CA1184341A - Oxygen permeable hard contact lens - Google Patents
Oxygen permeable hard contact lensInfo
- Publication number
- CA1184341A CA1184341A CA000420023A CA420023A CA1184341A CA 1184341 A CA1184341 A CA 1184341A CA 000420023 A CA000420023 A CA 000420023A CA 420023 A CA420023 A CA 420023A CA 1184341 A CA1184341 A CA 1184341A
- Authority
- CA
- Canada
- Prior art keywords
- methacrylate
- contact lens
- group
- acrylate
- general formula
- 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
Links
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000001301 oxygen Substances 0.000 title claims abstract description 27
- -1 fluoroalkyl acrylate Chemical compound 0.000 claims abstract description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 229920001577 copolymer Polymers 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 5
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract description 33
- 230000035699 permeability Effects 0.000 abstract description 18
- 239000000178 monomer Substances 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- 239000000463 material Substances 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000005250 alkyl acrylate group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 125000005401 siloxanyl group Chemical group 0.000 description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 2
- RSVZYSKAPMBSMY-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)F RSVZYSKAPMBSMY-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- YFICSDVNKFLZRQ-UHFFFAOYSA-N 3-trimethylsilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)C YFICSDVNKFLZRQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RZKKLXUEULTOGP-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)O[Si](C)(C)C RZKKLXUEULTOGP-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GFAGRTRAOGQRLM-UHFFFAOYSA-N (1,2-dihydroxy-6-silylhexan-3-yl) prop-2-enoate Chemical compound C(C=C)(=O)OC(C(O)CO)CCC[SiH3] GFAGRTRAOGQRLM-UHFFFAOYSA-N 0.000 description 1
- QPCSNRIUQIHITQ-UHFFFAOYSA-N (4-methyl-4-silylpentan-2-yl) prop-2-enoate Chemical compound C(C=C)(=O)OC(CC([SiH3])(C)C)C QPCSNRIUQIHITQ-UHFFFAOYSA-N 0.000 description 1
- MNSWITGNWZSAMC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl prop-2-enoate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)C=C MNSWITGNWZSAMC-UHFFFAOYSA-N 0.000 description 1
- JDVGNKIUXZQTFD-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)COC(=O)C=C JDVGNKIUXZQTFD-UHFFFAOYSA-N 0.000 description 1
- DFVPUWGVOPDJTC-UHFFFAOYSA-N 2,2,3,4,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)C(F)(F)F DFVPUWGVOPDJTC-UHFFFAOYSA-N 0.000 description 1
- OOHZIRUJZFRULE-UHFFFAOYSA-N 2,2-dimethylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)C OOHZIRUJZFRULE-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- FSVQAZDYQRQQKH-UHFFFAOYSA-N 2-methylbutan-2-yl prop-2-enoate Chemical compound CCC(C)(C)OC(=O)C=C FSVQAZDYQRQQKH-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- YRWXOUMXQCHHMC-UHFFFAOYSA-N 3-(1,3,5,7,2,4,6,8-tetraoxatetrasilocan-2-yl)propyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCCC[SiH]1O[SiH2]O[SiH2]O[SiH2]O1 YRWXOUMXQCHHMC-UHFFFAOYSA-N 0.000 description 1
- NWBTXZPDTSKZJU-UHFFFAOYSA-N 3-[dimethyl(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)C NWBTXZPDTSKZJU-UHFFFAOYSA-N 0.000 description 1
