TW457253B - Method for the preparation of copolymers of ethylene/norbornene-type monomers with nickel catalysis - Google Patents
Method for the preparation of copolymers of ethylene/norbornene-type monomers with nickel catalysis Download PDFInfo
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- TW457253B TW457253B TW087109263A TW87109263A TW457253B TW 457253 B TW457253 B TW 457253B TW 087109263 A TW087109263 A TW 087109263A TW 87109263 A TW87109263 A TW 87109263A TW 457253 B TW457253 B TW 457253B
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- ethylene
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 165
- 239000005977 Ethylene Substances 0.000 title claims abstract description 165
- 229920001577 copolymer Polymers 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 53
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000000178 monomer Substances 0.000 title claims abstract description 46
- 229910052759 nickel Inorganic materials 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006555 catalytic reaction Methods 0.000 title claims 2
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 58
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 34
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 34
- 239000003446 ligand Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 19
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
- 230000007935 neutral effect Effects 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011574 phosphorus Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims abstract description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 294
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 199
- 239000000243 solution Substances 0.000 claims description 113
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 238000011049 filling Methods 0.000 claims description 44
- -1 triphenylphosphine methylene compound Chemical class 0.000 claims description 41
- 239000007789 gas Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 230000002079 cooperative effect Effects 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 229910001220 stainless steel Inorganic materials 0.000 claims description 28
- 239000010935 stainless steel Substances 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- 230000009477 glass transition Effects 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 238000004611 spectroscopical analysis Methods 0.000 claims description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 150000002816 nickel compounds Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000005481 NMR spectroscopy Methods 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 7
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 claims description 7
- 229940116229 borneol Drugs 0.000 claims description 7
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 7
- 239000010931 gold Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 6
- 229910052704 radon Inorganic materials 0.000 claims description 6
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 5
- 238000005516 engineering process Methods 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- PCBPVYHMZBWMAZ-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)CC1C=C2 PCBPVYHMZBWMAZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- HOMQMIYUSVQSHM-UHFFFAOYSA-N cycloocta-1,3-diene;nickel Chemical compound [Ni].C1CCC=CC=CC1.C1CCC=CC=CC1 HOMQMIYUSVQSHM-UHFFFAOYSA-N 0.000 claims description 2
- 238000000855 fermentation Methods 0.000 claims description 2
- 230000004151 fermentation Effects 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 229910052700 potassium Chemical group 0.000 claims 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 9
- 239000011591 potassium Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052708 sodium Inorganic materials 0.000 claims 5
- 239000011734 sodium Substances 0.000 claims 5
- 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 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 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 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 235000014443 Pyrus communis Nutrition 0.000 claims 2
- 239000007983 Tris buffer Substances 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 claims 1
