TW425403B - Branched polyurethane (meth)acrylate prepolymers, opthal-mic mouldings derived therefrom and processes for their manufacture - Google Patents
Branched polyurethane (meth)acrylate prepolymers, opthal-mic mouldings derived therefrom and processes for their manufacture Download PDFInfo
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- TW425403B TW425403B TW087100320A TW87100320A TW425403B TW 425403 B TW425403 B TW 425403B TW 087100320 A TW087100320 A TW 087100320A TW 87100320 A TW87100320 A TW 87100320A TW 425403 B TW425403 B TW 425403B
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- alkylene
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- 238000000034 method Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 238000000465 moulding Methods 0.000 title claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims description 3
- 239000004814 polyurethane Substances 0.000 title claims description 3
- 229920002635 polyurethane Polymers 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 150000004820 halides Chemical class 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 21
- 229920005862 polyol Polymers 0.000 claims abstract description 21
- 238000004132 cross linking Methods 0.000 claims abstract description 18
- 150000003077 polyols Chemical class 0.000 claims abstract description 15
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 10
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 7
- 150000002016 disaccharides Chemical class 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- -1 aliphatic polyol Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 28
- 239000005977 Ethylene Substances 0.000 claims description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 24
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 230000002079 cooperative effect Effects 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000007334 copolymerization reaction Methods 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 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 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- SZJXEIBPJWMWQR-UHFFFAOYSA-N 2-methylpropane-1,1,1-triol Chemical compound CC(C)C(O)(O)O SZJXEIBPJWMWQR-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 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 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229920001281 polyalkylene Polymers 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- 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 description 2
- 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 2
- 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 2
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- GFMIDCCZJUXASS-UHFFFAOYSA-N hexane-1,1,6-triol Chemical compound OCCCCCC(O)O GFMIDCCZJUXASS-UHFFFAOYSA-N 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- FDZWELNHSHIIGQ-UHFFFAOYSA-N N=C=O.CCC(C)CC(C)(C)C Chemical compound N=C=O.CCC(C)CC(C)(C)C FDZWELNHSHIIGQ-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000600 disaccharide group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 claims 1
- LBUSGXDHOHEPQQ-UHFFFAOYSA-N propane-1,1,1-triol Chemical compound CCC(O)(O)O LBUSGXDHOHEPQQ-UHFFFAOYSA-N 0.000 claims 1
- 235000015170 shellfish Nutrition 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
- 229910052722 tritium Inorganic materials 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 20
- 239000005056 polyisocyanate Substances 0.000 abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 abstract description 10
- 229920005906 polyester polyol Polymers 0.000 abstract description 6
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 4
- 229920000570 polyether Polymers 0.000 abstract description 4
- 125000002348 vinylic group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000010408 film Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 230000002209 hydrophobic effect Effects 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229920001038 ethylene copolymer Polymers 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000036571 hydration Effects 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000000108 ultra-filtration Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000002993 cycloalkylene group Chemical group 0.000 description 4
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
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- 239000000017 hydrogel Substances 0.000 description 4
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- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
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- 150000002367 halogens Chemical group 0.000 description 3
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- 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
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 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
