WO2014177627A1 - Composé approprié pour le maquillage et/ou le soin des ongles - Google Patents

Composé approprié pour le maquillage et/ou le soin des ongles Download PDF

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Publication number
WO2014177627A1
WO2014177627A1 PCT/EP2014/058846 EP2014058846W WO2014177627A1 WO 2014177627 A1 WO2014177627 A1 WO 2014177627A1 EP 2014058846 W EP2014058846 W EP 2014058846W WO 2014177627 A1 WO2014177627 A1 WO 2014177627A1
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Prior art keywords
group
equal
hetero
linear
chosen
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PCT/EP2014/058846
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English (en)
Inventor
Guillaume Kergosien
Pascal Giustiniani
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L'oreal
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Publication of WO2014177627A1 publication Critical patent/WO2014177627A1/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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous
    • 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
    • A61K2800/94—Involves covalent bonding to the substrate

Definitions

  • the present invention relates to a compound that can be used in a cosmetic composition, especially of sol/gel type, for coating, such as making up and/or caring for keratin materials, in particular the nails.
  • compositions form films after application to keratin materials. After drying, a hybrid material is in fact formed by polycondensation and crosslinking at the nanometric scale.
  • patent application WO 98/44906 discloses a cosmetic or dermatological composition suitable for forming a coating on keratin materials via a reaction of sol/gel type obtained by mixing (A) at least one organometallic compound with (B) at least one functionalized organic polymer or at least one functionalized silicone polymer other than the first compound, and (C) an amount of water sufficient to hydrolyse the organometallic compound.
  • the coat of the composition deposited on the keratin materials may, if the reaction takes place slowly and if it does not dry quickly, prove to be tacky after its application and/or to be degraded on contact with foreign bodies, for instance a glass, a cigarette, an item of clothing or the skin, which will be an inconvenience to users.
  • a-alkoxysilane compounds are especially described in document US 2008/0 269 406.
  • Y is a monovalent or polyvalent, preferably linear, in particular divalent
  • C1-C100 hydrocarbon-based group which is optionally substituted, and/or interrupted with one or more heteroatoms, in particular O or S, preferably O, and/or with one or more groups chosen from a group C(X), X being O or S, a group N(R) with R being equal to H or R equal to a C1-C6 alkyl group such as methyl, N(R) preferably being equal to NH, an optionally substituted (hetero)cycloalkyl group or an optionally substituted (hetero)aryl group, and combinations thereof,
  • R 1 represents an H atom or a C1-C6 alkyl chain such as ethyl
  • R 2 and R 3 which may be identical or different, preferably identical, are chosen from a C1-C6 and in particular C2 alkoxy (or oxyalkylene) group, a linear or branched C1-C20 alkyl group, a group N(R) with R equal to H or to a C1-C6 alkyl group, preferably a C1-C6 and in particular C2 alkoxy (or oxyalkylene) group,
  • Xi and X3, which may be identical or different, preferably identical, represent a heteroatom, in particular O, S or an amino group N(R) with R chosen from H, a C1-C20 and better still C1-C6 alkyl group such as methyl, a (hetero)aryl group, a (hetero)cycloalkyl group, preferably Xi and X3 being an amino group N(R), preferably with R being equal to H, X 2 , which is preferably different from Xi and/or X 3 , preferably different from Xi and X3, represents a heteroatom, in particular O or S, or an amino group N(R) with R being equal to H or to a C1-C6 alkyl group, such as methyl, N(R) preferably being equal to NH, and more preferentially X2 representing O or S, preferably O,
  • X4 which may be identical to or different from Xi and/or X 3 , preferably identical to Xi and X3, is a heteroatom, in particular O, S or an amino group N(R) with R chosen from H, a C1-C20 and better still C1-C6 alkyl group such as methyl, a (hetero)aryl group, a (hetero)cycloalkyl group, or a group of formula (II) below:
  • R 6 represents an H atom or a C1-C6 alkyl chain such as ethyl
  • X4 preferably being an amino group N(R) and preferably with R being equal to H
  • ALKi represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain, preferably a Ci-C 4 o such as a C2-C20 alkylene chain
  • ALK1 preferentially represents a Ci-Cs such as a C6 alkylene chain.
  • Xi NH.
  • X 2 O.
  • X 3 O, S or NH and more preferentially NH.
  • the term "compound” should be understood as meaning the compounds as defined and also derivative(s) thereof.
  • a subject of the present invention is also a compound corresponding to the chemical formula (VIII) below:
  • R 1 , R 2 and R 3 which may be identical or different, represent H or a C1-C6 alkyl group, such as ethyl,
  • ALKi , ALK 2 and ALK 3 which may be identical or different, represent a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain, preferably a Ci-C 4 o such as a C2-C20 alkylene chain, ALKi preferentially represents a Ci-Cs such as a Ce alkylene chain, ALK 2 preferentially represents a Ci-Cs such as a Ci or Ce alkylene chain and ALK 3 represents a C1-C6 alkylene chain, in particular ethylene or propylene, preferably ethylene, optionally substituted with one or more hydroxyl groups,
  • CYCLO which may be identical or different, represents a (hetero)cyclic chain, in particular (hetero)cycloalkyl or (hetero)aryl, preferably with a C3-C6 and in particular Ce ring, more preferentially a Ce (hetero)cycloalkyl
  • q and p which may be identical or different, being equal to 0 or 1 , the sum q + p being other than 0, and q preferentially being equal to 0 or 1 and p being equal to 1 ,
  • n being other than 0, preferably being between 2 and 40, in particular between 4 and 20 and better still between 8 and 12,
  • Xi to X10 which may be identical or different, represent a heteroatom, in particular O or S, or an amino group N(R) with R equal to H or a C1-C6 alkyl group such as methyl, N(R) preferably being equal to N H, more preferentially, X2, X 4 , ⁇ , X 7 and X9 representing O or S, preferably O, more preferentially, Xi , X3, X5, Xs and X10 representing O or N(R) with R equal to H or a C1-C6 alkyl group such as methyl, preferably N(R), in particular NH; or more preferentially X2, ⁇ , X7, XS, X9 representing O or S, preferably O, more preferentially Xi , X3, X4, X5, X10 representing O or N(R) with R equal to H or a C1 -C6 alkyl group such as methyl, preferably N(R), in particular
  • a fourth subject of the present invention concerns the use of a compound as defined previously in cosmetics, in particular for coating the nails, especially for making up the nails.
