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WO2000018360A1 - Use of polymers obtainable from hydroxystyrene in hair compositions - Google Patents

Use of polymers obtainable from hydroxystyrene in hair compositions Download PDF

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Publication number
WO2000018360A1
WO2000018360A1 PCT/FR1999/002276 FR9902276W WO0018360A1 WO 2000018360 A1 WO2000018360 A1 WO 2000018360A1 FR 9902276 W FR9902276 W FR 9902276W WO 0018360 A1 WO0018360 A1 WO 0018360A1
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WIPO (PCT)
Prior art keywords
use according
monomer
hydroxystyrene
polymer
group
Prior art date
Application number
PCT/FR1999/002276
Other languages
French (fr)
Inventor
Christine Dupuis
Original Assignee
L'oreal
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Filing date
Publication date
Application filed by L'oreal filed Critical L'oreal
Priority to JP2000571882A priority Critical patent/JP2002525304A/en
Priority to AU56329/99A priority patent/AU5632999A/en
Priority to EP99943042A priority patent/EP1115368A1/en
Publication of WO2000018360A1 publication Critical patent/WO2000018360A1/en

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Classifications

    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8117—Homopolymers or copolymers of aromatic olefines, e.g. polystyrene; Compositions of derivatives of such polymers
    • 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

Definitions

  • the subject of the invention is the use of linear or branched polymers capable of being obtained by a process comprising a homo- or (co) -polymerization of at least one hydroxystyrene monomer, one of its precursors or the one of its salts in hair compositions, as a film-forming agent with a view to maintaining and / or shaping the hairstyle.
  • the most common hair products for fixing the hair on the cosmetics market are aerosol or pump spray compositions such as hairsprays, sprays or mousses, essentially consisting of a solution, most often alcoholic or hydroalcoholic and a film-forming polymer soluble in water or in alcohol, mixed with various cosmetic adjuvants.
  • compositions for maintaining and / or shaping the hair of the prior art which contain in their formulation styling polymers, can alter the cosmetic properties of the hair. These can, after application of such compositions, become rough, lose their natural softness or their pleasant appearance.
  • Polymers are therefore sought for hair compositions, in particular for maintaining and / or fixing the hairstyle, which provide the hair, in addition to satisfactory fixing, with good cosmetics, in particular good disentangling, softness and a feel. pleasant.
  • linear or branched polymers capable of being obtained by a process comprising a homo- or (co) -polymerization of at least one hydroxystyrene monomer, one of its precursors or one of its salts.
  • the subject of the invention is the use, in a hair cosmetic composition, of linear or branched polymers capable of being obtained by a process comprising a homo- or (co) -polymerization of at least one hydroxystyrene monomer, the one of its precursors or one of its salts, the phenyl group of the monomer comprising at least one hydroxyl moiety and being optionally substituted by one or more radicals selected from the group comprising alkyl radicals to C l2, alkoxyalkyl d to C 12 , halogens, SO 3 H, acyls (C 2 to C 12 ) amino, carboxy, carboxyalkyls C 1 to C 12 , as film-forming agents, for the purpose of maintaining and / or fixing the hairstyle.
  • Another object of the invention is a method for maintaining and / or fixing the hairstyle which includes this use.
  • linear or branched polymers particularly targeted by the present invention are those distributed by Clariant under the name PHS-E, PHS-PG, PHS-N or even PHS-PG-L.
  • the term "precursor of a hydroxystyrene monomer” means any phenolic derivative capable of leading to hydroxystyrene by the way of a degradation reaction in an acid medium, in particular by dehydration in an acid medium.
  • the precursor can be acetoxystyrene or 4-hydroxyphenylmethyl carbinol and the degradation reaction can, in this case, be diagrammed as follows:
  • PHS-E is a homopolymer corresponding to the formula:
  • PHS-E is obtained from acetoxystyrene by means of radical polymerization followed by hydrolysis. Its molecular mass is between 8,000 and 100,000 g / mol. PHS-E is a linear polymer.
  • PHS-PG is a polymer corresponding to the formula:
  • PHS-PG is obtained by polymerization catalyzed in an acid medium, from 4-hydroxyphé ⁇ ylméthyl carbinol. Its molecular mass is between 4000 and 7000 g / mol.
  • PHS-N is a polymer corresponding to the formula:
  • PHS-N is a polymer obtained by catalyzed polymerization in an acid medium of 4-hydroxyphenylmetylcarbinol. Its molecular mass is between 4,000 and 7,000 g / mol.
  • PHS-PG-L is a polymer having the same crude formula as PHS-E. However, the process for obtaining it is different since the polymerization is carried out from hydroxystyrene monomers.
  • the polymer is capable of being obtained by the copolymerization of:
  • the vinyl, acrylic or methacrylic monomers may contain one or more siloxane groups. In this case, they are chosen, in particular, from the group comprising:
  • - Ri represents H or CH 3 ,
  • - R 2 represents (CH 2 ) P , p being an integer which may be zero, - R 3 and R 4 represent, independently, CH 3 or an aliphatic, cycloaliphatic or aromatic group at d to C 12 ; the vinyl, allyl, ether ester or amide monomer of acrylic or methacrylic acid comprising one or more halogen groups, in particular chlorinated and / or fluorinated groups and / or comprising an absorbing group in UVA and / or UVB, in in particular the benzylidene camphor and benzotriazole groups, which may or may not be substituted.
  • the polymer is obtained by a homopolymerization reaction. This can advantageously be carried out from acetoxystyrene to obtain the poly-p-acetoxystyrene and be followed by hydrolysis. It can also be carried out in an acid medium from 4-hydroxyphenylmethyl carbinol.
  • the polymer is advantageously a homopolymer belonging to the family of poly-p-hydroxystyrene, and preferably poly-4-hydroxystyrene is chosen.
  • the polymer used according to the invention is advantageously chosen from those which have a molecular mass of between 5,000 and 300,000 g / mol, and preferably between 8,000 and 100,000 g / mol.
  • the polymer (s) are preferably present at concentrations of between 0.1 and 20% by weight, and more preferably, between 0.5 and 10% by weight relative to the total weight of the composition.
  • the polymers are used in a cosmetically acceptable medium which is preferably constituted by water or one or more cosmetically acceptable solvents such as monoalcohols, polyalcohols, glycol ethers or fatty acid esters, or water mixtures - solvent (s).
  • These solvents are preferably C ⁇ -C 4 alcohols.
  • these alcohols there may be mentioned ethanol, isopropanol, polyalcohols such as diethylene glycol, glycol ethers, such as monoalkyl ethers of glycol, of diethylene glycol, of propylene glycol or of dipropylene glycol. Ethanol is particularly preferred.
  • the polymers with at least one additive chosen from thickeners, fatty acid esters, fatty acid and glycerol esters, volatile or non-volatile silicones, modified or not, soluble or insoluble in the composition , surfactants, perfumes, preservatives, sunscreens, proteins, vitamins, polymers, vegetable, animal, mineral or synthetic oils and any other additive conventionally used in cosmetic compositions intended to be applied to the hair.
  • at least one additive chosen from thickeners, fatty acid esters, fatty acid and glycerol esters, volatile or non-volatile silicones, modified or not, soluble or insoluble in the composition , surfactants, perfumes, preservatives, sunscreens, proteins, vitamins, polymers, vegetable, animal, mineral or synthetic oils and any other additive conventionally used in cosmetic compositions intended to be applied to the hair.
  • additives are generally present in the composition according to the invention in proportions which may advantageously range from 0.001 to 20% by weight relative to the total weight of the composition.
  • the precise amount of each additive depends on its nature and is easily determined by those skilled in the art.
  • compositions can be packaged in various forms, in particular in pump dispensers or in aerosol containers, in order to ensure application of the composition in vaporized form or in the form of foam.
  • forms of packaging are indicated, for example, when it is desired to obtain a spray, a lacquer or a foam for fixing or treating hair.
  • the compositions in accordance with the invention can also be in the form of creams, gels, emulsions or waxes.
  • the composition formed with the polymer used according to the invention when packaged in the form of an aerosol, with a view to obtaining a lacquer or a foam, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n -butane, propane, isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures.
  • volatile hydrocarbons such as n -butane, propane, isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures.
  • Carbon dioxide, nitrous oxide, dimethyl ether (DME), nitrogen, compressed air can also be used as a propellant. You can also use a mixture of propellants.
  • dimethyl ether is used.
  • the propellant is present at a concentration between 5 and 90% by weight relative to the total weight of the composition in the aerosol device and, more particularly, at a concentration between 10 and 60%.
  • composition A comprises a conventional film-forming polymer
  • composition B comprises poly-4-hydroxystyrene.
  • Table 1 The formulations are summarized in Table 1 below. Table 1
  • a sensory test is carried out by implementing the protocol below.
  • the combination according to the invention has a significant advantage in disentangling, gently and in touch. It is noted that the composition according to the invention provides a marked improvement with regard to the ease of disentangling.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

The invention concerns the use of linear or branched polymers obtainable by a process consisting in homopolymerisation or (co)polymerisation of at least a hydroxystyrene monomer, one of its precursors or one of its salts, in cosmetic compositions for hair care, as film-forming agent for hair fixing and/or hair styling.

