CN111542348B - 人工晶状体用材料 - Google Patents
人工晶状体用材料 Download PDFInfo
- Publication number
- CN111542348B CN111542348B CN201880084545.1A CN201880084545A CN111542348B CN 111542348 B CN111542348 B CN 111542348B CN 201880084545 A CN201880084545 A CN 201880084545A CN 111542348 B CN111542348 B CN 111542348B
- Authority
- CN
- China
- Prior art keywords
- monomer
- acrylate
- mol
- intraocular lens
- methacrylate
- 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.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 68
- 239000000178 monomer Substances 0.000 claims abstract description 209
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 63
- 239000000203 mixture Substances 0.000 claims abstract description 51
- -1 alkoxyalkyl methacrylate Chemical compound 0.000 claims abstract description 47
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 238000002156 mixing Methods 0.000 claims abstract description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 9
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 7
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 claims description 5
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002861 polymer material Substances 0.000 claims description 3
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 2
- CKMWTCBLFNZFSS-UHFFFAOYSA-N [2-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl] prop-2-enoate Chemical compound C(C=C)(=O)OC1=C(C=CC=C1)C(C(F)(F)F)C(F)(F)F CKMWTCBLFNZFSS-UHFFFAOYSA-N 0.000 claims 4
- DCLHIBVYZVNRKW-UHFFFAOYSA-N (2-propan-2-ylphenyl) prop-2-enoate Chemical compound CC(C)C1=CC=CC=C1OC(=O)C=C DCLHIBVYZVNRKW-UHFFFAOYSA-N 0.000 claims 3
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims 2
- KGXXHMBLBNYRBN-UHFFFAOYSA-N (2-propylphenyl) prop-2-enoate Chemical compound CCCC1=CC=CC=C1OC(=O)C=C KGXXHMBLBNYRBN-UHFFFAOYSA-N 0.000 claims 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 claims 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 abstract description 15
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 15
- 210000000695 crystalline len Anatomy 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229960005323 phenoxyethanol Drugs 0.000 description 18
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 16
- 238000004090 dissolution Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000000413 hydrolysate Substances 0.000 description 5
- 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 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000003780 insertion Methods 0.000 description 4
- 230000037431 insertion Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 2
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 230000004313 glare Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WFRLANWAASSSFV-FPLPWBNLSA-N palmitoleoyl ethanolamide Chemical compound CCCCCC\C=C/CCCCCCCC(=O)NCCO WFRLANWAASSSFV-FPLPWBNLSA-N 0.000 description 2
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- DSTUKHPLWATFCG-UHFFFAOYSA-N (2-benzoylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C(=O)C1=CC=CC=C1 DSTUKHPLWATFCG-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- AFXKUUDFKHVAGI-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidin-2-one Chemical compound CN1CCC(=C)C1=O AFXKUUDFKHVAGI-UHFFFAOYSA-N 0.000 description 1