- RYRQMYPWGQPFSJ-UHFFFAOYSA-N 3-bis(trimethylsilyloxy)silylbutyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCCC([SiH](O[Si](C)(C)C)O[Si](C)(C)C)C RYRQMYPWGQPFSJ-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- QKXPVPOKNFDLOK-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylhexane-1,2,3-triol Chemical compound CCCC(O)(C(O)CO)[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C QKXPVPOKNFDLOK-UHFFFAOYSA-N 0.000 description 1
- GUFKIXXGBFDAEK-UHFFFAOYSA-N 3-tris[[methyl-bis(trimethylsilyloxy)silyl]oxy]silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C)(O[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C GUFKIXXGBFDAEK-UHFFFAOYSA-N 0.000 description 1
- UGXNQRLVNTUILQ-UHFFFAOYSA-N 3-tris[[methyl-bis(trimethylsilyloxy)silyl]oxy]silylpropyl prop-2-enoate Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)O[Si](O[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C)(O[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C)CCCOC(=O)C=C UGXNQRLVNTUILQ-UHFFFAOYSA-N 0.000 description 1
- KYNGJGFVBNEJMR-UHFFFAOYSA-N 6-tris(trimethylsilyloxy)silylhexane-1,2,3-triol Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCC(O)C(O)CO KYNGJGFVBNEJMR-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 241000876472 Umma Species 0.000 description 1
- GEEFZQNSLKHSGB-UHFFFAOYSA-N [1,2-dihydroxy-6-[methyl(trimethylsilyloxy)silyl]-3-(2-trimethylsilylethyl)hexan-3-yl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC(C(O)CO)(CCC[SiH](O[Si](C)(C)C)C)CC[Si](C)(C)C GEEFZQNSLKHSGB-UHFFFAOYSA-N 0.000 description 1
- PMAPYFKCKOQCLK-UHFFFAOYSA-N [1-[methyl(trimethylsilyloxy)silyl]-3-silylpropyl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC([SiH](O[Si](C)(C)C)C)CC[SiH3] PMAPYFKCKOQCLK-UHFFFAOYSA-N 0.000 description 1
- FAQPSTUYBXJPBF-UHFFFAOYSA-N [2,3,4,5,5,5-hexafluoro-2,4-bis(trifluoromethyl)pentyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(C(F)(F)F)C(F)C(F)(C(F)(F)F)C(F)(F)F FAQPSTUYBXJPBF-UHFFFAOYSA-N 0.000 description 1
- SQPVWJZAHUFSJY-UHFFFAOYSA-N [2,3,4,5,5,5-hexafluoro-2,4-bis(trifluoromethyl)pentyl] prop-2-enoate Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(F)C(F)(C(F)(F)F)COC(=O)C=C SQPVWJZAHUFSJY-UHFFFAOYSA-N 0.000 description 1
- SFDDRWJEFXXQOM-UHFFFAOYSA-N [2,6-dimethyl-5-propan-2-yl-5-(4,4,8,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocan-2-yl)heptan-3-yl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC(CC([SiH]1O[Si](O[SiH2]O[Si](O1)(C)C)(C)C)(C(C)C)C(C)C)C(C)C SFDDRWJEFXXQOM-UHFFFAOYSA-N 0.000 description 1
- QIBAATKHJHFZRV-UHFFFAOYSA-N [2,6-dimethyl-5-propan-2-yl-5-(4,4,8,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocan-2-yl)heptan-3-yl] prop-2-enoate Chemical compound C(C=C)(=O)OC(CC([SiH]1O[Si](O[SiH2]O[Si](O1)(C)C)(C)C)(C(C)C)C(C)C)C(C)C QIBAATKHJHFZRV-UHFFFAOYSA-N 0.000 description 1
- LLADBMLFLQXWOP-UHFFFAOYSA-N [2-hydroxy-2,3,4-trimethyl-7-silyloxysilyl-4-(2-trimethylsilylethoxy)heptan-3-yl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC(C(OCC[Si](C)(C)C)(CCC[SiH2]O[SiH3])C)(C(O)(C)C)C LLADBMLFLQXWOP-UHFFFAOYSA-N 0.000 description 1
- LAOFRXPBDSRTAR-UHFFFAOYSA-N [3-bis(trimethylsilyloxy)silyl-1,2-dihydroxy-2-[methyl-bis(trimethylsilyloxy)silyl]oxyhexan-3-yl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC(C(O)(CO)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C)(CCC)[SiH](O[Si](C)(C)C)O[Si](C)(C)C LAOFRXPBDSRTAR-UHFFFAOYSA-N 0.000 description 1
- YIZXDTGWEKFZMQ-UHFFFAOYSA-N [3-bis(trimethylsilyloxy)silyl-1,2-dihydroxy-2-methylhexan-3-yl] prop-2-enoate Chemical compound C(C=C)(=O)OC(C(O)(CO)C)(CCC)[SiH](O[Si](C)(C)C)O[Si](C)(C)C YIZXDTGWEKFZMQ-UHFFFAOYSA-N 0.000 description 1
- IBQRMZPPMFWIJZ-UHFFFAOYSA-N [3-ethyl-1,2-dihydroxy-6-[methyl(trimethylsilyloxy)silyl]-2-trimethylsilylhexan-3-yl] prop-2-enoate Chemical compound C(C=C)(=O)OC(C(O)(CO)[Si](C)(C)C)(CCC[SiH](O[Si](C)(C)C)C)CC IBQRMZPPMFWIJZ-UHFFFAOYSA-N 0.000 description 1
- VAHMONSDBBIGFL-UHFFFAOYSA-N [4,4,5,5,6,6,7,7,8,8,9,9,10,11,11,11-hexadecafluoro-2-hydroxy-10-(trifluoromethyl)undecyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)C(F)(F)F VAHMONSDBBIGFL-UHFFFAOYSA-N 0.000 description 1
- LZKRGSPBGVICLV-UHFFFAOYSA-N [4,4,5,5,6,7,7,7-octafluoro-2-hydroxy-6-(trifluoromethyl)heptyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CC(F)(F)C(F)(F)C(F)(C(F)(F)F)C(F)(F)F LZKRGSPBGVICLV-UHFFFAOYSA-N 0.000 description 1
- KUHFADVQXJEDRF-UHFFFAOYSA-N [4-bis(trimethylsilyloxy)silyl-2-[methyl(trimethylsilyloxy)silyl]butan-2-yl] 2-methylprop-2-enoate Chemical compound C[Si](C)(C)O[SiH](C)C(C)(OC(=O)C(C)=C)CC[SiH](O[Si](C)(C)C)O[Si](C)(C)C KUHFADVQXJEDRF-UHFFFAOYSA-N 0.000 description 1
- TZBHKVKXMZYBIU-UHFFFAOYSA-N [4-bis(trimethylsilyloxy)silyl-2-[methyl(trimethylsilyloxy)silyl]butan-2-yl] prop-2-enoate Chemical compound C[Si](C)(C)O[SiH](C)C(C)(OC(=O)C=C)CC[SiH](O[Si](C)(C)C)O[Si](C)(C)C TZBHKVKXMZYBIU-UHFFFAOYSA-N 0.000 description 1
- MTQNFATZKXLGSI-UHFFFAOYSA-N [6-bis(trimethylsilyloxy)silyl-1,2-dihydroxy-3-methylhexan-3-yl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C(O)CO)CCC[SiH](O[Si](C)(C)C)O[Si](C)(C)C MTQNFATZKXLGSI-UHFFFAOYSA-N 0.000 description 1
- YGDJUKOHFTZYQD-UHFFFAOYSA-N [6-bis(trimethylsilyloxy)silyl-1,2-dihydroxy-3-methylhexan-3-yl] prop-2-enoate Chemical compound C(C=C)(=O)OC(C(O)CO)(CCC[SiH](O[Si](C)(C)C)O[Si](C)(C)C)C YGDJUKOHFTZYQD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 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
- 230000005540 biological transmission Effects 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 238000010002 mechanical finishing Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP77133/1982 | 1982-05-08 | ||
| JP57077133A JPS58194014A (ja) | 1982-05-08 | 1982-05-08 | 酸素透過性硬質コンタクトレンズ |
| JP57137597A JPS5928127A (ja) | 1982-08-07 | 1982-08-07 | 酸素透過性硬質コンタクトレンズ |
| JP137597/1982 | 1982-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1184341A true CA1184341A (en) | 1985-03-19 |
Family
ID=26418225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000420023A Expired CA1184341A (en) | 1982-05-08 | 1983-01-21 | Oxygen permeable hard contact lens |
Country Status (6)
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5919918A (ja) * | 1982-07-27 | 1984-02-01 | Hoya Corp | 酸素透過性ハ−ドコンタクトレンズ |
| JPS59185310A (ja) * | 1983-04-06 | 1984-10-20 | Toyo Contact Lens Co Ltd | 酸素透過性軟質コンタクトレンズ用組成物 |
| US4508884A (en) * | 1983-05-25 | 1985-04-02 | Coopervision, Inc. | Oxygen permeable hard contact lens |
| US4616045A (en) * | 1983-06-23 | 1986-10-07 | Gbf, Inc. | Process of preparing an oxygen permeable, styrene based, contact lens material |
| US4528301A (en) * | 1983-06-23 | 1985-07-09 | Gbf, Inc. | Oxygen permeable, styrene based, contact lens material |
| JPS6020910A (ja) * | 1983-07-15 | 1985-02-02 | Shin Etsu Chem Co Ltd | 塩化ビニル系共重合体の製造方法 |
| US4602074A (en) * | 1983-12-20 | 1986-07-22 | Nippon Contact Lens Manufacturing Ltd. | Contact lens material |
