JP2015003934A - Uvフィルターカプセル - Google Patents
Uvフィルターカプセル Download PDFInfo
- Publication number
- JP2015003934A JP2015003934A JP2014208193A JP2014208193A JP2015003934A JP 2015003934 A JP2015003934 A JP 2015003934A JP 2014208193 A JP2014208193 A JP 2014208193A JP 2014208193 A JP2014208193 A JP 2014208193A JP 2015003934 A JP2015003934 A JP 2015003934A
- Authority
- JP
- Japan
- Prior art keywords
- filter
- soluble organic
- triazine
- phase
- polyethylene glycol
- 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
- 239000004904 UV filter Substances 0.000 title claims abstract description 116
- 239000002775 capsule Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 claims abstract description 171
- 238000002360 preparation method Methods 0.000 claims abstract description 43
- 239000006185 dispersion Substances 0.000 claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- -1 2H-benzotriazol-2-yl Chemical group 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000839 emulsion Substances 0.000 claims description 18
- 239000007983 Tris buffer Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 claims description 8
- 239000012703 sol-gel precursor Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 150000003918 triazines Chemical class 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000007764 o/w emulsion Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 5
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- ALBXRBNFWICCSC-UHFFFAOYSA-N 2-(5,5-dimethyl-1,1-diphenylhex-1-en-3-ylidene)propanedioic acid Chemical compound C=1C=CC=CC=1C(=CC(CC(C)(C)C)=C(C(O)=O)C(O)=O)C1=CC=CC=C1 ALBXRBNFWICCSC-UHFFFAOYSA-N 0.000 claims description 2
- HROUBOKCPRJCPY-UHFFFAOYSA-N 2-[1-(4-amino-2-propan-2-ylphenyl)-2-methylpropylidene]propanedioic acid Chemical compound CC(C)C1=C(C=CC(=C1)N)C(=C(C(=O)O)C(=O)O)C(C)C HROUBOKCPRJCPY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- TYRYZLMVZZMQDR-UHFFFAOYSA-N 2-[1,1-bis(2H-benzotriazol-4-yl)-2-methylidenebutyl]-3,4,5,6-tetramethylphenol Chemical class C=C(C(C1=C(C(=C(C(=C1C)C)C)C)O)(C1=CC=CC=2NN=NC=21)C1=CC=CC=2NN=NC=21)CC TYRYZLMVZZMQDR-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 abstract description 55
- 238000009472 formulation Methods 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 17
- 230000008569 process Effects 0.000 abstract description 4
- 239000003974 emollient agent Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 111
- 239000002202 Polyethylene glycol Substances 0.000 description 94
- 229920001223 polyethylene glycol Polymers 0.000 description 94
- 239000000049 pigment Substances 0.000 description 32
- 239000003921 oil Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
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- 239000000126 substance Substances 0.000 description 30
