CA1251882A - Produits tres permeables a l'oxygene pour verres de contact; compositions a base de ces produits - Google Patents

Produits tres permeables a l'oxygene pour verres de contact; compositions a base de ces produits

Info

Publication number: CA1251882A
Authority: CA; Canada
Prior art keywords: integer; parts; acrylic; methacrylate; contact lens
Prior art date: 1986-06-30
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.): Expired

Application number

CA000512768A

Other languages

English (en)

Inventor

Nick N. Novicky

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1986-06-30

Filing date

1986-06-30

Publication date

1989-03-28

1986-06-30 Application filed by Individual filed Critical Individual

1986-06-30 Priority to CA000512768A priority Critical patent/CA1251882A/fr

1989-03-28 Application granted granted Critical

1989-03-28 Publication of CA1251882A publication Critical patent/CA1251882A/fr

Status Expired legal-status Critical Current

Links

QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 33
239000000203 mixture Substances 0.000 title claims abstract description 33
239000001301 oxygen Substances 0.000 title claims abstract description 33
229910052760 oxygen Inorganic materials 0.000 title claims abstract description 33
239000000463 material Substances 0.000 title claims abstract description 30
239000000178 monomer Substances 0.000 claims abstract description 77
-1 unsaturated fluorocarbon ester Chemical class 0.000 claims abstract description 42
150000002148 esters Chemical class 0.000 claims abstract description 29
229920001870 copolymer plastic Polymers 0.000 claims abstract description 20
239000003795 chemical substances by application Substances 0.000 claims abstract description 9
150000003457 sulfones Chemical class 0.000 claims abstract description 8
238000010348 incorporation Methods 0.000 claims abstract description 7
239000001257 hydrogen Chemical group 0.000 claims description 31
229910052739 hydrogen Chemical group 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 25
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 24
229940063559 methacrylic acid Drugs 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
125000004122 cyclic group Chemical group 0.000 claims description 22
239000007983 Tris buffer Substances 0.000 claims description 21
125000005395 methacrylic acid group Chemical class 0.000 claims description 19
LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 16
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 13
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 13
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 13
OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 12
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 10
XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 10
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
230000035699 permeability Effects 0.000 claims description 8
125000005401 siloxanyl group Chemical group 0.000 claims description 8
HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 7
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
229940063557 methacrylate Drugs 0.000 claims description 7
229920003023 plastic Polymers 0.000 claims description 7
239000004033 plastic Substances 0.000 claims description 7
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 6
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 6
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-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
150000002431 hydrogen Chemical group 0.000 claims description 6
LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 5
UNIYDALVXFPINL-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propylsilicon Chemical compound CC(=C)C(=O)OCCC[Si] UNIYDALVXFPINL-UHFFFAOYSA-N 0.000 claims description 5
239000003431 cross linking reagent Substances 0.000 claims description 5
QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 4
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
QNSJTOZGJYPSNU-UHFFFAOYSA-N 2-tris(trimethylsilyloxy)silyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C QNSJTOZGJYPSNU-UHFFFAOYSA-N 0.000 claims description 4
