WO2018046531A1 - Procédé de traitement de fibres de kératine par l'utilisation de dérivés ortho-dihydroxy-1,2-diphényléthylène, de carbonates (d'hydrogène), et de sels métalliques particuliers - Google Patents

Procédé de traitement de fibres de kératine par l'utilisation de dérivés ortho-dihydroxy-1,2-diphényléthylène, de carbonates (d'hydrogène), et de sels métalliques particuliers Download PDF

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WO2018046531A1
WO2018046531A1 PCT/EP2017/072325 EP2017072325W WO2018046531A1 WO 2018046531 A1 WO2018046531 A1 WO 2018046531A1 EP 2017072325 W EP2017072325 W EP 2017072325W WO 2018046531 A1 WO2018046531 A1 WO 2018046531A1
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composition
salts
manganese
ortho
derivatives
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PCT/EP2017/072325
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English (en)
Inventor
Gwénaelle JEGOU
Francis Pruche
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L'oreal
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Priority claimed from FR1658269A external-priority patent/FR3055541A1/fr
Priority claimed from FR1658272A external-priority patent/FR3055632B1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2018046531A1 publication Critical patent/WO2018046531A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates to a process for treating keratin fibres, in particular human keratin fibres such as the hair, comprising the application o f one or more ortho-dihydroxy- 1 ,2-diphenylethylene derivatives in combination with one or more manganese and/or zinc derivatives, one or more (hydrogen) carbonates and one or more additional metal salts .
  • the first type of dyeing is "permanent" or oxidation dyeing, which uses dye compositions containing oxidation dye precursors, generally referred to as oxidation bases. These oxidation bases are co lourless or weakly coloured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • the second type of dyeing is " semi-permanent" dyeing or direct dyeing, which consists in applying direct dyes to the keratin fibres, the said dyes being co loured and co louring molecules that have an affinity for the fibres, and then leaving them to take, to allow the mo lecules to penetrate by diffusion to the interior of the fibre, and then rinsing the fibres.
  • the direct dyes generally used are chosen from nitrobenzene, anthraquinone, nitropyridine, azo , xanthene, acridine, azine and triarylmethane direct dyes .
  • the direct dyes may also be natural dyes .
  • the co lourings resulting therefrom are particularly chromatic co lourings, but 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 persistence with respect to washing.
  • BSW Black Shou Wu
  • Poligonum Multiflorum extract has been mentioned for obtaining blonde co louring, especially in patent application DE 197 16 074.
  • the Applicant has discovered, surprisingly, that the use o f one or more ortho-dihydroxy- 1 ,2-diphenylethylene derivatives with one or more metal salts in a medium comprising salts or oxides o f manganese and/or zinc, and (hydrogen) carbonates, made it possible to achieve the aims set out above.
  • a subj ect of the present invention is a process for treating keratin fibres, in particular human keratin fibres such as the hair, comprising the application, to said fibres, of one or more ortho- dihydroxy- 1 ,2-diphenylethylene derivatives, of one or more manganese and/or zinc derivatives chosen from manganese salts or oxides and zinc salts or oxides, of one or more (hydrogen) carbonates and of one or more additional divalent or trivalent metal salts other than the manganese salts and zinc salts .
  • composition (A) comprising the ortho-dihydroxy- 1 ,2-diphenylethylene derivative(s) and the manganese and/or zinc derivative(s),
  • composition (B) comprising the (hydrogen) carbonate(s), and
  • the present invention also relates to a multi-compartment device containing : in a first compartment, a composition (A) comprising one or more ortho-dihydroxy- 1 ,2-diphenylethylene derivatives and one or more manganese and/or zinc derivatives; in a second compartment, a composition (B) comprising one or more (hydrogen) carbonates; one or more additional divalent or trivalent metal salts other than the manganese salts and zinc salts being present in the composition (A) and/or in the composition (B) and/or in an additional separate composition (C) present in a third compartment.
  • a composition (A) comprising one or more ortho-dihydroxy- 1 ,2-diphenylethylene derivatives and one or more manganese and/or zinc derivatives
  • B comprising one or more (hydrogen) carbonates
  • additional divalent or trivalent metal salts other than the manganese salts and zinc salts being present in the composition (A) and/or in the composition (B) and/or in an additional separate
  • the treatment process according to the invention is a dyeing process which makes it possible to obtain a (re)pigmentation of the keratin fibres, which is both gradual and visible from the first application.
  • the process of the invention makes it possible to produce a real pigmentation or a re- pigmentation of the keratin fibres by returning to the original co lour or by providing shades thereto, or else by changing the co lour.
  • the process makes it possible to gradually re- pigment the hair, depending on the number o f applications. It also makes it possible to prevent or delay the appearance of grey hair.
  • the process o f the invention differs from oxidation dyeing processes because it does not employ the condensation of dye precursors in the presence o f an oxidizing agent. It also does not correspond to a direct dyeing process because it does not emplo y co loured mo lecules.
  • the ortho-dihydroxy- 1 ,2- diphenylethylene derivatives used in the present invention are not co loured mo lecules, unlike direct dyes .
  • the process according to the invention may be repeated, which makes it possible to gradually obtain a natural dark, or even black, co louring effect.
  • the process o f the invention especially makes it possible to obtain an excellent level o f dark pigmentation and good coverage of grey hair from three applications.
