JP2005508423A - 高い屈折率の芳香族ベースのプレポリマー前駆体 - Google Patents
高い屈折率の芳香族ベースのプレポリマー前駆体 Download PDFInfo
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- JP2005508423A JP2005508423A JP2003542256A JP2003542256A JP2005508423A JP 2005508423 A JP2005508423 A JP 2005508423A JP 2003542256 A JP2003542256 A JP 2003542256A JP 2003542256 A JP2003542256 A JP 2003542256A JP 2005508423 A JP2005508423 A JP 2005508423A
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- Prior art keywords
- acrylate
- group
- polymer composition
- methacrylate
- phenyl
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 22
- 239000002243 precursor Substances 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 claims abstract description 73
- 229920000642 polymer Polymers 0.000 claims abstract description 54
- -1 polysiloxane Polymers 0.000 claims abstract description 53
- 239000000178 monomer Substances 0.000 claims abstract description 35
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 5
- 210000004087 cornea Anatomy 0.000 claims description 5
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 4
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 claims description 4
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- ICGLGDINCXDWJB-UHFFFAOYSA-N 2-benzylprop-2-enamide Chemical compound NC(=O)C(=C)CC1=CC=CC=C1 ICGLGDINCXDWJB-UHFFFAOYSA-N 0.000 claims description 3
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 3
- IMOLAGKJZFODRK-UHFFFAOYSA-N 2-phenylprop-2-enamide Chemical compound NC(=O)C(=C)C1=CC=CC=C1 IMOLAGKJZFODRK-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 claims description 3
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 claims description 3
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 3
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 3
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims description 3
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 claims description 3
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 3
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 3
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 3
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- HAURRGANAANPSQ-UHFFFAOYSA-N cis-2,4,6-Trimethyl-2,4,6-triphenylcyclotrisiloxane Chemical compound O1[Si](C)(C=2C=CC=CC=2)O[Si](C)(C=2C=CC=CC=2)O[Si]1(C)C1=CC=CC=C1 HAURRGANAANPSQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
- 238000003754 machining Methods 0.000 claims 2
- JTSBEHSKHKENTD-UHFFFAOYSA-N 1-[methyl(trimethylsilyloxy)silyl]butane-1,3-diol Chemical group CC(O)CC(O)[SiH](C)O[Si](C)(C)C JTSBEHSKHKENTD-UHFFFAOYSA-N 0.000 claims 1
- QZWSOANAJGSJJT-UHFFFAOYSA-N 1-[methyl(trimethylsilyloxy)silyl]propane-1,3-diamine Chemical group C[Si](C)(C)O[SiH](C)C(N)CCN QZWSOANAJGSJJT-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000007943 implant Substances 0.000 abstract description 12
- 229920002100 high-refractive-index polymer Polymers 0.000 abstract 1
- 239000000463 material Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 230000000007 visual effect Effects 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000012467 final product Substances 0.000 description 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- HQTNTADNCBNEGC-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(2-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=CC=C(N2CCOCC2)C=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 HQTNTADNCBNEGC-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical class C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 5
