WO2017025244A1 - Procédé cosmétique permettant de traiter des matières de kératine - Google Patents

Procédé cosmétique permettant de traiter des matières de kératine Download PDF

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WO2017025244A1
WO2017025244A1 PCT/EP2016/065410 EP2016065410W WO2017025244A1 WO 2017025244 A1 WO2017025244 A1 WO 2017025244A1 EP 2016065410 W EP2016065410 W EP 2016065410W WO 2017025244 A1 WO2017025244 A1 WO 2017025244A1
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benzene
bis
composition
radical
tris
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PCT/EP2016/065410
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English (en)
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Andrew Greaves
Anne POTTER
Audrey Gueniche
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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
    • A61Q5/04—Preparations for permanent waving or straightening 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A61Q5/006—Antidandruff preparations

Definitions

  • the present invention relates to a process for treating keratin materials, using a composition comprising a chitosan polymer grafted with a group bearing a thiol function.
  • chitosan is a film-forming polymer commonly used especially in hair shaping haircare products. Chitosan is also described in document CA-A-2232422 as an antidandruff active agent. Chitosan is also used in deodorant products to reduce or prevent the formation of unpleasant body odour, and more particularly underarm odour, especially as described in US-A-2003/0 133 891 .
  • the aim of the present invention is to provide a cosmetic product comprising a chitosan- based polymer with improved cosmetic properties.
  • the aim of the invention is to optimize the cosmetic properties of chitosan, in particular the deodorant, antidandruff, softness and hair-disentangling properties.
  • This film has deodorant and antidandruff properties, gives the hair softness and makes it easier to comb. These cosmetic properties are more effective than those obtained with an unmodified chitosan.
  • the film obtained has good water resistance.
  • a subject of the present invention is a cosmetic process for treating keratin materials, comprising the topical application to the keratin materials of a composition, especially a cosmetic composition, comprising, in a physiologically acceptable medium, a chitosan polymer whose amino groups are grafted with groups bearing a thiol function of formula (I) as defined below.
  • the grafted chitosan polymer used in the process according to the invention is a polymer of formula (I):
  • L being a divalent hydrocarbon-based group comprising 2 carbon atoms
  • L being a linear, branched or cyclic, saturated or unsaturated divalent hydrocarbon- based group comprising from 3 to 20 carbon atoms, preferably from 3 to 10 carbon atoms, which may be interrupted with one or more non-adjacent heteroatoms chosen from sulfur, oxygen, or -NH-, -CO-, -CONH-, -COO-, -O-CO-N(Ra)-, in particular -O-CO-NH- or - N(Rb)-CO-N(Rc)- groups, in particular -NH-CO-NH-, said divalent group possibly being substituted with one or more groups chosen from hydroxyl, amine -N(Ra)(Rb)(Rc), thiol, carboxylic acid, esters -C0 2 Ra, amide -N(Ra)CO-(Rb), cyano, acyl(Ci-C 4 )amino and ureido -N(Ra)-CO-N(
  • Ra, Rb and Rc independently denoting a hydrogen atom or a linear or branched, preferably linear, Ci-C 6 alkyl radical;
  • n ranges from 5 to 2000.
  • grafted chitosan (I) may also be represented according to formula(la):
  • the grafted chitosan comprises a units bearing a free amino group, b units bearing an N-acetyl amino group and c units bearing an amino group grafted with a group -CO-L-SH; b ranges from 0 to 0.5, preferably from 0.05 to 0.30, and better still from 0.1 to 0.30;
  • the grafted chitosan has a degree of grafting (molar content) with groups (-CO- L-SH) ranging from 0.1 % to 50%, preferentially ranging from 1 % to 30% and more preferentially ranging from 1 % to 20%.
  • groups -CO- L-SH
  • L is a linear, branched or cyclic, saturated or unsaturated (including aromatic) C3-C20, preferably C3-C10, divalent hydrocarbon-based radical, which may be interrupted with one or more non-adjacent heteroatoms chosen from oxygen or with one or more non-adjacent groups chosen from -NH-, -CO-, -O-CO- and -NH-CO-.
  • the grafted chitosan (I) has a degree of acetylation (-CO-CH 3 ) ranging from 0% to 50% (especially from 0.1 % to 50%), preferably ranging from 5% to 30%, and more preferentially ranging from 10% to 30%.
  • n ranges from 5 to 1700, preferably from 5 to 280 and more
  • L denotes a divalent radical chosen from:
  • L denotes the divalent radical
  • the compounds (I) may be obtained according to a first preparation method (Scheme 1 ) by reacting a chitosan with a thiolactone (A): the primary amine group of chitosan, by reacting with the thiolactone function, forms an amide compound (I).
  • A thiolactone
  • This reaction is especially known with homocysteine thiolactone in the publication "Synthesis and characterization of chitosan-homocysteine thiolactone as a mucoadhesive polymer", K. Juntapram et al., Carbohydrate Polymers; 87 (2012) 2399-2408.
  • the reaction may take place in an aprotic or protic solvent.
  • the reaction takes place in water at a pH of between 4 and 9 and preferentially between 5 and 7.
  • the reaction may be performed at a temperature of between 5 and 80°C.
  • the reaction takes place at room temperature (25°C).
  • the compounds (I) may also be prepared according to a second preparation method (scheme 2) by reacting a chitosan with a thiolated carboxylic acid (B) to form the amide compound (I).
