CA2278566A1 - Moulded ophthalmic article - Google Patents
Moulded ophthalmic article Download PDFInfo
- Publication number
- CA2278566A1 CA2278566A1 CA002278566A CA2278566A CA2278566A1 CA 2278566 A1 CA2278566 A1 CA 2278566A1 CA 002278566 A CA002278566 A CA 002278566A CA 2278566 A CA2278566 A CA 2278566A CA 2278566 A1 CA2278566 A1 CA 2278566A1
- Authority
- CA
- Canada
- Prior art keywords
- alkylene
- formula
- signifies
- methyl
- component
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000002348 vinylic group Chemical group 0.000 claims abstract description 31
- 238000004132 cross linking Methods 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000004820 halides Chemical class 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 229920005862 polyol Polymers 0.000 claims abstract description 13
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 12
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- 150000003077 polyols Chemical class 0.000 claims abstract description 11
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 6
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 6
- 229920000570 polyether Polymers 0.000 claims abstract description 6
- 150000002016 disaccharides Chemical class 0.000 claims abstract description 4
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- -1 aliphatic polyol Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 32
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 238000000465 moulding Methods 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 6
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 6
- 239000004386 Erythritol Substances 0.000 claims description 6
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 6
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 6
- 235000019414 erythritol Nutrition 0.000 claims description 6
- 229940009714 erythritol Drugs 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000000600 sorbitol Substances 0.000 claims description 6
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 5
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 5
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229930195725 Mannitol Natural products 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000594 mannitol Substances 0.000 claims description 5
- 235000010355 mannitol Nutrition 0.000 claims description 5
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000001502 supplementing effect Effects 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 230000002209 hydrophobic effect Effects 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 239000000470 constituent Substances 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 238000000108 ultra-filtration Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000036571 hydration Effects 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000017 hydrogel Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- LTUOEBMGHCVNIA-UHFFFAOYSA-N (diisocyanatohydrazinylidene)-oxomethane Chemical group O=C=NN(N=C=O)N=C=O LTUOEBMGHCVNIA-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010019 resist printing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- LCPUCXXYIYXLJY-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)C(F)CC(F)(F)F LCPUCXXYIYXLJY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2210/00—Compositions for preparing hydrogels
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Eyeglasses (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97810056A EP0867456A1 (de) | 1997-02-04 | 1997-02-04 | Ophthalmischer Formkörper |
| EP97810056.8 | 1997-02-04 | ||
| PCT/EP1998/000547 WO1998033834A1 (en) | 1997-02-04 | 1998-02-02 | Moulded ophthalmic article |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2278566A1 true CA2278566A1 (en) | 1998-08-06 |
Family
