JP2007269939A - Gas-permeable material - Google Patents
Gas-permeable material Download PDFInfo
- Publication number
- JP2007269939A JP2007269939A JP2006096283A JP2006096283A JP2007269939A JP 2007269939 A JP2007269939 A JP 2007269939A JP 2006096283 A JP2006096283 A JP 2006096283A JP 2006096283 A JP2006096283 A JP 2006096283A JP 2007269939 A JP2007269939 A JP 2007269939A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- derivatives
- acrylate
- gas
- fumarate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 44
- 230000035699 permeability Effects 0.000 claims abstract description 32
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- -1 vinyl lactam Chemical class 0.000 claims description 104
- 239000007789 gas Substances 0.000 claims description 50
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 17
- 150000002291 germanium compounds Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- 239000012528 membrane Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 150000003926 acrylamides Chemical class 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000956 alloy Substances 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 claims 2
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000000704 physical effect Effects 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052732 germanium Inorganic materials 0.000 abstract 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 84
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 24
- 239000007983 Tris buffer Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 229920001296 polysiloxane Polymers 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 8
- 150000003440 styrenes Chemical class 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- MOGDWMJYYZNXJY-UHFFFAOYSA-N trimethyl(2-phenylethenyl)germane Chemical compound C[Ge](C)(C)C=CC1=CC=CC=C1 MOGDWMJYYZNXJY-UHFFFAOYSA-N 0.000 description 6
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 5
- AHNYHYYIECFEQY-UHFFFAOYSA-N 2-phenylethenylsilicon Chemical compound [Si]C=CC1=CC=CC=C1 AHNYHYYIECFEQY-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- OVIMYSKXYFPHIW-UHFFFAOYSA-N [GeH3]C=CC1=CC=CC=C1 Chemical compound [GeH3]C=CC1=CC=CC=C1 OVIMYSKXYFPHIW-UHFFFAOYSA-N 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 238000012258 culturing Methods 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 229920003192 poly(bis maleimide) Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- DSTUKHPLWATFCG-UHFFFAOYSA-N (2-benzoylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C(=O)C1=CC=CC=C1 DSTUKHPLWATFCG-UHFFFAOYSA-N 0.000 description 3
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 210000004087 cornea Anatomy 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- SOEDHYUFNWMILE-UHFFFAOYSA-N naphthalen-1-yl prop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C=C)=CC=CC2=C1 SOEDHYUFNWMILE-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- OPGGGHBKSIDFNA-VOTSOKGWSA-N (E)-4-[[dimethyl(trimethylsilyloxy)silyl]methoxy]-4-oxobut-2-enoic acid Chemical compound C[Si](C)(C)O[Si](C)(C)COC(=O)\C=C\C(O)=O OPGGGHBKSIDFNA-VOTSOKGWSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- KLQVCADYSBUVAV-UHFFFAOYSA-N 4-[(2,4-dimethylphenyl)diazenyl]-5-methyl-2-phenyl-4h-pyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=C(C)C=C1C KLQVCADYSBUVAV-UHFFFAOYSA-N 0.000 description 2
- IOORFPYTYAAIKH-UHFFFAOYSA-N 6-silylhexane-1,2,3-triol Chemical compound [SiH3]CCCC(O)C(O)CO IOORFPYTYAAIKH-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-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
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 2
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- FIONWRDVKJFHRC-UHFFFAOYSA-N trimethyl(2-phenylethenyl)silane Chemical compound C[Si](C)(C)C=CC1=CC=CC=C1 FIONWRDVKJFHRC-UHFFFAOYSA-N 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- VBQMOUFTQANISV-UHFFFAOYSA-N (2-butylphenyl)-phenylmethanone Chemical compound CCCCC1=CC=CC=C1C(=O)C1=CC=CC=C1 VBQMOUFTQANISV-UHFFFAOYSA-N 0.000 description 1
- AOJDGDCOHYXBHK-BQYQJAHWSA-N (E)-4-[3-[dimethyl(trimethylsilyloxy)silyl]propoxy]-4-oxobut-2-enoic acid Chemical compound C[Si](C)(C)O[Si](C)(C)CCCOC(=O)\C=C\C(O)=O AOJDGDCOHYXBHK-BQYQJAHWSA-N 0.000 description 1
- BVMFCKRIQQNYND-AATRIKPKSA-N (E)-4-oxo-4-(3-trimethylsilylpropoxy)but-2-enoic acid Chemical compound C[Si](C)(C)CCCOC(=O)\C=C\C(O)=O BVMFCKRIQQNYND-AATRIKPKSA-N 0.000 description 1
- BIFSSOLYGSDYJQ-SNAWJCMRSA-N (E)-4-oxo-4-(trimethylsilylmethoxy)but-2-enoic acid Chemical compound C[Si](C)(C)COC(=O)\C=C\C(O)=O BIFSSOLYGSDYJQ-SNAWJCMRSA-N 0.000 description 1
- CRCTZWNJRMZUIO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical group FC(F)(F)[CH]C(F)(F)F CRCTZWNJRMZUIO-UHFFFAOYSA-N 0.000 description 1
- SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical compound FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 description 1
- IIIXIRLDHADRIR-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(1,2,2-tribromoethenyl)benzene Chemical compound BrC(Br)=C(Br)C1=C(Br)C(Br)=C(Br)C(Br)=C1Br IIIXIRLDHADRIR-UHFFFAOYSA-N 0.000 description 1
- GZQZKLFXWPAMFW-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(1,2,2-trifluoroethenyl)benzene Chemical compound FC(F)=C(F)C1=C(F)C(F)=C(F)C(F)=C1F GZQZKLFXWPAMFW-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- FUXLBXOGNJUVFH-UHFFFAOYSA-N 1-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(=O)C=C1C1=CC=CC=C1 FUXLBXOGNJUVFH-UHFFFAOYSA-N 0.000 description 1
- KBJCVJSVRCLNKT-VOTSOKGWSA-N 1-O-[[dimethyl(trimethylsilyloxy)silyl]methyl] 4-O-(1,1,1,3,3,3-hexafluoropropan-2-yl) (E)-but-2-enedioate Chemical compound C[Si](C)(C)O[Si](C)(C)COC(=O)\C=C\C(=O)OC(C(F)(F)F)C(F)(F)F KBJCVJSVRCLNKT-VOTSOKGWSA-N 0.000 description 1
- PUKLCKVOVCZYKF-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O PUKLCKVOVCZYKF-UHFFFAOYSA-N 0.000 description 1
- FTFULVSESZARHS-UHFFFAOYSA-N 1-[2-chloro-4-[[3-chloro-4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(N2C(C=CC2=O)=O)C(Cl)=CC=1CC(C=C1Cl)=CC=C1N1C(=O)C=CC1=O FTFULVSESZARHS-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- DQGGHYHHYCKIMR-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]pyrrole-2,5-dione Chemical compound FC(F)(F)C1=CC=CC(N2C(C=CC2=O)=O)=C1 DQGGHYHHYCKIMR-UHFFFAOYSA-N 0.000 description 1
- AQGZJQNZNONGKY-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2C(C=CC2=O)=O)C=C1 AQGZJQNZNONGKY-UHFFFAOYSA-N 0.000 description 1
- PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- SXTILEHINBCKSS-UHFFFAOYSA-N 1-chloro-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(Cl)C(=O)C=C1C1=CC=CC=C1 SXTILEHINBCKSS-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
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- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- ZLLVQELIBCDLLZ-UHFFFAOYSA-N dimethyl-(2-phenylethenyl)-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)C=CC1=CC=CC=C1 ZLLVQELIBCDLLZ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- QOLYUNMUZIXQSB-UHFFFAOYSA-N diundecyl benzene-1,2-dicarboxylate;phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O.CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCC QOLYUNMUZIXQSB-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UJKWLAZYSLJTKA-UHFFFAOYSA-N edma Chemical compound O1CCOC2=CC(CC(C)NC)=CC=C21 UJKWLAZYSLJTKA-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 125000003800 germyl group Chemical group [H][Ge]([H])([H])[*] 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- FVFMYDCFRDYUCF-UHFFFAOYSA-N methyl(2-phenylethenyl)silane Chemical compound C[SiH2]C=CC1=CC=CC=C1 FVFMYDCFRDYUCF-UHFFFAOYSA-N 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- SDYRIBONPHEWCT-UHFFFAOYSA-N n,n-dimethyl-2-phenylethenamine Chemical compound CN(C)C=CC1=CC=CC=C1 SDYRIBONPHEWCT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000005401 siloxanyl group Chemical group 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940099373 sudan iii Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- JNGJFUPIRZYCBP-UHFFFAOYSA-N tetrakis(ethenylsulfanyl)germane Chemical compound C=CS[Ge](SC=C)(SC=C)SC=C JNGJFUPIRZYCBP-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- CDSLJYFOIXIQTC-UHFFFAOYSA-N triethyl(2-phenylethenyl)germane Chemical compound CC[Ge](CC)(CC)C=CC1=CC=CC=C1 CDSLJYFOIXIQTC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- OQKPOMJPLRKKFI-UHFFFAOYSA-N trimethyl(2-phenylethenylsilyloxy)silane Chemical compound C[Si](C)(C)O[SiH2]C=Cc1ccccc1 OQKPOMJPLRKKFI-UHFFFAOYSA-N 0.000 description 1
- AZNCEYAYEAKZTO-UHFFFAOYSA-N trimethyl(3-phenylprop-2-enyl)germane Chemical compound C[Ge](C)(C)CC=CC1=CC=CC=C1 AZNCEYAYEAKZTO-UHFFFAOYSA-N 0.000 description 1
- XGDIURLLECDZIR-UHFFFAOYSA-N trimethyl(4-phenylbut-3-enyl)germane Chemical compound C[Ge](C)(C)CCC=CC1=CC=CC=C1 XGDIURLLECDZIR-UHFFFAOYSA-N 0.000 description 1
- GHKGONFTOQNBDW-UHFFFAOYSA-N trimethyl(5-phenylpent-4-enyl)germane Chemical compound C[Ge](C)(C)CCCC=CC1=CC=CC=C1 GHKGONFTOQNBDW-UHFFFAOYSA-N 0.000 description 1
- UEPYASQNDSOKDY-UHFFFAOYSA-N trimethyl-(1-methylsilyl-2-phenyl-2-trimethylsilyloxyethenoxy)silane Chemical compound C[SiH2]C(O[Si](C)(C)C)=C(O[Si](C)(C)C)c1ccccc1 UEPYASQNDSOKDY-UHFFFAOYSA-N 0.000 description 1
- HBYSEOWYFDPNQA-UHFFFAOYSA-N trimethyl-(2-phenyl-1-silyloxysilyloxysilyloxysilylethenoxy)silane Chemical compound C[Si](C)(C)OC([SiH2]O[SiH2]O[SiH2]O[SiH3])=Cc1ccccc1 HBYSEOWYFDPNQA-UHFFFAOYSA-N 0.000 description 1
- VWYKMPSIISPSAM-UHFFFAOYSA-N trimethylgermylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Ge](C)(C)C VWYKMPSIISPSAM-UHFFFAOYSA-N 0.000 description 1
- VGOXVARSERTCRY-UHFFFAOYSA-N trimethylsilylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)C VGOXVARSERTCRY-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 125000005387 trisiloxy group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
- C12M23/00—Constructional details, e.g. recesses, hinges
- C12M23/24—Gas permeable parts
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
- C12M23/00—Constructional details, e.g. recesses, hinges
- C12M23/20—Material Coatings
Landscapes
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Microbiology (AREA)
- Sustainable Development (AREA)
- Biochemistry (AREA)
- Clinical Laboratory Science (AREA)
- Eyeglasses (AREA)
- Immunology (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本発明は、すぐれたガス透過性を有するガス透過性材料に関する。さらに詳しくは、すぐれたガス透過性を有するだけではなく、屈折率、硬度、強度等の機械的特性、寸法安定性にすぐれる酸素透過性材料に関する。 The present invention relates to a gas permeable material having excellent gas permeability. More specifically, the present invention relates to an oxygen-permeable material that has not only excellent gas permeability but also excellent mechanical properties such as refractive index, hardness, and strength, and dimensional stability.