- 238000003756 stirring Methods 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- 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 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 22
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
- 239000004615 ingredient Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000001727 in vivo Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 238000005259 measurement Methods 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 15
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[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)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 14
- WQXNXVUDBPYKBA-YFKPBYRVSA-N ectoine Chemical compound CC1=[NH+][C@H](C([O-])=O)CCN1 WQXNXVUDBPYKBA-YFKPBYRVSA-N 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 13
- 230000005855 radiation Effects 0.000 description 13
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- HNXNKTMIVROLTK-UHFFFAOYSA-N n,n-dimethyldecanamide Chemical compound CCCCCCCCCC(=O)N(C)C HNXNKTMIVROLTK-UHFFFAOYSA-N 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 10
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 235000006708 antioxidants Nutrition 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229930003935 flavonoid Natural products 0.000 description 10
- 150000002215 flavonoids Chemical class 0.000 description 10
- 235000017173 flavonoids Nutrition 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 230000004224 protection Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
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- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 9
- LQXBZWFNAKZUNM-UHFFFAOYSA-N 16-methyl-1-(16-methylheptadecoxy)heptadecane Chemical compound CC(C)CCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC(C)C LQXBZWFNAKZUNM-UHFFFAOYSA-N 0.000 description 9
- KIIBBJKLKFTNQO-WHFBIAKZSA-N 5-hydroxyectoine Chemical compound CC1=N[C@H](C(O)=O)[C@@H](O)CN1 KIIBBJKLKFTNQO-WHFBIAKZSA-N 0.000 description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 229940049964 oleate Drugs 0.000 description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 9
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 8
- OUUCZGCOAXRCHN-UHFFFAOYSA-N 1-hexadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC OUUCZGCOAXRCHN-UHFFFAOYSA-N 0.000 description 8
- WQXNXVUDBPYKBA-UHFFFAOYSA-N Ectoine Natural products CC1=NCCC(C(O)=O)N1 WQXNXVUDBPYKBA-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 8
- 230000003711 photoprotective effect Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
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- 239000008367 deionised water Substances 0.000 description 7
