WO2012130601A1 - Vernis à ongles photoréticulables exempts de monomères insaturés - Google Patents

Vernis à ongles photoréticulables exempts de monomères insaturés Download PDF

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Publication number
WO2012130601A1
WO2012130601A1 PCT/EP2012/054325 EP2012054325W WO2012130601A1 WO 2012130601 A1 WO2012130601 A1 WO 2012130601A1 EP 2012054325 W EP2012054325 W EP 2012054325W WO 2012130601 A1 WO2012130601 A1 WO 2012130601A1
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meth
photo
acrylate groups
cosmetic composition
formula
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PCT/EP2012/054325
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WO2012130601A9 (fr
Inventor
Guillaume Kergosien
Carl Riachi
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L'oreal
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Publication of WO2012130601A9 publication Critical patent/WO2012130601A9/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers
    • 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
    • A61K2800/81—Preparation or application process involves irradiation
    • 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
    • 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
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers

Definitions

  • the present invention relates to photo-crosslinkable, monomer-free cosmetic compositions, in particular nail varnishes, and also to a process for depositing a crosslinked coating in situ using these compositions.
  • Nail varnish compositions can be used as varnish base, as a nail makeup product, as a finishing composition, also known as a top coat, to be applied over the nail makeup product, or else as a cosmetic nailcare product. These compositions may be applied onto either human nails or false nails.
  • Liquid cosmetic compositions which, after deposition on the nail and exposure to actinic radiation undergo polymerization and/or crosslinking reactions in situ resulting in polymer networks that are usually crosslinked, are known in the field of nail varnishes.
  • Such photo-polymerizable and/or photo-crosslinkable compositions are described, for example, in patents CA 1 306 954, US 5 456 905, US 7 375 144 and FR 2 823 105.
  • compositions generally contain one or more polymers and/or prepolymers comprising polymerizable ethylenic double bonds, one or more reactive monomers containing double bond(s), at least one photo-initiator, optionally one or more agents for inhibiting the premature polymerization of the components, or alternatively photosensitizers for modifying the absorption spectrum of the photo-initiating system.
  • the main drawback of these compositions lies in the toxicity of the unsaturated monomers used. Specifically, these highly reactive, low molecular weight molecules diffuse readily into the subjacent and adjacent substrates, where they react with biological molecules.
  • the Applicant has sought to solve this toxicity problem of the photo- crosslinkable cosmetic compositions of the prior art by developing photo-crosslinkable cosmetic compositions containing, as sole polymerizable or crosslinkable reactive components, macromolecular compounds, i.e. reactive components whose molecular mass is high enough to prevent them from diffusing into the neighbouring biological substrates.
  • Patent US 7 375 144 describes photo-crosslinkable compositions free of monoacrylate monomers, which are capable of polymerizing under UV radiation.
  • the compositions described comprise large amounts of low molecular mass diacrylate compounds that can diffuse into the subjacent and adjacent substrates and react with biological molecules.
  • Patent FR 2 823 105 describes photo-crosslinkable compositions that are free of compounds with molecular masses of less than 500 g/mol. However, the described compositions do not make it possible to obtain compositions whose viscosity is suitable for them to be applied correctly to the nails, or do not make it possible to obtain films whose rigidity or cohesion is sufficient to obtain good wear properties on the nail.
  • photo-crosslinkable cosmetic compositions free of reactive monomers containing ethylenic double bond(s), comprising:
  • At least two polymers comprising ethylenic double bonds, the mean number of ethylenic double bonds per polymer molecule being greater than 1, the said at least two polymers comprising at least one polyester polymer containing (meth)acrylate groups and at least one polyether polymer containing (meth)acrylate groups, and
  • the polyester polymer(s) containing (meth)acrylate groups are present in a total content of greater than or equal to 40% by weight relative to the total weight of the photo- crosslinkable cosmetic composition.
  • the photo-crosslinkable cosmetic compositions free of reactive monomers containing ethylenic double bond(s) are free of (meth)acrylate monomers and of urethane (meth)acrylate monomers.
  • the said photo-crosslinkable cosmetic composition is a nail varnish.
  • a subject of the invention is also a cosmetic process for coating nails or false nails using these photo-crosslinkable cosmetic compositions defined previously.
  • - (poly)ol a monoalcohol or a polyol, preferably a diol, advantageously containing from 2 to 20 carbon atoms and more preferentially from 2 to 6 carbon atoms;
  • R being a Ci-C 6 alkylene, preferably -R-O- being (CH 2 -CH 2 -0) n or (CH 2 -CH 2 -CH 2 -0) n , n being an integer greater than 1, for example between 1 and 1000;
  • - (poly)hydroxylated one or more groups -OH.
