WO2018021455A1 - 眼内レンズ用材料 - Google Patents
眼内レンズ用材料 Download PDFInfo
- Publication number
- WO2018021455A1 WO2018021455A1 PCT/JP2017/027176 JP2017027176W WO2018021455A1 WO 2018021455 A1 WO2018021455 A1 WO 2018021455A1 JP 2017027176 W JP2017027176 W JP 2017027176W WO 2018021455 A1 WO2018021455 A1 WO 2018021455A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mass
- acrylate
- parts
- intraocular lens
- meth
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 101
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 59
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical group CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical group COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 239000000523 sample Substances 0.000 description 40
- -1 methacryloyl group Chemical group 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 24
- 229960005323 phenoxyethanol Drugs 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000010828 elution Methods 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- 239000004519 grease Substances 0.000 description 12
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 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 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 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
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000003780 insertion Methods 0.000 description 5
- 230000037431 insertion Effects 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 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 3
- 239000000470 constituent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 238000012360 testing method 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
- 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 2
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102100026735 Coagulation factor VIII Human genes 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- BKKVYNMMVYEBGR-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(OC(=O)C=C)C(Br)=C1Br BKKVYNMMVYEBGR-UHFFFAOYSA-N 0.000 description 1
- 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
- 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 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
- 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
- OJVAGVQSPOKZKM-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentyl acetate Chemical compound CC(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)F OJVAGVQSPOKZKM-UHFFFAOYSA-N 0.000 description 1
- RPHIWWKRMBRETN-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)C(F)(F)C(F)(F)COC(=O)C=C RPHIWWKRMBRETN-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
- 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
- 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 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
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- 241001391944 Commicarpus scandens Species 0.000 description 1
- 206010051819 Cyanopsia Diseases 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 229920005177 Duracon® POM Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 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
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 150000003926 acrylamides Chemical class 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005452 bending Methods 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000012937 correction 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
- 230000003247 decreasing effect Effects 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000009826 distribution Methods 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
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002237 fumaric acid derivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 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
- 239000002184 metal Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 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
- 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
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 238000002203 pretreatment Methods 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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 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
- 239000000984 vat dye Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
Classifications
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
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- 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
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- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
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- C08F222/145—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates the ester chains containing seven or more carbon atoms
Definitions
- the present invention relates to an intraocular lens material.
- an acrylic material is preferable because it has a high refractive index and opens slowly after being inserted into the eye.
- the shape recoverability is increased, the elongation rate of the lens is decreased, and if there is a scratch or the like, the material becomes a brittle material that can be easily torn.
- the material in order to insert the lens into the eye from the smallest incision, it is desirable that the material has a high elongation rate and does not crack or tear.
- Such intraocular lens materials include a polymer obtained by polymerizing a polymerization component containing a hydrophilic monomer including a hydroxyl group-containing alkyl (meth) acrylate, a (meth) acrylamide monomer and N-vinyl lactam. Therefore, a water absorption rate of 1.5 to 4.5% by mass has been proposed (see, for example, Patent Document 1).
- This intraocular lens material is excellent in flexibility and has a high refractive index, so that the lens can be thinned and can be inserted through the incision from a folded state, and it is also transparent. It is excellent and can suppress greaseing more.
- the present invention has been made in view of such a problem, and mainly provides an intraocular lens material capable of further reducing a hydrolyzate eluted from the intraocular lens material in an aqueous solution. Objective.
- the present inventors maintain desirable physical properties as an intraocular lens material by incorporating a specific methacrylate in an acrylate-based intraocular lens material.
- the inventors have found that the elution amount of the hydrolyzate in the aqueous solution can be further reduced, and at the same time, the present invention has been completed.
- the intraocular lens material disclosed in this specification includes an aromatic ring-containing acrylate structure, an alkoxyalkyl methacrylate structure having an alkoxyalkyl group having 4 or less carbon atoms, a hydrophilic structure based on a hydrophilic monomer, And a crosslinkable structure based on a functional monomer.
- the amount of hydrolyzate eluted from the intraocular lens material in an aqueous solution can be further reduced.
- the reason why such an effect is obtained is estimated as follows, for example.
- methacrylate has a hard characteristic as a material due to the presence of a methyl group as compared with acrylate, but it can hardly be attacked by water, so that hydrolysis resistance can be further improved.
- those having an alkoxyalkyl group having 4 or less carbon atoms are suitable for the number of carbon atoms, are not excessively hard, and are considered to have sufficient flexibility.
- alkoxyalkyl group having 4 or less carbon atoms are preferable from the viewpoints of the ability to suppress greening, reduction in tackiness, and flexibility.
- the alkoxyalkyl group may be represented by, for example, chemical formula (1).
- the intraocular lens material disclosed in the present embodiment includes an aromatic ring-containing acrylate structure, an alkoxyalkyl methacrylate structure having an alkoxyalkyl group having 4 or less carbon atoms, a hydrophilic structure based on a hydrophilic monomer, and a crosslinkable monomer And a crosslinkable structure.
- This intraocular lens material includes, as a base material, an aromatic ring-containing acrylate structure and an alkoxyalkyl methacrylate structure having an alkoxyalkyl group having 4 or less carbon atoms.
- the intraocular lens material may further include an alkyl acrylate structure having an alkyl group having 1 to 20 carbon atoms as a base material.
- a base material means the component which comprises the main structure of the material for intraocular lenses.
- This intraocular lens material may include an aromatic ring-containing acrylate structure A, an alkoxyalkyl methacrylate structure B, and an alkyl acrylate structure C as a base material, as shown in chemical formula (2).
