JP5405459B2 - 可溶性シリコーンプレポリマー - Google Patents
可溶性シリコーンプレポリマー Download PDFInfo
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- JP5405459B2 JP5405459B2 JP2010515175A JP2010515175A JP5405459B2 JP 5405459 B2 JP5405459 B2 JP 5405459B2 JP 2010515175 A JP2010515175 A JP 2010515175A JP 2010515175 A JP2010515175 A JP 2010515175A JP 5405459 B2 JP5405459 B2 JP 5405459B2
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- prepolymer
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- 229920001296 polysiloxane Polymers 0.000 title claims description 46
- -1 methoxyethyl Chemical group 0.000 claims description 99
- 239000000203 mixture Substances 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 229920000642 polymer Polymers 0.000 claims description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000005401 siloxanyl group Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 239000010703 silicon Substances 0.000 claims description 14
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 8
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 7
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000003021 water soluble solvent Substances 0.000 claims description 4
- HGMWQAGLTXDVEW-UHFFFAOYSA-N 1-ethenyl-3-(2-methylbutyl)aziridin-2-one Chemical compound CCC(C)CC1N(C=C)C1=O HGMWQAGLTXDVEW-UHFFFAOYSA-N 0.000 claims description 3
- SBEBZMZHYUEOPQ-UHFFFAOYSA-N 1-ethenyl-3-methylpiperidin-2-one Chemical compound CC1CCCN(C=C)C1=O SBEBZMZHYUEOPQ-UHFFFAOYSA-N 0.000 claims description 3
- HKOOECSKKYAKJJ-UHFFFAOYSA-N 1-ethenyl-3-pentan-2-ylaziridin-2-one Chemical compound CCCC(C)C1N(C=C)C1=O HKOOECSKKYAKJJ-UHFFFAOYSA-N 0.000 claims description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical group C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical group NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical group NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- FEXNALLEMIXMBU-UHFFFAOYSA-N (4-ethenylbenzoyl) 4-ethenylbenzoate Chemical compound C1=CC(C=C)=CC=C1C(=O)OC(=O)C1=CC=C(C=C)C=C1 FEXNALLEMIXMBU-UHFFFAOYSA-N 0.000 claims description 2
- JFUWJIKJUNAHEN-UHFFFAOYSA-N 1-ethenyl-3-ethylpyrrolidin-2-one Chemical compound CCC1CCN(C=C)C1=O JFUWJIKJUNAHEN-UHFFFAOYSA-N 0.000 claims description 2
- JBKFPCSZNWLZAS-UHFFFAOYSA-N 1-ethenyl-4-methylpiperidin-2-one Chemical compound CC1CCN(C=C)C(=O)C1 JBKFPCSZNWLZAS-UHFFFAOYSA-N 0.000 claims description 2
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- GAVHQOUUSHBDAA-UHFFFAOYSA-N 3-butyl-1-ethenylaziridin-2-one Chemical compound CCCCC1N(C=C)C1=O GAVHQOUUSHBDAA-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- FXPHJTKVWZVEGA-UHFFFAOYSA-N ethenyl hydrogen carbonate Chemical group OC(=O)OC=C FXPHJTKVWZVEGA-UHFFFAOYSA-N 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- YOSXAXYCARLZTR-UHFFFAOYSA-N prop-2-enoyl isocyanate Chemical compound C=CC(=O)N=C=O YOSXAXYCARLZTR-UHFFFAOYSA-N 0.000 claims description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000178 monomer Substances 0.000 description 45
- 238000006116 polymerization reaction Methods 0.000 description 36
- 125000000753 cycloalkyl group Chemical group 0.000 description 30
- 238000000034 method Methods 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 25
- 229910052760 oxygen Inorganic materials 0.000 description 25
- 239000001301 oxygen Substances 0.000 description 25
- 125000000392 cycloalkenyl group Chemical group 0.000 description 24
- 125000000304 alkynyl group Chemical group 0.000 description 21
- 238000004821 distillation Methods 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 20
- 125000001072 heteroaryl group Chemical group 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 230000035699 permeability Effects 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920003023 plastic Polymers 0.000 description 10
- 239000004033 plastic Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 238000010137 moulding (plastic) Methods 0.000 description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 150000001540 azides Chemical class 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 210000004087 cornea Anatomy 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000012719 thermal polymerization Methods 0.000 description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229910002808 Si–O–Si Inorganic materials 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 3
