WO2017108551A1 - Procédé de coloration des cheveux utilisant un colorant naturel, un agent oxydant, des substances grasses et des tensioactifs, composition et kit comprenant lesdits ingrédients - Google Patents

Procédé de coloration des cheveux utilisant un colorant naturel, un agent oxydant, des substances grasses et des tensioactifs, composition et kit comprenant lesdits ingrédients Download PDF

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WO2017108551A1
WO2017108551A1 PCT/EP2016/081102 EP2016081102W WO2017108551A1 WO 2017108551 A1 WO2017108551 A1 WO 2017108551A1 EP 2016081102 W EP2016081102 W EP 2016081102W WO 2017108551 A1 WO2017108551 A1 WO 2017108551A1
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formula
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Arno WAHLER
Marika Fila
Frédéric Simonet
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L'oreal
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • 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
    • A61K8/22—Peroxides; Oxygen; Ozone
    • 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
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium 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
    • A61K8/4973—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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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
    • A61K8/9755—Gymnosperms [Coniferophyta]
    • A61K8/9767—Pinaceae [Pine family], e.g. pine or cedar
    • 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]

Definitions

  • the present invention relates to a process of dyeing keratin fibres using i) a dyeing composition comprising one or more natural dye(s) as defined hereinafter, then ii) a second, oxidizing composition composition comprising a) one or more chemical oxidizing agent(s) such as hydrogen peroxide or a hydrogen peroxide-generating system, b) one or more fatty substance(s) and c) one or more non-ionic or cationic surfactant(s), it being possible for compositions i) and ii) to be applied simultaneously or sequentially.
  • a dyeing composition comprising one or more natural dye(s) as defined hereinafter
  • a second, oxidizing composition composition comprising a) one or more chemical oxidizing agent(s) such as hydrogen peroxide or a hydrogen peroxide-generating system, b) one or more fatty substance(s) and c) one or more non-ionic or cationic surfactant(s), it being possible for compositions i) and
  • the invention also relates to a dyeing composition
  • a dyeing composition comprising one or more natural dye(s) as defined hereinafter, a) one or more chemical oxidizing agent(s) such as hydrogen peroxide or a hydrogen peroxide-generating system, b) one or more fatty substance(s) and c) one or more non-ionic or cationic surfactant(s).
  • oxidation bases such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • couplers or colour modifiers the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
  • This oxidation dyeing process consists in applying to the keratin fibres bases or a mixture of bases and couplers with hydrogen peroxide (H 2 0 2 or aqueous hydrogen peroxide solution), as oxidizing agent, in leaving it to diffuse, and then in rinsing the fibres.
  • hydrogen peroxide H 2 0 2 or aqueous hydrogen peroxide solution
  • the colourings resulting therefrom are permanent, strong and resistant to external agents, especially to light, bad weather, washing, perspiration and rubbing.
  • the commercial hair dyes which contain them can exhibit disadvantages, such as staining and problems of odour, comfort and degradation of the keratin fibres. This is particularly the case with oxidation dyeing operations.
  • the standard dyes that are used are, in particular, dyes of the nitrobenzene, anthraquinone, nitropyridine, azo, xanthene, acridine, azine or triarylmethane type, or natural dyes. These dyes may be non-ionic, anionic, cationic or amphoteric. These dyes are coloured or colouring molecules that have affinity for keratin fibres. These compositions containing one or more direct dyes are applied to the keratin fibres for a time necessary to obtain the desired colouring, and are then rinsed out.
  • the colourings that result therefrom are chromatic colourings which are, however, only 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 the core of the fibre are responsible for their weak dyeing power and their poor fastness with respect to light, washing or perspiration.
  • a dyeing cosmetic composition i) comprising one or more cationic, anionic or neutral natural dye(s), in particular neutral natural dye(s), preferably chosen from ortho- diphenols (ODPs); and
  • an oxidizing cosmetic composition ii) comprising:
  • compositions i) and ii) can be applied simultaneously or sequentially, and
  • the fatty substance content of the oxidizing composition ii) does not exceed 10% relative to the weight of the composition ii).
  • Another subject of the invention is a composition for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising one or more cationic, anionic or neutral natural dye(s), in particular neutral natural dye(s), preferably chosen from ortho-diphenols (ODPs); a) one or more chemical oxidizing agent(s); b) one or more fatty substance(s); and c) one or more cationic and/or non-ionic surfactant(s);
  • the fatty substance content of the composition does not exceed 5% relative to the weight of the composition.
  • kits or devices comprising at least two separate compartments, in which one of the compartments contains the dyeing composition i) as defined above and another compartment contains the composition ii) as defined above.
  • the process according to the invention and and also the kit of the invention have the advantage of dyeing human keratin fibres, with persistent dyeing results.
  • the dyeing process according to the invention can produce colourings that are resistant to washing, perspiration and light without impairing the fibres.
  • the colour homogeneity between the root and the end of the fibres is good.
  • the dyeing process performed makes it possible to induce very satisfactory "build-up" and/or power of the colouring, while at the same time respecting the keratin fibre cosmetics, in particular in terms of feel.
  • the dyeing composition of the invention comprises at least one natural dye.
  • natural dyes or “dyes of natural origin” is intended to mean dyes derived from natural materials (plant, mineral or animal origin), for instance extracts, ground material and decoctions, which have a greater or smaller concentration of dyes.
  • the natural dyes may be chosen especially from spinulosin, orceins, polyphenols or ortho-diphenols (also referred to as ODPs in the rest of the description) and all extracts rich in ODPs, curcumin, indole derivatives such as isatin or indole-2,3-dione, indigoids including indigo, phthalocyanines and porphyrins in particular complexed to a metal, glycosyl or non-glycosyl iridoids, chromene dyes, anthraquinone and naphthoquinone dyes such as lawsone or henna, juglone, spinulosin, chromene or chroman dyes, such as neoflavanols and neoflavanones, flavanols; and anthocyanidols.
  • the dye(s) of natural origin according to the invention may or may not be salified. They can also be in the aglycone form (without bonded sugar) or in the form of glycosylated compounds.
  • glycosyl radical is intended to mean a radical derived from a monosaccharide or polysaccharide.
  • the dye(s) are chosen from ortho-diphenol(s): ODP(s) and polyphenols.
  • ODP(s) is intended to mean one or more compounds comprising one or more aromatic rings, at least one of which is a benzene ring substituted with at least two hydroxyl (OH) groups borne by two adjacent carbon atoms of said benzene group which is present in the structure of the ortho-diphenol(s).
  • the aromatic ring is more particularly a fused aryl or fused heteroaromatic ring, i.e. optionally comprising one or more heteroatoms, such as benzene, naphthalene, tetrahydronaphthalene, indane, indene, anthracene, phenanthrene, indole, isoindole, indoline, isoindoline, benzofuran, dihydrobenzofuran, chroman, isochroman, chromene, isochromene, quinoline, tetrahydroquinoline and isoquinoline, said aromatic ring comprising at least two hydroxyl groups borne by two adjacent carbon atoms of the aromatic ring.
  • the aromatic ring of the ortho-diphenol derivatives according to the invention is a benzene ring.
  • fused ring is intended to mean that at least two saturated or unsaturated and heterocyclic or non-heterocyclic rings have a shared bond, i.e. at least one ring is placed side-by-side with another ring.
  • the dye(s) of the invention represent an ODP of formula (II), or an oligomer, tautomer, optical isomer or geometrical isomer thereof, and also salts or solvates thereof, such as hydrates:
  • R 1 to R 4 which may be identical or different, represent: i) a hydrogen atom, ii) a halogen atom, or a group chosen from iii) hydroxyl, iv) carboxyl, v) (CrC 2 o)alkyl carboxylate or (CrC 2 o)alkoxycarbonyl, vi) optionally substituted amino, vii) optionally substituted linear or branched (Ci-C 2 o)alkyl, viii) optionally substituted linear or branched (C 2 -C 2 o)alkenyl, ix) optionally substituted cycloalkyl, x) (CrC 20 )alkoxy, xi) (Ci-C 20 )alkoxy(Ci-C 20 )alkyl, xii) (CrC 20 )alkoxyaryl, xiii) aryl which may optionally be substituted, xiv) aryl,
  • R 1 - R 2 , R 2 - R 3 or R 3 - R 4 form, together with the carbon atoms that bear them, a saturated or unsaturated, aromatic or non-aromatic ring, optionally containing one or more heteroatoms and optionally fused with one or more saturated or unsaturated rings optionally containing one or more heteroatoms.
  • the compound of formula (II) comprises from one to four rings.
  • One particular embodiment of the invention relates to one or more ODPs of formula (II), two adjacent substituents R 1 - R 2 , R 2 - R 3 or R 3 - R 4 of which cannot form, with the carbon atoms that bear them, a pyrrolyl radical.
  • R 2 and R 3 form a pyrrolyl or pyrrolidinyl radical fused to the benzene ring bearing the two hydroxyls.
  • saturated or unsaturated and optionally fused rings may also be optionally substituted
  • alky radicals are saturated, linear or branched, generally Ci-C 2 o, particularly d- Cio, hydrocarbon-based radicals, preferably Ci-C 6 alkyl radicals, such as methyl, ethyl, propyl, butyl, pentyl and hexyl;
  • alkenyP' radicals are unsaturated and linear or branched C 2 -C 2 o hydrocarbon- based radicals; preferably comprising at least one double bond, such as ethylene, propylene, butylene, pentylene, 2-methylpropylene and decylene;
  • aryP' radicals are monocyclic or fused or non-fused polycyclic carbon-based radicals preferentially comprising from 6 to 30 carbon atoms, at least one ring of which is aromatic; preferentially, the aryl radical is chosen from phenyl, biphenyl, naphthyl, indenyl, anthracenyl and tetrahydronaphthyl;
  • alkoxy radicals are alkyl-oxy radicals with alkyl as defined previously, preferably a C 1 -C 10 alkyl, such as methoxy, ethoxy, propoxy and butoxy;
  • alkoxyalky radicals are (Ci-C 2 o)alkoxy(Ci-C 2 o)alkyl radicals, such as methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, etc.;
  • cycloalky radicals are C 4 -C 8 cycloalkyl radicals, preferably cyclopentyl and cyclohexyl radicals; the cycloalkyl radicals may be substituted cycloalkyl radicals, in particular substituted with alkyl, alkoxy, carboxylic acid, hydroxyl, amine and ketone groups;
  • alkyi' or “alkenyP' radicals when they are “optionally substituted", may be substituted with at least one atom or group borne by at least one carbon atom chosen from: i) halogen; ii) hydroxyl; iii) (CrC 2 )alkoxy; iv) (Ci-Ci 0 )alkoxycarbonyl; v) (poly)hydroxy(C 2 -C 4 )alkoxy; vi) amino; vii) 5- or 6-membered heterocycloalkyl; viii) optionally cationic 5- or 6-membered heteroaryl, preferably imidazolium, optionally substituted with a (CrC 4 )alkyl radical, preferably methyl; ix) amino substituted with one or two identical or different Ci-C 6 alkyl radicals optionally bearing at least: a) one hydroxyl group, b) one amino group optionally substituted with one or two optionally substituted (CrC 3
  • aryP' or “heterocyclic” radicals or the aryl or heterocyclic part of the radicals, when they are “optionally substituted" may be substituted with at least one atom or group borne by at least one carbon atom chosen from:
  • (CrCio)alkyl preferably Ci-C 8 alkyl, optionally substituted with one or more radicals chosen from the following radicals: hydroxyl, (CrC 2 )alkoxy, (poly)hydroxy(C 2 - C 4 )alkoxy, acylamino, amino substituted with two identical or different C1-C4 alkyl radicals optionally bearing at least one hydroxyl group or it being possible for the two radicals to form, with the nitrogen atom to which they are attached, a saturated or unsaturated and optionally substituted 5- to 7-membered, preferably 5- or 6- membered, heterocycle optionally comprising another nitrogen or non-nitrogen heteroatom; ii) halogen; iii) hydroxyl; iv) C C 2 alkoxy; v) C1-C10 alkoxycarbonyl; vi) (poly)hydroxy(C 2 -C 4 )alkoxy; vii) amino; viii) 5- or 6-membered hetero
  • glycosyl radical is intended to mean a radical derived from a mono- or polysaccharide
  • radicals "containing one or more silicon atoms" are preferably polydimethylsiloxane, polydiphenylsiloxane, polydimethylphenylsiloxane or stearoxy dimethicone radicals;
  • heterocyclic radicals are radicals comprising, in at least one ring, one or more heteroatoms chosen in particular from O, N and S, preferably O or N, optionally substituted in particular with one or more alkyl, alkoxy, carboxyl, hydroxyl, amine or ketone groups.