| US4507452A (en) * | 1984-03-08 | 1985-03-26 | John D. McCarry | Silicone hydride contact lens and polymer |
| US4829137A (en) * | 1985-01-29 | 1989-05-09 | Bausch & Lomb Incorporated | Continuous-wear highly oxygen permeable contact lenses |
| AU593543B2 (en) * | 1985-01-29 | 1990-02-15 | Bausch & Lomb Incorporated | Continuous-wear lenses |
| US5002979A (en) * | 1985-01-29 | 1991-03-26 | Bausch & Lomb Incorporated | Extended-wear lenses |
| US5084537A (en) * | 1985-01-29 | 1992-01-28 | Bausch & Lomb, Incorporated | UV-absorbing extended-wear Lenses |
| WO1986004342A1 (en) * | 1985-01-29 | 1986-07-31 | Bausch And Lomb Incorporated | Oxygen-permeable lenses |
| CA1295078C (en) * | 1985-01-29 | 1992-01-28 | Nick Stoyan | Extended-wear lenses |
| JPS62123425A (ja) * | 1985-08-02 | 1987-06-04 | Sharp Corp | 液晶表示素子 |
| US4693446A (en) * | 1985-09-20 | 1987-09-15 | Techna Vision, Inc. | Gasket for molding plastic lenses |
| US4996275A (en) * | 1985-10-11 | 1991-02-26 | Polymer Technology Corporation | Fluorine containing polymeric compositions useful in contact lenses |
| US4868260A (en) * | 1985-10-25 | 1989-09-19 | Tomei Sangyo Kabushiki Kaisha | Hard contact lens material consisting of alkyl fumarate and silicon-alkyl fumarate copolymers |
| US5142009A (en) * | 1985-10-25 | 1992-08-25 | Tomei Sangyo Kabushiki Kaisha | Hard contact lens material |
| CA1222845A (en) * | 1986-02-06 | 1987-06-09 | Progressive Chemical Research Ltd. | Silicone-sulfone and silicone-fluorocarbon-sulfone gas permeable contact lenses and compositions thereof |
| US4752627A (en) * | 1986-08-13 | 1988-06-21 | Michael Froix | Clouding-resistant contact lens compositions |
| US4871785A (en) * | 1986-08-13 | 1989-10-03 | Michael Froix | Clouding-resistant contact lens compositions |
| US4861840A (en) * | 1986-12-03 | 1989-08-29 | Barnes-Hind, Inc. | Novel siloxanyl acrylic monomer and gas-permeable contact lenses made therefrom |
| WO1988005060A1 (en) * | 1987-01-07 | 1988-07-14 | Chang Sing Hsiung | Wettable, hydrophilic, soft and oxygen permeable copolymer compositions |
| US4780515A (en) * | 1987-02-05 | 1988-10-25 | Bausch & Lomb Incorporated | Continuous-wear lenses having improved physical properties |
| JPH0627911B2 (ja) * | 1987-06-06 | 1994-04-13 | 株式会社メニコン | コンタクトレンズ材料 |
| DE68900100D1 (de) * | 1988-02-26 | 1991-07-11 | Ciba Geigy Ag | Benetzbare, flexible, sauerstoffdurchlaessige kontaktlinse, bestehend aus blockcopolymeren mit polysiloxan-polyoxyalkylen-gliedern in der hauptkette, und verwendung hierfuer. |
| JP2746376B2 (ja) * | 1988-04-30 | 1998-05-06 | ホーヤ株式会社 | コンタクトレンズ |
| US4933406A (en) * | 1988-09-12 | 1990-06-12 | Nippon Oil And Fats Co., Ltd. | Contact lens article made of silicon- and fluorine-containing resin |
| US5177168A (en) * | 1989-10-17 | 1993-01-05 | Polymer Technology Corp. | Polymeric compositions useful in oxygen permeable contact lenses |
| US5032658A (en) * | 1989-10-17 | 1991-07-16 | Polymer Technology Corporation | Polymeric compositions useful in oxygen permeable contact lenses |
| ES2074687T3 (es) * | 1990-05-02 | 1995-09-16 | Ciba Geigy Ag | Nuevos polimeros y lentes de contacto duras, permeables a los gases, obtenidas con los mismos. |
| US5264878A (en) * | 1990-05-02 | 1993-11-23 | Ciba-Geigy Corporation | Polymers and hard, gas-permeable contact lenses made therefrom |
| JP3108550B2 (ja) * | 1992-11-11 | 2000-11-13 | 株式会社メニコン | 軟質眼用レンズ材料 |