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- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 7
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
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- 235000005875 quercetin Nutrition 0.000 description 6
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- RRFBTKHQZRCRSS-UHFFFAOYSA-N 1,3-bis(methoxymethyl)-5,5-diphenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(COC)C(=O)N(COC)C(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 RRFBTKHQZRCRSS-UHFFFAOYSA-N 0.000 description 5
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- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
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- 230000037394 skin elasticity Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
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- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229940033331 soy sterol Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
- 229940098760 steareth-2 Drugs 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
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- 239000011721 thiamine Substances 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
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- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
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- 238000002834 transmittance Methods 0.000 description 1
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- A—HUMAN NECESSITIES
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- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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Abstract
【解決手段】本発明は、ポリマーシェルならびにa)少なくとも1つの難溶解性有機UVフィルターおよびb)室温で40重量%を超える前記難溶解性有機UVフィルターを溶解することができる軟化剤を含むUVフィルターカプセルを提供する。
【選択図】なし
Description
ポリマーシェルならびに
a)少なくとも1つの難溶解性有機UVフィルターおよび
b)室温(20℃〜25℃)で40重量%を超える難溶解性有機UVフィルターを溶解することができる軟化剤
を含むUVフィルターカプセルに関する。
ステップa)において、水中油エマルジョンを、ポリマーシェルの生成のためのソル−ゲル前駆体、少なくとも1つの難溶解性UVフィルターおよび室温(20℃〜25℃)で40重量%を超える難溶解性有機UVフィルターを水溶液に溶解することができる軟化剤を含む混合物から調製し、
ステップb)において、ステップa)で調製されたエマルジョンを混合して、pH2〜4、好ましくは3〜4を有する水溶液を得、任意選択で
ステップc)において、反応生成物をソル−ゲル前駆体から分離する。
−カプセル壁(またはそれと同義にはポリマーシェル)の親水性は、UVフィルターの溶解度とは独立に調節することができる。したがって難溶解性有機UVフィルターは、純粋な水性製剤に組み込むことができる。これによって、難溶解性有機UVフィルターを、最終生成物としての化粧用または皮膚用組成物の油相および水相の両方に組み込むことが可能になる。したがって、化粧用製剤の全含量を増大することができる。
−難溶解性UVフィルターが有機相中に存在し、本発明に従ってカプセル化された難溶解性UVフィルターが水相中に存在する場合、いわゆる促進効果が観測される。特に、同じ難溶解性UVフィルターが、有機相中に存在し、水相中にカプセル形態で存在する場合、相乗効果、換言すれば促進効果が生じ、これは本発明に従ってカプセル化された難溶解性UVフィルターなしの製剤、およびそれを伴う製剤のインビボSPF値によって示され得る。
−文献には、有機UVフィルターの皮膚への浸透およびヒトの皮膚に直接適用した場合の刺激に関連する潜在可能性が繰返し議論されている。ここで提案する対応物質のカプセル化は、この作用を抑制する。
−一般に、個々のUVフィルターまたは他の成分のカプセル化は、結晶化プロセス、沈殿および凝集などの、個々の製剤の構成成分の互いの相互反応を抑制するので、それによって生じる製剤の問題を予防することができる。
