EP3946637A1 - Composition cosmetique pour cheveux - Google Patents
Composition cosmetique pour cheveuxInfo
- Publication number
- EP3946637A1 EP3946637A1 EP20726509.1A EP20726509A EP3946637A1 EP 3946637 A1 EP3946637 A1 EP 3946637A1 EP 20726509 A EP20726509 A EP 20726509A EP 3946637 A1 EP3946637 A1 EP 3946637A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mol
- resin
- acid
- composition
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 239000002537 cosmetic Substances 0.000 title claims abstract description 26
- 239000011347 resin Substances 0.000 claims abstract description 79
- 229920005989 resin Polymers 0.000 claims abstract description 79
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 28
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 14
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 14
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- 239000011976 maleic acid Substances 0.000 claims description 13
- 239000002562 thickening agent Substances 0.000 claims description 5
- 238000002834 transmittance Methods 0.000 claims description 5
- 238000005259 measurement Methods 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000004584 polyacrylic acid Substances 0.000 claims 1
- 238000012423 maintenance Methods 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 47
- 239000000499 gel Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl methacrylate Chemical compound 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229920006029 tetra-polymer Polymers 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- ZKYCLDTVJCJYIB-UHFFFAOYSA-N 2-methylidenedecanamide Chemical compound CCCCCCCCC(=C)C(N)=O ZKYCLDTVJCJYIB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 241001272720 Medialuna californiensis Species 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002610 basifying agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- WJMQFZCWOFLFCI-UHFFFAOYSA-N cyanomethyl prop-2-enoate Chemical compound C=CC(=O)OCC#N WJMQFZCWOFLFCI-UHFFFAOYSA-N 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SCQOZUUUCTYPPY-UHFFFAOYSA-N dimethyl-[(prop-2-enoylamino)methyl]-propylazanium;chloride Chemical compound [Cl-].CCC[N+](C)(C)CNC(=O)C=C SCQOZUUUCTYPPY-UHFFFAOYSA-N 0.000 description 1
- VVTXSHLLIKXMPY-UHFFFAOYSA-L disodium;2-sulfobenzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].OS(=O)(=O)C1=C(C([O-])=O)C=CC=C1C([O-])=O VVTXSHLLIKXMPY-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 238000000569 multi-angle light scattering Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/48—Thickener, Thickening system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/95—Involves in-situ formation or cross-linking of polymers
Definitions
- the present invention relates to the technical field of caring for and shaping the hair using cosmetic compositions.
- the subject of the invention is an aqueous cosmetic composition
- a fixing resin of a specific chemical nature comprising a fixing resin of a specific chemical nature, and the use of this resin to improve the resistance in a humid environment of said composition.
- the fixing agents used in hair gels are generally film-forming polymers which bind the hair together, thus facilitating their shaping.
- the fixing agents usually used are natural gums, such as guar gum, or else anionic or neutral polymers.
- the film must be transparent, more or less flexible depending on the desired effect but have a certain resistance, a certain strength. Also, the film must not crumble over time or under stress (combing, various friction) and not become sticky when the climatic conditions become humid.
- these polymers otherwise called resins, must make it possible to formulate clear compositions and having rheological characteristics in line with the packaging (aerosol, tube, jar) and consumer expectations (gel-like viscosity, pseudoplastic, non-sticky, drying. fast).
- the cosmetic compositions based on these polymers contain thickeners which provide the rheological properties mentioned above.
- Document WO 99/13836 describes solvent-based cosmetic compositions for hair containing a reduced level of volatile organic compound (VOC, or VOC in English) to meet environmental requirements. These compositions are based on a specific solvent combination comprising associated ethanol, either with methyl acetate or with butyl acetate.
- a fixing resin which may be, according to the examples disclosed, chosen from a series of polymers, and in particular from an octylacrylamide / acrylates / butylaminoethyl methacrylate copolymer, a vinyl acetate / crotonates / vinyl neodecanoate copolymer, a diglycol copolymer / cyclohexane dimethanol / isophthalates / sodium sulfoisophthalate.
