WO2014177627A1 - Compound suitable for making up and/or caring for the nails - Google Patents
Compound suitable for making up and/or caring for the nails Download PDFInfo
- 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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- 108010076876 Keratins Proteins 0.000 claims abstract description 12
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- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- FZUOVNMHEAPVBW-UHFFFAOYSA-L quinoline yellow ws Chemical compound [Na+].[Na+].O=C1C2=CC=CC=C2C(=O)C1C1=NC2=C(S([O-])(=O)=O)C=C(S(=O)(=O)[O-])C=C2C=C1 FZUOVNMHEAPVBW-UHFFFAOYSA-L 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- VRDAELYOGRCZQD-NFLRKZIHSA-M sodium;4-[(2z)-2-[(5e)-5-[(2,4-dimethylphenyl)hydrazinylidene]-4,6-dioxocyclohex-2-en-1-ylidene]hydrazinyl]benzenesulfonate Chemical compound [Na+].CC1=CC(C)=CC=C1N\N=C(/C(=O)C=C\1)C(=O)C/1=N\NC1=CC=C(S([O-])(=O)=O)C=C1 VRDAELYOGRCZQD-NFLRKZIHSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940099373 sudan iii Drugs 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 229920006250 telechelic polymer Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—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
The invention relates to a compound of chemical formula (I) below, in which formula (I): Y is a C1-C100 divalent hydrocarbon-based group, which is optionally substituted and/or interrupted with one or more heteroatoms, a is an integer between 1 and 8 and preferably equal to 2, R1 represents an H atom or a C1-C6 alkyl chain such as ethyl, R2 and R3 represent a C1-C6 and in particular C2 alkoxy group, X1, X3 and X4 being equal to NH, X2 being equal to O, X4 being equal to NH, ALK1 represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain, preferably a C1-C40 such as a C2-C20 alkylene chain, ALK1 preferentially represents a C1-C6 such as a C6 alkylene chain. The invention also relates to a cosmetic composition, to a particular use and to a process for coating keratin materials.
Description
Compound suitable for making up and/or caring for the nails
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.
The use of sol/gel techniques for the purposes of preparing cosmetic compositions is known per se. Such 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.
For example, 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.
There is a need to provide compounds or compositions that have not only stability properties before application to keratin materials, but also good reactivity.
There is also a need to provide compounds or compositions that afford long staying power after application.
There is also a need to provide compounds or compositions that give a smooth, uniform deposit.
Rapid drying of the film or coating obtained is also sought.
Specifically, 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.
In addition, properties of remanence on washing with water and with detergents are sought.
It is sought to obtain a strong, adherent film.
Finally, sheen properties of the deposited film may be sought.
The inventors have found that such advantages may be obtained by using particular a-alkoxysilane compounds. Such a-alkoxysilane compounds are especially described in document US 2008/0 269 406.
Thus, one subject of the present invention is a compound of chemical formula (I) below:
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,
R1 represents an H atom or a C1-C6 alkyl chain such as ethyl,
R2 and R3, 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,
X2, which is preferably different from Xi and/or X3, 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 X3, 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:
in which formula (II):
- R6 represents an H atom or a C1-C6 alkyl chain such as ethyl,
- R7 and R8, which may be identical or different, preferably identical, are chosen from a C1-C6 and in particular C2 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, and combinations thereof,
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-C4o such as a C2-C20 alkylene chain, ALK1 preferentially represents a Ci-Cs such as a C6 alkylene chain.
Preferably, Xi = NH. Preferably, X2 = O. Preferably, X3 = 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.
According to an independent aspect, or in combination with the characteristics described previously, a subject of the present invention is also a compound corresponding to the chemical formula (VIII) below:
(VIII) in which formula (VIII):
R1 , R2 and R3, which may be identical or different, represent H or a C1-C6 alkyl group, such as ethyl,
ALKi , ALK2 and ALK3, which may be identical or different, represent a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain, preferably a Ci-C4o such as a C2-C20 alkylene chain, ALKi preferentially represents a Ci-Cs such as a Ce alkylene chain, ALK2 preferentially represents a Ci-Cs such as a Ci or Ce alkylene chain and ALK3 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
and even more preferentially a cyclohexyl substituted with one or more Ci-C4 alkyl radicals, preferably methyl;
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, X4, ΧΘ, X7 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, ΧΘ, 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 NH. A third subject of the present invention concerns a cosmetic composition comprising at least one compound as defined previously.
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.
In the context of the present invention, the term:
- "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.
For example, 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.
- the term "bearing" means substituted with and/or ending with. - the term "independently" means identical or different.
The term "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. Regarding the derivatives of the carboxyl groups in particular, 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.
In this application and unless expressly mentioned:
A "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, "Ca-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.
A "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;
The term "(hetero)cycle" means a cyclic or heterocyclic group;
The term "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;
The term "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,
• Ci-C4 and preferably Ci-C2 alkyl,
• Ci-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy,
• alkylcarbonylamino (RC(O)-NR'-) in which the group R' is a hydrogen atom or a Ci-C4 alkyl group optionally bearing at least one hydroxyl group, and the group R is a C1-C2 alkyl group or an amino group substituted with two Ci-C4 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-C4 alkyl group or an amino group substituted with two Ci-C4 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;
• alkoxycarbonyl (RO-C(O)-) in which the group R is a Ci-C4 alkyl group or an amino group substituted with two Ci-C4 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;
in particular, 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-C4 and preferably C1-C2 alkyl groups, preferably two Ci substituents.