−特定の軟化剤の特定の選択、特にN,N−ジメチルデカンアミド(Spectrasolv DMDA)の選択によって、前述の少なくとも1つの難溶解性有機UVフィルター、特にエチルヘキシルトリアゾンの溶解度を、カプセル化中に一定に維持することができ、UVフィルターを結晶化させず、したがってカプセルの高量化を促進することができる。さらに、記載の系は温度安定性であり、その結果、生成中に有り得る温度変化の際にも、安定なカプセルが形成される。
−組成物の水相中に使用できる本発明に従ってカプセル化された難溶解性UVフィルターは、安定な組成物を達成するために必須のpH制御がここでは必要とされないので、例えばフェニルベンズイミダゾールスルホン酸などの水相中の通常の水性UVフィルターを有利に代替することができる。
−光防御特性を有する組成物、特に化粧用または皮膚用組成物の調製方法は、本発明のカプセルをさらなる成分と混合することを特徴とする。
−光防御特性を有する組成物、特に化粧用または皮膚用組成物の調製方法は、本発明のカプセルを含む事前分散液を、さらなる成分と混合することを特徴とする。
−水中油エマルジョンの形態の組成物、特に化粧用または皮膚用組成物の特定の調製方法は、前述の事前分散液を、油で乳化することを特徴とする。
−鉱油、ミネラルワックス、
−油、例えばカプリン酸またはカプリル酸のトリグリセリド、さらには天然油、例えばヒマシ油など、
−脂肪、ワックス、ならびに他の天然および合成脂肪性物質、好ましくは脂肪酸と低炭素数を有するアルコール、例えばイソプロパノール、プロピレングリコール、もしくはグリセロールとのエステル、または脂肪アルコールと低炭素数を有するアルカン酸もしくは脂肪酸とのエステル、
−シリコーン油、例えばジメチルポリシロキサン、ジエチルシロキサン、ジフェニルポリシロキサン、およびそれらの混合形態。
サン)を使用することも有利である。
ベンジリデンカンファー誘導体、例えば3−(4'−メチルベンジリデン)dl−カンファー(例えばEusolex(登録商標)6300)、3−ベンジリデンカンファー(例えばMexoryl(登録商標)SD)、N−{(2および4)−[(2−オキソボルン−3−イリデン)メチル]−ベンジル}アクリルアミドのポリマー(例えばMexoryl(登録商標)SW)、N,N,N−トリメチル−4−(2−オキソボルン−3−イリデンメチル)アニリニウムメチルサルフェート(例えばMexoryl(登録商標)SK)、または(2−オキソボルン−3−イリデン)トルエン−4−スルホン酸(例えばMexoryl(登録商標)SL)、
ベンゾイル−またはジベンゾイルメタン類、例えば1−(4−tert−ブチルフェニル)−3−(4−メトキシフェニル)プロパン−1,3−ジオン(例えばEusolex(登録商標)9020)、または4−イソプロピルジベンゾイルメタン(例えばEusolex(登録商標)8020)、
ベンゾフェノン類、例えば2−ヒドロキシ−4−メトキシベンゾフェノン(例えばEusolex(登録商標)4360)または2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸およびそのナトリウム塩(例えばUvinul(登録商標)MS−40)
、メトキシ桂皮酸エステル、例えばメトキシ桂皮酸オクチル(例えばEusolex(登録商標)2292)または例えば各異性体の混合物としての4−メトキシ桂皮酸イソペンチル(例えばNeo Heliopan(登録商標)E1000)、
サリチル酸誘導体、例えばサリチル酸2−エチルヘキシル(例えばEusolex(登録商標)OS)、サリチル酸4−イソプロピルベンジル(例えばMegasol(登録商標))、またはサリチル酸3,3,5−トリメチルシクロヘキシル(例えばEusolex(登録商標)HMS)、
4−アミノ安息香酸およびその誘導体、例えば4−アミノ安息香酸、4−(ジメチルアミノ)安息香酸2−エチルヘキシル(例えばEusolex(登録商標)6007)、またはエトキシル化4−アミノ安息香酸エチル(例えばUvinul(登録商標)P25)、フェニルベンズイミダゾールスルホン酸、例えば2−フェニルベンズイミダゾール−5−スルホン酸およびそのカリウム、ナトリウム、およびトリエタノールアミン塩(例えばEusolex(登録商標)232)、2,2−(1,4−フェニレン)ビスベンズイミダゾール−4,6−ジスルホン酸もしくはその塩(例えばNeoheliopan(登録商標)AP)、または2,2−(1,4−フェニレン)ビスベンズイミダゾール−6−スルホン酸、
ならびにさらなる物質、例えば
−2−シアノ−3,3−ジフェニルアクリル酸2−エチルヘキシル(例えばEusolex(登録商標)OCR)、
−3,3'−(1,4−フェニレンジメチレン)ビス(7,7−ジメチル−2−オキソビシクロ[2.2.1]へプト−1−イルメタンスルホン酸およびその塩(例えばMexoryl(登録商標)SX)、ならびに
−2,4,6−トリアニリノ−(p−カルボ−2'−エチルヘキシル−1'−オキシ)−1,3,5−トリアジン(例えばUvinul(登録商標)T150)、
−2−(4−ジエチルアミノ−2−ヒドロキシベンゾイル)安息香酸ヘキシル(例えばUvinul(登録商標)UVA Plus、BASF)。
−2−(2H−ベンゾトリアゾール−2−イル)−4−メチル−6−(2−メチル−3−(1,3,3,3−テトラメチル−1−(トリメチルシリルオキシ)ジシロキサニル)プロピル)フェノール(例えばSilatrizole(登録商標))、
−2−エチルヘキシル4,4'−[(6−[4−((1,1−ジメチルエチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミノ]ビス(ベンゾエート)(例えばUvasorb(登録商標)HEB)、
−ジメチコンジエチルベンザルマロネート(CAS番号207 574−74−1)、または
−2,2'−メチレンビス(6−(2H−ベンゾトリアゾール−2−イル)−4−(1,1,3,3−テトラメチルブチル)−フェノール)(CAS番号103 597−45−1)、
−2,2'−(1,4−フェニレン)ビス(1H−ベンズイミダゾール−4,6−ジスルホン酸、モノナトリウム塩)(CAS番号180 898−37−7)、ならびに
−2,4−ビス{[4−(2−エチルヘキシルオキシ)−2−ヒドロキシ]フェニル}−6−(4−メトキシフェニル)−1,3,5−トリアジン(CAS番号103 597−45−、187 393−00−6)。
