JP2000506554A - ポリシロキサン／ポリオールマクロマーから製造されるポリウレタン - Google Patents
ポリシロキサン／ポリオールマクロマーから製造されるポリウレタンInfo
- Publication number
- JP2000506554A JP2000506554A JP09523259A JP52325997A JP2000506554A JP 2000506554 A JP2000506554 A JP 2000506554A JP 09523259 A JP09523259 A JP 09523259A JP 52325997 A JP52325997 A JP 52325997A JP 2000506554 A JP2000506554 A JP 2000506554A
- Authority
- JP
- Japan
- Prior art keywords
- group
- polymer
- carbon atoms
- segment
- diisocyanate
- 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.)
- Ceased
Links
- -1 polysiloxane Polymers 0.000 title claims abstract description 136
- 229920005862 polyol Polymers 0.000 title claims abstract description 49
- 150000003077 polyols Chemical class 0.000 title claims abstract description 41
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 39
- 239000004814 polyurethane Substances 0.000 title description 3
- 229920002635 polyurethane Polymers 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 29
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
- 210000004087 cornea Anatomy 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 34
- 125000005442 diisocyanate group Chemical group 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 239000007943 implant Substances 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 18
- 230000000007 visual effect Effects 0.000 claims description 18
- 125000000732 arylene group Chemical group 0.000 claims description 17
- 150000001720 carbohydrates Chemical class 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000002723 alicyclic group Chemical group 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 230000009257 reactivity Effects 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000002894 organic compounds Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 239000012530 fluid Substances 0.000 claims description 7
- 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 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 5
- 239000011148 porous material Substances 0.000 claims description 5
- 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 description 5
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000008467 tissue growth Effects 0.000 claims description 4
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 claims description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 3
- LFHITXHDBPEMEZ-UHFFFAOYSA-N 3-isocyanatopropyl-[3-isocyanatopropyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound O=C=NCCC[Si](C)(C)O[Si](C)(C)CCCN=C=O LFHITXHDBPEMEZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 230000010261 cell growth Effects 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000000686 lactone group Chemical group 0.000 claims description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims 1
- 238000002513 implantation Methods 0.000 claims 1
- 235000004252 protein component Nutrition 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 18
- 239000002243 precursor Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 47
- 239000000047 product Substances 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 235000014633 carbohydrates Nutrition 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 238000004132 cross linking Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 14
- 150000002596 lactones Chemical class 0.000 description 14
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 14
- 239000004205 dimethyl polysiloxane Substances 0.000 description 13
- 230000035699 permeability Effects 0.000 description 13
- 229920000858 Cyclodextrin Polymers 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- 150000002513 isocyanates Chemical group 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 210000001519 tissue Anatomy 0.000 description 10
- 238000004448 titration Methods 0.000 description 10
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- KXLNRTHAZOEDNA-UHFFFAOYSA-N dibutyl(didodecyl)stannane Chemical compound CCCCCCCCCCCC[Sn](CCCC)(CCCC)CCCCCCCCCCCC KXLNRTHAZOEDNA-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 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 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