- 239000013626 chemical specie Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid group Chemical group C(CCCCCCCCC(=O)O)(=O)O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CRJHKHYPIUPQSX-UHFFFAOYSA-N 1-ethenyl-4,5-dimethylpyrrolidin-2-one Chemical compound CC1CC(=O)N(C=C)C1C CRJHKHYPIUPQSX-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 150000005347 biaryls Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
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- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
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- 230000008707 rearrangement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
- C08F220/387—Esters containing sulfur and containing nitrogen and oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
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Description
本出願は、2007年6月29日に出願した米国特許出願第11/771,999号に基づく優先権を主張するものであり、その全文は、参照により本明細書に組み込まれる。
本明細書及び添付する請求項において、単数形の「一つの(a)」、「一つの(an)」及び「該(the)」には、その文に明確な指摘のない限り、複数形の指示対象も含まれる。従って、例えば、「1つの成分(a component)」、「1つのポリマー(a polymer)」又は「1つの残基(a residue)」には、2つ以上のこれらの成分、ポリマー又は残基等の混合物が含まれる。
ある局面において、本発明は、1以上のシリコーンプレポリマーに関する。より具体的には、化合物は、所望しない収縮、伸長並びに従来のシリコーンモノマーが有し及び従来の重合技術に関連した関連問題を、比較的低分子量並びに低多分散性を有する架橋性のプレポリマーからヒドロゲルを生産することで克服できることを開示する。さらに、十分な酸素透過性を有しつつ、水溶液又は、例えばポリ(エチレングリコール)/ポリ(ビニルピロリドン)(PEG/PVP)等の親水性溶液への十分な溶解度を提供する構造を有するプレポリマーを調製することを開示する。
ある局面では、プレポリマーは、以下の式で表わされる構造:
を有する少なくとも1種のケイ素含有残基と、以下の式
で表わされる構造を有する重合可能な残基を含み;プレポリマーは、該プレポリマーの10重量%〜30重量%のケイ素を有しており;少なくとも1種のケイ素含有残基の少なくとも1つは、少なくとも1種の極性部位をさらに含む極性シリコーン含有残基であり;そして、プレポリマーは、該プレポリマーの30重量%〜90重量%の極性シリコーン含有残基を有している、化合物又は化合物の集合であり得る。
ある局面では、開示されたプレポリマーは1個以上のシロキサニル基を含む。特に記載のない限り、シロキサニル基は、当業者に公知のいかなるシロキサニル基であっても良い。
ある局面では、開示されたプレポリマーは1つ以上の親水性残基を含む。特に記載のない限り、親水性残基は当業者に公知のいかなる親水性残基であっても良い。ある局面では、親水性残基は開示されたプレポリマーに存在していなくても良い。
開示されたプレポリマーは1個以上の極性部分を含む。極性部分はヒドロキシル、アミド、カルボキシ、アミノ、カーボネート、カルバメート、スルホンアミド、スルホン酸基、ホスホン酸基、メトキシエチル、メトキシエトキシエチル、ヒドロキシエチル又はヒドロキシエトキシエチルである。
開示されたプレポリマーは1個以上の重合可能な残基または基を含む。重合可能残基は1個以上のエチレン性不飽和部位、例えば、メタクリロイルオキシ基、アクリロイルオキシ基、メタクリルアミド基、アクリルアミド基、スチリル基、ビニル基、ビニルカーボネート基、ビニルカルバメート基、アリルカーボネート基又はアリルカルバメート基を含む。
開示されたプレポリマーは、該プレポリマーを調製するために用いる重合反応の開始時及び終了時に生じる末端基を有していても良いと理解されるべきである。例えば、プレポリマーは、開始反応で生じ、そして以下の式で表わされる構造を有する末端基を有していても良い:
ある局面において、開示されたプレポリマーのケイ素含有量は10重量%〜30重量%であり得る。さらなる局面では、開示されたプレポリマーのケイ素含有量は13重量%〜20重量%であり得る。例えば、ケイ素含有量は15%〜20%、13%〜18%、15%〜18%、13%、15%、18%又は20%であり得る。開示されたケイ素含有量は、シリコーンプレポリマーの集合に対する平均ケイ素含有量を表わし得ることも理解される。
ある局面において、開示されたプレポリマーは、例えば、PEG/PVPのような水溶液又は親水性溶液に優れた溶解度を示す。多くの異なる溶媒中にプレポリマーの試料を保管する溶解度試験で、溶解度を測定することができる。ポリマーが溶解、膨潤、又は変化しないかどうかを観察することにより、プレポリマーが任意の溶媒系に溶解するかどうか及びどの程度溶解するかを確認することが可能である。Hansen Solubility Parameters;A User's Handbook、Charles M. Hansen、43〜53ページ、CRC Press 2000参照。例えば、既知の質量のプレポリマーを、過剰量の任意の溶媒系に一定時間(例えば、10分)さらしても良い。混合物は、超音波処理されても及び/又は高温にさらされても良い。その後、すべての不溶性プレポリマーをデカンテーション又はろ過で取り除き、溶媒系中の可溶物の割合を計算することができる。
ある局面において、開示されたプレポリマーは約10kDa〜約1000kDa、例えば、約10kDa〜約500kDa、約10kDa〜約300kDa、又は約10kDa〜約200kDaの平均分子量を有していても良い。ある局面において、開示されたプレポリマーの多分散性(Mw/Mn)は、約1.00〜約10.00であって良い。例えば、多分散性は、約1.00〜約9.00、約1.00〜約8.00、約1.00〜約7.00、約1.00〜約6.00、又は約1.00〜約5.00であって良い。さらなる局面では、多分散性は約8より小さくても良い。例えば、約7.5より小さく、約7より小さく、約6.5より小さく、約6より小さく、約5.5より小さく、約5より小さく、約4.5より小さく、約4より小さいくてもよい。
開示されたプレポリマーは、該プレポリマーが約10重量%〜約30重量%のケイ素含量を維持し、該プレポリマーの約30重量%〜約90重量%のシリコーン含有残基含量を維持する限り、さらなるコモノマーからの残基をさらに含んでいても良いことも意図される。このようなコモノマーの好ましい例として、(メタ)アクリル酸、イタコン酸、クロトン酸、ケイ皮酸、ビニル安息香酸、メチル(メタ)アクリレート及びエチル(メタ)アクリレート等のアルキル(メタ)アクリレート;ポリアルキレングリコールモノ(メタ)アクリレート、ポリアルキレングリコールモノアルキルエーテル(メタ)アクリレート、ポリアルキレングリコールビス(メタ)アクリレート、トリメチロールプロパントリス(メタ)アクリレート、ペンタエリスリトールテトラキス(メタ)アクリレート、両末端に(メタ)アクリロキシプロピル基を有するポリジメチルシロキサン、片方の末端に(メタ)アクリロキシプロピル基を有したポリジメチルシロキサン及び側鎖に複数の(メタ)アクリロイル基を有したポリジメチルシロキサン等の多官能性(メタ)アクリレート;トリフルオロエチル(メタ)アクリレート及びヘキサフルオロイソプロピル(メタ)アクリレート等のハロゲン化アルキル(メタ)アクリレート;2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート及び2,3-ジヒドロキシプロピル(メタ)アクリレート等のヒドロキシル基を有するヒドロキシアルキル(メタ)アクリレート;N,N-ジメチルアクリルアミド、N,N-ジエチルアクリルアミド、N,N-ジ-n-プロピルアクリルアミド、N,N-ジイソプロピルアクリルアミド、N,N-ジ-n-ブチルアクリルアミド、N-アクリロイルモルフォリン、N-アクリロイルピペリジン、N-アクリロイルピロリドン及びN-メチル(メタ)アクリルアミド等の(メタ)アクリルアミド;N-ビニル-N-メチルアセトアミド、N-ビニル-N-エチルアセトアミド、N-ビニル-N-エチルホルムアミド、N-ビニルホルムアミド、スチレン、α-メチルスチレン及びビニルピリジン等の芳香族ビニルモノマー;マレイミド;N-ビニルピロリドン等の複素環式ビニルモノマー;3-[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、3-[ビス(トリメチルシロキシ)メチルシリル]プロピル(メタ)アクリレート、3-[(トリメチルシロキシ)ジメチルシリル]プロピル(メタ)アクリレート、3-[トリス(トリメチルシロキシ)シリル]プロピル(メタ)アクリルアミド、3-[ビス(トリメチルシロキシ)メチルシリル]プロピル(メタ)アクリルアミド、3-[(トリメチルシロキシ)ジメチルシリル]プロピル(メタ)アクリルアミド、[トリス(トリメチルシロキシ)シリル]メチル(メタ)アクリレート、[ビス(トリメチルシロキシ)メチルシリル]メチル(メタ)アクリレート、[(トリメチルシロキシ)ジメチルシリル]メチル(メタ)アクリレート、[トリス(トリメチルシロキシ)シリル]メチル(メタ)アクリルアミド、[ビス(トリメチルシロキシ)メチルシリル]メチル(メタ)アクリルアミド、[(トリメチルシロキシ)ジメチルシリル]メチル(メタ)アクリルアミド、[トリス(トリメチルシロキシ)シリル]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)ジメチルシリル]スチレン、片方の末端に(メタ)アクリロキシプロピル基を有したポリジメチルシロキサン、並びに下記の式(C1-1)〜(C6-1)及び(C6-2)で表わされる化合物が挙げられる。
ある局面において、本発明はプレポリマーの製造方法に関する。プレポリマーに関して開示された化合物、構造、及び部位が、開示された方法に関連して用いられても良いと理解されるべきである。
ある局面において、該プレポリマーは、例えば、熱開始又は光開始重合若しくは架橋反応によりさらに調製するために用いることができる。したがって、さらなる局面では、本発明は、1つ以上の開示されたプレポリマーを重合又は架橋させることにより得られるポリマーに関する。
本発明は、十分な酸素透過性、満足できる親水性及び満足できる破壊耐性を有するプラスチック成型体を重合により製造可能な原料を提供する。該プラスチック成型体は、ドラッグデリバリー用の薬剤吸収剤、及びコンタクトレンズ、眼内レンズ、人工角膜及び眼鏡レンズ等の眼用レンズとして有用である。中でも、コンタクトレンズに特に好適である。
下記の実施例は、当業者に、本出願の請求項に係る化合物、組成物、製品、装置及び/又は方法を作製して評価する方法について完全な開示と記載を提供するために示されるものであり、単に本発明の例示として意図されているに過ぎず、本発明者らが彼らの発明と見なす範囲を制限することを意図するものではない。数値(例えば、量、温度等)については、正確を期するために尽力したが、誤差や偏差も考慮すべきである。特に他に表示のない限り、部(parts)は重量部であり、温度は℃であるか又は周囲温度であり、圧力は、大気圧であるか又はその前後である。
分子量:サイズ排除クロマトグラフィー(SEC)装置は、40℃のカラム・オーブン、PE Nelson 900 A/Dを備えたaPE LC-410ポンプ及びシリーズ200オートサンプラーから構成されている。検出器は、RI Merck L7490であることができる。カラムの組み合わせは、2種類のTosoHaas社製TSK-ゲル カラム(G4000PW+G2500PW)及びガードカラムからなることができる。溶離剤は、メタノール-水(75/25 wt/wt)から作ることができ、50mM塩化ナトリウム(NaCl)に調整された。注入量は150μlで、実行時間は60分であることができる。標準対照として、分子量ピークが960000〜194のPEG及びPEOを用い3次回帰で検量線を得ることができる。これらの標準ポリマーはPolymer Laboratories Inc(アマースト、マサチューセッツ)から購入できる(キャリブレーションキット PEG-10 部品番号 2070-0100;PEO 部品番号 2080-0101)。194のピーク分子量である添加された標準対照のPEGは、内部標準又は凝視点として用いられる明確な点でのフローシグナルを与える。添加されたNaClは、同様の役割を果たし、第2の凝視点を与える。ピーク積分は手動でなされ得る。積分開始点及び終了点を手動で全体のベースライン上の有意差から定量できる。2mg/mLのポリマー濃度を与える60mMNaClに調整するメタノール-水75/25wt/wtから、注入溶液を調製できる。ピークフローの対照を与えるために、1mg/mL濃度のサンプルにテトラエチレングリコールを加えることもできる。注入する前に、溶液を0.5μm使い捨てフィルター上でろ過することが好ましい。ポリマー試料の多分散、PdをPd=Mw/Mnと定義することができる。分子量のピークMpは、分子量分布曲線中の最も高いピーク分子量である。
含水率(%)=100×(Ww−Wd)/Ww
51.14gの以下の式(h)で表わされるシリコーンモノマー(SiMAA):
重合混合物の組成物を表1に示すように変えたことを除き、実施例1と同様の操作を繰り返した。表1に示されていないが、UV吸収剤、色素(r)、DBTDL及びBHTも、実施例1と同様の比率で使用した。
重合混合物の組成を表1に示すように変えたことを除き、実施例1と同様の操作を繰り返した。比較例1、3及び4中、UV吸収剤、色素(p)、DBTDL及びBHTも、実施例1と同様の比率で使用した。比較例2及び5中、溶解度だけが確認され、そして、官能基付与は行なわれなかった。
ポリエチレングリコール200に溶解させた0.49gのポリビニルピロリドンK90を含有している溶液4.49gに対し、実施例1〜4並びに比較例1及び2のいずれかで得たシリコーンプレポリマー又は未官能基化ポリマー5.51gを添加し、70℃に加熱しながらこれらの物質を混合し、その後、減圧することで脱気した。溶解性は視覚的に観察され、結果は表1に示した。
Claims (21)
- 以下の式で表わされる構造を有する少なくとも1つのシリコーン含有残基と、
Aは、シロキサニル基を表す)
以下の式で表わされる構造を有する少なくとも1つの重合可能残基:
Pは、1つ以上のエチレン性不飽和部位を含む有機基を表す)
とを有するシリコーンプレポリマーであって、
前記プレポリマーは、その10重量%〜30重量%のケイ素含量を有し;
少なくとも1つのシリコーン含有残基のうち少なくとも1つが、少なくとも1つの極性部位をさらに有する極性シリコーン含有残基であり、前記極性部位はヒドロキシル、アミド、カルボキシル、アミノ、カルボネート、カルバメート、スルホアミド、スルホン酸基、ホスホン酸基、メトキシエチル、メトキシエトキシエチル、ヒドロキシエチル又はヒドロキシエトキシエチルであり;及び
前記プレポリマーは、その30重量%〜90重量%の極性シリコーン含有残基を有する、
シリコーンプレポリマー。 - 以下の式で表わされる構造を有する親水性残基の少なくとも1つをさらに含み、該親水性残基がN,N-ジメチルアクリルアミド、2-ヒドロキシエチルメタクリレート、N-ビニルピロリドン、N-ビニルホルムアミド、N-ビニルアセトアミド、(メタ)アクリル酸、N-ビニル-2-ピペリドン、N-ビニル-2-カプロラクタム、N-ビニル-3-メチル-2-カプロラクタム、N-ビニル-3-メチル-2-ピペリドン、N-ビニル-4-メチル-2-ピペリドン、N-ビニル-4-メチル-2-カプロラクタム、N-ビニル-3-エチル-2-ピロリドン、N-ビニル-4,5-ジメチル-2-ピロリドン又はN-ビニルイミダゾールの1つ以上の残基である、請求項1記載のプレポリマー:
Bは、親水性基を表す)。 - 極性部位がヒドロキシルである、請求項1記載のプレポリマー。
- 重合可能残基が、1つ以上のメタクリロイルオキシ基、アクリロイルオキシ基、メタクリルアミド基、アクリルアミド基、スチリル基、ビニル基、ビニルカーボネート基、ビニルカルバメート基、アリルカーボネート基又はアリルカルバメート基を含む、請求項1記載のプレポリマー。
- 13重量%〜20重量%のケイ素含量を有する、請求項1記載のプレポリマー。
- 極性シリコーン単位の総量が、前記プレポリマーの固形含量に対して50重量%〜80重量%である、請求項1記載のプレポリマー。
- 重合可能単位の含量が、前記プレポリマーに対して0.1〜15mol%である、請求項1記載のプレポリマー。
- 前記プレポリマーが、水溶性溶媒中に該プレポリマーの固形含量に対して50重量%以上の溶解度を有する、請求項1記載のプレポリマー。
- 前記プレポリマーが、1重量%〜10重量%のポリビニルピロリドンを含む水溶性溶媒中に、該プレポリマーの固形含量に対して50重量%以上の溶解度を有する、請求項1記載のプレポリマー。
- 水溶性溶媒が、1つ以上のエチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコール、又はエチレングリコール-プロピレングリコールコポリマー又はそれらの混合物を含む、請求項16記載のプレポリマー。
- 請求項1記載のプレポリマーを重合することにより得られるポリマー。
- 請求項19記載のポリマーを含む眼用レンズ。
- 請求項19記載のポリマーを含むコンタクトレンズ。
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Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7838698B2 (en) | 2006-09-29 | 2010-11-23 | Johnson & Johnson Vision Care, Inc. | Hydrolysis-resistant silicone compounds |