  • These rings may comprise one or more oxo groups on the carbon atoms of the heterocycle; mention may in particular be made, among the heterocyclic radicals that may be used, of furyl, pyranyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl and thienyl groups; even more preferably, the heterocyclic groups are fused groups, such as benzofuryl, chromenyl, xanthenyl, indolyl, isoindolyl, quinolyl, isoquinolyl, chromanyl, isochromanyl, indolinyl, isoindolinyl, coumarinyl or isocoumarinyl groups, it being possible for these groups to be substituted, in particular with one or more OH groups.
  • the heterocyclic radicals that may be used, of furyl, pyranyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl and thi
  • the salts of the dyes of the invention may be salts of acids or of bases.
  • the acids can be mineral or organic.
  • the acid is hydrochloric acid, which results in chlorides.
  • the dyeing composition used in the process for dyeing keratin fibres comprises, as dye, one or more natural dyes.
  • the dye(s) of the invention according to a) is (are) chosen from: 1 ) anthocyanidins such as cyanidin, delphinidin or petunidin; 2) anthocyanins or anthocyans such as myrtillin; 3) ortho-hydroxybenzoates, for example gallic acid salts; 4) flavones such as luteolin; 5) hydroxystilbenes, for example tetrahydroxy-3,3',4,5'-stilbene, which are optionally oxylated (for example glucosylated); 6) curcumin; 7) indole derivatives such as isatin or indole-2,3-dione and indigo, preferably isatin; 8) phthalocyanines and porphyrins, in particular complexed with a metal, in particular chlorophyllin and more particularly that complexed with copper or magnesium, preferably cupric chlorophyllin; 9) glycosylated or non-glycosylated
  • the natural dye(s) are chosen from naphthoquinones, in particular juglone and lawsone, in particular those derived from leaves of shrubs of the genus Lawsonia from the family of Lythraceae, which is based on the principle of dyeing with the active agent lawsone: 2-hydroxy-1 ,4-naphthoquinone from henna.
  • Lawsone [83-72-7] (CI Natural Orange 6; CI 75420), also known as isojuglone, may be found in henna shrubs (Lawsonia alba, Lawsonia inermis).
  • the henna is in powder form.
  • the henna powder may be screened to obtain particles with upper limit sizes corresponding to the orifices or mesh sizes of the screen particularly between 35 and 80 mesh (US).
  • the size of the henna powder particles is fine.
  • a particle size of less than or equal to 500 ⁇ is more particularly intended.
  • the powder is constituted of fine particles with a size inclusively between 50 and 300 ⁇ and more particularly between 10 and 200 ⁇ . It is understood that said henna particles preferentially have a moisture content of between 0 and 10% by weight, relative to the total weight of the powders.
  • the dye(s) are chosen from indole derivatives such as isatin or indole-2,3-dione and indigo, preferably isatin.
  • the dye(s) are derived from the plants Isatis tinctoria, Calanthe discolor or Couroupita guianensis.
  • the dye(s) are curcumine or curcumin.
  • This is a compound that is naturally present in curry, which is a polyphenol of which the chemical name is (1 £,6£)-1 ,7-bis(4-hydroxy-3-methoxyphenyl)-1 ,6-heptadiene-3,5-dione, and also the tautomeric forms thereof.
  • the dye(s) of the invention are chosen from natural porphyrins and phthalocyanines, in particular those complexed with a metal, especially chlorophyllin and in particular that complexed with copper or magnesium, preferably copper chlorophyllin.
  • the dye(s) are chosen from glycosyl or non-glycosyl iridoids.
  • the dye(s) of the invention are chosen from (seco)iridoid-glycoside or non-glycosyl (seco)iridoid (also known as aglycone), extracted from plants such as Rubiaceae, Euphorbiaceae, Valerianaceae, Cornaceae, Gentianaceae, Caprifoliaceae, Oleaceae, Ericaceae, Loganiaceae, etc., preferably Rubiaceae.
  • the dye(s) of the invention are derived from extracts of the following plants: Veronica persica; Genipa americana; Apodytes dimidiata; Randia canthioides; Tarenna attenuata and preferably Genipa americana.
  • the dye(s) are chosen from chromene or chroman dyes.
  • chromene or chroman dyes mean dyes which comprise in their structure at least one bicycle of formula (B) below:
  • the dye(s) of the invention are of formula (B) and are preferentially chosen from neoflavonols and neoflavanones, particularly chosen from the dyes of the following formulae:
  • ⁇ z - represents a carbon-carbon single bond or a carbon-carbon double bond, the sequence of these z - bonds denotes two carbon-carbon single bonds and two carbon-carbon double bonds, said bonds being conjugated,
  • ⁇ X represents a group:
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 which may be identical or different, represent a hydrogen atom, a hydroxyl group, an optionally substituted alkyl group, an optionally substituted alkoxy group or an optionally substituted acyloxy group;
  • Rii, Ri2, Ri3, Ri6, Ri9 and R 2 o which may be identical or different, represent a hydrogen atom or a CrC 4 alkyl radical
  • Ri 4 , R-I5, R-I7 and Ri 8 which may be identical or different, represent a hydrogen atom, a hydroxyl radical or a C C 4 alkoxy radical.
  • alkyl radicals mentioned in the preceding definitions of the substituents are saturated and linear or branched hydrocarbon-based radicals, generally Ci-C 2 o, particularly C1-C1 0 , preferably Ci-C 6 hydrocarbon-based radicals, such as methyl, ethyl, propyl, butyl, pentyl and hexyl.
  • the alkoxy radicals are alkyl-oxy radicals with the alkyl radicals as defined above and preferably the alkoxy radicals are C1-C1 0 alkoxy radicals, such as methoxy, ethoxy, propoxy and butoxy.
  • the alkyl or alkoxy radicals when they are substituted, may be substituted with at least one substituent borne by at least one carbon atom chosen from i) a halogen atom or ii) a hydroxyl group; iii) a Ci-C 2 alkoxy group; iv) a C1-C1 0 alkoxycarbonyl group; v) a (poly)hydroxy(C 2 -C 4 )alkoxy group; vi) an amino group; vii) a 5- or 6-membered heterocycloalkyi group; viii) an optionally cationic 5- or 6-membered heteroaryl group, preferably imidazolium, optionally substituted with a (CrC 4 )alkyl radical, preferably methyl; ix) an amino radical substituted with one or two identical or different Ci-C 6 alkyl radicals optionally bearing at least: a) one hydroxyl group, b) one amino group optionally substituted with one or two optionally substitute
  • the alkyl or alkoxy radicals of formula (III) are unsubstituted.
  • the dyes of formula (III) comprise a radical R 6 representing a hydroxyl group.
  • Another particular embodiment of the invention relates to the dye(s)of formula (III) for which the radical Ri represents a hydrogen atom or a hydroxyl group.
  • the dye(s) of the invention are of formula (III) and chosen from haematoxylin, haematein, brazilin and brazilein; preferentially brazilin:
  • Brazilein is a conjugated form of a chroman compound of formula (A2).
  • the tautomeric structures (Ilia) and (lllb) illustrated above are found in the scheme below.
  • haematoxylin/haematein and brazilin/brazilein type examples that may be mentioned include haematoxylin (Natural Black 1 according to the INCI name) and brazilin (Natural Red 24 according to the INCI name), dyes of the indochroman family, which are commercially available. These can exist in an oxidized form and be obtained synthetically or by way of extraction of plants or vegetables known to be rich in these dyes.
  • the natural dye(s) of the invention may be used in the form of extracts.
  • Use may be made of the following plant extracts (genus and species): Haematoxylon campechianum, extracted from oxidized logwood (Haematoxylon campechianum) brasiletto (Haematoxylum brasiletto, rich in brazilin and protosappanin), Quebracho (Schinopsis lorentzii) Caesalpinia echinata, Caesalpinia sappan, Caesalpinia spinosa, and Caesalpina brasiliensis.
  • the extracts are obtained by extraction of various plant parts, such as, for example, the root, wood, bark or leaves.
  • the dye(s) of natural origin are of formula (II) and are obtained from logwood, pernambuco wood, sappan wood and Brazil wood.
  • the dyes are of formula (IV), preferably those for which R-n and Ri 3 represent an alkyl radical, preferably methyl.
  • Ri 2 , Ri 6 , R19 and R 20 denote, independently of each other, a hydrogen atom or an alkyl radical, preferably methyl.
  • Ri 4 and Ri 7 denote, independently of each other, a hydrogen atom or an alkoxy radical, preferably methoxy.
  • Ri 8 and Ri 5 denote, independently of each other, a hydrogen atom, a hydroxyl radical or an alkoxy radical, preferably methoxy.
  • a first particularly preferred family of dyes of natural origin of the invention that are suitable for use in the present invention is that of the dyes corresponding to formula (IV) above for which R 12 , R15, R16, R17, R19 and R 20 each represent a hydrogen atom.
  • Rn and R-I3 each represent a methyl radical and R14 represents a methoxy radical.
  • dyes of the invention of this first family are those for which R 18 represents a methoxy radical (santalin B) or a hydroxyl radical (santalin A).
  • a second particularly preferred family of dyes that are suitable for use in the present invention is that of the dyes corresponding to the formula (IV) above for which:
  • a preferred dye of this second family is that for which, in addition, R 19 represents a methyl radical, R 2 o, R12, Ri 4 , R18 and Ri 6 each represent a hydrogen atom and Ri 5 represents a hydroxyl radical (santarubin A).
  • a second preferred dye of this second family is that for which R 18 , R20, R12, Ri 4 and R16 represent a hydrogen atom, R 15 represents a methoxy radical and R19 represents a methyl radical (santarubin B).
  • a third family of preferred dyes of this second family is that for which R 2 o, R12, R-i 4 , Ris, R16 and R19 represent hydrogen and Ri 8 represents a hydroxyl radical (santarubin C).
  • the advantageous dye(s) of this second family is that for which R 15 represents a methoxy radical, Ri 8 and Ri 4 represent a hydrogen atom and R 2 o, R12, R16 and R19 represent a methyl radical (tetra-O-methylsantarubin).
  • the dye(s) of formula (IV) may be used in the form of extracts.
  • Use may be made of plant extracts of red woods, bringing together generally the species of red woods from Asia and West Africa of the genus Pterocarpus and of the genus Baphia.
