and hexyl.
  • the alkoxy radicals are alkyloxy radicals with the alkyl radicals as defined above, and preferably the alkoxy radicals are C1-C10, such as methoxy, ethoxy, propoxy and butoxy.
  • alkyl or alkoxy radicals When the alkyl or alkoxy radicals are substituted, they can be done so with at least one substituent borne by at least one carbon atom, chosen from:
  • - a 5- or 6-membered heteroaryl radical which is optionally cationic, preferably imidazolium, and optionally substituted with a (C 1 -C 4 ) alkyl radical, preferably methyl;
  • Ci-C 6 alkyl radicals an amino radical substituted with one or two Ci-C 6 alkyl radicals, which may be identical or different, optionally bearing at least:
  • alkyl radicals one amino group optionally substituted with one or two optionally substituted C 1 -C3 alkyl radicals, it being possible for said alkyl radicals to form, with the nitrogen atom to which they are attached, a saturated or unsaturated and optionally substituted 5- to 7-membered heterocycle optionally comprising at least one other heteroatom other than or the same as nitrogen,
  • R'R"R' M " for which R', R" and R'", which may be identical or different, represent a hydrogen atom, or a C 1 -C 4 alkyl group; and M " represents the counterion of the corresponding organic acid, inorganic acid or halide,
  • an acylamino radical (-NR-COR') in which the R radical is a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group, and the R' radical is a C 1 -C 2 alkyl radical;
  • R radicals which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group;
  • R'S0 2 -NR- an alkylsulphonylamino radical (R'S0 2 -NR-) in which the R radical represents a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group, and the R' radical represents a C 1 -C 4 alkyl radical or a phenyl radical;
  • R radicals (R) 2 N-S0 2 -) in which the R radicals, which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical optionally bearing at least one hydroxyl group;
  • a carboxylic radical in acid form or salified form preferably salified with an alkali metal or a substituted or unsubstituted ammonium
  • a phenylcarbonyloxy group optionally substituted with one or more hydroxyl groups
  • phenyl group optionally substituted with one or more hydroxyl groups .
  • glyco syl radical is intended to mean a radical derived from a monosaccharide or polysaccharide.
  • the alkyl or alkoxy radicals of formula (I) are not substituted.
  • the dyes of formula (I) comprise an R 6 radical representing a hydroxyl group .
  • Another particular embodiment of the invention concerns the dyes o f formula (I), for which the R 1 radical represents a hydrogen atom or a hydroxyl group .
  • composition according to the invention comprises one or more dyes of formula (I) chosen from haematoxylin, haematein, brazilin, brazilein, santalins and santarubins, and the tautomeric and/or mesomeric forms thereof, the stereoisomers thereof, the addition salts thereof with a cosmetically acceptable acid or base, and also the hydrates.
  • dyes of formula (I) chosen from haematoxylin, haematein, brazilin, brazilein, santalins and santarubins, and the tautomeric and/or mesomeric forms thereof, the stereoisomers thereof, the addition salts thereof with a cosmetically acceptable acid or base, and also the hydrates.
  • haematoxylin/haematein and brazilin/brazilein dyes mention may be made, by way of example, of haematoxylin (Natural Black 1 according to the INCI name) and brazilin (Natural Red 24 according to the INCI name), dyes from the family of indochromanes, which are commercially available. The latter may exist in an oxidized form and be obtained by synthesis processes or by processes for extraction from plants or vegetables known to be rich in these dyes.
  • the dyes of formula (I) can be used in the form of extracts. Use may be made of the following plant extracts (genus and species): Haematoxylon campechianum, Haematoxylon brasiletto, Caesalpinia echinata, Caesalpinia sappan, Caesalpinia spinosa and Caesalpina brasiliensis.
  • the extracts are obtained by extraction of various parts of plants, such as, for example, the root, wood, bark or leaf.
  • the natural dyes of formula (I) are derived from logwood, pernambuco wood, sappan wood or brazilwood.
  • the dyes used in the present invention are preferably those for which Rn and R represent an alkyl radical, preferably methyl.