- KUKRLSJNTMLPPK-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(C)C=CC1C2(C)C KUKRLSJNTMLPPK-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 241000206761 Bacillariophyta Species 0.000 claims 1
- GLVKGYRREXOCIB-UHFFFAOYSA-N Bornylene Natural products CC1CCC(C(C)(C)C)C=C1 GLVKGYRREXOCIB-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101000589305 Homo sapiens Natural cytotoxicity triggering receptor 2 Proteins 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- 102100032851 Natural cytotoxicity triggering receptor 2 Human genes 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 206010041308 Soliloquy Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 235000019504 cigarettes Nutrition 0.000 claims 1
- 210000004268 dentin Anatomy 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 101150102216 lcrV gene Proteins 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims 1
- WNFSFUSCVXIYGN-UHFFFAOYSA-N phenylaluminum Chemical compound [Al]C1=CC=CC=C1 WNFSFUSCVXIYGN-UHFFFAOYSA-N 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 235000015170 shellfish Nutrition 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 229940098465 tincture Drugs 0.000 claims 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 abstract description 3
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 18
- 238000001035 drying Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- 238000002309 gasification Methods 0.000 description 9
- 238000010348 incorporation Methods 0.000 description 9
- 239000013638 trimer Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 5
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 229910052722 tritium Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
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- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 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 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- BHAROVLESINHSM-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1 BHAROVLESINHSM-UHFFFAOYSA-N 0.000 description 1
- HUBXIUXSKNTDFV-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1.CC1=CC=CC=C1 HUBXIUXSKNTDFV-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 239000007861 trimeric product Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- VMYXUZSZMNBRCN-UHFFFAOYSA-N α-curcumene Chemical compound CC(C)=CCCC(C)C1=CC=C(C)C=C1 VMYXUZSZMNBRCN-UHFFFAOYSA-N 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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
-
- 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
- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/03—Multinuclear procatalyst, i.e. containing two or more metals, being different or not
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/871,245 US5929181A (en) | 1997-06-09 | 1997-06-09 | Method for preparation of copolymers of ethylene/norbornene-type monomers with nickel catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW457253B true TW457253B (en) | 2001-10-01 |
Family
ID=25357017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087109263A TW457253B (en) | 1997-06-09 | 1998-07-16 | Method for the preparation of copolymers of ethylene/norbornene-type monomers with nickel catalysis |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5929181A (https=) |
| EP (1) | EP0988330B1 (https=) |
| JP (1) | JP2002504945A (https=) |
| AU (1) | AU8058998A (https=) |
| DE (1) | DE69817814T2 (https=) |
| MY (1) | MY114477A (https=) |
| TW (1) | TW457253B (https=) |
| WO (1) | WO1998056837A1 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6103658A (en) | 1997-03-10 | 2000-08-15 | Eastman Chemical Company | Olefin polymerization catalysts containing group 8-10 transition metals, processes employing such catalysts and polymers obtained therefrom |
| US6200925B1 (en) | 1997-03-13 | 2001-03-13 | Eastman Chemical Company | Catalyst compositions for the polymerization of olefins |
| US6245871B1 (en) | 1997-04-18 | 2001-06-12 | Eastman Chemical Company | Group 8-10 transition metal olefin polymerization catalysts |
| US6174976B1 (en) | 1998-02-24 | 2001-01-16 | Eastman Chemical Company | Neutral nickel complexes for olefin polymerization |
