AU2011271228B2 - High refractive index, acrylic ophthalmic device materials with reduced glistenings - Google Patents
High refractive index, acrylic ophthalmic device materials with reduced glistenings Download PDFInfo
- Publication number
- AU2011271228B2 AU2011271228B2 AU2011271228A AU2011271228A AU2011271228B2 AU 2011271228 B2 AU2011271228 B2 AU 2011271228B2 AU 2011271228 A AU2011271228 A AU 2011271228A AU 2011271228 A AU2011271228 A AU 2011271228A AU 2011271228 B2 AU2011271228 B2 AU 2011271228B2
- Authority
- AU
- Australia
- Prior art keywords
- methacrylate
- acrylate
- device material
- monomer
- ethyl
- 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.)
- Ceased
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- 239000000463 material Substances 0.000 title claims abstract description 88
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 13
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 27
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims description 51
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 claims description 11
- 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 claims description 10
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 9
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 claims description 9
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 9
- 238000004132 cross linking Methods 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000006096 absorbing agent Substances 0.000 claims description 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 6
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 5
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
- MXNDNUJKPFXJJX-UHFFFAOYSA-N 4-phenylbutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCC1=CC=CC=C1 MXNDNUJKPFXJJX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- HYZJSTPCAKOIHY-UHFFFAOYSA-N (2-ethylphenyl) prop-2-eneperoxoate Chemical compound CCC1=CC=CC=C1OOC(=O)C=C HYZJSTPCAKOIHY-UHFFFAOYSA-N 0.000 claims description 2
- MYKCFTANKWJWDH-UHFFFAOYSA-N 2-(2-chlorophenyl)ethyl prop-2-enoate Chemical compound ClC1=CC=CC=C1CCOC(=O)C=C MYKCFTANKWJWDH-UHFFFAOYSA-N 0.000 claims description 2
- NCGHOOVBTJLVFY-UHFFFAOYSA-N 2-(2-methylphenyl)ethyl prop-2-enoate Chemical compound CC1=CC=CC=C1CCOC(=O)C=C NCGHOOVBTJLVFY-UHFFFAOYSA-N 0.000 claims description 2
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 claims description 2
- XHDUOAVFFNBVQL-UHFFFAOYSA-N 2-(3-chlorophenyl)ethyl prop-2-enoate Chemical compound ClC1=CC=CC(CCOC(=O)C=C)=C1 XHDUOAVFFNBVQL-UHFFFAOYSA-N 0.000 claims description 2
- YLLMOWFLCNIVRF-UHFFFAOYSA-N 2-(3-methylphenyl)ethyl prop-2-enoate Chemical compound CC1=CC=CC(CCOC(=O)C=C)=C1 YLLMOWFLCNIVRF-UHFFFAOYSA-N 0.000 claims description 2
- NTGCKQLQMLLOBM-UHFFFAOYSA-N 2-(3-phenylphenyl)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC(C=2C=CC=CC=2)=C1 NTGCKQLQMLLOBM-UHFFFAOYSA-N 0.000 claims description 2
- RXJDBBGJXISASI-UHFFFAOYSA-N 2-(4-benzylphenyl)ethyl prop-2-enoate Chemical compound C1=CC(CCOC(=O)C=C)=CC=C1CC1=CC=CC=C1 RXJDBBGJXISASI-UHFFFAOYSA-N 0.000 claims description 2
- UBUYTJHCXCSVML-UHFFFAOYSA-N 2-(4-bromophenyl)ethyl prop-2-enoate Chemical compound BrC1=CC=C(CCOC(=O)C=C)C=C1 UBUYTJHCXCSVML-UHFFFAOYSA-N 0.000 claims description 2
- AOSFJUASIQDDJG-UHFFFAOYSA-N 2-(4-chlorophenyl)ethyl prop-2-enoate Chemical compound ClC1=CC=C(CCOC(=O)C=C)C=C1 AOSFJUASIQDDJG-UHFFFAOYSA-N 0.000 claims description 2