  • the repeated applications may take place one after the other or be separated by several hours or even several days .
  • the process thus makes it possible to obtain good colouring intensity, especially good coverage of grey hair over the whole head of hair, and also good colour homogeneity along the keratin fibres .
  • the co lourings obtained in this way are not aggressive and are well tolerated by the keratin fibres.
  • the process according to the invention does not damage the keratin fibres and provides them with a good level o f conditioning, especially in terms o f manageability, softness, smoothness and disentangling.
  • Another subj ect of the present invention is a pigment obtained by the reaction of one or more ortho-dihydroxy- 1 ,2-diphenylethylene derivatives, of one or more manganese and/or zinc derivatives chosen from manganese salts or oxides and zinc salts or oxides, of one or more hydroxides and/or (hydrogen) carbonates, and of one or more additional metal salts other than the manganese salts and zinc salts.
  • the present invention also relates to a dyeing composition comprising said pigment.
  • substituted or “optionally substituted” is intended to mean conventional substituents o f the chemical radicals in question, such as alkyl, amino, aminoalkyl, hydroxyl, hydroxyalkyl, halogenated substituents, etc.
  • substituents such as alkyl, amino, aminoalkyl, hydroxyl, hydroxyalkyl, halogenated substituents, etc.
  • the present invention employs one or more ortho-dihydroxy- 1 ,2-diphenylethylene derivatives, especially present in the composition (A) .
  • Ortho-dihydroxy- 1 ,2-diphenylethylene derivatives denotes compounds comprising at least one ortho-dihydroxy- 1 ,2- diphenylethylene group in their chemical structure. They preferably comprise one ortho-dihydroxy- 1 ,2-diphenylethylene group or two ortho-dihydroxy- 1 ,2-diphenylethylene groups (especially in the case of ortho-dihydroxy- 1 ,2-diphenylethylene dimers) in their structure. These compounds may be compounds, the hydroxyl groups of which are protected, such as, for example, the corresponding glycosylated derivatives.
  • the ortho-dihydroxy-l,2-diphenylethylene derivative(s) used according to the present invention may be of natural or synthetic origin.
  • glycosylated derivatives such as 2,3,5,4'-tetrahydroxystilbene 2- ⁇ - ⁇ -D-glucoside; trans-3'- -glucopyranosyl-4,5'-dihydroxy-3- methoxystilbene; trans-3'- -glucopyranosyl-3,4,5'-trihydroxystilbene; and piceatannol 3-glucoside;
  • non-glycosylated derivatives such as trans-3-methoxy-3',4,5'- trihydroxystilbene; piceatannol (trans-3,3',4,5'-tetrahydroxystilbene); 5-[(lE)-2-phenylethenyl]-l,2,3-benzenetriol; 4-[(lZ)-2-(3,5- dihydroxyphenyl)ethenyl]-l,2-benzenediol; 5-[(lE)-2-(4- hydroxyphenyl)ethenyl]-l ,2,3-benzenetriol; 5-[(lE)-2-(3,4- dihydroxyphenyl)ethenyl]-l ,2,3-benzenetriol; 4-[(lE)-2-(2,4- dihydroxyphenyl)ethenyl]-l ,2-benzenediol; ⁇ -[[(2 ⁇ )-3-[2-[(1 ⁇ )-2-(3,4- dihydroxyphenyl)ethenyl]-3 ,
  • optical and/or geometric isomers the salts and/or solvates and the mixtures of such derivatives.
  • the ortho-dihydroxy- 1 ,2-diphenylethylene derivative(s) of use according to the present invention may also be in dimer form, such as those described in the Journal of Chemical Research (2004), (5), 339- 340, such as andalasin B, extracted from the roots of Morus macroura.
  • condensed tannins of ortho- dihydroxy-l,2-diphenylethylene such as those described in Tetrahedron Letters (1983), 24(38), 4147-50.
  • the ortho-dihydroxy- 1 ,2-diphenylethylene derivative(s) are chosen from glycosylated derivatives, and better still, the composition (A) comprises 2,3 ,5 ,4'-tetrahydroxystilbene 2- ⁇ - ⁇ - ⁇ - glucoside.
  • the ortho-dihydroxy- 1 ,2-diphenylethylene derivative(s) are o f natural origin.
  • the composition (A) comprises one or more extracts of plants which may be chosen, for example, from Polygonum multiflorum, Radix Poligoni Multiflori, Fallopia multiflora, Smilax china, Morus australis Poir, Cistanche tubulosa, Millettia erythrocalyx, Artocarpus lakoocha, Cissus assamica, Veratrum maackii, Vitis vinifera, Vitis labrusca, Smilax stans, Picea abies, and Guibourtia coleosperma, said extracts containing the ortho-dihydroxy- 1 ,2-diphenylethylene derivative(s) .
  • the ortho-dihydroxy- 1 ,2-diphenylethylene derivative(s) used in the present invention may be extracted from the plants mentioned above, according, for example, to the protocol described in patent application CN 1034055 16.
  • the total amount of the ortho-dihydroxy- 1 ,2-diphenylethylene derivatives present in the composition (A) preferably ranges from 0.00 1 % to 15 % by weight and more preferentially from 0.01 % to 10% by weight relative to the total weight of the composition (A) .