The term "(hetero)aryP' means an aryl or heteroaryl group;
The term "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;
The term "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, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, tetrazolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl, triazolyl, xanthyl and the ammonium salt thereof;
The "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:
• a Ci-C4 and preferably C1-C2 alkyl group optionally substituted with one or more groups chosen from hydroxyl, C1-C2 alkoxy, (poly)hydroxy(C2-C4)alkoxy, acylamino, amino substituted with two, identical or different, Ci-C4 alkyl groups, optionally bearing at least one hydroxyl group, or the two groups possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered and preferably 5- or 6-membered heterocycle optionally comprising another nitrogen or non-nitrogen heteroatom;
• a halogen atom such as chlorine, fluorine or bromine;
• a hydroxyl group;
• a C1-C2 alkoxy group;
• a C2-C4 (poly)hydroxyalkoxy group;
• an amino group;
• nitro;
• a 5- or 6-membered heterocycloalkyl group;
• an optionally cationic 5- or 6-membered heteroaryl group, preferentially imidazolium, optionally substituted with a (Ci-C4) alkyl group, preferentially methyl;
• an amino group substituted with one or two identical or different C1-C6 alkyl groups, optionally bearing at least:
i) one hydroxyl group,
ii) one amino group optionally substituted with one or two optionally substituted C1-C3 alkyl groups, 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,
• an acylamino group (-N(R)-C(O)R') in which the group R is a hydrogen atom or a Ci-C4 alkyl group optionally bearing at least one hydroxyl group and the group R' is a C1-C2 alkyl group;
• a carbamoyl group ((R)2N-C(O)-) in which the groups R, which may be identical or different, represent a hydrogen atom or a Ci-C4 alkyl group optionally bearing at least one hydroxyl group;
• a carboxylic acid or ester group, (-O-C(O)R') or (-C(O)OR'), in which the group R' is a hydrogen atom or a Ci-C4 alkyl group optionally bearing at least one hydroxyl group and the group R' is a C1-C2 alkyl group;
• the carboxylic group possibly being in acid or salified form (preferably salified with an alkali metal or a substituted or unsubstituted ammonium);
• an alkylsulfonylamino group (R'S(O)2-N(R)-) in which the group R represents a hydrogen atom or a Ci-C4 alkyl group optionally bearing at
least one hydroxyl group and the group R' represents a Ci-C4 alkyl group, or a phenyl group;
• an aminosulfonyl group ((R)2N-S(O)2-) in which the groups R, which may be identical or different, represent a hydrogen atom or a Ci-C4 alkyl group optionally bearing at least one hydroxyl group;
• a cyano group (CN);
• a (poly)haloalkyl group, preferentially trifluoromethyl (CF3);
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;
An "alky group is a linear or branched hydrocarbon-based group made up of a number of carbons, for example of C1-C10, preferably of C Cs; particularly of Ci-C4 such as methyl or ethyl;
An "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 C2-C10, in particular of C4-Cs comprising one, two or three double bonds, preferentially just one double bond;
The term "(optionally) substituted", assigned to the group concerned, means that the said group concerned (may be) is substituted with one or more group(s) chosen from the groups i) hydroxyl, ii) Ci-C4 alkoxy, iii) acylamino, iv) amino optionally substituted with one or two identical or different Ci-C4 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-; The term "(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 of the composition, preferably salified with alkali
metals, alkaline-earth metals or organic salts such as ammoniums, which are cosmetically acceptable, such as sodium or potassium;
The term "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;
The term "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-C4 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 CH2CH2OH;
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 -OCH2CH2OH.
ALPHA-ALKOXYSILANE COMPOUNDS
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,
R1 represents an H atom or a C1-C6 alkyl chain such as ethyl,
R2 and R3, 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,
X2, which is preferably different from Xi and/or X3, 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 X3, 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:
in which formula (II):
- R6 represents an H atom or a C1-C6 alkyl chain such as ethyl,
- R7 and R8, 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, in particular methyl, and combinations thereof,
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 (divalent radical), preferably a Ci-C4o such as a C2-C20 alkylene chain (divalent radical), ALK1 preferentially represents a Ci-Cs such as a Ce alkylene chain (divalent radical).
According to a particular embodiment, this compound corresponds to the chemical formula (III) below:
a is an integer between 1 and 8 and preferably equal to 2,
R2 and R3, 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, preferably a C1 -C6 and in particular C2 alkoxy (or oxyalkylene) group,
preferably, R2 = R3 = -OCH2CH3 or R2 = -CH3 and R3 = -OCH2CH3;
R4 is chosen from a hydrogen atom, a C1-C20 alkyl group, a (hetero)cycloalkyl group, a (hetero)aryl group or a grou of formula (IV) below:
in which formula (IV) R7 and R8, which may be identical or different, preferably identical, are chosen from a C1 -C6 and in particular C2 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, and combinations thereof,
preferably R4 = H;
R5 represents H, a C1-C20 and better still C1 -C6 alkyl group such as methyl, a (hetero)aryl group or a (hetero)cycloalkyl group, R5 preferably being equal to H.
ALKi represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain (divalent radical), preferably a Ci-C4o such as a C2-C20 alkylene chain (divalent radical), ALKi preferentially represents a Ci-Cs such as a C& alkylene chain (divalent radical).
According to a particular embodiment, a is greater than or equal to 1 , in particular is an integer between 1 and 8, and in particular is equal to 2.
in which formula (V):
b is between 1 and 20 and preferably between 2 and 8, R9 and R10, which may be identical or different, preferably identical, represent a hydrogen atom or a (Ci-C2o)alkyl group, preferably a hydrogen atom. According to a particular embodiment, Y comprises at least one optionally substituted C3-C8 and in particular Ce (hetero)cycloalkyl or (hetero)aryl group.
According to a particular embodiment, Y comprises at least one C1-C6 and in particular C2 oxyalkylene group, the oxyalkylene group(s) preferably linking, directly or indirectly, at least two C3-C8 and in particular Ce, optionally substituted (hetero)cycloalkyl or (hetero)aryl groups.
According to a particular embodiment, Y comprises at least one carbamate group, preferably linking, directly or indirectly, the oxyalkylene group(s) and at least one C3-C8 and in particular Ce, optionally substituted (hetero)cycloalkyl or (hetero)aryl group.