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
WUIJTQZXUURFQU-UHFFFAOYSA-N 1-methylsulfonylethene Chemical compound CS(=O)(=O)C=C WUIJTQZXUURFQU-UHFFFAOYSA-N 0.000 claims description 3
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 3
OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 3
125000005907 alkyl ester group Chemical group 0.000 claims description 3
OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 claims description 2
CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 2
RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 2
CFGHKOPUKMUFRX-UHFFFAOYSA-N 2-tris[dimethyl(trimethylsilyloxy)silyl]silyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si]([Si](C)(C)O[Si](C)(C)C)([Si](C)(C)O[Si](C)(C)C)[Si](C)(C)O[Si](C)(C)C CFGHKOPUKMUFRX-UHFFFAOYSA-N 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 2
GFHMGSFDHKDJSG-UHFFFAOYSA-N dicyclohexyl 2-methylidenebutanedioate Chemical compound C1CCCCC1OC(=O)C(=C)CC(=O)OC1CCCCC1 GFHMGSFDHKDJSG-UHFFFAOYSA-N 0.000 claims description 2
ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 claims description 2
NAPZWBMEGHXRJS-UHFFFAOYSA-N diphenyl 2-methylidenebutanedioate Chemical compound C=1C=CC=CC=1OC(=O)C(=C)CC(=O)OC1=CC=CC=C1 NAPZWBMEGHXRJS-UHFFFAOYSA-N 0.000 claims description 2
DFQSWFGKYUFIFW-UHFFFAOYSA-N dipropyl 2-methylidenebutanedioate Chemical compound CCCOC(=O)CC(=C)C(=O)OCCC DFQSWFGKYUFIFW-UHFFFAOYSA-N 0.000 claims description 2
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 2
WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 2
239000001294 propane Substances 0.000 claims description 2
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims description 2
TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
KYJKUYOMHYILIP-UHFFFAOYSA-N 2-[[dimethyl(trimethylsilyloxy)silyl]-bis(trimethylsilyloxy)silyl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](O[Si](C)(C)C)(O[Si](C)(C)C)[Si](C)(C)O[Si](C)(C)C KYJKUYOMHYILIP-UHFFFAOYSA-N 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
VDQMIADBOZHJOF-UHFFFAOYSA-N 2-silyloxyethyl 2,3,3-tris(trimethylsilyloxy)prop-2-enoate Chemical compound C[Si](OC(C(=O)OCCO[SiH3])=C(O[Si](C)(C)C)O[Si](C)(C)C)(C)C VDQMIADBOZHJOF-UHFFFAOYSA-N 0.000 claims 1
BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound 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 1
LRBRRBZQOCLNQH-UHFFFAOYSA-N C[Si](OC(CO[SiH2]OC(C(=C)C)=O)(O[Si](C)(C)C)O[Si](C)(C)C)(C)C Chemical compound C[Si](OC(CO[SiH2]OC(C(=C)C)=O)(O[Si](C)(C)C)O[Si](C)(C)C)(C)C LRBRRBZQOCLNQH-UHFFFAOYSA-N 0.000 claims 1
YEKQINRTTMFMRR-UHFFFAOYSA-N bis[2-[dimethyl(trimethylsilyloxy)silyl]ethyl] 2-methylidenebutanedioate Chemical compound C[Si](O[Si](C)(C)C)(C)CCOC(C(=C)CC(=O)OCC[Si](O[Si](C)(C)C)(C)C)=O YEKQINRTTMFMRR-UHFFFAOYSA-N 0.000 claims 1
229920000620 organic polymer Polymers 0.000 claims 1
238000000034 method Methods 0.000 abstract description 10
229920001577 copolymer Polymers 0.000 abstract description 7
238000004519 manufacturing process Methods 0.000 abstract description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229940102838 methylmethacrylate Drugs 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000012043 crude product Substances 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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 6
238000006116 polymerization reaction Methods 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
239000004342 Benzoyl peroxide Substances 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
235000019400 benzoyl peroxide Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
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 3
229920001155 polypropylene Polymers 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 2
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 2
239000005046 Chlorosilane Substances 0.000 description 2
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
229940114077 acrylic acid Drugs 0.000 description 2
BBCITGBFGUITMR-UHFFFAOYSA-N chloro-tris(trimethylsilyloxy)silane Chemical compound C[Si](C)(C)O[Si](Cl)(O[Si](C)(C)C)O[Si](C)(C)C BBCITGBFGUITMR-UHFFFAOYSA-N 0.000 description 2