- a, b, and c are arbitrary integers, and the aromatic ring-containing acrylate structure A, alkoxyalkyl methacrylate structure B, and alkyl acrylate structure C are arbitrarily bonded to a carbon chain.
- the adjacent structures may be appropriately different or the same.
- the functional group R 1 is a functional group including an aromatic ring
- the functional group R 2 is an alkoxyalkyl group having 4 or less carbon atoms including an alkoxy group
- the functional group R 3 is a functional group having 1 to 20 carbon atoms. It is an alkyl group.
- the acrylate having an acryloyl group and the methacrylate having a methacryloyl group are hereinafter collectively referred to as “(meth) acrylate”.
- the constituent site included in the polymer is specified by the name of the monomer, and the monomer exemplified in the explanation of the structure of the polymer has a structure in which the polymer group is bonded to another constituent site.
- (meth) acrylate exists in the polymer as “(meth) acrylate structure”, which means that other constituent sites in the double bond of (meth) acrylate Are bonded (polymerized).
- the aromatic ring-containing acrylate structure is a structure based on an aromatic ring-containing acrylate as a base monomer.
- This aromatic ring-containing acrylate may be a component having an action of improving the refractive index of the intraocular lens material.
- This aromatic ring-containing acrylate structure may have a phenoxy group, an alkylene group having 2 or less carbon atoms, and an acrylate bonding site.
- aromatic ring-containing acrylate examples include phenoxyethyl acrylate, phenylethyl acrylate, benzyl acrylate, phenyl acrylate, pentabromophenyl acrylate, and the like, and these can be used alone or in admixture of two or more.
- phenoxyethyl acrylate, phenylethyl acrylate, and benzyl acrylate are preferable because the effect of increasing the refractive index is large, and phenoxyethyl acrylate is particularly preferable from the viewpoint of further improving flexibility.
- the aromatic ring-containing acrylate is preferably in the range of 15 parts by mass or more and 80 parts by mass or less when the entire substrate is 100 parts by mass. Moreover, since it is desirable to have a high refractive index even in a water absorption state, it is more preferably 30 parts by mass or more and 80 parts by mass or less in 100 parts by mass of the base material.
- the alkoxyalkyl methacrylate structure having an alkoxyalkyl group having 4 or less carbon atoms is a structure based on an alkoxyalkyl methacrylate as a base monomer.
- the alkoxyalkyl group of this alkoxyalkyl methacrylate may be represented by the above chemical formula (1), for example.
- Examples of the alkoxy group include a methoxy group and an ethoxy group.
- Examples of the alkylene group to which the alkoxy group is bonded include a methylene group and an ethylene group.
- the alkoxyalkyl methacrylate is preferably one or more of methoxyethyl methacrylate and ethoxyethyl methacrylate, and more preferably ethoxyethyl methacrylate.
- This alkoxyalkyl methacrylate is preferably in the range of 10 parts by mass or more and 70 parts by mass or less when the entire substrate is 100 parts by mass, and the viewpoint that hydrolysis can be further suppressed and the viewpoint of easy folding. From 20 parts by mass to 100 parts by mass of the base material is more preferable.
- this intraocular lens material a structure based on 2-phenoxyethyl acrylate (POEA), ethyl acrylate (EA), and ethoxyethyl methacrylate (ETMA) is shown in chemical formula (3).
- a, b, and c are arbitrary integers, and the aromatic ring-containing acrylate structure A, the alkoxyalkyl methacrylate structure B, and the alkyl acrylate structure C are arbitrarily bonded to the carbon chain.
- the adjacent structures may be appropriately different or the same.
- the alkyl acrylate structure having an alkyl group having 1 to 20 carbon atoms is a structure based on an alkyl acrylate as a base monomer.
- the alkyl acrylate having 1 to 20 carbon atoms in the alkyl group may be a component having an action of improving the shape recoverability and flexibility of the intraocular lens material.
- alkyl acrylate examples include methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, pentyl acrylate, hexyl acrylate, heptyl acrylate, nonyl acrylate, stearyl acrylate, octyl acrylate, decyl acrylate, lauryl acrylate, pentadecyl acrylate, 2- Examples thereof include linear, branched or cyclic alkyl acrylates such as ethylhexyl acrylate, cyclopentyl acrylate, and cyclohexyl acrylate.
- alkyl acrylate examples include 2,2,2-trifluoroethyl acrylate, 2,2,3,3-tetrafluoropropyl acrylate, 2,2,3,3-tetrafluoro-t-pentyl acrylate, , 2,3,4,4,4-hexafluorobutyl acrylate, 2,2,3,4,4,4-hexafluoro-t-hexyl acrylate, 2,3,4,5,5,5-hexafluoro -2,4-bis (trifluoromethyl) pentyl acrylate, 2,2,3,3,4,4-hexafluorobutyl acrylate, 2,2,2,2 ', 2', 2'-hexafluoroisopropyl acrylate 2,2,3,3,4,4,4-heptafluorobutyl acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl acetate And fluorine-containing alkyl (meth) acrylates such as rate and the like
- alkyl acrylates having 1 to 5 carbon atoms in the alkyl group are preferred, and ethyl acrylate and butyl acrylate are particularly preferred from the viewpoint that the effect of improving shape recoverability and flexibility is great.
- This alkyl acrylate is preferably in the range of 0 to 35 parts by mass, with 100 parts by mass of the entire substrate.
