WO2024141526A1 - Process for treating keratin materials using at least one (co)polymer of polyvinyl alcohol (pva) bearing acetoacetate functions and at least one crosslinking agent - Google Patents
Process for treating keratin materials using at least one (co)polymer of polyvinyl alcohol (pva) bearing acetoacetate functions and at least one crosslinking agentInfo
- Publication number
- WO2024141526A1 WO2024141526A1 PCT/EP2023/087794 EP2023087794W WO2024141526A1 WO 2024141526 A1 WO2024141526 A1 WO 2024141526A1 EP 2023087794 W EP2023087794 W EP 2023087794W WO 2024141526 A1 WO2024141526 A1 WO 2024141526A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- formula
- chosen
- poly
- optionally
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 132
- 230000008569 process Effects 0.000 title claims abstract description 128
- 102000011782 Keratins Human genes 0.000 title claims abstract description 92
- 108010076876 Keratins Proteins 0.000 title claims abstract description 92
- 239000000463 material Substances 0.000 title claims abstract description 91
- 229920001577 copolymer Polymers 0.000 title claims abstract description 77
- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 60
- 229920002451 polyvinyl alcohol Polymers 0.000 title description 50
- 239000004372 Polyvinyl alcohol Substances 0.000 title description 27
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 title description 16
- 239000000203 mixture Substances 0.000 claims abstract description 417
- 239000002537 cosmetic Substances 0.000 claims abstract description 134
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 131
- 239000013543 active substance Substances 0.000 claims abstract description 122
- 150000004677 hydrates Chemical class 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 10
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- -1 acyclic hydrocarbon Chemical class 0.000 claims description 245
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 239000000049 pigment Substances 0.000 claims description 112
- 239000000460 chlorine Substances 0.000 claims description 80
- 210000004709 eyebrow Anatomy 0.000 claims description 78
- 210000000720 eyelash Anatomy 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 239000003795 chemical substances by application Substances 0.000 claims description 53
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 47
- 238000012216 screening Methods 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 239000003921 oil Substances 0.000 claims description 43
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 42
- 229940043267 rhodamine b Drugs 0.000 claims description 42
- 238000011282 treatment Methods 0.000 claims description 42
- 239000000982 direct dye Substances 0.000 claims description 36
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 229930195733 hydrocarbon Natural products 0.000 claims description 32
- 239000004215 Carbon black (E152) Substances 0.000 claims description 31
- 239000000975 dye Substances 0.000 claims description 29
- 229920006395 saturated elastomer Polymers 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 125000000129 anionic group Chemical group 0.000 claims description 25
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 150000002430 hydrocarbons Chemical class 0.000 claims description 23
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000003277 amino group Chemical group 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 125000002091 cationic group Chemical group 0.000 claims description 18
- 235000013980 iron oxide Nutrition 0.000 claims description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 claims description 15
- 229910052705 radium Inorganic materials 0.000 claims description 15
- 229910052701 rubidium Inorganic materials 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229920006294 polydialkylsiloxane Polymers 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 claims description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 8
- 239000000341 volatile oil Substances 0.000 claims description 8
- 229920001661 Chitosan Polymers 0.000 claims description 7
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- VVNRQZDDMYBBJY-UHFFFAOYSA-M sodium 1-[(1-sulfonaphthalen-2-yl)diazenyl]naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 VVNRQZDDMYBBJY-UHFFFAOYSA-M 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 229910021417 amorphous silicon Inorganic materials 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 125000005375 organosiloxane group Chemical group 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000006229 carbon black Substances 0.000 claims description 4
- FBZANXDWQAVSTQ-UHFFFAOYSA-N dodecamethylpentasiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C FBZANXDWQAVSTQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940087203 dodecamethylpentasiloxane Drugs 0.000 claims description 4
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 4
- 229920002545 silicone oil Polymers 0.000 claims description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 4
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 claims description 3
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- KQVJZDZLEDQCSD-UHFFFAOYSA-H dialuminum;2-[[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]benzenesulfonate Chemical compound [Al+3].[Al+3].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1.C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1.C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 KQVJZDZLEDQCSD-UHFFFAOYSA-H 0.000 claims description 3
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 claims description 3
- HSNQKJVQUFYBBY-UHFFFAOYSA-N dipentyl carbonate Chemical compound CCCCCOC(=O)OCCCCC HSNQKJVQUFYBBY-UHFFFAOYSA-N 0.000 claims description 3
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052618 mica group Inorganic materials 0.000 claims description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
- NOFQKTWPZFUCOO-UHFFFAOYSA-N 2,2,4,4,6-pentamethylheptane Chemical compound CC(C)CC(C)(C)CC(C)(C)C NOFQKTWPZFUCOO-UHFFFAOYSA-N 0.000 claims description 2
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 claims description 2
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 claims description 2
- PDWFFEHBPAYQGO-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-hexyl-dimethylsilane Chemical compound CCCCCC[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C PDWFFEHBPAYQGO-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 claims description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 2
- 229940094933 n-dodecane Drugs 0.000 claims description 2
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- SCRSFLUHMDMRFP-UHFFFAOYSA-N trimethyl-(methyl-octyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C SCRSFLUHMDMRFP-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 description 38
- 238000002156 mixing Methods 0.000 description 38
- 235000019198 oils Nutrition 0.000 description 38
- 239000002585 base Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 36
- 229920000642 polymer Polymers 0.000 description 32
- 150000003254 radicals Chemical class 0.000 description 30
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 23
- 150000003141 primary amines Chemical class 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- 239000002390 adhesive tape Substances 0.000 description 18
- 238000011156 evaluation Methods 0.000 description 17
- 229910052500 inorganic mineral Inorganic materials 0.000 description 16
- 239000011707 mineral Substances 0.000 description 16
- 235000010755 mineral Nutrition 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 150000002772 monosaccharides Chemical class 0.000 description 13
- 239000012860 organic pigment Substances 0.000 description 13
- 229920006295 polythiol Polymers 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 230000001464 adherent effect Effects 0.000 description 12
- 150000004676 glycans Chemical class 0.000 description 12
- 210000002374 sebum Anatomy 0.000 description 12
- 229920001282 polysaccharide Polymers 0.000 description 11
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 10
- 239000005017 polysaccharide Substances 0.000 description 10
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000005529 alkyleneoxy group Chemical group 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 9
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
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- 239000000243 solution Substances 0.000 description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000000980 acid dye Substances 0.000 description 7
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- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
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- 238000013467 fragmentation Methods 0.000 description 7
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- 229920000570 polyether Polymers 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001728 carbonyl compounds Chemical class 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001720 carbohydrates Chemical group 0.000 description 5
- 235000012730 carminic acid Nutrition 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
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- 239000002245 particle Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
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- PHBAKVPDAOWHDH-QUFRNCFNSA-N tricyclo[5.2.1.02,6]decanedimethanol diacrylate Chemical compound C12CCCC2[C@H]2C(COC(=O)C=C)C(COC(=O)C=C)[C@@H]1C2 PHBAKVPDAOWHDH-QUFRNCFNSA-N 0.000 description 1
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- 229940117985 trimethyl pentaphenyl trisiloxane Drugs 0.000 description 1
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Abstract
The present invention relates to a process for treating keratin materials, comprising the application to said keratin materials, in one or more successive steps, of at least i) one or more (co)polymers bearing at least one unit of formula (I), and also the optical or geometrical isomers thereof, and/or the solvates thereof, such as the hydrates, or a composition containing same in which formula (I) Ra, Rb, Rc, Rd and q are as defined in the description, ii) at least water, iii) at least one crosslinking agent and iv) optionally a cosmetic active agent.
Description
Description
Title: Process for treating keratin materials using at least one (co)polymer of polyvinyl alcohol (PVA) bearing acetoacetate functions and at least one crosslinking agent
Technical field
The present invention relates more particularly to the cosmetic field, notably to the treatment of keratin materials, in particular for caring for and/or making up the skin and/or the lips and/or the eyelashes and/or the eyebrows.
The aim is thus notably to propose novel treatment processes, notably cosmetic treatment processes, comprising the application to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, of at least one (co)polymer of polyvinyl alcohol (PVA) bearing acetoacetate functions, of water, of at least one crosslinking agent, and optionally of at least one cosmetic active agent, which are most particularly advantageous in terms of their technical performance, notably in terms of the resistance of the deposits they make it possible to obtain, and the sensorial experience they give the user.
Prior art
Cosmetic products conventionally require the use of one or more film-forming polymers in order to obtain a quality deposit of these products on keratin materials, and in particular to satisfy the expectations detailed below.
Thus, in the field of skin and/or lip makeup, it is most particularly expected that the deposit formed does not transfer on contact with the fingers or clothing.
It must also have good resistance to contact with water, notably rain or during showering or even perspiration, and also resistance to sebum, or even to contact with edible fats, notably edible oils when this deposit is formed on the lips. Moreover, this deposit must be comfortable or even glossy.
For this purpose, dispersions of polymer particles of nanometric size are used as filmforming agent in makeup products such as mascaras, eyeliners, eyeshadows or lipsticks, and in products for haircare application, and more particularly in their organic and notably oily phases.
However, the compositions of the prior art have unsatisfactory hold over time.
Compositions are known, notably film-forming cosmetic compositions, comprising at least one fatty phase and at least one copolymer obtained by polymerization of ethylenic monomers, some of which bear particular groups (see, for example, WO 2022/136104). Such compositions nevertheless require the presence of a fatty phase, which may reduce the field to certain applications. Furthermore, these compositions do not necessarily meet the need for naturalness expressed by certain consumers.
It is also known from patent EP 1 392 222 to use a cosmetic composition for caring for and/or treating keratin materials, comprising a supramolecular polymer including a polymer backbone and at least two groups that are capable of forming at least three hydrogen bonds. However, with this composition alternative, the persistence or water resistance performance obtained remain insufficient.
WO 2014/099108 also discloses compositions and processes for forming deposits on keratin substrates, which have good persistence over time, using compounds bearing acetoacetate functions and active agents functionalized so as to be covalently bonded to the keratin materials.
WO 2022/136114 describes a cosmetic aqueous dispersion containing at least i) one polymers having at least one acetoacetate unit of specific formula especially derived from acetoacetoxy ethyl methacrylate monomers, ii) at least one polyvinylpyrrolidone (PVP), and iii) water. Nevertheless, this type of dispersion is not always satisfactory, particularly in terms of fragmentation resistance, and/or resistance to oil and/or sebum.
Moreover, WO 06/042169 describes tissue adhesives, in medical and veterinary applications, formed by the reaction of poly hydroxy compounds derived with acetoacetate groups and/or polyamine compounds derived with acetoacetamide groups with an aminofunctional crosslinking compound.
In general, the treatments and processes described above do not make it possible to obtain deposits, on keratin materials, in particular on the skin and/or the lips, which satisfy all the abovementioned requirements, namely very good resistance to fragmentation, water and/or to fatty substances, notably for the lips, which are moreover comfortable to wear for the users, which make it possible to adjust the gloss of the deposits or which do not produce deposits that are visually unsightly.
Moreover, there is considerable consumer demand for compositions with a reduced environmental impact.
Moreover, in the field of cosmetic products, film-forming compounds that can be conveyed in water are sought for use in cosmetic treatments requiring less oil, or even aqueous formulations.
In particular, polyvinyl alcohol (PVA) is an interesting polymer for cosmetic applications. It is a film-forming polymer that can be conveyed in water, leading to deposits with good properties of resistance to fatty substances such as olive oil or sebum, etc.
However, PVA films have a major drawback, in that they are highly sensitive to water, which limits their suitability for application to keratin materials, in particular the skin and/or the lips.
Disclosure of the invention
There is thus still a need for a treatment process, notably a cosmetic process, intended for application to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, which allows a film-forming deposit to be obtained which is non-tacky, transfers little, if at all, is comfortable, and is persistent, in particular with respect to water and fatty substances, in particular oils.
There is also still a need for a treatment process, notably a cosmetic treatment process, which allows deposits to be obtained that are resistant to water and fatty substances, in particular sebum.
There is also still a need for a treatment process, notably a cosmetic treatment process, which allows deposits to be obtained whose gloss can be modulated and/or which are not visibly unsightly, and which are ideally invisible if they are not coloured.
There is also still a need for a treatment process, notably a cosmetic treatment, using aqueous or predominantly aqueous compositions and leading to water-resistant deposits.
The present invention is specifically directed towards meeting all or some of these needs.
Summary of the invention
These problems are solved by the use of a process, notably a cosmetic process, for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, comprising the application to said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, in one or more successive steps, of at least:
i) one or more (co)polymers bearing at least one unit of formula (I), and also the optical or geometrical isomers thereof, and/or the solvates thereof, such as hydrates, or a composition containing same:
in which formula (I):
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom,
- Rb and Rc, which may be identical or different, represent a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Rb and Rc represent a hydrogen atom, - Rd represents a linear or branched (Ci-C4)alkyl group; preferably, Rd represents a methyl group;
- p is an integer greater than or equal to 2, and optionally of at least one unit of formula (II):
in which formula (II):
- q denotes an integer greater than or equal to 2, and
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom; and optionally of at least one unit of formula (III):
in which formula (III):
- 1 represents an integer greater than or equal to 2, and
- R represents a linear or branched, saturated or unsaturated, aromatic or non-aromatic, cyclic or acyclic hydrocarbon-based chain comprising from 1 to 10 carbon atoms; preferably, R represents a (Ci-Ce)alkyl group, in particular methyl;
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom; and ii) water; iii) one or more crosslinking agents; and iv) optionally one or more cosmetic active agents chosen from a) dyestuffs other than rhodamine B, b) active agents for caring for keratin materials, c) UV- screening agents, and d) mixtures thereof.
According to a preferred embodiment, the treatment process according to the invention comprises the application of at least iv) a cosmetic active agent as defined above and hereinbelow, to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
According to a preferred embodiment, the process according to the invention comprises the application i) of at least one (co)polymer as defined previously, the optical or geometrical isomers thereof and/or the solvates thereof, such as the hydrates, or of a composition containing same, the application ii) of at least water, iii) at least one crosslinking agent and the application iv) of at least one cosmetic active agent chosen from a) dyestuffs other than rhodamine B, b) active agents for caring for keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, c) UV-screening agents, and d) mixtures thereof; more preferentially, a) the cosmetic active agent(s) are chosen from dyestuffs other than rhodamine B.
Water ii) may be applied at the same time as i), iii) or iv), when iv) is present, or else at the same time as i) and iii), and optionally iv).
Water ii) may also be applied before i), iii) and optionally iv).
According to a preferred embodiment, water is at least applied at the same time as i); in other words, i) and ii) are applied simultaneously, i) also possibly being applied in the presence or absence of ii) water, and when iv) is present, iv) also possibly being applied in the presence or absence of ii) water.
The application of ingredients i), ii), iii) and optionally iv) to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, leads to deposits on said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, which have very good water resistance.
The inventors have thus found, surprisingly, that the application of ingredients i), ii), iii) and optionally iv) to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, leads to deposits on said keratin materials, notably the skin, which have good resistance to external attacking factors, for instance water, oils, notably edible oils, sweat and/or sebum, and thus have very good hold over time.
Advantageously, the deposits obtained via the processes according to the invention are also very comfortable. They are not tacky and do not transfer. The deposits obtained via the processes according to the invention may also be glossy. The visual appearance of the deposits is moreover very satisfactory.
Definitions
For the purposes of the present invention, throughout the description, including the claims, and unless otherwise indicated:
- The term “(co)polymer” means a homopolymer or a copolymer.
- The term “copolymer” means a polymer formed by linking monomer units of different chemical structures; for example, a polymer consisting of at least one unit of formula (I) and of at least one unit of formula (II) and/or of formula (III) is a copolymer for the purposes of the invention.
- The term “cosmetic active agent” means an organic or organosilicon compound or a mineral compound which can be incorporated into a cosmetic composition to give an effect on keratin materials, whether this effect is immediate or provided by repeated applications.
Examples of cosmetic active agents according to the invention include a) dyestuffs chosen from pigments, direct, anionic, cationic, zwitterionic or neutral dyes, which are non- fluorescent or fluorescent but different from rhodamine B, or such as optical brighteners, or UVA and/or UVB screening agents and mixtures thereof, b) active agents for caring for keratin materials, notably the skin, such as anti-ageing active agents or those intended to benefit the skin, such as active agents acting on the barrier function, deodorant active agents, antiperspirant active agents, desquamating active agents, antioxidant active agents, moisturizing active agents, sebum-regulating active agents, active agents intended for combating the effects of pollution, antimicrobial or bactericidal active agents, fragrances, fluorescent colourless compounds such as optical brighteners, vitamins; and dyestuffs other than rhodamine B such as direct dyes or pigments, preferably pigments, c) UVA and/or UVB screening agents and d) the mixture of a) + b), or the mixture of a) + c), or the mixture of b) + c), or the mixture of a) + b) + c).
Preferentially, the cosmetic active agents are chosen from a) dyestuffs chosen from pigments, direct dyes other than rhodamine B (more particularly rhodamines), more preferentially the direct dyes are non-fluorescent, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof.
- For the purposes of the present invention, the term ‘fatty substance” means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably less than 1% and even more preferentially less than 0.1%); in addition, the fatty substances are soluble in organic solvents under the same temperature and pressure conditions, for instance in halogenated solvents such as chloroform or dichloromethane, lower alcohols such as ethanol or aromatic solvents such as benzene or toluene.
- The term “(hetero)aryl” means aryl or heteroaryl groups.
- The term “(hetero)cycloalkyl” means cycloalkyl or heterocycloalkyl groups.
- The “aryl” or “heteroaryl” radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from:
. a Ci-C6 and preferably C1-C4 (poly)(hydroxy)alkyl radical;
. a halogen atom such as chlorine, fluorine or bromine;
. a hydroxyl group;
. a C1-C2 alkoxy radical; a C2-C4 (poly)hydroxyalkoxy radical;
. an amino radical;
. an amino radical substituted with one or two identical or different Ci-Ce and preferably C1-C4 alkyl radicals;
. an acylamino radical (-N(R)-C(O)-R’) in which the radical R is a hydrogen atom;
. a C1-C4 alkyl radical and the radical R’ is a C1-C4 alkyl radical; a carbamoyl radical ((R)2N-C(O)-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical;
. an alkylsulfonylamino radical (R’-S(O)2-N(R)-) in which the radical R represents a hydrogen atom or a C1-C4 alkyl radical and the radical R’ represents a C1-C4 alkyl radical, or a phenyl radical;
. an aminosulfonyl radical ((R)2N-S(O)2-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical;
. a carboxylic radical in acid form or salified (preferably with an alkali metal or a substituted or unsubstituted ammonium) form;
. a cyano group (CN);
. a polyhalo(Ci-C4)alkyl group, preferentially trifluoromethyl (CF3).
- The cyclic or heterocyclic part of a non-aromatic radical may be substituted with at least one substituent borne by a carbon atom, chosen from the following groups:
. hydroxyl,
. C1-C4 alkoxy, C2-C4 (poly )hydroxy alkoxy;
. alkylcarbonylamino ((R-C(O)-NR’-), in which the radical R’ is a hydrogen atom or a C1-C4 alkyl radical and the radical R is a C1-C2 alkyl radical, amino substituted with one or two identical or different C1-C4 alkyl groups;
. alkylcarbonyloxy ((R-C(O)-O-), in which the radical R is a C1-C4 alkyl radical, amino substituted with one or two identical or different C1-C4 alkyl groups;
. alkoxycarbonyl ((R-O-C(O)-) in which the radical R is a C1-C4 alkyl radical, amino substituted with one or two identical or different C1-C4 alkyl groups;
- A cyclic or heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical, may also be substituted with one or more oxo groups.
- A hydrocarbon-based chain is unsaturated when it includes one or more double bonds and/or one or more triple bonds.
- An “aryl” radical represents a monocyclic or fused or non-fused polycyclic hydrocarbonbased group comprising from 6 to 14 carbon atoms, and at least one ring of which is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl.
- A “heteroaryl” radical represents a monocyclic or fused or non-fused polycyclic, 5- to 14- membered group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenoxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, thiadiazolyl, thiazolyl, thiazolopyridyl, thiazoylimidazolyl, thiopyrylyl and xanthylyl.
