CA2536762A1 - Process for manufacturing intraocular lenses with blue light absorption characteristics - Google Patents
Process for manufacturing intraocular lenses with blue light absorption characteristics Download PDFInfo
- Publication number
- CA2536762A1 CA2536762A1 CA002536762A CA2536762A CA2536762A1 CA 2536762 A1 CA2536762 A1 CA 2536762A1 CA 002536762 A CA002536762 A CA 002536762A CA 2536762 A CA2536762 A CA 2536762A CA 2536762 A1 CA2536762 A1 CA 2536762A1
- Authority
- CA
- Canada
- Prior art keywords
- methacrylate
- light absorption
- blue light
- ethyl methacrylate
- suitable material
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- 230000031700 light absorption Effects 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000000463 material Substances 0.000 claims description 33
- -1 polysiloxanes Polymers 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 239000001043 yellow dye Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 229920001296 polysiloxane Polymers 0.000 claims description 6
- 229910052724 xenon Inorganic materials 0.000 claims description 6
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 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 3
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 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
- UFEHZTGKQGVALB-UHFFFAOYSA-N (2-ethylsulfanylphenyl) 2-methylprop-2-enoate Chemical compound CCSC1=CC=CC=C1OC(=O)C(C)=C UFEHZTGKQGVALB-UHFFFAOYSA-N 0.000 claims description 2
- PAXZRCDQHAXYCI-UHFFFAOYSA-N (2-ethylsulfanylphenyl) prop-2-enoate Chemical compound CCSC1=CC=CC=C1OC(=O)C=C PAXZRCDQHAXYCI-UHFFFAOYSA-N 0.000 claims description 2
- IMNBHNRXUAJVQE-UHFFFAOYSA-N (4-benzoyl-3-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound OC1=CC(OC(=O)C(=C)C)=CC=C1C(=O)C1=CC=CC=C1 IMNBHNRXUAJVQE-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- ACZLUEDVQBUFQM-UHFFFAOYSA-N 2-(3-phenylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(C=2C=CC=CC=2)=C1 ACZLUEDVQBUFQM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 2
- BTGYQHGWZLBJOB-UHFFFAOYSA-N 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenoxy]propyl 2-methylprop-2-enoate Chemical compound CC(C)(C)C1=CC(OCCCOC(=O)C(=C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O BTGYQHGWZLBJOB-UHFFFAOYSA-N 0.000 claims description 2
- RLWDBZIHAUEHLO-UHFFFAOYSA-N 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propyl 2-methylprop-2-enoate Chemical compound CC(C)(C)C1=CC(CCCOC(=O)C(=C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O RLWDBZIHAUEHLO-UHFFFAOYSA-N 0.000 claims description 2
- 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 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 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- WJQBPCWUWOVPCP-UHFFFAOYSA-N [2-(ethylamino)phenyl] 2-methylprop-2-enoate Chemical compound CCNC1=CC=CC=C1OC(=O)C(C)=C WJQBPCWUWOVPCP-UHFFFAOYSA-N 0.000 claims description 2
- FSKSDAZAWNBWFW-UHFFFAOYSA-N [2-(ethylamino)phenyl] prop-2-enoate Chemical compound CCNC1=CC=CC=C1OC(=O)C=C FSKSDAZAWNBWFW-UHFFFAOYSA-N 0.000 claims description 2
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 2
- 239000012964 benzotriazole Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000000977 initiatory effect Effects 0.000 claims 2
- IMIRTMYIIZODPG-UHFFFAOYSA-N [2-(benzotriazol-2-yl)-4-methylphenyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C)C=C1N1N=C2C=CC=CC2=N1 IMIRTMYIIZODPG-UHFFFAOYSA-N 0.000 claims 1
- 210000001525 retina Anatomy 0.000 abstract description 7
- 238000000016 photochemical curing Methods 0.000 abstract description 3
- 230000000903 blocking effect Effects 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000007943 implant Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 208000002177 Cataract Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004087 cornea Anatomy 0.000 description 3
- 230000000254 damaging effect Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000013175 Crataegus laevigata Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000002847 Surgical Wound Diseases 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical class C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 2
- 208000002780 macular degeneration Diseases 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical group 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 229940124543 ultraviolet light absorber Drugs 0.000 description 2
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- DNPYHJOJVAOLLZ-UHFFFAOYSA-N 2-tert-butyl-6-(5-methoxybenzotriazol-2-yl)-4-[3-(2-methylprop-1-enylsilyl)propoxy]phenol Chemical compound N1=C2C=C(OC)C=CC2=NN1C1=CC(OCCC[SiH2]C=C(C)C)=CC(C(C)(C)C)=C1O DNPYHJOJVAOLLZ-UHFFFAOYSA-N 0.000 description 1
- BPPNCCZFDXFYAS-UHFFFAOYSA-N 2h-benzotriazole;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1=CC=CC2=NNN=C21 BPPNCCZFDXFYAS-UHFFFAOYSA-N 0.000 description 1
- OWJKJLOCIDNNGJ-UHFFFAOYSA-N 4-[[4-hydroxybutyl(dimethyl)silyl]oxy-dimethylsilyl]butan-1-ol Chemical compound OCCCC[Si](C)(C)O[Si](C)(C)CCCCO OWJKJLOCIDNNGJ-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000035965 Postoperative Complications Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 239000003618 borate buffered saline Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- RIQVSVGXJVQRNM-UHFFFAOYSA-N cyclopenta-2,4-dien-1-ylbenzene titanium(2+) Chemical class [Ti++].c1cc[c-](c1)-c1ccccc1.c1cc[c-](c1)-c1ccccc1 RIQVSVGXJVQRNM-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 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, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
- A61F2/142—Cornea, e.g. artificial corneae, keratoprostheses or corneal implants for repair of defective corneal tissue
-
- 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, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
- A61F2/16—Intraocular lenses
-
- 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, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
- A61F2/16—Intraocular lenses
- A61F2/1613—Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus
-
- 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, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
-
- 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, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
- A61F2/145—Corneal inlays, onlays, or lenses for refractive correction
-
- 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, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
- A61F2/16—Intraocular lenses
- A61F2/1613—Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus
- A61F2/1659—Intraocular lenses having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus having variable absorption coefficient for electromagnetic radiation, e.g. photochromic lenses
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- 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, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
- A61F2/16—Intraocular lenses
- A61F2002/16965—Lens includes ultraviolet absorber
- A61F2002/1699—Additional features not otherwise provided for
-
- 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
- A61F2240/00—Manufacturing or designing of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
- A61F2240/001—Designing or manufacturing processes
Abstract
A process for producing intraocular lenses (IOLs) capable of absorbing blue light and ultraviolet light using photo curing. Intraocular lenses so produced block blue light and ultraviolet light from reaching the retina of an eye implanted with the IOL. By blocking blue light and ultraviolet light from reaching the retina, the IOL thereby prevents potential damage to the retina.
Description
PROCESS FOR MANUFACTURING INTRAOCULAR
LENSES WITH BLUE LIGHT ABSORPTION CHARACTERISTICS
Field of the Invention:
The present invention relates to a process for manufacturing intraocular lenses with blue light absorption characteristics. More particularly, the present invention relates to a process for manufacturing intraocular lenses using in a lens material one or more visible light photointiators having suitable absorption above 500 nm to cure the lens material using a visible light source.
Background of the Invention:
Since the 1940's optical devices in the form of intraocular lens (10L) implants have been utilized as replacements for diseased or damaged natural ocular lenses. In most cases, an intraocular lens is implanted within an eye at the time of surgically removing the diseased or damaged natural lens, such as for example, in the case of cataracts. For decades, the preferred material for fabricating such intraocular lens implants was poly(methyl methacrylate), which is a rigid, glassy polymer.
Softer, more flexible IOL implants have gained in popularity in more recent years due to their ability to be compressed, folded, rolled or otherwise deformed. Such softer IOL implants may be deformed prior to insertion thereof through an incision in the cornea of an eye. Following insertion of the IOL in an eye, the IOL returns to its original pre-deformed shape due to the memory characteristics of the soft material. Softer, more flexible IOL implants as just described may be implanted into an eye through an incision that is much smaller, i.e., less than 4.0 mm, than that necessary for more rigid IOLs, i.e., 5.5 to 7.0 mm. A larger incision is necessary for more rigid IOL implants because the lens must be inserted through an incision in the cornea slightly larger than the diameter of the inflexible IOL optic portion. Accordingly, more rigid IOL
implants have become less popular in the market since larger incisions have been found to be associated with an increased incidence of postoperative complications, such as induced astigmatism.
With recent advances in small-incision cataract surgery, increased emphasis has been placed on developing soft, foldable materials suitable for use in artificial IOL implants. Mazzocco, U.S. Patent Number 4,573,998, discloses a deformable intraocular lens that can be rolled, folded or stretched to fit through a relatively small incision. The deformable lens is inserted while it is held in its distorted configuration, then released inside the chamber of the eye, whereupon the elastic property of the lens causes it to resume its molded shape. As suitable materials for the deformable lens, Mazzocco discloses polyurethane elastomers, silicone elastomers, hydrogel polymer compounds, organic or synthetic gel compounds and combinations thereof.
In recent years, blue light (400-500 nm) has been recognized as being potentially hazardous to the retina. Accordingly, yellow dyes to block blue light have been used in foldable intraocular lenses, in conjunction with ultraviolet light absorbers, to avoid potential damaging efFects. Freeman et al., U.S.
Patent Number 6,353,069, disclose high refractive index copolymers comprising two or more acrylate and/or methacrylate monomers with aromatic groups. Ophthalmic devices made of the copolymers may also include colored dyes, such as the yellow dyes disclosed in U.S. Patent Number 5,470,932. Such materials exhibit sufficient strength to allow devices made of them, such as intraocular lenses, to be folded or manipulated without fracturing.
Because of intense light absorption in the ultraviolet (UV) and blue light ranges for IOL materials containing blue light and UV light absorbers, it is difficult to cure the IOL materials using traditional photo initiators. Most photo initiators are inactive above 450 nm. Accordingly, IOL materials having blue light absorbers are generally fabricated by thermal cure. Thermal cure is generally more time consuming and thereby less economical than light curing of IOL
materials. In addition, precision may not be easily achieved if plastic molds are used in molding the lenses due to deformation of the molds during thermal cure.
Summary of the Invention:
Soft, foldable, high refractive index, intraocular lenses (IOLs) capable of absorbing blue light and ultraviolet (UV) light are prepared in accordance with the present invention through a curing process using visible light photo initiators having suitable absorption above 500 nm to enable curing using a visible light source. The blue light and UV light absorbing IOLs produced in accordance with the present invention protect an eye's retina from potentially damaging blue light and UV light, thereby possibly providing protection from macular degeneration.
Blue light and UV light absorbing IOLs of the present invention are manufactured from materials having ethylenically unsaturated groups such as acrylates, methacrylates, and the like. Suitable materials also include one or more high refractive index monomers, one or more blue light absorbing moieties, one or more UV light absorbing moieties, and one or more photo initiators having suitable absorption above 500 nm.
LENSES WITH BLUE LIGHT ABSORPTION CHARACTERISTICS
Field of the Invention:
The present invention relates to a process for manufacturing intraocular lenses with blue light absorption characteristics. More particularly, the present invention relates to a process for manufacturing intraocular lenses using in a lens material one or more visible light photointiators having suitable absorption above 500 nm to cure the lens material using a visible light source.
Background of the Invention:
Since the 1940's optical devices in the form of intraocular lens (10L) implants have been utilized as replacements for diseased or damaged natural ocular lenses. In most cases, an intraocular lens is implanted within an eye at the time of surgically removing the diseased or damaged natural lens, such as for example, in the case of cataracts. For decades, the preferred material for fabricating such intraocular lens implants was poly(methyl methacrylate), which is a rigid, glassy polymer.
Softer, more flexible IOL implants have gained in popularity in more recent years due to their ability to be compressed, folded, rolled or otherwise deformed. Such softer IOL implants may be deformed prior to insertion thereof through an incision in the cornea of an eye. Following insertion of the IOL in an eye, the IOL returns to its original pre-deformed shape due to the memory characteristics of the soft material. Softer, more flexible IOL implants as just described may be implanted into an eye through an incision that is much smaller, i.e., less than 4.0 mm, than that necessary for more rigid IOLs, i.e., 5.5 to 7.0 mm. A larger incision is necessary for more rigid IOL implants because the lens must be inserted through an incision in the cornea slightly larger than the diameter of the inflexible IOL optic portion. Accordingly, more rigid IOL
implants have become less popular in the market since larger incisions have been found to be associated with an increased incidence of postoperative complications, such as induced astigmatism.
With recent advances in small-incision cataract surgery, increased emphasis has been placed on developing soft, foldable materials suitable for use in artificial IOL implants. Mazzocco, U.S. Patent Number 4,573,998, discloses a deformable intraocular lens that can be rolled, folded or stretched to fit through a relatively small incision. The deformable lens is inserted while it is held in its distorted configuration, then released inside the chamber of the eye, whereupon the elastic property of the lens causes it to resume its molded shape. As suitable materials for the deformable lens, Mazzocco discloses polyurethane elastomers, silicone elastomers, hydrogel polymer compounds, organic or synthetic gel compounds and combinations thereof.
In recent years, blue light (400-500 nm) has been recognized as being potentially hazardous to the retina. Accordingly, yellow dyes to block blue light have been used in foldable intraocular lenses, in conjunction with ultraviolet light absorbers, to avoid potential damaging efFects. Freeman et al., U.S.
Patent Number 6,353,069, disclose high refractive index copolymers comprising two or more acrylate and/or methacrylate monomers with aromatic groups. Ophthalmic devices made of the copolymers may also include colored dyes, such as the yellow dyes disclosed in U.S. Patent Number 5,470,932. Such materials exhibit sufficient strength to allow devices made of them, such as intraocular lenses, to be folded or manipulated without fracturing.
Because of intense light absorption in the ultraviolet (UV) and blue light ranges for IOL materials containing blue light and UV light absorbers, it is difficult to cure the IOL materials using traditional photo initiators. Most photo initiators are inactive above 450 nm. Accordingly, IOL materials having blue light absorbers are generally fabricated by thermal cure. Thermal cure is generally more time consuming and thereby less economical than light curing of IOL
materials. In addition, precision may not be easily achieved if plastic molds are used in molding the lenses due to deformation of the molds during thermal cure.
Summary of the Invention:
Soft, foldable, high refractive index, intraocular lenses (IOLs) capable of absorbing blue light and ultraviolet (UV) light are prepared in accordance with the present invention through a curing process using visible light photo initiators having suitable absorption above 500 nm to enable curing using a visible light source. The blue light and UV light absorbing IOLs produced in accordance with the present invention protect an eye's retina from potentially damaging blue light and UV light, thereby possibly providing protection from macular degeneration.
Blue light and UV light absorbing IOLs of the present invention are manufactured from materials having ethylenically unsaturated groups such as acrylates, methacrylates, and the like. Suitable materials also include one or more high refractive index monomers, one or more blue light absorbing moieties, one or more UV light absorbing moieties, and one or more photo initiators having suitable absorption above 500 nm.
Accordingly, it is an object of the present invention to provide a process for the production of IOLs with blue light absorption properties.
Another object of the present invention is to provide a process for the production of IOLs having relatively high refractive indices and good clarity.
Another object of the present invention is to provide a process for the production of IOLs that are flexible.
Still another object of the present invention is to provide biocompatible IOLs with blue light absorption properties.
These and other objectives and advantages of the present invention, some of which are specifically described and others that are not, will become apparent from the detailed description and claims that follow.
Brief Description of the Drawings:
FIGURE 1 shows a sample ultraviolet-visible (UV-VIS) spectrum of photo initiator Irgacure-784T"" (Ciba Specialty Chemical, Hawthorne, New York) 0.1 % in methanol solvent.
Detailed Description of the Invention:
The present invention relates to a novel process for the production of high refractive index IOLs with blue light absorption properties to block blue light from reaching the retina of an eye implanted with the IOL. The subject process produces IOLs having blue light and UV light absorption capabilities through a photo curing process. The IOL materials of the present invention include visible light photo initiators having suitable absorption above 500 nm to enable curing in a relatively short period of time, preferably less than several hours, using a visible light source, such as for example a xenon lamp. The blue light and UV light absorbing IOLs produced in accordance with the present invention protect an eye's retina from potentially damaging blue light and UV
light, thereby possibly providing protection from macular degeneration.
IOLs of the present invention are produced from one or more monomers and/or prepolymers having ethylenically unsaturated groups such as acrylates, methacrylates, and the like.
Suitable IOL materials in accordance with the present invention also include one or more monomers or prepolymers having a high refractive index. Suitable monomers having a high refractive index include for example but are not limited to those containing various aromatic moieties. Examples of high refractive index monomers include but are not limited to 2-ethylphenoxy methacrylate, 2-ethylphenoxy acrylate, 2-ethylthiophenyl methacrylate, 2-ethylthiophenyl acrylate, 2-ethylaminophenyl methacrylate, 2-ethylaminophenyl acrylate, phenyl methacrylate, benzyl methacrylate, 2-phenylethyl methacrylate, 3-phenylpropyl methacrylate, 4-phenylbutyl methacrylate, 4-methylphenyl methacrylate, 4-methylbenzyl methacrylate, 2,2-methylphenylethyl methacrylate, 2,3-methylphenylethyl methacrylate, 2,4-methylphenylethyl methacrylate, 2-(4-propylphenyl)ethyl methacrylate, 2-(4-(1-methylethyl)phenyl)ethyl methacrylate, 2-(4-methoxyphenyl)ethyl methacrylate, 2-(4-cyclohexylphenyl)ethyl methacrylate, 2-(2-chlorophenyl)ethyl methacrylate, 2-(3-chlorophenyl)ethyl methacrylate, 2-(4-chlorophenyl)ethyl methacrylate, 2-(4-bromophenyl)ethyl methacrylate, 2-(3-phenylphenyl)ethyl methacrylate, 2-(4-phenylphenyl)ethyl methacrylate, 2-(4-benzylphenyl)ethyl methacrylate, and the like.
Suitable high refractive index prepolymers for use in accordance with the present invention include for example but are not limited to acrylate-capped prepolymers of polysiloxanes and methacrylate-capped prepolymers of polysiloxanes, wherein the prepolymers have a suitable number of aromatic moieties so that the refractive index of the prepolymers are at least 1.42.
Preferably, each polysiloxane unit of the prepolymer may have an average molecular weight of approximately 1,000 to 10,000 with the prepolymer molecular weight being higher than approximately 1,000, but lower than approximately 300,000.
Suitable IOL materials in accordance with the present invention also include blue light,absorbing moieties. Typical blue light absorbing moieties are reactive yellow dyes such as azo-based yellow dye. Examples of such blue light absorbing moieties are provided by but are not limited to those disclosed in D. L. Jinkerson, U.S. Patent Number 5,662,707, incorporated herein in its entirety by reference, as well as those disclosed in its corresponding co-pending patent applications.
Suitable IOL materials in accordance with the present invention also include UV light absorbing moieties. Suitable ultraviolet light absorbers include for example but are not limited to ~3-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2'-methacryloxy-5'-methylphenyl)benzotria~ole, 2-(2'-hydroxy-5'-methacryoxyethylphenyl)-2H-ben~otriazole, 2-[3'-tert-butyl-2'-hydroxy-5'-(3"-methacryloyloxypropyl)phenyl]-5-chlorobenzotriazole, 2-[3'-tert-butyl-5'-(3"-dimethylvinylsilylpropoxy)-2'-hydroxyphenyl]-5-methoxybenzotriazole and 2-[3'-tert-butyl-2'-hydroxy-5'-(3"-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole.
Suitable IOL materials in accordance with the present invention also include photointitiators having a suitable absorption above 500nm.
Examples of suitable photo intiators include but are not limited to substituted UV
photo initiators, conjugated ketones, triazine-yl derivatives, metal salts and the like. One particular preferred class of photo intiator for use in the present invention is titanocene derivatives which can be directly photolyzed upon exposure to a light source. An example of such a titanocene derivative is Irgacure-784T"" (Ciba Specialty Chemical, Hawthorne, New York), the UV-VIS
spectrum of which is illustrated in Figure 1. Irgacure-784 is a fluorinated diphenyl titanocene having the structure illustrated in Formula 1 below.
O
F
Ti F
OC~ F O ~ ~I
To be efficient in visible light polymerization of formulations containing yellow dye, the light source should have sufficient wattage and sufficient emission of light above 450 mn. The preferred light source for use in accordance with the present invention is a high intensity Xenon lamp, such as for example but not limited to Lamp Model RC-257, a pulsed lamp, available commercially from Xenon Corporation, Woburn, Massachussetts. Lamp Model RC-257 provides sufficient wattage and sufficient emission of light above 450 mn for efficient polymerization of formulations containing yellow dye. Using such a high intensity Xenon lamp allows for curing to be completed in less than 4 hours, preferably less than one hour, even more preferably in less than 30 minutes, depending on the intensity applied.
The process of the present invention for preparing flexible, high refractive index IOLs with blue light and UV light absorption capability is described in still greater detail in the examples provided below.
EXAMPLE 1 - Synthesis of N, N-bis- (2-hydroxyethyl)-(4-phenylazo) aniline, (Solvent Yellow 58):
The synthesis of N, N-bis- (2-hydroxyethyl)-(4-phenylazo) aniline is accomplished by the coupling of a diazonium salt of aniline with N-phenyl diethanolamine. A detailed procedure for synthesizing N, N-bis- (2-hydroxyethyl)-(4-phenylazo) aniline is disclosed in D. L. Jinkerson, U. S.
Patent Number 5,470,932.
EXAMPLE 2 - Synthesis of N, N-bis- (2-~acryloxyethyl)-(4'-nhenylazo)aniline:
A 1000 mL 3-neck, round bottom flask connected with a reflux condenser and a drying tube, is charged with 250 mL of methylene chloride, 5.7 grams (0.02 mole) of N, N-bis-(2-hydroxyethyl)-(4-phenylazo)aniline aniline and 4.04 grams of triethylamine. The contents are chilled using an ice bath.