R1は、−C(O)CH3、−CO2R3、−C(O)NH2、および−C(O)N(R4)2から選択され、
Xは、OまたはNHであり、
R2は、直鎖または分岐のC1〜30−アルキル基であり、
R3は、直鎖または分岐のC1〜20−アルキル基であり、
全てのR4は、互いに独立に、Hまたは直鎖もしくは分岐のC1〜8−アルキル基であり、
R5は、H、直鎖もしくは分岐のC1〜8−アルキル基、または直鎖もしくは分岐の−O−C1〜8−アルキル基であり、
R6は、C1〜8−アルキル基である。
但し光安定剤は、特に好ましくはビス(2−エチルヘキシル)2−(4−ヒドロキシ−3,5−ジメトキシベンジリデン)マロネートである。対応する光安定剤ならびにそれらの調製および使用は、国際特許出願WO 03/007906に記載されており、またその開示内容は本願の主題に明確に属する。言及した化合物はまた抗酸化剤である。
R1は、基−C(O)CH3、−CO2R3、−C(O)NH2および−C(O)N(R4)2から選択することができ、
Xは、OまたはNHを示し、
R2は、1〜30個のC原子を有する直鎖または分岐アルキルを示し、
R3は、1〜20個のC原子を有する直鎖または分岐アルキルを示し、
R4は、各場合において互いに独立に、Hまたは1〜8個のC原子を有する直鎖もしくは分岐アルキルを示し、
R5は、1〜8個のC原子を有する直鎖もしくは分岐アルキルまたは1〜8個のC原子を有する直鎖もしくは分岐アルコキシを示し、
R6は、1〜8個のC原子を有する直鎖または分岐アルキルを示す]、
好ましくは、2−(4−ヒドロキシ−3,5−ジメトキシベンジリデン)マロン酸および/または2−(4−ヒドロキシ−3,5−ジメトキシベンジル)マロン酸の誘導体、特に好ましくはビス(2−エチルヘキシル)2−(4−ヒドロキシ−3,5−ジメトキシベンジリデン)マロネート(例えば、Oxynex(登録商標)ST Liquid)および/またはビス(2−エチルヘキシル)2−(4−ヒドロキシ−3,5−ジメトキシベンジル)マロネート(例えば、RonaCare(登録商標)AP)である。
−H
−OR11
−直鎖もしくは分岐のC1−〜C20−アルキル基、
−直鎖もしくは分岐のC3−〜C20−アルケニル基、
−直鎖もしくは分岐のC1−〜C20−ヒドロキシアルキル基(但し、ヒドロキシル基は、
鎖中の第1または第2の炭素原子と結合することができ、さらにアルキル鎖は、酸素によ
って遮断されてもよい)、および/または
−C3−〜C10−シクロアルキル基および/またはC3−〜C12−シクロアルケニル基(但し、各環は、それぞれ−(CH2)n−基によって結合することもでき、n=1〜3である)
から選択され、
−全てのOR11は、互いに独立に、
−OH、
−直鎖もしくは分岐のC1−〜C20−アルコキシ基、
−直鎖もしくは分岐のC3−〜C20−アルケニルオキシ基、
−直鎖もしくは分岐のC1−〜C20−ヒドロキシアルコキシ基(但し、ヒドロキシル基(複数)は、鎖中の第1または第2の炭素原子と結合することができ、さらにアルキル鎖は、酸素によって遮断されてもよい)、および/または
−C3−〜C10−シクロアルコキシ基および/またはC3−〜C12−シクロアルケニルオキシ基(但し、各環は、それぞれ−(CH2)n−基によって結合することもでき、n=1〜3である)、および/または
−モノ−および/またはオリゴグリコシル基であり、
但し、R1〜R7の少なくとも4つの基はOHであり、隣接する−OH基の少なくとも2対は、分子として存在し、
またはR2、R5、およびR6はOHであり、基R1、R3、R4、およびR7〜10はHであり、
これらはドイツ特許出願DE−A−10244282に記載の通りである。
R1およびR2は、同一でも異なっていてもよく、
−H、−C(=O)−R7、−C(=O)−OR7、
−直鎖もしくは分岐のC1−〜C20−アルキル基、
−直鎖もしくは分岐のC3−〜C24−アルケニル基、
−直鎖もしくは分岐のC1−〜C26−ヒドロキシアルキル基(但し、ヒドロキシル基は、鎖中の第1または第2の炭素原子と結合することができ、さらにアルキル鎖は、酸素によ
って遮断されてもよい)、および/または
−C3−〜C10−シクロアルキル基および/またはC3−〜C12−シクロアルケニル基(但し、各環は、それぞれ−(CH2)n−基によって結合することもでき、n=1〜3である)
から選択され、
R3は、Hまたは直鎖もしくは分岐のC1−〜C20−アルキル基であり、
R4は、HまたはOR8であり、
R5およびR6は、同一でも異なっていてもよく、
−H、−OH、
−直鎖もしくは分岐のC1−〜C20−アルキル基、
−直鎖もしくは分岐のC3−〜C20−アルケニル基、および
−直鎖もしくは分岐のC1−〜C20−ヒドロキシアルキル基(但し、ヒドロキシル基は、鎖中の第1または第2の炭素原子と結合することができ、さらにアルキル鎖は、酸素によって遮断されてもよい)
から選択され、
R7は、H、直鎖もしくは分岐のC1−〜C20−アルキル基、ポリヒドロキシル化合物、例えば好ましくはアスコルビン酸基もしくはグリコシド基であり、
R8は、Hまたは直鎖もしくは分岐のC1−〜C20−アルキル基である(但し、置換基R1、R2、およびR4〜R6の少なくとも2つはHではなく、またはR1およびR2の少なくとも1つの置換基は、−C(=O)−R7もしくは−C(=O)−OR7である)。
である。
1.天然真珠光沢顔料、例えば、
a)「パールエッセンス」(魚鱗からのグアニン/ヒポキサンチン混合結晶)および
b)「真珠質層」(粉砕したムール貝の殻)など。
2.単結晶真珠光沢顔料、例えばオキシ塩化ビスマス(BiOCl)など。
3.層状基質顔料:例えばマイカ/金属酸化物。
えば、カラーインデックス(CI)番号19140、77007、77289、および77491などの色素)との混合物の形態である。
式中、p1、p2、p3、…piは、1、2、3、…i回グルコシル化された生成物の割合を重量パーセントで表す。本発明に従って有利に選択される生成物は、1〜2、特に有利には1.1〜1.5、特に非常に有利には1.2〜1.4、特に1.3のグリコシル化度を有する生成物である。
