CN113024716A - Ophthalmic material and method for producing same - Google Patents
Ophthalmic material and method for producing same Download PDFInfo
- Publication number
- CN113024716A CN113024716A CN201911346058.0A CN201911346058A CN113024716A CN 113024716 A CN113024716 A CN 113024716A CN 201911346058 A CN201911346058 A CN 201911346058A CN 113024716 A CN113024716 A CN 113024716A
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- China
- Prior art keywords
- acrylate
- methacrylate
- monomer
- monomers
- group
- 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.)
- Granted
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- 239000000463 material Substances 0.000 title claims abstract description 166
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000000178 monomer Substances 0.000 claims abstract description 147
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 80
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 37
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- -1 acryloyloxy group Chemical group 0.000 claims abstract description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-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
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 208000002177 Cataract Diseases 0.000 claims description 7
- 238000001514 detection method Methods 0.000 claims description 7
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 claims description 5
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 5
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 claims description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 5
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 5
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 claims description 5
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 claims description 5
- LCPUCXXYIYXLJY-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)C(F)CC(F)(F)F LCPUCXXYIYXLJY-UHFFFAOYSA-N 0.000 claims description 4
- DEQJNIVTRAWAMD-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)(F)CC(F)C(F)(F)OC(=O)C=C DEQJNIVTRAWAMD-UHFFFAOYSA-N 0.000 claims description 4
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 4
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 claims description 4
- RBFPEAGEJJSYCX-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CCOCCOCCOCCOC(=O)C(C)=C RBFPEAGEJJSYCX-UHFFFAOYSA-N 0.000 claims description 4
- WPDXVLVDHUDHPC-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound CCOCCOCCOCCOC(=O)C=C WPDXVLVDHUDHPC-UHFFFAOYSA-N 0.000 claims description 4
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 4
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 4
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 4
- QUKRIOLKOHUUBM-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C QUKRIOLKOHUUBM-UHFFFAOYSA-N 0.000 claims description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 4
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 claims description 4
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 210000004087 cornea Anatomy 0.000 claims description 4
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 claims description 4
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 4
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 4
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 4
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 4
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 4
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- VLSRKCIBHNJFHA-UHFFFAOYSA-N 2-(trifluoromethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C(F)(F)F VLSRKCIBHNJFHA-UHFFFAOYSA-N 0.000 claims description 3
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- VEPKQEUBKLEPRA-UHFFFAOYSA-N VX-745 Chemical compound FC1=CC(F)=CC=C1SC1=NN2C=NC(=O)C(C=3C(=CC=CC=3Cl)Cl)=C2C=C1 VEPKQEUBKLEPRA-UHFFFAOYSA-N 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 3
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 3
- 229920000223 polyglycerol Polymers 0.000 claims description 3
- 238000013268 sustained release Methods 0.000 claims description 3
- 239000012730 sustained-release form Substances 0.000 claims description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 claims description 3
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 2
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 claims description 2
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- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 21
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- IAMASUILMZETHW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCC(O)OC1=CC=CC=C1 IAMASUILMZETHW-UHFFFAOYSA-N 0.000 description 8
- 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 7
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 7
- 238000000748 compression moulding Methods 0.000 description 7
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- 230000009477 glass transition Effects 0.000 description 7
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- KCBRKYUMKFTTHC-UHFFFAOYSA-N [1-[1-(2-methylprop-2-enoyloxy)-2-[(2-methyl-3-prop-2-enoyloxyprop-2-enoyl)amino]-2-(prop-2-enoylamino)ethenoxy]-2-[(2-methyl-3-prop-2-enoyloxyprop-2-enoyl)amino]-2-(prop-2-enoylamino)ethenyl] 2-methylprop-2-enoate Chemical compound C(C=C)(=O)OC=C(C(=O)NC(=C(OC(C(=C)C)=O)OC(=C(NC(C=C)=O)NC(C(=COC(C=C)=O)C)=O)OC(C(=C)C)=O)NC(C=C)=O)C KCBRKYUMKFTTHC-UHFFFAOYSA-N 0.000 description 3
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
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- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-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
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- BRQMAAFGEXNUOL-UHFFFAOYSA-N 2-ethylhexyl (2-methylpropan-2-yl)oxy carbonate Chemical compound CCCCC(CC)COC(=O)OOC(C)(C)C BRQMAAFGEXNUOL-UHFFFAOYSA-N 0.000 description 1
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- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical group CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
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- 208000008516 Capsule Opacification Diseases 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
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- 238000000149 argon plasma sintering Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-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
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
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- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
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- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
- PZDUWXKXFAIFOR-UHFFFAOYSA-N hexadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C=C PZDUWXKXFAIFOR-UHFFFAOYSA-N 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
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- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 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 class 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 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000000079 pharmacotherapeutic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FZGSCNQUWMMDIG-UHFFFAOYSA-N phenyl(phosphanyl)methanone Chemical compound PC(=O)C1=CC=CC=C1 FZGSCNQUWMMDIG-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- 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
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/302—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and two or more oxygen atoms in the alcohol moiety
-
- 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
Abstract
The present invention relates to ophthalmic materials comprising the product of copolymerizing at least two monomers selected from the group consisting of: -a first monomer selected from aromatic acrylate monomers in which an aromatic group and an acryloyloxy group are linked through a flexible group selected from a linear or branched alkyl group, an ether bond, a sulfide bond, -a second monomer selected from a hydrophobic aliphatic acrylate monomer or a hydrophilic aliphatic acrylate monomer, wherein the weight ratio of the second monomer to the first monomer is 10-30: 70-90.
Description
Technical Field
The invention relates to an ophthalmic material, in particular to an intraocular lens material, and particularly relates to an intraocular lens material suitable for being prepared in a compression molding mode.
Background
The cataract patient can recover partial or all vision by removing the natural diseased crystalline lens and then implanting an artificial crystalline lens. Intraocular lens materials were first hard Polymethylmethacrylate (PMMA) materials and later soft (foldable) materials such as silicone, hydrophilic acrylates and hydrophobic acrylates were introduced. The processing and forming modes of the artificial lens are basically divided into two types: turning and molding. The turning method is that the polymerized and formed material is made into a blank with a certain size and shape, and then the blank is processed into the artificial lens by a precise turning technology; the mould pressing method is that various monomers, initiator, light absorbent and other various assistants which are composed of the materials are uniformly mixed and poured into a mould of the artificial lens, polymerization is initiated by heating or illumination, and the mould is opened to directly obtain the artificial lens after the polymerization is completed.
