SG186289A1 - 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
- SG186289A1 SG186289A1 SG2012091096A SG2012091096A SG186289A1 SG 186289 A1 SG186289 A1 SG 186289A1 SG 2012091096 A SG2012091096 A SG 2012091096A SG 2012091096 A SG2012091096 A SG 2012091096A SG 186289 A1 SG186289 A1 SG 186289A1
- Authority
- SG
- Singapore
- Prior art keywords
- methacrylate
- acrylate
- device material
- monomer
- polymeric device
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 89
- 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 28
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims description 52
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 15
- -1 2-3-methylphenylethyl Chemical group 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 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
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 9
- 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 8
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 claims description 8
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 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
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 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
- 229910052760 oxygen 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
- 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
- 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
- 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
- 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
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 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
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000009423 ventilation Methods 0.000 claims description 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
- WRIQURLBLGHVCP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CC)OC(=O)C(C)=C WRIQURLBLGHVCP-UHFFFAOYSA-N 0.000 claims 1
- HLDSNTBYNBFQQM-UHFFFAOYSA-N 2,2-diphenylethyl prop-2-enoate Chemical compound C=1C=CC=CC=1C(COC(=O)C=C)C1=CC=CC=C1 HLDSNTBYNBFQQM-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
- 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
- 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 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
- 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 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
- 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
- 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
- FNIWUDWOOTVEKP-UHFFFAOYSA-N 2-phenylpropyl prop-2-enoate Chemical compound C=CC(=O)OCC(C)C1=CC=CC=C1 FNIWUDWOOTVEKP-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
- 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 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-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
- 238000009472 formulation Methods 0.000 description 15
- 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 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QBCRMBFHJWFTMO-UHFFFAOYSA-N [2-hydroxy-3-[(4-methoxyphenyl)diazenyl]-5-methylphenyl]methyl 2-methylprop-2-enoate Chemical compound C1=CC(OC)=CC=C1N=NC1=CC(C)=CC(COC(=O)C(C)=C)=C1O QBCRMBFHJWFTMO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- 102100041003 Glutamate carboxypeptidase 2 Human genes 0.000 description 2
- 101000892862 Homo sapiens Glutamate carboxypeptidase 2 Proteins 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
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- 238000013461 design Methods 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- 239000012632 extractable Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
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- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 2
- 229920001481 poly(stearyl methacrylate) Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 229910001220 stainless steel Inorganic materials 0.000 description 2
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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
- CXKZIYUKNUMIBO-UHFFFAOYSA-N 1-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OC(C)C1=CC=CC=C1 CXKZIYUKNUMIBO-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
- NCGHOOVBTJLVFY-UHFFFAOYSA-N 2-(2-methylphenyl)ethyl prop-2-enoate Chemical compound CC1=CC=CC=C1CCOC(=O)C=C NCGHOOVBTJLVFY-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