- 150000003377 silicon compounds Chemical class 0.000 description 5
- 238000001542 size-exclusion chromatography Methods 0.000 description 5
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 4
- 208000002177 Cataract Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 208000002847 Surgical Wound Diseases 0.000 description 4
- 238000003848 UV Light-Curing Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- PQPVPZTVJLXQAS-UHFFFAOYSA-N hydroxy-methyl-phenylsilicon Chemical class C[Si](O)C1=CC=CC=C1 PQPVPZTVJLXQAS-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl 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])[H] 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BPPNCCZFDXFYAS-UHFFFAOYSA-N 2h-benzotriazole;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1=CC=CC2=NNN=C21 BPPNCCZFDXFYAS-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004904 UV filter Substances 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 229920006397 acrylic thermoplastic Polymers 0.000 description 3
- 210000002159 anterior chamber Anatomy 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 2
- OWJKJLOCIDNNGJ-UHFFFAOYSA-N 4-[[4-hydroxybutyl(dimethyl)silyl]oxy-dimethylsilyl]butan-1-ol Chemical compound OCCCC[Si](C)(C)O[Si](C)(C)CCCCO OWJKJLOCIDNNGJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FNBNJFFUNDJRAY-UHFFFAOYSA-N CC1=C(CP(C2=CC=CC=C2)=O)C(=CC(=C1)C)C Chemical compound CC1=C(CP(C2=CC=CC=C2)=O)C(=CC(=C1)C)C FNBNJFFUNDJRAY-UHFFFAOYSA-N 0.000 description 2
- SXNICUVVDOTUPD-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 SXNICUVVDOTUPD-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 208000035965 Postoperative Complications Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229920000249 biocompatible polymer Polymers 0.000 description 2
- 239000003618 borate buffered saline Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000001886 ciliary effect Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012632 extractable Substances 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- IMNBHNRXUAJVQE-UHFFFAOYSA-N (4-benzoyl-3-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound OC1=CC(OC(=O)C(=C)C)=CC=C1C(=O)C1=CC=CC=C1 IMNBHNRXUAJVQE-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- BTGYQHGWZLBJOB-UHFFFAOYSA-N 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenoxy]propyl 2-methylprop-2-enoate Chemical compound CC(C)(C)C1=CC(OCCCOC(=O)C(=C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O BTGYQHGWZLBJOB-UHFFFAOYSA-N 0.000 description 1
- RLWDBZIHAUEHLO-UHFFFAOYSA-N 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propyl 2-methylprop-2-enoate Chemical compound CC(C)(C)C1=CC(CCCOC(=O)C(=C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O RLWDBZIHAUEHLO-UHFFFAOYSA-N 0.000 description 1
- IGELQVCMNGAOQV-UHFFFAOYSA-N 4-[methyl(trimethylsilyloxy)silyl]butan-1-ol Chemical compound C[SiH](CCCCO)O[Si](C)(C)C IGELQVCMNGAOQV-UHFFFAOYSA-N 0.000 description 1
- JRISTPRFYXRIIK-UHFFFAOYSA-N CC1=CC(C)=C([PH2]=O)C(C)=C1 Chemical compound CC1=CC(C)=C([PH2]=O)C(C)=C1 JRISTPRFYXRIIK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000000871 endothelium corneal Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
- C08L51/085—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds on to polysiloxanes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S623/00—Prosthesis, i.e. artificial body members, parts thereof, or aids and accessories therefor