  • a content of extract ranging from 0. 1 % to 50% by weight and preferably from 0.5 % to 30% by weight relative to the total weight of the composition (A) is typically used.
  • the total amount of the ortho-dihydroxy- 1 ,2-diphenylethylene derivatives present in the composition (A) preferably ranges from 1 % to 99% by weight and more preferentially from 10% to 60% by weight relative to the total weight of the composition (A) .
  • the process according to the invention does not employ oxidation dyes or direct dyes other than the ortho-dihydroxy- 1 ,2-diphenylethylene derivatives and the (poly)phenols as described below.
  • Manganese and/or zinc derivatives are not employed.
  • the process o f the invention also comprises the application o f one or more manganese (Mn) and/or zinc (Zn) derivatives, chosen from the salts or the oxides .
  • Mn manganese
  • Zn zinc
  • These manganese and/or zinc derivative(s) are preferably contained in the composition (A) .
  • salts are intended to mean actual salts in the ionized form. These salts may be so lvated, in particular hydrated.
  • the derivatives are preferably salts .
  • the derivatives o f the invention are in oxidation state II, such as Mn(II) and Zn(II) .
  • the manganese and/or zinc salt(s) are advantageously chosen from chlorides, fluorides, iodides, bromides, sulfates, phosphates, nitrates, perchlorates, carbonates, carboxylates, and mixtures thereof.
  • the carboxylates o f use in the invention also include carboxylic acid salts comprising one or more hydroxyl radicals such as gluconates .
  • o f carboxylates By way o f example o f carboxylates, mention may be made, for example, o f acetate, tartrate, lysinate, glutamate, lactate, glycinate, aspartate, stearate, acetylacetate.
  • the manganese and zinc derivatives can be introduced in the so lid form into the compositions or else can be introduced in the form of aqueous so lution, such as a natural, mineral or spring water which is rich in these ions or else from seawater (Dead Sea water, especially). They can also originate from mineral compounds, such as earths, ochres, such as clays (for example green clay), or even from plant extracts containing them (cf. , for example, the document FR 2 8 14 943) .
  • manganese salts preference is given to manganese chloride, manganese carbonate, manganese difluoride, manganese acetate tetrahydrate, manganese lactate trihydrate, manganese phosphate, manganese iodide, manganese nitrate trihydrate, manganese bromide, manganese perchlorate tetrahydrate, manganese sulfate monohydrate, manganese gluconate and mixtures thereof.
  • zinc salts preference is given to zinc sulfate, zinc gluconate, zinc chloride, zinc lactate, zinc acetate, zinc glycinate, zinc aspartate and mixtures thereof.
  • the process of the invention employs one or more manganese salts, in particular Mn(II) metal salts.
  • the manganese salt(s) are chosen from manganese carboxylates, especially manganese gluconate, and manganese halides, such as manganese chloride, and mixtures thereof.
  • the manganese salt(s) are chosen from manganese chloride, manganese gluconate and mixtures thereof.
  • the total concentration of said derivative(s) in the composition (A) preferably ranges from 10 "3 to 10 " 1 mmo l. l “ 1 , and more preferentially from 10 "2 to 1 0 " 1 mmo l. l “ 1 .
  • the total concentration of said derivative(s) in the composition (A) ranges from 5. 10 "2 to 10 mmo l. l “ 1 , and more preferentially from 5. 10 " 1 to 1 mmol. l “ 1 .
  • composition (A) in liquid form.
  • the (hydrogen) carbonate(s) used in the process o f the invention are especially chosen from the compounds o f the fo llowing formulae :
  • the (hydrogen) carbonate(s) are chosen from alkali metal hydrogen carbonates, alkaline earth metal hydrogen carbonates, ammonium hydrogen carbonates and the mixtures thereof; and more preferentially from alkali metal hydrogen carbonates, alkaline earth metal hydrogen carbonates and mixtures thereof.
  • the hydrogen carbonates are chosen from sodium, potassium, magnesium and calcium hydrogen carbonates and the mixtures thereo f, and in particular sodium hydrogen carbonate and potassium hydrogen carbonate . Even more preferentially, the hydrogen carbonate used in the process o f the invention is sodium hydrogen carbonate.
  • hydrox carbonates may originate from a natural water, for example spring water from the Vichy basin or from La- Roche Posay or Badoit water (cf. for example, patent document FR 2 8 14 943) . Mention may particularly be made o f sodium carbonate Na 2 CC" 3 , and sodium hydrogen carbonate or sodium bicarbonate NaHCOs .
  • These hydrogen carbonates may also be generated in situ by any process making it possible to generate an HC O3 " salt.
  • the composition (B) may contain a total amount of the (hydrogen) carbonate(s) which preferably ranges from 0. 1 % to 15 % by weight and more preferentially from 0.5 % to 1 0% by weight relative to the total weight of the composition (B) .
  • the total mo lar concentration o f (hydrogen) carbonates is greater than the total mo lar concentration o f manganese salts and of zinc salts applied to the keratin fibres.
  • metal salt is intended to mean actual salts, that is to say in ionized form, o f the metals o f co lumns 3 to 14 of the periodic table o f the elements, other than manganese and zinc.
  • the additional metal salt(s) are preferably chosen from iron(II) salts and iron(III) salts .