- a fixing resin which may be, according to the examples disclosed, chosen from a series of polymers, and in particular from an octylacrylamide / acrylates / butylaminoethyl methacrylate copolymer, a vinyl acetate / crotonates / vinyl neodecanoate copolymer, a diglycol copolymer / cyclohexane dimethanol / isophthalates / sodium sulf
- Document EP 0 761 199 describes cosmetic compositions for the hair comprising a fixing agent and a particular acrylic copolymer.
- the fixing agent is chosen from anionic, cationic or amphoteric polymers, and among the list of anionic polymers are mentioned copolymers of acrylic or methacrylic acid without specifying either their chemical composition or their molecular weight.
- Acrylic copolymer is a tetrapolymer composed of alkyl acrylate, alkyl methacrylate, acrylic acid and methacrylic acid. The total amount of both acrylic acid and methacrylic acid monomers does not exceed 15% by weight. This tetrapolymer has a molecular weight of between 10,000 and 50,000 g / mol. These compositions exhibit acceptable moisture resistance but which can nevertheless be improved.
- Patent EP 0 589 241 describes a polymer used in the field of printed circuits, comprising at least 20 mol% of monomer units of methacrylic acid, monomers of methyl methacrylate and monomers of ethyl acrylate. This polymer is used in solution in methyl ethyl ketone. The polymer is not water soluble and therefore not suitable for an aqueous composition.
- EP 2 248 510 describes thickening polymers and their use in aqueous compositions. Said aqueous composition comprises two thickening polymers, including a first thickening polymer comprising from 10% to 50% by weight of methacrylic acid, and a second thickening polymer not comprising methacrylic acid.
- EP 1 402 877 describes aqueous compositions comprising a surfactant, clay, and a copolymer comprising monomers of acrylic acid, alkyl methacrylate, modified methacrylate, and optionally methacrylic acid.
- This resin comprises a copolymer comprising monomers of methacrylic acid, methyl methacrylate, hydroxyethyl methacrylate, and alkyl acrylate.
- the percentage of methacrylic acid monomers in the copolymer is preferably low, that is to say less than or equal to 18% by weight, ie 21.5% molar, so as not to degrade the retention of the hair curls (" curl retention ”in English).
- the Applicant has now discovered, surprisingly and unexpectedly, that a specific selection of a polymer, by the nature and the amounts of monomers constituting it, as well as a judicious choice of molecular weight, made it possible to achieve the objectives described above. .
- the present invention therefore provides an aqueous cosmetic composition for hair offering excellent hold properties in a humid environment over several hours, without a sticky effect and easy to remove during washing.
- the present invention relates to an aqueous cosmetic composition for hair comprising at least one fixing resin, said resin comprising:
- the resin being water-soluble and having a weight average molecular weight greater than or equal to 20,000 g / mol (> 20,000 g / mol).
- the sum of the molar percentages of the monomeric units of the resin is equal to 100%.
- Those skilled in the art will know how to adjust the respective percentages to reach 100%, and this with at least 30 mol% of methacrylic acid and / or one of its salts and at least 10 mol% of acrylic acid and / or maleic acid and / or itaconic acid, and / or one of their salts.
- said resin consists of, or essentially consists of:
- the resin being water-soluble and having a weight average molecular weight greater than or equal to 20,000 g / mol (> 20,000 g / mol).
- the term "consisting of” means that the resin comprises only monomeric units of methacrylic acid, and / or a salt thereof, at least 30% molar, and monomeric units of acrylic acid and / or acid. maleic and / or itaconic acid, and / or one of their salts, at least 10 mol%. The sum of these molar percentages is then equal to 100%.
- the present invention also relates to the use as a fixing agent of this resin in an aqueous cosmetic composition for hair, in particular for improving the resistance to humidity of this cosmetic composition.
- the term “fixing resin” is understood to mean a polymer making it possible to give a cosmetic composition a temporary holding effect, fixing the hairstyle but also holding the curls, even in a humid environment.
- the fixing resin will denote the “dry” polymer, and not the solution containing the polymer.
