WO2016064006A1 - Polymer containing phosphorylcholine, and cosmetic composition containing same - Google Patents
Polymer containing phosphorylcholine, and cosmetic composition containing same Download PDFInfo
- Publication number
- WO2016064006A1 WO2016064006A1 PCT/KR2014/010033 KR2014010033W WO2016064006A1 WO 2016064006 A1 WO2016064006 A1 WO 2016064006A1 KR 2014010033 W KR2014010033 W KR 2014010033W WO 2016064006 A1 WO2016064006 A1 WO 2016064006A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- phosphorylcholine
- trimethylammonio
- meth
- ethyl
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 121
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 title claims abstract description 57
- 229950004354 phosphorylcholine Drugs 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title claims description 54
- 239000002537 cosmetic Substances 0.000 title claims description 49
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000003999 initiator Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- -1 acryloyloxy Chemical group 0.000 claims description 53
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- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 14
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- 239000003431 cross linking reagent Substances 0.000 claims description 13
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- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- IYNRVIKPUTZSOR-HWKANZROSA-N ethenyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC=C IYNRVIKPUTZSOR-HWKANZROSA-N 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
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- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- RFIMISVNSAUMBU-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC=C RFIMISVNSAUMBU-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- WAPBZMSKSPCLSL-UHFFFAOYSA-N 2-methylidenedotriacontanoic acid prop-2-enoic acid Chemical compound C(CCCCCCCCCCCCCCCCCCCCCCCCCCCCC)C(C(=O)O)=C.C(C=C)(=O)O WAPBZMSKSPCLSL-UHFFFAOYSA-N 0.000 description 1
- OIEDDNJAEIOXEP-UHFFFAOYSA-N 2-methylideneicosanoic acid octadecyl prop-2-enoate Chemical compound C(CCCCCCCCCCCCCCCCC)C(C(=O)O)=C.C(C=C)(=O)OCCCCCCCCCCCCCCCCCC OIEDDNJAEIOXEP-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- FYSPKARCDVNGFL-UHFFFAOYSA-N 2-prop-2-enoyloxyprop-2-enoic acid Chemical compound OC(=O)C(=C)OC(=O)C=C FYSPKARCDVNGFL-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- XQGDBUCAFFJLKB-UHFFFAOYSA-N C(C)(C)C(C(=O)O)=C.C(C=C)(=O)OC(C)C Chemical compound C(C)(C)C(C(=O)O)=C.C(C=C)(=O)OC(C)C XQGDBUCAFFJLKB-UHFFFAOYSA-N 0.000 description 1
- QHAXBIUCFNMJSI-UHFFFAOYSA-N C(CC)C(C(=O)O)=C.C(C=C)(=O)OCCC Chemical compound C(CC)C(C(=O)O)=C.C(C=C)(=O)OCCC QHAXBIUCFNMJSI-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 241000208680 Hamamelis mollis Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- ICQGUVBTFBGASU-UHFFFAOYSA-N docosyl prop-2-enoate 2-methylidenetetracosanoic acid Chemical compound C(CCCCCCCCCCCCCCCCCCCCC)C(C(=O)O)=C.C(C=C)(=O)OCCCCCCCCCCCCCCCCCCCCCC ICQGUVBTFBGASU-UHFFFAOYSA-N 0.000 description 1
- MEDYMICOBSTWBO-UHFFFAOYSA-N dodecyl prop-2-enoate;2-methylidenetetradecanoic acid Chemical compound CCCCCCCCCCCCOC(=O)C=C.CCCCCCCCCCCCC(=C)C(O)=O MEDYMICOBSTWBO-UHFFFAOYSA-N 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- HXDBMSZZSWTGKB-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylidenebutanoic acid Chemical compound CCOC(=O)C=C.CCC(=C)C(O)=O HXDBMSZZSWTGKB-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 description 1
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- IQSHMXAZFHORGY-UHFFFAOYSA-N methyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound COC(=O)C=C.CC(=C)C(O)=O IQSHMXAZFHORGY-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000002357 osmotic agent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000037384 skin absorption Effects 0.000 description 1
- 231100000274 skin absorption Toxicity 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 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
- 229940118846 witch hazel Drugs 0.000 description 1
- 239000011787 zinc oxide 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
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F220/10—Esters
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/02—Homopolymers or copolymers of monomers containing phosphorus
Definitions
- the present invention relates to a polymer containing phosphorylcholine and a cosmetic composition comprising the same.
- the polymer containing acrylic acid or methacrylic acid is a variety of thickeners, dispersants, emulsifiers, superabsorbent polymer (superabsorbent polymer), etc. It is used for a purpose.
- the polymers of this type are known to have excellent ability to absorb and retain water and can swell tens of times more than their original volume.
- the polymers are skin irritant and have insufficient or very insufficient ability to protect the skin in long-term use. .
- there is a method of prescribing a skin protector together but there is a limit in reducing the stimulation of the viscosity regulator as well as insufficient efficacy.
- Patent Document 1 Republic of Korea Patent Publication No. 2010-0133452
- Patent Document 2 Republic of Korea Patent Publication No. 2010-0103565
- the present invention is derived from the above background, and one object of the present invention is to improve the disadvantages of the prior art and to provide a new polymer having very excellent properties in thickening, emulsion stability, absorbency, or dispersibility.
- the present invention also provides a more homogeneous polymer mixture by taking a structure in which heterogeneous polymer chains are entangled with each other when compared to a mixture simply mixing two or more kinds of polymers.
- the present invention to provide a cosmetic composition comprising a polymer having the new properties.
- the present invention provides a step of preparing a polymerized phosphorylcholine-based polymer including a phosphorylcholine-based monomer represented by the following formula (1), and the phosphorylcholine-based polymer, ⁇ , ⁇ -ethylenically unsaturated monomer, initiator It provides a method for producing a polymer entangled with a phosphoryl choline polymer chain comprising the step of preparing a reaction solution containing a polymerized ⁇ , ⁇ -ethylenically unsaturated monomer in the presence of a phosphoryl choline polymer.
- (meth) acryl is used herein to mean acryl or methacryl.
- Z represents a hydrogen atom or R 5 -O-CO-, where R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms), and Y represents An alkyleneoxy group having 1 to 20 carbon atoms, R 1 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and R 2 , R 3 and R 4 are the same or different groups and represent a hydrogen atom or a 1 to 6 carbon atom; Represents a hydrocarbon group or a hydroxy hydrocarbon group, m is an integer from 1 to 20, and n is an integer from 2 to 5.
- the polymer according to the present invention is a polymer having a phosphorylcholine polymer chain intertwined, and has a very good characteristic in thickening, absorbency, or dispersibility, and at the same time, compared with other polymers developed in the past, for example, acrylic acid polymers. It has an excellent effect on improved moisturizing power, skin barrier function improvement and good biocompatibility.
- a more homogeneous polymer mixture can be obtained by taking a structure in which heterogeneous polymer chains are entangled with each other when compared to a mixture in which two or more kinds of polymers are simply mixed.
- the cosmetic composition comprising the polymer according to the present invention can be used for a variety of skin care and hair care that has an effect on skin moisturizing, atopy improvement, inflammation relief, application and hair conditioning.
- a polymer according to an embodiment of the present invention is a polymer in which phosphorylcholine polymer chains are entangled, preparing a polymerized phosphorylcholine polymer including a phosphorylcholine monomer represented by Formula (1) below, And preparing a reaction solution containing the phosphorylcholine-based polymer, ⁇ , ⁇ -ethylenically unsaturated monomer, and initiator to polymerize ⁇ , ⁇ -ethylenically unsaturated monomer in the presence of phosphorylcholine-based polymer.
- Phosphorylcholine based polymer chains can be prepared from the process for producing the entangled polymer.
- the present inventors can be usefully used for thickening polymers of phosphorylcholine-based polymer chains, and give superior effects in terms of effects compared to known materials such as polyacrylic acid, and also universally in various technical fields. It has been found applicable.
- the content of the phosphorylcholine-based polymer in the final polymer prepared according to the present invention is not limited, but is preferably 0.1 to 30 parts by weight, more preferably 1 to 10 parts by weight relative to the total weight of 100 polymers.
- the content of the phosphorylcholine-based polymer is less than the above range, the moisturizing property and biocompatibility of the polymer are insufficient, and when the above range is exceeded, the thickening efficacy is lowered.
- the phosphorylcholine-based polymer according to one embodiment of the present invention is preferably polymerized including a phosphorylcholine-based monomer having a structure of the following formula (1).
- Generally known radical polymerization methods can be used and are not limited.
- Z represents a hydrogen atom or R 5 -O-CO-, wherein R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms, and Y represents a carbon atom
- R ⁇ 1> represents a hydrogen atom or a C1-C5 hydrocarbon group
- R ⁇ 2> , R ⁇ 3> and R ⁇ 4> represent the same or another group and represent a hydrogen atom, a C1-C6 hydrocarbon group, or a hydroxy hydrocarbon group.
- m is an integer of 1-20
- n is an integer of 2-5.
- the phosphorylcholine monomers represented by the formula (1) are, for example, the phosphorylcholine monomers are 2-((meth) acryloyloxy) ethyl-2 '-(trimethylammonio) ethylphosphate, 3- ((Meth) acryloyloxy) propyl-2 '-(trimethylammonio) ethyl phosphate, 4-((meth) acryloyloxy) butyl-2'-(trimethylammonio) ethyl phosphate, 5-(( Meta) acryloyloxy) pentyl-2 '-(trimethylammonio) ethylphosphate, 6 ((meth) acryloyloxy) hexyl-2'-(trimethylammonio) ethylphosphate, 2-((meth) acrylic Loyloxy) ethyl-2 '-(triethylammonio) ethylphosphate, 2-((meth) acrylo
- the blending ratio in the case of using another monomer capable of radical polymerization is preferably 5 to 1000 parts by weight of the other polymerizable monomer, preferably 10 to 100 parts by weight based on 100 parts by weight of the phosphorylcholine monomer.
- the blending ratio of the other polymerizable monomer exceeds 1000 parts by weight, there is a fear that the properties of the obtained polymer such as solubility or biocompatibility in the water-containing medium may not be sufficiently exhibited. The effect may not be expressed.
- Phosphorylcholine monomers according to the present invention are not particularly limited, but 2- (methacryloyloxy) ethyl-2 '-(trimethylammonio) ethylphosphate [2- (methacryloyloxy) ethyl in terms of absorbency and biocompatibility. -2 '-(trimethylammonio) ethylphosphate, also referred to as 2-methacryloyloxyethylphosphorylcholine, hereinafter abbreviated as MPC] is preferred, but not limited thereto.
- the phosphorylcholine polymer chain entangled polymer according to the present invention is obtained by polymerizing one or more ⁇ , ⁇ -ethylenically unsaturated monomers in the presence of a phosphorylcholine polymer. That is, it is produced by entangled with the polymer chain obtained from a phosphorylcholine type polymer chain and the (alpha), (beta)-ethylenically unsaturated monomer naturally in the superposition
- the ⁇ , ⁇ -ethylenically unsaturated monomer may be represented by the following formula (2).
- L is a hydrogen atom or R 8 -O-CO-, wherein R 8 hermit wish
- R 8 hermit wish
- R 6 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, a halogen atom, a hydroxy group, or a cyano group
- R 7 represents a hydrogen atom or a hydrocarbon group of 1 to 30 carbon atoms.
- the said (alpha), (beta)-ethylenically unsaturated monomer contains the (alpha), (beta)-ethylenically unsaturated carboxylic acid.
- the ⁇ , ⁇ -ethylenically unsaturated carboxylic acid includes monobasic acids or maleic acids such as acrylic acid, methacrylic acid, crotonic acid, and acryloxypropenoic acid. acid), fumaric acid, dibasic acid of itaconic acid, and the like, each of which may be used alone or in combination thereof.
- the monomer represented by the formula (2) examples include methyl acrylate (methyl acrylate), ethyl acrylate (ethyl acrylate), propyl acrylate (propyl acrylate), isopropyl acrylate (isopropyl acrylate), butyl acryl Butyl acrylate, isobutyl acrylate, octyl acrylate, heptyl acrylate, decyl acrylate, isodecyl acrylate, lauryl Acrylate (lauryl acrylate), stearyl acrylate (stearyl acrylate), behenyl acrylate (behenyl acrylate), melisyl acrylate (melissyl acrylate) and the corresponding methacrylates, and the like, and at least one of them Can be selected and used as a monomer.
- the crosslinking agent forms a network structure by forming a crosslink in the polymerization of the ⁇ , ⁇ -ethylenically unsaturated monomer so that the polymer chain obtained from the phosphorylcholine-based polymer chain and the ⁇ , ⁇ -ethylenically unsaturated monomer are more stably intertwined. It has a stable thickening effect even in a wide pH range.
- the type of crosslinking agent of the polymer according to the present invention is not particularly limited as long as it can be bound by a radical polymerization reaction.