  • the additional metal salt(s) are chosen from iron sulfate, iron fumarate, iron gluconate, iron acetylacetonate, iron oxalate, mixed salts, such as Mohr' s salt, and the mixtures thereo f; and better still, iron sulfate.
  • the additional metal salt(s) are present in the composition (A) .
  • the additional metal salt(s) are present in a composition (C) separate from the compositions (A) and (B) .
  • the total amount of the additional metal salt(s) preferably ranges from 0.001 % to 5 % by weight and more preferentially from 0.01 % to 4% by weight relative to the total weight of the composition containing same.
  • the process also comprises the use of an enzyme of ⁇ glucosidase type, in order to promote deglycosylation and therefore to optimize the co louring obtained.
  • an enzyme of ⁇ glucosidase type in order to promote deglycosylation and therefore to optimize the co louring obtained.
  • Use may also be made of any other means known for deglyco sylating, such as those described, for example, in Kinetics and mechanism o f 2,3 ,5 ,4'-tetrahydroxystilbene- 2-0-P-d-glycoside (THSG) degradation in aqueous solutions, J. Pharm. Biomed. Anal. 201 1 Apr 28 ;55 ( 1 ) :21 1 -5. Epub 2010 Dec 3 1 .
  • composition (A) comprising the glycosylated dihydroxy- 1 ,2- diphenylethylene, immediately before applying this composition to the fibres.
  • composition (A) comprising the glyco sylated dihydroxy- 1 ,2- diphenylethylene
  • an aqueous so lution at pH 5 to 9 if the initial composition did not contain water, to maintain this new composition as is from 10 min to 2 hours, preferably from 15 min to 1 hour before applying to the fibres, said enzyme possibly being eliminated from this composition just before applying to the fibres, by any means known to those skilled in the art.
  • glucosidases of natural origin are used, such as almond beta glucosidases, such as, in particular, sweet almond glucosidase EC 3.2. 1 .
  • the composition containing an enzyme o f ⁇ - glucosidase type is applied at a temperature of less than 55 °C and more preferentially from 30 to 40°C .
  • the pH of this composition may range from 5 to 9.
  • compositions o f use for the invention may optionally comprise one or more surfactants .
  • the surfactant(s) of use are preferably chosen from nonionic surfactants, anionic surfactants and amphoteric or zwitterionic surfactants .
  • the total amount of surfactant(s) present in the compositions according to the invention may range from 0. 1 % to 30% by weight, and preferably from 0.5 % to 20% by weight relative to the total weight of each composition containing same.
  • the surfactant(s) are preferably present in the composition (B) .
  • the process o f the invention may comprise the application, to the keratin fibres, of one or more additional phenol(s) other than the ortho-dihydroxy- 1 ,2-diphenylethylene derivatives.
  • the additional pheno l(s) are preferably contained in the composition (A) .
  • additional polyphenols are preferably chosen from ortho- diphenols, that is to say compounds comprising one or more aromatic rings, preferably benzene rings, comprising at least two hydroxyl groups (OH) borne by two adj acent carbon atoms of the same aromatic ring.
  • the ortho-dipheno l(s) of use in the invention are preferably not auto-oxidizable derivatives, especially auto-oxidizable derivatives with an indo le unit. More particularly, they are not 5 ,6- dihydroxyindole.
  • the aromatic ring may more particularly be a fused aryl or fused heteroaromatic ring, i. e. optionally comprising one or more heteroatoms, such as benzene, naphthalene, tetrahydronaphthalene, indane, indene, anthracene, phenanthrene, isoindo le, indo line, isoindo line, benzo furan, dihydrobenzo furan, chroman, isochroman, chromene, isochromene, quino line, tetrahydroquinoline and isoquino line, 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-dipheno l 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 common bond, that is to say that at least one ring is placed side-by-side with another ring.
  • the additional ortho-dipheno ls may or may not be salified. They may also be in the aglycone form (without bonded sugar) or in the form of glycosylated compounds .
  • composition (A) comprises one or more ortho-dipheno l(s) o f formula (I) below, or an oligomer thereof, in salified or non-salified form:
  • a saturated or unsaturated heterocyclic radical carrying or not carrying a cationic or anionic charge, optionally substituted and/or optionally fused with an aromatic ring, preferably a benzene ring, said aromatic ring being optionally substituted, in particular with one or more hydroxyl or glycosyloxy groups, a radical containing one or more silicon atoms,
  • the additional ortho-diphenol derivatives o f formula (I) are chosen from those in which two adjacent substituents Ri - R 2 , R 2 - R 3 or R 3 - R 4 cannot form, with the carbon atoms which bear them, a cyclic radical, in particular a pyrrolyl radical. More particularly, R 2 and R 3 cannot form a pyrro lyl radical fused to the benzene ring bearing the two hydroxyls .
  • the saturated or unsaturated and optionally fused rings may also be optionally substituted.
  • the alkyl radicals are saturated and linear or branched hydrocarbon radicals, generally C i -C 2 o hydrocarbon radicals, particularly C i -C i o hydrocarbon radicals, preferably C i -C 6 alkyl radicals such as methyl, ethyl, propyl, butyl, pentyl and hexyl.
  • the alkenyl radicals are unsaturated and linear or branched C 2 -C 2 o hydrocarbon radicals, preferably comprising at least one double bond, such as ethylene, propylene, butylene, pentylene, 2- methylpropylene and decylene.
