JP2022502530A - サンケア製剤 - Google Patents
サンケア製剤 Download PDFInfo
- Publication number
- JP2022502530A JP2022502530A JP2021513980A JP2021513980A JP2022502530A JP 2022502530 A JP2022502530 A JP 2022502530A JP 2021513980 A JP2021513980 A JP 2021513980A JP 2021513980 A JP2021513980 A JP 2021513980A JP 2022502530 A JP2022502530 A JP 2022502530A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- group
- meth
- acrylate
- monomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000178 monomer Substances 0.000 claims abstract description 101
- 239000000203 mixture Substances 0.000 claims abstract description 78
- 229920006163 vinyl copolymer Polymers 0.000 claims abstract description 63
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 54
- 238000009472 formulation Methods 0.000 claims abstract description 44
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 38
- 229920002959 polymer blend Polymers 0.000 claims abstract description 36
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 36
- 239000013543 active substance Substances 0.000 claims abstract description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 20
- 239000000412 dendrimer Substances 0.000 claims abstract description 16
- 229920000736 dendritic polymer Polymers 0.000 claims abstract description 16
- -1 hydroxypropyl Chemical group 0.000 claims description 51
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000005353 silylalkyl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 10
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical class CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 9
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 9
- 239000006100 radiation absorber Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 239000006096 absorbing agent Substances 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 6
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 claims description 4
- 229920001567 vinyl ester resin Polymers 0.000 claims description 4
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- KBKGPMDADJLBEM-UHFFFAOYSA-N 1-(4-pentylphenyl)ethanone Chemical compound CCCCCC1=CC=C(C(C)=O)C=C1 KBKGPMDADJLBEM-UHFFFAOYSA-N 0.000 claims description 2
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims description 2
- VHWSRELATOUTAG-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OCC(O)CO VHWSRELATOUTAG-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- HMKKFLSUPRUBOO-IUPFWZBJSA-N 3,4-dihydroxy-5-[3,4,5-tris[[(z)-octadec-9-enoyl]oxy]benzoyl]oxybenzoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC1=C(OC(=O)CCCCCCC\C=C/CCCCCCCC)C(OC(=O)CCCCCCC\C=C/CCCCCCCC)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(O)=O)O)=C1 HMKKFLSUPRUBOO-IUPFWZBJSA-N 0.000 claims description 2
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 241000723346 Cinnamomum camphora Species 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- 229940091181 aconitic acid Drugs 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001556 benzimidazoles Chemical class 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 229960000846 camphor Drugs 0.000 claims description 2
