JP5275021B2 - 発色団で被覆された金属酸化物粒子 - Google Patents
発色団で被覆された金属酸化物粒子 Download PDFInfo
- Publication number
- JP5275021B2 JP5275021B2 JP2008502279A JP2008502279A JP5275021B2 JP 5275021 B2 JP5275021 B2 JP 5275021B2 JP 2008502279 A JP2008502279 A JP 2008502279A JP 2008502279 A JP2008502279 A JP 2008502279A JP 5275021 B2 JP5275021 B2 JP 5275021B2
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- JP
- Japan
- Prior art keywords
- metal oxide
- oxide particles
- coated metal
- crosslinkable
- acid
- 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.)
- Expired - Fee Related
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- 239000002245 particle Substances 0.000 title claims abstract description 92
- 229910044991 metal oxide Inorganic materials 0.000 title claims abstract description 87
- 150000004706 metal oxides Chemical class 0.000 title claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 99
- 230000000694 effects Effects 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 239000002537 cosmetic Substances 0.000 claims abstract description 27
- 239000004904 UV filter Substances 0.000 claims description 50
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 47
- 238000000576 coating method Methods 0.000 claims description 28
- 239000004408 titanium dioxide Substances 0.000 claims description 22
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000006185 dispersion Substances 0.000 claims description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical group C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 239000010703 silicon Substances 0.000 claims description 10
- 239000011787 zinc oxide Substances 0.000 claims description 10
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002981 blocking agent Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 235000012239 silicon dioxide Nutrition 0.000 claims description 6
- 125000006850 spacer group Chemical group 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- 239000010936 titanium Chemical group 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000011701 zinc Chemical group 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000011247 coating layer Substances 0.000 claims description 3
- 239000011164 primary particle Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 238000003980 solgel method Methods 0.000 claims description 3
- 229910052726 zirconium Chemical group 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 229910052845 zircon Inorganic materials 0.000 claims 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 14