一般的に、産業界におけるガス透過性材料の用途として、
別途、産業界におけるガス透過性材料の用途の一つとして、コンタクトレンズが挙げられる。コンタクトレンズは角膜に直接接触して使用される医療機器であり、角膜に酸素を供給する必要があるため、主として酸素透過性に重点をおいて開発されたガス透過性材料である。酸素透過性コンタクトレンズにおいては、従来、シリコーン成分を主成分としており、その他の成分として、耐汚染性、強度、水濡れ性などを付与する目的で、それぞれの目標性能に合わせたモノマーが共重合成分として選択されている。 Separately, one of the uses of gas permeable materials in industry is contact lenses. A contact lens is a medical device that is used in direct contact with the cornea and needs to supply oxygen to the cornea. Therefore, the contact lens is a gas-permeable material developed mainly with an emphasis on oxygen permeability. Conventionally, oxygen-permeable contact lenses have a silicone component as the main component, and other components are copolymerized with monomers tailored to the target performance for the purpose of imparting contamination resistance, strength, water wettability, etc. Selected as an ingredient.
近年、眼用レンズなどの光学材料においては高屈折率化・高強度化によるレンズ厚みの薄型化が求められており、特にコンタクトレンズ材料においては透明性、高い屈折率、高い硬度、すぐれた機械的特性を維持しつつ、高い酸素透過性が求められている。 In recent years, optical materials such as ophthalmic lenses have been required to reduce the lens thickness by increasing the refractive index and the strength, and in particular, contact lens materials have transparency, high refractive index, high hardness, and excellent machinery. High oxygen permeability is required while maintaining the desired characteristics.
シリコーン成分は酸素透過性を向上させる効果があるため、シリコーン含有量を増加させると酸素透過性は向上する。しかし、その一方で屈折率や硬度、強度等の機械的性質が低下するという問題が存在する。 Since the silicone component has the effect of improving oxygen permeability, increasing the silicone content improves oxygen permeability. However, on the other hand, there is a problem that mechanical properties such as refractive index, hardness and strength are lowered.
この点を改善するため、具体的にコンタクトレンズを例に取り上げるならば、当初、ガス透過性を向上させるためにシリコーン系（メタ）アクリレートが用いられていたが、ポリマー組成中のシリコーン含有量を増やすことによってガス透過性は向上するものの、一方で屈折率や硬度、強度等の機械的性質が低下してしまうという問題が存在した。この問題を解決するため、
本発明では、すぐれたガス透過性を有するガス透過性材料を提供することを目的とする。さらに詳しくは、高い屈折率、高い硬度を有する物性バランスのとれたガス透過性材料を提供することを目的とする。 An object of the present invention is to provide a gas permeable material having excellent gas permeability. More specifically, an object of the present invention is to provide a gas permeable material having a high refractive index and a high hardness and balanced physical properties.
本発明は、一般式（Ｉ）で表される有機ゲルマニウム化合物を含んでなるガス透過性材料に関する。 The present invention relates to a gas permeable material comprising an organic germanium compound represented by the general formula (I).
式中、R1, R2, R3は、それぞれ独立して、炭素数1〜6の直鎖状または分枝状のアルキル基、R4はHまたはCH3、R5は炭素数1〜6の直鎖状または分枝状のアルキレン基、R6は直接結合、または炭素数1〜6の直鎖状または分枝状のアルキレン基を示す。 In the formula, R 1 , R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms, R 4 is H or CH 3 , and R 5 is 1 to C carbon atoms. 6 linear or branched alkylene groups, R 6 represents a direct bond, or a linear or branched alkylene group having 1 to 6 carbon atoms.
一般式（Ｉ）表される重合性有機ゲルマニウム化合物、および前記重合性有機ゲルマニウム化合物と共重合可能なモノマーとを、重合して得られる共重合体を含むガス透過性材料に関する。 The present invention relates to a gas permeable material containing a copolymer obtained by polymerizing a polymerizable organic germanium compound represented by the general formula (I) and a monomer copolymerizable with the polymerizable organic germanium compound.
前記共重合可能なモノマーは、（メタ）アクリレート誘導体、スチレン誘導体、フマレート誘導体、（メタ）アクリルアミド誘導体、ビニルラクタム誘導体、マレイミド誘導体、及び無水マレイン酸の群から選ばれる一種または二種以上であることが好ましい。 The copolymerizable monomer is one or more selected from the group consisting of (meth) acrylate derivatives, styrene derivatives, fumarate derivatives, (meth) acrylamide derivatives, vinyl lactam derivatives, maleimide derivatives, and maleic anhydride. Is preferred.
一般式（Ｉ）で表される重合性有機ゲルマニウム化合物を含むポリマー、および前記重合性有機ゲルマニウム化合物を含むポリマーと相溶可能なポリマーとを、相溶させて得られうるポリマーアロイからなるガス透過性材料に関する。 Gas permeation comprising a polymer containing a polymerizable organic germanium compound represented by the general formula (I) and a polymer alloy obtained by compatibilizing a polymer compatible with the polymer containing the polymerizable organic germanium compound. Related to sex materials.
前記相溶可能なポリマーが、（メタ）アクリレート誘導体、スチレン誘導体、フマレート誘導体、（メタ）アクリルアミド誘導体、ビニルラクタム誘導体、マレイミド誘導体、及び無水マレイン酸の群から選ばれる一種または二種以上であることが好ましい。 The compatible polymer is one or more selected from the group consisting of (meth) acrylate derivatives, styrene derivatives, fumarate derivatives, (meth) acrylamide derivatives, vinyl lactam derivatives, maleimide derivatives, and maleic anhydride. Is preferred.
本材料はガス透過性の中でも、特に酸素透過性に着目して用いられることが好ましい。 Among the gas permeability, this material is preferably used with particular attention to oxygen permeability.
前記材料はガス透過膜に用いられることが好ましい。 The material is preferably used for a gas permeable membrane.
前記材料は細胞を培養する培養容器に用いられることが好ましい。 The material is preferably used in a culture vessel for culturing cells.
前記材料は眼用レンズに用いられることが好ましい。 The material is preferably used for an ophthalmic lens.
前記材料は眼用レンズの中でも、特にコンタクトレンズに用いられることが好ましい。 Among the ophthalmic lenses, the material is particularly preferably used for contact lenses.
本発明のガス透過性の材料は、ガスの透過性が高いという効果を有する。さらに高い硬度、高い屈折率にもすぐれているという効果を有し、物性バランスにすぐれることから、従来のガス透過性の材料では、使用困難であった用途、分野でも使用可能となる新規なガス透過性材料である。それだけでなく、従来使用されていた用途、分野においても従来品に比べ、優れた製品を得ることが可能となる。 The gas-permeable material of the present invention has an effect of high gas permeability. In addition, it has the effect of being excellent in high hardness and high refractive index, and has a good balance of physical properties. Therefore, it is a novel material that can be used in applications and fields that are difficult to use with conventional gas-permeable materials. It is a gas permeable material. In addition, it is possible to obtain superior products in the applications and fields that have been used in the past as compared with the conventional products.
本発明のガス透過性材料は、一般式（Ｉ）で表される有機ゲルマニウム化合物を含んでなるものである。 The gas permeable material of the present invention comprises an organic germanium compound represented by the general formula (I).
式中、R1, R2, R3は、それぞれ独立して、炭素数1〜6の直鎖状または分枝状のアルキル基、R4はHまたはCH3、R5は炭素数1〜6の直鎖状または分枝状のアルキレン基、R6は直接結合、または炭素数1〜6の直鎖状または分枝状のアルキレン基を示す。 In the formula, R 1 , R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms, R 4 is H or CH 3 , and R 5 is 1 to C carbon atoms. 6 linear or branched alkylene groups, R 6 represents a direct bond, or a linear or branched alkylene group having 1 to 6 carbon atoms.
前記一般式（Ｉ）で表される化合物において、R5は直接結合すると加水分解しやすく、
材料の安定性が損なわれる。また、炭素数が7以上になると得られる材料が硬すぎて、脆くなるため、炭素数1〜6の直鎖状または分枝状のアルキレン基でなくてはならない。R6は直接結合でもよい。しかし、置換基がある場合は、R5と同様の理由で炭素数1〜6の直鎖状または分枝状のアルキレン基でなくてはならない。
In the compound represented by the general formula (I), R 5 is easily hydrolyzed when directly bonded,
The stability of the material is impaired. In addition, when the number of carbon atoms is 7 or more, the resulting material is too hard and brittle, so it must be a linear or branched alkylene group having 1 to 6 carbon atoms. R 6 may be a direct bond. However, when there is a substituent, it must be a linear or branched alkylene group having 1 to 6 carbon atoms for the same reason as R 5 .
なお、本明細書中において、「・・・（メタ）アクリレート」とは、「・・・アクリレート」および「メタクリレート」の２つの化合物を総称するものであり、また、その他の（メタ）アクリルアミド誘導体についても同様である。 In the present specification, “... (Meth) acrylate” is a general term for two compounds “... acrylate” and “methacrylate”, and other (meth) acrylamide derivatives. The same applies to.
一般式（Ｉ）で表される有機ゲルマニウム化合物の代表としては、例えば、トリメチルゲルミル（メタ）アクリレート、トリメチルゲルミルメチル（メタ）アクリレート、トリメチルゲルミルエチル（メタ）アクリレート、トリメチルゲルミルプロピル（メタ）アクリレート、トリエチルゲルミル（メタ）アクリレート、トリプロピルゲルミル（メタ）アクリレート、トリイソプロピルゲルミル（メタ）アクリレート、トリス（ｔｅｒｔ−ブチル）ゲルミル（メタ）アクリレート、トリペンチルゲルミル（メタ）アクリレート、トリヘキシルゲルミル（メタ）アクリレート、トリメチルゲルミルスチレン、トリメチルゲルミルメチルスチレン、トリメチルゲルミルエチルスチレン、トリメチルゲルミルプロピルスチレン、トリエチルゲルミルスチレン、トリプロピルゲルミルスチレン、トリイソプロピルゲルミルスチレン、トリス（ｔｅｒｔ−ブチル）ゲルミルスチレン、トリペンチルゲルミルスチレン、トリヘキシルゲルミルスチレンなどがあげられる。 Representative examples of the organic germanium compound represented by the general formula (I) include, for example, trimethylgermyl (meth) acrylate, trimethylgermylmethyl (meth) acrylate, trimethylgermylethyl (meth) acrylate, trimethylgermylpropyl ( (Meth) acrylate, triethylgermyl (meth) acrylate, tripropylgermyl (meth) acrylate, triisopropylgermyl (meth) acrylate, tris (tert-butyl) germyl (meth) acrylate, tripentylgermyl (meth) acrylate , Trihexylgermyl (meth) acrylate, trimethylgermylstyrene, trimethylgermylmethylstyrene, trimethylgermylethylstyrene, trimethylgermylpropylstyrene, triethylgermyl Styrene, tripropyl germyl styrene, triisopropyl germyl styrene, tris (tert- butyl) germyl styrene, tripentyl germyl styrene and trihexyl germyl styrene.