| US5760100B1 (en) * | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
| TW585882B (en) * | 1995-04-04 | 2004-05-01 | Novartis Ag | A method of using a contact lens as an extended wear lens and a method of screening an ophthalmic lens for utility as an extended-wear lens |
| FR2752463A1 (fr) * | 1996-08-14 | 1998-02-20 | Gervais Claude Rene | Lentille de contact rigide deformable |
| JP4066497B2 (ja) * | 1998-03-23 | 2008-03-26 | ダイキン工業株式会社 | 含フッ素共重合体を含んでなる化粧品 |
| JP4087947B2 (ja) | 1998-05-08 | 2008-05-21 | Ｈｏｙａヘルスケア株式会社 | ガス透過型ハードコンタクトレンズの製造方法 |
| US6488375B2 (en) | 1999-10-28 | 2002-12-03 | Ocular Sciences, Inc. | Tinted contact lens and method for making same |
| US6880932B2 (en) * | 1999-11-01 | 2005-04-19 | Praful Doshi | Tinted lenses and methods of manufacture |
| US7267846B2 (en) * | 1999-11-01 | 2007-09-11 | Praful Doshi | Tinted lenses and methods of manufacture |
| US7048375B2 (en) * | 1999-11-01 | 2006-05-23 | Praful Doshi | Tinted lenses and methods of manufacture |
| AU782256B2 (en) | 1999-11-01 | 2005-07-14 | Praful Doshi | Tinted lenses and methods of manufacture |
| JP5076256B2 (ja) * | 2000-09-05 | 2012-11-21 | 東レ株式会社 | モノマー組成物、それを用いたポリマーおよび眼用レンズ |
| JP5011601B2 (ja) * | 2000-10-12 | 2012-08-29 | 東レ株式会社 | ポリマーおよびそれを用いた眼用レンズ |
| ATE433455T1 (de) * | 2001-03-30 | 2009-06-15 | Johnson & Johnson Vision Care | Monomer, polymer und jeweils daraus erhaltene okularlinse und kontaktlinse |
| US6815074B2 (en) | 2001-05-30 | 2004-11-09 | Novartis Ag | Polymeric materials for making contact lenses |
| CA2451542A1 (en) * | 2001-06-18 | 2002-12-27 | Honeywell International Inc. | Fluorine-containing compounds and polymers derived therefrom |
| US20030165015A1 (en) * | 2001-12-05 | 2003-09-04 | Ocular Sciences, Inc. | Coated contact lenses and methods for making same |
| US20060226402A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Ophthalmic devices comprising photochromic materials having extended PI-conjugated systems |
| US20060227287A1 (en) * | 2005-04-08 | 2006-10-12 | Frank Molock | Photochromic ophthalmic devices made with dual initiator system |
| US8158037B2 (en) | 2005-04-08 | 2012-04-17 | Johnson & Johnson Vision Care, Inc. | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
| US9052438B2 (en) | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
| US7994356B2 (en) * | 2009-07-09 | 2011-08-09 | Bausch & Lomb Incorporated | Mono ethylenically unsaturated polycarbosiloxane monomers |
| US8772367B2 (en) * | 2011-03-21 | 2014-07-08 | Momentive Performance Materials Inc. | Siloxane monomers containing hydrolysis resistance carbosiloxane linkage, process for their preparation and thin films containing the same for contact lens application |
| EP2688892B1 (en) * | 2011-03-21 | 2020-11-18 | Momentive Performance Materials Inc. | Siloxane monomers containing hydrolysis resistance carbosiloxane linkage and thin films containing the same for contact lens application |
| US10391179B2 (en) * | 2011-03-21 | 2019-08-27 | Momentive Performance Materials Inc. | Organomodified carbosiloxane monomers containing compositions and uses thereof |
| JP6070193B2 (ja) | 2011-08-17 | 2017-02-01 | 東レ株式会社 | 医療デバイスおよびその製造方法 |
| KR20140134715A (ko) * | 2012-03-22 | 2014-11-24 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 유기-개질 실리콘 폴리머 |
| TW201918524A (zh) * | 2017-10-31 | 2019-05-16 | 鴻海精密工業股份有限公司 | 硬性透氧性眼用鏡片材料及硬性透氧性眼用鏡片 |