- 230000008569 process Effects 0.000 abstract description 6
- 230000009931 harmful effect Effects 0.000 abstract description 3
- -1 Polysiloxane Polymers 0.000 description 52
- 239000000516 sunscreening agent Substances 0.000 description 26
- 230000000475 sunscreen effect Effects 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 235000002639 sodium chloride Nutrition 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
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- 239000003995 emulsifying agent Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- 239000002585 base Substances 0.000 description 10
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 150000004703 alkoxides Chemical class 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 125000004423 acyloxy group Chemical group 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 6
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 description 6
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- UPOYFZYFGWBUKL-UHFFFAOYSA-N amiphenazole Chemical compound S1C(N)=NC(N)=C1C1=CC=CC=C1 UPOYFZYFGWBUKL-UHFFFAOYSA-N 0.000 description 6
- 229950001798 amiphenazole Drugs 0.000 description 6
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- 239000003974 emollient agent Substances 0.000 description 6
- 229960001679 octinoxate Drugs 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 6
- 229910052721 tungsten Inorganic materials 0.000 description 6
- 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 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- 239000004909 Moisturizer Substances 0.000 description 5
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
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- 239000003963 antioxidant agent Substances 0.000 description 5
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- 229920001577 copolymer Polymers 0.000 description 5
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- 238000010348 incorporation Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
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- 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 description 5
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- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- QMIBDVOQOZDSEN-UHFFFAOYSA-N 2-phenylbenzimidazole-2-sulfonic acid Chemical compound N1=C2C=CC=CC2=NC1(S(=O)(=O)O)C1=CC=CC=C1 QMIBDVOQOZDSEN-UHFFFAOYSA-N 0.000 description 4