  • a fifth subject of the present invention concerns a process for applying a compound as defined previously or a cosmetic composition as defined previously to keratin materials and in particular to the nails.
  • alkoxysilane denotes a compound comprising at least one silicon atom bearing at least one alkoxy group
  • “property of stability before application” denotes the ability to remain in liquid form at 25°C, and/or after one week of storage at 60°C, i.e. not to gel, before application to the keratin materials.
  • such a “liquid composition” may have, at 20°C, a viscosity ranging from 0.001 to 20 Pa/s, preferably from 0.01 to 10 Pa/s and even more preferably from 0.1 to 2 Pa/s.
  • This viscosity measurement may be performed at 20°C using a Rheomat RM180 viscometer equipped with a No. 4 spindle, the measurement being performed after 10 minutes of rotation of the spindle in the composition (after which time stabilization of the viscosity and of the spin speed are observed), at a shear rate of 200 s ⁇ 1 .
  • derivative(s) of the compounds in accordance with the invention especially means the salt(s) thereof, the solvate(s) thereof, such as the hydrate(s) thereof, the optical isomer(s) thereof, the geometric isomer(s) thereof, and the enantiomer(s) thereof.
  • this may, for example, be understood to mean the alkali or alkaline- earth metal carboxylates, such as sodium carboxylate and potassium carboxylate, and the carboxylates of organic salts, such as ammonium carboxylate.
  • hydrocarbon-based group or a “hydrocarbon-based chain” denotes a group or a chain containing carbon and hydrogen atoms, which is often referred to by a minimum number of carbons a and a maximum number of carbons b, "C a -Cb".
  • the optionally substituted "hydrocarbon-based group” is monovalent or polyvalent (multivalent), in particular divalent, saturated or unsaturated, linear or branched or cyclic, optionally bearing one or more (hetero)cyclic groups, optionally one or more (hetero)aryl groups, and containing from 2 to 100 carbon atoms.
  • hydrocarbon-based group or a “hydrocarbon-based chain” is "(poly) saturated' when it comprises one or more double bonds and/or one or more triple bonds, which may be conjugated or non-conjugated;
  • (hetero)cycle means a cyclic or heterocyclic group
  • cyclic means a "cycloalkyF group, i.e. which is non-aromatic, optionally substituted, monocyclic or polycyclic, fused or non-fused, containing from 5 to 10 carbon atoms or ring members, which may comprise one or more unsaturations, such as an optionally substituted cyclohexyl or cyclopentyl group;
  • heterocyclic means a non-aromatic, optionally substituted, monocyclic or polycyclic, fused or non-fused group, containing from 5 to 10 carbon atoms or ring members, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, morpholinyl, thiomorpholinyl, piperidyl, piperazinyl, pyrrolidinyl, tetrahydrofuryl, tetrahydrothiophenyl, azepanyl, thioazepanyl; preferentially pyrrolidinyl and morpholino.
  • the cyclic or heterocyclic part of a non-aromatic group may be substituted with at least one substituent borne by a carbon atom, chosen from the groups: • hydroxyl,
  • alkylcarbonylamino (RC(O)-NR'-) in which the group R' is a hydrogen atom or a Ci-C 4 alkyl group optionally bearing at least one hydroxyl group, and the group R is a C 1 -C 2 alkyl group or an amino group substituted with two Ci-C 4 alkyl groups, which may be identical or different, optionally bearing at least one hydroxyl group, the said alkyl groups possibly forming, with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • alkylcarbonyloxy (RC(O)-O-) in which the group R is a Ci-C 4 alkyl group or an amino group substituted with two Ci-C 4 alkyl groups, which may be identical or different, optionally bearing at least one hydroxyl group, the said alkyl groups possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7- membered heterocycle optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • the cyclic or heterocyclic, preferably cyclic, part of a non-aromatic group is substituted with several substituents borne by a carbon atom and more particularly two Ci-C 4 and preferably C 1 -C 2 alkyl groups, preferably two Ci substituents.
  • (hetero)aryP' means an aryl or heteroaryl group
  • aryV means a fused or non-fused, monocyclic or polycyclic group comprising from 5 to 10 carbon atoms or ring members, and in which at least one ring is aromatic; in particular, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl, and more preferentially a phenyl;
  • heteroaryP' represents a fused or non-fused, monocyclic or polycyclic group comprising from 5 to 10 carbon atoms or ring members, comprising from 1 to 2 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and at least one ring of which is aromatic; preferentially, a heteroaryl group is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthimidazolyl, naphthoxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopy
  • aryr or heteroaryP' groups or the aryl or heteroaryl part of a group may be substituted with at least one substituent borne by a carbon atom, chosen from:
  • halogen atom such as chlorine, fluorine or bromine
  • one amino group optionally substituted with one or two optionally substituted C1-C3 alkyl groups possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non- nitrogen heteroatom,
  • an acylamino group (-N(R)-C(O)R') in which the group R is a hydrogen atom or a Ci-C 4 alkyl group optionally bearing at least one hydroxyl group and the group R' is a C1-C2 alkyl group;
  • a cyclic or heterocyclic group, or a non-aromatic part of an aryl or heteroaryl group, may also be substituted with one or more oxo or carbonyl groups;
  • alky group is a linear or branched hydrocarbon-based group made up of a number of carbons, for example of C 1 -C 1 0, preferably of C Cs; particularly of Ci-C 4 such as methyl or ethyl;
  • alkeny group is a linear or branched hydrocarbon-based group made up of a number of carbons, comprising one or more conjugated or non-conjugated double bonds, for example of C 2 -C 1 0, in particular of C 4 -Cs comprising one, two or three double bonds, preferentially just one double bond;
  • (optionally) substituted means that the said group concerned (may be) is substituted with one or more group(s) chosen from the groups i) hydroxyl, ii) Ci-C 4 alkoxy, iii) acylamino, iv) amino optionally substituted with one or two identical or different Ci-C 4 alkyl radicals, the said alkyl radicals possibly forming, with the nitrogen atom that bears them, a heterocycle comprising from 5 to 7 ring members, optionally comprising another nitrogen or non-nitrogen heteroatom, v) phenyl, vi) (Ci-C6)alkoxycarbonyl, vii) (Ci-C6)alkylcarbonyloxy, viii) H-C(O)-O-;
  • (poly)hydroxy means one or more -OH group(s), given that when the hydroxyl(s) are directly attached to the (hetero)aryl, it may be in salified form, depending on the pH
  • carboxyP' means i) a -C(O)-OH group, and also the salts thereof according to the pH of the composition, for example salified with alkali metals, alkaline-earth metals, and organic salts such as ammoniums, which are cosmetically acceptable, such as sodium or potassium, ii) thiol derivatives thereof such as -C(S)-OH, iii) (thio)esterified derivatives thereof, and iv) (thio)amide derivatives thereof;
  • alkoxy means an alkyl-oxy or alkyl-O- group for which the alkyl radical is a linear or branched C1-C16, preferentially Ci-Cs and particularly Ci-C 4 hydrocarbon-based radical, such as methoxy or ethoxy, and when the alkoxy group is optionally substituted, this means that the alkyl group is optionally substituted as defined above;
  • a "(poly)hydroxyalkyP' group is an "alkyP' group as defined above, in which one or more hydrogen atoms are substituted or replaced with one or more hydroxyl groups; mention may be made of the group CH 2 CH 2 OH;
  • a "(poly)hydroxyalkoxy” group is an "alkoxy" group as defined above, in which one or more hydrogen atoms are substituted or replaced with one or more hydroxyl groups; mention may be made of the group -OCH 2 CH 2 OH.
  • a compound according to the present invention corresponds chemical formula (I) below: in which formula (I):
  • Y is a monovalent or polyvalent, preferably linear, in particular divalent, C1-C100 hydrocarbon-based group, which is optionally substituted, and/or interrupted with one or more heteroatoms, in particular O or S, preferably O, and/or with one or more groups chosen from a group C(X), X being O or S, a group N(R) with R being equal to H or R equal to a C1-C6 alkyl group such as methyl, N(R) preferably being equal to NH, an optionally substituted (hetero)cycloalkyl group or an optionally substituted (hetero)aryl group, and combinations thereof,
  • a is an integer between 1 and 8 and preferably equal to 2
  • R 1 represents an H atom or a C1-C6 alkyl chain such as ethyl
  • R 2 and R 3 which may be identical or different, preferably identical, are chosen from a C1-C6 and in particular C2 alkoxy (or oxyalkylene) group, a linear or branched C1-C20 alkyl group, a group N(R) with R equal to H or to a C1-C6 alkyl group, preferably a C1-C6 and in particular C2 alkoxy (or oxyalkylene) group,
  • Xi and X3 which may be identical or different, preferably identical, represent an optionally substituted heteroatom, in particular O, S or an amino group N(R) with R chosen from H, a C1-C20 and better still C1-C6 alkyl group such as methyl, a (hetero)aryl group, a (hetero)cycloalkyl group, preferably Xi and X3 being an amino group N(R), preferably with R being equal to H,
  • X 2 which is preferably different from Xi and/or X 3 , preferably different from Xi and X3, represents an optionally substituted heteroatom, in particular O or S, or an amino group N(R) with R being equal to H or to a C1-C6 alkyl group, such as methyl, N(R) preferably being equal to NH, and more preferentially X2 representing O or S, preferably O, X4, which may be identical to or different from Xi and/or X 3 , preferably identical to Xi and X3, is an optionally substituted heteroatom, in particular O, S or an amino group N(R) with R chosen from H, a C1-C20 and better still C1-C6 alkyl group such as methyl, a (hetero)aryl group, a (hetero)cycloalkyl group, or a group of formula (II) below:
  • ALKi represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain (divalent radical), preferably a Ci-C 4 o such as a C2-C20 alkylene chain (divalent radical), ALK1 preferentially represents a Ci-Cs such as a Ce alkylene chain (divalent radical).
  • R 2 and R 3 which may be identical or different, preferably identical, are chosen from a C 1 -C6 and in particular C 2 alkoxy (or oxyalkylene) group, a linear or branched C 1 -C 2 0 alkyl group, preferably a C 1 -C6 and in particular C 2 alkoxy (or oxyalkylene) group,
  • R 4 is chosen from a hydrogen atom, a C 1 -C 2 0 alkyl group, a (hetero)cycloalkyl group, a (hetero)aryl group or a grou of formula (IV) below:
  • R 7 and R 8 which may be identical or different, preferably identical, are chosen from a C 1 -C6 and in particular C 2 oxyalkylene group, a linear or branched C 1 -C 2 0 alkyl group, a group N(R) with R equal to H or to a C 1 -C6 alkyl group, and combinations thereof,
  • ALKi represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain (divalent radical), preferably a Ci-C 4 o such as a C 2 -C 2 0 alkylene chain (divalent radical), ALKi preferentially represents a Ci-Cs such as a C& alkylene chain (divalent radical).