  • the aryl radicals are monocyclic or fused or non-fused polycyclic carbon-based radicals, preferentially comprising from 6 to 30 carbon atoms, at least one ring o f which is aromatic; the choice is preferentially made, from the aryl radical, o f a phenyl, biphenyl, naphthyl, indenyl, anthracenyl and tetrahydronaphthyl.
  • the alkoxy radicals are alkyloxy radicals with alkyl as defined above, preferably C i -C i o alkyloxy radicals, such as methoxy, ethoxy, propoxy and butoxy.
  • the alkoxyalkyl radicals are preferably (C 1 -C20) alkoxy (C 1 -C20) alkyl radicals, such as methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, etc.
  • the cycloalkyl radicals are generally C 4 - C 8 cycloalkyl radicals, preferably the cyclopentyl and cyclohexyl radicals.
  • the cycloalkyl radicals can be substituted cyclo alkyl radicals, in particular substituted with alkyl, alkoxy, carboxylic acid, hydroxyl, amine and ketone groups .
  • the additional ortho-dipheno ls o f use in the process o f the invention may be natural or synthetic.
  • the natural ortho-dipheno ls include the compounds which may be present in nature and which are reproduced by chemical (semi)synthesis.
  • the process comprises the application o f one or more additional synthetic ortho-dipheno l(s) that do not exist in nature.
  • the additional ortho-diphenols are natural ortho-dipheno ls.
  • the additional natural ortho-dipheno ls of use in the process of the invention are chosen from:
  • anthocyanidins such as cyanidin, delphinidin, petunidin or pelargonidin
  • anthocyanins or anthocyans such as delphinidin 3 -0- glucoside, also referred to as myrtillin,
  • ortho-hydroxybenzoates for example gallic acid derivatives, and in particular gallates, for example propylgallate,
  • proanthocyanidins and especially the proanthocyanidins A l , A2, B l , B2, B3 and C I ,
  • catechin quercetin, brazilin (CAS 474-07-7), haematein, haematoxylin, chlorogenic, caffeic and gallic acids, catechol, L DOPA, pelargonidin, cyanidin, (-)-epicatechin, (-)- epigallo catechin, (-)-epigallocatechin 3 -gallate (EGCG), (+)-catechin, isoquercetin, pomiferin, esculetin, 6,7-dihydroxy-3 -(3 -hydroxy-2,4- dimethoxyphenyl)coumarin, santalin AC, mangiferin, butein, maritimetin, sulfuretin, robtein, betanidin, pericampylinone A.
  • the additional ortho-diphenol(s) according to the invention are chosen from flavano ls, flavono ls, ortho- hydroxybenzoates, iso flavones and neoflavones .
  • the natural ortho-dipheno ls are derived from, or are introduced in the form o f, extracts of animals, bacteria, fungi, algae, plants and fruits, used in their entirety or partially.
  • the extracts are derived from fruits, including citrus fruits, from vegetables, from trees, from shrubs and lichen. Use may also be made of mixtures of these extracts rich in ortho-dipheno ls as defined above.
  • the additional ortho-dipheno l(s) are natural ortho- diphenols derived from extracts of plants or plant parts. These extracts of plants or plant parts may be used directly in the process o f the invention.
  • 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.
  • Mention may be made, among the extracts of plants, of extracts of rose or tea leaves .
  • Mention may be made, among the extracts of fruit, o f 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, o f extracts of potato or of onion peel.
  • extracts of tree wood mention may be made o f extracts of pine bark and extracts of logwood.
  • Use may also be made of mixtures of plant extracts .
  • the ortho-dipheno l(s) are natural extracts rich in ortho-diphenols.
  • the additional ortho-dipheno l derivative(s) are so lely contained in natural extracts .
  • the polyphenol(s) used in the process according to the invention are chosen from catechin, quercetin, haematein, haematoxylin, brasilin, gallic acid, and natural extracts containing same, chosen especially from grape marc, pine bark, green tea, onion, cocoa bean, logwood, redwood and gall nut.
  • the extract used is preferably logwood.
  • the additional po lypheno l(s) are chosen from catechin, quercetin, gallic acid and haematoxylin.
  • the natural extracts containing the additional po lypheno ls according to the invention may be in the form of powders or liquids.
  • the extracts containing the additional po lypheno ls according to the invention are in the form of powders .
  • the synthetic or natural polypheno l(s) and/or the natural extract(s) containing same preferably represent(s) from 0.001 % to 20% by weight of the total weight of the composition containing same, preferably the composition (A) .
  • the content in the composition(s) containing same is preferably between 0.001 %) and 5 % by weight of each of these compositions .
  • the process according to the invention does not employ oxidation dyes or direct dyes other than the ortho-dihydroxy- 1 ,2-diphenylethylene derivatives and the additional polyphenols described above.
  • compositions used in the present invention may be in any form which is compatible with an application to keratin fibres, and especially the hair.
  • compositions (A) and (B) and, where appropriate, (C), of use in the invention may be in the form o f liquid or powder compositions.
  • the compositions (A) and (B) and, where appropriate, (C) are in the form of liquid compositions such as solutions .