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229940093609 tricaprylin Drugs 0.000 description 1
- GKAVWWCJCPVMNR-UHFFFAOYSA-N tridecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCC GKAVWWCJCPVMNR-UHFFFAOYSA-N 0.000 description 1
- 229940098385 triisostearin Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 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
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
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- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/29—Titanium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3669—Treatment with low-molecular organic compounds
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- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3684—Treatment with organo-silicon compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3692—Combinations of treatments provided for in groups C09C1/3615 - C09C1/3684
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/438—Thermochromatic; Photochromic; Phototropic
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/61—Surface treated
- A61K2800/62—Coated
- A61K2800/623—Coating mediated by organosilicone compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/65—Characterized by the composition of the particulate/core
- A61K2800/651—The particulate/core comprising inorganic material
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
Description
[式中、
Mは、金属または半金属元素(ケイ素、チタン、亜鉛、アルミニウムまたはジルコニウムなど)であり、好ましくはMはケイ素であり、
Rは、好ましくは10個以下の炭素原子を有する加水分解性置換基(アルコキシド、アリールオキシド、カルボン酸エステル、アシルオキシ基、ジケトナト基、加水分解性アザ基、または塩素など)であり、より好ましくは、10個以下の炭素原子を有するアルコキシドまたはアシルオキシ基、特に、メトキシドまたはエトキシドなどのC1〜C6アルコキシドであり、
Qは、非加水分解性基であり、好ましくは、C1〜C8アルキル基、例えば、メチルまたはエチルまたはオクチル基などの、10個以下の炭素原子を有する炭化水素基であり、
nは、2または3の整数、好ましくは3であり、
mは、1または2の整数であり、
qは、0または1の整数であり、
n+m+q=4であり、
Pは、UVフィルタ活性を与える分子の部分であり、好ましくは、Mに化学的に結合された一般式A−(B)b(C)c(D)d(E)e−で表され、
式中、
Aは、UV−Aおよび/またはUV−Bおよび/または広帯域フィルタ活性を有する発色団であり、−(B)b(C)c(D)d(E)e−は、スペーサー基であり、ここで、
Bは、20個以下、好ましくは1〜12個、最も好ましくは3〜12個の炭素原子を有する直鎖状または分枝状アルキレン基であり、
Cは、O、SまたはNHであり、
Dは、CONH−基であり、
Eは、20個以下、好ましくは1〜12個、最も好ましくは3〜12個の炭素原子を有する直鎖状または分枝状アルキレンまたはアルケニレン基であり、
bは、0または1であり、
cは、0または1であり、
dは、0または1であり、そして
eは、0または1である]
で表される発色団である。
・ アリルまたはプロパルギルを末端基とする分子Aと、トリエトキシシラン、メチルジクロロシラン(MDClS)またはトリクロロシラン(TClS)とのヒドロシリル化(このカップリング反応の結果、C−Si結合が生じる);
・ 3−(イソシアナトプロピル)トリエトキシシラン(ICPTEOS)へのヒドロキシルまたはアミノを末端基とする分子Aの付加(この結果、カルバメートまたはウレタン結合が生じる);
・ 3−(アミノプロピル)−トリエトキシシラン(APTEOS)を用いた、塩化アシルを末端基とする分子Mのアミド化;