ID=8230146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002278566A Abandoned CA2278566A1 (en) | 1997-02-04 | 1998-02-02 | Moulded ophthalmic article |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6165408A (https=) |
| JP (1) | JP4098367B2 (https=) |
| AR (1) | AR011612A1 (https=) |
| AT (1) | ATE202578T1 (https=) |
| AU (1) | AU727156B2 (https=) |
| CA (1) | CA2278566A1 (https=) |
| DE (1) | DE69800994T2 (https=) |
| ES (1) | ES2160403T3 (https=) |
| TW (1) | TW425403B (https=) |
| ZA (1) | ZA98865B (https=) |
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| ATE520661T1 (de) * | 2003-06-27 | 2011-09-15 | Univ Maryland | Heterocyclische verbindungen mit quaternärem stickstoff zum nachweis von wässrigen monosacchariden in physiologischen flüssigkeiten |
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| US7999023B2 (en) * | 2004-12-03 | 2011-08-16 | 3M Innovative Properties Company | Process for making pressure sensitive adhesive hydrogels |
| US7795359B2 (en) | 2005-03-04 | 2010-09-14 | Novartis Ag | Continuous process for production of polymeric materials |
| US9804295B2 (en) * | 2005-05-05 | 2017-10-31 | Novartis Ag | Ophthalmic devices for sustained delivery of active compounds |
| US20070037897A1 (en) * | 2005-08-12 | 2007-02-15 | Guigui Wang | Method for making contact lenses |
| EP1801140A1 (en) * | 2005-12-22 | 2007-06-27 | Mnemoscience GmbH | Macro-diacrylate |
| US7858000B2 (en) | 2006-06-08 | 2010-12-28 | Novartis Ag | Method of making silicone hydrogel contact lenses |
| DK2038310T3 (da) | 2006-07-12 | 2010-09-27 | Novartis Ag | Aktinisk tværbindelige copolymerer til fremstilling af kontaktlinser |
| KR101454041B1 (ko) * | 2006-11-06 | 2014-10-27 | 노파르티스 아게 | 안구 장치 및 그의 제조 및 사용 방법 |
| AR064286A1 (es) | 2006-12-13 | 2009-03-25 | Quiceno Gomez Alexandra Lorena | Produccion de dispositivos oftalmicos basados en la polimerizacion por crecimiento escalonado fotoinducida |
| WO2008116131A2 (en) | 2007-03-22 | 2008-09-25 | Novartis Ag | Prepolymers with dangling polysiloxane-containing polymer chains |
| TWI419719B (zh) | 2007-08-31 | 2013-12-21 | Novartis Ag | 隱形眼鏡產物 |
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| AU2011282603B2 (en) | 2010-07-30 | 2014-01-30 | Novartis Ag | Amphiphilic polysiloxane prepolymers and uses thereof |
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| JP6065988B2 (ja) | 2012-12-14 | 2017-01-25 | ノバルティス アーゲー | トリス（トリメチルシロキシ）シランビニル系モノマー及びその用途 |
| HUE040618T2 (hu) | 2013-10-31 | 2019-03-28 | Novartis Ag | Eljárás szemészeti lencsék elõállítására |
| HUE036795T2 (hu) | 2013-12-13 | 2018-07-30 | Novartis Ag | Eljárás kontaktlencse elõállítására |
| EP3134461B1 (en) | 2014-04-25 | 2018-02-14 | Novartis AG | Hydrophilized carbosiloxane vinylic monomers |
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| US10160141B2 (en) | 2014-11-25 | 2018-12-25 | Novartis Ag | Molds for making contact lenses |
| EP3268804B1 (en) | 2015-03-11 | 2020-11-04 | University of Florida Research Foundation, Inc. | Mesh size control of lubrication in gemini hydrogels |
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| WO2017093834A1 (en) | 2015-12-03 | 2017-06-08 | Novartis Ag | Contact lens packaging solutions |
| KR102604468B1 (ko) | 2015-12-15 | 2023-11-22 | 알콘 인코포레이티드 | 실리콘 하이드로겔 콘택트 렌즈 상에 안정한 코팅을 적용하기 위한 방법 |
| MY192377A (en) | 2015-12-15 | 2022-08-17 | Novartis Ag | Method for producing contact lenses with a lubricious surface |
| EP3419961B1 (en) | 2016-02-22 | 2020-09-02 | Alcon Inc. | Uv/visible-absorbing vinylic monomers and uses thereof |
| CA3116257C (en) | 2016-02-22 | 2024-01-16 | Alcon Inc. | Uv-absorbing vinylic monomers and uses thereof |
| US10809181B2 (en) | 2017-08-24 | 2020-10-20 | Alcon Inc. | Method and apparatus for determining a coefficient of friction at a test site on a surface of a contact lens |
| EP3676082A1 (en) | 2017-08-29 | 2020-07-08 | Alcon Inc. | Cast-molding process for producing contact lenses |