Through a dropping funnel, 7.24 g (0.04 mole) of acryloyl chloride is added into the flask over a period of 30 minutes. The ice bath is then removed and the contents are continuously stirred overnight. The mixture is then filtered and then condensed using a rotavapor. High performance liquid chromatography (HPLC) analysis indicates only one major product. The product is then passed through silica gel chromatography to give final purified product with a yield of at least 80 percent. The product is identified by nuclear magnetic resonance (NMR) and Mass Spectroscopy.
EXAMPLE 3 - Preparation of Hydroxybutyl-Terminated Copolymer of Dimethylsiloxane and Diphenylsiloxane (with 25 mole percent phenyl content 1,3-bis(hydroxybutyl)tetramethyl disiloxane (33.70 g, 0.118 mole), dimethyldimethoxysilane (403.18 g, 3.25 moles) and diphenyldimethoxysilane (272.33 g, 1.08 moles) were added in a one-liter round bottom flask. Water (78.29 g) and concentrated hydrochloric acid (11.9 mL) were then slowly added to the flask. The contents of the flask were refluxed for one hour. Methanol (253.3 mL) was distilled from the contents. Water (160 mL) and concentrated hydrochloric acid (130 mL) was added to the flask. The contents of the flask were refluxed for one hour. The contents of the flask were then poured into a separatory funnel. The silicone layer was separated, diluted with 500 mL ether and washed once with 250 mL water, twice with 250 mL 5-percent sodium bicarbonate aqueous solution and twice with 250 mL water. The final organic layer was dried with magnesium sulfate, and then vacuum stripped at 80 degrees Celsius (0.1 mm Hg) to give the crude product. The crude product was then dissolved in 50/50 cyclohexane/methylene chloride and then passed through a silica gel column with the same solvent mixture. The final product was collected in tetrahydrofuran (THF) by passing THF through the silica gel column. The THF
fractions were combined, dried and vacuum stripped to give the final product.
Size Exclusion Chromatography (SEC) measurements of the final product indicated less than three percent cyclics and a molecular weight of 2821 by titration.
EXAMPLE 4 - Preparation of Methacylate-Capped Prepolymer of Polysiloxane Containing Both Dimethylsiloxane and Diphenylsiloxane Units:
A 500-mL round bottom flask equipped with reflux condenser and nitrogen blanket was charged with isophorone diisocyanate (5.031 g, 0.0227 mole), the hydroxybutyl-terminated copolymer of dimethylsiloxane and the diphenylsiloxane from Example 3 (51.4465 g, 0.0189 mole), dibutyltin dilaurate (0.1811 g) and methylene chloride (150 mL). The flask contents were refluxed.
After about 90 hours of reflux, the isocyanate was found decreased to 16.2 percent (theoretical 16.7 percent) of original. The contents of the flask were allowed to cool to ambient temperature. HEMA (1.1572 g) and 1,1'-2-bi-naphthol (5.7 mg) were added to the flask and stirred. After seven days, NCO peak disappeared from IR spectrum and the reaction was terminated. The product was obtained at quantitative yield after removing solvent.
EXAMPLE 5 - Preparation of High Refractive Index Hydrogels Containing a Yellow Dye Moiety and UV Absorber Useful for IOL Application:
A formulation consists of 50 parts of prepolymer of Example 5, 20 parts of benzyl acrylate, 10 parts of benzyl methacrylate , 20 parts of N,N-dimethyl acrylamide, 0.25 parts benzotriazole methacrylate, 0.2 part N, N-bis-(2-[acryloxyethyl)-(4'-phenylazo)aniline as described in Example 2, and 1 parfi of Irgacure-784. The mix is cured between two silane-treated glass plates under a high intensity visible light lamp, Model RC-257 (Xenon Corporation) for 1 hour.
The cured films are then released, extracted in isopropanol for over 4 hours and dried in a vacuum oven at 70 degrees Celsius overnight. The dried films are then placed in a borate buffered saline overnight before characterization. The films have a thickness of 170-200 microns. The UV-VIS absorption of hydrogel films are then measured and have less than 1 % transmittance below 400 nm and less than 60 % transmittance but above 40 %, below 450 nm. Mechanical properties of the processed films can be adjusted by adjustment of the light intensity applied for curing.
Soft, foldable, relatively high refractive index of approximately 1.42 or greater, relatively high elongation of approximately 100 percent or greater, IOLs with blue light absorption properties are synthesized through the process of the present invention. The IOLs produced as described herein have the flexibility required to allow the same to be folded or deformed for insertion into an eye through the smallest possible surgical incision, i.e., 3.5 mm or smaller. It is unexpected that the subject IOLs described herein could possess the ideal physical properties disclosed herein. The ideal physical properties of the subject IOLs are unexpected due to difficulties previously associated with photo curing of blue light absorbing and UV light absorbing materials.
IOLs manufactured using the process of the present invention can be of any design capable of being rolled or folded for implantation through a relatively small surgical incision, i.e., 3.5 mm or less. Such IOLs may be manufactured to have an optic portion and haptic portions made of the same or differing materials. Once the materials) are selected, the same may be cast in molds of the desired shape, cured and removed from the molds. After such molding, the IOLs are treated in accordance with the process of the present invention and then cleaned, polished, packaged and sterilized by customary methods known to those skilled in the art. Alternatively, the materials may be cast in rods, cut into disks and lathed into the desired shape as known to those skilled in the art.
In addition to IOLs, the process of the present invention is also suitable for use in the production of other medical or ophthalmic devices such as contact lenses, keratoprostheses, capsular bag extension rings, corneal inlays, corneal rings and like devices.
IOLs manufactured using the process of the present invention are used as customary in the field of ophthalmology. For example, in a surgical cataract procedure, an incision is placed in the cornea of an eye. Through the corneal incision the cataractous natural lens of the eye is removed (aphakic application) and an IOL is inserted into the anterior chamber, posterior chamber or lens capsule of the eye prior to closing the incision. However, the subject ophthalmic devices may likewise be used in accordance with other surgical procedures known to those skilled in the field of ophthalmology.
While there is shown and described herein a process for producing IOLs with blue light and ultraviolet light absorption capabilities, it will be manifest to those skilled in the art that various modifications may be made without departing from the spirit and scope of the underlying inventive concept and that the same is not limited to particular processes and structures herein shown and described except insofar as indicated by the scope of the appended claims.
Another object of the present invention is to provide a process for the production of IOLs having relatively high refractive indices and good clarity.
Another object of the present invention is to provide a process for the production of IOLs that are flexible.
Still another object of the present invention is to provide biocompatible IOLs with blue light absorption properties.
These and other objectives and advantages of the present invention, some of which are specifically described and others that are not, will become apparent from the detailed description and claims that follow.
Brief Description of the Drawings:
FIGURE 1 shows a sample ultraviolet-visible (UV-VIS) spectrum of photo initiator Irgacure-784T"" (Ciba Specialty Chemical, Hawthorne, New York) 0.1 % in methanol solvent.
Detailed Description of the Invention:
The present invention relates to a novel process for the production of high refractive index IOLs with blue light absorption properties to block blue light from reaching the retina of an eye implanted with the IOL. The subject process produces IOLs having blue light and UV light absorption capabilities through a photo curing process. The IOL materials of the present invention include visible light photo initiators having suitable absorption above 500 nm to enable curing in a relatively short period of time, preferably less than several hours, using a visible light source, such as for example a xenon lamp. The blue light and UV light absorbing IOLs produced in accordance with the present invention protect an eye's retina from potentially damaging blue light and UV
light, thereby possibly providing protection from macular degeneration.
IOLs of the present invention are produced from one or more monomers and/or prepolymers having ethylenically unsaturated groups such as acrylates, methacrylates, and the like.
Suitable IOL materials in accordance with the present invention also include one or more monomers or prepolymers having a high refractive index. Suitable monomers having a high refractive index include for example but are not limited to those containing various aromatic moieties. Examples of high refractive index monomers include but are not limited to 2-ethylphenoxy methacrylate, 2-ethylphenoxy acrylate, 2-ethylthiophenyl methacrylate, 2-ethylthiophenyl acrylate, 2-ethylaminophenyl methacrylate, 2-ethylaminophenyl acrylate, phenyl methacrylate, benzyl methacrylate, 2-phenylethyl methacrylate, 3-phenylpropyl methacrylate, 4-phenylbutyl methacrylate, 4-methylphenyl methacrylate, 4-methylbenzyl methacrylate, 2,2-methylphenylethyl methacrylate, 2,3-methylphenylethyl methacrylate, 2,4-methylphenylethyl methacrylate, 2-(4-propylphenyl)ethyl methacrylate, 2-(4-(1-methylethyl)phenyl)ethyl methacrylate, 2-(4-methoxyphenyl)ethyl methacrylate, 2-(4-cyclohexylphenyl)ethyl methacrylate, 2-(2-chlorophenyl)ethyl methacrylate, 2-(3-chlorophenyl)ethyl methacrylate, 2-(4-chlorophenyl)ethyl methacrylate, 2-(4-bromophenyl)ethyl methacrylate, 2-(3-phenylphenyl)ethyl methacrylate, 2-(4-phenylphenyl)ethyl methacrylate, 2-(4-benzylphenyl)ethyl methacrylate, and the like.
Suitable high refractive index prepolymers for use in accordance with the present invention include for example but are not limited to acrylate-capped prepolymers of polysiloxanes and methacrylate-capped prepolymers of polysiloxanes, wherein the prepolymers have a suitable number of aromatic moieties so that the refractive index of the prepolymers are at least 1.42.
Preferably, each polysiloxane unit of the prepolymer may have an average molecular weight of approximately 1,000 to 10,000 with the prepolymer molecular weight being higher than approximately 1,000, but lower than approximately 300,000.
Suitable IOL materials in accordance with the present invention also include blue light,absorbing moieties. Typical blue light absorbing moieties are reactive yellow dyes such as azo-based yellow dye. Examples of such blue light absorbing moieties are provided by but are not limited to those disclosed in D. L. Jinkerson, U.S. Patent Number 5,662,707, incorporated herein in its entirety by reference, as well as those disclosed in its corresponding co-pending patent applications.
Suitable IOL materials in accordance with the present invention also include UV light absorbing moieties. Suitable ultraviolet light absorbers include for example but are not limited to ~3-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2'-methacryloxy-5'-methylphenyl)benzotria~ole, 2-(2'-hydroxy-5'-methacryoxyethylphenyl)-2H-ben~otriazole, 2-[3'-tert-butyl-2'-hydroxy-5'-(3"-methacryloyloxypropyl)phenyl]-5-chlorobenzotriazole, 2-[3'-tert-butyl-5'-(3"-dimethylvinylsilylpropoxy)-2'-hydroxyphenyl]-5-methoxybenzotriazole and 2-[3'-tert-butyl-2'-hydroxy-5'-(3"-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole.
Suitable IOL materials in accordance with the present invention also include photointitiators having a suitable absorption above 500nm.
Examples of suitable photo intiators include but are not limited to substituted UV
photo initiators, conjugated ketones, triazine-yl derivatives, metal salts and the like. One particular preferred class of photo intiator for use in the present invention is titanocene derivatives which can be directly photolyzed upon exposure to a light source. An example of such a titanocene derivative is Irgacure-784T"" (Ciba Specialty Chemical, Hawthorne, New York), the UV-VIS
spectrum of which is illustrated in Figure 1. Irgacure-784 is a fluorinated diphenyl titanocene having the structure illustrated in Formula 1 below.
O
F
Ti F
OC~ F O ~ ~I
To be efficient in visible light polymerization of formulations containing yellow dye, the light source should have sufficient wattage and sufficient emission of light above 450 mn. The preferred light source for use in accordance with the present invention is a high intensity Xenon lamp, such as for example but not limited to Lamp Model RC-257, a pulsed lamp, available commercially from Xenon Corporation, Woburn, Massachussetts. Lamp Model RC-257 provides sufficient wattage and sufficient emission of light above 450 mn for efficient polymerization of formulations containing yellow dye. Using such a high intensity Xenon lamp allows for curing to be completed in less than 4 hours, preferably less than one hour, even more preferably in less than 30 minutes, depending on the intensity applied.
The process of the present invention for preparing flexible, high refractive index IOLs with blue light and UV light absorption capability is described in still greater detail in the examples provided below.
EXAMPLE 1 - Synthesis of N, N-bis- (2-hydroxyethyl)-(4-phenylazo) aniline, (Solvent Yellow 58):
The synthesis of N, N-bis- (2-hydroxyethyl)-(4-phenylazo) aniline is accomplished by the coupling of a diazonium salt of aniline with N-phenyl diethanolamine. A detailed procedure for synthesizing N, N-bis- (2-hydroxyethyl)-(4-phenylazo) aniline is disclosed in D. L. Jinkerson, U. S.
Patent Number 5,470,932.
EXAMPLE 2 - Synthesis of N, N-bis- (2-~acryloxyethyl)-(4'-nhenylazo)aniline:
A 1000 mL 3-neck, round bottom flask connected with a reflux condenser and a drying tube, is charged with 250 mL of methylene chloride, 5.7 grams (0.02 mole) of N, N-bis-(2-hydroxyethyl)-(4-phenylazo)aniline aniline and 4.04 grams of triethylamine. The contents are chilled using an ice bath.
Through a dropping funnel, 7.24 g (0.04 mole) of acryloyl chloride is added into the flask over a period of 30 minutes. The ice bath is then removed and the contents are continuously stirred overnight. The mixture is then filtered and then condensed using a rotavapor. High performance liquid chromatography (HPLC) analysis indicates only one major product. The product is then passed through silica gel chromatography to give final purified product with a yield of at least 80 percent. The product is identified by nuclear magnetic resonance (NMR) and Mass Spectroscopy.
EXAMPLE 3 - Preparation of Hydroxybutyl-Terminated Copolymer of Dimethylsiloxane and Diphenylsiloxane (with 25 mole percent phenyl content 1,3-bis(hydroxybutyl)tetramethyl disiloxane (33.70 g, 0.118 mole), dimethyldimethoxysilane (403.18 g, 3.25 moles) and diphenyldimethoxysilane (272.33 g, 1.08 moles) were added in a one-liter round bottom flask. Water (78.29 g) and concentrated hydrochloric acid (11.9 mL) were then slowly added to the flask. The contents of the flask were refluxed for one hour. Methanol (253.3 mL) was distilled from the contents. Water (160 mL) and concentrated hydrochloric acid (130 mL) was added to the flask. The contents of the flask were refluxed for one hour. The contents of the flask were then poured into a separatory funnel. The silicone layer was separated, diluted with 500 mL ether and washed once with 250 mL water, twice with 250 mL 5-percent sodium bicarbonate aqueous solution and twice with 250 mL water. The final organic layer was dried with magnesium sulfate, and then vacuum stripped at 80 degrees Celsius (0.1 mm Hg) to give the crude product. The crude product was then dissolved in 50/50 cyclohexane/methylene chloride and then passed through a silica gel column with the same solvent mixture. The final product was collected in tetrahydrofuran (THF) by passing THF through the silica gel column. The THF
fractions were combined, dried and vacuum stripped to give the final product.
Size Exclusion Chromatography (SEC) measurements of the final product indicated less than three percent cyclics and a molecular weight of 2821 by titration.
EXAMPLE 4 - Preparation of Methacylate-Capped Prepolymer of Polysiloxane Containing Both Dimethylsiloxane and Diphenylsiloxane Units:
A 500-mL round bottom flask equipped with reflux condenser and nitrogen blanket was charged with isophorone diisocyanate (5.031 g, 0.0227 mole), the hydroxybutyl-terminated copolymer of dimethylsiloxane and the diphenylsiloxane from Example 3 (51.4465 g, 0.0189 mole), dibutyltin dilaurate (0.1811 g) and methylene chloride (150 mL). The flask contents were refluxed.
After about 90 hours of reflux, the isocyanate was found decreased to 16.2 percent (theoretical 16.7 percent) of original. The contents of the flask were allowed to cool to ambient temperature. HEMA (1.1572 g) and 1,1'-2-bi-naphthol (5.7 mg) were added to the flask and stirred. After seven days, NCO peak disappeared from IR spectrum and the reaction was terminated. The product was obtained at quantitative yield after removing solvent.
EXAMPLE 5 - Preparation of High Refractive Index Hydrogels Containing a Yellow Dye Moiety and UV Absorber Useful for IOL Application:
A formulation consists of 50 parts of prepolymer of Example 5, 20 parts of benzyl acrylate, 10 parts of benzyl methacrylate , 20 parts of N,N-dimethyl acrylamide, 0.25 parts benzotriazole methacrylate, 0.2 part N, N-bis-(2-[acryloxyethyl)-(4'-phenylazo)aniline as described in Example 2, and 1 parfi of Irgacure-784. The mix is cured between two silane-treated glass plates under a high intensity visible light lamp, Model RC-257 (Xenon Corporation) for 1 hour.
The cured films are then released, extracted in isopropanol for over 4 hours and dried in a vacuum oven at 70 degrees Celsius overnight. The dried films are then placed in a borate buffered saline overnight before characterization. The films have a thickness of 170-200 microns. The UV-VIS absorption of hydrogel films are then measured and have less than 1 % transmittance below 400 nm and less than 60 % transmittance but above 40 %, below 450 nm. Mechanical properties of the processed films can be adjusted by adjustment of the light intensity applied for curing.
Soft, foldable, relatively high refractive index of approximately 1.42 or greater, relatively high elongation of approximately 100 percent or greater, IOLs with blue light absorption properties are synthesized through the process of the present invention. The IOLs produced as described herein have the flexibility required to allow the same to be folded or deformed for insertion into an eye through the smallest possible surgical incision, i.e., 3.5 mm or smaller. It is unexpected that the subject IOLs described herein could possess the ideal physical properties disclosed herein. The ideal physical properties of the subject IOLs are unexpected due to difficulties previously associated with photo curing of blue light absorbing and UV light absorbing materials.
IOLs manufactured using the process of the present invention can be of any design capable of being rolled or folded for implantation through a relatively small surgical incision, i.e., 3.5 mm or less. Such IOLs may be manufactured to have an optic portion and haptic portions made of the same or differing materials. Once the materials) are selected, the same may be cast in molds of the desired shape, cured and removed from the molds. After such molding, the IOLs are treated in accordance with the process of the present invention and then cleaned, polished, packaged and sterilized by customary methods known to those skilled in the art. Alternatively, the materials may be cast in rods, cut into disks and lathed into the desired shape as known to those skilled in the art.
In addition to IOLs, the process of the present invention is also suitable for use in the production of other medical or ophthalmic devices such as contact lenses, keratoprostheses, capsular bag extension rings, corneal inlays, corneal rings and like devices.
IOLs manufactured using the process of the present invention are used as customary in the field of ophthalmology. For example, in a surgical cataract procedure, an incision is placed in the cornea of an eye. Through the corneal incision the cataractous natural lens of the eye is removed (aphakic application) and an IOL is inserted into the anterior chamber, posterior chamber or lens capsule of the eye prior to closing the incision. However, the subject ophthalmic devices may likewise be used in accordance with other surgical procedures known to those skilled in the field of ophthalmology.
While there is shown and described herein a process for producing IOLs with blue light and ultraviolet light absorption capabilities, it will be manifest to those skilled in the art that various modifications may be made without departing from the spirit and scope of the underlying inventive concept and that the same is not limited to particular processes and structures herein shown and described except insofar as indicated by the scope of the appended claims.
Claims (23)
1. A method for manufacturing medical devices comprising:
incorporating into a suitable material including one or more blue light absorption moieties and one or more ultraviolet light absorption moieties, one or more photo initiators having absorption above 500 nm and being capable of initiating a polymerization of said suitable material upon irradiation with visible light having wavelengths greater than about 500 nm; and exposing said material to said visible light for a period of time sufficient to effect said polymerization.
incorporating into a suitable material including one or more blue light absorption moieties and one or more ultraviolet light absorption moieties, one or more photo initiators having absorption above 500 nm and being capable of initiating a polymerization of said suitable material upon irradiation with visible light having wavelengths greater than about 500 nm; and exposing said material to said visible light for a period of time sufficient to effect said polymerization.
2. A method for manufacturing medical devices with blue light and ultraviolet light absorption properties comprising:
incorporating into a suitable material including one or more blue light absorption moieties and one or more ultraviolet light absorption moieties, one or more photo initiators having absorption above 500 nm and being capable of initiating a polymerization of said suitable material upon irradiation with visible light having wavelengths greater than about 500 nm; and exposing said material to said visible light for a period of time sufficient to effect said polymerization.
incorporating into a suitable material including one or more blue light absorption moieties and one or more ultraviolet light absorption moieties, one or more photo initiators having absorption above 500 nm and being capable of initiating a polymerization of said suitable material upon irradiation with visible light having wavelengths greater than about 500 nm; and exposing said material to said visible light for a period of time sufficient to effect said polymerization.
3. The method of claim 1 or 2 wherein said medical device is selected from the group consisting of contact lenses, keratoprostheses, capsular bag extension rings, corneal inlays and corneal rings.
4. The method of claim 1 or 2 wherein said medical device is an intraocular lens.
5. The method of claim 1 or 2 wherein said blue light absorption moieties are one or more reactive yellow dyes.
6. The method of claim 1 or 2 wherein said blue light absorption moieties are one or more azo-based yellow dyes.
7. The method of claim 1 or 2 wherein said suitable material is a material having ethylenically unsaturated groups.
8. The method of claim 1 or 2 wherein said suitable material is an acrylate or methacrylate material.
9. The method of claim 1 or 2 wherein said suitable material includes one or more high refractive index monomers.
10. The method of claim 1 or 2 wherein said wherein said suitable material includes one or more high refractive index monomers selected from the group consisting of 2-ethylphenoxy methacrylate, 2-ethylphenoxy acrylate, 2-ethylthiophenyl methacrylate, 2-ethylthiophenyl acrylate, 2-ethylaminophenyl methacrylate, 2-ethylaminophenyl acrylate, phenyl methacrylate, benzyl methacrylate, 2-phenylethyl methacrylate, 3-phenylpropyl methacrylate, 4-phenylbutyl methacrylate, 4-methylphenyl methacrylate, 4-methylbenzyl methacrylate, 2,2-methylphenylethyl methacrylate, 2,3-methylphenylethyl methacrylate, 2,4-methylphenylethyl methacrylate, 2-(4-propylphenyl)ethyl methacrylate, 2-(4-(1-methylethyl)phenyl)ethyl methacrylate, 2-(4-methoxyphenyl)ethyl methacrylate, 2-(4-cyclohexylphenyl)ethyl methacrylate, 2-(2-chlorophenyl)ethyl methacrylate, 2-(3-chlorophenyl)ethyl methacrylate, 2-(4-chlorophenyl)ethyl methacrylate, 2-(4-bromophenyl)ethyl methacrylate, 2-(3-phenylphenyl)ethyl methacrylate, 2-(4-phenylphenyl)ethyl methacrylate and 2-(4-benzylphenyl)ethyl methacrylate.
11. The method of claim 1 or 2 wherein said wherein said suitable material includes one or more high refractive index prepolymers selected from the group consisting of methacrylate-capped prepolymers of polysiloxanes and acrylate-capped prepolymers of polysiloxanes having a suitable number of aromatic moieties to provide a prepolymer with a refractive index of at least 1.42.
12. The method of claim 1 or 2 wherein said ultraviolet light absorption moieties are one or more benzotriazole compositions.
13. The method of claim 1 or 2 wherein said ultraviolet light absorption moieties are one or more benzotriazole compositions selected from the group consisting of .beta.-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2'-methacryloxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-5'-methacryoxyethylphenyl)-2H-benzotriazole, 2-[3'-tert-butyl-2'-hydroxy-5'-(3"-methacryloyloxypropyl)phenyl]-5-chlorobenzotriazole, 2-[3'-tent-butyl-5'-(3"-dimethylvinylsilylpropoxy)-2'-hydroxyphenyl]-5-methoxybenzotriazole and 2-[3'-tert-butyl-2'-hydroxy-5'-(3"-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole.
14. The method of claim 1 or 2 wherein said photo initiators are selected from the group consisting of substituted ultraviolet photo initiators, conjugated ketones, triazine-yl derivatives and metal salts.
15. The method of claim 1 or 2 wherein said photo initiators are selected from the group consisting of titanocene derivatives.
16. The method of claim 1 or 2 wherein said visible light is provided by a visible light source.
17. The method of claim 1 or 2 wherein said visible light is provided by a xenon lamp.
18. The method of claim 1 or 2 wherein said short period of time is less than several hours.
19. The method of claim 1 or 2 wherein said short period of time is about 2 hours or less.
20. A method of using the medical device produced through the method of claim 1 or 2 comprising:
implanting said medical device in an eye.
implanting said medical device in an eye.
21. A medical device produced through the method of claim 1 or 2.
22. An intraocular lens produced through the method of claim 1 or 2.
23
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US10/657,356 | 2003-09-08 | ||
PCT/US2004/026776 WO2005026787A1 (en) | 2003-09-08 | 2004-08-19 | Process for manufacturing intraocular lenses with blue light absorption characteristics |
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EP (1) | EP1664855B1 (en) |
JP (1) | JP2007504854A (en) |
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Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8500274B2 (en) | 2000-11-03 | 2013-08-06 | High Performance Optics, Inc. | Dual-filter ophthalmic lens to reduce risk of macular degeneration |
US8403478B2 (en) | 2001-11-02 | 2013-03-26 | High Performance Optics, Inc. | Ophthalmic lens to preserve macular integrity |
EP1818690A1 (en) * | 2006-02-14 | 2007-08-15 | Procornea Holding B.V. | Intraocular lenses essentially free from glistenings |
US8360574B2 (en) * | 2006-03-20 | 2013-01-29 | High Performance Optics, Inc. | High performance selective light wavelength filtering providing improved contrast sensitivity |
US20120075577A1 (en) | 2006-03-20 | 2012-03-29 | Ishak Andrew W | High performance selective light wavelength filtering providing improved contrast sensitivity |
US8113651B2 (en) * | 2006-03-20 | 2012-02-14 | High Performance Optics, Inc. | High performance corneal inlay |
US20070216861A1 (en) * | 2006-03-20 | 2007-09-20 | Andrew Ishak | Ophthalmic system combining ophthalmic components with blue light wavelength blocking and color-balancing functionalities |
US9377569B2 (en) | 2006-03-20 | 2016-06-28 | High Performance Optics, Inc. | Photochromic ophthalmic systems that selectively filter specific blue light wavelengths |
US7520608B2 (en) * | 2006-03-20 | 2009-04-21 | High Performance Optics, Inc. | Color balanced ophthalmic system with selective light inhibition |
US8882267B2 (en) | 2006-03-20 | 2014-11-11 | High Performance Optics, Inc. | High energy visible light filter systems with yellowness index values |
MX2009001978A (en) | 2006-08-23 | 2009-05-15 | High Performance Optics Inc | System and method for selective light inhibition. |
JP5448166B2 (en) * | 2006-10-13 | 2014-03-19 | アルコン,インコーポレイテッド | Intraocular lens with unique blue-purple cut-off and blue light transmission characteristics |
TWI453199B (en) | 2008-11-04 | 2014-09-21 | Alcon Inc | Uv/visible light absorbers for ophthalmic lens materials |
US8222360B2 (en) | 2009-02-13 | 2012-07-17 | Visiogen, Inc. | Copolymers for intraocular lens systems |
JP5544017B2 (en) | 2009-09-15 | 2014-07-09 | ノバルティス アーゲー | Prepolymer suitable for the production of UV-absorbing contact lenses |
US8770749B2 (en) | 2010-04-15 | 2014-07-08 | Oakley, Inc. | Eyewear with chroma enhancement |
RU2576622C2 (en) | 2010-07-30 | 2016-03-10 | Новартис Аг | Amphiphilic polysiloxane prepolymers and their application |
EP2625217B1 (en) | 2010-10-06 | 2018-07-04 | Novartis AG | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
JP5784131B2 (en) | 2010-10-06 | 2015-09-24 | ノバルティス アーゲー | Polymerizable chain-extended polysiloxane with pendant hydrophilic groups |
RU2576317C2 (en) | 2010-10-06 | 2016-02-27 | Новартис Аг | Silicone-containing prepolymers subjected to water processing and versions of application thereof |
CN102617784B (en) * | 2011-02-01 | 2016-08-17 | 爱博诺德(北京)医疗科技有限公司 | There is the acrylic polymeric material of high index of refraction |
CN104040412B (en) | 2011-10-20 | 2016-01-13 | 奥克利有限公司 | There are the glasses that colourity strengthens |
WO2013169987A1 (en) | 2012-05-10 | 2013-11-14 | Oakley, Inc. | Eyewear with laminated functional layers |
US9798163B2 (en) | 2013-05-05 | 2017-10-24 | High Performance Optics, Inc. | Selective wavelength filtering with reduced overall light transmission |
US9575335B1 (en) | 2014-01-10 | 2017-02-21 | Oakley, Inc. | Eyewear with chroma enhancement for specific activities |
US9683102B2 (en) | 2014-05-05 | 2017-06-20 | Frontier Scientific, Inc. | Photo-stable and thermally-stable dye compounds for selective blue light filtered optic |
CN115553973A (en) * | 2014-05-07 | 2023-01-03 | 土耳其科学技术研究理事会 | Artificial lens and preparation method thereof |
WO2016077431A2 (en) | 2014-11-13 | 2016-05-19 | Oakley, Inc. | Variable light attenuation eyewear with color enhancement |
US10871661B2 (en) | 2014-05-23 | 2020-12-22 | Oakley, Inc. | Eyewear and lenses with multiple molded lens components |
KR101540114B1 (en) * | 2014-07-15 | 2015-07-29 | (주)케미그라스 | Blue-light blocking lens and its manufacturing method |
NL2013786B1 (en) * | 2014-11-13 | 2016-10-07 | Original G B V | Quenched coating. |
US9905022B1 (en) | 2015-01-16 | 2018-02-27 | Oakley, Inc. | Electronic display for demonstrating eyewear functionality |
KR101612940B1 (en) * | 2015-09-15 | 2016-04-15 | (주)케미그라스 | Functional glasses lens having Fuction of Blocking UV Light And Blue Light |
WO2017145024A1 (en) | 2016-02-22 | 2017-08-31 | Novartis Ag | Uv-absorbing vinylic monomers and uses thereof |
US10268053B2 (en) | 2016-02-22 | 2019-04-23 | Novartis Ag | UV/visible-absorbing vinylic monomers and uses thereof |
KR101786302B1 (en) * | 2016-03-03 | 2017-10-17 | (주)메디오스 | The method for producing blue light blocking soft contact lens |
EP3323387B1 (en) * | 2016-11-22 | 2019-10-02 | REPER Sàrl | A biocompatible copolymer material and an ophthalmic implant consisting thereof |
CN106773319B (en) * | 2017-01-24 | 2019-09-27 | 深圳市华星光电技术有限公司 | Display device and preparation method thereof |
US11707354B2 (en) | 2017-09-11 | 2023-07-25 | Amo Groningen B.V. | Methods and apparatuses to increase intraocular lenses positional stability |
US11112622B2 (en) | 2018-02-01 | 2021-09-07 | Luxottica S.R.L. | Eyewear and lenses with multiple molded lens components |
US10935695B2 (en) | 2018-03-02 | 2021-03-02 | Johnson & Johnson Vision Care, Inc. | Polymerizable absorbers of UV and high energy visible light |
WO2020111170A1 (en) * | 2018-11-30 | 2020-06-04 | 富士フイルム株式会社 | Polymerizable composition and contact lens |
CN110152059B (en) * | 2019-05-07 | 2020-07-07 | 浙江大学 | Artificial lens containing antibiotic and its making method |
KR102199118B1 (en) | 2019-06-10 | 2021-01-06 | (주)지오메디칼 | Blue light blocking composition and the blue light blocking contact lens using the same and the manufacturing method thereof |
US11543683B2 (en) | 2019-08-30 | 2023-01-03 | Johnson & Johnson Vision Care, Inc. | Multifocal contact lens displaying improved vision attributes |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
JP2798468B2 (en) * | 1990-02-28 | 1998-09-17 | ホーヤ株式会社 | Contact lens material and method of manufacturing contact lens |
JP2559292B2 (en) * | 1990-11-06 | 1996-12-04 | 株式会社総合歯科医療研究所 | Resin composition for producing soft contact lens, soft contact lens and method for producing the same |
ES2094796T3 (en) * | 1990-11-07 | 1997-02-01 | Nestle Sa | POLYMERS AND THEIR USE FOR OPHTHALMIC LENSES. |
US5470932A (en) | 1993-10-18 | 1995-11-28 | Alcon Laboratories, Inc. | Polymerizable yellow dyes and their use in opthalmic lenses |
US6015842A (en) * | 1997-08-07 | 2000-01-18 | Alcon Laboratories, Inc. | Method of preparing foldable hydrophilic ophthalmic device materials |
US5891931A (en) | 1997-08-07 | 1999-04-06 | Alcon Laboratories, Inc. | Method of preparing foldable high refractive index acrylic ophthalmic device materials |
US6353069B1 (en) | 1998-04-15 | 2002-03-05 | Alcon Manufacturing, Ltd. | High refractive index ophthalmic device materials |
US5945465A (en) * | 1998-05-15 | 1999-08-31 | Bausch & Lomb Incorporated | Method for polymerizing contact lenses having UV absorbing properties |
US5914355A (en) * | 1998-05-15 | 1999-06-22 | Bausch & Lomb Incorporated | Method for making contact lenses having UV absorbing properties |
US6359024B2 (en) * | 1998-05-15 | 2002-03-19 | Bausch & Lomb Incorporated | Method for polymerizing contact lenses |
US6244707B1 (en) * | 1998-07-21 | 2001-06-12 | Wesley Jessen Corporation | UV blocking lenses and material containing benzotriazoles and benzophenones |
JP4225612B2 (en) | 1998-09-09 | 2009-02-18 | スター・ジャパン株式会社 | Ophthalmic lens material |
SE9803481D0 (en) * | 1998-10-13 | 1998-10-13 | Pharmacia & Upjohn Ab | Photocurable siloxane polymers |
EP1035142A1 (en) * | 1999-03-09 | 2000-09-13 | Nidek Co., Ltd. | Acrylic copolymer materials suitable for ophthalmic devices |
US6281319B1 (en) * | 1999-04-12 | 2001-08-28 | Surgidev Corporation | Water plasticized high refractive index polymer for ophthalmic applications |
US6632905B2 (en) * | 1999-09-02 | 2003-10-14 | Alcon Universal Ltd. | Covalently-bound, hydrophilic coating compositions for surgical implants |
US6406739B1 (en) * | 2000-01-12 | 2002-06-18 | Alcon Universal Ltd. | Coating compositions and methods for reducing edge glare in implantable ophthalmic lenses |
-
2003
- 2003-09-08 US US10/657,356 patent/US7276544B2/en active Active
-
2004
- 2004-08-19 CN CN2004800257119A patent/CN1849531B/en not_active Expired - Fee Related
- 2004-08-19 JP JP2006525347A patent/JP2007504854A/en active Pending
- 2004-08-19 WO PCT/US2004/026776 patent/WO2005026787A1/en active Search and Examination
- 2004-08-19 EP EP04781469A patent/EP1664855B1/en not_active Expired - Fee Related
- 2004-08-19 AU AU2004272996A patent/AU2004272996A1/en not_active Abandoned
- 2004-08-19 CA CA002536762A patent/CA2536762A1/en not_active Abandoned
- 2004-08-19 DE DE602004019948T patent/DE602004019948D1/en active Active
- 2004-08-19 KR KR1020067004686A patent/KR20060076290A/en not_active Application Discontinuation
Also Published As
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WO2005026787A1 (en) | 2005-03-24 |
US20050055090A1 (en) | 2005-03-10 |
AU2004272996A1 (en) | 2005-03-24 |
CN1849531B (en) | 2011-11-16 |
DE602004019948D1 (en) | 2009-04-23 |
EP1664855B1 (en) | 2009-03-11 |
KR20060076290A (en) | 2006-07-04 |
JP2007504854A (en) | 2007-03-08 |
CN1849531A (en) | 2006-10-18 |
EP1664855A1 (en) | 2006-06-07 |
US7276544B2 (en) | 2007-10-02 |
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Legal Events
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EEER | Examination request | ||
FZDE | Discontinued | ||
FZDE | Discontinued |
Effective date: 20090819 |