  • a is greater than or equal to 1 , in particular is an integer between 1 and 8, and in particular is equal to 2.
  • f is an integer equal to 1 ,
  • e is an integer equal to 1 ,
  • d is an integer greater than or equal to 1 , in particular between
  • X 5 and Xe which may be identical or different, preferably identical, both represent a heteroatom, in particular O, S or an amino group N(R) with R chosen from H, a C1-C20 and better still C1-C6 alkyl group such as methyl, a (hetero)aryl group, a (hetero)cycloalkyl group, preferably X 5 and Xe being an amino group N(R), preferably with R being equal to H,
  • R 11 and R 13 which may be identical or different, preferably identical, represent a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group, comprising from 1 to 50 carbon atoms, in particular an optionally substituted (hetero)cycloalkyl or (hetero)aryl group, which is preferably 5- to 10-membered
  • R 11 and R 13 which may be identical or different, are preferably chosen from the divalent radicals (1 ) to (6) below, and preferably denote the radical (6) below:
  • R 12 which may be identical to or different from R 11 and R 13 , preferably different from R 11 and R 13 , represents a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 50 carbon atoms, optionally interrupted by one or more ester groups, preferably a linear saturated hydrocarbon-based group and in particular a C1-C6 and in particular C2 or C 4 alkylene chain.
  • Y is chosen from the groups of formula (XI) below:
  • c represents an integer greater than or equal to 1 , in particular between 1 and 10 and preferably between 1 and 3;
  • R 11 and R 13 which may be identical or different, are chosen from the divalent radicals (1 ) to (6) below, and preferably denote radical (6) below:
  • R 12 represents a divalent hydrocarbon-based, in particular non-linear, C20-C50, preferably C32"C 4 o and especially C36 radical.
  • Y is chosen from the groups of formula (VII) below:
  • c represents an integer greater than or equal to 1 , in particular between 1 and 10, and preferably between 1 and 3;
  • R 1 1 and R 13 which may be identical or different, preferably identical, represent a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group, comprising from 1 to 50 carbon atoms, in particular an optionally substituted (hetero)cycloalkyl or (hetero)aryl group, which is preferably 5- to 10-membered, R 1 1 and R 13 are advantageously chosen from the divalent radicals (1 ) to (6) below, and preferably denote the radical (6) below:
  • R 12 which may be identical to or different from R 11 and R 13 , preferably different from R 11 and R 13 , represents a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 50 carbon atoms, preferably a linear saturated hydrocarbon-based group mentioned and in particular a C1-C6 and in particular C2 or C 4 alkylene chain.
  • R 12 represents a non-linear divalent C20-C50, preferably C32-C 4 o and especially C36 radical; when d is an integer between 8 and 12, R 12 represents a linear divalent C1-C6 and in particular C2 or C 4 radical.
  • Y is chosen from the groups of formula (XII) below:
  • c represents an integer greater than or equal to 1 , in particular between 1 and 10 and preferably between 1 and 3;
  • R 11 and R 13 which may be identical or different, preferably identical, represent a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group, comprising from 1 to 50 carbon atoms, in particular a (hetero)cycloalkyl or (hetero)aryl group, which is preferably 5- to 10-membered, and optionally substituted,
  • R 11 and R 13 are chosen from the divalent radicals (1 ) to (6) below, and preferably denote radical (6) below:
  • R 12 represents a divalent, in particular non-linear, C20-C50, preferably C32-C 4 o and especially C36 radical.
  • Y has a molar mass of less than 3000 g/mol, preferably less than 1500 g/mol and preferentially less than 1000 g/mol. According to another particular embodiment, Y has a molar mass of less than 6000 g/mol, preferably less than 4500 g/mol and preferentially less than 3000 g/mol.
  • ALKi represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, divalent hydrocarbon-based radical, preferably a saturated linear divalent C1 -C40, such as C2-C20, hydrocarbon-based radical, preferentially ALK1 represents a saturated linear divalent Ci-Cs such as a Ce hydrocarbon-based radical.
  • Z denotes a divalent radical of formula (6)
  • R 2 and R 3 which may be identical or different, are chosen from a Ci - C6 and in particular C2 alkoxy group, a linear or branched C1 -C20, in particular Ci - C6 and more particularly Ci alkyl group; preferably, R 2 denotes an ethoxy radical and R 3 is chosen from methyl and ethoxy.
  • a compound according to the invention may be obtained in the following manner.
  • a diisocyanate derivative is placed in contact, in a reactor under an argon atmosphere, with a polymer, preferentially a telechelic polymer, bearing one or more functions that are reactive towards isocyanates.
  • a catalyst may be added in this step.
  • a tin-based catalyst such as tin 2-ethyl-hexanoate will preferably be chosen.
  • the reaction may be performed in solvent medium, which is necessarily anhydrous and non- nucleophilic for instance, methyl tetrahydrofurane.
  • the solution is heated, with a temperature ranging from 25°C to 100°C.
  • the reaction time and temperature are set by the control of consumption of the isocyanate functions. The monitoring of this consumption takes place by assaying the isocyanate functions, which is known to those skilled in the art.
  • an a-silane, in particular dialkoxy or trialkoxy a- silane, derivative comprising a function (for example an amine function) that is reactive towards isocyanate functions is added to the prepared solution of prepolymer.
  • a trialkoxysilane derivative that may be mentioned is N-(6-aminohexyl)aminomethyltriethoxysilane.
  • the final product is obtained at the end of the reaction (total consumption of the amine), after distilling off the reaction solvents, in the form of a solution in a solvent chosen as vehicle, preferably a polar volatile solvent.
  • composition comprising a compound according to the invention is preferably anhydrous.
  • anhydrous refers to a composition comprising a content of less than or equal to 2% and in particular 1 % by weight of water relative to the total weight of the composition.