  • Ri 2 , Ri6, Ri and R 2 o denote, independently of one another, a hydrogen atom or an alkyl radical, preferably methyl.
  • Ri 4 and R17 denote, independently of one another, a hydrogen atom or an alkoxy radical, preferably methoxy.
  • Ris and R15 denote, independently of one another, a hydrogen atom, a hydroxyl radical or an alkoxy radical, preferably methoxy.
  • a first particularly preferred family of dyes suitable for the present invention is that of the dyes corresponding to formula (II) above for which Ri 2 , Ris, Ri6, Ri7, Ri and R 2 o each represent a hydrogen atom, Rn and R13 each represent a methyl radical and Ri 4 represents a methoxy radical.
  • the preferred dyes of this first family are those for which Ris represents a methoxy radical (santalin B) or a hydroxyl radical (santalin A).
  • a second particularly preferred family of dyes suitable for the present invention is that of the dyes corresponding to formula (II) above for which:
  • a preferred dye of this second family is that for which, in addition, Rig represents a methyl radical, R 2 o, R12, R14, Ri8 and Ri 6 each represent a hydrogen atom, and R15 represents the hydroxyl radical (santarubin A).
  • a second preferred dye of this second family is that for which Ri 8 , R20, R12, Ri4 and Ri 6 represent a hydrogen atom, R15 represents a methoxy radical and R19 represents a methyl radical (santarubin B).
  • a third preferred dye of this second family is that for which R 2 o,
  • Ri 2 , Ri4, Ri5, Ri6 and R19 represent hydrogen and Ris represents the hydroxyl radical (santarubin C).
  • Another preferred dye of this second family is that for which R15 represents a methoxy radical, Ris and R14 represent a hydrogen atom, and R 2 o, R12, Ri6 and R19 represent a methyl radical (tetra-O-methyl- cantarubin).
  • the dyes of formula (II) can be used in the form of extracts.
  • Use may be made of plant extracts of red woods, generally grouping together the Asian and West African red wood species of the Pterocarpus genus and of the Baphia genus.
  • These woods are, for example, Pterocarpus santalinus, Pterocarpus osun, Pterocarpus soyauxii, Pterocarpus erinaceus, Pterocarpus indicus or else Baphia nitida.
  • These woods can also be called padauk, sandalwood, narra wood, camwood or else barwood.
  • extracts, containing dyes of formula (II), that can be used in the present invention can, for example, be obtained from red sandalwood ⁇ Pterocarpus santalinus), by aqueous basic extraction, such as the product so ld under the trade name Santal Concentre SL 709C by the company Copiaa, or else by means of so lvent extraction o f sandalwood powder, such as the product sold under the trade name Santal Poudre SL PP by the same company Copiaa. Mention may also be made o f the aqueous-alcoho lic extract of red sandalwood powder from the company Alban Muller.
  • Extracts which are also suitable for the present invention can be obtained from woods such as camwood (Baphia nitida) or else barwood ⁇ Pterocarpus soyauxii, Pterocarpus erinaceus) : the latter is thus fractionated and then milled: a conventional alcoholic extraction or an extraction by perco lation is then carried out on this milled material in order to collect a pulverulent extract which is particularly suitable for the implementation of the present invention.
  • the salts o f the dyes o f formulae (I) and (II) of the invention can be salts of cosmetically acceptable acids or bases .
  • the acids may be mineral or organic.
  • the acid is hydrochloric acid, resulting in chlorides .
  • the bases may be mineral or organic .
  • the bases are alkali metal hydroxides such as sodium hydroxide, resulting in sodium salts.
  • the dye(s) of formulae (I) and (II) present in the composition according to the invention are derived from plant extracts. Mixtures of plant extracts can also be used.
  • the natural extracts o f the dyes according to the invention can be in the form o f powders or liquids.
  • the extracts are in the form o f a powder.
  • the chromene or chromane dyes used are chosen from haematein, haematoxylin, brazilein, brazilin and santalin A. Even more preferentially, use is preferably made o f the dyes o f formula (I), and most particularly haematein and brazilein.
  • the composition according to the invention comprises from 0.001 % to 20% by weight of dyes chosen from chromene dyes, chromane dyes, and mixtures thereof relative to the total weight of the composition, preferably from 0.01 % to 10%> by weight.
