CA2055397C - Bulk polymerization using specific metallocene catalysts for the preparation of cycloolefin polymers - Google Patents
Bulk polymerization using specific metallocene catalysts for the preparation of cycloolefin polymers Download PDFInfo
- Publication number
- CA2055397C CA2055397C CA002055397A CA2055397A CA2055397C CA 2055397 C CA2055397 C CA 2055397C CA 002055397 A CA002055397 A CA 002055397A CA 2055397 A CA2055397 A CA 2055397A CA 2055397 C CA2055397 C CA 2055397C
- Authority
- CA
- Canada
- Prior art keywords
- group
- cycloolefin
- formula
- polymerization
- different
- 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.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims abstract description 8
- 239000012968 metallocene catalyst Substances 0.000 title abstract description 6
- 238000012662 bulk polymerization Methods 0.000 title abstract description 5
- 150000001925 cycloalkenes Chemical class 0.000 claims abstract description 43
- -1 polycyclic olefins Chemical class 0.000 claims abstract description 40
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 27
- 229920001577 copolymer Polymers 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 22
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
- 239000005977 Ethylene Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- SVHPGKHHBXQFLQ-UHFFFAOYSA-L Cl[Zr](Cl)(C1C=CC=C1)(C1c2ccccc2-c2ccccc12)=C(c1ccccc1)c1ccccc1 Chemical compound Cl[Zr](Cl)(C1C=CC=C1)(C1c2ccccc2-c2ccccc12)=C(c1ccccc1)c1ccccc1 SVHPGKHHBXQFLQ-UHFFFAOYSA-L 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000010955 niobium Substances 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 229910052758 niobium Inorganic materials 0.000 claims description 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 229910052715 tantalum Inorganic materials 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- OGSNMYNEHSQLMI-UHFFFAOYSA-L [Cl-].[Cl-].CC=1C(C=CC=1)([Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)=C)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].CC=1C(C=CC=1)([Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)=C)C1=CC=CC=C1 OGSNMYNEHSQLMI-UHFFFAOYSA-L 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- MSAXHOHXSUCHRP-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C=1C(C=CC=1)([Hf+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)=C)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C=1C(C=CC=1)([Hf+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)=C)C1=CC=CC=C1 MSAXHOHXSUCHRP-UHFFFAOYSA-L 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 21
- 238000010348 incorporation Methods 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000007142 ring opening reaction Methods 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 51
- 150000001336 alkenes Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000566113 Branta sandvicensis Species 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- SCVXORFLOXDESF-UHFFFAOYSA-L Cl[Hf](Cl)(C1C=CC=C1)(C1c2ccccc2-c2ccccc12)=C(c1ccccc1)c1ccccc1 Chemical compound Cl[Hf](Cl)(C1C=CC=C1)(C1c2ccccc2-c2ccccc12)=C(c1ccccc1)c1ccccc1 SCVXORFLOXDESF-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- FJMJPZLXUXRLLD-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2]([SiH](C)C)C1C2=CC=CC=C2C=C1 Chemical compound [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2]([SiH](C)C)C1C2=CC=CC=C2C=C1 FJMJPZLXUXRLLD-UHFFFAOYSA-L 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 235000010210 aluminium Nutrition 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- QVLAWKAXOMEXPM-DICFDUPASA-N 1,1,1,2-tetrachloro-2,2-dideuterioethane Chemical compound [2H]C([2H])(Cl)C(Cl)(Cl)Cl QVLAWKAXOMEXPM-DICFDUPASA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- SLDJVBNUBVTHHL-UHFFFAOYSA-L [Cl-].[Cl-].C1C=CC=C1[Zr+2]C1=CC=CC1 Chemical compound [Cl-].[Cl-].C1C=CC=C1[Zr+2]C1=CC=CC1 SLDJVBNUBVTHHL-UHFFFAOYSA-L 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000005331 crown glasses (windows) Substances 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 102200025123 rs145047094 Human genes 0.000 description 1