According to a particular embodiment, Y is chosen from the groups of formula (VI) below:
R--X WL(O)--R— (0)f— W-Xg-R—
(VI)
in which formula (VI):
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
preferably between 4 and 20 and better still between 8 and 12,
c represents an integer greater than or equal to 1 , in particular between 1 and 10, preferably between 1 and 3;
X5 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 X5 and Xe being an amino group N(R), preferably with R being equal to H,
W1 and W2 represent a carbonyl group,
R11 and R13, 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, R11 and R13, which may be identical or different, are preferably chosen from the divalent radicals (1 ) to (6) below, and preferably denote the radical (6) below:
R12, which may be identical to or different from R11 and R13, preferably different from R11 and R13, 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 C4 alkylene chain.
According to a particular embodiment, Y is chosen from the groups of formula (XI) below:
in which: c represents an integer greater than or equal to 1 , in particular between 1 and 10 and preferably between 1 and 3;
X5 and Xe, which may be identical or different, preferably identical, both represent a heteroatom, in particular O, S or an N(R) amino group with R chosen from H, a C1 -C20 alkyl group, better still C1 -C6, such as methyl, a (hetero)aryl group, a (hetero)cycloalkyl group, preferably X5 and ΧΘ being an N(R) amino group, and preferably with R being equal to H,
R11 and R13, 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,
Preferably, R11 and R13, which may be identical or different, are chosen from the divalent radicals (1 ) to (6) below, and preferably denote radical (6) below:
R12 represents a divalent hydrocarbon-based, in particular non-linear, C20-C50, preferably C32"C4o and especially C36 radical.
According to a particular embodiment, Y is chosen from the groups of formula (VII) below:
in which formula (VII):
c represents an integer greater than or equal to 1 , in particular between 1 and 10, and preferably between 1 and 3;
d is an integer greater than or equal to 1 , in particular between 2 and 40, preferably between 4 and 20 and better still between 8 and 12,
R1 1 and R13, 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, R1 1 and R13 are advantageously chosen from the divalent radicals (1 ) to (6) below, and preferably denote the radical (6) below:
R12, which may be identical to or different from R11 and R13, preferably different from R11 and R13, 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 C4 alkylene chain.
Advantageously, when d = 1 , R12 represents a non-linear divalent C20-C50, preferably C32-C4o and especially C36 radical; when d is an integer between 8 and 12, R12 represents a linear divalent C1-C6 and in particular C2 or C4 radical.
According to a particular embodiment, Y is chosen from the groups of formula (XII) below:
(XII)
in which:
c represents an integer greater than or equal to 1 , in particular between 1 and 10 and preferably between 1 and 3;
R11 and R13, 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,
advantageously, R11 and R13 are chosen from the divalent radicals (1 ) to (6) below, and preferably denote radical (6) below:
R12 represents a divalent, in particular non-linear, C20-C50, preferably C32-C4o and especially C36 radical.
According to a particular embodiment, 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.
According to a particular variant of the invention, the compounds of the invention correspond to formula (X) below:
(X)
in which:
T denotes a heteroatom chosen from O, S or a radical NR in which R denotes a hydrogen atom or a Ci-C4 alkyl radical, in particular methyl; preferably, T denotes an oxygen atom or NH, and preferentially denotes an oxygen atom.
- ALkQ denotes a linear or branched C2-C100 divalent hydrocarbon- based radical optionally interrupted with one or more non-adjacent heteroatoms chosen from O, S or groups NR in which R denotes a hydrogen atom or a Ci-C4
alkyl radical, in particular methyl; preferably, ALK4 denotes a linear or branched C2-C50 hydrocarbon-based radical optionally interrupted with one or more non- adjacent oxygen atoms or NH groups. In particular, ALK4 denotes a divalent radical chosen from:
(i) a divalent radical -[(CH2)n-O-]m-(CH2)n- with n denoting a non-zero integer between 1 and 10 (limits inclusive), preferably between 1 and 5, m denoting a non-zero integer between 1 and 30, preferably between 1 and 20 and more particularly between 1 and 10.
(ii) a C2-C50, preferably C20-C50 and especially C32-C4o, in particular non- linear, alkylene radical, such as a C36 radical;
- 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 is chosen from the radicals (1 ) to (6) below:
preferably, Z denotes a divalent radical of formula (6);
- R2 and R3, 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, R2 denotes an ethoxy radical and R3 is chosen from methyl and ethoxy.
According to a more particular embodiment, 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 example of assaying is as follows:
Reagents:
Dibutylamine solution at 0.5 mol.l"1
-1
Ethanolic hydrogen chloride solution at 0.5 mol.l
Procedure:
Prepare two concordant blanks and note the masses of dibutylamine mCOntroi introduced and the equivalent volume Vb For the test, weigh out a mass miso of the isocyanate to be assayed
Weigh out about 10 ml of DBA and note the exact mass mreagent
Add 20 ml of toluene
Leave to stir for 20 minutes at room temperature
Add 100 ml of ethanol
• Back-titrate the excess of DBA with ethanolic hydrogen chloride and note the volume Veq
Calculation: lNco=[[[(Vb* mreagent)/ mCOntroi]- Veq]*[HCL]*56.1 ]/ miso
In the second step, 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. An example of 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.
The compounds of formula (X) may be prepared according to the reaction scheme below:
OCN-Z-NCO + H-T-ALK4-T-H
OCN-Z-N H-CQ-T-
mixture containing inter alia
COSMETIC COMPOSITION
A composition in accordance with the invention is preferably a cosmetic composition, comprising a compound as described previously, and is suitable for coating keratin materials, in particular the nails, and especially for making up and/or caring for keratin materials, in particular the nails.
The composition comprising a compound according to the invention is preferably anhydrous.
The term "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.
According to one particular embodiment, the composition according to the invention has a solids content of greater than or equal to 20% and preferably greater than 50%.
For the purposes of the present invention, the term "solids content" denotes the content of non-volatile matter after film formation.
The solids content (abbreviated as SC) of a composition according to the invention is measured using a "Halogen Moisture Analyzer HR 83" commercial halogen desiccator from Mettler Toledo. The measurement is performed on the basis of the weight loss of a sample dried by halogen heating, and thus represents the percentage of residual matter once the water and the volatile matter have evaporated off.
This technique is fully described in the machine documentation supplied by Mettler Toledo.
The measuring protocol is as follows:
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.
The values measured by means of the protocol described above may differ from the corresponding theoretical values by plus or minus 1 %.
The solids content is calculated in the following manner:
Solids content (expressed as weight percentage) = 100 (dry mass/wet mass). According to a preferred embodiment, 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,
(ii) at least one plasticizer which may be chosen especially from fatty alcohols and (poly)esters, in particular poly(carboxylic acid esters),
(iii) at least one film-forming polymer which may be chosen especially from cellulose derivatives, polyesters, polyurethanes and acrylic polymers or copolymers,
(iv) at least one pulverulent phase chosen in particular from at least one filler, at least one colouring agent, such as pigments, nacres, reflective particles and dyes that are soluble in polar solvents,
and mixtures thereof.
According to a particular embodiment, 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.
According to a particular embodiment, a composition in accordance with the present invention comprises at least one compound in accordance with the invention and at least one compound comprising at least one alkoxysilane group other than a compound of formula (I).
According to a particular embodiment, a composition in accordance with the present invention comprises at least one compound in accordance with the invention and at least one plasticizer.
According to a particular embodiment, 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. According to a particular embodiment, a composition in accordance with the present invention comprises at least one compound in accordance with the invention and at least one pulverulent phase.
According to a preferred embodiment, 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.
OTHER ALKOXYSILANE COMPOUND
According to one particular embodiment, the composition according to the present invention advantageously comprises at least one other compound comprising at least one alkoxysilane group, other than a compound of formula (I).
The term "compound comprising at least one alkoxysilane group" preferably denotes a compound of formula Si(OR2)4 or of formula R1 xSi(OR2)(4-X) or of formula [R1 y (OR2)z SiO((4-y-Z)/2)]n in which:
- R1 represents, independently, a nucleophilic group other than a silanol, or a (Ci-C2o)alkyl group, optionally substituted with at least one nucleophilic group other than a silanol,
- R2 represents, independently, a hydrogen atom or a (Ci-Cio)alkyl group,
- x represents 1 or 2,
- y represents, independently, 1 or 2,
- z represents, independently, 0, 1 or 2,
- the sum of y and z being less than or equal to 3,
- and n represents an integer between 2 and 1000.
POLAR VOLATILE SOLVENT
According to one particular embodiment, the composition according to the present invention also comprises at least one polar volatile solvent.
The term "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.
Among the 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-C4 ketones, C2-C4 aldehydes and C2-C4 short-chain esters.
FILM-FORMING POLYMER
According to one particular embodiment, the composition according to the invention may also comprise at least one film-forming polymer. In particular, when the composition according to the present invention is in the form of a nail varnish, such a film-forming polymer may advantageously be present in the composition.
For the purposes of the present invention, the term "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.
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.
According to the invention, 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. Among the polysaccharides that are suitable for use in the invention, examples that may be mentioned 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.
Use may in particular be made, as film-forming polymers, of the 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.
According to one particular embodiment, the film-forming polymer is chosen from polysaccharides or polysaccharide derivatives, preferably from nitrocellulose, and cellulose ethers and esters.
For example, 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.
According to one particular embodiment, the composition according to the invention comprises as film-forming polymer at least cellulose derivatives, polyesters or polyurethanes.
PLASTICIZER
According to one particular embodiment, the composition according to the invention comprises at least one plasticizer.
In particular, mention may be made, alone or as mixtures, of 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,
- glycol esters,
- 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,
- higher fatty acids such as oleic acid, linoleic acid or linolenic acid, and mixtures thereof,
- acid esters especially carboxylic acid esters such as monoesters of formula R1COOR2 in which Ri represents a linear or branched acid residue containing from 1 to 40 carbon atoms and R2 represents a hydrocarbon-based chain that is especially branched, containing from 1 to 40 carbon atoms provided that Ri + R2 > 10, triglycerides consisting of fatty acid esters and of glycerol esters in which the fatty acids may have chain lengths ranging from C4 to C24, 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 tris(2-ethylhexyl) trimellitate, L7,9-trimellitate and L8,10-trimellitate; phosphates, especially tricresyl phosphate, tributyl phosphate, triphenyl phosphate and tributoxyethyl phosphate; tartrates, especially dibutyl tartrate; adipates, especially such as diethyl adipate and diisobutyl adipate; carbonates; sebacates; benzyl benzoate, butyl acetylricinoleate, glyceryl acetylricinoleate, butyl glycolate, glyceryl triacetate and plasticizers of polyester type,
- camphor,
- N-ethyl-o,p-toluenesulfonamide,
- oxyethylenated derivatives such as oxyethylenated oils, especially plant oils such as castor oil,
- linear or branched hydrocarbons of mineral or synthetic origin, such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam®, and squalane, and mixtures thereof, and in particular hydrogenated polyisobutene,
- silicone oils. The 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,
- and mixtures thereof.
The type and amount of plasticizer may be chosen by a person skilled in the art on the basis of his general knowledge.
For example, 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.