  • composition according to the invention also comprises one or more zinc (Zn) salts.
  • the zinc salts according to the invention may be organic or mineral in nature.
  • the zinc salt is a salt o f an organic acid
  • the organic acid according to the invention contains one or more carboxylic and/or sulphonic acid functions.
  • the organic acid according to the invention may be saturated or unsaturated, linear, branched or cyclic.
  • the salt o f zinc and o f an organic acid according to the invention may especially be chosen from zinc gluconate, zinc lactate, zinc glycinate, zinc aspartate, zinc pyrrolidone carboxylate (more commonly referred to as zinc pidolate), zinc phenolsulphonate, zinc salicylate, zinc citrate, zinc acetate and mixtures thereo f.
  • mineral salts is intended to mean inorganic salts, i. e . salts which do not comprise, in their structure, any carbon atom bonded to at least one hydrogen atom.
  • the mineral salts are salts resulting from the action of a mineral acid or of a mineral base on zinc.
  • the salts mention may be made of zinc halides, such as chloride, fluoride and iodide, zinc sulphate, zinc phosphate, zinc nitrate, zinc carbonate and zinc perchlorate, and also mixtures thereof.
  • the mineral zinc salts used are zinc sulphate, zinc phosphate and zinc chloride.
  • the mineral zinc salts can be introduced in solid form into the compositions, or else can originate from a natural, mineral or spring water rich in these ions or else from sea water (in particular Dead Sea water). They can also originate from mineral compounds such as earths, rocks or ochres, for instance clays (for example green clay), or even from a plant extract containing same, as described, for example, in document FR 2 814943.
  • Zinkosite ZnS0 4 In particular, the zinc salts o f the invention are in oxidation state 2 : Zn(II) .
  • the zinc salts are chosen from zinc gluconate, zinc citrate, zinc glycinate, zinc phosphate, zinc sulphate and zinc chloride.
  • the composition according to the invention comprises from 0.001 % to 20% by weight of zinc salts relative to the total weight of the composition containing them, preferably from 0.05 to 10% by weight.
  • composition according to the invention also comprises specific liquid organic compounds .
  • liquid organic compound(s) which has (have) a Hansen so lubility parameter ⁇ value as defined above are, for examp le, described in the reference handbook "Hansen solubility parameters. A user's handbook, Charles M . HANSEN", CRC Press, 2000, pages 167 to 1 85.
  • This value takes into account the ⁇ so lubility parameter linked to the formation o f hydrogen bonds . It may be recalled that three major types of interactions exist in organic compounds : nonpo lar interactions, permanent dipole-dipole interactions and interactions o f hydrogen bond type, the latter being the subj ect of the parameter defining the organic so lvent in the present invention.
  • solvents which meet this definition, mention may be made of propylene glyco l derivatives, alkylene carbonates, benzyl alcoho l, 2-pentanol, and mixtures thereof.
  • alkylene carbonate By way of alkylene carbonate, mention may be made o f the compounds having the fo llowing chemical formula:
  • R H, C i -Cs alkyl or C i -C 4 hydroxyalkyl.
  • propylene carbonate is preferred.
  • the ⁇ value is preferably less than 14 MPa1 ⁇ 2 .
  • the value o f the ⁇ component is greater than 0 MPa1 ⁇ 2.
  • the value of ⁇ is greater than 3 MPa1 ⁇ 2, preferably greater than 4
  • the composition of the invention generally comprises an amount of liquid organic compounds which have a Hansen ⁇ parameter of less than 16 MPa1 ⁇ 2 of between 0. 1 % and 80%, preferably between 0.5 % and 50%, and even more preferably between 1 % and 30%, of the total weight of the composition.
  • composition according to the invention comprises benzoic acid and/or one or more salts thereo f.
  • the benzoic acid salts may be alkali metal or alkaline-earth metal salts, an ammonium salt, or salts of ions derived from an organic amine.
  • the benzoic acid salts are chosen from sodium benzoate and potassium benzoate.