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- 239000000725 suspension Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- JCZPMGDSEAFWDY-SQOUGZDYSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanamide Chemical compound NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO JCZPMGDSEAFWDY-SQOUGZDYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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- 125000003545 alkoxy group Chemical group 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
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- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 4
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- 229910052782 aluminium Inorganic materials 0.000 description 3
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- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- OSLGKRDOEMLAJV-UHFFFAOYSA-N benzyl n-prop-2-enylcarbamate Chemical compound C=CCNC(=O)OCC1=CC=CC=C1 OSLGKRDOEMLAJV-UHFFFAOYSA-N 0.000 description 3
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- VTPNPMGMYAMEJY-UHFFFAOYSA-N methyl 2-methylprop-2-enoate 2-methylprop-2-enoic acid 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate 3-tris[[dimethyl(trimethylsilyloxy)silyl]oxy]silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(O)=O.COC(=O)C(C)=C.CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C.CC(=C)C(=O)OCCC[Si](O[Si](C)(C)O[Si](C)(C)C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](C)(C)O[Si](C)(C)C VTPNPMGMYAMEJY-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000001087 myotubule Anatomy 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- ZCLAHGAZPPEVDX-MQHGYYCBSA-N panose Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@@H]1CO[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ZCLAHGAZPPEVDX-MQHGYYCBSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Substances OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
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- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000010019 resist printing Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 210000002536 stromal cell Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Silicon Polymers (AREA)
- Eyeglasses (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95810818.5 | 1995-12-22 | ||
| EP95810818 | 1995-12-22 | ||
| PCT/EP1996/005507 WO1997023532A1 (en) | 1995-12-22 | 1996-12-10 | Polyurethanes made from polysiloxane/polyol macromers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000506554A true JP2000506554A (ja) | 2000-05-30 |
| JP2000506554A5 JP2000506554A5 (OSRAM) | 2004-11-04 |
Family
ID=8221837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09523259A Ceased JP2000506554A (ja) | 1995-12-22 | 1996-12-10 | ポリシロキサン／ポリオールマクロマーから製造されるポリウレタン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6271332B1 (OSRAM) |
| EP (1) | EP0868457B1 (OSRAM) |
| JP (1) | JP2000506554A (OSRAM) |
| AT (1) | ATE223933T1 (OSRAM) |
| AU (1) | AU1369397A (OSRAM) |
| DE (1) | DE69623647T2 (OSRAM) |
| WO (1) | WO1997023532A1 (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007526941A (ja) * | 2004-02-23 | 2007-09-20 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | バイオマス由来材料を含有する架橋ポリマー |
| JPWO2021045203A1 (OSRAM) * | 2019-09-05 | 2021-03-11 | ||
| JPWO2021172468A1 (OSRAM) * | 2020-02-25 | 2021-09-02 | ||
| WO2023003043A1 (ja) * | 2021-07-21 | 2023-01-26 | 国立大学法人大阪大学 | シリコーン系高分子化合物及びシリコーン系高分子材料 |
| JP2023504179A (ja) * | 2019-12-02 | 2023-02-01 | ボシュ ＋ ロム アイルランド リミテッド | 直接圧縮成形された眼科用装置 |
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| US8527026B2 (en) | 1997-03-04 | 2013-09-03 | Dexcom, Inc. | Device and method for determining analyte levels |
| US6001067A (en) | 1997-03-04 | 1999-12-14 | Shults; Mark C. | Device and method for determining analyte levels |
| ATE326913T1 (de) | 1997-08-13 | 2006-06-15 | Solarant Medical Inc | Nichtinvasive geräte und systeme zum schrumpfen von geweben |
| US9023031B2 (en) | 1997-08-13 | 2015-05-05 | Verathon Inc. | Noninvasive devices, methods, and systems for modifying tissues |
| US6849671B2 (en) | 1998-03-02 | 2005-02-01 | Johnson & Johnson Vision Care, Inc. | Contact lenses |