ここで、共重合可能なモノマーの具体例として、（メタ）アクリレート誘導体としては、たとえば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、プロピル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、ｔｅｒｔ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｎ−ペンチル（メタ）アクリレート、ｔｅｒｔ−ペンチル（メタ）アクリレート、ヘキシル（メタ）アクリレート、２−メチルブチル（メタ）アクリレート、ヘプチル（メタ）アクリレート、オクチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、ノニル（メタ）アクリレート、デシル（メタ）アクリレート、ドデシル（メタ）アクリレート、ステアリル（メタ）アクリレート、シクロペンチル（メタ）アクリレート、シクロヘキシル（メタ）アクリレートなどのアルキル（メタ）アクリレート；ペンタメチルジシロキサニルメチル（メタ）アクリレート、ペンタメチルジシロキサニルプロピル（メタ）アクリレート、メチルビス（トリメチルシロキシ）シリルプロピル（メタ）アクリレート、トリス（トリメチルシロキシ）シリルプロピル（メタ）アクリレート、モノ[メチルビス（トリメチルシロキシ）シロキシ]ビス（トリメチルシロキシ）シリルプロピル（メタ）アクリレート、メチルビス（トリメチルシロキシ）シリルプロピルグリセロール（メタ）アクリレート、トリス（トリメチルシロキシ）シリルプロピルグリセロール（メタ）アクリレート、モノ[メチルビス（トリメチルシロキシ）シロキシ]ビス（トリメチルシロキシ）シリルプロピルグリセロール（メタ）アクリレート、トリメチルシリルエチルテトラメチルジシロキサニルプロピルグリセロール（メタ）アクリレート、トリメチルシリルメチル（メタ）アクリレート、トリメチルシリルプロピル（メタ）アクリレート、トリメチルシリルプロピルグリセロール（メタ）アクリレート、ペンタメチルジシロキサニルプロピルグリセロール（メタ）アクリレート、メチルビス（トリメチルシロキシ）シリルエチルテトラメチルジシロキサニルメチル（メタ）アクリレート、テトラメチルトリイソプロピルシクロテトラシロキサニルプロピル（メタ）アクリレート、テトラメチルトリイソプロピルシクロテトラシロキシビス（トリメチルシロキシ）シリルプロピル（メタ）アクリレートなどのシリコン含有（メタ）アクリレート；２，２，２−トリフルオロエチル（メタ）アクリレート、２，２，３，３−テトラフルオロプロピル（メタ）アクリレート、２，２，３，３，３−ペンタフルオロプロピル（メタ）アクリレート、２，２，２−トリフルオロ−１−トリフルオロメチルエチル（メタ）アクリレート、２，２，３，３−テトラフルオロ−ｔｅｒｔ−ペンチル（メタ）アクリレート、２，２，３，４，４，４−ヘキサフルオロブチル（メタ）アクリレート、２，２，３，３，４，４−ヘキサフルオロブチル（メタ）アクリレート、２，２，３，４，４，４−ヘキサフルオロ−ｔｅｒｔ−ヘキシル（メタ）アクリレート、２，２，３，３，４，４，４−ヘプタフルオロブチル（メタ）アクリレート、２，２，３，３，４，４，５，５−オクタフルオロペンチル（メタ）アクリレート、３，３，４，４，５，５，６，６−オクタフルオロヘキシル（メタ）アクリレート、２，３，４，５，５，５−ヘキサフルオロ−２，４−ビス（トリフルオロメチル）ペンチル（メタ）アクリレート、２，２，３，３，４，４，５，５，５−ノナフルオロペンチル（メタ）アクリレート、２，２，３，３，４，４，５，５，６，６，７，７−ドデカフルオロヘプチル（メタ）アクリレート、３，３，４，４，５，５，６，６，７，７，８，８−ドデカフルオロオクチル（メタ）アクリレート、３，３，４，４，５，５，６，６，７，７，８，８，８−トリデカフルオロオクチル（メタ）アクリレート、２，２，３，３，４，４，５，５，６，６，７，７，７−トリデカフルオロへプチル（メタ）アクリレート、３，３，４，４，５，５，６，６，７，７，８，８，９，９，１０，１０−ヘキサデカフルオロデシル（メタ）アクリレート、３，３，４，４，５，５，６，６，７，７，８，８，９，９，１０，１０，１０−ヘプタデカフルオロデシル（メタ）アクリレート、３，３，４，４，５，５，６，６，７，７，８，８，９，９，１０，１０，１１，１１−オクタデカフルオロウンデシル（メタ）アクリレート、３，３，４，４，５，５，６，６，７，７，８，８，９，９，１０，１０，１１，１１，１１−ノナデカフルオロウンデシル（メタ）アクリレート、３，３，４，４，５，５，６，６，７，７，８，８，９，９，１０，１０，１１，１１，１２，１２−エイコサフルオロドデシル（メタ）アクリレート、２−ヒドロキシ−４，４，５，５，６，７，７，７−オクタフルオロ−６−トリフルオロメチルヘプチル（メタ）アクリレート、２−ヒドロキシ−４，４，５，５，６，６，７，７，８，９，９，９−ドデカフルオロ−８−トリフルオロメチルノニル（メタ）アクリレート、２−ヒドロキシ−４，４，５，５，６，６，７，７，８，８，９，９，１０，１１，１１，１１−ヘキサデカフルオロ−１０−トリフルオロメチルウンデシル（メタ）アクリレートなどのフッ素含有アルキル（メタ）アクリレートなどがあげられる。特にシリコン含有（メタ）アクリレート、フッ素含有アルキル（メタ）アクリレートはガス透過性の向上にも寄与する。 Here, specific examples of the copolymerizable monomer include (meth) acrylate derivatives such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, tert -Butyl (meth) acrylate, isobutyl (meth) acrylate, n-pentyl (meth) acrylate, tert-pentyl (meth) acrylate, hexyl (meth) acrylate, 2-methylbutyl (meth) acrylate, heptyl (meth) acrylate, octyl (Meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acryl And alkyl (meth) acrylates such as cyclohexyl (meth) acrylate; pentamethyldisiloxanylmethyl (meth) acrylate, pentamethyldisiloxanylpropyl (meth) acrylate, methylbis (trimethylsiloxy) silylpropyl (meth) Acrylate, tris (trimethylsiloxy) silylpropyl (meth) acrylate, mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropyl (meth) acrylate, methylbis (trimethylsiloxy) silylpropylglycerol (meth) acrylate, tris ( Trimethylsiloxy) silylpropylglycerol (meth) acrylate, mono [methylbis (trimethylsiloxy) siloxy] bis (trimethylsiloxy) silylpropi Glycerol (meth) acrylate, trimethylsilylethyltetramethyldisiloxanylpropylglycerol (meth) acrylate, trimethylsilylmethyl (meth) acrylate, trimethylsilylpropyl (meth) acrylate, trimethylsilylpropylglycerol (meth) acrylate, pentamethyldisiloxanylpropyl Glycerol (meth) acrylate, methylbis (trimethylsiloxy) silylethyltetramethyldisiloxanylmethyl (meth) acrylate, tetramethyltriisopropylcyclotetrasiloxanylpropyl (meth) acrylate, tetramethyltriisopropylcyclotetrasiloxybis (trimethyl) Silicon-containing (meth) acrylates such as siloxy) silylpropyl (meth) acrylate 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 2,2,3,3,3-pentafluoropropyl (meth) acrylate, 2 , 2,2-trifluoro-1-trifluoromethylethyl (meth) acrylate, 2,2,3,3-tetrafluoro-tert-pentyl (meth) acrylate, 2,2,3,4,4,4- Hexafluorobutyl (meth) acrylate, 2,2,3,3,4,4-hexafluorobutyl (meth) acrylate, 2,2,3,4,4,4-hexafluoro-tert-hexyl (meth) acrylate 2,2,3,3,4,4,4-heptafluorobutyl (meth) acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl (meth) ) Acrylate, 3,3,4,4,5,5,6,6-octafluorohexyl (meth) acrylate, 2,3,4,5,5,5-hexafluoro-2,4-bis (tri Fluoromethyl) pentyl (meth) acrylate, 2,2,3,3,4,4,5,5,5-nonafluoropentyl (meth) acrylate, 2,2,3,3,4,4,5,5 , 6,6,7,7-dodecafluoroheptyl (meth) acrylate, 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorooctyl (meth) acrylate, 3, , 3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl (meth) acrylate, 2,2,3,3,4,4,5,5 6,6,7,7,7-tridecafluoroheptyl (meth) acrylate, 3,3,4 4,5,5,6,6,7,7,8,8,9,9,10,10-hexadecafluorodecyl (meth) acrylate, 3,3,4,4,5,5,6,6 , 7,7,8,8,9,9,10,10,10-heptadecafluorodecyl (meth) acrylate, 3,3,4,4,5,5,6,6,7,7,8, 8,9,9,10,10,11,11-octadecafluoroundecyl (meth) acrylate, 3,3,4,4,5,5,6,6,7,7,8,8,9, 9,10,10,11,11,11-nonadecafluoroundecyl (meth) acrylate, 3,3,4,4,5,5,6,6,7,7,8,8,9,9, 10,10,11,11,12,12-eicosafluorododecyl (meth) acrylate, 2-hydroxy-4,4,5,5,6,7, , 7-octafluoro-6-trifluoromethylheptyl (meth) acrylate, 2-hydroxy-4,4,5,5,6,6,7,7,8,9,9,9-dodecafluoro-8- Trifluoromethylnonyl (meth) acrylate, 2-hydroxy-4,4,5,5,6,6,7,7,8,8,9,9,10,11,11,11-hexadecafluoro-10 -Fluorine-containing alkyl (meth) acrylates such as trifluoromethylundecyl (meth) acrylate. In particular, silicon-containing (meth) acrylate and fluorine-containing alkyl (meth) acrylate also contribute to improvement of gas permeability.