According to one particular embodiment, the composition according to the invention comprises as plasticizer at least one fatty alcohol, or a carboxylic acid ester or polyester. PULVERULENT PHASE
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. Preferably, a pulverulent phase comprises at least one colouring agent. Fillers
The term "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 m2/g and in particular of at least 1 m2/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 m2/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
Plastic Powder D-400 and T-7 by the company Toshiki;
- 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;
- elastomeric crosslinked organopolysiloxane spherical powders, described especially in document JP-A-02 243 612, such as those sold under the name Trefil Powder E-506C by the company Dow Corning;
- the carnauba wax microbeads sold under the name Microcare 350® by the company Micro Powders and the paraffin wax microbeads sold under the name Microease 1 14S® by the company Micro Powders;
- metal soaps in powder form. Among these soaps, mention may be made 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 μιτι in size;
- micas or aluminosilicates of varied composition that are especially in the form of flakes from 2 to 200 μιτι and preferably 5-70 μιτι in size and from 0.1 to 5 μιτι and preferably 0.2-3 μιτι in thickness, these micas possibly being of natural origin (for example muscovite, margarite, roscoelite, lepidolite or biotite) or of synthetic origin;
- clays such as sericites, which belong to the same chemical and crystalline class as muscovite;
- kaolin or hydrated aluminium silicate, which is especially in the form of particles of isotropic forms generally less than 30 μιτι in size;
- boron nitrides;
- powders of tetrafluoroethylene polymers, such as Ceridust 9205 F from the company Clariant;
- precipitated calcium carbonate, especially in the form of particles greater than 10 m in size;
- magnesium carbonate and magnesium hydrogen carbonate;
- hydroxyapatite;
- powders of 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 μιτι in size;
- powders of spheronized, crosslinked or non-crosslinked synthetic polymers, for instance 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
- bismuth oxychloride powders,
- powders of organic materials of natural origin, for instance starches, especially corn starch, wheat starch or rice starch;
- and mixtures thereof.
A composition according to the invention is advantageously totally free of filler with a refractive index of greater than 1 .8.
As representatives of such fillers, mention may especially be made of titanium oxides, zinc oxides and bismuth oxychloride powders.
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.
According to one advantageous variant, a composition according to the invention may contain as filler a polyurethane powder and/or mica.
Advantageously, 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.
As stated above, 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
The term "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.
Among the 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:
- cochineal carmine,
- organic pigments of azo dyes, anthraquinone dyes, indigoid dyes, xanthene dyes, pyrene dyes, quinoline dyes, triphenylmethane dyes or fluoran dyes.
Among the organic pigments, mention may be made especially of the 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. 7, D&C Yellow No. 8, D&C Yellow No. 10, D&C Yellow No. 1 1 , FD&C Blue No. 1 , FD&C Green No. 3, FD&C Red No. 40, FD&C Yellow No. 5, FD&C Yellow No. 6.
The chemical materials corresponding to each of the organic dyestuffs mentioned previously are mentioned in the publication "International Cosmetic Ingredient Dictionary and Handbook", 1997 edition, pages 371 to 386 and 524 to 528, published by The Cosmetic, Toiletries and Fragrance Association, the content of which is incorporated into the present patent application by reference.
According to one particular embodiment of the invention, 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.
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.
According to a preferred variant, 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.
When it is a makeup product, 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.
According to another embodiment variant, a 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.
The term "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.
Examples of nacres that may be mentioned 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.
As illustrations of nacres that may be introduced into the composition, mention may be made of the gold-coloured nacres sold especially by the company Engelhard under the name Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronze nacres sold especially by the company Merck under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company Engelhard under the name Super bronze (Cloisonne); the orange nacres sold especially by the company Engelhard under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the name Passion orange (Colorona) and Matte orange (17449) (Microna); the brown nacres sold especially by the company Engelhard under the name Nu- antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); the nacres with a copper tint sold especially by the company Engelhard under the name Copper 340A (Timica); the nacres with a red tint sold especially by the company Merck under the name Sienna fine (17386) (Colorona); the nacres with a yellow tint sold especially by the company Engelhard under the name Yellow (4502) (Chromalite); the red nacres with a gold tint sold especially by the company Engelhard under the name Sunstone G012 (Gemtone); the pink nacres sold especially by the company Engelhard under the name Tan opale G005 (Gemtone); the black nacres with a gold tint sold especially by the company
Engelhard under the name Nu antique bronze 240 AB (Timica), the blue nacres sold especially by the company Merck under the name Matte blue (17433) (Microna), the white nacres with a silvery tint sold especially by the company Merck under the name Xirona Silver, and the golden-green pink-orange nacres sold especially by the company Merck under the name Indian summer (Xirona), and mixtures thereof.
Still as examples of nacres, mention may also be made of 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.
Finally, examples of nacres that may also be mentioned include polyethylene terephthalate glitter flakes, especially those sold by the company Meadowbrook Inventions under the name Silver 1 P 0.004X0.004 (silver flakes).
According to one particular variant, the 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.
The term "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, whatever their form, 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.
When 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.
When the reflective particles have a multilayer structure, they 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.
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.
Again as an example of reflective particles comprising a mineral substrate coated with a layer of metal, mention may also be made of particles comprising a silver-coated borosilicate substrate.
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.
Preferably, the pulverulent phase comprises at least one compound chosen from:
organic pigments such as, for example:
- the D&C pigments certified by the Food & Drug Administration as listed in the section "Color Additives - Batch Certified by the U.S. Food and Drug Administration" of the CTFA; mention may be made especially of Blue 1 and 4, Brown 1 , Ext. Violet 2, Ext. Yellow 7, Green 3, 5, 6 and 8, Orange 4, 5, 10 and 1 1 , Red 4, 6, 7, 17, 21 , 22, 27, 28, 30, 36 and 40, Violet 2, Yellow 5, 6, 7, 8, 10 and 1 1 ,
mineral pigments such as:
- iron oxide, zirconium oxide, cerium oxide, iron oxide or chromium oxide,
- ferric blue, manganese violet, ultramarine blue, pink or violet, chromium hydrate or chromium hydroxide,
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,
- polyethylene terephthalate glitter flakes,
- sericite,
- and mixtures thereof, and
reflective particles such as, for example:
- particles comprising a borosilicate substrate coated with a metallic layer.
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.
The liposoluble dyes are, for example, Sudan Red, DC Red 17, DC
Green 6, β-carotene, soybean oil, Sudan Brown, DC Yellow 1 1 , DC Violet 2, DC Orange 5 and quinoline yellow. The water-soluble dyes are, for example, beetroot juice or methylene blue. A composition according to the invention may take the form of a makeup composition product, in particular a nail varnish, a foundation, a liquid lipstick, a mascara, an anti-wrinkle composition or a skincare composition.
As skincare agent, a composition according to the invention may be used for resistance or beautifying purposes, for treating wounds, or for injecting or anti-wrinkle purposes for filling hollow areas of the skin.
A composition according to the invention is more preferentially a nail varnish, the said nail varnish possibly being transparent or coloured.
As nail varnishes, mention may be made of a varnish base or a nailcare product.
A composition according to the invention comprises a physiologically acceptable medium.
The term "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.
Thus, the composition according to the present invention may be applied either by finger or by using a brush or a felt-tip pen. Such a pen is described, for example, in document FR 2 909 844.
An example of preparation of a compound according to the invention and of a composition comprising such a compound will now be described.
Example of preparation of a cosmetic composition according to the invention incorporating a compound according to the invention
The example given below is presented as a non-limiting illustration of the invention.
22.2 g of isophorone diisocyanate IPDI (4098-71 -9), 100 μΙ of catalyst tin 2- ethylhexanoate and 255 g of MeTHF (dried over sieves) were placed in a tared 500 ml reactor under an argon atmosphere. The solution was heated to 55°C. 20 g of PEG-400 (reference 81 172 from Aldrich) were added over 30 minutes. At the end of the addition, the mixture was heated to 65°C until an isocyanate index of 19 was obtained, which corresponds to the theoretical consumption of 50% of the isophorone diisocyanate).
29.5 g of N-(6-aminohexyl)aminomethyltriethoxysilane (15129-36-9) were dissolved in 30 g of MeTHF and added to the preceding solution over 30 minutes at room temperature, still under a controlled atmosphere. The mild exothermicity was controlled with a bath of cold water. The solution became more viscous. 200 g of ethanol were added and the MeTHF was distilled off. The operation was repeated until the MeTHF was removed.
A solution with a solids content equal to 25% was finally obtained. This solution was maintained under an anhydrous atmosphere.
The solution obtained contains the expected polymer of following structure:
After deposition of the solution obtained on a contrast card available from the company Byk-Gardner, the formation of a film was observed within a few minutes. This film is smooth, glossy and scratch-resistant. The gloss was measured using a
glossmeter available from the company Byk-Gardner. The scratch resistance was evaluated by scratching the surface of the film with a fingernail .
Example 2:
22.2 g of isophorone diisocyanate IPDI, 100 μΙ of tin 2-ethylhexanoate catalyst and 270 g of MeTHF (dried over sieves) were placed in a 500 ml reactor under an argon atmosphere. The solution was heated to 55°C. 26.7 g of non-linear C36 diol dimer (Pripol® 2033 from Croda) diluted in 30 g of MeTHF were added over 40 minutes. At the end of the addition, the mixture was heated at 65°C until half of the isophorone diisocyanate was consumed.
29.2 g of N-(6-aminohexyl)aminomethyltriethoxysilane were diluted in 30 g of MeTHF and this mixture was then added over 45 minutes to the reactor at room temperature (to react with the second half of the isophorone diisocyanate). The mixture was left to react for 2 hours and monitoring that all the isocyanate groups have reacted was performed by infrared measurement. Next, 200 g of isopropanol were added, the mixture was heated for 1 hour at 60°C, and the temperature was then increased to distil off the MeTHF. When half of the amount of MeTHF was distilled off, 100 g of isopropanol were added and the distillation was continued. The operation was repeated until all of the MeTHF was removed. A solution containing a mixture of compounds of formula (I) with a solids content of 21 % in isopropanol was finally obtained. The solution obtained contains the compound having the following formula:
with Pripol denoting the non-linear C36 divalent radical of the diol dimer Pripol 2033.
Example 3:
22.2 g of isophorone diisocyanate, 100 μΙ of tin 2-ethylhexanoate catalyst and 300 g of MeTHF (dried over sieves) were placed in a 500 ml reactor under an argon atmosphere. The solution was heated to 55°C. 33 g of poly(tetrahydrofuran)
of mass 660 (Aldrich, CAS: 25190-06-1 ) diluted in 30 g of MeTHF were added over 40 minutes. At the end of the addition, the mixture was heated at 65°C until half of the isophorone diisocyanate was consumed.
29.2 g of N-(6-aminohexyl)aminomethyltriethoxysilane were diluted in 30 g of MeTHF and this mixture was then added over 45 minutes to the reactor at room temperature (to react with the second half of the isophorone diisocyanate). The mixture was left to react for 2 hours and monitoring that all the isocyanate groups have reacted was performed by infrared measurement. Next, 200 g of isopropanol were added, the mixture was heated for 1 hour at 60°C, and the temperature was then increased to distil off the MeTHF. When half of the amount of MeTHF was distilled off, 100 g of isopropanol were added and the distillation was continued. The operation was repeated until all of the MeTHF was removed. A solution containing a mixture of compounds of formula (I) with a solids content of 18% in isopropanol was finally obtained.
The mixture obtained comprises the compound having the following formula:
Example 4:
A nail varnish having the following composition (in weight percentages) is prepared:
- solution comprising compound (I) obtained according to Example 1 99%
- pigment Red 27 1 % The solution of Example 1 is replaced with the solution of Example 3 or of
Example 4.
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.