  • the term “anhydrous” especially means that water is preferably not deliberately added to the compositions, but may be present in trace amount in the various compounds used in the compositions.
  • the composition according to the invention has a solids content of greater than or equal to 20% and preferably greater than 50%.
  • sample Approximately 2 g of the composition, referred to hereinbelow as the sample, are spread out on a metal crucible, which is placed in the halogen desiccator mentioned above. The sample is then subjected to a temperature of 120°C for 1 hour. The wet mass of the sample, corresponding to its initial mass, and the dry mass of the sample, corresponding to its mass after halogen heating, are measured using a precision balance.
  • a cosmetic composition in accordance with the present invention comprises an additional compound chosen from: (i) at least one compound comprising at least one alkoxysilane group other than a compound as defined previously,
  • At least one film-forming polymer which may be chosen especially from cellulose derivatives, polyesters, polyurethanes and acrylic polymers or copolymers,
  • a composition in accordance with the present invention comprises at least one compound in accordance with the invention and at least one polar volatile solvent.
  • a composition in accordance with the present invention comprises at least one compound in accordance with the invention and at least one film-forming polymer.
  • a composition in accordance with the present invention comprises at least one compound in accordance with the invention and at least one pulverulent phase.
  • a composition in accordance with the present invention comprises at least one compound in accordance with the invention and at least one polar volatile solvent, at least one plasticizer, at least one film-forming polymer and at least one pulverulent phase, in particular at least one colouring agent.
  • the composition according to the present invention also comprises at least one polar volatile solvent.
  • polar volatile solvent denotes, in the present invention, a compound which is liquid at room temperature, which comprises at least one polar group such as a hydroxyl, ester, ketone, ether or aldehyde group, and which has a vapour pressure greater than 1 mbar at 20°C.
  • polar volatile solvents that may be used in the compositions in accordance with the invention, mention may be made especially of lower monoalcohols containing from 1 to 5 carbon atoms such as ethanol and isopropanol, C3-C 4 ketones, C2-C 4 aldehydes and C2-C 4 short-chain esters.
  • the composition according to the invention may also comprise at least one film-forming polymer.
  • a film-forming polymer may advantageously be present in the composition.
  • film-forming polymer denotes a polymer that is capable, by itself or in the presence of an auxiliary film-forming agent, of forming an isolable and especially continuous and adherent film, on a support.
  • This support may especially be the nails.
  • a single film-forming polymer or a mixture of film-forming polymers may be used in the composition.
  • film-forming polymers that are soluble or dispersible in an organic solvent may be used.
  • a film-forming polymer that is suitable for use in the invention may be chosen in particular from:
  • polysaccharides include cellulose esters and ethers, such as nitrocellulose, cellulose acetate, cellulose acetobutyrate, cellulose acetopropionate and ethyl cellulose, or alternatively optionally modified guar gum, such as ethylguar;
  • - 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.
  • toluenesulfonamide-formaldehyde resins Ketjentflex MS80 from Akzo or Santolite MHP or Santolite MS 80 from Faconnier or Resimpol 80 from Pan Americana, the alkyd resin Beckosol ODE 230-70-E from Dainippon, the acrylic resin Acryloid B66 from Rohm & Haas, the polyurethane resin Trixene PR 4127 from Baxenden or the acetophenone/formaldehyde resin sold under the reference Synthetic Resin SK by Degussa.
  • Ketjentflex MS80 from Akzo or Santolite MHP or Santolite MS 80 from Faconnier or Resimpol 80 from Pan Americana
  • the alkyd resin Beckosol ODE 230-70-E from Dainippon
  • acrylic resin Acryloid B66 from Rohm & Haas
  • the polyurethane resin Trixene PR 4127 from Baxenden
  • the film-forming polymer is chosen from polysaccharides or polysaccharide derivatives, preferably from nitrocellulose, and cellulose ethers and esters.
  • the content of film-forming polymer may range from 0.1 % to 30% by weight, especially from 0.5% to 20% by weight and in particular from 1 % to 10% by weight relative to the total weight of the composition.
  • the composition according to the invention comprises as film-forming polymer at least cellulose derivatives, polyesters or polyurethanes.
  • the composition according to the invention comprises at least one plasticizer.
  • plasticizers such as:
  • glycols containing from 2 to 8 carbon atoms such as glycerol, propylene glycol, 1 ,3-butylene glycol and dipropylene glycol,
  • glycol derivatives such as diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol butyl ether or diethylene glycol hexyl ether, ethylene glycol ethyl ether, ethylene glycol butyl ether and ethylene glycol hexyl ether,
  • propylene glycol derivatives and in particular propylene glycol phenyl ether, propylene glycol diacetate, dipropylene glycol butyl ether, tripropylene glycol butyl ether, propylene glycol methyl ether, dipropylene glycol ethyl ether, tripropylene glycol methyl ether, diethylene glycol methyl ether and propylene glycol butyl ether,
  • - fatty alcohols that are liquid at room temperature, with a branched and/or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance 2-octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2- butyloctanol and 2-undecylpentadecanol,
  • - acid esters especially carboxylic acid esters such as monoesters of formula R 1 COOR 2 in which Ri represents a linear or branched acid residue containing from 1 to 40 carbon atoms and R 2 represents a hydrocarbon-based chain that is especially branched, containing from 1 to 40 carbon atoms provided that Ri + R 2 > 10, triglycerides consisting of fatty acid esters and of glycerol esters in which the fatty acids may have chain lengths ranging from C 4 to C 24 , citrates, especially triethyl citrate, tributyl citrate, triethyl acetyl citrate, tributyl acetyl citrate and tris(2-ethylhexyl) acetyl citrate; phthalates, especially diethyl phthalate, dibutyl phthalate, dioctyl phthalate, dipentyl phthalate and dimethoxyethyl phthalate; trimellitates especially such as tri
  • silicone oils that may be used in the composition may be non-volatile polydimethylsiloxanes (PDMSs), polydimethylsiloxanes comprising alkyl or alkoxy groups that are pendent and/or at the end of a silicone chain, these groups each containing from 2 to 24 carbon atoms, phenyl silicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes and 2-phenylethyl trimethylsiloxysilicates, and dimethicones or phenyl trimethicones with a viscosity of less than or equal to 100 cSt, and mixtures thereof,
  • PDMSs non-volatile polydimethylsiloxanes
  • polydimethylsiloxanes comprising alkyl or alkoxy groups that are
  • plasticizer The type and amount of plasticizer may be chosen by a person skilled in the art on the basis of his general knowledge.