スチレン誘導体としては、たとえば、スチレン；ｏ−メチルスチレン、ｍ−メチルスチレン、ｐ−メチルスチレン、ｐ−エチルスチレン、ｏ−ヒドロキシスチレン、ｍ−ヒドロキシスチレン、ｐ−ヒドロキシスチレン、トリメチルスチレン、ｔｅｒｔ−ブチルスチレン、パーブロモスチレン、ジメチルアミノスチレン、α−メチルスチレンなどのスチレン誘導体；トリス（トリメチルシロキシ）シリルスチレン、トリメチルシリルスチレン、ペンタメチルジシロキサニルスチレン、ヘプタメチルトリシロキサニルスチレン、ノナメチルテトラシロキサニルスチレン、ペンタデカメチルヘプタシロキサニルスチレン、ヘンエイコサメチルデカシロキサニルスチレン、ヘプタコサメチルトリデカシロキサニルスチレン、ヘントリアコンタメチルペンタデカシロキサニルスチレン、ビス（トリメチルシロキシ）メチルシリルスチレン、トリメチルシロキシ（ペンタメチルジシロキシ）メチルシリルスチレン、トリス（ペンタメチルジシロキシ）シリルスチレン、（トリス（トリメチルシロキシ）シロキサニル）ビス（トリメチルシロキシ）シリルスチレン、ビス（ヘプタメチルトリシロキシ）メチルシリルスチレン、トリス（メチルビス（トリメチルシロキシ）シロキシ）シリルスチレン、トリメチルシロキシ（ビス（トリス（トリメチルシロキシ）シロキシ））シリルスチレン、ヘプタキス（トリメチルシロキシ）トリシロキサニルスチレン、ノナメチルテトラシロキシ（ウンデカメチルペンタシロキシ）メチルシリルスチレン、トリス（トリス（トリメチルシロキシ）シロキシ）シリルスチレン、（トリス（トリメチルシロキシ）ヘキサメチルテトラシロキシ）（トリス（トリメチルシロキシ）シロキシ）トリメチルシロキシシリルスチレン、ノナキス（トリメチルシロキシ）テトラシロキサニルスチレン、ビス（トリデカメチルヘキサシロキシ）メチルシリルスチレンなどのシリコン含有スチレン誘導体；４−ビニルベンジル−２’，２’，２’−トリフルオロエチルエーテル、４−ビニルベンジル−２’，２’，３’，３’，４’，４’，４’−ヘプタフルオロブチルエーテル、４−ビニルベンジル−３’，３’，３’，−トリフルオロプロピルエーテル、４−ビニルベンジル−３’，３’，４’，４’，５’，５’，６’，６’，６’−ノナフルオロヘキシルエーテル、４−ビニルベンジル−４’，４’，５’，５’，６’，６’，７’，７’，８’，８’，８’−ウンデカフルオロオクチルエーテル、ｏ−フルオロスチレン、ｍ−フルオロスチレン、ｐ−フルオロスチレン、トリフルオロスチレン、パーフルオロスチレン、ｐ−トリフルオロメチルスチレン、ｏ−トリフルオロメチルスチレン、ｍ−トリフルオロメチルスチレンなどのフッ素含有スチレン誘導体などがあげられる。特にシリコン含有スチレン誘導体、フッ素含有スチレン誘導体はガス透過性の向上にも寄与する。 Examples of the styrene derivative include styrene; o-methylstyrene, m-methylstyrene, p-methylstyrene, p-ethylstyrene, o-hydroxystyrene, m-hydroxystyrene, p-hydroxystyrene, trimethylstyrene, tert-butyl. Styrene derivatives such as styrene, perbromostyrene, dimethylaminostyrene, α-methylstyrene; tris (trimethylsiloxy) silylstyrene, trimethylsilylstyrene, pentamethyldisiloxanylstyrene, heptamethyltrisiloxanylstyrene, nonamethyltetrasiloxy Sanyl styrene, pentadecamethyl hepacyloxanyl styrene, heneicosamethyl decacyloxanyl styrene, heptacosamethyl tridecacyloxanyl styrene, hentria contour methyl pe Tadecasiloxanyl styrene, bis (trimethylsiloxy) methylsilylstyrene, trimethylsiloxy (pentamethyldisiloxy) methylsilylstyrene, tris (pentamethyldisiloxy) silylstyrene, (tris (trimethylsiloxy) siloxanyl) bis (trimethylsiloxy) ) Silylstyrene, bis (heptamethyltrisiloxy) methylsilylstyrene, tris (methylbis (trimethylsiloxy) siloxy) silylstyrene, trimethylsiloxy (bis (tris (trimethylsiloxy) siloxy)) silylstyrene, heptakis (trimethylsiloxy) trisiloxy Sanylstyrene, nonamethyltetrasiloxy (undecamethylpentasiloxy) methylsilylstyrene, tris (tris (trimethylsiloxy) siloxy) silyl Such as styrene, (tris (trimethylsiloxy) hexamethyltetrasiloxy) (tris (trimethylsiloxy) siloxy) trimethylsiloxysilylstyrene, nonakis (trimethylsiloxy) tetrasiloxanylstyrene, bis (tridecamethylhexacyloxy) methylsilylstyrene Silicon-containing styrene derivatives; 4-vinylbenzyl-2 ′, 2 ′, 2′-trifluoroethyl ether, 4-vinylbenzyl-2 ′, 2 ′, 3 ′, 3 ′, 4 ′, 4 ′, 4′- Heptafluorobutyl ether, 4-vinylbenzyl-3 ′, 3 ′, 3 ′,-trifluoropropylether, 4-vinylbenzyl-3 ′, 3 ′, 4 ′, 4 ′, 5 ′, 5 ′, 6 ′, 6 ′, 6′-nonafluorohexyl ether, 4-vinylbenzyl-4 ′, 4 ′, 5 ′, 5 ′, ', 6', 7 ', 7', 8 ', 8', 8'-undecafluorooctyl ether, o-fluorostyrene, m-fluorostyrene, p-fluorostyrene, trifluorostyrene, perfluorostyrene, p And fluorine-containing styrene derivatives such as -trifluoromethylstyrene, o-trifluoromethylstyrene, and m-trifluoromethylstyrene. In particular, silicon-containing styrene derivatives and fluorine-containing styrene derivatives contribute to the improvement of gas permeability.
フマレート誘導体としては、たとえば、ビス（トリメチルシリルプロピル）フマレート、ビス（ペンタメチルジシロキサニルプロピル）フマレート、ビス（テトラメチル（トリメチルシロキシ）ジシロキサニルプロピル）フマレート、ビス（（トリメチルビス（トリメチルシロキシ）ジシロキサニル）プロピル）フマレート、トリフルオロエチル（トリメチルシリルメチル）フマレート、トリフルオロエチル（トリメチルシリルプロピル）フマレート、ヘキサフルオロイソプロピル（トリメチルシリルメチル）フマレート、ヘキサフルオロイソプロピル（トリメチルシリルプロピル）フマレート、オクタフルオロペンチル（トリメチルシリルメチル）フマレート、オクタフルオロペンチル（トリメチルシリルプロピル）フマレート、トリフルオロエチル（ペンタメチルジシロキサニルメチル）フマレート、トリフルオロエチル（ペンタメチルジシロキサニルプロピル）フマレート、ヘキサフルオロイソプロピル（ペンタメチルジシロキサニルメチル）フマレート、ヘキサフルオロイソプロピル（ペンタメチルジシロキサニルプロピル）フマレート、オクタフルオロペンチル（ペンタメチルジシロキサニルメチル）フマレート、オクタフルオロペンチル（ペンタメチルジシロキサニルプロピル）フマレート、トリフルオロエチル（テトラメチル（トリメチルシロキシ）ジシロキサニルメチル）フマレート、トリフルオロエチル（テトラメチル（トリメチルシロキシ）ジシロキサニルプロピル）フマレート、ヘキサフルオロイソプロピル（テトラメチル（トリメチルシロキシ）ジシロキサニルメチル）フマレート、ヘキサフルオロイソプロピル（テトラメチル（トリメチルシロキシ）ジシロキサニルプロピル）フマレート、オクタフルオロペンチル（テトラメチル（トリメチルシロキシ）ジシロキサニルメチル）フマレート、オクタフルオロペンチル（テトラメチル（トリメチルシロキシ）ジシロキサニルプロピル）フマレート、トリフルオロエチル（トリス（トリメチルシロキシ）シリルメチル）フマレート、トリフルオロエチル（トリス（トリメチルシロキシ）シリルプロピル）フマレート、ヘキサフルオロイソプロピル（トリス（トリメチルシロキシ）シリルメチル）フマレート、ヘキサフルオロイソプロピル（トリス（トリメチルシロキシ）シリルプロピル）フマレート、オクタフルオロペンチル（トリス（トリメチルシロキシ）シリルメチル）フマレート、オクタフルオロペンチル（トリス（トリメチルシロキシ）シリルプロピル）フマレート、イソプロピル（トリメチルシリルプロピル）フマレート、シクロヘキシル（トリメチルシリルプロピル）フマレート、イソプロピル（ペンタメチルジシロキサニルプロピル）フマレート、シクロヘキシル（ペンタメチルジシロキサニルプロピル）フマレート、イソプロピル（テトラメチル（トリメチルシロキシ）ジシロキサニルプロピル）フマレート、シクロヘキシル（テトラメチル（トリメチルシロキシ）ジシロキサニルプロピル）フマレート、イソプロピル（（トリメチルビス（トリメチルシロキシ）ジシロキサニル）プロピル）フマレート、シクロヘキシル（（トリメチルビス（トリメチルシロキシ）ジシロキサニル）プロピル）フマレートなどのシリコン含有フマレートなどがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Examples of the fumarate derivatives include bis (trimethylsilylpropyl) fumarate, bis (pentamethyldisiloxanylpropyl) fumarate, bis (tetramethyl (trimethylsiloxy) disiloxanylpropyl) fumarate, bis ((trimethylbis (trimethylsiloxy) ) Disiloxanyl) propyl) fumarate, trifluoroethyl (trimethylsilylmethyl) fumarate, trifluoroethyl (trimethylsilylpropyl) fumarate, hexafluoroisopropyl (trimethylsilylmethyl) fumarate, hexafluoroisopropyl (trimethylsilylpropyl) fumarate, octafluoropentyl (trimethylsilylmethyl) Fumarate, octafluoropentyl (trimethylsilylpropyl) fumarate, triflu Roethyl (pentamethyldisiloxanylmethyl) fumarate, trifluoroethyl (pentamethyldisiloxanylpropyl) fumarate, hexafluoroisopropyl (pentamethyldisiloxanylmethyl) fumarate, hexafluoroisopropyl (pentamethyldisiloxanyl) Propyl) fumarate, octafluoropentyl (pentamethyldisiloxanylmethyl) fumarate, octafluoropentyl (pentamethyldisiloxanylpropyl) fumarate, trifluoroethyl (tetramethyl (trimethylsiloxy) disiloxanylmethyl) fumarate, Trifluoroethyl (tetramethyl (trimethylsiloxy) disiloxanylpropyl) fumarate, hexafluoroisopropyl (tetramethyl (trimethylsiloxy) disiloxy Nylmethyl) fumarate, hexafluoroisopropyl (tetramethyl (trimethylsiloxy) disiloxanylpropyl) fumarate, octafluoropentyl (tetramethyl (trimethylsiloxy) disiloxanylmethyl) fumarate, octafluoropentyl (tetramethyl (trimethylsiloxy) Disiloxanylpropyl) fumarate, trifluoroethyl (tris (trimethylsiloxy) silylmethyl) fumarate, trifluoroethyl (tris (trimethylsiloxy) silylpropyl) fumarate, hexafluoroisopropyl (tris (trimethylsiloxy) silylmethyl) fumarate, hexafluoro Isopropyl (tris (trimethylsiloxy) silylpropyl) fumarate, octafluoropentyl (tris (trimethyl Siloxy) silylmethyl) fumarate, octafluoropentyl (tris (trimethylsiloxy) silylpropyl) fumarate, isopropyl (trimethylsilylpropyl) fumarate, cyclohexyl (trimethylsilylpropyl) fumarate, isopropyl (pentamethyldisiloxanylpropyl) fumarate, cyclohexyl (pentamethyl) Disiloxanylpropyl) fumarate, isopropyl (tetramethyl (trimethylsiloxy) disiloxanylpropyl) fumarate, cyclohexyl (tetramethyl (trimethylsiloxy) disiloxanylpropyl) fumarate, isopropyl ((trimethylbis (trimethylsiloxy) disiloxanyl) ) Propyl) fumarate, cyclohexyl ((trimethylbis (trimethylsiloxy) disi Kisaniru) propyl) silicon-containing fumarate, such as fumarate and the like. These may be used alone or in admixture of two or more.
