JP5563277B2 - 含水性眼用レンズ - Google Patents
含水性眼用レンズ Download PDFInfo
- Publication number
- JP5563277B2 JP5563277B2 JP2009250468A JP2009250468A JP5563277B2 JP 5563277 B2 JP5563277 B2 JP 5563277B2 JP 2009250468 A JP2009250468 A JP 2009250468A JP 2009250468 A JP2009250468 A JP 2009250468A JP 5563277 B2 JP5563277 B2 JP 5563277B2
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- JP
- Japan
- Prior art keywords
- monomer
- meth
- acrylate
- hydrophilic monomer
- combination
- 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.)
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- 239000000178 monomer Substances 0.000 claims description 145
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 111
- -1 trimethylsiloxy group Chemical group 0.000 claims description 98
- 229920001296 polysiloxane Polymers 0.000 claims description 76
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 72
- 239000000017 hydrogel Substances 0.000 claims description 39
- 229960003237 betaine Drugs 0.000 claims description 37
- 125000000129 anionic group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 17
- 125000002091 cationic group Chemical group 0.000 claims description 16
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000003505 polymerization initiator Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 8
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 8
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical group CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 claims description 8
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical group [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 claims description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 7
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical group CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 6
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 6
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims description 5
- 229940072049 amyl acetate Drugs 0.000 claims description 5
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 5
- SJBHHYCVWDNTMV-UHFFFAOYSA-N butyl decaneperoxoate Chemical group CCCCCCCCCC(=O)OOCCCC SJBHHYCVWDNTMV-UHFFFAOYSA-N 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 4
- UZMZRFVLRULBOV-UHFFFAOYSA-N 2-[dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azaniumyl]acetate Chemical group CC(=C)C(=O)OCC[N+](C)(C)CC([O-])=O UZMZRFVLRULBOV-UHFFFAOYSA-N 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229940023490 ophthalmic product Drugs 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- 229910052760 oxygen Inorganic materials 0.000 description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 17