- the content of the crosslinking agent according to the present invention is 0.01 to 10 parts by weight per 100 parts by weight of the ⁇ , ⁇ -ethylenically unsaturated monomer, preferably 0.05 to 5 parts by weight per 100 parts by weight of the ⁇ , ⁇ -ethylenically unsaturated monomer. If the amount is less than 0.01 part by weight, the thickening effect of the polymer is insignificant, and if the content of the crosslinking agent is more than 10 parts by weight, a portion of the polymer may not be swelled in water, which may cause difficulty in reducing the efficacy.
- the radical polymerization initiator of the present invention for example, azo initiators such as azobisisobutyronitrile (AIBN), azobisdimethylvaleronitrile, benzoyl peroxide, lauroyl peroxide ( Lauroyl peroxide, Potassium persulfate, di (2-ethylhexyl) peroxydicarbonate, di (secbutyl) peroxydicarbonate, di (sec) Di (isopropyl) peroxydicarbonate, di (cyclohexyl) peroxydicarbonate, di (cetyl) peroxydicarbonate, di (n-propyl) Peroxy carbonate such as di (npropyl) peroxydicarbonate].
- AIBN azobisisobutyronitrile
- azobisdimethylvaleronitrile benzoyl peroxide
- lauroyl peroxide Lauroyl peroxide
- Potassium persulfate di (2-ethylhe
- the polymerization initiators include Duzot's Vazo 52G, Vazo 64G, Vazo 67G, Vazo 88G, etc., and the selection of the initiator includes a half life time of each temperature of the initiator and a boiling point of the organic solvent. Choose in consideration of.
- a solvent may be used in the polymerization reaction, and an appropriate solvent is selected according to the polymerization method. It can be prepared by various methods such as suspension polymerization using an organic solvent as a reaction medium, reverse phase emulsion polymerization, precipitation polymerization or solution polymerization using water as a reaction medium.
- the solvent is not limited but may be used in a 1 to 30 times weight ratio to the total weight of the monomers.
- the organic solvent for example, toluene, benzene, cyclohexane, ethyl acetate, n-hexane, methyl ethyl ketone, etc. may be selected and used, and one or more organic solvents may be mixed and used in an appropriate amount. For example, it can be used as a mixed solvent mixed in a weight ratio of 1:99 to 99: 1.
- the polymer of the present invention can be prepared by a method such as suspension polymerization using an organic solvent as a reaction medium, reverse phase emulsion polymerization, precipitation polymerization or solution polymerization using water as a reaction medium, and these polymerization methods are generally radical polymerization reactions.
- a method such as suspension polymerization using an organic solvent as a reaction medium, reverse phase emulsion polymerization, precipitation polymerization or solution polymerization using water as a reaction medium, and these polymerization methods are generally radical polymerization reactions.
- the precipitation polymerization method will be described as an example of the present invention.
- phosphorylcholine-based polymer is added to the organic solvent in the reactor, and then ⁇ , ⁇ -ethylenically unsaturated monomer, crosslinking agent and polymerization initiator are added and dissolved, followed by purging with nitrogen or an inert gas (polymerization reaction and / or aging reaction). Up to) and the temperature is raised to about 50 ⁇ 90 °C polymerization for about 3 to 10 hours.
- the polymer in the form of powder may be obtained by removing the organic solvent by filtration under reduced pressure at about 70 to 110 ° C. after the polymerization reaction is completed.
- the preparation of the polymer is preferably performed under an inert gas atmosphere such as nitrogen, carbon dioxide, or helium.
- the organic solvent is not particularly limited but is preferably one capable of dissolving the monomer, more preferably one capable of dissolving the crosslinking agent and may be selected from one or more of the aforementioned organic solvents.
- the radical reaction under the organic solvent causes chain growth of a predetermined size or more, and the polymerization reaction is terminated while being precipitated without dissolving in the organic solvent depending on the polar value of the organic solvent used by the grown polymer.
- the length of the polymer chain can be adjusted according to the mixing ratio of the mixed solvent.
- water when water is used as a solvent, it can also manufacture by emulsion polymerization.
- the cosmetic composition is an article used in the human body to clean and beautify the human body to add charm and brighten the appearance, or to maintain or promote the health of the skin and hair, and includes a personal hygiene care article such as a cleaner or a bath solvent. It is a broad concept to include.
- the polymer of the present invention is added as a component of the cosmetic composition and can be used for the use of flame resistant thickeners and / or emulsifiable thickeners. It can also serve as a moisturizer and impart excellent biocompatibility to cosmetic compositions.
- the cosmetic composition comprising the polymer of the present invention as an active ingredient may be specifically used for skin care or hair care, and when used for skin care, it may show improved skin absorption and skin barrier function improvement, and hair When used for care, it may show improved solubility and protection of damaged hair.
- the polymer content in the cosmetic composition may have a variety of ranges depending on the use and formulation of the cosmetic composition, it is preferably from 0.01 to 10% by weight based on the total weight of the composition in terms of usability (for example applicability), moisturizing feeling and the like.
- Cosmetic compositions according to the invention are conventionally used in a variety of components in addition to the aqueous medium and the above polymers, such as preservatives, osmotic agents, pH adjusters, buffers, stabilizers, aluminum hydroxide, aluminum phosphate, surfactants, liposomes, thickeners and the like and cosmetic compositions
- the ingredients used may include, but are not limited to, antioxidants, stabilizers, solubilizers, conventional adjuvants such as vitamins, pigments and flavors, and carriers and the like.
- the content of the polymer of the present invention is 0.001-30% by weight, preferably 0.01-10% by weight relative to the total weight of the cosmetic composition.
- Cosmetic compositions of the invention may be prepared in any formulation conventionally prepared in the art, including, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing, It may be formulated as an oil, powder foundation, emulsion foundation, wax foundation, spray, and the like, but is not limited thereto. More specifically, it may be prepared in the form of a flexible lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
- the formulation of the present invention is a paste, cream or gel
- animal oil, vegetable oil, wax, paraffin, starch, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier component.
- the formulation of the present invention is a powder or a spray
- lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, in particular in the case of a spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.
- a solvent, solubilizer or emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 Fatty acid esters of, 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.
- liquid carrier diluents such as water, ethanol or propylene glycol
- suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, and microcrystals are used as carrier components.
- Castle cellulose, aluminum metahydroxy, bentonite, agar and the like can be used.
- the formulation of the present invention is a surfactant-containing cleansing agent
- a surfactant-containing cleansing agent as a carrier component, an aliphatic alcohol sulfate, an aliphatic alcohol ether sulfate, a sulfosuccinic acid monoester, isethionate, an imidazolinium derivative, a methyltaurate, a sarcosinate, a fatty acid amide ether Sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.
- the cosmetic composition for hair care in addition to the above polymers, suitable carriers, surfactants, fragrances, opacifiers, bonding aids (proteins), aerosol propellents, gelling agents (gelling) It may include one or more conventional additives such as agent), and may be prepared in various formulations including shampoo, rinse, hair fixative wax, hair care conditioner and the like.
- the cosmetic method of the present invention refers to all cosmetic methods for applying the cosmetic composition of the present invention to human skin. That is, all the methods known in the art for applying the cosmetic composition to the skin belong to the cosmetic method of the present invention.
- the cosmetic composition of the present invention may be used alone or in duplicate, or may be used in combination with other cosmetic compositions other than the present invention.
- the cosmetic composition with excellent skin protection effect according to the present invention can be used according to a conventional method of use, the number of times of use can be varied according to the user's skin condition or taste.
- the cosmetic composition of the present invention is a soap, surfactant-containing cleansing or surfactant-free cleansing formulation, it may be wiped off, peeled off or washed with water after application to the skin.
- the soap is liquid soap, powdered soap, solid soap or oil soap
- the surfactant-containing cleansing formulation is a cleansing foam, cleansing water, cleansing towel or cleansing pack
- the surfactant-free cleansing formulation is a cleansing cream , Cleansing lotion, cleansing water or cleansing gel, but is not limited thereto.
- the obtained phosphorylcholine polymer had a 1.0 wt% neutralization viscosity of 54,000 cps and was neutralized with UV-Vis.
- Transparency measurement with a spectometer (420nm, 10 mm cell) showed a transmittance of 90%.
- the obtained phosphorylcholine-based polymer had a neutralization viscosity of 1.0 wt% of 32,000 cps and was neutralized with UV-Vis.
- the transparency was measured by spectometer (420nm, 10 mm cell) and showed 85% transmittance.
- Preparation Example 1 a polymerization reaction was performed without a phosphorylcholine polymer to obtain an acrylic polymer, and then 10 g of phosphorylcholine polymer was added to the slurry and mixed to prepare a final polymer in which an acrylic polymer and a phosphorylcholine polymer were mixed. Got it.
- the flexible component was prepared by mixing the composition component and the composition ratio, and the moisturizing effect and the skin barrier function improvement effect, the inflammation relieving effect, and the emulsification property of the cosmetic were evaluated using the polymer.
- Example 2 After dividing 30 healthy women into three groups (A, B, C) at 25 ° C., 45% relative humidity and no air flow, the cosmetics of Example 1 were applied to group A for group B. After applying the cosmetic of Comparative Example 1, Comparative Example 2, the appropriate amount was applied to the upper arm of the arm three times a day for 6 weeks, the TEWAMETER TM300 (C + K electronic GmbH Transdermal moisture loss (TEWL), ie TEWL (TEWL) value change TEWL over time, and CORNEOMETER CM 820 PC (C + K electronic GmbH. Germany). The moisturizing effect was measured by quantifying the moisture content of the skin from 0 to 150 according to the change in electrical conductivity. The results are shown in Table 2.
- the cosmetic table containing the polymer having the structure of the present invention (Example 1) was found to have a significantly improved transdermal moisture loss compared to the comparative examples, the polymer exhibits a moisturizing effect.
- the corneometer value measured the moisture content of the skin was found that the Example shows a high increase. That is, the cosmetic table containing the polymer of the present invention was measured to have a high skin moisture content, and the skin transdermal moisture loss was improved, and it can be seen that the effect of improving the moisturizing and skin barrier function of the cosmetic containing the polymer of the present invention is very effective.
- the cosmetic composition of Comparative Example 2 was formulated according to Table 1, and applied to the area of the upper left arm of the arm at 2 X 2 cm 2 (2 times / day, 0.2 g / time) for 2 weeks, and a skin erythema meter (Mexameter MX18, C + K Electronics GmbH Germany) measured the degree of skin erythema and observed the degree of inflammation relief due to the SDS-induced irritation.
- the cosmetic composition containing the polymer of the present invention (Example 1) has an anti-inflammatory effect compared to cosmetics containing no polymer of the present invention and a conventional witch hazel extract It was excellent.
- the polymer according to the present invention has very good properties in thickening, absorbency, or dispersibility, and at the same time shows excellent effects in improved moisturizing power, skin barrier function and excellent biocompatibility, so that it can be used for various skin care and hair care applications. Industrially useful
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Abstract
The present invention provides a method for preparing a polymer containing phosphorylcholine, comprising the steps of: preparing a phosphorylcholine-based polymer containing a phosphorylcholine-based monomer and polymerized thereby; and preparing a reaction solution containing the phosphorylcholine-based polymer, an α,β-ethylenically unsaturated monomer and an initiator so as to polymerize the α,β-ethylenically unsaturated monomer in the presence of the phosphorylcholine-based polymer.
Description
본 발명은 포스포릴콜린을 함유하는 중합체 및 이를 포함하는 화장료 조성물에 관한 것이다.The present invention relates to a polymer containing phosphorylcholine and a cosmetic composition comprising the same.
대한민국 공개특허 제2010-0133452호 및 대한민국 공개특허 제2010-0103565호와 같이, 아크릴산 또는 메타크릴산을 포함하는 중합체는 제약 또는 화장료 분야에서 증점제, 분산제, 유화제, 초흡수성 중합체(superabsorbent polymer) 등 다양한 용도로 사용되고 있다. 그러나 상기 계통의 중합체는 물을 흡수하고 보유하는 능력이 우수하며 본래 부피보다 수십 배로 팽윤할 수 있는 것으로 알려져 있지만 피부자극성이 있고 또한 장기 사용에서는 충분히 피부를 보호하는 기능이 없거나 또는 매우 부족한 단점이 있다. 이를 극복하기 위한 수단으로는 피부 보호제를 함께 처방하는 방법이 있으나, 효능이 미흡할 뿐만 아니라 점도 조절제의 자극을 원천적으로 감소시키는 데는 한계가 있어 왔다.As in the Republic of Korea Patent Publication No. 2010-0133452 and the Republic of Korea Patent Publication No. 2010-0103565, the polymer containing acrylic acid or methacrylic acid is a variety of thickeners, dispersants, emulsifiers, superabsorbent polymer (superabsorbent polymer), etc. It is used for a purpose. However, the polymers of this type are known to have excellent ability to absorb and retain water and can swell tens of times more than their original volume. However, the polymers are skin irritant and have insufficient or very insufficient ability to protect the skin in long-term use. . As a means for overcoming this, there is a method of prescribing a skin protector together, but there is a limit in reducing the stimulation of the viscosity regulator as well as insufficient efficacy.