- 102220038055 rs61743568 Human genes 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000009757 thermoplastic moulding Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/602—Component covered by group C08F4/60 with an organo-aluminium compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4036264 | 1990-11-14 | ||
| DE4036264.7 | 1990-11-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2055397A1 CA2055397A1 (en) | 1992-05-15 |
| CA2055397C true CA2055397C (en) | 2004-04-20 |
Family
ID=6418254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002055397A Expired - Lifetime CA2055397C (en) | 1990-11-14 | 1991-11-13 | Bulk polymerization using specific metallocene catalysts for the preparation of cycloolefin polymers |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11577443B2 (en) | 2016-03-11 | 2023-02-14 | Polyplastics USA, Inc | Injection stretch blow-molding (ISBM) enhancement for semi-crystalline polyolefin containers utilizing alicyclic polyolefins |
Families Citing this family (72)
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|---|---|---|---|---|
| US5744664A (en) * | 1990-07-05 | 1998-04-28 | Hoechst Aktiengesellschaft | Cycloolefin copolymers (COCS) as substrate material for liquid-crystal displays |
| ATE173746T1 (de) * | 1991-02-27 | 1998-12-15 | Ticona Gmbh | Verfahren zur herstellung von cycloolefin(co)polymeren mit enger molekulargewichtsverteilung |
| EP0594147A1 (de) * | 1992-10-24 | 1994-04-27 | Hoechst Aktiengesellschaft | Cycloolefin-Copolymerisate (COC) als Substratmaterial für Flüssigkristalldisplays |
| DE4304285A1 (de) * | 1993-02-12 | 1994-08-18 | Hoechst Ag | Cycloolefincopolymere mit hoher Reißfestigkeit und niedriger optischer Dämpfung |
| DE59402624D1 (de) * | 1993-02-12 | 1997-06-12 | Hoechst Ag | Verfahren zur Herstellung von Cycloolefincopolymeren |
| EP0610850A1 (de) * | 1993-02-12 | 1994-08-17 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Cycloolefinpolymeren |
| US6214951B1 (en) | 1993-02-12 | 2001-04-10 | Hoechst Aktiengesellschaft | Cycloolefin copolymers having high tear strength and low optical attenuation |
| TW369545B (en) * | 1993-02-12 | 1999-09-11 | Hoechst Ag | Process for preparing cycloolefin copolymers |
| EP0610843B1 (de) * | 1993-02-12 | 1999-05-19 | Ticona GmbH | Verfahren zur Herstellung von Cycloolefinpolymeren |
| TW274100B (enrdf_load_stackoverflow) | 1993-02-12 | 1996-04-11 | Hoechst Ag | |
| DE4304308A1 (de) * | 1993-02-12 | 1994-08-18 | Hoechst Ag | Steife Cycloolefincopolymer-Folie |
| DE4304291A1 (de) * | 1993-02-12 | 1994-08-18 | Hoechst Ag | Cycloolefincopolymere mit niedriger Schmelzeviskosität und niedriger optischer Dämpfung |
| DE4304309A1 (de) * | 1993-02-12 | 1994-08-18 | Hoechst Ag | Biegsame Cycloolefincopolymer-Folie |
| DE4410559A1 (de) * | 1994-03-26 | 1995-09-28 | Hoechst Ag | Orientierte Polyolefinfolie mit amorphem Polymer, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE4422157A1 (de) * | 1994-06-24 | 1996-01-04 | Hoechst Ag | Verfahren zur Herstellung von Cycloolefincopolymeren |
| DE4426185A1 (de) | 1994-07-23 | 1996-01-25 | Hoechst Ag | Siegelfähige orientierte Polyolefin-Mehrschichtfolie, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE4426184A1 (de) | 1994-07-23 | 1996-01-25 | Hoechst Ag | Nicht siegelfähige orientierte Polyolefin-Mehrschichtfolie, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19536043A1 (de) * | 1995-09-28 | 1997-04-10 | Hoechst Ag | Polyolefinfolie mit Cycloolefinpolymer, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19539093A1 (de) | 1995-10-20 | 1997-04-24 | Hoechst Ag | Metallisierte Polyolefinfolie |