（メタ）アクリルアミド誘導体としては、たとえば、Ｎ，Ｎ−ジメチル（メタ）アクリルアミド、Ｎ，Ｎ−ジエチル（メタ）アクリルアミド、Ｎ，Ｎ−メチル（エチル）（メタ）アクリルアミド、Ｎ，Ｎ−メチル（プロピル）（メタ）アクリルアミドなどがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Examples of (meth) acrylamide derivatives include N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N, N-methyl (ethyl) (meth) acrylamide, and N, N-methyl (propyl). ) (Meth) acrylamide and the like, and these may be used alone or in admixture of two or more.
ビニルラクタム誘導体としては、たとえば、N-ビニルピロリドン、Ｎ−ビニルピロリドン、Ｎ−ビニル−３−メチルピロリドン、Ｎ−ビニルカプロラクタム、Ｎ−ビニルピペリドンなどがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Examples of vinyl lactam derivatives include N-vinyl pyrrolidone, N-vinyl pyrrolidone, N-vinyl-3-methylpyrrolidone, N-vinyl caprolactam, N-vinyl piperidone, and these are used alone or in combination of two or more. Can be used.
マレイミド誘導体としては、たとえばトリメチルシリルメチルマレイミド 、トリメチルシリルエチルマレイミド
、トリメチルシリルプロピルマレイミド 、Ｎ−トリストリメチルシロキシシリルメチルマレイミド 、Ｎ−（３−トリストリメチルシロキシシリルプロピル）マレイミド 、Ｎ−（２，２，２−トリフルオロエチル）マレイミド
、Ｎ−（２−トリフルオロメチル）フェニルマレイミド 、Ｎ−（３−トリフルオロメチル）フェニルマレイミド
、Ｎ−（４−トリフルオロメチル）フェニルマレイミド 、Ｎ−（４−パーフルオロプロピル）フェニルマレイミド
、Ｎ−（４−パーフルオロイソプロピル）フェニルマレイミド 、Ｎ−（４−パーフルオロブチル）フェニルマレイミド
、Ｎ−（４−パーフルオロオクチル）フェニルマレイミド 、Ｎ−（３，５−ビス（トリフルオロメチル））フェニルマレイミド
、Ｎ−（３，５−ビス（トリフルオロメチル））ベンジルマレイミド 、Ｎ−（パーフルオロオクチル）フェニルマレイミド
、Ｎ−（３，５−ビス（２，２，２−トリフルオロエチル））フェニルマレイミド 、Ｎ−フェニルマレイミド
、Ｎ−クロロフェニルマレイミド 、Ｎ−メチルフェニルマレイミド 、Ｎ−ヒドロキシフェニルマレイミド 、Ｎ−メトキシフェニルマレイミド 、Ｎ−カルボキシフェニルマレイミド 、Ｎ−ニトロフェニルマレイミド 、Ｎ−トリブロモフェニルマレイミド 、Ｎ−メチルマレイミド 、Ｎ−エチルマレイミド 、Ｎ−プロピルマレイミド 、Ｎ−ブチルマレイミド 、Ｎ−シクロヘキシルマレイミド などのＮ−アルキルマレイミド 、Ｎ−ナフチルマレイミド 、Ｎ−ラウリルマレイミド 、Ｎ，Ｎ´−エチレンビスマレイミド 、Ｎ，Ｎ´−ヘキサメチレンビスマレイミド 、Ｎ，Ｎ´−ｍ−フェニレンビスマレイミド
、Ｎ，Ｎ´−ｐ−フェニレンビスマレイミド 、Ｎ，Ｎ´−４，４´−ジフェニルエーテルビスマレイミド
、Ｎ，Ｎ´−メチレンビス（３−クロロ−ｐ−フェニレン）ビスマレイミド 、Ｎ，Ｎ´−４，４´−ジフェニルスルホンビスマレイミド
、Ｎ，Ｎ´−４，４´−ジシクロヘキシルメタンビスマレイミド 、Ｎ，Ｎ´−α，α´−４，４´−ジメチレンシクロヘキサンビスマレイミド
、Ｎ，Ｎ´−４，４´−ジフェニルシクロヘキサンビスマレイミド 、２−ヒドロキシエチルマレイミド
、マレイミド などがあげられ、これらは単独でまたは２種以上を混合して用いることができる。
Examples of maleimide derivatives include trimethylsilylmethylmaleimide, trimethylsilylethylmaleimide, trimethylsilylpropylmaleimide, N-tristrimethylsiloxysilylmethylmaleimide, N- (3-tristrimethylsiloxysilylpropyl) maleimide, N- (2,2,2-trimethyl). Fluoroethyl) maleimide, N- (2-trifluoromethyl) phenylmaleimide, N- (3-trifluoromethyl) phenylmaleimide, N- (4-trifluoromethyl) phenylmaleimide, N- (4-perfluoropropyl) Phenylmaleimide, N- (4-perfluoroisopropyl) phenylmaleimide, N- (4-perfluorobutyl) phenylmaleimide, N- (4-perfluorooctyl) phenylmaleimide N- (3,5-bis (trifluoromethyl)) phenylmaleimide, N- (3,5-bis (trifluoromethyl)) benzylmaleimide, N- (perfluorooctyl) phenylmaleimide, N- (3,5 -Bis (2,2,2-trifluoroethyl)) phenylmaleimide, N-phenylmaleimide, N-chlorophenylmaleimide, N-methylphenylmaleimide, N-hydroxyphenylmaleimide, N-methoxyphenylmaleimide, N-carboxyphenylmaleimide N-alkylmaleimide such as N-nitrophenylmaleimide, N-tribromophenylmaleimide, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, N-naphthylma Reimide, N-laurylmaleimide, N, N′-ethylenebismaleimide, N, N′-hexamethylenebismaleimide, N, N′-m-phenylenebismaleimide, N, N′-p-phenylenebismaleimide, N, N'-4,4'-diphenyl ether bismaleimide, N, N'-methylenebis (3-chloro-p-phenylene) bismaleimide, N, N'-4,4'-diphenylsulfone bismaleimide, N, N'- 4,4′-dicyclohexylmethane bismaleimide, N, N′-α, α′-4,4′-dimethylenecyclohexane bismaleimide, N, N′-4,4′-diphenylcyclohexane bismaleimide, 2-hydroxyethyl Maleimide, maleimide and the like can be mentioned, and these can be used alone or in admixture of two or more.
また、相溶可能なポリマーの具体例としては、それぞれ前記の共重合可能なモノマーが単独重合したポリマーがあげられる。その他、相溶可能なポリマーとしてポリエチレン及びその誘導体、ポリプロピレン及びその誘導体、ポリ塩化ビニル及びその誘導体、ポリ酢酸ビニル及びその誘導体、ポリプロピオン酸及びその誘導体、ポリアクリロニトリル及びその誘導体、ポリブタジエン及びその誘導体、ポリアミド及びその誘導体等の一般的な成形材料があげられる。相溶可能なポリマーは１種または２種以上を混合して用いることができる。 Specific examples of the compatible polymer include polymers obtained by homopolymerizing the above copolymerizable monomers. Other compatible polymers include polyethylene and its derivatives, polypropylene and its derivatives, polyvinyl chloride and its derivatives, polyvinyl acetate and its derivatives, polypropionic acid and its derivatives, polyacrylonitrile and its derivatives, polybutadiene and its derivatives, General molding materials such as polyamide and derivatives thereof are listed. The compatible polymers can be used alone or in combination of two or more.
ガス透過膜は、ガスを透過することを特徴とし、その特徴を利用して用いられる膜を意味する。ガス分離膜、酸素富化膜等を含む。 The gas permeable membrane is characterized by being permeable to gas and means a membrane used by utilizing the feature. Includes gas separation membranes, oxygen-enriched membranes and the like.
細胞を培養する培養容器は、酸素供給の装置等を必要とせずに、細胞の代謝に必要な酸素等の気体を定常的かつ充分に供給することができ、細胞汚染がなく、輸送も簡便な細胞培養容器を意味する。容器の少なくとも一部がガス透過性材料によって形成された容器である。 A culture vessel for culturing cells can supply a gas such as oxygen necessary for cell metabolism constantly and sufficiently without the need for an oxygen supply device, and is free from cell contamination and easy to transport. Mean cell culture vessel. At least a part of the container is a container formed of a gas permeable material.
眼用レンズは、眼鏡レンズ、眼内レンズ、コンタクトレンズ等の主として眼用に用いられるレンズを意味する。 The ophthalmic lens means a lens mainly used for the eye, such as a spectacle lens, an intraocular lens, and a contact lens.
コンタクトレンズは、角膜に直接接触して用いられるレンズであり、硬質及び軟質であるものを含み、また、含水及び非含水であるものを含む。 Contact lenses are lenses that are used in direct contact with the cornea, including those that are hard and soft, and those that are hydrated and non-hydrated.
本発明においては、他に架橋剤、重合性および非重合性の紫外線吸収剤、重合性および非重合性の色素、重合開始剤、可塑剤等の一般的に用いられる添加剤を用いることもできる。これらは、それぞれ一種または二種以上を用いることができる。製品の付加価値を高めるために必要な、一般的に用いられるものが使用可能であり、特に以下の例示に限定されるものではない。 In the present invention, other commonly used additives such as a crosslinking agent, a polymerizable and non-polymerizable ultraviolet absorber, a polymerizable and non-polymerizable dye, a polymerization initiator, and a plasticizer can also be used. . These may be used alone or in combination of two or more. Commonly used ones necessary for increasing the added value of the product can be used, and are not particularly limited to the following examples.