| JP7560865B2 (ja) * | 2018-01-31 | 2024-10-03 | ケラメッド インコーポレーテッド | 眼内インプラント用の抗微生物性ポリマ |
| CN113166423B (zh) | 2018-12-31 | 2023-02-17 | 美国陶氏有机硅公司 | 支链有机硅化合物、制备支链有机硅化合物的方法以及包含支链有机硅化合物的组合物 |
| CN115052932A (zh) * | 2018-12-31 | 2022-09-13 | 美国陶氏有机硅公司 | 组合物、制备共聚物的方法及其方法和最终用途 |
| KR20210110843A (ko) | 2018-12-31 | 2021-09-09 | 다우 실리콘즈 코포레이션 | 분지형 유기규소 화합물, 이의 제조 방법, 및 이로 형성된 공중합체 |
| JP2022515662A (ja) | 2018-12-31 | 2022-02-21 | ダウ シリコーンズ コーポレーション | アクリレート官能性分枝状有機ケイ素化合物、それを調製する方法、及びそれによって形成されたコポリマー |
| JP7579257B2 (ja) | 2018-12-31 | 2024-11-07 | ダウ シリコーンズ コーポレーション | 分岐状有機ケイ素化合物、その調製方法、及びそれを含む組成物 |
| US12215117B2 (en) | 2018-12-31 | 2025-02-04 | Dow Silicones Corporation | Method of preparing acryloxy-functional organosilicon compounds |
| KR20210114430A (ko) | 2018-12-31 | 2021-09-23 | 다우 실리콘즈 코포레이션 | 분지형 유기규소 화합물, 그의 제조 방법, 및 그로 형성된 공중합체 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950315A (en) * | 1971-06-11 | 1976-04-13 | E. I. Du Pont De Nemours And Company | Contact lens having an optimum combination of properties |
| US3808179A (en) * | 1972-06-16 | 1974-04-30 | Polycon Laboratories | Oxygen-permeable contact lens composition,methods and article of manufacture |
| US3808178A (en) * | 1972-06-16 | 1974-04-30 | Polycon Laboratories | Oxygen-permeable contact lens composition,methods and article of manufacture |
| US4120570A (en) * | 1976-06-22 | 1978-10-17 | Syntex (U.S.A.) Inc. | Method for correcting visual defects, compositions and articles of manufacture useful therein |
| US4182822A (en) * | 1976-11-08 | 1980-01-08 | Chang Sing Hsiung | Hydrophilic, soft and oxygen permeable copolymer composition |
| CA1103838A (en) * | 1977-10-12 | 1981-06-23 | Kyoichi Tanaka | Polymer for contact lens and contact lens made thereof |
| JPS584327B2 (ja) * | 1978-07-15 | 1983-01-26 | 東洋コンタクトレンズ株式会社 | コンタクトレンズ |
| US4216303A (en) * | 1979-01-26 | 1980-08-05 | George F. Tsuetaki | Oxygen-permeable contact lens compositions, methods and articles of manufacture |
| US4242483A (en) * | 1979-08-13 | 1980-12-30 | Novicky Nick N | Oxygen permeable hard and semi-hard contact lens compositions, methods and articles of manufacture |
| WO1982003397A1 (en) * | 1981-03-24 | 1982-10-14 | John D Mccarry | Silicone methacrylate hydrogels for contact lenses |
| US4440918A (en) * | 1982-01-18 | 1984-04-03 | Minnesota Mining And Manufacturing Company | Contact lens containing a fluorinated telechelic polyether |
| JPS5919918A (ja) * | 1982-07-27 | 1984-02-01 | Hoya Corp | 酸素透過性ハ−ドコンタクトレンズ |
-
1983
- 1983-01-20 AU AU10629/83A patent/AU546039B2/en not_active Expired
- 1983-01-21 CA CA000420023A patent/CA1184341A/en not_active Expired
- 1983-01-21 US US06/459,981 patent/US4433125A/en not_active Expired - Lifetime
- 1983-02-08 DE DE3304089A patent/DE3304089C3/de not_active Expired - Lifetime
- 1983-02-10 FR FR8302136A patent/FR2526551B1/fr not_active Expired
- 1983-02-17 GB GB08304377A patent/GB2119951B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3304089C3 (de) | 1994-08-11 |
| FR2526551A1 (fr) | 1983-11-10 |
| AU546039B2 (en) | 1985-08-08 |
| US4433125A (en) | 1984-02-21 |
| GB2119951B (en) | 1986-09-17 |
| DE3304089C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-08-11 |
| AU1062983A (en) | 1983-11-10 |
| FR2526551B1 (fr) | 1987-07-03 |
| GB2119951A (en) | 1983-11-23 |
| GB8304377D0 (en) | 1983-03-23 |
| DE3304089A1 (de) | 1983-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20030121 |