- A “cyclic” or “cycloalkyl” radical is a monocyclic or fused or non-fused polycyclic, nonaromatic cyclic hydrocarbon -based radical containing from 5 to 14 carbon atoms, which may include one or more unsaturations; the cycloalkyl is preferably a cyclohexyl group.
- A “heterocyclic” or “heterocycloalkyl” radical is a monocyclic or fused or non-fused polycyclic 3- to 9-membered non-aromatic cyclic radical, including from 1 to 4 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms; preferably, the heterocycloalkyl is chosen from epoxide, piperazinyl, piperidyl, morpholinyl and dithiolane.
- An “alkyl” radical is a linear or branched, in particular Ci-Ce and preferably C1-C4 saturated hydrocarbon-based radical.
- An “alkoxy” radical is an alkyl-oxy radical for which the alkyl radical is a linear or branched Ci-Ce and preferentially C1-C4 hydrocarbon-based radical.
- A “(poly)(hydroxy)alkyl” radical denotes a Ci-Ce and preferably C1-C4 alkyl radical optionally substituted with one or more hydroxyl radicals, preferably substituted with from 1 to 4 hydroxyl groups, more particularly between 1 and 3.
- A “sugar” radical is a monosaccharide or disaccharide radical. Sugar radicals that may be mentioned include: sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose or lactose.
- The term “monosaccharide” refers to a mono-oside sugar comprising at least 5 carbon atoms of formula CX(H2O)X with x an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x is equal to 6; they may be of D or L configuration, and of alpha or beta anomer, and also the salts thereof and the solvates thereof such as hydrates.
- The term “disaccharide” refers to a di-oside sugar which is a compound constituted of two saccharides bonded together via O-oside bonds, said compounds being constituted of two monosaccharide units (also known as mono-osides) as defined previously, said monosaccharide units comprising at least 5 carbon atoms, preferably 6; in particular, the mono-oside units are linked together via a 1,4 or 1,6 bond as a (alpha) or p (beta) anomer, it being possible for each oside unit to be of L or D configuration, and also the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from two saccharides (or monosaccharides) having the general formula: -[Cx(H2O)y)]2- or -[(CH2<3)X]2-, with x being an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive, preferably x is equal to 6, and y is an integer representing x - 1.
- The term “polysaccharide” refers to a polysaccharide sugar which is a polymer constituted of several saccharides bonded together via O-oside bonds, said polymers being constituted of monosaccharide units (also known as mono-osides) as defined previously, said monosaccharide units comprising at least 5 carbon atoms, preferably 6; in particular, the monosaccharide units are linked together via a 1,4 or 1,6 bond as a (alpha) or p (beta) anomer, it being possible for each oside unit to be of L or D configuration, and also the salts thereof and the solvates thereof such as the hydrates of said monosaccharides; more particularly, they are polymers formed from a certain number of saccharides (or monosaccharides) having the general formula: -[Cx(H2O)y)]w- or -[(CH2O)X]W-, where x is an integer greater than or equal to 5, preferably x is greater than or equal to 6, in particular x is between 5 and 7 inclusive and preferably x is equal to 6, and y is an integer which represents x - 1, and w is an integer greater than or equal to 2, particularly between 3 and 3000 inclusive, more particularly between 5 and 2500, preferentially between 10 and 2300, particularly between 15 and 1000 inclusive, more particularly between 20 and 500, preferentially between 25 and 200.
- An “anionic counterion” is an anion or an anionic group associated with the cationic charge; more particularly, the anionic counterion is chosen from: i) halides such as chloride or bromide; ii) nitrates; iii) sulfonates, including Ci-Ce alkylsulfonates: Alk-StOj O’ such as methanesulfonate or mesylate and ethanesulfonate; iv) arylsulfonates: Ar-StOj O’ such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-O-S(O)O" such as methyl sulfate and ethyl sulfate; x) aryl sulfates: Ar-O-S(O)O" such as benzene sulfate and toluene sulfate; xi) alkoxy sulfates: Alk- O-S(O)2O" such as methoxy sulfate and ethoxy sulfate; xii) aryloxy sulfates: Ar-O-StOj O’; xiii) phosphate; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate.
- The “solvates” represent hydrates and also the combination with linear or branched C1-C4 alcohols such as ethanol, isopropanol or n-propanol.
- The term “UV-A screening agent” means a chromophore derived from a compound which screens out (or absorbs) UV-A ultraviolet rays at a wavelength of between 320 and 400 nm. A distinction may be made between short UV-A screening agents (which absorb rays at a wavelength of between 320 and 340 nm) and long UV-A screening agents (which absorb rays at a wavelength of between 340 and 400 nm).
- The term “UV-B screening agent” means a chromophore derived from a compound which screens out (or absorbs) UV-B ultraviolet rays at a wavelength of between 280 and 320 nm.
- The term “chromophore” means a radical derived from a colourless or coloured compound that is capable of absorbing UV and/or visible radiation at a wavelength kabs of between 250 and 800 nm. Preferably, the chromophore is coloured, i.e. it absorbs wavelengths in the visible range, i.e. preferably between 400 and 800 nm. Preferably, the chromophores appear coloured to the eye, particularly between 400 and 700 nm (Ullmann’s Encyclopedia, 2005, Wiley-VcH, Verlag “Dyes, General Survey”, § 2.1 Basic Principle of Color);
- The term “anhydrous composition” means that said composition contains an amount of less than 5% by weight of water, preferentially less than 3% by weight of water, better still less than 1% by weight of water, relative to the total weight of the composition in question; even more preferentially, the composition under consideration is free of water.
- The terms “colouring agent” and “dyestuff' are equivalent.
The expression “including a” should be understood as being synonymous with “including at least one”, unless otherwise mentioned.
The expressions “between... and...", “comprises from ... to...”, “formed from ... to...” and “ranging from... to...” should be understood as being inclusive of the limits, unless otherwise specified.
It is understood that the treatment processes according to the invention, and also the compositions used, are non-therapeutic.
Detailed description
TREATMENT PROCESS
The first subject of the invention is a treatment process in one or more steps using, on keratin materials, notably on the skin and/or the lips and/or the eyelashes and/or the eyebrows, notably the skin: i) at least one or more (co)polymers, as defined previously and hereinbelow, or a composition containing same; ii) at least water; iii) at least one crosslinking agent, in particular as defined hereinbelow; and iv) optionally at least one cosmetic active agent, in particular as defined hereinbelow.
According to a particular embodiment of the invention, the treatment process according to the invention involves the simultaneous application of ingredients i), ii), iii), and optionally iv).
According to another particular embodiment of the invention, the treatment process according to the invention comprises at least two steps in which ingredients i), ii), iii), and optionally iv), are applied in separate and successive steps to the keratin materials, in particular the skin and/or the lips and/or the eyelashes and/or the eyebrows, it being understood that the cosmetic active agent(s) iv) may be present together with ingredients i) and (ii) and/or with the ingredient(s) iii), which are themselves optionally combined with ii) water.
According to a particular embodiment, ingredient(s) i) and ii) are applied simultaneously to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, and the ingredient(s) iii) are then applied to said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, it being understood that the
ingredient(s) ii) may also be applied with iii) and/or with iv), when iv) is present, and that the ingredient(s) iv), when present, may be applied together with i) and ii) and/or iii), preferably with i) and ii).
According to another particular embodiment, the ingredient(s) iii) are applied to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, and ingredients i) and ii) are then applied together to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, it being understood that ingredient ii) may also be applied with iii) and/or with iv), when iv) is present, and that the ingredient(s) iv) may be applied with iii) and/or with i) and ii), when iv) is present.
According to a particular embodiment of the invention, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, is a cosmetic treatment process for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows.
According to one embodiment of the invention, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, according to the invention using ingredients i), ii), iii) and optionally iv), is a skincare process.
According to one embodiment of the invention, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, is a process for making up the skin, the lips, the eyelashes and/or the eyebrows. According to this embodiment, the process comprises at least one cosmetic active agent chosen from dyestuffs other than rhodamine B, preferably pigments.
According to one embodiment of the invention, the process according to the invention is a process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, comprising the application to said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, of at least:
- a composition, termed “Cl”, comprising i) at least one (co)polymer as defined previously and hereinbelow, and ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; preferably, composition “Cl” does not comprise iii) any crosslinking agent;
- a composition, termed “C2”, comprising i) at least one (co)polymer, as defined previously, ii) water, iii) at least one crosslinking agent as defined hereinbelow, and
optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; preferably, composition “C2” does not comprise iv) any cosmetic active agent;
- a composition termed “C3” comprising i) at least one (co)polymer as defined previously and hereinbelow, ii) water, iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, and iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow;
- a composition, termed “C4”, comprising iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; preferably, composition “C4” does not comprise i) at least one (co)polymer as defined previously and hereinbelow; and/or
- a composition, termed “C5”, comprising iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; and optionally ii) water; preferably, composition “C5” does not comprise i) at least one (co)polymer as defined previously and hereinbelow, and does not comprise iii) at least one crosslinking agent; it being understood that the process uses together or separately i) at least one (co)polymer as defined previously and hereinbelow, ii) water, iii) at least one crosslinking agent, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and that compositions “Cl”, “C2”, “C3”, “C4” and “C5” may also comprise one or more fatty substances v), in particular as defined previously and hereinbelow.
According to one aspect of the invention, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, uses a composition, termed “C3”, comprising i) at least one (co)polymer, as defined previously and hereinbelow, ii) water, iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, and iv) at least one cosmetic active agent, in particular as defined hereinbelow, notably chosen from a) colouring agents other than rhodamine B, such as pigments, direct dyes, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV- screening agents, and d) mixtures thereof, and notably at least one colouring agent other than rhodamine B, more particularly at least one pigment.
According to another aspect, the process for treating keratin materials, in particular the skin and/or the lips and/or the eyelashes and/or the eyebrows, according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, uses a composition termed “Cl” and a composition termed “C4”, said composition “Cl” comprising i) at least one (co)polymer, as defined previously and hereinbelow, ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and said composition “C4” comprising iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally ii) water, and optionally iv) at least one cosmetic active agent, it being understood that at least one of the two compositions “Cl” or “C4” comprises iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; in particular, composition “Cl” or composition “C4” comprises iv) at least one cosmetic active agent; more particularly, composition “Cl” comprises iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and composition “C4” does not comprise any cosmetic active agent.
According to another aspect, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, uses a composition termed “C2” and a composition termed “C4”, said composition “C2” comprising i) at least one (co)polymer, as defined previously and hereinbelow, ii) water, iii) at least one crosslinking agent, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and said composition “C4” comprising iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; it being understood that at least one of the two compositions “C2” or “C4” comprises iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; in particular, composition “C2” or composition “C4” comprises iv) at least one cosmetic active agent; more particularly, composition “C2” comprises iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and composition “C4” does not comprise any cosmetic active agent.
According to another aspect, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, uses a composition termed “Cl”, a composition termed “C4” and a composition termed “C5”, said composition “Cl” comprising i) at least one (co)polymer, as defined previously and hereinbelow, ii) water and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, said composition “C4” comprising iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and said composition “C5” comprising iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally ii) water; in particular, compositions “Cl” and “C4” do not comprise any cosmetic active agent.
According to another aspect, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, uses a composition termed “C2”, a composition termed “C4” and a composition termed “C5”, said composition “C2” comprising i) at least one (co)polymer, as defined previously and hereinbelow, ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, said composition “C4” comprising iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and said composition “C5” comprising iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally ii) water; in particular, compositions “C2” and “C4” do not comprise any cosmetic active agent.
According to another aspect, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows according to the invention, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, uses a composition termed “C3” and a composition termed “C5”, said composition “C3” comprising i) at least one (co)polymer, as defined previously and hereinbelow, ii) water, iii) at least one crosslinking agent, in particular as defined previously
and hereinbelow, and iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and said composition “C5” comprising iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow, and optionally ii) water. According to a variant of the process of the invention, ingredient(s) i), ii), and optionally iv) are applied together, i.e. simultaneously, to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows during a first step, and then during a subsequent step, ingredient(s) iii), and optionally iv), are applied to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows; preferably, said process uses iv) either during the first step or during the second step; preferably, iv) is applied together with i) and ii) during the first step.
According to a particular embodiment, the process according to the invention comprises two successive steps of applying to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, two different compositions, preferably at least one of which compositions comprises iv) at least one cosmetic active agent as defined.
According to a particular embodiment of the process, during the first step a composition “Cl” or “C2”, preferably composition “Cl”, is applied to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, and a composition “C4” is then applied to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrow; preferably, at least one of the compositions used comprises iv) at least one cosmetic active agent as defined.
According to yet another variant of the process of the invention, ingredient(s) iii) and optionally iv) and/or ii) is/are applied to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, and ingredient(s) i), ii) and optionally iv) at least one cosmetic active agent, in particular as defined previously, are then applied to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows; preferably, said process uses iv) either during the first step or during the second step; preferably, iv) is applied together with i), and ii) during the second step. In particular, composition “C4” is applied to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, and composition “Cl” is then applied; preferably, composition “C4” and/or composition “Cl”, preferably composition “Cl”, comprises iv) at least one cosmetic active agent as defined.
According to another variant of the process according to the invention, a composition “Cl” containing i), ii) water and optionally iv), is applied, and sequentially a composition “C4” containing iii), and optionally iv), composition “Cl” preferably being applied before composition “C4”; preferably, at least one of the compositions “Cl” and/or “C4” contains iv), and preferably “Cl” contains iv).
Compositions “Cl”, “C2”, “C3”, “C4” and/or “C5” of the process according to the invention, which comprise at least one fatty substance, notably at least one oil, and water, may be in the form of a direct or inverse emulsion.
The compositions “C3” of the process according to the invention may thus be applied directly as such to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, or may even be formed directly on the surface of the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
According to the invention, three application methods known as the “one-gesture application mode”, the “two-gesture application mode” and the “three-gesture application mode” are thus distinguished.
According to one embodiment of the process of the invention, the process is performed in one gesture by applying composition “C3”, as defined previously, to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
Thus, according to one embodiment, the treatment process according to the invention comprises a single step of applying composition “C3” to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
The term “one-gesture application mode” means the direct application to the target keratin materials, notably the target skin and/or lips and/or eyelashes and/or eyebrows, of a single composition in accordance with the invention, namely composition “C3”.
After application of composition “C3”, a persistent, non-tacky deposit is advantageously obtained. The deposit obtained is also resistant to edible oils, water, sebum and friction.
According to another embodiment of the process of the invention, the process is performed in two gestures.
The term “two-gesture application mode” means the successive application, to keratin materials, notably the skin and/or lips and/or eyelashes and/or eyebrows, of two different compositions, for example “Cl” and “C4”, or “C2” and “C4”, or “C3” and “C5”, preferably “Cl” then “C4”, “C2” then “C4”, or “C3” then “C5”, more preferentially “Cl” then “C4”;
preferably, at least one of the compositions “Cl” and/or “C2” and/or “C4” comprises iv) at least one cosmetic active agent.
According to another embodiment, the process of the invention is performed in three gestures.
The term “three-gesture application mode” means the sequential application of three different compositions “Cl” to “C5”, preferably at least one of the compositions used containing iv) at least one cosmetic active agent as defined. According to this application mode, for example according to one embodiment, sequential application is performed on keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, of a) a composition “Cl”, and P) a composition “C4”, and y) a composition “C5”; preferably, composition “Cl” is applied before composition “C4” or “C5”.
According to another embodiment, sequential application is performed on keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, of a) a composition “C2”, and P) a composition “C4”, and y) a composition “C5”; preferably, composition “C2” is applied before composition “C4” or “C5”.
In the two- or three-gesture application modes, the composition applied first, for example “Cl” or “C2”, is conventionally described as a “base coat”, and the composition(s) superimposed thereon, generally described as a “top coat”; preferably, at least one of the compositions used contains iv) at least one cosmetic active agent as defined.
After application of the various compositions “Cl” to “C5”, a persistent, non-tacky deposit is advantageously obtained. The deposit obtained is also resistant to edible oils and to water. According to a particular embodiment, the compositions are applied to dry keratin materials, notably to dry skin and/or lips and/or eyelashes and/or eyebrows.
According to a particular embodiment, the compositions are applied to moist or wet keratin materials, notably to moist or wet skin and/or lips and/or eyelashes and/or eyebrows, i.e. to keratin materials, notably skin and/or lips and/or eyelashes and/or eyebrows, containing water on the surface.
According to one aspect, the present invention relates to a process, notably a cosmetic process, for keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, in particular for caring for and/or making up the skin, the lips, the eyelashes and/or the eyebrows, comprising a step of applying to said keratin materials, notably said skin or said lips or said eyelashes or said eyebrows, a composition “C3”, notably containing at least
one dyestuff other than rhodamine B, in particular as defined previously, and more particularly at least one pigment.
According to another of its aspects, the present invention relates to a cosmetic treatment process for caring for and/or making up keratin materials, notably the skin, the lips, the eyelashes and/or the eyebrows, comprising the successive application of at least:
- a composition, termed “Cl”, comprising i) at least one (co)polymer as defined previously and hereinbelow, ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; and then
- a composition, termed “C4”, comprising iii) at least one crosslinking agent, in particular as defined previously and hereinbelow, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously and hereinbelow; at least one of the compositions “Cl” and/or “C4” containing at least one dyestuff other than rhodamine B, in particular as defined previously and hereinbelow, preferably at least one pigment, and more preferentially composition “Cl” comprises at least one pigment.
According to another of its aspects, the present invention relates to a cosmetic treatment process for caring for and/or making up keratin materials, notably the skin, the lips, the eyelashes and/or the eyebrows, comprising the sequential application of at least:
- a composition “Cl” or “C2” as defined previously; and
- a composition “C4” as defined previously; and
- a composition “C5” as defined previously; it being understood that compositions “Cl” and/or “C2” and/or “C4” and/or “C5” contain at least one dyestuff other than rhodamine B, in particular as defined hereinbelow, preferably at least one pigment. Preferably, composition “C5” comprises at least one pigment.
Polyvinyl alcohol (PVA) (co)uolymers functionalized with acetoacetate functions
As indicated above, the treatment process according to the invention comprises the application to keratin materials, in particular the skin and/or the lips and/or the eyelashes and/or the eyebrows, i) of at least one (co)polymer bearing at least one unit of formula (I), optionally at least one unit of formula (II) and optionally at least one unit of formula (III), or a composition containing same.
Thus, the treatment process according to the invention comprises the application to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, of at least: i) one or more (co)polymers, and also the optical or geometrical isomers thereof and/or the solvates thereof, such as the hydrates, bearing at least one unit of formula (I), or a composition containing same:
in which formula (I):
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom,
- Rb and Rc, which may be identical or different, represent a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Rb and Rc represent a hydrogen atom,
- Rd represents a linear or branched (Ci-C4)alkyl group; preferably, Rd represents a methyl group;
- p is an integer greater than or equal to 2, and optionally of at least one unit of formula (II):
in which formula (II):
- q denotes an integer greater than or equal to 2, and
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom; and optionally of at least one unit of formula (III):
in which formula (III):
- 1 represents an integer greater than or equal to 2, and
- R represents a linear or branched, saturated or unsaturated, aromatic or non-aromatic, cyclic or acyclic hydrocarbon-based chain comprising from 1 to 10 carbon atoms; preferably, R represents a (Ci-Ce)alkyl group, in particular methyl;
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom; ii) water; iii) one or more crosslinking agents; and iv) optionally one or more cosmetic active agents chosen from a) dyestuffs other than rhodamine B, b) active agents for caring for keratin materials, c) UV- screening agents, and d) mixtures thereof.
Preferably, the (co)polymer(s) of the invention are copolymers.
According to one preferred embodiment, the (co)polymer(s) according to the invention comprise at least one unit of formula (I) and at least one unit of formula (II).
According to another particular embodiment, the (co)polymer(s) according to the invention comprise at least one unit of formula (I) and at least one unit of formula (III).
According to a preferred embodiment, the (co)polymer(s) according to the invention comprise at least one unit of formula (I), at least one unit of formula (II) and at least one unit of formula (III).