- This alkyl acrylate is treated as one of the substrates, but is not necessarily an essential component. From the viewpoint of flexibility and shape recoverability, the ratio can be adjusted as appropriate.
- the hydrophilic structure is a structure based on a hydrophilic monomer.
- This hydrophilic monomer is a component that imparts hydrophilicity to the intraocular lens material, and may be a component that has an action of promoting a decrease in the greaseing of the intraocular lens material.
- the hydrophilic monomer may include one or more of a hydroxyl group-containing alkyl (meth) acrylate having 1 to 20 carbon atoms in the alkyl group, a (meth) acrylamide monomer, and N-vinyl lactam. Moreover, it is good also as what contains another hydrophilic monomer.
- hydroxyl-containing alkyl (meth) acrylate examples include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, hydroxypentyl (meth) acrylate and other hydroxyalkyl (meth) acrylates, dihydroxypropyl Examples thereof include dihydroxyalkyl (meth) acrylates such as (meth) acrylate, dihydroxybutyl (meth) acrylate, and dihydroxypentyl (meth) acrylate.
- Examples of (meth) acrylamide monomers include N, N-dialkyl (meth) acrylamides such as N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, and N, N-dipropyl (meth) acrylamide.
- N, N-dimethylaminopropyl (meth) acrylamide, and N, N-dialkylaminoalkyl (meth) acrylamide such as N, N-diethylaminopropyl (meth) acrylamide.
- Examples of N-vinyl lactam include N-vinyl pyrrolidone, N-vinyl piperidone, N-vinyl caprolactam and the like.
- hydrophilic monomers examples include diethylene glycol mono (meth) acrylate, triethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, (meth) acrylic acid, 1-methyl-3-methylene-2- Examples include pyrrolidinone, maleic anhydride, maleic acid, maleic acid derivatives, fumaric acid, fumaric acid derivatives, aminostyrene, and hydroxystyrene.
- the hydrophilic monomer mentioned above can be used individually or in mixture of 2 or more types.
- hydrophilic monomers a hydroxyl group-containing alkyl (meth) acrylate or (meth) acrylamide monomer is preferable, and 2-hydroxyethyl methacrylate is particularly preferable because it has a large effect of promoting the reduction of grease.
- the content of the hydrophilic monomer is preferably in the range of 15 to 35 parts by mass with respect to 100 parts by mass of the entire substrate. In this range, the effect of promoting the reduction of grease can be fully expressed, and no significant burden or trouble occurs in folding in a dry state.
- the crosslinkable structure is a structure based on a crosslinkable monomer.
- This crosslinkable monomer controls the flexibility of the material for the intraocular lens, imparts good mechanical strength, further improves the shape recovery property, and allows the polymerization components such as hydrophilic monomers and other polymerizable monomers to interact with each other. It is good also as a component which has the effect
- crosslinkable monomer examples include butanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, and dipropylene.
- crosslinkable monomers can be used alone or in admixture of two or more.
- butanediol di (meth) acrylate and ethylene are effective in controlling flexibility, imparting good mechanical strength, and improving shape recovery and copolymerization.
- One or more of glycol di (meth) acrylates are particularly preferred.
- the content of the crosslinkable monomer is preferably in the range of 2 parts by mass to 4 parts by mass with respect to 100 parts by mass of the entire substrate. When the content is 2 parts by mass or more, it is preferable from the viewpoint of imparting shape recoverability and suppressing occurrence of grease. In addition, when the content is 4 parts by mass or less, the intraocular lens material is preferable from the viewpoint of having an elongation rate that can withstand insertion from a small incision.
- This intraocular lens material may contain other additive components such as ultraviolet absorbers and pigments.
- the ultraviolet absorber include benzophenones such as 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-octoxybenzophenone, and 2- (2′-hydroxy-5′-methacryloxyethyleneoxy-t-butyl). Phenyl) -5-methyl-benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 5-chloro-2 (3'-t-butyl-2'-hydroxy-5'-methylphenyl) ) Benzotriazoles such as benzotriazole, salicylic acid derivatives, hydroxyacetophenone derivatives and the like.
- the blending amount of the ultraviolet absorber is preferably in the range of 0.05 part by mass or more and 3 parts by mass or less with respect to 100 parts by mass of the whole substrate.
- the pigment is preferably a yellow to orange pigment.
- the dye include dyes described in JP-A-2006-291006, oil-soluble dyes such as CI solvent yellow and CI solvent orange described in the color index (CI), CI disperse yellow, and CI disperse orange. And disperse dyes and vat dyes.
- the blending amount of the pigment is preferably in the range of 0.01 parts by mass or more and 3 parts by mass or less with respect to 100 parts by mass of the whole substrate.
- This intraocular lens material may be polymerized by adding, for example, a radical polymerization initiator or a photopolymerization initiator.
- a radical polymerization initiator may be blended and then heated, or an electromagnetic wave such as microwaves, ultraviolet rays, or radiation ( ⁇ rays) may be irradiated.
- the radical polymerization initiator include azobisisobutyronitrile, azobisdimethylvaleronitrile, benzoyl peroxide, t-butyl hydroperoxide, cumene hydroperoxide, and the like.
- a photoinitiator and a sensitizer are preferable to add further.
- the photopolymerization initiator include benzoin compounds such as methyl orthobenzoylbenzoate, phenone compounds such as 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, Examples include thioxanthone compounds such as phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime, 2-chlorothioxanthone, dibenzosvalon, 2-ethylanthraquinone, benzophenone acrylate, benzophenone, benzyl, etc.
- the amount of the polymerization initiator or sensitizer used is in the range of 0.01 parts by mass or more and 2 parts by mass or less with respect to 100 parts by mass of the whole substrate in order to advance the polymerization reaction at a sufficient rate. Is preferred.
- the intraocular lens material of the present invention is molded into an intraocular lens, it can be performed by, for example, a cutting method or a mold method.
- This intraocular lens material is a material that does not easily generate grease.
- the number of occurrences of greaseing is preferably 15 or less per lens.
- the number of occurrences of greaseing is preferably 6 or less per plate, and more preferably 2 or less.
- This intraocular lens material has an elongation that can withstand insertion from a small incision. Specifically, when the material is evaluated by the experimental method described in this specification, the elongation is preferably 170% or more. In addition, this elongation is preferably 600% or less from the viewpoint of the shape recoverability of the intraocular lens material.
- the elution rate of phenoxyethyl alcohol (POEtOH) which is a hydrolyzate from the material when stored in water at 100 ° C. for 30 days is preferably 0.13 mass% or less, and 0.10 The mass% or less is more preferable.
- the elution rate of POEtOH from the material when stored in water at 100 ° C. for 60 days is preferably 0.80 mass% or less, and more preferably 0.70 mass% or less.
- the elution rate of POEtOH from the material when stored in water at 100 ° C. for 90 days is preferably 3.30% by mass or less, and more preferably 2.80% by mass or less. A smaller elution rate is more preferable.
- This intraocular lens material preferably has a water absorption (mass%) in the range of 1.5 mass% to 4.5 mass%.
- the water absorption is 1.5% by mass or more, the occurrence of grease can be suppressed, and when it is 4.5% by mass or less, the decrease in flexibility and the decrease in shape recoverability can be further suppressed.
- the intraocular lens material of the present invention is excellent in flexibility and has a high refractive index, so that the lens can be thinned and can be folded and inserted through a small incision. It has excellent transparency and can suppress the occurrence of grease.
- hydrolyzate eluted from the intraocular lens material in an aqueous solution can be further reduced.
- the reason why such an effect is obtained is that, for example, alkoxyalkyl methacrylate having an alkoxyalkyl group having 4 or less carbon atoms is contained with respect to the acrylate of the base material.
- methacrylate has a hard characteristic as a material due to the presence of a methyl group as compared with acrylate, but it is presumed that hydrolysis resistance can be further improved because it is less susceptible to water attack. Increased methacrylate structure often facilitates the occurrence of greasening.
- the polymerization components shown in Tables 2 to 4 are used and injected into a desired plate-shaped mold and subjected to the same steps as described above, and plate-shaped intraocular lens materials (Experimental Examples 15 to 60) are obtained. Obtained.
- two types of thickness samples were appropriately prepared as plate samples having the same number (composition).
- the plate having a thickness of 0.5 mm or 0.8 mm described below is a plate made from a mold using a spacer having a thickness of 0.5 mm or 0.8 mm.
- the dried plate was cut into a diameter of 6 mm or 8 mm to obtain a measurement plate.
- POEtOH elution rate The concentration and elution rate of phenoxyethyl alcohol (POEtOH, POEA hydrolyzate) were determined for the extract 30 days after the hydrolysis treatment by the following procedure. After recording the bottle mass W 11 before collecting the extract, the extract was collected from the bottle, and the bottle mass W 12 after collecting the extract was recorded. The collected extract, standard solution, and their blank (distilled water) were analyzed using HPLC. After the analysis, the baseline water correction was performed by subtracting the chromatogram of distilled water from the chromatogram of the collected aqueous solution and standard solution. The peak area of POEtOH was calculated from the corrected chromatogram. A calibration curve was prepared from the POEtOH concentration of the standard solution and the peak area.
- the concentration of POEtOH in the extract was calculated.
- the elution rate of POEtOH per 1 g of the sample was calculated from the following equation (1).
- the extract volume was calculated from equation (2).
- the extract was collected again. As in the case of 30 days of treatment, the bottle mass W 21 before collecting the extract was recorded, the POEtOH concentration in the extract was quantified by HPLC analysis, and the elution rate of POEtOH was calculated from the formula (3). The extract volume was calculated from equation (4). Similarly, the elution rate of POEtOH after a total of 90 days after the hydrolysis treatment was also calculated.
- a lens-shaped sample having a diameter of 6 mm and a center thickness of 0.8 mm ⁇ 0.1 mm or a plate sample having a diameter of 6 mm and a thickness of 0.5 mm was used.
- the sample was immersed in water at 35 ° C. for 17 hours or more and then immersed in water at 25 ° C. for 2 hours, and then the appearance was observed with a stereomicroscope.
- the plate sample the sample was immersed in 35 ° C. water for 22 hours and then immersed in 25 ° C. water for 2 hours, and then the appearance was observed with a stereomicroscope.
- the appearance was observed by performing 2 or 3 specimens per one type of sample, and the number of occurrences of griening (bright spots) was examined.
- the magnification was about 10 to 60 times. The magnification was adjusted as appropriate within the above range so that the grease could be easily observed.
- Refractive index Using an Abbe refractometer, the refractive index by the Hg-e line of the sample was determined. Measurement was performed on a dry sample (25 ° C.) or a water-absorbed sample (35 ° C.). As a sample, a plate having a diameter of 6 mm and a thickness of 0.8 mm was used.
- FIG. 1 is a side view of an indenter 10 and a jig 11 used for measuring a compressive load.