- SBRAKXRWNCYIPW-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)ethyl prop-2-enoate Chemical compound C1=CC(CCOC(=O)C=C)=CC=C1C1CCCCC1 SBRAKXRWNCYIPW-UHFFFAOYSA-N 0.000 claims description 2
- VZSSEIYYXSLLNB-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethyl prop-2-enoate Chemical compound COC1=CC=C(CCOC(=O)C=C)C=C1 VZSSEIYYXSLLNB-UHFFFAOYSA-N 0.000 claims description 2
- NQURUJFRSFIIAA-UHFFFAOYSA-N 2-(4-methylphenyl)ethyl prop-2-enoate Chemical compound CC1=CC=C(CCOC(=O)C=C)C=C1 NQURUJFRSFIIAA-UHFFFAOYSA-N 0.000 claims description 2
- LQQHDTFYKUFAPF-UHFFFAOYSA-N 2-(4-phenylphenyl)ethyl prop-2-enoate Chemical compound C1=CC(CCOC(=O)C=C)=CC=C1C1=CC=CC=C1 LQQHDTFYKUFAPF-UHFFFAOYSA-N 0.000 claims description 2
- BPPOSMLSWFCOHX-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)ethyl prop-2-enoate Chemical compound CC(C)C1=CC=C(CCOC(=O)C=C)C=C1 BPPOSMLSWFCOHX-UHFFFAOYSA-N 0.000 claims description 2
- APNXLWNPHUNKTR-UHFFFAOYSA-N 2-(4-propylphenyl)ethyl prop-2-enoate Chemical compound CCCC1=CC=C(CCOC(=O)C=C)C=C1 APNXLWNPHUNKTR-UHFFFAOYSA-N 0.000 claims description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 2
- ROJWTNWAEYEKMO-UHFFFAOYSA-N 2-phenylmethoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCC1=CC=CC=C1 ROJWTNWAEYEKMO-UHFFFAOYSA-N 0.000 claims description 2
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 claims description 2
- SJOIDEGZPXSHOC-UHFFFAOYSA-N 3-phenylmethoxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC1=CC=CC=C1 SJOIDEGZPXSHOC-UHFFFAOYSA-N 0.000 claims description 2
- PKBZUGSITIBLFK-UHFFFAOYSA-N 3-phenylpropyl prop-2-enoate Chemical compound C=CC(=O)OCCCC1=CC=CC=C1 PKBZUGSITIBLFK-UHFFFAOYSA-N 0.000 claims description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims description 2
- FBOYEYXUKAKVDL-UHFFFAOYSA-N 5-phenylpentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCC1=CC=CC=C1 FBOYEYXUKAKVDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007943 implant Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 2
- 238000009423 ventilation Methods 0.000 claims description 2
- IGVCHZAHFGFESB-UHFFFAOYSA-N 4-phenylbutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCC1=CC=CC=C1 IGVCHZAHFGFESB-UHFFFAOYSA-N 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 2
- RCTZKJGLWRCHMI-UHFFFAOYSA-N (2-ethylphenyl) 2-methylprop-2-eneperoxoate Chemical compound CCC1=CC=CC=C1OOC(=O)C(C)=C RCTZKJGLWRCHMI-UHFFFAOYSA-N 0.000 claims 1
- AOUAMFARIYTDLK-UHFFFAOYSA-N (4-methylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C)C=C1 AOUAMFARIYTDLK-UHFFFAOYSA-N 0.000 claims 1
- ZALFZMYXGFDRIW-UHFFFAOYSA-N (4-methylphenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=C(C)C=C1 ZALFZMYXGFDRIW-UHFFFAOYSA-N 0.000 claims 1
- HEKMZTKFODLXOP-UHFFFAOYSA-N (4-methylphenyl)methyl prop-2-enoate Chemical compound CC1=CC=C(COC(=O)C=C)C=C1 HEKMZTKFODLXOP-UHFFFAOYSA-N 0.000 claims 1
- OGBWMWKMTUSNKE-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CCCCCC(OC(=O)C(C)=C)OC(=O)C(C)=C OGBWMWKMTUSNKE-UHFFFAOYSA-N 0.000 claims 1
- ITKPEKLPFWJSOJ-UHFFFAOYSA-N 2-(2-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1Cl ITKPEKLPFWJSOJ-UHFFFAOYSA-N 0.000 claims 1
- YEQRGDXTQPUPMJ-UHFFFAOYSA-N 2-(2-methylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1C YEQRGDXTQPUPMJ-UHFFFAOYSA-N 0.000 claims 1
- CAWQOFMAJKVFII-UHFFFAOYSA-N 2-(3-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(Cl)=C1 CAWQOFMAJKVFII-UHFFFAOYSA-N 0.000 claims 1
- JPTHRABUTMVMHR-UHFFFAOYSA-N 2-(3-methylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(C)=C1 JPTHRABUTMVMHR-UHFFFAOYSA-N 0.000 claims 1