According to a preferred embodiment, the (co)polymer(s) according to the invention comprise from 0.01 mol% to 42 mol% of units of formula (I), preferably from 0.1 mol% to 40 mol% of units of formula (I), and more preferentially from 1 mol% to 30 mol% of units of formula (I), better still from 5 mol% to 28 mol% of units of formula (I), even better still from 10 mol% to 25 mol% of units of formula (I).
According to a preferred embodiment, the (co)polymer(s) according to the invention comprise from 48 mol% to 99.99 mol% of units of formula (II), in particular from 60 mol% to 99.99 mol% of units of formula (II), in particular from 70 mol% to 99.99 mol% of units of formula (II), in particular from 69.9 mol% to 99.9 mol% of units of formula (II), preferably from 69 mol% to 99 mol% of units of formula (II), more preferentially from 65 mol% to 95 mol% of units of formula (II), and better still from 65 mol% to 90 mol% of units of formula (II).
According to a preferred embodiment, the (co)polymer(s) according to the invention comprise from 0% to 30 mol% of units of formula (III), preferably from 0% to 28 mol% of units of formula (III), and more preferentially from 0.1 mol% to 26 mol% of units of formula (III).
According to a preferred embodiment, the (co)polymer(s) according to the invention comprise:
- from 1 mol% to 30 mol% of units of formula (I),
- from 49 mol% to 99 mol% of units of formula (II),
- from 0% to 26 mol% of units of formula (III).
According to a preferred embodiment, the (co)polymer(s) according to the invention comprise:
- from 1 mol% to 25 mol% of units of formula (I),
- from 49 mol% to 99 mol% of units of formula (II),
- from 0% to 26 mol% of units of formula (III).
According to a particularly preferred embodiment, the (co)polymer(s) according to the invention comprise:
- from 6 mol% to 25 mol% of units of formula (I),
- from 50 mol% to 89 mol% of units of formula (II),
- from 5 mol% to 25 mol% of units of formula (III).
According to a preferred embodiment, the (co)polymer(s) according to the invention have a mass-average molecular weight ranging from 1000 g/mol to 1 000 000 g/mol, preferably from 5000 g/mol to 500 000 g/mol, and more preferentially from 10 000 g/mol to 300 000 g/mol.
According to a particular embodiment, the (co)polymer(s) as defined above are present in a composition, notably in a composition “Cl”, “C2” or “C3”, in a content ranging from
0.001% to 50% by weight, preferably from 0.01% to 30% by weight, and more preferentially from 0.1% to 25% by weight, relative to the total weight of said composition.
The (co)polymer(s) of formula (I) according to the invention may be prepared by functionalizing polyvinyl alcohol (PVA), to obtain polyvinyl alcohol bearing acetoacetate functions.
The functionalization of the poly(vinyl alcohol) may be performed by a transesterification reaction with an acetoacetate ester derivative (IV) using a compound of formula -[CH2- C(Ra)(OH)]p- or -[CH2-C(Ra)(OH)]p-[CH2-C(Ra)(-O-C(O)-R)-]t to give the (co)polymer(s) according to the invention, as illustrated in the following schemes:
in which schemes:
- R, Ra, Rb, Rc, Rd, p and t are as defined previously;
- Re represents a linear or branched, saturated or unsaturated, aromatic or non-aromatic, cyclic or acyclic hydrocarbon-based chain comprising from 1 to 10 carbon atoms; preferably, Re represents a (Ci-Ce)alkyl group, in particular methyl, ethyl, n-propyl, isopropyl or tert-butyl, more preferentially tert-butyl;
- p’ is a non-zero integer less than or equal to p, preferably strictly less than p, and corresponding to the number of repeating units bearing groups -O-C(O)-C(Rb)(Rc)-C(O)- Rd grafted in place of the hydroxyl group, p being as defined previously;
- p” is an integer greater than or equal to 0, it being understood that, preferably, the sum of p’ + p” = p.
Preferably, p’ is non-zero and is less than or equal to p multiplied by 0.4, more preferentially p’ is less than or equal to p multiplied by 0.3.
Preferably p” is non-zero and preferably less than or equal to p multiplied by 0.6, more preferentially p” is less than or equal to p multiplied by 0.7.
According to a particular embodiment, p’ is between (0.001 multiplied by p) and (0.3 multiplied by p).
More particularly, the compound of formula (IV) is chosen from methyl acetoacetate, ethyl acetoacetate, isopropyl acetoacetate and tert-butyl acetoacetate. Preferably, the compound of formula (IV) is tert-butyl acetoacetate.
In particular, the (co)polymer(s) according to the invention may be prepared from polyvinyl alcohol (PVA) compounds of formula (II), which are partially or totally hydrolysed, notably those sold under the reference Kuraray Poval by the company Kuraray, notably the POVAL range, or else those sold by the company Sigma-Aldrich (see, for example, https://www. sigmaaldrich.com/FR/en/search/poly(vinyl- alcohol)?focus=products&page=l&perpage=30&sort=relevance&term=poly%28vinyl%20 alcohol%29&type=product).
It may in particular be polyvinyl alcohol chosen from:
- poly(vinyl alcohols) with an average molecular weight Mw of 89 000-98 000, more than 99% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 30000 to 70000, from 87% to 90% hydrolysed;
- poly (vinyl alcohols) with an average molecular weight Mw of 13 000-23 000, from 87% to 89% hydrolysed;
- poly (vinyl alcohols) with an average molecular weight Mw of 9000-10 000, 80% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 146 000-186 000, more than 99% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 85 000-124 000, over 99% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 31 000-50 000, from 98% to 99% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 31 000-50 000, from 87% to 89% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 85 000-124000, from 87% to 89% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 146 000-186 000, from 87% to 89% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 13 000-23 000, 98% hydrolysed;
- poly(vinyl alcohols) with an average molecular weight Mw of 130 000, over 99% hydrolysed;
- fully hydrolysed - poly(vinyl alcohol);
- poly(vinyl alcohol) sold by the company Sigma-Aldrich under the reference 4-88 Emprove® Essantial;
- poly(vinyl alcohol) sold by the company Sigma-Aldrich under the reference 8-88 Emprove® Essantial (CAS No. 9002-89-5, Mw equal to 67 000); or
- poly (vinyl alcohol) sold by the company Sigma- Aldrich under the reference 40-88 Emprove® Essantial.
Preferably, the (co)polymer(s) according to the invention may be prepared from partially hydrolysed poly(vinyl alcohols), more preferentially 88% hydrolysed.
In particular, this may be the poly(vinyl alcohol) sold by the company Sigma- Aldrich under the reference 8-88 Emprove® Essantial.
CROSSLINKING AGENT
The treatment process according to the invention as described previously comprises the application to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or
1 the eyebrows, (i) of at least one or more (co)polymers as defined previously, and (iii) of at least one crosslinking agent.
For the purposes of the invention, the term “crosslinking agent”, also termed “R”, denotes a compound that is capable of establishing at least one covalent bond with at least one acetoacetate function of the (co)polymer(s) used in the treatment process according to the invention, and thus of crosslinking this/these compound(s).
Preferably, the term “crosslinking agent”, also termed “R”, denotes a compound that is capable of establishing at least one covalent bond with an acetoacetate function of the (co)polymer(s) used in the treatment process according to the invention and thus of crosslinking this/these compound(s).
For the purposes of the present invention, it is understood that the terms “crosslinking agent” and “crosslinker” are equivalent.
Compositions “C2”, “C3” and “C4” as defined previously contain at least iii) a crosslinking agent.
The compositions of the invention may comprise a fatty phase, an aqueous phase or may be in the form of a direct or inverse emulsion. Composition “C4” may be an aqueous composition.
Composition “Cl” is an aqueous composition and more preferentially does not contain v) any fatty substances.
According to a particular embodiment, composition “C3” is an aqueous composition and does not contain v) any fatty substances.
The crosslinking agent(s) iii) are preferably present in a mass content ranging from 0.2% to 60% by weight, in particular ranging from 0.5% to 40% by weight, more particularly from 1% to 20% by weight, even more particularly from 1% to 10% relative to the total weight of the composition containing same.
In particular, the crosslinking agent(s) iii) and the (co)polymer(s) i) as defined previously are preferably present in a mass content ranging from 1% to 35% by weight, relative to the total weight of the composition comprising same.
More precisely, the crosslinking agent(s) iii) that are suitable for use in the invention may be chosen from compounds bearing amine, thiol, acrylate and/or carbonyl functions, such as a ketone or aldehyde function.
Thus, according to a particular embodiment, the crosslinking agent iii) is chosen from (poly)amine, (poly)thiol, (poly)carbonyl and (poly)acrylate compounds and mixtures thereof, preferably chosen from (poly)amine, (poly)thiol and (poly)acrylate compounds and mixtures thereof, and more preferentially chosen from (poly)amine, (poly)thiol compounds and mixtures thereof, and more preferentially chosen from (poly)amine compounds.
The term “(poly)amine, (poly)thiol, (poly)carbonyl and (poly)acrylate compounds” is intended to denote compounds including at least one primary or secondary amine, thiol, carbonyl (such as a ketone or aldehyde function) or acrylate function, respectively.
A) (Poly)amine compounds
According to a preferred embodiment, the crosslinking agent R is chosen from (poly)amine compounds.
The (poly)amine compound may be chosen in particular from polyamine compounds bearing several primary and/or secondary amine groups or from amino alkoxysilanes, and more particularly from amino alkoxysilane compounds, diamine compounds, triamine compounds, and mixtures thereof.
The (poly)amine compound may be a compound comprising from 2 to 20 carbon atoms, notably a nonpolymeric compound; they may be acyclic or cyclic, linear or branched, saturated or unsaturated, conjugated or non-conjugated, aromatic or non-aromatic, optionally interrupted with one or more heteroatoms chosen from O, S, Si(R’)2, N(R”) preferably O, Si(R’)2, or combinations thereof such as -Si(R’)2-O- or -O-Si(R’)2-, with R’, which may be identical or different, representing a (Ci-C4)alkyl group such as methyl, and R” representing a hydrogen atom or a (Ci-C4)alkyl group, preferably a hydrogen atom.
The term “non-polymeric compound” means a compound which is not directly obtained via a monomer polymerization reaction.
(Poly)amine compounds that may be mentioned in particular include N-methyl-1,3- diaminopropane, N-propyl-l,3-diaminopropane, N-isopropyl-l,3-diaminopropane, N- cyclohexyl- 1 ,3-diaminopropane, 2-(3-aminopropylamino)ethanol, 3-(2- aminoethyljaminopropylamine, bis (3 - aminopropyl) amine, methylbis(3- aminopropyljamine, N-(3-aminopropyl)- 1 ,4-diaminobutane, N,N- dimethyldipropylenetriamine, l,2-bis(3-aminopropylamino)ethane, N,N’-bis(3- aminopropyl)- 1 ,3-propanediamine, ethylenediamine, 1 ,3-propylenediamine, 1,4-
butylenediamine, lysine, cystamine, xylenediamine, tris(2-aminoethyl)amine, 1,3- bis(aminomethyl)cyclohexane, 1 ,4-bis(aminomethyl)cyclohexane, diaminopropanol, 4,7,10-trioxa-l,13-tridecanediamine, spermidine and C36-alkylenediamines (Priamine™ 1071, 1073, 1074, 1075, respectively), preferably spermidine.
According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine compounds, i.e. they contain only one primary and/or secondary amine group, preferably a primary amine group (NH2).
The (poly)amine compound(s) may be chosen from amino alkoxysilanes, notably of formula RTSi(OR’2)z(R’3)x in which:
- RT is a linear or branched, saturated or unsaturated, cyclic or acyclic Ci-Ce hydrocarbon-based chain substituted with a group chosen from primary amine groups NH2 or secondary amine groups -N(H)R with R representing a C1-C4 alkyl, an aryl or a benzyl substituted with an amino group or with a C1-C4 aminoalkyl group; RT may be interrupted in its chain with a heteroatom (O, S, NH) or a carbonyl group (CO), R being linked to the silicon atom directly via a carbon atom,
- R’2 and R , which may be identical or different, represent a linear or branched (Ci- Ce) alkyl group,
- z denotes an integer ranging from 1 to 3, and
- x denotes an integer ranging from 0 to 2, with z + x = 3.
In particular, R’ 1 is an acyclic chain. Preferably, RT is a linear or branched, saturated or unsaturated Ci-Ce hydrocarbon-based chain substituted with an amine -NH2 or -N(H)R group, with R representing a Ci-Ce alkyl, a C3-C6 cycloalkyl or a Ce aromatic group. More preferentially, RT is a saturated linear Ci-Ce hydrocarbon-based chain substituted with an amine group NH2. Even more preferentially, RT is a saturated linear C2-C4 hydrocarbonbased chain substituted with an amine group NH2.
In particular, R’2 represents an alkyl group comprising from 1 to 4 carbon atoms; preferably, R’2 represents a linear alkyl group comprising from 1 to 4 carbon atoms and more preferentially R’2 represents an ethyl group.
In particular, R represents an alkyl group comprising from 1 to 4 carbon atoms; preferably, RT represents a linear alkyl group comprising from 1 to 4 carbon atoms and more preferentially RT represents methyl or ethyl groups. Preferably, z is equal to 3.
In particular, the (poly)amine compound(s) are chosen from amino alkoxysilanes including only one primary and/or secondary, preferably primary (NH2), amine group, such as 3- aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3- aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m- aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, and N-(2- aminoethylaminomethyl)phenethyltrimethoxysilane.
Preferably, the (poly)amine compound(s) are chosen from 3 -aminopropyltriethoxy silane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, and N-(2-aminoethyl)-3-aminopropyltriethoxysilane, and more preferentially 3- aminopropyltriethoxysilane (APTES), in particular the product sold by Sigma Aldrich.
The (poly)amine compound may also be chosen from amino polymers, notably having a weight-average molecular weight ranging from 500 g.inof1 to 1 000000 g.mol’1, preferably ranging from 500 g.mol’1 to 500000 g.mol’1, and preferentially ranging from 500 g.mol’1 to 100000 g.mol’1.
According to a particular embodiment of the invention, the (poly)amine compound(s) are monoamine compounds and are chosen from polydialkylsiloxanes notably of formula (IV): H2N-ALK-Si(R’2)(R’3)-O-[ Si(R’2)(R’3)-O]n- Si(R’2)(R’3)-R’4 (IV) in which formula (IV):
- Aik represents a (C1-C4) alkylene group which is linear or branched, preferably linear, such as propylene,
- R’2 and R’3, which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, such as methyl, and
- R’4 represents a linear or branched (Ci-Ce)alkyl group, preferably C4, such as n-butyl, n represents an integer greater than or equal to 2, preferably the value of n is such that the weight-average molecular weight of the polydimethylsiloxane ranges from 500 to 3000 g.mol’1. As examples of polydimethylsiloxanes (IV), mention may be made of the products sold under the names MCR-A11 and MCR-A12 by the company Gelest.
According to a particular embodiment of the invention, the (poly)amine compound(s) are diamine compounds, i.e. they contain two primary and/or secondary amine groups, preferably primary amine groups (NH2).
More particularly, they are chosen from the compounds of formula (V) or (VI):
. ALK[(O-ALK’)m-NH2]2 (V)
or
. H2N-ALK-Si(R’)2-[O-Si(R’)2]m-O-Si(R)2-ALK’-NH2 (VI) in which formulae (V) and (VI):
- ALK and ALK’, which may be identical or different, represent a linear or branched (Ci- C6)alkylene group, preferably a linear group such as propylene,
- R’, which may be identical or different, represents a (Ci-C4)alkyl group such as methyl,
- m represents an integer greater than or equal to 0; preferably, the value of m is such that the weight- average molecular weight of compound (V) or (VI) ranges from 500 g.mor1 to 55 000 g.mol’1.
As examples of compounds of formula (VI), mention may be made of those sold under the names DMS-A11, DMS-A12, DMS-A15, DMS-A21, DMS-A31, DMS-A32 and DMS-A35 by the company Gelest.
The (poly)amines compound(s) that are diamines are particularly polyether diamines notably of formula H2N-ALK-O-[ALK’-O]m-ALK”-NH2 with ALK, ALK’ and ALK”, which may be identical or different, representing a linear or branched (Ci-C6))alkylene group, and m representing an integer greater than or equal to 0, such as 4,7,10-trioxa-l,13- tridecanediamine or the compounds known under the reference Jeffamine from the company Hunstman, and more particularly a,co-diamino polyethylene glycol and/or polypropylene glycol (with an amine function at the end of the chain) such as the products sold under the names Jeffamine D-230, D-400, D-2000, D-4000, ED-600, ED-9000 and ED-2003.
According to a particular embodiment of the invention, the (poly)amine compound(s) are triamine compounds, i.e. they contain three primary and/or secondary amine groups, preferably primary amine groups (NH2). More particularly, they are chosen from polyether triamines notably of formula ALK”’[(O-ALK’)m-NH2]3 with ALK’ as defined previously and ALK”’ representing a linear or branched trivalent (Ci-C6)alkylene group, and m representing an integer greater than or equal to 0.
As (poly)amine compounds that are triamine compounds, mention may be made in particular of polyether triamines, and notably a,co-diamino polyethylene glycol and/or polypropylene glycol (with an amine function at the end of the chain) such as the products sold under the names Jeffamine T-403.
According to another particular embodiment of the invention, the (poly)amine compound(s) include more than three primary and/or secondary amine groups, preferably primary amine groups (NH2).
In this variant, the (poly)amine compound(s) are chosen from poly(meth)acrylates or poly(meth)acrylamides bearing lateral primary or secondary amine functions, such as poly(3-aminopropyl)methacrylamide and poly (2- aminoethyl) methacrylate.
Preferably, the (poly)amine compounds are chosen from chitosans (notably poly(D- glucosamine)) and polydimethylsiloxanes comprising primary amine groups at the end of the chain and/or on side chains.
According to this variant, the (poly)amine compound(s) are chosen in particular from poly((C2-C5)alkyleneimines), and preferably polyethylenimines and polypropyleneimines, notably poly(ethyleneimine), in particular the product sold under reference 408700 by the company Aldrich Chemical or under the trade name Lupasol by BASF, notably with a molecular weight of between 1200 and 25 000; poly(allylamine), in particular the product sold under reference 479136 by the company Aldrich Chemical; polyvinylamines and copolymers thereof, notably with vinylamides, in particular vinylamine/vinylformamide copolymers such as those sold under the name Lupamin® 9030 by the company BASF; polyamine acids containing NH2 groups, such as polylysine, in particular the product sold by the company JNC Corporation (formerly Chisso); amino dextran, in particular the product sold by the company CarboMer Inc; amino polyvinyl alcohol, in particular the product sold by the company CarboMer Inc; acrylamido(Ci-C6)alkylamine-based copolymers, notably acrylamidopropylamine-based copolymers; and poly(D-glucosamine), for example sold under the reference Kionutrime CSG® by the company Kytozyme.
According to a particular embodiment, the polydimethylsiloxanes comprising primary amine groups at the end of the chain and/or on side chains are chosen from the compounds of formula (VII) below: Ra-Si(Rb)(Rc)-O-[Si(Rb)(Rc)-O]m-[Si(ALK1-NH2)(Ra)-O]n-Si(Rb)(Rc)-Ra (VII) in which formula (VII):
Ra, which may be identical or different, represents a hydroxyl or (Ci-C4)alkyl group,
- Rb and Rc, which may be identical or different, preferably identical, represent a (Ci-C4)alkyl group, such as methyl,
- ALK1 represents a linear or branched (Ci-Ce) alkylene group, optionally interrupted with an N(H) group,
- m and n are integers greater than or equal to 1 ; preferably, m and n are such that the weightaverage molecular mass of the compound of formula (VII) ranges from 1000 g.mor1 to 500000 g.mor1.
According to a preferred variant, formula (VII) is such that Ra, Rb and Rc represent a methyl group, ALK1 represents a propylene group, n and m are such that the weight- average molecular weight of the polydimethylsiloxane ranges from 1000 g.mor1 to 55 000 g.mor1. As examples of polydimethylsiloxanes of formula (VI), mention may be made of those sold under the names AMS-132, AMS-152, AMS-162, AMS-163, AMS-191 and AMS-1203 by the company Gelest.
According to another variant, formula (VII) is such that Ra represents a hydroxyl or (Ci- C4)alkyl group, such as methyl, ALK1 represents a (Cs-C6)alkylene group substituted with an NH group; preferably, ALK1 represents -(CH2)3-N(H)-(CH2)2-, and m and n are such that the weight- average molecular mass of the compound of formula (VI) ranges from 5000 g.mol'1 to 500000 g.mor1.
As amine polymer, mention may also be made of a,co-diamino polytetrahydrofurans (or polytetramethylene glycol) and a,co-diamino polybutadienes.
According to a particular embodiment of the invention, the (poly)amine compounds are chosen from hyperbranched polymers comprising at least one amino group and dendrimers bearing at least one amino group, such as PAMAM polyamidoamine dendrimers with an ethylenediamine core and a terminal amine function.
According to a preferred embodiment, the composition comprises a crosslinking agent R chosen from (poly)amine compounds, in particular chosen from chitosans, aminoalkoxysilanes, polydimethylsiloxanes comprising primary amine groups at the end of the chain or on side chains, amodimethicones, polyglucosamines, spermidine and mixtures thereof.
More preferentially, the composition comprises a crosslinking agent R chosen from chitosans, aminoalkoxysilanes and polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains such as amodimethicones, and even more preferentially chosen from poly(D-glucosamine), 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-
aminoethyl)-3-aminopropyltriethoxysilane, spermidine and polydimethylsiloxanes comprising terminal amino groups at the end of the chain, such as bis-cetearyl amodimethicone .
According to a preferred embodiment, the crosslinking agent R is chosen from (poly)thiol compounds, also known as “(poly)mercapto” compounds.
The (poly)thiol compound may in particular be organic or inorganic, preferably organic.
In a preferred embodiment, the (poly)thiol compound is silicon-based, i.e. it includes one or more thiol groups and it also includes at least one siloxane chain.
In a particular embodiment, the (poly)thiol compound is inorganic. Mention may be made, for example, of poly thiol silicones.
The (poly)thiol compound may in particular be chosen from non-polymeric (poly)thiol compounds.
For the purposes of the present invention, the term “non-polymeric compounds” means compounds which are not directly obtained via a monomer polymerization reaction.
According to one embodiment of the invention, the (poly)thiol compound(s) are organic, non-polymeric and of formula (VIII) below and also the solvates thereof such as hydrates: L(SH)q (VIII) in which formula (VIII):
- q denotes an integer greater than or equal to 2; preferably, q is between 2 and 10 inclusive and preferably between 2 and 5;
- L denotes a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, multivalent (at least divalent) group, in particular comprising between 1 and 500 carbon and/or silicon atoms, more particularly between 2 and 40 carbon and/or silicon atoms, even more particularly between 3 and 30 carbon and/or silicon atoms, preferably between 6 and 20 carbon atoms; L being optionally interrupted and/or terminated with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof such as -O-, -O-C(X)-, -N(R)-C(X)-, -Si(Rc)(Rd)-O- with R representing a hydrogen atom or a (Ci-Ce)alkyl group such as methyl; and/or L being optionally substituted with one or more groups chosen from: -N(Ra)Rb and -(X’)a-C(X)-(X”)b-Ra; with X, X’ and X”, which may be identical or different, representing an oxygen or sulfur atom, or a group N(Rb); a and b
being 0 or 1, preferably the sum of a + b being 1; Ra and Rb, which may be identical or different, represent a hydrogen atom or a (Ci-Ce)alkyl or aryl(Ci-C4)alkyl group, such as benzyl, preferably Ra and Rb represent a hydrogen atom; and Rc and Rd, which may be identical or different, represent a (Ci-Ce)alkyl, aryl(Ci-C4)alkyl or (Ci-C6)alkoxy group.
According to a particular embodiment of the invention, the (poly)thiol compound(s) are chosen from polythiol compounds, notably polythiol compounds comprising from 2 to 20 carbon atoms.
According to a preferred embodiment, the (poly)thiol compound(s) are non-polymeric and notably of formula (VIII) defined above, in which q is an integer greater than or equal to 2, preferably q is an integer between 2 and 10 inclusive and preferably between 2 and 5.
The (poly)thiol compounds that are suitable for use in the invention are preferably dithiol compounds.
Preferably, L denotes a Cs-Cis multivalent radical, which is notably linear. Preferentially, the liposoluble polythiol is a notably linear Cs-Cis dithiol. Preferably, the Cs-Cis chain is a hydrocarbon-based chain, i.e. formed from carbon and hydrogen. In particular, the liposoluble polythiol is a linear Cs-Ci6 and notably C10-C14 dithiol. As (poly)thiol compounds of formula (VII), mention may be made more particularly of 1,8-octanedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 1,14-tetradecanedithiol, 1,16-hexadecanedithiol and 1,18-octadecanedithiol. Use is preferably made of 1,10-decanedithiol, 1,12- dodecanedithiol and/or 1,14-tetradecanedithiol, preferentially 1,12-dodecanedithiol.
According to another particular embodiment of the invention, the (poly)thiol compound(s) are chosen from thiolated alkoxysiloxanes, such as those of formula (VIII’) below: R’i-Si(OR’2)z(R’3)x (VIII’) in which formula (VIII’):
- RT is a linear or branched, saturated or unsaturated, cyclic or acyclic C1-C12 hydrocarbonbased chain substituted with one or more groups chosen from thiol groups; and aryl, aryloxy, arylthio, arylamino, the aryl group being substituted with one or more thiol groups, or thiol(Ci-C6)alkyl, preferably thiol(Ci-C6)alkyl; and RT is optionally interrupted in its hydrocarbon-based chain with one or more heteroatoms such as O, S, N, a carbonyl group C(O), or a combination thereof such as ester -C(O)-O-, or amide -C(O)-N(H)-, R being bonded to the silicon atom directly via a carbon atom,
- R’2 and R’3, which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, such as methyl,
- z denotes an integer ranging from 1 to 3, and
- x denotes an integer ranging from 0 to 2, with z + x = 3.
Preferably, R’2 represents a linear or branched, preferably linear, alkyl group comprising from 1 to 4 carbon atoms, such as ethyl.
Preferably, R’3 represents a linear or branched, preferably linear, alkyl group comprising from 1 to 4 carbon atoms, such as methyl or ethyl.
Preferably, R’i is an acyclic chain, in particular R’i is a linear or branched, saturated or unsaturated, preferably saturated, Ci-Ce hydrocarbon-based chain substituted with one or more thiol groups, preferably substituted with one thiol group.
Preferably, R’i is a saturated linear Ci-Ce hydrocarbon-based chain substituted with a thiol group, and R’2 represents an alkyl group comprising from 1 to 4 carbon atoms.
Preferably, R’3 represents an alkyl group comprising from 1 to 4 carbon atoms.
Preferably, z is equal to 3.
According to a more particular embodiment of the invention, the thiolated alkoxy siloxanes are chosen from those of formula (IX) below: (R1O)(R2)(R3)Si-[CH(R4)]t-[N(R’4)-L1]p-SH (IX) in which formula (IX):
- p is 0 or 1 ;
- 1 is an integer between 1 and 4, preferably 2;
- R1 represents a (Ci-Ce)alkyl radical;
- R2 and R3, which may be identical or different, preferably identical, are chosen from a (Ci- Ce)alkyl group, in particular a C1-C4 alkyl group, such as methyl, and a (Ci-C6)alkoxy group, in particular a (Ci-C4)alkoxy group, such as methoxy;
- R4 and R’4, which may be identical or different, represent a hydrogen atom or a (Ci-Ce)alkyl group, such as methyl;
- L1 represents a divalent, saturated, linear or branched C1-C20 hydrocarbon-based radical. According to a particular embodiment of the invention, the thiolated alkoxysiloxanes are chosen from those of formula (IX’) below:
(R’1O)(R’2)(R’3)Si-CH(R4)-CH(R5)-(L2)q-SH (IX’)
in which formula (IX’):
- q is equal to 0 or 1 ;
- X represents an oxygen or sulfur atom, preferably a sulfur atom;
- R’1 denotes a (Ci-Ce)alkyl radical;
- R’2 and R’3, which may be identical or different, preferably identical, are chosen from a (Ci-C6)alkoxy group, in particular a C1-C4 alkoxy group, and a (Ci-Ce)alkyl radical;
- R5 represents a hydrogen atom or a C1-C4 alkyl group optionally substituted with an amino, thiol or hydroxyl group;
- R4 represents a hydrogen atom or a C1-C4 alkyl group, in particular methyl;
- L2 represents a linear or branched, saturated C1-C20 divalent hydrocarbon-based group, optionally interrupted with a heteroatom such as -N(H)-, and/or optionally substituted with one or more hydroxyl, thiol or amino groups.
Preferably, the thiolated alkoxy silane(s) are chosen from 4-(trimethoxy silyl)- 1 -butanol, 3- (trimethoxy silyl)- 1 -propanol, 3-(triethoxy silyl)- 1 -propanol, 11 -(trimethoxy silyl)- 1- undecanethiol, 4-(trimethoxysilyl)-2-butanethiol, 2-(triethoxysilyl)ethanethiol, 3- (triethoxy silyl)- 1 -propanethiol, 2-(trimethoxysilyl)ethanethiol, 3-(trimethoxy silyl)- 1- propanethiol and 3-(dimethoxymethylsilyl)-l -propanethiol.
More preferentially, the thiolated alkoxysilane(s) are chosen from 2- (triethoxysilyl)ethanethiol (18236-15-2) and 3-(triethoxysilyl)-l-propanethiol (14814-09-6). According to a preferred embodiment of the invention, the (poly)thiol compound(s) are chosen from polymeric (poly)thiol compounds.
The polymeric (poly)thiol compounds may be star, comb, brush and dendritic homopolymers or copolymers bearing thiol units. The polymers may be of natural origin such as polysaccharides or polypeptides, or of synthetic origin such as acrylic polymers, polyesters or poly glycols. The thiol units may be present as terminal and/or side groups.
Examples that may be mentioned include the polymers described in the following articles: Polymers containing groups of biological activity, C.G. Overberger et al., Polytechnic Institute of Brooklyn, http://pac.iupac.org/publications/pac/pdf/1962/pdf/0402x0521.pdf; EP 1 247 515 A2; US 3 676 440; and EP 1 572 778.
The polymeric (poly)thiol compounds of the invention are preferably organic and/or silicone compounds, more preferentially of formula (X): POLY(SH)q (X)
in which formula (X):
- q is greater than or equal to 2, preferably greater than or equal to 3;
- POLY denotes a polymer-based radical, preferably carbon-based or silicone-based; POLY being optionally interrupted with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof such as -O-, -O-C(X)-, -N(R)-C(X)-, -Si(Rc)(Rd)-O- with R representing a hydrogen atom or a (Ci-C6)alkyl group such as methyl; and/or POLY being optionally substituted with one or more halogen atoms, or a group chosen from Ra(Rb)N- and -(X’)a-C(X)-(X”)b-Ra; X, X’ and X”, which may be identical or different, represent an oxygen or sulfur atom or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; Ra and Rb, which may be identical or different, represent a hydrogen atom or a (Ci- Cio)alkyl or aryl(Ci-C4)alkyl group, such as benzyl, preferably Ra and Rb represent a hydrogen atom; and Rc and Rd, which may be identical or different, represent a (Ci-Cio)alkyl, aryl(Ci-C4)alkyl or (Ci-Cio)alkoxy group.
The methods for preparing the polymeric (poly)thiol compounds used according to the invention are known to those skilled in the art; several methods are reported hereinbelow in a non-limiting manner. The polymeric (poly)thiol compounds used according to the invention may be obtained by polymerization or polycondensation of monomer units bearing thiol or protected thiol functions, optionally as a copolymerization or co-polycondensation of monomer units free of thiol or protected thiol functions.
According to one embodiment of the invention, the polymeric (poly)thiol compounds used according to the invention are polymers which are soluble in cosmetic media, particularly in aqueous or aqueous-alcoholic media. They are more preferentially obtained from amino polymers and the ammonium salts thereof or from poly hydroxylated polymers.
According to another embodiment of the invention, the thiolated polymers used according to the invention are polymers that are soluble in lipophilic media.
According to one embodiment of the invention, the polythiol compound is a polymeric compound of formula (X) in which q denotes an integer greater than or equal to 2, and POLY denotes a carbon-based and/or silicon-based, preferably silicon-based, polymeric radical, POLY also possibly containing one or more heteroatoms chosen from O, N or S, and/or one or more functions chosen from (thio)ester, (thio)ketone, (thio)amide, (thio)urea and (thio)carbamate functions, and/or possibly being substituted with one or more linear or
branched (Ci-Cio)alkyl or linear or branched (Ci-Cio)alkoxy groups, it being understood that when POLY is substituted, the thiol functions may be borne by the substituent(s).
The weight-average molecular weight of the polythiol polymer compounds, such as those of formula (X), is generally between 500 and 400 000 g.mol’1, preferably between 500 and 150000 g.mol’1.
According to a particular embodiment of the invention, the polythiol compounds are chosen from poly organo siloxanes including thiol groups on end chains, such as those of formula (XI) below:
HS-L4-Si(Ra)(Rb)-O-[Si(Ra)(Rb)-O]n-Si(Ra)(Rb)-L5-SH (XI) in which formula (XI):
- Ra and Rb, which may be identical or different, preferably identical, represent a group from among: (Ci-C4)alkyl such as methyl, (Ci-C4)alkoxy such as methoxy, aryl such as phenyl, aryloxy such as phenoxy, aryl(Ci-C4)alkyl such as benzyl, or aryl(Ci-C4)alkoxy such as benzoxy, preferably (Ci-C4)alkyl such as methyl;
- n represents an integer greater than or equal to 1 and more particularly the value of n is such that the weight- average molecular weight of the silicone ranges from 500 to 55 000 g.mol’1; in particular, n is an integer ranging from 1 to 100, preferably ranging from 5 to 50 and preferentially ranging from 10 to 30, and
- L4 and L5, which may be identical or different, preferably identical, represent a linear or branched, saturated or unsaturated, optionally cyclic hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, and in particular represent a covalent bond or a (Ci-C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene, (Ci-C6)alkylenoxy(Ci- C6)alkylene, (Ci-C6)alkylenoxy(Ci-C6)alkylenoxy or oxy(Ci-C6)alkylenoxy(Ci-C6)alkylene group, preferably a (Ci-C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene or (Ci- Ce) alky lenoxy (C i -Ce) alkylene group .
Preferentially, the (poly)thiol compounds are polythiol polyorganosiloxanes, more preferentially polythiol poly dimethylsiloxanes, notably chosen from those of formula (XII): HS-L4-Si(CH3)2-O-[Si(CH3)2-O]n-Si(CH3)2-L5-SH (XII) in which formula (XII):
- L4 and L5 are as defined previously in formula (IX), in particular L4 and L5 represent a (Ci- C6)alkylene, (Ci-C6)alkylenoxy, oxy(Ci-C6)alkylene or (Ci-C6)alkylenoxy(Ci-C6)alkylene
group, more preferentially a divalent group chosen from -R2-, -O-R2-, -R2-O- and -R2- O-R2-, preferably -R2-O-R2-, with R2 representing a linear or branched, preferably linear, (C2-C6)alkylene group, such as ethylene or n-propylene, preferably n-propylene; and
- n is as defined in formula (XI).
As polythiol compounds of formula (XII), mention may be made of mercaptosiloxanes or thiolated siloxanes in which the thiol functions are at the chain ends, sold by the company Shin-Etsu under the reference X-22-167B, and mercaptosiloxanes in which the mercapto functions are pendent, sold by the company Shin-Etsu under the reference KF-2001, or polydimethylsiloxanes in which the thiol functions are at the chain ends, via thio-n-propyl, 80-120 groups, sold by the company Gelest under the name DMS-SM 21.
Preferentially, the polythiol compounds are polyorganosiloxanes including thiol groups on side chains, such as those of formula (XIII): Ra-Si(Rb)(Rd)-O-[Si(Ra)(Rb)-O]m-[Si(Rb)(ALKi-SH)-O]n-Si(Rb)(Rd)-Ra (XIII) in which formula (XIII):
- Ra and Rb are as defined in formula (XI) and Rd is as defined for Ra and Rb, preferably Ra, Rb and Rd, which are identical, represent a (Ci-Ce)alkyl group, such as methyl;
- Rd may also represent a (Ci-Ce)alkyl group substituted with a (Ci -Chalky lamino or amino or thiol group, preferably (Ci-C4)alkyl such as methyl;
- ALKi represents a linear or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, a (thio)carbonyl group C(X) with X representing O or S, or combinations thereof such as -O- , -O-C(O)- or -C(O)-O-; preferably, ALKi represents a (Ci-C6)alkylene and more preferentially (Ci-C4)alkylene group such as propylene;
- n and m, which may be identical or different, represent an integer greater than 2 and more particularly the values of m and n are such that the weight- average molecular weight of said poly organo siloxane is between 1000 and 55 000 g.mol'1.
As examples of polythiol compounds of formula (XIII), mention may be made of those sold by the company Genesee Polymers under the names GP-367, GP-71-SS, GP-800 and GP- 710s, preferably GP-367, sold by the company Genesee Polymers.
The polythiolated compounds are notably polydimethylsiloxanes including at least two thiol groups, for instance the products SMS-022, SMS-042 and SMS-992 sold by the company
Gelest in https://www.gpcsilicones.com/products/silicone-fluids/mercapto-functional, https://www.shinetsusilicone-global.com/products/type/oil/detail/search/deg07.shtml, and
1053_Reactive Silicones_Silanes/Silicones - Gelest.
According to a particular embodiment of the invention, the (poly)thiol compounds are chosen from hyperbranched polymers comprising at least one thiol group and dendrimers bearing at least one thiol group, such as thiolated PAMAM dendrimers.
Preferably, the (poly)thiol compounds used according to the invention are chosen from polydiallylsiloxanes, notably polydimethylsiloxanes, including at least two thiol groups such as those of formula (XIII).
According to a particular embodiment, the crosslinking agent is a (poly)acrylate compound. The term ^(poly)acrylate” means a compound which comprises at least one acrylate ester group H2C=C(Re)-C(0)-Y- with Re representing a hydrogen atom or a (Ci-C4)alkyl group, such as methyl, preferably Re representing a hydrogen atom, and Y representing an oxygen atom or an amino group -N(H)-, preferably an oxygen atom.
More particularly, the (poly)acrylate(s) of the invention are of formula (XIV): L[-Y-C(0)-C(Re)=CH2]q (XIV) in which formula (XIV) q and L are as defined in formula (VIII), Y and Re being as defined previously, preferably Y = O and Re = H.
According to a preferred embodiment, the compounds of formula (XIV) are such that L represents a di- or trivalent, preferably trivalent, hydrocarbon-based chain comprising from 1 to 8 carbon atoms, q is 2 or 3, preferably 3, Y represents O, and Re represents a hydrogen atom.
According to a particular embodiment, the (poly)acrylate compounds are chosen from polyorganosiloxanes including at least one acrylate group on the side chain, such as those of formula (XV): Ra-Si(Rb)(Rd)-O-[Si(Ra)(Rb)-O]m-[Si(Rb)(ALKi-Y-C(O)-C(Re)=CH2)-O]n-Si(Rb)(Rd)-Ra (XV) in which formula (XV):
- Ra, Rb and Rd are as defined for formula (XIII), preferably Ra, Rb and Rd represent a (Ci- Ce)alkyl group, such as methyl,
- ALKi is as defined for formula (XIII), preferably ALKi represents a (Ci-C6)alkylene group, more preferentially a (Ci-C4)alkylene group, such as propylene,
- n and m, which may be identical or different, represent an integer greater than 2 and more particularly the values of m and n are such that the weight- average molecular weight of said poly organo siloxane is between 1000 and 55 000 g.mol’1.
- Y is as defined previously, and is preferably an oxygen atom.