  • They may be aqueous solutions, in particular aqueous-alcoho lic so lutions. They generally comprise water or a mixture of water and o f one or more so lvents, for example chosen from the lower C i to C 4 alcoho ls, such as ethano l, isopropanol, tert-butano l or n-butano l; polyo ls such as glycerol, propylene glycol and polyethylene glyco ls, and the mixtures thereof.
  • the total amount of the so lvent(s) preferably ranges from 0.01 % to 50% by weight and more preferentially from 0.05 % to 30% by weight relative to the weight o f each composition containing same.
  • composition which contains the metal salt is in the form o f a so lution, the latter must not flo cculate.
  • suitable pH to prevent flocculation o f the composition, as a function o f the metal salt.
  • composition (A) When it is aqueous, the composition (A) has an acid pH, preferably ranging from 3 to 7. When it is aqueous, composition (B) has a rather basic pH, preferably between 7. 1 and 9.5. When it is aqueous, the composition (C) has a rather acid pH, ranging from 2 to 7, preferably from 3 to 4.
  • compositions of use in the invention may comprise one or more additives, among which mention may be made o f cationic, anionic, nonionic and amphoteric polymers or the mixtures thereo f, thickeners, anti-dandruff agents, antiseborrheic agents, agents for preventing hair lo ss and/or promoting hair regrowth, vitamins and provitamins including pantheno l, sunscreens, sequestrants, plasticizers, so lubilizers, acidifying agents, opacifiers or nacreous agents, hydroxy acids, fragrances, preserving agents, or fillers, preferentially o f natural origin.
  • fillers mention may be made o f pigments such as iron oxides derived from ochres, carbon black, chlorophyll or polymerized anthocyanins .
  • the above additives may be present in an amount, for each o f them, o f between 0 and 20% by weight relative to the total weight of each composition containing same, for a liquid composition.
  • the above additives may be present in an amount, for each o f them, o f between 0 and 80% by weight relative to the total weight of each composition containing same, for a solid composition.
  • compositions (A), (B) and where appropriate (C) are applied to dry or wet keratin fibres and preferably to wet keratin fibres.
  • the additional metal salt(s) as defined above are present in a composition (C) separate from the compositions (A) and (B) and the three compositions (A), (B) and (C) are applied successively to the keratin fibres.
  • the process more preferentially comprises the application, to the keratin fibres :
  • composition (B) - of the composition (B) .
  • compositions (A) and (B) may also be mixed extemporaneously before their application to the keratin fibres. They may thus be kept, before application to the hair, in a compartment which does not contain oxygen. Oxygen from the air will then act directly on the hair. This embodiment makes it possible to reduce the number of steps to obtain pigmentation of the hair.
  • the additional metal salt(s) as defined above are present in the composition (A), and the process comprises the application o f the composition (A), followed by the application of the composition (B) .
  • compositions (A), (B) and optionally (C) is advantageously left in place on the keratin fibres for a duration ranging from 30 seconds to 1 hour, and more preferentially from 30 seconds to 30 minutes .
  • the process of the present invention may be repeated several times, especially from 2 to 50 times, preferably from 3 to 30 times, depending on the desired degree of co louring.
  • the process of the invention is carried out by re-applying the compositions (A), (B) and optionally (C) several times, to obtain, over time, a natural and visible co louring.
  • the compositions according to the invention may be applied after each shampoo operation, or for example once or twice per week.
  • the process of the invention may also comprise a step o f rinsing after the application of the compositions (A) and (B) or after application o f the compositions (A), (B) and (C) .
  • the process comprises a single final rinsing step .
  • the keratin fibres are only rinsed after the application o f the final composition.
  • the present invention relates to a multi-compartment device comprising :
  • composition (C) optionally, a third compartment containing the composition (C) as defined above.
  • the latter contains a compartment comprising a composition resulting from the mixing o f the composition (A) with the composition (B), this compartment not containing oxygen.
  • the device according to the present invention may also comprise : - an additional compartment containing the composition (C) as defined above, and/or
  • compositions o f the compartments are intended to be applied successively to the keratin fibres according to the process as described above.
  • the present invention relates also to a pigment obtained by the reaction o f one or more ortho-dihydroxy- 1 ,2-diphenylethylene derivatives as defined above, of one or more manganese and/or zinc derivatives chosen from manganese salts or oxides and zinc salts or oxides as defined above, of one or more hydroxides and/or (hydrogen) carbonates as defined above, and o f one or more additional metal salts other than the manganese salts and zinc salts as defined above.
  • the hydroxides are chosen in particular from the hydroxides o f sodium, potassium and calcium.
  • a catalytic amount of Mn 2+ and/or Zn 2+ salt is added to a so lution of ortho-dihydroxy- 1 ,2-diphenylethylene derivative in water and after 1 to 30 minutes, a so lution of sodium bicarbonate or calcium hydroxide is added. After 1 to 24 hours, a solution containing Fe 2 + salts is added. It is then left to stand for a period of time ranging from 1 minute to 24 hours and then a brown to black precipitate is iso lated by filtration, centrifugation or freeze-drying. This precipitate is optionally washed with water or with an organic so lvent such as ethano l, acetone or isopropanol and then dried.
  • an organic so lvent such as ethano l, acetone or isopropanol
  • filtration fo llowed by drying can be carried out at the end o f the synthesis process.