  • the plasticizer content may range from 0.01 % to 10% and in particular from 1 % to 5% by weight relative to the total weight of the composition.
  • the composition according to the invention comprises as plasticizer at least one fatty alcohol, or a carboxylic acid ester or polyester.
  • a composition according to the present invention may comprise a pulverulent phase.
  • the content of the said pulverulent phase may be between 0.01 % and 40% by weight, in particular between 0.1 % and 30% by weight and more particularly between 0.1 % and 20% by weight relative to the total weight of the composition.
  • the pulverulent phase may comprise at least one filler and/or at least one colouring agent.
  • a pulverulent phase comprises at least one colouring agent.
  • fillers should be understood as meaning colourless or white, mineral or synthetic particles of any form, which are insoluble in the medium of the composition, irrespective of the temperature at which the composition is manufactured.
  • the additional fillers may be chosen from fillers such as:
  • - silica microspheres especially of open porosity or, preferably, hollow silica microspheres, such as the products Silica Beads SB 700/HA or Silica Beads SB 700 from the company Maprecos; these microspheres may be impregnated with a cosmetic active agent; - microporous polymer microspheres, which have a structure similar to that of a sponge; they generally have a specific surface area of at least 0.5 m 2 /g and in particular of at least 1 m 2 /g, the said specific surface area having no upper limit other than that resulting from the practical possibility of making microspheres of very high porosity: the specific surface area may, for example, be up to 1000 m 2 /g or even more.
  • Microspheres that may be mentioned include acrylic polymer microspheres, such as those made of crosslinked acrylate copolymer Polytrap 6603 Adsorber from the company RP Scherer, and those made of polymethyl methacrylate Micropearl M 100 from the company SEPPIC;
  • polyurethane powder such as the powdered copolymer of hexamethylene diisocyanate and of trimethylol hexyl lactone sold under the names
  • - polymer microcapsules that comprise a single closed cavity and form a reservoir, which may contain a liquid, especially a cosmetic active agent; they are prepared via known processes such as those described in patents US-A-3 615 972 and EP-A-056 219.
  • They may be made, for example, of polymers or copolymers of ethylenically unsaturated acid, amine or ester monomers, of urea- formaldehyde polymers or of vinylidene chloride polymers or copolymers; by way of example, mention may be made of microcapsules made of methyl acrylate or methacrylate polymers or copolymers, or alternatively of copolymers of vinylidene chloride and of acrylonitrile; among these polymers, mention will be made especially of those containing 20-60% by weight of units derived from vinylidene chloride, 20-60% by weight of units derived from acrylonitrile and 0-40% by weight of other units such as units derived from an acrylic and/or styrene monomer; crosslinked acrylic polymers or copolymers may also be used;
  • metal soaps in powder form are especially of metal soaps of fatty acids containing from 12 to 22 carbon atoms and in particular those containing from 12 to 18 carbon atoms.
  • the metal of the metal soap may especially be zinc or magnesium.
  • the fatty acid may be chosen especially from lauric acid, myristic acid, stearic acid and palmitic acid.
  • the metal soaps that may be used include zinc laurate, magnesium stearate, magnesium myristate and zinc stearate, and mixtures thereof;
  • - talcs or hydrated magnesium silicates especially in the form of particles generally less than 40 ⁇ in size;
  • micas or aluminosilicates of varied composition that are especially in the form of flakes from 2 to 200 ⁇ and preferably 5-70 ⁇ in size and from 0.1 to 5 ⁇ and preferably 0.2-3 ⁇ in thickness, these micas possibly being of natural origin (for example muscovite, margarite, roscoelite, lepidolite or biotite) or of synthetic origin;
  • non-expanded synthetic polymers such as polyethylene, polyesters (for example polyethylene isophthalate or terephthalate) and polyamides (for example Nylon), in the form of particles less than 50 ⁇ in size;
  • polyamide powders such as poly-a-alanine powder or Nylon powder, for example Orgasol powder from the company Atochem, polyacrylic acid or polymethacrylic acid powder, powders of polystyrene crosslinked with divinylbenzene, and silicone resin powders, and
  • - powders of organic materials of natural origin for instance starches, especially corn starch, wheat starch or rice starch;
  • a composition according to the invention is advantageously totally free of filler with a refractive index of greater than 1 .8.
  • the additional fillers may be present in the composition in a content ranging from 0.01 % to 20% by weight and preferably ranging from 0.1 % to 5% by weight relative to the total weight of the composition.
  • a composition according to the invention may contain as filler a polyurethane powder and/or mica.
  • a composition according to the invention may comprise a total content of fillers ranging from 0.01 % to 20% by weight, preferably ranging from 0.1 % to 10% by weight and preferentially ranging from 0.1 % to 5% by weight, relative to the total weight of the composition.
  • a composition according to the invention may also comprise, in its pulverulent phase, a colouring agent.
  • the colouring agent or dyestuff according to the invention is preferably chosen from pigments, nacres, reflective particles and dyes that are soluble in polar solvents, and mixtures thereof.
  • pigments should be understood as meaning white or coloured, mineral or organic particles of any form, which are insoluble in the physiological medium and are intended to colour the composition.