  • the composition according to the invention comprises from 0.001 % to 20% by weight of benzoic acid and/or one or more salts thereo f, relative to the total weight of the composition containing them, preferably from 0.05 % to 10% by weight.
  • composition according to the invention may be in various galenical forms, such as a lotion, a foam, a cream or a gel or any other form suitable for carrying out dyeing of keratin fibres. It may also be packaged in a pump dispenser without propellant or pressurized in an aerosol container in the presence of a propellant and form a foam.
  • composition according to the invention may comprise a medium suitable for dyeing, also known as dyeing vehicle, which can contain water, a mixture of water and one or more organic solvents or else a mixture of organic solvents.
  • a medium suitable for dyeing also known as dyeing vehicle, which can contain water, a mixture of water and one or more organic solvents or else a mixture of organic solvents.
  • the cosmetic composition(s) according to the invention contain(s) water.
  • liquid organic compounds having a ⁇ of less than 16, defined above, and also , for example, of C 1 - C 4 lower alkano ls, such as ethanol and isopropano l; polyo ls and polyo l ethers, for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, and hexylene glyco l.
  • C 1 - C 4 lower alkano ls such as ethanol and isopropano l
  • polyo ls and polyo l ethers for instance 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, and hexylene glyco l.
  • the organic so lvents other than the liquid organic compounds having a ⁇ o f less than 1 6 are present in proportions preferably o f 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.
  • composition according to the invention can comprise one or more additional direct dyes .
  • direct dyes are, for examp le, chosen from those conventionally used in direct dyeing, and among which mention may be made o f all the aromatic and/or nonaromatic dyes commonly used, such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes other than the chromanes and chromenes of the invention, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine, triarylmethane or indoamine direct dyes, methines, styryls, porphyrins, metalloporphyrins, phthalocyanines, methinecyanines and fluorescent dyes .
  • aromatic and/or nonaromatic dyes commonly used, such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes other than the chromanes and chromenes of the invention, neutral
  • o f lawsone juglone, indigo, isatin, curcumin, spinulo sin, apigenidine or orceins.
  • Use may also be made o f extracts or decoctions containing these natural dyes, and in particular cataplasms or extracts based on henna, chlorophyllin, sorghum extract or laccaic acid.
  • the additional direct dye(s) in the composition according to the invention preferably represent from 0.001 % to 10% by weight approximately o f the total weight of the composition.
  • composition according to the invention can also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, non-ionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, non-ionic, amphoteric or zwitterionic polymers or blends thereof, inorganic or organic thickeners, and in particular anionic, cationic, non-ionic and amphoteric polymeric associative thickeners, antioxidants, penetration agents, equestrants, fragrances, buffers, dispersants, conditioning agents such as, for example, vo latile or non-vo latile and modified or unmo dified silicones, film- forming agents, ceramides, preservatives or opacifiers .
  • adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, non-ionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic
  • Said adjuvants are preferably chosen from surfactants, such as anionic or non-ionic surfactants or mixtures thereof, and inorganic or organic thickeners.
  • the above adjuvants are generally present in an amount of, for each of them, between 0.01 % and 40% by weight, relative to the weight of the composition, preferably between 0. 1 % and 20%> by weight, relative to the weight of the composition according to the invention.
  • the pH of this aqueous dye composition is between 2 and 12, and even more preferably between 4 and 12, and particularly between 7 and 12.
  • This pH can be adjusted to the desired value by means of acidifying or basifying agents commonly used in the dyeing of keratin fibres or else using conventional buffer systems.
  • acidifying agents of the compositions used in the invention mention may, for example, be made o f mineral or organic acids such as hydrochloric acid, orthophosphoric acid and sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, and sulphonic acids.
  • o f aqueous ammonia alkali metal carbonates, alkano lamines, such as mono-, di- and triethano lamines, and also derivatives thereo f, sodium hydroxide or potassium hydroxide and the compounds o f formula (III) below: ⁇
  • W is a propylene residue optionally substituted with a hydroxyl group or a C 1 -C 4 alkyl radical; and R a , R b , R c and R d , which may be identical or different, represent a hydrogen atom, a C 1 - C 4 alkyl radical or a C 1 -C 4 hydroxyalkyl radical.