使用される式Iの好ましい化合物は、N,N−ジメチルデカンアミド Spectrasolv DMDA(Jiangsu Feixang ChemicalsまたはLehmann&Voss)である。好ましい難溶解性有機UVフィルターは、エチルヘキシルトリアゾンである。
一般に、カプセルの大きさを測定する。
装置:Malvern Mastersizer 2000とHydro 2000G分散ユニット
サンプルの秤量は、使い捨てピペットを使用して、直接添加して実施する。
分散媒:水
サンプル調製:なし
分散助剤:なし
撹拌器速度:800rpm
ポンプ速度:1800rpm
超音波:なし
粒子の屈折率:1.55
吸光:0.001
分散媒の屈折率:1.33
測定時間[秒/スナップ]:5/5000
バックグラウンド測定時間[秒/スナップ]:8/8000
諸測定の回数:1
オブスキュレーション[%]:8〜12
インビボSPF(日焼け防止指数)を、COLIPA 001−2003に公開されている国際法によって測定した(詳細については例6を参照)。[COLIPA 欧州化粧品トイレタリー香水協会]。
エチルヘキシルトリアゾン400g、ジメチルカプラミド(Spectrasolv DMDA)400gおよびオルトケイ酸テトラエチル240gの溶液を、乳化ツール(Ultra Turax)を使用して、冷却しながら界面活性剤溶液[脱イオン水448gおよび塩化セチルトリメチルアンモニウム(CTAC)11g]中で乳化する。得られたエマルジョンを、塩酸を含有する水に撹拌しながら添加する。得られた混合物を、室温で48〜72時間撹拌する。次いで、アルキルシランの加水分解時に形成したエタノールの濃度を、蒸留によって低減する。脱イオン水300g中PVP20gを添加した後、クエン酸Na溶液を使用して、残渣のpHを3.4〜3.6に調節し、混合物を脱イオン水で作製する。
粒径:d(0.50)=0.53μm、d(0.90)=1.39μm
実施例2
例1と比較して、市販の公知の溶媒を使用して、UVフィルターカプセルを生成した。
サンプル溶液:正確に秤量した生成物約30mgを、100mlの容量フラスコ中、メタノール40mlで分散させる。この混合物を、超音波浴中で5分間混合する。冷却した後、混合物を、メタノールで印に到達させる。混合物を、その測定に対応するように希釈する。注入前に、Anotop(登録商標)25シリンジフィルター(孔径0.02μm)を使用して混合物を濾過する。
室温(20℃〜25℃)における様々な溶媒へのエチルヘキシルトリアゾンの溶解度および水分散液中の含量
ビス−エチルヘキシルオキシフェノールメトキシフェニルトリアジン240g、ジメチルカプラミド(Spectrasolv DMDA)560gおよびオルトケイ酸テトラエチル240gの溶液を、乳化ツール(Ultra Turax)を使用して、冷却しながら界面活性剤溶液[脱イオン水448gおよび塩化セチルトリメチルアンモニウム(CTAC)11g]中で乳化する。得られたエマルジョンを、塩酸を含有する水に撹拌しながら添加する。得られた混合物を、室温で48〜72時間撹拌する。次いで、アルキルシランの加水分解時に形成したエタノールの濃度を、蒸留によって低減する。脱イオン水300g中PVP20gを添加した後、クエン酸Na溶液を使用して、残渣のpHを3.4〜3.6に調節し、混合物を脱イオン水で作製する。
実施例4:製剤例
A)ヒドロゲル
最初にLubrajelを入れ、撹拌しながら他の構成成分を添加する。
インビボSPF:4.6;UVA−PF:1
B)水中油
Carbopolを除く相Aを混合し、Eusolex(登録商標)9020を溶解する。必要に応じて約50℃に温める。Carbopolを入れ、事前に溶解させた相B中で、撹拌しながら乳化する。ホモジナイズする。相Cを添加した後、再度簡単にホモジナイズする。
インビボSPF:14.3;UVA−PF:4.5
C)油中水
Eusolex(登録商標)T−2000を含まない相Aを混合し、80℃に加熱する。次いでEusolex(登録商標)T−2000を、加熱した油相に撹拌しながらゆっくり添加する。相Bを調製し、75℃に加熱する。次いで相Bを、撹拌しながら相Aにゆっくり添加する。ホモジナイズし、冷却する。相Cを、35℃未満で添加する。
インビボSPF:35.4;UVA−PF:4.5
D−1)水中油
相Aを混合し、80℃に加熱する。固体UVフィルターが溶解したかどうか調べる。相Bを混合し、同様に80℃に加熱する。相Bを相A中で撹拌しながら乳化し、3分間ホモジナイズする。撹拌しながら冷却し、クエン酸を使用してpHを調節し、約30℃においてEusolex(登録商標)UV−Pearls(商標)、Uvinul T 150および保存剤を入れる。
D−2)水中油
Carbopolを除く相Aを混合し、Tinosorb Sを溶解する。必要に応じ
て約60℃に温める。Carbopolを入れ、事前に溶解した相Bを、撹拌しながら乳
化する。ホモジナイズする。相Cを添加した後、再度簡単にホモジナイズする。
インビボSPF:10;UVA−PF:7.1
E)油中水
Eusolex(登録商標)T−2000を含まない相Aを、撹拌しながら混合し、Tinosorb Sが溶解するまで80℃で加熱する。次いでEusolex(登録商標)T−2000を、加熱した油相に撹拌しながらゆっくり添加する。相Bを調製し、75℃に加熱する。次いで相Bを、撹拌しながら相Aにゆっくり添加する。ホモジナイズし、冷却する。相Cを35℃未満で添加する。
インビボSPF:36.5;UVA−PF:12
F)油中水
相B:Keltrolを水に分散させる。残りの構成成分を添加し、混合する。相AおよびBを、別個に80℃に加熱する。相Bを、相A中で乳化する。ホモジナイズする。撹拌しながら冷却し、相Cを使用して35℃未満でpHを約6.0に調節する。
インビボSPF:21.3;UVA−PF:9.9
実施例5:
インビトロSPFの測定
化粧用組成物のインビトロSPFを測定する。この測定が基づく基本的な測定原理は、UV光に対する保護のための物質を含む組成物によるUV透過の測定である。ここで組成物は、規定された層の厚さの適切な基材(substrate)に適用され、その吸光度を、適切なUV光度計でナノメートルずつ測定する。インビトロ光防御因子を、以下の式から算出する。
サンプル調製:測定するサンプルのできるだけ多くの小滴を、適切なピペットまたはスパチュラを使用して基材に適用し、均質に分布させる。ここで、基材の風袋重量、湿潤状態の適用速度および平衡(室温で20分)後の適用速度を記録すべきである。平衡化は、暗室中で実施する。各サンプルを、少なくとも3つの基材で測定する。