Description

UTILISATION DE POLYMERES SUSCEPTIBLES D'ETRE OBTENUS A PARTIR D' HYDROXYSTYRENE DANS DES COMPOSITIONS CAPILLAIRES USE OF POLYMERS SUSCEPTIBLE OF BEING OBTAINED FROM HYDROXYSTYRENE IN HAIR COMPOSITIONS
L'invention a pour objet l'utilisation de polymères linéaires ou branchés susceptibles d'être obtenus par un procédé comprenant une homo- ou une (co)-polymérisation d'au moins un monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels dans des compositions capillaires, comme agent filmogène en vue de maintenir et/ou de mettre en forme la coiffure.The subject of the invention is the use of linear or branched polymers capable of being obtained by a process comprising a homo- or (co) -polymerization of at least one hydroxystyrene monomer, one of its precursors or the one of its salts in hair compositions, as a film-forming agent with a view to maintaining and / or shaping the hairstyle.
Les produits capillaires pour la fixation des cheveux les plus répandus sur le marché de la cosmétique sont des compositions à pulvériser en aérosol ou en flacon pompe tels que les laques, les sprays ou les mousses, essentiellement constituées d'une solution le plus souvent alcoolique ou hydroalcoolique et d'un polymère filmogène soluble dans l'eau ou dans l'alcool, en mélange avec divers adjuvants cosmétiques.The most common hair products for fixing the hair on the cosmetics market are aerosol or pump spray compositions such as hairsprays, sprays or mousses, essentially consisting of a solution, most often alcoholic or hydroalcoholic and a film-forming polymer soluble in water or in alcohol, mixed with various cosmetic adjuvants.
De nombreuses compositions de maintien et/ou de mise en forme des cheveux de l'art antérieur, qui contiennent dans leur formulation des polymères de coiffage, peuvent altérer les propriétés cosmétiques des cheveux. Ceux-ci peuvent, après application de telles compositions, devenir rêches, perdre leur douceur naturelle ou leur aspect agréable.Numerous compositions for maintaining and / or shaping the hair of the prior art, which contain in their formulation styling polymers, can alter the cosmetic properties of the hair. These can, after application of such compositions, become rough, lose their natural softness or their pleasant appearance.
On recherche donc des polymères pour les compositions capillaires, notamment pour le maintien et/ou la fixation de la coiffure, qui procurent à la chevelure, outre une fixation satisfaisante, de bonnes cosmétiques, en particulier un bon démêlage, de la douceur et un toucher agréable.Polymers are therefore sought for hair compositions, in particular for maintaining and / or fixing the hairstyle, which provide the hair, in addition to satisfactory fixing, with good cosmetics, in particular good disentangling, softness and a feel. pleasant.
De manière surprenante et inattendue, la Demanderesse a découvert qu'il était possible de répondre aux problèmes ci-dessus en utilisant des polymères linéaires ou branchés susceptibles d'être obtenus par un procédé comprenant une homo- ou une (co)-polymérisation d'au moins un monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels. L'invention a pour objet l'utilisation, dans une composition cosmétique capillaire, de polymères linéaires ou branchés susceptibles d'être obtenus par un procédé comprenant une homo- ou une (co)-polyméhsation d'au moins un monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels, le groupe phényl de ce monomère comprenant au moins un motif hydroxyle et étant éventuellement substitué par un ou plusieurs radicaux choisis dans le groupe comprenant les radicaux alkyles en Ci à Cl2, alcoxyalkyles en d à C12 , halogènes, S03H, acyles (C2 à C12) amino, carboxy, carboxyalkyles en Ci à C12, comme agents filmogènes, en vue du maintien et/ou de la fixation de la coiffure.Surprisingly and unexpectedly, the Applicant has discovered that it is possible to respond to the above problems by using linear or branched polymers capable of being obtained by a process comprising a homo- or (co) -polymerization of at least one hydroxystyrene monomer, one of its precursors or one of its salts. The subject of the invention is the use, in a hair cosmetic composition, of linear or branched polymers capable of being obtained by a process comprising a homo- or (co) -polymerization of at least one hydroxystyrene monomer, the one of its precursors or one of its salts, the phenyl group of the monomer comprising at least one hydroxyl moiety and being optionally substituted by one or more radicals selected from the group comprising alkyl radicals to C l2, alkoxyalkyl d to C 12 , halogens, SO 3 H, acyls (C 2 to C 12 ) amino, carboxy, carboxyalkyls C 1 to C 12 , as film-forming agents, for the purpose of maintaining and / or fixing the hairstyle.
Un autre objet de l'invention est un procédé pour maintenir et/ou fixer la coiffure qui comprend cette utilisation.Another object of the invention is a method for maintaining and / or fixing the hairstyle which includes this use.
Les polymères linéaires ou branchés particulièrement visés par la présente invention sont ceux distribués par Clariant sous l'appellation PHS-E, PHS-PG, PHS-N ou encore PHS-PG-L.The linear or branched polymers particularly targeted by the present invention are those distributed by Clariant under the name PHS-E, PHS-PG, PHS-N or even PHS-PG-L.
Au sens de la présente invention, on entend par "précurseur d'un monomère hydroxystyrene" tout dérivé phénolique susceptible de conduire à l'hydroxystyrène par la voie d'une réaction de dégradation en milieu acide, notamment par déshydratation en milieu acide. A titre d'exemple, le précurseur peut être l'acétoxystyrène ou le 4-hydroxyphénylméthyl carbinol et la réaction de dégradation peut, dans ce cas, être schématisée de la façon suivante:For the purposes of the present invention, the term "precursor of a hydroxystyrene monomer" means any phenolic derivative capable of leading to hydroxystyrene by the way of a degradation reaction in an acid medium, in particular by dehydration in an acid medium. By way of example, the precursor can be acetoxystyrene or 4-hydroxyphenylmethyl carbinol and the degradation reaction can, in this case, be diagrammed as follows:
acide.acid.
Figure imgf000004_0001
Figure imgf000004_0002
Le PHS-E est un homopolymère répondant à la formule:
Figure imgf000004_0001
Figure imgf000004_0002
PHS-E is a homopolymer corresponding to the formula:
Figure imgf000005_0001
Figure imgf000005_0001
Le PHS-E est obtenu à partir de l'acétoxystyrène au moyen d'une polymérisation radicalaire suivie d'une hydrolyse. Sa masse moléculaire est comprise entre 8 000 et 100 000 g/mol. Le PHS-E est un polymère linéaire.PHS-E is obtained from acetoxystyrene by means of radical polymerization followed by hydrolysis. Its molecular mass is between 8,000 and 100,000 g / mol. PHS-E is a linear polymer.
Le PHS-PG est un polymère répondant à la formule:PHS-PG is a polymer corresponding to the formula:
Figure imgf000005_0002
Figure imgf000005_0002
Le PHS-PG est obtenu par polymérisation catalysée en milieu acide, à partir du 4-hydroxyphéπylméthyl carbinol. Sa masse moléculaire est comprise entre 4000 et 7000 g/mol.PHS-PG is obtained by polymerization catalyzed in an acid medium, from 4-hydroxyphéπylméthyl carbinol. Its molecular mass is between 4000 and 7000 g / mol.
Le PHS-N est un polymère répondant à la formule: PHS-N is a polymer corresponding to the formula:
Figure imgf000006_0001
Figure imgf000006_0001
Le PHS-N est un polymère obtenu par polymérisation catalysée en milieu acide du 4-hydroxyphénylmétylcarbinol. Sa masse moléculaire est comprise entre 4 000 et 7 000 g/mol.PHS-N is a polymer obtained by catalyzed polymerization in an acid medium of 4-hydroxyphenylmetylcarbinol. Its molecular mass is between 4,000 and 7,000 g / mol.
Le PHS-PG-L est un polymère présentant la même formule brute que le PHS- E. Toutefois, le procédé d'obtention est différent puisque la polymérisation est effectuée à partir de monomères hydroxystyrene.PHS-PG-L is a polymer having the same crude formula as PHS-E. However, the process for obtaining it is different since the polymerization is carried out from hydroxystyrene monomers.
Selon un premier mode de réalisation des compositions conformes à l'invention, le polymère est susceptible d'être obtenu par la copolymérisation de:According to a first embodiment of the compositions in accordance with the invention, the polymer is capable of being obtained by the copolymerization of:
(i) au moins un monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels, le groupe phényl de ce monomère comprenant au moins un motif hydroxyle et étant éventuellement substitué par un ou plusieurs radicaux choisis dans le groupe comprenant les radicaux alkyles en d à Cι2, alcoxyalkyles en Ci à Cι2 , halogènes, S03H, acyles (C2 à Cι2) amino, carboxy, carboxyalkyles en Ci à Ci2, et (ii) au moins un autre monomère copolymérisable avec ledit monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels, cet autre monomère étant choisi dans le groupe comprenant les monomères acrylique, méthacrylique ou leurs dérivés, notamment les acrylates ou méthacrylates d'alkyle linéaire, cyclique ou ramifié en Ci à C10l tels que les acrylates ou méthacrylates de méthyle, d'éthyle, de propyle, de butyle, d'isobutyle, de tertiobutyle, et d'éthyl-2-hexyle, les acrylamides ou méthacrylamides N- substituées ou N,N'-substituées, les monomères de vinyle tels que les halogénures de vinyle, les esters de vinyle, notamment le benzoate de vinyle, le tertiobenzoate de vinyle ou l'acétate de vinyle.(i) at least one hydroxystyrene monomer, one of its precursors or one of its salts, the phenyl group of this monomer comprising at least one hydroxyl unit and being optionally substituted by one or more radicals chosen from the group comprising alkyl radicals of 2 to Cι, alkoxyalkyl -C Cι 2, halogen, S0 3 H, acyl (C 2 Cι 2) amino, carboxy, carboxyalkyl Ci -C i2, and (ii) at least one other monomer copolymerizable with said hydroxystyrene monomer, one of its precursors or one of its salts, this other monomer being chosen from the group comprising acrylic, methacrylic monomers or their derivatives, in particular acrylates or methacrylates of straight, cyclic or branched -C 10l such as acrylates or methacrylates of methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, and 2-ethyl-hexyl, the N-substituted or N, N'-substituted acrylamides or methacrylamides, vinyl monomers such as vinyl halides, vinyl esters, in particular vinyl benzoate, vinyl tert-benzoate or vinyl acetate.
Les monomères vinyliques, acryliques ou méthacryliques peuvent comporter un ou plusieurs groupes siloxane. Dans ce cas, ils sont choisis, en particulier, dans le groupe comprenant:The vinyl, acrylic or methacrylic monomers may contain one or more siloxane groups. In this case, they are chosen, in particular, from the group comprising:
les monomères de formule CH2=C(CH3)-C-0-(CH2)3-Si-0-Si(CH3)2-CH3,the monomers of formula CH2 = C (CH 3 ) -C-0- (CH 2 ) 3-Si-0-Si (CH 3 ) 2 -CH 3 ,
- les macromonomères siliconés à terminaison monofonctionnelle vinylique, allylique, ester éther ou amide de l'acide acrylique ou méthacrylique, de formule CH2=C(Rι)-C-X-R2-Si(CH3)(R )-O-Si(CH3)2-R3, dans laquelle:- silicone macromonomers with vinyl, allyl monofunctional termination, ether ester or amide of acrylic or methacrylic acid, of formula CH 2 = C (Rι) -CXR 2 -Si (CH 3 ) (R) -O-Si (CH 3 ) 2-R3, in which:
- Ri représente H ou CH3,- Ri represents H or CH 3 ,
- X représente O ou NH,- X represents O or NH,
- R2 représente (CH2)P, p étant un entier pouvant être nul, - R3 et R4 représentent, de manière indépendante, CH3 ou un groupe aliphatique, cycloaliphatique ou aromatique en d à C12; le monomère vinylique, allylique, ester éther ou amide de l'acide acrylique ou méthacrylique comportant un ou plusieurs groupes halogènes, en particulier chlorés et/ou fluorés et/ou comportant un groupe absorbant dans l'UVA et/ou l'UVB, en particulier les groupements benzylidene camphre et benzotriazole, substitués ou non. Selon un deuxième mode de réalisation de l'invention, le polymère est obtenu par une réaction d'homopolymerisation. Celle-ci peut être effectuée avantageusement à partir d' acétoxystyrène pour obtenir le poly-p- acétoxystyrène et être suivie d'une hydrolyse. Elle peut également être effectuée en milieu acide à partir du 4-hydroxyphénylméthyl carbinol.- R 2 represents (CH 2 ) P , p being an integer which may be zero, - R 3 and R 4 represent, independently, CH 3 or an aliphatic, cycloaliphatic or aromatic group at d to C 12 ; the vinyl, allyl, ether ester or amide monomer of acrylic or methacrylic acid comprising one or more halogen groups, in particular chlorinated and / or fluorinated groups and / or comprising an absorbing group in UVA and / or UVB, in in particular the benzylidene camphor and benzotriazole groups, which may or may not be substituted. According to a second embodiment of the invention, the polymer is obtained by a homopolymerization reaction. This can advantageously be carried out from acetoxystyrene to obtain the poly-p-acetoxystyrene and be followed by hydrolysis. It can also be carried out in an acid medium from 4-hydroxyphenylmethyl carbinol.
Selon ce mode de réalisation de l'invention, le polymère est avantageusement un homopolymère appartenant à la famille des poly-p-hydroxystyrène, et de préférence on choisit le poly-4-hydroxystyrène.According to this embodiment of the invention, the polymer is advantageously a homopolymer belonging to the family of poly-p-hydroxystyrene, and preferably poly-4-hydroxystyrene is chosen.
Conformément à l'invention, on peut utiliser:In accordance with the invention, it is possible to use:
- uniquement un homopolymère linéaire,- only a linear homopolymer,
- uniquement un homopolymère branché, ou encore - un mélange d'homopolymères linéaires et d'homopolymères branchés.- only a branched homopolymer, or - a mixture of linear homopolymers and branched homopolymers.
Le polymère utilisé selon l'invention est avantageusement choisi parmi ceux qui présentent une masse moléculaire comprise entre 5 000 et 300 000 g/mol, et de préférence comprise entre 8 000 et 100 000 g/mol.The polymer used according to the invention is advantageously chosen from those which have a molecular mass of between 5,000 and 300,000 g / mol, and preferably between 8,000 and 100,000 g / mol.
Dans les compositions conformes à l'invention, le ou les polymères sont, de préférence, présents à des concentrations comprises entre 0,1 et 20 % en poids, et plus préférentiellement, comprises entre 0,5 et 10 % en poids par rapport au poids total de la composition.In the compositions in accordance with the invention, the polymer (s) are preferably present at concentrations of between 0.1 and 20% by weight, and more preferably, between 0.5 and 10% by weight relative to the total weight of the composition.
Les polymères sont utilisés dans un milieu cosmétiquement acceptable qui est de préférence constitué par de l'eau ou un ou plusieurs solvants cosmétiquement acceptables tels que des monoalcools, des polyalcools, des éthers de glycol ou des esters d'acides gras, ou des mélanges eau-solvant(s). Ces solvants sont, de préférence, des alcools en Cι-C4. Parmi ces alcools, on peut citer Péthanol, Pisopropanol, les polyalcools tels que le diéthylèneglycol, les éthers de glycol, tels que les monoalkyléthers de glycol, de diéthylèneglycol, de propylèneglycol ou de dipropylèneglycol. L'éthanol est particulièrement préféré.The polymers are used in a cosmetically acceptable medium which is preferably constituted by water or one or more cosmetically acceptable solvents such as monoalcohols, polyalcohols, glycol ethers or fatty acid esters, or water mixtures - solvent (s). These solvents are preferably Cι-C 4 alcohols. Among these alcohols, there may be mentioned ethanol, isopropanol, polyalcohols such as diethylene glycol, glycol ethers, such as monoalkyl ethers of glycol, of diethylene glycol, of propylene glycol or of dipropylene glycol. Ethanol is particularly preferred.
On peut également utiliser les polymères avec au moins un additif choisi parmi les épaississants, les esters d'acides gras, les esters d'acides gras et de glycérol, les silicones volatiles ou non volatiles, modifiées ou non, solubles ou insolubles dans la composition, les tensioactifs, les parfums, les conservateurs, les filtres solaires, les protéines, les vitamines, les polymères, les huiles végétales, animales, minérales ou synthétiques et tout autre additif classiquement utilisé dans les compositions cosmétiques destinées à être appliquées sur les cheveux.It is also possible to use the polymers with at least one additive chosen from thickeners, fatty acid esters, fatty acid and glycerol esters, volatile or non-volatile silicones, modified or not, soluble or insoluble in the composition , surfactants, perfumes, preservatives, sunscreens, proteins, vitamins, polymers, vegetable, animal, mineral or synthetic oils and any other additive conventionally used in cosmetic compositions intended to be applied to the hair.
Ces additifs sont en général présents dans la composition selon l'invention dans des proportions pouvant aller, avantageusement, de 0,001 à 20 % en poids par rapport au poids total de la composition. La quantité précise de chaque additif est fonction de sa nature et est déterminée facilement par l'homme de l'art.These additives are generally present in the composition according to the invention in proportions which may advantageously range from 0.001 to 20% by weight relative to the total weight of the composition. The precise amount of each additive depends on its nature and is easily determined by those skilled in the art.