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000003754 machining Methods 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
ZPQFAVDVWVKUOJ-UHFFFAOYSA-N 1-ethenylsulfonylbutane Chemical compound CCCCS(=O)(=O)C=C ZPQFAVDVWVKUOJ-UHFFFAOYSA-N 0.000 description 1
BJEWLOAZFAGNPE-UHFFFAOYSA-N 1-ethenylsulfonylethane Chemical compound CCS(=O)(=O)C=C BJEWLOAZFAGNPE-UHFFFAOYSA-N 0.000 description 1
GKRDUERMXXKTEG-UHFFFAOYSA-N 1-ethenylsulfonylpentane Chemical compound CCCCCS(=O)(=O)C=C GKRDUERMXXKTEG-UHFFFAOYSA-N 0.000 description 1
DBCLLYFDDUBSML-UHFFFAOYSA-N 1-ethenylsulfonylpropane Chemical compound CCCS(=O)(=O)C=C DBCLLYFDDUBSML-UHFFFAOYSA-N 0.000 description 1
TUAJZTAVXLCEGA-UHFFFAOYSA-N 1-hydroxyethyl prop-2-enoate Chemical compound CC(O)OC(=O)C=C TUAJZTAVXLCEGA-UHFFFAOYSA-N 0.000 description 1
PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
UFAVJQDLGJFYFY-UHFFFAOYSA-N 2-(benzenesulfonyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCS(=O)(=O)C1=CC=CC=C1 UFAVJQDLGJFYFY-UHFFFAOYSA-N 0.000 description 1
ICMDXJQURWMJCS-UHFFFAOYSA-N 2-butylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCCCS(=O)(=O)CCOC(=O)C(C)=C ICMDXJQURWMJCS-UHFFFAOYSA-N 0.000 description 1
QQLBBMXUMAPIEQ-UHFFFAOYSA-N 2-ethenylsulfonylethoxybenzene Chemical compound C=CS(=O)(=O)CCOC1=CC=CC=C1 QQLBBMXUMAPIEQ-UHFFFAOYSA-N 0.000 description 1
WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
FHPGUDZEMVTLRC-UHFFFAOYSA-N 2-ethylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCS(=O)(=O)CCOC(=O)C(C)=C FHPGUDZEMVTLRC-UHFFFAOYSA-N 0.000 description 1
GWPLOKPTQDEXNA-UHFFFAOYSA-N 2-methylsulfonylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCS(C)(=O)=O GWPLOKPTQDEXNA-UHFFFAOYSA-N 0.000 description 1
KAIOBIMIFKUTKB-UHFFFAOYSA-N 2-pentylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCCCCS(=O)(=O)CCOC(=O)C(C)=C KAIOBIMIFKUTKB-UHFFFAOYSA-N 0.000 description 1
PDJRFRQHLPDXNB-UHFFFAOYSA-N 2-propylsulfonylethyl 2-methylprop-2-enoate Chemical compound CCCS(=O)(=O)CCOC(=O)C(C)=C PDJRFRQHLPDXNB-UHFFFAOYSA-N 0.000 description 1
JBUAEPKXUUMQKW-UHFFFAOYSA-N 2-silyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[SiH3] JBUAEPKXUUMQKW-UHFFFAOYSA-N 0.000 description 1
DOGMJCPBZJUYGB-UHFFFAOYSA-N 3-trichlorosilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](Cl)(Cl)Cl DOGMJCPBZJUYGB-UHFFFAOYSA-N 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
101150069031 CSN2 gene Proteins 0.000 description 1
101100172874 Caenorhabditis elegans sec-3 gene Proteins 0.000 description 1
102100026735 Coagulation factor VIII Human genes 0.000 description 1
101100285518 Drosophila melanogaster how gene Proteins 0.000 description 1
101100275895 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) csnB gene Proteins 0.000 description 1
101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
229910003849 O-Si Inorganic materials 0.000 description 1
229910003872 O—Si Inorganic materials 0.000 description 1
229910018557 Si O Inorganic materials 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
RZKKLXUEULTOGP-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)O[Si](C)(C)C RZKKLXUEULTOGP-UHFFFAOYSA-N 0.000 description 1
229940048053 acrylate Drugs 0.000 description 1
LFOBOFBSSXPQGD-UHFFFAOYSA-N chloro-dimethyl-trimethylsilyloxysilane Chemical group C[Si](C)(C)O[Si](C)(C)Cl LFOBOFBSSXPQGD-UHFFFAOYSA-N 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
210000004087 cornea Anatomy 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
JHGHTBSOZYDUJC-UHFFFAOYSA-N ethenylsulfonylcyclohexane Chemical compound C=CS(=O)(=O)C1CCCCC1 JHGHTBSOZYDUJC-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 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
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
230000004304 visual acuity Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Eyeglasses (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000512768A 1986-06-30 1986-06-30 Produits tres permeables a l'oxygene pour verres de contact; compositions a base de ces produits Expired CA1251882A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000512768A CA1251882A (fr)	1986-06-30	1986-06-30	Produits tres permeables a l'oxygene pour verres de contact; compositions a base de ces produits