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- 230000000875 corresponding effect Effects 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- 235000012054 meals Nutrition 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229920002120 photoresistant polymer Polymers 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
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97810056A EP0867456A1 (de) | 1997-02-04 | 1997-02-04 | Ophthalmischer Formkörper |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW425403B true TW425403B (en) | 2001-03-11 |
Family
ID=8230146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087100320A TW425403B (en) | 1997-02-04 | 1998-01-09 | Branched polyurethane (meth)acrylate prepolymers, opthal-mic mouldings derived therefrom and processes for their manufacture |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6165408A (enExample) |
| JP (1) | JP4098367B2 (enExample) |
| AR (1) | AR011612A1 (enExample) |
| AT (1) | ATE202578T1 (enExample) |
| AU (1) | AU727156B2 (enExample) |
| CA (1) | CA2278566A1 (enExample) |
| DE (1) | DE69800994T2 (enExample) |
| ES (1) | ES2160403T3 (enExample) |
| TW (1) | TW425403B (enExample) |
| ZA (1) | ZA98865B (enExample) |
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| US7998412B2 (en) | 2000-01-07 | 2011-08-16 | Smart Holograms Limited | Ophthalmic device comprising a holographic sensor |
| US7005143B2 (en) * | 2002-04-12 | 2006-02-28 | 3M Innovative Properties Company | Gel materials, medical articles, and methods |
| US6777290B2 (en) * | 2002-08-05 | 2004-08-17 | Micron Technology, Inc. | Global column select structure for accessing a memory |
| EP1534767B1 (en) * | 2002-08-14 | 2007-11-28 | Novartis AG | Radiation-curable prepolymers |
| US7235195B2 (en) * | 2002-09-06 | 2007-06-26 | Novartis Ag | Method for making opthalmic devices |
| US20050085585A1 (en) * | 2002-10-23 | 2005-04-21 | Quinn Michael H. | Polymerizable materials |
| ATE520661T1 (de) * | 2003-06-27 | 2011-09-15 | Univ Maryland | Heterocyclische verbindungen mit quaternärem stickstoff zum nachweis von wässrigen monosacchariden in physiologischen flüssigkeiten |
| WO2005015184A1 (en) * | 2003-07-30 | 2005-02-17 | Novartis Ag | Reflection hologram sensor in contact lens |
| DE602004028020D1 (de) * | 2003-08-07 | 2010-08-19 | Eyesense Ag | Ophthalmischer sensor |
| US20050056954A1 (en) * | 2003-09-12 | 2005-03-17 | Devlin Brian Gerrard | Method for making contact lenses |
| 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 |
| ES2346812T3 (es) | 2006-07-12 | 2010-10-20 | Novartis Ag | Copolimeros actinicamente entrelazables para la fabricacion de lentes de contacto. |
| CA2914805C (en) * | 2006-11-06 | 2017-12-12 | Alcon Inc. | Ocular devices and methods of making and using thereof |
| AR064286A1 (es) | 2006-12-13 | 2009-03-25 | Quiceno Gomez Alexandra Lorena | Produccion de dispositivos oftalmicos basados en la polimerizacion por crecimiento escalonado fotoinducida |
| EP2129513B1 (en) | 2007-03-22 | 2016-08-03 | Novartis AG | Prepolymers with dangling polysiloxane-containing polymer chains |
| TWI551305B (zh) | 2007-08-31 | 2016-10-01 | 諾華公司 | 相對黏稠封裝溶液之用途 |
| CN101903807B (zh) | 2007-12-20 | 2013-01-09 | 诺瓦提斯公司 | 隐形眼镜的制造方法 |
| CN101980855B (zh) * | 2008-04-02 | 2013-06-12 | 诺瓦提斯公司 | 使用立体光刻和单个模具表面制造接触透镜的方法和系统 |
| TWI506333B (zh) | 2008-12-05 | 2015-11-01 | Novartis Ag | 用以傳遞疏水性舒適劑之眼用裝置及其製造方法 |
| AU2009333223B2 (en) * | 2008-12-30 | 2012-02-23 | Novartis Ag | Tri-functional UV-absorbing compounds and use thereof |
| JP5575881B2 (ja) * | 2009-05-22 | 2014-08-20 | ノバルティス アーゲー | 化学線架橋性シロキサン含有コポリマー |
| EP2432821B1 (en) | 2009-05-22 | 2017-08-30 | Novartis AG | Actinically-crosslinkable siloxane-containing copolymers |
| MY158359A (en) | 2009-09-15 | 2016-09-30 | Novartis Ag | Prepolymers suitable for making ultra-violet absorbing contact lenses |
| TWI522395B (zh) | 2010-07-30 | 2016-02-21 | 諾華公司 | 兩親性聚矽氧烷預聚物及其用途 |
| EP2625216B1 (en) | 2010-10-06 | 2019-06-05 | Novartis AG | Polymerisable chain-extended polysiloxanes with pendant hydrophilic groups |
| NZ606787A (en) | 2010-10-06 | 2014-11-28 | Novartis Ag | Water-processable silicone-containing prepolymers and uses thereof |
| WO2012047964A1 (en) | 2010-10-06 | 2012-04-12 | Novartis Ag | Chain-extended polysiloxane crosslinkers with dangling hydrophilic polymer chains |
| EP2637847B1 (en) | 2010-11-10 | 2014-07-23 | Novartis AG | Method for making contact lenses |
| EP2652532B1 (en) | 2010-12-13 | 2016-06-08 | Novartis AG | Ophthalmic lenses modified with functional groups and methods of making thereof |
| EP2931733B1 (en) | 2012-12-14 | 2016-10-05 | Novartis AG | Tris(trimethyl siloxy)silane vinylic monomers and uses thereof |
| WO2014093764A1 (en) | 2012-12-14 | 2014-06-19 | Novartis Ag | Amphiphilic siloxane-containing (meth)acrylamides and uses thereof |
| US9103965B2 (en) | 2012-12-14 | 2015-08-11 | Novartis Ag | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
| CA2889894C (en) | 2012-12-14 | 2017-09-12 | Novartis Ag | Actinically-crosslinkable amphiphilic prepolymers |
| HUE040618T2 (hu) | 2013-10-31 | 2019-03-28 | Novartis Ag | Eljárás szemészeti lencsék elõállítására |
| MY183117A (en) | 2013-12-13 | 2021-02-15 | Alcon Inc | Method for making contact lenses |
| JP6355821B2 (ja) | 2014-04-25 | 2018-07-11 | ノバルティス アーゲー | カルボシロキサンビニル系モノマー |
| CA2940207C (en) | 2014-04-25 | 2019-09-10 | Novartis Ag | Hydrophilized carbosiloxane vinylic monomers |
| US11002884B2 (en) | 2014-08-26 | 2021-05-11 | Alcon Inc. | Method for applying stable coating on silicone hydrogel contact lenses |
| 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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| MY186090A (en) | 2015-12-03 | 2021-06-21 | Alcon Inc | Contact lens packaging solutions |
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| US10081142B2 (en) | 2015-12-15 | 2018-09-25 | Novartis Ag | Method for producing contact lenses with a lubricious surface |
| US10268053B2 (en) | 2016-02-22 | 2019-04-23 | Novartis Ag | UV/visible-absorbing vinylic monomers and uses thereof |
| JP6546352B2 (ja) | 2016-02-22 | 2019-07-17 | ノバルティス アーゲー | Ｕｖ吸収ビニルモノマーおよびその使用 |
| EP3447475B1 (en) | 2017-08-24 | 2020-06-17 | Alcon Inc. | Method and apparatus for determining a coefficient of friction at a test site on a surface of a contact lens |
| WO2019043577A1 (en) | 2017-08-29 | 2019-03-07 | Novartis Ag | CASTING MOLDING PROCESS FOR PRODUCING CONTACT LENSES |
| MY201826A (en) | 2017-12-13 | 2024-03-19 | Alcon Inc | Method for producing mps-compatible water gradient contact lenses |
| WO2019142132A1 (en) | 2018-01-22 | 2019-07-25 | Novartis Ag | Cast-molding process for producing uv-absorbing contact lenses |
| US11061169B2 (en) | 2018-11-15 | 2021-07-13 | Alcon Inc. | Contact lens with phosphorylcholine-modified polyvinylalcohols therein |
| EP3953744B1 (en) | 2019-04-10 | 2025-08-13 | Alcon Inc. | Method for producing coated contact lenses |
| US11602910B2 (en) | 2019-05-28 | 2023-03-14 | Alcon Inc. | Pad transfer printing method for making colored contact lenses |
| EP4146717A1 (en) * | 2020-05-06 | 2023-03-15 | Universiteit Gent | Shape-memory polymers |
| HUE069913T2 (hu) | 2020-11-04 | 2025-04-28 | Alcon Inc | Eljárás fotokróm kontaktlencsék elõállítására |
| HUE070248T2 (hu) | 2020-11-04 | 2025-05-28 | Alcon Inc | Eljárás fotokróm kontaktlencsék elõállítására |
| EP4304842B1 (en) | 2021-03-08 | 2026-05-06 | Alcon Inc. | Method for making photofunctional contact lenses |
| US12194698B2 (en) | 2021-03-24 | 2025-01-14 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
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| US12358188B2 (en) | 2022-04-26 | 2025-07-15 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
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| EP4529621A1 (en) | 2022-05-23 | 2025-04-02 | Alcon Inc. | Uv/hevl-filtering contact lenses |
| KR20240172202A (ko) | 2022-05-25 | 2024-12-09 | 알콘 인코포레이티드 | 내장형 히드로겔 콘택트 렌즈의 제조 방법 |
| 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 |
| TW202513285A (zh) | 2023-06-01 | 2025-04-01 | 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 |
| WO2026083258A1 (en) | 2024-10-15 | 2026-04-23 | Alcon Inc. | Composite contact lenses with ultrathin objects |
| US20260118700A1 (en) | 2024-10-29 | 2026-04-30 | Alcon Inc. | Diffractive multifocal contact lens |
| US20260219423A1 (en) | 2025-01-29 | 2026-07-30 | Alcon Inc. | Controlled release of dry eye relief agent from contact lens |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (enExample) * | 1992-02-18 | 1995-12-01 | Takeda Pharm Industry Co Ltd | |
| EP0579503B1 (en) * | 1992-07-17 | 1997-11-05 | Ethicon Inc. | Radiation-curable, urethane-acrylate prepolymers and crosslinked polymers |
-
1998
- 1998-01-09 TW TW087100320A patent/TW425403B/zh active
- 1998-02-02 ES ES98908040T patent/ES2160403T3/es not_active Expired - Lifetime
- 1998-02-02 JP JP53255098A patent/JP4098367B2/ja not_active Expired - Fee Related
- 1998-02-02 AT AT98908040T patent/ATE202578T1/de active
- 1998-02-02 AU AU66190/98A patent/AU727156B2/en not_active Ceased
- 1998-02-02 AR ARP980100452A patent/AR011612A1/es unknown
- 1998-02-02 DE DE69800994T patent/DE69800994T2/de not_active Expired - Lifetime
- 1998-02-02 US US09/355,769 patent/US6165408A/en 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 |
|---|---|
| ATE202578T1 (de) | 2001-07-15 |
| DE69800994D1 (de) | 2001-08-02 |
| DE69800994T2 (de) | 2001-11-29 |
| JP4098367B2 (ja) | 2008-06-11 |
| CA2278566A1 (en) | 1998-08-06 |
| JP2001509915A (ja) | 2001-07-24 |
| AU6619098A (en) | 1998-08-25 |
| ZA98865B (en) | 1998-08-04 |
| AR011612A1 (es) | 2000-08-30 |
| ES2160403T3 (es) | 2001-11-01 |
| US6165408A (en) | 2000-12-26 |
| AU727156B2 (en) | 2000-12-07 |
| HK1024008A1 (en) | 2000-09-29 |
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