前記架橋剤の具体例としては、たとえば、ブタンジオールジ（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、トリエチレングリコールジ（メタ）アクリレート、プロピレングリコールジ（メタ）アクリレート、ジプロピレングリコールジ（メタ）アクリレート、アリル（メタ）アクリレート、ビニル（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、メタクリロイルオキシエチルアクリレート、ジビニルベンゼン、ジアリルフタレート、アジピン酸ジアリル、トリアリルイソシアヌレート、α−メチレン−Ｎ−ビニルピロリドン、４−ビニルベンジル（メタ）アクリレート、３−ビニルベンジル（メタ）アクリレート、２，２−ビス（ｐ−（メタ）アクリロイルオキシフェニル）ヘキサフルオロプロパン、２，２−ビス（ｍ−（メタ）アクリロイルオキシフェニル）ヘキサフルオロプロパン、２，２−ビス（ｏ−（メタ）アクリロイルオキシフェニル）ヘキサフルオロプロパン、２，２−ビス（ｐ−（メタ）アクリロイルオキシフェニル）プロパン、２，２−ビス（ｍ−（メタ）アクリロイルオキシフェニル）プロパン、２，２−ビス（ｏ−（メタ）アクリロイルオキシフェニル）プロパン、１，４−ビス（２−（メタ）アクリロイルオキシヘキサフルオロイソプロピル）ベンゼン、１，３−ビス（２−（メタ）アクリロイルオキシヘキサフルオロイソプロピル）ベンゼン、１，２−ビス（２−（メタ）アクリロイルオキシヘキサフルオロイソプロピル）ベンゼン、１，４−ビス（２−（メタ）アクリロイルオキシイソプロピル）ベンゼン、１，３−ビス（２−（メタ）アクリロイルオキシイソプロピル）ベンゼン、１，２−ビス（２−（メタ）アクリロイルオキシイソプロピル）ベンゼンなどがあげられる。これらの架橋剤は、単独でまたは２種以上を混合して用いることができる。 Specific examples of the crosslinking agent include, for example, butanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and propylene glycol di (meth) acrylate. , Dipropylene glycol di (meth) acrylate, allyl (meth) acrylate, vinyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, methacryloyloxyethyl acrylate, divinylbenzene, diallyl phthalate, diallyl adipate, triallyl isocyanurate , Α-methylene-N-vinylpyrrolidone, 4-vinylbenzyl (meth) acrylate, 3-vinylbenzyl (meth) acrylate, 2,2-bis (p- (me ) Acryloyloxyphenyl) hexafluoropropane, 2,2-bis (m- (meth) acryloyloxyphenyl) hexafluoropropane, 2,2-bis (o- (meth) acryloyloxyphenyl) hexafluoropropane, 2,2 -Bis (p- (meth) acryloyloxyphenyl) propane, 2,2-bis (m- (meth) acryloyloxyphenyl) propane, 2,2-bis (o- (meth) acryloyloxyphenyl) propane, 1, 4-bis (2- (meth) acryloyloxyhexafluoroisopropyl) benzene, 1,3-bis (2- (meth) acryloyloxyhexafluoroisopropyl) benzene, 1,2-bis (2- (meth) acryloyloxyhexa) Fluoroisopropyl) benzene, 1,4-bis (2- (Meth) acryloyloxyisopropyl) benzene, 1,3-bis (2- (meth) acryloyloxyisopropyl) benzene, 1,2-bis (2- (meth) acryloyloxyisopropyl) benzene and the like. These crosslinking agents can be used alone or in admixture of two or more.
重合性の紫外線吸収剤とは、たとえば、２−ヒドロキシ−４−（メタ）アクリロイルオキシベンゾフェノンなどのベンゾフェノン系重合性紫外線吸収剤、２−（２′ヒドロキシ−５′−（メタ）アクリロイルオキシエトキシ−３′−ｔ−ブチルフェニル）−５−メチル−２Ｈ−ベンゾトリアゾールなどのベンゾトリアゾール系重合性紫外線吸収剤などがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Examples of the polymerizable ultraviolet absorber include benzophenone-based polymerizable ultraviolet absorbers such as 2-hydroxy-4- (meth) acryloyloxybenzophenone, 2- (2′hydroxy-5 ′-(meth) acryloyloxyethoxy-), and the like. 3'-t-butylphenyl) -5-methyl-2H-benzotriazole and other benzotriazole-based polymerizable ultraviolet absorbers can be used, and these can be used alone or in admixture of two or more.
非重合性の紫外線吸収剤とは、たとえば、ベンゾフェノン系重合性紫外線吸収剤として、２−ヒドロキシ−４−（メタ）アクリロイルオキシベンゾフェノン、２−ヒドロキシ−４−（メタ）アクリロイルオキシ−５−ｔｅｒｔ−ブチルベンゾフェノン、２−ヒドロキシ−４−（メタ）アクリロイルオキシ−２’，４’−ジクロロベンゾフェノン、２−ヒドロキシ−４−（２’−ヒドロキシ−３’−（メタ）アクリロイルオキシプロポキシ）ベンゾフェノンなどがあげられる。ベンゾトリアゾール系重合性紫外線吸収剤としては、２−（５−クロロ−２Ｈ−ベンゾトリアゾール−２−イル）−６−（１，１−ジメチルエチル）−４−メチルフェノール、２−（２’−ヒドロキシ−５’−（メタ）アクリロイルオキシエチルフェニル）−２Ｈ−ベンゾトリアゾール、２−（２’−ヒドロキシ−５’−（メタ）アクリロイルオキシエチルフェニル）−５−クロロ−２Ｈ−ベンゾトリアゾール、２−（２’−ヒドロキシ−５’−（メタ）アクリロイルオキシプロピルフェニル）−２Ｈ−ベンゾトリアゾール、２−（２’−ヒドロキシ−５’−（メタ）アクリロイルオキシプロピル−３’−ｔｅｒｔ−ブチルフェニル）−５−クロロ−２Ｈ−ベンゾトリアゾールなどがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Non-polymerizable UV absorbers include, for example, 2-hydroxy-4- (meth) acryloyloxybenzophenone, 2-hydroxy-4- (meth) acryloyloxy-5-tert- as benzophenone-based polymerizable UV absorbers. Butylbenzophenone, 2-hydroxy-4- (meth) acryloyloxy-2 ′, 4′-dichlorobenzophenone, 2-hydroxy-4- (2′-hydroxy-3 ′-(meth) acryloyloxypropoxy) benzophenone It is done. Examples of the benzotriazole-based polymerizable UV absorber include 2- (5-chloro-2H-benzotriazol-2-yl) -6- (1,1-dimethylethyl) -4-methylphenol, 2- (2′- Hydroxy-5 ′-(meth) acryloyloxyethylphenyl) -2H-benzotriazole, 2- (2′-hydroxy-5 ′-(meth) acryloyloxyethylphenyl) -5-chloro-2H-benzotriazole, 2- (2'-hydroxy-5 '-(meth) acryloyloxypropylphenyl) -2H-benzotriazole, 2- (2'-hydroxy-5'-(meth) acryloyloxypropyl-3'-tert-butylphenyl)- 5-chloro-2H-benzotriazole and the like are used, and these are used alone or in admixture of two or more. It is possible.
重合性の色素とは、たとえば、１−フェニルアゾ−４−（メタ）アクリロイルオキシナフタレン、１−フェニルアゾ−２−ヒドロキシ−３−（メタ）アクリロイルオキシナフタレン、１−ナフチルアゾ−２−ヒドロキシ−３−（メタ）アクリロイルオキシナフタレンなどのアゾ系重合性色素；１，５−ビス（（メタ）アクリロイルアミノ）−９，１０−アントラキノン、１−（４′−ビニルベンゾイルアミド）−９，１０−アントラキノン、４−アミノ−１−（４′−ビニルベンゾイルアミド）−９，１０−アントラキノンなどのアントラキノン系重合性色素；ｏ−ニトロアニリノメチル（メタ）アクリレートなどのニトロ系重合性色素；（メタ）アクリロイル化テトラアミノ銅フタロシアニン、（メタ）アクリロイル化（ドデカノイル化テトラアミノ銅フタロシアニン）などのフタロシアニン系重合性色素などがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Examples of the polymerizable dye include 1-phenylazo-4- (meth) acryloyloxynaphthalene, 1-phenylazo-2-hydroxy-3- (meth) acryloyloxynaphthalene, 1-naphthylazo-2-hydroxy-3- ( Azo polymerizable dyes such as (meth) acryloyloxynaphthalene; 1,5-bis ((meth) acryloylamino) -9,10-anthraquinone, 1- (4'-vinylbenzoylamide) -9,10-anthraquinone, 4 -Anthraquinone polymerizable dyes such as amino-1- (4'-vinylbenzoylamide) -9,10-anthraquinone; Nitro polymerizable dyes such as o-nitroanilinomethyl (meth) acrylate; (meth) acryloylation Tetraamino copper phthalocyanine, (meth) acryloylation (dodecanoylation) Raamino copper phthalocyanine) such as phthalocyanine polymerizable dyes and the like, it can be used alone or in admixture of two or more.
非重合性の色素とは、たとえば、１，４−ビス［（４−メチルフェニル）アミノ］−９，１０−アントラキノン（Ｄ＆Ｃ Ｇｒｅｅｎ Ｎｏ．６）、１−［［４−（フェニルアゾ）フェニル］アゾ］−２−ナフタレノール（Ｄ＆Ｃ
Ｒｅｄ Ｎｏ．１７）、１−ヒドロキシ−４−［（４−メチルフェニル）アミノ］−９，１０−アントラキノン（Ｄ＆Ｃ
Ｖｉｏｌｅｔ Ｎｏ．２）、２−（２−キノリル）−１，３−インダンジオン（Ｄ＆Ｃ Ｙｅｌｌｏｗ Ｎｏ．１１）、４−［（２，４−ジメチルフェニル）アゾ］−２，４−ジヒドロ−５−メチル−２−フェニル−３Ｈ−ピラゾール−３−オン（Ｃ．Ｉ．
Ｓｏｌｖｅｎｔ Ｙｅｌｌｏｗ １８）、２−（１，３−ジオキソ−２−インダニル）−３−ヒドロキシキノリン（ＭＡＣＲＯＬＥＸ（商標）Ｙｅｌｌｏｗ−Ｇ）などがあげられ、これらは単独でまたは２種以上を混合して用いることができる。
Non-polymerizable dyes include, for example, 1,4-bis [(4-methylphenyl) amino] -9,10-anthraquinone (D & C Green No. 6), 1-[[4- (phenylazo) phenyl] azo ] -2-Naphthalenol (D & C
Red No. 17), 1-hydroxy-4-[(4-methylphenyl) amino] -9,10-anthraquinone (D & C
Violet No. 2), 2- (2-quinolyl) -1,3-indandione (D & C Yellow No. 11), 4-[(2,4-dimethylphenyl) azo] -2,4-dihydro-5-methyl-2 -Phenyl-3H-pyrazol-3-one (C.I.
Solvent Yellow 18), 2- (1,3-dioxo-2-indanyl) -3-hydroxyquinoline (MACROLEX (trademark) Yellow-G), and the like are used alone or in combination of two or more. be able to.