따라서, 기존의 점도 조절제가 갖는 장점을 살리면서, 피부자극성을 감소시키고 더 나아가 피부보호기능을 가지는 새로운 중합체를 제조함으로써 화장료 분야에 폭넓게 사용될 수 있는 물질 및 그 물질을 함유하는 화장료 조성물이 요구가 있다.Therefore, there is a need for a material that can be widely used in the cosmetic field and cosmetic composition containing the material by reducing the skin irritation and producing a new polymer having a skin protection function while taking advantage of the existing viscosity modifier. .
따라서 상기의 (메타)아크릴계 중합체가 가지는증점 기능의 장점을 살리고 피부자극성 개선 기능이나 피부보호기능을 가지는 새로운 구조의 중합체를 제조함으로써, 화장료 분야에 폭넓게 사용될 수 있는 물질 및 그 물질을 함유한 화장료 조성물이 요청된다. Therefore, by utilizing the advantages of the thickening function of the above-mentioned (meth) acrylic polymer and manufacturing a polymer having a new structure having a skin irritation improving function or a skin protection function, a substance that can be widely used in the cosmetic field and a cosmetic composition containing the material Is requested.
(특허문헌 1) 대한민국 공개특허 제2010-0133452호(Patent Document 1) Republic of Korea Patent Publication No. 2010-0133452
(특허문헌 2) 대한민국 공개특허 제2010-0103565호(Patent Document 2) Republic of Korea Patent Publication No. 2010-0103565
본 발명은 상기와 같은 배경 하에서 도출된 것으로서, 본 발명의 일 목적은 종래의 단점을 개선하고 증점, 유화 안정성, 흡수성, 또는 분산성에서 매우 우수한 특성을 가지는 새로운 중합체를 제공하는 것이다. SUMMARY OF THE INVENTION The present invention is derived from the above background, and one object of the present invention is to improve the disadvantages of the prior art and to provide a new polymer having very excellent properties in thickening, emulsion stability, absorbency, or dispersibility.
본 발명의 또 다른 목적은 기존의 증점 기능 이외에 우수한 생체 적합성, 향상된 보습력, 피부 장벽 기능 개선 등의 특성을 가지는 새로운 중합체를 제공하는 것이다. It is another object of the present invention to provide a new polymer having properties such as excellent biocompatibility, improved moisturizing power, improved skin barrier function, etc. in addition to the existing thickening function.
또한 본 발명은 두 종류 이상의 중합체를 단순히 혼합한 혼합물과 비교할 때 이종의 중합체 사슬들이 서로 얽혀 있는 구조를 취하여 보다 균질한 중합체 혼합물을 제공하는 것이다.The present invention also provides a more homogeneous polymer mixture by taking a structure in which heterogeneous polymer chains are entangled with each other when compared to a mixture simply mixing two or more kinds of polymers.
또한 본 발명은 상기 새로운 특성을 가지는 중합체를 포함하는 화장료 조성물을 제공하는 것이다.In another aspect, the present invention to provide a cosmetic composition comprising a polymer having the new properties.
본 발명의 상기 일 목적을 해결하기 위하여, In order to solve the above object of the present invention,
본 발명은 하기의 화학식 (1)로 표시되는 포스포릴콜린계 단량체를 포함하여 중합된 포스포릴콜린계 중합체를 준비하는 단계, 및 상기 포스포릴콜린계 중합체, α,β-에틸렌계 불포화 단량체, 개시제가 포함된 반응액을 준비하여 포스포릴콜린계 중합체 존재하에 α,β-에틸렌계 불포화 단량체를 중합하는 단계를 포함하여 이루어진, 포스포릴콜린계 중합체 사슬이 얽힌 중합체의 제조방법 등을 제공한다. The present invention provides a step of preparing a polymerized phosphorylcholine-based polymer including a phosphorylcholine-based monomer represented by the following formula (1), and the phosphorylcholine-based polymer, α, β-ethylenically unsaturated monomer, initiator It provides a method for producing a polymer entangled with a phosphoryl choline polymer chain comprising the step of preparing a reaction solution containing a polymerized α, β-ethylenically unsaturated monomer in the presence of a phosphoryl choline polymer.
본 명세서에서 “(메타)아크릴” 이라는 용어는 아크릴 또는 메타크릴을 의미하는 것으로 표시된 것이다.The term "(meth) acryl" is used herein to mean acryl or methacryl.
[화학식 (1)][Formula (1)]
(화학식 (1)에서 Z는 수소원자 또는 R5-O-CO-(여기서, R5는 수소원자, 탄소수 1~10의 알킬기 또는 탄소수 1~10의 히드록시알킬기를 나타낸다)를 나타내고, Y는 탄소수 1~20의 알킬렌옥시기를 나타낸다. 또한, R1은 수소원자 또는 탄소수 1~5의 탄화수소기를 나타내고, R2, R3 및 R4는 동일 또는 다른 기로서, 수소원자, 탄소수 1~6의 탄화수소기 또는 히드록시 탄화수소기를 나타낸다. 또한, m은 1~20의 정수이고, n은 2~5의 정수이다.)(In formula (1), Z represents a hydrogen atom or R 5 -O-CO-, where R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms), and Y represents An alkyleneoxy group having 1 to 20 carbon atoms, R 1 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and R 2 , R 3 and R 4 are the same or different groups and represent a hydrogen atom or a 1 to 6 carbon atom; Represents a hydrocarbon group or a hydroxy hydrocarbon group, m is an integer from 1 to 20, and n is an integer from 2 to 5.
본 발명에 따른 중합체는 포스포릴콜린계 중합체 사슬이 얽힌 중합체로서, 종래에 개발된 다른 중합체, 예를 들면 아크릴산계 중합체와 비교할 때, 증점, 흡수성, 또는 분산성에서 매우 우수한 특성을 가지면서, 동시에 향상된 보습력, 피부 장벽 기능 개선 및 우수한 생체 적합성에서 우수한 효과를 나타낸다. 또한, 두 종류 이상의 중합체를 단순히 혼합한 혼합물과 비교할 때 이종의 중합체 사슬들이 서로 얽혀 있는 구조를 취하여 보다 균질한 중합체 혼합물을 얻을 수 있다.The polymer according to the present invention is a polymer having a phosphorylcholine polymer chain intertwined, and has a very good characteristic in thickening, absorbency, or dispersibility, and at the same time, compared with other polymers developed in the past, for example, acrylic acid polymers. It has an excellent effect on improved moisturizing power, skin barrier function improvement and good biocompatibility. In addition, a more homogeneous polymer mixture can be obtained by taking a structure in which heterogeneous polymer chains are entangled with each other when compared to a mixture in which two or more kinds of polymers are simply mixed.
또한, 본 발명에 따른 중합체를 포함하는 화장료 조성물은 피부보습, 아토피 개선, 염증 완화, 발림성 및 모발 컨디셔닝에 효과를 갖는 다양한 스킨케어 및 헤어케어의 용도로 사용될 수 있다.In addition, the cosmetic composition comprising the polymer according to the present invention can be used for a variety of skin care and hair care that has an effect on skin moisturizing, atopy improvement, inflammation relief, application and hair conditioning.
이하, 본 발명을 실시예를 통하여 구체적으로 설명한다. 다만, 하기 실시예는 본 발명을 보다 명확히 예시하기 위한 것일 뿐이므로, 비록 한정적, 단정적 표현이 존재하여도 본 발명의 보호범위를 한정하는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are only intended to more clearly illustrate the present invention, but the present invention does not limit the protection scope of the present invention even though there is limited or assertive expression.
본 발명의 일실시예에 따른 중합체는 포스포릴콜린계 중합체 사슬이 얽힌 중합체로서, 하기의 화학식 (1)로 표시되는포스포릴콜린계 단량체를 포함하여 중합된 포스포릴콜린계 중합체를 준비하는 단계, 및 상기 포스포릴콜린계 중합체, α,β-에틸렌계 불포화 단량체, 개시제가 포함된 반응액을 준비하여 포스포릴콜린계 중합체 존재하에 α,β-에틸렌계 불포화 단량체를 중합하는 단계를 포함하여 이루어진, 포스포릴콜린계 중합체 사슬이 얽힌 중합체의 제조방법으로부터 제조될 수 있다.A polymer according to an embodiment of the present invention is a polymer in which phosphorylcholine polymer chains are entangled, preparing a polymerized phosphorylcholine polymer including a phosphorylcholine monomer represented by Formula (1) below, And preparing a reaction solution containing the phosphorylcholine-based polymer, α, β-ethylenically unsaturated monomer, and initiator to polymerize α, β-ethylenically unsaturated monomer in the presence of phosphorylcholine-based polymer. Phosphorylcholine based polymer chains can be prepared from the process for producing the entangled polymer.
본 발명자는 포스포릴콜린계 중합체 사슬이 얽힌 중합체가 증점 용도로 유용하게 사용될 수 있으면서, 기존의 폴리아크릴산 등의 공지의 물질에 비하여 효과면에서 월등한 효과를 부여하며, 또한 다양한 기술분야에 유니버셜하게 적용될 수 있음을 알게되었다.The present inventors can be usefully used for thickening polymers of phosphorylcholine-based polymer chains, and give superior effects in terms of effects compared to known materials such as polyacrylic acid, and also universally in various technical fields. It has been found applicable.
본 발명에 따라 최종 제조되는 중합체 내에서 포스포릴콜린계 중합체의 함량은 제한되지 않으나 전체 중합체 100 중량 대비 0.1 ~ 30 중량부가 좋으며, 더욱 바람직하게는 1 ~ 10 중량부가 좋다. 포스포릴콜린계 중합체의 함량이 상기 범위 미만인 경우 중합체의 보습성 및 생체 적합성이 미비하고, 상기 범위를 초과하면 증점 효능이 저하된다.The content of the phosphorylcholine-based polymer in the final polymer prepared according to the present invention is not limited, but is preferably 0.1 to 30 parts by weight, more preferably 1 to 10 parts by weight relative to the total weight of 100 polymers. When the content of the phosphorylcholine-based polymer is less than the above range, the moisturizing property and biocompatibility of the polymer are insufficient, and when the above range is exceeded, the thickening efficacy is lowered.
이하에서 보다 상세히 설명한다.It will be described in more detail below.
포스포릴콜린계 중합체Phosphorylcholine polymer
본 발명의 일실시예에 따른 포스포릴콜린계 중합체는 하기 화학식 (1)의 구조를 가지는 포스포릴콜린계 단량체를 포함하여 중합된 것이 바람직하다. 일반적으로 알려진 라디칼 중합 방법을 사용할 수 있으며 제한되지 않는다.The phosphorylcholine-based polymer according to one embodiment of the present invention is preferably polymerized including a phosphorylcholine-based monomer having a structure of the following formula (1). Generally known radical polymerization methods can be used and are not limited.
[화학식 (1)][Formula (1)]
화학식 (1)에서 Z는 수소원자 또는 R5-O-CO-(여기서, R5는 수소원자, 탄소수 1~10의 알킬기 또는 탄소수 1~10의 히드록시알킬기를 나타낸다)를 나타내고, Y는 탄소수 1~20의 알킬렌옥시기를 나타낸다. 또한, R1은 수소원자 또는 탄소수 1~5의 탄화수소기를 나타내고, R2, R3 및 R4는 동일 또는 다른 기로서, 수소원자, 탄소수 1~6의 탄화수소기 또는 히드록시 탄화수소기를 나타낸다. 또한, m은 1~20의 정수이고, n은 2~5의 정수이다.In formula (1), Z represents a hydrogen atom or R 5 -O-CO-, wherein R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms, and Y represents a carbon atom The alkyleneoxy group of 1-20 is shown. In addition, R <1> represents a hydrogen atom or a C1-C5 hydrocarbon group, and R <2> , R <3> and R <4> represent the same or another group and represent a hydrogen atom, a C1-C6 hydrocarbon group, or a hydroxy hydrocarbon group. In addition, m is an integer of 1-20, n is an integer of 2-5.