- a solution containing the polymer is used, said solution generally containing 15 to 25% of polymer, by weight relative to the weight of the solution. This is called a solution containing 15 to 25% of active material, by weight relative to the weight of the solution.
- the amounts of fixing resin will be given as a percentage by weight of active material, unless this is contraindicated.
- the fixing resin comprises at least 30 mol% of monomer units of methacrylic acid and / or one of its salts, preferably at least 40 mol%, more preferably at least 50 mol%, again more preferably at least 60 mol% and even more preferably at least 70 mol%.
- the fixing resin comprises less than 99 mol% of monomer units of methacrylic acid and / or one of its salts, preferably less than 95 mol%, more preferably less than 90 mol%, again more preferably less than 80 mol%.
- the salts of methacrylic acid include in particular the salts of an alkaline earth metal (preferably calcium or magnesium) or of an alkali metal (preferably sodium or lithium) or ammonium (in particular quaternary ammonium).
- an alkaline earth metal preferably calcium or magnesium
- an alkali metal preferably sodium or lithium
- ammonium in particular quaternary ammonium
- the fixing resin comprises at least 1 mol% of monomeric units of acrylic acid and / or maleic acid and / or itaconic acid and / or one of their salts, preferably less 10 mol%, more preferably at least 20 mol%.
- the fixing resin comprises less than 80 mol% of monomeric units of acrylic acid and / or maleic acid and / or itaconic acid and / or one of their salts, preferably less 70 mol%, more preferably less than 60 mol%, even more preferably less than 50 mol%, even more preferably less than 40 mol% and even more preferably less than 30 mol%.
- molar percentage is meant molar percentages based on all the moles of monomer of the resin or of the polymer.
- the amount of branching agent or of crosslinking agent is not taken into account to determine all the moles of monomer of the resin (or of the polymer).
- the fixing resin comprises monomeric units of methacrylic acid and / or one of its salts, monomeric units of acrylic acid and / or maleic acid and / or itaconic acid and / or one of their salts, and optionally nonionic monomers and / or cationic monomers.
- the fixing resin comprises monomeric units of methacrylic acid and / or one of its salts, monomeric units of acrylic acid and / or one of its salts, and optionally nonionic monomers and / or cationic monomers.
- the fixing resin is preferably a copolymer of methacrylic acid and acrylic acid, and / or their salts.
- the resin is a copolymer comprising only monomeric units of methacrylic acid and acrylic acid, and / or their salts.
- alkaline earth metal preferably calcium or magnesium
- alkali metal preferably sodium or lithium
- ammonium in particular quaternary ammonium
- the preferred salts are the sodium salts.
- the weight average molecular weight of the resin is preferably greater than or equal to 60,000 g / mol, more preferably greater than or equal to 100,000 g / mol.
- It is preferably less than or equal to 2,000,000 g / mol ( ⁇ 2 million g / mol), more preferably less than or equal to 1,000,000 g / mol, even more preferably less than or equal to 500,000 g / mol, again more preferably less than or equal to 300,000 g / mol.
- the weight average molecular weight is determined in a conventional manner by size exclusion chromatography. It is measured, for example, on an Agilent 1260 Inf ⁇ nity system equipped with a Dawn HELOS, OPtilab T-Rex multi-angle light scattering detector and 3 columns in series: Shodex SB 807-G, Shodex SB 807-HQ and Shodex 805-HQ.
- the fixing resin is preferably a water-soluble polymer.
- water-soluble polymer means a polymer which gives an aqueous solution when it is dissolved with stirring at 25 ° C. at a concentration of 20 gL 1 in water.
- the fixing resin can also comprise at least nonionic and / or cationic monomeric units. In this case, it is preferable to limit the amount of these monomers to less than 20 mol%, preferably to less than 10 mol%.
- the nonionic monomers are preferably selected from the group comprising acrylamide, methacrylamide, N-vinylformamide, and N-vinylpyrrolidone.
- Acrylamide is preferred.
- the fixing resin is devoid of hydroxylated monomers, for example of hydroxypropyl acrylate and / or alkyl (meth) acrylate type.