  • the invention also relates to a process for dyeing keratin fibres, such as human keratin fibres, and in particular the hair, comprising the application, to said fibres, of a composition as defined above.
  • the dyeing process is carried out in one single step, by application to the keratin fibres o f a cosmetic dye composition comprising :
  • composition containing no chemical oxidizing agent other than the oxygen in the air containing no chemical oxidizing agent other than the oxygen in the air
  • composition o f zinc phosphate in combination with a composition o f zinc phosphate at 1 g% of zinc element.
  • the cosmetic composition defined above can be applied as it is to the keratin fibres. It can also be ready-to-use and result from extemporaneous mixing of at least two compositions, which may be provided in a dyeing kit.
  • At least one of said compositions containing, together or separately, the ingredients is aqueous .
  • the leave-in time is generally fixed between 3 and 120 minutes, preferably between 10 and 60 minutes, and more preferably between 15 and 45 minutes.
  • the dyeing process is carried out, in several steps, by application to the keratin fibres of several cosmetic dye compositions containing, together or separately, in said composition(s), the fo llowing ingredients :
  • composition containing no chemical oxidizing agent other than the oxygen in the air containing no chemical oxidizing agent other than the oxygen in the air
  • composition o f zinc phosphate in combination with a composition o f zinc phosphate at 1 g% of zinc element.
  • steps can be optionally separated by intermediate rinsing.
  • wringing-out with a towel or paper can be carried out in order to remove the surplus composition.
  • the first step consists in applying to said fibres a cosmetic composition i) comprising the chosen chromene and chromane dye(s), and mixtures thereof as defined above, and one or more liquid organic compounds having a value for the Hansen parameter ⁇ at 25 °C o f less than 16Mpa 1 ⁇ 2 , and benzoic acid and/or one or more salts thereof, and then a second step consists in applying to said fibres a cosmetic composition ii) comprising one or more zinc salts as defined above.
  • the first step consists in applying to said fibres a composition ii) comprising one or more zinc salts as defined above, and then a second step consists in applying to said fibres a second cosmetic composition i) comprising the chosen chromene and chromane dye(s), and mixtures thereo f as defined above, and one or more liquid organic compounds having a value for the Hansen parameter ⁇ at 25 °C of less than 16Mpa 1 ⁇ 2 , and benzoic acid and/or one or more salts thereof.
  • At least one o f the compositions used in the process o f the invention is anhydrous and can be in pulverulent or pasty form.
  • composition When the composition is in pulverulent form, it can contain pulverulent ingredients other than the compounds present in compositions i) and ii) .
  • composition when in the form o f a paste, it can optionally contain one or more inert organic liquids, preferably chosen from liquid petroleum j elly, po lydecenes and fatty esters which are liquid at ambient temperature (25 °C) and at atmospheric pressure (760 mmHg) .
  • inert organic liquids preferably chosen from liquid petroleum j elly, po lydecenes and fatty esters which are liquid at ambient temperature (25 °C) and at atmospheric pressure (760 mmHg) .
  • the leave-in time after application of the cosmetic composition for the first step is generally fixed between 3 and 120 minutes, preferably between 10 and 60 minutes, and more preferably between 10 and 45 minutes .
  • the leave-in time after application of the second cosmetic composition for the second step is generally fixed between 3 and 120 minutes, preferably between 3 and 60 minutes, and more preferably between 5 and 30 minutes .
  • the application temperature is generally between ambient temperature ( 15 to 25 ° C) and 80° C, and more particularly between 15 and 45 °C .
  • the composition according to the invention it is advantageously possible, after application of the composition according to the invention, to subj ect the head o f hair to a heat treatment by heating at a temperature of between 30 and 60°C .
  • this operation can be carried out using a hairstyling hood, a hair dryer, a dispenser of infrared rays and other conventional heating devices .
  • Use may also be made, both as means for heating and for smoothing the head o f hair, o f a heating iron at a temperature of between 60 and 220°C , and preferably between 120 and 200°C .
  • the invention also relates to the use of the composition according to the invention, for dyeing keratin fibres, such as human keratin fibres, and in particular the hair.