US9056880B2 (en) | 2006-09-29 | 2015-06-16 | Johnson & Johnson Vision Care, Inc. | Process for producing hydrolysis-resistant silicone compounds |
US7897654B2 (en) * | 2007-12-27 | 2011-03-01 | Johnson & Johnson Vision Care Inc. | Silicone prepolymer solutions |
WO2011034801A1 (en) * | 2009-09-15 | 2011-03-24 | Novartis Ag | Prepolymers suitable for making ultra-violet absorbing contact lenses |
WO2011075377A1 (en) * | 2009-12-14 | 2011-06-23 | Novartis Ag | Methods for making silicone hydrogel lenses from water-based lens formulations |
JP5834405B2 (ja) * | 2009-12-28 | 2015-12-24 | 東レ株式会社 | シリコーンプレポリマー、シリコーンポリマー、眼用レンズおよびコンタクトレンズ |
US9522980B2 (en) | 2010-05-06 | 2016-12-20 | Johnson & Johnson Vision Care, Inc. | Non-reactive, hydrophilic polymers having terminal siloxanes and methods for making and using the same |
MX349540B (es) | 2010-07-30 | 2017-08-02 | Novartis Ag * | Prepolímeros de polisiloxano anfifílicos y usos de los mismos. |
JP5784131B2 (ja) | 2010-10-06 | 2015-09-24 | ノバルティス アーゲー | ペンダント親水性基を持つ重合しうる鎖延長ポリシロキサン |
AU2011312206B2 (en) | 2010-10-06 | 2014-04-24 | Novartis Ag | Water-processable silicone-containing prepolymers and uses thereof |
EP2625217B1 (en) | 2010-10-06 | 2018-07-04 | Novartis AG | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
CN103827733A (zh) * | 2011-02-28 | 2014-05-28 | 库柏维景国际控股公司 | 具有高可冷冻水含量的硅酮水凝胶隐形眼镜 |
US9170349B2 (en) | 2011-05-04 | 2015-10-27 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
US10209534B2 (en) | 2012-03-27 | 2019-02-19 | Johnson & Johnson Vision Care, Inc. | Increased stiffness center optic in soft contact lenses for astigmatism correction |
US10073192B2 (en) | 2012-05-25 | 2018-09-11 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
US9244196B2 (en) | 2012-05-25 | 2016-01-26 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
EP2922929A1 (en) | 2012-11-20 | 2015-09-30 | 3M Innovative Properties Company | Laminates and articles comprising a block copolymer coating comprising polyorganosiloxane and polyolefin |
WO2014081682A1 (en) | 2012-11-20 | 2014-05-30 | 3M Innovative Properties Company | Block copolymer comprising polyorganosiloxane block and polyolefin block |
WO2014121030A2 (en) | 2013-01-31 | 2014-08-07 | Momentive Performance Materials Inc. | Water soluble silicone material |
US10692096B2 (en) * | 2013-03-15 | 2020-06-23 | Thermodynamic Design, Llc | Customizable data management system |
US9851472B2 (en) | 2015-03-27 | 2017-12-26 | Momentive Performance Materials Inc. | Silicone-based hydrophilic copolymer and hydrogel compositions comprising the same |
US9470625B1 (en) * | 2015-05-28 | 2016-10-18 | National Chung Cheng University | Method of examining purity of dendrimers |
US11125916B2 (en) | 2016-07-06 | 2021-09-21 | Johnson & Johnson Vision Care, Inc. | Silicone hydrogels comprising N-alkyl methacrylamides and contact lenses made thereof |
BR112019000204A2 (pt) * | 2016-07-06 | 2019-04-16 | Johnson & Johnson Vision Care, Inc. | óptica central de dureza aumentada em lentes de contato macias para correção de astigmatismo |
US11154637B2 (en) | 2018-11-07 | 2021-10-26 | Industrial Technology Research Institute | Biodegradable sealant and use of a biodegradable sealant in manufacture of an agent for biological tissue adhesion or repair |
JP7145122B2 (ja) * | 2019-06-06 | 2022-09-30 | 信越化学工業株式会社 | シロキサン及びその製造方法 |
Family Cites Families (139)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US583110A (en) * | 1897-05-25 | Girder-rail | ||
US2793223A (en) * | 1954-05-20 | 1957-05-21 | Dow Corning | Acryloxy methyl siloxanes |
US2956044A (en) * | 1956-08-06 | 1960-10-11 | Dow Corning | Acryloxymethylsilicon polymers |
US3001975A (en) | 1957-04-05 | 1961-09-26 | Rohm & Haas | Monoepoxidation of esters, monomers, and polymers thereof |
US3057902A (en) * | 1960-08-31 | 1962-10-09 | Union Carbide Corp | Ester solvents and basic catalysts employed in an addition process |
FR1532373A (fr) * | 1967-05-03 | 1968-07-12 | Kodak Pathe | Nouvelles compositions et nouveaux produits photopolymérisables et procédé de reproduction d'images utilisant ces nouveaux produits |
JPS491570B1 (ja) * | 1968-10-31 | 1974-01-14 | ||
US3699081A (en) | 1969-08-30 | 1972-10-17 | Sumitomo Chemical Co | Method for stabilizing acrylamide |