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- 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
- 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
- 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
- 125000001181 organosilyl group Chemical group [SiH3]* 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
- 238000001356 surgical procedure 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
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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)
- Public Health (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Eyeglasses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35696310P | 2010-06-21 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| SG186289A1 true SG186289A1 (en) | 2013-01-30 |
Family
ID=44485011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012091096A SG186289A1 (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 (enExample) |
| EP (1) | EP2582409B1 (enExample) |
| JP (1) | JP5363683B2 (enExample) |
| KR (1) | KR101353975B1 (enExample) |
| CN (1) | CN102946913B (enExample) |
| AR (1) | AR081963A1 (enExample) |
| AU (1) | AU2011271228B2 (enExample) |
| BR (1) | BR112012032626A2 (enExample) |
| CA (1) | CA2801076C (enExample) |
| ES (1) | ES2523387T3 (enExample) |
| IL (1) | IL223487A (enExample) |
| MX (1) | MX2012015178A (enExample) |
| NZ (1) | NZ603881A (enExample) |
| PH (1) | PH12012502514A1 (enExample) |
| RU (1) | RU2571091C2 (enExample) |
| SG (1) | SG186289A1 (enExample) |
| TW (1) | TWI473823B (enExample) |
| WO (1) | WO2011163126A1 (enExample) |
| ZA (1) | ZA201209331B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN104136050B (zh) * | 2012-02-15 | 2015-12-02 | 诺华股份有限公司 | 含多臂peg大分子单体的眼科和耳鼻喉科装置材料 |
| 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 |
| US9289531B2 (en) | 2013-12-04 | 2016-03-22 | Novartis Ag | Soft acrylic materials with 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) |
| EP3200840B1 (en) | 2014-12-16 | 2021-11-17 | Alcon Inc. | Low-water content acrylate-acrylamide copolymers for ophthalmic devices |
| CA2965740C (en) * | 2014-12-16 | 2019-11-26 | Alcon Inc. | Hydrophobic acrylate-acrylamide copolymers for ophthalmic devices |
| AU2016220438B2 (en) | 2015-02-16 | 2019-06-06 | 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 |
| US20190185629A1 (en) * | 2016-08-05 | 2019-06-20 | Microoptx Inc. | Polymeric devices and methods of making |
| EP3363794A1 (en) * | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Bis-compounds for optically active devices |
| WO2018224935A1 (en) * | 2017-06-05 | 2018-12-13 | Novartis Ag | High refractive index, high abbe number intraocular lens materials |
| CA3096853A1 (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 |
| EP3745999B1 (en) * | 2018-01-31 | 2026-04-29 | Menicon Co., Ltd. | Intraocular lens |
| CN120617622A (zh) * | 2019-03-07 | 2025-09-12 | 徳雷安控股有限公司 | 人工晶体组合物 |
| US11708440B2 (en) | 2019-05-03 | 2023-07-25 | Johnson & Johnson Surgical Vision, Inc. | High refractive index, high Abbe compositions |
| KR102894609B1 (ko) | 2019-05-03 | 2025-12-04 | 존슨 앤드 존슨 서지컬 비전, 인코포레이티드 | 고 굴절률, 고 아베 조성물 |
| 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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| 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 |
| ATE228862T1 (de) | 1995-06-07 | 2002-12-15 | Alcon Lab Inc | Material für ophtalmische linsen mit hohem brechungsindex |
| US6353069B1 (en) | 1998-04-15 | 2002-03-05 | Alcon Manufacturing, Ltd. | High refractive index ophthalmic device materials |
| JP2002511597A (ja) * | 1998-04-15 | 2002-04-16 | アルコン ラボラトリーズ， インコーポレイテッド | 高屈折率眼科用デバイス材料 |
| 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 |
| CA2347537C (en) * | 1999-09-03 | 2009-01-20 | 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 |
| US8153156B2 (en) | 2002-11-13 | 2012-04-10 | The United States Of America As Represented By The Department Of Veteran Affairs | Hydrogel nanocompsites for ophthalmic applications |
| JP4431372B2 (ja) | 2003-11-28 | 2010-03-10 | 株式会社ニデック | 眼内レンズ |
| US7157538B2 (en) * | 2004-08-13 | 2007-01-02 | Alcon, Inc. | Covalently-bound, hydrophilic coating compositions for surgical implants |