- the cationic monomers are preferably chosen from the group comprising quaternized or salified dimethylaminoethyl acrylate (AD AME); quaternized or salified dimethylaminoethyl methacrylate (MADAME); dimethyldiallylammonium chloride (DADMAC); acrylamido propyltrimethyl ammonium chloride (APTAC); and methacrylamido propyltrimethyl ammonium chloride (MAPTAC).
- AD AME quaternized or salified dimethylaminoethyl acrylate
- MADAME quaternized or salified dimethylaminoethyl methacrylate
- DDADMAC dimethyldiallylammonium chloride
- ATAC acrylamido propyltrimethyl ammonium chloride
- MATAC methacrylamido propyltrimethyl ammonium chloride
- ADAME and MADAME monomers for example by means of acid (in particular hydrochloric acid) or of an alkyl halide of the RX type, R being an alkyl group and X being a halogen (especially methyl chloride).
- a branching agent or a crosslinking agent is, for example, chosen from methylene-bis-acrylamide (MBA), ethylene glycol diacrylate, tetraallyl ammonium polyethylene glycol chloride, diacrylamide, cyanomethyl acrylate, epoxides and mixtures thereof.
- MVA methylene-bis-acrylamide
- ethylene glycol diacrylate ethylene glycol diacrylate
- tetraallyl ammonium polyethylene glycol chloride diacrylamide
- diacrylamide diacrylamide
- cyanomethyl acrylate epoxides and mixtures thereof.
- a free radical chain transfer agent also known as a chain limiter.
- the use of a chain transfer agent is particularly advantageous for controlling the molecular weight of the polymer obtained.
- a transfer agent there may be mentioned methanol, isopropanol, sodium hypophosphite, 2-mercaptoethanol, sodium methallylsulphonate, and mixtures thereof.
- a person skilled in the art will know how to adjust the amounts of branching agent and optionally of transfer agent so as to preferably obtain a water-soluble resin.
- the resin or polymer does not require the development of a particular polymerization process. Indeed, it can be obtained using all the polymerization techniques well known to those skilled in the art. It can in particular be solution polymerization; gel polymerization; precipitation polymerization; emulsion polymerization (aqueous or reverse); suspension polymerization; reactive extrusion polymerization; water-in-water polymerization; or micellar polymerization.
- the preferred polymerization technique is solution polymerization. It indeed makes it possible to obtain polymers having a molecular weight in line with the desired effects and benefits.
- Polymerization is generally free radical polymerization.
- free radical polymerization is meant in particular free radical polymerization by means of UV, azo, redox or thermal initiators as well as controlled radical polymerization (CRP) techniques or matrix polymerization techniques.
- the aqueous cosmetic composition for the care and shaping of the hair is aqueous cosmetic composition for the care and shaping of the hair
- an aqueous composition refers to a composition containing water in a proportion such that the main phase is aqueous.
- aqueous cosmetic composition consisting of water and fixing resin is advantageously transparent.
- the term “transparent composition” is understood to mean a composition whose transmittance value measured at 420 nm is greater than 85%.
- the transmittance measurement is carried out at 420 nm, for example in a cell (advantageously a 1.5 mL polystyrene cell), with an optical path of 10 mm, at 25 ° C, for a solution comprising 2.4 g / L of resin in water.
- This measurement is carried out by means of a spectrophotometer, for example a spectrophotometer of the Hach Lange DR 600 type.
- composition according to the invention may be in the form of a gel, a solution, a spray, or a lacquer, without this being limiting.
- the composition is in the form of a gel. It is advantageously transparent according to the definition above.
- the aqueous cosmetic composition according to the invention preferably comprises between 0.05 and 10% by weight of the fixing resin, preferentially between 0.1 and 5% by weight, even more preferably between 0.15 and 1% by weight.
- the composition comprises:
- this aqueous cosmetic composition is advantageously transparent.
- composition according to the invention comprises water. It can also comprise a mixture of water and cosmetically acceptable solvents such as monoalcohols, polyalcohols, glycol ethers. Mention may more particularly be made of lower alcohols such as ethanol, isopropanol, polyalcohols such as diethylene glycol, glycol ethers.
- the water concentration is generally between 50 and 99% by weight relative to the total weight of the composition. It is preferably at least 60% by weight, preferably at least 80% and even more preferably at least 90%.
- any type of thickening agent can be used, including anionic, cationic, amphoteric polymers, with preference being given to crosslinked acrylic polyacids.
- Carbomers are particularly preferred. Their amount is generally between 0.01 and 10% by weight, preferably between 0.05 and 5% by weight.
- the pH of the compositions according to the invention is generally between 2 and 9, and in particular between 3 and 8. It can be adjusted to the value chosen by means of basifying or acidifying agents usually used in cosmetics for this type of application. .
- composition according to the invention When the composition according to the invention is pressurized in aerosol form in order to obtain a lacquer, it comprises at least one propellant which can be chosen from volatile hydrocarbons such as n-butane, propane, isobutane , pentane, chlorinated and / or fluorinated hydrocarbons and their mixtures. Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof can also be used as the propellant.
- volatile hydrocarbons such as n-butane, propane, isobutane , pentane, chlorinated and / or fluorinated hydrocarbons and their mixtures.
- Carbon dioxide, nitrous oxide, dimethyl ether, nitrogen, compressed air and mixtures thereof can also be used as the propellant.
- the propellant concentration is generally between 10 and 50% by weight relative to the total weight of the pressurized composition.
- compositions according to the invention may also contain surfactants, preservatives, sequestrants, softeners, colorants, viscosity modifiers, foam modifiers, anti-foam agents, pearlescent agents, moisturizers, anti-dandruff agents, agents antiseborrheics, sun filters, proteins, vitamins, plasticizers, hydroxy acids, and fragrances.
- compositions according to the invention can also contain other conditioning agents. These can then be chosen from natural or synthetic oils and waxes, fatty alcohols, esters of polyhydric alcohols, glycerides, silicone gums and resins or mixtures of these different compounds.
- compositions used according to the invention are, for example, rinsed or non-rinsed hair compositions, gels or solutions. They are, for example, styling lotions, brushing lotions, fixing compositions (lacquers) and styling.
- the lotions can be packaged in various forms, in particular in vaporizers, pump-dispenser bottles or in aerosol containers in order to ensure application of the composition in vaporized form.
- the compositions in gel form are for example packaged in the form of jars, preferably transparent.
- Figure 1 illustrates the change in the percentage of curl hold (TB) (or “curl retention”) over time of compositions containing a fixing resin.
- 203.0 g of water and 50 mg of sodium hypophosphite are introduced into a jacketed reactor equipped with mechanical stirring with pale half-moon, a condenser and a temperature sensor.
- the medium is heated to 83 ° C.
- a solution containing acrylic acid (AA) and methacrylic acid (AM A) or hydroxypropyl acrylate (HP A) comonomer is added over a period of 120 minutes.
- AA and AMA or HPA are shown in Table 1.
- a 10.0% by weight sodium persulfate solution is added over a period of 135 minutes.
- the medium is cooled to 60 ° C and 156.8 g of water is added to the medium.
- the pH is adjusted between 2.2 and 3.0 then the medium is stirred for an additional hour.
- the product is then filtered at 300 mhi.
- Polymeric solutions corresponding to Examples 2 to 6 are obtained, the compositions and the average molecular weights by weight (Mw) of which are detailed in Table 1.
- the resin of the composition of Example 1 for its part contains only monomers of acrylic acid.
- EDTA ethylenediaminetetraacetic acid
- the clarity of the gels is determined by measuring the transmittance of light on a Hach Lange DR 600 spectrophotometer. These measurements were carried out at 420 nm in 1.5 mL PS cuvettes, at 25 ° C., for a solution comprising 2.4 g / L of resin in water.
- the viscosity of the gels is determined at 23 ° C. with a Brookfield RVT viscometer at a speed of 20 revolutions / min. Those skilled in the art know how to choose the modulus depending on the viscosity of the gels. In the present case, and given the composition of the gel and the desired texture, module 7 is used.