  • kits or devices can be used for carrying out the process according to the invention.
  • the kit can comprise at least two compartments :
  • a first compartment comprising a cosmetic composition i) containing the chosen chromene and chromane dye(s), and mixtures thereo f, as defined above, and mixtures thereof and one or more liquid organic compounds having a value for the Hansen parameter ⁇ at 25 ° C o f less than 16 MPa 2 , and benzoic acid and/or one or more salts thereo f, and
  • a second compartment comprising a cosmetic composition ii) containing one or more zinc salts as defined above.
  • the kit also comprises an additional composition comprising one or more treating agents .
  • compositions of the kit are packaged in separate compartments, optionally accompanied by suitable application means, which may be identical or different, such as fine brushes, brushes or sponges .
  • the kit mentioned above can also be equipped with a means for delivering the desired mixture onto the hair, for example such as the devices described in patent FR 2 586 913.
  • a means for delivering the desired mixture onto the hair for example such as the devices described in patent FR 2 586 913.
  • Pairs of locks of natural and permanent-waved hair containing 90% white hairs are treated successively with:

Abstract

La présente invention concerne une composition pour la coloration de fibres kératiniques, telles que des fibres kératiniques humaines, et en particulier les cheveux, qui comprend: - un ou plusieurs colorants choisis parmi des colorants chromènes, les colorants chromanes, et leurs mélanges, - un ou plusieurs sels de zinc, - un ou plusieurs composés organiques qui sont liquides à 25°C et à pression atmosphérique (760 mmHg) et qui ont une valeur pour le paramètre de Hansen δΗ à 25°C inférieure à 16 MPa½, et - de l'acide benzoïque et/ou un ou plusieurs sels de celui-ci, la composition ne contenant pas d'agent oxydant chimique autre que l'oxygène présent dans l'air. La présente invention concerne également un procédé d'utilisation et l'utilisation associée.
PCT/EP2011/057517 2010-05-11 2011-05-10 Composition de coloration capillaire comprenant des colorants chromanes et/ou chromènes WO2011141462A1 (fr)

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FR1053685A FR2959934B1 (fr) 2010-05-11 2010-05-11 Composition de coloration capillaire comprenant des colorants chromaniques et/ou chromeniques
FR1053685 2010-05-11
US34842410P 2010-05-26 2010-05-26
US61/348,424 2010-05-26

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014102338A2 (fr) * 2012-12-27 2014-07-03 L'oreal Procédé de coloration de cheveux utilisant un colorant chromène ou chromane, un composé organique particulier, un agent oxydant, un agent alcalin et un sel métallique
WO2014102324A1 (fr) * 2012-12-27 2014-07-03 L'oreal Procédé de coloration utilisant un colorant et un sel chaotropique
EP3703648A4 (fr) * 2017-11-03 2021-09-29 Emerald Kalama Chemical, LLC Compositions antimicrobiennes

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FR2549721A1 (fr) 1983-07-28 1985-02-01 Secta Labo Cosmetologie Y Roch Procede et compositions pour la coloration des phaneres
FR2586913A1 (fr) 1985-09-10 1987-03-13 Oreal Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede
GB2190104A (en) * 1986-05-07 1987-11-11 Oreal Dyeing human hair with brazilin or haematoxylin in conjuntion with a cupric salt
EP0335403A2 (fr) 1988-03-30 1989-10-04 Sansho Seiyaku Co., Ltd. Composition pour la teinture des cheveux
DE4209897C1 (de) 1992-03-26 1993-10-21 Schoenox Nobel Gmbh Baustoffmischung für Schaummörtel sowie Verfahren zur Herstellung von Schaummörtel und Verwendungen der Baustoffmischung
FR2722685A1 (fr) 1994-07-22 1996-01-26 Oreal Utilisation d'un sel de manganese, de zinc et de cobalt dans un procede de teinture en un temps mettant en oeuvre un compose indolique