インビトロSPF[PMMA、0.75mg/cm2]
例C=23.0
例D=4.5
実施例6:
COLIPA(国際的な日焼け防止指数(SPF)試験法、COLIPA、2006年5月)に従うインビボSPF値の測定
UV源:300ワットのキセノンアーク燈太陽シミュレータ(モデル601−300マルチポート、Solar Light Co.Inc.、米国ペンシルベニア州フィラデルフィア)
方法
MED(最小紅斑線量)の測定のための予備試験
6つの異なるUV放射線量(直径1cmの点)を、試験対象の背中の領域に対して使用する。MEDを、放射の16〜24時間後に、保護されていない試験対象の皮膚上で、各場合目視により測定する。
本試験
本試験は、各場合、背中領域35cm2に対して実施する。
生成物の適用および標準
生成物70mgを各領域に適用して、2mg/cm2(+/−2.5%)の生成物の量を得、手袋を使用して生成物を分布させる。
待ち時間
生成物の適用が完了した後、15分の待ち時間を観測した後、放射を開始する。
結果
SPF値の測定については、各場合6人の試験対象で測定した結果を使用する。SPF値を、以下の製剤について示す。
相Aの成分を80℃に加熱する。相Bの成分を、撹拌しながら室温で分散させ、相Aに添加する。相Cの成分をホモジナイズし、相AおよびBの混合物に添加し、再度ホモジナイズする。相DおよびEの成分を、相A+B+Cの混合物に添加し、再度ホモジナイズし、その後室温に冷却する。
粘度:42600mPa・s
pH:6.5
COLIPAによるインビボSPF 6.0
相Aの成分を80℃に加熱する。相Bの成分を、撹拌しながら室温で分散させ、相Aに添加する。相Cの成分をホモジナイズし、相AおよびBの混合物に添加し、再度ホモジナイズする。相DおよびEの成分を、相A+B+Cの混合物に添加し、再度ホモジナイズし、その後室温に冷却する。
粘度:3450mPa・s
pH:6.5
インビボSPF COLIPA 6.7
相AおよびBの成分を、互いに別個に、それぞれ80℃に加熱し、その後混合し、簡単にホモジナイズする。混合物を40℃に冷却し、再度ホモジナイズする。相Cの成分を、相AおよびBの混合物に添加し、全てを一緒にホモジナイズする。
粘度(Brookfield SP6):3350mPas
pH:7.0
インビボSPF COLIPA 6.6
相AおよびBの成分を、互いに別個に、それぞれ80℃に加熱し、その後混合し、簡単にホモジナイズする。相Cの成分を、相AおよびBの混合物に添加し、全てを一緒にホモジナイズする。混合物を40℃に冷却し、再度ホモジナイズする。相Dの成分を、相A+B+Cの混合物に添加し、全てを一緒にホモジナイズする。
粘度(Brookfield SP6):7450mPa・s
pH:7.3
インビボSPF COLIPA 6.4
相Aを、80℃で1時間鹸化する。相Bを、80℃で溶融および混合する。相Cの成分を混合し、80℃に加熱する(カプセルなし)。本発明のカプセルと相Cを混合し、ホモジナイズする。相A+BとCと混合し、ホモジナイズする。相Dを添加する。撹拌しながら室温に冷却し、相Eを添加し、その後ホモジナイズする。
インビボSPF COLIPA 12
(UV)APF 4
相Aを、80℃で1時間鹸化する。相Bを、80℃で溶融および混合する。相Cの成分を混合し、80℃に加熱する。相A+BをCと混合し、ホモジナイズする。相Dを添加する。撹拌しながら室温に冷却し、相Eを添加し、その後ホモジナイズする。
インビボSPF COLIPA 8
(UV)APF 3.8
相AおよびBを、80℃に別個に加熱する。相Bを、撹拌しながら相Aに添加し、簡単にホモジナイズする。相Cを混合相A+Bに添加し、ホモジナイズする。40℃に冷却し、ホモジナイズする。相Cを添加し、ホモジナイズする。
粘度(Brookfield SP6):3350mPa・s
pH値:7.0
インビボSPF COLIPA 6
相Aおよび相Bを互いに別個に、それぞれ80℃に加熱する。相Bを、撹拌しながら相Aに添加し、簡単にホモジナイズする。撹拌しながら40℃に冷却し、相Cを添加し、ホモジナイズする。
粘度(Brookfield SP6):7450mPa・s
pH値:7.3
インビボSPF COLIPA 6
相Aを80℃に加熱する。相Bを、室温で撹拌しながら分散させる。相Bを相A中でホモジナイズする。相Cを、相A+Bに添加し、ホモジナイズする。相DおよびEを添加した後、再度ホモジナイズする。
SPFインビトロ 6
相Aを80℃に加熱する。相Bを、室温で撹拌しながら分散させる。相Bを、相A中でホモジナイズする。相Cを相A+Bに添加し、ホモジナイズする。相DおよびEを添加した後、再度ホモジナイズする。
相Aを80℃に加熱する。相Bを溶融相Aに添加し、ホモジナイズする。相Cを、透明になるまでホモジナイズする。相Cを、相A+Bに添加し、ホモジナイズする。撹拌しながら40℃に冷却する。相Dを添加し、簡単にホモジナイズし、撹拌しながら室温に冷却する。
インビボSPF COLIPA 30
相Aを80℃に加熱する。相Bを溶融相Aに添加し、ホモジナイズする。相Cを、透明になるまでホモジナイズする。相Cを、相A+Bに添加し、ホモジナイズする。撹拌しながら40℃に冷却する。相Dを添加し、簡単にホモジナイズし、撹拌しながら室温に冷却する。
インビボSPF COLIPA 33
(UV)APFインビトロ 11
Claims (19)
- ポリマーシェルならびに
a)少なくとも1つの難溶解性有機UVフィルターおよび
b)室温で40重量%を超える前記難溶解性有機UVフィルターを溶解することができる軟化剤
を含むUVフィルターカプセル。 - a)で言及した前記少なくとも1つの難溶解性有機UVフィルターが、トリアジン誘導体、ジアリールブタジエン誘導体、ヒドロキシベンゾフェノン誘導体および/またはメチレンビスベンゾトリアゾリルテトラメチルブチルフェノール誘導体である