More particularly, the (poly)acrylate compound may be chosen from 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, bis(trimethylolpropane) tetraacrylate, glyceryl 1,3- diglycerolate diacrylate, glyceryl propoxylate (1PO/OH) triacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol ethoxylate diacrylate, hydroxypivalyl hydroxypivalate, neopentyl glycol diacrylate, neopentyl glycol propoxylate (1PO/OH) diacrylate, pentaery thrityl tetraacrylate, pentaerythrityl triacrylate, poly(propylene glycol) diacrylate, tricyclo[5.2.1.02,6]decanedimethanol diacrylate, trimethylolpropane ethoxylate (1EO/OH) methyl ether diacrylate, trimethylolpropane propoxylate triacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, tri(propylene glycol) diacrylate, and tris [2- (acryloyloxy)ethyl] isocyanurate.
The (poly)acrylate compound may also be chosen from N,N’ -methylenebisacrylamide.
According to this embodiment, the (poly)acrylate compound is combined in its implementation with an amine catalyst as described, for example, in Progress in coating 129, 21-25 (2019) and Progress in coating 135, 510-516 (2019). Preferably, the amine catalyst(s) are chosen from piperidine, DMAP (dimethylaminopyridine), DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), more preferentially chosen from DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8- diazabicyclo[5.4.0]undec-7-ene).
More particularly, the (poly)acrylate compounds are chosen from those of formula (XIV), notably trimethylolpropane triacrylate, and those of formula (XV), notably copolymers of dimethylsiloxane and acryloxypropylmethylsiloxane.
D) (Poly)carbonyl compounds
According to a particular embodiment, the crosslinking agent R is a (poly)carbonyl compound.
In particular, the (poly)carbonyl compound is chosen from terephthalaldehyde, 5,5- dimethyl-l,3-cyclohexanedione, phenylglyoxal, isophthalaldehyde, 4- acetylbenzaldehyde, 4,4-diformyltriphenylamine, 2-acetylbenzaldehyde, 3-(2-furoyl)quinoline-2- carboxaldehyde, 3 -acetylbenzaldehyde, 9-(2-ethylhexyl)carbazole-3,6-dicarboxaldehyde, phthaldialdehyde, 1,3-cyclohexanedione, 4,4’-biphenyldicarboxaldehyde, benzene- 1,3,5- tricarboxaldehyde, and nonionic or anionic oxidized polysaccharides such as oxidized inulins, notably those of formula (II) as defined hereinbelow. In particular, the (poly)carbonyl compounds include a saturated or unsaturated, aromatic C5-C7 carbocycle, preferably aromatic, such as phenyl, or non-aromatic and saturated such as cyclohexyl, more preferentially unsaturated and aromatic, such as terephthaldehyde.
According to a particular embodiment, the (poly)carbonyl compound(s) are chosen from nonionic or anionic oxidized polysaccharides comprising one or more aldehyde groups, and optionally one or more anionic groups.
These anionic groups are preferably carboxyl or carboxylate groups.
The nonionic or anionic oxidized polysaccharides according to the invention may be represented by formula (II) below:
P-(CHO)m (COOQ)n (II) in which formula (II):
- P represents a polysaccharide chain preferably consisting of monosaccharides comprising 5 carbon atoms or more than 5 carbon atoms, preferably 6 or more than 6 carbon atoms and more particularly 6 carbon atoms;
- Q is chosen from a hydrogen atom, the ions derived from an alkali metal or an alkaline- earth metal such as sodium or potassium, ammonia, organic amines such as monoethanolamine, diethanolamine, triethanolamine and 3-amino-l,2-propanediol and basic amino acids such as lysine, arginine, sarcosine, ornithine and citrulline;
- m + n is greater than or equal to 1 ;
- m is such that the degree of substitution of the polysaccharide with one or more aldehyde groups (DS(CHO)) is within the range from 0.001 to 2 and preferably from 0.005 to 1.5;
- n is such that the degree of substitution of the polysaccharide with one or more carboxylic groups (DS(COOX)) is within the range from 0 to 2 and preferably from 0.001 to 1.5.
The expression “degree of substitution DS(CHO) or DS(COOX) of the polysaccharides according to the invention” means the ratio between the number of carbons oxidized to give an aldehyde or carboxylic group for all the repeating units and the number of elementary monosaccharides (even opened by preoxidation) constituting the polysaccharide. The groups CHO and COOX may be obtained during the oxidation of certain carbon atoms, for example on the carbon atoms 2, 3 or 6, of a saccharide unit containing 6 carbon atoms.
Preferably, the oxidation may take place on carbons 2 and 3, more particularly of 0.01% to 75% by number, and preferably of 0.1% to 50% by number of the rings that may have been opened.
The polysaccharide chain, represented by P, is preferably chosen from celluloses, starches, maltodextrins, guar gums, xanthan gums, pullulan gums, agar-agar gums, carrageenan gums, gellan gums, acacia gums, polyxylans and tragacanth gums, and derivatives thereof.
The term “derivative” means the compounds obtained by chemical modification of the mentioned compounds. They may be esters, amides or ethers of said compounds.
The oxidation may take place according to a process known in the art, for example according to the process described in FR 2 842 200, in document FR 2 854 161 or in the article “Hydrophobic films from maize bran hemicelluloses” by E. Fredon et al., Carbohydrate Polymers 49, pages 1 to 12 (2002).
Another oxidation process is described in the article “Water soluble oxidized starches by peroxide reaction extrusion” Industrial Crops and Products 7, R.E. Wing, J.L. Willet, 45- 52 (1997).
According to this embodiment, the (poly)carbonyl compound is combined in its implementation with an amine catalyst as described in the articles Progress in coating 129, 21-25 (2019) wa Progress in coating 135, 510-516 (2019). Preferably, the amine catalyst(s) are chosen from piperidine, DMAP (dimethylaminopyridine), DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), more preferentially chosen from DBU (1,8- diazabicyclo[5.4.0]undec-7-ene), DABCO (l,4-diazabicyclo[2.2.2]octane) and DBN (1,5- diazabicyclo[4.3.0]non-5-ene), and in particular the catalyst is DBU (1,8- diazabicyclo[5.4.0]undec-7-ene).
According to a preferred embodiment, the crosslinking agent is chosen from (poly)amine compounds A), (poly)thiol compounds B) and (poly)acrylate compounds C), preferably from (poly)amine compounds A) and (poly)thiol compounds B), and more preferentially from (poly)amine compounds A).
In particular, said (poly)amine compounds A) are chosen from a) chitosans, such as poly(D- glucosamine), b) polyether diamines, particularly polyethylene glycol a,co-diamines (bearing an amine function at the end of the chain), c) polyether triamines, such as polyetheramines (or Jeffamine), d) aminoalkoxysilanes, such as APTES, and e) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)- terminated poly(dimethoxysiloxane) (PDMS-diNth) and amodimethicones comprising amine groups on side chains, such as bis-cetearyl amodimethicone; notably the product sold by Momentive Performance Materials.
According to a preferred embodiment, said (poly)amine compounds A) are chosen from a) chitosans, such as poly(D-glucosamine), c) polyether triamines, such as polyetheramine (or Jeffamine), and e) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular poly dimethylsiloxanes comprising primary amine groups, such as bis(3-aminopropyl)-terminated poly(dimethoxysiloxane) (PDMS-diNth) and amodimethicones comprising amine groups on side chains, such as bis-cetearyl amodimethicone, notably the product sold by Momentive Performance Materials.
In particular, said (poly)thiol compounds B) are chosen from a) polydialkylsiloxanes bearing thiol functions, and b) alkoxysilanes bearing thiol functions, and in particular are chosen from a) poly dialkylsiloxanes bearing thiol functions, preferentially poly dimethylsiloxanes comprising thiol groups on the side chain (such as mercaptopropyl), notably those of formula (XIII).
In particular, said (poly)acrylate C) compounds are chosen from those of formula (XIV), notably trimethylolpropane triacrylate, and those of formula (XV), notably copolymers of dimethylsiloxane and acryloxypropylmethylsiloxane, preferably trimethylolpropane triacrylate.
According to a preferred embodiment, the crosslinking agent(s) are chosen from:
A) (poly)amine compounds chosen from: ia) chitosans such as poly(D-glucosamine),
ib) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly bis(3-aminopropyl)-terminated poly (dimethoxy siloxane) (PDMS-diNth) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone ;
B) (poly)thiol compounds chosen from: iia) polydialkylsiloxanes bearing thiol functions, and iib) alkoxysilanes bearing thiol functions, and in particular chosen from iia) polydialkylsiloxanes bearing thiol functions, preferably from polydimethylsiloxanes comprising thiol groups on the side chain, in particular mercaptopropyl, and more particularly chosen from the compounds of formula (XIII): Ra-Si(Rb)(Rd)-O-[Si(Ra)(Rb)-O]m-[Si(Rb)(ALKi-SH)-O]n-Si(Rb)(Rd)-Ra (XIII) in which formula (XIII):
- Ra and Rb, which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, in particular methyl, a (Ci-C4)alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(Ci-C4)alkyl group, in particular benzyl, or an aryl(Ci-C4)alkoxy group, in particular benzoxy, preferably a (Ci-C4)alkyl group, more preferentially methyl,
- Rd represents a (Ci-C4)alkyl group, in particular methyl, a (Ci-C4)alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(Ci-C4)alkyl group, in particular benzyl, an aryl(Ci-C4)alkoxy group, in particular benzoxy, or a (Ci-Ce)alkyl group substituted with a (Ci-C4)alkylamino, amino or thiol group, and preferably a (Ci-C4)alkyl group, more preferentially methyl, and preferably Ra, Rb and Rd are identical and represent a (Ci-Ce)alkyl group, more preferentially methyl,
- ALKi represents a linear or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, a (thio)carbonyl group C(X) with X representing O or S, or combinations thereof, in particular -O-, -O-C(O)- or -C(O)-O-; preferably, ALKi represents a (Ci-C6)alkylene and more preferentially (C1-C4) alkylene group, even more preferentially propylene,
- n and m, which may be identical or different, represent an integer greater than 2, and in particular the values of m and n are such that the weight-average molecular weight of said poly organo siloxane is between 1000 and 55 000 g.mol’1; and
C) the (poly)acrylate compounds of formula (XIV): L[-Y-C(O)-C(Re)=CH2]q (XIV) in which formula (XIV):
- q represents an integer greater than or equal to 2, in particular n is between 2 and 10 inclusive and preferably between 2 and 5,
- L denotes a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, multivalent (at least divalent) group, in particular comprising between 1 and 500 carbon and/or silicon atoms, more particularly between 2 and 40 carbon and/or silicon atoms, even more particularly between 3 and 30 carbon and/or silicon atoms, preferably between 6 and 20 carbon atoms; L being optionally interrupted and/or terminated with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof, in particular -O-, -O-C(X)-, -N(R)-C(X)-, -Si(Rc)(Rd)-O- with R representing a hydrogen atom or a (Ci-Ce)alkyl group, in particular methyl; and/or L being optionally substituted with one or more groups chosen from: -N(Ra)Rb and -(X’)a-C(X)-(X”)b-Ra; withX, X’ andX”, which may be identical or different, representing an oxygen or sulfur atom, or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; Ra and Rb, which may be identical or different, represent a hydrogen atom, a (Ci-Ce)alkyl group or an aryl(Ci-C4) alkyl group, in particular benzyl, preferably Ra and Rb represent a hydrogen atom, and Rc and Rd, which may be identical or different, represent a (Ci-Ce)alkyl, aryl(Ci-C4)alkyl or (Ci-Ce/alkoxy group,
- Re represents a hydrogen atom or a (Ci-C4)alkyl group, in particular methyl; preferably, Re represents a hydrogen atom, and
- Y represents an oxygen atom or an amino group -N(H)-, preferably an oxygen atom, preferably Y is an oxygen atom and Re is a hydrogen atom, preferably L represents a di- or trivalent, preferably trivalent, hydrocarbon-based chain comprising from 1 to 8 carbon atoms, q is 2 or 3, preferably 3, and more preferentially, the compounds of formula (XIV) are trimethylolpropane triacrylate.
COSMETIC ACTIVE AGENTS iv)
According to a particular embodiment, the process of the invention also comprises the application of iv) at least one cosmetic active agent to keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
More particularly, in the treatment process according to the invention, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises one or more cosmetic active agents.
In particular, the cosmetic active agent(s) iv) are chosen from: a) dyestuffs (or colouring agents) other than rhodamine B, in particular chosen from pigments, anionic, cationic, zwitterionic or neutral, non-fluorescent or fluorescent direct dyes other than rhodamine B, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof.
According to a particular embodiment, the at least one cosmetic agent is chosen from dyestuffs other than rhodamine B, preferably chosen from pigments, anionic, cationic, zwitterionic or neutral, non-fluorescent or fluorescent direct dyes other than rhodamine B, and mixtures thereof, more preferentially pigments.
Needless to say, a person skilled in the art will take care to select this or these optional cosmetic active agent(s), and/or the amount thereof, such that the advantageous properties of the corresponding composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
According to a particular embodiment, the process of the invention uses one or more dyestuffs other than rhodamine B.
More particularly, in the process of the invention, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises at least one particulate or non-particulate, water- soluble or water- insoluble dyestuff other than rhodamine B, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition considered.
For obvious reasons, this amount is liable to vary significantly with regard to the intensity of the desired colour effect and of the colour intensity afforded by the dyestuffs under
consideration, and its adjustment clearly falls within the competence of a person skilled in the art.
Preferably, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” comprises at least one dyestuff other than rhodamine B, chosen from pigments, anionic, cationic, zwitterionic or neutral, non-fluorescent or fluorescent direct dyes other than rhodamine B (more particularly other than fluorescent dyes), and mixtures thereof, more preferentially pigments.
More preferentially, the pigment(s) of the invention are chosen from carbon black, iron oxides, in particular yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, in particular blue and violet triarylmethane pigments, in particular Blue 1 Lake, azo pigments, in particular red azo pigments, more particularly D&C Red 7, an alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and even more preferentially chosen from red iron oxides, yellow iron oxides and azo pigments, in particular red azo pigments, more particularly D&C Red 7.
Pigments
For the purposes of the invention, the term “pigment” means any compound that is capable of imparting colour to keratin materials. These compounds have a solubility in water at 25 °C and at atmospheric pressure (760 mmHg) of less than 0.05% by weight, and preferably less than 0.01% by weight.
As pigments that are suitable for use in the invention, mention may notably be made of the organic and/or mineral pigments known in the art, notably those described in Kirk-Othmer’s Encyclopedia of Chemical Technology and in Ullmann’s Encyclopedia of Industrial Chemistry.
These pigments may be synthetic or natural.
These pigments may be in pigment powder or paste form.
They may be coated or uncoated.
These pigments may be chosen, for example, from mineral pigments, organic pigments, lakes, pigments with special effects such as nacres or glitter flakes, and mixtures thereof. A pigment that is suitable for use in the invention may be chosen from mineral pigments.
The term “mineral pigment” means any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on inorganic pigments. Among the mineral pigments that are
useful in the present invention, mention may be made of manganese violet, ultramarine blue, chromium hydrate, ferric blue and titanium, zirconium or cerium oxides or dioxides, and also of zinc, iron or chromium oxides.
It may also be a pigment having a structure that may be, for example, of sericite/brown iron oxide/titanium dioxide/silica type. Such a pigment is sold, for example, under the reference Coverleaf NS or JS by the company Chemicals and Catalysts, and has a contrast ratio in the region of 30. They may also be pigments having a structure that may be, for example, of silica microsphere type containing iron oxide. An example of a pigment having this structure is the product sold by the company Miyoshi under the reference PC Ball PC-LL-100 P, this pigment consisting of silica microspheres containing yellow iron oxide.
Advantageously, the pigments may be iron oxides and/or titanium dioxides.
A pigment that is suitable for use in the invention may be chosen from organic pigments.
The term “ organic pigment” means any pigment that satisfies the definition in Ullmann’s encyclopaedia in the chapter on organic pigments. Among the organic pigments that are useful in the present invention, mention may be made of nitroso, nitro, azo, xanthene, pyrene, quinoline, anthraquinone, triphenylmethane, fluorane, phthalocyanine, metal-complex, isoindolinone, isoindoline, quinacridone, perinone, perylene, diketopyrrolopyrrole, indigo, thioindigo, dioxazine, triphenylmethane and quinophthalone compounds. In particular, the white or coloured organic pigments may be chosen from carmine, carbon black, aniline black, azo yellow, quinacridone, phthalocyanine blue, the blue pigments codified in the Color Index under the references CI 42090, 69800, 69825, 74100, 74160, the yellow pigments codified in the Color Index under the references CI 11680, 11710, 19140, 20040, 21100, 21108, 47000, 47005, the green pigments codified in the Color Index under the references CI 61565, 61570, 74260, the orange pigments codified in the Color Index under the references CI 11725, 45370, 71105, the red pigments codified in the Color Index under the references CI 12085, 12120, 12370, 12420, 12490, 14700, 15525, 15580, 15620, 15630, 15800, 15850, 15865, 15880, 26100, 45380, 45410, 58000, 73360, 73915, 75470, the pigments obtained by oxidative polymerization of indole or phenol derivatives as described in patent FR 2 679 771.
Examples that may also be mentioned include pigment pastes of organic pigments, such as the products sold by the company Hoechst under the names: Cosmenyl Yellow IOG: Yellow 3 pigment (CI 11710); Cosmenyl G yellow: Yellow 1 pigment (CI 11680); Cosmenyl GR
orange: Orange 43 pigment (CI 71105); Cosmenyl R red: Red 4 pigment (CI 12085); Cosmenyl FB carmine: Red 5 pigment (CI 12490); Cosmenyl RL violet: Violet 23 pigment (CI 51319); Cosmenyl A2R blue: Blue 15.1 pigment (CI 74160); Cosmenyl GG green: Green 7 pigment (CI 74260); Cosmenyl R black: Black 7 pigment (CI 77266).
The pigments in accordance with the invention may also be in the form of composite pigments, as described in patent EP 1 184 426. These composite pigments may particularly be composed of particles including an inorganic core, at least one binder for attaching the organic pigments to the core, and at least one organic pigment which at least partially covers the core.
The organic pigment may also be a lake.
The term “lake” refers to dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
The inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate and aluminium. Among the dyes adsorbed on organic substrates, mention may be made of carminic acid. Mention may also be made of the dyes known under the following names: D & C Red 21 (CI 45 380), D & C Orange 5 (CI 45 370), D & C Red 27 (CI 45 410), D & C Orange 10 (CI 45 425), D & C Red 3 (CI 45 430), D & C Red 4 (CI 15 510), D & C Red 33 (CI 17 200), D & C Yellow 5 (CI 19 140), D & C Yellow 6 (CI 15 985) D & C Green 5 (CI 61 570), D & C Yellow 10 (CI 77 002), D & C Green 3 (CI 42053), D & C Blue 1 (CI 42090), FDC Red 4, D & C Red 6, D & C Red 22, D & C Red 28, D & C Red 30, D & C Orange 4, D & C Yellow 8, D & C Green 5, D & C Red 17, D & C Green 6, D & C Yellow 11, D & C Violet 2, Sudan red, carotenes (P-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin, betanin (beet), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocianine, black carrot, hibiscus, elderberry), riboflavin, beet juice and caramel.
An example of a lake that may be mentioned is the product known under the following name: D&C Red 7 (CI 15 850:1).
The pigment may also be a pigment with special effects.
The term “pigments with special effects” refers to pigments that generally create a coloured appearance (characterized by a certain shade, a certain vivacity and a certain level of luminance) that is non-uniform and that changes as a function of the conditions of
observation (light, temperature, angles of observation, etc.). They thereby differ from coloured pigments, which afford a standard uniform opaque, semi-transparent or transparent shade.
Several types of special effect pigments exist: those with a low refractive index, such as fluorescent or photochromic pigments, and those with a higher refractive index, such as nacres, interference pigments or glitter flakes.
The size of the pigment used in the composition according to the present invention is generally between 10 nm and 200 pm, preferably between 20 nm and 80 pm and more preferentially between 30 nm and 50 pm.
The pigments may be dispersed in the composition by means of a dispersant.