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000512768A CA1251882A (fr)	1986-06-30	1986-06-30	Produits tres permeables a l'oxygene pour verres de contact; compositions a base de ces produits

Publications (1)

Publication Number	Publication Date
CA1251882A true CA1251882A (fr)	1989-03-28

Family

ID=4133464

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000512768A Expired CA1251882A (fr)	1986-06-30	1986-06-30	Produits tres permeables a l'oxygene pour verres de contact; compositions a base de ces produits

Country Status (1)

Country	Link
CA (1)	CA1251882A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5777052A (en) *	1996-06-28	1998-07-07	Dow Corning Toray Slicone Co., Ltd.	Silicone modified vinyl polymers and method for the preparation thereof
EP2138889A1 (fr) *	2008-06-26	2009-12-30	Lachezar Komitov	Couche d'alignement pour LCD
CN114516942A (zh) *	2020-11-18	2022-05-20	亨泰光学股份有限公司	硬式透氧隐形眼镜高分子材料及其聚合方法

1986
- 1986-06-30 CA CA000512768A patent/CA1251882A/fr not_active Expired

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5777052A (en) *	1996-06-28	1998-07-07	Dow Corning Toray Slicone Co., Ltd.	Silicone modified vinyl polymers and method for the preparation thereof
EP2138889A1 (fr) *	2008-06-26	2009-12-30	Lachezar Komitov	Couche d'alignement pour LCD
WO2009156483A1 (fr) *	2008-06-26	2009-12-30	Lachezar Komitov	Couche d’alignement pour lcd
TWI493261B (zh) *	2008-06-26	2015-07-21	Lachezar Komitov	用於液晶材料之配向層的聚合物、表面導向子配向層材料、液晶裝置及其製造方法
CN114516942A (zh) *	2020-11-18	2022-05-20	亨泰光学股份有限公司	硬式透氧隐形眼镜高分子材料及其聚合方法

Legal Events

Date	Code	Title	Description
2006-06-30	MKEX	Expiry

Publication	Publication Date	Title
US4948855A (en)	1990-08-14	Comfortable, oxygen permeable contact lenses and the manufacture thereof
US4748224A (en)	1988-05-31	Silicone-sulfone and silicone-fluorocarbon-sulfone gas permeable contact lenses and compositions thereof
US4343927A (en)	1982-08-10	Hydrophilic, soft and oxygen permeable copolymer compositions
US5496871A (en)	1996-03-05	Fumarate and fumaramide siloxane hydrogel compositions
EP1355963B1 (fr)	2006-04-12	Biomateriaux polymeriques contenant des monomeres de silsesquioxane
CA2027748C (fr)	1998-01-06	Compositions polymeriques pour les lentilles de contact permeables a l'oxygene
CA1318446C (fr)	1993-05-25	Lentilles corneennes, materiel et methode de fabrication
JP3167132B2 (ja)	2001-05-21	共重合法及びそれにより製造された光学共重合体
US4861850A (en)	1989-08-29	Ophthalamic device from fluoro-silicon polymers
US4625007A (en)	1986-11-25	Silicone-containing contact lens material and contact lenses made thereof
EP0186033B1 (fr)	1992-08-19	Matériel pour des lentilles de contact
US5084537A (en)	1992-01-28	UV-absorbing extended-wear Lenses
GB2163173A (en)	1986-02-19	Oxygen permeable hard contact lens of silicon copolymer
EP0293467A1 (fr)	1988-12-07	Nouveau monomere acrylique de siloxanyl et lentilles de contact permeables aux gaz realisees avec ledit monomere
CA1251882A (fr)	1989-03-28	Produits tres permeables a l'oxygene pour verres de contact; compositions a base de ces produits
US4829137A (en)	1989-05-09	Continuous-wear highly oxygen permeable contact lenses
EP0436727B1 (fr)	1995-06-07	Lentille de contact
EP0215817B1 (fr)	1991-03-13	Lentilles pouvant etre portees en continu
JPS61285425A (ja)	1986-12-16	コンタクトレンズ材料
US5093447A (en)	1992-03-03	Ophthalmic device formed of a copolymer plastic material from ethylenic siloxanylalkoxy ester
CA1300797C (fr)	1992-05-12	Lentilles conrneennes confortables, permeables a l'oxygene et leur fabrication
EP0397683B1 (fr)	1994-03-16	Compositions pour fabriquer des lentilles de contact perfectionnees permeables aux gaz
WO1986004343A1 (fr)	1986-07-31	Lentilles a port prolonge
JP2793363B2 (ja)	1998-09-03	コンタクトレンズ
JPH02269306A (ja)	1990-11-02	フッ素系コンタクトレンズ