- the indenter 10 and the jig 11 are polyoxymethylene (Duracon) and have a cylindrical shape.
- the indenter 10 and the jig 11 were attached to a creep meter (RE2-33005S manufactured by Yamaden).
- a double-sided tape (3M Scotch Brand Tape core series 2-0300) was attached to the sample installation portion on the upper surface of the jig 11, and the sample 12 was installed.
- the portion of the sample table (base) to which the jig 11 was attached was moved up and down to bring the indenter 10 and the sample 12 into contact with each other.
- the sample stage was raised by 3.2 mm from the contact position at a compression speed of 0.5 mm / sec, and the sample was buckled. The load when it rose by 3 mm was taken as the compression load value.
- a plate having a diameter of 8 mm and a thickness of 0.8 mm was used.
- a jig for measuring adhesiveness was attached to the sample stage (base) part of the creep meter.
- a part of the jig was removed, a sample was put on a part of the removed jig, and the jig and sample integrated together were attached to a creep meter.
- the sample stage was moved to bring the sample into contact with the metal probe (curvature radius 2.5 mm) and a force of 0.05 N was applied, and the stage was stopped at that position.
- the sample and the probe were separated at a separation speed of 1 mm / sec, and the load applied to the probe at that time was measured with a creep meter (RE2-33005S manufactured by Yamaden).
- a value obtained by subtracting the load after the probe was separated from the sample (the load after desorption) from the measured maximum load was calculated as an adhesive value.
- the adhesion value was evaluated as “A” when the value was 0 N or more and less than 0.16 N, “B” when 0.16 N or more and less than 0.30 N, and “C” when 0.30 N or more.
- the measurement was performed using a dumbbell-shaped test piece (see FIG. 2) having a total length (L 0 ) of about 20 mm, a parallel part length (L) of 6 mm, a parallel part width (W) of 1.5 mm, and a thickness of 0.8 mm.
- the sample was immersed in constant temperature water at 25 ° C. and allowed to stand for 1 minute, and then pulled at a rate of 100 mm / min until breaking.
- Table 5 shows the results of the lens-shaped experimental examples 1 to 14, and Tables 6 to 9 show the results of the plate-shaped experimental examples 15 to 60. From the results in Tables 6 to 9, it was found that hydrolysis can be suppressed by increasing the methacrylate structure, and that alkoxy methacrylate is suitable as such a methacrylate component.
- Experimental Examples 1 to 6 in Table 5 are compositions in which the content of acrylate (POEA, EA) as a base material is reduced from the composition described in Patent Document 1, and POEMA, EHMA, and LMA are added.
- Experimental Examples 1 to 3 to which LMA was added were materials that had high tackiness, were brittle and easily broken, and were susceptible to greaseing.
- Experimental Example 4 to which EHMA was added was a material that easily generated grease.
- Experimental Examples 5 and 6 to which POEMA was added greaseing was likely to occur and was a hard material.
- Experimental Examples 7 to 14 to which ETMA which is alkoxy methacrylate was added were materials having low adhesiveness and not brittle.
- Experimental Examples 15 to 17 in Table 6 are compositions in which the content of acrylate (POEA, EA) as a base material is reduced from the composition described in Patent Document 1 and EMA, BMA, and LMA are added.
- EMA acrylate
- BMA hydrolysis seemed to be suppressed
- BMA dissolution of POEtOH was small and hydrolysis seemed to be suppressed
- Experimental Example 17 to which LMA was added was a material that had high tackiness, was brittle and easily torn, and easily generated grease.
- the preferred addition amount of alkoxy methacrylate is preferably 10 parts by mass or more and 70 parts by mass or less, and more preferably 20 parts by mass or more and 40 parts by mass or less in 100 parts by mass of the base material.
- the minimum amount of alkoxy methacrylate is preferably in the above range mainly from the viewpoint of inhibiting hydrolysis, and the maximum amount of alkoxy methacrylate is preferably in the above range from the viewpoint of easy folding and avoiding a significant burden or hindrance to folding.
- the aromatic ring containing acrylate of a base material 30 mass parts or more in 100 mass parts of base materials are preferable from a viewpoint that the refractive index in a hydration state is 1.50 or more as an intraocular lens material.
- a higher refractive index of the material can achieve a desired refractive power with a thinner lens, and a thinner lens is advantageous for insertion into the eye in a folded state.
- the compressive load in Table 8 shows a value when the experimental example 54 is 1.
- Experimental Example 54 is a material that can be folded in Patent Document 1 but has been evaluated to require a considerable extra force. When the compressive load value was equal to or greater than the value of this material, it was judged that there was a possibility that a significant burden or trouble would occur in folding.
- Experimental Examples 50 to 53 shown in Table 8 although the dissolution of POEtOH was reduced by containing ETMA and the effect of suppressing hydrolysis was obtained, the content of ETMA or HEMA was large, and the folding was good. It wasn't.
- a crosslinkable monomer from the viewpoint of suppressing generation
- the invention disclosed in this specification can be used for applications related to intraocular lenses.
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Abstract
Description
CnH2n+1OCmH2m- (但し(n+m)≦4を満たす) … 化学式(1)
実験例で用いた化合物の略称を以下に示す。
<基材>
POEA :2-フェノキシエチルアクリレート
EA :エチルアクリレート
POEMA:フェノキシエチルメタクリレート
EMA :エチルメタクリレート
BMA :ブチルメタクリレート
EHMA :エチルへキシルメタクリレート
LMA :ラウリルメタクリレート
MTMA :メトキシエチルメタクリレート
ETMA :エトキシエチルメタクリレート
<親水性モノマー>
HEMA:2-ヒドロキシエチルメタクリレート
<架橋性モノマー>
BDDA:1,4-ブタンジオールジアクリレート
表1に示す重合成分、及び重合開始剤として2,2’-アゾビス(2,4-ジメチルバレロニトリル)を、基材全体の100質量部に対して0.5質量部混合し、これを所望のレンズ形状の鋳型内に注入した。この鋳型を80℃のオーブン中に入れて40分間にわたって加熱重合成形を行った。得られた重合体を鋳型から脱型し、溶出処理を行った後、60℃のオーブン内で乾燥させ、レンズ形状の眼内レンズ用材料(実験例1~14)を得た。また、同様に、表2~4に示す重合成分を用い、所望のプレート形状の鋳型内に注入し上述と同様の工程を行い、プレート形状の眼内レンズ用材料(実験例15~60)を得た。必要な測定項目にあわせ、同じ番号(組成)のプレート試料として2種類の厚さの試料を適宜作製した。以下記載の厚さ0.5mmまたは0.8mmのプレートとは、厚さ0.5mmまたは0.8mmのスペーサーを用いた鋳型から作製されたプレートである。試験の目的に合わせ、乾燥したプレートを直径6mmまたは8mmにくり抜いて測定用のプレートとした。
(加水分解処理)
予め試料を60℃にて乾燥し、処理前質量W0を測定した。100mL耐圧瓶に蒸留水50mLを入れ、試料を浸漬した。100℃の乾燥機に耐圧瓶を入れ保存した。試料として直径6mm厚さ0.5mmのプレートを10枚使用した。瓶の風袋質量W01、蒸留水添加後の瓶質量W02、試料浸漬後の瓶質量W03を記録した。
以下の手順によって、加水分解処理30日後の抽出液について、フェノキシエチルアルコール(POEtOH,POEAの加水分解物)の濃度と溶出率を求めた。抽出液採取前の瓶質量W11を記録後、瓶から抽出液を採取し、抽出液採取後の瓶質量W12を記録した。採取した抽出液、標準液、及びそれらのブランク(蒸留水)をHPLCを用いて分析した。分析後、採取した水溶液及び標準溶液のクロマトグラムから蒸留水のクロマトグラムを差し引き、ベースライン補正を行った。補正したクロマトグラムからPOEtOHのピーク面積を算出した。標準液のPOEtOH濃度とピーク面積から検量線を作成した。抽出液のPOEtOHのピーク面積と得られた検量線をもとに、抽出液中のPOEtOHの濃度を算出した。得られたPOEtOHの濃度を用いて、試料1gあたりのPOEtOHの溶出率を次式(1)より算出した。抽出液容量については式(2)より算出した。抽出液容量の算出にあたっては、100℃の加熱により変化した質量のうち試料の質量変化は抽出液のそれに比べて無視できる程小さいこと、抽出液の大部分は水のため密度を1g/1mLとして計算して差し支えないとの考えが前提にある。処理30日の抽出液分析後、再び瓶を100℃の乾燥機に入れた。加水分解処理の合計60日後に、抽出液を再び採取した。処理30日の際と同様に、抽出液採取前の瓶質量W21を記録し、抽出液中のPOEtOH濃度をHPLC分析にて定量し、POEtOHの溶出率を式(3)より算出した。抽出液容量については式(4)より算出した。また、同様に加水分解処理の合計90日後のPOEtOHの溶出率も算出した。
POEtOH溶出率(%)=抽出液中のPOEtOH濃度(ppm)×10-6×抽出液容量V1S(mL)/処理前質量W0(g)×100 …数式(1)
抽出液容量V1S(mL≒g)=[W02(g)-W01(g)]-[W03(g)-W11(g)] …数式(2)
POEtOH溶出率(%)=抽出液中のPOEtOH濃度(ppm)×10-6×抽出液容量V2S(mL)/処理前質量W0(g)×100 …数式(3)
抽出液容量V2S(mL≒g)=V1S(mL≒g)-[W11(g)-W12(g)]-[W12(g)-W21(g)] …数式(4)
この測定において、直径6mm、中心厚み0.8mm±0.1mmのレンズ形状の試料あるいは直径6mm、厚さ0.5mmのプレートの試料を使用した。レンズ形状の試料については、試料を35℃の水中に17時間以上浸漬し、次いで25℃の水中に2時間浸漬した後、実体顕微鏡にて外観を観察した。プレートの試料については、試料を35℃の水中に22時間浸漬し、次いで25℃の水中に2時間浸漬した後、実体顕微鏡にて外観を観察した。外観の観察は、1種の試料につき2あるいは3検体行い、グリスニング(輝点)の発生個数を調べた。倍率は約10~60倍であった。グリスニングを観察しやすいよう上記範囲で倍率を適宜調節し観察した。
25℃における平衡含水状態及び乾燥状態での試料の質量を測定し、吸水率(質量%)を算出した。吸水率は、25℃における平衡含水状態での試料の質量Ww、乾燥状態での試料の質量Wdとにより、次式(5)より算出した。試料として、直径6mm厚さ0.8mmのプレートを5枚使用した。
吸水率(質量%)=(Ww-Wd)/Wd×100 …数式(5)
アッベ屈折計を用いて試料のHg-e線による屈折率を求めた。乾燥状態の試料(25℃)あるいは吸水状態の試料(35℃)で測定した。試料として、直径6mm厚さ0.8mmのプレートを使用した。
以下の手順で直径6mm厚さ0.5mmのプレートを圧縮し座屈(曲げ座屈)させ、6mmから3mmへ試料が折りたたまれた際の荷重値を圧縮荷重値として測定した。測定前の試料を23℃50%RHの環境下に放置し状態調節をした。図1は、圧縮荷重の測定に使用した圧子10及び治具11を側面から見た図である。圧子10及び治具11はポリオキシメチレン(ジュラコン)であり、円柱状である。圧子10及び治具11をクリープメータ(山電製RE2-33005S)に取り付けた。治具11上面の試料設置部分に両面テープ(3M Scotch Brand Tape core series 2-0300)をつけておき、試料12を設置した。治具11を取り付けた試料台(土台)部分を上下させ、圧子10と試料12とを接触させた。圧縮速度0.5mm/secで接触位置から3.2mm試料台部分を上昇させ、試料を座屈させた。3mm上昇した際の荷重を圧縮荷重値とした。
この測定において、直径8mm、厚さ0.8mmのプレートを使用した。クリープメータの試料台(土台)部分に粘着性測定用の治具を取り付けた。治具の一部を取り外し、取り外した治具の一部に試料をはめ、治具と試料が一体になったものをクリープメータに取り付けた。試料台を動かし、試料と金属製プローブ(曲率半径2.5mm)が接触して0.05Nの力がかかった状態とし、その位置で台を停止させた。停止してから約5秒後に引き離し速度1mm/secで試料とプローブを引き離し、その際プローブにかかる荷重をクリープメータ(山電製RE2-33005S)で測定した。測定された最大荷重から、プローブが試料から離れた後の荷重(脱離後の荷重)を差し引いた値を、粘着性の値として算出した。粘着性の値が、0N以上0.16N未満を「A」、0.16N以上0.30N未満を「B」、0.30N以上を「C」として評価した。
全長(L0)約20mm、平行部長さ(L)6mm、平行部幅(W)1.5mm、厚さ0.8mmのダンベル形状の試験片(図2参照)を用いて測定した。25℃の恒温水に試料を浸漬して1分間静置した後、100mm/分の速度で破断するまで引っ張った。ソフトウェアを用いて、最大荷重時の歪み(=伸び率(%))を求めた。
レンズ形状の実験例1~14の結果を表5に、プレート形状の実験例15~60の結果を表6~9に示す。表6~9の結果から、メタクリレート構造の増加により加水分解の抑制が可能であること、及びそのようなメタクリレート成分としてアルコキシメタクリレートが好適であることがわかった。表5の実験例1~6は、特許文献1に記載の組成から基材であるアクリレート(POEA、EA)の含量を減らし、POEMA、EHMA、LMAを添加した組成である。LMAを添加した実験例1~3は粘着性が高く、脆く破れやすく、グリスニングの発生しやすい材料であった。EHMAを添加した実験例4はグリスニングの発生しやすい材料であった。POEMAを添加した実験例5及び6はグリスニングが発生しやすく、硬い材料であった。それらに比べアルコキシメタクリレートであるETMAを添加した実験例7~14は、粘着性が低く、脆くない材料であった。
Claims (8)
- 芳香環含有アクリレート構造と、
炭素数が4以下のアルコキシアルキル基を有するアルコキシアルキルメタクリレート構造と、
親水性モノマーに基づく親水性構造と、
架橋性モノマーに基づく架橋性構造と、
を備えた眼内レンズ用材料。 - 前記アルコキシアルキルメタクリレート構造は、メトキシエチルメタクリレート構造及びエトキシエチルメタクリレート構造のうち1以上である、請求項1に記載の眼内レンズ用材料。
- 前記アルコキシアルキルメタクリレート構造は、前記芳香環含有アクリレート構造と前記アルコキシアルキルメタクリレート構造とを含む基材全体を100質量部としたときに、10質量部以上70質量部以下の範囲で含まれる、請求項1又は2に記載の眼内レンズ用材料。
- 前記アルコキシアルキルメタクリレート構造は、前記芳香環含有アクリレート構造と前記アルコキシアルキルメタクリレート構造とを含む基材全体を100質量部としたときに、20質量部以上40質量部以下の範囲で含まれる、請求項1~3のいずれか1項に記載の眼内レンズ用材料。
- 前記親水性構造は、前記芳香環含有アクリレート構造と前記アルコキシアルキルメタクリレート構造とを含む基材全体の100質量部に対して15質量部以上35質量部以下の範囲で含まれる、請求項1~4のいずれか1項に記載の眼内レンズ用材料。
- 前記架橋性構造は、前記芳香環含有アクリレート構造と前記アルコキシアルキルメタクリレート構造とを含む基材全体の100質量部に対して2質量部以上4質量部以下の範囲で含まれる、請求項1~5のいずれか1項に記載の眼内レンズ用材料。
- 前記基材は、アルキル基の炭素数が1~20のアルキルアクリレート構造を更に含む、請求項1~6のいずれか1項に記載の眼内レンズ用材料。
- 前記芳香環含有アクリレート構造は、フェノキシ基と、炭素数2以下のアルキレン基とアクリレート結合部位とを有する、請求項1~7のいずれか1項に記載の眼内レンズ用材料。
Priority Applications (22)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112018077175-9A BR112018077175B1 (pt) | 2016-07-28 | 2017-07-27 | Material para lentes intraoculares |
KR1020197024695A KR102075327B1 (ko) | 2016-07-28 | 2017-07-27 | 안내 렌즈용 재료 |
PL17834457T PL3461506T3 (pl) | 2016-07-28 | 2017-07-27 | Materiał dla soczewki wewnątrzgałkowej |
AU2017303210A AU2017303210B2 (en) | 2016-07-28 | 2017-07-27 | Material for intraocular lenses |
SG11201811739YA SG11201811739YA (en) | 2016-07-28 | 2017-07-27 | Material for intraocular lenses |
CA3031618A CA3031618C (en) | 2016-07-28 | 2017-07-27 | Material for intraocular lenses |
RU2019100023A RU2694208C1 (ru) | 2016-07-28 | 2017-07-27 | Материал для интраокулярных линз |
CN201780004124.9A CN108367096B (zh) | 2016-07-28 | 2017-07-27 | 眼内透镜用材料 |
JP2018505751A JP6315646B1 (ja) | 2016-07-28 | 2017-07-27 | 眼内レンズ用材料 |
DK17834457.8T DK3461506T3 (da) | 2016-07-28 | 2017-07-27 | Materiale til intraokulære linser |
EP17834457.8A EP3461506B1 (en) | 2016-07-28 | 2017-07-27 | Material for intraocular lenses |
US15/772,273 US10117965B1 (en) | 2016-07-28 | 2017-07-27 | Intraocular lens material |
UAA201900523A UA119961C2 (uk) | 2016-07-28 | 2017-07-27 | Матеріал для інтраокулярних лінз |