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 description 1
- PLXOUIVCSUBZIX-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)COC(=O)C=C PLXOUIVCSUBZIX-UHFFFAOYSA-N 0.000 description 1
- VHJHZYSXJKREEE-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl prop-2-enoate Chemical compound FC(F)C(F)(F)COC(=O)C=C VHJHZYSXJKREEE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- YOIZTLBZAMFVPK-UHFFFAOYSA-N 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC(C(O)C(O)=O)=CC=C1O YOIZTLBZAMFVPK-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- IDCQTWRQPQAEQJ-UHFFFAOYSA-N 2-methylidene-4-phenylbutanoic acid 2-phenylethyl prop-2-enoate Chemical compound C1(=CC=CC=C1)CCC(C(=O)O)=C.C(C=C)(=O)OCCC1=CC=CC=C1 IDCQTWRQPQAEQJ-UHFFFAOYSA-N 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- SRUHSYGFKGCING-UHFFFAOYSA-N BrC1=C(C(=C(C(=C1C(C(=O)O)=C)Br)Br)Br)Br.C(C=C)(=O)OC1=C(C(=C(C(=C1Br)Br)Br)Br)Br Chemical compound BrC1=C(C(=C(C(=C1C(C(=O)O)=C)Br)Br)Br)Br.C(C=C)(=O)OC1=C(C(=C(C(=C1Br)Br)Br)Br)Br SRUHSYGFKGCING-UHFFFAOYSA-N 0.000 description 1
- CNCZDQLNZDZQFR-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(=O)O)=C.C(C=C)(=O)OC1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(C(=O)O)=C.C(C=C)(=O)OC1=CC=CC=C1 CNCZDQLNZDZQFR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- ZVYGUCWDWWHVTD-UHFFFAOYSA-N FC(CC(C(=O)O)=C)(C(C(C(F)F)(F)F)(F)F)F.C(C=C)(=O)OCC(C(C(C(F)F)(F)F)(F)F)(F)F Chemical compound FC(CC(C(=O)O)=C)(C(C(C(F)F)(F)F)(F)F)F.C(C=C)(=O)OCC(C(C(C(F)F)(F)F)(F)F)(F)F ZVYGUCWDWWHVTD-UHFFFAOYSA-N 0.000 description 1
- HOOWLHHIWQXSRB-UHFFFAOYSA-N FC(CC(C(=O)O)=C)(C(C(F)(F)F)F)F.C(C=C)(=O)OCC(C(C(F)(F)F)F)(F)F Chemical compound FC(CC(C(=O)O)=C)(C(C(F)(F)F)F)F.C(C=C)(=O)OCC(C(C(F)(F)F)F)(F)F HOOWLHHIWQXSRB-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- NFSAGZMETYAGKX-UHFFFAOYSA-N O(C1=CC=CC=C1)CCC(C(=O)O)=C.C(C=C)(=O)OCCOC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)CCC(C(=O)O)=C.C(C=C)(=O)OCCOC1=CC=CC=C1 NFSAGZMETYAGKX-UHFFFAOYSA-N 0.000 description 1
- GVMYIWIPPADCPW-UHFFFAOYSA-N OC(=O)C(=C)Cc1ccccc1.C=CC(=O)OCc1ccccc1 Chemical compound OC(=O)C(=C)Cc1ccccc1.C=CC(=O)OCc1ccccc1 GVMYIWIPPADCPW-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 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
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 description 1
- 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
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000002237 fumaric acid derivatives Chemical class 0.000 description 1
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- KCAMXZBMXVIIQN-UHFFFAOYSA-N octan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCC(CC)OC(=O)C(C)=C KCAMXZBMXVIIQN-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- GOZDOXXUTWHSKU-UHFFFAOYSA-N pentadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C=C GOZDOXXUTWHSKU-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001052 yellow pigment 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
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/14—Eye parts, e.g. lenses, corneal implants; Implanting instruments specially adapted therefor; Artificial eyes
- A61F2/16—Intraocular lenses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