重合開始剤のうち、ラジカル重合開始剤の代表例としては、たとえばアゾビスイソブチロニトリル、アゾビスジメチルバレロニトリル、ベンゾイルパーオキサイド、ｔｅｒｔ−ブチルハイドロパーオキサイド、クメンパーオキサイドなどがあげられる。重合開始剤の代表例としては、たとえばメチルオルソベンゾイルベンゾエート、メチルベンゾイルフォルメート、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル、ベンゾイン−ｎ−ブチルエーテルなどのベンゾイン系光重合開始剤；２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、ｐ−イソプロピル−α−ヒドロキシイソブチルフェノンなどのフェノン系光重合開始剤；１−ヒドロキシシクロヘキシルフェニルケトン；１−フェニル−１，２−プロパンジオン−２−（ｏ−エトキシカルボニル）オキシム；２−クロロチオキサンソン、２−メチルチオキサンソンなどのチオキサンソン系光重合開始剤；ジベンゾスバロン；２−エチルアンスラキノン；ベンゾフェノンアクリレート；ベンゾフェノン；ベンジルなどがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Among the polymerization initiators, representative examples of radical polymerization initiators include azobisisobutyronitrile, azobisdimethylvaleronitrile, benzoyl peroxide, tert-butyl hydroperoxide, cumene peroxide, and the like. Representative examples of the polymerization initiator include benzoin photopolymerization initiators such as methyl orthobenzoyl benzoate, methyl benzoyl formate, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzoin-n-butyl ether; Phenone photopolymerization initiators such as 2-hydroxy-2-methyl-1-phenylpropan-1-one and p-isopropyl-α-hydroxyisobutylphenone; 1-hydroxycyclohexyl phenyl ketone; 1-phenyl-1,2- Propanedione-2- (o-ethoxycarbonyl) oxime; thioxanthone photopolymerization initiators such as 2-chlorothioxanthone and 2-methylthioxanthone; dibenzosvalon; 2-ethylanthraquino ; Benzophenone acrylate; benzophenone; benzyl and the like, they can be used alone or in admixture of two or more.
可塑剤とは、たとえば、リン酸トリブチル、リン酸トリ（2-エチルヘキシル）、リン酸トリフェニル等のリン酸エステル；フタル酸ビス（2-エチルヘキシル）、フタル酸ジイソノニル、フタル酸ジイソデシル、フタル酸ジウンデシル等のフタル酸エステル；アジピン酸ビス（2-エチルヘキシル）、アジピン酸ジイソノニル等のアジピン酸エステルなどがあげられ、これらは単独でまたは２種以上を混合して用いることができる。 Examples of plasticizers include phosphate esters such as tributyl phosphate, tri (2-ethylhexyl) phosphate, triphenyl phosphate; bis (2-ethylhexyl) phthalate, diisononyl phthalate, diisodecyl phthalate, diundecyl phthalate Phthalic acid esters such as bis (2-ethylhexyl) adipate and diisononyl adipate, and the like. These can be used alone or in admixture of two or more.
また、重合方法においては熱重合、紫外線等を用いた光重合等の一般的な重合方法を用いてよく、特に限定されるものではない。成形方法においても、モールド成形、スピンキャスト成形、射出成形、圧縮成形、ブロー成形、押出成形等の一般的な成形方法を用いてよく、特に限定されるものではない。必要に応じて、切削、研磨等の二次加工を行ってもよい。 The polymerization method may be any general polymerization method such as thermal polymerization or photopolymerization using ultraviolet rays, and is not particularly limited. Also in the molding method, a general molding method such as mold molding, spin cast molding, injection molding, compression molding, blow molding, extrusion molding or the like may be used, and it is not particularly limited. You may perform secondary processes, such as cutting and grinding | polishing, as needed.
本発明のガス透過性の材料は、高いガス透過性を有している。また、高い屈折率、高い硬度を有する物性バランスにすぐれたものである。したがって、従来のガス透過性の材料では、使用困難であった用途、分野でも使用可能となる。それだけでなく、従来使用されていた用途、分野においても従来品に比べ、優れた製品を得ることが可能となる。特に、センサー等に用いられるガス透過膜、細胞を培養する培養容器、眼用レンズに広く利用することができる。その中でも特に、コンタクトレンズに好適に利用することができる。 The gas permeable material of the present invention has high gas permeability. In addition, it has an excellent balance of physical properties with high refractive index and high hardness. Therefore, the conventional gas-permeable material can be used in applications and fields that are difficult to use. In addition, it is possible to obtain superior products in the applications and fields that have been used in the past as compared with the conventional products. In particular, it can be widely used for gas permeable membranes used in sensors, culture vessels for culturing cells, and ophthalmic lenses. Among these, it can utilize suitably for a contact lens especially.
以下、実施例により本発明を具体的に説明するが、本発明はこれらの実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to these Examples.
合成例１ トリメチルゲルミルスチレン（GeSt）の合成
ジムロート冷却管及び滴下ロートを装着した300 mLの三口丸底フラスコに、Mg
3.3 g (0.14 mol) を入れ、窒素置換を行った後、脱水テトラヒドロフランを30 mL，1,2-ジブロモエタンを2〜3滴加えしばらく攪拌した。4-クロロスチレン
16 g (0.12 mol) のテトラヒドロフラン溶液20 mLを滴下ロートに入れ、少量滴下して反応を活性化させた後、50〜60℃のオイルバス中にて滴下を開始した。滴下終了後、テトラヒドロフランを15
mL加え、60〜70℃のオイルバス中で2〜3時間熟成した。
次に、ジムロート冷却管及び滴下ロートを装着した500 mLの三口丸底フラスコにトリメチルクロロゲルマン
14.9 g (0.097 mol) とテトラヒドロフラン50 mLを入れ、窒素置換を行った。この滴下ロートに先ほど反応させた、グリニヤード試薬を入れ、室温下で滴下した。滴下終了後、室温で2〜3時間攪拌を続け反応を終了した。
反応溶液を加水分解後、1 Lの分液ロートを用いて、エーテルで抽出を行った。反応混合物から2回抽出を行い、その後蒸留水で3回洗浄を行った。エーテル層を分取し、無水硫酸ナトリウムを入れて乾燥後、溶媒を留去し、シリカゲルカラムで精製を行った。得られた生成物の1H-NMRを測定し、純度99％以上のトリメチルゲルミルスチレンであることを確認した。
Synthesis Example 1 Trimethylgermylstyrene (GeSt) Synthesis A 300 mL three-necked round bottom flask equipped with a Dimroth condenser and a dropping funnel was charged with Mg.
After putting 3.3 g (0.14 mol) and replacing with nitrogen, 30 mL of dehydrated tetrahydrofuran and 2 to 3 drops of 1,2-dibromoethane were added and stirred for a while. 4-chlorostyrene
20 mL of a 16 g (0.12 mol) tetrahydrofuran solution was placed in a dropping funnel and a small amount of the solution was added to activate the reaction, and then the dropping was started in an oil bath at 50 to 60 ° C. After completion of dropping, add 15
mL was added and aged in an oil bath at 60 to 70 ° C. for 2 to 3 hours.
Next, a trimethylchlorogermane was placed in a 500 mL three-necked round bottom flask equipped with a Dimroth condenser and a dropping funnel.
14.9 g (0.097 mol) and 50 mL of tetrahydrofuran were added, and nitrogen substitution was performed. The green yard reagent which had been reacted previously was put into the dropping funnel and dropped at room temperature. After completion of the dropwise addition, stirring was continued at room temperature for 2 to 3 hours to complete the reaction.
The reaction solution was hydrolyzed and extracted with ether using a 1 L separatory funnel. The reaction mixture was extracted twice and then washed with distilled water three times. The ether layer was separated, dried over anhydrous sodium sulfate, the solvent was distilled off, and purification was performed with a silica gel column. 1 H-NMR of the obtained product was measured and confirmed to be trimethylgermylstyrene having a purity of 99% or more.
実施例１（トリメチルゲルミルスチレン（GeSt）の懸濁重合）
100mL三口フラスコに蒸留水30mLを入れ、分散剤として完全ケン化ポリビニルアルコール0.2g, 及び部分ケン化ポリビニルアルコール0.01gを加え加熱して溶解させた。放冷後過酸化ベンゾイル0.05gを溶解させたGeSt 10gを投入し、約200rpmの回転速度で、オイルバス中80℃に設定し、5時間重合を行った。重合後得られた粒径ポリマーをろ別し、充分に水洗・乾燥して、GeStポリマーを得た。
サイズ排除クロマトグラフィー（カラム：Shodex製 GPC LF-804 Length 300mm×I.D. 8.0 mm、検出器RI、THF 0.3%溶液）にて分子量を測定した結果、ポリスチレン換算で、重量平均分子量が約38万、分子量分布 約2.8（Mw/Mn）であった。
次に、圧縮成形機（APPLIED POWER JAPAN製 ENERPAC S.E MODEL ESE-781-00）を使用し、真鍮製のプレート成形型にGeStポリマーを適当量入れ、温度250℃, 圧力500kgにて圧縮成形し、プレートを得た。
Example 1 (Suspension polymerization of trimethylgermylstyrene (GeSt))
30 mL of distilled water was placed in a 100 mL three-necked flask, 0.2 g of fully saponified polyvinyl alcohol and 0.01 g of partially saponified polyvinyl alcohol were added as a dispersant, and dissolved by heating. After allowing to cool, 10 g of GeSt in which 0.05 g of benzoyl peroxide was dissolved was added, and the polymerization was carried out for 5 hours by setting at 80 ° C. in an oil bath at a rotation speed of about 200 rpm. The particle size polymer obtained after the polymerization was filtered off, washed thoroughly with water and dried to obtain a GeSt polymer.
As a result of measuring the molecular weight with size exclusion chromatography (column: GPC LF-804 Length 300mm x ID 8.0 mm, manufactured by Shodex, detector RI, THF 0.3% solution), the polystyrene-equivalent weight average molecular weight is about 380,000, molecular weight The distribution was about 2.8 (Mw / Mn).
Next, using a compression molding machine (ENERPAC SE MODEL ESE-781-00 manufactured by APPLIED POWER JAPAN), an appropriate amount of GeSt polymer is put into a brass plate mold, and compression molded at a temperature of 250 ° C and a pressure of 500 kg. A plate was obtained.
実施例２
トリメチルゲルミルスチレン（GeSt）7重量部、スチレン3重量部、及び前記モノマーの合計重量部に対し0.3％の割合で重合開始剤２，２’−アゾビス（２，４−ジメチルバレロニトリル）を加えて溶解し、シリコーンコートした内径約13mmのガラス製試験管に調合物を注入した。窒素パージ後密栓して、恒温水槽中で40℃で24時間放置し、その後50℃で8時間予備重合を行った後、熱風循環式乾燥機に移し、50〜120℃まで徐々に13時間かけて昇温して重合を完結させた。得られた棒材をダイヤモンド旋盤にて所望の形状に加工し試験試料を得て、各物性値を評価した。
実施例３〜６、比較例１〜３の配合組成と各物性値を表1、2に示した。実施例３〜５および比較例１〜２の試験試料は実施例２と同様の方法で調製した。実施例６および比較例３の試験試料は実施例２と同様の方法で調製した後、常温の蒸留水中に24時間浸漬し、その後、60℃に温調した生理食塩水中に6時間浸漬して試験試料とした。
Example 2
Polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) was added at a ratio of 0.3% with respect to 7 parts by weight of trimethylgermylstyrene (GeSt), 3 parts by weight of styrene, and the total weight part of the monomers. The composition was poured into a glass test tube having an inner diameter of about 13 mm which had been dissolved and coated with silicone. After purging with nitrogen, close the cap, leave it in a constant temperature water bath at 40 ° C for 24 hours, then perform prepolymerization at 50 ° C for 8 hours, then transfer it to a hot air circulation dryer and gradually take it from 50 to 120 ° C over 13 hours. The temperature was raised to complete the polymerization. The obtained bar was processed into a desired shape with a diamond lathe to obtain a test sample, and each physical property value was evaluated.