Bien entendu, l'homme de l'art veillera à choisir le ou les éventuels composés à ajouter à la composition selon l'invention de manière telle que les propriétés avantageuses attachées intrinsèquement à la composition conforme à l'invention ne soient pas, ou substantiellement pas, altérées par l'addition envisagée.Of course, those skilled in the art will take care to choose the optional compound (s) to be added to the composition according to the invention in such a way that the advantageous properties intrinsically attached to the composition according to the invention are not, or substantially not, altered by the proposed addition.
Ces compositions peuvent être conditionnées sous diverses formes, notamment dans des flacons pompes ou dans des récipients aérosols, afin d'assurer une application de la composition sous forme vaporisée ou sous forme de mousse. De telles formes de conditionnement sont indiquées, par exemple, lorsqu'on souhaite obtenir un spray, une laque ou une mousse pour la fixation ou le traitement des cheveux. Les compositions conformes à l'invention peuvent aussi se présenter sous la forme de crèmes, de gels, d'émulsions ou de cires.These compositions can be packaged in various forms, in particular in pump dispensers or in aerosol containers, in order to ensure application of the composition in vaporized form or in the form of foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray, a lacquer or a foam for fixing or treating hair. The compositions in accordance with the invention can also be in the form of creams, gels, emulsions or waxes.
Lorsque la composition formée avec le polymère utilisé selon l'invention est conditionnée sous forme d'aérosol, en vue d'obtenir une laque ou une mousse, elle comprend au moins un agent propulseur qui peut être choisi parmi les hydrocarbures volatils tels que le n-butane, le propane, l'isobutane, le pentane, un hydrocarbure chloré et/ou fluoré et leurs mélanges. On peut également utiliser en tant qu'agent propulseur le gaz carbonique, le protoxyde d'azote, le diméthyléther (DME), l'azote, l'air comprimé. On peut aussi utiliser un mélange de propulseurs. De préférence, on utilise le diméthyl éther.When the composition formed with the polymer used according to the invention is packaged in the form of an aerosol, with a view to obtaining a lacquer or a foam, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n -butane, propane, isobutane, pentane, a chlorinated and / or fluorinated hydrocarbon and their mixtures. Carbon dioxide, nitrous oxide, dimethyl ether (DME), nitrogen, compressed air can also be used as a propellant. You can also use a mixture of propellants. Preferably, dimethyl ether is used.
Avantageusement, l'agent propulseur est présent à une concentration comprise entre 5 et 90 % en poids par rapport au poids total de la composition dans le dispositif aérosol et, plus particulièrement, à une concentration comprise entre 10 et 60 %.Advantageously, the propellant is present at a concentration between 5 and 90% by weight relative to the total weight of the composition in the aerosol device and, more particularly, at a concentration between 10 and 60%.
L'invention va être plus complètement illustrée à l'aide de l'exemple non limitatif suivant.The invention will be more fully illustrated with the aid of the following nonlimiting example.
Tous les pourcentages sont des pourcentages relatifs en poids par rapport au poids total de la composition.All the percentages are relative percentages by weight relative to the total weight of the composition.
EXEMPLE (Comparatif en flacon pompe):EXAMPLE (Comparative in pump bottle):
On a préparé les deux compositions de coiffage suivantes A et B. La composition A comprend un polymère filmogène classique, tandis que la composition B comprend du poly-4-hydroxystyrène. Les formulations sont résumées dans le tableau 1 ci-après. Tableau 1The following two styling compositions A and B were prepared. Composition A comprises a conventional film-forming polymer, while composition B comprises poly-4-hydroxystyrene. The formulations are summarized in Table 1 below. Table 1
Figure imgf000011_0001
Figure imgf000011_0001
On réalise un test sensoriel en mettant en œuvre le protocole ci-après.A sensory test is carried out by implementing the protocol below.
On vaporise par demie tête les compositions A et B conditionnées dans un équipement flacon pompe sur un panel de 7 modèles. Après séchage, on obtient un pouvoir laquant identique et on évalue la facilité de démêlage, la douceur et le toucher pour chacune de ces compositions. Pour chacun des 3 critères, l'expérimentateur attribue une note entre 0 et 50 et on calcule la moyenne sur le panel. Cette moyenne est rapportée dans le tableau 2 ci-après.Half a head is sprayed with compositions A and B packaged in pump bottle equipment on a panel of 7 models. After drying, an identical lacquering power is obtained and the ease of disentangling, the softness and the feel for each of these compositions is evaluated. For each of the 3 criteria, the experimenter assigns a score between 0 and 50 and the average is calculated on the panel. This average is reported in Table 2 below.
Tableau 2Table 2
Figure imgf000011_0002
Figure imgf000011_0002
Par conséquent, l'association selon l'invention présente un avantage significatif en démêlage, en douceur et en toucher. On remarque que la composition conforme à l'invention procure une nette amélioration en ce qui concerne la facilité de démêlage. Consequently, the combination according to the invention has a significant advantage in disentangling, gently and in touch. It is noted that the composition according to the invention provides a marked improvement with regard to the ease of disentangling.