- 239000001301 oxygen Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000035699 permeability Effects 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
- 238000002156 mixing Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000009832 plasma treatment Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- GJFVMCSNEKFOLR-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethylamino)acetic acid Chemical compound C=CC(=O)OCCNCC(=O)O GJFVMCSNEKFOLR-UHFFFAOYSA-N 0.000 description 2
- UVHHURULWXETLK-UHFFFAOYSA-N 2-(3-prop-2-enoyloxypropylamino)acetic acid Chemical compound C=CC(=O)OCCCNCC(=O)O UVHHURULWXETLK-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- FRSLHNAVGFDJRN-UHFFFAOYSA-N 2-[3-(prop-2-enoylamino)propylamino]acetic acid Chemical compound C=CC(=O)NCCCNCC(=O)O FRSLHNAVGFDJRN-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- RGXDTJFXJVLDCV-UHFFFAOYSA-N 3-(2-prop-2-enoyloxyethylamino)propanoic acid Chemical compound C=CC(=O)OCCNCCC(=O)O RGXDTJFXJVLDCV-UHFFFAOYSA-N 0.000 description 2
- WCICPQPUOQXUSA-UHFFFAOYSA-N 3-(2-prop-2-enoyloxyethylazaniumyl)propane-1-sulfonate Chemical compound O=C(OCC[NH2+]CCCS(=O)(=O)[O-])C=C WCICPQPUOQXUSA-UHFFFAOYSA-N 0.000 description 2
- KEKNFQUOMBWNNK-UHFFFAOYSA-N 3-(3-prop-2-enoyloxypropylamino)propane-1-sulfonic acid Chemical compound C=CC(=O)OCCCNCCCS(=O)(=O)O KEKNFQUOMBWNNK-UHFFFAOYSA-N 0.000 description 2
- GKVLNMYEIQABEZ-UHFFFAOYSA-N 3-(3-prop-2-enoyloxypropylamino)propanoic acid Chemical compound C=CC(=O)OCCCNCCC(=O)O GKVLNMYEIQABEZ-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- ISOVAHDCMDPEDJ-UHFFFAOYSA-N C=CC(=O)NCCCNCCC(=O)O Chemical compound C=CC(=O)NCCCNCCC(=O)O ISOVAHDCMDPEDJ-UHFFFAOYSA-N 0.000 description 2
- KVVTWCASUCEURQ-UHFFFAOYSA-N C=CC(=O)NCCCNCS(=O)(=O)O Chemical compound C=CC(=O)NCCCNCS(=O)(=O)O KVVTWCASUCEURQ-UHFFFAOYSA-N 0.000 description 2
- CELKZFVZJZQMQT-UHFFFAOYSA-N C=CC(=O)OCCCNCS(=O)(=O)O Chemical compound C=CC(=O)OCCCNCS(=O)(=O)O CELKZFVZJZQMQT-UHFFFAOYSA-N 0.000 description 2
- DZLMEQJCZUPPPW-UHFFFAOYSA-N C=CC(=O)OCCNCS(=O)(=O)O Chemical compound C=CC(=O)OCCNCS(=O)(=O)O DZLMEQJCZUPPPW-UHFFFAOYSA-N 0.000 description 2
- LYLSUALFIRYWAQ-UHFFFAOYSA-N C=CC(=O)OCNCCC(=O)O Chemical compound C=CC(=O)OCNCCC(=O)O LYLSUALFIRYWAQ-UHFFFAOYSA-N 0.000 description 2
- ZLLLSGCCDJRTJK-UHFFFAOYSA-N C=CC(=O)OCNCCCS(=O)(=O)O Chemical compound C=CC(=O)OCNCCCS(=O)(=O)O ZLLLSGCCDJRTJK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- IYTXKIXETAELAV-UHFFFAOYSA-N Nonan-3-one Chemical compound CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 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 2