  • These woods are, for example, Pterocarpus santalinus, Pterocarpus osun, Pterocarpus soyauxii, Pterocarpus erinaceus, Pterocarpus indicus or else Baphia nitida.
  • These woods may also be called padauk, sandalwood, narra wood, camwood or else barwood.
  • extracts that may be used, containing dyes of formula (IV), in the present invention may be obtained, for example, from red sandalwood (Pterocarpus santalinus) by aqueous basic extraction, such as the product sold under the trade name Santal Concentre SL 709C by COPIAA, or else by means of solvent extraction of sandalwood powder, such as the product sold under the trade name Santal Poudre SL PP by COPIAA. Mention may also be made of the aqueous/alcoholic extract of powdered red sandalwood from Alban Muller.
  • Extracts 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 split up and then ground: a conventional alcoholic extraction or one by percolation is subsequently carried out on this ground material in order to collect a pulverulent extract particularly suitable for the implementation of the present invention.
  • woods such as camwood (Baphia nitida) or else barwood (Pterocarpus soyauxii, Pterocarpus erinaceus): the latter is thus split up and then ground: a conventional alcoholic extraction or one by percolation is subsequently carried out on this ground material in order to collect a pulverulent extract particularly suitable for the implementation of the present invention.
  • the dye(s) of formulae (III) and (IV) of the invention may be salts of acids or bases that are cosmetically acceptable.
  • the acids can be mineral or organic.
  • the acid is hydrochloric acid, which results in chlorides.
  • the bases can be mineral or organic.
  • the bases are alkali metal hydroxides, such as sodium hydroxide, resulting in sodium salts.
  • the dye(s) are chosen from dihydroxyflavonoids, preferably of formula (V) and also the organic or mineral acid or base salts thereof, the optical isomers, geometrical isomers and tautomers thereof, and the solvates thereof such a
  • R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 , R 13 and R 14 which may be identical or different, represent a hydrogen or a halogen atom, or a group chosen from i) hydroxyl, ii) (CrC 6 )alkyl, iii) (d- C 6 )alkoxy, iv) (CrC 6 )alkylthio, v) carboxyl, vi) alkyl carboxylate or alkoxycarbonyl, vii) optionally substituted amino, viii) optionally substituted, linear or branched alkenyl, ix) optionally substituted cycloalkyi, x) optionally substituted aryl, xi) a group containing one or more silicon atoms, xii) (di)((hydroxy)(Ci-C 6 )alkyl)amino, xiii) glucosyl, xiv)
  • R 5 , R 6 , R 7 , R 8 and R 9 which may be identical or different, representing a hydrogen atom, or a group chosen from a hydroxyl group, a (CrC 6 )alkyl group, or a group R-Z-C(X)-Y- as defined previously,
  • the unit (V) constitutes the polymeric unit of a polyphenol which will be linked to the other units of said polyphenol via positions 4, 6 or 8 of the chroman ring, in which case R 1 , or R 3 and R 6 form a covalent bond with the other units of said polyphenol; • or else R 5 with R 6 and/or R 7 with R 8 form, together with the atom which bears them, an oxo group;
  • R 9 when is a double bond between the oxygen atom and the carbon atom in position 2, then R 9 is absent and when is a double bond between the carbon atoms in positions 3 and 4, then R 5 and R 7 are absent;
  • the compound of formula (V) when borne by the oxygen atom is a double bond, then the compound of formula (V) is cationic and an organic or mineral anionic counterion, such as halide, is associated therewith.
  • At least two radicals of the compounds of formula (V) chosen from R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 , R 13 and R 14 , which are contiguous, represent a hydroxyl group.
  • the group R-Z-C(X)-Y- of the compounds of formula (V) represents a 3,4,5- trihydroxyphenyl-1 -carbonyloxy (-O-gallate).
  • the radicals R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 , R 13 and R 14 are chosen from a hydrogen atom and hydroxyl, glycosyloxy and alkoxy groups.
  • the dye(s) c) of the invention are chosen from:
  • the flavanols of formula (Va) which preferably comprise at least two ortho hydroxyl groups, such as catechin, extracted from pine bark, epicatechin gallate, and cocoa flavonols, especially epicatechin, flavonols, in particular flavan-3-ols from green tea, and oligomers and polymers thereof known as proanthocyanidols or fused tannins such as theaflavin, theaflavin 3'-0-gallate, theaflavin 3,3'-0-digallate, proanthocyanidins A1 , A2, B1 , B2, B3 and C1 such as profisetinidin and procyanidin, and mixtures of the preceding
  • formula (Va) which preferably comprise at least two ortho hydroxyl groups, such as catechin, extracted from pine bark, epicatechin gallate, and cocoa flavonols, especially epicatechin, flavonols, in particular flavan-3-ols from green tea, and oligomers and poly
  • R 7 , R 8 which may be identical or different, represent a hydrogen atom or a group chosen from hydroxyl or (CrC 6 )alkyl or a group R-Z-C(X)-Y- as defined previously, preferably O-gallate, it being understood that at least one of the two groups R 7 ou R 8 represents a hydroxyl group or R-Z-C(X)-Y- as defined previously;
  • R 5 and R 6 which may be identical or different, represent a hydrogen atom or a hydroxyl group or R 6 and R 8 form a bond or the unit (Va) constitutes the polymeric unit that will be linked to the other units via position 4, 6 or 8, in which case R 1 , or R 3 and R 6 form a bond; the radicals R 1 , R 2 , R 3 , R 4 , R 10 , R ' R 12 , R 13 and R 14 being as defined previously for formula (V);
  • proanthocyanidin compounds examples that may be mentioned include profisetinidin and procyanidin, the formulae of which are represented;
  • the flavonols of formula (Vb) which comprise at least two ortho hydroxyl groups, such as quercetin, luteolin, myricetol or fisetin, and/or two meta hydroxyl groups, such as morin, heterosides thereof or methoxylated derivatives thereof such as rhamnetin (which preferably comprise at least two ortho hydroxyl groups):
  • the flavones of formula (Vc) which comprise at least two ortho hydroxyl groups, such as luteolin, and heterosides thereof such as luteolol 7-O-glucoside, baicalin and orientin:
  • dihydroflavonols or dihydroxyflavanonols of formula (Vd) which comprise at least two ortho hydroxyl groups, such as dihydroquercetol, and heterosides thereof such as dihydroquercetol 3-O-rhamoside:
  • anthocyanidols or anthocyanides, or anthocyanidins
  • formula (Vg) which comprise at least two ortho hydroxyl groups, such as cyanidol, delphinidin, aurantinidin, luteolinidin, heterosides thereof, such as dihydroxyanthocyans (or dihydroxyanthocyanosides, or anthocyanins on the English model), oligomers and polymers thereof such as proanthocyanins, preferably anthocyanodols and especially from bilberry, and 3-deoxyanthocyanidins especially from sorghum;
  • R represents a hydrogen atom or a hydroxyl group; ydroxyl group or the phenoxy group according to
  • Ri, R 2 , and R 3 which may be identical or different, represent a hydrogen atom or a hydroxyl or (CrC 6 ) alkoxy group, such as methoxy;
  • R 4 represents a hydrogen atom, or a hydroxyl or -O-glycoside group; or alternatively the radicals R, Y and R' form, together with the carbon atoms that bear them, a heterocyclic group fused to ring A, of formula ( ⁇ ), ( ⁇ ) or ( ⁇ ') below:
  • R 5 represents a hydrogen atom or a hydroxyl or -O-glycoside group
  • R 6 to R 10 which may be identical or different, represent a hydrogen atom hydroxyl group, preferably R 6 and R 10 represent a hydrogen atom, R 7 , R 8 ai represent a hydrogen atom or a hydroxyl group;
  • Z represents a hydrogen atom or the group ( ⁇ ) below:
  • the dye(s) according to the invention is (are) compounds of formula (a), and more particularly polyphenols such as tannic acid.
  • the dye(s) according to the invention may in particular be a mixture of proanthocyanidin derivatives such as profisetinidin and procyanidin and of compounds of formula (a), and more particularly polyphenols such as tannic acid.
  • the dye(s) of the invention are derived from plant extracts. Use may also be made of mixtures of plant extracts.
  • the natural extracts of dyes according to the invention may be in the form of powders or liquids.
  • the extracts are in powder form.
  • the natural dye(s) c) of the invention is (are) chosen from:
  • anthraquinones chosen from those of formulae (A1) and (A2) as defined previously; more preferentially, the anthraquinones and extracts containing them are chosen from: garance or Rubia tinctorum or Rubia cordifolia; kermesic acid; carmine; the aluminium salt of carminic acid; carminic acid and its non-glycosyl form; 1 ,2,4- trihydroxyanthraquinone or purpurin; laccaic acid A, B, C or D; and anthragallol or 1 ,2,3-trihydroxyanthraquinone;
  • ⁇ neoflavanols or neoflavanones chosen from those of formulae (III) and (IV) as defined previously; more particularly chosen from haematoxylin and haematein, brazilin and brazilein; preferentially brazilin and the following plant extracts (genus and species): Haematoxylon campechianum, extracted from oxidized logwood (Haematoxylon campechianum), brasiletto (Haematoxylum brasiletto, rich in brazilin and protosappanin), Quebracho ⁇ Schinopsis lorentzii), Caesalpinia echinata, Caesalpinia sappan, Caesalpinia spinosa, and Caesalpina brasiliensis.
  • glycosyl or non-glycosyl iridoids such as (seco)iridoid-glycosides or non-glycosyl (seco)iridoids extracted from plants such as Rubiaceae or Genipa americana;
  • the flavonols (Va) are chosen from catechin, extracted from pine bark, epicatechin gallate, and cocoa flavonols, especially epicatechin, flavan-3-ols from green tea, and oligomers thereof and mixtures thereof;
  • the flavonols of formula (Vb) as defined previously are preferably chosen from quercetin, luteolin and morin, and the heterosides thereof;
  • the anthocyanidols of formula (Vg) are chosen from those from bilberry and 3-deoxyanthocyanidins from sorghum;
  • the natural dye(s) of the invention are chosen from catechin, quercetin, brazilin, haematein, haematoxylin, chlorogenic acid, caffeic acid, gallic acid, catechol, gallic acid, L-DOPA, pelargonidin, cyanidin, (-)-epicatechin, (-)-epigallocatechin,
  • EGCG epigalloc
  • the natural dye(s) are chosen from natural indole or indoline compounds.
  • the invention may then be performed using one or more natural extracts of animals, bacteria, fungi, algae or plants comprising one or more indole or indoline compounds.
  • the dye(s) is (are) derived from an extract of beetroot, especially red beetroot.
  • the extract of beetroot or Beta vulgaris is preferentially an extract obtained from beetroot, especially from the periphery or outer part of beetroot, more particularly from beetroot skin or peel (Eur. Food. Technol., Tytti S. Kujala et al., 214, 505-510 (2002)).
  • red beetroot skin more particularly denotes the peripheral part of the tuber situated between the epidermis and the pericarp (cf. Hermann et al., Journal of Experimental Botany, Vol. 58, No. 1 1 , pp. 3047 - 3060, 2007).
  • the extracts are obtained by extracting various plant parts, for instance the root, the leaves or the peel. Preferentially, the extract is obtained from extraction of red beetroot peel.
  • the extraction is performed via standard methods known to those skilled in the art. Mention may be made, for example, of the method described in Eur. Food Technol., Tytti S. Kujala et al., 214, 505-510 (2002).
  • the natural red beetroot extracts according to the invention may be in the form of powders or liquids.
  • the extracts of the invention are in the form of powders, such as red beetroot peel extract powders.