| FR2779940B1 (fr) * | 1998-06-19 | 2000-11-03 | Ioltechnologie Production | Implant formant lentille intraoculaire monobloc bi-materiaux |
| US6599559B1 (en) * | 2000-04-03 | 2003-07-29 | Bausch & Lomb Incorporated | Renewable surface treatment of silicone medical devices with reactive hydrophilic polymers |
| US7306591B2 (en) | 2000-10-02 | 2007-12-11 | Novasys Medical, Inc. | Apparatus and methods for treating female urinary incontinence |
| US20030032874A1 (en) | 2001-07-27 | 2003-02-13 | Dexcom, Inc. | Sensor head for use with implantable devices |
| US8364229B2 (en) | 2003-07-25 | 2013-01-29 | Dexcom, Inc. | Analyte sensors having a signal-to-noise ratio substantially unaffected by non-constant noise |
| US7613491B2 (en) | 2002-05-22 | 2009-11-03 | Dexcom, Inc. | Silicone based membranes for use in implantable glucose sensors |
| US7226978B2 (en) | 2002-05-22 | 2007-06-05 | Dexcom, Inc. | Techniques to improve polyurethane membranes for implantable glucose sensors |
| US9763609B2 (en) | 2003-07-25 | 2017-09-19 | Dexcom, Inc. | Analyte sensors having a signal-to-noise ratio substantially unaffected by non-constant noise |
| WO2005011520A2 (en) | 2003-07-25 | 2005-02-10 | Dexcom, Inc. | Oxygen enhancing membrane systems for implantable devices |
| US7591801B2 (en) | 2004-02-26 | 2009-09-22 | Dexcom, Inc. | Integrated delivery device for continuous glucose sensor |
| US7920906B2 (en) | 2005-03-10 | 2011-04-05 | Dexcom, Inc. | System and methods for processing analyte sensor data for sensor calibration |
| US9247900B2 (en) | 2004-07-13 | 2016-02-02 | Dexcom, Inc. | Analyte sensor |
| US8808228B2 (en) | 2004-02-26 | 2014-08-19 | Dexcom, Inc. | Integrated medicament delivery device for use with continuous analyte sensor |
| US8277713B2 (en) | 2004-05-03 | 2012-10-02 | Dexcom, Inc. | Implantable analyte sensor |
| US7946984B2 (en) | 2004-07-13 | 2011-05-24 | Dexcom, Inc. | Transcutaneous analyte sensor |
| US20060200245A1 (en) * | 2005-03-07 | 2006-09-07 | Sdgi Holdings, Inc. | Materials, devices, and methods for in-situ formation of composite intervertebral implants |
| US8133178B2 (en) | 2006-02-22 | 2012-03-13 | Dexcom, Inc. | Analyte sensor |
| US8744546B2 (en) | 2005-05-05 | 2014-06-03 | Dexcom, Inc. | Cellulosic-based resistance domain for an analyte sensor |
| WO2007120381A2 (en) | 2006-04-14 | 2007-10-25 | Dexcom, Inc. | Analyte sensor |
| US20200037874A1 (en) | 2007-05-18 | 2020-02-06 | Dexcom, Inc. | Analyte sensors having a signal-to-noise ratio substantially unaffected by non-constant noise |
| US20080306434A1 (en) | 2007-06-08 | 2008-12-11 | Dexcom, Inc. | Integrated medicament delivery device for use with continuous analyte sensor |
| EP4159114B1 (en) | 2007-10-09 | 2024-04-10 | DexCom, Inc. | Integrated insulin delivery system with continuous glucose sensor |
| US11730407B2 (en) | 2008-03-28 | 2023-08-22 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8583204B2 (en) | 2008-03-28 | 2013-11-12 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8682408B2 (en) | 2008-03-28 | 2014-03-25 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| WO2010033724A2 (en) | 2008-09-19 | 2010-03-25 | Dexcom, Inc. | Particle-containing membrane and particulate electrode for analyte sensors |
| KR101724984B1 (ko) | 2010-07-30 | 2017-04-07 | 노파르티스 아게 | 가교된 친수성 코팅을 갖는 실리콘 히드로겔 렌즈 |
| SG11201400228WA (en) | 2011-10-12 | 2014-05-29 | Novartis Ag | Method for making uv-absorbing ophthalmic lenses by coating |
| WO2014039495A1 (en) | 2012-09-05 | 2014-03-13 | University Of Miami | Novel keratoprosthesis, and system and method of corneal repair using same |
| EP2932314B1 (en) | 2012-12-17 | 2017-02-01 | Novartis AG | Method for making improved uv-absorbing ophthalmic lenses |
| SG11201603699SA (en) | 2013-12-17 | 2016-07-28 | Novartis Ag | A silicone hydrogel lens with a crosslinked hydrophilic coating |
| EP3122828B1 (en) | 2014-03-26 | 2025-10-15 | 3M Innovative Properties Company | Polyurethane compositions, films, and methods thereof |
| HUE046948T2 (hu) | 2014-08-26 | 2020-03-30 | Novartis Ag | Eljárás stabil bevonat felvitelére szilikon hidrogél kontaktlencsékre |
| WO2017103793A1 (en) | 2015-12-15 | 2017-06-22 | Novartis Ag | Method for applying stable coating on silicone hydrogel contact lenses |
| DK3700416T3 (da) | 2017-10-24 | 2024-09-30 | Dexcom Inc | På forhånd forbundne analytsensorer |
| US11331022B2 (en) | 2017-10-24 | 2022-05-17 | Dexcom, Inc. | Pre-connected analyte sensors |
| CN117492232A (zh) | 2017-12-13 | 2024-02-02 | 爱尔康公司 | 周抛和月抛水梯度接触镜片 |
| KR102598533B1 (ko) * | 2018-08-24 | 2023-11-03 | 현대자동차주식회사 | 디-글루카로-1,4:6,3-다이락톤의 제조방법 |
| CN118806984A (zh) * | 2023-04-17 | 2024-10-22 | 杭州启明医疗器械股份有限公司 | 可植入材料及其合成方法和人工心脏瓣膜 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3535283A1 (de) * | 1985-10-03 | 1987-04-09 | Byk Chemie Gmbh | Polyestergruppenhaltige polysiloxane fuer lacke und formmassen und die verwendung hierfuer |
| US4737558A (en) | 1985-11-25 | 1988-04-12 | Alcon Laboratories, Inc. | Siloxane copolymers for ophthalmic applications |
| US5221724A (en) * | 1987-08-12 | 1993-06-22 | Wisconsin Alumni Research Foundation | Polysiloxane polyurea urethanes |
| US4942212A (en) * | 1988-01-20 | 1990-07-17 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Polyurethane resin and heat-sensitive recording medium |
| US4983702A (en) | 1988-09-28 | 1991-01-08 | Ciba-Geigy Corporation | Crosslinked siloxane-urethane polymer contact lens |
| US4883854A (en) | 1988-09-30 | 1989-11-28 | Medtronic, Inc. | Hydroxyl functional monomers |
| US4962178A (en) | 1988-11-03 | 1990-10-09 | Ciba-Geigy Corporation | Novel polysiloxane-polyurethanes and contact lens thereof |
| JPH02228323A (ja) | 1989-03-02 | 1990-09-11 | Dainichiseika Color & Chem Mfg Co Ltd | シロキサン変性ポリエステル系樹脂及びその製造方法 |
| US5196458A (en) * | 1991-10-15 | 1993-03-23 | Johnson & Johnson Vision Products, Inc. | Soft, high oxygen permeability ophthalmic lens |
| US5589563A (en) * | 1992-04-24 | 1996-12-31 | The Polymer Technology Group | Surface-modifying endgroups for biomedical polymers |
| DE59305382D1 (de) | 1992-08-05 | 1997-03-20 | Ciba Geigy Ag | Kontaktlinsen aus lipophilisierten Cyclodextrinen |
| DE4243799A1 (de) * | 1992-12-23 | 1994-06-30 | Bayer Ag | Siloxanblockcopolymer-modifizierte thermoplastische Polyurethane |
| ES2165925T3 (es) * | 1994-10-04 | 2002-04-01 | Minnesota Mining & Mfg | Composiciones reactivas de poliuretano en dos partes y revestimientos opcionalmente autorregenerables y resistentes al rayado preparados a partir de las mismas. |
| US6039913A (en) * | 1998-08-27 | 2000-03-21 | Novartis Ag | Process for the manufacture of an ophthalmic molding |
-
1996
- 1996-12-10 JP JP09523259A patent/JP2000506554A/ja not_active Ceased
- 1996-12-10 WO PCT/EP1996/005507 patent/WO1997023532A1/en not_active Ceased
- 1996-12-10 AT AT96943907T patent/ATE223933T1/de not_active IP Right Cessation
- 1996-12-10 AU AU13693/97A patent/AU1369397A/en not_active Abandoned
- 1996-12-10 DE DE69623647T patent/DE69623647T2/de not_active Expired - Lifetime
- 1996-12-10 EP EP96943907A patent/EP0868457B1/en not_active Expired - Lifetime
- 1996-12-10 US US09/091,394 patent/US6271332B1/en not_active Expired - Lifetime
Cited By (9)
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|---|---|---|---|---|
| JP2007526941A (ja) * | 2004-02-23 | 2007-09-20 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | バイオマス由来材料を含有する架橋ポリマー |
| JPWO2021045203A1 (OSRAM) * | 2019-09-05 | 2021-03-11 | ||
| WO2021045203A1 (ja) * | 2019-09-05 | 2021-03-11 | 国立大学法人大阪大学 | 高分子材料及びその製造方法 |
| JP7653148B2 (ja) | 2019-09-05 | 2025-03-28 | 国立大学法人大阪大学 | 高分子材料及びその製造方法 |
| JP2023504179A (ja) * | 2019-12-02 | 2023-02-01 | ボシュ ＋ ロム アイルランド リミテッド | 直接圧縮成形された眼科用装置 |
| JPWO2021172468A1 (OSRAM) * | 2020-02-25 | 2021-09-02 | ||
| WO2021172468A1 (ja) * | 2020-02-25 | 2021-09-02 | 株式会社 資生堂 | ホスト基及び／又はゲスト基を有するシロキサン結合含有高分子化合物を含む樹脂材料 |
| JP7721090B2 (ja) | 2020-02-25 | 2025-08-12 | 株式会社 資生堂 | ホスト基及び／又はゲスト基を有するシロキサン結合含有高分子化合物を含む樹脂材料 |
| WO2023003043A1 (ja) * | 2021-07-21 | 2023-01-26 | 国立大学法人大阪大学 | シリコーン系高分子化合物及びシリコーン系高分子材料 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69623647T2 (de) | 2003-05-28 |
| US6271332B1 (en) | 2001-08-07 |
| ATE223933T1 (de) | 2002-09-15 |
| WO1997023532A1 (en) | 1997-07-03 |
| EP0868457B1 (en) | 2002-09-11 |
| EP0868457A1 (en) | 1998-10-07 |
| AU1369397A (en) | 1997-07-17 |
| DE69623647D1 (en) | 2002-10-17 |
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