- 230000000694 effects Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- LSTDYDRCKUBPDI-UHFFFAOYSA-N palmityl acetate Chemical compound CCCCCCCCCCCCCCCCOC(C)=O LSTDYDRCKUBPDI-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- MPXHLFZVRCWKOH-UHFFFAOYSA-N (2-benzoyl-4-tert-butylphenyl) prop-2-enoate Chemical compound CC(C)(C)c1ccc(OC(=O)C=C)c(c1)C(=O)c1ccccc1 MPXHLFZVRCWKOH-UHFFFAOYSA-N 0.000 description 1
- DSTUKHPLWATFCG-UHFFFAOYSA-N (2-benzoylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C(=O)C1=CC=CC=C1 DSTUKHPLWATFCG-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical group C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- QEZDYNRKJXCIFE-WAYWQWQTSA-N (z)-3-carbonoperoxoylhept-2-enoic acid Chemical group CCCC\C(=C\C(O)=O)C(=O)OO QEZDYNRKJXCIFE-WAYWQWQTSA-N 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-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
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
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- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical compound C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 description 1
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 description 1
- FBQZJBMRDNLFQO-UWVGGRQHSA-N bis[(3S)-3-methoxybutyl] ethanediperoxoate Chemical compound CO[C@@H](C)CCOOC(=O)C(=O)OOCC[C@H](C)OC FBQZJBMRDNLFQO-UWVGGRQHSA-N 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- DTGWMJJKPLJKQD-UHFFFAOYSA-N butyl 2,2-dimethylpropaneperoxoate Chemical group CCCCOOC(=O)C(C)(C)C DTGWMJJKPLJKQD-UHFFFAOYSA-N 0.000 description 1
- RHZIVIGKRFVETQ-UHFFFAOYSA-N butyl 2-methylpropaneperoxoate Chemical group CCCCOOC(=O)C(C)C RHZIVIGKRFVETQ-UHFFFAOYSA-N 0.000 description 1
- DDMBAIHCDCYZAG-UHFFFAOYSA-N butyl 7,7-dimethyloctaneperoxoate Chemical group CCCCOOC(=O)CCCCCC(C)(C)C DDMBAIHCDCYZAG-UHFFFAOYSA-N 0.000 description 1
- JWKNCJFGBOQAQL-UHFFFAOYSA-N butyl dodecaneperoxoate Chemical group CCCCCCCCCCCC(=O)OOCCCC JWKNCJFGBOQAQL-UHFFFAOYSA-N 0.000 description 1
- NHEUUFQZSIJBCY-UHFFFAOYSA-N butylperoxy 2-ethylhexyl carbonate Chemical group CCCCOOOC(=O)OCC(CC)CCCC NHEUUFQZSIJBCY-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940049297 cetyl acetate Drugs 0.000 description 1
- 229940074979 cetyl palmitate Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 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 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QQQMUBLXDAFBRH-UHFFFAOYSA-N dodecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)O QQQMUBLXDAFBRH-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- HOKAWVDPFJBMEJ-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate hydrate Chemical compound O.C(C(=C)C)(=O)OCC HOKAWVDPFJBMEJ-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- JHOSFAWABWXPSA-UHFFFAOYSA-M ethyl-dimethyl-(2-methylprop-2-enoyloxymethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CC[N+](C)(C)COC(=O)C(C)=C JHOSFAWABWXPSA-UHFFFAOYSA-M 0.000 description 1
- QUUVXPUXYIWGHA-UHFFFAOYSA-M ethyl-dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CC[N+](C)(C)CCOC(=O)C(C)=C QUUVXPUXYIWGHA-UHFFFAOYSA-M 0.000 description 1
- XPBSEOOJTGAFHS-UHFFFAOYSA-N ethyl-dimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CC[N+](C)(C)CCCNC(=O)C(C)=C XPBSEOOJTGAFHS-UHFFFAOYSA-N 0.000 description 1
- GJQLBGWSDGMZKM-UHFFFAOYSA-N ethylhexyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(CC)CCCCC GJQLBGWSDGMZKM-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 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
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- NQUPKCJGWCPODR-UHFFFAOYSA-N hexaneperoxoic acid Chemical group CCCCCC(=O)OO NQUPKCJGWCPODR-UHFFFAOYSA-N 0.000 description 1
- MBOQKJVESPQPMS-UHFFFAOYSA-N hexyl 7,7-dimethyloctaneperoxoate Chemical group CCCCCCOOC(=O)CCCCCC(C)(C)C MBOQKJVESPQPMS-UHFFFAOYSA-N 0.000 description 1
- QZEJHHGVNNHHSU-UHFFFAOYSA-N hexyl benzenecarboperoxoate Chemical group CCCCCCOOC(=O)C1=CC=CC=C1 QZEJHHGVNNHHSU-UHFFFAOYSA-N 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940075495 isopropyl palmitate Drugs 0.000 description 1
- 229940113915 isostearyl palmitate Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- PZWZMVCYWFZOHE-UHFFFAOYSA-N methyl 2-[(1-methoxy-1-oxobutan-2-yl)diazenyl]butanoate Chemical compound COC(=O)C(CC)N=NC(CC)C(=O)OC PZWZMVCYWFZOHE-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CCRIVCWOXSIYEP-UHFFFAOYSA-N methyl prop-2-enoate;hydrochloride Chemical compound Cl.COC(=O)C=C CCRIVCWOXSIYEP-UHFFFAOYSA-N 0.000 description 1
- FSQHDIAYKNDZFC-UHFFFAOYSA-N methyl sulfate;trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium Chemical compound COS([O-])(=O)=O.CC(=C)C(=O)NCCC[N+](C)(C)C FSQHDIAYKNDZFC-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- DCBBWYIVFRLKCD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-methylprop-2-enamide Chemical compound CN(C)CCNC(=O)C(C)=C DCBBWYIVFRLKCD-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
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 description 1
- DFMIMUDDPBAKFS-UHFFFAOYSA-N n-ethenyl-n-ethylformamide Chemical compound CCN(C=C)C=O DFMIMUDDPBAKFS-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-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
- 239000012299 nitrogen atmosphere Substances 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
- XNTUJOTWIMFEQS-UHFFFAOYSA-N octadecanoyl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCCCC XNTUJOTWIMFEQS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
- 229940077397 octyldodecyl lactate Drugs 0.000 description 1