Claims
1 . Compound of chemical formula (I) below:
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,
R1 represents an H atom or a C1-C6 alkyl chain such as ethyl,
R2 and R3, which may be identical or different, preferably identical, are chosen from a C1-C6 and in particular C2 alkoxy 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 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,
X2, which is preferably different from Xi and/or X3, 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 X3, 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:
in which formula (II):
- R6 represents an H atom or a C1-C6 alkyl chain such as ethyl,
- R7 and R8, which may be identical or different, preferably identical, are chosen from a C1-C6 and in particular C2 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, and combinations thereof,
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-C4o such as a C2-C20 alkylene chain, ALK1 preferentially represents a Ci-Cs such as a C6 alkylene chain.
2. Compound according to Claim 1 , in which:
Xi = NH; X2 = O; X3 = O or S or NH, and preferably NH.
in which formula (III):
a is an integer between 1 and 8 and preferably equal to 2,
R2 and R3, which may be identical or different, preferably identical, are chosen from a C1-C6 and in particular C2 alkoxy group, a linear or branched C1-C20 alkyi group, a group N(R) with R equal to H or to a C1-C6 alkyi group, preferably a C1-C6 and in particular C2 alkoxy group, preferentially R2 = R3 = -OCH2CH3 or R2 = -CH3 and R3 = -OCH2CH3;
R4 is chosen from a hydrogen atom, a C1-C20 alkyi group, a (hetero)cycloalkyl group, a (hetero)aryl group or a grou of formula (IV) below:
in which formula (IV) R7 and R8, which may be identical or different, preferably identical, are chosen from a C1-C6 and in particular C2 oxyalkylene group, a linear or branched C1-C20 alkyi group, a group N(R) with R equal to H or to a C1-C6 alkyi group, and combinations thereof, preferably R4 = H;
R5 represents H, a C1-C20 and better still C1-C6 alkyi group such as methyl, a (hetero)aryl group or a (hetero)cycloalkyl group, R5 preferably being equal to H.
ALKi represents a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain, preferably a Ci-C4o such as a C2-C20 alkylene chain, ALK1 preferentially represents a Ci-Cs such as a C6 alkylene chain.
4. Compound according to any one of Claims 1 to 3, in which ALKi is chosen from the groups of formula (V) below:
in which formula (V):
b is between 1 and 20 and preferably between 2 and 8
R9 and R10, which may be identical or different, preferably identical, represent a hydrogen atom or a (Ci-C2o)alkyl group, preferably a hydrogen atom.
5. Compound according to any one of the preceding claims, in which Y comprises at least one optionally substituted C3-C8 and in particular C6
(hetero)cycloalkyl or (hetero)aryl group.
6. Compound according to any one of the preceding claims, in which Y comprises at least one C1-C6 and in particular C2 oxyalkylene group, the oxyalkylene group(s) preferably linking, directly or indirectly, at least two C3-C8 and in particular C6, optionally substituted (hetero)cycloalkyl or (hetero)aryl groups.
7. Compound according to any one of the preceding claims, in which Y comprises at least one carbamate group, preferably linking, directly or indirectly, the oxyalkylene group(s) and at least one C3-C8 and in particular C6, optionally substituted (hetero)cycloalkyl or (hetero)aryl group.
8. Compound according to any one of the preceding claims, in which Y is chosen from the groups of formula (VI) below:
(VI)
in which formula (VI):
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 2 and 40, preferably between 4 and 20 and better still between 8 and 12,
c represents an integer greater than or equal to 1 , in particular between 1 and 10, preferably between 1 and 3;
X5 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 X5 and Xe being an amino group N(R), preferably with R being equal to H,
W1 and W2 represent a carbonyl group,
R11 and R13, 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, R11 and R13 are preferably chosen from the divalent radicals (1 ) and (6) below, and preferably denote the radical (6):
which may be identical to or different from R11 and R13, preferably different R1 1 and R13, represents a polyether group, a polyester group or 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 mentioned and in particular a C1-C6 and in particular C2 alkylene chain; preferably represents a C20-C50, preferably C32-C4o and especially C36, in particular non-linear, divalent radical.
9. Compound according to any one of Claims 1 to 7, in which Y is chosen from the groups of formula (XI) below:
in which:
c represents an integer greater than or equal to 1 , in particular between 1 and 10 and preferably between 1 and 3;
R11 and R13, 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, and are preferentially chosen from the divalent radicals (1 ) to (6) below, and preferably denote radical (6) below:
R12 represents a divalent, in particular non-linear, C20-C50, preferably C32-C4o and especially C36 radical.
10. Compound according to any one of the preceding claims, in which Y is chosen from the groups of formula (VII) below:
in which formula (VII):
c represents an integer greater than or equal to 1 , in particular between 1 and 10, and preferably between 1 and 3,
d is an integer greater than or equal to 1 , in particular between 2 and 40, preferably between 4 and 20 and better still between 8 and 12,
R11 and R13, 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; are preferably chosen from the divalent radicals (1 ) to (6) below and preferably denote the radical (6):
R12, which may be identical to or different from R11 and R13, preferably different from R11 and R13, represents a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising from 1 to 50 carbon atoms, optionally interrupted with one or more ester groups, preferably a linear saturated hydrocarbon-based group mentioned and in particular a C1-C6 and in particular C2 or C4 alkylene chain.
1 1 . Compound according to any one of Claims 1 to 9, in which Y is chosen from the groups of formula (XII) below:
(XII)
in which:
c represents an integer greater than or equal to 1 , in particular between 1 and 10 and preferably between 1 and 3;
R11 and R13, 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; and are preferably chosen from the divalent radicals (1 ) to (6) below, and preferably denote radical (6) below:
R12 represents a divalent, in particular non-linear, C20-C50, preferably C32-C4o and especially C36 radical.