MYPI2018002446A MY190775A (en) | 2016-07-28 | 2017-07-27 | Material for intraocular lenses |
KR1020197001212A KR20190010713A (ko) | 2016-07-28 | 2017-07-27 | 안내 렌즈용 재료 |
ES17834457T ES2831002T3 (es) | 2016-07-28 | 2017-07-27 | Material para lentes intraoculares |
NZ749600A NZ749600A (en) | 2016-07-28 | 2017-07-27 | Material for intraocular lenses |
MX2019001108A MX2019001108A (es) | 2016-07-28 | 2017-07-27 | Material para lentes intraoculares. |
ZA2018/08052A ZA201808052B (en) | 2016-07-28 | 2018-11-28 | Material for intraocular lenses |
PH12018502646A PH12018502646A1 (en) | 2016-07-28 | 2018-12-13 | Material for intraocular lenses |
IL263939A IL263939B (en) | 2016-07-28 | 2018-12-24 | Material for intraocular lenses |
HK19100249.8A HK1257888A1 (zh) | 2016-07-28 | 2019-01-08 | 眼內透鏡用材料 |
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JP2016148426 | 2016-07-28 | ||
JP2016-148426 | 2016-07-28 |
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PCT/JP2017/027176 WO2018021455A1 (ja) | 2016-07-28 | 2017-07-27 | 眼内レンズ用材料 |
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US (1) | US10117965B1 (ja) |
EP (1) | EP3461506B1 (ja) |
JP (1) | JP6315646B1 (ja) |
KR (2) | KR20190010713A (ja) |
CN (1) | CN108367096B (ja) |
AU (1) | AU2017303210B2 (ja) |
BR (1) | BR112018077175B1 (ja) |
CA (1) | CA3031618C (ja) |
DK (1) | DK3461506T3 (ja) |
ES (1) | ES2831002T3 (ja) |
HK (1) | HK1257888A1 (ja) |
IL (1) | IL263939B (ja) |
MX (1) | MX2019001108A (ja) |
MY (1) | MY190775A (ja) |
NZ (1) | NZ749600A (ja) |
PH (1) | PH12018502646A1 (ja) |
PL (1) | PL3461506T3 (ja) |
RU (1) | RU2694208C1 (ja) |
SG (1) | SG11201811739YA (ja) |
UA (1) | UA119961C2 (ja) |
WO (1) | WO2018021455A1 (ja) |
ZA (1) | ZA201808052B (ja) |
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WO2020138346A1 (ja) | 2018-12-28 | 2020-07-02 | 株式会社ニデック | 軟質眼内レンズ材料および軟質眼内レンズ |
WO2020261502A1 (ja) | 2019-06-27 | 2020-12-30 | 株式会社メニコン | フォトクロミックポリマーを含む眼用医療機器およびその製造方法 |
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JP7001823B2 (ja) * | 2018-01-31 | 2022-02-04 | 株式会社メニコン | 眼内レンズ |
US11578158B2 (en) * | 2018-01-31 | 2023-02-14 | Menicon Co., Ltd. | Material for intraocular lens |
US11708440B2 (en) | 2019-05-03 | 2023-07-25 | Johnson & Johnson Surgical Vision, Inc. | High refractive index, high Abbe compositions |
CN112292100A (zh) | 2019-05-03 | 2021-01-29 | 强生外科视力公司 | 高反应指数、高色散系数的组合物 |
CN116925281A (zh) * | 2019-12-24 | 2023-10-24 | 爱博诺德(北京)医疗科技股份有限公司 | 眼科材料及其制备方法 |
KR102387402B1 (ko) * | 2020-03-03 | 2022-04-14 | 건양대학교 산학협력단 | 반짝임 변성이 감소된 소수성 아크릴 인공수정체의 제조방법 |
FR3114029B1 (fr) * | 2020-09-17 | 2022-08-26 | Jean Terrisse | Copolymère acrylique absorbant les uv pour la réalisation de lentilles intraoculaires souples |
US11795252B2 (en) | 2020-10-29 | 2023-10-24 | Johnson & Johnson Surgical Vision, Inc. | Compositions with high refractive index and Abbe number |
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