| DE19917790A1 (de) * | 1999-04-20 | 2000-11-02 | Hoechst Trespaphan Gmbh | Biaxial orientierte Folie für die Herstellung von Keramikkondensatoren |
| DE19929809A1 (de) | 1999-06-30 | 2001-01-04 | Ticona Gmbh | Kontinuierliches Verfahren zur Herstellung eines amorphen Polyolefins mit breiter Molmassenverteilung und einheitlicher Glastemperatur |
| DE10009646A1 (de) | 2000-03-01 | 2001-09-13 | Ticona Gmbh | Neues Polymergemisch |
| DE10012137A1 (de) | 2000-03-13 | 2001-09-20 | Mitsubishi Polyester Film Gmbh | Biaxial orientierte Polyesterfolie enthaltend ein Cycloolefincopolymer, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10022942A1 (de) | 2000-05-11 | 2001-11-15 | Mitsubishi Polyester Film Gmbh | Weisse, zumindest einseitig matte, biaxial orientierte Polyesterfolie mit Cycloolefincopolymer, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10026177A1 (de) | 2000-05-26 | 2001-11-29 | Mitsubishi Polyester Film Gmbh | Weiße, hochglänzende Polyesterfolie enthaltend Cycloolefincopolymer (COC), Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10035328A1 (de) | 2000-07-20 | 2002-01-31 | Mitsubishi Polyester Film Gmbh | Opake Polyesterfolie enthaltend Cycloolefincopolymer (COC) mit guter Oberflächenhaftung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6696524B2 (en) | 2001-02-20 | 2004-02-24 | E. I. Du Pont De Nemours And Company | Low Tg ethylene-based polymer, cycloolefin polymer blends |
| US6670423B2 (en) | 2001-02-20 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Polar ethylene-based polymer, cycloolefin polymer blends |
| DE10137924B4 (de) | 2001-08-07 | 2005-12-01 | Ticona Gmbh | Langfaserverstärkte Polyolefin-Kunststoff Struktur, Verfahren zu seiner Herstellung und daraus hergestellte Formkörper |
| US6713582B2 (en) | 2001-12-14 | 2004-03-30 | Uniroyal Chemical Company, Inc. | Process for the oligomerization of α-olefins having low unsaturation, the resulting polymers, and lubricants containing same |
| WO2003055678A1 (en) * | 2001-12-21 | 2003-07-10 | E.I. Du Pont De Nemours And Company | Multilayer film |
| DE10223663A1 (de) | 2002-05-28 | 2003-12-11 | Mitsubishi Polyester Film Gmbh | Transparente Polyesterfolie mit verbesserter Wasserdampfbarriere, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10223662A1 (de) | 2002-05-28 | 2003-12-11 | Mitsubishi Polyester Film Gmbh | Transparente Polyesterfolie mit verbesserter Wasserdampfbarriere, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10242730A1 (de) | 2002-09-13 | 2004-03-25 | Ticona Gmbh | Thermoformbare Folie mit hoher Wärmeformbeständigkeit und Wasserdampfbarriere |
| US7223459B2 (en) | 2003-04-22 | 2007-05-29 | Mitsubishi Polyester Film Gmbh | Coextruded, hot-sealable and peelable polyester film, process for its production and its use |
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| US7288312B2 (en) | 2003-04-22 | 2007-10-30 | Mitsubishi Polyester Film Gmbh | Coextruded, hot-sealable and peelable polyester film having low peeling resistance, process for its production and its use |
| US7144615B2 (en) | 2003-04-22 | 2006-12-05 | Mitsubishi Polyester Film Gmbh | Coextruded, hot-sealable and peelable polyester film, process for its production and its use |
| US7141293B2 (en) | 2003-04-22 | 2006-11-28 | Mitsubishi Polyester Film Gmbh | Coextruded, hot-sealable and peelable polyester film having high peeling resistance, process for its production and its use |
| US7186452B2 (en) | 2003-04-22 | 2007-03-06 | Mitsubishi Polyester Film Gmbh | Coextruded, hot-sealable and peelable polyester film having high peeling resistance, process for its production and its use |