  • a second preparation method (scheme 2) by reacting a chitosan with a thiolated carboxylic acid (B) to form the amide compound (I).
  • Such a reaction between an amine and a carboxylic acid is known to those skilled in the art and described in publications such as "Catalytic amide formation from non-activated carboxylic acids and amines", Chem. Soc. Rev., 2014, 43, 2714-2742; “Evolution of amide bond formation” ARKIVOC 2010 (viii) 189-250; "Amide bond formation: beyond the myth of coupling reagents", Chem. Soc. Rev., 2009, 38, 606-631.
  • a thiolated activated carboxylic acid B' may be used instead of compound B.
  • the reaction is a reaction between a primary amine (that of chitosan) and an activated carboxylic acid ( ⁇ ') to form annamide.
  • This reaction is known to those skilled in the art and described in numerous reviews such as March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th Edition (ISBN: 978-0-470-46259-1 ).
  • a carboxylic acid (activated or non-activated) comprising a protected thiol group (B) may be used instead of compound B.
  • the amine group of chitosan reacts with the carboxylic acid to form an amide, and in a second stage, the protected thiol group is then released via a deprotection reaction.
  • This deprotection reaction is described in many articles such as March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th Edition (ISBN: 978-0-470-46259-1 ), Protecting groups, J. Chem. Soc, Perkin Trans. 1 , 1999, 1589-1615 and Protecting groups, J. Chem. Soc, Perkin Trans. 1 , 1998, 4005.
  • reaction between chitosan and compound (B) or ( ⁇ ') or (B") may be performed directly in an aprotic or protic solvent.
  • the reaction is performed in water at a pH of between 4 and 9 and preferably between 5 and 7.
  • the reaction is performed at a temperature of between 5 and 80°C.
  • the reaction is performed at room temperature (25°C).
  • a subject of the invention is also a composition
  • a composition comprising, in a physiologically acceptable medium, a grafted chitosan (I) or (la) as defined previously and a cosmetic additive chosen from emulsifiers, preserving agents, fragrances, thickeners, oils, waxes, film- forming polymers and dyestuffs.
  • composition used according to the invention is generally suitable for topical application to keratin materials, in particular to the skin and the hair, and thus generally comprises a physiologically acceptable medium, i.e. a medium that is compatible with the skin and/or its integuments. It is preferably a cosmetically acceptable medium, i.e. a medium which has a pleasant colour, odour and feel and which does not cause any unacceptable discomfort (stinging, tautness or redness) liable to discourage the consumer from using this composition.
  • physiologically acceptable medium i.e. a medium that is compatible with the skin and/or its integuments.
  • a cosmetically acceptable medium i.e. a medium which has a pleasant colour, odour and feel and which does not cause any unacceptable discomfort (stinging, tautness or redness) liable to discourage the consumer from using this composition.
  • the grafted chitosan (I) or (la) may be present in the composition used according to the invention in a content ranging from 0.1 % to 10% by weight, preferably ranging from 0.5% to 10% by weight, preferentially ranging from 1 % to 8% by weight and more preferentially ranging from 1 % to 6% by weight relative to the total weight of the composition.
  • composition according to the invention may be in any galenical form conventionally used for topical application and especially in the form of dispersions of aqueous gel or lotion type, emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersing a fatty phase in an aqueous phase (O/W) or vice versa (W/O), or suspensions or emulsions of soft, semi-solid or solid consistency of the cream or gel type, or alternatively multiple emulsions (W/O/W or 0/W/O), microemulsions, vesicular dispersions of ionic and/or nonionic type, or wax/aqueous phase dispersions.
  • these compositions are prepared according to the usual methods.
  • the composition is in the form of an O/W emulsion or an aqueous gel.
  • the composition used according to the invention comprises water, in particular in a content which can range from 10% to 99% by weight and preferably ranging from 50% to 99% by weight, relative to the total weight of the composition.
  • the process comprises the following steps:
  • composition especially a cosmetic composition, comprising the grafted chitosan (I), optionally leaving the composition to stand for a time of between 5 seconds and 10 minutes;
  • a step of rinsing the keratin materials for example with water.
  • the process comprises:
  • composition A a cosmetic composition, containing same
  • composition B grafted chitosan polymer (I) (composition B), the reducing agent (II) being different from the grafted chitosan (I).
  • the process comprises:
  • composition especially a cosmetic composition, comprising at least one grafted chitosan polymer (I) and at least one reducing agent (II), preferably a reducing agent (II),
  • a subject of the invention is also a kit comprising a first composition (composition B), especially a cosmetic composition, comprising at least one grafted chitosan (I) as previously defined and a second composition (composition A), especially a cosmetic composition, comprising at least one reducing agent as previously defined, the first and second compositions each being packaged in a separate packaging assembly.
  • composition packaging assembly is, in a known manner, any packaging that is suitable for storing cosmetic compositions (in particular a bottle, tube, spray bottle or aerosol bottle).
  • Such a kit allows the process for treating keratin materials according to the invention to be performed.
  • the reducing agent may be selected from thiol reducing agents and non-thiol reducing agents.
  • a thiol reducing agent denotes a compound comprising one or more thiol (SH) groups. This thiol may be a monothiol or a polythiol as described hereinafter.
  • polythiol compound means any compound bearing two or more than two thiol groups SH. It may be a non-polymeric organic molecule bearing two or more than two thiol groups, or a polymer bearing two or more than two thiol groups.
  • the polythiol compound may be aromatic or heteroaromatic or may contain an aromatic radical.
  • the thiol compound used according to the invention may also contain one or more heteroatoms chosen from O, N and S and/or one or more functions chosen from ester, ketone, amide, urea and isocyanurate functions.
  • the polythiol compound according to the invention may also contain one or more heteroatoms chosen from O, N and S and/or one or more functions chosen from ester and ketone functions.
  • the thiol compound according to the invention denotes a non-polymeric organic compound and may be represented by formula (I la)
  • n denotes an integer greater than or equal to 1 , preferably between 1 and 10, preferably between 1 and 4 (limits included),
  • salts thereof such as those formed from acid or base.
  • salts of the compound of formula (lla) when it comprises a quaternizable nitrogen atom, mention may be made of:
  • salts obtained by addition of compound (lla) to a mineral acid chosen especially from hydrochloric, boric, hydrobromic, hydriodic, sulfuric, nitric, carbonic, phosphoric, triflic or tetrafluoroboric acid; or b) the salts obtained by addition of compound (lla) to an organic acid, chosen especially from acetic, propionic, succinic, fumaric, lactic, glycolic, citric, gluconic, salicylic, tartaric, terephthalic, methanesulfonic, ethanesulfonic, benzenesulfonic, toluenesulfonic, methoxysulfinic, ethoxysulfinic, tolueneoxysulfinic or phenoxysulfinic acid.
  • a mineral acid chosen especially from hydrochloric, boric, hydrobromic, hydriodic, sulfuric, nitric, carbonic, phosphoric, triflic or
  • a mineral base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonate or hydrogen carbonate
  • organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may be made especially of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol and 2-amino-2-(hydroxymethyl)- 1 ,3-propanediol. Mention may also be made of lysine or 3-(dimethylamino)propylamine.
  • the salts of the compounds of formula (lla) may be chosen from alkali metal or alkaline-earth metal salts such as sodium, potassium, calcium or magnesium salts; ammonium salts.
  • the salts of the compounds of formula (lla) may be chosen from halides such as chloride or bromide; citrate, acetate, succinate, phosphate, lactate, tartrate.
  • cyclic radical is intended to mean a hydrocarbon-based saturated monocyclic or heterocyclic radical, a saturated or aromatic polycyclic radical, for example biphenyl, or condensed rings, for instance the naphthyl radical.
  • the molar mass of the compounds of formula (lla) is generally between 70 and 1500 g/mol and preferably between 70 and 500 g/mol.
  • W denotes a linear or branched saturated, or aromatic, C2-C20 monovalent radical, it being possible for W to also contain one or more heteroatoms such as O, N, S or Si, and/or one or more functions chosen from carboxylic acid, ester and amide functions, and/or to be substituted with one or more linear or branched C1 -C4 alkyl, hydroxyl, amino, (C1 -C6 alkyl) amino, carboxylic acid, carboxylate, or linear or branched C1 -C4 alkoxy groups, it being understood that, when the W radical is substituted, the thiol functions may be borne by the substituent(s).
  • the monothiol compound may be chosen, for example, from
  • thioglycolic acid thiolactic acid, thiomalic acid, 2-mercaptopropionic acid, 3- mercaptopropionic acid, thiosalicylic acid, thiopropionic acid, glutathione, cysteine, N- acetyl cysteine, homocysteine and mercaptosuccinic acid, and Ci-C 4 alcohol esters thereof, cysteamine, N-acetyl cysteamine, thioglycerol, 2-mercaptoethanol, 1 -mercapto-2- propanol, 3-mercapto-1 -propanol, 2-(trimethylsilyl)ethanethiol, (3- mercaptopropyl)triethoxysilane,
  • n and m being integers ranging from 1 to 4, ortho-aminothiophenol, meta-aminothiophenol, and para-aminothiophenol.
  • the thiol (lla) is chosen from cysteine, cysteamine, thioglycolic acid and (3-mercaptopropyl)triethoxysilane.
  • the polythiol compound of the invention denotes, for example
  • the compound bearing a thiol unit may be chosen, for example, from 1 ,1 ,1 -tris(mercaptomethyl)ethane, 2-ethyl-2-mercaptomethyl-1 ,3- propanedithiol, and 1 ,2,3-propanetrithiol.
  • the compound bearing a thiol unit may be chosen, for example, from
  • bis(mercapto(C 2 -Ci2)alkyl) ethers and sulfides such as bis(2- mercaptoethyl) ether, bis(2-mercaptoethyl)sulfide, bis(2-mercaptoethylthio-3- mercaptopropane)sulfide,
  • compound (I la) is chosen from 1 ,2-bis(2- mercaptoethylthio)propanethiol, 1 ,2,3-tris(2-mercaptoethylthio)propane and tetrakis(2- mercaptoethylthiomethyl)methane.
  • the compound bearing a thiol unit, of formula (I la) is such that n denotes an integer greater than or equal to 2 and W denotes a linear or branched C3-C20, preferably linear or branched C2-C12, hydrocarbon-based saturated multivalent (at least divalent) radical, said radical containing at least one ester function.
  • the compound bearing a thiol unit may be chosen, for example, from
  • esters of polyols such as ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(thioglycolate), trimethylolpropane tris(thioglycolate), trimethylolpropane tris(beta-mercaptopropionate), pentaerythritol tetrakis(thioglycolate), pentaerythritol tetrakis(beta-mercaptopropionate), dipentaerylthritol hexakis(beta-mercaptoproprionate), trimethylolpropane tris(2- mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), pen
  • the compound bearing a thiol unit is chosen from trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3- mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutanate) and dipentaerythritol hex-3-mercaptopropionate.
  • the compound bearing a thiol unit is pentaerythritol tetrakis(3- mercaptopropionate).
  • the compound bearing a thiol unit may be chosen, for example, from tetrakis(2-mercaptoethylthiomethyl)methane and bis(2-mercaptoethylthio- 3-mercaptopropane)sulfide.
  • the compound bearing a thiol unit may be chosen, for example, from 1 ,4-cyclohexanedithiol, 1 ,4-bis(mercaptomethyl)cyclohexane, 1 ,1 - cyclohexanedithiol, 1 ,2-cyclohexanedithiol, 1 ,1 -bis(mercaptomethyl)cyclohexane, and 2,5- dimercapto-1 ,4-dithiane.
  • the compound bearing a thiol unit may be chosen, for example, from polythiols of the isocyanurate class, described in patents US 3 676 440 and US 201 1 023 0585, such as tris((mercaptopropionyloxy)ethyl)isocyanurate.
  • the compound bearing a thiol unit denotes tris((mercaptopropionyloxy)ethyl)isocyanurate.
  • the compound bearing a thiol unit may be chosen, for example, from
  • compound (lla) is chosen from 1 ,2,3-trimercaptobenzene, 1 ,2,4-trimercaptobenzene, 1 ,3,5-trimercaptobenzene, 1 ,2,3-tris(mercaptomethyl)benzene, 1 ,2,4-tris(mercaptomethyl)benzene, 1 ,3,5-tris(mercaptomethyl)benzene, 1 ,2,3-tris(2- mercaptoethyl)benzene, 1 ,2,4-tris(2-mercaptoethyl)benzene, 1 ,3,5-tris(2- mercaptoethyl)benzene, 1 ,2,3-tris(2-mercaptoethyleneoxy)benzene, 1 ,2,4-tris(2- mercaptoethyleneoxy)benzene, 1 ,3,5-tris(2-mercaptoethyleneoxy)benzene, 1 ,2,3,4- tetramercaptobenzene
  • the compound bearing a thiol unit may be chosen, for example, from: triglycerides of fatty acids or vegetable oils modified with thiol groups by chemical reaction, for instance thiolated soybean oils and hydroxylated and thiolated soybean oils, in particular the polymercaptan® products from the company Chevron Phillips, such as polymercaptan 358 (mercaptanized soybean oil) and polymercaptan 407 (mercapto hydroxy soybean oil).
  • the compound bearing a thiol unit may be chosen, for example, from dithiothreitol and 2,3-dimercapto-1 -propanol.
  • the compound bearing a thiol unit, of formula (I) may be meso-2,3-dimercaptosuccinic acid and Ci-C 4 alcohol esters thereof.
  • n denotes an integer ranging from 1 to 4 (limits included)
  • the compounds of formula (lla) are chosen from the compounds of the first embodiment, such as, in particular, thioglycolic acid, thiolactic acid, thiomalic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, thiosalicylic acid, thiopropionic acid, glutathione, cysteine, N-acetyl cysteine, homocysteine and mercaptosuccinic acid, and C1 -C4 alcohol esters thereof, cysteamine, N-acetyl cysteamine, thioglycerol, 2-mercaptoethanol, 1 -mercapto-2-propanol and 3-mercapto-1 - propanol, and C1 -C4 esters thereof, 2-(trimethylsilyl)ethanethiol, (3- mercaptopropyl)triethoxysilane,
  • the compounds of formula (I la) denote cysteine, thioglycolic acid, (3-mercaptopropyl)triethoxysilane, pentaerythritol tetrakis(3- mercaptopropionate) and dithiothreitol.
  • the thiol reducing agent used according to the invention denotes a polymeric compound and may be represented by formula (lib) POL(SH)n (lib)
  • n denotes an integer greater than or equal to 5, preferably between 5 and 5000, preferably between 5 and 1000,
  • POL denotes a multivalent (at least pentavalent) carbon-based or silicone polymeric radical, it being possible for POL to also contain one or more heteroatoms such as O, N or S, and/or one or more functions chosen from ester, ketone, amide, urea and carbamate functions, and/or to be substituted with one or more linear or branched C-I-C-IO alkyl or linear or branched C-I-C-IO alkoxy groups, it being understood that, when POL is substituted, the thiol functions may be borne by the substituent(s), with the proviso that POL does not denote a chitosan.
  • the molar mass of the compounds of formula (lib) is generally between 500 and 400 000 g/mol and preferably between 500 and 150 000 g/mol.
  • POL can denote a multivalent radical of homopolymer or copolymer type
  • POL can denote a polymeric radical of star, comb, brush or dendritic type.
  • the POL radical may be of natural origin (such as polysaccharides, peptides) or synthetic origin (such as acrylic polymers, polyesters, polyglycols).
  • the thiol functions (-SH) may be end and/or pendant groups.
  • the thiol compound of formula (lib) is such that POL denotes a hydrocarbon-based polymeric radical.
  • the compounds bearing a thiol unit, of formula (lib) such as poly(vinylmercaptan), poly(4-mercaptostyrene), poly(vinylbenzylmercaptan), poly(4-mercaptostyrene)-co-poly(methyl methacrylate), and also polymers containing amide functions in the polymer, such as poly(thiolated hexamethylene adipamide).
  • the thiol compound of formula (II) also denotes the compounds of formula (II) such that POL denotes a radical termed dendrimer or polymer which is branched or hyperbranched, and the thiol groups are end groups.
  • POL denotes a radical termed dendrimer or polymer which is branched or hyperbranched
  • the thiol groups are end groups.
  • the compound bearing a thiol unit, of formula (lib) may also denote a hyperbranched or dendritic polymer modified with thiol functions, as described in application F 2 761 691.
  • Polymers of polypropylene ether glycol bis(beta-mercaptopropionate) type can also be used. They are prepared from polypropylene ether glycol (e.g., Pluracol P201 , Wyandotte Chemical Corp.) and beta-mercaptopropionic acid by esterification reaction and are known to those skilled in the art.
  • Some polymers bearing a thiol unit, of formula (lib), are also commercially available, such as the Thiocure® products from the company Bruno Brock, Thiocure® ETTMP 1300 (Ethoxylated-Trimethylolpropane Tri-3-Mercaptopropionate (CAS# 345352-19-4) and Thiocure® ETTMP 700 (Ethoxylated-Trimethylolpropane Tri-3-Mercaptopropionate (CAS# 345352-19-4);
  • the compound of formula (lib) is such that POL denotes a silicone-based polymeric radical.
  • silicone polythiols examples include silicone polythiols.
  • the silicone polythiols are in particular polydimethylsiloxanes comprising two or more than two thiol groups such as, for example, the SMS-022, SMS-042 and SMS-992 products sold by the company Gelest Inc.
  • the monothiol compound is chosen from thioglycolic acid, thiolactic acid, thiomalic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, thiosalicylic acid, thiopropionic acid, glutathione, cysteine, N-acetyl cysteine, homocysteine and mercaptosuccinic acid, and C1-C4 alcohol esters thereof;
  • cysteamine N-acetyl cysteamine, thioglycerol, 2-mercaptoethanol, 1 -mercapto-2-propanol and 3-mercapto-1 -propanol, and C1-C4 esters thereof, 2-(trimethylsilyl)ethanethiol, (3-mercaptopropyl)triethoxysilane, the compounds of formula:
  • n and m being integers ranging from 1 to 4,
  • ortho-aminothiophenol meta-aminothiophenol and para-aminothiophenol.
  • the thiol (II) is chosen from cysteine, cysteamine, thioglycolic acid and salts thereof, and (3-mercaptopropyl)triethoxysilane.
  • the thiol is chosen from cysteine, cysteamine, thioglycolic acid and salts thereof, (3-mercaptopropyl)triethoxysilane, dithiothreitol and pentaerythritol tetra(3- mercaptopropionate).
  • non-thiol reducing agent denotes herein a reducing agent not bearing any thiol groups.
  • the non-thiol reducing agent may preferably be chosen from the group comprising sulfites, bisulfites, sulfinates, phosphines, sugars, reductones and hydrides.
  • the non-thiol reducing agent may be selected from ammonium sulfites and bisulfites, and also from metal sulfites and bisulfites, better still alkali metal or alkaline-earth metal sulfites and bisulfites, and even better still sodium sulfites and bisulfites.
  • Sulfinates that may be mentioned include sulfinic acid salts and benzenesulfinic acid salts, such as the sodium salts thereof.
  • the sulfinic acid derivatives described in FR-A-2 814 948 may also be used.
  • a preferred sulfinate compound is the disodium salt of 2-hydroxy- 2-sulfinatoacetic acid.
  • Phosphines that may be mentioned include monophosphine and diphosphines, as described in FR-A-2 870 1 19. According to a particular embodiment of the present invention, the phosphine(s) may be chosen from the compounds of formula (I) below:
  • linker which represents a covalent bond or a divalent hydrocarbon- based radical optionally comprising one or more heteroatoms chosen from an oxygen atom, a sulfur atom, a nitrogen atom and a silicon atom;
  • - m is an integer equal to 0 or 1 ;
  • - p is an integer equal to 0 or 1 ;
  • R31 , R32 and R33 which may be identical or different, represent:
  • hydrocarbon-based monovalent radical optionally comprising one or more heteroatoms chosen from a sulfur atom, an oxygen atom, a nitrogen atom, a phosphorus atom and a silicon atom, optionally substituted with one or more radicals chosen from:
  • an aromatic or heteroaromatic ring which is unsubstituted or substituted with one or more radicals chosen from a halogen atom, a hydroxyl radical, an alkoxy radical and a mono- or di(alkyl)amino radical,
  • a radical which increases the solubility of the phosphine in water such as sulfonate, sulfinate, phosphonate or carboxylate radicals,
  • the linker L is attached to one of the radicals R31 , R32 or R33, and acid-addition salts thereof.
  • the substituents are chosen from a halo, a hydroxyl, an alkyl, a haloalkyl, an alkoxy, an amino, a mono- or dialkylamino, a mono- or dihydroxyalkylamino and a carboxyl.
  • the p-methoxyphenyl radical is a substituted aryl radical.
  • the radicals R31 , R32 and R33 do not simultaneously represent a hydrogen atom.
  • At least one of the radicals R31 , R32 and R33 denotes, as hydrocarbon-based radical, an optionally substituted alkyl radical.
  • R31 , R32 and R33 are chosen from a hydrogen atom; an alkyl radical; a cycloalkyi radical optionally substituted with one or more alkyl radicals; an alkoxy radical; an alkoxyalkyl radical; a haloalkyl radical; a cyanoalkyl radical; a hydroxyalkyl radical; a carboxyalkyl radical; a halogen atom; a hydroxyl radical; a carboxyl radical; an alkenyl radical; a mono- or dialkylamino radical; an N-aryl-N-alkylaminoalkyl radical; an aryl radical optionally substituted with one or more radicals chosen from an alkyl radical, an alkoxy radical, a mono- or dialkylamino radical, a mono- or dialkylaminoalkyl radical, a haloalkyl radical, a hydroxyl radical, a carboxyl radical, a halogen
  • R31 , R32 and R33 may be chosen from a hydrogen atom; a methyl radical; an ethyl radical; a propyl radical; an isopropyl radical; an N-butyl radical; an isobutyl radical; a tert-butyl radical; an octyl radical; a cyclohexyl radical; a cyclopentyl radical; a methoxy radical; an ethoxy radical; a methoxypropyl radical; a chloroethyl radical; a cyanoethyl radical; a hydroxymethyl radical; a hydroxypropyl radical; a carboxyethyl radical; a chlorine atom; a hydroxyl radical; a carboxyl radical; a trifluoromethyl radical; a chloromethyl radical; an allyl radical; a vinyl radical; a dimethylamino radical; a diethylamino radical; a di(isopropy
  • phosphines that may be used in the context of the invention may optionally be salified with strong mineral acids, for instance HCI, HBr, H 2 S0 4 or HBF 4 , or organic acids, for example acetic acid, lactic acid, tartaric acid, citric acid or succinic acid.
  • strong mineral acids for instance HCI, HBr, H 2 S0 4 or HBF 4
  • organic acids for example acetic acid, lactic acid, tartaric acid, citric acid or succinic acid.
  • the phosphine(s) that may be used in the context of the invention are chosen from monophosphines.
  • q is then preferably equal to 1.
  • monophosphines examples include tri(hydroxymethyl)phosphine; tri(hydroxypropyl)phosphine; bis(hydroxymethyl)(phenyl)phosphine; allyldiphenylphosphine; benzyldiphenylphosphine; bis(3,4,5-trimethoxyphenyl)chlorophosphine; bis(3,4,5-trimethoxyphenyl)phosphine; benzyloxy(diisopropylamino)methylphosphine; bis(diisopropylamino)chlorophosphine; bis(2-cyanoethyl)phosphine; bis(3,5-di-tert-butylphenyl)chlorophosphine; bis(3,5-di-tert- butylphenyl)phosphine; bis(diethylamino)methylphosphine; bis(diethylamino)chlorophosphine; bis(die
  • the monophosphines are chosen from trihydroxymethylphosphine; trihydroxypropylphosphine; and bis(hydroxymethyl)phenylphosphine.
  • the phosphine(s) that may be used in the context of the invention are diphosphines.
  • q is preferably equal to 2.
  • p is equal to 0 and the linker L is a covalent bond or a divalent radical that is chosen from a binaphthylene radical; a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a meta-dimethylenebenzene radical; an N-methyl-N'-methyl hydrazo radical; a vinylene radical; and a diethyleneoxy radical.
  • a binaphthylene radical a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a meta-dimethylenebenzene radical; an N-methyl-N'-methyl hydrazo radical; a vinylene radical; and a diethyleneoxy radical.
  • diphosphines that may be used in the context of the invention, mention may be made of 2,2'-bis(dicyclohexylphosphino)-1 ,1 '-binaphthyl; 2,2'-bis[bis(3,5- dimethylphenylphosphino)]-1 ,1 '-binaphthyl; 1 ,4-bis[bis(3,5- dimethylphenyl)phosphino]butane; 1 ,2-bis[bis(3,5-dimethylphenyl)phosphino]ethane; bis[bis(3,5-dimethylphenyl)phosphino]methane; 1 ,5-bis[bis(3,5- dimethylphenyl)phosphino]pentane; 1 ,3-bis[bis(3,5-dimethylphenyl)phosphino]propane; 2,2'-bis[bis(3,5-ditrifluoromethylphenyl)phosphino]-1
  • the phosphine(s) that may be used in the context of the invention are soluble in a cosmetically acceptable medium.
  • the phosphine(s) that may be used in the context of the invention are water- soluble.
  • water-soluble refers to any phosphine whose solubility in water is greater than 0.01 % by weight at 20°C.
  • the phosphine is trihydroxymethylphosphine.
  • Sugars that may be mentioned include ribose, glucose, maltose, galactose, lactose and xylose.
  • Reductones that may be mentioned include ascorbic acid and erythorbic acid.
  • Hydrides that may be mentioned include boron hydrides such as sodium borohydride, lithium hydride and phosphorous hydride. Hydride precursors, and in particular boron hydrides, such as diborane, tetraborane, pentaborane, decaborane and dodecaborane, may be used.
  • the preferred non-thiol reducing agents are chosen from sulfites, bisulfites and phosphines.
  • the reducing agent may be present in the composition (especially composition A) used according to the invention in a content ranging from 0.1 % to 50% by weight, relative to the total weight of the composition, especially from 0.1 % to 10% by weight and preferably ranging from 1 % to 10% by weight.
  • the reducing agent or the composition containing same, applied to the keratin materials is advantageously left on for a time ranging from 1 minute to one hour, preferably ranging from 3 to 30 minutes, and preferentially ranging from 5 to 15 minutes.
  • a step of rinsing with water optionally as a mixture with a surfactant, may be performed.
  • the known surfactants suitable for cleansing keratin materials may be used.
  • a step of removing the excess water at the surface of the treated keratin materials may be performed, for example using a towel or an absorbent paper.
  • the step of applying a composition, in particular a cosmetic composition, comprising the grafted chitosan (I) is performed.
  • the process comprises the following steps (in the order indicated):
  • composition comprising a reducing agent (II), and preferably a thiol reducing agent of formula (II), leaving the composition to stand for a time ranging from 1 minute to one hour;
  • the process is performed with the rinsing step.
  • the process comprises the following steps (in the order indicated):
  • composition comprising a reducing agent (II), and preferably a thiol reducing agent of formula (II) and a grafted chitosan (I), leaving the composition to stand for a time ranging from 1 minute to one hour;
  • the process is performed with a rinsing step.
  • the process according to the invention may comprise a step of applying a composition comprising a chemical oxidizing agent (composition C), this step being performed after the step of applying the grafted chitosan (I).
  • composition of the invention preferentially contains one or more chemical oxidizing agents.
  • the chemical oxidizing agents are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, and persalts such as perborates and persulfates. Hydrogen peroxide is particularly preferred.
  • the chemical oxidizing agent(s) are chosen from hydrogen peroxide, urea peroxide, alkali metal peroxides such as sodium peroxide,
  • alkali metal bromates for instance persulfates, perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates. lodate salts
  • the chemical oxidizing agent is advantageously hydrogen peroxide.
  • the chemical oxidizing agent may be present in a content ranging from 0.1 % to 50% by weight, even more preferentially from 0.5% to 20% by weight and better still from 1 % to 15% by weight, relative to the weight of the composition.
  • a subject of the present invention is also a cosmetic process for treating human body odour, in particular underarm odour and possibly human perspiration, comprising the topical application to the skin of a composition, especially a cosmetic composition, comprising, in a physiologically acceptable medium, a chitosan polymer whose amino groups are grafted with groups bearing a thiol function of formula (I) as defined previously.
  • a cosmetic composition comprising, in a physiologically acceptable medium, a chitosan polymer whose amino groups are grafted with groups bearing a thiol function of formula (I) as defined previously.
  • the process performed according to the invention makes it possible to mask, absorb, improve and/or reduce the unpleasant odour resulting from the decomposition of human sweat.
  • the application of the cosmetic composition used according to the invention is performed according to the usual techniques, for example by application (in particular of creams, gels, sera or lotions) to the skin intended to be treated, in particular the skin of the armpits or the feet.
  • a subject of the invention is also a cosmetic process for combating the formation of dandruff on the scalp, especially that caused by yeast of the genus Malassezia, characterized in that it comprises the application to the scalp of a composition, especially a cosmetic composition, comprising a chitosan polymer whose amino groups are grafted with groups bearing a thiol function of formula (I) as defined previously.
  • a subject of the invention is also the use of a chitosan polymer whose amino groups are grafted with groups bearing a thiol function of formula (I) as defined previously, as an antidandruff agent.
  • a subject of the invention is also a cosmetic hair treatment process comprising the topical application to the hair of a composition, especially a cosmetic composition, comprising a chitosan polymer whose amino groups are grafted with groups bearing a thiol function of formula (I) as defined previously.
  • the treatment process may be a process for giving the hair softness and/or for making the hair easy to comb.
  • n 28 000 daltons
  • the reaction mixture was then introduced into a dialysis tube (Spectra/Por Dialysis Membrane MWCO 3500; NFW 54 mm, Diam. 34 mm, vol./length 9.3 ml/cm; Spectrumlabs.com ref 132725) and dialysed in 2 litres of water for 3 days, replacing the water twice a day.
  • the aqueous solution was lyophilized to give a fibrous solid yellow product.
  • Polymer 1 is thus a film-forming polymer.
  • composition 1 water
  • Composition 2 aqueous solution containing 5% by weight of AM of chitosan Zenvivo Protect from Clariant
  • Composition 3 aqueous solution containing 5% by weight of AM of polymer 1 Preparation of the substrate
  • Pieces of human stratum corneum are stuck onto Scotch tape (reference 1526886 from the company Office Depot), taking care that the external surface of the stratum corneum is not in contact directly on the Scotch tape.
  • the substrates are then cut into strips approximately 2 cm long and 1 cm wide and used with the adhesive tape at the lower part and the outer surface of the stratum corneum at the upper part.
  • the outer surface of the stratum corneum was cleaned with a wipe impregnated with ethanol.
  • Examples 1 to 3 100 ⁇ of each of the compositions 1 to 3 were applied, respectively, to the surface of the stratum corneum and left to stand for 10 minutes, and were then rinsed off with 13 ml of aqueous 0.9 M NaCI solution, and the surface was then wiped with absorbent paper. The treated strips of stratum corneum were cut into small pieces about 3 mm 3 mm in size and placed in a plastic bottle. 100 ⁇ of human sweat were added, and the bottle was closed and shaken. The bottle was then placed in an incubator for 24 hours (37°C, 5% C0 2 ). A panel of five people then evaluated the sweat odour perceived on opening each bottle (Examples 1 to 3).
  • a deodorant having the following composition is prepared:
  • Example 1 1 g - hydroxyethylcellulose (Natrosol® 250 HHR CS from Ashland) 0.2 g
  • composition obtained is applied to the skin of the armpits. A decrease in sweat- mediated odour is observed.
  • the antidandruff activity of Polymer 1 was evaluated and compared on reconstructed human skin colonized with the strains Malasezzia restricta and Malassezia globosa.
  • the strains Malassezia restricta CBS 7877 and Malassezia globosa CBS 7874 were purchased from the CBS collection centre and were received on an agar slope.
  • compositions were prepared:
  • Composition A A:
  • Composition B is a composition of Composition B:
  • the strains Malassezia restricta and Malassezia globosa were applied to the reconstructed skins and were cultured at 32°C in the ambient air for 24 hours.
  • the microorganisms were recovered and cultured on LNm agar to count them. The number of colonies was counted (average of 3 tests).
  • composition C polymer 1
  • composition B unmodified chitosan
  • composition A vehicle for the colonies of both M restricta and M globosa.
  • Polymer 1 has good antidandruff efficacy on M. restricta and M. globosa.
  • Example 7 antidandruff lotion
  • An antidandruff lotion comprising the following ingredients is prepared:
  • the lotion applied to the hair and the scalp makes it possible to reduce the appearance of dandruff.
  • composition 1 A water
  • Composition 1 B (outside the invention): aqueous solution containing 2% by weight of chitosan Zenvivo Protect from Clariant
  • Composition 1 C (invention): aqueous solution containing 2% by weight of polymer 1
  • the compositions were prepared one hour before use, and had a spontaneous pH of 5.
  • the compositions were shaken just before use.
  • the treated locks were then rinsed with water and then washed with 2 g of shampoo (aqueous solution containing 1 % by weight of sodium lauryl sulfate) for 45 seconds, and then rinsed again with water and left to dry in the open air overnight. This whole treatment was performed twice.
  • shampoo aqueous solution containing 1 % by weight of sodium lauryl sulfate
  • compositions 1 A, 1 B and 1 C described in the preceding example were used.
  • the compositions were prepared one hour before use, and shaken just before use.
  • Composition 2 was also prepared: aqueous ammonium thioglycolate solution (1 M); spontaneous pH about 8 2.7 g of composition 2 were applied to three locks of bleached hair (2.7 g of hair per lock) and left to stand for 5 minutes. The treated locks were then rinsed with water and then dried manually. 5.4 g of composition 1 C were applied to a lock of bleached hair (2.7 g of hair per lock) and left to stand for 5 minutes. The treated locks were then rinsed with water and then dried manually. A post-treatment was then performed by applying 5 g of aqueous hydrogen peroxide solution (10 volumes) and leaving to stand for 5 minutes.
  • the treated locks were then rinsed with water and then washed with 2 g of shampoo (aqueous solution containing 1 % by weight of sodium lauryl sulfate) for 45 seconds, and then rinsed again with water and left to dry in the open air overnight. This whole washing treatment was performed twice.
  • shampoo aqueous solution containing 1 % by weight of sodium lauryl sulfate
  • composition 1 C firstly with composition 1A and then with composition 1 B for comparison.

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Abstract

L'invention concerne un procédé cosmétique pour traiter des matières de kératine, comprenant : (i) l'application, sur les matières de kératine, d'une composition comprenant un polymère (I) : dans laquelle R' représente indépendamment H ou un groupe acétyle ou un groupe -CO-L-SH, le polymère contenant au moins un groupe R'=-CO-L-SH, L étant un groupe à base d'hydrocarbure bivalent comprenant de 2 à 20 atomes de carbone, n est dans la plage de 5 à 2000. L'invention concerne l'application pour le traitement d'odeur corporelle humaine, pour lutter contre la formation de pellicules sur le cuir chevelu, conférer une souplesse aux cheveux et/ou rendre les cheveux faciles à peigner.
PCT/EP2016/065410 2015-08-07 2016-06-30 Procédé cosmétique permettant de traiter des matières de kératine WO2017025244A1 (fr)

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CN111620960A (zh) * 2020-06-19 2020-09-04 河北科技大学 一种氨基酸改性半乳甘露聚糖及其制备方法和应用
CN111936117A (zh) * 2017-11-17 2020-11-13 生活实验公司 含角蛋白材料的共价处理
WO2024043020A1 (fr) * 2022-08-23 2024-02-29 住友化学株式会社 Composé et agent d'extraction métallique

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WO2019164841A1 (fr) * 2018-02-20 2019-08-29 Living Proof, Inc. Traitement covalent avec des thiols de matériaux contenant de la kératine

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111936117A (zh) * 2017-11-17 2020-11-13 生活实验公司 含角蛋白材料的共价处理
CN111620960A (zh) * 2020-06-19 2020-09-04 河北科技大学 一种氨基酸改性半乳甘露聚糖及其制备方法和应用
CN111620960B (zh) * 2020-06-19 2021-12-10 河北科技大学 一种氨基酸改性半乳甘露聚糖及其制备方法和应用
WO2024043020A1 (fr) * 2022-08-23 2024-02-29 住友化学株式会社 Composé et agent d'extraction métallique

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