・ 第一級または第二級アミン(一方、アミンは複素環のメンバーであり得る)による、3−(クロロプロピル)−トリエトキシシラン(CPTEOS)などにおける塩素の求核置換
によって変性される。
などのベンゾフェノン誘導体、
などのp−アミノ安息香酸誘導体、
などのベンゾオキサゾール誘導体、
などのカンファー誘導体、
などのケイ皮酸またはベンザルマロネート誘導体、
などのベンズイミダゾール誘導体
などのオクトクリレン誘導体
などのベンゾトリアゾール誘導体
などのジヒドロピリジン誘導体
などのtert−ブチルジベンゾイルメタン誘導体であり、
式中、R’は、水素、ヒドロキシ、直鎖または分枝鎖C1〜20−アルキル、−アルコキシまたはC2〜20−アルケニルである。
(式中、Alkは、C1〜C6ルキル基、好ましくはメチルまたはエチルである)
などの式Si(R)r(Q)qS(式中、Rは、上記の加水分解性基、特に、10個以下の炭素原子を有するアルコキシ基またはアシルオキシ基であり、Qは、上記の非加水分解性基、特に、C1〜C6アルキル基(例えば、メチル)であり、Sは、該発色団と反応可能な反応性基、特に、水素原子、基−(CH2)o−NCO、基−(CH2)o−Clまたは基−(CH2)o−NH2であり、rは、2または3であり、qは、0または1であり、oは、1〜6である)で表されるシラン分子を、例えば、
(式中、R’は、水素、ヒドロキシ、直鎖または分枝鎖C1〜20−アルキル、−アルコキシまたはC2〜20−アルケニルであるがこれらに限定されるものではない)
から選択される発色団と反応させることによって得られる。
− 2−シアノ−3,3−ジフェニルアクリル酸2−エチルヘキシル(オクトクリレン、パルソール(登録商標)340)、2−シアノ−3,3−ジフェニルアクリル酸エチルなどのアクリレート;
− 4−メチルベンジリデンカンファー(パルソール(登録商標)5000)、3−ベンジリデンカンファー、メト硫酸ベンザルコニウムカンファー、ポリアクリルアミドメチルベンジリデンカンファー、スルホベンジリデンカンファー、スルホメチルベンジリデンカンファー、テレフタリデンジカンファースルホン酸などのカンファー誘導体;
− メトキシケイ皮酸オクチル(パルソール(登録商標)MCX)、メトキシケイ皮酸エトキシエチル、メトキシケイ皮酸ジエタノールアミン(パルソール(登録商標)ヒドロ)、メトキシケイ皮酸イソアミルなどのシンナメート誘導体ならびにシロキサンに結合されたケイ皮酸誘導体;
− p−アミノ安息香酸、p−ジメチルアミノ安息香酸2−エチルヘキシル、N−オキシプロピレン−p−アミノ安息香酸エチル、p−アミノ安息香酸グリセリルなどのp−アミノ安息香酸誘導体、
− ベンゾフェノン−3、ベンゾフェノン−4、2,2’,4,4’−テトラヒドロキシ−ベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジメトキシベンゾフェノンなどのベンゾフェノン;
− 4−メトキシベンザルマロン酸ジ−(2−エチルヘキシル)などのベンザルマロン酸のエステル;
− 欧州特許公報EP 0895 776号明細書に記載のような2−(4−エトキシアニリノメチレン)プロパン二酸ジエチルエステルなどの2−(4−エトキシアニリノメチレン)プロパン二酸のエステル;
− 欧州特許公報EP 0358584 B1号明細書、EP 0538431 B1号明細書およびEP 0709080 A1号明細書に記載のようなベンザルマロネート基を含有するオルガノシロキサン化合物;
− ドロメトリゾールトリシロキサン(メギゾリル(Mexoryl)XL);
− 微粒子化されたTiO2などの顔料。「微粒子化された」という用語は、約5nm〜約200nm、特に約15nm〜約100nmの粒径を指す。TiO2粒子はまた、例えば酸化アルミニウムまたは酸化ジルコニウムなどの金属酸化物、または例えばポリオール、メチコーン、ステアリン酸アルミニウム、アルキルシランなどの有機コーティングによって被覆され得る。かかるコーティングは、当該技術分野で周知である。
− 例えば、2−フェニルベンズイミダゾールスルホン酸およびその塩(パルソール(登録商標)HS)などのイミダゾール誘導体。2−フェニルベンズイミダゾールスルホン酸の塩は、例えば、ナトリウム塩またはカリウム塩などのアルカリ塩、アンモニウム塩、モルホリン塩、モノエタノールアミン塩、ジエタノールアミン塩のような第一級、第二級および第三級アミンの塩。
− サリチル酸イソプロピルベンジル、サリチル酸ベンジル、サリチル酸ブチル、サリチル酸オクチル(ネオ・ヘリオパンOS)、サリチル酸イソオクチルまたはサリチル酸ホモメチル(ホモサレート、ヘリオパン)などのサリチレート誘導体;
− オクチルトリアジン(ユビナールT−150)、ジオクチルブタミドトリアゾン(UVアブソーブHEB)、ビスエトキシフェノールメトキシフェニルトリアジン(チノソーブS)などのトリアジン誘導体;
− カプセル化されたメトキシシンナメート(エウソレックスUV−パール(Eusolex UV−pearls))などのカプセル化されたUVフィルタ。
− 4−tert−ブチル−4’−メトキシジベンゾイル−メタン(パルソール(登録商標)1789)、ジメトキシジベンゾイルメタン、イソプロピルジベンゾイルメタンなどのジベンゾイルメタン誘導体;
− 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(チノソーブM)などのベンゾトリアゾール誘導体;
− 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)(ネオ・ヘリオパン(Neoheliopan)AP)などのフェニレン−1,4−ビス−ベンズイミダゾールスルホン酸または塩;