-
- 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
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- 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
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- 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
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Materials For Medical Uses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Prostheses (AREA)
Abstract
本发明提供一种耐水解性得到提高的人工晶状体用材料。本发明的人工晶状体用材料是将包含基础单体、亲水性单体及交联性单体的单体组合物聚合而获得,所述基础单体包含含芳香环的丙烯酸酯单体、以及具有碳数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯单体,并且所述单体组合物中所含的所有单体成分中的、甲基丙烯酸酯单体相对于丙烯酸酯单体的摩尔基准调配比例为0.25~1.00。
Description
技术领域
本发明涉及一种人工晶状体用材料。
背景技术
人工晶状体(intraocular lenses)是白内障手术时插入眼中来代替晶体的晶状体(lens)。为了可自极小的切开创口插入眼内,开发有柔软且可折叠的材料,且由于柔软性优异、具有高折射率,因此近年来丙烯酸系材料成为主流。
例如,专利文献1中提出有:一种人工晶状体用材料,包含使聚合成分聚合而获得的聚合物,且吸水率为1.5质量%~4.5质量%,所述聚合成分含有包含含羟基的(甲基)丙烯酸烷基酯、(甲基)丙烯酰胺单体及N-乙烯基内酰胺等的亲水性单体。所述人工晶状体用材料由于柔软性优异、具有高折射率,因此可使晶状体变薄,可在折叠状态下自切开创口插入,进而,可抑制闪光(glistening)而具有优异的透明性。
现有技术文献
专利文献
专利文献1:日本专利特开平11-56998号公报
发明内容
发明所要解决的问题
所述丙烯酸系人工晶状体用材料有时在水溶液中发生水解,虽为微量,但有时水解物在眼内溶出。本发明是鉴于所述问题而成,因此,本发明的主要目的在于提供一种耐水解性得到提高的人工晶状体用材料。
解决问题的技术手段
本发明人等人对所述问题进行了研究,结果得知,通过在包含含芳香环的丙烯酸酯单体、亲水性单体及交联性单体的单体组合物中调配特定的甲基丙烯酸烷氧基烷基酯单体(alkoxyalkyl methacrylate monomer),可获得抑制闪光的产生、并且耐水解性提高的人工晶状体材料。另一方面,还明确:因使用甲基丙烯酸烷氧基烷基酯单体,而聚合物材料的柔软性降低,从而折叠时可能会产生问题。因此,本发明人等人进而继续研究,结果发现,通过将单体组合物中的丙烯酸酯单体与甲基丙烯酸酯单体的调配比例设为规定的范围,可获得维持适于折叠的柔软性、并且耐水解性提高的聚合物材料。
即,本发明的人工晶状体材料是将包含基础单体、亲水性单体及交联性单体的单体组合物聚合而获得,所述基础单体包含含芳香环的丙烯酸酯单体、以及具有碳数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯单体,并且所述单体组合物中所含的所有单体成分中的、甲基丙烯酸酯单体相对于丙烯酸酯单体的摩尔基准调配比例为0.25~1.00。
在一个实施方式中,所述甲基丙烯酸烷氧基烷基酯单体为选自甲基丙烯酸甲氧基乙酯及甲基丙烯酸乙氧基乙酯中的一种以上。
在一个实施方式中,在将所述单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述甲基丙烯酸烷氧基烷基酯单体的调配量为1摩尔%~30摩尔%。
在一个实施方式中,在将所述单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述亲水性单体的调配量为10摩尔%~40摩尔%。
在一个实施方式中,在将所述单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述交联性单体的调配量为0.1摩尔%~5摩尔%。
在一个实施方式中,所述含芳香环的丙烯酸酯单体具有苯氧基、碳数2以下的亚烷基及丙烯酸酯键结部位。
在一个实施方式中,所述单体组合物还包含具有碳数为1~20的烷基的丙烯酸烷基酯单体。
在一个实施方式中,在将所述单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述丙烯酸烷基酯单体的调配量为15摩尔%~45摩尔%。
在一个实施方式中,所述人工晶状体材料的断裂应力为4.5MPa~11.0MPa。
发明的效果
根据本发明,可获得维持适于折叠的柔软性、并且耐水解性提高的人工晶状体用材料。
附图说明
图1是断裂应力测定中使用的试验片的说明图。
具体实施方式
以下,对本发明的优选的实施方式进行说明,但本发明并不限定于这些实施方式。
在一个实施方式中,本发明的人工晶状体用材料是将包含基础单体、亲水性单体及交联性单体的单体组合物聚合而获得,所述基础单体包含含芳香环的丙烯酸酯单体、以及具有碳数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯单体。单体组合物优选为进而包含具有碳数为1~20的烷基的丙烯酸烷基酯单体作为基础单体。换句话说,本发明的人工晶状体用材料包含源自所述各单体的重复单元。
所述人工晶状体材料具有维持适于折叠的柔软性、并且耐水解性优异这一特征。获得此种效果的理由并不确定,如以下般推测。即,推测:甲基丙烯酸酯结构因甲基的存在而较丙烯酸酯结构而言不易受到水的侵蚀(attack),因此,通过在基础单体中调配甲基丙烯酸酯单体,可提高所获得的材料的耐水解性。另一方面,由于在基础单体中调配甲基丙烯酸酯单体,因此材料的柔软性会降低,但通过使用具有碳数4以下的烷氧基烷基的甲基丙烯酸酯单体作为甲基丙烯酸酯单体、以及将单体组合物中的丙烯酸酯单体与甲基丙烯酸酯单体的调配比例调整为特定的范围,可作为人工晶状体材料发挥理想的柔软性(折叠性能)。另外,所述人工晶状体材料还可为闪光得到抑制、具有高折射率、和/或柔软性与强度的平衡优异的材料。
A.单体组合物
A-1.基础单体
基础单体包含含芳香环的丙烯酸酯单体、以及具有碳数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯单体。视需要,基础单体可进而包含具有碳数为1~20的烷基的丙烯酸烷基酯单体。在本说明书中,所谓基础单体,是指构成人工晶状体用材料的主要结构的单体。
在将单体组合物中所含的所有单体成分设为100摩尔%时,单体组合物中的基础单体的调配量可设为59.9摩尔%~89.9摩尔%,优选为可为75摩尔%~85摩尔%。
A-1-1.含芳香环的丙烯酸酯单体
所述含芳香环的丙烯酸酯单体具有提高人工晶状体用材料的折射率的作用。含芳香环的丙烯酸酯单体可具有苯氧基、碳数2以下的亚烷基及丙烯酸酯键结部位。作为含芳香环的丙烯酸酯单体的具体例,可列举:丙烯酸苯氧基乙酯(phenoxyethyl acrylate)、丙烯酸苯基乙酯(phenylethyl acrylate)、丙烯酸苄基酯(benzyl acrylate)、丙烯酸苯基酯(phenyl acrylate)、丙烯酸五溴苯基酯(pentabromophenyl acrylate)等。含芳香环的丙烯酸酯单体可单独使用仅一种,也可组合使用两种以上,从共聚性或安全性的观点来看,所使用的所述单体的种类理想的是少,优选为可单独使用仅一种。
从即便单独使用时提高折射率的效果也大的方面来看,优选为丙烯酸苯氧基乙酯、丙烯酸苯基乙酯以及丙烯酸苄基酯,从进一步提高柔软性的方面来看,特别优选为丙烯酸苯氧基乙酯。
在将单体组合物中所含的所有单体成分设为100摩尔%时,含芳香环的丙烯酸酯单体的调配量可设为25摩尔%~55摩尔%。从即便在吸水状态下也显示出高折射率的观点来看,优选为30摩尔%~50摩尔%,更优选为35摩尔%~45摩尔%。若含芳香环的丙烯酸酯单体的调配量过多,则因其为体积大的结构,而有柔软性或形状恢复性降低的担忧。另一方面,若含芳香环的丙烯酸酯单体的调配量过少,则有无法获得所期望的折射率的担忧。
A-1-2.甲基丙烯酸烷氧基烷基酯单体(alkoxyalkyl methacrylate monomer)
所述甲基丙烯酸烷氧基烷基酯单体的烷氧基烷基可由下述化学式(1)表示。作为烷氧基,例如可列举甲氧基、乙氧基等。作为所述烷氧基所键结的亚烷基,可列举亚甲基、亚乙基等。作为甲基丙烯酸烷氧基烷基酯单体,优选为甲基丙烯酸甲氧基乙酯以及甲基丙烯酸乙氧基乙酯,从柔软性的观点来看,更优选为甲基丙烯酸乙氧基乙酯。甲基丙烯酸烷氧基烷基酯单体可单独使用或混合使用两种以上。
CnH2n+1OCmH2m-(其中,n及m分别为1以上的整数,且满足(n+m)≦4)…化学式(1)
在将单体组合物中所含的所有单体成分设为100摩尔%时,甲基丙烯酸烷氧基烷基酯单体的调配量可设为1摩尔%~30摩尔%。从适宜抑制水解的观点及折叠容易性的观点来看,所述调配量优选为2摩尔%~25摩尔%,更优选为5摩尔%~20摩尔%。在所述基础单体中,若甲基丙烯酸酯单体相对于丙烯酸酯单体的调配量增加,则有容易产生闪光等问题的倾向。其理由并不确定,推测为:在丙烯酸酯单体与甲基丙烯酸酯单体中,由于聚合速度不同而容易产生相分离(共聚性差),结果,容易产生闪光。相对于此,在本发明中,通过选择所述特定的甲基丙烯酸烷氧基烷基酯单体,即便以所述调配量使用甲基丙烯酸酯单体,也可维持闪光抑制能力。
A-1-3.丙烯酸烷基酯单体
所述丙烯酸烷基酯单体可助于人工晶状体用材料的形状恢复性及柔软性的进一步的提高。另外,由于可提高单体相互的共聚性,因此可获得更高的闪光抑制能力。
作为丙烯酸烷基酯单体,例如可列举:丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸丁酯、丙烯酸戊酯、丙烯酸己酯、丙烯酸庚酯、丙烯酸壬酯、丙烯酸硬脂基酯、丙烯酸辛酯、丙烯酸癸酯、丙烯酸月桂基酯、丙烯酸十五烷基酯、丙烯酸2-乙基己酯、丙烯酸环戊酯、丙烯酸环己酯等直链状、分支链状或环状的丙烯酸烷基酯单体等。另外,丙烯酸2,2,2-三氟乙酯、丙烯酸2,2,3,3-四氟丙酯、丙烯酸2,2,3,3-四氟-叔戊酯(2,2,3,3-tetrafluoro-t-pentyl acrylate)、丙烯酸2,2,3,4,4,4-六氟丁酯(2,2,3,4,4,4-hexafluorobutylacrylate)、丙烯酸2,2,3,4,4,4-六氟-叔己酯(2,2,3,4,4,4-hexafluoro-t-hexylacrylate)、丙烯酸2,3,4,5,5,5-六氟-2,4-双(三氟甲基)戊酯(2,3,4,5,5,5-hexafluoro-2,4-bis(trifluoromethyl)pentyl acrylate)、丙烯酸2,2,3,3,4,4-六氟丁酯(2,2,3,3,4,4-hexafluorobutyl acrylate)、丙烯酸2,2,2,2',2',2'-六氟异丙酯(2,2,2,2',2',2'-hexafluoroisopropyl acrylate)、丙烯酸2,2,3,3,4,4,4-七氟丁酯(2,2,3,3,4,4,4-heptafluorobutyl acrylate)、丙烯酸2,2,3,3,4,4,5,5-八氟戊酯(2,2,3,3,4,4,5,5-octafluoropentyl acrylate)等氟取代丙烯酸烷基酯单体也可包含于丙烯酸烷基酯单体中。丙烯酸烷基酯单体可单独使用或混合使用两种以上。
从形状恢复性及柔软性的提高效果大的方面来看,优选为烷基的碳数为1~5的丙烯酸烷基酯单体,更优选为丙烯酸乙酯以及丙烯酸丁酯,从共聚性的观点来看,特别优选为丙烯酸乙酯。
在将单体组合物中所含的所有单体成分设为100摩尔%时,丙烯酸烷基酯单体的调配量可设为0摩尔%~60摩尔%。所述调配量优选为15摩尔%~45摩尔%,更优选为20摩尔%~40摩尔%。
A-2.亲水性单体
亲水性单体可对人工晶状体用材料赋予亲水性。另外,通过调整亲水性单体的调配量,可维持柔软性及强度、并且可抑制闪光的产生。其机制并不确定,推测为:通过在材料中存在一定量的亲水性单体,可防止聚合物中的水分凝聚(闪光)。
作为亲水性单体,可列举:烷基的碳数为1~20的含羟基的(甲基)丙烯酸烷基酯、(甲基)丙烯酰胺以及N-乙烯基内酰胺(N-vinyllactam)。亲水性单体可单独使用或混合使用两种以上。再者,在本说明书中,“(甲基)丙烯酸酯”是指丙烯酸酯和/或甲基丙烯酸酯。
作为含羟基的(甲基)丙烯酸烷基酯,例如可列举:(甲基)丙烯酸羟基乙酯、(甲基)丙烯酸羟基丙酯、(甲基)丙烯酸羟基丁酯、(甲基)丙烯酸羟基戊酯等(甲基)丙烯酸羟基烷基酯,(甲基)丙烯酸二羟基丙酯、(甲基)丙烯酸二羟基丁酯、(甲基)丙烯酸二羟基戊酯等(甲基)丙烯酸二羟基烷基酯。
作为(甲基)丙烯酰胺,例如可列举:N,N-二甲基(甲基)丙烯酰胺、N,N-二乙基(甲基)丙烯酰胺、N,N-二丙基(甲基)丙烯酰胺等N,N-二烷基(甲基)丙烯酰胺,N,N-二甲基氨基丙基(甲基)丙烯酰胺、N,N-二乙基氨基丙基(甲基)丙烯酰胺等N,N-二烷基氨基烷基(甲基)丙烯酰胺。
作为N-乙烯基内酰胺,例如可列举:N-乙烯基吡咯烷酮、N-乙烯基哌啶酮、N-乙烯基己内酰胺等。
亲水性单体并不限定于所述单体。作为其他可使用的亲水性单体,例如可列举:二乙二醇单(甲基)丙烯酸酯(diethylene glycol mono(meth)acrylate)、三乙二醇单(甲基)丙烯酸酯(triethylene glycol mono(meth)acrylate)、丙二醇单(甲基)丙烯酸酯、(甲基)丙烯酸、1-甲基-3-亚甲基-2-吡咯烷酮(1-methyl-3-methylene-2-pyrrolidinone)、马来酸酐、马来酸、马来酸衍生物、富马酸(fumaric acid)、富马酸衍生物、氨基苯乙烯(aminostyrene)、羟基苯乙烯(hydroxystyrene)等。
从促进闪光降低的作用大的方面来看,作为亲水性单体,优选为含羟基的(甲基)丙烯酸烷基酯以及(甲基)丙烯酰胺,特别优选为甲基丙烯酸2-羟基乙酯(2-hydroxyethylmethacrylate)。
在将单体组合物中所含的所有单体成分设为100摩尔%时,亲水性单体的调配量可设为10摩尔%~40摩尔%,优选为10摩尔%~25摩尔%。若为所述范围,则可充分抑制闪光的产生,并且可维持柔软性。
A-3.交联性单体
交联性单体可助于人工晶状体用材料的柔软性。具体而言,可赋予良好的机械强度,并且可提高形状恢复性。另外,可提高单体彼此的共聚性。
作为交联性单体,例如可列举:丁二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、富马酸二烯丙酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸乙烯酯、三羟甲基丙烷三(甲基)丙烯酸酯、(甲基)丙烯酸甲基丙烯酰氧基乙酯、二乙烯基苯、邻苯二甲酸二烯丙酯、己二酸二烯丙酯、二异氰酸三烯丙酯、α-亚甲基-N-乙烯基吡咯烷酮、(甲基)丙烯酸4-乙烯基苄基酯、(甲基)丙烯酸3-乙烯基苄基酯、2,2-双((甲基)丙烯酰氧基苯基)六氟丙烷、2,2-双((甲基)丙烯酰氧基苯基)丙烷、1,4-双(2-(甲基)丙烯酰氧基六氟异丙基)苯、1,3-双(2-(甲基)丙烯酰氧基六氟异丙基)苯、1,2-双(2-(甲基)丙烯酰氧基六氟异丙基)苯、1,4-双(2-(甲基)丙烯酰氧基异丙基)苯、1,3-双(2-(甲基)丙烯酰氧基异丙基)苯、1,2-双(2-(甲基)丙烯酰氧基异丙基)苯等。其中,可优选使用丁二醇二(甲基)丙烯酸酯(butanediol di(meth)acrylate)以及乙二醇二(甲基)丙烯酸酯(ethylene glycoldi(meth)acrylate)中的一种以上。从控制柔软性、赋予良好的机械强度、提高形状恢复性及共聚性的效果大的方面来看,特别优选为丁二醇二(甲基)丙烯酸酯。交联性单体可单独使用或混合使用两种以上。
在将单体组合物中所含的所有单体成分设为100摩尔%时,交联性单体的调配量可设为0.1摩尔%~5摩尔%。所述调配量优选为0.5摩尔%~4摩尔%,更优选为1摩尔%~3摩尔%。若为所述范围,则可赋予形状恢复性、并且可抑制闪光产生。另外,作为人工晶状体材料,可赋予可耐受自小切口插入的伸长率。
A-4.单体调配比例
单体组合物中的、所有甲基丙烯酸酯单体相对于所有丙烯酸酯单体的摩尔基准调配比例(甲基丙烯酸酯/丙烯酸酯)为0.25~1.00,优选为0.30~0.70,更优选为0.35~0.65。通过将丙烯酸酯单体与甲基丙烯酸酯单体的调配比例设为所述范围内,可获得具有维持适于折叠的柔软性、并且耐水解性优异这一特征的人工晶状体材料。
A-5.聚合引发剂
单体组合物视需要包含聚合引发剂。作为聚合引发剂,根据聚合方法,可使用自由基聚合引发剂、光聚合引发剂等任意适当的聚合引发剂。
作为自由基聚合引发剂,例如可列举:偶氮二异丁腈(azobisisobutyronitrile)、偶氮双二甲基戊腈(azobisdimethylvaleronitrile)、过氧化苯甲酰、叔丁基过氧化氢、氢过氧化枯烯(cumene hydroperoxide)等。在利用光线等进行聚合时,优选为添加光聚合引发剂或敏化剂。作为光聚合引发剂,例如可列举:邻苯甲酰基苯甲酸甲酯(methylorthobenzoyl benzoate)等安息香系化合物,2-羟基-2-甲基-1-苯基丙烷-1-酮等苯酮(phenone)系化合物,1-羟基环己基苯基酮、1-苯基-1,2-丙二酮-2-(邻乙氧基羰基)肟、2-氯噻吨酮等噻吨酮系化合物,二苯并环庚酮(dibenzosuberone)、2-乙基蒽醌、二苯甲酮丙烯酸酯、二苯甲酮、苯偶酰等。
聚合引发剂或敏化剂的调配量可在不损及本发明的效果的范围内适当设定。
A-6.其他添加成分
人工晶状体用材料视需要也可包含紫外线吸收剂、色素等其他添加成分。添加成分可代表性地通过添加至单体组合物中而调配至人工晶状体用材料中。
作为紫外线吸收剂,例如可列举:2-羟基-4-甲氧基二苯甲酮、2-羟基-4-辛氧基二苯甲酮等二苯甲酮类,2-(2'-羟基-5'-甲基丙烯酸基氧基亚乙基氧基-叔丁基苯基)-5-甲基-苯并三唑、2-(2'-羟基-5'-甲基苯基)苯并三唑、5-氯-2-(3'-叔丁基-2'-羟基-5'-甲基苯基)苯并三唑等苯并三唑类,水杨酸衍生物类,羟基苯乙酮衍生物类等。紫外线吸收剂的调配量可在不损及本发明的效果的范围内设定为任意适当的值。
关于色素,例如在校正青视症(cyanopia)时,理想的是黄色或橙色的色素。作为色素,例如可列举:日本专利特开2006-291006号公报中记载的染料、或染料索引(colorindex,CI)中记载的CI溶剂黄(solvent yellow)、CI溶剂橙(solvent orange)等油溶性染料、CI分散黄(disperse yellow)、CI分散橙(disperse orange)等分散染料、还原系染料等。色素的调配量可在不损及本发明的效果的范围内设定为任意适当的值。
B.人工晶状体用材料的制造方法
人工晶状体用材料可通过将所述单体组合物聚合而获得。关于聚合方法,例如可在调配自由基聚合引发剂后进行加热,也可照射微波、紫外线、放射线(γ射线)等电磁波。加热条件或照射条件可根据单体组合物的组成等来适当设定。
聚合可在铸模内进行,也可通过对聚合后所获得的材料进行切削加工而加工为所期望的形状。
C.人工晶状体材料的特性
在本发明的人工晶状体材料中,闪光的产生得到抑制。在将人工晶状体材料加工为人工晶状体时,闪光的产生数量优选为每1片人工晶状体为15个以下。另外,在实施例中记载的板的情况下,闪光的产生数量优选为每1片板为6个以下,更优选为2个以下。
人工晶状体材料的断裂应力优选为4.5MPa~11.0MPa,更优选为5.0MPa~10.5MPa。若断裂应力小于4.5MPa,则强度变弱,晶状体插入时有破损的担忧。另外,存在耐水解性不充分的情况。另一方面,若断裂应力超过11.0MPa,则存在柔软性降低而难以小地折叠的情况。
人工晶状体材料的伸长率优选为170%以上。若伸长率为170%以上,则适宜自小切口插入。另外,从形状恢复性的观点来看,所述伸长率优选为600%以下。
在水中且在100℃下保存30天时的、来自人工晶状体材料的水解物(例如,苯氧基乙基醇(POEtOH))的溶出率优选为0.13质量%以下,更优选为0.10质量%以下。另外,在水中且在100℃下保存60天时的、来自人工晶状体材料的水解物的溶出率优选为0.80质量%以下,更优选为0.70质量%以下。另外,在水中且在100℃下保存90天时的、来自人工晶状体材料的水解物的溶出率优选为3.30质量%以下,更优选为2.80质量%以下。
在干燥状态(25℃)及吸水状态(35℃)两种状态下,人工晶状体用材料的折射率优选为1.50以上。
人工晶状体用材料的吸水率(质量%)优选为1.5质量%~4.5质量%的范围。若吸水率为1.5质量%以上,则可抑制闪光的产生,若吸水率为4.5质量%以下,则可进一步抑制柔软性的降低或形状恢复性的降低。
实施例
以下,通过实施例对本发明进行具体说明,但本发明并不受这些实施例的限定。再者,各处理及各特性的测定方法如下所述。
(水解处理)
预先使试样在60℃下干燥,测定处理前质量W0。在100mL耐压瓶中放入蒸馏水50mL,浸渍试样。在100℃的干燥机中放入耐压瓶并保存。作为试样,使用10片直径为6mm、厚度为0.5mm的板。记录瓶的皮重(tare weight)W01、蒸馏水添加后的瓶质量W02、试样浸渍后的瓶质量W03。
(POEtOH溶出率)
根据以下顺序,对于水解处理30天后的提取液,求出苯氧基乙基醇(POEtOH,丙烯酸2-苯氧基乙酯(2-phenoxyethyl acrylate,POEA)的水解物)的浓度与溶出率。记录提取液采集前的瓶质量W11后,自瓶中采集提取液,记录提取液采集后的瓶质量W12。对所采集的提取液、标准液、以及这些的空白(blank)(蒸馏水),使用高效液相色谱法(HighPerformance Liquid Chromatography,HPLC)进行分析。分析后,自所采集的水溶液及标准溶液的色谱图中减去蒸馏水的色谱图,进行基线校正。根据校正后的色谱图算出POEtOH的峰面积。根据标准液的POEtOH浓度与峰面积制成校准曲线。基于提取液的POEtOH的峰面积与所获得的校准曲线,算出提取液中的POEtOH的浓度。使用所获得的POEtOH的浓度,并利用以下式(1)算出每1g试样的POEtOH的溶出率。提取液容量是利用式(2)算出。在算出提取液容量时,前提是如下观点:在通过100℃的加热而发生变化的质量中,试样的质量变化与提取液的质量变化相比小至可忽视的程度;由于提取液的大部分是水,因此可将密度设为1g/1mL来计算。对处理30天的提取液进行分析后,再次将瓶放入100℃的干燥机中。水解处理合计60天后,再次采集提取液。与处理30天时同样地,记录提取液采集前的瓶质量W21,通过HPLC分析对提取液中的POEtOH浓度进行定量,利用式(3)算出POEtOH的溶出率。提取液容量是利用式(4)算出。另外,也同样算出水解处理合计90天后的POEtOH的溶出率。
POEtOH溶出率(%)=提取液中的POEtOH浓度(ppm)×10-6×提取液容量V1S(mL)/处理前质量W0(g)×100…数式(1)
提取液容量V1S(mL≒g)=[W02(g)-W01(g)]-[W03(g)-W11(g)]…数式(2)
POEtOH溶出率(%)=提取液中的POEtOH浓度(ppm)×10-6×提取液容量V2S(mL)/处理前质量W0(g)×100…数式(3)
提取液容量V2S(mL≒g)=V1S(mL≒g)-[W11(g)-W12(g)]-[W12(g)-W21(g)]…数式(4)
(断裂应力)
使用总长(L0)约20mm、平行部长度(L)6mm、平行部宽度(W)1.5mm、厚度0.8mm的哑铃形状的试验片(参照图1)进行测定。在25℃的恒温水中浸渍试样并静置1分钟后,以100mm/分钟的速度进行拉伸直至断裂为止。使用软件,求出断裂应力。
(闪光)
在所述测定中,使用直径6mm、中心厚度0.8mm±0.1mm的晶状体形状的试样或者直径6mm、厚度0.5mm的板试样。对于晶状体形状的试样,将试样在35℃的水中浸渍17小时以上,继而在25℃的水中浸渍2小时后,利用立体显微镜观察外观。对于板试样,将试样在35℃的水中浸渍22小时,继而在25℃的水中浸渍2小时后,利用立体显微镜观察外观。外观的观察是对一种试样的2个或3个标本进行,调查闪光(亮点)的产生个数。倍率为约10倍~60倍。为了容易观察闪光,而在所述范围内适宜调节倍率来进行观察。
(吸水率)
测定25℃下的平衡含水状态及干燥状态下的试样的质量,算出吸水率(质量%)。吸水率是根据25℃下的平衡含水状态下的试样的质量Ww、干燥状态下的试样的质量Wd并利用下述式(5)来算出。作为试样,使用5片直径为6mm、厚度为0.8mm的板。
吸水率(质量%)=(Ww-Wd)/Wd×100…数式(5)
(折射率)
使用阿贝(Abbe)折射计求出试样的利用Hg-e射线而得的折射率。利用干燥状态的试样(25℃)或吸水状态的试样(35℃)进行测定。作为试样,使用直径6mm、厚度0.8mm的板。
[实施例1~实施例6及比较例1~比较例9板形状的人工晶状体用材料的制作]
单体组合物为于表1所示的比例的各单体成分中加入聚合引发剂而获得。使用2,2'-偶氮双(2,4-二甲基戊腈)作为聚合引发剂。单体组合物中所述聚合引发剂的质量份为相对于基础单体100质量份而为0.5质量份。将所获得的单体组合物注入至所期望的板形状的铸模内。将所述铸模放入80℃的烘箱中,历时40分钟进行加热聚合成形。使所获得的聚合物自铸模脱模,进行溶出处理后,在60℃的烘箱内进行干燥,获得板形状的人工晶状体用材料。此时,根据必要的测定项目,适宜制作两种厚度的试样作为相同组成的板试样。所述厚度0.5mm或0.8mm的板是由使用厚度0.5mm或0.8mm的垫片(spacer)的铸模制作而成的板。根据试验的目的,将干燥后的板以直径6mm或8mm挖出而制成测定用的板。
[表1]
[使用成分]
以下示出表中记载的化合物的简称。
<基础单体>
POEA:丙烯酸2-苯氧基乙酯
EA:丙烯酸乙酯
POEMA:甲基丙烯酸苯氧基乙酯
EHMA:甲基丙烯酸乙基己酯
LMA:甲基丙烯酸月桂基酯
ETMA:甲基丙烯酸乙氧基乙酯
<亲水性单体>
HEMA:甲基丙烯酸2-羟基乙酯
<交联性单体>
BDDA:1,4-丁二醇二丙烯酸酯
关于所获得的人工晶状体用材料,评价各特性。将结果示于表2中。
[表2]
1)直径6mm、厚度0.5mm的板中的测定结果(试验数n=3的平均值)。如根据表1及表2而明确般,并用含芳香环的丙烯酸酯单体、以及具有碳数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯单体作为基础单体的实施例1~实施例6及比较例4~比较例9中,获得耐水解性提高的人工晶状体材料。另外,这些人工晶状体材料还抑制了闪光的产生。进而,单体组合物中的甲基丙烯酸酯单体相对于丙烯酸酯单体的摩尔基准调配比例为0.25~1.00的范围内的实施例1~实施例6中,获得柔软且可适宜折叠、并且具有可耐受向眼内的插入的强度的人工晶状体材料。另一方面,预想到:比较例4~比较例9的人工晶状体材料的柔软性低而难以折叠,或者折叠时的负荷大。
[比较例10~比较例12晶状体形状的人工晶状体用材料的制作]
使用表3所示的单体成分、以及使用所期望的晶状体形状的铸模,除此以外,与实施例1同样地进行而获得晶状体形状的人工晶状体用材料。另外,关于所获得的人工晶状体用材料,进行闪光评价。将结果示于表3中。
[表3]
1)晶状体中的测定结果(试验数n=2或3的平均值)。
如表3所示般,在并未并用含芳香环的丙烯酸酯单体、以及具有碳数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯单体时,所获得的人工晶状体材料为容易产生闪光的材料。
[试验例1~试验例3]
另外,将表4所示的单体组合物聚合而获得的聚合物材料也可适宜用作本发明的人工晶状体材料。
[表4]
产业上的可利用性
本说明书中所公开的发明可在与人工晶状体相关的用途中使用。
Claims (5)
1.一种人工晶状体用材料,其包含聚合物材料,所述聚合物材料是将包含基础单体、亲水性单体及交联性单体的单体组合物聚合而获得,所述基础单体包含含芳香环的丙烯酸酯单体、具有碳数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯单体以及具有碳数为1~20的烷基的丙烯酸烷基酯单体,所述亲水性单体为烷基的碳数为1~20的含羟基的甲基丙烯酸烷基酯,并且
所述含芳香环的丙烯酸酯单体为选自丙烯酸苯氧基乙酯、丙烯酸苯基乙酯以及丙烯酸苄基酯的一种,
所述交联性单体为选自丁二醇二丙烯酸酯、乙二醇二丙烯酸酯、二乙二醇二丙烯酸酯、三乙二醇二丙烯酸酯、丙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、2,2-双(丙烯酰氧基苯基)六氟丙烷、2,2-双(丙烯酰氧基苯基)丙烷、1,4-双(2-丙烯酰氧基六氟异丙基)苯、1,3-双(2-丙烯酰氧基六氟异丙基)苯、1,2-双(2-丙烯酰氧基六氟异丙基)苯、1,4-双(2-丙烯酰氧基异丙基)苯、1,3-双(2-丙烯酰氧基异丙基)苯以及1,2-双(2-丙烯酰氧基异丙基)苯中的一种以上,
在将单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述含芳香环的丙烯酸酯单体的调配量为30摩尔%~50摩尔%,
在将单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述甲基丙烯酸烷氧基烷基酯单体的调配量为5摩尔%~25摩尔%,
在将单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述丙烯酸烷基酯单体的调配量为20摩尔%~40摩尔%,
所述单体组合物中所含的所有单体成分中的、甲基丙烯酸酯单体相对于丙烯酸酯单体的摩尔基准调配比例为0.25~1.00。
2.根据权利要求1所述的人工晶状体用材料,其中所述甲基丙烯酸烷氧基烷基酯单体为选自甲基丙烯酸甲氧基乙酯及甲基丙烯酸乙氧基乙酯中的一种以上。
3.根据权利要求1或2所述的人工晶状体用材料,其中在将所述单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述亲水性单体的调配量为10摩尔%~40摩尔%。
4.根据权利要求1或2所述的人工晶状体用材料,其中在将所述单体组合物中所含的所有单体成分设为100摩尔%时,所述单体组合物中的所述交联性单体的调配量为0.1摩尔%~5摩尔%。
5.根据权利要求1或2所述的人工晶状体用材料,其中断裂应力为4.5MPa~11.0MPa。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2018/003227 WO2019150490A1 (ja) | 2018-01-31 | 2018-01-31 | 眼内レンズ用材料 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN111542348A CN111542348A (zh) | 2020-08-14 |
CN111542348B true CN111542348B (zh) | 2022-07-05 |
Family
ID=65270515
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201880084545.1A Active CN111542348B (zh) | 2018-01-31 | 2018-01-31 | 人工晶状体用材料 |
Country Status (15)
Country | Link |
---|---|
US (1) | US11578158B2 (zh) |
EP (1) | EP3747474A4 (zh) |
JP (1) | JP6466031B1 (zh) |
KR (1) | KR102452916B1 (zh) |
CN (1) | CN111542348B (zh) |
AU (1) | AU2018406934B2 (zh) |
BR (1) | BR112020015350B1 (zh) |
CA (1) | CA3088101A1 (zh) |
IL (1) | IL275569B2 (zh) |
MX (1) | MX2020007560A (zh) |
PH (1) | PH12020551139A1 (zh) |
RU (1) | RU2760281C1 (zh) |
SG (1) | SG11202006172WA (zh) |
UA (1) | UA127148C2 (zh) |
WO (1) | WO2019150490A1 (zh) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006113290A1 (en) * | 2005-04-13 | 2006-10-26 | Benz Research & Development Corporation | Polymers for intraocular lenses |
CN106632926A (zh) * | 2011-09-29 | 2017-05-10 | 三菱化学株式会社 | 氢化嵌段共聚物、树脂组合物、膜及容器 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3195662B2 (ja) * | 1992-08-24 | 2001-08-06 | 株式会社メニコン | 眼用レンズ材料 |
JP3641110B2 (ja) * | 1997-08-20 | 2005-04-20 | 株式会社メニコン | 軟質眼内レンズ用材料 |
US6267784B1 (en) | 1998-05-01 | 2001-07-31 | Benz Research And Development Corporation | Intraocular lens and haptics made of a copolymer |
JP2003144538A (ja) * | 2002-11-22 | 2003-05-20 | Menicon Co Ltd | 軟質眼内レンズ用材料 |
JP4291296B2 (ja) | 2005-04-08 | 2009-07-08 | 株式会社メニコン | 新規重合性染料およびそれを含む眼用レンズ |
ATE503783T1 (de) | 2005-12-01 | 2011-04-15 | Coronis Gmbh | Polymerzusammensetzung mit hohem brechungsindex |
JP2009045329A (ja) | 2007-08-22 | 2009-03-05 | Hoya Corp | 眼内レンズの製造方法および眼内レンズ |
JP2011246673A (ja) * | 2010-05-31 | 2011-12-08 | Nidek Co Ltd | 眼内レンズ |
WO2012004744A2 (en) | 2010-07-05 | 2012-01-12 | Polymer Technologies International (Eou) | Polymeric composition for ocular devices |
ES2804031T3 (es) | 2011-09-16 | 2021-02-02 | Benz Res And Development Corporation | Lente intraocular hidrófoba |
BR112014026853B1 (pt) | 2012-04-27 | 2021-05-11 | Kowa Company, Ltd | corante que absorve uv polimerizável estável para lente intraocular |
US20180021475A1 (en) * | 2015-01-29 | 2018-01-25 | Menicon Co., Ltd | Intraocular lens material and method for preserving intraocular lens material |
CA3031618C (en) | 2016-07-28 | 2019-10-22 | Menicon Co., Ltd | Material for intraocular lenses |
CN106632826B (zh) * | 2016-10-31 | 2019-01-11 | 四川大学 | 一种可折叠人工晶状体材料及其制备方法 |
JP7001823B2 (ja) * | 2018-01-31 | 2022-02-04 | 株式会社メニコン | 眼内レンズ |
-
2018