- 229930008380 camphor Natural products 0.000 claims description 2
- 229940114081 cinnamate Drugs 0.000 claims description 2
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 2
- 229940018557 citraconic acid Drugs 0.000 claims description 2
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 229940120503 dihydroxyacetone Drugs 0.000 claims description 2
- 229960004960 dioxybenzone Drugs 0.000 claims description 2
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- UONUEPNDJQOXAG-UHFFFAOYSA-N ethyl 4-[bis(3-hydroxypropyl)amino]benzoate Chemical compound CCOC(=O)C1=CC=C(N(CCCO)CCCO)C=C1 UONUEPNDJQOXAG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims description 2
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims description 2
- 229940005650 monomethyl fumarate Drugs 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 2
- 229960001860 salicylate Drugs 0.000 claims description 2
- 150000003512 tertiary amines Chemical group 0.000 claims description 2
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- 229940099259 vaseline Drugs 0.000 claims description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims 1
- GTAUOHWUYZSOIB-UHFFFAOYSA-N 4-(dimethylamino)-2-pentylbenzoic acid Chemical compound CCCCCC1=CC(N(C)C)=CC=C1C(O)=O GTAUOHWUYZSOIB-UHFFFAOYSA-N 0.000 claims 1
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 claims 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 1
- 230000002745 absorbent Effects 0.000 claims 1
- 239000002250 absorbent Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000005399 allylmethacrylate group Chemical group 0.000 claims 1
- UBNYRXMKIIGMKK-UHFFFAOYSA-N amiloxate Chemical compound COC1=CC=C(C=CC(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-UHFFFAOYSA-N 0.000 claims 1
- 239000002981 blocking agent Substances 0.000 claims 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 abstract description 6
- 238000010586 diagram Methods 0.000 abstract 1
- 238000000338 in vitro Methods 0.000 description 12
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 230000000475 sunscreen effect Effects 0.000 description 7
- 239000000516 sunscreening agent Substances 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
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- NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 206010015150 Erythema Diseases 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 description 4
- 239000003623 enhancer Substances 0.000 description 4
- 230000009931 harmful effect Effects 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 3
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 3
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- 235000010445 lecithin Nutrition 0.000 description 1