ことを特徴とする、請求項1または2に記載のUVフィルターカプセル。 - a)で言及した前記少なくとも1つの難溶解性有機UVフィルターが、2,4,6−トリス−[アニリノ−(p−カルボ−2'−エチル−1'−ヘキシルオキシ)]−1,3,5−トリアジン、ジオクチルブタミドトリアゾン、ビスエチルヘキシルオキシフェノールメトキシフェニルトリアジン、2,4,6−トリス(ジエチル−4'−アミノベンザルマロネート)−s−トリアジン、2,4,6−トリス(ジメチル−4'−アミノベンザルマロネート)−s−トリアジン、2,4,6−トリス(ジイソプロピル−4−アミノベンザルマロネート)−s−トリアジン、2,4,6−トリス[3'−ベンゾトリアゾール−2−イル)−2'−ヒドロキシ−5'−メチル)フェニルアミノ]−s−トリアジンおよび2,4,6−トリス[3'−ベンゾトリアゾール−2−イル)−2'−ヒドロキシ−5'−tert−オクチル)フェニルアミノ]−s−トリアジンを含む群から選択されるトリアジン誘導体である、請求項1から3の一項または複数項に記載のUVフィルターカプセル。
- a)で言及した前記少なくとも1つの難溶解性有機UVフィルターが、2,4,6−トリス[アニリノ−(p−カルボ−2'−エチル−1'−ヘキシルオキシ)]−1,3,5−トリアジン、ジオクチルブタミドトリアゾンまたはビスエチルヘキシルオキシフェノールメトキシフェニルトリアジンから選択されるトリアジン誘導体である、請求項1から4の一項または複数項に記載のUVフィルターカプセル。
- a)で言及した前記少なくとも1つの難溶解性有機UVフィルターが、1,1−ジカルボキシ(2',2'−ジメチルプロピル)−4,4−ジフェニルブタジエンである、請求項1から3および請求項6の一項または複数項に記載のUVフィルターカプセル。
- a)で言及した前記少なくとも1つの難溶解性有機UVフィルターが、ヘキシル2−(4−ジエチルアミノ−2−ヒドロキシベンゾイル)ベンゾエートである、請求項1から3の一項または複数項および請求項8に記載のUVフィルターカプセル。
- a)で言及した前記少なくとも1つの難溶解性有機UVフィルターが、メチレンビスベンゾトリアゾリルテトラメチルブチルフェノール誘導体である、請求項1から3の一項または複数項に記載のUVフィルターカプセル。
- a)で言及した前記少なくとも1つの難溶解性有機UVフィルターが、2,2'−メチレンビス[6−(2H−ベンゾトリアゾール−2−イル)−4−(1,1,3,3−テトラメチルブチル)フェノール]である、請求項1から3および請求項10の一項または複数項に記載のUVフィルターカプセル。
- 前記UVフィルターカプセルが、a)で言及した前記少なくとも1つの難溶解性UVフィルターおよびb)で言及した前記軟化剤を、重量パーセント比10:90〜90:10、好ましくは重量パーセント比30:70〜70:30で含有することを特徴とする、請求項1から11の一項または複数項に記載のUVフィルターカプセル。
- 請求項1から12の一項または複数項に記載のUVフィルターカプセルを含む分散液。
- 水性である、請求項13に記載の分散液。
- UVフィルターカプセルの割合が、分散液の総量に対して5〜80重量%である、請求項13または14に記載の分散液。
- 少なくとも1つの難溶解性有機UVフィルターおよび少なくとも1つの適切な賦形剤を含む組成物であって、前記難溶解性有機UVフィルターの少なくとも幾らかが、請求項1から12までの少なくとも一項に記載のUVフィルターカプセルの形態にカプセル化される
ことを特徴とする組成物。 - 請求項1から12の一項もしくは複数項に記載のUVフィルターカプセルまたは請求項13から15の一項もしくは複数項に記載の分散液の、組成物の調製への使用。
- 請求項1から12の一項もしくは複数項に記載のUVフィルターカプセルまたは請求項
13から15の一項もしくは複数項に記載の分散液が、さらなる成分と混合される
ことを特徴とする、組成物の調製方法。 - ステップa)において、水中油エマルジョンを、ポリマーシェルの生成のためのソル−ゲル前駆体、少なくとも1つの難溶解性UVフィルターおよび室温で40重量%を超える前記難溶解性有機UVフィルターを水溶液に溶解することができる軟化剤を含む混合物から調製し、
ステップb)において、ステップa)で調製された前記エマルジョンを混合して、pH2〜4を有する水溶液を得、任意選択で
ステップc)において、反応生成物を前記ソル−ゲル前駆体から分離し、前記UVフィルターカプセルを単離する
ことを特徴とする、請求項1から12の一項または複数項に記載のUVフィルターカプセルの生成方法。
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DE102007035567A DE102007035567A1 (de) | 2007-07-26 | 2007-07-26 | UV-Filter-Kapsel |
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EP (1) | EP2170253B1 (ja) |
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CN101795662B (zh) | 2013-01-02 |
KR20100052489A (ko) | 2010-05-19 |
JP5869087B2 (ja) | 2016-02-24 |
BRPI0814313A2 (pt) | 2016-10-11 |
BRPI0814313B1 (pt) | 2017-04-04 |
JP2010534623A (ja) | 2010-11-11 |
KR101529341B1 (ko) | 2015-06-16 |
DE102007035567A1 (de) | 2009-01-29 |
WO2009012871A3 (de) | 2010-01-28 |
WO2009012871A2 (de) | 2009-01-29 |
CN101795662A (zh) | 2010-08-04 |
EP2170253B1 (de) | 2014-09-24 |
US20100209463A1 (en) | 2010-08-19 |
EP2170253A2 (de) | 2010-04-07 |
ES2522909T3 (es) | 2014-11-19 |
US20170105910A1 (en) | 2017-04-20 |
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