- compositions C’I to C’6 are all transparent because they have a clarity greater than 85% T. Their viscosity and their rheological property are very good.
- compositions C’I to C’6 containing respectively the resins of Examples 1 to 6.
- a lock of European type hair is immersed in the hydroalcoholic resin solution and the excess solution is removed by passing the lock over its entire length between two fingers. The lock is then combed once and then wound on a sulk.
- the locks on the looper are then placed for 24 hours at 23 ° C and 50% relative humidity.
- the wicks are unwound and placed in an oven with controlled humidity at 90% at 25 ° C.
- the length of the bit at to serves as a reference (Li) for calculating the percentage of loop resistance (% TB), also known as the percentage of curl retention (% CR).
- the length of the wicks is measured at different time intervals (Lt).
- the percentage of curl retention is calculated using the following relationship:
- % TB [(L - Lt) / (L - Li)] * 100
- compositions C'3 and C'4 respectively containing the resins of Examples 3 45% mol AMA) and 4 (71% mol AMA), offer excellent resistance to humidity, although greater than those obtained with compositions C'I and C'2, containing the resins of Examples 1 (0 mol% AMA) and 2 (8.5 mol% AMA).
- Composition C'2 exhibits poorer curl hold than composition C'I.
- compositions C’5 and C’6 offer very poor resistance to humidity.
- the observation of the C’6 curve compared to the C’3 curve allows us to say that the substitution of AMA by HPA strongly degrades the resistance to humidity.
- curve C’5 Observation of curve C’5 compared to curve C’3 highlights the importance of the molecular weight of the resin on the resistance to humidity of the composition containing it. Indeed, composition C’5 containing an AA / AMA 45/55 copolymer with a weight average molecular weight of less than 20,000 g / mol does not make it possible to increase the curl strength.
- compositions C’3 and C’4 according to the invention do not exhibit any tacky effect and are easy to remove during washing, thus satisfying the desired criteria.
- a homopolymer of methacrylic acid (example 7), that is to say containing 100 mol% of monomeric units of methacrylic acid, is prepared according to the method described in the scientific publication "High Molecular Weight Poly (methacrylic acid) with Narrow Polydispersity by RAFT Polymerization ”- Macromolecules, 2009, 42, pages 1494-1499.
- the polymer obtained corresponds to Example 7.
- Another polymer is prepared by the same method except that 12 mol% of methacrylic acid is replaced by 12 mol% of acrylic acid.
- the polymer obtained corresponds to Example 8.
- the polymer of Example 7 has such a high viscosity that it is too difficult to handle for use by formulators of cosmetic compositions.
- Example 8 can be handled.
- a C'8 hair gel composition is made with the polymer of Example 8 according to the formulation in Table 2.
- the gel viscosity is 52,000 cps, and the clarity 91%.
- the same wet strength test as in part 3 / is carried out, and the loop resistance at 300 minutes is 93%, which is very satisfactory and demonstrates the technical effect of the polymers of the invention.
- polymers of lines 2, 5 and 8 of Table 1 of document EP1402877 are produced. They are denoted respectively Examples 9, 11 and 13.
- a polymer 10 is produced as the polymer 9 in which 10 mol% of ethyl acrylate are replaced by 10 mol% of acrylic acid.
- Polymer 12 is made like polymer 11 in which 25 mole% ethyl acrylate is replaced by 25 mole% methacrylic acid.
- a polymer 14 is made such as polymer 13 in which 25 mole% of methyl acrylate is replaced by 25 mole% of methacrylic acid.
- Table 4 summarizes the composition of polymers 9 to 14.
- the values of acrylic acid (AA), methacrylic acid (AMA), ethyl acrylate (EA), methyl acrylate (MA) and Lipol 1 are expressed in mol%.
- the values of diallyl phthalate (DAP) and n-dodecyl mercaptan (DDM) are expressed in% by mass.
- the molecular weight of Lipol 1 is 1188 g / mol.
- Lipol 1 is a lipophilically modified monomer having a linear saturated alkyl group of 18 carbon atoms connected via 20 ethylene oxide residues to a methacryloyl group.