− 欧州特許公報EP 1046391号明細書に記載のような2−(4−ジエチルアミノ−2−ヒドロキシ−ベンゾイル)−安息香酸ヘキシルエステルなどのアミノ置換されたヒドロキシベンゾフェノン
− 微粒子化されたZnOまたはTiO2などの顔料。「微粒子化された」という用語は、約5nm〜約200nm、特に約15nm〜約100nmの粒径を指す。粒子はまた、例えば酸化アルミニウムまたは酸化ジルコニウムなどの他の金属酸化物、または例えばポリオール、メチコーン、ステアリン酸アルミニウム、アルキルシランなどの有機コーティングによって被覆され得る。かかるコーティングは、当該技術分野で周知である。
− 欧州特許公報EP 0 514 491 B1号明細書およびEP 0 780 119 A1号明細書に記載のような3,3−ジフェニルアクリレート誘導体;
− 米国特許第5,605,680号明細書に記載のようなベンジリデンカンファー誘導体;
− 欧州特許公報EP 0358584 B1号明細書、EP 0538431 B1号明細書およびEP 0709080 A1号明細書に記載のようなベンザルマロネート基を含有するオルガノシロキサン
によって安定化される、パルソール(登録商標)1789などのジベンゾイルメタン誘導体を指す。
鉱油および鉱ろう;
カプリン酸またはカプリル酸のトリグリセリドなどの油、好ましくはヒマシ油;
油またはろうおよび他の天然もしくは合成油、好ましい実施形態では、脂肪酸と、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、グリセリンとのエステル、または脂肪アルコールと、カルボン酸もしくは脂肪酸とのエステル;
安息香酸アルキル;ならびに/あるいは
ジメチルポリシロキサン、ジエチルポリシロキサン、ジフェニルポリシロキサン、シクロメチコーンおよびそれらの混合物などのシリコーン油。
[実施例1]
2−(4−ヒドロキシベンジリデン)マロン酸ジエチルエステル
還流冷却器、ディーン・スターク管および油浴を備えた、磁気撹拌器を有する250mlの丸底フラスコに、10g(81mmol)の4−ヒドロキシベンズアルデヒド、150mlのトルエン、0.97ml(10mmol)のピペリジンおよび0.8g(6.5mmol)の安息香酸を装入し、反応物を45℃に加熱する。次いで、20mlのトルエン中の13.7ml(90mmol)マロン酸ジエチルを滴下して加える。反応物を還流させ、水をディーン・スターク管内に集めた。16時間後、反応物を冷まし、水で3回および希釈したNaCl−溶液で1回洗浄した。NaSO4で乾燥させた後、有機相を濃縮し、カラム・クロマトグラフィー(ヘキサン/EtOAc)で精製して、18.6g(86.2%)の2−(4−ヒドロキシベンジリデン)マロン酸ジエチルエステルを得る。
2−[[4−[3−(トリエトキシシリル)プロピル)アミノカルボニル)オキシ)ベンジリデン)マロン酸ジエチルエステル
70mlのテトラヒドロフラン中の上記のように調製した5g(19mmol)の2−(4−ヒドロキシベンジリデン)−マロン酸ジエチルエステルおよび数滴のジブチル錫ジラウレート触媒を攪拌した溶液に、5.6ml(22mmol)の3−イソシアナトプロピル−トリエトキシシラン(ICTEOS)を窒素雰囲気下で加えた。反応混合物を、遊離した2−(4−ヒドロキシベンジリデン)マロン酸ジエチルエステルが薄層クロマトグラフィーによって検出できなくなるまで40℃で攪拌した。テトラヒドロフランを蒸発させた後、粗生成物をカラム・クロマトグラフィー(ヘキサン/EtOAc)で精製して、8.7g(90%)の2−[[4−[3−(トリエトキシシリル)プロピル)アミノカルボニル)オキシ)ベンジリデン)−マロン酸ジエチルエステルを無色油として得た。UV(エタノール)、290nm(21068)。
UV−Aおよび/またはUV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有する架橋性発色団と、任意に、UV−Aおよび/またはUV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有さない架橋性モノマーの少なくとも1種とによる金属酸化物のコーティングを、パーキン・エルマー・スペクトラム・ワン(Perkin Elmer Spectrum One)、すなわち得られた透過赤外吸収スペクトルの分析によるFT−IR分光計を用いたFT−IR分光法によって以下のように検証した。Si−O−Siの伸縮振動に帰属されるピークが、1000〜1200cm−1で観察された。架橋性発色団の組込みが、発色団のカルボニル基に帰属するピークが1650〜1720cm−1にあることによって実証される。オクチルトリメトキシシランを、UVフィルタ活性を有さない架橋性モノマーとして用いた場合、さらなる−CH2/−CH3の伸縮振動が、2800〜3000cm−1で観察される。
非処理の二酸化チタンは、UV光で照射した際に強い黄色変化を生じる。色が濃くなるにしたがい、二酸化チタンの反応度の高さが増している。これは、表面処理の有効性についての有効な分析試験である。
9gの発熱性二酸化チタン(P25、デグサ)に、オクチルトリメトキシシランと実施例2の2−[[4−[3−(トリエトキシシリル)プロピル)アミノカルボニル)オキシ)ベンジリデン)マロン酸ジエチルエステルとの混合物1gを、5:1(w/w)の比率で加える。次いで、その粉末を十分に混合し、100℃に加熱する。この間に、エタノールおよびメタノールを除去する。97%の理論量(重量)のアルコールを蒸留して取り除いたとき、反応物を冷却し、白色固体を、N,N−ジメチルホルムアミド、メタノール、ジクロロメタンおよびジエチルエーテルで記載の順に3回洗浄して、非処理のシリル化試薬を除去する。IR ν(C=O):1649。