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- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- ULYOZOPEFCQZHH-UHFFFAOYSA-N n-(methoxymethyl)prop-2-enamide Chemical compound COCNC(=O)C=C ULYOZOPEFCQZHH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 229960001173 oxybenzone Drugs 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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Abstract
Description
オーバーヘッド撹拌機、熱電対、凝縮装置、ならびにモノマーおよび開始剤を添加するための入口を備えた1リットルの丸底フラスコに、脱イオン水(150.0g)、ドデシル硫酸ナトリウム界面活性剤(3.3gの23%DS−4)、および炭酸ナトリウム(1.1g)を入れた。次に、フラスコの内容物を撹拌し、85℃で加熱した。脱イオン水(81.1g)およびドデシル硫酸ナトリウム界面活性剤(3.1gの23%DS−4)を容器に入れ、攪拌することにより、モノマーエマルジョンを調製した。界面活性剤を水に取り込んだ後、ブチルアクリレート(BA)(50g)、エチルヘキシルアクリレート(EHA)(100g)、メチルメタクリレート(MMA)(96.3g)、メタクリル酸(MAA)(3.8g)、およびアリルメタクリレート(ALMA)(0.2g)を容器内の攪拌混合物にゆっくりと添加した。過硫酸ナトリウム(0.25g)および脱イオン水(22g)を別の容器に入れることにより、共供給触媒溶液も調製した。フラスコの内容物が85℃の温度に達したとき、上で調製した10gのモノマーエマルジョンをフラスコに入れ、続いて脱イオン水リンス(10g)水リンス、続いて過硫酸ナトリウムの開始剤溶液(0.9g)を脱イオン水(5.7g)に入れた。最初の重合後および85℃で、上で調製したモノマーエマルジョンのフラスコへのモノマーエマルジョン共供給を開始し、1.97g/分の速度で15分間、次に3.93g/分の速度でさらに75分間行った。同時に、モノマーエマルジョン共供給を用いて、触媒共供給を開始し、0.24g/分の速度で92分間行った。共供給の完了時に、フラスコの内容物を追跡して、残留モノマーの量を低減し、生成物の単段ポリマーを得た。
オーバーヘッド撹拌機、熱電対、凝縮装置、ならびにモノマーおよび開始剤を添加するための入口を備えたフラスコに、以下の構造を有するカルボシロキサンデンドリマー(150部)を入れた。
サンスケア製剤を、表1に記載されている製剤実施例G1およびG2に従うジェネリック製剤を有するように調製した。カルボマーおよびいくらかの脱イオン水をフラスコに添加し、カルボマーが水和するまで混合した後に、残りの第I相成分を添加した。次に、フラスコの内容物を混合しながら75℃で加熱した。第II相の成分を75℃で加熱しながら別個の容器で組み合わせて、溶解するまで混合した。次に、第II相の成分をフラスコの内容物に添加し、均一になるまで混合した。次に、第III相の成分をフラスコの内容物に添加し、均一になるまで混合した。次に、フラスコの内容物を加熱源から取り出し、冷却した。フラスコの内容物が60℃未満に冷却されたら、第IV相の成分をフラスコの内容物に添加し、均一になるまで混合した。フラスコの内容物が40℃未満に冷却されたら、第V相の成分をフラスコの内容物に添加し、フラスコの内容物が周囲の室温に達するまで混合し続けた。次に、フラスコの内容物を、必要に応じて、5.5〜7.5のpHにpH調整した。
(a)比較例C1〜C2および実施例1〜3、ならびに(b)比較例C3〜C4および実施例4〜6のサンケア製剤を、製剤実施例G1およびG2に従って、表2に記載されるように様々な試験ポリマーを用いて調製した。
比較例C1〜C4および実施例1〜6に従って調製したサンケア製剤を各々、インビトロSPF測定の前に1週間沈降させた。次に、サンケア製剤の各々のインビトロSPF性能を、以下のプロトコルに従ってインビトロ技術を使用して3回試験した。
次に、比較例C1〜C4および実施例1〜6に従って調製した適用されたサンケア製剤を用いた、上で考察した元のインビトロSPF測定からの試験基材を各々、300rpmの速度でプロペラ攪拌させながら、制御された温度の水浴(30℃)に1時間浸漬した。次に、基材を水浴から取り出し、周囲の実験室条件下で20〜30分間乾燥させた後、各サンケア製剤のインビトロSPFを測定し、元のインビトロSPF測定と比較し、1時間のSPF保持を表4に報告されているように計算した。次に、基材を各々、記載された条件下でさらに1時間、制御された温度の水浴に浸漬した。次に、基材を水浴から取り出し、周囲の実験室条件下で20〜30分間乾燥させた後、各サンケア製剤のインビトロSPFを測定し、元のインビトロSPF測定と比較し、2時間のSPF保持を表4に報告されているように計算した。
Claims (10)
- ポリマーブレンドであって、
単段ポリマーと、
シリコーングラフト化ビニルコポリマーと、を含み、
前記単段ポリマーが、
90〜99.8重量%のモノエチレン性不飽和非イオン性モノマーの構造単位と、
0.19〜10重量%のモノエチレン性不飽和カルボン酸モノマーの構造単位と、
0.01〜2重量%の分子あたり少なくとも2つのエチレン性不飽和基を有する多エチレン性不飽和モノマーの構造単位と、を含み、
前記シリコーングラフト化ビニルコポリマーが、
前記シリコーングラフト化ビニルコポリマーの重量に基づいて、25〜95重量%のビニルモノマーの構造単位と、
前記シリコーングラフト化ビニルコポリマーの重量に基づいて、5〜75重量%の式(I)のカルボシロキサンデンドリマーの構造単位と、を含み、
式中、R2がC2−10アルキレン基であり、各R3が独立してC1−10アルキル基であり、各Zが独立して水素、C1−10アルキル基、アリール基、および式(II)のシリルアルキル基からなる群から選択され、aが0〜3であり、Yが式(III)、(IV)、および(V)からなる群から選択され、
式中、各R4およびR6が独立して水素またはメチル基であり、各R5およびR8が独立してC1−10アルキレン基であり、各R7が独立してC1−10アルキル基であり、bが0〜4であり、cが0または1である、ポリマーブレンド。 - サンケア製剤であって、
30〜92重量%の皮膚科学的に許容される担体と、
固形分に基づいて、0.1〜10重量%の請求項1に記載のポリマーブレンドと、
0.1〜70重量%のサンケア活性物質と、を含む、サンケア製剤。 - 前記皮膚科学的に許容される担体が、水を含む、請求項2に記載のサンケア製剤。
- 前記サンケア活性物質が、物理的遮断剤および化学吸収剤からなる群から選択されるUV放射吸収剤である、請求項3に記載のサンケア製剤。
- 前記サンケア活性物質が、赤色ワセリン、二酸化チタン、酸化亜鉛、1−(4−メトキシフェノール)−3−(4−tert−ブチルフェニル)プロパン−1,3−ジオン、2−ヒドロキシ−4−メトキシベンゾフェノン、ジオキシベンゾン、スリソベンゾン、メンチルアントラニレート、パラ−アミノ安息香酸、アミルパラジメチルアミノ安息香酸、オクチルパラ−ジメチルアミノベンゾエート、エチル4−ビス(ヒドロキシプロピル)パラ−アミノアミノベンゾエート、ポリエチレングリコール(PEG−25)パラ−アミノベンゾエート、エチル4−ビス(ヒドロキシプロピル)アミノベンゾエート、ジエタノールアミンパラ−メチオキシシンナメート、2−エトキシエチルパラ−メトキシシンナメート、エチルヘキシルパラ−メトキシシンナメート、オクチルパラ−メトキシシンナメート、イソアミルパラ−メトキシシンナメート、2−エチルヘキシル−2−シアノ−3,3−ジフェニル−アクリレート、2−エチルヘキシル−2−シアノ−3,3−ジフェニル−2−プロペノエート、2−エチルヘキシル−2−ヒドロキシベンゾエート、ホモメンチルサリチレート、グリセリルアミノベンゾエート、トリエタノールアミンサリチレート、ジガロイルトリオレエート、ジヒドロキシアセトンを含むローソン、2−フェニルベンズイミダゾール−5−スルホン酸、4−メチルベンジリジンカンフル、アボベンゾン、トリアジン、ベンゾトリアゾール、ビニル基含有アミド、桂皮酸アミド、スルホン化ベンズイミダゾール)、3,3,5−トリメチルシクロヘキシル2−ヒドロキシベンゾエート、およびそれらの混合物からなる群から選択される、UV放射吸収剤である、請求項4に記載のサンケア製剤。
- 前記サンケア活性物質が、1−(4−メトキシフェノール)−3−(4−tert−ブチルフェニル)プロパン−1,3−ジオン、2−エチルヘキシル2−ヒドロキシベンゾエート、2−エチルヘキシル−2−シアノ−3,3−ジフェニル−2−プロペノエート、および2−ヒドロキシ−4−メトキシベンゾフェノンを含むUV吸収剤の混合物であるUV放射吸収剤である、請求項5に記載のサンケア製剤。
- 前記モノエチレン性不飽和非イオン性モノマーが、(i)C1−5アルキル(メタ)アクリレートと(ii)C6−22アルキル(メタ)アクリレートとの混合物からなる群から選択され、
前記モノエチレン性不飽和カルボン酸モノマーが、(メタ)アクリル酸、(メタ)アクリロキシプロピオン酸、イタコン酸、アコニット酸、マレイン酸、無水マレイン酸、フマル酸、クロトン酸、シトラコン酸、無水マレイン酸、マレイン酸モノメチル、フマル酸モノメチル、イタコン酸モノメチル、ならびに対応する無水物、アミド、およびエステルなどの他の誘導体からなる群から選択され、
前記分子あたり少なくとも2つのエチレン性不飽和基を有する多エチレン性不飽和モノマーが、ジビニル芳香族化合物、ジ−(メタ)アクリレートエステル、トリ−(メタ)アクリレートエステル、テトラ−(メタアクリレート)エステル、ジ−アリルエーテル、トリ−アリルエーテル、テトラ−アリルエーテル、ジ−アリルエステル、トリ−アリルエステル、テトラ−アリルエステル、アリル(メタ)アクリレート、およびそれらの混合物からなる群から選択され、
前記ビニルモノマーが、C1−3アルキル(メタ)アクリレート、C4−20アルキル(メタ)アクリレート、低級脂肪酸のビニルエステル、高級脂肪酸のビニルエステル、芳香族ビニルモノマー、アミノ官能性ビニルモノマー、アミド官能性ビニルモノマー、ヒドロキシル官能性ビニルモノマー、フッ素化ビニルモノマー、エポキシ官能性ビニルモノマー、エーテル結合含有ビニルモノマー、ラジカル重合性不飽和基を含有するアルコキシシラン、不飽和基官能化シリコーン化合物、ブタジエン、塩化ビニル、塩化ビニリデン、アクリロニトリル、メタクリロニトリル、フマル酸ジブチル、無水マレイン酸、無水ドデシルコハク酸、ラジカル重合性不飽和カルボン酸、スルホン酸残基を含有するラジカル重合性不飽和モノマー、(メタ)アクリル酸に由来する第四級アンモニウム塩、第三級アミン基を含有するアルコールのメタクリレートエステル、およびそれらの混合物からなる群から選択され、
前記カルボシロキサンデンドリマーが、式(I)のものであり、式中、各R1がメチル基であり、R2がC2アルキレン基であり、aが0であり、各Zがメチル基であり、Yが式(III)のものであり、式中、R4がメチル基であり、R5がC3アルキレン基である、請求項6に記載のサンケア製剤。 - 前記モノエチレン性不飽和非イオン性モノマーが、(i)35〜75重量%のC1−4アルキル(メタ)アクリレート(前記C1−4アルキル(メタ)アクリレートが、30〜40重量%のメチル(メタ)アクリレートと60〜70重量%のn−ブチル(メタ)アクリレートとの混合物である)と、(ii)25〜65重量%のC8−22アルキル(メタ)アクリレート(前記C8−22アルキル(メタ)アクリレートが、2−エチルヘキシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、およびそれらの混合物からなる群から選択される)との混合物からなる群から選択され、
前記モノエチレン性不飽和カルボン酸モノマーが、アクリル酸、メタクリル酸、イタコン酸、クロトン酸、およびそれらの混合物からなる群から選択され、
前記分子あたり少なくとも2つのエチレン性不飽和基を有する多エチレン性不飽和モノマーが、ジビニルベンゼン(DVB)、アリルメタクリレート(ALMA)、エチレングリコールジメタクリレート(EGDMA)、ヘキサン−1,6−ジオールジアクリレート(HDDA)、ブチレングリコールジメタクリレート(BGDMA)、およびそれらの混合物からなる群から選択される、請求項7に記載のサンケア製剤。 - 前記モノエチレン性不飽和非イオン性モノマーが、(i)58〜61重量%のC1−4アルキル(メタ)アクリレート(前記C1−4アルキル(メタ)アクリレートが、33〜35重量%のメチル(メタ)アクリレートと65〜67重量%のn−ブチル(メタ)アクリレートとの混合物である)と、(ii)39〜42重量%のC8−22アルキル(メタ)アクリレート(前記C8−22アルキル(メタ)アクリレートが、2−エチルヘキシルアクリレートである)との混合物からなる群から選択され、
前記モノエチレン性不飽和カルボン酸モノマーが、メタクリル酸であり、
前記分子あたり少なくとも2つのエチレン性不飽和基を有する多エチレン性不飽和モノマーが、アリルメタクリレート(ALMA)である、請求項8に記載のサンケア製剤。 - 前記ビニルモノマーがメチルメタクリレートおよびブチルアクリレートを含み、前記サンケア製剤が5.5〜7.5のpHを有する、請求項9に記載のサンケア製剤。
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