  • the pigment thus prepared can be used in various applications where it is desired to have a brown to black pigment, such as, but not limited to , makeup products, sunscreen compositions and hair co louring products .
  • a subject of the present invention is therefore compositions, in particular dyeing compositions, containing the pigment as described above.
  • the three parameters respectively denote the intensity of the colour (L*), the green/red colour axis (a*) and the blue/yellow colour axis (b*).
  • L* the intensity of the colour
  • a* green/red colour axis
  • b* blue/yellow colour axis
  • Example 1 according to the invention a. Compositions tested
  • compositions Al and B were prepared from ingredients whose contents are indicated in the tables below.
  • composition Al Composition Al :
  • Black shou wu is a natural extract enriched in THSG, prepared according to the preparation process described in patent application CN 103405516, and which contains from 15% to 30% by weight of THSG. It contains a total amount of polyphenols including THSG of 25% to 50% by weight.
  • THSG denotes 2,3,5,4'-tetrahydroxystilbene 2- ⁇ - ⁇ - ⁇ - glucoside, which is a derivative of ortho-dihydroxy- 1 ,2- diphenylethylene of formula:
  • compositions Al and B thus obtained were then applied, according to the protocol below, to locks of 100% grey Chinese hair, washed beforehand.
  • composition Al by means of a brush at an amount of 500 ⁇ of solution Al on 0.5 g locks. The locks were then left to take at 22°C for 15 minutes.
  • composition B namely 500 ⁇ per 0.5 g lock. After 15 minutes leaving to take at 22°C , the locks of hair were rinsed in water then left to dry.
  • the table below represents the co louring intensity values, evaluated in the L * a*b * system (mean value for 3 locks) .
  • Example 2 according to the invention a. Compositions tested
  • compositions A2, B and C were prepared from ingredients whose contents are indicated in the tables below.
  • Composition A2
  • compositions A2, B and C thus obtained were then applied, according to the protocol below, to locks of Chinese hair ( 100% or 50% grey), washed beforehand.
  • composition A2 was firstly applied by means of a brush at an amount of 500 ⁇ of so lution A2 to locks each weighing 0.5 g. The lo cks were then left to take at 22°C for 15 minutes .
  • composition B An identical amount of composition B was then applied, namely 500 ⁇ per 0.5 g lock. After 15 minutes leaving to take at 22°C, 1 ml of composition C was applied to the locks, and left to take for one minute.
  • the co lourings are significantly darker and more intense after 30 applications .
  • Example 3 comparative process without application of Fe salt a. Compositions tested
  • compositions A2 and B were prepared from ingredients whose contents are indicated in the tables of example 2 above. b. Procedure
  • compositions A2 and B obtained in this way were then applied to locks of 100% grey Chinese hair washed beforehand, according to the protocol of example 1 . d. Results
  • the table below represents the co louring intensity values, evaluated in the L * a*b * system (mean value for 3 locks) .
  • This comparative example shows that the presence o f the additional salt, in combination with the ortho-dihydroxy- 1 ,2- diphenylethylene derivative, the manganese and/or zinc salt(s) and the hydrogen carbonate, is necessary in order to obtain an intense dark co louring o f the hair.
  • Example 4 use of piceatannol - comparative tests a. Compositions tested
  • compositions A3 and A4 were prepared from ingredients whose contents are indicated in the table below.
  • Piceatannol corresponds to 4- [(E)-2-(3 ,5 - dihydroxyphenyl)ethenyl]benzene- 1 ,2-dio l, which is an ortho- dihydroxy- 1 ,2-diphenylethylene derivative of formula: b.
  • the 100% grey locks of hair are treated according to the protocol of example 1, with the compositions A3 or A4 and the composition B described in example 1. The protocol was carried out once.
  • the table below represents the colouring intensity values, evaluated in the L*a*b* system (mean value for 3 locks).
  • Example 5 preparation of a pigment from an extract of Black shou wu l g of B lack shou wu extract described in example 1 is added to 100 ml of a 10 "2 mo l/1 solution o f manganese gluconate. The mixture is left stirring for 1 hour at ambient temperature and in air. Then, 10 ml of a solution containing 8% by weight of active material o f KHCO3 are added. The mixture is stirred for 2 hours at ambient temperature and in air. An iron sulphate so lution o f 5 % by weight of active material is then added. The mixture is left under stirring for 24 hours. The precipitate obtained is filtered. The latter is washed 3 times with 50 ml of water before being dried.
  • the pigment thus obtained is inso luble in water, ethano l, acetone, isopropano l and DMSO in a test which consists in adding 100 mg of pigment in 10 ml of so lvent at ambient temperature.
  • Example 6 composition o f wax/water mascara
  • the fo llowing wax/water mascara composition was prepared:
  • This composition was applied to locks of hair (0.5 g) . After 8 hours at room temperature, the locks were cleaned with a make-up remover for mascara (La Roche Posay Respectissime make-up remover water proof) and then rinsed with water. The same operation was repeated several times with the above composition.
  • a make-up remover for mascara La Roche Posay Respectissime make-up remover water proof
  • the co lours of the lo cks obtained were evaluated in the CIE L * a* b* system, using a Mino lta Spectrophotometer CM2600D co lorimeter.

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Abstract

L'invention concerne un procédé de traitement des fibres de kératine en particulier les fibres de kératine humaines telles que les cheveux, comprenant l'application sur lesdites fibres d'un ou plusieurs dérivés ortho-dihydroxy-1,2-diphényléthylène, d'un ou de plusieurs sels de manganèse et/ou d'un ou de plusieurs sels de zinc, d'un ou de plusieurs carbonates d'hydrogène et d'un ou de plusieurs sels métalliques divalents ou trivalents supplémentaires autres que les sels de manganèse et les sels de zinc. La présente invention concerne également un dispositif à plusieurs compartiments approprié permettant la mise en œuvre de ce procédé.
PCT/EP2017/072325 2016-09-06 2017-09-06 Procédé de traitement de fibres de kératine par l'utilisation de dérivés ortho-dihydroxy-1,2-diphényléthylène, de carbonates (d'hydrogène), et de sels métalliques particuliers WO2018046531A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1658269 2016-09-06
FR1658269A FR3055541A1 (fr) 2016-09-06 2016-09-06 Procede de traitement des fibres keratiniques mettant en oeuvre des derives d'ortho-dihydroxy-1,2-diphenylethylene, des (hydrogeno)carbonates et des sels metalliques particuliers
FR1658272 2016-09-06
FR1658272A FR3055632B1 (fr) 2016-09-06 2016-09-06 Nouveaux pigments naturels et leur utilisation en cosmetique

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19716074A1 (de) 1997-04-17 1998-10-22 Henkel Kgaa Naturhaarfärbemittel
EP1013260A2 (fr) * 1998-12-22 2000-06-28 L'oreal Utilisation d'hydroxystilbènes pour la teinture, composition prête à l'emploi les contenant et procédé de teinture
FR2814943A1 (fr) 2000-10-09 2002-04-12 Oreal Composition de coloration, procede d'obtention et utilisation pour la coloration de la peau et/ou des fibres keratiniques
CN101658559A (zh) * 2009-09-09 2010-03-03 华南理工大学 检测何首乌中二苯乙烯苷和蒽醌类成分的毛细管电泳方法
WO2010082001A2 (fr) * 2009-01-16 2010-07-22 L'oreal Produit pour la prévention ou le traitement du blanchissement des cheveux
FR2976794A1 (fr) * 2011-06-23 2012-12-28 Oreal Procede de coloration capillaire mettant en œuvre au moins un orthodiphenol, un sel de manganese ou de zinc, du peroxyde d'hydrogene, du (bi)carbonate, un agent alcalin et un sel de scandium
FR2981570A1 (fr) * 2011-10-21 2013-04-26 Oreal Procede de coloration capillaire a partir d'orthodiphenols particuliers et de cyclodextrines
CN103405516A (zh) 2013-07-24 2013-11-27 桂林莱茵生物科技股份有限公司 一种水溶性好的何首乌提取物及其制备方法
WO2016101259A1 (fr) * 2014-12-26 2016-06-30 L'oreal Procédé pour la prévention ou le traitement du grisonnement des cheveux comprenant l'application d'un extrait de plante comprenant du (e) -2,3,5,4'-tétrahydroxy-stilbène -2-o-glucoside et son utilisation

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19716074A1 (de) 1997-04-17 1998-10-22 Henkel Kgaa Naturhaarfärbemittel
EP1013260A2 (fr) * 1998-12-22 2000-06-28 L'oreal Utilisation d'hydroxystilbènes pour la teinture, composition prête à l'emploi les contenant et procédé de teinture
FR2814943A1 (fr) 2000-10-09 2002-04-12 Oreal Composition de coloration, procede d'obtention et utilisation pour la coloration de la peau et/ou des fibres keratiniques
WO2010082001A2 (fr) * 2009-01-16 2010-07-22 L'oreal Produit pour la prévention ou le traitement du blanchissement des cheveux
CN101658559A (zh) * 2009-09-09 2010-03-03 华南理工大学 检测何首乌中二苯乙烯苷和蒽醌类成分的毛细管电泳方法
FR2976794A1 (fr) * 2011-06-23 2012-12-28 Oreal Procede de coloration capillaire mettant en œuvre au moins un orthodiphenol, un sel de manganese ou de zinc, du peroxyde d'hydrogene, du (bi)carbonate, un agent alcalin et un sel de scandium
FR2981570A1 (fr) * 2011-10-21 2013-04-26 Oreal Procede de coloration capillaire a partir d'orthodiphenols particuliers et de cyclodextrines
CN103405516A (zh) 2013-07-24 2013-11-27 桂林莱茵生物科技股份有限公司 一种水溶性好的何首乌提取物及其制备方法
WO2016101259A1 (fr) * 2014-12-26 2016-06-30 L'oreal Procédé pour la prévention ou le traitement du grisonnement des cheveux comprenant l'application d'un extrait de plante comprenant du (e) -2,3,5,4'-tétrahydroxy-stilbène -2-o-glucoside et son utilisation

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Title
J. PHARM. BIOMED. ANAL., vol. 55, no. 1, 28 April 2011 (2011-04-28), pages 211 - 5
JOURNAL OF CHEMICAL RESEARCH, vol. 5, 2004, pages 339 - 340
TETRAHEDRON LETTERS, vol. 24, no. 38, 1983, pages 4147 - 50

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