JP6615349B2 - 両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー - Google Patents
両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー Download PDFInfo
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- JP6615349B2 JP6615349B2 JP2018527978A JP2018527978A JP6615349B2 JP 6615349 B2 JP6615349 B2 JP 6615349B2 JP 2018527978 A JP2018527978 A JP 2018527978A JP 2018527978 A JP2018527978 A JP 2018527978A JP 6615349 B2 JP6615349 B2 JP 6615349B2
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- Prior art keywords
- meth
- vinyl
- lens
- acrylamide
- acrylate
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- -1 methacryloyl groups Chemical group 0.000 claims description 99
- 229920002554 vinyl polymer Polymers 0.000 claims description 90
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 83
- 239000000178 monomer Substances 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 65
- 229920001296 polysiloxane Polymers 0.000 claims description 53
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 50
- 239000000017 hydrogel Substances 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 36
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 36
- 239000000463 material Substances 0.000 claims description 32
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 30
- 230000005855 radiation Effects 0.000 claims description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000004971 Cross linker Substances 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 18
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- 239000002202 Polyethylene glycol Substances 0.000 claims description 15
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 15
- 238000000465 moulding Methods 0.000 claims description 15
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 14
- 230000035699 permeability Effects 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 10
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 9
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 230000002209 hydrophobic effect Effects 0.000 claims description 7
- 239000012633 leachable Substances 0.000 claims description 7
- 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 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 6
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 6
- KYKIFKUTBWKKRE-UHFFFAOYSA-N n-ethenylpropan-2-amine Chemical compound CC(C)NC=C KYKIFKUTBWKKRE-UHFFFAOYSA-N 0.000 claims description 6
- 239000012867 bioactive agent Substances 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- SLEUYUDFUTZVCU-UHFFFAOYSA-N n-[3-[methyl-bis(trimethylsilyloxy)silyl]propyl]prop-2-enamide Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)CCCNC(=O)C=C SLEUYUDFUTZVCU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 claims description 3
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 claims description 3
- UEIPWOFSKAZYJO-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-[2-(2-ethenoxyethoxy)ethoxy]ethane Chemical compound C=COCCOCCOCCOCCOC=C UEIPWOFSKAZYJO-UHFFFAOYSA-N 0.000 claims description 3
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical group OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 claims description 2
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical compound CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 claims description 2
