WO2012130600A1 - Vernis à ongles photoréticulables exempts de monomères insaturés - Google Patents

Vernis à ongles photoréticulables exempts de monomères insaturés Download PDF

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WO2012130600A1
WO2012130600A1 PCT/EP2012/054323 EP2012054323W WO2012130600A1 WO 2012130600 A1 WO2012130600 A1 WO 2012130600A1 EP 2012054323 W EP2012054323 W EP 2012054323W WO 2012130600 A1 WO2012130600 A1 WO 2012130600A1
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photo
formula
meth
alkyl group
cosmetic composition
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PCT/EP2012/054323
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WO2012130600A9 (fr
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Guillaume Kergosien
Carl Riachi
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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
    • 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
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—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
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • 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
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K2800/95—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.
  • 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 number of ethylenic double bonds per polymer molecule being greater than 1, the said at least two polymers comprising at least one epoxyacrylate polymer and at least one polyether polymer containing (meth)acrylate groups, and
  • the epoxyacrylate polymer(s) 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;
  • 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 epoxyacrylate polymer(s) 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.
  • a composition in accordance with the present invention comprises polymers bearing ethylenic double bonds and having a suitable molar mass.
  • composition according to the invention comprises at least one epoxyacrylate polymer and at least one polyether polymer bearing (meth)acrylate groups.
  • An epoxyacrylate polymer in accordance with the invention preferably comprises on average two (meth)acrylate functions.
  • Such a polymer preferably has a molecular mass of between 400 g/mol and 1500 g/mol and preferably between 400 g/mol and 600 g/mol.
  • This polymer is preferably obtained by reaction between: - one or more (meth)acrylic acids and derivatives thereof preferably chosen from:
  • At least one di epoxide preferably chosen from:
  • oils bearing at least 2 epoxide groups such as epoxidized soybean oil, epoxidized linseed oil or epoxidized vernonia oil,
  • the epoxyacrylate polymer 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 epoxyacrylate polymer as described previously and a primary or secondary amine.
  • the epoxyacrylate polymer according to the invention is derived from the reaction between (meth)acrylic acid and bisphenol A diglycidyl ether.
  • the epoxyacrylate polymer(s) 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, preferably 50% by weight and advantageously between 60% and 80% by weight relative to the total weight of the photo-crosslinkable cosmetic composition, limits inclusive.
  • Such polymers are sold, for example, under the names CN104, CN11 1, CN1 16 and CN151 by the company Sartomer, under the names Ebecryl ® 600, Ebecryl ® 341 1, Ebecryl ® 3420, Ebecryl ® 3500, Ebecryl ® 3600, Ebecryl ® 3700, Ebecryl ® 3701, Ebecryl ® 3702, Ebecryl ® 3703, Ebecryl ® 3708, Ebecryl ® 3720, Ebecryl ® 6040 and Ebecryl ® LEO 10601 by the company Cytec, and under the names Photomer ® 3005, Photomer ® 3015 and Photomer ® 3072 by the company Cognis.
  • Polyether polymer containing (meth)acrylate groups are sold, for example, under the names CN104, CN11 1, CN1 16 and CN151 by the company Sartomer, under the names Ebecryl ® 600, Ebecryl
  • 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
  • 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 the compounds of formula (I) below:
  • ALK 1 and ALK 2 which may be identical or different, represent a (Ci-C 6 )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 6 )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;
  • - x 3 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 (Ci-C 6 )alkyl group such as ethyl or propyl;
  • - 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 iv) a group of formula (V) below:
  • ALK 7 and ALK 8 which may be identical or different, represent a (Ci-C 6 )alkyl group such as ethyl or propyl;
  • - x 7 and x 8 which may be identical or different, represent an integer greater than or equal to 1, for instance between 1 and 1000 inclusive;
  • R 7 and R 8 which may be identical or different, represent a hydrogen atom or a (Ci- C 6 )alkyl group such as methyl;
  • - ALK 9 represents a (Ci-C 6 )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 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):
  • ⁇ 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-
  • ⁇ 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 R 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 (III') being identical to formula (III) or only different in that it has in X a substitution with an amino group CH 2 R 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 R a R b as defined previously; or iv) a group of formula (V) below:
  • 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'):
  • 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.
  • 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.
  • (meth)acrylate groups are preferably present in a total content of greater than or equal to 50%) by weight relative to the total weight of the photo-crosslinkable cosmetic composition, and advantageously between 55% and 99.9% by weight relative to the total weight of the photo-crosslinkable cosmetic composition, limits inclusive.
  • (meth)acrylate groups are preferably present in the composition in a respective total content such that the weight ratio of the epoxyacrylate polymer(s) to the polyether polymer(s) containing (meth)acrylate groups is between 2 and 4, limits inclusive.
  • the polyether polymer(s) containing (meth)acrylate groups ensure solvation of the polyacrylate polymer(s), 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.
  • 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.
  • copolymerizable photoinitiators examples 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 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 epoxyacrylate polymer(s) and of the polyether containing (meth)acrylate groups, and preferably between 0.5% and 3% by weight relative to the total weight of the epoxyacrylate polymer(s) 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 an 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.
  • 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:
  • 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.
  • 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 0.1%) by weight relative to the total weight of the composition, and advantageously ranging from 0.2% to 1%> by weight relative to the total weight of the composition.
  • the composition comprises pigments and/or dyes
  • 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.
  • a volatile solvent such as a volatile organic solvent
  • 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.
  • 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. For nail varnishes, it will generally be sought to obtain satisfactory results for an exposition time between 1 and 20 minutes and preferably between 2 and 10 minutes.
  • 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 photo-crosslinkable 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.
  • a transparent nitrocellulose topcoat varnish coat is then applied to the surface of the deposit.
  • a glossy film with good staying power on the nail is obtained.
  • weight percentages given for a compound or a family of compounds are always expressed as weight of solids of the compound in question.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Epidemiology (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical & Material Sciences (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 de doubles liaisons éthyléniques par molécule de polymère étant supérieur à 1 et lesdits au moins deux polymères comprenant au moins un polymère d'époxyacrylate 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/EP2012/054323 2011-03-15 2012-03-13 Vernis à ongles photoréticulables exempts de monomères insaturés WO2012130600A1 (fr)

Applications Claiming Priority (4)

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FR1152113A FR2972632B1 (fr) 2011-03-15 2011-03-15 Vernis a ongles photoreticulables exempts de monomeres insatures
FR1152113 2011-03-15
US201161476340P 2011-04-18 2011-04-18
US61/476,340 2011-04-18

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN102942681A (zh) * 2012-10-23 2013-02-27 江苏三木化工股份有限公司 3g通信光纤用改性环氧大豆油丙烯酸酯及其制备方法
WO2015000470A1 (fr) * 2013-07-04 2015-01-08 Polystone-Chemical Gmbh Gel servant à préparer un revêtement pour un ongle
WO2015049523A1 (fr) * 2013-10-04 2015-04-09 Akcros Chemicals Limited Compositions de revêtement pour les ongles durcissables aux uv

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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
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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
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
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102942681A (zh) * 2012-10-23 2013-02-27 江苏三木化工股份有限公司 3g通信光纤用改性环氧大豆油丙烯酸酯及其制备方法
WO2015000470A1 (fr) * 2013-07-04 2015-01-08 Polystone-Chemical Gmbh Gel servant à préparer un revêtement pour un ongle
WO2015049523A1 (fr) * 2013-10-04 2015-04-09 Akcros Chemicals Limited Compositions de revêtement pour les ongles durcissables aux uv

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FR2972632A1 (fr) 2012-09-21
WO2012130600A9 (fr) 2012-12-06

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