- 2018-01-31 US US16/960,098 patent/US11578158B2/en active Active
- 2018-01-31 CA CA3088101A patent/CA3088101A1/en not_active Abandoned
- 2018-01-31 MX MX2020007560A patent/MX2020007560A/es unknown
- 2018-01-31 IL IL275569A patent/IL275569B2/en unknown
- 2018-01-31 AU AU2018406934A patent/AU2018406934B2/en not_active Ceased
- 2018-01-31 SG SG11202006172WA patent/SG11202006172WA/en unknown
- 2018-01-31 JP JP2018522816A patent/JP6466031B1/ja active Active
- 2018-01-31 RU RU2020124081A patent/RU2760281C1/ru active
- 2018-01-31 CN CN201880084545.1A patent/CN111542348B/zh active Active
- 2018-01-31 KR KR1020207021665A patent/KR102452916B1/ko active IP Right Grant
- 2018-01-31 UA UAA202004734A patent/UA127148C2/uk unknown
- 2018-01-31 WO PCT/JP2018/003227 patent/WO2019150490A1/ja active Application Filing
- 2018-01-31 BR BR112020015350-8A patent/BR112020015350B1/pt active IP Right Grant
- 2018-01-31 EP EP18903559.5A patent/EP3747474A4/en active Pending
-
2020
- 2020-07-27 PH PH12020551139A patent/PH12020551139A1/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006113290A1 (en) * | 2005-04-13 | 2006-10-26 | Benz Research & Development Corporation | Polymers for intraocular lenses |
CN106632926A (zh) * | 2011-09-29 | 2017-05-10 | 三菱化学株式会社 | 氢化嵌段共聚物、树脂组合物、膜及容器 |
Also Published As
Publication number | Publication date |
---|---|
CA3088101A1 (en) | 2019-08-08 |
US20210061933A1 (en) | 2021-03-04 |
CN111542348A (zh) | 2020-08-14 |
JPWO2019150490A1 (ja) | 2020-02-06 |
IL275569A (en) | 2020-08-31 |
BR112020015350B1 (pt) | 2022-11-29 |
WO2019150490A1 (ja) | 2019-08-08 |
AU2018406934A1 (en) | 2020-07-16 |
KR20200103074A (ko) | 2020-09-01 |
NZ765784A (en) | 2023-11-24 |
US11578158B2 (en) | 2023-02-14 |
EP3747474A1 (en) | 2020-12-09 |
JP6466031B1 (ja) | 2019-02-06 |
KR102452916B1 (ko) | 2022-10-07 |
UA127148C2 (uk) | 2023-05-17 |
EP3747474A4 (en) | 2021-09-08 |
MX2020007560A (es) | 2020-09-03 |
IL275569B1 (en) | 2023-07-01 |
PH12020551139A1 (en) | 2021-05-31 |
SG11202006172WA (en) | 2020-07-29 |
BR112020015350A2 (pt) | 2020-12-08 |
RU2760281C1 (ru) | 2021-11-23 |
IL275569B2 (en) | 2023-11-01 |
AU2018406934B2 (en) | 2020-12-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6315646B1 (ja) | 眼内レンズ用材料 | |
DE69330059T2 (de) | Zusammensetzung für weiche Okularlinsen | |
US6326448B1 (en) | Soft intraocular lens material | |
JP3641110B2 (ja) | 軟質眼内レンズ用材料 | |
EP1030194B1 (en) | Material for a soft intraocular lens | |
AU2018405527B2 (en) | Intraocular lens | |
DE69015835T2 (de) | Zusammensetzung für okulare Linsen. | |
EP3251703A1 (en) | Material for intraocular lenses and method for preserving material for intraocular lenses | |
CN111542348B (zh) | 人工晶状体用材料 | |
DE69625420T2 (de) | Wasserabsorbierendes Material für weiche Okularlinse, wasserabsorbierende Okularlinse und Verfahren zu deren Herstellung | |
DE69633046T2 (de) | Zusammensetzung für Kontaktlinse mit geringer Wasserabsorption, Gegenstand und Kontaktlinse mit geringer Wasserabsorption und Verfahren zur Herstellung | |
JP2022071514A (ja) | コントラスト改善機能を有する眼科用材料 | |
JP4502638B2 (ja) | コンタクトレンズ材料 | |
JP4414750B2 (ja) | コンタクトレンズ材料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 40026216 Country of ref document: HK |
|
GR01 | Patent grant | ||
GR01 | Patent grant |