| TW562810B (en) * | 1998-04-16 | 2003-11-21 | Mitsui Chemicals Inc | Catalyst for olefinic polymerization and method for polymerizing olefine |
| JP2002521534A (ja) * | 1998-07-27 | 2002-07-16 | バセル テクノロジー カンパニー ビー．ブイ． | 重合方法 |
| US6117959A (en) * | 1998-09-02 | 2000-09-12 | Eastman Chemical Company | Polyolefin catalysts |
| FR2784110B1 (fr) * | 1998-10-06 | 2003-08-01 | Atochem Elf Sa | Procede de polymerisation des olefines en presence d'eau |
| US6521793B1 (en) | 1998-10-08 | 2003-02-18 | Symyx Technologies, Inc. | Catalyst ligands, catalytic metal complexes and processes using same |
| US6420503B1 (en) * | 1999-02-05 | 2002-07-16 | Sumitomo Bakelite Co. Ltd. | Norbornene sulfonamide polymers |
| US6620896B1 (en) | 1999-02-23 | 2003-09-16 | Eastman Chemical Company | Mixed olefin polymerization catalysts, processes employing such catalysts, and polymers obtained therefrom |
| US6204216B1 (en) * | 1999-04-15 | 2001-03-20 | Equistar Chemicals, L.P. | Olefin polymerization catalysts containing amine derivatives |
| US6914105B1 (en) * | 1999-11-12 | 2005-07-05 | North Carolina State University | Continuous process for making polymers in carbon dioxide |
| US6806332B2 (en) * | 1999-11-12 | 2004-10-19 | North Carolina State University | Continuous method and apparatus for separating polymer from a high pressure carbon dioxide fluid stream |
| US6521724B2 (en) | 2000-03-10 | 2003-02-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
| US20040082464A1 (en) * | 2000-03-31 | 2004-04-29 | Romano Anna Maria | Complex polymerization catalysts for the homopolymerization of ethylene and for the copolymerization of ethylene |
| US6350837B1 (en) | 2000-06-09 | 2002-02-26 | Eastman Chemical Company | Copolymerization of norbornene and functional norbornene monomers |
| US6538087B2 (en) | 2000-07-28 | 2003-03-25 | Promerus, Llc | Polymeric compositions for forming optical waveguides; optical waveguides formed therefrom; and methods for making same |
| FR2814169B1 (fr) * | 2000-09-19 | 2005-07-08 | Atofina | Catalyseur pour la polymerisation des olefines |
| US6974657B2 (en) * | 2000-10-18 | 2005-12-13 | E. I. Du Pont De Nemours And Company | Compositions for microlithography |
| CN1498360A (zh) | 2000-11-29 | 2004-05-19 | 纳幕尔杜邦公司 | 聚合物掺混物及其在用于微细光刻的光刻胶组合物中的应用 |
| KR20020056602A (ko) * | 2000-12-29 | 2002-07-10 | 노기호 | 황을 포함하는 고리형 올레핀 공중합체 및 그의 제조방법 |
| JP4844705B2 (ja) * | 2001-03-23 | 2011-12-28 | Ｊｓｒ株式会社 | 環状オレフィン付加（共）重合体およびその製造方法 |
| US6825148B2 (en) | 2001-04-10 | 2004-11-30 | Shell Oil Company | Nickel-containing ethylene oligomerization catalyst and use thereof |
| EP1293521B1 (en) | 2001-09-13 | 2008-02-13 | JSR Corporation | Cyclic olefin addition copolymer and process for producing same, crosslinkable composition, crosslinked product and process for producing same, and optically transparent material and application thereof |
| US20030130452A1 (en) * | 2001-10-12 | 2003-07-10 | Johnson Lynda Kaye | Copolymers of ethylene with various norbornene derivatives |
| WO2003076450A1 (en) * | 2002-03-06 | 2003-09-18 | E.I. Du Pont De Nemours And Company | Catalysts for olefin polymerization |
| WO2003099887A1 (en) * | 2002-05-29 | 2003-12-04 | Jsr Corporation | Cycloolefin addition copolymer and optical transparent material |
| ATE359322T1 (de) * | 2003-01-28 | 2007-05-15 | Cryovac Inc | Cycloolefinpolymer für hochmodulige folien |
| US7087687B2 (en) * | 2003-08-21 | 2006-08-08 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| US7101654B2 (en) * | 2004-01-14 | 2006-09-05 | Promerus Llc | Norbornene-type monomers and polymers containing pendent lactone or sultone groups |
| US7199074B2 (en) * | 2004-06-14 | 2007-04-03 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| US7172986B2 (en) * | 2004-06-14 | 2007-02-06 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| JP5430066B2 (ja) * | 2004-07-07 | 2014-02-26 | プロメラス， エルエルシー | 絶縁樹脂組成物及びその使用 |
| US7435701B2 (en) * | 2005-05-27 | 2008-10-14 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| US7410899B2 (en) * | 2005-09-20 | 2008-08-12 | Enthone, Inc. | Defectivity and process control of electroless deposition in microelectronics applications |