UST908001I4 (en) | 1971-02-14 | 1973-03-27 | Defensive publication | |
DE2207495A1 (de) * | 1971-02-20 | 1972-08-24 | Dainippon Printing Co Ltd | Flachdruckplatten und Verfahren zu ihrer Herstellung |
BE787750A (fr) | 1971-08-20 | 1973-02-19 | Union Carbide Corp | Procede pour inhiber la polymerisation d'acrylates et methacrylates pendant leur distillation |
US3859320A (en) * | 1972-05-22 | 1975-01-07 | Ici Ltd | Fluorine-containing organosilicon compounds |
US3808178A (en) * | 1972-06-16 | 1974-04-30 | Polycon Laboratories | Oxygen-permeable contact lens composition,methods and article of manufacture |
JPS5622325B2 (ja) | 1973-06-08 | 1981-05-25 | ||
US3959358A (en) * | 1975-01-08 | 1976-05-25 | Nalco Chemical Company | Polymerization inhibition of acrylate esters |
US4120570A (en) * | 1976-06-22 | 1978-10-17 | Syntex (U.S.A.) Inc. | Method for correcting visual defects, compositions and articles of manufacture useful therein |
US4144137A (en) | 1976-12-13 | 1979-03-13 | Rohm And Haas Company | Method for removal of polymerization inhibitor |
US4117001A (en) * | 1977-07-05 | 1978-09-26 | Phillips Petroleum Company | Pyrolysis of heavies formed in production of unsaturated dinitriles |
GB1604519A (en) * | 1977-07-25 | 1981-12-09 | Bausch & Lomb | Polysiloxane polymers and contact lens and other biomedical articles formed therefrom |
JPS5455455A (en) * | 1977-10-12 | 1979-05-02 | Toyo Contact Lens Co Ltd | Contact lens |
JPS584327B2 (ja) * | 1978-07-15 | 1983-01-26 | 東洋コンタクトレンズ株式会社 | コンタクトレンズ |
JPS5466853A (en) * | 1977-11-08 | 1979-05-29 | Toyo Contact Lens Co Ltd | Soft contact lens |
US4402887A (en) * | 1978-03-14 | 1983-09-06 | Dainippon Ink And Chemicals Inc. | Sheet-like articles of polyvinyl chloride |
JPS6017377B2 (ja) | 1979-07-31 | 1985-05-02 | 信越化学工業株式会社 | 重合性オルガノポリシロキサンの製造方法 |
US4260725A (en) * | 1979-12-10 | 1981-04-07 | Bausch & Lomb Incorporated | Hydrophilic contact lens made from polysiloxanes which are thermally bonded to polymerizable groups and which contain hydrophilic sidechains |
US4259467A (en) * | 1979-12-10 | 1981-03-31 | Bausch & Lomb Incorporated | Hydrophilic contact lens made from polysiloxanes containing hydrophilic sidechains |
US4395496A (en) * | 1981-11-16 | 1983-07-26 | Uco Optics, Inc. | Cured cellulose ester, method of curing same, and use thereof |
US4463149A (en) * | 1982-03-29 | 1984-07-31 | Polymer Technology Corporation | Silicone-containing contact lens material and contact lenses made thereof |
US4602074A (en) | 1983-12-20 | 1986-07-22 | Nippon Contact Lens Manufacturing Ltd. | Contact lens material |
JPS60146219A (ja) * | 1984-01-11 | 1985-08-01 | Toray Ind Inc | 樹脂の製造方法 |
JPS60239491A (ja) * | 1984-05-15 | 1985-11-28 | Kanegafuchi Chem Ind Co Ltd | 珪素含有メタクリル酸エステルの安定化方法 |
DE3517612A1 (de) * | 1985-05-15 | 1987-01-02 | Titmus Eurocon Kontaktlinsen | Modifizierter siliconkautschuk und seine verwendung als material fuer eine optische linse sowie optische linse aus diesem material |
DE3684774D1 (de) * | 1985-12-19 | 1992-05-14 | Nippon Catalytic Chem Ind | Verfahren zur hemmung der polymerisierung von maleimiden. |
US4861850A (en) * | 1986-02-06 | 1989-08-29 | Progressive Chemical Research, Ltd. | Ophthalamic device from fluoro-silicon polymers |
JPS63216044A (ja) | 1987-03-05 | 1988-09-08 | Nippon Zeon Co Ltd | パタ−ン形成材料 |
JPS63301919A (ja) | 1987-06-02 | 1988-12-08 | Seiko Epson Corp | コンタクトレンズ |
DE3729457A1 (de) | 1987-09-03 | 1989-03-16 | Bayer Ag | Kontaktoptische gegenstaende |
US5128484A (en) * | 1987-12-28 | 1992-07-07 | Sokubai Kagaku Kogyo, Co., Ltd. | Acrylonitrile maleimides solution composition of improved shelf life and method for production thereof |
JP2842443B2 (ja) * | 1988-09-30 | 1999-01-06 | 東レ・ダウコーニング・シリコーン株式会社 | 片方の末端に重合性官能基を有するオルガノポリシロキサンの製造方法 |
US5070215A (en) | 1989-05-02 | 1991-12-03 | Bausch & Lomb Incorporated | Novel vinyl carbonate and vinyl carbamate contact lens material monomers |
US5079319A (en) * | 1989-10-25 | 1992-01-07 | Ciba-Geigy Corporation | Reactive silicone and/or fluorine containing hydrophilic prepolymers and polymers thereof |
US5010141A (en) * | 1989-10-25 | 1991-04-23 | Ciba-Geigy Corporation | Reactive silicone and/or fluorine containing hydrophilic prepolymers and polymers thereof |
CA2038117A1 (en) * | 1990-03-29 | 1991-09-30 | Mahfuza B. Ali | Controllable radiation curable photoiniferter prepared adhesives for attachment of microelectronic devices and a method of attaching microelectronic devices therewith |
US5057578A (en) * | 1990-04-10 | 1991-10-15 | E. I. Du Pont De Nemours And Company | Silicone-containing block copolymers and macromonomers |
US5244981A (en) * | 1990-04-10 | 1993-09-14 | Permeable Technologies, Inc. | Silicone-containing contact lens polymers, oxygen permeable contact lenses and methods for making these lenses and treating patients with visual impairment |
US5314960A (en) * | 1990-04-10 | 1994-05-24 | Permeable Technologies, Inc. | Silicone-containing polymers, oxygen permeable hydrophilic contact lenses and methods for making these lenses and treating patients with visual impairment |
JP2622186B2 (ja) | 1990-07-18 | 1997-06-18 | 株式会社クラレ | 有機珪素化合物の蒸留方法 |
US5329034A (en) * | 1990-08-09 | 1994-07-12 | Sagami Chemical Research Center | Silanol compounds, polymerizable monomers and polymers having mesogenic groups |
US5371147A (en) * | 1990-10-11 | 1994-12-06 | Permeable Technologies, Inc. | Silicone-containing acrylic star polymers, block copolymers and macromonomers |
US5219965A (en) * | 1990-11-27 | 1993-06-15 | Bausch & Lomb Incorporated | Surface modification of polymer objects |
EP0540027B1 (en) * | 1991-10-31 | 1999-06-09 | Daicel Chemical Industries, Ltd. | Compositions, expoxidized compositions, a heat-curable resin composition, an epoxy resin composition, radically polymerized composition, a curable resin composition and a polymer having epoxy groups |
US5358995A (en) * | 1992-05-15 | 1994-10-25 | Bausch & Lomb Incorporated | Surface wettable silicone hydrogels |
JPH0632791A (ja) | 1992-07-15 | 1994-02-08 | Kuraray Co Ltd | ケイ素含有化合物 |
JPH0641336A (ja) * | 1992-07-23 | 1994-02-15 | Toray Ind Inc | プラスティック成形品の製造方法 |
US5336797A (en) * | 1992-12-30 | 1994-08-09 | Bausch & Lomb Incorporated | Siloxane macromonomers |
US5321108A (en) * | 1993-02-12 | 1994-06-14 | Bausch & Lomb Incorporated | Fluorosilicone hydrogels |
JPH06239912A (ja) * | 1993-02-18 | 1994-08-30 | Nippon Shokubai Co Ltd | 重合体の製造方法 |
EP0695770A4 (en) * | 1993-04-20 | 1997-12-17 | Sagami Chem Res | COPOLYMER WITH LIQUID CRYSTAL GROUP IN THE SIDE CHAIN |
JP2869304B2 (ja) | 1993-08-18 | 1999-03-10 | 信越化学工業株式会社 | シラノール基含有オルガノポリシロキサンの製造方法 |
JPH07216091A (ja) * | 1994-01-27 | 1995-08-15 | Toray Dow Corning Silicone Co Ltd | シロキサニル・ホスフェートの製造方法 |
JP3445370B2 (ja) * | 1994-07-18 | 2003-09-08 | 東レ・ダウコーニング・シリコーン株式会社 | メタクリロキシプロピルジメチルクロロシランの製造方法 |
US5888356A (en) * | 1994-08-19 | 1999-03-30 | Huels Aktiengesellschaft | Inhibition of polymerization of vinylaromatic or vinylaliphatic |
JPH08259574A (ja) | 1995-03-22 | 1996-10-08 | Toray Dow Corning Silicone Co Ltd | 脂環式エポキシ基含有ラジカル重合性オリゴシロキサンおよびその製造方法 |
JP3479378B2 (ja) | 1995-04-06 | 2003-12-15 | 株式会社メニコン | 眼用レンズ材料 |
US5824195A (en) | 1995-07-10 | 1998-10-20 | Chisso Corporation | Process for distilling crude acrylic silane solution |
JPH09297285A (ja) * | 1996-03-04 | 1997-11-18 | Menicon Co Ltd | 眼用レンズおよびその製法 |
IT1283082B1 (it) * | 1996-05-30 | 1998-04-07 | Hoechst Sara Spa | Procedimento per la sintesi di resine contenenti insaturazoni di tipo (met)acrilico induribili mediante radiazioni o calore e |
WO1998000456A1 (en) * | 1996-07-02 | 1998-01-08 | Ciba Speciality Chemicals Holding Inc. | Process for curing a polymerizable composition |
CN1192961A (zh) * | 1996-12-06 | 1998-09-16 | 东丽株式会社 | 医用塑料物品 |
US6242153B1 (en) * | 1997-03-27 | 2001-06-05 | Fuji Photo Film Co., Ltd. | Positive photoresist composition for far ultraviolet ray exposure |
JP3746871B2 (ja) * | 1997-04-14 | 2006-02-15 | Jsr株式会社 | 液状硬化性樹脂組成物 |
CA2236189A1 (en) * | 1997-05-15 | 1998-11-15 | Givaudan-Roure (International) Sa | Fragrance precursor compounds |
KR100281513B1 (ko) * | 1997-05-22 | 2001-02-15 | 울프 크라스텐센, 스트라쎄 로텐베르그 | 특히 당 라디칼 또는 당유도체인 폴리하이드록시오가닐 라디칼 및 폴리옥시 알킬렌 라디칼로 구성되는 오카노 폴리실록산 |
US5831110A (en) * | 1997-10-23 | 1998-11-03 | Chisso Corporation | Fluorine-containing siloxane compound and process for production thereof |
US6822016B2 (en) * | 2001-09-10 | 2004-11-23 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing internal wetting agents |
