KR20000064810A - 알파-올레핀-시클로올레핀 공중합체 및 그의제조 방법 - Google Patents
알파-올레핀-시클로올레핀 공중합체 및 그의제조 방법 Download PDFInfo
- Publication number
- KR20000064810A KR20000064810A KR1019980707757A KR19980707757A KR20000064810A KR 20000064810 A KR20000064810 A KR 20000064810A KR 1019980707757 A KR1019980707757 A KR 1019980707757A KR 19980707757 A KR19980707757 A KR 19980707757A KR 20000064810 A KR20000064810 A KR 20000064810A
- Authority
- KR
- South Korea
- Prior art keywords
- olefin
- dcpd
- ethylene
- copolymer
- formula
- 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.)
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 308
- 238000002360 preparation method Methods 0.000 title description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 246
- 238000000034 method Methods 0.000 claims abstract description 80
- 239000004711 α-olefin Substances 0.000 claims abstract description 55
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 10
- 150000001925 cycloalkenes Chemical class 0.000 claims abstract description 8
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims description 309
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 246
- 239000005977 Ethylene Substances 0.000 claims description 246
- 238000006116 polymerization reaction Methods 0.000 claims description 199
- 238000006243 chemical reaction Methods 0.000 claims description 130
- -1 polyethylene Polymers 0.000 claims description 108
- 230000009477 glass transition Effects 0.000 claims description 60
- 239000000178 monomer Substances 0.000 claims description 59
- 239000003054 catalyst Substances 0.000 claims description 57
- 229920000642 polymer Polymers 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 54
- 238000005984 hydrogenation reaction Methods 0.000 claims description 52
- 239000004698 Polyethylene Substances 0.000 claims description 50
- 229920000573 polyethylene Polymers 0.000 claims description 50
- 238000002844 melting Methods 0.000 claims description 26
- 230000008018 melting Effects 0.000 claims description 26
- 230000003287 optical effect Effects 0.000 claims description 26
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 19
- 229910052726 zirconium Inorganic materials 0.000 claims description 19
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 17
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- 150000001639 boron compounds Chemical class 0.000 claims description 11
- 230000009257 reactivity Effects 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 229910052735 hafnium Inorganic materials 0.000 claims description 7
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 7
- 239000010936 titanium Substances 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 230000000630 rising effect Effects 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 239000012968 metallocene catalyst Substances 0.000 claims description 4
- 210000000988 bone and bone Anatomy 0.000 claims description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 68
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 229910007926 ZrCl Inorganic materials 0.000 description 42
- 238000007334 copolymerization reaction Methods 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 40
- 238000004132 cross linking Methods 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 30
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- 238000005259 measurement Methods 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 25
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 24
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 24
- 238000001228 spectrum Methods 0.000 description 24
- 230000004044 response Effects 0.000 description 22
- 229920001519 homopolymer Polymers 0.000 description 20
- 239000011980 kaminsky catalyst Substances 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical class ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 10
- 230000007423 decrease Effects 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 230000000977 initiatory effect Effects 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- AGKZDUBMFACJPR-UHFFFAOYSA-L C12=CC=CC=C2C2=CC=CC=C2C1[Zr](Cl)(Cl)(=C(C)C)C1C=CC=C1 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1[Zr](Cl)(Cl)(=C(C)C)C1C=CC=C1 AGKZDUBMFACJPR-UHFFFAOYSA-L 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 229910052720 vanadium Inorganic materials 0.000 description 7
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 230000037048 polymerization activity Effects 0.000 description 5
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 4
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VCFVRHAQERGNFA-UHFFFAOYSA-L C1=CC2=CC=CC=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C2=CC=CC=C2C=C1 Chemical compound C1=CC2=CC=CC=C2C1[Zr](Cl)(Cl)(=[Si](C)C)C1C2=CC=CC=C2C=C1 VCFVRHAQERGNFA-UHFFFAOYSA-L 0.000 description 3
- XJONFIGVOQMBIP-UHFFFAOYSA-L Cl[Zr](Cl)C1C=CC=C1 Chemical compound Cl[Zr](Cl)C1C=CC=C1 XJONFIGVOQMBIP-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- JUPWRUDTZGBNEX-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O JUPWRUDTZGBNEX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- KPWMGUMUJVLSHH-UHFFFAOYSA-L CC(C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC2=CC=CC=C12 Chemical compound CC(C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC2=CC=CC=C12 KPWMGUMUJVLSHH-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000011112 process operation Methods 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- HJSXRRURKUSSJW-UHFFFAOYSA-N C(=O)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Rh] Chemical compound C(=O)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Rh] HJSXRRURKUSSJW-UHFFFAOYSA-N 0.000 description 1
- GHUNGDAEQRFFMV-UHFFFAOYSA-L CC(C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC=C1 Chemical compound CC(C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC=C1 GHUNGDAEQRFFMV-UHFFFAOYSA-L 0.000 description 1
- QHRNQYRMFRBDIV-UHFFFAOYSA-L C[Si](C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C2=CC=CC=C2C2=C1C=CC=C2 Chemical compound C[Si](C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C2=CC=CC=C2C2=C1C=CC=C2 QHRNQYRMFRBDIV-UHFFFAOYSA-L 0.000 description 1
- VLVZTVXICGANAR-UHFFFAOYSA-L C[Si](C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC2=CC=CC=C12 Chemical compound C[Si](C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC2=CC=CC=C12 VLVZTVXICGANAR-UHFFFAOYSA-L 0.000 description 1
- LMNJIRLUFGKYMP-UHFFFAOYSA-L C[Si](C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC=C1 Chemical compound C[Si](C)=[Zr](Cl)(Cl)(C1C=CC=C1)C1C=CC=C1 LMNJIRLUFGKYMP-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JWQSTZWYWMAWBB-UHFFFAOYSA-L Cl[Zr](Cl)(=C)(C1C=CC=C1)C1C=CC2=CC=CC=C12 Chemical compound Cl[Zr](Cl)(=C)(C1C=CC=C1)C1C=CC2=CC=CC=C12 JWQSTZWYWMAWBB-UHFFFAOYSA-L 0.000 description 1
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- 101150096839 Fcmr gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- ZDAKWHXZQMVUMO-UHFFFAOYSA-L [Br-].[Br-].C(C)(C)=[Zr+2](C1C=CC=C1)C1C2=CC=CC=C2C=2C=CC=CC1=2 Chemical compound [Br-].[Br-].C(C)(C)=[Zr+2](C1C=CC=C1)C1C2=CC=CC=C2C=2C=CC=CC1=2 ZDAKWHXZQMVUMO-UHFFFAOYSA-L 0.000 description 1
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- TXOXEOBJRGXKED-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1 TXOXEOBJRGXKED-UHFFFAOYSA-L 0.000 description 1
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- FYJSPPTWYHZSHN-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)[Si](=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)[Si](=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1)C1=CC=CC=C1 FYJSPPTWYHZSHN-UHFFFAOYSA-L 0.000 description 1
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- WNNMRCUQZOIGMB-UHFFFAOYSA-L [Cl-].[Cl-].C=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C=[Zr+2](C1C2=CC=CC=C2C=2C=CC=CC1=2)C1C=CC=C1 WNNMRCUQZOIGMB-UHFFFAOYSA-L 0.000 description 1
- NBICYCZLCAMSBG-UHFFFAOYSA-L [Co+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O Chemical compound [Co+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O NBICYCZLCAMSBG-UHFFFAOYSA-L 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 238000012648 alternating copolymerization Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000037118 bone strength Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- MLIYPCQSOXNTLJ-UHFFFAOYSA-N carbon monoxide;ruthenium dihydride;triphenylphosphane Chemical compound [RuH2].[O+]#[C-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MLIYPCQSOXNTLJ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- CYKLGTUKGYURDP-UHFFFAOYSA-L copper;hydrogen sulfate;hydroxide Chemical compound O.[Cu+2].[O-]S([O-])(=O)=O CYKLGTUKGYURDP-UHFFFAOYSA-L 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- QRUYYSPCOGSZGQ-UHFFFAOYSA-L cyclopentane;dichlorozirconium Chemical compound Cl[Zr]Cl.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 QRUYYSPCOGSZGQ-UHFFFAOYSA-L 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical group C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
- C08F210/18—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers with non-conjugated dienes, e.g. EPT rubbers
-
- 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
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1849197 | 1997-01-31 | ||
| JP97-18491 | 1997-01-31 | ||
| JP97-51638 | 1997-03-06 | ||
| JP5163897 | 1997-03-06 | ||
| PCT/JP1998/000366 WO1998033830A1 (en) | 1997-01-31 | 1998-01-29 | Alpha-olefin-cycloolefin copolymers and process for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000064810A true KR20000064810A (ko) | 2000-11-06 |
Family
ID=26355168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980707757A Withdrawn KR20000064810A (ko) | 1997-01-31 | 1998-01-29 | 알파-올레핀-시클로올레핀 공중합체 및 그의제조 방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6191243B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP0891382B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2000509754A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20000064810A (cg-RX-API-DMAC7.html) |
| CN (2) | CN1134469C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE241652T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2249714A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69814991T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2195312T3 (cg-RX-API-DMAC7.html) |
| TW (1) | TW440571B (cg-RX-API-DMAC7.html) |
| WO (1) | WO1998033830A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0964005A1 (en) * | 1998-06-10 | 1999-12-15 | Teijin Limited | Process for producing hydrogenated alpha-olefin-dicyclopentadiene copolymer, method for molding the same and optical material |
| DE19850898A1 (de) * | 1998-11-05 | 2000-05-11 | Bayer Ag | Verfahren zur Herstellung von EP(D)M |
| US20030088932A1 (en) * | 2001-11-09 | 2003-05-15 | Vernon Gardiner | Toothbrush |
| US20080069973A1 (en) * | 2004-09-15 | 2008-03-20 | Teijin Limited | Retardation Film |
| JP4712455B2 (ja) * | 2005-06-29 | 2011-06-29 | 帝人株式会社 | 光学用フィルム |
| WO2007004321A1 (ja) * | 2005-06-30 | 2007-01-11 | Mitsui Chemicals, Inc. | 環状オレフィン系樹脂組成物の製造方法および環状オレフィン系樹脂組成物 |
| CN101528787A (zh) * | 2006-07-14 | 2009-09-09 | 埃克森美孚化学专利公司 | 乙烯/二聚环戊二烯共聚物及其官能化衍生物 |
| EP2052022A1 (en) * | 2006-08-04 | 2009-04-29 | ExxonMobil Chemical Patents Inc. | Polymer compositions comprising cyclic olefin copolymers and polyolefin modifiers |
| WO2008018951A1 (en) * | 2006-08-04 | 2008-02-14 | Exxonmobil Chemical Patents Inc. | Polymer compositions comprising cyclic olefin polymers, polyolefin modifiers, and fillers |
| US8519056B2 (en) | 2007-06-01 | 2013-08-27 | Exxonmobil Chemical Patents Inc. | Blends of co-precipitated hydrogenated ethylene-dicyclpentadiene and elastomeric polymers to provide impact modified structural polyolefins |
| KR100906165B1 (ko) * | 2008-02-12 | 2009-07-06 | 주식회사 코오롱 | 환상올레핀계 고분자 화합물 및 그 제조 방법 |
| US11248113B2 (en) * | 2018-11-30 | 2022-02-15 | Exxonmobil Chemical Patents Inc. | Cyclic olefin copolymers and films prepared therefrom |
| JPWO2021060551A1 (cg-RX-API-DMAC7.html) * | 2019-09-27 | 2021-04-01 | ||
| CN116217772B (zh) * | 2023-01-10 | 2024-05-28 | 中国科学院长春应用化学研究所 | 一种环烯烃共聚物及其制备方法 |
Family Cites Families (7)
| 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 |
| JPH01282214A (ja) * | 1988-05-09 | 1989-11-14 | Mitsui Toatsu Chem Inc | ポリジシクロペンタジエンの製造法 |
| JPH0816129B2 (ja) * | 1988-11-14 | 1996-02-21 | 日本ゼオン株式会社 | ノルボルネン系開環重合体の製造方法 |
| DE3922546A1 (de) | 1989-07-08 | 1991-01-17 | Hoechst Ag | Verfahren zur herstellung von cycloolefinpolymeren |
| US5552489A (en) * | 1994-07-22 | 1996-09-03 | Exxon Chemical Patents Inc. | Tackifiers and a process to obtain tackifiers |
| ES2126948T3 (es) | 1994-11-17 | 1999-04-01 | Ciba Geigy Ag | Procedimiento de polimerizacion de olefinas ciclicas y composicion fotopolimerizable. |
| EP0792306B1 (de) | 1994-11-17 | 1998-12-09 | Ciba SC Holding AG | Verfahren zur polymerisation von cyclischen olefinen und photopolymerisierbare zusammensetzung |
-
1998
- 1998-01-29 WO PCT/JP1998/000366 patent/WO1998033830A1/en not_active Ceased
- 1998-01-29 AT AT98901040T patent/ATE241652T1/de not_active IP Right Cessation
- 1998-01-29 ES ES98901040T patent/ES2195312T3/es not_active Expired - Lifetime
- 1998-01-29 CN CNB988004089A patent/CN1134469C/zh not_active Expired - Fee Related
- 1998-01-29 US US09/142,786 patent/US6191243B1/en not_active Expired - Fee Related
- 1998-01-29 DE DE69814991T patent/DE69814991T2/de not_active Expired - Lifetime
- 1998-01-29 CA CA002249714A patent/CA2249714A1/en not_active Abandoned
- 1998-01-29 EP EP98901040A patent/EP0891382B1/en not_active Expired - Lifetime
- 1998-01-29 JP JP10532716A patent/JP2000509754A/ja not_active Ceased
- 1998-01-29 KR KR1019980707757A patent/KR20000064810A/ko not_active Withdrawn
- 1998-02-02 TW TW087101248A patent/TW440571B/zh not_active IP Right Cessation
-
2000
- 2000-04-12 CN CN00106576A patent/CN1280140A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998033830A1 (en) | 1998-08-06 |
| EP0891382B1 (en) | 2003-05-28 |
| TW440571B (en) | 2001-06-16 |
| DE69814991D1 (de) | 2003-07-03 |
| ES2195312T3 (es) | 2003-12-01 |
| US6191243B1 (en) | 2001-02-20 |
| CA2249714A1 (en) | 1998-07-31 |
| CN1280140A (zh) | 2001-01-17 |
| ATE241652T1 (de) | 2003-06-15 |
| EP0891382A1 (en) | 1999-01-20 |
| CN1134469C (zh) | 2004-01-14 |
| DE69814991T2 (de) | 2004-02-26 |
| JP2000509754A (ja) | 2000-08-02 |
| CN1222920A (zh) | 1999-07-14 |
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