Tables 1 and 2 show formulation compositions and physical property values of Examples 3 to 6 and Comparative Examples 1 to 3. Test samples of Examples 3 to 5 and Comparative Examples 1 and 2 were prepared in the same manner as in Example 2. The test samples of Example 6 and Comparative Example 3 were prepared in the same manner as in Example 2, and then immersed in distilled water at room temperature for 24 hours, and then immersed in physiological saline adjusted to 60 ° C. for 6 hours. A test sample was obtained.
なお、表１中及び表２中の略語は、以下の化合物を示す。
ＭＡＵＳ：
In addition, the abbreviation in Table 1 and Table 2 shows the following compounds.
MAUS:
GeSt：トリメチルゲルミルスチレン
GeMA：トリメチルゲルミルメチルメタクリレート GELEST, INC製 試薬グレード
SiSt：トリメチルシリルスチレン
St：スチレン
MMA：メチルメタクリレート
3FEMA：トリフルオロエチルメタクリレート
EDMA：エチレングリコールジメタクリレート
ADVN：２，２’−アゾビス（２，４−ジメチルバレロニトリル）
SiMA：トリメチルシリルメチルメタクリレート
NVP：Ｎ−ビニル−２−ピロリドン
HMPPO：２−ヒドロキシ−２−メチル−プロピオフェノン
GeSt: Trimethylgermylstyrene
GeMA: Trimethylgermylmethyl methacrylate GELEST, INC reagent grade
SiSt: Trimethylsilylstyrene
St: Styrene
MMA: Methyl methacrylate
3FEMA: trifluoroethyl methacrylate
EDMA: Ethylene glycol dimethacrylate
ADVN: 2,2′-azobis (2,4-dimethylvaleronitrile)
SiMA: Trimethylsilylmethyl methacrylate
NVP: N-vinyl-2-pyrrolidone
HMPPO: 2-hydroxy-2-methyl-propiophenone
[透明性]
(株)島津製作所製 紫外・可視分光光度計UV-3150を用いて、380〜780nmの範囲での可視光線透過率を測定した。試験試料は旋盤にて加工後、研磨した直径約14mm厚み約0.2mmのプレートを用いた。対照は蒸留水とした。
[transparency]
The visible light transmittance in the range of 380 to 780 nm was measured using an ultraviolet / visible spectrophotometer UV-3150 manufactured by Shimadzu Corporation. As a test sample, a plate having a diameter of about 14 mm and a thickness of about 0.2 mm was used after being processed by a lathe. The control was distilled water.
[ガス透過性]
実施例１〜５及び比較例１〜２については、GTG （Gas to Gas法）ANALYZER （REHDER
DEVELOPMENT COMPANY製）を用いて、35℃における酸素透過係数を測定した。試験試料は旋盤にて直径約12mm, 厚み約0.2mm〜0.5mmに加工したプレートを用いた。測定時間は5分とした。得られた測定値を、ISO9912-2にて規格化された(株)メニコン製コンタクトレンズ「メニコンEX」（酸素透過係数= 64）の測定値を用いて換算した。なお、ガス透過性は酸素透過係数の値（単位：(cm2/sec)・(mLO2/(mL・mmHg) )）を示し、特に酸素透過係数の値に10-11を乗じた数値である。
実施例６及び比較例３については、理科精機工業（株）製の製科研式フィルム酸素透過率計を用いて、３５℃の生理食塩水中にて酸素透過係数を測定した。試験試料は旋盤にて、含水時に直径約14mm、厚み約0.2mmになるように加工したプレートを用いた。得られた測定値を、同様に測定したテトラフルオロエチレンフィルム（酸素透過係数＝14.1）の測定値を用いて換算した。単位は上記と同じである。
[Gas permeability]
About Examples 1-5 and Comparative Examples 1-2, GTG (Gas to Gas method) ANALYZER (REHDER
DEVELOPMENT COMPANY) was used to measure the oxygen transmission coefficient at 35 ° C. The test sample used was a plate processed to a diameter of about 12 mm and a thickness of about 0.2 mm to 0.5 mm on a lathe. The measurement time was 5 minutes. The obtained measured value was converted using the measured value of the contact lens “Menicon EX” (oxygen permeability coefficient = 64) manufactured by Menicon Co., Ltd., standardized by ISO9912-2. The gas permeability indicates the value of oxygen permeability coefficient (unit: (cm 2 / sec) · (mLO 2 / (mL · mmHg))), especially the value obtained by multiplying the value of oxygen permeability coefficient by 10-11. is there.
For Example 6 and Comparative Example 3, the oxygen transmission coefficient was measured in physiological saline at 35 ° C. using a Kakenken film oxygen permeability meter manufactured by Rika Seiki Kogyo Co., Ltd. As a test sample, a plate processed to have a diameter of about 14 mm and a thickness of about 0.2 mm with a lathe was used. The obtained measured value was converted using the measured value of a tetrafluoroethylene film (oxygen permeability coefficient = 14.1) measured in the same manner. The unit is the same as above.
[屈折率]
(株)アタゴ製 アッベ屈折計 TYPE 2Tを用いて、温度25℃，湿度50%での屈折率を測定した。実施例１〜５及び比較例１〜２については、接触液として1−ブロモナフタレンを用いた。試験試料は旋盤にて直径約12mm, 厚み約1mmに加工したプレートを用いた。
実施例６及び比較例３については、接触液を使用せずに測定した。試験試料は旋盤にて、含水時に直径約14mm、厚み約0.2mmになるように加工したプレートを用いた。
[Refractive index]
The refractive index at 25 ° C. and 50% humidity was measured using an Abbe refractometer TYPE 2T manufactured by Atago Co., Ltd. For Examples 1 to 5 and Comparative Examples 1 and 2, 1-bromonaphthalene was used as the contact liquid. The test sample used was a plate processed to a diameter of about 12 mm and a thickness of about 1 mm on a lathe.
About Example 6 and Comparative Example 3, it measured without using a contact liquid. As a test sample, a plate processed to have a diameter of about 14 mm and a thickness of about 0.2 mm with a lathe was used.
[硬度]
(株)アカシ製 ロックウェルスーパーフィシャル硬度計 形式ASDを用いて、温度25℃，湿度50%での硬度を測定した。試験試料は旋盤にて直径約12mm, 厚み約4mmに加工したブロックを用いた。
[hardness]
The hardness at a temperature of 25 ° C. and a humidity of 50% was measured using a Rockwell superficial hardness tester model ASD manufactured by Akashi Co., Ltd. The test sample used was a block machined to a diameter of about 12 mm and a thickness of about 4 mm on a lathe.
[含水率]
ザルトリウス(株)製 電子天びんR200Dを用いて35℃における含水率を測定した。試験試料は旋盤にて直径約12mm, 厚み約2mmに加工したプレートを用い、含水率（重量％）を次式に基づいて算出した。
含水率（重量％）＝｛（Ｗ−Ｗｏ）／Ｗ｝×１００
ただし、Ｗは水和処理後の平衡含水状態での試験片の重量（ｇ）、Ｗo は水和処理後、乾燥器中にて乾燥した乾燥状態での試験片の重量（ｇ）を表わす。
[Moisture content]
The water content at 35 ° C. was measured using an electronic balance R200D manufactured by Sartorius Co., Ltd. The test sample was a plate processed with a lathe to have a diameter of about 12 mm and a thickness of about 2 mm, and the moisture content (% by weight) was calculated based on the following formula.
Water content (% by weight) = {(W−Wo) / W} × 100
Here, W represents the weight (g) of the test piece in an equilibrium water-containing state after hydration treatment, and Wo represents the weight (g) of the test piece in a dry state after hydration treatment and dried in a drier.
実施例１は、比較例１と比べ、ガス透過性および硬度にすぐれていることがわかる。実施例２〜５は、シリコーン成分を含む比較例２と比べ、ガス透過性および屈折率はほぼ同等であるが、硬度にすぐれていることがわかる。 It can be seen that Example 1 is superior to Comparative Example 1 in gas permeability and hardness. It can be seen that Examples 2 to 5 have almost the same gas permeability and refractive index as compared with Comparative Example 2 containing a silicone component, but are excellent in hardness.
表２には、本発明を含水ゲルに応用した場合の物性値比較を示した。通常の含水ゲルの場合、含水率とガス透過性は比例関係にある。つまり、含水率が高いほどガス透過性も高くなる。比較例３はシリコーンを含む含水ゲルであるため、通常の含水ゲルよりガス透過性が高くなっている。実施例６はその比較例３に比べて含水率は9％少ないにもかかわらず、なおもガス透過性が20％以上高くなっていることがわかる。 Table 2 shows a comparison of physical properties when the present invention is applied to a hydrogel. In the case of a normal water-containing gel, the water content and the gas permeability are in a proportional relationship. That is, the higher the moisture content, the higher the gas permeability. Since Comparative Example 3 is a hydrous gel containing silicone, the gas permeability is higher than that of a normal hydrous gel. Although Example 6 has a water content of 9% less than that of Comparative Example 3, it can be seen that the gas permeability is still 20% or more higher.
本発明のガス透過性材料は、ガス透過膜、細胞を培養する培養容器、眼用レンズに適用することができる。 The gas permeable material of the present invention can be applied to a gas permeable membrane, a culture vessel for culturing cells, and an ophthalmic lens.
Claims (10)
R2, R3は、それぞれ独立して、炭素数1〜6の直鎖状または分枝状のアルキル基、R4はHまたはCH3、R5は炭素数1〜6の直鎖状または分枝状のアルキレン基、R6は直接結合、または炭素数1〜6の直鎖状または分枝状のアルキレン基を示す。 A gas permeable material comprising a polymerizable organic germanium compound represented by the general formula (I).
R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms, R 4 is H or CH 3 , and R 5 is a linear chain having 1 to 6 carbon atoms or A branched alkylene group, R 6 represents a direct bond, or a linear or branched alkylene group having 1 to 6 carbon atoms.
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| JP2019530680A (en) * | 2016-09-23 | 2019-10-24 | 株式会社メニコン | Nail cosmetic composition, method of use thereof and nail cosmetic resin |
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| JPS63273640A (en) * | 1987-05-06 | 1988-11-10 | Agency Of Ind Science & Technol | Production of substituted polyphenylene oxide |
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| JP3761676B2 (en) * | 1997-07-11 | 2006-03-29 | 株式会社メニコン | Cell culture vessel |
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| JPS60142324A (en) * | 1983-12-28 | 1985-07-27 | Toyo Contact Lens Co Ltd | Oxygen permeable hard contact lens |
| JPS63171619A (en) * | 1986-12-08 | 1988-07-15 | エアー．プロダクツ．アンド．ケミカルス．インコーポレーテッド | Polymer film separating gas mixture, manufacture thereof and method of gas mixture separation thereof |
| JPS63273640A (en) * | 1987-05-06 | 1988-11-10 | Agency Of Ind Science & Technol | Production of substituted polyphenylene oxide |
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| JP2019530680A (en) * | 2016-09-23 | 2019-10-24 | 株式会社メニコン | Nail cosmetic composition, method of use thereof and nail cosmetic resin |
| JP7105225B2 (en) | 2016-09-23 | 2022-07-22 | 株式会社メニコン | Gel nail cosmetic composition, method of use thereof, nail cosmetic composition and nail cosmetic resin |
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