9gの発熱性二酸化チタン(P25、デグサ)に、オクチルトリメトキシシランと実施例2の2−[[4−[3−(トリエトキシシリル)プロピル)アミノカルボニル)オキシ)ベンジリデン)マロン酸ジエチルエステルとの混合物1gを、10:1(w/w)の比率で加える。次いで、その粉末を十分に混合し、100℃に加熱する。この間に、エタノールおよびメタノールを除去する。97%の理論量のアルコールを蒸留して取り除いたとき、反応物を冷まし、白色固体を、N,N−ジメチルホルムアミド、メタノール、ジクロロメタンおよびジエチルエーテルで記載の順に3回洗浄する。IR ν(C=O):1650。
9gの発熱性二酸化チタン(P25、デグサ)に、オクチルトリメトキシシランと実施例2の2−[[4−[3−(トリエトキシシリル)プロピル)アミノカルボニル)オキシ)ベンジリデン)マロン酸ジエチルエステルとの混合物1gを、15:1(w/w)の比率で加える。次いで、その粉末を十分に混合し、100℃に加熱する。この間に、エタノールおよびメタノールを除去する。97%の理論量のアルコールを蒸留したときに、薄層クロマトグラフフィー(ヘキサン/酢酸エチル 1:1)を行い、これにより全ての架橋性発色団が消失したことが示される。反応物を冷まし、白色固体を、N,N−ジメチルホルムアミド、メタノール、ジクロロメタンおよびジエチルエーテルで記載の順に3回洗浄する。乾燥させた後、コーティングの有効性を、40MEDでの照射によって実証し、これにより、被覆していない二酸化チタンと比較して低減した着色が示された。IR ν(C=O):1651。
70mlの水中の5gの発熱性二酸化チタン(P25、デグサ)の分散液に、テトラエトキシシラン(TEOS)と実施例2の2−[[4−[3−(トリエトキシシリル)プロピル)アミノカルボニル)オキシ)−ベンジリデン)マロン酸ジエチルエステルとの混合物5gを、5:1(w/w)の比率で加え、室温で15分間攪拌する。その後、1.5mlの水酸化アンモニウム水溶液(28〜30重量%)を加え、反応混合物を80℃で終夜攪拌する。懸濁液をろ過し、わずかに灰色がかった固体を、N,N−ジメチルホルムアミド、メタノール、ジクロロメタンおよびジエチルエーテルで記載の順に3回洗浄する。IR ν(C=O):1650。
1%の塩化セチルトリアンモニウム水溶液50g中の5gの発熱性二酸化チタン(P25、デグサ)の分散液に、テトラエトキシシラン(TEOS)と実施例2の2−[[4−[3−(トリエトキシシリル)プロピル)アミノカルボニル)オキシ)ベンジリデン)マロン酸ジエチルエステルとの混合物2gを、5:1(w/w)の比率で加え、室温で15分間攪拌する。その後、pH11.3の50gの水酸化ナトリウム水溶液を加え、得られた混合物を、室温で1時間攪拌する。懸濁液をろ過し、わずかに黄色がかった固体を、N,N−ジメチルホルムアミド、メタノール、ジクロロメタンおよびジエチルエーテルで記載の順に3回洗浄する。IR ν(C=O):1710。
O/W型日焼け止め乳液
部分A)およびB)を攪拌しながら85℃に加熱する。均質になったら、部分B)をA)にかき混ぜながら加える。攪拌しながら周囲温度に冷却して、部分C)を加える。小粒径が得られるまで均質化する。
ウォータープルーフの日焼け止め乳液
部分A)およびB)を攪拌しながら85℃に加熱する。均質になったら、部分B)をA)にかき混ぜながら加える。攪拌しながら周囲温度に冷却して、部分C)を加える。小粒径が得られるまで均質化する。
乳幼児用の日焼け止め乳液
部分A)およびB)を攪拌しながら85℃に加熱する。均質になったら、部分B)をA)にかき混ぜながら加える。攪拌しながら周囲温度に冷却して、部分C)を加える。小粒径が得られるまで均質化する。
保護効果の高い日焼け止め乳液
部分A)およびB)を攪拌しながら85℃に加熱する。均質になったら、部分B)をA)にかき混ぜながら加える。攪拌しながら周囲温度に冷却して、部分C)およびD)を加える。小粒径が得られるまで均質化する。
ウォーターフリーの日焼け止めジェル
部分A)およびB)を攪拌しながら混合する。均質になったら、部分C)およびD)をかき混ぜながら加える。
[日焼け止めジェル]
部分A)およびB)を攪拌しながら85℃に加熱する。均質になったら、部分B)をA)にかき混ぜながら加える。攪拌しながら周囲温度に冷却して、部分C)およびD)を加える。小粒径が得られるまで均質化する。
保護効果の高いWO型日焼け止め乳液
部分A)、B)およびC)を攪拌しながら85℃に加熱する。均質になったら、部分B)およびC)をA)にかき混ぜながら加える。攪拌しながら周囲温度に冷却して、部分D)およびE)を加える。小粒径が得られるまで均質化する。
顔料を含むW/O型乳液
部分A)、B)およびC)を攪拌しながら85℃に加熱する。均質になったら、部分B)およびC)をA)にかき混ぜながら加える。攪拌しながら周囲温度に冷却して、部分D)およびE)を加える。小粒径が得られるまで均質化する。
ビタミンCを含む日中用保護クリーム
Claims (19)
- 被覆金属酸化物粒子を製造するための方法であって、
UV−Aおよび/またはUV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有する架橋性発色団のうちの少なくとも1種と、任意に、UVフィルタ活性を有さない架橋性モノマーのうちの少なくとも1種との架橋性基の反応で架橋されたポリマーのコーティング層によって金属酸化物粒子が被覆され、