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- RJOLAZNRAQUHFQ-UHFFFAOYSA-N C(C=C)(=O)OCCOCCCOCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C Chemical compound C(C=C)(=O)OCCOCCCOCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C RJOLAZNRAQUHFQ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 claims description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 2
- WRAABIJFUKKEJQ-UHFFFAOYSA-N cyclopentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC1 WRAABIJFUKKEJQ-UHFFFAOYSA-N 0.000 claims description 2
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 claims description 2
- PGRZLADNCDNGTC-UHFFFAOYSA-N trimethyl-(methyl-propyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C PGRZLADNCDNGTC-UHFFFAOYSA-N 0.000 claims description 2
- 101710141544 Allatotropin-related peptide Proteins 0.000 claims 6
- ZTHJQCDAHYOPIK-UHFFFAOYSA-N 3-methylbut-2-en-2-ylbenzene Chemical compound CC(C)=C(C)C1=CC=CC=C1 ZTHJQCDAHYOPIK-UHFFFAOYSA-N 0.000 claims 1
- VYGUBTIWNBFFMQ-UHFFFAOYSA-N [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O Chemical compound [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O VYGUBTIWNBFFMQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- LGJRTURUUIZFIN-UHFFFAOYSA-N n-ethenyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC=C LGJRTURUUIZFIN-UHFFFAOYSA-N 0.000 claims 1
- 125000005375 organosiloxane group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 238000004381 surface treatment Methods 0.000 description 7
- 238000005266 casting Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 238000010546 Norrish type I reaction Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229910000078 germane Inorganic materials 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000002861 polymer material Substances 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
- RLWDBZIHAUEHLO-UHFFFAOYSA-N 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propyl 2-methylprop-2-enoate Chemical compound CC(C)(C)C1=CC(CCCOC(=O)C(=C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O RLWDBZIHAUEHLO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- 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
- 239000007864 aqueous solution Substances 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 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
- 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
- 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
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 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
- 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
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 2
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- PQOSNJHBSNZITJ-UHFFFAOYSA-N 3-methyl-3-heptanol Chemical compound CCCCC(C)(O)CC PQOSNJHBSNZITJ-UHFFFAOYSA-N 0.000 description 2
- JEWXYDDSLPIBBO-UHFFFAOYSA-N 3-methyl-3-octanol Chemical compound CCCCCC(C)(O)CC JEWXYDDSLPIBBO-UHFFFAOYSA-N 0.000 description 2
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 2
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229930186217 Glycolipid Natural products 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
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- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- BEPGHZIEOVULBU-UHFFFAOYSA-N n,n'-diethylpropane-1,3-diamine Chemical compound CCNCCCNCC BEPGHZIEOVULBU-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- XQIPKPDCWQTNJY-UHFFFAOYSA-N n,n-bis[3-[3-[tert-butyl(dimethyl)silyl]propoxy]-2-hydroxypropyl]-2-methylprop-2-enamide Chemical compound CC(C)(C)[Si](C)(C)CCCOCC(O)CN(C(=O)C(=C)C)CC(O)COCCC[Si](C)(C)C(C)(C)C XQIPKPDCWQTNJY-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- AYGYHGXUJBFUJU-UHFFFAOYSA-N n-[2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NCCNC(=O)C=C AYGYHGXUJBFUJU-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
- RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 description 1
- 229960004398 nedocromil Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- FZGSCNQUWMMDIG-UHFFFAOYSA-N phenyl(phosphanyl)methanone Chemical compound PC(=O)C1=CC=CC=C1 FZGSCNQUWMMDIG-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 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
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 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
- 230000035484 reaction time Effects 0.000 description 1
- 229950004535 rebamipide Drugs 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 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
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 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
- 238000001029 thermal curing Methods 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
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- KAKFZMMRKBQABS-UHFFFAOYSA-N trimethyl(silyloxysilyloxy)silane Chemical compound C[Si](C)(C)O[SiH2]O[SiH3] KAKFZMMRKBQABS-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
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/40—Esters of unsaturated alcohols, e.g. allyl (meth)acrylate
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- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
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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
- 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
-
- 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
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- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/06—Crosslinking by radiation
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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。
で表され、式中:X0が、OまたはNR’であり、ここで、R’が、ヒドロゲルまたはC1〜C10アルキルであり、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0.003〜約0.20(好ましくは、約0.005〜約0.080、さらにより好ましくは、約0.01〜約0.030)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)または(3)
のものであり、式中:q1が、0または1であり;n1が、3〜9の整数であり;R7が、C2〜C6置換もしくは非置換アルキレンジラジカルであり;R8およびR9が、互いに独立して、水素またはメチル(好ましくは、メチル)であり;Halが、ClまたはBr(好ましくは、Br)である。
(式中、X0、R2およびR3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ジオルガノシロキサンは、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(4)のヒドロシロキサン含有ポリジオルガノシロキサンは、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。
(例えば、2−ブロモイソブチリルブロミド、2−クロロイソブチリルクロリド、2−ブロモプロピオニルブロミド、2−クロロプロピオニルクロリド)または
(例えば、2−ブロモ酪酸無水物、2−クロロ酪酸無水物、2−ブロモプロピオン酸無水物、2−クロロプロピオン酸無水物)の市販のATRP開始剤と反応されて、式(1)のα,ω−ジメタクリルオキシ末端ポリジオルガノシロキサンビニル架橋剤が得られる。
Claims (20)
- (1)2つの末端メタクリロイル基を有する少なくとも1つの第1のポリジオルガノシロキサンポリマー鎖;および
(2)少なくとも1つの第1の親水性ポリマー鎖;
(3)少なくとも1つの第2の親水性ポリマー鎖;および
(4)少なくとも1つの第2のポリジオルガノシロキサンポリマー鎖(その少なくとも1つの末端が、前記第2の親水性ポリマー鎖に共有結合される)
を含む両親媒性分枝鎖状ポリジオルガノシロキサンマクロマーであって、
前記少なくとも1つの第1のポリジオルガノシロキサンポリマー鎖および前記少なくとも1つの第2のポリジオルガノシロキサンポリマー鎖がいずれも、ATRP開始剤を有する1つの置換基を有する1つ以上のATRP含有シロキサン単位を含むα,ω−ジメタクリロイル末端ポリジオルガノシロキサンビニル架橋剤に由来し、
前記少なくとも1つの第1の親水性ポリマー鎖が、前記少なくとも1つの第1の親水性ポリマー鎖の2つの末端の一方において前記少なくとも1つの第1または第2のポリジオルガノシロキサンポリマー鎖の単一のATRP含有シロキサン単位に共有結合され、前記少なくとも1つの第1の親水性ポリマー鎖の末端の他方において1つの第1の末端基を有し、
前記少なくとも1つの第2の親水性ポリマー鎖が、(a)前記少なくとも1つの第2の親水性ポリマー鎖の末端の一方において前記少なくとも1つの第1のポリジオルガノシロキサンポリマー鎖の単一のATRP含有シロキサン単位に共有結合され、(b)前記少なくとも1つの第2の親水性ポリマー鎖の末端の他方において1つの第2の末端基を有し、(c)前記少なくとも1つの第2のポリジオルガノシロキサンポリマー鎖の末端の一方に共有結合され、