US7461937B2 (en) * | 2001-09-10 | 2008-12-09 | Johnson & Johnson Vision Care, Inc. | Soft contact lenses displaying superior on-eye comfort |
US5962548A (en) * | 1998-03-02 | 1999-10-05 | Johnson & Johnson Vision Products, Inc. | Silicone hydrogel polymers |
US7052131B2 (en) * | 2001-09-10 | 2006-05-30 | J&J Vision Care, Inc. | Biomedical devices containing internal wetting agents |
US6218503B1 (en) * | 1998-05-15 | 2001-04-17 | Bausch & Lomb Incorporated | Silicone-containing prepolymers |
JP4103175B2 (ja) * | 1998-05-20 | 2008-06-18 | 東レ株式会社 | 眼用レンズ用ポリマーの製造法 |
JP4103174B2 (ja) * | 1998-05-20 | 2008-06-18 | 東レ株式会社 | 眼用レンズ用ポリマーの製造方法 |
EP0965593B2 (en) | 1998-06-19 | 2008-12-03 | Shin-Etsu Chemical Co., Ltd. | Distillation of (meth)acryloxybearing alkoxysilane |
US6344495B1 (en) * | 1998-07-31 | 2002-02-05 | Dai Nippon Printing Co., Ltd. | Photo-curable resin composition and method for forming concave-convex pattern |
US5959117A (en) | 1998-08-10 | 1999-09-28 | Bausch & Lomb | Monomers useful for contact lens materials |
US6031059A (en) * | 1998-09-30 | 2000-02-29 | Johnson & Johnson Vision Products, Inc. | Optically transparent hydrogels and processes for their production |
JP2000191730A (ja) | 1998-12-24 | 2000-07-11 | Toray Ind Inc | 眼用レンズ用モノマー、眼用レンズ用ポリマーおよびそれを用いたコンタクトレンズ |
DE19860361A1 (de) * | 1998-12-24 | 2000-06-29 | Espe Dental Ag | Vernetzbare Monomere auf Cyclosiloxanbasis, deren Herstellung und deren Verwendung in polymerisierbaren Massen |
JP4144088B2 (ja) | 1998-12-24 | 2008-09-03 | 東レ株式会社 | コンタクトレンズ用ポリマーおよびそれを用いたコンタクトレンズ |
JP4236342B2 (ja) * | 1999-07-30 | 2009-03-11 | 東レ・ダウコーニング株式会社 | カルボシロキサンデンドリマーおよびデンドリマー含有有機重合体 |
JP4123648B2 (ja) | 1999-08-05 | 2008-07-23 | 東レ株式会社 | ポリマーおよびそれを用いた眼用レンズ |
US6732162B1 (en) * | 1999-11-15 | 2004-05-04 | Internet Pictures Corporation | Method of providing preprocessed images for a plurality of internet web sites |
US6649722B2 (en) * | 1999-12-10 | 2003-11-18 | Novartis Ag | Contact lens |
ES2328009T5 (es) * | 1999-12-16 | 2013-12-12 | Coopervision International Holding Company, Lp | Lente de contacto blanda con capacidad de ser utilizada a largo plazo |
JP4524838B2 (ja) * | 2000-02-07 | 2010-08-18 | 東レ株式会社 | 眼用レンズ |
DE60104457T2 (de) | 2000-02-10 | 2005-08-04 | Nippon Shokubai Co., Ltd. | Verfahren zur Herstellung alpha, beta-ungesättigter Carbonsäureester sowie Katalysator zur Verwendung in diesem Verfahren |
JP4438162B2 (ja) * | 2000-02-24 | 2010-03-24 | 東レ株式会社 | 眼用レンズ用ポリマーの製造法および眼用レンズ |
JP4273612B2 (ja) * | 2000-03-03 | 2009-06-03 | 東レ株式会社 | 眼用レンズ |
US6372815B1 (en) * | 2000-04-18 | 2002-04-16 | Ocular Sciences Inc | Ophthalmic lenses and compositions, and methods for producing same |
US6177585B1 (en) * | 2000-05-19 | 2001-01-23 | Dow Corning Corporation | Bimetallic platinum catalysts for hydrosilations |
JP5011601B2 (ja) * | 2000-10-12 | 2012-08-29 | 東レ株式会社 | ポリマーおよびそれを用いた眼用レンズ |
JP4058978B2 (ja) * | 2001-03-30 | 2008-03-12 | 東レ株式会社 | ポリマー、それを用いた眼用レンズおよびコンタクトレンズ |
US7112641B2 (en) * | 2001-03-30 | 2006-09-26 | Johnson & Johnson Vision Care, Inc. | Monomer, polymers, and ophthalmic lenses and contact lenses made by using the same |
EP1386924B1 (en) | 2001-03-30 | 2009-06-10 | Johnson & Johnson Vision Care, Inc. | Monomer, polymer, and ocular lens and contact lens each obtained therefrom |
EP1424339A4 (en) * | 2001-08-06 | 2006-08-02 | Johson & Johnson Vision Care I | MONOMERS, POLYMERS AND OPHTHALMIC LENSES |
DE60143171D1 (de) | 2001-08-17 | 2010-11-11 | Johnson & Johnson Vision Care | Verfahren zur herstellung eines polymers für eine augenoptische linse und augenoptische linse |
WO2003042222A1 (fr) * | 2001-10-02 | 2003-05-22 | Johnson & Johnson Vision Care, Inc. | Monomere, polymere et lentille oculaire les comprenant |
US7169874B2 (en) * | 2001-11-02 | 2007-01-30 | Bausch & Lomb Incorporated | High refractive index polymeric siloxysilane compositions |
US6864341B2 (en) * | 2001-11-02 | 2005-03-08 | Bausch & Lomb Incorporated | High refractive index aromatic-based prepolymer precursors |
KR100419864B1 (ko) * | 2001-11-15 | 2004-03-04 | 한국화학연구원 | 신규 가교제와 이를 함유하는 가교형 고체 고분자 전해질 |
US6787615B2 (en) * | 2002-01-25 | 2004-09-07 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis of oligomeric poly(silarylene-siloxane-acetylene)'s and their conversion to high temperature plastics, elastomers, and coatings |