Claims

REVENDICATIONS
1. Utilisation, dans une composition cosmétique capillaire, de polymères linéaires ou branchés susceptibles d'être obtenus par un procédé comprenant une homo- ou une (co)-polymérisation d'au moins un monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels, le groupe phényl de ce monomère comprenant au moins un motif hydroxyle et étant éventuellement substitué par un ou plusieurs radicaux choisis dans le groupe comprenant les radicaux alkyles en Ci à C12, alcoxyalkyles en Ci à Cι2 , halogènes, S03H, acyles (C2 à C12) amino, carboxy, carboxyalkyles en d à C12, comme agents filmogènes, en vue du maintien et/ou de la fixation de la coiffure.1. Use, in a hair cosmetic composition, of linear or branched polymers capable of being obtained by a process comprising a homo- or a (co) -polymerization of at least one hydroxystyrene monomer, one of its precursors or l a salt thereof, the phenyl of this monomer group comprising at least one hydroxyl moiety and being optionally substituted by one or more radicals selected from the group comprising alkyl radicals Ci to C12 alkoxyalkyl -C Cι 2, halogen, S0 3 H, acyls (C 2 to C 12 ) amino, carboxy, carboxyalkyls d to C 12 , as film-forming agents, with a view to maintaining and / or fixing the hairstyle.
2. Utilisation selon la revendication 1 , caractérisée par le fait que le polymère présente une masse moléculaire comprise entre 5 000 et 300 000, et de préférence comprise entre 8 000 et 100 000.2. Use according to claim 1, characterized in that the polymer has a molecular weight between 5,000 and 300,000, and preferably between 8,000 and 100,000.
3. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le polymère filmogène est susceptible d'être obtenu par la copolymérisation de:3. Use according to any one of the preceding claims, characterized in that the film-forming polymer is capable of being obtained by the copolymerization of:
(i) au moins un monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels, le groupe phényl de ce monomère comprenant au moins un motif hydroxyle et étant éventuellement substitué par un ou plusieurs radicaux choisis dans le groupe comprenant les radicaux alkyles en d à Cι , alcoxyalkyles en Ci à Cι2, halogènes, S03H, acyles (C2 à C12) amino, carboxy, carboxyalkyles en Ci à Cι2, et(i) at least one hydroxystyrene monomer, one of its precursors or one of its salts, the phenyl group of this monomer comprising at least one hydroxyl unit and being optionally substituted by one or more radicals chosen from the group comprising alkyl radicals in D to Cι, alkoxyalkyls in Ci in Cι 2 , halogens, S0 3 H, acyls (C 2 in C 12 ) amino, carboxy, carboxyalkyls in Ci in Cι 2 , and
(ii) au moins un autre monomère copolymérisable avec ledit monomère hydroxystyrene, l'un de ses précurseurs ou l'un de ses sels, cet autre monomère étant choisi dans le groupe comprenant les monomères acrylique, méthacrylique ou leurs dérivés, notamment les acrylates ou méthacrylates d'alkyle linéaires, cycliques ou ramifiés en Ci à C10, les acrylamides ou méthacrylamides N-substituées ou N,N'-substituées, les monomères de vinyle tels que les halogénures de vinyle, les esters de vinyle, notamment le benzoate de vinyle, le tertiobenzoate de vinyle ou l'acétate de vinyle.(ii) at least one other monomer copolymerizable with said hydroxystyrene monomer, one of its precursors or one of its salts, this other monomer being chosen from the group comprising acrylic, methacrylic monomers or their derivatives, in particular linear, cyclic or branched C1 to C10 alkyl acrylates or methacrylates, N-substituted or N, N'-substituted acrylamides or methacrylamides, vinyl monomers such as vinyl halides, vinyl esters, in particular vinyl benzoate, vinyl tert-benzoate or vinyl acetate.
4. Utilisation selon l'une quelconque des revendications 1 ou 2, caractérisée par le fait que le polymère est obtenu par homopolymérisation pour obtenir un polymère du type poly-p-hydroxystyrène, éventuellement substitué, et de préférence le poly-4-hydroxystyrène.4. Use according to any one of claims 1 or 2, characterized in that the polymer is obtained by homopolymerization to obtain a polymer of the poly-p-hydroxystyrene type, optionally substituted, and preferably poly-4-hydroxystyrene.
5. Utilisation selon l'une quelconque des revendications précédentes, caractérisée en ce que le polymère est présent dans la composition cosmétique capillaire à une concentration comprise entre 0,1 et 20 % en poids, et de préférence comprise entre 0,5 et 10 % en poids par rapport au poids total de la composition.5. Use according to any one of the preceding claims, characterized in that the polymer is present in the hair cosmetic composition at a concentration between 0.1 and 20% by weight, and preferably between 0.5 and 10% by weight relative to the total weight of the composition.
6. Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que la composition contient, en outre, des additifs cosmétiques conventionnels choisis dans le groupe comprenant les corps gras, les agents épaississants, les adoucissants, les agents anti-mousse, les agents hydratants, les agents antiperspirants, les agents alcalinisants, les colorants, les pigments, les parfums, les conservateurs, les tensioactifs, les polymères hydrocarbonés, les silicones volatiles ou non, modifiées ou non, les polyols, les protéines et les vitamines.6. Use according to any one of the preceding claims, characterized in that the composition also contains conventional cosmetic additives chosen from the group comprising fatty substances, thickening agents, softeners, anti-foaming agents, moisturizing agents, antiperspirants, alkalizing agents, dyes, pigments, perfumes, preservatives, surfactants, hydrocarbon polymers, volatile or unmodified or unmodified silicones, polyols, proteins and vitamins.
7. Utilisation selon l'une quelconque des revendications précédentes, pour la fabrication d'un produit capillaire pour maintenir et/ou fixer la coiffure.7. Use according to any one of the preceding claims, for the manufacture of a hair product for maintaining and / or fixing the hairstyle.
8. Utilisation selon la revendication 7, où le produit est à application non rincée. 8. Use according to claim 7, in which the product is applied without rinsing.
9. Procédé pour maintenir et/ou fixer la coiffure, caractérisé par le fait qu'il comprend une utilisation selon l'une quelconque des revendications précédentes. 9. A method for maintaining and / or fixing the hairstyle, characterized in that it comprises a use according to any one of the preceding claims.
PCT/FR1999/002276 1998-09-25 1999-09-24 Use of polymers obtainable from hydroxystyrene in hair compositions WO2000018360A1 (en)