  • the mean number of ethylenic double bonds borne by the polymers forming the crosslinked polymer network of the final cured coating must be greater than 1.
  • a polymerizable system formed from molecules (monomers, oligomers or polymers) each bearing only one double bond forms, after reaction of all of the double bonds, a macromolecular system containing linear or branched but non- crosslinked chains. Only the presence of a certain fraction of molecules bearing at least two double bonds and acting, as a result, as crosslinking agent makes it possible to obtain a crosslinked polymer system.
  • the mean number of fractions per polymer molecule is preferably greater than or equal to 2 and advantageously between 2 and 6, limits inclusive.
  • the harmlessness of the photo-crosslinkable cosmetic compositions of the present invention is due to the fact that the polymers comprising one or more ethylenic double bonds have a molecular mass that is sufficient to prevent them from diffusing towards and into the neighbouring biological substrates.
  • the term "sufficient molecular mass” means a weight-average molecular mass of greater than or equal to 400. In particular, the weight-average molecular mass may range from 400 to 5000.
  • the polyester polymer(s) containing (meth)acrylate groups and the polyether polymer(s) containing (meth)acrylate groups according to the invention each have a weight-average molecular mass of greater than or equal to 400, especially ranging from 450 to 5000 and preferably ranging from 500 to 3000.
  • Photo-crosslinkable polymers A composition in accordance with the present invention comprises polymers bearing ethylenic double bonds and having a suitable molar mass.
  • a composition in accordance with the present invention comprises more specifically in combination at least one polyester polymer containing (meth)acrylate groups and at least one polyether polymer containing (meth)acrylate groups. a) Polyester containing (meth)acrylate group(s)
  • a polyester polymer containing (meth)acrylate groups in accordance with the invention preferably comprises on average from 4 to 6 (meth)acrylate groups, and more preferentially on average 6 (meth)acrylate groups.
  • Such a polymer preferably has a molecular mass preferably greater than 800 g/mol and more preferentially between 1000 g/mol and 3000 g/mol.
  • This polymer may be chosen from:
  • polyesters This is a group of polymers of polyester type bearing one or more ethylenic double bonds, distributed randomly in the main polymer chain. These unsaturated polyesters are preferably obtained by polycondensation of a mixture:
  • linear or branched aliphatic or cycloaliphatic diols especially comprising from 2 to 50 carbon atoms and preferably from 2 to 20 carbon atoms, such as ethylene glycol, di ethylene glycol, propylene glycol, 1,4-butanediol or
  • cyclohexanedimethanol of aromatic diols containing from 6 to 50 carbon atoms and preferably from 6 to 20 carbon atoms such as bisphenol A and bisphenol B, and/or of diol dimers derived from the reduction of the fatty acid dimers as defined previously, and
  • polyesters containing (meth)acrylate side and/or end groups This is a group of polymers of polyester type obtained by polycondensation of a mixture:
  • polymerizable ethylenic double bonds - of linear or branched aliphatic or cycloaliphatic diols especially comprising from 2 to 50 carbon atoms and preferably from 2 to 20 carbon atoms, such as ethylene glycol, di ethylene glycol, propylene glycol, 1,4-butanediol or cyclohexanedimethanol, of aromatic diols containing from 6 to 50 carbon atoms and preferably from 6 to 20 carbon atoms, such as bisphenol A and bisphenol B, and
  • polyesters differ from those described above in point (1) by the fact that the ethylenic double bonds are not located in the main chain but on side groups or at the end of the chains. These ethylenic double bonds are those of the (meth)acrylate groups present in the polymer.
  • the said at least one polyester polymer containing (meth)acrylate groups is preferably a polyester containing (meth)acrylate groups bearing one or, preferably, several (meth)acrylate side and/or end groups.
  • the polyester polymer containing (meth)acrylate groups as defined previously may be partially modified by reaction with an amino group, as described in patent application US 2009/0 098 304.
  • Such polymers may especially be obtained by reaction between some of the ethylenic groups of the polyester polymer containing (meth)acrylate group(s) as described previously and a primary or secondary amine.
  • Such polyesters are sold, for example, by the company Cytec under the names Ebecryl 870 and Ebecryl 1870: molecular mass 1500 g/mol, on average 6 acrylate functions per molecule, Ebecryl 450: molar mass 1600 g/mol, on average 6 acrylate functions per molecule, Ebecryl 657 and Ebecryl 1657: molar mass 1500 g/mol, on average 4 acrylate functions per molecule, Ebecryl LEO 10801 : molar mass 1500 g/mol, on average 6 acrylate functions per molecule.
  • the said at least one polyester polymer containing (meth)acrylate groups is preferably present in the composition in a content ranging from 40% to 80% by weight relative to the total weight of the composition.
  • Polyether polymer containing (meth)acrylate groups are preferably present in the composition in a content ranging from 40% to 80% by weight relative to the total weight of the composition.
  • a polyether polymer containing (meth)acrylate groups in accordance with the invention preferably comprises at least 2 (meth)acrylate functions, preferably from 2 to 4 (meth)acrylate functions and more preferentially from 2.5 to 3.5 (meth)acrylate functions.
  • Such a polymer preferably has a molecular mass of between 400 g/mol and 1500 g/mol and more preferentially between 500 g/mol and 1000 g/mol.
  • This polymer is preferably obtained by esterification with the (meth)acrylic acid, on the one hand, or with all of the end hydroxyl groups derived from Ci -6 alkylene glycol homopolymers or copolymers, such as polyethylene glycol, polypropylene glycol, copolymers of ethylene oxide and of propylene oxide preferably having a weight-average molecular mass of less than 10 000 g/mol, polyethoxylated or polypropoxylated glycerols, polyethoxylated or polypropoxylated trimethylolpropanes, polyethoxylated or polypropoxylated pentaerythritols, polyethoxylated or polypropoxylated bis- trimethylolpropanes and polyethoxylated or polypropoxylated bis-pentaerythritols.
  • Such polymers are especially described in US patent No. 5 543 557.
  • the polyether polymer(s) containing (meth)acrylate groups are obtained by esterification with the (meth)acrylic acid, on the one hand, or all of the end hydroxyl groups derived from (poly)hydroxylated, preferably polyhydroxylated, and (poly)alkoxylated, preferably polyalkoxylated, compounds.
  • polyether polymer containing (meth)acrylate groups is chosen from ipounds of formula (I) below:
  • ALK 1 and ALK 2 which may be identical or different, represent a (Cj-C6)alkyl group such as ethyl or propyl;
  • ⁇ x 1 and x 2 which may be identical or different, represent an integer greater than or equal to 1 , for instance between 1 and 1000 inclusive;
  • R 1 and R 2 which may be identical or different, represent a hydrogen atom or a (Ci- C ⁇ alkyl group such as methyl;
  • R' preferably representing: i) a group of formula (II) below:
  • ALK 3 represents a (Ci-C 6 )alkyl group such as ethyl or propyl;
  • RECTIFIED SHEET RULE 91 ISA/EP - x represents an integer greater than or equal to 1 , for instance between 1 and 1000 inclusive;
  • R 3 represents a hydrogen atom or a (Ci-C 6 )alkyl group such as methyl
  • ALK 4 represents a (C
  • - x 4 represents an integer greater than or equal to 1, for instance between 1 and 1000 inclusive;
  • R 4 represents a hydrogen atom or a (Ci-C 6 )alkyl group such as methyl
  • ALK 5 and ALK 6 which may be identical or different, represent a (Ci-C 6 )alkyl group such as ethyl or propyl; or
  • ALK 7 and ALK 8 which may be identical or different, represent a (Ci-C6)alkyl group such as ethyl or propyl;
  • - and x which may be identical or different, represent an integer greater than or equal to 1, for instance between 1 and 1000 inclusive;
  • R and R which may be identical or different, represent a hydrogen atom or a (Ci- C 6 )alkyl group such as methyl;
  • R' being a hydrogen atom or a (Ci-C 6 )alkyl group such as ethyl, or an alkoxy group such as methoxy, or the group of formula (VI):
  • - ALK represents a (Cj-C6)alkyl group such as ethyl or propyl;
  • - x 9 represents an integer greater than or equal to 1 , for instance between 1 and 1000 inclusive;
  • - R 9 represents a hydrogen atom or a (Ci-C 6 )alkyl group such as methyl;
  • R" representing a hydrogen atom or a (Ci-C 6 )alkyl group such as ethyl, or an alkoxy group such as methoxy, or the group of formula (VII):
  • ALK 10 represents a (Ci-C 6 )alkyl group such as ethyl or propyl;
  • - x 10 represents an integer greater than or equal to 1, for instance between 1 and 1000 inclusive;
  • R 10 represents a hydrogen atom or a (Ci-C 6 )alkyl group such as methyl
  • the polyether polymer containing (meth)acrylate groups is chosen from polyethoxylated or polypropoxylated glyceryl triacrylates, polyethoxylated or polypropoxylated trimethylolpropane triacrylates, polyethoxylated or polypropoxylated bis- trimethylolpropane tetraacrylates, and polyethoxylated or polypropoxylated dipentaerythrityl pentaacrylates, and mixtures thereof.
  • Such polymers are sold by the company Cytec under the name Ebecryl ® LEO 10501; molecular mass 470 g/mol, on average 3 acrylate functions per molecule.
  • Polypropoxylated glyceryl triacrylates are sold, for example, under the names SR 9019 and SR 9020 by the company Sartomer, or under the names OTA-480 and Ebecryl ® 53 by the company Cytec.
  • Polyethoxylated trimethylolpropane triacrylates are sold, for example, under the names SR 454, SR 499, SR 502 and SR 415 by the company Sartomer, or under the names TMPEOTA and Ebecryl ® 160 by the company Cytec.
  • Polypropoxylated trimethylolpropane triacrylates are sold, for example, under the name SR 492 by the company Sartomer.
  • At least some, or all, of the ethylenic groups of the polyether polymer(s) containing (meth)acrylate groups are modified by reaction with an amino group.
  • Such polymers may advantageously correspond to formula ( ⁇ ) below.
  • the polyether polymer containing (meth)acrylate groups as defined previously may be partially modified by reaction with an amino group, as described in patent application US 2009/0 098 304.
  • Such polymers may especially be obtained by reaction between some of the ethylenic groups of the polyether polymer containing (meth)acrylate groups as described previously and a primary or secondary amine, according to the following reaction scheme (Michael addition):
  • ALK and ALK which may be identical or different, represent a (Ci-C6)alkyl group such as ethyl or propyl; x and x , which may be identical or different, represent an integer greater than or equal to 1, for instance between 1 and 1000 inclusive;
  • R 1 and R 2 which may be identical or different, represent a hydrogen atom or a (C C 6 )alkyl group such as methyl;
  • X which may be identical or different, represent a CH 2 group when is a double bond, or X represents an amino group CH 2 NR a R b when is a single bond with R a representing an alkyl optionally substituted, with a hydroxyl, alkoxy, tertiary amine or aryl, and R b representing a hydrogen or an alkyl optionally substituted with a hydroxide, alkoxy, tertiary amine or aryl.
  • R a and R b may be linked together to form a ring;
  • R' preferably representing: i) a group of formula ( ⁇ ) below:
  • Formula ( ⁇ ) being identical to formula (II) or only different in that it has in X a substitution with an amino group CH ⁇ NRaR b as defined previously; ii) a group of formula ( ⁇ ) below:
  • Formula ( ⁇ ) being identical to formula (III) or only different in that it has in X a substitution with an amino group CH 2 NR a R b as defined previously;
  • Formula (IV) being identical to formula (IV) or only different in that it has in X a substitution with an amino group CH 2 NR a Rb as defined previously; or iv) a group of formula (V) below:
  • Formula (V) being identical to formula (V) or only different in that it has in X a substitution with an amino group CH 2 NR a R b as defined previously;
  • R" representing a hydrogen atom or a (C 1 -C 6 )alkyl group such as ethyl, or an alkoxy group such as methoxy, or the group of formula (VII'):
  • Formula (VII') being identical to formula (VI) or only different in that it has in X a substitution with an amino group CH 2 R a R b as defined previously;
  • reaction between the (meth)acrylate and the amine does not require either catalyst or solvent.
  • the mole ratio between the amine and the ethylenic groups of the polyether polymer containing (meth)acrylate groups is between 0.01 : 1 and 0.5: 1.
  • Such polymers are sold, for example, by the company Cytec under the names Ebecryl ® LEO 10551 : molar mass 500 g/mol, on average 2.5 acrylate functions per molecule, Ebecryl ® LEO 10552: molar mass 1000 g/mol, on average 3.5 acrylate functions per molecule, or alternatively such polyether polymers modified by reaction with an amino group of suitable molar mass are sold, for example, under the names CN501 and CN550 by the company Sartomer, or under the names Ebecryl ® 80, Ebecryl ® 81 and Ebecryl ® 83 by the company Cytec, and under the names Photomer ® 5662 and Photomer ® 5930 by the company Cognis.
  • Ebecryl ® LEO 10551 molar mass 500 g/mol, on average 2.5 acrylate functions per molecule
  • Ebecryl ® LEO 10552 molar mass 1000 g/mol, on average 3.5 acrylate functions per
  • the said at least one polyether polymer containing (meth)acrylate groups is chosen from polyethers containing (meth)acrylate groups partially modified by reaction with an amino group.
  • the polyether polymer(s) containing (meth)acrylate groups are preferably present in a total content of greater than or equal to 10% by weight relative to the total weight of the photo-crosslinkable cosmetic composition, and advantageously between 20% and 40% by weight relative to the total weight of the photo-crosslinkable cosmetic composition, limits inclusive.
  • polyester polymer(s) containing (meth)acrylate groups and the polyether polymer(s) containing (meth)acrylate groups are preferably present in a total content of greater than or equal to 40% by weight relative to the total weight of the photo- crosslinkable cosmetic composition, and advantageously between 50% and 70% by weight relative to the total weight of the photo-crosslinkable cosmetic composition, limits inclusive.
  • the polyester polymer(s) containing (meth)acrylate groups and the polyether polymer(s) containing (meth)acrylate groups are preferably present in the composition in a respective total content such that the weight ratio of the polyester polymer(s) containing (meth)acrylate groups to the polyether polymer(s) containing (meth)acrylate groups is between 1 and 3, limits inclusive.
  • the polyether polymer(s) containing (meth)acrylate groups ensure solvation of the polyester polymer(s) containing (meth)acrylate groups, thus enabling satisfactory fluidization thereof and thereby leads to a nail varnish composition that has good mechanical properties in terms of rigidity and/or cohesion once the applied nail varnish has crosslinked.
  • the photoinitiators that may be used in the cosmetic compositions of the present invention are also known in the art and are described, for example, in the following articles: "Les photoinitiateurs dans la reticulation des revetements [Photoinitiators in the crosslinking of coatings]", G. Li Bassi, Double Liaison - Chimie des Peintures, No.
  • photoinitiators include • the -hydroxy ketones sold, for example, under the names Darocur ® 1173 and 4265, Irgacure ® 184, 2959 and 500 by the company BASF, and Additol ® CPK by the company Cytec,
  • the aromatic ketones sold for example, under the name Esacure ® TZT by Lamberti. Mention may also be made of the thioxanthones sold, for example, under the name Esacure ® ITX by Lamberti, and quinones. These aromatic ketones usually require the presence of a hydrogen-donating compound such as tertiary amines and especially alkanolamines. Mention may be made especially of the tertiary amine Esacure ® EDB sold by the company Lamberti.
  • acylphosphine oxides for instance the bis-acylphosphine oxides (BAPOs) sold, for example, under the names Irgacure ® 819, 1700 and 1800, Darocur ® 4265, Lucirin ® TPO and Lucirin ® TPO-L by the company BASF.
  • BAPOs bis-acylphosphine oxides
  • the photoinitiators of this group have the advantage, over the standard photoinitiators mentioned above, of being able to be integrated, via the double bonds, into the macromolecular system. This possibility reduces the content of residual free photoinitiators that have not undergone a photoinduced radical cleavage and consequently improves the harmlessness of the cosmetic compositions.
  • copolymenzable photoinitiators that may be mentioned include the benzophenone acryl derivatives sold by the company Cytec under the names Ebecryl ® P36 and Ebecryl ® P37.
  • polymer photoinitiators or photoinitiators attached to a high molecular weight molecule.
  • the choice of such a high-mass photoinitiator has the same advantage as the selection of exclusively polymeric copolymerizable components, namely better safety of the photo-crosslinkable cosmetic compositions due to the absence of small, highly reactive molecules capable of diffusing to the neighbouring biological substrates.
  • the weight-average molecular weight of the photoinitiator is preferably at least equal to 500 g/mol.
  • the polymer to which the photoinitiator group is attached may optionally comprise one or more ethylenic double bonds optionally enabling the integration, into the macromolecular network, of photoinitiator molecules that have not undergone photo- induced scission.
  • photo-crosslinkable cosmetic compositions of the present invention use is preferably made of a mixture of photoinitiators that absorb light at different wavelengths. It is thus possible to adapt the absorption spectrum of the photo-crosslinkable cosmetic compositions to the emission spectrum of the light sources used.
  • the content of photoinitiator(s) used depends on a large number of factors such as, for example, the reactivity of the various components of the mixture, the presence of pigments or dyes, the desired crosslinking density, the intensity of the light source or the exposure time.
  • the radical photoinitiator(s) are preferably present in a total content of greater than or equal to 0.1% by weight relative to the total weight of the composition and preferably between 1% and 5% by weight relative to the total weight of the composition.
  • the radical photoinitiator(s) are present in a total content of greater than or equal to 0.1% by weight relative to the total weight of the polyester polymer(s) containing (meth)acrylate groups and of the polyether containing (meth)acrylate groups, and preferably between 0.5% and 3% by weight relative to the total weight of the polyester polymer(s) containing (meth)acrylate groups and of the polyether(s) containing (meth)acrylate groups.
  • the cosmetic compositions of the present invention comprise at least one film-forming polymer.
