CN108367096A - 眼内透镜用材料 - Google Patents
眼内透镜用材料 Download PDFInfo
- Publication number
- CN108367096A CN108367096A CN201780004124.9A CN201780004124A CN108367096A CN 108367096 A CN108367096 A CN 108367096A CN 201780004124 A CN201780004124 A CN 201780004124A CN 108367096 A CN108367096 A CN 108367096A
- Authority
- CN
- China
- Prior art keywords
- mass parts
- intraocular lens
- acrylate
- lens material
- alkyl ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 122
- 239000000178 monomer Substances 0.000 claims abstract description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 25
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 150000002148 esters Chemical group 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical group CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 claims description 3
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical group COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001118 alkylidene 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 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 239000000523 sample Substances 0.000 description 42
- -1 methacrylic acid alkane Chemical class 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 16
- 150000001721 carbon Chemical group 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 238000004090 dissolution Methods 0.000 description 14
- 125000005250 alkyl acrylate group Chemical group 0.000 description 13
- 239000002253 acid Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 230000006835 compression Effects 0.000 description 9
- 238000007906 compression Methods 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 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
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 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
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000005395 methacrylic acid group Chemical group 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
- 230000007423 decrease Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000413 hydrolysate Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- WFRLANWAASSSFV-FPLPWBNLSA-N palmitoleoyl ethanolamide Chemical compound CCCCCC\C=C/CCCCCCCC(=O)NCCO WFRLANWAASSSFV-FPLPWBNLSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012360 testing method Methods 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
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-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
- 150000001336 alkenes Chemical class 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000009738 saturating 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
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-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
- 230000008859 change Effects 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical group C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 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
- 230000010148 water-pollination Effects 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
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical class C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 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
- 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 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
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-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
- LANHEKZGKDEWLK-UHFFFAOYSA-N 2-methylideneheptanoic acid Chemical compound CCCCCC(=C)C(O)=O LANHEKZGKDEWLK-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-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
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 1
- RMCLKZFGXBSDIO-UHFFFAOYSA-N 3,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(O)O RMCLKZFGXBSDIO-UHFFFAOYSA-N 0.000 description 1
- FHCANPHHJPWZLM-UHFFFAOYSA-N 5,5,6,7,7,7-hexafluoroheptane-2,3-diol Chemical class FC(CC(C(C)O)O)(C(C(F)(F)F)F)F FHCANPHHJPWZLM-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
- BSZBOPWVLRGLOT-UHFFFAOYSA-N C(C=C)(=O)O.CCCCCCCCCCCCCCC Chemical compound C(C=C)(=O)O.CCCCCCCCCCCCCCC BSZBOPWVLRGLOT-UHFFFAOYSA-N 0.000 description 1
- HKCHAFBEVYOZDV-UHFFFAOYSA-N C(CCC)C(C(C)O)O.[F] Chemical compound C(CCC)C(C(C)O)O.[F] HKCHAFBEVYOZDV-UHFFFAOYSA-N 0.000 description 1
- WXHUAFLHJRQPED-UHFFFAOYSA-N CC(C(CC(C(C(F)F)(F)F)(F)F)O)O Chemical class CC(C(CC(C(C(F)F)(F)F)(F)F)O)O WXHUAFLHJRQPED-UHFFFAOYSA-N 0.000 description 1
- NZZYRDJKIYACTL-UHFFFAOYSA-N CC=CC(=O)OC1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)OC(C=CC)=O Chemical compound CC=CC(=O)OC1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)OC(C=CC)=O NZZYRDJKIYACTL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-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
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 238000005452 bending 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
- 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
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 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 class 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-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
- 230000002950 deficient Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
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Abstract
本说明书中公开的眼内透镜用材料具备含芳香环的丙烯酸酯结构,具有碳原子数为4以下的烷氧基的甲基丙烯酸烷氧基烷基酯结构,基于亲水性单体的亲水性结构和基于交联性单体的交联性结构。
Description
技术领域
本发明涉及眼内透镜用材料。
背景技术
以往,伴随着小切口白内障手术的进步,开发了适合作为眼内透镜的、柔软且能够折叠的软型的材料。其中,丙烯酸系的材料具有高折射率,插入眼内后,缓慢地展开,因此优选。但是,若增大形状恢复性,则透镜的伸长率变小,如果有缺陷则成为容易开裂的脆的材料。另一方面,为了从极小的切开创口向眼内插入透镜,优选为伸长率大、不会龟裂或开裂的材料。
作为这种眼内透镜用材料,提出了由使含有亲水性单体的聚合成分聚合而得到的聚合体构成的、吸水率为1.5~4.5质量%的材料,该亲水性单体包含含羟基的(甲基)丙烯酸烷基酯、(甲基)丙烯酰胺单体和N-乙烯基内酰胺等(例如,参照专利文献1)。该眼内透镜用材料由于柔软性优异且具有高折射率,因此可以减薄透镜,能够由折叠的状态介由切开创口插入,并且透明性优异,且能够进一步抑制反光。
现有技术文献
专利文献
专利文献1:日本特开平11-56998号公报
发明内容
然而,该专利文献1的眼内透镜用材料中,丙烯酸系的弹性体有时会引起酯的水解,虽然是微量的但有时会有水解物溶出。一直在寻求能够进一步减少来自这种眼内透镜的水解物的溶出量的材料。
本发明是鉴于这样的课题而进行的,目的在于提供一种能够进一步减少水溶液中的从眼内透镜用材料中溶出的水解物的眼内透镜用材料。
本发明的发明人等为了实现上述目的进行了深入研究,结果发现通过使以丙烯酸酯为基材的眼内透镜用材料中含有特定的甲基丙烯酸酯,能够在维持或者提高作为眼内透镜材料理想的物性的同时,进一步减少水溶液中的水解物的溶出量,从而完成了本发明。
即,本说明书中公开的眼内透镜用材料具有含芳香环的丙烯酸酯结构,具有碳原子数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯结构,基于亲水性单体的亲水性结构和基于交联性单体的交联性结构。
该眼内透镜用材料中,能够进一步减少水溶液中的从眼内透镜用材料中溶出的水解物的溶出量。得到这样的效果的理由例如推测如下。例如,推测甲基丙烯酸酯与丙烯酸酯相比,由于甲基的存在而具有作为材料较硬的特征,但不易受到水的攻击,因此能够进一步提高耐水解性。此外,推测在具有碳原子数4以下的烷氧基烷基的材料中,碳原子数是合适的,不会过硬,具有充分的柔软性。进而,推测从反光抑制能力、降低粘合性、柔软性的观点出发,优选具有碳原子数4以下的烷氧基烷基的材料。这里,烷氧基烷基例如可以为由化学式(1)表示的基团。
CnH2n+1OCmH2m-(其中满足(n+m)≤4)…化学式(1)
附图说明
图1是从侧面观察压缩负荷的测定中使用的压头10和夹具11的图。
图2是伸长率测定中使用的试验片的说明图。
具体实施方式
本实施方式中公开的眼内透镜用材料具备含芳香环的丙烯酸酯结构,具有碳原子数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯结构,基于亲水性单体的亲水性结构和基于交联性单体的交联性结构。该眼内透镜用材料包含含芳香环的丙烯酸酯结构、具有碳原子数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯结构作为基材。此外,该眼内透镜用材料、可以进一步含有烷基的碳原子数为1~20的丙烯酸烷基酯结构作为基材。这里,基材是指构成眼内透镜用材料的主要结构的成分。如化学式(2)所示,该眼内透镜用材料可以包含含芳香环的丙烯酸酯结构A、甲基丙烯酸烷氧基烷基酯结构B和丙烯酸烷基酯结构C作为基材。该化学式(2)中,a、b、c是任意的整数,含芳香环的丙烯酸酯结构A、甲基丙烯酸烷氧基烷基酯结构B和丙烯酸烷基酯结构C任意地与碳链键合,邻接的结构可以适当地不同或可以相同。此外,官能团R1是含有芳香环的官能团,官能团R2是含有烷氧基的碳原子数4以下的烷氧基烷基,官能团R3是碳原子数1~20的烷基。应予说明,在此,将具有丙烯酰基的丙烯酸酯和具有甲基丙烯酰基的甲基丙烯酸酯以下统称为“(甲基)丙烯酸酯”。此外,以下为了方便说明,由单体的名称特定聚合物中所含的构成部位,聚合物的结构的说明中例示的单体设为其聚合基团与其它构成部位键合的结构。例如,聚合物的结构的说明中,作为“(甲基)丙烯酸酯”而例示的单体在聚合物中作为“(甲基)丙烯酸酯结构”存在,其为在(甲基)丙烯酸酯的双键上键合(聚合)有其它构成部位的结构。
该眼内透镜用材料中,含芳香环的丙烯酸酯结构是基于作为基材单体的含芳香环的丙烯酸酯的结构。该含芳香环的丙烯酸酯可以为具有提高眼内透镜用材料的折射率的作用的成分。该含芳香环的丙烯酸酯结构可以具有苯氧基、碳原子数2以下的亚烷基和丙烯酸酯键合位点。作为该含芳香环的丙烯酸酯,例如,可举出丙烯酸苯氧基乙酯、丙烯酸苯基乙酯、丙烯酸苄酯、丙烯酸苯酯、丙烯酸五溴苯酯等,它们可以单独使用或混合使用2种以上。其中,从提高折射率的效果大的方面出发,优选为丙烯酸苯氧基乙酯、丙烯酸苯基乙酯和丙烯酸苄酯中的1种以上,从进一步提高柔软性的方面出发,特别优选为丙烯酸苯氧基乙酯。该含芳香环的丙烯酸酯在将基材整体设为100质量份时,优选为15质量份~80质量份的范围。此外,优选在吸水状态下也具有高的折射率,因此理想的是更优选在基材100质量份中为30质量份~80质量份。
该眼内透镜用材料中,具有碳原子数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯结构是基于作为基材单体的甲基丙烯酸烷氧基烷基酯的结构。该甲基丙烯酸烷氧基烷基酯的烷氧基烷基例如可以由上述化学式(1)表示。作为烷氧基,例如可举出甲氧基、乙氧基等。作为该烷氧基所键合的亚烷基,可举出亚甲基、亚乙基等。该甲基丙烯酸烷氧基烷基酯优选为甲基丙烯酸甲氧基乙酯和甲基丙烯酸乙氧基乙酯中的1种以上,更优选为甲基丙烯酸乙氧基乙酯。该甲基丙烯酸烷氧基烷基酯在将基材整体设为100质量份时,优选为10质量份~70质量份的范围,从能够进一步抑制水解的观点和折叠的容易性的观点出发,更优选在基材100质量份中为20质量份~40质量份。该眼内透镜用材料中,作为其一个例子,将以丙烯酸2-苯氧基乙酯(POEA)、丙烯酸乙酯(EA)和甲基丙烯酸乙氧基乙酯(ETMA)为基材的结构示于化学式(3)。该化学式(3)中,a、b、c是任意的整数,含芳香环的丙烯酸酯结构A、甲基丙烯酸烷氧基烷基酯结构B和丙烯酸烷基酯结构C任意地与碳链键合,邻接的结构可以适当地不同或可以相同。
该眼内透镜用材料中,烷基的碳原子数为1~20的丙烯酸烷基酯结构是基于作为基材单体的丙烯酸烷基酯的结构。该烷基的碳原子数为1~20的丙烯酸烷基酯可以为具有提高眼内透镜用材料的形状恢复性和柔软性的作用的成分。作为该丙烯酸烷基酯,例如,可举出丙烯酸甲酯、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、丙烯酸硬脂酯、丙烯酸辛酯、丙烯酸癸酯、丙烯酸月桂酯、丙烯酸十五烷酯、丙烯酸2-乙基己酯、丙烯酸环戊酯、丙烯酸环己酯等直链状、支链状或环状的丙烯酸烷基酯等。此外,作为丙烯酸烷基酯,例如可举出2,2,2-三氟乙基丙烯酸酯、2,2,3,3-四氟丙基丙烯酸酯、2,2,3,3-四氟-叔戊基丙烯酸酯、2,2,3,4,4,4-六氟丁基丙烯酸酯、2,2,3,4,4,4-六氟-叔己基丙烯酸酯、2,3,4,5,5,5-六氟-2,4-双(三氟甲基)戊基丙烯酸酯、2,2,3,3,4,4-六氟丁基丙烯酸酯、2,2,2,2′,2′,2′-六氟异丙基丙烯酸酯、2,2,3,3,4,4,4-七氟丁基丙烯酸酯、2,2,3,3,4,4,5,5-八氟戊基丙烯酸酯等含氟烷基(甲基)丙烯酸酯等。它们可以单独使用或混合使用2种以上。其中,从形状恢复性和柔软性的提高效果大的方面出发,优选为烷基的碳原子数为1~5的丙烯酸烷基酯,特别优选使用丙烯酸乙酯、丙烯酸丁酯。该丙烯酸烷基酯在将基材整体设为100质量份时优选为0质量份~35质量份的范围。该丙烯酸烷基酯作为基材之一进行处理,但未必是必需成分。从柔软性、形状恢复性的观点出发,能够以上述比例进行适当调整。
该眼内透镜用材料中,亲水性结构是基于亲水性单体的结构。该亲水性单体是对眼内透镜用材料给予亲水性的成分,可以为具有促进眼内透镜用材料的反光的下降的作用的成分。作为该亲水性单体,例如,可以包含烷基的碳原子数为1~20的含羟基的(甲基)丙烯酸烷基酯、(甲基)丙烯酰胺单体和N-乙烯基内酰胺中的1种以上。此外,也可以包含其它亲水性单体。作为含羟基的(甲基)丙烯酸烷基酯,例如可举出(甲基)丙烯酸羟基乙基酯、(甲基)丙烯酸羟基丙基酯、(甲基)丙烯酸羟基丁基酯、(甲基)丙烯酸羟基戊基酯等(甲基)丙烯酸羟基烷基酯、(甲基)丙烯酸二羟基丙基酯、(甲基)丙烯酸二羟基丁基酯、(甲基)丙烯酸二羟基戊基酯等(甲基)丙烯酸二羟基烷基酯。作为(甲基)丙烯酰胺单体,例如可举出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,例如可举出N-乙烯基吡咯烷酮、N-乙烯基哌啶酮、N-乙烯基己内酰胺等。作为其它亲水性单体,例如可举出二乙二醇单(甲基)丙烯酸酯、三乙二醇单(甲基)丙烯酸酯、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、马来酸酐、马来酸、马来酸衍生物、富马酸、富马酸衍生物、氨基苯乙烯、羟基苯乙烯等。上述亲水性单体可以单独使用或混合使用2种以上。这些亲水性单体中,从促进反光的下降的作用大的方面出发,优选为含羟基的(甲基)丙烯酸烷基酯、(甲基)丙烯酰胺单体,特别优选为甲基丙烯酸2-羟基乙基酯。亲水性单体的含量优选相对于基材整体的100质量份为15质量份~35质量份的范围。在该范围,可以充分地体现促进反光的下降的效果,并且不会对干燥状态下的折叠产生显著的负担、障碍。
该眼内透镜用材料中,交联性结构是基于交联性单体的结构。该交联性单体可以是具有控制眼内透镜用材料的柔软性、赋予良好的机械强度、进一步提高形状恢复性、以及提高亲水性单体、其它聚合性单体等聚合成分彼此的共聚性的作用的成分。作为该交联性单体,例如可举出丁二醇二(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)丙烯酸烯丙基酯、(甲基)丙烯酸乙烯基酯、三羟甲基丙烷三(甲基)丙烯酸酯、甲基丙烯酰氧基乙基(甲基)丙烯酸酯、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。它们可以单独使用或混合使用2种以上。这些交联性单体中,从控制柔软性、赋予良好的机械强度、提高形状恢复性和共聚性的效果大的方面出发,特别优选为丁二醇二(甲基)丙烯酸酯和乙二醇二(甲基)丙烯酸酯中的1种以上。交联性单体的含量优选相对于基材整体的100质量份为2质量份~4质量份的范围。从赋予形状恢复性、抑制反光产生的观点出发,优选该含量为2质量份以上。此外,从作为眼内透镜材料具有能够承受从小切口插入的伸长率的观点出发,优选该含量为4质量份以下。
该眼内透镜用材料也可以含有紫外线吸收剂、色素等其它添加成分。作为紫外线吸收剂,例如可举出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′-甲基丙烯酰氧基乙烯氧基-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。紫外线吸收剂的配合量例如优选设为相对于基材整体的100质量份为0.05质量份~3质量份的范围。色素例如在纠正蓝视症时,优选为黄色或橙色的色素。作为色素,例如可举出日本特开2006-291006号公报所记载的染料、颜色索引(CI)所记载的CI溶剂黄、CI溶剂橙等油溶性染料、CI分散黄、CI分散橙等分散染料、还原系染料等。色素的配合量优选相对于基材整体的100质量份为0.01质量份~3质量份的范围。
该眼内透镜用材料例如可以添加自由基聚合引发剂、光聚合引发剂进行聚合而得到。聚合方法例如可以配合自由基聚合引发剂后进行加热,也可以照射微波、紫外线、放射线(γ射线)等电磁波。作为自由基聚合引发剂,例如可举出偶氮二异丁腈、偶氮双(二甲基戊腈)、过氧化苯甲酰、叔丁基过氧化氢、过氧化氢异丙苯等。应予说明,在利用光线等进行聚合时,优选进一步添加光聚合引发剂、敏化剂。作为光聚合引发剂,例如可举出邻苯甲酰苯甲酸甲酯等苯偶姻系化合物、2-羟基-2-甲基-1-苯基丙烷-1-酮等苯酮系化合物、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(ジベンゾスバロン)、2-乙基蒽醌、二苯甲酮丙烯酸酯、二苯甲酮、苯偶酰等。为了以充分的速度进行聚合反应,聚合引发剂、敏化剂的使用量优选相对于基材整体的100质量份为0.01质量份~2质量份的范围。将本发明的眼内透镜用材料成型为眼内透镜时,例如,可以通过切削加工法、铸模(模具)法等进行。
该眼内透镜材料是不易产生反光的材料。以本说明书所记载的实验方法评价材料时,在透镜的情况下,反光的产生数优选为每片透镜15个以下。此外,用相同方法进行评价时,在板的情况下,反光的产生数优选为每片板6个以下,更优选为2个以下。
该眼内透镜材料具有能够耐受从小切口插入的伸长率。具体而言,以本说明书所记载的实验方法评价材料时,伸长率优选为170%以上。此外,该伸长率从眼内透镜用材料的形状恢复性的观点出发,优选为600%以下。
该眼内透镜材料中,在水中以100℃保存30天时的、来自材料的水解物即苯氧基乙基醇(POEtOH)的溶出率优选为0.13质量%以下,更优选为0.10质量%以下。此外,该眼内透镜材料中,在水中以100℃保存60天时的、来自材料的POEtOH的溶出率优选为0.80质量%以下,更优选为0.70质量%以下。此外,该眼内透镜材料中,在水中以100℃保存90天时的、来自材料的POEtOH的溶出率优选为3.30质量%以下,更优选为2.80质量%以下。这些溶出率越少越优选。
该眼内透镜用材料优选吸水率(质量%)为1.5质量%~4.5质量%的范围。吸水率为1.5质量%以上时,可以抑制反光的产生,在4.5质量%以下时,可以进一步抑制柔软性的下降、形状恢复性的下降。如此,本发明的眼内透镜用材料的柔软性优异,且具有高折射率,因此可以减薄透镜,能够以折叠的状态从小的切开创口插入,并且透明性优异,且能够抑制反光的产生。
以上详述的本实施方式的眼内透镜用材料中,可以进一步减少水溶液中的从眼内透镜用材料中溶出的水解物。推测得到这样的效果的理由例如是因为相对于基材的丙烯酸酯,含有具有碳原子数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯。一般而言,甲基丙烯酸酯与丙烯酸酯相比,由于甲基的存在而具有作为材料较硬的特征,但不易受到水的攻击,因此能够进一步提高耐水解性。甲基丙烯酸酯结构的增加容易使反光屡屡发生。对其机理尚不明确,但推测由于丙烯酸和甲基丙烯酸的聚合速度不同,因此容易发生相分离,其结果容易产生反光。但是,推测在本实施方式的眼内透镜用材料中,通过使用甲基丙烯酸烷氧基烷基酯作为甲基丙烯酸酯,从而不会丧失反光抑制能力。此外,推测从反光抑制能力、降低粘合性、柔软性的观点出发而优选碳原子数4以下的甲基丙烯酸烷氧基烷基酯。
应予说明,本发明并不限定于上述实施方式,当然只要属于本发明的技术范围,就能够以各种方式实施。
实施例
以下,将具体地制作本发明的眼内用透镜的例子作为实验例进行说明。应予说明,实验例7~14、18、20、21、23、24、26~29、31、32、34、35、37~43、45~53、55、57、59、60相当于本发明的实施例,实验例1~6、15~17、19、22、25、30、33、36、44、54、56、58相当于比较例。应予说明,本发明不受下述实施例限定,当然只要属于本发明的技术范围就能够以各种方式实施。
[使用成分]
以下示出实验例中使用的化合物的简称。
<基材>
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
EMA:甲基丙烯酸乙酯
BMA:甲基丙烯酸丁酯
EHMA:甲基丙烯酸乙基己酯
LMA:甲基丙烯酸月桂酯
MTMA:甲基丙烯酸甲氧基乙酯
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
[板形状和透镜形状的眼内透镜用材料的制作]
将表1所示的聚合成分和作为聚合引发剂的2,2’-偶氮双(2,4-二甲基戊腈)相对于基材整体的100质量份混合0.5质量份,将其注入所希望的透镜形状的铸模内。将该铸模放入80℃的烘箱中,用40分钟进行加热聚合成型。将得到的聚合体从铸模脱模,进行溶出处理后,在60℃的烘箱内使其干燥,得到透镜形状的眼内透镜用材料(实验例1~14)。此外,同样地使用表2~4所示的聚合成分,注入所希望的板形状的铸模内,进行与上述同样的工序,得到板形状的眼内透镜用材料(实验例15~60)。根据必要的测定项目,适当地制作2种厚度的试样作为相同编号(组成)的板试样。以下记载的厚度0.5mm或0.8mm的板是由使用厚度0.5mm或0.8mm的垫片的铸模制作的板。根据试验的目的,将干燥的板打通成直径6mm或8mm而制成测定用的板。
[表1]
[表2]
[表3]
[表4]
<物性测定>
(水解处理)
预先将试样以60℃进行干燥,测定处理前质量W0。在100mL耐压瓶中加入蒸馏水50mL,浸渍试样。将耐压瓶放入100℃的干燥机中保存。作为试样,使用10片直径6mm厚度0.5mm的板。记录瓶的皮重质量W01、添加蒸馏水后的瓶质量W02、浸渍试样后的瓶质量W03。
(POEtOH溶出率)
通过以下步骤对水解处理30天后的萃取液,求出苯氧基乙基醇(POEtOH,POEA的水解物)的浓度和溶出率。记录提取萃取液前的瓶质量W11后,从瓶中提取萃取液,记录提取萃取液后的瓶质量W12。使用HPLC对所提取的萃取液、标准液和它们的空白(蒸馏水)进行分析。分析后,从提取出的水溶液和标准溶液的色谱中减去蒸馏水的色谱,进行基线校正。由经校正的色谱算出POEtOH的峰面积。由标准液的POEtOH浓度和峰面积作成校准曲线。基于萃取液的POEtOH的峰面积和所得的校准曲线,算出萃取液中的POEtOH的浓度。使用所得的POEtOH的浓度,由下式(1)算出每1g试样的POEtOH的溶出率。对于萃取液容量,由式(2)算出。在算出萃取液容量时,以如下想法为前提:通过100℃的加热而变化的质量中的试样的质量变化与萃取液的质量变化相比,小到可以忽略不计;萃取液的大部分为水,因此可以将密度设为1g/1mL进行计算。对处理30天的萃取液进行分析后,再次将瓶放入100℃的干燥机。水解处理的合计60天后,再次提取萃取液。与处理30天时同样地记录提取萃取液前的瓶质量W21,通过HPLC分析对萃取液中的POEtOH浓度进行定量,由式(3)算出POEtOH的溶出率。对于萃取液容量,由式(4)算出。此外,也同样地算出水解处理的合计90天后的POEtOH的溶出率。
POEtOH溶出率(%)=萃取液中的POEtOH浓度(ppm)×10-6×萃取液容量V1S(mL)/处理前质量W0(g)×100…数学式(1)
萃取液容量V1S(mL≈g)=[W02(g)-W01(g)]-[W03(g)-W11(g)]…数学式(2)
POEtOH溶出率(%)=萃取液中的POEtOH浓度(ppm)×10-6×萃取液容量V2S(mL)/处理前质量W0(g)×100…数学式(3)
萃取液容量V2S(mL≈g)=V1S(mL≈g)-[W11(g)-W12(g)]-[W12(g)-W21(g)]…数学式(4)
(反光)
该测定中,使用直径6mm、中心厚度0.8mm±0.1mm的透镜形状的试样或者直径6mm、厚度0.5mm的板的试样。对于透镜形状的试样,将试样在35℃的水中浸渍17小时以上,接着,在25℃的水中浸渍2小时后,通过实体显微镜观察外观。对于板的试样,将试样在35℃的水中浸渍22小时,接着,在25℃的水中浸渍2小时后,通过实体显微镜观察外观。外观的观察是对1种试样取2或3个被测样品,研究反光(亮点)的产生个数。倍率约为10~60倍。以容易观察反光的方式在上述范围适当调节倍率并观察。
(吸水率)
测定在25℃的平衡含水状态和干燥状态下的试样的质量,算出吸水率(质量%)。吸水率是由在25℃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根据下式(5)算出。作为试样,使用5片直径6mm厚度0.8mm的板。
吸水率(质量%)=(Ww-Wd)/Wd×100…数学式(5)
(折射率)
使用阿贝折射仪求出试样的基于Hg-e线的折射率。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。
(压缩负荷(板))
按以下步骤将直径6mm厚度0.5mm的板压缩使其压弯(弯曲压弯),将测定试样从6mm折叠到3mm时的负荷值作为压缩负荷值。将测定前的试样在23℃、50%RH的环境下放置进行状态调节。图1是从侧面观察压缩负荷的测定中使用的压头10和夹具11的图。压头10和夹具11为聚甲醛(DURACON),为圆柱状。将压头10和夹具11安装于蠕变计(山电制的RE2-33005S)。在夹具11上表面的试样设置部分贴上双面胶带(3MScotch Brand Tape coreseries 2-0300),设置试样12。使安装有夹具11的试样台(基座)部分升降,使压头10与试样12接触。以压缩速度0.5mm/sec使试样台部分从接触位置上升3.2mm,压弯试样。将上升3mm时的负荷作为压缩负荷值。
(粘合性)
该测定中,使用直径8mm、厚度0.8mm的板。在蠕变计的试样台(基座)部分安装粘合性测定用的夹具。取下夹具的一部分,将试样嵌入取下的夹具的一部分中,夹具和试样成为一体并安装于蠕变计。移动试样台,成为试样与金属制的探针(曲率半径2.5mm)接触而施加0.05N的力的状态,使台在该位置停止。停止后约5秒后以拉开速度1mm/sec将试样与探针拉开,用蠕变计(山电制的RE2-33005S)测定此时对探针施加的负荷。算出从所测定的最大负荷减去探针离开试样后的负荷(脱离后的负荷)而得的值作为粘合性的值。将粘合性的值为0N以上且小于0.16N评价为“A”,将0.16N以上且小于0.30N评价为“B”,将0.30N以上评价为“C”。
(拉伸试验)
使用全长(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2)进行测定。在25℃的恒温水中浸渍试样而静置1分钟后,以100mm/分钟的速度拉伸至断裂为止。使用软件求出最大负荷时的形变(=伸长率(%))。
(结果和考察)
将透镜形状的实验例1~14的结果示于表5,将板形状的实验例15~60的结果示于表6~9。由表6~9的结果可知通过增加甲基丙烯酸酯结构能够抑制水解,并且优选为甲基丙烯酸烷氧基酯作为这种甲基丙烯酸酯成分。表5的实验例1~6是从专利文献1所记载的组成中减少作为基材的丙烯酸酯(POEA、EA)的含量、且添加POEMA、EHMA、LMA的组成。添加了LMA的实验例1~3是粘合性高、脆且容易破裂、容易产生反光的材料。添加了EHMA的实验例4是容易产生反光的材料。添加了POEMA的实验例5和6是容易产生反光且硬的材料。与它们相比,添加了作为甲基丙烯酸烷氧基酯的ETMA的实验例7~14是粘合性低、不脆的材料。
表6的实验例15~17是从专利文献1所记载的组成中减少作为基材的丙烯酸酯(POEA、EA)的含量的、添加了EMA、BMA、LMA的组成。添加了EMA的实验例15是POEtOH的溶出少、水解被抑制、但明显难以作为眼内透镜材料而容易地折叠的材料。添加了BMA的实验例16是POEtOH的溶出少、水解被抑制、但容易产生反光的材料。添加了LMA的实验例17是粘合性高、脆且容易破裂、容易产生反光的材料。与它们相比,添加了作为甲基丙烯酸烷氧基酯的MTMA或ETMA的多个实验例是POEtOH的溶出少、水解被抑制、粘合性不高的材料。此外,与6同样为较少产生反光的、不脆的材料。
由表5~9的结果可知作为甲基丙烯酸烷氧基酯的合适的添加量,优选在基材100质量份中为10质量份~70质量份,更优选为20质量份~40质量份。甲基丙烯酸烷氧基酯的最小量主要从抑制水解的观点出发优选为上述范围,甲基丙烯酸烷氧基酯的最大量从折叠的容易性、不对折叠产生显著负担、障碍的观点出发优选为上述范围。
对于基材的含芳香环的丙烯酸酯,从作为眼内透镜材料的水合状态下的折射率为1.50以上的观点出发,优选在基材100质量份中为30质量份以上。材料的折射率越高,越能够以更薄的透镜实现所希望的折射能力,透镜越薄,对在折叠的状态下插入眼内越有利。
对于亲水性单体,从抑制反光产生的观点出发,相对于基材整体的100质量份,优选为15质量份以上,为了在干燥状态下对折叠不产生显著的负担、障碍,优选为35质量份以下。在干燥状态下容易弯曲是指能够进行插入器具中的保存·流通·使用。表8的压缩负荷表示将实验例54设为1时的值。实验例54是在专利文献1中被评价为能够折叠但需要相当的多余的力的材料。压缩负荷值为该材料的值以上时,判断为存在对折叠产生显著负担、障碍的可能性。表8所示的实验例50~53中,通过含有ETMA,可得到减少POEtOH的溶出、抑制水解的效果,但ETMA或HEMA的含量多,对折叠并不良好。
对于交联性单体,从抑制反光的产生的观点和插入眼内后的形状恢复性的观点出发,相对于基材整体的100质量份,优选为2质量份以上,为了避免成为伸长率小且容易破裂的材料,优选为4质量份以下。
[表5]
1)透镜的测定结果。
试验数n=2或3的平均值
[表9]
该申请将2016年7月28日提出申请的日本专利申请第2016-148426号作为主张优先权的基础,本说明书中通过引用包含其全部内容。
产业上的可利用性
本说明书中公开的发明可以用于与眼内透镜相关的用途。
符号说明
10 压头,11 冶具,12 试样。
Claims (8)
1.一种眼内透镜用材料,具备:
含芳香环的丙烯酸酯结构,
具有碳原子数为4以下的烷氧基烷基的甲基丙烯酸烷氧基烷基酯结构,
基于亲水性单体的亲水性结构,和
基于交联性单体的交联性结构。
2.根据权利要求1所述的眼内透镜用材料,其中,所述甲基丙烯酸烷氧基烷基酯结构为甲基丙烯酸甲氧基乙酯结构和甲基丙烯酸乙氧基乙酯结构中的1个以上。
3.根据权利要求1或2所述的眼内透镜用材料,其中,在将含有所述含芳香环的丙烯酸酯结构和所述甲基丙烯酸烷氧基烷基酯结构的基材整体设为100质量份时,在10质量份~70质量份的范围含有所述甲基丙烯酸烷氧基烷基酯结构。
4.根据权利要求1~3中任一项所述的眼内透镜用材料,其中,在将含有所述含芳香环的丙烯酸酯结构和所述甲基丙烯酸烷氧基烷基酯结构的基材整体设为100质量份时,在20质量份~40质量份的范围含有所述甲基丙烯酸烷氧基烷基酯结构。
5.根据权利要求1~4中任一项所述的眼内透镜用材料,其中,在相对于含有所述含芳香环的丙烯酸酯结构和所述甲基丙烯酸烷氧基烷基酯结构的基材整体的100质量份为15质量份~35质量份的范围含有所述亲水性结构。
6.根据权利要求1~5中任一项所述的眼内透镜用材料,其中,在相对于含有所述含芳香环的丙烯酸酯结构和所述甲基丙烯酸烷氧基烷基酯结构的基材整体的100质量份为2质量份~4质量份的范围含有所述交联性结构。
7.根据权利要求1~6中任一项所述的眼内透镜用材料,其中,所述基材进一步含有烷基的碳原子数为1~20的丙烯酸烷基酯结构。
8.根据权利要求1~7中任一项所述的眼内透镜用材料,其中,所述含芳香环的丙烯酸酯结构具有苯氧基、碳原子数2以下的亚烷基和丙烯酸酯键合位点。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113024716A (zh) * | 2019-12-24 | 2021-06-25 | 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 |
CN113195563A (zh) * | 2018-12-28 | 2021-07-30 | 株式会社尼德克 | 软质眼内透镜材料和软质眼内透镜 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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JP7274577B2 (ja) | 2019-06-27 | 2023-05-16 | 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 |
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 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1155845A (zh) * | 1995-06-07 | 1997-07-30 | 阿尔康实验室公司 | 改进的高折光指数眼科透镜材料 |
WO2006113290A1 (en) * | 2005-04-13 | 2006-10-26 | Benz Research & Development Corporation | Polymers for intraocular lenses |
CN101855256A (zh) * | 2007-10-10 | 2010-10-06 | 美商班兹研发公司 | 具有高水含量和稳定性的水凝胶 |
WO2012004746A2 (en) * | 2010-07-05 | 2012-01-12 | Polymer Technologies International (Eou) | Refractive-diffractive ophthalmic device and compositions useful for producing same |
CN103596602A (zh) * | 2011-06-03 | 2014-02-19 | 诺瓦提斯公司 | 疏水性丙烯酸眼内透镜材料 |
CN103946251A (zh) * | 2011-09-16 | 2014-07-23 | 宾视研发公司 | 疏水性人工晶状体 |
CN105384867A (zh) * | 2014-08-20 | 2016-03-09 | 广东东阳光药业有限公司 | 一种制备疏水性人工晶体的聚合物 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
BRPI0516646A (pt) * | 2004-11-30 | 2008-09-16 | Advanced Medical Optics Inc | composições poliméricas biocompatìveis para uso na preparação de lentes intra-oculares na cámara posterior |
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 |
TWI426931B (zh) * | 2007-10-03 | 2014-02-21 | Alcon Inc | 眼科與耳鼻喉科裝置材料(一) |
TWI461186B (zh) * | 2007-10-05 | 2014-11-21 | Alcon Inc | 眼科與耳鼻喉科裝置材料(二) |
WO2009070438A1 (en) * | 2007-11-30 | 2009-06-04 | Bausch & Lomb Incorporated | Optical material and method for modifying the refractive index |
FR2930731B1 (fr) * | 2008-04-30 | 2014-06-27 | Acrylian | Materiau polymere acrylique, hydrophobe pour lentille intraoculaire |
US9144491B2 (en) * | 2011-06-02 | 2015-09-29 | University Of Rochester | Method for modifying the refractive index of an optical material |
FR3013050B1 (fr) * | 2013-11-13 | 2015-12-11 | O&O Mdc Ltd | Procede de fabrication d'un materiau polymere acrylique hydrophobe pour dispositif ophtalmologique |
WO2016002936A1 (ja) | 2014-07-04 | 2016-01-07 | 日本ゼオン株式会社 | アクリルゴム、アクリルゴム組成物、アクリルゴム架橋物及びシール部材 |
-
2017
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1155845A (zh) * | 1995-06-07 | 1997-07-30 | 阿尔康实验室公司 | 改进的高折光指数眼科透镜材料 |
WO2006113290A1 (en) * | 2005-04-13 | 2006-10-26 | Benz Research & Development Corporation | Polymers for intraocular lenses |
CN101855256A (zh) * | 2007-10-10 | 2010-10-06 | 美商班兹研发公司 | 具有高水含量和稳定性的水凝胶 |
WO2012004746A2 (en) * | 2010-07-05 | 2012-01-12 | Polymer Technologies International (Eou) | Refractive-diffractive ophthalmic device and compositions useful for producing same |
CN103596602A (zh) * | 2011-06-03 | 2014-02-19 | 诺瓦提斯公司 | 疏水性丙烯酸眼内透镜材料 |
CN103946251A (zh) * | 2011-09-16 | 2014-07-23 | 宾视研发公司 | 疏水性人工晶状体 |
CN105384867A (zh) * | 2014-08-20 | 2016-03-09 | 广东东阳光药业有限公司 | 一种制备疏水性人工晶体的聚合物 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN113195563A (zh) * | 2018-12-28 | 2021-07-30 | 株式会社尼德克 | 软质眼内透镜材料和软质眼内透镜 |
CN113195563B (zh) * | 2018-12-28 | 2022-12-23 | 株式会社尼德克 | 软质眼内透镜材料和软质眼内透镜 |
CN115975105A (zh) * | 2018-12-28 | 2023-04-18 | 株式会社尼德克 | 软质眼内透镜材料和软质眼内透镜 |
CN113024716A (zh) * | 2019-12-24 | 2021-06-25 | 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 |
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