- Y10S623/902—Method of implanting
- Y10S623/905—Eye
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S623/00—Prosthesis, i.e. artificial body members, parts thereof, or aids and accessories therefor
- Y10S623/902—Method of implanting
- Y10S623/905—Eye
- Y10S623/907—Method of manipulating parts of intraocular lens structure for implantation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- General Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Veterinary Medicine (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Silicon Polymers (AREA)
- Eyeglasses (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/004,418 US6864341B2 (en) | 2001-11-02 | 2001-11-02 | High refractive index aromatic-based prepolymer precursors |
| PCT/US2002/033437 WO2003040214A1 (en) | 2001-11-02 | 2002-10-17 | High refractive index aromatic-based prepolymer precursors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005508423A true JP2005508423A (ja) | 2005-03-31 |
| JP2005508423A5 JP2005508423A5 (enExample) | 2007-06-14 |
Family
ID=21710696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003542256A Withdrawn JP2005508423A (ja) | 2001-11-02 | 2002-10-17 | 高い屈折率の芳香族ベースのプレポリマー前駆体 |
Country Status (9)
| Country | Link |
|---|---|
| US (5) | US6864341B2 (enExample) |
| EP (1) | EP1448673B1 (enExample) |
| JP (1) | JP2005508423A (enExample) |
| KR (1) | KR20050037428A (enExample) |
| CN (1) | CN1301283C (enExample) |
| AT (1) | ATE422514T1 (enExample) |
| CA (1) | CA2465500A1 (enExample) |
| DE (1) | DE60231140D1 (enExample) |
| WO (1) | WO2003040214A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015502764A (ja) * | 2011-09-16 | 2015-01-29 | ベンズ リサーチ アンド ディベロップメント コーポレーション | 眼内レンズ用の紫外光吸収材料およびその使用 |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8041815B2 (en) * | 2001-09-21 | 2011-10-18 | Microsoft Corporation | Systems and methods for managing network connectivity for mobile users |
| US6864341B2 (en) * | 2001-11-02 | 2005-03-08 | Bausch & Lomb Incorporated | High refractive index aromatic-based prepolymer precursors |
| EP1588686B1 (en) | 2004-04-23 | 2010-08-18 | Intercos S.p.A. | Cosmetic compositions and their use |
| US7279538B2 (en) * | 2005-04-01 | 2007-10-09 | Bausch & Lomb Incorporated | Aromatic-based polysiloxane prepolymers and ophthalmic devices produced therefrom |
| WO2006127100A1 (en) * | 2005-05-26 | 2006-11-30 | Dow Corning Corporation | Process and silicone encapsulant composition for molding small shapes |
| US7423108B2 (en) * | 2005-12-16 | 2008-09-09 | Bausch & Lomb Incorporated | High refractive-index siloxy-containing monomers and polymers, and ophthalmic devices comprising such polymers |
| MY144041A (en) * | 2006-01-17 | 2011-07-29 | Dow Corning | Thermally stable transparent silicone resin compositions and methods for their preparation and use |
| JP2009525507A (ja) * | 2006-02-01 | 2009-07-09 | ダウ・コーニング・コーポレイション | 耐衝撃性光導波路およびその製造方法 |
| KR20080104279A (ko) * | 2006-02-24 | 2008-12-02 | 다우 코닝 코포레이션 | 실리콘으로 캡슐화된 발광 장치 및 실리콘 제조용의 경화성실리콘 조성물 |
| US8569538B2 (en) * | 2006-06-30 | 2013-10-29 | Johnson & Johnson Vision Care, Inc. | Acryloyl materials for molded plastics |
| US8053539B2 (en) | 2006-06-30 | 2011-11-08 | Johnson & Johnson Vision Care Inc. | Siloxanyl materials for molded plastics |
| US7838698B2 (en) | 2006-09-29 | 2010-11-23 | Johnson & Johnson Vision Care, Inc. | Hydrolysis-resistant silicone compounds |
| US20080081850A1 (en) * | 2006-09-29 | 2008-04-03 | Kazuhiko Fujisawa | Process for producing hydrolysis-resistant silicone compounds |
| US9056880B2 (en) | 2006-09-29 | 2015-06-16 | Johnson & Johnson Vision Care, Inc. | Process for producing hydrolysis-resistant silicone compounds |
| US20080119627A1 (en) * | 2006-11-22 | 2008-05-22 | Masataka Nakamura | Methods for purifying siloxanyl monomers |
| TWI449520B (zh) * | 2007-04-30 | 2014-08-21 | Alcon Inc | 含有伸苯基－矽氧烷大分子單體之眼科及耳鼻喉科裝置材料 |
| US8080622B2 (en) | 2007-06-29 | 2011-12-20 | Johnson & Johnson Vision Care, Inc. | Soluble silicone prepolymers |
| WO2009070438A1 (en) | 2007-11-30 | 2009-06-04 | Bausch & Lomb Incorporated | Optical material and method for modifying the refractive index |
| US7897654B2 (en) * | 2007-12-27 | 2011-03-01 | Johnson & Johnson Vision Care Inc. | Silicone prepolymer solutions |
| US7850878B2 (en) * | 2007-12-31 | 2010-12-14 | Bausch & Lomb Incorporated | Method of forming a biomedical device including an ophthalmic device |
| US8940219B2 (en) | 2007-12-31 | 2015-01-27 | Ronald D. Spoor | Ophthalmic device formed by additive fabrication and method thereof |
| MX339104B (es) | 2009-03-04 | 2016-05-12 | Perfect Ip Llc | Sistema para formar y modificar lentes y lentes formados por medio del mismo. |
| US8646916B2 (en) | 2009-03-04 | 2014-02-11 | Perfect Ip, Llc | System for characterizing a cornea and obtaining an opthalmic lens |
| US8292952B2 (en) | 2009-03-04 | 2012-10-23 | Aaren Scientific Inc. | System for forming and modifying lenses and lenses formed thereby |
| CN102759806B (zh) * | 2011-04-28 | 2014-04-30 | 星欧光学股份有限公司 | 具有孔隙的高透氧隐形眼镜及其制造方法 |
| US9314600B2 (en) | 2012-04-15 | 2016-04-19 | Bioconnect Systems, Inc. | Delivery system for implantable flow connector |
| JP2017514964A (ja) | 2014-05-07 | 2017-06-08 | チュビタック （ターキー ビリムセル ヴィ テクノロジク アラスティルマ クルム）Ｔｕｂｉｔａｋ （Ｔｕｒｋｉｙｅ Ｂｉｌｉｍｓｅｌ Ｖｅ Ｔｅｋｎｏｌｏｊｉｋ Ａｒａｓｔｉｒｍａ Ｋｕｒｕｍｕ） | 眼内レンズ（ｉｏｌ）を生産するための組成物及びレンズ製造方法 |
| JP6351385B2 (ja) * | 2014-06-03 | 2018-07-04 | 株式会社メニコン | コンタクトレンズの製造方法 |
| JP6351384B2 (ja) * | 2014-06-03 | 2018-07-04 | 株式会社メニコン | コンタクトレンズおよびその製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| BE477645A (enExample) * | 1967-06-16 | |||
| US3996189A (en) | 1975-04-29 | 1976-12-07 | American Optical Corporation | Optically clear filled silicone elastomers |
| US3996187A (en) | 1975-04-29 | 1976-12-07 | American Optical Corporation | Optically clear filled silicone elastomers |
| GB1604519A (en) | 1977-07-25 | 1981-12-09 | Bausch & Lomb | Polysiloxane polymers and contact lens and other biomedical articles formed therefrom |
| US4418165A (en) | 1980-06-03 | 1983-11-29 | Dow Corning Corporation | Optically clear silicone compositions curable to elastomers |
| NL8400727A (nl) * | 1984-03-07 | 1985-10-01 | Philips Nv | Optische glasvezel voorzien van een kunststofbedekking en werkwijze voor de vervaardiging daarvan. |
| US4647282A (en) | 1985-08-27 | 1987-03-03 | Moskovsky Nauchno-Issledovatelsky Institut Mikrokhirurgii Glaza | Material for ocular prosthetics |
| US4868251A (en) | 1986-12-24 | 1989-09-19 | Allergan, Inc. | Ultraviolet light absorbing silicone compositions |
| US5236970A (en) * | 1987-02-05 | 1993-08-17 | Allergan, Inc. | Optically clear reinforced silicone elastomers of high optical refractive index and improved mechanical properties for use in intraocular lenses |
| US5034461A (en) * | 1989-06-07 | 1991-07-23 | Bausch & Lomb Incorporated | Novel prepolymers useful in biomedical devices |
| ATE100802T1 (de) | 1989-11-10 | 1994-02-15 | Thor Chemie Gmbh | Stabilisierte waessrige loesungen von 3isothiazolinonen. |
| JP3187464B2 (ja) * | 1991-07-31 | 2001-07-11 | 東レ・ダウコーニング・シリコーン株式会社 | ジフェニルシロキサン・ジメチルシロキサン共重合体およびその製造方法 |
| US5233007A (en) | 1992-04-14 | 1993-08-03 | Allergan, Inc. | Polysiloxanes, methods of making same and high refractive index silicones made from same |
| US5512609A (en) | 1992-04-14 | 1996-04-30 | Allergan, Inc. | Reinforced compositions and lens bodies made from same |
| US5444106A (en) * | 1992-04-21 | 1995-08-22 | Kabi Pharmacia Ophthalmics, Inc. | High refractive index silicone compositions |
| JPH08183856A (ja) * | 1994-12-27 | 1996-07-16 | Toray Dow Corning Silicone Co Ltd | ポリイミド樹脂およびその製造方法 |
| TR200101048T2 (tr) | 1998-10-13 | 2001-07-23 | Pharmacia Groningen B.V. | Enjekte edilebilir göz-içi lensleri |
| US6066172A (en) * | 1998-10-13 | 2000-05-23 | Pharmacia & Upjohn Ab | Injectable intraocular lens |
| US6864341B2 (en) * | 2001-11-02 | 2005-03-08 | Bausch & Lomb Incorporated | High refractive index aromatic-based prepolymer precursors |
| US6777522B2 (en) * | 2001-11-02 | 2004-08-17 | Bausch & Lomb Incorporated | High refractive index aromatic-based prepolymers |
-
2001
- 2001-11-02 US US10/004,418 patent/US6864341B2/en not_active Expired - Fee Related
-
2002
- 2002-10-17 CA CA002465500A patent/CA2465500A1/en not_active Abandoned
- 2002-10-17 CN CNB028219260A patent/CN1301283C/zh not_active Expired - Fee Related
- 2002-10-17 JP JP2003542256A patent/JP2005508423A/ja not_active Withdrawn
- 2002-10-17 KR KR1020047006546A patent/KR20050037428A/ko not_active Withdrawn
- 2002-10-17 AT AT02802797T patent/ATE422514T1/de not_active IP Right Cessation
- 2002-10-17 EP EP02802797A patent/EP1448673B1/en not_active Expired - Lifetime
- 2002-10-17 WO PCT/US2002/033437 patent/WO2003040214A1/en not_active Ceased
- 2002-10-17 DE DE60231140T patent/DE60231140D1/de not_active Expired - Lifetime
-
2004
- 2004-01-26 US US10/765,438 patent/US7132493B2/en not_active Expired - Fee Related
- 2004-01-26 US US10/765,401 patent/US7132492B2/en not_active Expired - Fee Related
- 2004-01-26 US US10/765,425 patent/US6951914B2/en not_active Expired - Fee Related
- 2004-01-26 US US10/765,630 patent/US6844414B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015502764A (ja) * | 2011-09-16 | 2015-01-29 | ベンズ リサーチ アンド ディベロップメント コーポレーション | 眼内レンズ用の紫外光吸収材料およびその使用 |
| US9561302B2 (en) | 2011-09-16 | 2017-02-07 | Benz Research & Development Corp. | Ultraviolet light absorbing materials for intraocular lens and uses thereof |
| US10172705B2 (en) | 2011-09-16 | 2019-01-08 | Benz Research And Development Corp. | Ultraviolet light absorbing materials for intraocular lens and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040158020A1 (en) | 2004-08-12 |
| US20040155373A1 (en) | 2004-08-12 |
| US20050165246A1 (en) | 2005-07-28 |
| EP1448673B1 (en) | 2009-02-11 |
| US6864341B2 (en) | 2005-03-08 |
| EP1448673A1 (en) | 2004-08-25 |
| ATE422514T1 (de) | 2009-02-15 |
| US6844414B2 (en) | 2005-01-18 |
| CN1582312A (zh) | 2005-02-16 |
| US7132493B2 (en) | 2006-11-07 |
| US20030130465A1 (en) | 2003-07-10 |
| CN1301283C (zh) | 2007-02-21 |
| WO2003040214A1 (en) | 2003-05-15 |
| CA2465500A1 (en) | 2003-05-15 |
| DE60231140D1 (de) | 2009-03-26 |
| KR20050037428A (ko) | 2005-04-21 |
| US7132492B2 (en) | 2006-11-07 |
| US20040158019A1 (en) | 2004-08-12 |
| US6951914B2 (en) | 2005-10-04 |
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