  • film-forming polymer denotes a polymer that is capable, by itself (i.e. in the absence of an auxiliary film-forming agent or of external stimulus, for instance UV) of forming an isolable and especially continuous and adherent film, on a support, especially on the nails.
  • a single film-forming polymer or a mixture of film-forming polymers may be used in the composition.
  • This film-forming polymer may be chosen from the group formed by synthetic polymers of radical type or of polycondensate type, and polymers of natural origin, and mixtures thereof.
  • a film-forming polymer that is suitable for use in the invention may be chosen in particular from:
  • polysaccharide derivatives such as cellulose or guar gum derivatives.
  • a preferential polysaccharide derivative that is suitable for use in the invention may be nitrocellulose or a polysaccharide ester or alkyl ether.
  • polysaccharide ester or alkyl ether denotes a polysaccharide formed from repeating units comprising at least two identical or different rings having a degree of substitution per saccharide unit of between 1.9 and 3, preferably between 2.2 and 2.9 and more particularly between 2.4 and 2.8.
  • substitution denotes the functionalization of the hydroxyl groups into ester and/or alkyl ether functions, and/or the functionalization the carboxylic groups into ester functions.
  • it may be a polysaccharide that is partially or totally substituted with ester and/or alkyl ether groups.
  • the hydroxyl groups may be substituted with ester and/or C 2 -C 4 alkyl ether functions.
  • cellulose esters such as cellulose acetobutyrates or cellulose acetopropionates
  • cellulose alkyl ethers such as ethylcelluloses, and ethyl guars
  • - synthetic polymers such as polyurethanes, acrylic polymers, vinyl polymers, polyvinyl butyrals, alkyd resins and ketone/aldehyde resins, resins derived from aldehyde condensation products, such as arylsulfonamide-formaldehyde resins, for instance toluenesulfonamide-formaldehyde resin, arylsulfonamide-epoxy resins or ethyl tosylamide resins; - polymers of natural origin, such as plant resins, such as dammar resins, elemi gums, copal resins, and benzoin; gums such as shellac, sandarac gum and gum mastic.
  • arylsulfonamide-formaldehyde resins for instance toluenesulfonamide-formaldehyde resin, arylsulfonamide-epoxy resins or ethyl tosylamide resin
  • Use may especially be made, as film-forming polymers, of the toluenesulfonamide/formaldehyde resins Ketjentflex MS80 from the company Akzo or Santolite MHP, Santolite MS 80 from the company Faconnier or Resimpol 80 from the company Pan Americana, the alkyd resin Beckosol ODE 230-70-E from the company Dainippon, the acrylic resin Acryloid B66 from the company Rohm & Haas, the polyurethane resin Trixene PR 4127 from the company Baxenden or the acetophenone/formaldehyde resin sold under the reference Synthetic Resin SK by Degussa.
  • Ketjentflex MS80 from the company Akzo or Santolite MHP
  • Santolite MS 80 from the company Faconnier or Resimpol 80 from the company Pan Americana
  • the alkyd resin Beckosol ODE 230-70-E from the company Dainippon
  • the acrylic resin Acryloid B66 from the company
  • the film-forming polymer is chosen from poly saccharides and polysaccharide derivatives, preferably from nitrocellulose and polysaccharide ethers and esters, especially C 2 -C 4 ethers and esters, and is more preferentially chosen from cellulose acetobutyrates, cellulose acetopropionates, ethylcelluloses and ethyl guars, and mixtures thereof.
  • the film-forming polymer is chosen from cellulose derivatives such as nitrocellulose, cellulose acetobutyrate and ethylcellulose.
  • a composition according to the invention comprises a total content of film-forming polymer(s) of greater than or equal to 5%, in particular between 5% and 30% by weight, especially between 7.5% and 25% by weight and in particular between 10% and 20% by weight relative to the total weight of the nail varnish.
  • the photo-crosslinkable cosmetic compositions of the present invention may comprise at least one solvent chosen from physiologically acceptable organic solvents.
  • the said at least one organic solvent may be chosen in particular from: a) ketones that are liquid at room temperature, such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone and acetone,
  • alcohols that are liquid at room temperature such as ethanol, isopropanol, diacetone alcohol, 2-butoxyethanol or cyclohexanol,
  • glycols that are liquid at room temperature, such as ethylene glycol, propylene glycol or pentylene glycol and glycerol,
  • propylene glycol ethers that are liquid at room temperature, such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and dipropylene glycol mono-n-butyl ether,
  • short-chain esters comprising in total from 3 to 8 carbon atoms
  • short-chain esters comprising in total from 3 to 8 carbon atoms
  • alkanes that are liquid at room temperature, such as decane, heptane, dodecane and cyclohexane,
  • aromatic hydrocarbons that are liquid at room temperature, such as toluene and xylene,
  • the content of solvent in the composition may range from 5% to 50% by weight and preferably from 10% to 30% by weight relative to the total weight of the composition.
