JP6017572B2 - コーティングによるuv吸収性眼用レンズの製造方法 - Google Patents
コーティングによるuv吸収性眼用レンズの製造方法 Download PDFInfo
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- JP6017572B2 JP6017572B2 JP2014535808A JP2014535808A JP6017572B2 JP 6017572 B2 JP6017572 B2 JP 6017572B2 JP 2014535808 A JP2014535808 A JP 2014535808A JP 2014535808 A JP2014535808 A JP 2014535808A JP 6017572 B2 JP6017572 B2 JP 6017572B2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- JNDVNJWCRZQGFQ-UHFFFAOYSA-N 2-methyl-N,N-bis(methylamino)hex-2-enamide Chemical compound CCCC=C(C)C(=O)N(NC)NC JNDVNJWCRZQGFQ-UHFFFAOYSA-N 0.000 claims description 2
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- DFENKTCEEGOWLB-UHFFFAOYSA-N n,n-bis(methylamino)-2-methylidenepentanamide Chemical compound CCCC(=C)C(=O)N(NC)NC DFENKTCEEGOWLB-UHFFFAOYSA-N 0.000 claims description 2
- ZEMHQYNMVKDBFJ-UHFFFAOYSA-N n-(3-hydroxypropyl)prop-2-enamide Chemical compound OCCCNC(=O)C=C ZEMHQYNMVKDBFJ-UHFFFAOYSA-N 0.000 claims description 2
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 31
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- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 4
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241001415846 Procellariidae Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000012724 UV-induced polymerization Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- CKIDCRFWPRVLEU-UHFFFAOYSA-N [3-(benzotriazol-2-yl)-4-hydroxyphenyl] prop-2-enoate Chemical compound OC1=CC=C(OC(=O)C=C)C=C1N1N=C2C=CC=CC2=N1 CKIDCRFWPRVLEU-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-O azetidin-1-ium Chemical group C1C[NH2+]C1 HONIICLYMWZJFZ-UHFFFAOYSA-O 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 239000012867 bioactive agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- RLYNGYDVXRKEOO-SQQVDAMQSA-N but-2-enoic acid;(e)-but-2-enoic acid Chemical compound CC=CC(O)=O.C\C=C\C(O)=O RLYNGYDVXRKEOO-SQQVDAMQSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 229920003064 carboxyethyl cellulose Polymers 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- WROHVVIPQXODQM-LYSKQWNXSA-N carboxymethyl-β-cyclodextrin sodium salt Chemical compound