- 150000001451 organic peroxides Chemical group 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- HPUOAJPGWQQRNT-UHFFFAOYSA-N pentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1 HPUOAJPGWQQRNT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- MHWRYTCHHJGQFQ-UHFFFAOYSA-N prop-2-enoic acid hydrate Chemical compound O.OC(=O)C=C MHWRYTCHHJGQFQ-UHFFFAOYSA-N 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 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
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 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
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- WDUXKFKVDQRWJN-UHFFFAOYSA-N triethoxysilylmethyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C=C WDUXKFKVDQRWJN-UHFFFAOYSA-N 0.000 description 1
- USFMMZYROHDWPJ-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound CC(=C)C(=O)OCC[N+](C)(C)C USFMMZYROHDWPJ-UHFFFAOYSA-N 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- NFUDTVOYLQNLPF-UHFFFAOYSA-M trimethyl-[3-(2-methylprop-2-enoyloxy)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCCC[N+](C)(C)C NFUDTVOYLQNLPF-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Processes Of Treating Macromolecular Substances (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Eyeglasses (AREA)
Description
イオン性モノマーの配合量は0.1〜15重量%であり、好ましくは0.5〜10重量%である。イオン性モノマーの含有量が0.1重量%未満であると、得られたシリコーンハイドロゲル眼用レンズの表面に親水性が付与されず、また、15重量%を超えると疎水性成分との相溶性が低下し好ましくない。
以下、本発明の好ましい実施例を説明するが、この実施例は本発明の理解のために提供されるものであって、本発明の範囲がかかる実施例のみに限定されるものではない。
実施例及び比較例における膨潤状態のシリコーンハイドロゲル眼用レンズの評価方法として、以下の試験、評価基準を採用した。
膨潤後のシリコーンハイドロゲル眼用レンズを37±2℃の生理食塩水に24時間浸漬し、その後取り出したときのレンズ表面の水濡れ性を目視にて評価した。
「プラスチックの引っ張り試験法(JIS K 7113)」に基づき試験片を調整し、膨潤したものをサンプルとして伸縮性及び強度を測定した。
シリコーンハイドロゲル眼用レンズの透明性を目視にて評価した。
[酸素透過係数]
シリコーンハイドロゲル眼用レンズ成形体の酸素透過量の評価として、コンタクトレンズ製造・輸入承認申請マニュアル(日本コンタクトレンズ協会)に記載の「改良電極法によるDk値測定作業手順書」に基づき酸素透過係数(Dk値)を測定した。
シリコーン含有(メタ)アクリレートとして3−[トリス(トリメチルシロキシ)シリル]プロピルメタクリレート(SiMA 信越化学工業株式会社製)、ポリシロキサンマクロモノマーとしてα,ω−ジ(3−メタクリロキシプロピル)ポリジメチルシロキサン(FM−7725 チッソ株式会社製)、親水性モノマーとしてN−ビニルピロリドン(NVP)、N,N−ジメチルアクリルアミド(DMAA)、2−ヒドロキシエチルメタクリレート(HEMA)、アニオン性モノマーとしてメタクリル酸(MAA)、カチオン性モノマーとしてメタクリルアミドプロピルトリメチルアンモニウムクロライド(MAPTAC)、双性イオンモノマーとしてN,N−ジメチル−N−メタクリロイルオキシエチル−N−カルボキシメチル−アンモニウムベタイン(GLBT 大阪有機化学工業社製)、非親水性成分としてトリデシルメタクリレート(TDMA)、2−エチルヘキシルアクリレート(EHA)、エチレングリコールジメタクリレート(ED)を表1に示す配合量で混合した後に、両親媒性物質である酢酸ブチル(BuOAc)、酢酸アミル(AmOAc)、メチルイソブチルケトン(MIBK)、メチルイソプロピルケトン(MIPK)、ターシャリーブチルアルコール(t−BuOH)を表1に示す配合量で添加し、重合開始剤として、ターシャリーブチルパーオキシデカノエート(t−BuND)又は2,2'−アゾビスイソブチロニトリル(AIBN)を表1に示す配合量で添加した。
本発明の必須成分である両親媒性物質を使用せず、その他成分については実施例1と同様の手順で原料の調製を行った。しかしながら、均一溶液を得られず、シリコーンハイドロゲル眼用レンズを作製するに至らなかった。
用いた両親媒性物質の沸点が70℃以下である以外、その他成分については実施例1と同様の手順で原料の調製を行った。攪拌時均一溶液となったが、得られたシリコーンハイドロゲル眼用レンズは白化しており、また表面は著しく撥水していた。