This dispersant may be a surfactant, an oligomer, a polymer or a mixture of several thereof, bearing one or more functionalities with strong affinity for the surface of the particles to be dispersed. In particular, they may become physically or chemically attached to the surface of the pigments. These dispersants also contain at least one functional group that is compatible with or soluble in the continuous medium. In particular, esters of 12- hydroxy stearic acid in particular and of Cs to C20 fatty acid and of polyols such as glycerol or diglycerol are used, such as poly(12-hydroxystearic acid) stearate with a molecular weight of approximately 750 g/mol, such as the product sold under the name Solsperse 21 000 by the company Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) sold under the reference Dehymyls PGPH by the company Henkel, or polyhydroxystearic acid such as the product sold under the reference Arlacel Pl 00 by the company Uniqema, and mixtures thereof. As other dispersants that may be used in the compositions of the invention, mention may be made of quaternary ammonium derivatives of polycondensed fatty acids, for instance Solsperse 17 000 sold by the company Avecia, and polydimethylsiloxane/oxypropylene mixtures such as those sold by the company Dow Coming under the references DC2-5185 and DC2-5225 C. The pigments used in the composition may be surface-treated with an organic agent. According to a particular embodiment, the dispersant(s) are of amino silicone type other than the alkoxysilanes described previously and are cationic. Preferably, the pigment(s) is (are) chosen from mineral, mixed mineral-organic, or organic pigments.
According to a particular embodiment, the pigment(s) according to the invention are organic pigments, preferentially organic pigments surface-treated with an organic agent chosen from silicone compounds.
According to another embodiment of the invention, the pigment(s) according to the invention are mineral pigments.
Direct d es
According to a particular embodiment of the invention, the cosmetic active agent is a dyestuff chosen from one or more direct dyes other than rhodamine B.
The term “direct dye” means natural and/or synthetic dyes, other than oxidation dyes. These are dyes which will spread superficially over the keratin material. They may be ionic or nonionic, anionic, cationic, zwitterionic or nonionic, preferably cationic or nonionic.
Among the direct dyes that are suitable for use in the invention, mention may be made of azo direct dyes; (poly)methine dyes such as cyanines, hemicyanines and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes other than rhodamine B; porphyrin dyes; phthalocyanine dyes and natural direct dyes, alone or in the form of mixtures.
The direct dyes are preferably cationic direct dyes. Mention may be made of the hydrazono cationic dyes of formulae (A) and (B) below and the azo cationic dyes of formulae (C) and (D) below:
Het+-C(Ra)=N-N(Rb)-Ar, Q’ (A)
Het+-N(Ra)-N=C(Rb)-Ar, Q’ (B)
Het+-N=N-Ar, Q’ (C)
Ar+-N=N-Ar”, Q' (D) in which formulae (A) to (D):
- Het+ represents a cationic heteroaryl radical, preferentially bearing an endocyclic cationic charge, such as imidazolium, indolium or pyridinium, which is optionally substituted, preferentially with at least one (Ci-Cs)alkyl group such as methyl;
- Ar+ represents an aryl radical, such as phenyl or naphthyl, bearing an exocyclic cationic charge, preferentially ammonium, particularly tri(Ci-Cs)alkylammonium, such as trimethylammonium;
- Ar represents an aryl group, notably phenyl, which is optionally substituted, preferentially with one or more electron-donating groups such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, (di)(Ci-Cs)(alkyl)amino optionally substituted on the
alkyl group(s) with a hydroxyl group, aryl(Ci-Cs)alkylamino, and optionally substituted N- (Ci-C8)alkyl-N-aryl(Ci-C8)alkylamino or alternatively Ar represents a julolidine group;
- Ar’ ’ represents an optionally substituted (hetero)aryl group, such as phenyl or pyrazolyl, which are optionally substituted, preferentially with one or more (Ci-Cs)alkyl, hydroxyl, (di)(Ci-C8)(alkyl)amino, (Ci-Cs)alkoxy or phenyl groups;
- Ra and Rb, which may be identical or different, represent a hydrogen atom or a (Ci-Cs)alkyl group, which is optionally substituted, preferentially with a hydroxyl group; or else the substituent Ra with a substituent of Het+ and/or Rb with a substituent of Ar form, together with the atoms that bear them, a (hetero)cycloalkyl; in particular, Ra and Rb represent a hydrogen atom or a (Ci-C4)alkyl group optionally substituted with a hydroxyl group;
- Q" represents an organic or mineral anionic counterion, such as a halide or an alkyl sulfate. In particular, mention may be made of the azo and hydrazono direct dyes bearing endocyclic cationic charges of formulae (A) to (D) as defined previously, more particularly the cationic direct dyes bearing an endocyclic cationic charge described in patent applications WO 95/15144, WO 95/01772 and EP 714 954,
Preferably, the direct dyes are chosen from the compounds of formulae (E) and (F) below:
in which formulae (E) and (F):
- R1 represents a (Ci-C4)alkyl group such as methyl;
- R2 and R3, which may be identical or different, represent a hydrogen atom or a (Ci-C4)alkyl group, such as methyl;
- R4 represents a hydrogen atom or an electron-donating group such as optionally substituted (Ci-Cs)alkyl, optionally substituted (Ci-Cs)alkoxy, or (di)(Ci-Cs)(alkyl)amino optionally substituted on the alkyl group(s) with a hydroxyl group; in particular, R4 is a hydrogen atom;
- Z represents a CH group or a nitrogen atom, preferentially CH;
- Q" is an anionic counterion as defined previously, in particular a halide, such as chloride, or an alkyl sulfate, such as methyl sulfate or mesyl.
In particular, the dyes of formulae (E) and (F) are chosen from Basic Red 51, Basic Yellow 87 and Basic Orange 31 or derivatives thereof with Q" being an anionic counterion as defined previously, particularly a halide such as chloride, or an alkyl sulfate such as methyl sulfate or mesyl. The direct dyes may be chosen from anionic direct dyes.
The anionic direct dyes of the invention are dyes commonly referred to as “acid” direct dyes owing to their affinity for alkaline substances.
The term “anionic direct dye” means any direct dye including in its structure at least one CO2R’ or SO3R’ substituent with R’ denoting a hydrogen atom or a cation originating from a metal or an amine, or an ammonium ion.
The anionic direct dyes may be chosen from direct nitro acid dyes, azo acid dyes, azine acid dyes, triarylmethane acid dyes other than rhodamine B, indoamine acid dyes, anthraquinone acid dyes, indigoid dyes and natural acid dyes.
Among the natural direct dyes that may be used according to the invention, mention may be made of lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin and orceins. Use may also be made of extracts or decoctions containing these natural dyes and particularly hennabased poultices or extracts.
Preferably, the direct dyes are chosen from anionic direct dyes.
The dyestuffs, preferably the pigments, may be present in concentrations ranging from 0.01% to 30% by weight, preferably from 0.02% to 20% by weight and more particularly from 0.05% to 15% by weight relative to the total weight of the composition containing them.
The direct dye(s) may be present in concentrations ranging from 0.001% to 10% by weight and preferably from 0.005% to 5% by weight relative to the total weight of the composition containing them.
Preferably, the cosmetic active agent(s), in particular the dyestuff(s) and more particularly the pigment(s), are introduced into at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5”.
Care active agents
According to a particular embodiment, the process of the invention uses one or more care active agents.
More particularly, in the process of the invention, according to one embodiment, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises one or more care active agents, preferably in a proportion of at least 0.01% by weight relative to the total weight of the composition considered. In particular, the care active agent may be at least one hydrophilic active agent and/or one lipophilic active agent, and preferably a hydrophilic care active agent.
The term “hydrophilic active agent” means a water-soluble or water-dispersible active agent that is capable of forming hydrogen bonds.
The cosmetic care active agent(s) may notably be chosen from: a) vitamins and derivatives thereof, notably esters thereof, in particular tocopherol (vitamin E) and esters thereof (such as tocopheryl acetate), ascorbic acid (vitamin C) and derivatives thereof; b) humectants, in particular urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides and xylitylglucoside, and in particular glycerol; c) C-glycoside compounds; d) antioxidant compounds; e) anti-ageing active agents, in particular hyaluronic acid compounds, and notably sodium hyaluronate, retinol and derivatives thereof, salicylic acid compounds and in particular n-octanoyl-5-salicylic acid (capryloyl salicylic acid), caffeine, adenosine, c-P-d-xylopyranoside-2-hydroxypropane and the sodium salt of 3-hydroxy-2-pentylcyclopentyl)acetic acid; f) skincare agents chosen from allantoin, panthenol and protein hydrolysates; g) polyphenols, notably escin, ruscus, diosmin, hesperidin and resveratrol, and h) mixtures thereof.
In particular, in the process of the invention, according to one embodiment, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises a moisturizer (also known as a humectant agent). Preferably, the care active agent is a moisturizer, and in particular is glycerine (glycerol).
The care active agent(s) may in particular be present, in the composition containing same, in a content ranging from 0.01% to 30% by weight, relative to the weight of the composition, and preferably from 0.02% to 25% by weight.
According to one embodiment of the process of the invention, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5” used comprises, as cosmetic active agent, at least one UV- screening agent.
The UV-screening agent is a UV-screening agent normally used in cosmetics.
It may be chosen from the positive list contained in Annex VI of (EC) Regulation No. 1223/2009, which specifies the list of UV-screening agents permitted in cosmetics.
The UV-screening agents that are suitable for use in the invention may be of varied nature. They may be lipophilic, hydrophilic or insoluble organic agents.
The term “lipophilic UV-screening agent” means any cosmetic or dermatological screening agent that can be fully dissolved in molecular form in a liquid fatty phase or that can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.
The term “hydrophilic UV-screening agent” means any cosmetic or dermatological screening agent that can be fully dissolved in molecular form in a liquid aqueous phase or that can be dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.
The term “insoluble UV-screening agent” means any cosmetic or dermatological screening agent which is not defined either as a lipophilic UV-screening agent or as a hydrophilic UV- screening agent, and which is in the form of particles in aqueous phase or liquid fatty phase. The UV-screening agents of the composition according to the invention may afford UVA and/or UVB photoprotection.
According to a preferred embodiment, the compositions, which are preferably cosmetic compositions, may comprise at least one organic and/or mineral UV-screening agent (for screening out the UV radiation of sunlight).
In particular, the UV-screening agent(s) are chosen from bis-resorcinyl triazine derivatives, dibenzoylmethane derivatives, benzylidenecamphor derivatives, and mixtures thereof. The organic UV-screening agents may also be chosen from anthranilic derivatives; cinnamic derivatives; salicylic derivatives; benzophenone derivatives; phenylbenzotriazole
derivatives; benzalmalonate derivatives, notably those mentioned in patent US 5 624 663; phenylbenzimidazole derivatives; imidazolines; 4,4-diarylbutadiene derivatives; bis- benzazolyl derivatives, as described in patents EP 6 693 23 and US 2 463 264; p- aminobenzoic acid (PABA) derivatives; methylenebis(hydroxyphenylbenzotriazole) derivatives, as described in patent applications US 5 237 071, US 5 166 355, GB 2 303 549, DE 197 26, 184 and EP 893 119; benzoxazole derivatives, such as those described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844; screening polymers and screening silicones such as those notably described in patent application WO 93/04665; a-alkylstyrene -based dimers such as those described in patent application DE 198 55 649; 4,4-diarylbutadienes such as those described in patent applications EP 0 967 200, DE 197 46 654, DE 197 55 649, EP 1 008 586, EP 1 133 980 and EP 133 981; other merocyanine derivatives such as those described in patent applications WO 04/006878, WO 05/058269 and WO 06/032741, and mixtures thereof.
According to a particular embodiment, the concentration of the organic UV- screening agents in the compositions ranges from 1% to 50% by weight, preferably from 1% to 40% by weight, for example from 5% to 35% by weight, relative to the total weight of the composition.
The UV-screening agent(s) may be mineral UV-screening agents, which are generally pigments. The pigments may or may not be coated.
Thus, the mineral UV-screening agents may be chosen from coated or uncoated pigments, and in particular from coated titanium oxide pigments, silicone-treated titanium oxides, uncoated titanium oxide pigments, uncoated zinc oxide pigments, coated zinc oxide pigments, uncoated cerium oxide pigments, uncoated iron oxide pigments, coated iron oxide pigments, and mixtures thereof.
According to a particular embodiment, compositions “Cl” to “C5” are free of mineral UV- screening agents.
According to a particular embodiment, the amount of the mineral UV-screening agent(s) present in compositions “Cl”, “C2”, “C3”, “C4” or “C5” may range from 0.01% to 20% by weight relative to the total weight of the composition containing same. It ranges, for example, from 1% to 15% by weight, relative to the total weight of the composition.
According to a particular embodiment, at least one of the compositions “Cl” to “C5” also comprises one or more organic UV-screening agents and one or more mineral UV-screening agents.
According to a particular embodiment, the compositions comprise a combination of UV- screening agents as described in patent FR 2 977 490, patent application WO 2013/004777 or patent application US 2014/0134120.
Preferably, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, and compositions “Cl”, “C2”, “C3”, “C4” or “C5” use or comprise one or more dyestuffs other than rhodamine B, preferably chosen from pigments, anionic, cationic, zwitterionic or neutral, non-fluorescent or fluorescent direct dyes, other than rhodamine B, and mixtures thereof; more preferentially, the pigment(s) of the invention are chosen from carbon black, iron oxides, notably yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, notably blue and violet triarylmethane pigments, such as Blue 1 Lake, azo pigments, notably red azo pigments, such as D&C Red 7, an alkali metal salt of lithol red, such as the calcium salt of lithol red B, even more preferentially red iron oxides, yellow iron oxides and azo pigments, notably red azo pigments, such as D&C Red 7.
FATTY PHASE - FATTY SUBSTANCES
According to a particular embodiment, the process of the invention also uses v) one or more fatty substances, in particular one or more oils, preferably volatile oils.
In particular, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5”, in particular at least composition “C4”, used in the process of the invention contains a fatty phase.
In particular, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5”, in particular at least composition “C4”, used in the process of the invention comprises one or more fatty substances, in particular one or more oils, preferably volatile oils.
The term “oil” refers to a fatty substance that is liquid at room temperature (20°C) and atmospheric pressure (760 mmHg).
The term “hydrocarbon-based oil” means an oil formed essentially from, or even constituted of, carbon and hydrogen atoms, and possibly oxygen and nitrogen atoms, and not containing
any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
According to one embodiment of the invention, the oil(s) v) are chosen from volatile oils, in particular:
- hydrocarbon-based oils containing from 8 to 16 carbon atoms, in particular branched Cs-Ci6 alkanes, in particular isoalkanes, more particularly isoalkanes (also known as isoparaffins), preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, alone or as mixtures, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular C11-C16 alkanes, alone or as mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins, in particular n-dodecane (C12) and n-tetradecane (C14), the undecanetridecane mixture, mixtures of n-undecane (Cn) and n-tridecane (C13), and mixtures thereof and also mixtures of n-undecane (Cn) and n-tridecane (C13), and volatile C5-C12 cyclic, nonaromatic alkanes;
- short-chain esters containing from 3 to 8 carbon atoms in total, in particular ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate;
- carbonate hydrocarbon-based oils of structure R’ I-O-C(O)-O-R’2 in which R’i and R’2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen more preferentially from dibutyl carbonate or dipentyl carbonate;
- ether oils of formula R1-O-R2 in which Ri and R2, independently of each other, denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;
- silicone oils, in particular comprising from 2 to 7 silicon atoms, and optionally including alkyl or alkoxy groups containing from 1 to 10 carbon atoms, in particular dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof; more preferentially, the volatile oil(s) v) are chosen from Cs-Ci6 alkanes, in particular branched alkanes, preferably isododecane.
In particular, at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5”, in particular at least composition “C4”, used in the process according to the invention comprises one or more non-volatile oils, preferably chosen from:
- non-volatile fluoro oils, in particular chosen from fluorinated polyethers, fluoro silicone oils and fluorosilicones;
- non-volatile silicone oils, in particular chosen from non-volatile silicones having the following INCI names: dimethicone, dimethiconol, trimethyl pentaphenyl trisiloxane, tetramethyl tetraphenyl trisiloxane, diphenyl dimethicone, trimethylsiloxyphenyl dimethicone, phenyl trimethicone, diphenylsiloxy phenyl trimethicone; and also mixtures thereof;
- non-volatile apolar hydrocarbon-based oils, in particular chosen from linear or branched compounds of mineral or synthetic origin: i) liquid paraffin, ii) squalane, isoeicosane, iii) mixtures of linear, saturated hydrocarbons, more particularly C15-C28 hydrocarbons, in particular mixtures whose INCI names are (Cis-Ci9)Alkane, (C18-C21) Alkane, (C21- C28) Alkane, iv) hydrogenated or non-hydrogenated polybutenes; v) hydrogenated or nonhydrogenated polyisobutenes, preferably hydrogenated, vi) hydrogenated or nonhydrogenated polydecenes, vii) decene/butene copolymers, butene/isobutene copolymers and viii) mixtures thereof;
- non-volatile polar hydrocarbon-based oils, which may be chosen from: i) saturated, unsaturated, linear or branched C10-C26 fatty alcohols, preferably monoalcohols; in particular, the C10-C26 alcohols are fatty alcohols, which are preferably branched when they comprise at least 16 carbon atoms; preferably, the fatty alcohol comprises from 10 to 24 carbon atoms, and more preferentially from 12 to 22 carbon atoms, in particular such as lauryl alcohol, isostearyl alcohol, oleyl alcohol, 2-butyloctanol, 2-undecylpentadecanol, 2- hexyldecyl alcohol, isocetyl alcohol, octyldodecanol and mixtures thereof; ii) triglycerides consisting of fatty acid esters of glycerol, in particular the fatty acids of which may have chain lengths ranging from C4 to C36, and notably from Cis to C36, these oils possibly being linear or branched, and saturated or unsaturated; by way of example, mention may notably be made of heptanoic or octanoic triglycerides, caprylic/capric acid triglycerides, plant oils such as wheatgerm oil, sunflower oil, grapeseed oil, sesame seed oil, com oil, apricot kernel oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil,
alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil, groundnut oil, coconut oil, argan oil, kaya oil; the liquid fraction of shea butter, and the liquid fraction of cocoa butter; and also mixtures thereof; iii) linear aliphatic hydrocarbon-based esters of formula R-C(O)-OR’ in which R-C(O)-O- represents the carboxylic acid residue containing from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, aliphatic hydrocarbon-based esters of alkylene glycol, in particular ethylene glycol or propylene glycol; the total number of carbon atoms in particular being at least 10; notably chosen from isoamyl laurate, cetostearyl octanoate, isopropyl myristate, isopropyl palmitate, isopropyl stearate or isostearate, ethyl palmitate, 2-ethylhexyl palmitate, isostearyl isostearate, octyl stearate, isostearyl heptanoate, octanoates, decanoates or ricinoleates of alcohols or of polyalcohols, such as propylene glycol dioctanoate, cetyl octanoate or tridecyl octanoate, 2- ethylhexyl palmitate, alkyl benzoate, polyethylene glycol diheptanoate, propylene glycol bis(2-ethylhexanoate) and mixtures thereof, hexyl laurate, neopentanoic acid esters, such as isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate or 2- octyldodecyl neopentanoate, isononanoic acid esters, in particular isononyl isononanoate, isotridecyl isononanoate or octyl isononanoate, oleyl erucate, isopropyl lauroyl sarcosinate, diisopropyl sebacate, isocetyl stearate, isodecyl neopentanoate, isostearyl behenate or myristyl myristate; iv) hydroxylated esters, in particular polyglyceryl-2 triisostearate; v) aromatic esters, in particular tridecyl trimellitate, C12-C15 alcohol benzoate, the 2- phenylethyl ester of benzoic acid, and butyloctyl salicylate; vi) linear fatty acid esters with a total carbon number ranging from 35 to 70, in particular pentaerythrityl tetrapelargonate; vii) esters of C24-C28 branched fatty acids or fatty alcohols, in particular triisoarachidyl citrate, pentaerythrityl tetraisononanoate, glyceryl triisostearate, glyceryl tris(2- decyltetradecanoate), pentaerythrityl tetraisostearate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetrakis(2-decyltetradecanoate); viii) the polyesters obtained by condensation of dimer and/or trimer of unsaturated fatty acid and of diol, in particular those with the INCI name Dilinoleic Acid/Butanediol Copolymer
or Dilinoleic Acid/Propanediol Copolymer; the polyesters obtained by condensation of fatty acid dimer and of diol dimer, in particular dimer dilinoleyl dimer dilinoleate; ix) synthetic ethers containing from 10 to 40 carbon atoms, in particular dicaprylyl ether; x) dialkyl carbonates, the two alkyl chains possibly being identical or different, in particular dicaprylyl carbonate; xi) vinylpyrrolidone copolymers, in particular vinylpyrrolidone/1 -hexadecene copolymer; and xii) mixtures thereof;
- the non-volatile carbonate oils may be chosen from the carbonates of formula Rs-O- C(O)-O-Rg, with Rs and R9, which may be identical or different, representing a linear or branched C4 to C12 and preferentially Ce to C10 alkyl chain; the carbonate oils may be dicaprylyl carbonate (or dioctyl carbonate), bis(2-ethylhexyl) carbonate, dipropylheptyl carbonate, dibutyl carbonate, dineopentyl carbonate, dipentyl carbonate, dineoheptyl carbonate, diheptyl carbonate, diisononyl carbonate or dinonyl carbonate and preferably dioctyl carbonate;
- oils known as non-volatile ether oils of formula R1-O-R2 in which Ri and R2 independently denote a linear, branched or cyclic C6-C24 alkyl group, preferably a Ce-Cis alkyl group, and preferably a Cs-Ci2 alkyl group. It may be preferable for Ri and R2 to be identical. Linear alkyl groups that may be mentioned include a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, a behenyl group, a docosyl group, a tricosyl group and a tetracosyl group. Branched alkyl groups that may be mentioned include a 1,1 -dimethylpropyl group, a 3-methylhexyl group, a 5-methylhexyl group, an ethylhexyl group, a 2-ethylhexyl group, a 5-methyloctyl group, a 1-ethylhexyl group, a 1-butylpentyl group, a 2-butyloctyl group, an isotridecyl group, a 2-pentylnonyl group, a 2-hexyldecyl group, an isostearyl group, a 2-heptylundecyl group, a 2-octyldodecyl group, a 1,3- dimethylbutyl group, a l-(l-methylethyl)-2-methylpropyl group, a 1,1,3,3-tetramethylbutyl group, a 3,5,5-trimethylhexyl group, a l-(2-methylpropyl)-3-methylbutyl group, a 3,7- dimethyloctyl group and a 2-(l,3,3-trimethylbutyl)-5,7,7-trimethyloctyl group. As cyclic alkyl groups, mention may be made of a cyclohexyl group, a 3 -methylcyclohexyl group and a 3,3,5-trimethylcyclohexyl group, dilauryl ether, diisostearyl ether, dioctyl ether,
nonylphenyl ether, dodecyl dimethylbutyl ether, cetyl dimethylbutyl ether, cetyl isobutyl ether and mixtures thereof.