前記架橋性発色団のうちの少なくとも1種が、式M(R)n(P)m(Q)q[式中、Mが、ケイ素、チタン、亜鉛、アルミニウムまたはジルコニウムであり、Rが、加水分解性基であり、Pが、UV−A、UV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有する発色団であり、Qが、非加水分解性基であり、nが、2または3であり、mが、1または2であり、qが、0または1であり、ここでn+m+q=4である]で表されるモノマーであり、
前記金属酸化物粒子が二酸化チタン、酸化亜鉛、酸化ジルコン、酸化鉄、酸化セリウム、上記のものの混合物、ならびに上記のものと酸化アルミニウム、および/または二酸化ケイ素との混合物の群から選択される金属酸化物の粒子である、被覆金属酸化物粒子の製造方法。 - 金属酸化物粒子が、UV−Aおよび/またはUV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有する架橋性発色団のうちの少なくとも1種と、UVフィルタ活性を有さない架橋性モノマーのうちの少なくとも1種との架橋性基の反応で架橋されたポリマーのコーティング層によって被覆される請求項1に記載の被覆金属酸化物粒子の製造方法。
- 前記金属酸化物粒子が、ゾル−ゲル法によって被覆される請求項1または請求項2に記載の被覆金属酸化物粒子の製造方法。
- 前記金属酸化物粒子が、それらを水性分散液の形態で、塩基の存在下で、UV−Aおよび/またはUV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有する架橋性発色団のうちの少なくとも1種と、任意に、UVフィルタ活性を有さない架橋性モノマーのうちの少なくとも1種と接触させることによって被覆される請求項1〜3のいずれか一項に記載の被覆金属酸化物粒子の製造方法。
- 前記発色団Pが、Mに化学的に結合された一般式A−(B)b(C)c(D)d(E)e−
[式中、
Aが、UV−Aおよび/またはUV−Bフィルタおよび/または広帯域活性を有する発色団であり、−(B)b(C)c(D)d(E)e−がスペーサー基であり、ここで、
Bが、20個以下の炭素原子を有する直鎖状または分枝状アルキレン基であり、
Cが、O、SまたはNHであり、
Dが、CONH−基であり、
Eが、20個以下の炭素原子を有する直鎖状または分枝状アルキレンまたはアルケニレン基であり、
bが、0または1であり、
cが、0または1であり、
dが、0または1であり、そして
eが、0または1である]
で表される請求項1〜4のいずれか一項に記載の被覆金属酸化物粒子の製造方法。 - 前記Mが、ケイ素である請求項1〜5のいずれか一項に記載の被覆金属酸化物粒子の製造方法。
- 前記被覆金属酸化物粒子を製造するために用いられる全ての架橋性化合物が、ケイ素含有モノマーである請求項6に記載の被覆金属酸化物粒子の製造方法。
- UV−Aおよび/またはUV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有する架橋性発色団のうちの少なくとも1種が、少なくとも2個のC1〜6−アルコキシ基を含むシランモノマーである請求項1〜6のいずれか一項に記載の被覆金属酸化物粒子の製造方法。
- 金属酸化物粒子を製造するために用いられる全てのモノマーが、少なくとも2個のC1〜6−アルコキシ基を含むシランモノマーである請求項8に記載の被覆金属酸化物粒子の製造方法。
- UV−Aおよび/またはUV−Bおよび/またはUV−Cおよび/または広帯域フィルタ活性を有する架橋性発色団の量が、最終コーティング中のUV吸収剤部分の濃度が0.05〜20重量%であるようなものである請求項1〜9のいずれか一項に記載の被覆金属酸化物粒子の製造方法。
- 前記金属酸化物が、二酸化チタンまたは酸化亜鉛、または上記のものの混合物、あるいは上記のものと酸化アルミニウム、および/または酸化鉄、および/または二酸化ケイ素との混合物である請求項1〜10のいずれか一項に記載の被覆金属酸化物粒子の製造方法。
- 前記被覆酸化物粒子の一次粒径が、2〜100nmの範囲にある請求項1〜11のいずれか一項に記載の被覆金属酸化物粒子の製造方法。
- 請求項1〜12のいずれか一項に記載の方法によって得られる被覆金属酸化物粒子。
- 請求項13に記載の被覆金属酸化物粒子を含む化粧用または皮膚用の組成物。
- さらに他のUV−A遮断剤および/またはUV−B遮断剤および/または広帯域遮断剤が存在する請求項14に記載の化粧用または皮膚用の組成物。
- 0.01重量%〜25重量%の前記被覆金属酸化物粒子を含む請求項14または15に記載の化粧用または皮膚用の組成物。
- UVフィルタの安定化のための請求項13に記載の被覆金属酸化物粒子の使用。
- 前記UVフィルタが、ジベンゾイルメタンまたはその誘導体である請求項17に記載の使用。
- 紫外線からヒトの皮膚または頭髪を保護するための請求項13に記載の被覆金属酸化物粒子の使用。
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EP05006432 | 2005-03-23 | ||
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PCT/EP2006/002185 WO2006099952A2 (en) | 2005-03-23 | 2006-03-09 | Chromophore coated metal oxide particles |
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US20100184887A1 (en) * | 2007-07-02 | 2010-07-22 | Basf Se | Hybrid nanoparticles |
