JP2005508414A - 高屈折率芳香族ベースプレポリマー - Google Patents
高屈折率芳香族ベースプレポリマー Download PDFInfo
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- JP2005508414A JP2005508414A JP2003542245A JP2003542245A JP2005508414A JP 2005508414 A JP2005508414 A JP 2005508414A JP 2003542245 A JP2003542245 A JP 2003542245A JP 2003542245 A JP2003542245 A JP 2003542245A JP 2005508414 A JP2005508414 A JP 2005508414A
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- Prior art keywords
- group
- acrylate
- alkyl
- methacrylate
- monomers
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 68
- -1 polysiloxanes Polymers 0.000 claims abstract description 59
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 12
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- 210000004087 cornea Anatomy 0.000 claims description 6
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 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
- 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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-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
- 125000005250 alkyl acrylate group Chemical group 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
- 239000004202 carbamide Substances 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
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- 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
- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 238000003754 machining Methods 0.000 claims 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 21
- 230000000704 physical effect Effects 0.000 abstract description 9
- 238000009472 formulation Methods 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000007943 implant Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000003287 optical effect Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 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
- 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 5
- 239000002243 precursor Substances 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
- 239000002775 capsule Substances 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 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 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
- 239000000047 product Substances 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 239000004904 UV filter Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 3
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 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
- 238000001356 surgical procedure Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 2
- 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 208000035965 Postoperative Complications Diseases 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 210000002159 anterior chamber Anatomy 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 229920000249 biocompatible polymer Polymers 0.000 description 2
- 239000003618 borate buffered saline Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000001886 ciliary effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 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 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012632 extractable Substances 0.000 description 2
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates 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
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 2
- 229910000077 silane Inorganic materials 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
- 239000006097 ultraviolet radiation absorber Substances 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
- DHIVLKMGKIZOHF-UHFFFAOYSA-N 1-fluorooctane Chemical compound CCCCCCCCF DHIVLKMGKIZOHF-UHFFFAOYSA-N 0.000 description 1
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 1
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 description 1
- VDEYGKYGGKVVDS-UHFFFAOYSA-N 3-[3-tert-butyl-4-hydroxy-5-(5-methoxybenzotriazol-2-yl)phenoxy]propyl 2-methylprop-2-enoate Chemical compound N1=C2C=C(OC)C=CC2=NN1C1=CC(OCCCOC(=O)C(C)=C)=CC(C(C)(C)C)=C1O VDEYGKYGGKVVDS-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
- UZPLADUPKTWUAG-UHFFFAOYSA-N 4-fluoroheptane Chemical compound CCCC(F)CCC UZPLADUPKTWUAG-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- IMIRTMYIIZODPG-UHFFFAOYSA-N [2-(benzotriazol-2-yl)-4-methylphenyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C)C=C1N1N=C2C=CC=CC2=N1 IMIRTMYIIZODPG-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 238000004026 adhesive bonding Methods 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