  • the red beetroot extract(s) used as ingredient c) in one or more composition(s) that are useful in the process according to the invention preferably represent from 0.001 % to 20% by weight relative to the total weight of the composition(s) containing said extract(s).
  • the dye(s) of the invention are chromene or chroman dyes and more preferentially the dye(s) of the invention are chosen from haematein, haematoxylin, brazilein, brazilin and santalin A.
  • carboxylate is intended to mean carboxylic acid salt.
  • both forms may be used in the compositions according to the invention, as may the racemates.
  • the natural dye(s) are derived from extracts of animals, bacteria, fungi, algae, plants and fruit, used in their entirety or partially.
  • the extracts are derived from fruits, including citrus fruits, from vegetables, from trees and from shrubs. Use may also be made of mixtures of these extracts, which are rich in natural dyes, especially in ODPs as defined previously.
  • the natural dye(s) of the invention are derived from extracts of plants or of plant parts.
  • the extracts are obtained by extraction of various plant parts, such as, for example, the root, the wood, the bark, the leaf, the flower, the fruit, the seed, the pod or the peel.
  • extracts of tea leaves in particular of Japanese green tea, and of rose.
  • Mention may be made, among the extracts of fruit, of extracts of apple, extracts of grape (in particular of grape seed) or extracts of cocoa beans and/or pods.
  • Mention may be made, among the extracts of vegetables, of extracts of potato or of onion peel.
  • extracts of tree wood mention may be made of extracts of pine bark and extracts of logwood and extracts of quebracho wood.
  • the ortho-diphenol derivative(s) are natural extracts, rich in ODPs.
  • the dye(s) of the invention are solely natural extracts.
  • the natural dye(s) according to the invention is (are) chosen from catechin, quercetin, haematein, haematoxylin, brazilin, brazilein, gallic acid and tannic acid, and natural extracts containing them chosen from grape marc, pine bark, green tea, onion, cocoa bean, logwood, redwood and gall nut, and quebracho wood, more preferentially quebracho wood.
  • the natural extracts according to the invention may be in the form of powders or liquids.
  • the extracts of the invention are provided in the form of powders.
  • the natural dye(s) is (are) preferably present in a total amount ranging from 0.001 % to 80% by weight relative to the total weight of the dyeing composition, in particular ranging from 0.005% to 20% by weight relative to the total weight of the dyeing composition, preferentially from 0.01 % to 10% by weight and better still from 0.01 % to 5% by weight relative to the total weight of the composition containing them.
  • the content in the composition i) containing them is preferably between 0.001 % and 5% by weight of composition i) containing them.
  • the content in composition i) containing the extract(s) per se is preferably between 0.1 % and 20% by weight of composition i) containing them.
  • Oxidizing cosmetic composition a) Oxidizing agent
  • the oxidizing composition ii) of the invention comprises a) at least one chemical oxidizing agent.
  • chemical oxidizing agent is intended to mean an oxidizing agent other than atmospheric oxygen.
  • chemical oxidizing agent is intended more particularly to mean:
  • alkali metal or quaternary ammonium persalts such as perborates, persulfates, percarbonates, peroxodiphosphates or Oxone®;
  • the oxidizing agent is chosen in particular from sodium perborate, sodium persulfate, potassium persulfate, ammonium persulfate, sodium percarbonate and potassium percarbonate;
  • Ci-C 6 and aromatic C 6 -C 2 o organic peracids and their percarboxylate forms such as performic acid, peracetic acid, perbenzoic acid derivatives, trifluoroacetic acid or peroxyphthalic acid, peroxymaleic acid, peroxypropionic acid; the oxidizing agent is in particular peracetic acid;
  • organic peroxides such as dioxirane, Ci-C 6 alkyl peroxides, benzoyl peroxide, peroxo(CrC 6 )alkyl carboxylates, bis(tri)(CrC 6 )alkylsilyl peroxides, such as bis(trimethylsilyl) peroxide, Ci-C 6 alkyl peroxydicarbonates and sodium nonanoyloxybenzenesulfonate, as described in the documents WO 1995000625 and US 4 412 934;
  • oxidizing anions such as nitrites, nitrates, hypochlorites, hypobromites, hypoiodites, chlorites, bromites, iodites, chlorates, bromates, iodates or periodates;
  • the oxidizing agent is chosen in particular from alkali metal hypochlorite or periodate, such as sodium hypochlorite or sodium periodate;
  • a6) stable N-oxy (NO ) radicals such as the 2,2,6,6-tetra(Ci-C 6 )alkylpiperidino-oxy radical, 2,2,6,6-tetra(Ci-C 6 )alkylmorpholino-oxy radical, Fremy nitrosodisulfonate salts or morpholine N-oxide; in particular, the oxidizing agent is chosen from the 2,2,6,6-tetramethylpiperidinyloxy radical; a7) hypervalent iodine derivatives, such as iodotriacetate, iodosobenzene, iodobenzenetriacetate, iodoperbenzoic acid derivatives, periodinanes, and alkyl and benzoyl hypoiodites.
  • NO stable N-oxy
  • the oxidizing agent is chosen from iodotriacetate, iodosobenzene, iodobenzenetriacetate, iodoperbenzoic acid and Dess-Martin periodinane;
  • the optional supports for these oxidizing agents a1 ) to a8) may be chosen from silica, alumina, charcoal and charged or neutral polymers;
  • polymeric complexes which can release hydrogen peroxide, such as polyvinylpyrrolidone/H 2 02, in particular in the form of powders, and the other polymeric complexes described in US 5 008 093, US 3 376 1 10 and US 5 183
  • oxidases which produce hydrogen peroxide in the presence of a suitable substrate (for example glucose in the case of glucose oxidase or uric acid with uricase);
  • metal peroxides which generate hydrogen peroxide in water, such as calcium peroxide or magnesium peroxide;
  • the chemical oxidizing agent(s) is (are) chosen from a9) hydrogen peroxide or hydrogen peroxide-generating systems, more particularly H 2 0 2 .
  • the process uses one or more system(s) which generate hydrogen peroxide chosen from a9-1 ) urea peroxide; a9-2) polymeric complexes which can release hydrogen peroxide chosen from polyvinylpyrrolidone/H 2 0 2 ; a9-3) oxidases; a9-5) perborates and a9-6) percarbonates.
  • the composition comprising the chemical oxidizing agent(s), in particular a) the hydrogen peroxide or the hydrogen peroxide generator(s) can also include various adjuvants conventionally used in hair dyeing compositions and as defined hereinbelow at the point entitled "cosmetic composition".
  • the chemical oxidizing agent(s), in particular the hydrogen peroxide or the hydrogen peroxide-generating system(s) used preferably represent(s) from 0.001 % to 12% by weight, expressed as hydrogen peroxide, relative to the total weight of composition ii) containing them, and even more preferentially from 0.2% to 4% by weight, better still from 0.5% to 3% by weight.
  • the oxidizing composition ii) of the invention also comprises b) at least one fatty substance.
  • fatty substance is intended to mean an organic compound that is insoluble in water at ordinary ambient temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1 % and even more preferentially less than 0.1 %). They bear in their structure at least one hydrocarbon-based chain including at least 6 carbon atoms or a sequence of at least two siloxane groups.
  • the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, ethanol, benzene, liquid petroleum jelly or decamethylcyclopentasiloxane.
  • fatty substances are neither polyoxyethylenated nor polyglycerolated. They are different from fatty acids since salified fatty acids constitute soaps which are generally soluble in aqueous media.
  • the fatty substances are in particular chosen from C 6 -Ci 6 hydrocarbons or hydrocarbons comprising more than 16 carbon atoms and in particular alkanes, oils of animal origin, oils of plant origin, glycerides or fluoro oils of synthetic origin, fatty alcohols, fatty acid and/or fatty alcohol esters, non-silicone waxes, and silicones.
  • the fatty alcohols, fatty esters and fatty acids more particularly contain one or more linear or branched, saturated or unsaturated hydrocarbon-based groups comprising 6 to 30 carbon atoms, which are optionally substituted, in particular, with one or more (in particular 1 to 4) hydroxyl groups. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • C 6 -Ci 6 alkanes they are linear or branched, and possibly cyclic. Examples that may be mentioned include hexane, dodecane and isoparaffins such as isohexadecane and isodecane.
  • the linear or branched hydrocarbons containing more than 16 carbon atoms may be chosen from liquid paraffins, petroleum jelly, liquid petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam®.
  • the fatty substance(s) used in the process of the invention is (are) chosen from volatile linear alkanes.
  • one or more volatile linear alkane(s) is intended to mean, without preference, “one or more volatile linear alkane oil(s)”.
  • a volatile linear alkane that is suitable for the invention is liquid at ambient temperature (about 25°C) and at atmospheric pressure (101 325 Pa or 760 mmHg).
  • volatile linear alkane that is suitable for the invention is intended to mean a linear alkane that can evaporate on contact with the skin in less than one hour, at ambient temperature (25°C) and atmospheric pressure (101 325 Pa), which is liquid at ambient temperature, in particular having an evaporation rate ranging from 0.01 to 15 mg/cm 2 /minute, at ambient temperature (25°C) and atmospheric pressure (101 325 Pa).
  • the volatile linear alkanes that are suitable for the invention have an evaporation rate ranging from 0.01 to 3.5 mg/cm 2 /minute and better still from 0.01 to 1 .5 mg/cm 2 /minute, at ambient temperature (25°C) and atmospheric pressure (101 325 Pa).
  • the volatile linear alkanes that are suitable for the invention have an evaporation rate ranging from 0.01 to 0.8 mg/cm 2 /minute, preferentially from 0.01 to 0.3 mg/cm 2 /minute and even more preferentially from 0.01 to 0.12 mg/cm 2 /minute, at ambient temperature (25°C) and atmospheric pressure (101 325 Pa).
  • the evaporation rate of a volatile alkane in accordance with the invention may in particular be evaluated by means of the protocol described in WO 06/013 413, and more particularly by means of the protocol described below.
  • the volatile hydrocarbon-based solvent is allowed to evaporate freely, without stirring it, with ventilation provided by means of a fan (Papst-Motoren, reference 8550 N, rotating at 2700 rpm) placed in a vertical position above the crystallizing dish containing the volatile hydrocarbon-based solvent, the blades being directed towards the crystallizing dish, 20 cm away from the bottom of the dish.
  • a fan Paperst-Motoren, reference 8550 N, rotating at 2700 rpm
  • the weight of volatile hydrocarbon-based solvent remaining in the crystallizing dish is measured at regular time intervals.
  • the evaporation profile of the solvent is then obtained by plotting the curve of the amount of product evaporated (in mg/cm 2 ) as a function of the time (in min).
  • the evaporation rate is then calculated, which corresponds to the tangent to the origin of the curve obtained.
  • the evaporation rates are expressed in mg of volatile solvent evaporated per unit of surface area (cm 2 ) and per unit of time (minutes).
  • the volatile linear alkanes that are suitable for the invention have a non-zero vapour pressure (also known as saturation vapour pressure), at ambient temperature, in particular a vapour pressure ranging from 0.3 Pa to 6000 Pa.
  • a non-zero vapour pressure also known as saturation vapour pressure
  • the volatile linear alkanes that are suitable for the invention have a vapour pressure ranging from 0.3 to 2000 Pa and better still from 0.3 to 1000 Pa, at ambient temperature (25°C).
  • the volatile linear alkanes that are suitable for the invention have a vapour pressure ranging from 0.4 to 600 Pa, preferentially from 1 to 200 Pa and even more preferentially from 3 to 60 Pa, at ambient temperature (25°C).