前記第1および第2の末端基が、互いに独立して、(メタ)アクリルオキシ基、(メタ)アクリルオキシ−C2〜C4アルコキシ基、(メタ)アクリルアミド−C2〜C4アルコキシ基、(メタ)アクリルオキシ−C2〜C4アルキルアミノ基、(メタ)アクリルアミド−C2〜C4アルキルアミノ基、C1〜C6置換もしくは非置換アルコキシ基、C2〜C6置換もしくは非置換アルカノイルオキシ基、またはC1〜C6置換もしくは非置換アルキルアミノ基であり、前記第1および第2の親水性ポリマー鎖が、(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、ジメチルアミノエチル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリルアミド、N−ビニル−2−ピロリドン、N−ビニル−N−メチ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−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、ヒドロキシエチル(メタ)アクリレート、ヒドロキシエチル(メタ)アクリルアミド、ヒドロキシプロピル(メタ)アクリルアミド、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、およびそれらの混合物からなる群から選択される少なくとも1つの親水性ビニルモノマーのモノマー単位から構成される、両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー。 - 前記第1および第2の親水性ポリマー鎖が、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、N−ビニル−N−メチルアセトアミド、ヒドロキシエチル(メタ)アクリレート、ヒドロキシエチル(メタ)アクリルアミド、グリセロールメタクリレート(GMA)、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、およびそれらの組合せからなる群から選択される少なくとも1つの親水性ビニルモノマーのモノマー単位から構成される、請求項1に記載の両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー。
- ATRP開始剤を有する1つの置換基を有する1つ以上のATRP含有シロキサン単位を含む前記α,ω−ジメタクリルオキシ末端ポリジオルガノシロキサンビニル架橋剤が、式(1)
で表され、式中:X0が、OまたはNR’であり、ここで、R’が、ヒドロゲルまたはC1〜C10アルキルであり、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、0.003〜0.20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)または(3)
のものであり、式中:q1が、0または1であり;n1が、3〜9の整数であり;R7が、C2〜C6置換もしくは非置換アルキレンジラジカルであり;R8およびR9が、互いに独立して、水素またはメチルであり;Halが、ClまたはBrである、請求項1または2に記載の両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー。 - 式(1)中、ω1/υ1が、0.005〜0.080である、請求項3に記載の両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー。
- 式(2)および(3)中、R8およびR9が、互いに独立して、メチルである、請求項3または4に記載の両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー。
- 式(2)および(3)中、HalがBrである、請求項3〜5のいずれか一項に記載の両親媒性分枝鎖状ポリジオルガノシロキサンマクロマー。
- 請求項1〜6のいずれか一項に記載の両親媒性分枝鎖状ポリジオルガノシロキサンマクロマーの単位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70バーラーの酸素透過性(Dk)、25重量%〜70重量%の含水量、0.20MPa〜1.2MPaの弾性率を有する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、請求項1〜6のいずれか一項に記載の少なくとも1つの両親媒性分枝鎖状ポリジオルガノシロキサンマクロマーおよび少なくとも1つのフリーラジカル開始剤を含む工程と;
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を含み、
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70バーラーの酸素透過性(Dk)、25重量%〜70重量%の含水量、0.2MPa〜1.2MPaの弾性率を有する
方法。 - 前記レンズ形成組成物が、0〜4℃の温度で透明である、請求項8に記載の方法。
- 前記レンズ形成組成物が、シロキサン含有ビニルモノマー、親水性ビニルモノマー、疎水性ビニルモノマー、非シリコーンビニル架橋剤、UV吸収ビニルモノマー、可視性ティント剤、抗菌剤、生物活性剤、浸出性潤滑剤、浸出性涙液安定剤、およびそれらの混合物をさらに含む、請求項8または9に記載の方法。
- 前記レンズ形成組成物が、シロキサン含有ビニルモノマーを含む、請求項8〜10のいずれか一項に記載の方法。
- 前記シロキサン含有ビニルモノマーが、3−(メタ)アクリルオキシ−2−ヒドロキシプロピルオキシ)プロピルビス(トリメチルシロキシ)メチルシラン、3−(メタ)アクリルオキシエトキシプロピルオキシプロピルビス(トリメチルシロキシ)メチルシラン、3−(メタ)アクリルアミドプロピル−ビス(トリメチルシロキシ)メチルシラン、3−N−メチル(メタ)アクリルアミドプロピルビス(トリメチルシロキシ)メチルシラン、様々な分子量のモノ−(メタ)アクリルオキシ末端ポリジメチルシロキサン、様々な分子量のモノ−(メタ)アクリルアミド末端ポリジメチルシロキサン、またはそれらの組合せである、請求項11に記載の方法。
- 前記レンズ形成組成物が、親水性ビニルモノマーを含む、請求項8〜12のいずれか一項に記載の方法。
- 親水性ビニルモノマーが、親水性N−ビニルモノマーである、請求項13に記載の方法。
- 前記親水性N−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14に記載の方法。
- 前記レンズ形成組成物が、非シリコーンビニル架橋剤を含む、請求項8〜15のいずれか一項に記載の方法。
- 前記非シリコーンビニル架橋剤が、テトラ(エチレングリコール)ジ−(メタ)アクリレート、トリ(エチレングリコール)ジ−(メタ)アクリレート、エチレングリコールジ−(メタ)アクリレート、ジ(エチレングリコール)ジ−(メタ)アクリレート、グリセロールジメタクリレート、アリル(メタ)アクリレート、N,N’−メチレンビス(メタ)アクリルアミド、N,N’−エチレンビス(メタ)アクリルアミド、N,N’−ジヒドロキシエチレンビス(メタ)アクリルアミド、イソシアヌル酸トリアリル、テトラエチレングリコールジビニルエーテル、トリエチレングリコールジビニルエーテル、ジエチレングリコールジビニルエーテル、エチレングリコールジビニルエーテル、またはそれらの組合せである、請求項16に記載の方法。
- 前記レンズ形成組成物が、1,2−プロピレングリコール、400ダルトン以下の分子量を有するポリエチレングリコール、またはそれらの混合物に溶解される全ての成分の溶液である、請求項8〜17のいずれか一項に記載の方法。
- 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用ビニルモノマーを含む、請求項8〜17のいずれか一項に記載の方法。
- 前記硬化工程が、熱により行われる、請求項8〜19のいずれか一項に記載の方法。
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