- HFNQLYDPNAZRCH-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O.OC(O)=O HFNQLYDPNAZRCH-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 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 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- 210000000871 endothelium corneal Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid 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
- 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
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Silicon Polymers (AREA)
- Eyeglasses (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/004,484 US6777522B2 (en) | 2001-11-02 | 2001-11-02 | High refractive index aromatic-based prepolymers |
| PCT/US2002/032774 WO2003040200A1 (en) | 2001-11-02 | 2002-10-15 | High refractive index aromatic-based prepolymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005508414A true JP2005508414A (ja) | 2005-03-31 |
| JP2005508414A5 JP2005508414A5 (enExample) | 2006-01-05 |
Family
ID=21711030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003542245A Pending JP2005508414A (ja) | 2001-11-02 | 2002-10-15 | 高屈折率芳香族ベースプレポリマー |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US6777522B2 (enExample) |
| EP (1) | EP1444275A1 (enExample) |
| JP (1) | JP2005508414A (enExample) |
| KR (1) | KR20050036888A (enExample) |
| CN (1) | CN1310978C (enExample) |
| AR (1) | AR037171A1 (enExample) |
| CA (1) | CA2465495A1 (enExample) |
| WO (1) | WO2003040200A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012527509A (ja) * | 2009-05-22 | 2012-11-08 | ノバルティス アーゲー | 化学線架橋性シロキサン含有コポリマー |
| JP2015093865A (ja) * | 2013-11-14 | 2015-05-18 | 信越化学工業株式会社 | 眼科デバイス製造用モノマー |
| KR20190025704A (ko) * | 2016-07-06 | 2019-03-11 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | 난시 교정을 위한 소프트 콘택트 렌즈 내의 증가된 강직도의 중심 광학부 |
| US11829008B2 (en) | 2012-03-27 | 2023-11-28 | Johnson & Johnson Vision Care, Inc. | Increased stiffness center optic in soft contact lenses for astigmatism correction |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6864341B2 (en) * | 2001-11-02 | 2005-03-08 | Bausch & Lomb Incorporated | High refractive index aromatic-based prepolymer precursors |
| KR20070042548A (ko) * | 2004-07-28 | 2007-04-23 | 카네카 코포레이션 | 투명성, 이형성이 우수한 열가소성 수지 조성물 |
| EP1777265A1 (en) | 2004-07-28 | 2007-04-25 | Kaneka Corporation | Thermoplastic resin composition |
| SE0403093D0 (sv) * | 2004-12-20 | 2004-12-20 | Amo Groningen Bv | New polysiloxanes; synthesis and use thereof |
| WO2006068950A2 (en) * | 2004-12-22 | 2006-06-29 | Bausch & Lomb Incorporated | Drug delivery device comprising crosslinked polyurethane-siloxane-containing copolymers |
| US7279538B2 (en) * | 2005-04-01 | 2007-10-09 | Bausch & Lomb Incorporated | Aromatic-based polysiloxane prepolymers and ophthalmic devices produced therefrom |
| US8071697B2 (en) * | 2005-05-26 | 2011-12-06 | Dow Corning Corporation | Silicone encapsulant composition for molding small shapes |
| KR101325792B1 (ko) * | 2006-01-17 | 2013-11-04 | 다우 코닝 코포레이션 | 열 안정성 투명 실리콘 수지 조성물 및 이의 제조 방법 및용도 |
| CN101336383B (zh) * | 2006-02-01 | 2012-05-09 | 陶氏康宁公司 | 抗冲击的光波导管及其制造方法 |
| KR20080104279A (ko) * | 2006-02-24 | 2008-12-02 | 다우 코닝 코포레이션 | 실리콘으로 캡슐화된 발광 장치 및 실리콘 제조용의 경화성실리콘 조성물 |
| US7951897B2 (en) * | 2007-01-26 | 2011-05-31 | Bausch & Lomb Incorporated | Synthesis of cationic siloxane prepolymers |
| 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 |
| US8730246B2 (en) * | 2007-05-04 | 2014-05-20 | Autodesk, Inc. | Real-time goal space steering for data-driven character animation |
| WO2009070438A1 (en) | 2007-11-30 | 2009-06-04 | Bausch & Lomb Incorporated | Optical material and method for modifying the refractive index |
| US8940219B2 (en) | 2007-12-31 | 2015-01-27 | Ronald D. Spoor | Ophthalmic device formed by additive fabrication and method thereof |
| US8070475B2 (en) | 2007-12-31 | 2011-12-06 | Bausch & Lomb Incorporated | Casting mold for forming a biomedical device including an ophthalmic device |
| US10026210B2 (en) * | 2008-01-10 | 2018-07-17 | Autodesk, Inc. | Behavioral motion space blending for goal-oriented character animation |
| US7781554B2 (en) * | 2008-03-05 | 2010-08-24 | Bausch & Lomb Incorporated | Polysiloxanes and polysiloxane prepolymers with vinyl or epoxy functionality |
| US8350860B2 (en) * | 2008-05-28 | 2013-01-08 | Autodesk, Inc. | Real-time goal-directed performed motion alignment for computer animated characters |
| US8292952B2 (en) | 2009-03-04 | 2012-10-23 | Aaren Scientific Inc. | System for forming and modifying lenses and lenses formed thereby |
| JP5462288B2 (ja) * | 2009-03-04 | 2014-04-02 | パーフェクト アイピー エルエルシー | レンズを形成および修正するためのシステムならびにそれによって形成されたレンズ |
| US8646916B2 (en) | 2009-03-04 | 2014-02-11 | Perfect Ip, Llc | System for characterizing a cornea and obtaining an opthalmic lens |
| US20110189284A1 (en) * | 2009-12-21 | 2011-08-04 | University Of Bristol | Peptide Fibres |