  • a volatile linear alkane that is suitable for use in the invention may have a flash point that is within the range from 30 to 120°C and more particularly from 40 to 100°C.
  • the flash point is in particular measured according to standard ISO 3679.
  • the volatile linear alkanes that are suitable for the invention may be linear alkanes comprising from 7 to 15 carbon atoms, preferably from 8 to 14 carbon atoms and better still from 9 to 14 carbon atoms.
  • the volatile linear alkanes that are suitable for the invention may be linear alkanes comprising from 10 to 14 carbon atoms and even more preferentially from 1 1 to 14 carbon atoms.
  • a volatile linear alkane that is suitable for the invention may advantageously be of plant origin.
  • the volatile linear alkane or the mixture of volatile linear alkanes present in the composition according to the invention comprises at least one 14 C (carbon-14) carbon isotope.
  • the 14 C isotope may be present in a 14 C/ 12 C isotope ratio by number (or 14 C/ 12 C ratio) of greater than or equal to 1 x10 "16 , preferably greater than or equal to 1 x10 "15 , more preferably greater than or equal to 7.5 ⁇ 10 "14 and better still greater than or equal to 1 .5x10 "13 .
  • the 14 C/ 12 C ratio ranges from 6x10 "13 to 1.2x10 "12 .
  • the amount of 14 C isotopes in the volatile linear alkane or the mixture of volatile linear alkanes may be determined via methods known to those skilled in the art such as the Libby counting method, liquid scintillation spectrometry or else accelerator mass spectrometry.
  • Such an alkane may be obtained, directly or in several steps, from a plant raw material, such as an oil, a butter, a wax, etc.
  • alkanes that are suitable for the invention, mention may be made of the alkanes described in patent applications WO 2007/068 371 and WO 2008/155 059. These alkanes are obtained from fatty alcohols, which are themselves obtained from copra oil or palm oil.
  • linear alkanes that are suitable for the invention, mention may be made of n-heptane (C7), n-octane (C8), n-nonane (C9), n-decane (C10), n-undecane (C1 1 ), n-dodecane (C12), n-tridecane (C13), n-tetradecane (C14), and n-pentadecane (C15) and mixtures thereof.
  • the volatile linear alkane is chosen from n-nonane, n-undecane, n-dodecane, n-tridecane and n- tetradecane, and mixtures thereof.
  • n-dodecane (C12) and n-tetradecane (C14) sold, respectively, under the references Parafol 12-97 and Parafol 14-97 by Sasol, and also mixtures thereof.
  • One embodiment consists in using only one volatile linear alkane.
  • a mixture of at least two different volatile linear alkanes differing from each other by a carbon number n of at least 1 , in particular differing from each other by a carbon number of 1 or 2, may be used.
  • a mixture of at least two different volatile linear alkanes comprising from 10 to 14 carbon atoms and differing from each other by a carbon number of at least 1 .
  • a mixture of two different volatile linear alkanes comprising from 10 to 14 carbon atoms and differing from each other by a carbon number of at least 2, is used.
  • a mixture of at least two different volatile linear alkanes comprising from 10 to 14 carbon atoms and differing from each other by a carbon number of at least 2, and in particular a mixture of volatile linear alkanes C1 1/C13 or a mixture of volatile linear alkanes C12/C14, is used.
  • mixtures combining more than two volatile linear alkanes according to the invention for instance a mixture of at least three different volatile linear alkanes comprising from 7 to 15 carbon atoms and differing from each other by a carbon number of at least 1 , may be used in the invention.
  • said two volatile linear alkanes preferably represent more than 95% and better still more than 99% by weight of the mixture.
  • the volatile linear alkane having the smallest carbon number is predominant in the mixture.
  • a mixture of volatile linear alkanes in which the volatile linear alkane having the largest carbon number is predominant in the mixture is used.
  • said mixture of volatile linear alkanes may also contain:
  • volatile linear alkanes that are suitable for the invention may be used in the form of an n-undecane/n-tridecane mixture.
  • the mixture of alkanes is an n-undecane/n- tridecane mixture.
  • such a mixture may be obtained according to Example 1 or Example 2 of application WO 2008/155 059.
  • the n-dodecane sold under the reference Parafol 12-97 by Sasol is used.
  • the n-tetradecane sold under the reference Parafol 14-97 by Sasol is used.
  • n-dodecane and n-tetradecane is used.
  • liquid fatty acid triglycerides comprising from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, maize oil, soybean oil, marrow oil, grapeseed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, jojoba oil, shea butter oil and caprylic/capric acid triglycerides, for instance those sold by Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by Dynamit Nobel.
  • Fluoro oils that may be mentioned include perfluoromethylcyclopentane and perfluoro-1 ,3-dimethylcyclohexane, sold under the names Flutec® PC1 and Flutec® PC3 by BNFL Fluorochemicals; perfluoro-1 ,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050® and PF 5060® by 3M, or alternatively bromoperfluorooctyl sold under the name Foralkyl® by Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethyl perfluoromorpholine sold under the name PF 5052® by 3M.
  • the fatty alcohols that may be used in the cosmetic compositions of the invention are saturated or unsaturated, and linear or branched, and comprise from 6 to 30 carbon atoms and more particularly from 8 to 30 carbon atoms. Mention may be made, for example, of cetyl alcohol, stearyl alcohol and a mixture thereof (cetearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol.
  • the wax(es) that may be used in the cosmetic compositions of the invention are chosen especially from carnauba wax, candelilla wax, esparto grass wax, paraffin wax, ozokerite, plant waxes, for instance olive tree wax, rice wax, hydrogenated jojoba wax or the absolute waxes of flowers such as the essential wax of blackcurrant blossom sold by Bertin (France), animal waxes, for instance beeswaxes, or modified beeswaxes (cerabellina); other waxes or waxy starting materials that may be used according to the invention are especially marine waxes such as the product sold by Sophim under the reference M82, and polyethylene waxes or polyolefin waxes in general.
  • esters of saturated or unsaturated, linear or branched Ci-C 2 6 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched Ci-C 2 6 aliphatic mono- or polyalcohols the total carbon number of the esters more particularly being greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; Ci 2 -Ci 5 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methyl acetyl ricinoleate; myristyl stea
  • esters of C4-C22 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols and esters of mono-, di- or tricarboxylic acids and of C 2 -C 2 6 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • esters mentioned above it is preferred to use ethyl, isopropyl, myristyl, cetyl or stearyl palmitates, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate or cetyl octanoate.
  • alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stea
  • composition may also comprise, as fatty ester, sugar esters and diesters of C 6 - C 30 and preferably C12-C22 fatty acids.
  • sugar esters and diesters of C 6 - C 30 and preferably C12-C22 fatty acids.
  • sugar esters are intended to mean oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and that comprise at least 4 carbon atoms.
  • sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar and fatty acid esters may be chosen in particular from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 3 o and preferably C12-C22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • esters according to this variant may also be chosen from mono-, di-, tri- and tetraesters, polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters.
  • monoesters and diesters and especially sucrose, glucose or methylglucose monooleate or dioleate, stearate, behenate, oleopalmitate, linoleate, linolenate or oleostearate.
  • esters or mixtures of esters of sugar and of fatty acid examples include:
  • Crodesta respectively denoting sucrose palmitate/stearates formed from 73% monoester and 27% diester and triester, from 61 % monoester and 39% diester, triester and tetraester, from 52% monoester and 48% diester, triester and tetraester, from 45% monoester and 55% diester, triester and tetraester, from 39% monoester and 61 % diester, triester and tetraester, and sucrose monolaurate; - the products sold under the name Ryoto Sugar Esters, for example referenced B370 and corresponding to sucrose behenate formed from 20% monoester and 80% diester- tri ester-polyester;
  • sucrose mono-dipalmito-stearate sold by Goldschmidt under the name Tegosoft® PSE.
  • the silicones that may be used in the cosmetic composition (A) according to the present invention are volatile or non-volatile, cyclic, linear or branched silicones, which are unmodified or modified with organic groups, having a viscosity from 5x10 "6 to 2.5 m 2 /s at 25°C, and preferably 1 x10 "5 to 1 m 2 /s.
  • the silicones that may be used in accordance with the invention may be in the form of oils, waxes, resins or gums, preferably silicone oils.
  • the silicone is chosen from polydialkylsiloxanes, especially polydimethylsiloxanes (PDMSs), and organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • PDMSs polydimethylsiloxanes
  • organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • Organopolysiloxanes are defined in greater detail in Walter Noll's Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • the silicones are more particularly chosen from those with a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes containing from 3 to 7 and preferably 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes containing from 3 to 7 and preferably 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union Carbide, and Silbione® 70045 V5 by Rhodia, and mixtures thereof.
  • Non-volatile polydialkylsiloxanes are preferably used.
  • silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes bearing trimethylsilyl end groups.
  • the viscosity of the silicones is measured at 25°C according to ASTM Standard 445 Appendix C.
  • oils of the 200 series from Dow Corning, such as DC200 with a viscosity of 60
  • CTFA dimethiconol
  • the silicone gums that may be used in accordance with the invention are especially polydialkylsiloxanes and preferably polydimethylsiloxanes with high number-average molecular weights of between 200 000 and 1 000 000, used alone or as a mixture in a solvent.
  • This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.
  • Products that may be used more particularly in accordance with the invention are mixtures such as:
  • CTFA hydroxy-terminated polydimethylsiloxane or dimethiconol
  • CFA cyclic polydimethylsiloxane
  • the product SF 1236 is the mixture of a gum SE 30 defined above with a viscosity of 20 m 2 /s and of an oil SF 96 with a viscosity of 5x10 "6 m 2 /s. This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96.
  • organopolysiloxane resins that may be used in accordance with the invention are crosslinked siloxane systems containing the following units:
  • R represents an alkyl containing 1 to 16 carbon atoms.
  • R denotes a C C 4 lower alkyl group, more particularly methyl.
  • organomodified silicones that may be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
  • the organomodified silicones may be polydiarylsiloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized by the organofunctional groups mentioned previously.
  • the polyalkylarylsiloxanes are particularly chosen from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity ranging from 1 ⁇ 10 "5 to 5* 10 "2 m 2 /s at 25°C.
  • oils of the SF series from General Electric such as SF 1023, SF 1 154, SF 1250 and SF 1265.
  • organomodified silicones mention may be made of polyorganosiloxanes including:
  • C 6 -C 24 alkyl groups such as the products known as dimethicone copolyol sold by Dow Corning under the name DC 1248 or the oils Silwet® L 722, L 7500, L 77 and L 71 1 by Union Carbide, and the (Ci 2 )alkylmethicone copolyol sold by Dow Corning under the name Q2 5200; - substituted or unsubstituted amino groups, such as the products sold under the names GP 4 Silicone Fluid and GP 7100 by Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by Dow Corning.
  • the substituted amino groups are, in particular, Ci-C 4 aminoalkyl groups;
  • the fatty substances do not comprise any C 2 -C 3 oxyalkylene units or any glycerol units.
  • the fatty substances are not fatty acids and in particular salified fatty acids or soaps which are water-soluble compounds.
  • the fatty substances are advantageously chosen from C 6 -Ci 6 hydrocarbons or hydrocarbons comprising more than 16 carbon atoms, and in particular alkanes, oils of plant origin, fatty alcohols, fatty acid and/or fatty alcohol esters, and silicones, or mixtures thereof.