US6846892B2 (en) | 2002-03-11 | 2005-01-25 | Johnson & Johnson Vision Care, Inc. | Low polydispersity poly-HEMA compositions |
US6803406B2 (en) * | 2002-03-29 | 2004-10-12 | National Starch And Chemical Investmnet Holding Corporation | Electron donors, electron acceptors and adhesion promoters containing disulfide |
US20040024709A1 (en) * | 2002-08-05 | 2004-02-05 | Yu Paul D. | System and method for determining the identity of a party associated with a transaction |
EP1546159B1 (en) * | 2002-08-16 | 2014-06-18 | Dow Corning Corporation | Enzyme catalyzed method of forming organosilicon esters |
JP4273885B2 (ja) | 2002-09-06 | 2009-06-03 | 東レ株式会社 | シリコーンモノマー組成物の製造方法 |
US7108893B2 (en) | 2002-09-23 | 2006-09-19 | Delphi Technologies, Inc. | Spray system with combined kinetic spray and thermal spray ability |
US6922118B2 (en) * | 2002-11-01 | 2005-07-26 | Hrl Laboratories, Llc | Micro electrical mechanical system (MEMS) tuning using focused ion beams |
US6809155B2 (en) * | 2002-11-20 | 2004-10-26 | National Starch And Chemical Investment Holding Corporation | Unsaturated compounds containing silane, electron donor and electron acceptor functionality |
US20040114101A1 (en) * | 2002-12-13 | 2004-06-17 | Ocular Sciences, Inc. | Contact lenses with color shifting properties |
US6933401B2 (en) | 2003-06-30 | 2005-08-23 | Frank Molock | Process for the production of vicinal diesters from epoxides |
US8373000B2 (en) | 2003-06-30 | 2013-02-12 | Johnson & Johnson Vision Care, Inc. | Process for the production of bis(trimethylsilyloxy)silylalkylglycerol methacrylates |
US7368589B2 (en) * | 2003-10-31 | 2008-05-06 | Johnson & Johnson Vision Care, Inc. | Purification of silicone containing compounds by supercritical fluid extraction |
US7683206B2 (en) | 2004-02-27 | 2010-03-23 | Toray Industries, Inc. | Silicone compound and process for producing the same |
JP4539131B2 (ja) * | 2004-03-16 | 2010-09-08 | 住友化学株式会社 | 有機ケイ素系化合物、及びその製造方法 |
WO2005102675A2 (en) * | 2004-04-21 | 2005-11-03 | Novartis Ag | Curable colored inks for making colored silicone hydrogel lenses |
JP4556491B2 (ja) | 2004-05-26 | 2010-10-06 | 三菱化学株式会社 | 重合禁止剤、これを含有する組成物、及び前記重合禁止剤を用いる易重合性化合物の製造方法 |
JP4826150B2 (ja) | 2004-06-22 | 2011-11-30 | 東レ株式会社 | シリコーンモノマーの製造方法 |
US20060047134A1 (en) * | 2004-08-25 | 2006-03-02 | Frank Molock | Process for the production of (trimethylsilyloxy)silylalkylglycerol methacrylates |
US7249848B2 (en) * | 2004-09-30 | 2007-07-31 | Johnson & Johnson Vision Care, Inc. | Wettable hydrogels comprising reactive, hydrophilic, polymeric internal wetting agents |
JP2008537966A (ja) * | 2005-03-17 | 2008-10-02 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | 単分散および狭分散の単官能性シリコーンを製造するための方法 |
US7279538B2 (en) * | 2005-04-01 | 2007-10-09 | Bausch & Lomb Incorporated | Aromatic-based polysiloxane prepolymers and ophthalmic devices produced therefrom |
US8053539B2 (en) * | 2006-06-30 | 2011-11-08 | Johnson & Johnson Vision Care Inc. | Siloxanyl materials for molded plastics |
US8569538B2 (en) | 2006-06-30 | 2013-10-29 | Johnson & Johnson Vision Care, Inc. | Acryloyl materials for molded plastics |
US7838698B2 (en) | 2006-09-29 | 2010-11-23 | Johnson & Johnson Vision Care, Inc. | Hydrolysis-resistant silicone compounds |
CN101541815A (zh) | 2006-09-29 | 2009-09-23 | 庄臣及庄臣视力保护公司 | 制备抗水解的聚硅氧烷化合物的方法 |
US20080081850A1 (en) * | 2006-09-29 | 2008-04-03 | Kazuhiko Fujisawa | Process for producing hydrolysis-resistant silicone compounds |
US20080119627A1 (en) * | 2006-11-22 | 2008-05-22 | Masataka Nakamura | Methods for purifying siloxanyl monomers |
JP5669396B2 (ja) * | 2006-12-13 | 2015-02-12 | ノバルティス アーゲー | 化学線硬化性シリコーンヒドロゲルコポリマーおよびその使用 |
JP2011507563A (ja) | 2007-12-14 | 2011-03-10 | ボーシュ アンド ローム インコーポレイティド | バイオメディカルデバイス |
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US8080622B2 (en) | 2011-12-20 |
AR067383A1 (es) | 2009-10-07 |
TWI486381B (zh) | 2015-06-01 |
US20120065348A1 (en) | 2012-03-15 |
US20090005528A1 (en) | 2009-01-01 |
EP2164882A4 (en) | 2013-07-24 |
JP2010532417A (ja) | 2010-10-07 |
WO2009006285A1 (en) | 2009-01-08 |
TW200914496A (en) | 2009-04-01 |
US8399539B2 (en) | 2013-03-19 |
EP2164882A1 (en) | 2010-03-24 |
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