| US10830923B2 (en) | 2017-12-13 | 2020-11-10 | Alcon Inc. | Method for producing MPS-compatible water gradient contact lenses |
| HUE059157T2 (hu) | 2018-01-22 | 2022-10-28 | Alcon Inc | Formaöntéses eljárás UV-t elnyelõ kontaktlencse elõállítására |
| WO2020100090A1 (en) | 2018-11-15 | 2020-05-22 | Alcon Inc. | Contact lens with phosphorylcholine-modified polyvinylalcohols therein |
| SG11202108875UA (en) | 2019-04-10 | 2021-10-28 | Alcon Inc | Method for producing coated contact lenses |
| MY206069A (en) | 2019-05-28 | 2024-11-27 | Alcon Inc | Pad transfer printing method for making colored contact lenses |
| WO2022097049A1 (en) | 2020-11-04 | 2022-05-12 | Alcon Inc. | Method for making photochromic contact lenses |
| EP4240578B1 (en) | 2020-11-04 | 2024-12-18 | Alcon Inc. | Method for making photochromic contact lenses |
| US12111443B2 (en) | 2021-03-08 | 2024-10-08 | Alcon Inc. | Method for making photochromic contact lenses |
| WO2022201072A1 (en) | 2021-03-24 | 2022-09-29 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| KR20230144622A (ko) | 2021-04-01 | 2023-10-16 | 알콘 인코포레이티드 | 내장형 히드로겔 콘택트 렌즈 |
| WO2022208448A1 (en) | 2021-04-01 | 2022-10-06 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| EP4514594A1 (en) | 2022-04-26 | 2025-03-05 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| EP4514595A1 (en) | 2022-04-26 | 2025-03-05 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| KR20240163713A (ko) | 2022-05-09 | 2024-11-19 | 알콘 인코포레이티드 | 내장형 히드로겔 콘택트 렌즈의 제조 방법 |
| JP2025517724A (ja) | 2022-05-23 | 2025-06-10 | アルコン インク． | Ｕｖ／ｈｅｖｌフィルタリングコンタクトレンズ |
| TW202413071A (zh) | 2022-05-25 | 2024-04-01 | 瑞士商愛爾康公司 | 用於製造嵌入式水凝膠接觸鏡片之方法 |
| TW202500366A (zh) | 2023-03-22 | 2025-01-01 | 瑞士商愛爾康公司 | 用於製造嵌入式水凝膠接觸鏡片之方法 |
| EP4719752A1 (en) | 2023-06-01 | 2026-04-08 | Alcon Inc. | Method for making embedded silicone hydrogel contact lenses |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5039458A (en) * | 1987-12-21 | 1991-08-13 | W. R. Grace & Co.-Conn. | Method of making a hydrophilic, biocompatible, protein non-adsorptive contact lens |
| EP0379462B1 (en) * | 1989-01-11 | 1995-02-22 | Ciba-Geigy Ag | Vinylic macromers containing perfluoropolyalkylether and polyalkylether segments, polymers, copolymers and ophthalmic devices made therefrom |
| US5196458A (en) * | 1991-10-15 | 1993-03-23 | Johnson & Johnson Vision Products, Inc. | Soft, high oxygen permeability ophthalmic lens |
| TW264487B (https=) * | 1992-02-18 | 1995-12-01 | Takeda Pharm Industry Co Ltd | |
| DE69315003T2 (de) * | 1992-07-17 | 1998-03-12 | Ethicon Inc | Strahlenhärtbare Urethan-Acrylatprepolymere und vernetzte Polymere |
-
1998
- 1998-01-09 TW TW087100320A patent/TW425403B/zh active
- 1998-02-02 AU AU66190/98A patent/AU727156B2/en not_active Ceased
- 1998-02-02 JP JP53255098A patent/JP4098367B2/ja not_active Expired - Fee Related
- 1998-02-02 AR ARP980100452A patent/AR011612A1/es unknown
- 1998-02-02 DE DE69800994T patent/DE69800994T2/de not_active Expired - Lifetime
- 1998-02-02 AT AT98908040T patent/ATE202578T1/de active
- 1998-02-02 US US09/355,769 patent/US6165408A/en not_active Expired - Lifetime
- 1998-02-02 ES ES98908040T patent/ES2160403T3/es not_active Expired - Lifetime
- 1998-02-02 CA CA002278566A patent/CA2278566A1/en not_active Abandoned
- 1998-02-03 ZA ZA98865A patent/ZA98865B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA98865B (en) | 1998-08-04 |
| AU6619098A (en) | 1998-08-25 |
| AR011612A1 (es) | 2000-08-30 |
| HK1024008A1 (en) | 2000-09-29 |
| TW425403B (en) | 2001-03-11 |
| ATE202578T1 (de) | 2001-07-15 |
| JP2001509915A (ja) | 2001-07-24 |
| JP4098367B2 (ja) | 2008-06-11 |
| ES2160403T3 (es) | 2001-11-01 |
| US6165408A (en) | 2000-12-26 |
| AU727156B2 (en) | 2000-12-07 |
| DE69800994D1 (de) | 2001-08-02 |
| DE69800994T2 (de) | 2001-11-29 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |