JP6654234B2 - その場で油生成を伴うエチレンコポリマー - Google Patents
その場で油生成を伴うエチレンコポリマー Download PDFInfo
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- JP6654234B2 JP6654234B2 JP2018510506A JP2018510506A JP6654234B2 JP 6654234 B2 JP6654234 B2 JP 6654234B2 JP 2018510506 A JP2018510506 A JP 2018510506A JP 2018510506 A JP2018510506 A JP 2018510506A JP 6654234 B2 JP6654234 B2 JP 6654234B2
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- Prior art keywords
- ethylene
- olefin
- copolymer
- oil
- oligomer
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- 229920001038 ethylene copolymer Polymers 0.000 title claims description 103
- 238000011065 in-situ storage Methods 0.000 title description 7
- 230000015572 biosynthetic process Effects 0.000 title description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 128
- 239000005977 Ethylene Substances 0.000 claims description 128
- 239000003054 catalyst Substances 0.000 claims description 127
- -1 diene compound Chemical class 0.000 claims description 111
- 229920000642 polymer Polymers 0.000 claims description 110
- 239000000203 mixture Substances 0.000 claims description 105
- 239000004711 α-olefin Substances 0.000 claims description 93
- 238000006116 polymerization reaction Methods 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 68
- 150000001336 alkenes Chemical class 0.000 claims description 65
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 59
- 230000008569 process Effects 0.000 claims description 50
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 39
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 36
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 35
- 241001441571 Hiodontidae Species 0.000 claims description 27
- 239000004606 Fillers/Extenders Substances 0.000 claims description 23
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 claims description 18
- 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 5
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims description 5
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 description 91
- 239000003921 oil Substances 0.000 description 58
- 239000012190 activator Substances 0.000 description 47
- 150000001993 dienes Chemical group 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 42
- 239000000178 monomer Substances 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 36
- 229920006213 ethylene-alphaolefin copolymer Polymers 0.000 description 35
- 229920001971 elastomer Polymers 0.000 description 29
- 229910052735 hafnium Inorganic materials 0.000 description 25
- 229910052726 zirconium Chemical group 0.000 description 24
- 229920002554 vinyl polymer Polymers 0.000 description 20
- 229920002943 EPDM rubber Polymers 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 239000000806 elastomer Substances 0.000 description 17
- 239000010936 titanium Substances 0.000 description 17
- 229910052719 titanium Inorganic materials 0.000 description 16
- 238000009826 distribution Methods 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 12
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- 239000005060 rubber Substances 0.000 description 12
- 229910052723 transition metal Inorganic materials 0.000 description 12
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 238000004073 vulcanization Methods 0.000 description 11
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- 239000012968 metallocene catalyst Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 9
- 238000010348 incorporation Methods 0.000 description 9
- 150000003624 transition metals Chemical class 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 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 6
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000000149 argon plasma sintering Methods 0.000 description 6
- 230000002902 bimodal effect Effects 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical group C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000002516 radical scavenger Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 5
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 239000002685 polymerization catalyst Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- FUDNBFMOXDUIIE-UHFFFAOYSA-N 3,7-dimethylocta-1,6-diene Chemical compound C=CC(C)CCC=C(C)C FUDNBFMOXDUIIE-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- NMLGKEDSNASIHM-UHFFFAOYSA-N (2,3,4,5,6,7,8-heptafluoronaphthalen-1-yl)oxyboronic acid Chemical compound FC1=C(F)C(F)=C2C(OB(O)O)=C(F)C(F)=C(F)C2=C1F NMLGKEDSNASIHM-UHFFFAOYSA-N 0.000 description 3
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical class ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 3
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 3
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 3
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 3
- YXRZFCBXBJIBAP-UHFFFAOYSA-N 2,6-dimethylocta-1,7-diene Chemical compound C=CC(C)CCCC(C)=C YXRZFCBXBJIBAP-UHFFFAOYSA-N 0.000 description 3
- UFERIGCCDYCZLN-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-1h-indene Chemical compound C1C=CCC2CC=CC21 UFERIGCCDYCZLN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229940069096 dodecene Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000010734 process oil Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- RJUCIROUEDJQIB-GQCTYLIASA-N (6e)-octa-1,6-diene Chemical compound C\C=C\CCCC=C RJUCIROUEDJQIB-GQCTYLIASA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 2
- FUJQSNBYXCNHEW-UHFFFAOYSA-N 1-ethenylcyclododecene Chemical compound C=CC1=CCCCCCCCCCC1 FUJQSNBYXCNHEW-UHFFFAOYSA-N 0.000 description 2
- KTNBSFJZASJUKB-UHFFFAOYSA-N 1-ethenylcyclooctene Chemical compound C=CC1=CCCCCCC1 KTNBSFJZASJUKB-UHFFFAOYSA-N 0.000 description 2
- PPWUTZVGSFPZOC-UHFFFAOYSA-N 1-methyl-2,3,3a,4-tetrahydro-1h-indene Chemical compound C1C=CC=C2C(C)CCC21 PPWUTZVGSFPZOC-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- FZUNCODNAAEALR-UHFFFAOYSA-N 2-tert-butylperoxy-2-methylpropane;1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1.CC(C)(C)OOC(C)(C)C FZUNCODNAAEALR-UHFFFAOYSA-N 0.000 description 2
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 2
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 2
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-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
- IZLXZVWFPZWXMZ-UHFFFAOYSA-N 5-cyclohexylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1=CC2CC1CC2=C1CCCCC1 IZLXZVWFPZWXMZ-UHFFFAOYSA-N 0.000 description 2
- BDEXHIMNEUYKBS-UHFFFAOYSA-N 5-cyclopent-2-en-1-ylbicyclo[2.2.1]hept-2-ene Chemical compound C1=CCCC1C1C(C=C2)CC2C1 BDEXHIMNEUYKBS-UHFFFAOYSA-N 0.000 description 2
- VSQLAQKFRFTMNS-UHFFFAOYSA-N 5-methylhexa-1,4-diene Chemical compound CC(C)=CCC=C VSQLAQKFRFTMNS-UHFFFAOYSA-N 0.000 description 2
- WTQBISBWKRKLIJ-UHFFFAOYSA-N 5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C)CC1C=C2 WTQBISBWKRKLIJ-UHFFFAOYSA-N 0.000 description 2
- CJQNJRMLJAAXOS-UHFFFAOYSA-N 5-prop-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CC)CC1C=C2 CJQNJRMLJAAXOS-UHFFFAOYSA-N 0.000 description 2
- UGJBFMMPNVKBPX-UHFFFAOYSA-N 5-propan-2-ylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C(C)C)CC1C=C2 UGJBFMMPNVKBPX-UHFFFAOYSA-N 0.000 description 2
- YKCNBNDWSATCJL-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hepta-2,5-diene Chemical compound C1=CC2C=CC1O2 YKCNBNDWSATCJL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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Description
本出願は、2015年8月25日に出願された米国特許仮出願第62/209,560号の優先権を主張し、同出願の内容は参照によって本明細書に組み込まれる。
技術分野
いくつかの様相では、本発明は油展されたエチレンアルファオレフィンコポリマー、またはエチレンアルファオレフィンおよびジエンコポリマーに関する。この油はオレフィンオリゴマーを含んでおり、エチレンコポリマーの重合プロセスの際にその場で(in−situ)製造される。1つの様相では、オリゴマーは、1個以上のビニル鎖末端基を有し、エチレンアルファオレフィンコポリマー鎖またはエチレンアルファオレフィンおよびジエンコポリマー鎖中に組み入れられて、側鎖(分枝とも呼ばれる。)を形成する。本発明は、さらなる様相では、エチレン、アルファオレフィンおよびオレフィンオリゴマーを含んでいる、エチレンアルファオレフィンコポリマーまたはエチレンアルファオレフィンおよびジエンコポリマーに関し、その場合にオレフィンオリゴマーの全ての不飽和鎖末端基の少なくとも50%はビニル鎖末端基である。
エキステンダー油中のおよび/またはエチレンコポリマー中に組み込まれたオレフィンオリゴマー
a.190℃の温度での粘度(ブルックフィールド粘度とも呼ばれる。)は、90,000mPa・秒以下、または80,000以下、または70,000以下、または60,000以下、または50,000以下、または40,000以下、または30,000以下、または20,000以下、または10,000以下、または8,000以下、または5,000以下、または4,000以下、または3,000以下、または1,500以下、または250〜15,000mPa・秒、または500〜5,500mPa・秒、または500〜3,000mPa・秒であり、および/または60℃での粘度は、8,000mPa・秒以下、または7,000以下、または6,000以下、または5,000以下、または4,000以下、または3,000以下、または1,500以下、または250〜6,000 Pa・秒、または500〜5,500mPa・秒、または500〜3,000mPa・秒、または500〜1,500mPa・秒である。
b.60℃の温度での粘度は、ASTM D3236によって測定された200mPa・秒以上、好ましくは400mPa・秒以上(たとえば500mPa・秒以上、または1,000mPa・秒以上さえ)である。60℃での粘度はまた、20,000mPa・秒未満、15,000mPa・秒未満、または10,000mPa・秒未満であってもよい。
c.Mnは、(1H NMRによって測定された)200g/モル以上(たとえば200g/モル〜100,000g/モル、たとえば200g/モル〜75,000g/モル、たとえば200g/モル〜60,000g/モル、たとえば300g/モル〜60,000g/モル、またはたとえば350g/モル〜30,000g/モル)である。
d.重量平均分子量(Mw)は、(GPCによって測定された)300g/モル以上である。
e.MWDは、1.8以上、2.0以上、より好ましくは2.5以上である。
f.数平均鎖長は、4,000炭素原子長未満、好ましくは3,000炭素原子長未満、より好ましくは2,000炭素原子長未満である。あるいは、数平均鎖長は、20炭素原子〜2,000炭素原子長である。
g.全ての不飽和鎖末端基の少なくとも50%、好ましくは60%以上、より好ましくは70%以上、さらにより好ましくは80%以上、または90%以上さえはビニル鎖末端基である。
h.分岐指数g’visは0.98以下、好ましくは0.95以下である。
i.オレフィンオリゴマーは、25℃で液相状態にあり、室温で脂肪族および芳香族溶媒に可溶性である。
j.オレフィンオリゴマーは無定形であり、DSC測定によって検出可能な融解ピークを有し、5J/g以下の融解熱を有する。
エチレンコポリマー
重合プロセス
a.少なくともプロピレンおよび任意的に1種以上の追加のアルファオレフィンを第1の触媒と接触させて、全ての不飽和鎖末端基基準で少なくとも50%のビニル鎖末端基を有するオレフィンオリゴマー(「ビニル停止基」オリゴマーとも呼ばれる。)を形成する工程;および
b.当該オレフィンオリゴマーの少なくとも一部およびエチレンおよび1種以上の追加のアルファオレフィンを、第2の触媒と接触させて、エチレンアルファオレフィンコポリマーまたはエチレンアルファオレフィンおよびジエンコポリマーを成形する工程。
(i)全不飽和オレフィン鎖末端基基準で少なくとも50%のビニル鎖末端基を含んでいるプロピレンオリゴマーを製造するのに十分な条件の下で第1の重合ゾーンでプロピレンを重合する工程;および
(ii)当該プロピレンオリゴマーの少なくとも一部を、前記第1の重合ゾーンから分離された第2の重合ゾーンでエチレン、プロピレンおよび任意的なジエンモノマーと、当該モノマーおよびオリゴマーを重合させるのに十分な条件の下で接触させて、油展されたエチレンアルファオレフィンコポリマーまたはエチレンアルファオレフィンおよびジエンコポリマーを製造する工程。いくつかの実施形態では、プロピレンオリゴマーの一部は、その場で(in situ)エキステンダー油の少なくとも一部を形成する。ある実施形態では、プロピレンオリゴマーのさらなる部分は、エチレンアルファオレフィンコポリマーまたはエチレンアルファオレフィンおよびジエンコポリマー中に組み入れられる。
オリゴマーおよびエチレンコポリマーを製造するための触媒系
この式で、Mはハフニウムまたはジルコニウム、好ましくはハフニウムであり;
Xはそれぞれ独立して、1〜20個の炭素原子を有する置換または非置換のヒドロカルビル基、ヒドリド、アミド、アルコキシド、スルフィド、ホスフィド、ハライド、ジエン、アミン、ホスフィン、エーテルおよびこれらの組み合わせ(2個のXが、縮合環または縮合環系の一部を形成してもよい。)から成る群から選ばれ;好ましくはXはそれぞれ独立して、ハライドおよびC1〜C6のヒドロカルビル基から選ばれ、好ましくはXはそれぞれメチル、エチル、プロピル、ブチル、フェニル、ベンジル、クロライド、ブロマイドまたはヨーダイド基であり;
R8はそれぞれ独立して置換または非置換のC1〜C10のアルキル基であり;好ましくはメチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、ノニル、デシル基またはこれらの異性体であり; 好ましくはメチル、n−プロピルまたはn−ブチル基であり;または好ましくはメチル基であり;
R9はそれぞれ独立して置換または非置換のC1〜C10のアルキル基であり;好ましくはメチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、ノニル、デシルまたはこれらの異性体であり;好ましくはメチル、n−プロピルまたはブチル基であり;または好ましくはn−プロピル基であり;
R10はそれぞれ水素であり;
R11、R12およびR13はそれぞれ独立して水素または置換もしくは非置換のヒドロカルビル基、ヘテロ原子またはヘテロ原子含有基であり;好ましくはR11、R12およびR13はそれぞれ水素であり;
Tは、式R2 aJによって表される架橋基であり、JはC、SiまたはGe、好ましくはSiであり;
Raはそれぞれ独立して水素、ハロゲンまたはC1〜C20のヒドロカルビル基、たとえばメチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、フェニル、ベンジル、置換フェニル基であり、2個のRaは環状構造、たとえば芳香族、部分的に飽和、もしくは飽和の環または縮合環系を形成することができ;
さらに、任意の2個の隣接するR基は縮合環または多中心縮合環系を形成してもよく、その環は部分的に飽和、または飽和の芳香族であってもよいことを条件とする。Tはまた上でR2 aTとして定義された架橋基であってもよく;さらに、任意の隣接するR11、R12およびR13基は縮合環または多中心縮合環系を形成してもよく、その環は部分的に飽和、または飽和の芳香族であってもよいことを条件とする。
rac−ジメチルシリルビス(2−メチル,3−プロピルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−プロピルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−エチル,3−プロピルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−エチル,3−プロピルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−エチルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−メチル, 3−エチルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−イソプロピルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−イソプロピルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−ブチルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−ブチルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−プロピルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−プロピルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−エチル,3−プロピルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−エチル,3−プロピルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−エチルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−エチルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−イソプロピルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−イソプロピルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−ブチルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−プロピルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−プロピル,3−メチルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−プロピル,3−メチルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−プロピル,3−エチルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−プロピル,3−エチルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−プロピル,3−ブチルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−プロピル,3−ブチルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−ブチルインデニル)ハフニウムジメチル、
rac−ジメチルシリルビス(2−メチル,3−ブチルインデニル)ジルコニウムジメチル、
rac−ジメチルシリルビス(2,3−ジメチル)ハフニウムジメチル、
rac−ジメチルシリルビス(2,3−ジメチル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−プロピル,3−メチルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−プロピル,3−メチルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−プロピル,3−エチルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−プロピル,3−メチルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−プロピル,3−ブチルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−プロピル,3−ブチルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−ブチルインデニル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2−メチル,3−ブチルインデニル)ジルコニウムジメチル、
rac−ジメチルゲルマニルビス(2,3−ジメチル)ハフニウムジメチル、
rac−ジメチルゲルマニルビス(2,3−ジメチル)ジルコニウムジメチルおよび
シクロテトラメチレンシリレン−ビス(2,4,7−トリメチルインデン−1−イル)ハフニウムジメチル。
この式で、Mはハフニウムまたはジルコニウムであり;
Xはそれぞれ独立して、1〜20個の炭素原子を有するヒドロカルビル基、ヒドリド、アミド、アルコキシド、スルフィド、ホスフィド、ハライド、ジエン、アミン、ホスフィン、エーテルおよびこれらの組み合わせ(2個のXが、縮合環または縮合環系の一部を形成してもよい。)から成る群から選ばれ;R1はそれぞれ独立してC1〜C10のアルキル基であり;R2はそれぞれ独立してC1〜C10のアルキル基であり;R3はそれぞれ水素であり;R4、R5およびR6はそれぞれ独立して水素または置換ヒドロカルビルもしくは非置換ヒドロカルビル基またはヘテロ原子であり;Tは架橋基であり;隣接するR4、R5およびR6基のいずれかも縮合環または多中心縮合環系を形成してもよく、これらの環は部分的に飽和、または飽和の芳香族であってもよい。
1)以下のa)およびb)を接触させる工程:
a)1種以上のオレフィン、および
b)以下の式によって表される遷移金属触媒化合物:
この式で、
Mはハフニウムまたはジルコニウムであり;
Xはそれぞれ独立して、1〜20個の炭素原子を有するヒドロカルビル基、ヒドリド、アミド、アルコキシド、スルフィド、ホスフィド、ハロゲン、ジエン、アミン、ホスフィン、エーテルおよびこれらの組み合わせから成る群から選ばれ;
R1およびR3はそれぞれ独立してC1〜C8のアルキル基であり;
R2、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13およびR14は、それぞれ独立して水素、または1〜8個の炭素原子を有する置換または非置換のヒドロカルビル基であり、
ただしR10〜R14基のうちの少なくとも3個が水素ではない;および
2)2011年3月25日に出願された米国特許出願第13/072,249号(これは参照によって本明細書に組み込まれる。)に記載された300g/モル以上のMnおよび(全不飽和を基準として)少なくとも30%のビニル鎖末端基を有するビニル停止オリゴマーを得る工程。
任意的な捕捉剤または共活性剤
重合反応の配置および条件
追加のコンパウンド
エチレンコポリマーを加硫する工程
試験方法
a.ローターは、30.48±0.03mmの直径、2.8±0.03mmの厚さ(鋸歯状の切り込みの頂上)および11mm以下のシャフト直径を有しなければならない。
b.ローターは、鋸歯状の面および端であって、1.6mmの中心上でカットされた0.8mmの幅および0.25〜0.38mmの深さの角溝を備えるものを有しなければならない。鋸歯状の切り込みは互いに直角の2組の溝から成る(正方形の断面線を形成する)。
c.ローターディスクの中心線がダイキャビティの中心線と±0.25 mmの許容範囲内で一致するように、ローターはダイキャビティの中心に配置されるものとする。スペーサーまたはシムが、シャフトを中間点に上げるために使用されてもよい。
d.摩耗点(ローターの上面の中心にある円錐形の突起)は、ローターの面と平らに機械加工されるものとする。
c=KDRIIDRI/(dn/dc)