Preferably, the non-volatile oil(s) are chosen from hydrogenated or non-hydrogenated polyisobutenes, preferably hydrogenated, in particular the non-volatile compounds of the Parleam® range; mixtures of C15-C19 alkanes, and from linear aliphatic hydrocarbon-based esters of formula R-C(O)-OR’ in which R-C(0)-0 represents a carboxylic acid residue containing from 2 to 40 carbon atoms, and R’ represents a hydrocarbon-based chain containing from 1 to 40 carbon atoms, as defined previously, in particular isononyl isononanoate.
More preferentially, the process of the invention uses one or more hydrocarbon-based oils containing from 8 to 16 carbon atoms, and notably branched Cs-Ci6 alkanes, in particular isoalkanes, preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, alone or as mixtures, and more preferentially isododecane.
In particular, the amount of oil(s) in at least one of the compositions “Cl”, “C2”, “C3”, “C4” or “C5”, in particular at least composition “C4”, used in the process according to the invention ranges from 1% to 99% by weight, relative to the total weight of the composition, more particularly from 2% to 98% by weight, preferentially from 3% to 97%, better still from 5% to 95% by weight, relative to the total weight of the composition.
According to a particular embodiment, the cosmetic active agents iv) are chosen from a) dyestuffs chosen from pigments, direct dyes other than rhodamine B, more particularly other than rhodamines, more preferentially the direct dyes are non-fluorescent, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, and d) mixtures thereof. According to this embodiment, composition(s) “Cl” to “C5” do not contain any screening agents as defined previously.
According to another particular embodiment, the cosmetic active agents iv) are chosen from a) dyestuffs chosen from pigments, direct dyes other than rhodamine B, more particularly other than rhodamines, more preferentially the direct dyes are non-fluorescent, and mixtures thereof, c) UV- screening agents and d) mixtures thereof. According to this embodiment, composition(s) “Cl” to “C5” do not contain any care active agents as defined previously.
According to a preferred embodiment, the cosmetic active agent(s) iv) are chosen from colouring agents other than rhodamine B, as defined previously, in particular chosen from
anionic, cationic, zwitterionic or neutral, non-fluorescent or fluorescent direct dyes other than rhodamine B, or pigments, more preferentially from pigments. According to this embodiment, composition(s) “Cl” to “C5” do not contain any screening agents or care active agents as defined previously.
COMPOSITIONS
According to the invention, the process for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows according to the invention, uses water. Thus, compositions “Cl”, “C2” and “C3” used in the process of the invention comprise water, and compositions “C4” and “C5” optionally comprise water.
Thus, in particular, composition “Cl” is aqueous or aqueous-alcoholic. Preferably, composition “Cl” is aqueous.
In particular, composition “C2” is aqueous or aqueous-alcoholic. Preferably, composition “C2” is aqueous.
In particular, composition “C3” is aqueous or aqueous-alcoholic. Preferably, composition “C3” is aqueous.
In particular, composition “C4” is aqueous or aqueous-alcoholic. Preferably, composition “C4” is aqueous.
In particular, composition “C5” is aqueous or aqueous-alcoholic.
According to a particular embodiment, compositions “Cl”, “C2”, “C3” and “C4” are aqueous.
According to a particular embodiment, compositions “Cl”, “C2” and “C3” are aqueous- alcoholic. In particular, they comprise a water/polar solvent mixture, preferably a water/polar protic solvent mixture, such as an ethanol/water mixture, in particular in a solvent/water volume ratio of between 1/99 and 99/1, more particularly between 10/90 and 90/10, even more particularly between 20/80 and 80/20, preferably 40/60 to 60/40, such as 50/50.
According to a particular embodiment, compositions “Cl”, “C2”, “C3”, “C4” or “C5” may be in water-in-oil emulsion or oil-in-water emulsion form.
According to a particular embodiment, compositions “C4” or “C5” may be in anhydrous, water-in-oil emulsion or oil-in-water emulsion form.
According to a particular embodiment, composition “C4” is anhydrous. In particular, composition “C4” is anhydrous, and comprises at least one oil, in particular a volatile oil, preferably isododecane.
The compositions “Cl” to “C5” used in the process of the invention may also comprise one or more solvents, other than water.
According to a particular embodiment of the invention, the (co)polymer(s) i) as defined previously are used in a medium containing at least one solvent, preferably at least one polar and/or protic solvent, other than water.
According to this embodiment, composition “Cl” and/or “C2” and/or “C3” and/or “C4” and/or “C5” used in the process of the invention comprises one or more solvents, preferably one or more polar and/or protic solvents other than water.
According to this embodiment, preferably, composition “Cl” and/or “C2” and/or “C3” and/or “C4” and/or “C5” used in the process of the invention comprises at least one polar and/or protic solvent chosen from monoalcohols containing from 2 to 6 carbon atoms, in particular chosen from ethanol, propanol, n-butanol, isopropanol, isobutanol, tert-butanol, pentanol and hexanol, preferably n-butanol or ethanol, and even more preferentially ethanol.
According to one embodiment, composition “Cl” and/or “C2” and/or “C3” and/or “C4” and/or “C5” and/or “C5” used in the process of the invention comprises one or more solvents other than water, in a content of less than 70% by weight, more preferentially less than 50% by weight and even more preferentially less than 40% by weight, relative to the total weight of water.
Organic solvents that may also be mentioned include polyols that are miscible with water at room temperature (25°C), notably chosen from polyols notably containing from 2 to 10 carbon atoms, preferably containing from 2 to 6 carbon atoms, such as glycerol, propylene glycol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol or diglycerol; polyol ethers, such as 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether or diethylene glycol monomethyl ether; and also aromatic alcohols, such as benzyl alcohol, and mixtures thereof. According to a particular embodiment, the composition considered also comprises one or more polyols notably chosen from polyols notably containing from 2 to 10 carbon atoms, preferably containing from 2 to 6 carbon atoms, preferably glycerol.
The compositions “Cl”, “C2”, “C3”, “C4” or “C5” used in the process of the invention may also comprise one or more adjuvants commonly used in cosmetics, in particular chosen from thickeners, film-forming agents, gelling agents, trace elements, softeners, sequestrants, fragrances, basifying or acidifying agents, dispersants, preserving agents, fillers, surfactants, polymers other than i), or mixtures thereof.
Another subject of the invention is a composition “C3” comprising i) at least one (co)polymer as defined previously, ii) water; iii) at least one crosslinking agent, in particular as defined previously, and iv) at least one cosmetic active agent other than rhodamine B, preferably at least one dyestuff other than rhodamine B, and more preferentially at least one pigment, as defined previously.
Another subject of the invention is the cosmetic use of composition “C3” as defined previously, for the treatment of keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
A composition “Cl”, “C2”, “C3”, “C4” or “C5” is generally suitable for application to keratin materials, in particular application to the skin and/or the lips, and thus generally comprises a physiologically acceptable medium, i.e. a medium that is compatible with keratin materials, in particular application to the skin and/or the lips.
Said compositions “Cl” to “C5” are cosmetic compositions, compounds i), iii), optionally iv) and optionally v) being in a cosmetically acceptable medium, i.e. a medium which has a pleasant colour, odour and feel and does not give rise to unacceptable discomfort, i.e. stinging or tautness, liable to discourage the user from applying this composition.
A composition “Cl”, “C2”, “C3”, “C4” or “C5” may be in the form of a makeup product, in particular a coloured makeup product, for the skin, in particular a foundation, optionally having care properties, a blusher, a face powder, an eyeshadow, a concealer, an eyeliner; a lip makeup product such as a lipstick, optionally having care properties, a lip gloss or lip pencils; a makeup product for the integuments such as the nails or eyelashes, in particular in the form of a cake mascara, or for the eyebrows and the hair, or a product for the temporary tattooing of bodily skin.
A composition “Cl”, “C2”, “C3”, “C4” or “C5” may be in the form of a care product for the skin, in particular a colourless product, such as a care cream or a care fluid.
According to a particular embodiment, a composition “Cl”, “C2”, “C3”, “C4” or “C5” is in the form of: either a coloured product for the lips; or a skincare product, which may be coloured, in particular a cream or a fluid having moisturizing and/or filling and/or tensor properties.
KIT
According to yet another of its aspects, the present invention is also directed towards a multicompartment kit or device, notably a cosmetic kit or device, comprising:
- at least one compartment containing at least i) at least one (co)polymer as defined previously, ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously, in particular comprising composition “Cl” as defined previously;
- at least one compartment different from the one which contains i) and containing iii) at least one crosslinking agent, in particular as defined previously, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular as defined previously, in particular comprising composition “C4” as defined previously; and
- optionally, at least one compartment different from those containing i) and iii), and containing iv) at least one cosmetic active agent, in particular as defined previously, which may be identical to or different from that/those optionally contained in the compartments comprising i) and iii); preferably, at least one of the compartments contains iv) at least one cosmetic active agent other than rhodamine B.
The invention is illustrated in greater detail by the examples presented below. Unless otherwise indicated, the amounts indicated are expressed as mass percentages.
Example
Methods and Measurements
Skin application a) One -step protocol
The polyvinyl alcohol compounds bearing acetoacetate functions, the crosslinking agents and optionally the cosmetic active agents are mixed together using a Speed Mixer (2 minutes
- 3500 rpm) before application. The system remains fluid long enough to allow application to the substrate.
The compositions are applied to a Bioskin type vitro support from Maprecos (Bioskin plate #10) (elastomeric skin- simulating support) using a film spreader (wet thickness of 100 pm). The deposit is left to dry for 24 hours.
After 24 hours of drying, the deposits are evaluated according to the protocols described hereinbelow. b) Two-step protocol
A first composition, termed the “base coat”, is applied to a Bioskin type vitro support from Maprecos (Bioskin plate #10) (elastomeric skin- simulating support) using a film spreader (wet thickness of 100 pm). The deposit is left to dry for 24 hours.
After this first gesture, a second composition, termed the “top coat”, is applied in the same manner.
The deposit is left to dry for 24 hours.
The deposits are evaluated according to the protocols described hereinbelow.
Resistance to olive oil/sebum/water
0.5 mL of olive oil, sebum or water is applied to the film of formulation. After 5 minutes, the olive oil, sebum or water is removed by wiping 15 times with cotton wool. The deterioration of the film following contact with the drop of attacking agent is thus examined. In the case of a two-step protocol, for each combination, evaluations are performed on the “base coat” composition alone after drying, and on the system of “base coat” + “top coat” compositions after drying, the objective being to observe the cosmetic properties improved by such combinations.
The resistance is evaluated according to the following scale:
+++: Cosmetic property evaluated as highly effective, no attack of the deposit, which is as it was originally;
++: Cosmetic property evaluated as moderately effective, a little transfer but the deposit is as it was originally;
+: Cosmetic property evaluated as poor, the deposit is slightly altered and some transfer is observed.
0: Cosmetic property evaluated as unsatisfactory, the deposit is completely degraded and there is a lot of transfer to the cotton wool.
Resistance to adhesive tape
A piece of adhesive tape (Scotch® Magic™ 810 from 3M; w = 19 mm, L = 5 cm) is applied to the deposit. A weight of approximately 1070 g is placed on the piece of adhesive tape for 30 seconds. The piece of adhesive tape is then removed and mounted on a slide holder so as to properly observe the result. The adhesion of the film to the support is thus evaluated.
Fragmentation test of formulations on Bioskin
As for the tests of resistance to olive oil/sebum/water and to adhesive tape, films are applied to a sample of Bioskin. After drying for one day, the Bioskin plate is stretched ten times using manual force.
Next, the result is observed on the film (fragmentation or no fragmentation).
The evaluation is carried out as follows:
+++: Cosmetic property evaluated as highly effective;
++: Cosmetic property evaluated as moderately effective;
+: Cosmetic property evaluated as somewhat effective;
0: Cosmetic property evaluated as ineffective.
Example 1: Preparation of a polyvinyl alcohol bearing 20% mol acetoacetate functions
113.6 g of Mowiol 8-88 PVA (sold by Sigma Aldrich) and 400 g of DMSO are placed in a 1 L reactor.
71.81 g (0.2 eq.) of tert-butyl acetoacetate (sold by Sigma- Aldrich) are added after dissolving the medium.
The medium is heated at 120°C for 7 hrs, until a hot yellow viscous solution is obtained.
Several precipitations in 5 litres of acetone are performed to remove the DMSO.
The precipitate is redissolved in heated water for 72 hours to a solids content of 7%. The solution is then concentrated to 25% on a rotary evaporator.
Example 2: Preparation of a polyvinyl alcohol bearing 10% mol acetoacetate functions (Compound 2)
The synthesis is represented by the same preparation scheme as described in Example 1.
28.4 g of Mowiol 4-88 PVA (sold by Sigma Aldrich) and 100 g of DMSO are placed in a 1 L reactor.
8.97 g (0.1 eq.) of tert-butyl acetoacetate (sold by Sigma- Aldrich) are added after dissolving the medium.
The medium is heated at 120°C for 7 hrs, until a hot yellow viscous solution is obtained.
Several precipitations in 5 litres of acetone are performed to remove the DMSO.
The precipitate is redissolved in heated water for 72 hours then the solution is freeze-dried to obtain a water-soluble powder. of a polyvinyl alcohol bearing 25% mol acetoacetate functions
The synthesis is represented by the same preparation scheme as described in Example 1.
28.4 g of Mowiol 4-88 PVA (sold by Sigma Aldrich) and 100 g of DMSO are placed in a 1 L reactor.
22.4 g (0.25 eq.) of tert-butyl acetoacetate (sold by Sigma- Aldrich) are added after dissolving the medium.
The medium is heated at 120°C for 7 hrs, until a hot yellow viscous solution is obtained.
Several precipitations in 5 litres of acetone are performed to remove the DMSO.
The precipitate is redissolved in heated water for 72 hours then the solution is freeze-dried to obtain a water-soluble powder. of a polvvinvl alcohol bearing 30% mol acetoacetate functions
The synthesis is represented by the same preparation scheme as described in Example 1.
28.4 g of Mowiol 4-88 PVA (sold by Sigma Aldrich) and 100 g of DMSO are placed in a 1 L reactor.
26.9 g (0.30 eq.) of tert-butyl acetoacetate (sold by Sigma- Aldrich) are added after dissolving the medium.
The medium is heated at 120°C for 7 hrs, until a hot yellow viscous solution is obtained.
Several precipitations in 5 litres of acetone are performed to remove the DMSO.
The precipitate is redissolved in heated water for 72 hours then the solution is freeze-dried to obtain a water-soluble powder.
Example 5: Preparation of compositions A and B
Composition A according to the invention comprising the polyvinyl alcohol compound bearing acetoacetate functions of Example 1 and a crosslinking agent, and comparative composition B, comprising the polyvinyl alcohol compound bearing acetoacetate functions of Example 1 but free of crosslinking agent, are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition.
Table 1
Compositions A and B are prepared by simply mixing the ingredients detailed in Table 1 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 6: One-step application of compositions A and B to the skin
Compositions A and B are applied according to the one-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 2
It is seen that the application of composition A via the process of the invention allows significantly improved water resistance to be obtained relative to the application of composition B.
It is also seen that the application of formula A according to the invention allows an improved cohesive and adherent deposit to be obtained relative to the application of composition B (comparative).
Compositions C and D are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 3
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 3 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 8: Two-step application of compositions C and D to the skin
Compositions C and D are applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 4
It is seen that the application of formula D (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of comparative composition C (base coat only).
It is also seen that the application of formula D according to the invention allows a significantly improved cohesive and adherent deposit to be obtained relative to the application of composition C (comparative).
Water-resistant deposits are thus obtained by applying formula D (base coat and top coat) according to the process of the invention.
Example 9: Preparation of compositions E and F
Compositions E and F are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 5
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 5 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 10: Two-step application of compositions E and F to the skin
Compositions E and F are applied according to the two-step skin application protocol as described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
The evaluation results are summarized in the table below:
Table 6
It is seen that the application of formula F (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of composition E (base coat only).
It is also seen that the application of formula F according to the invention allows a significantly improved cohesive and adherent deposit to be obtained relative to the application of composition E (comparative).
Example 11: Preparation of compositions G and H
Compositions G and H are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 7
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 7 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 12: Two-step application of compositions G and H to the skin
Compositions G and H are applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 8
It is seen that the application of formula H (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of composition G (base coat only).
It is also seen that the application of formula H according to the invention allows a significantly improved cohesive and adherent deposit to be obtained relative to the application of composition G (comparative).
Compositions I and J are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 9
Composition I is prepared by simply mixing the ingredients detailed in Table 9 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Composition J is prepared by simply mixing the first two ingredients detailed in Table 9 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature, then by simply hand mixing the crosslinking agent detailed in Table 9.
Compositions I and J are applied according to the one-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 10
It is seen that the application of composition J via the process of the invention allows significantly improved water resistance to be obtained relative to the application of composition I.
It is also seen that the application of formula J according to the invention allows an improved cohesive and adherent deposit to be obtained relative to the application of composition I (comparative).
Example 15: Preparation of compositions K and L
Compositions K and L are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 11
Composition K is prepared by simply mixing the ingredients detailed in Table 11 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. Composition L is prepared by simply mixing the first two ingredients detailed in Table 11 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature, then by simply hand mixing the crosslinking agent detailed in Table 11. Example 16: One-step application of compositions K and L to the skin
Compositions K and L are applied according to the one-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols. The evaluation results are summarized in the table below:
Table 12
It is seen that the application of composition L via the process of the invention allows significantly improved water resistance to be obtained relative to the application of composition K.