| US10160854B1 (en) | 2015-08-03 | 2018-12-25 | Gl Chemtec Vision Inc. | Hydrogel materials |
| US11125916B2 (en) | 2016-07-06 | 2021-09-21 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels comprising N-alkyl methacrylamides and contact lenses made thereof |
| EP3515960B1 (en) | 2016-09-19 | 2022-06-01 | Dow Silicones Corporation | Personal care compositions including a polyurethane-polyorganosiloxane copolymer |
| CN109890864B (zh) | 2016-09-19 | 2021-08-31 | 美国陶氏有机硅公司 | 聚氨酯-聚有机硅氧烷共聚物及用于其制备的方法 |
| WO2018052645A1 (en) | 2016-09-19 | 2018-03-22 | Dow Corning Corporation | Skin contact adhesive and methods for its preparation and use |
| US20240026049A1 (en) | 2022-07-21 | 2024-01-25 | Envision Biomedical LLC | Dual-phase zwitterionic monomers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4153641A (en) * | 1977-07-25 | 1979-05-08 | Bausch & Lomb Incorporated | Polysiloxane composition and contact lens |
| US4418165A (en) | 1980-06-03 | 1983-11-29 | Dow Corning Corporation | Optically clear silicone compositions curable to elastomers |
| US4537943A (en) | 1983-07-21 | 1985-08-27 | Innovative Surgical Products, Inc. | Correction of defects in the eye and compositions therefor |
| US4647282A (en) | 1985-08-27 | 1987-03-03 | Moskovsky Nauchno-Issledovatelsky Institut Mikrokhirurgii Glaza | Material for ocular prosthetics |
| US4737558A (en) | 1985-11-25 | 1988-04-12 | Alcon Laboratories, Inc. | Siloxane copolymers for ophthalmic applications |
| US4868251A (en) | 1986-12-24 | 1989-09-19 | Allergan, Inc. | Ultraviolet light absorbing silicone compositions |
| DE3710240A1 (de) * | 1987-03-27 | 1988-10-06 | Siemens Ag | Optische glasfaser mit einer primaerbeschichtung aus acrylsaeureestergruppenhaltigen organopolysiloxanen |
| JPH0627910B2 (ja) * | 1987-05-08 | 1994-04-13 | 株式会社メニコン | コンタクトレンズ材料 |
| JPH0761357B2 (ja) | 1988-03-28 | 1995-07-05 | ホーヤ株式会社 | 眼内レンズ |
| JP2804279B2 (ja) * | 1989-01-28 | 1998-09-24 | 株式会社メニコン | 眼用レンズ材料 |
| 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 |
| EP0796723B1 (en) * | 1995-09-06 | 2001-12-05 | Menicon Co., Ltd. | Process for producing optic lens and optic lens obtained thereby |
| US6039913A (en) | 1998-08-27 | 2000-03-21 | Novartis Ag | Process for the manufacture of an ophthalmic molding |
-
2001
- 2001-11-02 US US10/004,484 patent/US6777522B2/en not_active Expired - Fee Related
-
2002
- 2002-10-15 WO PCT/US2002/032774 patent/WO2003040200A1/en not_active Ceased
- 2002-10-15 CA CA002465495A patent/CA2465495A1/en not_active Abandoned
- 2002-10-15 CN CNB028219244A patent/CN1310978C/zh not_active Expired - Fee Related
- 2002-10-15 JP JP2003542245A patent/JP2005508414A/ja active Pending
- 2002-10-15 KR KR1020047006537A patent/KR20050036888A/ko not_active Withdrawn
- 2002-10-15 EP EP20020784099 patent/EP1444275A1/en not_active Withdrawn
- 2002-10-31 AR ARP020104144A patent/AR037171A1/es not_active Application Discontinuation
-
2004
- 2004-07-12 US US10/889,321 patent/US6864342B2/en not_active Expired - Fee Related
-
2005
- 2005-01-31 US US11/048,501 patent/US7074873B2/en not_active Expired - Lifetime
- 2005-01-31 US US11/048,466 patent/US7098288B2/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012527509A (ja) * | 2009-05-22 | 2012-11-08 | ノバルティス アーゲー | 化学線架橋性シロキサン含有コポリマー |
| US11829008B2 (en) | 2012-03-27 | 2023-11-28 | Johnson & Johnson Vision Care, Inc. | Increased stiffness center optic in soft contact lenses for astigmatism correction |
| JP2015093865A (ja) * | 2013-11-14 | 2015-05-18 | 信越化学工業株式会社 | 眼科デバイス製造用モノマー |
| KR20190025704A (ko) * | 2016-07-06 | 2019-03-11 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | 난시 교정을 위한 소프트 콘택트 렌즈 내의 증가된 강직도의 중심 광학부 |
| JP2019522238A (ja) * | 2016-07-06 | 2019-08-08 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッドＪｏｈｎｓｏｎ ＆ Ｊｏｈｎｓｏｎ Ｖｉｓｉｏｎ Ｃａｒｅ， Ｉｎｃ． | 乱視矯正用のソフトコンタクトレンズにおける剛性が増加した光心 |
| JP7086924B2 (ja) | 2016-07-06 | 2022-06-20 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | 乱視矯正用のソフトコンタクトレンズにおける剛性が増加した光心 |
| KR102494793B1 (ko) * | 2016-07-06 | 2023-02-03 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | 난시 교정을 위한 소프트 콘택트 렌즈 내의 증가된 강직도의 중심 광학부 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030134977A1 (en) | 2003-07-17 |
| AR037171A1 (es) | 2004-10-27 |
| CN1310978C (zh) | 2007-04-18 |
| KR20050036888A (ko) | 2005-04-20 |
| WO2003040200A1 (en) | 2003-05-15 |
| CA2465495A1 (en) | 2003-05-15 |
| US20040254326A1 (en) | 2004-12-16 |
| US7074873B2 (en) | 2006-07-11 |
| EP1444275A1 (en) | 2004-08-11 |
| US20050171314A1 (en) | 2005-08-04 |
| US7098288B2 (en) | 2006-08-29 |
| US6777522B2 (en) | 2004-08-17 |
| CN1582307A (zh) | 2005-02-16 |
| US20050128425A1 (en) | 2005-06-16 |
| US6864342B2 (en) | 2005-03-08 |
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