  • the fatty substance is an oil (a compound that is liquid at a temperature of 25°C and at atmospheric pressure).
  • the liquid fatty substance is preferably chosen from liquid petroleum jelly, C 6 -Ci 6 alkanes, volatile linear alkanes, polydecenes, liquid fatty acid and/or fatty alcohol esters, and liquid fatty alcohols, or mixtures thereof.
  • the fatty substance is chosen from oil, liquid esters of a fatty acid and/or of a fatty alcohol, liquid fatty alcohols, and mixtures thereof.
  • the fatty substances are chosen from fatty substances that are solid at a temperature of 25°C and at atmospheric pressure.
  • the solid fatty substance is preferably chosen from solid esters of a fatty acid and/or of a fatty alcohol, solid fatty alcohols, or mixtures thereof.
  • the oxidizing composition ii) comprises one or more fatty substances chosen from esters of a fatty acid and/or of a fatty alcohol, and fatty alcohols, even better still from solid esters of a fatty acid and/or of a fatty alcohol, and solid fatty alcohols.
  • the process according to the invention uses one or more fatty substances in the oxidizing composition ii), chosen from esters of a fatty acid and of fatty alcohols, fatty alcohols and silicones; preferably chosen from esters of saturated or unsaturated, linear or branched Ci-C 2 6 aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched Ci-C 2 6 aliphatic monoalcohols or polyalcohols, the total number of carbons of the esters being more particularly greater than or equal to 10; esters of C 4 -C 2 2 dicarboxylic or tricarboxylic acids and of C1-C22 alcohols, and esters of C2-C26 monocarboxylic, dicarboxylic or tricarboxylic acids and of C 2 -C 2 6 di-, tri-, tetra- or pentahydroxy alcohols; esters and diesters of sugars of linear or branched, saturated or unsaturated C 6 -C
  • the oxidizing composition ii) may have a total content of solid fatty substance ranging from 0.1 % to 30% by weight, preferably ranging from 1 % to 20% by weight relative to the total weight of composition ii).
  • the oxidizing composition has a total content of fatty substance of less than or equal to 10% by weight, preferably ranging from 0.1 % to 10% by weight, even more preferentially ranging from 0.2% to 5% by weight, relative to the total weight of the oxidizing composition.
  • the oxidizing composition has a content of liquid fatty substances of less than equal to 10% by weight, preferably less than or equal to 5% by weight.
  • composition comprising b) the fatty substance(s) may also contain various adjuvants conventionally used in hair dyeing compositions and as defined hereinafter under the heading "cosmetic composition".
  • Cosmetic composition b) Surfactant
  • the oxidizing composition ii) of the invention also comprises c) at least one non-ionic or cationic surfactant or mixture thereof.
  • the oxidizing composition of the invention contains at least one non-ionic surfactant.
  • non-ionic surfactants include fatty alcohols, a-diols and alkylphenols, these three types of compound being polyethoxylated, polypropoxylated and/or polyglycerolated and containing a fatty chain comprising, for example, 8 to 22 carbon atoms, the number of ethylene oxide or propylene oxide groups possibly ranging especially from 2 to 50 and the number of glycerol groups possibly ranging especially from 2 to 30.
  • polyethoxylated fatty amides preferably having from 2 to 30 mol of ethylene oxide, polyglycerolated fatty amides containing on average
  • the non-ionic surfactant(s) is (are) chosen from:
  • fatty chain is intended to mean a linear or branched, saturated or unsaturated hydrocarbon-based chain comprising from 6 to 30 carbon atoms and preferably from 8 to 24 carbon atoms.
  • alkylpolyglycosides these compounds are well known and may be represented more particularly by the following general formula:
  • ⁇ Ri represents a linear or branched alkyl and/or alkenyl radical comprising from about 8 to 24 carbon atoms, or an alkylphenyl radical of which the linear or branched alkyl radical comprises from 8 to 24 carbon atoms;
  • R 2 represents an alkylene radical comprising from about 2 to 4 carbon atoms
  • G represents a sugar unit comprising from 5 to 6 carbon atoms
  • ⁇ t is an integer between 0 and 10 inclusive, preferably between 0 and 4 and in particular between 0 and 4;
  • Preferred alkylpolyglycosides according to the present invention are compounds of formula (XIV) in which Ri more particularly denotes a linear or branched, saturated or unsaturated alkyl radical comprising from 8 to 18 carbon atoms, t denotes a value ranging from 0 to 3 and even more particularly equal to 0, and G may denote glucose, fructose or galactose, preferably glucose.
  • the degree of polymerization i.e. the value of v in formula (XXI), may range from 1 to 15 and preferably from 1 to 4.
  • the average degree of polymerization is more particularly between 1 and 2 and even more preferentially from 1 .1 to 1 .5.
  • glycoside bonds between the sugar units are of 1 -6 or 1 -4 type and preferably of 1 - 4 type.
  • Compounds of formula (XIV) are in particular represented by the products sold by Cognis under the name Plantaren® (600 CS/U, 1200 and 2000) or Plantacare® (818, 1200 and 2000). It is also possible to use the products sold by SEPPIC under the names Triton CG 1 10 (or Oramix CG 1 10) and Triton CG 312 (or Oramix® NS 10), the products sold by BASF under the name Lutensol GD 70 or those sold by Chem Y under the name AG10 LK.
  • the mono- or polyglycerolated surfactants preferably comprise on average from 1 to 30 glycerol groups, more particularly from 1 to 10 and in particular from 1 .5 to 5 glycerol groups.
  • the monoglycerolated or polyglycerolated surfactants are preferably chosen from the compounds of the following formulae: RO[CH 2 CH(CH 2 OH)0] m H, RO[CH 2 CH(OH)CH 2 0] m H or RO[CH(CH 2 OH)CH 2 0] m H; in which formulae:
  • R represents a linear or branched, saturated or unsaturated, hydrocarbon-based radical comprising from 8 to 40 carbon atoms and preferably from 10 to 30 carbon atoms; and m is a number between 1 and 30, preferably between 1 and 10, more particularly from 1 .5 to 6.
  • R may optionally comprise heteroatoms, for instance oxygen and nitrogen.
  • R may optionally comprise one or more hydroxyl and/or ether and/or amide groups.
  • R preferably denotes optionally mono- or polyhydroxylated Ci 0 -C 2 o alkyl and/or alkenyl radicals.
  • Use may be made, for example, of the polyglycerolated (3.5 mol) hydroxylauryl ether sold under the name Chimexane® NF from Chimex.
  • the (poly)ethoxylated fatty alcohols which are suitable for implementing the invention are selected more particularly from alcohols containing from 8 to 30 carbon atoms, and preferably from 12 to 22 carbon atoms.
  • the (poly)ethoxylated fatty alcohols more particularly contain one or more linear or branched, saturated or unsaturated hydrocarbon-based groups, comprising 8 to 30 carbon atoms, which are optionally substituted, in particular with one or more (in particular 1 to 4) hydroxyl groups. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • the (poly)ethoxylated fatty alcohol(s) preferably have the following formula: with
  • R a representing a linear or branched Ci-C 40 alkyl or linear or branched C 2 -C 3 o alkenyl (preferentially C 8 -C 3 o alkyl) group and
  • - n representing an integer between 1 and 200 inclusive, preferentially between 2 and 50 and more particularly between 2 and 30 inclusive, such as 20.
  • the (poly)ethoxylated fatty alcohols are more particularly fatty alcohols comprising from 8 to 22 carbon atoms and oxyethylenated with 1 to 30 mol of ethylene oxide (1 to 30 EO).
  • fatty alcohols comprising from 8 to 22 carbon atoms and oxyethylenated with 1 to 30 mol of ethylene oxide (1 to 30 EO).
  • non-ionic surfactants use is preferably made of C 6 -C 24 alkyl polyglucosides and (poly)ethoxylated fatty alcohols, and and use is more particularly made of C 8 -Ci 6 alkyl polyglucosides.
  • the amount of non-ionic surfactants preferably ranges from 0.5% to 25% by weight, in particular from 1 % to 20% by weight and more particularly from 2% to 10% by weight relative to the total weight of the composition of the invention.
  • the composition comprises one or more cationic surfactants. Mention may be made, for example, of optionally polyoxyalkylenated primary, secondary or tertiary fatty amine salts, quaternary ammonium salts, and mixtures thereof.
  • quaternary ammonium salts examples include:
  • R 8 to Rn groups which may be identical or different, each represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the R 8 to Rn groups comprising from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms.
  • the aliphatic groups may comprise heteroatoms such as, in particular, oxygen, nitrogen, sulfur and halogens.
  • the aliphatic groups are chosen, for example, from C1-C30 alkyl, C1-C30 alkoxy, polyoxy(C 2 -C 6 )alkylene, C1-C30 alkylamide, (Ci 2 -C22)alkylamido(C2-C 6 )alkyl, (C12- C 2 2)alkylacetate and Ci-C 30 hydroxyalkyl,
  • X " is an anionic counterion chosen from halides, phosphates, acetates, lactates, (CrC 4 )alkyl sulfates, and (Ci-C 4 )alkyl- or (d- C 4 )alkylarylsulfonates.
  • quaternary ammonium salts of formula (XV) preference is given firstly to tetraalkylammonium chlorides, for instance dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, benzyldimethylstearylammonium chloride, or else, secondly, distearoylethylhydroxyethylmethylammonium methosulfate, dipalmitoylethylhydroxyethylammonium methosulfate or distearoylethylhydroxyethylammonium methosulfate, or else, lastly, palmitylamidopropyltrimethylammonium chloride or stearamidopropyldimethyl(myristyl acetate)ammonium chloride,
  • Ri 2 represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow;
  • Ri 3 represents a hydrogen atom, a C C 4 alkyl group or an alkenyl or alkyl group comprising from 8 to 30 carbon atoms;
  • Ri 4 represents a C C 4 alkyl group
  • Ri 5 represents a hydrogen atom or a C C 4 alkyl group
  • X " represents an anionic counterion, chosen from halides, phosphates, acetates, lactates, (Ci-C 4 )alkyl sulfates, (Ci-C 4 )alkyl- or (d- C 4 )alkylarylsulfonates.
  • Ri 2 and Ri 3 preferably denote a mixture of alkenyl or alkyl groups containing from 12 to 21 carbon atoms, for example fatty acid derivatives of tallow, R 14 denotes a methyl group, Ri 5 denotes a hydrogen atom.
  • R 14 denotes a methyl group
  • Ri 5 denotes a hydrogen atom.
  • Ri 6 denotes an alkyl group comprising approximately from 16 to 30 carbon atoms, which is optionally hydroxylated and/or interrupted by one or more oxygen atoms;
  • Ri 7 is chosen from hydrogen, an alkyl group comprising from 1 to 4 carbon atoms or a group -(CH 2 )3-N + (R 16a )(R 17 a)(Ri8a); Rie a , i 7a , Ris a , Rie, R19, R20 and R 21 , which may be identical or different, are chosen from hydrogen and an alkyl group comprising from 1 to 4 carbon atoms, and
  • X " represents an anionic counterion chosen from halides, acetates, phosphates, nitrates, (Ci-C 4 )alkyl sulfates, (Ci-C 4 )alkyl- or (CrC 4 )alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate.