- XUXKNMQGQVAAJA-UHFFFAOYSA-N 2-(4-benzylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1CC1=CC=CC=C1 XUXKNMQGQVAAJA-UHFFFAOYSA-N 0.000 claims 1
- XHMBRNYBXTUYJN-UHFFFAOYSA-N 2-(4-bromophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(Br)C=C1 XHMBRNYBXTUYJN-UHFFFAOYSA-N 0.000 claims 1
- DANPNQMLVGTTRA-UHFFFAOYSA-N 2-(4-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(Cl)C=C1 DANPNQMLVGTTRA-UHFFFAOYSA-N 0.000 claims 1
- WRAODFTZIJZVJH-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1C1CCCCC1 WRAODFTZIJZVJH-UHFFFAOYSA-N 0.000 claims 1
- IOFBPLNRQQDCSU-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethyl 2-methylprop-2-enoate Chemical compound COC1=CC=C(CCOC(=O)C(C)=C)C=C1 IOFBPLNRQQDCSU-UHFFFAOYSA-N 0.000 claims 1
- HKGJTSSOXHQYDQ-UHFFFAOYSA-N 2-(4-methylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(C)C=C1 HKGJTSSOXHQYDQ-UHFFFAOYSA-N 0.000 claims 1
- XKTDLXROKPMKQF-UHFFFAOYSA-N 2-(4-phenylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1C1=CC=CC=C1 XKTDLXROKPMKQF-UHFFFAOYSA-N 0.000 claims 1
- VZHXURTZSGZTOY-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(C)C1=CC=C(CCOC(=O)C(C)=C)C=C1 VZHXURTZSGZTOY-UHFFFAOYSA-N 0.000 claims 1
- WIGVBGZTCYJIIS-UHFFFAOYSA-N 2-(4-propylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(CCOC(=O)C(C)=C)C=C1 WIGVBGZTCYJIIS-UHFFFAOYSA-N 0.000 claims 1
- CWVFILUMTNJKBN-UHFFFAOYSA-N 2-phenylmethoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCC1=CC=CC=C1 CWVFILUMTNJKBN-UHFFFAOYSA-N 0.000 claims 1
- DJENTNKTVLSRNS-UHFFFAOYSA-N 3-phenylmethoxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOCC1=CC=CC=C1 DJENTNKTVLSRNS-UHFFFAOYSA-N 0.000 claims 1
- RXXZODOCQIRRQA-UHFFFAOYSA-N 3-phenylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1=CC=CC=C1 RXXZODOCQIRRQA-UHFFFAOYSA-N 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- RXPPWNDYCIQFQB-UHFFFAOYSA-N 5-phenylpentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCC1=CC=CC=C1 RXPPWNDYCIQFQB-UHFFFAOYSA-N 0.000 claims 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 description 20
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- 238000009472 formulation Methods 0.000 description 15
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- OJNXPAPLAAGFBJ-UHFFFAOYSA-N (4-methylphenyl) prop-2-enoate Chemical compound CC1=CC=C(OC(=O)C=C)C=C1 OJNXPAPLAAGFBJ-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- BQMWZHUIGYNOAL-UHFFFAOYSA-N 1-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)C1=CC=CC=C1 BQMWZHUIGYNOAL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HLTVXJZFIFRXDB-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-methyl-6-(2-methylprop-2-enyl)phenol Chemical compound CC(=C)CC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O HLTVXJZFIFRXDB-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- HBOYQHJSMXAOKY-UHFFFAOYSA-N 3-[methyl-bis(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C HBOYQHJSMXAOKY-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910016455 AlBN Inorganic materials 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
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- ROWSHEZYONOOTN-UHFFFAOYSA-N [2-hydroxy-5-methoxy-3-[5-(trifluoromethyl)benzotriazol-2-yl]phenyl]methyl 2-methylprop-2-enoate Chemical compound COC1=CC(COC(=O)C(C)=C)=C(O)C(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C1 ROWSHEZYONOOTN-UHFFFAOYSA-N 0.000 description 1