  • the pigments may be white or coloured, and mineral and/or organic.
  • mineral pigments that may be mentioned are titanium dioxide, optionally surface-treated, zirconium oxide or cerium oxide, and also zinc oxide, iron (black, yellow or red) oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue, and metal powders, for instance aluminium powder and copper powder.
  • the organic pigments may be chosen from the materials below, and mixtures thereof:
  • D&C certified pigments known under the following names: D&C Blue No. 4, D&C Brown No. 1 , D&C Green No. 5, D&C Green No. 6, D&C Orange No. 4, D&C Orange No. 5, D&C Orange No. 10, D&C Orange No. 1 1 , D&C Red No. 6, D&C Red No. 7, D&C Red No. 17, D&C Red No. 21 , D&C Red No. 22, D&C Red No. 27, D&C Red No. 28, D&C Red No. 30, D&C Red No. 31 , D&C Red No. 33, D&C Red No. 34, D&C Red No. 36, D&C Violet No. 2, D&C Yellow No.
  • the pigments may be treated or coated with a treatment agent.
  • the treatment agent may be chosen from alkoxysilanes, silicones such as methicones, dimethicones, and perfluoroalkylsilanes; fatty acids such as stearic acid; metal soaps such as aluminium dimyristate, the aluminium salt of hydrogenated tallow glutamate, perfluoroalkyi phosphates, perfluoroalkylsilanes, perfluoroalkylsilazanes, polyhexafluoropropylene oxides, polyorganosiloxanes comprising perfluoroalkyi perfluoropolyether groups, amino acids, N-acylamino acids or salts thereof; lecithin, isopropyl triisostearyl titanate, and mixtures thereof.
  • silicones such as methicones, dimethicones, and perfluoroalkylsilanes
  • fatty acids such as stearic acid
  • metal soaps such as aluminium dimyristate, the aluminium
  • the N-acylamino acids may comprise an acyl group containing from 8 to 22 carbon atoms, for instance a 2-ethylhexanoyl, caproyl, lauroyl, myristoyl, palmitoyl, stearoyl or cocoyl group.
  • the salts of these compounds may be the aluminium, magnesium, calcium, zirconium, zinc, sodium or potassium salts.
  • the amino acid may be, for example, lysine, glutamic acid or alanine.
  • a composition according to the invention may comprise a content of pigments ranging from 0.01 % to 70% by weight, preferably ranging from 0.1 % to 50% by weight and preferentially ranging from 0.01 % to 40% by weight, relative to the total weight of the composition.
  • a pigment content ranging from 0.01 % to 40% by weight, preferably from 0.1 % to 30% by weight and in particular from 0.1 % to 20% by weight relative to the total weight of the said composition will generally be used.
  • composition according to the invention may be free of pigments.
  • the pulverulent phase according to the invention may also comprise, or may even be formed from, nacres and/or reflective particles.
  • nacre should be understood as meaning coloured particles of any form, which may or may not be iridescent, especially produced by certain molluscs in their shell, or alternatively synthesized, and which have a colour effect via optical interference.
  • nacres examples include nacreous pigments such as titanium mica coated with an iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, and nacreous pigments based on bismuth oxychloride. They may also be mica particles at the surface of which are superimposed at least two successive layers of metal oxides and/or of organic colorants.
  • the nacres may more particularly have a yellow, pink, red, bronze, orangey, brown, gold and/or coppery colour or tint.
  • nacres that may be introduced into the composition
  • particles comprising a borosilicate substrate coated with titanium oxide.
  • Particles having a glass substrate coated with titanium oxide are especially sold under the name Metashine MC1080RY by the company Toyal.
  • nacres examples include polyethylene terephthalate glitter flakes, especially those sold by the company Meadowbrook Inventions under the name Silver 1 P 0.004X0.004 (silver flakes).
  • compositions according to the invention may comprise from 0 to 40%, for example 0.1 % to 20% and better still 0.5% to 10% by weight of nacres. More preferentially, they contain less than 40% by weight of nacres. According to one particular embodiment, the composition according to the invention is free of nacres. Finally, the colouring agent according to the invention may be chosen from reflective particles.
  • reflective particles denotes particles whose size, structure, especially the thickness of the layer(s) of which they are made and their physical and chemical nature, and surface state allow them to reflect incident light. This reflection may, where appropriate, have an intensity sufficient to create at the surface of the composition or of the mixture, when it is applied to the support to be made up, points of overbrightness that are visible to the naked eye, i.e. more luminous points that contrast with their environment by appearing to sparkle.
  • the reflective particles may be selected so as not to significantly alter the colouration effect generated by the colouring agents with which they are combined, and more particularly so as to optimize this effect in terms of colour yield. They may more particularly have a yellow, pink, red, bronze, orangey, brown, gold and/or coppery colour or tint.
  • These particles may have varied forms and may especially be in platelet or globular form, in particular in spherical form.
  • the reflective particles may or may not have a multilayer structure and, in the case of a multilayer structure, may have, for example, at least one layer of uniform thickness, in particular of a reflective material.
  • the reflective particles do not have a multilayer structure, they may be composed, for example, of metal oxides, especially titanium or iron oxides obtained synthetically.
  • the reflective particles may comprise, for example, a natural or synthetic substrate, especially a synthetic substrate at least partially coated with at least one layer of a reflective material, especially of at least one metal or metallic material.
  • the substrate may be made of one or more organic and/or mineral materials.
  • glasses More particularly, it may be chosen from glasses, ceramics, graphite, metal oxides, aluminas, silicas, silicates, especially aluminosilicates and borosilicates, and synthetic mica, and mixtures thereof, this list not being limiting.
  • the reflective material may comprise a layer of metal or of a metallic material.
  • Reflective particles are described especially in documents JP-A- 09188830, JP-A-10158450, JP-A-10158541 , JP-A-07258460 and JP-A-05017710.