  • Such compounds are, for example, Finquat CT-P, sold by Finetex (Quaternium 89), and Finquat CT, sold by Finetex (Quaternium 75);
  • R 2 2 is chosen from CrC 6 alkyl groups and CrC 6 hydroxyalkyi or dihydroxyalkyi groups,
  • ⁇ R23 is chosen from:
  • ⁇ R25 is chosen from:
  • Ci-C 6 hydrocarbon-based groups R 29 - linear or branched, saturated or unsaturated Ci-C 6 hydrocarbon-based groups R 29 ,
  • R24, R26 and R 2 8 which are identical or different, are chosen from saturated or unsaturated and linear or branched C7-C21 hydrocarbon groups;
  • ⁇ r, s and t which may be identical or different, are integers of from 2 to 6,
  • ⁇ y is an integer having a value from 1 to 10,
  • ⁇ x and z which may be identical or different, are integers from 0 to 10,
  • ⁇ X " represents an organic or inorganic anionic counterion
  • the alkyl groups R 22 may be linear or branched, and more particularly linear.
  • R 22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.
  • the sum x + y + z is from 1 to 10.
  • R 23 is a hydrocarbon-based group R 27 , it may be long and contain from 12 to 22 carbon atoms, or may be short and contain from 1 to 3 carbon atoms.
  • R 25 is a hydrocarbon-based group R 29 , it preferably contains 1 to 3 carbon atoms.
  • R 24 , R26 and R 2 e which are identical or different, are chosen from saturated or unsaturated and linear or branched Cn-C 2 i hydrocarbon-based groups, and more particularly from saturated or unsaturated and linear or branched Cn- C21 alkyl and alkenyl groups.
  • x and z which may be identical or different, have the value 0 or 1.
  • y is equal to 1 .
  • r, s and t which may be identical or different, are equal to 2 or 3, and even more particularly are equal to 2.
  • the anionic counterion X " is preferably a halide, preferably chloride, bromide or iodide; a (C 1 -C 4 )alkyl sulfate or a (CrC 4 )alkyl- or (Ci-C 4 )alkylarylsulfonate.
  • a halide preferably chloride, bromide or iodide
  • a (C 1 -C 4 )alkyl sulfate or a (CrC 4 )alkyl- or (Ci-C 4 )alkylarylsulfonate preferably a halide, preferably chloride, bromide or iodide
  • a (C 1 -C 4 )alkyl sulfate or a (CrC 4 )alkyl- or (Ci-C 4 )alkylarylsulfonate preferably a halide, preferably chloride, bromide or io
  • the anionic counterion X " is even more particularly chloride, methyl sulfate or ethyl sulfate.
  • R22 denotes a methyl or ethyl group
  • - R23 is chosen from:
  • - R25 is chosen from:
  • R 24 , R26 and R 2 e which may be identical or different, are chosen from linear or branched, saturated or unsaturated C13-C17 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C13-C17 alkyl and alkenyl groups.
  • hydrocarbon-based radicals are linear.
  • acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a plant oil such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
  • This esterification is followed by a quaternization by means of an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • Such compounds are sold, for example, under the names Dehyquart ® by Henkel, Stepanquat ® by Stepan, Noxamium ® by CECA or Rewoquat ® WE 18 by Rewo-Witco.
  • composition according to the invention may contain, for example, a mixture of quaternary ammonium monoester, diester and triester salts with a weight majority of diester salts.
  • ammonium salts containing at least one ester function that are described in patents US-A-4 874 554 and US-A-4 137 180.
  • Use may be made of behenoylhydroxypropyltrimethylammonium chloride sold by Kao under the name Quatarmin BTC 131.
  • ammonium salts comprising at least one ester functional group comprise two ester functional groups.
  • cationic surfactants that may be present in the composition according to the invention, it is more particularly preferred to choose cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxyethylmethylammonium salts, and mixtures thereof, and more particularly behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, and dipalmitoylethylhydroxyethylammonium methosulfate, and mixtures thereof.
  • the composition of the invention contains at least one cationic surfactant.
  • the surfactant(s) are preferably present in the composition ii) in an amount ranging from 0.01 % to 20% by weight, preferably from 0.05% to 10% by weight and better still from 0.1 % to 5% and particularly from 0.5% to 2% relative to the total weight of the oxidizing composition.
  • the composition comprising c) the surfactant(s) may also contain various adjuvants conventionally used in hair dyeing compositions and as defined hereinafter under the heading "cosmetic composition".
  • the dyeing process according to the present invention also uses in its dyeing composition i) one or more metal catalysts.
  • Metal catalysts are compounds that comprise one or more metals in their structure.
  • the metals are chosen from transition metals and rare-earth metals, and alloys thereof.
  • the metals are chosen from transition metals and rare-earth metals.
  • transition metals mention may in particular be made of manganese, iron, cobalt, copper, zinc, platinum, nickel, titanium, silver, zirconium, chromium, molybdenum, tungsten, gold and vanadium, and among said metals, most particularly manganese.
  • rare-earth metals mention may particularly be made of cerium.
  • the metal catalysts are especially catalysts based on transition metals and on rare-earth metals, and more particularly manganese-based, vanadium-based or cerium- based catalysts.
  • the metal catalysts used may be chosen from metal salts, metal oxides and metal complexes, and mixtures thereof.
  • metal complexes is intended to mean systems in which the metal ion, i.e. the central atom, is bonded to one or more electron donors, called ligands, via chemical bonds. Examples that may be mentioned include porphyrins and phthalocyanines, which are especially cationic.
  • the metal catalysts used in the dyeing process are chosen from metal salts.
  • metal salts is intended to mean salts derived from the action of an acid on a metal.
  • the metal catalysts used in the dyeing process are chosen from transition metal salts, such as manganese salts, and rare-earth metal salts, such as cerium salts, and also mixtures thereof.
  • the metal salts may be mineral or organic salts.
  • the metal salts are mineral and may be chosen from halides, carbonates, sulfates and phosphates, in particular optionally hydrated halides.
  • the metal salts are in oxidation state II and bear two (poly)hydroxy acid-based ligands.
  • (poly)hydroxy acid is intended to mean any carboxylic acid which comprises a hydrocarbon-based chain which is linear or branched, and saturated or unsaturated, preferably saturated and/or linear, comprising from 1 to 10 carbon atoms and from 1 to 9 hydroxyl groups, and comprising from 1 to 4 carboxylic groups -C(0)-OH, at least one of said -C(0)-OH functions of which is in the carboxylate form -C(0)-0 " complexed with the metal atom, preferably Mn(ll). More particularly, the metal salt is complexed with two carboxylate groups such as that of formula (I): and also the solvates thereof, such as the hydrates, and enantiomers thereof,
  • -M represents a metal (II) or metal 2+ in oxidation state 2
  • the metal catalysts are particularly chosen from organic acid salts of transition metals, especially of manganese, and mineral salts of rare-earth metals, especially of cerium.
  • the manganese is not a manganese oxide, but a manganese salt.
  • the organic metal salts may be more particularly chosen from organic acid salts such as citrates, lactates, glycolates, gluconates, acetates, propionates, fumarates, oxalates and tartrates, especially gluconates.
  • the metal catalysts are chosen from manganese gluconate and cerium chloride heptahydrate, in particular manganese gluconate.
  • the metal catalyst(s) are chosen from the compounds of formula (I) and more particularly represent(s) manganese gluconate.
  • the metal catalysts may be present in a content ranging from 0.001 % to 10% by weight, preferably in a content ranging from 0.001 % to 1 % by weight, better still ranging from 0.01 % to 0.5% by weight relative to the total weight of the dyeing composition.
  • the basifying agent is the basifying agent
  • the dyeing process uses one or more basifying agents.
  • the basifying agent(s) is (are) in the dyeing composition i) with the natural dye(s) as defined previously.
  • basifying agents are bases that can increase the pH of the composition(s) in which they are present.
  • the basifying agent is a Bransted, Lowry or Lewis base. It may be mineral or organic.
  • said agent is chosen from i) (bi)carbonates, ii) aqueous ammonia, iii) alkanolamines such as monoethanolamine, diethanolamine, triethanolamine and derivatives thereof, iv) oxyethylenated and/or oxypropylenated ethylenediamines, v) mineral or organic hydroxides, vi) alkali metal silicates such as sodium metasilicates, vii), amino acids, preferably basic amino acids such as arginine, lysine, ornithine, citrulline and histidine, and viii) the compounds of formula (XIX) below: a ⁇ b
  • W is a (CrC 8 )alkylene divalent radical optionally substituted with at least one hydroxyl group or at least one (CrC 4 )alkyl radical and/or optionally interrupted with at least one heteroatom such as oxygen or sulfur or with a group -N(R e )-;
  • R a , R b , R c , R d and R e which may be identical or different, represent a hydrogen atom or a (C C 4 )alkyl or hydroxy(CrC 4 )alkyl radical, preferentially W represents a propylene radical.
  • the mineral or organic hydroxides are preferably chosen from a) hydroxides of an alkali metal, b) hydroxides of an alkaline-earth metal, for instance sodium hydroxide or potassium hydroxide, c) hydroxides of a transition metal, such as hydroxides of metals from groups III, IV, V and VI, d) hydroxides of lanthanides or actinides, quaternary ammonium hydroxides and guanidinium hydroxide.
  • the hydroxide may be formed in situ, for instance guanidine hydroxide, formed by reacting calcium hydroxide with guanidine carbonate.
  • bicarbonates also known as hydrogen carbonates, of the following formulae:
  • R' + , HC0 3 " with R' representing a hydrogen atom, an alkali metal, an ammonium group R" 4 N + - or a phosphonium group R" 4 P + - where R", which are identical or different, represent a hydrogen atom or an optionally substituted (CrC 6 )alkyl group, such as hydroxyethyl, and, when R' represents a hydrogen atom, the hydrogencarbonate is then known as dihydrogencarbonate (C0 2 , H 2 0); and
  • the basifying agent is chosen from alkali metal or alkaline-earth metal (bi)carbonates and amino acids such as arginine; preferentially alkali metal (bi)carbonates and amino acids.
  • the basifying agent(s) is (are) chosen from aqueous ammonia, carbonates and hydrogen carbonates.
  • the basifying agent(s) as defined previously preferably represent from 0.001 % to 10% by weight relative to the weight of the composition(s) containing them, and more particularly from 0.005% to 8% by weight of the composition.
  • compositions are made:
  • compositions according to the invention generally comprise water or a mixture of water and of one or more organic solvents or a mixture of organic solvents.
  • organic solvent is intended to mean an organic substance that is capable of dissolving or dispersing another substance without chemically modifying it.
  • Ci-C 4 lower alkanols such as ethanol and isopropanol
  • polyols and polyol ethers such as 2- butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, hexylene glycol, and also aromatic alcohols, such as benzyl alcohol or phenoxyethanol.
  • the organic solvents are present in proportions preferably of between 1 % and 40% by weight approximately and more preferably still between 5% and 30% by weight approximately, relative to the total weight of the dyeing composition.
  • compositions i) and ii) of the dyeing process in accordance with the invention may also contain various adjuvants conventionally used in hair dyeing compositions, such as anionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, non- ionic, amphoteric or zwitterionic polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic, non-ionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance volatile or non-volatile, modified or unmodified silicones, film-forming agents, ceramides, preservatives and opacifiers.
  • adjuvants conventionally used in hair dyeing compositions, such as anionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, non- ionic, amphoteric or zwitterionic
  • Said adjuvants are preferably chosen from surfactants such as anionic or zwitterionic surfactants or mixtures thereof and mineral or organic thickeners.
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 40% by weight relative to the weight of the composition, and preferably between 0.1 % and 20% by weight relative to the weight of the composition i) or ii) which contains them. Needless to say, those skilled in the art will take care to select this or these optional additional compound(s) such that the advantageous properties intrinsically associated with the compositions i) or ii) that are useful in the dyeing process in accordance with the invention are not, or are not substantially, adversely affected by the envisaged addition(s).