  • the composition comprises a solvent chosen from alcohols that are liquid at room temperature, short-chain esters comprising in total from 3 to 8 carbon atoms, and a mixture thereof.
  • the composition is free of solvent.
  • the photo-crosslinkable cosmetic compositions of the present invention may also contain adjuvants, or additives, chosen especially from pigments and dyes, plasticizers, coalescers, preserving agents, waxes, thickeners, fragrances, UV-screening agents, cosmetic nailcare active agents, spreading agents, antifoams and dispersants.
  • the said photo-crosslinkable cosmetic compositions of the present invention comprise at least one colouring agent chosen from pigments and preferably from metal oxides, such as iron oxides.
  • the colouring agent(s) are present in a total content of greater than or equal to
  • the absorption spectrum of the pigments and/or dyes used should in particular be adapted to that of the photoinitiators, or, conversely, the absorption spectrum of the photoinitiators should be adapted to that of the pigments and/or dyes used, so as to avoid these two types of compound absorbing light at the same wavelengths.
  • the absorption of light by the pigments and/or dyes would make the photoinitiators present virtually ineffective beyond a certain depth of coating.
  • a subject of the present invention is also a cosmetic process for coating natural nails or false nails. This process comprises:
  • a step of applying a photo-crosslinkable cosmetic composition containing, in a physiologically acceptable medium, (a) one or more oligomers and/or polymers comprising ethylenic double bonds, the mean number of ethylenic double bonds per oligomer and/or polymer molecule being greater than 1, and (b) at least one radical photoinitiator, so as to form a film on nails or false nails, and
  • the film is exposed to the radiation after evaporation of the solvent or of the water.
  • One embodiment of the process according to the invention consists in successively performing the steps of applying the composition and exposing the film several times, in particular twice in succession.
  • this process comprises a preliminary step of applying a transparent coat to ensure good adhesion (or base coat) under the photo-crosslinkable cosmetic composition.
  • this coat for ensuring good adhesion which is free of colouring agent, is transparent and the cosmetic composition comprises a colouring agent.
  • this coating for ensuring good adhesion is also a photo-crosslinkable cosmetic composition.
  • this process comprises a subsequent step of applying a transparent protective coat (or topcoats) over the photo-crosslinkable cosmetic composition.
  • this protective coat which is free of colouring agent, is transparent and the cosmetic composition comprises a colouring agent.
  • this protective coat is also a photo-crosslinkable cosmetic composition.
  • the keratin substrate (nails, false nails, eyelashes, false eyelashes, hair and hair prostheses) onto which is deposited the photo-crosslinkable cosmetic composition is already covered with a first non-crosslinkable cosmetic coating, such as a standard base coat or nail varnish.
  • the photo-crosslinkable cosmetic composition then constitutes a protective coat (top coat) for the first non-crosslinkable cosmetic coating.
  • the composition may also be deposited alone onto the nail to protect it.
  • the photo- crosslinkable cosmetic composition is preferably uncoloured, i.e. free of pigments and dyes.
  • the radiation suitable for crosslinking the cosmetic compositions of the present invention has a wavelength between 210 nm and 600 nm, preferably between 250 nm and 400 nm, preferably between 350 nm and 400 nm.
  • the use of lasers may also be envisaged.
  • use is made of a UV lamp and in particular a mercury-vapour lamp, the mercury optionally being doped with other elements, such as gallium, making it possible to modify the emission spectrum of the light source.
  • the exposure time of the deposited film to the radiation depends on various factors such as the chemical nature and the content of the reactive components or else the desired crosslinking density.
  • This curing time preferably does not correspond to total crosslinking of the system, i.e. the reaction of all of the double bonds present.
  • Such a process may use a UV lamp with a power rating of about 36 W.
  • a nail varnish was prepared, having the following composition:
  • composition of the example is applied to the nails in the form of a film about 50 ⁇ thick, and this film is irradiated for 2 minutes with UV radiation emitted by a Philips Original UVA lamp (36 W) sold by the company Philips, the effective wavelength range of which is from 340 to 365 nm.