12. Compound according to any one of the preceding claims, in which Y has a molar mass of less than 3000 g/mol, preferably less than 1500 g/mol and preferentially less than 1000 g/mol.
13. Compound according to any one of Claims 1 to 1 1 , in which Y has a molar mass of less than 6000 g/mol, preferably less than 4500 g/mol and preferentially less than 3000 g/mol.
14. Compound according to any one of the preceding claims, characterized in that n is equal to 2.
(VIII) in which formula (VIII):
R1 , R2 and R3, which may be identical or different, represent H or a C1-C6 alkyl group, such as ethyl,
ALKi , ALK2 and ALK3, which may be identical or different, represent a linear or branched, preferably linear, saturated or unsaturated, preferably saturated, hydrocarbon-based chain, preferably a Ci-C4o such as a C2-C20 alkylene chain, ALKi preferentially represents a Ci-Cs such as a C6 alkylene chain, ALK2 preferentially represents a Ci-Cs such as a C6 alkylene chain and ALK3 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 C6 ring, more preferentially a C6 (hetero)cycloalkyl
or alternatively a cyclohexyl substituted with one or more Ci-C4 alkyl radicals, preferably methyl;
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 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 Xio, 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 NH, more preferentially, X2, X4, ΧΘ, XZ 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, ΧΘ, 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 NH.
16. Compound corresponding to formula (X) below:
(X)
in which:
T denotes a heteroatom chosen from O, S or a radical NR in which R denotes a hydrogen atom or a Ci-C4 alkyl radical, in particular methyl; preferably, T denotes an oxygen atom or NH, and preferentially denotes an oxygen atom.
- ALK4 denotes a linear or branched C2-C100 divalent hydrocarbon-based radical optionally interrupted with one or more non-adjacent heteroatoms chosen from O, S or groups NR in which R denotes a hydrogen atom or a Ci-C4 alkyl radical, in particular methyl; preferably, ALK4 denotes a linear or branched C2-C50 hydrocarbon-based radical optionally interrupted with one or more non-adjacent
oxygen atoms or NH groups, in particular, ALK4 denotes a divalent radical chosen from:
(i) a divalent radical -[(CH2)n-O-]m-(CH2)n- with n denoting a non-zero integer between 1 and 10 (limits inclusive), preferably between 1 and 5, m denoting a non-zero integer between 1 and 30, preferably between 1 and 20 and more particularly between 1 and 10.
(ii) a C2-C50, preferably C20-C50 and especially C32-C4o, in particular non¬ linear, alkylene radical, such as a C36 radical; - 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-C2o, hydrocarbon-based radical, preferentially ALKi represents a saturated linear divalent d-Ce such as a C6 hydrocarbon- based radical.
- Z is chosen from the radicals (1 ) to (6) below:
preferably, Z denotes a divalent radical of formula (6);
- R2 and R3, which may be identical or different, are chosen from a Ci-C6 and in particular C2 alkoxy group, a linear or branched Ci-C2o, in particular C1-C-6 and more particularly Ci alkyl group; preferably, R2 denotes an ethoxy radical and R3 is chosen from methyl and ethoxy.
17. Cosmetic composition comprising at least one compound according to any one of the preceding claims. 18. Cosmetic composition according to Claim 12, in which the compound(s) are present in the composition in a content of greater than or equal to 2% by weight, in particular 5% by weight, more particularly 10% by weight, preferably 20% by weight and even more preferentially 50% by weight, relative to the total weight of the composition.
19. Cosmetic composition according to Claim 12 or 13, characterized in that it is anhydrous.
20. Cosmetic composition according to Claim 12, 13 or 14, having a solids content of greater than or equal to 20%.
21 . Composition according to any one of Claims 12 to 15, comprising an additional compound chosen from:
(i) at least one compound comprising at least one alkoxysilane group,
(ii) at least one plasticizer which may be chosen especially from fatty alcohols and (poly)esters, in particular poly(carboxylic acid esters),
(iii) at least one film-forming polymer which may be chosen especially from cellulose derivatives, polyesters, polyurethanes and acrylic polymers or copolymers,
(iv) at least one pulverulent phase chosen in particular from at least one filler, at least one colouring agent, such as pigments, nacres, reflective particles and dyes that are soluble in polar solvents,
and mixtures thereof. 22. Composition according to any one of Claims 12 to 16, which may take the form of a makeup composition, in particular a nail varnish, a foundation, a lipstick,
in particular a liquid lipstick, a mascara, an anti-wrinkle composition or a skincare composition.
23. Use of a compound according to any one of Claims 1 to 1 1 , in cosmetics, in particular for coating the nails.
24. Non-therapeutic cosmetic process, comprising at least one step consisting in applying at least one compound according to any one of Claims 1 to 1 1 or a cosmetic composition according to any one of Claims 12 to 17 to keratin materials, in particular to the nails.
Applications Claiming Priority (2)
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FR1354005 | 2013-04-30 | ||
FR1354005A FR3005052B1 (en) | 2013-04-30 | 2013-04-30 | COMPOUND SUITABLE FOR MAKE-UP AND / OR NAIL CARE |
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WO2014177627A1 true WO2014177627A1 (en) | 2014-11-06 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP2014/058846 WO2014177627A1 (en) | 2013-04-30 | 2014-04-30 | Compound suitable for making up and/or caring for the nails |
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WO (1) | WO2014177627A1 (en) |
Cited By (3)
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CN107531732A (en) * | 2015-06-12 | 2018-01-02 | 大金工业株式会社 | Surface conditioning agent |
KR20180005681A (en) * | 2015-06-12 | 2018-01-16 | 다이킨 고교 가부시키가이샤 | Surface treatment agent |
CN109715135A (en) * | 2016-09-23 | 2019-05-03 | 株式会社目立康 | Nail beautifier composition, its application method and nail beautifier resin |
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FR3005052A1 (en) | 2014-10-31 |
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