  • the cosmetic compositions i) and ii) of the invention may be in various galenical forms, such as a powder, a lotion, a mousse, a cream or a gel, or in any other form that is suitable for dyeing keratin fibres. They may also be packaged in a pump-dispenser bottle without propellant or under pressure in an aerosol can in the presence of a propellant and form a foam. pH of the compositions:
  • the pH of the cosmetic composition ii) comprising the ingredients a) to c) is acidic, i.e. it has a pH of less than 7.0, preferably less than 5.0, in particular has a pH of between 2 and 6 inclusive, more particularly between 0.5 and 3.5, preferably between 3 and 5.
  • the pH of the cosmetic composition i) containing one or more alkaline agents is alkaline, i.e. greater than 7, preferably between 8 and 12 and more particularly between 8 and 1 1 inclusive.
  • the pH of these compositions may be adjusted to the desired value by means of basifying agents as defined previously or by using acidifying agents usually used in the dyeing of keratin fibres, or alternatively by means of standard buffer systems.
  • acidifying agents for the compositions used in the invention examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids as defined previously, for instance acetic acid, tartaric acid, citric acid or lactic acid, or sulfonic acids.
  • the invention also relates to a cosmetic composition
  • a cosmetic composition comprising one or more cationic, anionic or neutral natural dye(s) as defined previously, in particular chosen from ortho- diphenols (ODPs) and the ingredients a) to c) as defined previously.
  • ODPs ortho- diphenols
  • This composition is preferably prepared by mixing the dyeing composition i) as defined previously and the oxidizing composition ii) as defined previously. In particular, the mixing is carried out in a 1 to 1 amount (100 g of dyeing composition per 100 g of oxidizing composition).
  • the natural dye(s) is (are) preferably present in a total amount ranging from 0.0005% to 40% by weight relative to the total weight of the ready-to-use composition, in particular ranging from 0.0025% to 10% by weight relative to the total weight of the ready-to-use composition, preferentially from 0.05% to 5% by weight and better still from 0.01 % to 2.5% by weight relative to the total weight of the ready-to-use composition.
  • the content in the ready- to-use composition is preferably between 0.0005% and 2.5% by weight of said ready-to- use composition.
  • the content in the ready-to-use composition containing the extract(s) per se is preferably between 0.05% and 10% by weight of the ready-to-use composition containing them.
  • the chemical oxidizing agent(s), in particular the hydrogen peroxide or the hydrogen peroxide-generating system(s) used preferably represent(s) from 0.0005% to 6% by weight, expressed as hydrogen peroxide, relative to the total weight of the ready-to-use composition containing them, and even more preferentially from 0.1 % to 2% by weight, better still from 0.25% to 1 .5% by weight relative to the total weight of the ready-to-use composition containing them.
  • the ready-to-use composition may have a total content of fatty substance ranging from 0.05% to 15% by weight, preferably ranging from 0.5% to 10% by weight relative to the total weight of the ready-to-use composition.
  • the ready-to-use composition has a total content of fatty substance of less than or equal to 5% by weight, preferably ranging from 0.05% to 5% by weight, and even more particularly ranging from 0.1 % to 2.5% by weight, relative to the total weight of the ready-to-use composition.
  • the ready-to-use composition has a content of liquid fatty substances of less than or equal to 10% by weight, preferably less than or equal to 5% by weight.
  • the surfactant(s) are preferably present in the ready-to-use composition in an amount ranging from 0.005% to 10% by weight, preferably from 0.025% to 5% by weight and better still from 0.05% to 2.5% and particularly from 0.25% to 1 % relative to the total weight of the ready-to-use composition.
  • a subject of the present invention is a process for treating keratin fibres, in particular human keratin fibres such as the hair, in which said fibres are treated:
  • a dyeing cosmetic composition comprising one or more cationic, anionic or neutral natural dye(s) chosen as defined previously, in particular chosen from ortho- diphenols (ODPs); and
  • an oxidizing cosmetic composition ii) comprising:
  • compositions i) and ii) possibly being applied simultaneously, i.e. together, or sequentially.
  • compositions i) and ii) are applied simultaneously, that is to say they are mixed at the time of use before application to the keratin fibres.
  • compositions i) and ii) are applied sequentially, that is to say they are applied one after the other, in any order, that is to say composition i) applied before composition ii) or composition ii) applied before composition i) , preferably i) before ii), with or without intermediate rinsing, preferably without intermediate rinsing.
  • fibres are subjected to or passed through water, soaked in water one or more successive times, in particular tap water.
  • the leave-on time of the composition i) and/or ii) and/or of the mixture i) + ii) as defined previously on the keratin fibres is between 1 minute and 2 hours, more particularly between 15 minutes and 1 hour, preferably between 30 and 45 minutes.
  • the leave-on time of the composition i) and/or ii) and/or of the mixture i )+ ii) as defined previously on the keratin fibres is at a temperature of between 20°C and 50°C, more preferentially between ambient temperature (25°C) and 40°C.
  • rinsing can optionally be carried out, optionally followed by shampooing.
  • shampooing is carried out after the process of the invention, it will be followed by rinsing, preferably with tap water, preferably until the residual rinsing water of the keratin fibres is visually clear and transparent, identical to the water before treatment of the keratin fibres.
  • compositions i) and/or ii) and/or of the mixture i) + ii) as defined previously there is no rinsing.
  • the dyeing process of the invention can implement drying by heat treatment by heating at a temperature of between 30 and 60°C.
  • Use may also be made, as a means for both heating and for straightening the head of hair, of a heating iron at a temperature of between 60 and 220°C and preferably between 120 and 200°C.
  • drying is intended to mean the action of evaporating the organic solvents and/or water present in one or more compositions used in the process of the invention.
  • the drying can be carried out with a source of heat (convection, conduction or radiation) by sending out, for example, a stream of hot gas, such as air, necessary for the evaporation of the solvent or solvents.
  • a source of heat convection, conduction or radiation
  • Mention may be made, as source of heat, of a hairdryer, a hairstyling hood, a hair-straightening iron, an infrared ray dispenser or other conventional heating appliances.
  • a specific form of the invention relates to a dyeing process which is carried out at ambient temperature (20°C).
  • compositions i) and ii) are ready-to-use compositions that may result from the extemporaneous mixing of two or more compositions present in dyeing kits.
  • kits or devices comprising several separate compartments, in which is a dyeing composition i) as defined above and, in another compartment, the oxidizing composition ii) as defined above.
  • the kit comprises at least 3 separate compartments in which one compartment comprises the dyeing composition i),
  • Another compartment comprises the ingredients a) and b) as defined previously, and another compartment comprises the ingredient c) as defined previously, or else
  • another compartment comprises the ingredient a) as defined previously and another compartment comprises b) and c) as defined previously, or else
  • one compartment comprises the ingredient b) as defined previously and another compartment comprises a) and c) as defined previously.
  • the ingredients a), b) and c) can be mixed at the time of use in order to produce the oxidizing composition ii) as defined previously.
  • the kit comprises at least 4 separate compartments, in which one compartment comprises the dyeing composition, another compartment comprises the ingredient a) as defined previously, another compartment comprises the ingredient b) as defined previously, another compartment comprising the ingredient c) as defined previously.
  • the ingredients a), b) and c) can be mixed at the time of use in order to produce the oxidizing composition ii) as defined previously.
  • compositions are prepared from the following ingredients in the following proportions, indicated in grams:
  • the dyeing composition i) of Table 1 is mixed with each of the oxidizing compositions 1 , 2 and 3, in a 1 +1 weight ratio.
  • Each of the mixtures is then applied to a lock of natural hair containing 90% grey hairs.
  • the hair is then dried, without having performed a final rinsing.
  • the dyeing obtained with the dyeing process according to the invention i.e. which uses the oxidizing compositions 2 and 3, is visually stronger and more aesthetic than the process which uses the comparative oxidizing composition 1 .
  • the comparative oxidizing composition 1 results in a coarse feel to the hair, which is not the case with the oxidizing compositions 2 and 3 according to the invention.
  • the composition 3 results in hair that is not lank.
  • compositions are prepared from the following ingredients in the following proportions, indicated in grams of active material:
  • the dyeing composition i) of Table 1 is mixed with each of the oxidizing compositions 4, 5 and 6, in a 1 +1 weight ratio.
  • Each of the mixtures is then applied to a lock of natural hair containing 90% grey hairs.
  • the hair is then dried, without having performed a final rinsing.
  • the colour of the locks was then evaluated in the CIE L * a * b * system using a Minolta Spectrophotometer CM3600D colorimeter.
  • L * a * b * system the three parameters denote, respectively, the colour intensity (L * ), the green/red colour axis (a * ) and the blue/yellow colour axis (b * ).
  • L * the darker or more intense the colour.
  • the Mix 1 leads to a significantly lower value of L * , than the comparative ones, therefore the mix 1 leads to a colouration more intense in comparison with the Mix 2 and Mix 3.

Abstract

La présente invention concerne un procédé de coloration de fibres kératiniques utilisant i) une composition de coloration comprenant un ou plusieurs colorants naturels tels que définis dans la description, ii) une seconde composition d'oxydation comprenant a) un ou plusieurs agents oxydants chimiques tels que du peroxyde d'hydrogène ou un système produisant du peroxyde d'hydrogène, b) une ou plusieurs substances grasses et c) un ou plusieurs tensioactifs non ioniques ou cationiques, lesdites compositions i) et ii) pouvant être appliquées simultanément ou l'une après l'autre ; de préférence, la teneur en substances grasses de la composition d'oxydation ii) est inférieure ou égale à 10 % par rapport au poids de la composition ii).
PCT/EP2016/081102 2015-12-21 2016-12-15 Procédé de coloration des cheveux utilisant un colorant naturel, un agent oxydant, des substances grasses et des tensioactifs, composition et kit comprenant lesdits ingrédients WO2017108551A1 (fr)

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WO2019121503A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
WO2019121504A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
WO2023227292A1 (fr) 2022-05-25 2023-11-30 Henkel Ag & Co. Kgaa Procédé de coloration en deux étapes pour une coloration améliorée des cheveux avec des colorants naturels
WO2023227293A1 (fr) * 2022-05-25 2023-11-30 Henkel Ag & Co. Kgaa Procédé de coloration en deux étapes pour augmenter l'intensité de colorations avec des colorants naturels

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US11090255B2 (en) * 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
WO2023212371A2 (fr) * 2022-04-28 2023-11-02 L'oreal Compositions appropriées en tant que fixations
FR3137566A1 (fr) * 2022-07-05 2024-01-12 L'oreal Compositions convenables comme fixateurs

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WO2019121503A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
WO2019121504A3 (fr) * 2017-12-22 2019-08-01 L'oreal Dispositif à compartiments multiples comprenant au moins un joint cassable interne
WO2023227292A1 (fr) 2022-05-25 2023-11-30 Henkel Ag & Co. Kgaa Procédé de coloration en deux étapes pour une coloration améliorée des cheveux avec des colorants naturels
DE102022205252A1 (de) 2022-05-25 2023-11-30 Henkel Ag & Co. Kgaa Zweistufiges Färbeverfahren zur verbesserten Haarfärbung mit Naturfarbstoffen
WO2023227293A1 (fr) * 2022-05-25 2023-11-30 Henkel Ag & Co. Kgaa Procédé de coloration en deux étapes pour augmenter l'intensité de colorations avec des colorants naturels
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