- the polymers 9 to 14 are used in the hair gel composition of Table 2, and the gel compositions obtained are respectively denoted C'9 to C '14.
- the viscosity of the gels and their clarity were measured according to the same. previously described methods. The results are reported in Table 5.
- Table 5 Viscosities and clarities of styling gels C'9 to C '14. The same resistance test in a humid environment as in part 3 / is carried out, and the results of loop resistance at 300 minutes are given in table 6.
- Example 9 Increasing the proportion of acrylic acid from 7.13mol% to 15 mol% in Example 9 makes it possible to improve the loop resistance by more than 10%. Increasing the proportion of acrylic acid from 11.58 mol% to 36.58 mol% in Example 11 makes it possible to improve the loop resistance by more than 30%. Increasing the proportion of acrylic acid from 10.55 mol% to 30.55 mol% in Example 13 makes it possible to improve the loop resistance by more than 31%.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1903581A FR3094641B1 (fr) | 2019-04-03 | 2019-04-03 | Composition cosmétique transparente pour cheveux |
PCT/FR2020/050562 WO2020201655A1 (fr) | 2019-04-03 | 2020-03-16 | Composition cosmetique pour cheveux |
Publications (1)
Publication Number | Publication Date |
---|---|
EP3946637A1 true EP3946637A1 (fr) | 2022-02-09 |
Family
ID=67185487
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP20726509.1A Pending EP3946637A1 (fr) | 2019-04-03 | 2020-03-16 | Composition cosmetique pour cheveux |
Country Status (7)
Country | Link |
---|---|
US (1) | US20220192965A1 (fr) |
EP (1) | EP3946637A1 (fr) |
JP (1) | JP2022528492A (fr) |
CN (1) | CN113710327A (fr) |
FR (1) | FR3094641B1 (fr) |
MX (1) | MX2021012136A (fr) |
WO (1) | WO2020201655A1 (fr) |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4196190A (en) * | 1976-07-19 | 1980-04-01 | Rohm And Haas Company | Acrylic hair setting resins having high resistance to moisture and rapid removability from the hair with shampoo |
US4543249A (en) * | 1980-03-27 | 1985-09-24 | American Cyanamid Co. | Hair spray compositions containing methylmethacrylate-methacrylic acid copolymers |
DE69324640T2 (de) * | 1992-09-23 | 1999-10-14 | Du Pont | Photoempfindliches dielektrisches Schichtmaterial und untereinander verbundene Mehrschichtschaltungen |
FR2737660B1 (fr) | 1995-08-11 | 1997-09-12 | Oreal | Composition cosmetique a pouvoir fixant et/ou conditionneur contenant un copolymere acrylique particulier |
EP1014918B1 (fr) | 1997-09-17 | 2006-04-05 | Eastman Chemical Company | Composition pulverisable fixatrice de cheveux et compositions pulverisables de consommation perfectionnees a composes organiques volatils reduits |
DE69934461T2 (de) * | 1998-09-11 | 2007-09-27 | Rohm And Haas Co. | Festigende Haarformungs-Zusammensetzungen |
DE60303752T2 (de) * | 2002-09-30 | 2006-09-21 | Rohm And Haas Co. | Verdickungsmittel für wässerige Systeme mit einem hohen Gehalt an grenzflächenaktiven Mitteln |
EP2248510A1 (fr) * | 2009-05-07 | 2010-11-10 | Rohm and Haas Company | Composition aqueuse épaissie |
CA2980822A1 (fr) * | 2015-04-20 | 2016-10-27 | Akzo Nobel Chemicals International B.V. | Copolymeres et compositions de fixateur pour cheveux acryliques |
-
2019
- 2019-04-03 FR FR1903581A patent/FR3094641B1/fr active Active
-
2020
- 2020-03-16 EP EP20726509.1A patent/EP3946637A1/fr active Pending
- 2020-03-16 MX MX2021012136A patent/MX2021012136A/es unknown
- 2020-03-16 JP JP2021558955A patent/JP2022528492A/ja active Pending
- 2020-03-16 CN CN202080026506.3A patent/CN113710327A/zh active Pending
- 2020-03-16 US US17/441,884 patent/US20220192965A1/en active Pending
- 2020-03-16 WO PCT/FR2020/050562 patent/WO2020201655A1/fr unknown