O([C@@H]([C@H]([C@@H]1O)O)O[C@H]2[C@@H](O)[C@@H]([C@@H](O[C@@H]3[C@@H](COCC(O)=O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@@H](COCC(O)=O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@@H](COCC(O)=O)O[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3[C@@H](COCC(O)=O)O[C@@H]([C@H]([C@@H]3O)O)O3)O[C@@H]2COCC(O)=O)O)[C@H](COCC(O)=O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@H]3[C@@H](COCC(O)=O)O1 WROHVVIPQXODQM-LYSKQWNXSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- DLGJWSVWTWEWBJ-HGGSSLSASA-N chondroitin Chemical compound CC(O)=N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@H](O)C=C(C(O)=O)O1 DLGJWSVWTWEWBJ-HGGSSLSASA-N 0.000 description 1
- 229940059329 chondroitin sulfate Drugs 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
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- 238000006073 displacement reaction Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- ZQTYQMYDIHMKQB-UHFFFAOYSA-N exo-norborneol Chemical compound C1CC2C(O)CC1C2 ZQTYQMYDIHMKQB-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010501 iterative synthesis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229940099563 lactobionic acid Drugs 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 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
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080307 sodium salt n-(carbonyl-methoxypolyethylene glycol 2000)-1,2-distearoyl-sn-glycero-3-phosphoethanolamine Drugs 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000007704 wet chemistry method Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B05D5/06—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain multicolour or other optical effects
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
- B29D11/00125—Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00634—Production of filters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00865—Applying coatings; tinting; colouring
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
Landscapes
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Eyeglasses (AREA)
- Optical Filters (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Description
UV吸収性眼用レンズ、特にUV吸収性コンタクトレンズは、典型的には、重合しうるUV吸収剤、並びに少なくとも1種のビニルモノマー、マクロマー及び/又はプレポリマーを包含するレンズ形成組成物の成形用型中での熱−又はUV−誘導性ラジカル重合を伴う、いわゆる注型成形プロセスにより大量生産される。そのUV吸収性部分に共有結合したエチレン不飽和基を包含する、共重合しうるベンゾトリアゾール、ベンゾフェノン及びトリアジンUV吸収剤が知られており、これまで使用されてきた。これらのUV吸収剤は、眼用レンズのポリマーマトリックス中に組み込むことができる。しかし重合していないUV吸収剤は、得られる眼用レンズが使用に要求される生体適合性を有することを保証するため、抽出プロセスにより除去しなければならない。更に、レンズの生産が、熱誘導性重合プロセスの加工サイクルより短いサイクルを持つUV誘導性重合プロセスに頼るとき、既知の重合しうるUV吸収剤の使用に関連した幾つかの不都合が存在する。第1に、レンズへのUV吸収剤の組み込み効率は定かでないかもしれない。第2に、レンズ形成組成物中に存在するUV吸収剤が、重合を開始させるのに利用可能なUV線の量を減少させることがあり、生じるレンズへのUV吸収剤の共有結合による組み込みの効率を低下させることさえありうる。未反応のUV吸収剤は、一般に1種以上の抽出プロセスでレンズから除去しなければならない。第3に、UV吸収剤は、レンズ形成組成物の無効な又は不均一な光重合をもたらすかもしれない。
1つの態様において、本発明は、UV吸収性眼用レンズの製造方法であって、眼用レンズ、好ましくはコンタクトレンズを得る工程;眼用レンズを、第1の有機溶媒及びUV吸収性ポリマーを含むコーティング溶液に、眼用レンズ上にUV吸収性コーティングを形成するのに充分な時間浸漬する工程(ここで、UV吸収性ポリマーは、UV吸収性モノマー単位及び少なくとも約50%、好ましくは少なくとも約60%、更に好ましくは少なくとも約70%、更になお好ましくは少なくとも約80%、最も好ましくは少なくとも約90モル%のカルボキシル含有モノマー単位を含む);及び場合により、しかし、好ましくは、反応性官能基を有する親水性ポリマー又はポリマー材料を、UV吸収性コーティング上に共有結合させることによって、ヒドロゲルコーティングを形成する工程(ここで、ヒドロゲルコーティングは、UV吸収性コーティング上に、UV吸収性コーティングの1個のカルボキシル基と親水性ポリマー又はポリマー材料の1個の反応性官能基との間にそれぞれ形成される結合を介して共有結合される)を含む方法を提供する。
)。
本方法が開示及び記述される前に、当然のことながら後述の態様は、具体的な化合物、工程、又は使用に限定されない(これらは当然変化しうるため)。また当然のことながら、本明細書に使用される用語は、特定の態様を説明することのみを目的としており、限定することを意図しない。
、アリル、ビニル:
、スチレニル、又は他のC=C含有基を包含する。
で示される正に荷電した基のことをいう。
[式中、nは、1〜5の整数であり、そしてR1、R2及びR3は、相互に独立に、C1−C8アルキル又はC1−C8ヒドロキシアルキルである]で示される両性イオン基のことをいう。
[式中、
R1及びR2は、相互に独立に、水素、C2−C12直鎖若しくは分岐アルキル基、ハロゲン(Cl又はBr)、C6〜C24アリール基、C7〜C24アルキルアリール基、C7〜C24アリールアルキル、又はC1−C12直鎖若しくは分岐アルコキシ基であり;
L1は、共有結合又は−Xa−E1−Xb−E2−Xc−の二価基であり、ここで、Xaは、共有結合、−O−、カルボニル:
、−(RaO)n−の二価基(ここで、Raは、直鎖又は分岐C1−C12−アルキレンであり、そしてnは、1〜10である)、下記式:
(ここで、R”は、H又はC1−C8アルキルである)であり、E1及びE2は、相互に独立に、共有結合、−(RaO)n−の二価基(ここで、Ra及びnは、上記と同義である)、下記式:
(ここで、R”は、H又はC1−C8アルキルである)、C1〜C12直鎖若しくは分岐アルキレン二価基、40個以下の炭素原子を持つシクロアルキル二価基、40個以下の炭素原子を持つアルキルシクロアルキル二価基、40個以下の炭素原子を持つアルキルアリール二価基、40個以下の炭素原子を持つアリールアルキレン二価基、又は式:−C(O)L2C(O)−を有するジカルボニル基(ここで、L2は、C1〜C12直鎖若しくは分岐アルキレン二価基又は−(Re1−O)w1−(Re2−O)w2−(Re3−O)w3−であり、ここで、Re1、Re2、及びRe3は、相互に独立に、直鎖又は分岐C1−C4−アルキレンであり、そしてw1、w2及びw3は、相互に独立に、0〜20の数であり、ただし(w1+w2+w3)の合計は、1〜60である)であり、そしてXb及びXcは、相互に独立に、共有結合、カルボニル、下記式:
(ここで、R”は、上記と同義である)であり;そして
Yは、アズラクトン基、エポキシ基、イソシアナト基、アジリジン基、又は−NHR’のアミノ基(ここで、R’は、水素又はC1−C12非置換若しくは置換の直鎖若しくは分岐アルキル基である)である]により表される。
[式中、
R3は、水素、C1−C12直鎖若しくは分岐アルキル基、ハロゲン、C6〜C24アリール基、C7〜C24アルキルアリール基、C7〜C24アリールアルキル、又はC1−C12直鎖若しくは分岐アルコキシ基であり;
L3は、共有結合又は−Xa−E1−Xb−E2−Xc−の二価基であり、ここで、Xaは、共有結合、−O−、カルボニル:
、−(RaO)n−の二価基(ここで、Raは、直鎖又は分岐C1−C12−アルキレンであり、そしてnは、1〜10である)、下記式:
(ここで、R”は、H又はC1−C8アルキルである)であり、E1及びE2は、相互に独立に、共有結合、−(RaO)n−の二価基(ここで、Ra及びnは、上記と同義である)、下記式:
(ここで、R”は、H又はC1−C8アルキルである)、C1〜C12直鎖若しくは分岐アルキレン二価基、40個以下の炭素原子を持つシクロアルキル二価基、40個以下の炭素原子を持つアルキルシクロアルキル二価基、40個以下の炭素原子を持つアルキルアリール二価基、40個以下の炭素原子を持つアリールアルキレン二価基、又は式:−C(O)L2C(O)−を有するジカルボニル基(ここで、L2は、C1〜C12直鎖若しくは分岐アルキレン二価基又は−(Re1−O)w1−(Re2−O)w2−(Re3−O)w3−であり、ここで、Re1、Re2、及びRe3は、相互に独立に、直鎖又は分岐C1−C4−アルキレンであり、そしてw1、w2及びw3は、相互に独立に、0〜20の数であり、ただし(w1+w2+w3)の合計は、1〜60である)であり、そしてXb及びXcは、相互に独立に、共有結合、カルボニル、下記式:
(ここで、R”は、上記と同義である)であり;そして
Y1は、アズラクトン基、エポキシ基、イソシアナト基、アジリジン基、又は−NHRのアミノ基(ここで、Rは、水素又はC1−C12非置換若しくは置換の直鎖若しくは分岐アルキル基である)である]により表される。
(ここで、R”は、H又はC1−C8アルキルである)であり、E1及びE2は、相互に独立に、共有結合、−(RaO)n−の二価基(ここで、Raは、直鎖又は分岐C1−C12−アルキレンであり、そしてnは、1〜10である)、C1〜C12直鎖若しくは分岐アルキレン二価基、12個以下の炭素原子を持つシクロアルキル二価基、20個以下の炭素原子を持つアルキルシクロアルキル二価基、20個以下の炭素原子を持つアルキルフェニル二価基、又は20個以下の炭素原子を持つフェニルアルキレン二価基であり、Xb及びXcは、相互に独立に、共有結合、カルボニル、下記式:
(ここで、R”は、上記と同義である)であり;そしてYは、−NHRのアミノ基(ここで、Rは、水素又はC1−C6非置換若しくは置換の直鎖若しくは分岐アルキル基である)である]。
本実施例は、以下のスキーム1に示されるとおり、マイケル付加による本発明のアミノ官能基化UV吸収性化合物の調製法を説明する。
Norbloc(即ち、メタクリル酸2−[3−(2H−ベンゾトリアゾール−2−イル)−4−ヒドロキシフェニル]エチル)は、Aldrich(カタログ番号413437-100G)から受領した。システアミン塩酸塩は、Fluka(カタログ番号30078)から受領した。0.1Nヨウ素水溶液は、Acros(カタログ番号124220010)から受領した。
アミノ官能基化Norbloc(生成物)は、1H−NMRにより特性決定した;生成物と出発物質とのスペクトルの比較では、5.5及び6.1ppmのメタクリラートプロトンの消失が見られた。生成物の官能基もアミノ基滴定により決定した;結果は、2.21meq/g(理論値2.5meq/g)でアミノ官能基を示した。生成物の純度もまたHPLC分析により求めた;アミノ官能基化Norblocの保持時間は、335nmの検出波長でメタクリラート出発物質のNorblocの保持時間より短かった。HPLC分析による生成物の典型的な純度は、アミノ官能基物質85〜95%の間であり、Norbloc(出発物質)を主要な不純物として含んでいた。
PDMS架橋剤Iの調製
4Lビーカーで、Na2CO3 24.13g、NaCl 80g及び脱イオン水1.52kgを混合して溶解した。別の4Lビーカーで、ビス−3−アミノプロピル−ポリジメチルシロキサン(Shin-Etsu、MW約11500)700gをヘキサン1000gに溶解した。4L反応器にタービン撹拌器の付いたオーバーヘッド撹拌機及びマイクロ流量調整器の付いた250mL滴下ロートを取り付けた。次に2つの溶液を反応器に仕込んで、激しく撹拌しながら15分間混合することにより、乳濁液を生成した。塩化アクリロイル14.5gをヘキサン100mLに溶解して、滴下ロートに仕込んだ。この塩化アクリロイル溶液を乳濁液に激しい撹拌下で1時間かけて滴下により加えた。添加の終了後、乳濁液を30分間撹拌し、次に撹拌を停止して、一晩相を分離させた。水相をデカントして、有機相を水に溶解した2.5% NaCl 2.0kgの混合物で2回洗浄した。次に有機相を硫酸マグネシウムで乾燥し、1.0μmサイズ排除のフィルターで濾過して、ロータリーエバポレーターで濃縮した。生じた油状物を高真空乾燥により一定重量になるまで更に精製した。滴定による生じた生成物の分析によって、0.175mEq/gのC=C二重結合が明らかになった。
4Lビーカーで、Na2CO3 61.73g、NaCl 80g及び脱イオン水1.52kgを混合して溶解した。別の4Lビーカーで、ビス−3−アミノプロピル−ポリジメチルシロキサン(Shin-Etsu、MW約4500)700gをヘキサン1000gに溶解した。4L反応器にタービン撹拌器の付いたオーバーヘッド撹拌機及びマイクロ流量調整器の付いた250mL滴下ロートを取り付けた。次に2つの溶液を反応器に仕込んで、激しく撹拌しながら15分間混合することにより、乳濁液を生成した。塩化アクリロイル36.6gをヘキサン100mLに溶解して、滴下ロートに仕込んだ。この塩化アクリロイル溶液を乳濁液に激しい撹拌下で1時間かけて滴下により加えた。添加の終了後、乳濁液を30分間撹拌し、次に撹拌を停止して、一晩相を分離させた。水相をデカントして、有機相を水に溶解した2.5% NaCl 2.0kgの混合物で2回洗浄した。次に有機相を硫酸マグネシウムで乾燥し、1.0μmサイズ排除に濾過して、ロータリーエバポレーターで濃縮した。生じた油状物を高真空乾燥により一定重量になるまで更に精製した。滴定による生じた生成物の分析によって、0.435mEq/gのC=C二重結合が明らかになった。
2Lジャケット付き反応器に、加熱/冷却ループ、還流冷却器、N2注入口/真空アダプター、補給チューブアダプター及びオーバーヘッド機械式撹拌機を取り付けた。上で調製したPDMS架橋剤I 90.00g及び上で調製したPDMS架橋剤II 30.00gを1−プロパノール480gに溶解することにより溶液を生成した。この溶液を反応器に仕込んで、8℃に冷却した。15mBar未満まで空気を抜き、真空で15分間保持し、次に乾燥窒素で再加圧することにより、溶液を脱気した。この脱気手順を合計3回繰り返した。反応器を乾燥窒素のブランケット下で保持した。
上で調製した架橋性コポリマー18.83gを1−プロパノールおよそ200mLに溶解して、総溶液重量約70gまで濃縮し、0.45μmサイズ排除に濾過した。固形分26.53%の溶液67.94gを回収した。2−ヒドロキシ−4’−ヒドロキシエチル−2−メチルプロピオフェノン(IRGACURE(登録商標)-2959、Ciba Specialty Chemicals)の1%溶液4.503gを加えて、次にこの溶液を濃縮して60%固体を有する最終配合物とした。この配合物200mgをポリ(プロピレン)コンタクトレンズ成形用型に分注して、成形用型を閉じた。次に成形用型を2.18mW/cm2の強度を有する紫外線源で15秒間照射した。次に成形用型を開いて、コンタクトレンズを成形用型半体から取り出した。
本実施例は、PAA−F50と表される式(1)(式中、m:n≒160:1)のフルオレセイン修飾ポリアクリル酸を使用することにより本発明の方法を説明する。
Bruker Avance 400 NMR分光計により1H−NMR分光分析を実行した。UV−Vis分光分析には、Perkin Elmer Lambda 25分光計を利用した。
Xフルオレセイン=100×A×MA/[w×εF(491nm)×d+A×(MA−MF)][Mol-%] (1)。
式中、w[g/L]は、溶液中のPAA−F50の濃度であり;MA(72g/mol)及びMF(419g/mol)は、コポリマーPAA−F50中の反復モノマー単位、それぞれアクリル酸及びフルオレセイン修飾アクリル酸(即ち、6−アクリロイルアミド−フルオレセイン)のモル質量である。Aは、491nmでの対応するUV吸光度であり;εF(491nm)は、491nmの波長でのコポリマー中のフルオレセイン部分の吸光係数(これは6−アミノフルオレセインの吸光係数(εAF(491nm)=76290[l/(mol×cm)])と等しいと仮定した)であり;dは、UV測定キュベットの幅である。
実施例2で調製したコンタクトレンズを水浴からPAA−F50の溶液(1−プロパノールに溶解、HCOOHで約2.0にpHを調整;0.36g/l PAA−F50、標識程度:0.59Mol-%)を含有する浴に移すと、PAA−F50はレンズ中に絶え間なく拡散した。このレンズへのPAA−F50の拡散は、レンズの着色により反映させたが、レンズ色の強度は処理時間の増大につれて増大した(図1を参照のこと)。拡散及び着色の増大はまた、UV−Vis分光光度法によりモニターすることができた。PAA−F50のフルオレセイン部分に帰属する490nmの吸光度は、時間と共に増大した(図2を参照のこと)。レンズ上のPAA−F50コーティングの形成は、最初にコンタクトレンズをPAA−F50溶液(上で調製)に約1時間浸漬し、次にPAA−F50コーティングレンズをリン酸緩衝生理食塩水(PBS)に移して保存することによって実証した。緩衝液は、数週間の保存後でもほぼ無色を保った。
本実施例は、本発明の好ましい実施態様により、表面にUV吸収性コーティングを持つコンタクトレンズの調製方法を説明する。
Bruker Avance 400 NMR分光計により1H−NMR分光分析を実行した。UV−Vis分光分析には、Perkin Elmer Lambda 25分光計を利用した。アクリル酸は、Fluka(番号017309111)から供給された。
XNorbloc[Mol-%]=100×[3×A芳香族/(7×A1−4×A芳香族)]
[式中、A1は、1.02〜3.15ppmの間のプロトンの面積の積分であり、そしてA芳香族は、6.5〜8.15ppmの間の芳香族シグナルの面積の積分である]にしたがい1H−NMRの積分に基づいて、XNorbloc=8.1[Mol-%]であった。
実施例2で調製したコンタクトレンズをPAA−N20の溶液(1−プロパノールに溶解した0.36g/L PAA−N20、HCOOHで約2.0にpHを調整)に約30分間浸漬し、次にリン酸緩衝生理食塩水(PBS)で濯いでその中に保存した。表面にPAA−N20コーティングを持つ生じたコンタクトレンズのUVスペクトルは、レンズの光透過率がUV−B−及びUV−A帯域(即ち、280nmと380nmの間の帯域)で効率的にブロックされたことを明確に示した(図3を参照のこと)。
青色光吸収剤であるポリ[アクリル酸−コ−メタクリロイルオキシメチル−1−(4−ニトロフェニル)ピロリジン](PAA−L20)の調製
PAA−L20と表される式(3)の青色光吸収性ポリマーは、約XXkDの分子量を有しており、約12.3モル%の青色光吸収性モノマー単位((S)−2−メタクリロイルオキシメチル−1−(4−ニトロフェニル)ピロリジン)を含む。これは、以下に記述される手順により調製した。
X青色[Mol-%]=100×[3×A2/(2×A1−6×A2)]
[式中、A1は、1.0〜2.8ppmの間のプロトンの面積の積分であり、そしてA2は、7.7〜8.4ppmの間の芳香族シグナルの面積の積分である]にしたがい1H−NMRの積分により算出して、X青色=12.3[Mol-%]であった。
鎖延長ポリジメチルシロキサン架橋剤の調製
第1工程において、α,ω−ビス(2−ヒドロキシエトキシプロピル)ポリジメチルシロキサン(Mn=2000、Shin-Etsu、KF-6001a)49.85gをイソホロンジイソシアナート(IPDI)11.1gと無水メチルエチルケトン(MEK)150g中でジラウリン酸ジブチルスズ(DBTDL)0.063gの存在下で反応させることにより、α,ω−ビス(2−ヒドロキシエトキシプロピル)ポリジメチルシロキサンをイソホロンジイソシアナートでキャップした。この反応液を40℃で4.5時間保持して、IPDI−PDMS−IPDIを形成した。第2工程では、α,ω−ビス(2−ヒドロキシエトキシプロピル)ポリジメチルシロキサン(Mn=3000、Shin-Etsu、KF-6002)164.8gと無水MEK 50gとの混合物を、DBTDL更に0.063gを加えたIPDI−PDMS−IPDI溶液に滴下により加えた。反応器を40℃で4.5時間保持して、HO−PDMS−IPDI−PDMS−IPDI−PDMS−OHを形成した。次にMEKを減圧下で除去した。第3工程では、メタクリル酸イソシアナトエチル(IEM)7.77g及びDBTDL更に0.063gの添加により、第3工程で末端ヒドロキシル基をメタクリロイルオキシエチル基でキャップして、IEM−PDMS−IPDI−PDMS−IPDI−PDMS−IEMを形成した。
以下の組成を有するように成分を1−プロパノールに溶解することによってレンズ配合物を調製した:上で調製した約32重量%のCE−PDMSマクロマー、約21重量%のTRIS−Am、約23重量%のDMA、約0.6重量%L−PEG(N−(カルボニル−メトキシポリエチレングリコール−2000)−1,2−ジステアロイル−sn−グリセロ−3−ホスホエタノールアミン、ナトリウム塩)、約1重量%のDarocur 1173、約0.1重量%のビジティント(visitint)(TRIS中の5%銅フタロシアニン青色色素分散液)、約0.8重量%のDMPC(1,2−ジミリストイル−sn−グリセロ−3−ホスホコリン)、約200ppmのH−TEMPO(4−ヒドロキシ−2,2,6,6−テトラメチル−1−ピペリジニルオキシ)、及び22重量%の1−プロパノール。
上で調製したレンズ配合物から、米国特許第7,384,590号及び7,387,759号(図1〜6)の図1〜6に示される成形用型と類似の再利用可能な成形用型(石英雌型半体及びガラス雄型半体)で注型成形によりレンズを調製した。成形用型中のレンズ配合物は、UV照射(13.0mW/cm2)で約24秒間照射した。成形したレンズをMEKで抽出した。
上で調製したコンタクトレンズを、PAA−N20溶液(1−プロパノールに溶解した3.6g/LのPAA−N20、HCOOHでpH≒2.0に調整)を含有する浴に約20分間浸漬し、1−プロパノールで濯いで、次いでPAA−L20溶液(3.6g/L PAA−L20、HCOOHでpH≒2.0に調整)の浴に浸漬した。図4は、得られたコンタクトレンズがUV光を280〜380nmの間の範囲だけでなく、380〜480nmの範囲も、即ち、UV吸収剤クラス1特性を持つレンズに対する基準をはずれても吸収することを示した。これはまた、青色光吸収性レンズの特性を満たした。
Claims (12)
- UV吸収性コンタクトレンズの製造方法であって、
コンタクトレンズを得る工程;
コンタクトレンズを、第1の有機溶媒及び第1の有機溶媒に溶解したUV吸収性ポリマーを含むコーティング溶液に、コンタクトレンズ上にUV吸収性コーティングを形成するのに充分な時間浸漬する工程;からなり、
ここで、UV吸収性ポリマーは、UV吸収性モノマー単位及び少なくとも50モル%のカルボキシル含有モノマー単位を含み、かつ、
UV吸収性ポリマーが、UV吸収性化合物を、少なくとも50モル%のカルボキシル含有モノマー単位を有する前駆体ポリマーと、カップリング反応において反応させることにより得られ、UV吸収性化合物が、式(I)、(II)、(III)、又は(IV):
[式中、
R1、R2及びR3は、相互に独立に、水素、C1−C12直鎖若しくは分岐アルキル基、ハロゲン、C6〜C24アリール基、C7〜C24アルキルアリール基、C7〜C24アリールアルキル、又はC1−C12直鎖若しくは分岐アルコキシ基であり;
L1及びL3は、相互に独立に、共有結合又は−Xa−E1−Xb−E2−Xc−の二価基であり、ここで、Xaは、共有結合、−O−、カルボニル:
、−(RaO)n−の二価基(ここで、Raは、直鎖又は分岐C1−C12−アルキレンであり、そしてnは、1〜10である)、又は下記式:
(ここで、R”は、H又はC1−C8アルキルである)であり、E1及びE2は、相互に独立に、共有結合、−(RaO)n−の二価基(ここで、Ra及びnは、上記と同義である)、下記式:
(ここで、R”は、H又はC1−C8アルキルである)、C1〜C12直鎖若しくは分岐アルキレン二価基、40個以下の炭素原子を持つシクロアルキル二価基、40個以下の炭素原子を持つアルキルシクロアルキル二価基、40個以下の炭素原子を持つアルキルアリール二価基、40個以下の炭素原子を持つアリールアルキレン二価基、又は式:−C(O)L2C(O)−を有するジカルボニル基(ここで、L2は、C1〜C12直鎖若しくは分岐アルキレン二価基又は−(Re1−O)w1−(Re2−O)w2−(Re3−O)w3−であり、ここで、Re1、Re2、及びRe3は、相互に独立に、直鎖又は分岐C1−C4−アルキレンであり、そしてw1、w2及びw3は、相互に独立に、0〜20の数であり、ただし(w1+w2+w3)の合計は、1〜60である)であり、そしてXb及びXcは、相互に独立に、共有結合、カルボニル、下記式:
(ここで、R”は、上記と同義である)であり;そして
Y及びY1は、相互に独立に、アズラクトン基、エポキシ基、イソシアナト基、アジリジン基、又は−NHRのアミノ基(ここで、Rは、水素又はC1−C20非置換若しくは置換の直鎖若しくは分岐アルキル基である)である]により表される、方法。 - 前駆体ポリマーが、(1)アクリル酸又はC1−C12アルキルアクリル酸のホモポリマー;(2)アクリル酸とC1−C12アルキルアクリル酸とのコポリマー;(3)カルボキシル含有ビニルモノマーとアミノ含有ビニルモノマーとのコポリマー(ここで、カルボキシル含有ビニルモノマーは、アクリル酸又はC1−C12アルキルアクリル酸又はこれらの組合せであり、アミノ含有ビニルモノマーは、(メタ)アクリル酸アミノ−C2−C6アルキル、(メタ)アクリル酸C1−C6アルキルアミノ−C2−C6アルキル、アリルアミン、ビニルアミン、アミノ−C2−C6アルキル(メタ)アクリルアミド、C1−C6アルキルアミノ−C2−C6アルキル(メタ)アクリルアミド、及びこれらの組合せよりなる群から選択される);あるいは(4)カルボキシル含有ビニルモノマーと1種以上の親水性ビニルモノマーとのコポリマー(ここで、カルボキシル含有ビニルモノマーは、アクリル酸又はC1−C12アルキルアクリル酸又はこれらの組合せであり、1種以上の親水性ビニルモノマーは、カルボキシル又はアミノ基を含まず、そしてアクリルアミド、メタクリルアミド、N,N−ジメチルアクリルアミド、N,N−ジメチルメタクリルアミド、N−ビニルピロリドン、メタクリル酸N,N−ジメチルアミノエチル、アクリル酸N,N−ジメチルアミノエチル、N,N−ジメチルアミノプロピルメタクリルアミド、N,N−ジメチルアミノプロピルアクリルアミド、メタクリル酸グリセロール、3−アクリロイルアミノ−1−プロパノール、N−ヒドロキシエチルアクリルアミド、N−[トリス(ヒドロキシメチル)メチル]−アクリルアミド、N−メチル−3−メチレン−2−ピロリドン、1−エチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、1−エチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、5−エチル−3−メチレン−2−ピロリドン、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸ヒドロキシプロピル、1500ダルトン以下の重量平均分子量を有するC1−C4−アルコキシポリエチレングリコール(メタ)アクリラート、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、アリルアルコール、ビニルアルコール、及びこれらの組合せよりなる群から選択される)である、請求項1に記載の方法。
- 前駆体ポリマーが、ポリアクリル酸、ポリメタクリル酸、ポリ(C2−C12アルキルアクリル酸)、ポリ(アクリル酸−コ−メタクリル酸)、ポリ[C2−C12アルキルアクリル酸−コ−(メタ)アクリル酸]、ポリ(N,N−2−アクリルアミドグリコール酸)、ポリ[(メタ)アクリル酸−コ−アクリルアミド]、ポリ[(メタ)アクリル酸−コ−ビニルピロリドン]、ポリ[C2−C12アルキルアクリル酸−コ−アクリルアミド]、ポリ[C2−C12アルキルアクリル酸−コ−ビニルピロリドン]、加水分解ポリ[(メタ)アクリル酸−コ−酢酸ビニル]、加水分解ポリ[C2−C12アルキルアクリル酸−コ−酢酸ビニル]、又はこれらの組合せである、請求項1に記載の方法。
- 第1の有機溶媒が、少なくとも60重量%の量でコーティング溶液中に存在し、UV吸収性コーティングを表面に持つコンタクトレンズを、水と多くとも50重量%の第2の有機溶媒との混合物で濯ぐ工程を更に含む、請求項1〜3のいずれか1項に記載の方法。
- 反応性官能基を有する親水性ポリマー又はポリマー材料を、UV吸収性コーティング上に共有結合させることによって、ヒドロゲルコーティングを形成する工程を更に含み、ヒドロゲルコーティングが、UV吸収性コーティング上に、UV吸収性コーティングの1個のカルボキシル基と親水性ポリマー又はポリマー材料の1個の反応性官能基との間にそれぞれ形成される結合を介して共有結合される、請求項1〜4のいずれか1項に記載の方法。
- 親水性ポリマー及び親水性ポリマー材料の反応性官能基が、アゼチジニウム基、エポキシ基、イソシアナト基、アジリジン基、アズラクトン基、アミノ基、カルボキシル基、及びこれらの組合せである、請求項5に記載の方法。
- ヒドロゲルコーティングが、部分架橋ポリマー材料をUV吸収性コーティング上に架橋することにより形成され、部分架橋ポリマー材料が、水溶性であり、そして三次元ネットワーク及びこのネットワーク内の反応性官能基(アゼチジニウム基、エポキシ基、イソシアナト基、アジリジン基、アズラクトン基、アミノ基、カルボキシル基、及びこれらの組合せよりなる群から選択される)を含む、請求項5に記載の方法。
- 部分架橋ポリマー材料が、(i)エピクロロヒドリン官能基化ポリアミン又はポリアミドアミンに由来する20%〜95重量%の第1のポリマー鎖、(ii)アミノ基、カルボキシル基、チオール基、及びこれらの組合せよりなる群から選択される少なくとも1個の反応性官能基を有する少なくとも1種の親水性増強剤に由来する、5%〜80重量%の親水性部分又は第2のポリマー鎖(ここで、親水性部分又は第2のポリマー鎖は、第1のポリマー鎖に、エピクロロヒドリン官能基化ポリアミン又はポリアミドアミンの1個のアゼチジニウム基と、親水性増強剤の1個のアミノ、カルボキシル又はチオール基との間にそれぞれ形成される1個以上の共有結合を介して共有結合している)、並びに(iii)第1のポリマー鎖の一部又は第1のポリマー鎖に共有結合しているペンダント若しくは末端基である、アゼチジニウム基を含む、請求項7に記載の方法。
- 親水性ポリマー材料を共有結合させる工程が、UV吸収性コーティングを表面に持つコンタクトレンズを、密封レンズパッケージ中に部分架橋ポリマー材料を包含するパッケージング溶液中で118℃〜125℃の温度で20〜90分間オートクレーブ処理することにより実施される、請求項8に記載の方法。
- ヒドロゲルコーティングを形成するための親水性ポリマー又は親水性ポリマー材料が、UV吸収性部分を含む、請求項5〜9のいずれか1項に記載の方法。
- UV吸収性コーティングが、更に青色光吸収性ポリマーを含む、請求項1〜10のいずれか1項に記載の方法。
- コンタクトレンズが、90度以下の平均水接触角を有することを特徴とする表面湿潤性を有する、シリコーンヒドロゲルコンタクトレンズである、請求項1〜11のいずれか1項に記載の方法。
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SG11201400228WA (en) | 2014-05-29 |
CN103917899A (zh) | 2014-07-09 |
EP2766750B1 (en) | 2016-02-03 |
JP2014534467A (ja) | 2014-12-18 |
CA2851668C (en) | 2016-08-16 |
US9005700B2 (en) | 2015-04-14 |
HUE029018T2 (en) | 2017-02-28 |
MY164605A (en) | 2018-01-30 |
CN103917899B (zh) | 2018-04-03 |
CA2851668A1 (en) | 2013-04-18 |
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