本発明の必須成分であるイオン性モノマーを添加せず、その他成分については実施例1と同様の手順でレンズを作製し評価した。得られたシリコーンハイドロゲル眼用レンズ表面は著しく撥水していた。
Claims (10)
- 下記一般式(3)
で示されるポリシロキサンマクロモノマーと、
イオン性モノマー及び親水性モノマーを含む単量体混合物と、
重合開始剤と、
を両親媒性物質に溶解して得た溶液での共重合反応で得られるシリコーンハイドロゲル眼用レンズであって、
前記単量体混合物は、親水性モノマーとアニオン性モノマーと非親水性モノマーの組み合わせ、シリコーン含有(メタ)アクリレートと前記親水性モノマーと前記アニオン性モノマーと前記非親水性モノマーとの組み合わせ、前記シリコーン含有(メタ)アクリレートと前記親水性モノマーと前記アニオン性モノマーとの組み合わせ、前記親水性モノマーと前記アニオン性モノマーとカチオン性モノマーと前記非親水性モノマーとの組み合わせ、前記親水性モノマーと双性イオンモノマーと前記非親水性モノマーとの組み合わせからなる一群から選択され、及び、
前記ポリシロキサンマクロモノマーの配合量は25〜40重量部であり、かつ、前記単量体混合物の配合量は75〜60重量部であることを特徴とする、前記シリコーンハイドロゲル眼用レンズ。 - 前記両親媒性物質は、沸点70〜200℃の有機溶媒であり、単量体混合物の総量100重量%に対して20〜70重量%であり、かつ、酢酸エステル、分岐鎖状ケトン、前記酢酸エステルと分岐鎖状アルコールとの組み合わせ及び前記分岐鎖状ケトンと前記分岐鎖状アルコールとの組み合わせからなる一群から選択されることを特徴とする請求項1に記載のシリコーンハイドロゲル眼用レンズ。
- 前記両親媒性物質のうち、前記酢酸エステルは酢酸ブチル又は酢酸アミルであり、前記分岐鎖状ケトンはメチルイソブチルケトン又はメチルイソプロピルケトンであり、前記分岐鎖状アルコールはターシャリーブチルアルコールであることを特徴とする請求項2に記載のシリコーンハイドロゲル眼用レンズ。
- 前記単量体混合物は、
前記親水性モノマーが、N−ビニルピロリドン、N,N−ジメチルアクリルアミド及び2−ヒドロキシエチルメタクリレートからなる一群から選択されたものであり、
前記非親水性モノマーが、トリデシルメタクリレート、2−エチルヘキシルアクリレート及びエチレングリコールジメタクリレートからなる一群から選択されたものであり、
前記シリコーン含有(メタ)アクリレートが、3−[トリス(トリメチルシロキシ)シリル]プロピルメタクリレートであり、
前記アニオン性モノマーが、メタクリル酸であり、
前記カチオン性モノマーが、メタクリルアミドプロピルトリメチルアンモニウムクロライドであり、
前記双性イオンモノマーがN,N−ジメチル−N−メタクリロイルオキシエチル−N−カルボキシメチル−アンモニウムベタインであることを特徴とする請求項1〜3のいずれか1項に記載のシリコーンハイドロゲル眼用レンズ。 - 前記重合開始剤は、ターシャリーブチルパーオキシデカノエート又は2,2'−アゾビスイソブチロニトリルであることを特徴とする請求項1〜4のいずれか1項に記載のシリコーンハイドロゲル眼用レンズ。
- 下記一般式(3)
で示されるポリシロキサンマクロモノマーと、イオン性モノマー及び親水性モノマーを含む単量体混合物と、重合開始剤と、を両親媒性物質に溶解して溶液を得る手順と、
該溶液で共重合反応をさせる手順と、
を備えることを特徴とするシリコーンハイドロゲル眼用レンズの製造方法であって、
前記単量体混合物は、親水性モノマーとアニオン性モノマーと非親水性モノマーの組み合わせ、シリコーン含有(メタ)アクリレートと前記親水性モノマーと前記アニオン性モノマーと前記非親水性モノマーとの組み合わせ、前記シリコーン含有(メタ)アクリレートと前記親水性モノマーと前記アニオン性モノマーとの組み合わせ、前記親水性モノマーと前記アニオン性モノマーとカチオン性モノマーと前記非親水性モノマーとの組み合わせ、前記親水性モノマーと双性イオンモノマーと前記非親水性モノマーとの組み合わせからなる一群から選択され、及び、
前記ポリシロキサンマクロモノマーの配合量は25〜40重量部であり、かつ、前記単量体混合物の配合量は75〜60重量部であることを特徴とする、前記シリコーンハイドロゲル眼用レンズの製造方法。 - 前記両親媒性物質は、沸点70〜200℃の有機溶媒であり、単量体混合物の総量100重量%に対して20〜70重量%であり、かつ、酢酸エステル、分岐鎖状ケトン、前記酢酸エステルと分岐鎖状アルコールとの組み合わせ及び前記分岐鎖状ケトンと前記分岐鎖状アルコールとの組み合わせからなる一群から選択されることを特徴とする請求項6に記載のシリコーンハイドロゲル眼用レンズの製造方法。
- 前記両親媒性物質のうち、前記酢酸エステルは酢酸ブチル又は酢酸アミルであり、前記分岐鎖状ケトンはメチルイソブチルケトン又はメチルイソプロピルケトンであり、前記分岐鎖状アルコールはターシャリーブチルアルコールであることを特徴とする請求項7に記載のシリコーンハイドロゲル眼用レンズの製造方法。
- 前記単量体混合物は、
前記親水性モノマーが、N−ビニルピロリドン、N,N−ジメチルアクリルアミド及び2−ヒドロキシエチルメタクリレートからなる一群から選択されたものであり、前記非親水性モノマーが、トリデシルメタクリレート、2−エチルヘキシルアクリレート及びエチレングリコールジメタクリレートからなる一群から選択されたものであり、
前記シリコーン含有(メタ)アクリレートが、3−[トリス(トリメチルシロキシ)シリル]プロピルメタクリレートであり、
前記アニオン性モノマーが、メタクリル酸であり、
前記カチオン性モノマーが、メタクリルアミドプロピルトリメチルアンモニウムクロライドであり、
前記双性イオンモノマーがN,N−ジメチル−N−メタクリロイルオキシエチル−N−カルボキシメチル−アンモニウムベタインであることを特徴とする請求項6〜8のいずれか1項に記載のシリコーンハイドロゲル眼用レンズの製造方法。 - 前記重合開始剤は、ターシャリーブチルパーオキシデカノエート又は2,2'−アゾビスイソブチロニトリルであることを特徴とする請求項6〜9のいずれか1項に記載のシリコーンハイドロゲル眼用レンズの製造方法。
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