Also Published As
Publication number | Publication date |
---|---|
MX2021012136A (es) | 2021-11-03 |
JP2022528492A (ja) | 2022-06-13 |
CN113710327A (zh) | 2021-11-26 |
FR3094641B1 (fr) | 2021-05-14 |
US20220192965A1 (en) | 2022-06-23 |
WO2020201655A1 (fr) | 2020-10-08 |
FR3094641A1 (fr) | 2020-10-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1765893B1 (fr) | Nouveaux copolymeres ethyleniques, compositions les comprenant et procedes de preparation et de traitement | |
CA2414483A1 (fr) | Polymeres radicalaires cationiques ou amphoteres auto-adhesifs et leur utilisation en cosmetique | |
FR2511232A1 (fr) | Procede d'ondulation ou de defrisage de cheveux et produit utilisable a cette fin | |
EP0494022B1 (fr) | Nouveaux copolymères à base de N-alkyl acrylamide, leur préparation et leur utilisation comme agents épaississants, notamment dans des compositions de shampooing | |
EP1051146A1 (fr) | Composition de coiffage comprenant un polymere aux caracteristiques particulieres et un polymere filmogene ionique | |
FR2791989A1 (fr) | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation | |
EP1768643A2 (fr) | Compositions cosmetiques contenant au moins un tensioactif et au moins un copolymere ethylenique a greffons polyvethyleneglycol | |
EP1043345A1 (fr) | Composition notamment cosmétique ou pharmaceutique comprenant des polymères ayant une structure en étoiles, lesdits polymères et leur utilisation | |
FR2521004A1 (fr) | Procede pour defriser ou onduler les cheveux et leur conditionnement simultane et composition pour l'ondulation des cheveux | |
JPS60108409A (ja) | カチオン性両性四元共重合体 | |
FR3076730A1 (fr) | Agent cosmétique pour la mise en forme temporaire de fibres kératiniques comportant un agent filmogène | |
FR3044902A1 (fr) | Procede de traitement des fibres keratiniques utilisant une composition aqueuse comprenant une association d'alcoxysilanes particuliers | |
WO2020201655A1 (fr) | Composition cosmetique pour cheveux | |
EP1592721B1 (fr) | Polymeres hyperbranches a basse temperature de transition vitreuse et leurs utilisations en cosmetique | |
FR2848430A1 (fr) | Composition capillaire comprenant un copolymere filmogene a gradient, composition aerosol la comprenant et procedes de traitement | |
FR2844185A1 (fr) | Composition de maquillage des fibres keratiniques presentant un extrait sec en solides eleve combine a un profil adhesif particulier | |
FR3025098A1 (fr) | Composition cosmetique de type gel facilement demaquillable | |
EP1591100A1 (fr) | Composition de vernis à ongles comprenant un polymère ayant des unités LCST | |
FR2850659A1 (fr) | Polymeres hyperbranches a faible temperature de transition vitreuse et leurs utilisations en cosmetique | |
FR2903596A1 (fr) | Composition cosmetique comprenant au moins un polymere thermogelifiant particulier en association avec un polymere fixant synthetique solubilise dans l'eau. | |
FR2903600A1 (fr) | Mascara contenant un polymere thermogelifiant | |
CA2304391A1 (fr) | Composition cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation notamment en capillaire | |
FR3141342A1 (fr) | Composition comprenant un complexe polyionique à base d’acide hyaluronique et un polymère superabsorbant | |
FR3131690A1 (fr) | Composition comprenant une particule de complexe polyionique | |
WO2021130264A1 (fr) | Composition transparente pour le soin du cheveu et/ou de la peau |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20211001 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
RAP3 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: SNF GROUP |
|
P01 | Opt-out of the competence of the unified patent court (upc) registered |
Effective date: 20230527 |