| DE10352432A1 (de) | 2003-11-10 | 2005-06-09 | Mitsubishi Polyester Film Gmbh | Weiße, heißsiegelbare, peelfähige Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10352444A1 (de) | 2003-11-10 | 2005-06-09 | Mitsubishi Polyester Film Gmbh | Haftvermittelte, heißsiegelbare und peelfähige Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10352430A1 (de) | 2003-11-10 | 2005-06-09 | Mitsubishi Polyester Film Gmbh | Peelfähige Polyesterfolie mit verbesserter Sauerstoffbarriere, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10352431A1 (de) | 2003-11-10 | 2005-06-09 | Mitsubishi Polyester Film Gmbh | Peelfähige Polyesterfolie mit selbsttätiger Entlüftung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US7288316B2 (en) | 2003-11-21 | 2007-10-30 | Topas Advanced Polymers, Inc. | Cycloolefin copolymer heat sealable films |
| JP2004195246A (ja) * | 2004-02-13 | 2004-07-15 | Mitsunobu Miyagi | レーザプローブ |
| EP2079782B1 (de) | 2006-10-05 | 2012-05-23 | Treofan Germany GmbH & Co.KG | Simultan verstreckte opake folie aus pla |
| DE102007006825A1 (de) | 2007-02-07 | 2008-08-14 | Evonik Röhm Gmbh | Kunststoffformkörper mir anisotroper Lichtstreuung |
| DE102007055491A1 (de) | 2007-11-21 | 2009-06-04 | Mitsubishi Polyester Film Gmbh | Niedrigsiegelnde Polyesterfolie für polare Substrate |
| KR101043657B1 (ko) * | 2008-09-23 | 2011-06-22 | 김명호 | 와이어제품 성형장치 |
| WO2010096593A2 (en) | 2009-02-18 | 2010-08-26 | Northwestern University | Beam pen lithography |
| US8900719B2 (en) | 2010-04-14 | 2014-12-02 | Avery Dennison Corporation | Blends of ethylene copolymers and propylene based plastomers in multilayer films for low noise and RF welding |
| US9452593B2 (en) | 2010-04-15 | 2016-09-27 | Topas Advanced Polymers, Inc. | Melt blends of amorphous cycloolefin polymers and partially crystalline cycloolefin elastomers with improved toughness |
| DE102010030074A1 (de) | 2010-06-15 | 2011-12-15 | Evonik Degussa Gmbh | Kunststoff-Photovoltaik-Modul und Verfahren zu seiner Herstellung |
| EP2598330A1 (en) | 2010-07-27 | 2013-06-05 | Exxonmobil Oil Corporation | Film composition and method of making the same |
| EP2915665A1 (en) | 2011-12-22 | 2015-09-09 | Avery Dennison Corporation | Flexible Barrier Films Containing Cyclic Olefins |
| CN108189498B (zh) | 2012-01-31 | 2020-06-23 | 纳幕尔杜邦公司 | 包含环烯烃共聚物的多层膜 |
| KR102325932B1 (ko) | 2016-05-12 | 2021-11-17 | 에스에이치피피 글로벌 테크놀러지스 비.브이. | 고온 성능을 갖는 커패시터 필름, 이의 제조 방법 및 물품 |
| AR109065A1 (es) | 2016-07-28 | 2018-10-24 | Dow Global Technologies Llc | Estructuras multicapa, películas multicapa y envases formados a partir de ellas |
| US10951875B2 (en) | 2018-07-03 | 2021-03-16 | Raxium, Inc. | Display processing circuitry |
| DE102018215422A1 (de) | 2018-09-11 | 2020-03-12 | Mitsubishi Polyester Film Gmbh | Heißsiegelbare Polyesterfolie für die Herstellung von Menüschalen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE102019200365A1 (de) | 2019-01-14 | 2020-07-16 | Mitsubishi Polyester Film Gmbh | Packung aus Polyester mit einer thermoformbaren Unterfolie und einer siegel- und peelbaren Oberfolie, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US11710445B2 (en) | 2019-01-24 | 2023-07-25 | Google Llc | Backplane configurations and operations |
| US11637219B2 (en) | 2019-04-12 | 2023-04-25 | Google Llc | Monolithic integration of different light emitting structures on a same substrate |
| US11238782B2 (en) | 2019-06-28 | 2022-02-01 | Jasper Display Corp. | Backplane for an array of emissive elements |
| US11626062B2 (en) | 2020-02-18 | 2023-04-11 | Google Llc | System and method for modulating an array of emissive elements |
| CN115362491B (zh) | 2020-04-06 | 2025-04-08 | 谷歌有限责任公司 | 显示组件 |