| US7714090B2 (en) * | 2005-03-09 | 2010-05-11 | Hoya Corporation | (Meth)acrylate compound and process for the production thereof, (meth)acrylate copolymer and process for the production of (meth)acrylate copolymer, and soft intraocular lens |
| CN1995077A (zh) * | 2006-01-05 | 2007-07-11 | 苏州六六明人工晶体有限公司 | 疏水性透明丙烯酸酯共聚物及其应用 |
| US7789509B2 (en) | 2006-06-01 | 2010-09-07 | Advanced Vision Science, Inc. | Non- or reduced glistenings intraocular lens and method of manufacturing same |
| WO2007149083A1 (en) | 2006-06-21 | 2007-12-27 | Bausch & Lomb Incorporated | Polymerizable surfactants and their use as device forming comonomers |
| TWI399228B (zh) * | 2006-07-21 | 2013-06-21 | Alcon Inc | 低黏性的眼科與耳鼻喉科裝置材料（二） |
| US7714039B2 (en) | 2006-07-21 | 2010-05-11 | Alcon, Inc. | Low-tack ophthalmic and otorhinolaryngological device materials |
| FR2913116B1 (fr) * | 2007-02-23 | 2009-08-28 | Essilor Int | Procede de fabrication d'un article optique revetu d'un revetement anti-reflets ou reflechissant ayant des proprietes d'adhesion et de resistance a l'abrasion ameliorees |
| ES2365290T3 (es) | 2007-07-25 | 2011-09-28 | Alcon, Inc. | Materiales para dispositivo oftálmico de alto índice de refracción. |
| TW200920330A (en) | 2007-10-02 | 2009-05-16 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials containing an alkyl ethoxylate |
| TW200916130A (en) | 2007-10-02 | 2009-04-16 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials containing an alkylphenol ethoxylate |
| TWI426931B (zh) | 2007-10-03 | 2014-02-21 | Alcon Inc | 眼科與耳鼻喉科裝置材料（一） |
| TWI426932B (zh) | 2007-10-05 | 2014-02-21 | Alcon Inc | 眼科與耳鼻喉科裝置材料（三） |
| TWI461186B (zh) * | 2007-10-05 | 2014-11-21 | Alcon Inc | 眼科與耳鼻喉科裝置材料（二） |
| TW201000155A (en) | 2008-05-06 | 2010-01-01 | Alcon Inc | High refractive index ophthalmic device materials |
| EP2470578B1 (en) | 2009-08-24 | 2014-11-12 | Novartis AG | Ophthalmic and otorhinolaryngological device materials |
-
2011
- 2011-06-17 TW TW100121212A patent/TWI473823B/zh not_active IP Right Cessation
- 2011-06-20 NZ NZ603881A patent/NZ603881A/en not_active IP Right Cessation
- 2011-06-20 PH PH1/2012/502514A patent/PH12012502514A1/en unknown
- 2011-06-20 EP EP11729519.6A patent/EP2582409B1/en active Active
- 2011-06-20 AU AU2011271228A patent/AU2011271228B2/en not_active Ceased
- 2011-06-20 CA CA2801076A patent/CA2801076C/en not_active Expired - Fee Related
- 2011-06-20 MX MX2012015178A patent/MX2012015178A/es active IP Right Grant
- 2011-06-20 BR BR112012032626A patent/BR112012032626A2/pt not_active Application Discontinuation
- 2011-06-20 RU RU2013102497/04A patent/RU2571091C2/ru not_active IP Right Cessation
- 2011-06-20 US US13/164,290 patent/US8449610B2/en active Active
- 2011-06-20 SG SG2012091096A patent/SG186289A1/en unknown
- 2011-06-20 CN CN201180030684.4A patent/CN102946913B/zh not_active Expired - Fee Related
- 2011-06-20 WO PCT/US2011/041070 patent/WO2011163126A1/en not_active Ceased
- 2011-06-20 KR KR1020137000765A patent/KR101353975B1/ko not_active Expired - Fee Related
- 2011-06-20 ES ES11729519.6T patent/ES2523387T3/es active Active
- 2011-06-20 JP JP2013516654A patent/JP5363683B2/ja active Active
- 2011-06-21 AR ARP110102145A patent/AR081963A1/es not_active Application Discontinuation
-
2012
- 2012-12-06 IL IL223487A patent/IL223487A/en not_active IP Right Cessation
- 2012-12-10 ZA ZA2012/09331A patent/ZA201209331B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP5363683B2 (ja) | 2013-12-11 |
| ZA201209331B (en) | 2014-02-26 |
| KR101353975B1 (ko) | 2014-01-22 |
| ES2523387T3 (es) | 2014-11-25 |
| TW201206965A (en) | 2012-02-16 |
| WO2011163126A1 (en) | 2011-12-29 |
| CA2801076C (en) | 2014-06-10 |
| EP2582409B1 (en) | 2014-09-10 |
| US8449610B2 (en) | 2013-05-28 |
| US20110313518A1 (en) | 2011-12-22 |
| BR112012032626A2 (pt) | 2016-10-25 |
| JP2013529505A (ja) | 2013-07-22 |
| IL223487A (en) | 2014-07-31 |
| CN102946913B (zh) | 2015-01-07 |
| CA2801076A1 (en) | 2011-12-29 |
| TWI473823B (zh) | 2015-02-21 |
| MX2012015178A (es) | 2013-01-24 |
| EP2582409A1 (en) | 2013-04-24 |
| AU2011271228A1 (en) | 2012-12-20 |
| AR081963A1 (es) | 2012-10-31 |
| PH12012502514A1 (en) | 2017-08-09 |
| CN102946913A (zh) | 2013-02-27 |
| RU2571091C2 (ru) | 2015-12-20 |
| RU2013102497A (ru) | 2014-07-27 |
| KR20130090873A (ko) | 2013-08-14 |
| AU2011271228B2 (en) | 2013-09-12 |
| NZ603881A (en) | 2014-02-28 |
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