- CKIDCRFWPRVLEU-UHFFFAOYSA-N [3-(benzotriazol-2-yl)-4-hydroxyphenyl] prop-2-enoate Chemical class OC1=CC=C(OC(=O)C=C)C=C1N1N=C2C=CC=CC2=N1 CKIDCRFWPRVLEU-UHFFFAOYSA-N 0.000 description 1
- YPMNWQTVWVHXIQ-UHFFFAOYSA-N [methyl-bis(trimethylsilyloxy)silyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C YPMNWQTVWVHXIQ-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 210000000871 endothelium corneal Anatomy 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- RXRHXOLQBOFMDI-UHFFFAOYSA-N methoxymethane;2-methylprop-2-enoic acid Chemical compound COC.CC(=C)C(O)=O RXRHXOLQBOFMDI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-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
- 238000010998 test method Methods 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- NYHMLROEJNBVEF-UHFFFAOYSA-N tris(trimethylsilyloxy)silylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C NYHMLROEJNBVEF-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
- A61F2/16—Intraocular lenses
- A61F2/1602—Corrective lenses for use in addition to the natural lenses of the eyes or for pseudo-phakic eyes
-
- 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
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
- A61F2/16—Intraocular lenses
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- 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
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Eyeglasses (AREA)
- Prostheses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35696310P | 2010-06-21 | 2010-06-21 | |
| US61/356,963 | 2010-06-21 | ||
| PCT/US2011/041070 WO2011163126A1 (en) | 2010-06-21 | 2011-06-20 | High refractive index, acrylic ophthalmic device materials with reduced glistenings |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2011271228A1 AU2011271228A1 (en) | 2012-12-20 |
| AU2011271228B2 true AU2011271228B2 (en) | 2013-09-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011271228A Ceased AU2011271228B2 (en) | 2010-06-21 | 2011-06-20 | High refractive index, acrylic ophthalmic device materials with reduced glistenings |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8449610B2 (https=) |
| EP (1) | EP2582409B1 (https=) |
| JP (1) | JP5363683B2 (https=) |
| KR (1) | KR101353975B1 (https=) |
| CN (1) | CN102946913B (https=) |
| AR (1) | AR081963A1 (https=) |
| AU (1) | AU2011271228B2 (https=) |
| BR (1) | BR112012032626A2 (https=) |
| CA (1) | CA2801076C (https=) |
| ES (1) | ES2523387T3 (https=) |
| IL (1) | IL223487A (https=) |
| MX (1) | MX2012015178A (https=) |
| NZ (1) | NZ603881A (https=) |
| PH (1) | PH12012502514A1 (https=) |
| RU (1) | RU2571091C2 (https=) |
| SG (1) | SG186289A1 (https=) |
| TW (1) | TWI473823B (https=) |
| WO (1) | WO2011163126A1 (https=) |
| ZA (1) | ZA201209331B (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI517861B (zh) | 2011-02-08 | 2016-01-21 | 諾華公司 | 低黏度疏水性眼科裝置材料 |
| TWI513768B (zh) | 2011-06-01 | 2015-12-21 | Novartis Ag | 疏水性丙烯酸系眼內水晶體材料 |
| TWI551646B (zh) | 2011-06-03 | 2016-10-01 | 諾華公司 | 疏水性丙烯酸系眼內水晶體材料 |
| CN103183822B (zh) * | 2011-12-28 | 2016-03-30 | 辽宁奥克化学股份有限公司 | 一种不饱和氨酯聚氧烷基醚及其制备方法 |
| WO2013122584A1 (en) * | 2012-02-15 | 2013-08-22 | Novartis Ag | Ophthalmic and otorhinolaryngological device materials containing a multi-arm peg macromer |
| GB201314455D0 (en) * | 2013-08-13 | 2013-09-25 | Contamac Ltd | Monomers for use in a polymerizable composition and high refractive index polymer for opthalmic applications |
| CA2928011C (en) | 2013-12-04 | 2019-03-26 | Alcon Inc. | Soft acrylic materials comprising a poly(phenylether)-containing monomer having a high refractive index and minimized glistening |