The turning method is mostly adopted for the artificial lens on the market at present, although the processing cost is higher than that of the die pressing method. Only a few, such as Alcon in the united states, use compression molding. The molding method has high requirements on materials because the liquid monomer can shrink during the curing and molding process, and the deformation caused by the shrinkage is a fatal factor for the intraocular lens product with high-precision optical design, so that the imaging quality of the molded intraocular lens is seriously reduced, and even the molded intraocular lens cannot be imaged.
Although Alcon materials have low cure shrinkage and are particularly suitable for intraocular lens manufacture by compression molding, there are many reports in the literature that their materials exhibit "flash points" after implantation in the eye, which can seriously affect the postoperative vision of patients (Miyata A, Yaguchi S. Equisium water content and glistenings in acrylic intraocular lenses, J Cataract Refract surg. 2004 Aug; 30(8): 1768-72); werner L, Glistenings and surface light scattering in intraannular lenses J Cataract Refract Surg 2010; 36: 1398-. The reason for this is probably that the two main constituent monomers of the material, namely phenylethyl methacrylate and phenylethyl acrylate, all contain aromatic side groups, and have a large steric hindrance effect, so that a microscopic cavity structure with a large size is formed inside the material. Once the intraocular lens is implanted into an eye, aqueous humor in the eye can easily enter the cavities inside the material after a certain period of time, for example, more than half a year, and the aqueous cavities show a phenomenon of "Glistening" under the observation of a slit lamp, because the refractive index of the material itself is much higher than that of water.
Based on the above analysis, it is necessary to develop a material with suitable shrinkage rate suitable for molding, and at the same time, the material does not have microscopic cavities (or is filled) capable of initiating flash points, and will achieve the advantages in the intraocular lens market from the aspects of cost and use effect.
Disclosure of Invention
The molding method is used for preparing the artificial lens, and the basic conditions to be met by the material of the artificial lens firstly comprise the following steps: the curing shrinkage rate is low, and the monomer can meet the design of a precise optical surface after being molded in an artificial lens mold; the surface energy is suitable, and after the curing and forming in the mold, a certain adhesive force can be formed on the surface of the mold so as to facilitate the subsequent operation process, such as demolding in the subsequent process; the material with hydrophobic property is preferred, so that the generation of secondary cataract (PCO) is avoided; other properties suitable for intraocular lens materials include, but are not limited to: suitable refractive index (1.4-1.6), hardness suitable for micro-incision surgical procedures (adjustable by glass transition temperature or water content), sufficient mechanical strength and elastic modulus, and the like.
Acrylate materials have very good optical properties and biocompatibility, so that intraocular lens products on the market at present are mainly made of acrylate materials, including hydrophilic acrylate and hydrophobic acrylate, and the molecular structural formula of the intraocular lens products can be represented as follows:
wherein R is selected from H or CH3The choice of the Z group can be considered to be infinite, and the appropriate functional group can be selected according to the desired characteristics.
According to the ophthalmic material of the present invention, a specific acrylate is used as the first monomer. In the first monomer, the larger the molecular weight of the Z group, the more complicated the molecular structure, and the more rigid the molecule or chemical bond, the larger the steric hindrance effect, that is, the larger the space required between the molecules, and therefore the smaller the volume shrinkage rate of the monomer after polymerization, curing and molding, and for example, a group having an aromatic structure such as a benzene ring, etc., therefore, a monomer having a Z group having a complicated structure and rigidity is selected to be more suitable for molding. For the present IOL product, the stiffer Z group is not selected as the better, since the IOL ultimately needs to be implanted into the eye for a long time in the aqueous environment, especially if there are a large number of microscopic, bulky cavities in the hydrophobic acrylate material, which can allow a small amount of water to enter the interior of the material, which can result in a "flash point" due to the large difference in refractive index between the material and water. Thus, the Z group of the selected acrylate monomers of the present invention itself requires some flexibility, including but not limited to the attachment of the aromatic group to the acryloyloxy group by a flexible group such as a linear or branched alkyl, ether, sulfide, etc., such as phenylethyl acrylate (PEA), phenylethyl methacrylate (PEMA), phenoxyethyl acrylate (POEA), phenoxyethyl methacrylate, phenoxydiethylene glycol acrylate (P (2EO) A), methylphenoxydiethylene glycol acrylate, phenoxypolyethylene glycol acrylate (P (nEO) A), methylphenoxypolyethylene glycol acrylate, etc.; preferably phenoxyethyl acrylate (POEA), phenoxydiethylene glycol acrylate (P (2EO) A), phenoxytriethylene glycol acrylate (P (3EO) A); more preferred are phenoxyethyl acrylate, phenoxyethyl methacrylate, phenoxydiethylene glycol acrylate, methylphenoxydiethylene glycol acrylate, and mixtures thereof.
In accordance with embodiments of the ophthalmic materials of the present invention, since the selected Z group still has a large steric hindrance, the polymerized material can still generate a "sparkle point", and therefore, it is necessary to add an additional acrylate monomer containing a more flexible aliphatic Z group to "fill" the microscopic cavities formed by the aromatic Z group to eventually eliminate the "sparkle point" phenomenon. Thus, the present invention relates to the use of specific acrylates as second monomers. In the second monomer, the aliphatic Z group is still selected from the group consisting of C8-18 linear or branched, saturated or unsaturated alkyl groups, taking into account the combination of cure shrinkage and filling ability for microscopic cavities. Hydrophobic aliphatic acrylate monomers, isooctyl methacrylate, isooctyl acrylate, isodecyl methacrylate, lauryl acrylate, tetradecyl methacrylate, tetradecyl acrylate, hexadecyl methacrylate, hexadecyl acrylate, octadecyl methacrylate, octadecyl acrylate, ethyl 2-perfluorodecyl methacrylate, 2- (perfluorooctyl) ethyl acrylate, and mixtures thereof.