| US7482412B2 (en) * | 2006-10-10 | 2009-01-27 | Jsr Corporation | Process for manufacturing cycloolefin addition polymer |
| US20090085427A1 (en) * | 2007-10-01 | 2009-04-02 | The Regents Of The University Of Michigan | Electrical power generation from fluid flow |
| US8906508B2 (en) | 2012-05-30 | 2014-12-09 | Nike, Inc. | Method of toughening thermoplastic polyurethane and articles comprising toughened thermoplastic polyurethane |
| US8716421B2 (en) | 2012-06-25 | 2014-05-06 | Promerus, Llc | Norbornene-type formate monomers and polymers and optical waveguides formed therefrom |
| WO2014025735A1 (en) | 2012-08-07 | 2014-02-13 | Promerus, Llc | Cycloalkylnorbornene monomers, polymers derived therefrom and their use in pervaporation |
| TWI732111B (zh) | 2017-03-28 | 2021-07-01 | 日商住友電木股份有限公司 | 感光性組成物、彩色濾光片及由其衍生之微透鏡 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3330815A (en) * | 1964-03-24 | 1967-07-11 | Union Carbide Corp | Novel polynorbornenes, process for production thereof, and products produced therefrom |
| NL135975C (https=) * | 1968-12-18 | |||
| US3644564A (en) * | 1969-12-19 | 1972-02-22 | Shell Oil Co | Ethylene oligomerization in the presence of complex nickel-fluorine-containing catalysts |
| US3661803A (en) * | 1970-01-15 | 1972-05-09 | Shell Oil Co | Ethylene polymerization in the presence of complex nickel catalysts containing a glycolic acid,thiogly colic,or thtolactic acid ligand |
| BE775698A (nl) * | 1970-12-02 | 1972-05-23 | Shell Int Research | Werkwijze voor het polymeriseren van etheen |
| US3686351A (en) * | 1971-07-16 | 1972-08-22 | Shell Oil Co | Alpha-olefin production |
| US4537982A (en) * | 1982-08-03 | 1985-08-27 | Bayer Aktiengesellschaft | Production of organic nickel compounds |
| US4698403A (en) * | 1985-10-15 | 1987-10-06 | E. I. Du Pont De Nemours And Company | Nickel-catalyzed copolymerization of ethylene |
| US4948856A (en) * | 1987-05-22 | 1990-08-14 | B. F. Goodrich Company | Homogeneous addition copolymers of ethylene and cycloolefin monomers and method for producing same |
| JPH0463807A (ja) * | 1990-03-06 | 1992-02-28 | Idemitsu Kosan Co Ltd | ノルボルネン系重合体およびその製造方法ならびに該重合体からなるフィルムおよびその製造方法 |
| DE69132693T3 (de) * | 1990-10-05 | 2010-01-21 | Idemitsu Kosan Co. Ltd. | Copolymere von Cycloolefinen, daraus hergestellte Zusammensetzungen und Formteile |
| US5468819A (en) * | 1993-11-16 | 1995-11-21 | The B.F. Goodrich Company | Process for making polymers containing a norbornene repeating unit by addition polymerization using an organo (nickel or palladium) complex |
| KR100418168B1 (ko) * | 1995-01-24 | 2004-02-14 | 이.아이,듀우판드네모아앤드캄파니 | 중합 방법 |
| US5677405A (en) * | 1995-05-24 | 1997-10-14 | The B.F. Goodrich Company | Homopolymers and copolymers of cationically polymerizable monomers and method of their preparation |
| US5705503A (en) * | 1995-05-25 | 1998-01-06 | Goodall; Brian Leslie | Addition polymers of polycycloolefins containing functional substituents |
| US5714556A (en) * | 1995-06-30 | 1998-02-03 | E. I. Dupont De Nemours And Company | Olefin polymerization process |
| CN100384889C (zh) * | 1997-01-14 | 2008-04-30 | 纳幕尔杜邦公司 | 烯烃聚合 |
-
1997
- 1997-06-09 US US08/871,245 patent/US5929181A/en not_active Expired - Lifetime
-
1998
- 1998-06-04 DE DE69817814T patent/DE69817814T2/de not_active Expired - Fee Related
- 1998-06-04 EP EP98928896A patent/EP0988330B1/en not_active Expired - Lifetime
- 1998-06-04 AU AU80589/98A patent/AU8058998A/en not_active Abandoned
- 1998-06-04 JP JP50287099A patent/JP2002504945A/ja not_active Ceased
- 1998-06-04 WO PCT/US1998/011554 patent/WO1998056837A1/en not_active Ceased
- 1998-06-08 MY MYPI98002550A patent/MY114477A/en unknown
- 1998-07-16 TW TW087109263A patent/TW457253B/zh active
-
1999
- 1999-05-06 US US09/305,942 patent/US6197984B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HK1027116A1 (en) | 2001-01-05 |
| DE69817814T2 (de) | 2004-07-15 |
| US5929181A (en) | 1999-07-27 |
| EP0988330A1 (en) | 2000-03-29 |
| AU8058998A (en) | 1998-12-30 |
| WO1998056837A1 (en) | 1998-12-17 |
| DE69817814D1 (de) | 2003-10-09 |
| EP0988330B1 (en) | 2003-09-03 |
| JP2002504945A (ja) | 2002-02-12 |
| MY114477A (en) | 2002-10-31 |
| US6197984B1 (en) | 2001-03-06 |
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