| WO2015170278A1 (en) | 2014-05-07 | 2015-11-12 | Tubitak | A formulation and lens manufacturing process for the production of intraocular lens (iol) |
| WO2016100190A1 (en) * | 2014-12-16 | 2016-06-23 | Novartis Ag | Low-water content acrylate-acrylamide copolymers for ophthalmic devices |
| US9864102B2 (en) | 2014-12-16 | 2018-01-09 | Novartis Ag | Hydrophobic acrylate-acrylamide copolymers for ophthalmic devices |
| CA2971877C (en) | 2015-02-16 | 2019-10-01 | Alcon Inc. | Wet-pack intraocular lens materials with high refractive index |
| CN105536053B (zh) * | 2015-12-29 | 2018-10-02 | 哈尔滨工业大学 | 一种作为人工晶状体材料的亲水性形状记忆水凝胶 |
| CN110088158A (zh) * | 2016-08-05 | 2019-08-02 | 迈克罗欧普提克斯股份有限公司 | 聚合物装置及制造方法 |
| EP3363794A1 (en) * | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Bis-compounds for optically active devices |
| EP3634508B1 (en) * | 2017-06-05 | 2021-10-27 | Alcon Inc. | High refractive index, high abbe number intraocular lens materials |
| WO2019126080A1 (en) * | 2017-12-18 | 2019-06-27 | Dan Sachs | Devices, systems and methods for therapeutic muscle stimulation |
| TW201927263A (zh) | 2017-12-18 | 2019-07-16 | 瑞士商諾華公司 | 觸覺力分佈得到改善的眼內透鏡平台 |
| TW201927262A (zh) | 2017-12-20 | 2019-07-16 | 瑞士商諾華公司 | 具有前偏置光學設計之眼內透鏡 |
| CN111491588A (zh) * | 2018-01-31 | 2020-08-04 | 株式会社目立康 | 人工晶状体 |
| JP7728703B2 (ja) * | 2019-03-07 | 2025-08-25 | テレオン ホールディング ビー．ヴイ． | 眼内レンズ組成物 |
| JP2022531027A (ja) | 2019-05-03 | 2022-07-06 | ジョンソン・アンド・ジョンソン・サージカル・ビジョン・インコーポレイテッド | 高反応性指数、高アッベ組成物 |
| US11708440B2 (en) | 2019-05-03 | 2023-07-25 | Johnson & Johnson Surgical Vision, Inc. | High refractive index, high Abbe compositions |
| US11795252B2 (en) | 2020-10-29 | 2023-10-24 | Johnson & Johnson Surgical Vision, Inc. | Compositions with high refractive index and Abbe number |
| CN113527567B (zh) * | 2021-07-26 | 2023-01-24 | 康小林 | 疏水性无闪光点高折光率眼科聚合物材料 |
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| US5693095A (en) * | 1995-06-07 | 1997-12-02 | Alcon Laboratories, Inc. | High refractive index ophthalmic lens materials |
| US20090093592A1 (en) * | 2007-10-05 | 2009-04-09 | Alcon, Inc. | Ophthalmic and otorhinolaryngological device materials |
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| US4304895A (en) | 1973-06-20 | 1981-12-08 | Wesley-Jessen, Inc. | Ultraviolet absorbing corneal contact lenses |
| US4528311A (en) | 1983-07-11 | 1985-07-09 | Iolab Corporation | Ultraviolet absorbing polymers comprising 2-hydroxy-5-acrylyloxyphenyl-2H-benzotriazoles |
| US5290892A (en) | 1990-11-07 | 1994-03-01 | Nestle S.A. | Flexible intraocular lenses made from high refractive index polymers |
| US5331073A (en) | 1992-11-09 | 1994-07-19 | Allergan, Inc. | Polymeric compositions and intraocular lenses made from same |
| US5470932A (en) | 1993-10-18 | 1995-11-28 | Alcon Laboratories, Inc. | Polymerizable yellow dyes and their use in opthalmic lenses |
| US6353069B1 (en) | 1998-04-15 | 2002-03-05 | Alcon Manufacturing, Ltd. | High refractive index ophthalmic device materials |
| CN1290352A (zh) * | 1998-04-15 | 2001-04-04 | 阿尔康实验室公司 | 高折射率眼科装置用材料 |
| US8247511B2 (en) * | 1999-04-12 | 2012-08-21 | Advanced Vision Science, Inc. | Water plasticized high refractive index polymer for ophthalmic applications |
| US6281319B1 (en) * | 1999-04-12 | 2001-08-28 | Surgidev Corporation | Water plasticized high refractive index polymer for ophthalmic applications |
| WO2001018396A1 (en) * | 1999-09-03 | 2001-03-15 | Baxter International Inc. | Programmable, fluid pressure actuated blood processing systems and methods |
| ATE291045T1 (de) | 1999-09-07 | 2005-04-15 | Alcon Inc | Material für faltbare ophtalmische und otorhinolaryngologische gegenstände |
| FR2808201B1 (fr) | 2000-04-26 | 2002-07-26 | Ass Pour Les Transferts De Tec | Lentille souple intraoculaire a caracteristiques d'hydrophilicite ameliorees et son procede d'obtention |
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-
2011
- 2011-06-17 TW TW100121212A patent/TWI473823B/zh not_active IP Right Cessation
- 2011-06-20 EP EP11729519.6A patent/EP2582409B1/en active Active
- 2011-06-20 BR BR112012032626A patent/BR112012032626A2/pt not_active Application Discontinuation
- 2011-06-20 NZ NZ603881A patent/NZ603881A/en not_active IP Right Cessation
- 2011-06-20 AU AU2011271228A patent/AU2011271228B2/en not_active Ceased
- 2011-06-20 MX MX2012015178A patent/MX2012015178A/es active IP Right Grant
- 2011-06-20 WO PCT/US2011/041070 patent/WO2011163126A1/en not_active Ceased
- 2011-06-20 CN CN201180030684.4A patent/CN102946913B/zh not_active Expired - Fee Related
- 2011-06-20 PH PH1/2012/502514A patent/PH12012502514A1/en unknown
- 2011-06-20 SG SG2012091096A patent/SG186289A1/en unknown
- 2011-06-20 JP JP2013516654A patent/JP5363683B2/ja active Active
- 2011-06-20 US US13/164,290 patent/US8449610B2/en active Active
- 2011-06-20 RU RU2013102497/04A patent/RU2571091C2/ru not_active IP Right Cessation
- 2011-06-20 KR KR1020137000765A patent/KR101353975B1/ko not_active Expired - Fee Related
- 2011-06-20 CA CA2801076A patent/CA2801076C/en not_active Expired - Fee Related
- 2011-06-20 ES ES11729519.6T patent/ES2523387T3/es active Active
- 2011-06-21 AR ARP110102145A patent/AR081963A1/es not_active Application Discontinuation
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2012
- 2012-12-06 IL IL223487A patent/IL223487A/en not_active IP Right Cessation
- 2012-12-10 ZA ZA2012/09331A patent/ZA201209331B/en unknown
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| US5693095A (en) * | 1995-06-07 | 1997-12-02 | Alcon Laboratories, Inc. | High refractive index ophthalmic lens materials |
| US20090093592A1 (en) * | 2007-10-05 | 2009-04-09 | Alcon, Inc. | Ophthalmic and otorhinolaryngological device materials |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110313518A1 (en) | 2011-12-22 |
| CN102946913B (zh) | 2015-01-07 |
| TWI473823B (zh) | 2015-02-21 |
| NZ603881A (en) | 2014-02-28 |
| BR112012032626A2 (pt) | 2016-10-25 |
| IL223487A (en) | 2014-07-31 |
| AR081963A1 (es) | 2012-10-31 |
| SG186289A1 (en) | 2013-01-30 |
| KR101353975B1 (ko) | 2014-01-22 |
| EP2582409A1 (en) | 2013-04-24 |
| AU2011271228A1 (en) | 2012-12-20 |
| ES2523387T3 (es) | 2014-11-25 |
| RU2013102497A (ru) | 2014-07-27 |
| MX2012015178A (es) | 2013-01-24 |
| KR20130090873A (ko) | 2013-08-14 |
| CN102946913A (zh) | 2013-02-27 |
| RU2571091C2 (ru) | 2015-12-20 |
| WO2011163126A1 (en) | 2011-12-29 |
| JP5363683B2 (ja) | 2013-12-11 |
| CA2801076A1 (en) | 2011-12-29 |
| ZA201209331B (en) | 2014-02-26 |
| CA2801076C (en) | 2014-06-10 |
| PH12012502514A1 (en) | 2017-08-09 |
| EP2582409B1 (en) | 2014-09-10 |
| US8449610B2 (en) | 2013-05-28 |
| JP2013529505A (ja) | 2013-07-22 |
| TW201206965A (en) | 2012-02-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: ALCON INC. Free format text: FORMER OWNER(S): NOVARTIS AG |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |