JP6708737B2 - 親水性置換基を有する重合性ポリシロキサン - Google Patents
親水性置換基を有する重合性ポリシロキサン Download PDFInfo
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- JP6708737B2 JP6708737B2 JP2018527765A JP2018527765A JP6708737B2 JP 6708737 B2 JP6708737 B2 JP 6708737B2 JP 2018527765 A JP2018527765 A JP 2018527765A JP 2018527765 A JP2018527765 A JP 2018527765A JP 6708737 B2 JP6708737 B2 JP 6708737B2
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- Prior art keywords
- vinyl
- hydrophilic
- lens
- meth
- silicone hydrogel
- Prior art date
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- -1 Polysiloxane Polymers 0.000 title claims description 92
- 229920001296 polysiloxane Polymers 0.000 title claims description 89
- 229920002554 vinyl polymer Polymers 0.000 claims description 162
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 158
- 239000000178 monomer Substances 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 66
- 239000000017 hydrogel Substances 0.000 claims description 65
- 239000000463 material Substances 0.000 claims description 51
- 239000004971 Cross linker Substances 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 48
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 239000001301 oxygen Substances 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 34
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 27
- 230000035699 permeability Effects 0.000 claims description 27
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 26
- 230000005855 radiation Effects 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 24
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 21
- 238000000465 moulding Methods 0.000 claims description 19
- 239000003431 cross linking reagent Substances 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229920001519 homopolymer Polymers 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- 229920002401 polyacrylamide Polymers 0.000 claims description 10
- 229920001282 polysaccharide Polymers 0.000 claims description 10
- 239000005017 polysaccharide Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 7
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 7
- KYKIFKUTBWKKRE-UHFFFAOYSA-N n-ethenylpropan-2-amine Chemical compound CC(C)NC=C KYKIFKUTBWKKRE-UHFFFAOYSA-N 0.000 claims description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 7
- 229920002125 Sokalan® Polymers 0.000 claims description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 6
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 6
- 239000004584 polyacrylic acid Substances 0.000 claims description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 239000004642 Polyimide Substances 0.000 claims description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
- 150000004676 glycans Chemical class 0.000 claims description 5
- 229920000669 heparin Polymers 0.000 claims description 5
- 229960002897 heparin Drugs 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920001721 polyimide Polymers 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 4
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 3
- VZPULCFQAMRUMH-UHFFFAOYSA-N 1-ethyl-3-methylidenepyrrolidin-2-one Chemical compound CCN1CCC(=C)C1=O VZPULCFQAMRUMH-UHFFFAOYSA-N 0.000 claims description 3
- CXNYYQBHNJHBNH-UHFFFAOYSA-N 1-ethyl-5-methylidenepyrrolidin-2-one Chemical compound CCN1C(=C)CCC1=O CXNYYQBHNJHBNH-UHFFFAOYSA-N 0.000 claims description 3
- AFXKUUDFKHVAGI-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidin-2-one Chemical compound CN1CCC(=C)C1=O AFXKUUDFKHVAGI-UHFFFAOYSA-N 0.000 claims description 3
- ZZDBHIVVDUTWJC-UHFFFAOYSA-N 1-methyl-5-methylidenepyrrolidin-2-one Chemical compound CN1C(=C)CCC1=O ZZDBHIVVDUTWJC-UHFFFAOYSA-N 0.000 claims description 3
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 claims description 3
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 claims description 3
- XVUWMCJNMDQXKX-UHFFFAOYSA-N 5-ethyl-3-methylidenepyrrolidin-2-one Chemical compound CCC1CC(=C)C(=O)N1 XVUWMCJNMDQXKX-UHFFFAOYSA-N 0.000 claims description 3
- VDORPYPVQAFLTR-UHFFFAOYSA-N 5-methyl-3-methylidenepyrrolidin-2-one Chemical compound CC1CC(=C)C(=O)N1 VDORPYPVQAFLTR-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 3
- WRAABIJFUKKEJQ-UHFFFAOYSA-N cyclopentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC1 WRAABIJFUKKEJQ-UHFFFAOYSA-N 0.000 claims description 3
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 17
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 239000004205 dimethyl polysiloxane Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000002953 phosphate buffered saline Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004381 surface treatment Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 210000004087 cornea Anatomy 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 238000010546 Norrish type I reaction Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000003570 air Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- PAKCOSURAUIXFG-UHFFFAOYSA-N 3-prop-2-enoxypropane-1,2-diol Chemical group OCC(O)COCC=C PAKCOSURAUIXFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000012935 Averaging Methods 0.000 description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 3
- 230000010220 ion permeability Effects 0.000 description 3
- 239000012633 leachable Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 2
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- UEIPWOFSKAZYJO-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-[2-(2-ethenoxyethoxy)ethoxy]ethane Chemical compound C=COCCOCCOCCOCCOC=C UEIPWOFSKAZYJO-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 2
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 2
- LPCWIFPJLFCXRS-UHFFFAOYSA-N 1-ethylcyclopentan-1-ol Chemical compound CCC1(O)CCCC1 LPCWIFPJLFCXRS-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-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
- SMCPCQHSVZGAAI-UHFFFAOYSA-N 2-(5-chlorobenzotriazol-2-yl)-6-methoxy-4-prop-2-enylphenol Chemical compound COC1=CC(CC=C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O SMCPCQHSVZGAAI-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 2
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 description 2
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- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 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
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical compound NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 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
- 239000002352 surface water Substances 0.000 description 1
- 230000008961 swelling Effects 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
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- SVTUWEUXLNHYPF-UHFFFAOYSA-N trimethyl-[propyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound CCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C SVTUWEUXLNHYPF-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2210/00—Compositions for preparing hydrogels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Eyeglasses (AREA)
- Dispersion Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
Description
、アリル、ビニル、スチレニル、または他のC=C含有基が挙げられる。
(式中:
υ1が、30〜500の整数であり、ω1が、1〜75の整数であり、ただし、ω1/υ1が、約0.035〜約0.25(好ましくは、約0.040〜約0.18、さらにより好ましくは、約0.045〜約0.18)であり;
X0が、OまたはNR’であり、ここで、R’が、水素またはC1〜C10−アルキルであり;
R1が、水素またはメチルであり;
R2およびR3が、互いに独立して、置換もしくは非置換C2〜C6アルキレン二価基または−R5−O−R6−の二価基であり、ここで、R5およびR6が、互いに独立して、置換もしくは非置換C2〜C6アルキレン二価基であり;
R4が、式(2)
の一価基であり、
q1が、0または1であり;
n1が、2〜4の整数であり;
R7が、水素、メチル、または
の基であり;
R8が、エチルまたは
の基であり;
ただし、R7およびR8の少なくとも1つが、
の基である)
のポリマーである。
(式中、X0、R1、R2、R3、υ1、およびω1が、上に定義されるとおりである)のヒドロシロキサン含有ポリシロキサンは、当業者に公知の任意の方法にしたがって調製される。説明のための例として、式(3)のヒドロシロキサン含有ポリシロキサンは、鎖末端ブロックとしての1,3−ビス[3−(メタ)アクリルオキシプロピル]テトラメチルジシロキサン(など)の存在下でおよび触媒の存在下で、オクタメチルシクロテトラシロキサン(D4)と1,3,5,7−テトラメチルシクロテトラシロキサン(H4)との混合物の重合から調製され得る。D4対H4のモル比を制御することによって、υ1/ω1の所望の値を得ることができる。
(式中:
υ1が、30〜500の整数であり、ω1が、1〜75の整数であり、ただし、ω1/υ1が、約0.035〜約0.25であり;
X0が、OまたはNR’であり、ここで、R’が、水素またはC1〜C10−アルキルであり;
R1が、水素またはメチルであり;
R2およびR3が、互いに独立して、置換もしくは非置換C1〜C10アルキレン二価基または−R5−O−R6−の二価基であり、ここで、R5およびR6が、互いに独立して、置換もしくは非置換C1〜C10アルキレン二価基であり;
R4が、式(2)
の一価基であり、
q1が、0または1であり;
n1が、2〜4の整数であり;
R7が、水素、メチル、または
の基であり;
R8が、エチルまたは
の基であり;
ただし、R7およびR8の少なくとも1つが、
の基である)
のポリマーである、発明1に記載の親水化ポリジオルガノシロキサンビニル架橋剤。
シロキサン含有ビニルモノマーの単位と;
少なくとも1つの親水性ビニルモノマーの単位と;
架橋ポリマー材料に共有結合されていないが、架橋ポリマー材料内に物理的に取り込まれた親水性ポリマーと
を含む架橋ポリマー材料を含むシリコーンヒドロゲルコンタクトレンズであって、
完全に水和されるとき、少なくとも約70バーラーの酸素透過性(Dk)、約25重量%〜約70重量%の含水量、約0.2MPa〜約1.2MPaの弾性率、少なくとも約15秒の水破壊時間、および約90°以下の水接触角を有するシリコーンヒドロゲルコンタクトレンズ。
室温で、および任意であるが好ましくは約0〜約4℃の温度で透明であるレンズ形成組成物を調製する工程であって、レンズ形成組成物が、(a)約5重量%〜約35重量%の、発明1〜9のいずれか1つに記載の親水化ポリジオルガノシロキサンビニル架橋剤、(b)シロキサン含有ビニルモノマー、(c)約30重量%〜約60重量%の少なくとも1つの親水性ビニルモノマー、(d)エチレン性不飽和基を含まない親水性ポリマー、および(e)少なくとも1つのラジカル開始剤を含み、ただし、上に列挙された重合性成分および任意のさらなる重合性成分が合計して100重量%になる工程と;
レンズ形成組成物を成形型に導入する工程であって、成形型が、コンタクトレンズの前面を画定する第1の成形面を有する第1の成形型半部と、コンタクトレンズの後面を画定する第2の成形面を有する第2の成形型半部とを有し、前記第1および第2の成形型半部は、前記第1および第2の成形面の間に空洞が形成されるように互いを受け入れるように構成される工程と;
レンズ成形型中のレンズ形成組成物を熱または化学線により硬化して、シリコーンヒドロゲルコンタクトレンズを形成する工程であって、シリコーンヒドロゲルコンタクトレンズが、少なくとも約70バーラーの酸素透過性(Dk)、約25重量%〜約70重量%の含水量、約0.2MPa〜約1.2MPaの弾性率、少なくとも約15秒の水破壊時間、および約90°以下の水接触角を有する工程と
を含む方法。
酸素透過性測定
規定されない限り、レンズおよびレンズ材料の見掛けの酸素透過性(Dkapp)、見掛けの酸素透過率(Dk/t)、固有の(またはエッジ補正された(edge−corrected))酸素透過性(Dkc)が、米国特許出願公開第2012/0026457A1号明細書(全体が、参照により本明細書に援用される)の実施例1に記載される手順にしたがって決定される。
レンズのイオン透過性が、米国特許第5,760,100号明細書(全体が、参照により本明細書に援用される)に記載される手順にしたがって測定される。以下の実施例において報告されるイオン透過性の値は、対照材料としてのレンズ材料、Alsaconに対する相対イオノフラックス拡散係数(D/Dref)である。Alsaconは、0.314×10−3mm2/分のイオノフラックス拡散係数を有する。
レンズの潤滑性が、0〜4の摩擦評価尺度でレンズ表面の滑りやすさを定性的に特性評価する指感触(finger−felt)潤滑性試験を使用することによって評価される。摩擦評価が高いほど、滑りやすさ(または潤滑性)が低い。
コンタクトレンズにおける水接触角(WCA)は、コンタクトレンズの表面湿潤性の一般的な尺度である。特に、低い水接触角は、より湿潤性の表面に対応する。コンタクトレンズの平均接触角(液滴)は、AST,Inc.(Boston,Massachusettsに所在)製のVCA 2500 XE接触角測定デバイスを用いて測定される。この機器は、前進接触角(θa)または後退接触角(θr)または液滴(静的)接触角を測定することが可能である。規定されない限り、水接触角は、液滴(静的)接触角である。測定は、十分に水和されたコンタクトレンズにおいて、以下のように拭き取り乾燥(blot−drying)した直後に行われる。コンタクトレンズを、バイアルから取り出し、レンズ表面から緩く結合された包装添加剤を除去するために、約200mlの新鮮な脱イオン水で3回洗浄する。次に、レンズを、糸くずの出ない清潔な布(Alpha Wipe TX1009)の上に置き、よく拭き取って、表面の水を除去し、接触角測定台に取り付け、乾燥空気を吹き付けて乾燥させ、最後に、液滴接触角を、製造業者によって提供されるソフトウェアを用いて自動的に測定する。接触角を測定するのに使用される脱イオン水は、18MΩcmを超える抵抗率を有し、使用される液滴体積は2μlである。典型的に、コーティングされていないシリコーンヒドロゲルレンズ(オートクレーブ後)は、約120°の液滴接触角を有する。ピンセットおよび台を、イソプロパノールでよく洗浄し、コンタクトレンズと接触させる前に脱イオン水ですすぐ。
レンズ(オートクレーブ後)の表面親水性が、水膜がレンズ表面で壊れ始めるのに必要な時間を決定することによって評価される。簡潔には、レンズをバイアルから取り出し、それぞれ30分間の少なくとも2回のすすぎのためにPBS(リン酸緩衝生理食塩水)に入れ、次に、レンズ表面から緩く結合された包装添加剤を除去するために、新鮮なPBSに移す。レンズを溶液から取り出し、明るい光源に対して保持する。水膜が壊れて(脱水)、下にあるレンズ材料が露出するのに必要な時間を視覚的に観察する。コーティングされていないレンズは、典型的に、PBSから取り出すと直ぐに壊れ、0秒のWBUTを割り当てられる。10秒以上のWBUTを示すレンズは、親水性表面を有すると見なされ、眼における十分な湿潤性(涙液膜を支持する能力)を示すことが予測される。
レンズを、20秒間にわたってRENU(登録商標)多目的レンズケア溶液(または別の多目的レンズケア溶液)とともに(使い捨ての粉なしゴム手袋を着用した)指で擦り、次に、生理食塩水ですすぐ。上記の手順を、所与の回数、例えば、1〜30回(すなわち、洗浄および浸漬サイクルを模倣する指擦り試験の反復回数)繰り返す。
297.9gのオクタメチルシクロテトラシロキサン(分子量296.62)、12.0gの1,3,5,7−テトラメチルシクロテトラシロキサン(分子量240.51)、9.7gの1,3−ビス(3−メタクリルオキシプロピル)テトラメチルジシロキサン(分子量386.63)、および0.9gのトリフルオロメタンスルホン酸(分子量150.08)を、500mLの丸底フラスコ中で秤量する。反応を35℃で24時間行った後、170mLの0.5%の炭酸水素ナトリウムを加える。収集された有機部分を、脱イオン水(サイクル当たり170mL)で5回さらに抽出する。無水MgSO4を、収集された有機溶液に加えた後、約350mLのさらなるCHCl3を加え、次に、溶液を一晩撹拌する。ろ過の後、溶媒を、ロータリーエバポレータ(Rotovap)、続いて高真空によって除去する。102gの最終生成物(前駆体)が得られる。
小型の反応器を、加熱器および乾燥管付きの空気冷却機に連結する。21gのトルエン、15gの上記の前駆体、および5.03gの3−アリルオキシ−1,2−プロパンジオールを反応器に加える。溶液温度が30℃で安定した後、152μLのカールシュテット触媒(キシレン中2Pt%)を加える。2時間後、IRに基づいて100%のSi−Hの転化が達成される。次に、溶液をフラスコに移し、ロータリーエバポレータ(Rotovop)を用いて濃縮した後、アセトニトリル/水混合物(75/25)中で3回沈殿させる。ロータリーエバポレータ(Rotovop)、続いて高真空による溶媒の除去の後、12gの濁った液体が得られた。
Claims (20)
- (1)
(i)ジメチルシロキサン単位;及び
(ii)親水化シロキサン単位、
を含むポリジオルガノシロキサンポリマー鎖であって、
前記親水化シロキサン単位のそれぞれが、
1つのメチル置換基;及び
少なくとも2つのカルボキシ基を有する1つの一価C10〜C50有機置換基;を有し、
前記ジメチルシロキサン単位に対する、前記親水化シロキサン単位のモル比が、約0.035〜約0.25である、
ポリジオルガノシロキサンポリマー鎖と;
(2)2つの末端(メタ)アクリロイル基と;
を含み、
少なくとも約3000ダルトンの平均分子量を有する、
親水化ポリジオルガノシロキサンビニル架橋剤。 - 前記親水化ポリジオルガノシロキサンビニル架橋剤が、式(1)
(式中:
υ1が、30〜500の整数であり、ω1が、1〜75の整数であり、ただし、ω1/υ1が、約0.035〜約0.25であり;
X0が、OまたはNR’であり、ここで、R’が、水素またはC1〜C10−アルキルであり;
R1が、水素またはメチルであり;
R2およびR3が、互いに独立して、置換もしくは非置換C1〜C10アルキレン二価基または−R5−O−R6−の二価基であり、ここで、R5およびR6が、互いに独立して、置換もしくは非置換C1〜C10アルキレン二価基であり;
R4が、式(2)
の一価基であり、
q1が、0または1であり;
n1が、2〜4の整数であり;
R7が、水素、メチル、または
の基であり;
R8が、エチルまたは
の基であり;
ただし、R7およびR8の少なくとも1つが、
の基である)のポリマーである、請求項1に記載の親水化ポリジオルガノシロキサンビニル架橋剤。 - 請求項1〜5のいずれか一項に記載の親水化ポリジオルガノシロキサンビニル架橋剤の単位と;
シロキサン含有ビニルモノマーの単位と;
少なくとも1つの親水性ビニルモノマーの単位と;
前記架橋ポリマー材料に共有結合されていないが、前記架橋ポリマー材料内に物理的に取り込まれた親水性ポリマーと;
を含む架橋ポリマー材料を含むシリコーンヒドロゲルコンタクトレンズであって、
完全に水和されるとき、少なくとも約70バーラーの酸素透過性(Dk)、約25重量%〜約70重量%の含水量、約0.2MPa〜約1.2MPaの弾性率、少なくとも約15秒の水破壊時間、および約90°以下の水接触角を有するシリコーンヒドロゲルコンタクトレンズ。 - 前記親水性ビニルモノマーが、N−ビニルピロリドン、N,N−ジメチル(メタ)アクリルアミド、(メタ)アクリルアミド、ヒドロキシルエチル(メタ)アクリルアミド、ヒドロキシエチル(メタ)アクリレート、グリセロールメタクリレート(GMA)、ポリエチレングリコール(メタ)アクリレート、最大で1500の数平均分子量を有するポリエチレングリコールC1〜C4−アルキルエーテル(メタ)アクリレート、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、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、エチルアクリル酸、またはそれらの組合せである、請求項6に記載のシリコーンヒドロゲルコンタクトレンズ。
- 前記親水性ビニルモノマーが、N−ビニルピロリドン、N−ビニル−N−メチルアセトアミド、またはそれらの組合せである、請求項7に記載のシリコーンヒドロゲルコンタクトレンズ。
- 前記架橋ポリマー材料が、シリコーンを含まない疎水性ビニルモノマーの単位、非シリコーンビニル架橋剤の単位、UV吸収ビニルモノマーの単位、またはそれらの組合せをさらに含む、請求項6〜8のいずれか一項に記載のシリコーンヒドロゲルコンタクトレンズ。
- 前記親水性ポリマーが、ポリビニルアルコール、ポリアミド、ポリイミド、ポリラクトン、N−ビニルピロリドンのホモポリマー、N−ビニルピロリドンと1つ以上の親水性ビニルコモノマーとのコポリマー、N−ビニル−N−メチルアセトアミドのホモポリマー、N−ビニル−N−メチルアセトアミドと1つ以上の親水性ビニルコモノマーとのコポリマー、ポリアクリルアミド、ポリメタクリルアミド、アクリルアミドと1つ以上の親水性ビニルモノマーとのコポリマー、メタクリルアミドと1つ以上の親水性ビニルモノマーとのコポリマー、ポリエチレンオキシド、ポリ−N−N−ジメチルアクリルアミド、ポリアクリル酸、ポリ(2−エチルオキサゾリン)、ヘパリン多糖類、多糖類、またはそれらの混合物である、請求項6〜9のいずれか一項に記載のシリコーンヒドロゲルコンタクトレン
ズ。 - 前記親水性ポリマーの数平均分子量Mwが、5,000〜500,000ダルトンである、請求項10に記載のシリコーンヒドロゲルコンタクトレンズ。
- 前記親水性ポリマーが、ポリビニルピロリドン、ポリ(N−ビニル−N−メチルアセトアミド)、ポリアクリルアミド、ポリ−N−N−ジメチルアクリルアミド、またはそれらの組合せである、請求項10または11に記載のシリコーンヒドロゲルコンタクトレンズ。
- シリコーンヒドロゲルコンタクトレンズを製造するための方法であって、
室温で、および任意選択であるが好ましくは約0〜約4℃の温度で透明であるレンズ形成組成物を調製する工程であって、前記レンズ形成組成物が、
(a)約5重量%〜約35重量%の、請求項1〜5のいずれか一項に記載の親水化ポリジオルガノシロキサンビニル架橋剤、
(b)シロキサン含有ビニルモノマー、
(c)約30重量%〜約60重量%の少
なくとも1つの親水性ビニルモノマー、
(d)エチレン性不飽和基を含まない親水性ポリマー、および
(e)少なくとも1つのフリーラジカル開始剤を含み、
ただし、上に列挙された重合性成分および任意のさらなる重合性成分が合計して100重量%になる工程と;
前記レンズ形成組成物を成形型に導入する工程であって、前記成形型が、コンタクトレンズの前面を画定する第1の成形面を有する第1の成形型半部と、前記コンタクトレンズの後面を画定する第2の成形面を有する第2の成形型半部とを有し、前記第1および第2の成形型半部は、前記第1および第2の成形面の間に空洞が形成されるように互いを受け入れるように構成される工程と;
前記レンズ成形型中の前記レンズ形成組成物を熱または化学線により硬化して、シリコーンヒドロゲルコンタクトレンズを形成する工程であって、前記シリコーンヒドロゲルコンタクトレンズが、少なくとも約70バーラーの酸素透過性(Dk)、約25重量%〜約70重量%の含水量、約0.2MPa〜約1.2MPaの弾性率、少なくとも約15秒の水破壊時間、および約90°以下の水接触角を有する工程と、を含む方法。 - 前記レンズ形成組成物が、無溶媒液体混合物であり、C1〜C10アルキルメタクリレート、イソボルニルメタクリレート、イソボルニルアクリレート、シクロペンチルメタクリレート、シクロペンチルアクリレート、シクロヘキシルメタクリレート、シクロヘキシルアクリレート、スチレン、2,4,6−トリメチルスチレン(TMS)、およびt−ブチルスチレン(TBS)、およびそれらの組合せからなる群から選択される混合ビニルモノマー(好ましくは、前記混合ビニルモノマーは、メチルメタクリレートである)を含む、請求項13に記載の方法。
- 前記レンズ形成組成物が、有機溶媒を含む、請求項13に記載の方法。
- 前記レンズ形成組成物中に存在する全てのシリコーン含有重合性成分の総量は、約65%以下である、請求項13〜15のいずれか一項に記載の方法。
- 前記親水性ビニルモノマーが、親水性N−ビニルモノマーであり、好ましくは、N−ビニルピロリドン、N−ビニル−N−メチルアセトアミド、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、またはそれらの組合せであり、さらにより好ましくは、N−ビニルピロリドン、N−ビニル−N−メチルアセトアミド、またはそれらの組合せである、請求項13〜16のいずれか一項に記載の方法。
- 前記親水性ポリマーが、ポリビニルアルコール、ポリアミド、ポリイミド、ポリラクトン、N−ビニルピロリドンのホモポリマー、N−ビニルピロリドンと1つ以上の親水性ビニルコモノマーとのコポリマー、N−ビニル−N−メチルアセトアミドのホモポリマー、N−ビニル−N−メチルアセトアミドと1つ以上の親水性ビニルコモノマーとのコポリマー、ポリアクリルアミド、ポリメタクリルアミド、アクリルアミドと1つ以上の親水性ビニルモノマーとのコポリマー、メタクリルアミドと1つ以上の親水性ビニルモノマーとのコポリマー、ポリエチレンオキシド、ポリ−N−N−ジメチルアクリルアミド、ポリアクリル酸、ポリ(2−エチルオキサゾリン)、ヘパリン多糖類、多糖類、またはそれらの混合物である、請求項13〜17のいずれか一項に記載の方法。
- 前記親水性ポリマーの数平均分子量Mwが、5,000〜500,000ダルトンである、請求項17に記載の方法。
- 前記親水性ポリマーが、ポリビニルピロリドン、ポリ(N−ビニル−N−メチルアセトアミド)、ポリアクリルアミド、ポリ−N−N−ジメチルアクリルアミド、またはそれらの組合せである、請求項17または18に記載の方法。
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