JP2009120700A (ja) * | 2007-11-14 | 2009-06-04 | Niigata Univ | 機能性微粒子及びその製造方法、並びにこれを配合してなる被覆性組成物 |
WO2009101016A2 (de) * | 2008-02-12 | 2009-08-20 | Basf Se | Modifizierte hybride nanopartikel |
DE102008028664A1 (de) * | 2008-06-09 | 2009-12-10 | Beiersdorf Ag | Sonnenschutzmittel mit hohem UV-A-Schutz |
MX312760B (es) * | 2008-07-18 | 2013-08-29 | Basf Se | Particulas de oxido de zinc modificado. |
EP3673893A1 (en) | 2010-08-27 | 2020-07-01 | Sienna Biopharmaceuticals, Inc. | Compositions and methods for targeted thermomodulation |
US9572880B2 (en) | 2010-08-27 | 2017-02-21 | Sienna Biopharmaceuticals, Inc. | Ultrasound delivery of nanoparticles |
JP5952676B2 (ja) * | 2012-04-27 | 2016-07-13 | 花王株式会社 | 疎水化処理した酸化亜鉛粒子の製造方法 |
WO2014028007A1 (en) * | 2012-08-14 | 2014-02-20 | Empire Technology Development Llc | Uv absorbers on pigments |
WO2014058904A1 (en) | 2012-10-11 | 2014-04-17 | Nanocomposix, Inc. | Silver nanoplate compositions and methods |
ES2962589T3 (es) * | 2016-06-27 | 2024-03-20 | Dsm Ip Assets Bv | Composiciones que comprenden micropigmentos |
EP3678633B1 (en) * | 2017-09-05 | 2022-01-05 | Vizor, LLC | Hydroxy cinnamate and silanol adduct coated inorganic sunscreen agents |
US10696819B2 (en) * | 2017-10-19 | 2020-06-30 | International Business Machines Corporation | Ultraviolet light stabilizing polymeric filler materials |
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US5315022A (en) * | 1988-07-08 | 1994-05-24 | Shiseido Company Ltd. | Silicone type cinnamic acid derivative, preparation method thereof, UV-ray absorber, and external skin treatment agent |
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DE10333029A1 (de) * | 2003-07-21 | 2005-02-17 | Merck Patent Gmbh | Nanopartikuläres UV-Schutzmittel |
KR101123520B1 (ko) * | 2003-12-04 | 2012-03-13 | 디에스엠 아이피 어셋츠 비.브이. | 자외선 필터 활성을 갖는 미세캡슐 및 그의 제조방법 |
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ATE484552T1 (de) | 2010-10-15 |
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EP1861465B1 (en) | 2010-10-13 |
CN101146872B (zh) | 2012-08-29 |
EP1861465A2 (en) | 2007-12-05 |
DE602006017524D1 (de) | 2010-11-25 |
JP2008535959A (ja) | 2008-09-04 |
KR20070113249A (ko) | 2007-11-28 |
WO2006099952A3 (en) | 2007-01-25 |
US20090291107A1 (en) | 2009-11-26 |
AU2006226649A1 (en) | 2006-09-28 |
KR101264453B1 (ko) | 2013-05-14 |
WO2006099952A2 (en) | 2006-09-28 |
AU2006226649B2 (en) | 2011-08-25 |
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