It is also seen that the application of formula L according to the invention allows an improved cohesive and adherent deposit to be obtained relative to the application of composition K (comparative).
Example 17: Preparation of compositions M and N
Compositions M and N are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 13
Composition M is prepared by simply mixing the ingredients detailed in Table 13 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Composition N is prepared by simply mixing the first two ingredients detailed in Table 13 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature, then by simply hand mixing the crosslinking agent detailed in Table 13.
Example 18: One-step application of compositions M and N to the skin
Compositions M and N are applied according to the one-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 14
It is seen that the application of composition N via the process of the invention allows significantly improved water resistance to be obtained relative to the application of composition M.
It is also seen that the application of formula M according to the invention allows an improved cohesive and adherent deposit to be obtained relative to the application of composition N (comparative).
Example 19: Preparation of compositions O and P
Compositions O and P are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Composition O is prepared by simply mixing the ingredients detailed in Table 15 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Composition P is prepared by simply mixing the first two ingredients detailed in Table 15 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature, then by simply hand mixing the crosslinking agent detailed in Table 15.
Example 20: One-step application of compositions O and P to the skin
Compositions O and P are applied according to the one-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols. The evaluation results are summarized in the table below:
Table 16
It is seen that the application of composition P via the process of the invention allows significantly improved water resistance to be obtained relative to the application of composition O. It is also seen that the application of formula O according to the invention allows an improved cohesive and adherent deposit to be obtained relative to the application of composition P (comparative).
Example 21; Preparation of formulas O and R Formulas Q and R are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 17
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 17 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 22: Two-step application of formulas O and R to the skin
Formulas Q and R are applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 18
It is seen that the application of formula R (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of comparative composition Q (base coat only).
It is also seen that the application of formula R according to the invention allows a significantly improved cohesive and adherent deposit to be obtained relative to the application of composition Q (comparative).
Water-resistant deposits are thus obtained by applying formula R (base coat and top coat) according to the process of the invention.
Example 23: Preparation of formulas S and T
Formulas S and T are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 19
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 19 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 24: Two-step application of compositions S and T to the skin
Compositions S and T are applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 20 It is seen that the application of formula T (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of comparative composition S (base coat only).
It is also seen that the application of formula T according to the invention allows a significantly improved cohesive and adherent deposit to be obtained relative to the application of composition S (comparative).
Water-resistant deposits are thus obtained by applying formula T (base coat and top coat) according to the process of the invention.
Example 25: Preparation of formulas U and V Formulas U and V are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 21
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 21 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 26: Two-step application of formulas U and V to the skin
Formulas U and V are applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 22
It is seen that the application of formula V (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of comparative composition U (base coat only).
It is also seen that the application of formula V according to the invention allows a significantly improved cohesive and adherent deposit to be obtained relative to the application of composition U (comparative).
Water-resistant deposits are thus obtained by applying formula V (base coat and top coat) according to the process of the invention.
Example 27; Preparation of formulas W and X
Formulas W and X are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 23
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 23 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 28: Two-step application of formulas W and X to the skin
Formulas W and X are applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water and adhesive tape resistance protocols.
Table 24
It is seen that the application of formula X (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of comparative composition W (base coat only).
It is also seen that the application of formula X according to the invention allows a significantly improved cohesive and adherent deposit to be obtained relative to the application of composition W (comparative).
Water-resistant deposits are thus obtained by applying formula X (base coat and top coat) according to the process of the invention.
Example 29: Preparation of formulas A A and AB
Formulas AA and AB are prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 25
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 27 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 30: Two-step application of formulas AA and AB to the skin
Formulas AA and AB are applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water resistance protocol. The evaluation results are summarized in the table below:
Table 26
It is seen that the application of formula AB (base coat and top coat) according to the process of the invention allows significantly improved water resistance to be obtained relative to the application of comparative composition AA (base coat only). Water-resistant deposits are thus obtained by applying formula AB (base coat and top coat) according to the process of the invention.
Example 31: Preparation of formulas AD (invention) vs. comparative AH (AH is according to WO 2022/136114) Formulas AD is prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 27
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 29 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature. Example 32: Two-step application of formula AD to the skin
Formula AD is applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water resistance protocol.
It is seen that the application of formula AD (base coat and top coat) according to the process of the invention allows a very good resistance vs. adhesive tape test, fragmentation, water, olive oil, and sebum. Example 33: Preparation of formula AH
Formula AH is prepared using the contents indicated in the table below. The contents are expressed as weight percentages relative to the total weight of the composition under consideration.
Table 29
The “base coat” and “top coat” compositions are prepared by simply mixing the ingredients detailed in Table 33 using a Speed Mixer (mixing equipment which uses centrifugal force) for 2 minutes, at 3500 rpm and at room temperature.
Example 38: Two-step application of formula AH to the skin
Formula AH is applied according to the two-step skin application protocol described previously.
The deposits are then evaluated according to the water resistance protocol. The evaluation results are summarized in the table below:
Table 30
It appears from table 28 and 30 of AD (invention) and AH (according to WO 2022/136114) respectively, that composition AD according to the invention which differs from AH by the nature of the polymer with acetoacetate functions show a significant better resistance to fragmentation, oil and sebum, than the resistance of AH.
Claims
1. Process, notably a cosmetic process, for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, comprising the application to said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, in one or more successive steps, of at least: i) one or more (co)polymers bearing at least one unit of formula (I), and also the optical or geometrical isomers thereof, and/or the solvates thereof, such as hydrates, or a composition containing same:
in which formula (I):
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom,
- Rb and Rc, which may be identical or different, represent a hydrogen atom or a linear or branched (Ci-C alkyl group; preferably, Rb and Rc represent a hydrogen atom,
- Rd represents a linear or branched (Ci-C alkyl group; preferably, Rd represents a methyl group;
- p is an integer greater than or equal to 2, and optionally of at least one unit of formula (II):
in which formula (II):
- q denotes an integer greater than or equal to 2, and
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom; and optionally of at least one unit of formula (III):
in which formula (III):
- 1 represents an integer greater than or equal to 2, and
- R represents a linear or branched, saturated or unsaturated, aromatic or non-aromatic, cyclic or acyclic hydrocarbon-based chain comprising from 1 to 10 carbon atoms; preferably, R represents a (Ci-Ce)alkyl group, in particular methyl;
- Ra represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group; preferably, Ra represents a hydrogen atom; and ii) water; iii) one or more crosslinking agents; and iv) optionally one or more cosmetic active agents chosen from a) dyestuffs other than rhodamine B, b) active agents for caring for keratin materials, c) UV- screening agents, and d) mixtures thereof.
2. Treatment process according to the preceding claim, in which the (co)polymer(s) comprise at least one unit of formula (I) and at least one unit of formula (II), or at least one unit of formula (I) and at least one unit of formula (III).
3. Treatment process according to either of the preceding claims, in which the (co)polymer(s) comprise at least one unit of formula (I), at least one unit of formula (II) and at least one unit of formula (III).
4. Treatment process according to any one of the preceding claims, in which the (co)polymer(s) comprise:
- from 1 mol% to 30 mol% of units of formula (I),
- from 49 mol% to 99 mol% of units of formula (II),
- from 0% to 26 mol% of units of formula (III).
5. Treatment process according to any one of the preceding claims, in which the (co)polymer(s) are present in a composition in a content ranging from 0.001% to 50% by weight, preferably from 0.01% to 30% by weight and more preferentially from 0.1% to 25% by weight, relative to the total weight of said composition.
6. Treatment process according to any one of the preceding claims, in which the crosslinking agent(s) iii) are chosen from (poly)amine, (poly)thiol, (poly)carbonyl and (poly)acrylate compounds and mixtures thereof, preferably chosen from (poly)amine, (poly)thiol and (poly)acrylate compounds and mixtures thereof, and more preferentially chosen from (poly)amine, (poly)thiol compounds and mixtures thereof, and more preferentially chosen from (poly)amine compounds.
7. Treatment process according to any one of the preceding claims, in which the crosslinking agent(s) iii) are chosen from:
A) (poly)amine compounds chosen from: ia) chitosans such as poly(D-glucosamine), ib) polydialkylsiloxanes comprising primary amine groups at the end of the chain or on side chains, in particular polydimethylsiloxanes comprising primary amine groups, more particularly bis(3-aminopropyl)-terminated poly (dimethoxy siloxane) (PDMS-diNth) and amodimethicones comprising amine groups on side chains, more particularly bis-cetearyl amodimethicone ;
B) (poly)thiol compounds chosen from: iia) polydialkylsiloxanes bearing thiol functions, and iib) alkoxysilanes bearing thiol functions, and in particular chosen from iia) polydialkylsiloxanes bearing thiol functions, preferably from polydimethylsiloxanes comprising thiol groups on the side chain, in particular mercaptopropyl, and more particularly chosen from the compounds of formula (XIII): Ra-Si(Rb)(Rd)-O-[Si(Ra)(Rb)-O]m-[Si(Rb)(ALKi-SH)-O]n-Si(Rb)(Rd)-Ra (XIII) in which formula (XIII):
- Ra and Rb, which may be identical or different, preferably identical, represent a (Ci- C4)alkyl group, in particular methyl, a (Ci-C4)alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(Ci-C4)alkyl group, in particular benzyl, or an aryl(Ci-C4)alkoxy group, in particular benzoxy, and preferably a (Ci-C4)alkyl group, more preferentially methyl,
- Rd represents a (Ci-C4)alkyl group, in particular methyl, a (Ci-C4)alkoxy group, in particular methoxy, an aryl group, in particular phenyl, an aryloxy group, in particular phenoxy, an aryl(Ci-C4)alkyl group, in particular benzyl, an aryl(Ci-C4)alkoxy group, in particular benzoxy, or a (Ci-Ce)alkyl group substituted with a (Ci-C4)alkylamino, amino or thiol group, and preferably a (Ci-C4)alkyl group, more preferentially methyl, and preferably Ra, Rb and Rd are identical and represent a (Ci-Ce)alkyl group, more preferentially methyl,
- ALKi represents a linear or branched, optionally cyclic, saturated or unsaturated divalent hydrocarbon-based chain comprising from 1 to 100 carbon atoms, optionally interrupted with one or more heteroatoms such as oxygen, sulfur or nitrogen, in particular oxygen, a (thio)carbonyl group C(X) with X representing O or S, or combinations thereof, in particular -O-, -O-C(O)- or -C(O)-O-; preferably, ALKi represents a (Ci-C6)alkylene and more preferentially (C1-C4) alkylene group, even more preferentially propylene,
- n and m, which may be identical or different, represent an integer greater than 2, and in particular the values of m and n are such that the weight-average molecular weight of said poly organo siloxane is between 1000 and 55 000 g.mol’1; and
C) the (poly)acrylate compounds of formula (XIV): L[-Y-C(O)-C(Re)=CH2]q (XIV) in which formula (XIV):
- q represents an integer greater than or equal to 2, in particular n is between 2 and 10 inclusive and preferably between 2 and 5,
- L denotes a linear or branched, saturated or unsaturated, or (hetero)cyclic, saturated or unsaturated, multivalent (at least divalent) group, in particular comprising between 1 and 500 carbon and/or silicon atoms, more particularly between 2 and 40 carbon and/or silicon atoms, even more particularly between 3 and 30 carbon and/or silicon atoms, preferably between 6 and 20 carbon atoms; L being optionally interrupted and/or terminated with one or more heteroatoms or groups chosen from O, S, N, Si, C(X), and combinations thereof, in particular -O-, -O-C(X)-, -N(R)-C(X)-, -Si(Rc)(Rd)-O- with R representing a hydrogen atom or a (Ci-Ce)alkyl group, in particular methyl; and/or L being optionally substituted with one or more groups chosen from: -N(Ra)Rb and -(X’)a-C(X)-(X”)b-Ra; withX, X’ andX”, which may be identical or different, representing an oxygen or sulfur atom, or a group N(Rb); a and b being 0 or 1, preferably the sum of a + b being 1; Ra and Rb, which may be identical or
different, represent a hydrogen atom, a (Ci-C6)alkyl group or an aryl(Ci-C4) alkyl group, in particular benzyl, preferably Ra and Rb represent a hydrogen atom, and Rc and Rd, which may be identical or different, represent a (Ci-Ce)alkyl, aryl(Ci-C4)alkyl or (Ci-C6)alkoxy group,
- Re represents a hydrogen atom or a (Ci-C4)alkyl group, in particular methyl; preferably, Re represents a hydrogen atom, and
- Y represents an oxygen atom or an amino group -N(H)-, preferably an oxygen atom, preferably Y is an oxygen atom and Re is a hydrogen atom, preferably L represents a di- or bivalent, preferably trivalent, hydrocarbon-based chain comprising from 1 to 8 carbon atoms, q is 2 or 3, preferably 3, and more preferentially, the compounds of formula (XIV) are trimethylolpropane triacrylate.
8. Treatment process according to any one of the preceding claims, in which iv) at least one cosmetic active agent is also applied to the keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
9. Treatment process according to the preceding claim, in which the cosmetic agent(s) iv) are chosen from: a) dyestuffs other than rhodamine B, in particular chosen from pigments, anionic, cationic, zwitterionic or neutral, non-fluorescent or fluorescent direct dyes other than rhodamine B, and mixtures thereof, b) active agents for caring for keratin materials, preferably the skin, c) UV-screening agents, and d) mixtures thereof; preferably, the cosmetic agent(s) iv) are chosen from a) dyestuffs other than rhodamine B, preferably chosen from pigments, anionic, cationic, zwitterionic or neutral non-fluorescent or fluorescent direct dyes other than rhodamine B, and mixtures thereof; more preferentially, the pigment(s) are chosen from carbon black, iron oxides, in particular yellow, red and black iron oxides, and micas coated with iron oxide, triarylmethane pigments, in particular blue and violet triarylmethane pigments, in particular Blue 1 Lake, azo pigments, in particular red azo pigments, more particularly D&C Red 7, an alkali metal salt of lithol red, in particular the calcium salt of lithol red B, and even more preferentially from red iron oxides, yellow iron oxides and azo pigments, in particular red azo pigments, more particularly D&C Red 7.
10. Treatment process according to any one of the preceding claims, in which use is also made of v) at least one fatty substance, in particular at least one oil, preferably at least one volatile oil.
11. Treatment process according to the preceding claim, in which use is also made of v) at least one fatty substance chosen from volatile oils chosen from:
- hydrocarbon-based oils containing from 8 to 16 carbon atoms, in particular branched Cs-Ci6 alkanes, in particular isoalkanes, more particularly isoalkanes (also known as isoparaffins), preferably C13-C16 isoparaffins, isododecane, isodecane, isohexadecane, for example the oils sold under the trade names Isopar or Permethyl, alone or as mixtures, preferably isododecane (also known as 2,2,4,4,6-pentamethylheptane), linear alkanes, in particular C11-C16 alkanes, alone or as mixtures, in particular hexane, decane, undecane, tridecane, isoparaffins, in particular n-dodecane (C12) and n-tetradecane (C14), the undecanetridecane mixture, mixtures of n-undecane (Cn) and n-tridecane (C13), and mixtures thereof and also mixtures of n-undecane (Cn) and n-tridecane (C13), and volatile C5-C12 cyclic, nonaromatic alkanes;
- short-chain esters containing from 3 to 8 carbon atoms in total, in particular ethyl acetate, methyl acetate, propyl acetate or n-butyl acetate;
- carbonate hydrocarbon-based oils of structure RT-O-C(O)-O-R’2 in which RT and R’2 independently denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group, advantageously chosen more preferentially from dibutyl carbonate or dipentyl carbonate;
- ether oils of formula R1-O-R2 in which Ri and R2, independently of each other, denote a linear, branched or cyclic C4-C8 alkyl group, preferably a C4-C8 alkyl group;
- silicone oils, in particular comprising from 2 to 7 silicon atoms, and optionally including alkyl or alkoxy groups containing from 1 to 10 carbon atoms, in particular dimethicones of viscosity 5 and 6 cSt, cyclopentadimethylsiloxane, dodecamethylpentasiloxane, cyclohexadimethylsiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, and mixtures thereof; more preferentially, the volatile oil(s) v) are chosen from Cs-Ci6 alkanes, in particular branched alkanes, preferably isododecane.
12. Process, notably a cosmetic process, for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, according to any one of the preceding claims, for caring for and/or making up keratin materials, notably the skin, the lips, the eyelashes and/or the eyebrows, comprising the application to said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, of at least:
- a composition, termed “Cl”, comprising i) at least one (co)polymer according to any one of Claims 1 to 5, and ii) water, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9;
- a composition, termed “C2”, comprising i) at least one (co)polymer according to any one of Claims 1 to 5, ii) water, iii) at least one crosslinking agent, in particular according to either of Claims 6 and 7, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9; preferably, composition “C2” does not comprise iv) any cosmetic active agent;
- a composition, termed “C3”, comprising ii) at least one (co)polymer according to any one of Claims 1 to 5, ii) water, iii) at least one crosslinking agent, in particular according to either of Claims 6 and 7, and iv) at least one cosmetic active agent, in particular according to Claim 9;
- a composition, termed “C4”, comprising iii) at least one crosslinking agent, in particular according to either of Claims 6 and 7, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9;
- a composition, termed “C5”, comprising iv) at least one cosmetic active agent, in particular according to Claim 9; and optionally ii) water; preferably, composition “C5” does not comprise i) at least one (co)polymer according to any one of Claims 1 to 5, and does not comprise iii) at least one crosslinking agent; it being understood that:
. the process uses, together or separately, i) at least one (co)polymer according to any one of Claims 1 to 5, ii) water, iii) at least one crosslinking agent, in particular according to either of Claims 6 and 7, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9; and
. compositions “Cl”, “C2”, “C3”, “C4” and “C5” may also comprise one or more fatty substances v), in particular according to either of Claims 10 and 11.
13. Treatment process according to the preceding claim, characterized in that it comprises a single step of applying composition “C3” to said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
14. Treatment process according to Claim 12, characterized in that it comprises two successive steps of applying to said keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows, two different compositions, preferably composition “Cl” and then composition “C4”; preferably, at least one of the compositions used comprises iv) at least one cosmetic active agent, in particular according to Claim 9.
15. Cosmetic treatment process for caring for and/or making up keratin materials, notably the skin, the lips, the eyelashes and/or the eyebrows, comprising the successive application of at least:
- a composition, termed “Cl”, comprising i) at least one (co)polymer according to any one of Claims 1 to 5, ii) water, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9; and then
- a composition, termed “C4”, comprising iii) at least one crosslinking agent, in particular according to either of Claims 6 and 7, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9; at least one of the compositions “Cl” and/or “C4” containing at least one dyestuff other than rhodamine B, in particular according to Claim 9, preferably at least one pigment, and more preferentially composition “Cl” comprises at least one pigment.
16. Composition “C3” comprising i) at least one (co)polymer according to any one of Claims 1 to 5, ii) water, iii) at least one crosslinking agent, in particular according to either of Claims 6 and 7, and iv) at least one cosmetic active agent other than rhodamine B, in particular according to Claim 9, preferably at least one dyestuff other than rhodamine B, and more preferentially at least one pigment.
17. Cosmetic use of composition “C3” according to Claim 16, for treating keratin materials, notably the skin and/or the lips and/or the eyelashes and/or the eyebrows.
18. Multi-compartment kit, notably a cosmetic kit, comprising:
- at least one compartment containing at least i) at least one (co)polymer according to any one of Claims 1 to 5, ii) water, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9, in particular comprising composition “Cl” according to Claim 12;
- at least one compartment different from the one which contains i) and containing iii) at least one crosslinking agent, in particular according to either of Claims 6 and 7, optionally ii) water, and optionally iv) at least one cosmetic active agent, in particular according to Claim 9, in particular comprising composition “C4” according to Claim 12; and - optionally, at least one compartment different from those containing i) and iii), and containing iv) at least one cosmetic active agent, in particular according to Claim 9, which may be identical to or different from that/those optionally contained in the compartments comprising i) and iii); preferably, at least one of the compartments contains iv) at least one cosmetic active agent other than rhodamine B.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FRFR2214552 | 2022-12-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2024141526A1 true WO2024141526A1 (en) | 2024-07-04 |
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