この式で、KDRIは、600〜10Mの範囲の分子量を有する一連の単分散ポリスチレン標準物を用いてDRIを較正することによって決定された定数であり、(dn/dc)はその系の屈折率増分である。屈折率nは、145℃でのTCBおよびλ=690nmの場合にn=1.500である。本発明および添付された特許請求の範囲の目的のためには、エチレン−プロピレンコポリマーについて(dn/dc)= 0.1048、およびEPDMについて(dn/dc)= 0.01048〜0.0016ENBであり、ここでENBはエチレン−プロピレン−ジエンターポリマー中の重量パーセントでのENB含有量である。(dn/dc)の値は、他のポリマーおよびコポリマーについては別に0.1とされる。SEC方法のこの記載の全体にわたって使用されるパラメーターの単位は次の通りである:濃度はg/cm3で表され、分子量はg/モルで表され、固有粘度はdL/gで表される。
この式で、ΔR(θ)は散乱角θで測定された超過レーリー散乱強度であり、cはDRI分析から測定されたポリマー濃度であり、A2は第二ビリアル係数(本発明の目的のためには、エチレンホモポリマーについてA2=0.0015、およびエチレン−プロピレンコポリマーについてA2=0.0015−0.00001EEであり、EEはそのエチレン−プロピレンコポリマー中の重量パーセントでのエチレン含有量である。)である。P(θ)は単分散ランダムコイルのための形状因子であり、Koは以下の系の光学定数である:
この式で、NAはアボガドロ数であり、(dn/dc)はその系の屈折率増分である。屈折率nは、145℃でのTCBおよびλ=690nmの場合にn=1.500である。
ηs=c[η]+0.3(c[η])2
この式で、cは濃度であり、DRIの出力から決定された。
この式で、総和は積算限界間のクロマトグラフのスライスiにわたってされる。
等しい分子量および同じ組成の直鎖状ポリマーの固有粘度は、Mark−Houwinkの式を使用して計算され、この式で、Kおよびαは、直鎖状のエチレン/プロピレンコポリマーおよび直鎖状のエチレン−プロピレン−ジエンターポリマーの組成に基いて標準較正手順を使用して決定された。Mvは、LS分析によって測定された分子量に基いた粘度平均分子量である。同様の分子量およびコモノマー含有量を有する直鎖状標準物を選択すること、係数kおよび指数αを決定することの指針として、Macromolecules、2001年、第34巻、6812〜6820頁およびMacromolecules、2005年、第38巻、7181〜7183頁を見よ。
実施例1〜5における油展されたエチレンコポリマーは、2基のリアクターが直列に配置された連続撹拌槽リアクター装置でつくられた。第1のリアクターは0.5リットルであり、第2のリアクターは1リットルであった。リアクターは両方とも、撹拌器、温度調節器を備えた水冷/スチーム加熱要素および圧力調節器を装備したステンレス鋼製オートクレーブであった。リアクターは、反応混合物の沸点圧力を超える圧力に維持されて、反応物を液相に維持した。リアクターは液満で操作された。溶媒およびモノマーは最初に、アルミナおよびモレキュラーシーブの床で精製された。重合においてより低い活性の兆候がある場合はいつでも、精製塔は周期的に再生された。全ての液体供給原料はPulsaフィードポンプによってリアクターに送り込まれた。全ての液体流量はBrooks質量調節器を使用して調節された。エチレンは、冷却された溶媒/モノマー混合物中に溶解されたガスとして供給された。精製された溶媒およびモノマーは次に、多岐管を通してリアクターに供給される前に、冷却器を通すことによって約−15℃にまで冷却された。溶媒およびモノマーは多岐管の中で混合され、単一の管を通ってリアクターに供給された。同様に、活性化された触媒溶液が、別個のISCOシリンジポンプを使用して供給された。
Claims (10)
- 油展されたエチレンアルファオレフィン組成物であって、
オレフィンオリゴマーの一部を含んでいるエキステンダー油;および
エチレンコポリマーであって、前記エチレンコポリマーが前記オレフィンオリゴマーの他の部分をポリマー鎖単位として組み込んでいるエチレンコポリマー;
を含んでおり、
前記オレフィンオリゴマーが200g/モル〜15,000g/モルのMnを有し;かつ
前記組成物が、100超のせん断減粘性比、35度未満の位相角、40ムーニー単位超のムーニー大粘度(1+4@125℃)および500ムーニー単位・秒超のムーニー大緩和面積を有する、
油展されたエチレンアルファオレフィン組成物。 - 2種のエチレンコポリマーを含んでおり、第1のエチレンコポリマーが50,000g/モル未満の重量平均分子量を有し、かつ第2のエチレンコポリマーが100,000g/モル超の重量平均分子量を有する、請求項1に記載の組成物。
- 前記第1のエチレンコポリマーが、前記第2のエチレンコポリマーのエチレン含有量よりも少ないエチレン含有量を有し、前記第1のエチレンコポリマーと前記第2のエチレンコポリマーとのエチレン含有量の差が、5重量%超である、請求項2に記載の組成物。
- 30重量%〜80重量%のエチレン含有量を有する、請求項1に記載の組成物。
- 前記オリゴマーが無定形である、請求項1に記載の組成物。
- 請求項1に記載された油展されたエチレンアルファオレフィン組成物を製造するプロセスであって、
a.プロピレンと、任意的に(i)エチレンおよび(ii)1種以上のC4〜C20アルファオレフィンのうちの1種以上とを第1の触媒と接触させて、全ての不飽和鎖末端基を基準として少なくとも50%のビニル鎖末端基を有するオレフィンオリゴマーを製造する工程;および
b.前記オレフィンオリゴマーの少なくとも一部と少なくとも第2のC2〜C20のアルファオレフィンとを第2の触媒と接触させて、油展されたエチレン組成物を製造する工程;
を含む、プロセス。 - 前記第1の触媒が前記第2の触媒とは異なる、請求項6に記載のプロセス。
- 前記オレフィンオリゴマーおよび前記油展されたエチレン組成物が、直列に配置された個別の重合リアクターの中で製造される、請求項7に記載のプロセス。
- 前記油展されたエチレン組成物がジエン化合物を含んでおり、前記ジエン化合物が、5−エチリデン−2−ノルボルネン(ENB)、ビニルノルボルネン(VNB)、1,4−ヘキサジエン、ジシクロペンタジエンおよびこれらの組み合わせから成る群の少なくとも1種から選ばれる、請求項7に記載のプロセス。
- 前記オレフィンオリゴマーが第1のリアクターで製造され、前記オレフィンオリゴマーの少なくとも一部が第2のリアクター中に移送され、かつ前記油展されたエチレン組成物が第2のリアクターで製造される、請求項7に記載のプロセス。
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