  • reflective particles comprising a mineral substrate coated with a layer of metal
  • Particles with a silver-coated glass substrate in the form of platelets, are sold under the name Microglass Metashine REFSX 2025 PS by the company Toyal.
  • Particles with a glass substrate coated with nickel/chromium/molybdenum alloy are sold under the name Crystal Star GF 550 and GF 2525 by this same company.
  • Use may also be made of particles comprising a metal substrate, such as silver, aluminium, iron, chromium, nickel, molybdenum, gold, copper, zinc, tin, magnesium, steel, bronze or titanium, the said substrate being coated with at least one layer of at least one metal oxide, such as titanium oxide, aluminium oxide, iron oxide, cerium oxide, chromium oxide, silicon oxides and mixtures thereof.
  • Examples that may be mentioned include aluminium powder, bronze powder or copper powder coated with S1O2 sold under the name Visionaire by the company Eckart.
  • the pulverulent phase comprises at least one compound chosen from:
  • organic pigments such as, for example:
  • mineral pigments such as:
  • nacres such as, for example:
  • mica coated with titanium oxide mica coated with titanium oxide and iron oxide, and mica coated with an amino acid such as lauroyl lysine,
  • a composition according to the invention may also comprise water- soluble or liposoluble dyes in a content ranging from 0.01 % to 10% by weight and especially ranging from 0.01 % to 5% by weight relative to the total weight of the composition.
  • a composition according to the invention is more preferentially a nail varnish, the said nail varnish possibly being transparent or coloured.
  • nail varnishes mention may be made of a varnish base or a nailcare product.
  • physiologically acceptable medium means a non-toxic medium that may be applied to human keratin materials and that has a pleasant appearance, odour and feel.
  • composition according to the present invention may be applied either by finger or by using a brush or a felt-tip pen.
  • a brush or a felt-tip pen is described, for example, in document FR 2 909 844.
  • the solution obtained contains the expected polymer of following structure:
  • the mixture obtained comprises the compound having the following formula:
  • the varnish composition After application to false nails, the varnish composition forms, on contact with air, a scratch-resistant, glossy crosslinked film. It is understood that, in the context of the present invention, the weight percentages given for a compound or a family of compounds are always expressed as weight of solids of the compound in question. Throughout the application, the wording "comprising one" or “including one” means “comprising at least one” or “including at least one”, unless otherwise specified.

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Abstract

L'invention concerne un composé de formule chimique (I) ci-dessous. Dans la formule (I) : Y est un groupe hydrocarboné divalent en C1 à C100, qui est éventuellement substitué et/ou interrompu par un ou plusieurs hétéroatomes, a est un nombre entier compris entre 1 et 8 et, de préférence, égal à 2, R1 représente un atome H ou une chaîne alkyle en C1 à C6 telle qu'un groupe éthyle, R2 et R3 représentent un groupe alcoxy en C1 à C6 et, en particulier, en C2, X1, X3 et X4 étant égaux à NH, X2 étant égal à O, X4 étant égal à NH, ALK1 représente une chaîne hydrocarbonée linéaire ou ramifiée, de préférence, linéaire, saturée ou insaturée, de préférence saturée, de préférence, une chaîne alkylène en C1 à C40 telle qu'en C2 à C20, ALK1 représente préférentiellement une chaîne alkylène en C1 à C6 telle qu'en C6. L'invention concerne également une composition cosmétique, une utilisation particulière et un procédé pour le revêtement de matériaux kératiniques.
PCT/EP2014/058846 2013-04-30 2014-04-30 Composé approprié pour le maquillage et/ou le soin des ongles WO2014177627A1 (fr)

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KR20180005681A (ko) * 2015-06-12 2018-01-16 다이킨 고교 가부시키가이샤 표면 처리제
CN109715135A (zh) * 2016-09-23 2019-05-03 株式会社目立康 美甲用化妆品组合物、其使用方法和美甲用化妆品树脂

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KR102045664B1 (ko) * 2015-06-12 2019-11-15 다이킨 고교 가부시키가이샤 표면 처리제
CN107531732A (zh) * 2015-06-12 2018-01-02 大金工业株式会社 表面处理剂
KR20180005682A (ko) * 2015-06-12 2018-01-16 다이킨 고교 가부시키가이샤 표면 처리제
EP3309165A4 (fr) * 2015-06-12 2019-03-06 Daikin Industries, Ltd. Agent de traitement de surface
EP3309164A4 (fr) * 2015-06-12 2019-03-20 Daikin Industries, Ltd. Agent de traitement de surface
US11155672B2 (en) 2015-06-12 2021-10-26 Daikin Industries, Ltd. Surface treatment agent
KR20180005681A (ko) * 2015-06-12 2018-01-16 다이킨 고교 가부시키가이샤 표면 처리제
KR102084634B1 (ko) * 2015-06-12 2020-03-04 다이킨 고교 가부시키가이샤 표면 처리제
CN107531732B (zh) * 2015-06-12 2020-10-30 大金工业株式会社 表面处理剂
US10696788B2 (en) 2015-06-12 2020-06-30 Daikin Industries, Ltd. Surface treatment agent
EP3512493A4 (fr) * 2016-09-23 2020-04-15 Menicon Co., Ltd. Composition cosmétique pour ongles, son procédé d'utilisation, et résine cosmétique pour ongles
CN109715135A (zh) * 2016-09-23 2019-05-03 株式会社目立康 美甲用化妆品组合物、其使用方法和美甲用化妆品树脂
US11278489B2 (en) 2016-09-23 2022-03-22 Menicon Co., Ltd. Cosmetic composition for nails, method of using same, and cosmetic resin for nails
CN109715135B (zh) * 2016-09-23 2023-01-24 株式会社目立康 美甲用化妆品组合物、其使用方法和美甲用化妆品树脂

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