FR2814943A1 (fr) 2000-10-09 2002-04-12 Oreal Composition de coloration, procede d'obtention et utilisation pour la coloration de la peau et/ou des fibres keratiniques
EP1210931A1 (fr) 2000-12-04 2002-06-05 L'oreal Composition de coloration des fibres keratiniques
EP1424060A1 (fr) 2002-11-29 2004-06-02 L'oreal Agent de coloration des matières kératiniques humaines à au moins deux composants et procédés de coloration
WO2007130777A2 (fr) * 2006-05-01 2007-11-15 Advanced Cosmetic Technologies Llc Composition de coloration de fibres de kératine et procédé de coloration des cheveux au moyen de cette dernière
EP1915981A1 (fr) * 2006-10-26 2008-04-30 L'Oréal Procédé pour protéger la couleur de fibres kératiniques teintes artificiellement vis-à-vis du lavage et de la lumière ; procédés de coloration

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FR2586913A1 (fr) 1985-09-10 1987-03-13 Oreal Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede
GB2190104A (en) * 1986-05-07 1987-11-11 Oreal Dyeing human hair with brazilin or haematoxylin in conjuntion with a cupric salt
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DE4209897C1 (de) 1992-03-26 1993-10-21 Schoenox Nobel Gmbh Baustoffmischung für Schaummörtel sowie Verfahren zur Herstellung von Schaummörtel und Verwendungen der Baustoffmischung
FR2722685A1 (fr) 1994-07-22 1996-01-26 Oreal Utilisation d'un sel de manganese, de zinc et de cobalt dans un procede de teinture en un temps mettant en oeuvre un compose indolique
FR2814943A1 (fr) 2000-10-09 2002-04-12 Oreal Composition de coloration, procede d'obtention et utilisation pour la coloration de la peau et/ou des fibres keratiniques
EP1210931A1 (fr) 2000-12-04 2002-06-05 L'oreal Composition de coloration des fibres keratiniques
EP1424060A1 (fr) 2002-11-29 2004-06-02 L'oreal Agent de coloration des matières kératiniques humaines à au moins deux composants et procédés de coloration
WO2007130777A2 (fr) * 2006-05-01 2007-11-15 Advanced Cosmetic Technologies Llc Composition de coloration de fibres de kératine et procédé de coloration des cheveux au moyen de cette dernière
EP1915981A1 (fr) * 2006-10-26 2008-04-30 L'Oréal Procédé pour protéger la couleur de fibres kératiniques teintes artificiellement vis-à-vis du lavage et de la lumière ; procédés de coloration

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014102338A2 (fr) * 2012-12-27 2014-07-03 L'oreal Procédé de coloration de cheveux utilisant un colorant chromène ou chromane, un composé organique particulier, un agent oxydant, un agent alcalin et un sel métallique
WO2014102324A1 (fr) * 2012-12-27 2014-07-03 L'oreal Procédé de coloration utilisant un colorant et un sel chaotropique
FR3000385A1 (fr) * 2012-12-27 2014-07-04 Oreal Procede de coloration capillaire mettant en oeuvre un colorant chromenique ou chromanique, un compose organique particulier, un agent oxydant, un agent alcalin et un sel metallique
FR3000388A1 (fr) * 2012-12-27 2014-07-04 Oreal Procede de coloration mettant en oeuvre un colorant et un sel chaotropique
WO2014102338A3 (fr) * 2012-12-27 2014-10-30 L'oreal Procédé de coloration de cheveux utilisant un colorant chromène ou chromane, un composé organique particulier, un agent oxydant, un agent alcalin et un sel métallique
CN104884035A (zh) * 2012-12-27 2015-09-02 欧莱雅 采用色烯或色满染料、特定的有机化合物、氧化剂、碱剂及金属盐的头发着色方法
US9993412B2 (en) 2012-12-27 2018-06-12 L'oreal Hair colouring method employing a chromene or chroman dye, a particular organic compound, an oxidizing agent, an alkaline agent and a metal salt
EP3703648A4 (fr) * 2017-11-03 2021-09-29 Emerald Kalama Chemical, LLC Compositions antimicrobiennes
US11917993B2 (en) 2017-11-03 2024-03-05 Lanxess Corporation Antimicrobial compositions

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FR2959934A1 (fr) 2011-11-18

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