  • the lamp is placed at a distance of about 50 cm from the nails and, during the exposure time, the hands are inclined alternately in one direction and in the other so as to distribute the radiation uniformly over the entire surface of the nails. This operation is repeated twice more, so as to deposit three crosslinked coats on the nails.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention porte sur une composition cosmétique photoréticulable qui est exempte de monomères réactifs ayant une masse moléculaire inférieure à 400 g/mol et comprenant une ou plusieurs doubles liaisons éthyléniques, comprenant : au moins deux polymères comprenant des doubles liaisons éthyléniques, le nombre moyen de doubles liaisons éthyléniques par molécule de polymère étant supérieur à 1 et lesdits au moins deux polymères comprenant au moins un polymère polyester contenant des groupes (méth)acrylates et au moins un polymère polyéther contenant des groupes (méth)acrylates; et au moins un photoinitiateur radicalaire. L'invention porte également sur un procédé cosmétique pour le revêtement des ongles ou de faux ongles utilisant une telle composition.
PCT/EP2012/054325 2011-03-15 2012-03-13 Vernis à ongles photoréticulables exempts de monomères insaturés WO2012130601A1 (fr)

Applications Claiming Priority (4)

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FR1152117A FR2972636B1 (fr) 2011-03-15 2011-03-15 Vernis a ongles photoreticulables exempts de monomeres insatures
FR1152117 2011-03-15
US201161476338P 2011-04-18 2011-04-18
US61/476,338 2011-04-18

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WO2012130601A1 true WO2012130601A1 (fr) 2012-10-04
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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1306954C (fr) 1986-04-07 1992-09-01 Yosh Hokama Vernis a ongles resistant et durable, et methode de fabrication connexe
US5456905A (en) 1988-08-23 1995-10-10 Ultraset Limited Partnership Quick-drying nail coating method and composition
US5543557A (en) 1990-07-02 1996-08-06 Perstorp Ab Acrylate monomer having a reduced primary irritation index and a method of making same
US5888649A (en) * 1996-01-11 1999-03-30 Avery Dennison Corporation Radiation-curable release coating compositions
EP0959066A2 (fr) 1998-05-20 1999-11-24 Basf Aktiengesellschaft Utilisation des amides d'acides gras polymérisés en tant qu'agent épaississant
FR2823105A1 (fr) 2001-04-06 2002-10-11 Oreal Vernis a ongle photoreticulables exempts de monomeres insatures
WO2006138198A1 (fr) * 2005-06-16 2006-12-28 Eastman Chemical Company Revetements resistant a l'abrasion
US20090098304A1 (en) 2005-06-10 2009-04-16 Vincent Stone Low extractable radiation curable compositions containing aminoacrylates

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Publication number Priority date Publication date Assignee Title
CA1306954C (fr) 1986-04-07 1992-09-01 Yosh Hokama Vernis a ongles resistant et durable, et methode de fabrication connexe
US5456905A (en) 1988-08-23 1995-10-10 Ultraset Limited Partnership Quick-drying nail coating method and composition
US5543557A (en) 1990-07-02 1996-08-06 Perstorp Ab Acrylate monomer having a reduced primary irritation index and a method of making same
US5888649A (en) * 1996-01-11 1999-03-30 Avery Dennison Corporation Radiation-curable release coating compositions
EP0959066A2 (fr) 1998-05-20 1999-11-24 Basf Aktiengesellschaft Utilisation des amides d'acides gras polymérisés en tant qu'agent épaississant
FR2823105A1 (fr) 2001-04-06 2002-10-11 Oreal Vernis a ongle photoreticulables exempts de monomeres insatures
US20090098304A1 (en) 2005-06-10 2009-04-16 Vincent Stone Low extractable radiation curable compositions containing aminoacrylates
WO2006138198A1 (fr) * 2005-06-16 2006-12-28 Eastman Chemical Company Revetements resistant a l'abrasion
US7375144B2 (en) 2005-06-16 2008-05-20 Eastman Chemical Company Abrasion resistant coatings

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Title
G. LI BASSI: "Les photoinitiateurs dans la reticulation des revetements", DOUBLE LIAISON - CHIMIE DES PEINTURES, November 1985 (1985-11-01), pages 34 - 41
HENRI STRUB: "Applications industrielles de la polymerisation photoinduite", L'ACTUALITE CHIMIQUE, February 2000 (2000-02-01), pages 5 - 13
MARC, J.M. ABADIE: "Photopolymeres: considerations theoriques et reaction de prise", DOUBLE LIAISON - CHIMIE DES PEINTURES, 1992, pages 28 - 34
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S. KNAUS, J POLYM. SCI., PART A = POLYM. CHEM., vol. 33, 1995, pages 929
S. KNAUS, PURE APPL. CHEM., vol. A33, no. 7, 1996, pages 869

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FR2972636B1 (fr) 2013-03-01
FR2972636A1 (fr) 2012-09-21
WO2012130601A9 (fr) 2012-12-06

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