화학식 (1)로 표시되는 포스포릴콜린계 단량체는 예를 들면, 상기 포스포릴콜린계 단량체는 2-((메타)아크릴로일옥시)에틸-2'-(트리메틸암모니오)에틸포스페이트, 3-((메타)아크릴로일옥시)프로필-2'-(트리메틸암모니오)에틸포스페이트, 4-((메타)아크릴로일옥시)부틸-2'-(트리메틸암모니오)에틸포스페이트, 5-((메타)아크릴로일옥시)펜틸-2'-(트리메틸암모니오)에틸포스페이트, 6((메타)아크릴로일옥시)헥실-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)에틸-2'-(트리에틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)에틸-2'-(트리프로필암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)에틸-2'(트리부틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)프로필-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)부틸-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)펜틸-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)헥실-2'-(트리메틸암모니오)에틸포스페이트, 에틸(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 부틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 히드록시에틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 에틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 부틸(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 히드록시에틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트 등이 있고, 이들은 단독 또는 혼합물로 사용될 수 있다. 또한, 라디칼 중합이 가능한 다른 단량체가 더 포함되어 중합될 수 있다. 일례로 스티렌, 메틸스티렌, 클로로메틸스티렌, 메틸아크릴레이트, 메틸메타크릴레이트, 에틸아크릴레이트, 에틸메타크릴레이트, 부틸아크릴레이트, 부틸메타크릴레이트, 아크릴산, 메타크릴산, 아크릴산아미드, 메타크릴산아미드, 2-히드록시에틸아크릴레이트, 2-히드록시메타크릴레이트, 에틸비닐에테르, 부틸비닐에테르, N-비닐피롤리돈, 염화비닐, 염화비닐리덴, 에틸렌, 프로필렌, 이소부티렌, 아크릴로니트릴 등을 들 수 있다. 라디칼 중합이 가능한 다른 단량체를 사용하는 경우의 배합 비율은 포스포릴콜린계 단량체 100중량부에 대하여, 다른 중합성 단량체 5~1000중량부, 바람직하게는 10~100중량부의 범위가 바람직하다. 다른 중합성단량체의 배합비율이 1000중량부를 초과하는 경우에는 얻어진 중합체의 물함유 매체에 대한 용해성이나생체적합성 등의 특성이 충분히 발휘할 수 없는 염려가 있고, 5중량부 미만에서는 다른 중합성 단량체를 공중합시키는 효과가 발현하지 않을 수 있다.The phosphorylcholine monomers represented by the formula (1) are, for example, the phosphorylcholine monomers are 2-((meth) acryloyloxy) ethyl-2 '-(trimethylammonio) ethylphosphate, 3- ((Meth) acryloyloxy) propyl-2 '-(trimethylammonio) ethyl phosphate, 4-((meth) acryloyloxy) butyl-2'-(trimethylammonio) ethyl phosphate, 5-(( Meta) acryloyloxy) pentyl-2 '-(trimethylammonio) ethylphosphate, 6 ((meth) acryloyloxy) hexyl-2'-(trimethylammonio) ethylphosphate, 2-((meth) acrylic Loyloxy) ethyl-2 '-(triethylammonio) ethylphosphate, 2-((meth) acryloyloxy) ethyl-2'-(tripropylammonio) ethylphosphate, 2-((meth) acrylic Loyloxy) ethyl-2 '(tributylammonio) ethylphosphate, 2-((meth) acryloyloxy) propyl-2'-(trimethylammonio) ethylphosphate, 2-((meth) acryloyl jade Butyl-2'- (Trimethylammonio) ethylphosphate, 2-((meth) acryloyloxy) pentyl-2 '-(trimethylammonio) ethylphosphate, 2-((meth) acryloyloxy) hexyl-2'-(trimethyl Ammonio) ethyl phosphate, ethyl (2'-trimethylammonio ethylphosphorylethyl) fmaleate, butyl- (2'-trimethylammonio ethylphosphorylethyl) fmaleate, hydroxyethyl- (2'-trimethylammonio Ethylphosphorylethyl) phmaleate, ethyl- (2'-trimethylammonio ethylphosphorylethyl) phmaleate, butyl (2'-trimethylammonio ethylphosphorylethyl) phmaleate, hydroxyethyl- (2'-trimethyl Ammonio ethylphosphorylethyl) fmaleate and the like, which can be used alone or in mixture. In addition, other monomers capable of radical polymerization may be further included and polymerized. For example, styrene, methyl styrene, chloromethyl styrene, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, acrylic acid, methacrylic acid, acrylic acid amide, methacrylic acid Amide, 2-hydroxyethyl acrylate, 2-hydroxy methacrylate, ethyl vinyl ether, butyl vinyl ether, N-vinylpyrrolidone, vinyl chloride, vinylidene chloride, ethylene, propylene, isobutylene, acrylo Nitrile, and the like. The blending ratio in the case of using another monomer capable of radical polymerization is preferably 5 to 1000 parts by weight of the other polymerizable monomer, preferably 10 to 100 parts by weight based on 100 parts by weight of the phosphorylcholine monomer. When the blending ratio of the other polymerizable monomer exceeds 1000 parts by weight, there is a fear that the properties of the obtained polymer such as solubility or biocompatibility in the water-containing medium may not be sufficiently exhibited. The effect may not be expressed.
본 발명에 따른 포스포릴콜린계 단량체는 크게 제한되지 않으나, 흡수성 및 생체 적합성의 점에서 2-(메타크릴로일옥시)에틸-2'-(트리메틸암모니오)에틸포스페이트[2-(methacryloyloxy)ethyl-2'-(trimethylammonio)ethylphosphate, 2-메타클리로일옥시에틸포스폴린콜린(2-methacryloyloxyethylphosphorylcholine)이라고도 함, 이하, MPC로 약칭함]가 바람직하지만 이에 한정되는 것은 아니다.Phosphorylcholine monomers according to the present invention are not particularly limited, but 2- (methacryloyloxy) ethyl-2 '-(trimethylammonio) ethylphosphate [2- (methacryloyloxy) ethyl in terms of absorbency and biocompatibility. -2 '-(trimethylammonio) ethylphosphate, also referred to as 2-methacryloyloxyethylphosphorylcholine, hereinafter abbreviated as MPC] is preferred, but not limited thereto.
α,β-에틸렌계 불포화 단량체α, β-ethylenically unsaturated monomer
본 발명에 따른 포스포릴콜린계 중합체 사슬이 얽힌 중합체는포스포릴콜린계 중합체 존재하에서 하나 또는 둘이상의 α,β-에틸렌계 불포화 단량체를 중합함으로써 얻어진다. 즉, 중합 과정에서 자연스럽게 포스포릴콜린계 중합체 사슬과 α,β-에틸렌계 불포화 단량체로부터 얻어지는 중합체 사슬이 서로 얽히도록 하여 제조된 것이다. 상기 α,β-에틸렌계 불포화 단량체는 하기 화학식 (2)로 표현될 수 있다.The phosphorylcholine polymer chain entangled polymer according to the present invention is obtained by polymerizing one or more α, β-ethylenically unsaturated monomers in the presence of a phosphorylcholine polymer. That is, it is produced by entangled with the polymer chain obtained from a phosphorylcholine type polymer chain and the (alpha), (beta)-ethylenically unsaturated monomer naturally in the superposition | polymerization process. The α, β-ethylenically unsaturated monomer may be represented by the following formula (2).
[화학식 (2)][Formula (2)]
상기 구조식에서 L은 수소원자 또는 R8-O-CO-이고, 상기 R8은수소원자, 탄소수 1~10의 알킬기 또는 탄소수 1~10의 히드록시알킬기를 나타내고, X는 
, 
, 
또는 
에서 선택되는 어느 하나이며, r은 1~10의 정수이다. 또한, R6은 수소원자, 탄소수 1~5의 알킬기, 할로겐원자, 히드록시기, 또는 시아노기를 나타내고, R7은 수소원자 또는 탄소수 1~30의 탄화수소기를 나타낸다.In the above structural formula and L is a hydrogen atom or R 8 -O-CO-, wherein R 8 hermit wish Here, represents a hydroxyalkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 10, X is , , or Is any one selected from, and r is an integer of 1 to 10. R 6 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, a halogen atom, a hydroxy group, or a cyano group, and R 7 represents a hydrogen atom or a hydrocarbon group of 1 to 30 carbon atoms.
상기 α,β-에틸렌계 불포화 단량체는 α,β-에틸렌계 불포화 카르복실산을 포함하는 것이 바람직하다. α,β-에틸렌계 불포화 카르복실산에는 아크릴산(acrylic acid), 메타크릴산(methacrylic acid), 크로톤산(crotonic), 아크릴옥시프로페논산(acyloxypropenoic acid) 등의 1염기산 또는 말레산(maleic acid), 푸마르산(fumaric acid), 이타콘산(itaconic acid)의 2염기산 등이 있으며, 이들 각각을 단독으로 사용할 수도 있고, 이들을 혼합하여 사용할 수도 있다.It is preferable that the said (alpha), (beta)-ethylenically unsaturated monomer contains the (alpha), (beta)-ethylenically unsaturated carboxylic acid. The α, β-ethylenically unsaturated carboxylic acid includes monobasic acids or maleic acids such as acrylic acid, methacrylic acid, crotonic acid, and acryloxypropenoic acid. acid), fumaric acid, dibasic acid of itaconic acid, and the like, each of which may be used alone or in combination thereof.
또한, 상기 화학식 (2)로 표시되는 단량체의 구체적인 예로는 메틸 아크릴레이트(methyl acrylate), 에틸 아크릴레이트(ethyl acrylate), 프로필 아크릴레이트(propyl acrylate), 이소프로필 아크릴레이트(isopropyl acrylate), 부틸 아크릴레이트(butyl acrylate), 이소부틸 아크릴레이트(isobutyl acrylate), 옥틸 아크릴레이트(octyl acrylate), 헵틸 아크릴레이트(heptyl acrylate), 데실 아크릴레이트(decyl acrylate), 이소데실 아크릴레이트(isodecyl acrylate), 라우릴 아크릴레이트(lauryl acrylate), 스테아릴 아크릴레이트(stearyl acrylate), 베헤닐 아크릴레이트(behenyl acrylate), 멜리실 아크릴레이트(melissyl acrylate) 및 이에 대응되는 메타크릴레이트 등이 있고, 이들 중에서 적어도 1종 이상을 선택하여 단량체로 사용할 수 있다.In addition, specific examples of the monomer represented by the formula (2) include methyl acrylate (methyl acrylate), ethyl acrylate (ethyl acrylate), propyl acrylate (propyl acrylate), isopropyl acrylate (isopropyl acrylate), butyl acryl Butyl acrylate, isobutyl acrylate, octyl acrylate, heptyl acrylate, decyl acrylate, isodecyl acrylate, lauryl Acrylate (lauryl acrylate), stearyl acrylate (stearyl acrylate), behenyl acrylate (behenyl acrylate), melisyl acrylate (melissyl acrylate) and the corresponding methacrylates, and the like, and at least one of them Can be selected and used as a monomer.
가교제Crosslinking agent
본 발명에서는 2개 이상의 불포화 에틸렌 결합기를 가진 적어도 1종의 가교제를 포함할 수 있다. 본 발명에서 가교제는 α,β-에틸렌계 불포화 단량체의 중합시 가교 결합을 형성시켜 네트워크 구조를 형성하여 포스포릴콜린계 중합체 사슬과 α, β-에틸렌계 불포화 단량체로부터 얻어지는 중합체 사슬이 보다 안정적으로 얽히도록 하고, 넓은 pH 범위에서도 안정적인 증점 효과를 가지게 한다. In the present invention, at least one crosslinking agent having two or more unsaturated ethylene bond groups may be included. In the present invention, the crosslinking agent forms a network structure by forming a crosslink in the polymerization of the α, β-ethylenically unsaturated monomer so that the polymer chain obtained from the phosphorylcholine-based polymer chain and the α, β-ethylenically unsaturated monomer are more stably intertwined. It has a stable thickening effect even in a wide pH range.
본 발명에 따른 중합체의 가교결합제는 라디칼 중합 반응에 의해 결합할 수 있는 것이라면 그 종류는 크게 제한되지 않으며, 예를 들면 에틸렌 글리콜 디아크릴레이트(ethylene glycol diacrylate), 에틸렌 글리콜 디메타크릴레이트(ethylene glycol dimethacrylate), 프로필렌 글리콜 디아크릴레이트(propylene glycol diacrylate),프로필렌 글리콜 디메타크릴레이트(propylene glycol dimethacrylate), 부틸렌 글리콜 디아크릴레이트(butylene glycol diacrylate), 부틸렌 글리콜 디메타크릴레이트(butylene glycol dimethacrylate), 헥실렌 글리콜 디아크릴레이트(hexylene glycol diacrylate), 헥실렌 클리콜 디메타크릴레이트(hexylene glycol dimethacrylate), 디에틸렌 글리콜 디아크릴레이트(diethylene glycol diacrylate), 디에틸렌 글리콜 디메타크릴레이트(diethylene glycol dimethacrylate), 트리에틸렌 글리콜 디아크릴레이트(triethylene glycol diacrylate), 트리에틸렌 글리콜 디메타크릴레이트(triethylene glycol dimethacrylate), 테트라에틸렌 글리콜 디아크릴레이트(tetraethylene glycol diacrylate), 테트라에틸렌 글리콜 디메타크릴레이트(tetraethylene glycol dimethacrylate), 알릴 아크릴레이트(allyl acrylate), 알릴 메타크릴레이트(allyl methacrylate), 메타알릴 아크릴레이트(methallyl acrylate), 알릴 에타크릴레이트(allyl ethacrylate), 에타알릴 아크릴레이트(ethallyl acrylate), 메타알릴 메타크릴레이트(methallyl methacrylate), 디알릴 프탈레이트(diallyl phthalate), 디알릴 말레이트(diallyl maleate), 디알릴 석시네이트(diallyl succinate), 트리아릴 포스페이트(triallyl phosphate), 디알릴 옥살레이트(diallyl oxalate), 디알릴말로네이트(diallyl malonate), 디알릴 시트레이트(diallyl citrate), 디알릴 푸마레이트(diallyl fumarate), 디비닐 벤젠(divinyl benzene), 트리비닐 벤젠(trivinyl bezene), 비닐 크로토네이트(vinyl crotonate), N,N-메틸렌-비스-아크릴아마이드(N,N-methylene-bis-acrylamide), 트리메틸올프로판 디알릴 에테르(trimethylolpropane diallyl ether) 또는 트리메틸올프로판 트리알릴 에테르(trimethylolpropane triallyl ether), 디알릴 펜타에리쓰리톨 에테르(diallyl pentaerythritol ether), 트리알릴 펜타에리쓰리톨 에테르(triallyl pentaerythritol ether), 테트라알릴 펜타에리쓰리톨 에테르(tetraallyl pentaerythritol ether), 디알릴 수크로오스 에테르(diallyl sucrose ether), 트리알릴 수크로오스 에테르(triallyl sucrose ether), 또는 테트라알릴 수크로오스 에테르(tetraallyl sucrose ether), 펜타알릴 수크로오스 에테르(pentaallyl sucroseether), 헥사알릴 수크로오스 에테르(hexaallyl sucrose ether) 등이 있고, 이들을 단독 또는 혼합하여 사용할 수 있다.The type of crosslinking agent of the polymer according to the present invention is not particularly limited as long as it can be bound by a radical polymerization reaction. For example, ethylene glycol diacrylate, ethylene glycol dimethacrylate (ethylene glycol) dimethacrylate), propylene glycol diacrylate, propylene glycol dimethacrylate, butylene glycol diacrylate, butylene glycol dimethacrylate , Hexylene glycol diacrylate, hexylene glycol dimethacrylate, hexylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate (diethylene glycol dimethacrylate ), Triethylene glycol diacrylate Triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, allyl acrylate acrylate, allyl methacrylate, methallyl acrylate, allyl ethacrylate, ethallyl acrylate, methallyl methacrylate, dimethyl Allyl phthalate, diallyl maleate, diallyl succinate, triallyl phosphate, diallyl oxalate, diallyl malonate Diallyl citrate, diallyl fumarate, divinyl benzene vinyl benzene, trivinyl bezene, vinyl crotonate, N, N-methylene-bis-acrylamide, trimethylolpropane diallyl ether trimethylolpropane diallyl ether or trimethylolpropane triallyl ether, diallyl pentaerythritol ether, triallyl pentaerythritol ether, tetraallyl pentaerythritol ether, tetraallyl pentaerythritol ether (tetraallyl pentaerythritol ether), diallyl sucrose ether, triallyl sucrose ether, or tetraallyl sucrose ether, tetraallyl sucrose ether, pentaallyl sucrose ether, hexaallyl sucrose ether (hexaallyl sucrose ether) and the like, and these may be used alone or in combination.
본 발명에 따른 가교제의 함량은 α,β-에틸렌계 불포화 단량체100 중량부당 0.01~10 중량부, 바람직하게는 α,β-에틸렌계 불포화 단량체100 중량부당 0.05~5 중량부인데, 가교제의 함량이 0.01 중량부 미만인 경우 중합체의 증점 효과가 미비하고, 가교제의 함량이 10 중량부를 초과하면 중합체의 일부가 물에 스웰링되지 못하여 효능이 저하되는 어려움이 발생한다. The content of the crosslinking agent according to the present invention is 0.01 to 10 parts by weight per 100 parts by weight of the α, β-ethylenically unsaturated monomer, preferably 0.05 to 5 parts by weight per 100 parts by weight of the α, β-ethylenically unsaturated monomer. If the amount is less than 0.01 part by weight, the thickening effect of the polymer is insignificant, and if the content of the crosslinking agent is more than 10 parts by weight, a portion of the polymer may not be swelled in water, which may cause difficulty in reducing the efficacy.
본 발명의 라디칼 중합개시제는, 예를 들면 아조비스이소부틸로니트릴(Azobisisobutyronitrile, AIBN), 아조비스디메틸발레로니트릴(Azobisdimethylvaleronitrile) 등과 같은 아조 개시제, 벤조일퍼옥사이드(Benzoyl peroxide), 라우로일퍼옥사이드(Lauroyl peroxide), 포타지움퍼설페이트(Potassium persulfate), 디(2-에틸헥실)퍼옥시디카보네이트[di(2ethylhexyl)peroxydicarbonate], 디(sec-부틸)퍼옥시디카보네이트[di(secbutyl)peroxydicarbonate], 디(이소프로필)퍼옥시디카보네이트[di(isopropyl)peroxydicarbonate], 디(시클로헥실)퍼옥시디카보네이트[di(cyclohexyl)peroxydicarbonate], 디(세틸)퍼옥시디카보네이트[di(cetyl)peroxydicarbonate], 디(n-프로필)퍼옥시디카보네이트[di(npropyl)peroxydicarbonate] 등과 같은 퍼옥시카보네이트 등이 있다. 상기 중합 개시제의 상업적인 상품으로는 Dupont사의 Vazo 52G, Vazo 64G, Vazo 67G, Vazo 88G 등이 있고, 개시제의 선택은 개시제의 각 온도별 반감기(Half life time)와 유기 용매의 끓는점(Boiling point) 등을 고려하여 선택한다.The radical polymerization initiator of the present invention, for example, azo initiators such as azobisisobutyronitrile (AIBN), azobisdimethylvaleronitrile, benzoyl peroxide, lauroyl peroxide ( Lauroyl peroxide, Potassium persulfate, di (2-ethylhexyl) peroxydicarbonate, di (secbutyl) peroxydicarbonate, di (sec) Di (isopropyl) peroxydicarbonate, di (cyclohexyl) peroxydicarbonate, di (cetyl) peroxydicarbonate, di (n-propyl) Peroxy carbonate such as di (npropyl) peroxydicarbonate]. Commercial products of the polymerization initiators include Duzot's Vazo 52G, Vazo 64G, Vazo 67G, Vazo 88G, etc., and the selection of the initiator includes a half life time of each temperature of the initiator and a boiling point of the organic solvent. Choose in consideration of.
한편, 중합 반응시 용매가 사용될 수 있으며, 중합 방법에 따라 적절한 용매가 선택된다. 유기 용제를 반응 매질로 사용하는 현탁 중합, 역상 에멀젼 중합, 침전 중합 또는 물을 반응 매질로 사용하는 용액 중합 등 다양한 방법으로 제조가 가능하다. 용매는 제한되지 않으나 단량체 총중량 대비 1~30배 중량비로 사용될 수 있다. 유기 용매로는 예를 들면 톨루엔, 벤젠, 시클로헥산, 에틸아세테이트, n-헥산, 메틸 에틸 케톤 등이 있으며, 이 중 하나를 선택하여 사용할 수도 있고, 1개 이상의 유기 용매를 적당량 혼합하여 사용한다. 예를 들면 1:99에서 99:1의 중량비로 혼합한 혼합용매로도 사용이 가능하다.Meanwhile, a solvent may be used in the polymerization reaction, and an appropriate solvent is selected according to the polymerization method. It can be prepared by various methods such as suspension polymerization using an organic solvent as a reaction medium, reverse phase emulsion polymerization, precipitation polymerization or solution polymerization using water as a reaction medium. The solvent is not limited but may be used in a 1 to 30 times weight ratio to the total weight of the monomers. As the organic solvent, for example, toluene, benzene, cyclohexane, ethyl acetate, n-hexane, methyl ethyl ketone, etc. may be selected and used, and one or more organic solvents may be mixed and used in an appropriate amount. For example, it can be used as a mixed solvent mixed in a weight ratio of 1:99 to 99: 1.
이하에서는 본 발명의 중합체의 제조방법에 대하여 설명한다.Hereinafter, the manufacturing method of the polymer of this invention is demonstrated.
본 발명의 중합체는 유기 용제를 반응 매질로 사용하는 현탁 중합, 역상 에멀젼 중합, 침전 중합 또는 물을 반응 매질로 사용하는 용액 중합 등의 방법으로 제조가 가능하며, 이들 중합 방법은 일반적으로 라디칼 중합 반응을 이용한다. 이하, 본 발명의 하나의 예로서 침전 중합 방법에 대해 설명한다.The polymer of the present invention can be prepared by a method such as suspension polymerization using an organic solvent as a reaction medium, reverse phase emulsion polymerization, precipitation polymerization or solution polymerization using water as a reaction medium, and these polymerization methods are generally radical polymerization reactions. Use Hereinafter, the precipitation polymerization method will be described as an example of the present invention.
먼저 반응기에 유기 용매에 포스포릴콜린계 중합체를 첨가한 후, α, β-에틸렌계 불포화 단량체, 가교제, 중합 개시제를 첨가하고 용해시킨 후, 질소나 불활성 기체로 퍼지(중합 반응 and/or 숙성 반응까지 계속)하고 약 50~90℃로 승온시켜 약 3~10시간 동안 중합반응시킨다. 중합반응이 완료된 슬러지를 여과 후 약 70~110℃에서 감압 증발에 의해 유기 용매를 제거함으로써 분말 형태인 중합체를 얻을 수 있다. First, phosphorylcholine-based polymer is added to the organic solvent in the reactor, and then α, β-ethylenically unsaturated monomer, crosslinking agent and polymerization initiator are added and dissolved, followed by purging with nitrogen or an inert gas (polymerization reaction and / or aging reaction). Up to) and the temperature is raised to about 50 ~ 90 ℃ polymerization for about 3 to 10 hours. The polymer in the form of powder may be obtained by removing the organic solvent by filtration under reduced pressure at about 70 to 110 ° C. after the polymerization reaction is completed.
이때, 중합체의 제조는 바람직하게는 질소, 이산화탄소, 또는 헬륨 등과 같은 불활성 가스 분위기하에서 행해진다. 유기 용매는 특별히 제한되지 않으나 단량체를 용해시킬 수 있는 것이 바람직하고, 가교제를 용해시킬수 있는 것이 더 바람직하며 전술한 유기 용매 중에서 하나 이상 선택될 수 있다. 유기용제 하에서의 라디칼 반응은 일정 사이즈 이상의 사슬 성장(propagation)이 일어나게 되며, 성장한 고분자가 사용한 유기용제의 극성 값에 따라서 유기용제에 녹지 않고 침전되면서 중합반응이 종결(termination)된다. 이러한 고분자 사슬의 길이를 혼합용매의 혼합 비율에 따라 조절할 수 있다. 또한, 물을 용매로 사용하는 경우에는 에멀젼 중합하여 제조할 수도 있다.At this time, the preparation of the polymer is preferably performed under an inert gas atmosphere such as nitrogen, carbon dioxide, or helium. The organic solvent is not particularly limited but is preferably one capable of dissolving the monomer, more preferably one capable of dissolving the crosslinking agent and may be selected from one or more of the aforementioned organic solvents. The radical reaction under the organic solvent causes chain growth of a predetermined size or more, and the polymerization reaction is terminated while being precipitated without dissolving in the organic solvent depending on the polar value of the organic solvent used by the grown polymer. The length of the polymer chain can be adjusted according to the mixing ratio of the mixed solvent. Moreover, when water is used as a solvent, it can also manufacture by emulsion polymerization.
화장료 조성물Cosmetic composition
본 발명의 다른 측면은 전술한 중합체를 유효성분으로 포함하는 화장료 조성물에 관한 것이다. 본 발명에서 화장료 조성물은 인체를 청결, 미화하여 매력을 더하고 용모를 밝게 변화시키거나 피부, 모발의 건강을 유지 또는 증진하기 위하여 인체에 사용되는 물품으로서, 세정제, 목욕 용제와 같은 개인 위생 관리 물품을 포함하는 광의의 개념이다.Another aspect of the invention relates to a cosmetic composition comprising the above-described polymer as an active ingredient. In the present invention, the cosmetic composition is an article used in the human body to clean and beautify the human body to add charm and brighten the appearance, or to maintain or promote the health of the skin and hair, and includes a personal hygiene care article such as a cleaner or a bath solvent. It is a broad concept to include.
본 발명의 중합체는 화장료 조성물의 일 성분으로 첨가되며 내염성 증점제 또는/및 유화성 증점제의 용도로 사용될 수 있다. 또한, 보습제로서의 역할을 하며 화장료 조성물에 우수한 생체 적합성을 부여할 수 있다. 본 발명의 중합체를 유효 성분으로 포함하는 화장료 조성물은 구체적으로 스킨케어용 또는 헤어케어용의 용도로 사용될 수 있는데, 스킨케어용으로 사용되는 경우 향상된 피부 흡수 및 피부 장벽 기능 개선을 보일 수 있으며, 헤어케어용으로 사용되는 경우 향상된 용해성 및 손상 모발의 보호 효과 등을 보일 수 있다. 상기 화장료 조성물 내의 중합체 함량은 화장료 조성물의 용도 및 제형에 따라 다양한 범위를 가질수 있으며, 사용감(예를 들어 발림성), 보습감 등의 관점에서 조성물 전체 중량을 기준으로 0.01~10 중량%인 것이 바람직하다.The polymer of the present invention is added as a component of the cosmetic composition and can be used for the use of flame resistant thickeners and / or emulsifiable thickeners. It can also serve as a moisturizer and impart excellent biocompatibility to cosmetic compositions. The cosmetic composition comprising the polymer of the present invention as an active ingredient may be specifically used for skin care or hair care, and when used for skin care, it may show improved skin absorption and skin barrier function improvement, and hair When used for care, it may show improved solubility and protection of damaged hair. The polymer content in the cosmetic composition may have a variety of ranges depending on the use and formulation of the cosmetic composition, it is preferably from 0.01 to 10% by weight based on the total weight of the composition in terms of usability (for example applicability), moisturizing feeling and the like.
본 발명에 따른 화장료 조성물은 수상 매질 및 상기의 중합체 외에 다양한 성분들, 예컨대 보존제, 삼투제, pH 조절제, 완충제, 안정제, 수산화알루미늄, 인산 알루미늄, 계면활성제, 리포솜, 증점제 등 및 화장료 조성물에 통상적으로 이용되는 성분들, 예컨대 항산화제, 안정화제, 용해화제, 비타민, 안료 및 향료와 같은 통상적인 보조제, 그리고 담체 등을 포함할 수 있으며, 이에 제한되지 않는다. 본 발명의 바람직한 구현예에 따르면, 본 발명의 중합체의 함량은 화장료 조성물의 총 중량에 대하여 0.001-30 중량%, 바람직하게는 0.01-10 중량%이다. Cosmetic compositions according to the invention are conventionally used in a variety of components in addition to the aqueous medium and the above polymers, such as preservatives, osmotic agents, pH adjusters, buffers, stabilizers, aluminum hydroxide, aluminum phosphate, surfactants, liposomes, thickeners and the like and cosmetic compositions The ingredients used may include, but are not limited to, antioxidants, stabilizers, solubilizers, conventional adjuvants such as vitamins, pigments and flavors, and carriers and the like. According to a preferred embodiment of the present invention, the content of the polymer of the present invention is 0.001-30% by weight, preferably 0.01-10% by weight relative to the total weight of the cosmetic composition.
본 발명의 화장료 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클렌징, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화 될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 유연 화장수, 영양 화장수, 영양 크림, 마사지 크림, 에센스, 아이 크림, 클렌징 크림, 클렌징 폼, 클렌징 워터, 팩, 스프레이 또는 파우더의 제형으로 제조될 수 있다. 본 발명의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물성유, 식물성유, 왁스, 파라핀, 전분, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다. 본 발명의 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로히드로카본, 프로판/부탄 또는 디메틸에테르와 같은 추진체를 포함할 수 있다. 본 발명의 제형이 용액 또는 유탁액인 경우에는 담체 성분으로서 용매, 용해화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌글리콜, 1,3-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다. 본 발명의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소 결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 등이 이용될 수 있다. 본 발명의 제형이 계면활성제 함유 클렌징인 경우에는 담체 성분으로서 지방족 알코올 설페이트, 지방족 알코올에테르 설페이트, 설포숙신산 모노에스테르, 이세티오네이트, 이미다졸리늄 유도체, 메틸타우레이트, 사르코시네이트, 지방산 아미드 에테르 설페이트, 알킬아미도베타인, 지방족 알코올, 지방산 글리세리드, 지방산 디에탄 올아미드, 식물성 유, 라놀린 유도체 또는 에톡실화 글리세롤 지방산 에스테르 등이 이용될 수 있다. 또한, 본 발명에 따른 헤어케어용 화장료 조성물은 상기의 중합체 외에 적절한 캐리어, 계면활성제, 향료, 유백제(opacifier), 결합보조제(combing aids), 단백질, 에어로졸 촉진제(aerosol propellents), 겔화제(gelling agent) 등 통상의 첨가제를 1종 이상 포함할 수 있고, 샴푸, 린스, 헤어 고정용 왁스, 헤어케어용 컨디셔너 등을 포함한 각종 제형으로 제조될 수 있다.Cosmetic compositions of the invention may be prepared in any formulation conventionally prepared in the art, including, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing, It may be formulated as an oil, powder foundation, emulsion foundation, wax foundation, spray, and the like, but is not limited thereto. More specifically, it may be prepared in the form of a flexible lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder. When the formulation of the present invention is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier component. When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, in particular in the case of a spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether. When the formulation of the present invention is a solution or emulsion, a solvent, solubilizer or emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 Fatty acid esters of, 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan. When the formulation of the present invention is a suspension, liquid carrier diluents such as water, ethanol or propylene glycol, suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, and microcrystals are used as carrier components. Castle cellulose, aluminum metahydroxy, bentonite, agar and the like can be used. When the formulation of the present invention is a surfactant-containing cleansing agent, as a carrier component, an aliphatic alcohol sulfate, an aliphatic alcohol ether sulfate, a sulfosuccinic acid monoester, isethionate, an imidazolinium derivative, a methyltaurate, a sarcosinate, a fatty acid amide ether Sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used. In addition, the cosmetic composition for hair care according to the present invention, in addition to the above polymers, suitable carriers, surfactants, fragrances, opacifiers, bonding aids (proteins), aerosol propellents, gelling agents (gelling) It may include one or more conventional additives such as agent), and may be prepared in various formulations including shampoo, rinse, hair fixative wax, hair care conditioner and the like.
본 발명의 화장 방법은 본 발명의 화장료 조성물을 사람의 피부에 도포하는 모든 화장 방법을 일컫는다. 즉, 화장료 조성물을 피부에 도포하는 당업계에 공지된 모든 방법이 본 발명의 화장 방법에 속한다. 본 발명의 화장료 조성물은 단독 또는 중복 도포하여 사용하거나, 본 발명 이외의 다른 화장료 조성물과 중복 도포하여 사용할 수 있다. 또한 본 발명에 따른 피부 보호 효과가 우수한 화장료 조성물은 통상적인 사용방법에 따라 사용될 수 있으며, 사용자의 피부 상태 또는 취향에 따라 그 사용횟수를 달리할 수 있다. 본 발명의 화장료 조성물이 비누, 계면활성제 함유 클렌징 또는 계면활성제 비함유 클렌징 제형일 경우, 피부에 도포한 후 닦아내거나 떼거나 물로 씻어낼 수도 있다. 구체적인 예로서, 상기 비누는 액상비누, 가루비누, 고형비누 또는 오일비누이며, 상기 계면활성제 함유 클렌징 제형은 클렌징폼, 클렌징 워터, 클렌징 수건 또는 클렌징 팩이며, 상기 계면활성제 비함유 클렌징 제형은 클렌징크림, 클렌징 로션, 클렌징 워터 또는 클렌징 겔이며, 이에 한정되는 것은 아니다. 본 발명의 상기 유효성분을 포함하는 화장료 조성물을 사람의 피부에 도포하는 화장방법을 수행하면, 피부보습효과 및 아토피 개선 효과를 얻을 수 있다.The cosmetic method of the present invention refers to all cosmetic methods for applying the cosmetic composition of the present invention to human skin. That is, all the methods known in the art for applying the cosmetic composition to the skin belong to the cosmetic method of the present invention. The cosmetic composition of the present invention may be used alone or in duplicate, or may be used in combination with other cosmetic compositions other than the present invention. In addition, the cosmetic composition with excellent skin protection effect according to the present invention can be used according to a conventional method of use, the number of times of use can be varied according to the user's skin condition or taste. When the cosmetic composition of the present invention is a soap, surfactant-containing cleansing or surfactant-free cleansing formulation, it may be wiped off, peeled off or washed with water after application to the skin. As a specific example, the soap is liquid soap, powdered soap, solid soap or oil soap, the surfactant-containing cleansing formulation is a cleansing foam, cleansing water, cleansing towel or cleansing pack, the surfactant-free cleansing formulation is a cleansing cream , Cleansing lotion, cleansing water or cleansing gel, but is not limited thereto. When the cosmetic method including the active ingredient of the present invention is applied to the skin of a person, the skin moisturizing effect and atopy improvement effect can be obtained.
이하, 본 발명에 따른 중합체의 제조 및 제조된 중합체를 이용한 화장료 조성물에 대하여 제조예 및 실시예를 통하여 설명하며, 본 발명은 실시예에 한정되는 것이 아니며 당업자가 다양하게 그 기술적 사상을 기반으로 하여 변경하여 발명할 수 있는 것도 포함한다.Hereinafter, the preparation of the polymer according to the present invention and the cosmetic composition using the produced polymer will be described with reference to the preparation examples and examples, the present invention is not limited to the examples and those skilled in the art based on various technical ideas It also includes what can be changed and invented.
1. 포스포릴콜린계 중합체의 준비1. Preparation of phosphorylcholine polymer
MPC 10g 과 개시제(AIBN) 0.03g을 에탄올 90g에 용해하고, 1시간 질소를 불어넣어 버블링 후, 65℃까지 승온하고 6시간 중합하였다. 중합완료된 중합체 용액을 멤브레인을 이용하여 에탄올과 잔류모노머 등을 제거하여 최종적으로 포스포릴콜린계 중합체를 얻었다. 10 g of MPC and 0.03 g of initiator (AIBN) were dissolved in 90 g of ethanol, and nitrogen was blown in for 1 hour, followed by bubbling, and the temperature was raised to 65 ° C and polymerized for 6 hours. The polymer-polymerized polymer solution was removed by using a membrane to remove ethanol and residual monomer, and finally a phosphorylcholine polymer was obtained.
2. 포스포릴콜린계 중합체 사슬이 얽힌 중합체의 제조2. Preparation of Phosphorylcholine Polymer Chain Intertwined Polymers
<제조예 1><Manufacture example 1>
상기 얻어진 포스포릴콜린계 중합체 10g과 아크릴산 100g을 혼합용제(Cyclohexane+Ethylacetate=50:50) 110g에 넣어서 개시제(AIBN) 0.02g, 가교제(APE, Allyl Pentaerythritol) 1g을 첨가후 1시간동안 질소 버블링 후, 50℃에서 10시간 동안 중합을 진행하였다. 중합 완료 후 슬러지를 80℃에서 진공건조하여 최종적으로 포스포릴콜린계 중합체 사슬이 얽힌 중합체를 제조하였다. 10 g of the obtained phosphorylcholine-based polymer and 100 g of acrylic acid were added to 110 g of a mixed solvent (Cyclohexane + Ethylacetate = 50: 50), followed by nitrogen bubbling for 1 hour after addition of 0.02 g of an initiator (AIBN) and 1 g of a crosslinking agent (APE, Allyl Pentaerythritol). Thereafter, polymerization was performed at 50 ° C. for 10 hours. After completion of the polymerization, the sludge was vacuum dried at 80 ° C. to finally prepare a polymer in which the phosphorylcholine polymer chain was entangled.
수득한 포스포릴콜린계 중합체는 1.0 중량% 중화점도가 54,000cps 이었고, 중화된 상태에서 UV-Vis. spectometer로 투명도 측정시(420nm, 10 mm cell) 90%의 투과도를 보였다.The obtained phosphorylcholine polymer had a 1.0 wt% neutralization viscosity of 54,000 cps and was neutralized with UV-Vis. Transparency measurement with a spectometer (420nm, 10 mm cell) showed a transmittance of 90%.
<제조예 2><Manufacture example 2>
상기 제조예 1에서, 메틸 아크릴레이트 10g을 더 첨가하여 중합반응을 진행한 것을 제외하고는 동일하게 실시하였다. In Preparation Example 1, the polymerization was carried out in the same manner except that 10 g of methyl acrylate was further added.
수득한 포스포릴콜린계 중합체는1.0 중량% 중화점도가 32,000cps 이었고, 중화된 상태에서 UV-Vis. spectometer로 투명도 측정시(420nm, 10 mm cell) 85%의 투과도를 보였다.The obtained phosphorylcholine-based polymer had a neutralization viscosity of 1.0 wt% of 32,000 cps and was neutralized with UV-Vis. The transparency was measured by spectometer (420nm, 10 mm cell) and showed 85% transmittance.
<제조예3><Production Example 3>
*상기 제조예 1에서, 포스포릴콜린계 중합체 15g을 사용한 것을 제외하고는 동일하게 실시하였다. * The same procedure as in Preparation Example 1 was performed except that 15 g of phosphorylcholine polymer was used.
<제조예4><Production Example 4>
상기 제조예 1에서, 가교제를 펜타에리쓰리톨 트리알릴 에테르(pentaerythritol triallyl ether)를 사용한 것을 제외하고는 동일하게 실시하였다. In Preparation Example 1, the crosslinking agent was carried out in the same manner except that pentaerythritol triallyl ether was used.
<제조예5>Production Example 5
상기 제조예 1에서, 가교제 없이 중합반응을 진행한 것을 제외하고는 동일하게 실시하였다.In Preparation Example 1, except that the polymerization was carried out without a crosslinking agent was carried out in the same manner.
<비교제조예 1><Comparative Production Example 1>
상기 제조예 1에서, 포스포릴콜린계 중합체 없이 중합반응을 진행하여 아크릴 중합체를 얻었다. In Preparation Example 1, the polymerization was carried out without the phosphorylcholine polymer to obtain an acrylic polymer.
<비교제조예 2><Comparative Production Example 2>
상기 제조예 1에서, 포스포릴콜린계 중합체 없이 중합반응을 진행하여 아크릴 중합체를 얻은 후 그 슬러리에 포스포릴콜린계 중합체 10g을 첨가, 혼합하여 아크릴 중합체와 포스포릴콜린계 중합체가 혼합된 최종 중합체를 얻었다.In Preparation Example 1, a polymerization reaction was performed without a phosphorylcholine polymer to obtain an acrylic polymer, and then 10 g of phosphorylcholine polymer was added to the slurry and mixed to prepare a final polymer in which an acrylic polymer and a phosphorylcholine polymer were mixed. Got it.
3. 실시예 : 화장료 조성물의 제조3. Example: Preparation of Cosmetic Composition
상기 제조예에서 제조한 중합체를 이용하여 조성성분 및 조성비로 혼합하여 유연화장수를 제조하고, 이를 이용하여화장료의 보습 및 피부 장벽기능 개선효과와 염증완화 효과 및 유화성 등을 평가하였다. Using the polymer prepared in the above preparation example, the flexible component was prepared by mixing the composition component and the composition ratio, and the moisturizing effect and the skin barrier function improvement effect, the inflammation relieving effect, and the emulsification property of the cosmetic were evaluated using the polymer.
(실시예 1)(Example 1)
상기 제조예 1에서 제조한 중합체를 이용하여 하기 표 1과 같은 조성성분 및 조성비로 혼합하여 하기와 같은 조성으로 유연화장수를 제조하고, 이를 이용하여화장료의 보습 및 피부 장벽기능 개선효과와 염증완화 효과를 평가하였다. Using the polymer prepared in Preparation Example 1 by mixing in the composition components and composition ratios as shown in Table 1 to produce a flexible longevity with the composition as follows, by using the moisturizing and skin barrier function improvement effect and inflammation relief effect of the cosmetic Was evaluated.
표 1
Table 1
| 성분 | 함량(중량%) |
| 제조예 및 비교제조예의 중합체 | 0.3 |
| 바셀린 | 7.0 |
| 유동파라핀 | 10.0 |
| 10.0밀납 | 2.0 |
| 폴리솔베이트 60 | 2.0 |
| 솔비탄세스퀴올레이트 | 2.5 |
| 스쿠알란 | 3.0 |
| 프로필렌글리콜 | 6.0 |
| 글리세린 | 4.0 |
| 트리에탄올아민 | 0.5 |
| 카르복시비닐폴리머 | 0.5 |
| 토코페릴아세테이트 | 0.1 |
| 향 | 0.01 |
| 정제수 | to 100 |
| ingredient | Content (% by weight) |
| Polymer of Preparation Example and Comparative Preparation Example | 0.3 |
| vaseline | 7.0 |
| Liquid paraffin | 10.0 |
| 10.0 wax | 2.0 |
| Polysorbate 60 | 2.0 |
| Sorbitan sesquioleate | 2.5 |
| Squalane | 3.0 |
| Propylene glycol | 6.0 |
| glycerin | 4.0 |
| Triethanolamine | 0.5 |
| Carboxy Vinyl Polymer | 0.5 |
| Tocopheryl Acetate | 0.1 |
| incense | 0.01 |
| Purified water | to 100 |
(실시예 2)(Example 2)
상기 실시예 1에서 제조예 1의 중합체 대신에 제조예 2의 중합체를 사용한 것을 제외하고는 동일하게 실시하였다.Except for using the polymer of Preparation Example 2 instead of the polymer of Preparation Example 1 in Example 1 was carried out in the same manner.
(실시예 3)(Example 3)
상기 실시예 1에서 제조예 1의 중합체 대신에 제조예 3의 중합체를 사용한 것을 제외하고는 동일하게 실시하였다.Except for using the polymer of Preparation Example 3 instead of the polymer of Preparation Example 1 in Example 1 was carried out in the same manner.
(실시예 4)(Example 4)
상기 실시예 1에서 제조예 1의 중합체 대신에 제조예 4의 중합체를 사용한 것을 제외하고는 동일하게 실시하였다.Except for using the polymer of Preparation Example 4 instead of the polymer of Preparation Example 1 in Example 1 was carried out in the same manner.
(실시예 5)(Example 5)
상기 실시예 1에서 제조예 1의 중합체 대신에 제조예 5의 중합체를 사용한 것을 제외하고는 동일하게 실시하였다.Except for using the polymer of Preparation Example 5 instead of the polymer of Preparation Example 1 in Example 1 was carried out in the same manner.
(비교실시예 1)Comparative Example 1
상기 실시예 1에서 제조예 1의 중합체 대신에 비교제조예 1의 중합체를 사용한 것을 제외하고는 동일하게 실시하였다.Except for using the polymer of Comparative Preparation Example 1 in place of the polymer of Preparation Example 1 in Example 1 was the same.
(비교실시예 2)Comparative Example 2
상기 실시예 1에서 제조예 1의 중합체 대신에 비교제조예 2의 중합체를 사용한 것을 제외하고는 동일하게 실시하였다.Except for using the polymer of Comparative Preparation Example 2 in place of the polymer of Preparation Example 1 in Example 1 was carried out in the same manner.
보습 및 피부 장벽기능 개선효과Moisturizing and skin barrier function improvement effect
25℃, 상대습도 45%, 공기의 흐름이 없는 실내에서, 건강한 여성 30명을 3개 그룹(A,B,C)으로 나눈 후, A그룹을 대상으로는 실시예 1의 화장료를, B그룹을 대상으로는 비교실시예 1의 화장료를, C그룹을 대상으로는 비교실시예 2의 화장료를, 적당량을 팔의 상박에 하루에 3회 6주간 도포한 후, TEWAMETER TM300(C+K electronic GmbH. Germany)를 이용하여 경피수분손실량 즉, TEWL(Transepidermal Water Loss)값을 시간 변화에 따른 TEWL 값 변화량 TEWL로 측정하고, CORNEOMETER CM 820 PC(C+K electronic GmbH. Germany)를 이용하여 표피 수분량에 따른 전기전도도의 변화로 0에서 150까지 피부의 수분량을 수치화하여 보습효과를 측정하였으며, 그 결과를 표 2에 나타내었다. After dividing 30 healthy women into three groups (A, B, C) at 25 ° C., 45% relative humidity and no air flow, the cosmetics of Example 1 were applied to group A for group B. After applying the cosmetic of Comparative Example 1, Comparative Example 2, the appropriate amount was applied to the upper arm of the arm three times a day for 6 weeks, the TEWAMETER TM300 (C + K electronic GmbH Transdermal moisture loss (TEWL), ie TEWL (TEWL) value change TEWL over time, and CORNEOMETER CM 820 PC (C + K electronic GmbH. Germany). The moisturizing effect was measured by quantifying the moisture content of the skin from 0 to 150 according to the change in electrical conductivity. The results are shown in Table 2.
표 2
TABLE 2
| 구분 | ΔTEWL | Corneometer Value |
| 실시예 1 | - 2.5(-20%) | 65 |
| 비교실시예 1 | 5.4(43.2%) | 28 |
| 비교실시예 2 | 1.3(10.4%) | 36 |
| division | ΔTEWL | Corneometer value |
| Example 1 | 2.5 (-20%) | 65 |
| Comparative Example 1 | 5.4 (43.2%) | 28 |
| Comparative Example 2 | 1.3 (10.4%) | 36 |
상기 표 2의 결과로부터 알 수 있듯이 본 발명의 구조를 가지는 중합체를 포함하는 화장표(실시예 1)는 비교실시예들에 비해 경피수분 손실량이 매우 개선되어 중합체가 보습효과를 나타냄을 알 수 있었다. 또한, 피부의 수분량을 측정한 Corneometer value 에서도 실시예가 높은 증가를 보임을 알 수 있었다. 즉, 본 발명의 중합체를 포함하는 화장표가 피부 수분량이 높게 측정되었으며 또한 피부 경피수분 손실량이 개선되어 본 발명의 중합체를 포함하는 화장료의 보습 및 피부 장벽 기능 개선 효과가 매우 효과적임을 알 수 있다.As can be seen from the results of Table 2, the cosmetic table containing the polymer having the structure of the present invention (Example 1) was found to have a significantly improved transdermal moisture loss compared to the comparative examples, the polymer exhibits a moisturizing effect. . In addition, the corneometer value measured the moisture content of the skin was found that the Example shows a high increase. That is, the cosmetic table containing the polymer of the present invention was measured to have a high skin moisture content, and the skin transdermal moisture loss was improved, and it can be seen that the effect of improving the moisturizing and skin barrier function of the cosmetic containing the polymer of the present invention is very effective.
염증완화 효과Anti-inflammatory effect
여성 30명을 먼저 시험 대상 화장료 적용 부위에 SDS 5% 용액을 4시간 동안 폐쇄첩포한 다음, 3그룹으로 나누어 A그룹에는 실시예 1의 화장료를, B그룹에는 비교실시예 1의 화장료를, C그룹에는 비교실시예 2의 화장료를 상기 표 1에 따라 제형하여 팔의 상박 왼쪽 2 X 2 ㎠의 면적에(2회/일, 0.2g/회) 2주간 도포하고, 피부홍반 측정기(Mexameter MX18, C+K Electronics GmbH Germany)로 피부 홍반 정도를 측정함으로써 SDS도포로 유발된 자극으로 인한 염증 완화 정도를 관찰하였다.Thirty women were first closed with an SDS 5% solution for 4 hours at the cosmetic application site, and then divided into three groups, the cosmetic of Example 1 in Group A, and the cosmetic of Comparative Example 1 in Group B, and In the group, the cosmetic composition of Comparative Example 2 was formulated according to Table 1, and applied to the area of the upper left arm of the arm at 2 X 2 cm 2 (2 times / day, 0.2 g / time) for 2 weeks, and a skin erythema meter (Mexameter MX18, C + K Electronics GmbH Germany) measured the degree of skin erythema and observed the degree of inflammation relief due to the SDS-induced irritation.
표 3
TABLE 3
| 실시예 1 | 홍반도 | 비교실시예 1 | 홍반도 | 비교실시예 2 | 홍반도 |
| 피검자 1 | 191 | 피검자 11 | 241 | 피검자 21 | 322 |
| 피검자 2 | 200 | 피검자 12 | 265 | 피검자 22 | 326 |
| 피검자 3 | 220 | 피검자 13 | 249 | 피검자 23 | 298 |
| 피검자 4 | 185 | 피검자 14 | 220 | 피검자 24 | 272 |
| 피검자 5 | 165 | 피검자 15 | 221 | 피검자 25 | 333 |
| 피검자 6 | 135 | 피검자 16 | 227 | 피검자 26 | 397 |
| 피검자 7 | 185 | 피검자 17 | 245 | 피검자 27 | 365 |
| 피검자 8 | 220 | 피검자 18 | 232 | 피검자 28 | 341 |
| 피검자 9 | 218 | 피검자 19 | 231 | 피검자 29 | 351 |
| 피검자 10 | 130 | 피검자 20 | 267 | 피검자 30 | 241 |
| 평균 | 185 | 평균 | 240 | 평균 | 325 |
| Example 1 | Red peninsula | Comparative Example 1 | Red peninsula | Comparative Example 2 | Red peninsula |
| Subject 1 | 191 | Subject 11 | 241 | Subject 21 | 322 |
| Subject 2 | 200 | Subject 12 | 265 | Subject 22 | 326 |
| Subject 3 | 220 | Subject 13 | 249 | Subject 23 | 298 |
| Subject 4 | 185 | Subject 14 | 220 | Subject 24 | 272 |
| Subject 5 | 165 | Subject 15 | 221 | Subject 25 | 333 |
| Subject 6 | 135 | Subject 16 | 227 | Subject 26 | 397 |
| Subject 7 | 185 | Subject 17 | 245 | Subject 27 | 365 |
| Subject 8 | 220 | Subject 18 | 232 | Subject 28 | 341 |
| Subject 9 | 218 | Subject 19 | 231 | Subject 29 | 351 |
| Subject 10 | 130 | Subject 20 | 267 | Subject 30 | 241 |
| Average | 185 | Average | 240 | Average | 325 |
상기 표 3에서 알 수 있는 바와 같이, 본 발명의 중합체를 포함하는 화장료(실시예 1)는 본 발명의 중합체를 전혀 포함하지 않는 화장료와 종래의 위치하젤 추출물을 함유하는 화장료에 비해서 염증완화 효과가 뛰어남을 알 수 있었다.As can be seen in Table 3, the cosmetic composition containing the polymer of the present invention (Example 1) has an anti-inflammatory effect compared to cosmetics containing no polymer of the present invention and a conventional witch hazel extract It was excellent.
본 발명에 따른 중합체는 증점, 흡수성, 또는 분산성에서 매우 우수한 특성을 가지면서, 동시에 향상된 보습력, 피부 장벽 기능 개선 및 우수한 생체 적합성에서 우수한 효과를 나타내어 다양한 스킨케어 및 헤어케어의 용도로 사용될 수 있어 산업적으로 유용하다.The polymer according to the present invention has very good properties in thickening, absorbency, or dispersibility, and at the same time shows excellent effects in improved moisturizing power, skin barrier function and excellent biocompatibility, so that it can be used for various skin care and hair care applications. Industrially useful
Claims (9)
- 하기의 화학식 (1)로 표시되는포스포릴콜린계 단량체를 포함하여 중합된 포스포릴콜린계중합체를 준비하는 단계; 및 Preparing a polymerized phosphorylcholine-based polymer including a phosphorylcholine-based monomer represented by Formula (1) below; And상기 포스포릴콜린계 중합체, α,β-에틸렌계 불포화 단량체, 개시제가 포함된 반응액을 준비하여 포스포릴콜린계 중합체 존재하에 α,β-에틸렌계 불포화 단량체를 중합하는 단계;를 포함하여 이루어진, 포스포릴콜린을 함유하는 중합체의 제조방법.And preparing a reaction solution including the phosphorylcholine polymer, α, β-ethylenically unsaturated monomer and an initiator to polymerize α, β-ethylenically unsaturated monomer in the presence of a phosphorylcholine polymer. Process for producing a polymer containing phosphoryl choline.[화학식 (1)][Formula (1)](화학식 (1)에서 Z는 수소원자 또는 R5-O-CO-(여기서, R5는 수소원자, 탄소수 1~10의 알킬기 또는 탄소수 1~10의 히드록시알킬기를 나타낸다)를 나타내고, Y는 탄소수 1~20의 알킬렌옥시기를 나타낸다. 또한, R1은 수소원자 또는 탄소수 1~5의 탄화수소기를 나타내고, R2, R3 및 R4는 동일 또는 다른 기로서, 수소원자, 탄소수 1~6의 탄화수소기 또는 히드록시 탄화수소기를 나타낸다. 또한, m은 1~20의 정수이고, n은 2~5의 정수이다.)(In formula (1), Z represents a hydrogen atom or R 5 -O-CO-, where R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms), and Y represents An alkyleneoxy group having 1 to 20 carbon atoms, R 1 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms, and R 2 , R 3 and R 4 are the same or different groups and represent a hydrogen atom or a 1 to 6 carbon atom; Represents a hydrocarbon group or a hydroxy hydrocarbon group, m is an integer from 1 to 20, and n is an integer from 2 to 5.
- 제1항에 있어서, The method of claim 1,상기 반응액에는 2개 이상의 불포화 에틸렌 결합기를 가진 가교제를 더 포함하는 것을 특징으로 하는, 포스포릴콜린을 함유하는 중합체의 제조방법.The reaction solution further comprises a crosslinking agent having two or more unsaturated ethylene bond groups, a method for producing a polymer containing phosphoryl choline.
- 제1항에 있어서,The method of claim 1,상기 포스포릴콜린계 단량체는 2-((메타)아크릴로일옥시)에틸-2'-(트리메틸암모니오)에틸포스페이트, 3-((메타)아크릴로일옥시)프로필-2'-(트리메틸암모니오)에틸포스페이트, 4-((메타)아크릴로일옥시)부틸-2'-(트리메틸암모니오)에틸포스페이트, 5-((메타)아크릴로일옥시)펜틸-2'-(트리메틸암모니오)에틸포스페이트, 6((메타)아크릴로일옥시)헥실-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)에틸-2'-(트리에틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)에틸-2'-(트리프로필암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)에틸-2'(트리부틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)프로필-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)부틸-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)펜틸-2'-(트리메틸암모니오)에틸포스페이트, 2-((메타)아크릴로일옥시)헥실-2'-(트리메틸암모니오)에틸포스페이트, 에틸(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 부틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 히드록시에틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 에틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 부틸(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트, 히드록시에틸-(2'-트리메틸암모니오 에틸포스포릴에틸)프말레이트에서 선택되는 1종 이상인 것을 특징으로 하는, 포스포릴콜린을 함유하는 중합체의 제조방법.The phosphorylcholine monomers include 2-((meth) acryloyloxy) ethyl-2 '-(trimethylammonio) ethyl phosphate, 3-((meth) acryloyloxy) propyl-2'-(trimethylammonium) 5) ethylphosphate, 4-((meth) acryloyloxy) butyl-2 '-(trimethylammonio) ethylphosphate, 5-((meth) acryloyloxy) pentyl-2'-(trimethylammonio) Ethyl phosphate, 6 ((meth) acryloyloxy) hexyl-2 '-(trimethylammonio) ethyl phosphate, 2-((meth) acryloyloxy) ethyl-2'-(triethylammonio) ethylphosphate 2-((meth) acryloyloxy) ethyl-2 '-(tripropylammonio) ethyl phosphate, 2-((meth) acryloyloxy) ethyl-2' (tributylammonio) ethyl phosphate, 2-((meth) acryloyloxy) propyl-2 '-(trimethylammonio) ethyl phosphate, 2-((meth) acryloyloxy) butyl-2'-(trimethylammonio) ethyl phosphate, 2- ((Meth) acryloyl jade ) Pentyl-2 '-(trimethylammonio) ethyl phosphate, 2-((meth) acryloyloxy) hexyl-2'-(trimethylammonio) ethyl phosphate, ethyl (2'-trimethylammonio ethylphosphorylethyl ) Fmaleate, Butyl- (2'-trimethylammonioethylphosphorylethyl) phmaleate, hydroxyethyl- (2'-trimethylammonio ethylphosphorylethyl) fmaleate, ethyl- (2'-trimethylammonio ethyl Phosphorylethyl) fmaleate, butyl (2'-trimethylammonio ethylphosphorylethyl) fmaleate, hydroxyethyl- (2'-trimethylammonio ethylphosphorylethyl) fmaleate Method of producing a polymer containing phosphoryl choline.
- 제1항에 있어서,The method of claim 1,상기α, β-에틸렌계 불포화 단량체가 하기 화학식 (2)로 표시되는 것을 특징으로 하는, 포스포릴콜린을 함유하는 중합체의 제조방법.A method for producing a polymer containing phosphorylcholine, wherein the α, β-ethylenically unsaturated monomer is represented by the following general formula (2).[화학식 (2)][Formula (2)](상기 구조식에서 L은 수소원자 또는 R8-O-CO-이고, 상기 R8은수소원자, 탄소수 1~10의 알킬기 또는 탄소수 1~10의 히드록시알킬기를 나타내고, X는,,또는에서 선택되는 어느 하나이며, r은 1~10의 정수이다. 또한, R6은 수소원자, 탄소수 1~5의 알킬기, 할로겐원자, 히드록시기, 또는 시아노기를 나타내고, R7은 수소원자 또는 탄소수 1~30의 탄화수소기를 나타낸다.)(In the above structural formula and L is a hydrogen atom or R 8 -O-CO-, wherein R 8 hermit wish Here, represents a hydroxyalkyl group having 1 to 10 carbon atoms or an alkyl group having 1 to 10, X is,,orIs any one selected from, and r is an integer of 1 to 10. R 6 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a hydroxyl group, or a cyano group, and R 7 represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.)
- 제2항에 있어서, The method of claim 2,상기 가교제는 에틸렌 글리콜 디아크릴레이트, 에틸렌 글리콜 디메타크릴레이트, 프로필렌 글리콜 디아크릴레이트, 프로필렌 글리콜 디메타크릴레이트, 부틸렌 글리콜 디아크릴레이트, 부틸렌 글리콜 디메타크릴레이트, 헥실렌 글리콜 디아크릴레이트, 헥실렌 클리콜 디메타크릴레이트, 디에틸렌 글리콜 디아크릴레이트, 디에틸렌 글리콜 디메타크릴레이트, 트리에틸렌 글리콜 디아크릴레이트, 트리에틸렌 글리콜 디메타크릴레이트, 테트라에틸렌 글리콜 디아크릴레이트, 테트라에틸렌 글리콜 디메타크릴레이트, 알릴 아크릴레이트, 알릴 메타크릴레이트, 메타알릴 아크릴레이트, 알릴 에타크릴레이트(allyl ethacrylate), 에타알릴 아크릴레이트, 메타알릴 메타크릴레이트, 디알릴 프탈레이트, 디알릴 말레이트, 디알릴 석시네이트, 트리아릴 포스페이트, 디알릴 옥살레이트, 디알릴말로네이트, 디알릴 시트레이트, 디알릴 푸마레이트, 디비닐 벤젠, 트리비닐 벤젠, 비닐 크로토네이트, N,N-메틸렌-비스-아크릴아마이드, 트리메틸올프로판 디알릴 에테르 또는 트리메틸올프로판 트리알릴 에테르, 디알릴 펜타에리쓰리톨 에테르, 트리알릴 펜타에리쓰리톨 에테르, 테트라알릴 펜타에리쓰리톨 에테르, 디알릴 수크로오스 에테르, 트리알릴 수크로오스 에테르, 테트라알릴 수크로오스 에테르, 펜타알릴 수크로오스 에테르, 및 헥사알릴 수크로오스 에테르로 이루어진 군으로부터 선택되는 하나 또는 둘 이상을 포함하는 것을 특징으로 하는, 포스포릴콜린을 함유하는 중합체의 제조방법.The crosslinking agent is ethylene glycol diacrylate, ethylene glycol dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, butylene glycol diacrylate, butylene glycol dimethacrylate, hexylene glycol diacrylate , Hexylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol Dimethacrylate, allyl acrylate, allyl methacrylate, methallyl acrylate, allyl ethacrylate, etaallyl acrylate, methallyl methacrylate, diallyl phthalate, diallyl malate, diallyl Succinate, triaryl phosphate, Diallyl oxalate, diallyl malonate, diallyl citrate, diallyl fumarate, divinyl benzene, trivinyl benzene, vinyl crotonate, N, N-methylene-bis-acrylamide, trimethylolpropane diallyl ether Or trimethylolpropane triallyl ether, diallyl pentaerythritol ether, triallyl pentaerythritol ether, tetraallyl pentaerythritol ether, diallyl sucrose ether, triallyl sucrose ether, tetraallyl sucrose ether, pentaallyl sucrose A method for producing a polymer containing phosphorylcholine, characterized in that it comprises one or two or more selected from the group consisting of ether, and hexaallyl sucrose ether.
- 제1항 내지 제5항 중 어느 한 항의 제조방법으로 제조된, 포스포릴콜린을 함유하는 중합체.A polymer containing phosphorylcholine prepared by the process according to any one of claims 1 to 5.
- 제6항의 중합체를 유효 성분으로 포함하는 화장료 조성물.A cosmetic composition comprising the polymer of claim 6 as an active ingredient.
- 제7항에 있어서,The method of claim 7, wherein상기 조성물은 피부보습용, 피부 장벽 기능 개선용, 아토피 개선용 또는 염증 완화용인 화장료 조성물.The composition is for moisturizing the skin, improving skin barrier function, improving atopy or reducing the cosmetic composition for inflammation.
- 제7항에 있어서,The method of claim 7, wherein상기 조성물은 발림성 및 모발 컨시셔닝 효과를 부여하는 헤어케어용인 것을 특징으로 하는 화장료 조성물.The composition is a cosmetic composition, characterized in that for hair care to give the application and hair conditioning effect.
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| CN116284548A (en) * | 2023-05-24 | 2023-06-23 | 广东工业大学 | A kind of phosphorylcholine tetrapolymer with multiple self-inversion and its preparation method and application |
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| JPH06157270A (en) * | 1992-11-17 | 1994-06-03 | Pola Chem Ind Inc | Cosmetic |
| JP3532692B2 (en) * | 1995-04-03 | 2004-05-31 | 日本油脂株式会社 | Phosphorylcholine group-containing polymer aqueous solution and production method |
| JP2005325057A (en) * | 2004-05-14 | 2005-11-24 | Doctor Program Kk | Makeup cosmetic |
| JP2010043018A (en) * | 2008-08-12 | 2010-02-25 | Sunstar Inc | Skin care composition |
| KR20130118487A (en) * | 2012-04-20 | 2013-10-30 | 주식회사 케이씨아이 | Crosslinked copolymers based on monomers containing phosphorylcholine-like groups, and their cosmetic formulations |
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| JPH06157270A (en) * | 1992-11-17 | 1994-06-03 | Pola Chem Ind Inc | Cosmetic |
| JP3532692B2 (en) * | 1995-04-03 | 2004-05-31 | 日本油脂株式会社 | Phosphorylcholine group-containing polymer aqueous solution and production method |
| JP2005325057A (en) * | 2004-05-14 | 2005-11-24 | Doctor Program Kk | Makeup cosmetic |
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| CN116284548A (en) * | 2023-05-24 | 2023-06-23 | 广东工业大学 | A kind of phosphorylcholine tetrapolymer with multiple self-inversion and its preparation method and application |
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