| US11538431B2 (en) | 2020-06-29 | 2022-12-27 | Google Llc | Larger backplane suitable for high speed applications |
| KR20230098903A (ko) | 2020-12-21 | 2023-07-04 | 구글 엘엘씨 | 자동시청 3d 디스플레이용 고밀도 픽셀 어레이 |
| DE102023100507A1 (de) | 2023-01-11 | 2024-07-11 | Mitsubishi Polyester Film Gmbh | Koextrudierte, heißsiegelbare und peelfähige Polyesterfolie, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE102023100500A1 (de) | 2023-01-11 | 2024-07-11 | Mitsubishi Polyester Film Gmbh | Polyesterverpackung bestehend aus thermoformbarer Unterfolie und peelfähiger Oberfolie, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE102023108752A1 (de) | 2023-04-05 | 2024-10-10 | Mitsubishi Polyester Film Gmbh | Mehrschichtige, coextrudierte Polyesterfolie mit verringerter Durchstossfestigkeit zur Verwendung als Blisterabdeckfolie |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5003019A (en) * | 1987-03-02 | 1991-03-26 | Mitsui Petrochemical Industries, Ltd. | Cyclo-olefinic random copolymer, olefinic random copolymer, and process for producing cyclo-olefinic random copolymers |
| DE3726325A1 (de) * | 1987-08-07 | 1989-02-16 | Hoechst Ag | Verfahren zur herstellung eines olefinpolymers |
| DE68911435T2 (de) * | 1988-09-05 | 1994-04-28 | Idemitsu Kosan Co | Verfahren zur Herstellung eines Polymers. |
| DE3835044A1 (de) * | 1988-10-14 | 1990-04-19 | Hoechst Ag | Verfahren zur herstellung von cycloolefinpolymeren |
| DE3922546A1 (de) * | 1989-07-08 | 1991-01-17 | Hoechst Ag | Verfahren zur herstellung von cycloolefinpolymeren |
| DE3927257A1 (de) | 1989-08-18 | 1991-02-21 | Hoechst Ag | Verfahren zur herstellung eines polyolefins |
-
1991
- 1991-10-30 TW TW080108552A patent/TW227005B/zh not_active IP Right Cessation
- 1991-11-07 DE DE59108971T patent/DE59108971D1/de not_active Expired - Lifetime
- 1991-11-07 AT AT91119005T patent/ATE165372T1/de not_active IP Right Cessation
- 1991-11-07 ES ES91119005T patent/ES2117632T3/es not_active Expired - Lifetime
- 1991-11-07 EP EP91119005A patent/EP0485893B1/de not_active Expired - Lifetime
- 1991-11-12 HU HU913539A patent/HUT59429A/hu unknown
- 1991-11-13 CA CA002055397A patent/CA2055397C/en not_active Expired - Lifetime
- 1991-11-13 NO NO91914439A patent/NO914439L/no unknown
- 1991-11-13 CS CS913442A patent/CS344291A3/cs unknown
- 1991-11-13 ZA ZA918990A patent/ZA918990B/xx unknown
- 1991-11-13 AU AU87777/91A patent/AU641291B2/en not_active Ceased
- 1991-11-14 KR KR1019910020205A patent/KR100230915B1/ko not_active Expired - Lifetime
- 1991-11-14 JP JP29928391A patent/JP3247130B2/ja not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11577443B2 (en) | 2016-03-11 | 2023-02-14 | Polyplastics USA, Inc | Injection stretch blow-molding (ISBM) enhancement for semi-crystalline polyolefin containers utilizing alicyclic polyolefins |
| US12330363B2 (en) | 2016-03-11 | 2025-06-17 | Polyplastics Usa, Inc. | Injection stretch blow-molding (ISBM) enhancement for semi-crystalline polyolefin containers utilizing alicyclic polyolefins |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59108971D1 (de) | 1998-05-28 |
| HU913539D0 (en) | 1992-01-28 |
| NO914439L (no) | 1992-05-15 |
| ATE165372T1 (de) | 1998-05-15 |
| AU641291B2 (en) | 1993-09-16 |
| CA2055397A1 (en) | 1992-05-15 |
| ZA918990B (en) | 1992-07-29 |
| KR920009859A (ko) | 1992-06-25 |
| HUT59429A (en) | 1992-05-28 |
| TW227005B (enrdf_load_stackoverflow) | 1994-07-21 |
| NO914439D0 (no) | 1991-11-13 |
| CS344291A3 (en) | 1992-09-16 |
| EP0485893B1 (de) | 1998-04-22 |
| AU8777791A (en) | 1992-05-21 |
| EP0485893A1 (de) | 1992-05-20 |
| JP3247130B2 (ja) | 2002-01-15 |
| KR100230915B1 (ko) | 1999-11-15 |
| ES2117632T3 (es) | 1998-08-16 |
| JPH04268312A (ja) | 1992-09-24 |
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