According to another embodiment of the ophthalmic material according to the invention, Z groups of lower molecular weight are also selectable. Optionally, in order to eliminate this group of contradictions when using a lower molecular weight Z group and causing a material to have a larger curing shrinkage, a hydrophilic acrylate monomer capable of forming a continuous phase inside the material is additionally introduced, a small amount of water capable of forming a continuous phase in the intraocular lens material is used to assist the aliphatic monomer to further fill up microscopic cavities and avoid a "flash point" phenomenon, and the amount of the hydrophilic acrylate monomer capable of forming a continuous phase inside the material is within the range of the present invention, so that not only enough water can form a continuous phase inside the material, but also other intraocular metabolic substances cannot enter the intraocular lens material to form turbidity. The lower molecular weight Z group may be selected from at least one of the following monomers: methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, butyl methacrylate, butyl acrylate, hexyl methacrylate, hexyl acrylate, isopropyl methacrylate, isopropyl acrylate, isobutyl methacrylate, isobutyl acrylate, tert-butyl methacrylate, tert-butyl acrylate, ethoxyethoxyethoxyethyl methacrylate, ethoxyethoxyethoxyethyl acrylate, ethoxyethyl methacrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, methoxyethyl acrylate, trifluoroethyl methacrylate, trifluoroethyl acrylate, hexafluorobutyl methacrylate, hexafluorobutyl acrylate. The hydrophilic aliphatic monomer may be selected from the group consisting of glycidyl methacrylate, glycidyl acrylate, polyethylene glycol (meth) acrylate monoester, methoxypolyethylene glycol (meth) acrylate monoester, ethoxypolyethylene glycol (meth) acrylate monoester, polypropylene glycol (meth) acrylate monoester, polyglycerol (meth) acrylate monoester, and mixtures thereof. Hydrophilic acrylate monomers capable of forming a continuous phase within the material may be selected from, for example, hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, hydroxypropyl acrylate; or a hydrophilic monomer having other polymerizable groups, wherein the polymerizable groups include vinyl, allyl, butenyl, ethynyl, acryloxy, methacryloxy, acrylamido, methacrylamido, vinylether, and the like, wherein the hydrophilic monomer may be selected from vinylpyrrolidone, dimethylacrylamide, acrylic acid, methacrylic acid, 2- (trifluoromethyl) acrylic acid, phenylacrylic acid, acrylamide, methacrylamide, N-methylolacrylamide, N-methylolmethacrylamide, or derivatives thereof, and the like.
The preparation of the material is obtained by copolymerizing at least two acrylate monomers selected from the following group:
a first monomer selected from aromatic acrylate monomers in which an aromatic group is linked to an acryloyloxy group by a flexible group selected from linear or branched alkyl, ether bond, sulfide bond,
-a second monomer selected from a hydrophobic aliphatic acrylate monomer or a hydrophilic aliphatic acrylate monomer,
wherein the weight ratio of the second monomer to the first monomer is 10-30:70-90, 10-20:80-90, or 20-30:70-80, or 10-15:85-90, or 25-30: 70-75.
In one embodiment of the present invention, the aromatic acrylate monomer has the molecular formula:
R1= H or C1-6 alkyl, preferably H or CH3；
R2Is a linear or branched, saturated or unsaturated C1-6 alkylene group, preferably a C2-4 alkylene group,
n is 1 to 4, preferably 1 to 3, or 1, or 2.
In one embodiment of the present invention, the hydrophobic aliphatic acrylate monomer or the hydrophilic aliphatic acrylate monomer has a molecular structural formula of:
wherein:
- R3is H or C1-6 alkyl, preferably H or CH3；
- R4Is a linear or branched, saturated or unsaturated C1-6 alkylene group;
-m is 0 to 8, inclusive, or 0, 1, 2, 3, 4, 5, 6, 7 or 8;
- R5is a linear or branched, saturated or unsaturated C1-18 alkylene group, preferably a linear or branched, saturated or unsaturated C8-18 alkylene group;
-a is hydroxy or hydrogen;
with the following conditions: r4And R5Is not higher than 18.
The ophthalmic material has at least one property selected from the group consisting of:
a. the refractive index at 35 ℃ is from 1.49 to 1.56, preferably from 1.50 to 1.54, more preferably from 1.52 to 1.54.
b. The glass transition temperature (as determined by DSC testing) is in the range of 6 to 35 deg.C, preferably 8 to 20 deg.C, more preferably 10 to 18 deg.C.
c. The shrinkage rate of the monomer after curing and molding through polymerization reaction is less than 1 percent, preferably less than 0.5 percent, and more preferably less than 0.2 percent
d. The water content at 35 ℃ is 1 to 4wt%, preferably 1.5 to 4wt%, more preferably 2 to 3 wt%.
e. No 'flash point' phenomenon exists in the material for at least more than half a year under the simulated intraocular state.
Methods used in the art to assess the internally generated sparkle point of a material are generally as follows: the material is soaked in balanced salt solution simulating the state of eyes, is placed for 3 months, 6 months and 12 months at the temperature of 37 +/-1 ℃, then is placed under a microscope with the magnification of more than 20 times to observe the condition and the quantity of 'Glistening' in the material, and refers to the international standard 'BS EN ISO 11979-2 ocular implant' related to intraocular lenses.
The inventor of the invention finds that in the process of restoring the intraocular lens to the room temperature from the temperature condition of 37 +/-1 ℃, when the water content of the material is lower than 1%, the atomization phenomenon can be rapidly generated in the material within a short time, and when the material is placed in the environment to be continuously balanced for a period of time, the atomization phenomenon also disappears; this phenomenon hardly occurs when the water content of the material is higher than 1%. Therefore, the researchers of the invention analyze and think that the hydrophilicity of the material per se has special significance for eliminating flash points generated by long-term placement in the aqueous humor environment of the eyes. But the present inventors have come toThe step analysis considers that in order to keep the hydrophobic characteristic which is required to be possessed by the artificial lens material so as to obtain higher refractive index and low occurrence probability of posterior capsule, the water content of the material is not higher than 4%, and when the water content of the material is higher than 4%, the material shows obvious hydrophilic characteristic and has lower surface water contact angle and the like; the inventor also finds that particularly after the water content of the material exceeds 4%, the refractive index of the material is affected in a complex way, and the refractive index and the water content of the acrylate material with low water content have the following relationship:
in which V iswIs the water content of the material, nwIs the refractive index of water, npFor the refractive index of the acrylate polymer in dry state, when the water content of the material exceeds 4%, the difference between the refractive index of the material at the time of complete dehydration and the refractive index at the equilibrium state after complete hydration exceeds 0.01, and the fluctuation of the refractive index of 0.01 significantly affects the accurate precision of the optical power of the intraocular lens, so that, as in the material of the present invention, the use of the material with the water content exceeding 4% should be avoided for the optical result of the intraocular lens constituted by the main hydrophobic material, and the refractive index n at the time of complete dehydration is preferred0And refractive index n in equilibrium state after complete hydration1Materials having a difference of not more than 0.01, or preferably n0And n1A material having a difference of not more than 0.006, or preferably n0And n1The difference between them does not exceed 0.003.
The ophthalmic materials, such as intraocular lens materials, provided by the present invention, may also contain, if necessary, one or more desired additives or functional agents, such as hydrophilic acrylates, cross-linking agents, ultraviolet absorbers, blue-light absorbers, pharmacotherapeutic agents, and the like.
In accordance with another embodiment of the present invention, ophthalmic materials, such as intraocular lens materials, are provided which may contain a crosslinking agent, wherein the crosslinking agent is selected from polymerizable monomers having two or more functionalities including: ethylene glycol dimethacrylate, ethylene glycol diacrylate, butylene glycol dimethacrylate, butylene glycol diacrylate, hexanediol dimethacrylate, hexanediol diacrylate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylate, triethylene glycol diacrylate, polyethylene glycol dimethacrylate, polyethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, bisphenol A glycerol dimethacrylate, bisphenol A glycerol diacrylate, pentanediol dimethacrylate, methacrylic anhydride, acrylic anhydride, N '-methylenebisacrylamide, N' -methylenebismethacrylamide, propylene glycol dimethacrylate, ethylene glycol dimethacrylate, propylene glycol dimethacrylate, ethylene glycol dimethacrylate, divinylbenzene, or derivatives of the foregoing, or mixtures of the foregoing. Ethylene glycol dimethacrylate is preferred.
According to another embodiment of the present invention, there is provided an ophthalmic material such as an intraocular lens material comprising an ultraviolet absorber, wherein the ultraviolet absorber is selected from compounds having a high absorption function for ultraviolet rays having a wavelength range of 380 nm or less. Benzophenone compounds and/or benzotriazole compounds with high safety are preferable. More preferred are benzophenone-based compounds and/or benzotriazole-based compounds containing a polymerizable group selected from vinyl, allyl, butenyl, ethynyl, acryloxy, methacryloxy, acrylamido, methacrylamido, vinyl ether-based and the like, and mixtures thereof.
According to another embodiment of the present invention, the ophthalmic material, such as an intraocular lens material, may comprise a blue-light absorber, wherein the blue-light absorber is selected from compounds having a selective filtering function on blue light having a wavelength ranging from 400 to 500 nm. Preferably a yellow dye compound with a molecular structural formula containing azo groups. More preferred are yellow dye compounds containing a polymerizable group selected from vinyl, allyl, butenyl, ethynyl, acryloxy, methacryloxy, acrylamido, methacrylamido, vinyl ether groups, and the like, and mixtures thereof.
According to another embodiment of the present invention, the present invention provides ophthalmic materials, such as intraocular lens materials, obtained by polymerizing an aliphatic acrylate monomer as the second monomer and an aromatic acrylate monomer as the first monomer, optionally with additives. Wherein the polymerization mode is selected from bulk polymerization, and a free radical bulk polymerization mode is preferred. The radical polymerization initiator is selected from azo initiators, and/or peroxy initiators, preferably dilauroyl peroxide, bis (4-tert-butylcyclohexyl) peroxydicarbonate, dicetyl peroxydicarbonate, ditetradecyl peroxydicarbonate, azobisisobutyronitrile, azobisisovaleronitrile, azobisisoheptonitrile, dicumyl peroxide, benzoyl peroxide, 2, 5-dimethyl-2, 5-di (tert-butylperoxy) hexane, 2-ethylhexyl tert-butylperoxycarbonate, tert-amyl peroxy-2-ethylhexanoate, tert-amyl peroxy (2-ethylhexyl) carbonate, 2, 5-dimethyl-2, 5-bis (2-ethylhexanoic peroxy) hexane, 2, 5-dimethyl-2, 5-di-tert-butylperoxy-3-hexyne, tert-butyl peroxy (2-ethylhexanoate), 1-di-tert-butylperoxycyclohexane, tert-butyl neodecanoate peroxypivalate, tert-butyl 2-ethylbutane peroxycarboxylate, 1-di-tert-butylperoxy-3, 3, 5-trimethylcyclohexane, 3,6, 9-triethyl-3, 6, 9-trimethyl-1, 4, 7-triperoxonane, bis (3,5, 5-trimethylhexanoyl) peroxide, 1,3, 3-tetramethylbutyl peroxy-2-ethylhexanoate, tert-butylperoxy-3, 5, 5-trimethylhexanoate, tert-butylhydroperoxide, di-tert-butane peroxide, tert-butyl peroxybenzoate, T-butyl peroxyisopropyl formate, di (2-ethylhexyl) dicarbonate peroxide, t-butyl peroxyacetate, hydroxy cumene peroxide, diisopropylbenzene hydroperoxide, t-butylcumene peroxide, tert-amyl hydroperoxide, or a mixture of the foregoing. Azobisisobutyronitrile, and mixtures thereof, are preferred.
According to another embodiment of the present invention, the ophthalmic material, such as an intraocular lens material, is obtained by polymerizing an aliphatic acrylate monomer as a second monomer, an aromatic acrylate monomer as a first monomer, and optionally an additive, such as a hydrophilic acrylate monomer, a crosslinking agent, an ultraviolet absorber, a blue light absorber, and the like. Wherein the polymerization mode is selected from bulk polymerization, and a free radical bulk polymerization mode is preferred. The free radical polymerization initiator is selected from ultraviolet or visible light initiators, selected from benzoylphosphine type initiators, including but not limited to 2,4, 6-trimethylbenzoyldiphenylphosphine oxide; bis- (2, 6-dichlorobenzoyl) -4-N-propylphenylphosphine oxide; bis- (2, 6-dichlorobenzoyl) -4-N-butylphenyl phosphine oxide and the like, selected from diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, riboflavin and the like, selected from the series of initiator types sold under the trade name Darocur or Irgacur, preferably Darocur1173, and mixtures thereof.
According to another embodiment of the present invention, the ophthalmic material such as intraocular lens is prepared by mixing various monomers and additives (such as initiator, uv absorber, blue light absorber, etc.) and other additives, pouring into a specific mold, heating or irradiating to initiate polymerization, opening the mold to obtain blank for further processing or directly obtaining medical devices or equipment such as intraocular lens.
According to another embodiment of the present invention, the above materials are prepared by a method selected from, but not limited to: turning method, half-die half-pressing half-turning method and die pressing forming method; preferred compression molding methods include, for example, but are not limited to:
one of the optical profile is compression molded and the other is lathe formed;
-all optic contours are compression molded, and haptic structures are otherwise machined;
all optic and haptic structures are molded directly in one shot.
According to another embodiment of the present invention, the above materials can be used to make ophthalmic medical devices or apparatus, including but not limited to intraocular lenses, including aphakic and phakic intraocular lenses, contact lenses, orthokeratology lenses, iris hooks, intraocular lenses, artificial corneas, intracorneal rings, capsular bag tension rings, intracorneal lenses, glaucoma drainage valves, drug delivery vehicles, intraocular fillers, fundus fillers, eyeglasses, goggles, medical device lenses or medical treatment devices, or medical detection devices.
Drawings
Figure 1 shows the DSC profile for the Tg test of example 1.
FIG. 2 shows MTF for testing optical imaging quality of example 11And (4) mapping.
Detailed Description
Specifically, the present invention relates to the following aspects:
1. an ophthalmic material comprising the product of copolymerizing at least two monomers selected from the group consisting of:
a first monomer chosen from aromatic acrylate monomers in which the aromatic group is linked to the acryloyloxy group by a flexible group chosen from linear or branched alkyl, ether, sulfide,
-a second monomer selected from a hydrophobic aliphatic acrylate monomer or a hydrophilic aliphatic monomer,
wherein the weight ratio of the second monomer to the first monomer is 10-30: 70-90.
2. The ophthalmic material according to item 1, wherein the aromatic acrylate monomer has a molecular structural formula of:
R1= H or C1-6 alkyl, preferably H or CH3；
R2Is a linear or branched, saturated or unsaturated C1-6 alkylene group, preferably a C2-4 alkylene group,
n is 1 to 4, preferably 1 to 3, or 1, or 2.
3. The ophthalmic material according to any of the preceding claims, wherein the aromatic acrylate monomer is selected from the group consisting of: phenoxyethyl acrylate (POEA), phenoxyethyl methacrylate; phenoxy diethylene glycol acrylate (P (2EO) a); phenoxy triethylene glycol acrylate (P (3EO) a), phenoxy triethylene glycol methacrylate; phenoxy tetraethylene glycol triacetate (P (4EO) a), phenoxy tetraethylene glycol methacrylate, and mixtures thereof; more preferably, phenoxyethyl acrylate (POEA), phenoxydiethylene glycol acrylate (P (2EO) a), and mixtures thereof.
4. An ophthalmic material according to any of the preceding claims, wherein the hydrophobic aliphatic acrylate monomer or the hydrophilic aliphatic monomer has the molecular structure:
wherein:
- R3is H or C1-6 alkyl, preferably H or CH3；
- R4Is a linear or branched, saturated or unsaturated C1-6 alkylene group;
-m is 0 to 8, inclusive, or 0, 1, 2, 3, 4, 5, 6, 7 or 8;
- R5is a linear or branched, saturated or unsaturated C1-18 alkylene group, preferably a linear or branched, saturated or unsaturated C8-18 alkylene group;
-a is hydroxy or hydrogen;
with the following conditions: r4And R5Is not higher than 18.
5. An ophthalmic material according to any of the preceding claims, wherein the hydrophobic aliphatic acrylate monomer is selected from at least one of the following monomers: methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, butyl methacrylate, butyl acrylate, hexyl methacrylate, hexyl acrylate, isopropyl methacrylate, isopropyl acrylate, isobutyl methacrylate, isobutyl acrylate, tert-butyl methacrylate, tert-butyl acrylate, ethoxyethoxyethoxyethyl methacrylate, ethoxyethoxyethyl acrylate, ethoxyethyl methacrylate, methoxyethyl acrylate, isooctyl methacrylate, isooctyl acrylate, isodecyl methacrylate, lauryl acrylate, myristyl methacrylate, myristyl acrylate, cetyl methacrylate, cetyl acrylate, stearyl methacrylate, and mixtures thereof, Octadecyl acrylate, trifluoroethyl methacrylate, trifluoroethyl acrylate, hexafluorobutyl methacrylate, hexafluorobutyl acrylate, 2-perfluorodecyl ethyl methacrylate, 2- (perfluorooctyl) ethyl acrylate, and mixtures thereof.
6. An ophthalmic material according to any of the preceding claims, wherein the second monomer is selected from long chain branched hydrophobic aliphatic acrylate monomers, wherein:
-the long chain branched hydrophobic aliphatic acrylate monomer is selected from at least one of the following monomers: isooctyl methacrylate, isooctyl acrylate, isodecyl methacrylate, lauryl acrylate, tetradecyl methacrylate, tetradecyl acrylate, hexadecyl methacrylate, hexadecyl acrylate, octadecyl methacrylate, octadecyl acrylate, ethyl 2-perfluorodecyl methacrylate, 2- (perfluorooctyl) ethyl acrylate, and mixtures thereof;
7. an ophthalmic material according to any of the preceding claims, wherein the second monomer is selected from short-chain branched hydrophobic aliphatic acrylate monomers, wherein:
-the short-chain branched hydrophobic aliphatic acrylate monomer is selected from at least one of the following monomers: methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, butyl methacrylate, butyl acrylate, hexyl methacrylate, hexyl acrylate, isopropyl methacrylate, isopropyl acrylate, isobutyl methacrylate, isobutyl acrylate, t-butyl methacrylate, t-butyl acrylate, ethoxyethoxyethoxyethyl methacrylate, ethoxyethoxyethoxyethyl acrylate, ethoxyethyl methacrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, methoxyethyl acrylate, trifluoroethyl methacrylate, trifluoroethyl acrylate, hexafluorobutyl methacrylate, hexafluorobutyl acrylate, and mixtures thereof.
8. The ophthalmic material according to any of the preceding claims, wherein the second monomer is selected from hydrophilic aliphatic monomers, wherein:
-the hydrophilic aliphatic monomer is selected from the group consisting of glycidyl methacrylate, glycidyl acrylate, polyethylene glycol (meth) acrylate monoester, methoxypolyethylene glycol (meth) acrylate monoester, ethoxypolyethylene glycol (meth) acrylate monoester, polypropylene glycol (meth) acrylate monoester, polyglycerol (meth) acrylate monoester, and mixtures thereof.
9. An ophthalmic material according to any of the preceding claims wherein the hydrophilic aliphatic monomer has a molecular weight of less than 500 g/mol.
10. An ophthalmic material according to any of the preceding claims wherein the co-polymerised monomers further comprise a hydrophilic acrylate monomer which enables the formation of a continuous phase within the material.
11. An ophthalmic material according to any of the preceding claims, wherein when the second monomer is selected from short-chain branched hydrophobic aliphatic acrylate monomers, the co-polymerized monomers further comprise hydrophilic acrylate monomers which enable the formation of a continuous phase within the material.
12. An ophthalmic material according to any of the preceding claims, wherein the hydrophilic acrylate monomers capable of forming a continuous phase inside the material are selected from hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, hydroxypropyl acrylate, glycerol monomethacrylate, glycerol monoacrylate, vinylpyrrolidone, dimethylacrylamide, acrylic acid, methacrylic acid, 2- (trifluoromethyl) acrylic acid, phenylacrylic acid, acrylamide, methacrylamide, N-methylolacrylamide, N-methylolmethacrylamide, or derivatives of the aforementioned, and mixtures thereof.
13. An ophthalmic material according to any of the preceding claims, which is the product of copolymerization of at least two monomers selected from the group consisting of:
-the first monomer is selected from phenoxyethyl acrylate, phenoxyethyl methacrylate, phenoxydiethylene glycol acrylate;
-the second monomer is selected from isodecyl acrylate, isodecyl methacrylate, lauryl acrylate, tetradecyl methacrylate, tetradecyl acrylate.
14. An ophthalmic material according to any of the preceding claims, which is the product of copolymerization of at least three monomers selected from the group consisting of:
-a first monomer selected from phenoxyethyl acrylate, phenoxyethyl methacrylate, phenoxydiethylene glycol acrylate;
-a second monomer selected from the group consisting of ethyl methacrylate, ethyl acrylate, butyl methacrylate, butyl acrylate, ethoxyethoxyethyl methacrylate, ethoxyethoxyethoxyethyl acrylate, ethoxyethyl methacrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, methoxyethyl acrylate;
-hydrophilic acrylate monomers capable of forming a continuous phase inside said material, selected from hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, hydroxypropyl acrylate.
15. An ophthalmic material according to any of the preceding claims, which is the product of copolymerization of at least two monomers selected from the group consisting of:
-the first monomer is selected from phenoxyethyl acrylate, phenoxyethyl methacrylate, phenoxydiethylene glycol acrylate;
the second monomer is selected from polyethylene glycol (meth) acrylate monoesters, methoxypolyethylene glycol (meth) acrylate monoesters, ethoxypolyethylene glycol (meth) acrylate monoesters, polypropylene glycol (meth) acrylate monoesters.
16. The ophthalmic material according to item 1, wherein the weight ratio of the second monomer to the first monomer is 10-20:80-90, or 20-30:70-80, or 10-15:85-90, or 25-30: 70-75.
17. The ophthalmic material according to any of the preceding claims, further comprising UV absorbers, blue-light absorbers, colouring dyes, fluorescers, pharmaceutical agents.
18. An ophthalmic material according to any of the preceding claims, wherein the radial shrinkage of the ophthalmic material during the compression curing molding of the intraocular lens is less than 1%, preferably less than 0.5%.
19. An ophthalmic material according to any of the preceding claims, wherein the refractive index at 35 ℃ is in the range 1.49 to 1.56, or 1.50 to 1.54, or 1.52 to 1.54.
20. An ophthalmic material according to any of the preceding claims, wherein the glass transition temperature is from 6 to 35 ℃, or from 8 to 20 ℃, or from 10 to 18 ℃.
21. An ophthalmic material according to any of the preceding claims, wherein the weight ratio of hydrophilic acrylate monomers capable of forming a continuous phase inside the material relative to the sum of the first and second monomers is 5: 95; preferably, 10: 90; or 15: 85; even 20: 80.
22. An ophthalmic material according to any of the preceding claims, wherein the ophthalmic material has a water content of 1-4wt%, preferably 1.5-4wt%, more preferably 2-3wt% at 35 ℃.
23. A medical device or apparatus prepared from the ophthalmic material of any one of the preceding claims, wherein the device or apparatus is selected from the group consisting of: the intraocular lens can also be used for manufacturing a contact lens, a keratoplasty lens, an iris retractor, an intraocular lens, an artificial cornea, an intracorneal ring, a capsular bag tension ring, an intracorneal lens, a glaucoma drainage valve, a drug sustained release carrier, an intraocular filler, a fundus filler, spectacles, goggles, a medical device lens or a medical treatment device such as a device for treating ophthalmic diseases, for example, a device for treating posterior cataract, or a medical detection device such as a medical detection device having a fluorescent characteristic.
24. The method of making a medical device or apparatus of item 23, comprising the step of using direct compression molding of the ophthalmic material.
25. The production method according to the aforementioned item 24, which comprises the steps of mixing the monomer and the initiator, injecting the mixture into a mold, initiating polymerization by heating or light irradiation, and opening the mold to directly obtain the medical device or apparatus.
26. The method of making a medical device or apparatus of item 23, comprising the step of shaping the ophthalmic material using a lathe turning process.
27. The production method according to the aforementioned item 23, which comprises a step of forming the ophthalmic material into a blank and then processing into a medical device or apparatus by a turning technique.
28. An intraocular lens made from a material according to any one of claims 1 to 22, wherein the method of making comprises the step of compression molding at least one optical portion profile directly; preferably all of the optic faces are compression molded directly, and the haptic structures are otherwise machined; more preferably, the entire optic face and haptic structures are compression molded directly in one compression.
29. Use of a material according to any one of items 1 to 22 in the manufacture of a medical device or apparatus, wherein the device or apparatus is selected from: the intraocular lens can also be used for manufacturing a contact lens, a keratoplasty lens, an iris retractor, an intraocular lens, an artificial cornea, an intracorneal ring, a capsular bag tension ring, an intracorneal lens, a glaucoma drainage valve, a drug sustained release carrier, an intraocular filler, a fundus filler, spectacles, goggles, a medical device lens or a medical treatment device such as a device for treating ophthalmic diseases, for example, a device for treating posterior cataract, or a medical detection device such as a medical detection device having a fluorescent characteristic.
Examples
The present invention will be described in more detail by way of specific examples, which are provided for illustration only and are not intended to limit the present invention.
The test method of the embodiment of the invention comprises the following steps:
all the monomers in the embodiments are purified, the corresponding monomers are mixed according to the corresponding proportion in a 250ml (milliliter) beaker, an initiator and a light absorbent are added, nitrogen is introduced, the mixture is fully and uniformly stirred and filtered by a polytetrafluoroethylene microporous filter membrane with the aperture of 0.2-0.8 mu m (micrometer), the mixture is injected into a female mold of the artificial lens, the mold cavity of the female mold is filled, then a male mold is placed on the female mold, and after the male mold is closed, the male mold is placed in an oven with the set temperature for polymerization reaction for at least 6 hours. And taking out the polymer formed in the mold, naturally cooling to room temperature, placing the blank in a vacuum drying oven at a set temperature, and removing unreacted residual small molecular monomers to obtain the material.
Method for testing water content of prepared material
The testing method comprises placing the prepared material in normal saline, placing in a constant temperature incubator at 35 deg.C, balancing for at least 7 days to make the material fully hydrated to balance, taking out, quickly wiping off surface water, and testing wet weight m1. Then the material is put in a vacuum oven at 60-100 ℃, fully dried to constant weight and weighed to obtain dry weight m2. And (4) calculating the water content of the material in the hydration equilibrium state according to the formula I.
Water content =
(III)
Method for testing glass transition temperature of prepared material
The testing method relates to that a differential scanning calorimetry analyzer with the model number Q20 produced by a American TA instrument is adopted, the glass transition temperature of an analysis material is calculated by self-contained software according to the sample amount of 10mg (milligram) and the temperature rise rate of 10 ℃ per minute and the temperature scanning range of-40-60 ℃.
Refractive index measurement method of prepared material
A method for measuring the refractive index (refractive index) of a material relates to that an Abbe refractometer is used for testing the refractive index of the material in a hydration state, a testing method well known by a person skilled in the art is adopted, the Abbe refractometer is connected with a constant-temperature water bath kettle, the temperature of the constant-temperature water bath kettle is set to 35 ℃ during testing, the prepared material is hydrated by using normal saline, and the prepared material is put into a constant-temperature incubator at 35 ℃ for balancing for 7 days, so that the material is fully hydrated to the refractive index of the tested material after balancing. And taking out the hydrated material sheet, quickly wiping off the surface moisture, and placing the hydrated material sheet on an Abbe refractometer test platform to read data.
Shrinkage testing method of prepared material
The shrinkage of the material from monomer cured to polymer material was tested by L1 for the diameter of the iol mold as measured using an optical projector and L2 for the diameter of the molded, cured iol as measured using an optical projector. And calculating the radial curing shrinkage of the material according to formula II.
Shrinkage =
(IV)
Method for testing flash point in prepared material
The test method comprises soaking the material in balanced salt solution simulating intraocular state, standing at 37 + -1 deg.C for 3 months, 6 months and 12 months, and observing the occurrence and amount of Glistening in the material under microscope with magnification of 20 times or more.
Intraocular lens optical imaging quality MTF test
The test method relates to the evaluation of imaging quality by testing the Modulation Transfer Function (MTF) of an intraocular lens according to the relevant international standard 'BS EN ISO 11979-2 ocular implant, intraocular lens, optical characteristics and test method' by using an intraocular lens whose optical part is molded directly. Intraocular lens measurement at 100mm using a TRIOPTIC optical gauge-1(mm. mu.m)-1) Placing the artificial lens in a model eye, measuring a Modulation Transfer Function (MTF) by using monochromatic light, wherein the light source wavelength is 546 nm +/-10 nm (nanometers), the size of the artificial lens has small deviation from the size of the artificial lens in an intraocular state at room temperature, and measuring at room temperature; where the test MTF value is greater than or equal to 0.43, the intraocular lens can be considered to have acceptable imaging quality, with the higher the MTF value, the better the imaging quality of the intraocular lens.
Examples 1 to 9
Hereinafter, the present invention will be described in more detail by way of specific examples, which are provided by way of illustration only and are not intended to limit the present invention.
Examples 1 to 9 shown in Table 1 illustrate the materials of the present invention. All examples in table 1 were prepared in the following manner and all monomers were purified by distillation under reduced pressure. Respectively mixing aromatic acrylate monomers and aliphatic acrylate monomers according to corresponding proportions in a 250ml beaker, wherein the monomers comprise hydrophilic monomers and crosslinking monomers (ethylene glycol dimethacrylate EGDMA is taken as an example), adding an initiator (azobisisobutyronitrile AIBN is taken as an example) and a light absorber (2- (4-benzoyl-3-hydroxyphenoxy) ethyl 2-acrylate UV416 is taken as an example), fully stirring uniformly and filtering, degassing and inflating by using nitrogen for 3 cycles, injecting a proper amount of monomer solution into an artificial lens female die, then placing a male die on the female die, closing the dies, placing the dies in an oven with a set temperature of 50-100 ℃ for polymerization reaction for at least 6 hours, and carrying out curing molding; cooling to room temperature, opening the mold, taking out the molded intraocular lens blank, transferring the molded intraocular lens blank to a vacuum drying oven at a set temperature to remove unreacted residual small molecular monomers, and measuring the curing shrinkage rate (radial direction), glass transition temperature and the like of the material; hydrating the prepared material by using normal saline, and balancing in a constant-temperature incubator at 35 ℃ for 7 days to fully hydrate the material to balance and then testing the refractive index and the water content of the material; after the blank material is further processed into an artificial lens, the MTF value is tested, then the artificial lens is soaked in balanced salt solution simulating the intraocular state, the artificial lens is placed at the temperature of 37 +/-1 ℃ for 6 months, a microscope with the magnification of more than 20 times is used for observing whether a 'Glistening point (Glistening') appears in the material, and the MTF value of the artificial lens is tested again. The various utensils and molds used in the above-described implementation process are cleaned, dried and sterilized before use.
Comparative examples 1 to 6
The materials of comparative examples 1 to 6 shown in Table 2 were prepared in the same manner as in examples 1 to 9, and all the monomers were purified by distillation under reduced pressure.
Table 2 comparative example 1
Comparative example 1: obtained by copolymerizing the first monomers PEA and PEMA, the curing shrinkage is low, but has a sparkling point.
| PEA | PEMA | S% | Tg/℃ | RI | Water% | MTF1 | Flash point | MTF2 | |
| Comparative example 1 | 50 | 40 | 0.23 | 14 | 1.56 | 0.3% | 0.53 | Is provided with | 0.33 |
PEA: acrylic acid phenyl ethyl ester
PEMA: and (3) phenylethyl methacrylate.
Table 3 comparative example 2
Comparative example 2: the second monomer EA + EMA or EMA + LMA is copolymerized to obtain the high-shrinkage-rate crystal, and the compression molding crystal cannot be realized.
| EA | EMA | S% | Tg/℃ | RI | Water% | MTF1 | Flash point | MTF2 | |
| Comparative example 2 | 50 | 40 | 3.1 | 10 | 1.48 | 0.4% | 0.23 | Is free of | 0.25 |
EA: acrylic acid ethyl ester
EMA: and (3) ethyl methacrylate.
TABLE 4 comparative examples 3-4
Comparative examples 3 to 4: obtained by copolymerization of POEA and EA, the dual effect cannot be achieved by adjusting the ratio: when the first monomer content is high, the requirement of low curing shrinkage rate and flash points is met; when the content of the second monomer is high, the flash point is avoided, but the shrinkage rate is high, and the compression molding cannot be carried out.
| POEA | LMA | EA | S% | Tg/℃ | RI | Water% | MTF1 | Flash point | MTF2 | |
| Example 1 | 86 | 10 | 0.47 | 13 | 1.56 | 0.3 | 0.52 | Is free of | 0.51 | |
| Comparative example 3 | 86 | 10 | 0.28 | 16 | 1.56 | 0.3% | 0.53 | Is provided with | 0.33 | |
| Comparative example 4 | 60 | 36 | 1.28 | 10 | 1.52 | 0.4% | 0.29 | Is free of | 0.31 |
POEA: phenoxyethyl acrylate
EA: and (3) ethyl acrylate.
TABLE 5 comparison of inventive example 7 with comparative examples 5 to 6
Embodiment 7 of the present invention: obtained by POEA + EA + HEMA copolymerization; excellent performance is obtained: and the curing shrinkage can be ensured to be low, and the flash point can be ensured to be avoided (the water content is 2-3%, and the material is not subjected to hydrophobic-hydrophilic essential change).
Comparative examples 5 to 6: obtained by POEA + HEMA copolymerization, the double effect cannot be achieved by adjusting the ratio: when the proportion of the hydrophilic monomer is low, the curing shrinkage rate is low, but the flash point cannot be eliminated through the water content; when the hydrophilic ratio is high, the curing shrinkage is high and the molding cannot be performed.
| POEA | HEMA | EA | S% | Tg/℃ | RI | Water% | MTF1 | Flash point | MTF2 | |
| Example 7 | 60 | 10 | 26 | 0.48 | 15 | 1.52 | 2.0 | 0.52 | Is free of | 0.52 |
| Comparative example 5 | 86 | 10 | 0 | 0.25 | 27 | 1.55 | 1.1% | 0.52 | Is provided with | 0.34 |
| Comparative example 6 | 60 | 36 | 0 | 1.21 | 34 | 1.51 | 2.5% | 0.28 | Is free of | 0.27 |
POEA: phenoxyethyl acrylate
EA: acrylic acid ethyl ester
HEMA: hydroxyethyl methacrylate.
It can be seen from the comparative examples that when the aliphatic monomer content in the material is lower, the material can have lower shrinkage, but the simulation will generate more (serious) flash point phenomenon in the environment of the eyes for a long time; in addition, when the material has a high water content, although the flash point phenomenon can be eliminated, the refractive index of the material is low, the glass transition temperature is high, and the realization of foldability of the material is not favorable.
As can be seen from the data in tables 1-5 above, intraocular lenses made from the ophthalmic materials of the present invention combine lower shrinkage with elimination of the flare phenomenon.
Claims (10)
1. An ophthalmic material comprising the product of copolymerizing at least two monomers selected from the group consisting of:
a first monomer chosen from aromatic acrylate monomers in which the aromatic group is linked to the acryloyloxy group by a flexible group chosen from linear or branched alkyl, ether, sulfide,
-a second monomer selected from a hydrophobic aliphatic acrylate monomer or a hydrophilic aliphatic acrylate monomer,
wherein the weight ratio of the second monomer to the first monomer is 10-30: 70-90.
2. The ophthalmic material of claim 1 wherein the aromatic acrylate monomer has the molecular structure:
R1= H or C1-6 alkyl, preferably H or CH3；
R2Is a linear or branched, saturated or unsaturated C1-6 alkylene group, preferably a C2-4 alkylene group,
n is 1 to 4, preferably 1 to 3, or 1, or 2.
3. An ophthalmic material according to any of the preceding claims, wherein the hydrophobic or hydrophilic aliphatic acrylate monomer has the molecular formula:
wherein:
- R3is H or C1-6 alkyl, preferably H or CH3；
- R4Is a linear or branched, saturated or unsaturated C1-6 alkylene group;
-m is 0 to 8, inclusive, or 0, 1, 2, 3, 4, 5, 6, 7 or 8;
- R5is a linear or branched, saturated or unsaturated C1-18 alkylene group, preferably a linear or branched, saturated or unsaturated C8-18 alkylene group;
-a is hydroxy or hydrogen;
with the following conditions: r4And R5Is not higher than 18.
4. An ophthalmic material according to any of the preceding claims, wherein the second monomer is selected from long chain branched hydrophobic aliphatic acrylate monomers, wherein:
-the long chain branched hydrophobic aliphatic acrylate monomer is selected from at least one of the following monomers: isooctyl methacrylate, isooctyl acrylate, isodecyl methacrylate, lauryl acrylate, tetradecyl methacrylate, tetradecyl acrylate, hexadecyl methacrylate, hexadecyl acrylate, octadecyl methacrylate, octadecyl acrylate, ethyl 2-perfluorodecyl methacrylate, 2- (perfluorooctyl) ethyl acrylate, and mixtures thereof.
5. An ophthalmic material according to any of the preceding claims, wherein the second monomer is selected from short-chain branched hydrophobic aliphatic acrylate monomers, wherein:
-the short-chain branched hydrophobic aliphatic acrylate monomer is selected from at least one of the following monomers: methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, butyl methacrylate, butyl acrylate, hexyl methacrylate, hexyl acrylate, isopropyl methacrylate, isopropyl acrylate, isobutyl methacrylate, isobutyl acrylate, t-butyl methacrylate, t-butyl acrylate, ethoxyethoxyethoxyethyl methacrylate, ethoxyethoxyethoxyethyl acrylate, ethoxyethyl methacrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, methoxyethyl acrylate, trifluoroethyl methacrylate, trifluoroethyl acrylate, hexafluorobutyl methacrylate, hexafluorobutyl acrylate, and mixtures thereof.
6. An ophthalmic material according to any of the preceding claims, wherein the second monomer is selected from hydrophilic aliphatic acrylic monomers, wherein:
-the hydrophilic aliphatic monomer is selected from the group consisting of glycidyl methacrylate, glycidyl acrylate, polyethylene glycol (meth) acrylate monoester, methoxypolyethylene glycol (meth) acrylate monoester, ethoxypolyethylene glycol (meth) acrylate monoester, polypropylene glycol (meth) acrylate monoester, polyglycerol (meth) acrylate monoester, and mixtures thereof.
7. An ophthalmic material according to any of the preceding claims wherein the copolymerised monomers further comprise a hydrophilic acrylate monomer which enables the formation of a continuous phase within the material.
8. An ophthalmic material according to any of the preceding claims wherein when the second monomer is selected from short-chain branched hydrophobic aliphatic acrylate monomers, the co-polymerized monomers further comprise hydrophilic acrylate monomers which enable the formation of a continuous phase within the material.
9. An ophthalmic material according to any of the preceding claims wherein the hydrophilic acrylate monomers capable of forming a continuous phase within the material are selected from hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, hydroxypropyl acrylate, glyceryl monomethacrylate, glyceryl monoacrylate, vinylpyrrolidone, dimethylacrylamide, acrylic acid, methacrylic acid, 2- (trifluoromethyl) acrylic acid, phenylacrylic acid, acrylamide, methacrylamide, N-methylolacrylamide, N-methylolmethacrylamide, or derivatives thereof, and mixtures thereof.
10. A medical device or apparatus prepared from the ophthalmic material of any one of the preceding claims, wherein the device or apparatus is selected from the group consisting of: the intraocular lens can also be used for manufacturing a contact lens, a keratoplasty lens, an iris retractor, an intraocular lens, an artificial cornea, an intracorneal ring, a capsular bag tension ring, an intracorneal lens, a glaucoma drainage valve, a drug sustained release carrier, an intraocular filler, a fundus filler, spectacles, goggles, a medical device lens or a medical treatment device such as a device for treating ophthalmic diseases, for example, a device for treating posterior cataract, or a medical detection device such as a medical detection device having a fluorescent characteristic.
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