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JP2000571882A JP2002525304A (en) 1998-09-25 1999-09-24 Use of polymers obtainable from hydroxystyrene in hair compositions
AU56329/99A AU5632999A (en) 1998-09-25 1999-09-24 Use of polymers obtainable from hydroxystyrene in hair compositions
EP99943042A EP1115368A1 (en) 1998-09-25 1999-09-24 Use of polymers obtainable from hydroxystyrene in hair compositions

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FR9812040A FR2783710B1 (en) 1998-09-25 1998-09-25 USE OF POLYMERS SUSCEPTIBLE OF BEING OBTAINED FROM HYDROXYSTYRENE IN HAIR COMPOSITIONS
FR98/12040 1998-09-25

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US7371800B2 (en) * 2004-05-05 2008-05-13 Dupont Electronic Polymers L.P. Derivatized novolak polyhydroxystyrene from hydroxyphenylmethylcarbinol
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Citations (3)

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Publication number Priority date Publication date Assignee Title
GB2072508A (en) * 1980-02-27 1981-10-07 Maruzen Oil Co Ltd An antifungal and antibacterial agent
EP0605951A1 (en) * 1992-11-24 1994-07-13 Advanced Genetic Technologies Corporation A nail lacquer composition
WO1994022929A1 (en) * 1993-04-02 1994-10-13 Hoechst Celanese Corporation Amphoteric copolymer derived from vinylpyridine & acetoxystyrene

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2072508A (en) * 1980-02-27 1981-10-07 Maruzen Oil Co Ltd An antifungal and antibacterial agent
EP0605951A1 (en) * 1992-11-24 1994-07-13 Advanced Genetic Technologies Corporation A nail lacquer composition
WO1994022929A1 (en) * 1993-04-02 1994-10-13 Hoechst Celanese Corporation Amphoteric copolymer derived from vinylpyridine & acetoxystyrene

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FR2783710A1 (en) 2000-03-31

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