TWI460193B - 以乙烯基為終端之高級烯烴的聚合物及其製造方法 - Google Patents

以乙烯基為終端之高級烯烴的聚合物及其製造方法 Download PDF

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Publication number: TWI460193B
Authority: TW; Taiwan
Prior art keywords: group; polymer; higher olefin; mol; mole
Prior art date: 2011-03-25

Application number

TW101108460A

Other languages

English (en)

Chinese (zh)

Other versions

TW201300431A (zh

Inventor

Matthew W Holtcamp

Charles J Ruff

Donna J Crowther

John R Hagadorn

Patrick Brant

Original Assignee

Exxonmobil Chem Patents Inc

Priority date (The priority date 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 date listed.)

2011-03-25

Filing date

2012-03-13

Publication date

2014-11-11

2011-03-25 Priority claimed from US13/072,288 external-priority patent/US8426659B2/en

2012-03-13 Application filed by Exxonmobil Chem Patents Inc filed Critical Exxonmobil Chem Patents Inc

2013-01-01 Publication of TW201300431A publication Critical patent/TW201300431A/zh

2014-11-11 Application granted granted Critical

2014-11-11 Publication of TWI460193B publication Critical patent/TWI460193B/zh

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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 55
238000000034 method Methods 0.000 title claims description 53
229920002554 vinyl polymer Polymers 0.000 title claims description 42
229920000098 polyolefin Polymers 0.000 title claims description 22
-1 R 21 Chemical compound 0.000 claims description 283
229920000642 polymer Polymers 0.000 claims description 164
150000001336 alkenes Chemical class 0.000 claims description 140
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 101
239000005977 Ethylene Substances 0.000 claims description 101
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 96
229910052739 hydrogen Inorganic materials 0.000 claims description 92
239000001257 hydrogen Substances 0.000 claims description 92
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 80
239000012190 activator Substances 0.000 claims description 76
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 75
239000003054 catalyst Substances 0.000 claims description 75
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 72
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
125000001183 hydrocarbyl group Chemical group 0.000 claims description 70
150000001875 compounds Chemical class 0.000 claims description 60
239000000203 mixture Substances 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 54
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 53
229920001577 copolymer Polymers 0.000 claims description 46
125000004122 cyclic group Chemical group 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 41
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 41
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 41
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 37
125000005842 heteroatom Chemical group 0.000 claims description 37
239000000178 monomer Substances 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
229920006395 saturated elastomer Polymers 0.000 claims description 35
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 34
125000003118 aryl group Chemical group 0.000 claims description 34
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 32
229910052726 zirconium Chemical group 0.000 claims description 31
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 30
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 30
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 27
DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims description 26
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 25
150000001450 anions Chemical class 0.000 claims description 24
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 22
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 20
229940069096 dodecene Drugs 0.000 claims description 20
150000004820 halides Chemical class 0.000 claims description 19
230000007935 neutral effect Effects 0.000 claims description 19
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 18
150000004703 alkoxides Chemical class 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 18
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
150000004678 hydrides Chemical class 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 17
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 16
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 16
150000003568 thioethers Chemical class 0.000 claims description 16
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 15
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 15
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 14
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 14
239000004913 cyclooctene Substances 0.000 claims description 14
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 13
229910052684 Cerium Inorganic materials 0.000 claims description 13
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
229910052796 boron Inorganic materials 0.000 claims description 12
HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 claims description 12
239000012954 diazonium Substances 0.000 claims description 12
150000001989 diazonium salts Chemical class 0.000 claims description 12
150000001993 dienes Chemical class 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 11
239000013638 trimer Substances 0.000 claims description 11
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 claims description 10
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 10
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
239000000314 lubricant Substances 0.000 claims description 9
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 8
125000000746 allylic group Chemical group 0.000 claims description 7
125000006612 decyloxy group Chemical group 0.000 claims description 7
229920001519 homopolymer Polymers 0.000 claims description 7
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
239000000539 dimer Substances 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
239000007983 Tris buffer Substances 0.000 claims description 3
239000007848 Bronsted acid Substances 0.000 claims description 2
WREUEIJSHIDLBG-UHFFFAOYSA-N CCN(CC)C1=CC=CC=C1.CCN(CC)C1=CC=CC=C1.CCN(CC)C1=CC=CC=C1.OB(O)O Chemical compound CCN(CC)C1=CC=CC=C1.CCN(CC)C1=CC=CC=C1.CCN(CC)C1=CC=CC=C1.OB(O)O WREUEIJSHIDLBG-UHFFFAOYSA-N 0.000 claims description 2
229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
DUKURNFHYQXCJG-JEOLMMCMSA-N alpha-L-Fucp-(1->4)-[beta-D-Galp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](NC(C)=O)[C@H](O[C@@H]2[C@H]([C@H](O[C@@H]3[C@H](OC(O)[C@H](O)[C@H]3O)CO)O[C@H](CO)[C@@H]2O)O)O[C@@H]1CO DUKURNFHYQXCJG-JEOLMMCMSA-N 0.000 claims description 2
230000001050 lubricating effect Effects 0.000 claims description 2
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 9
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical group [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 3
QDLFVXRWLQSBTF-UHFFFAOYSA-N 1,1,2-triethylhydrazine Chemical compound CCNN(CC)CC QDLFVXRWLQSBTF-UHFFFAOYSA-N 0.000 claims 1
LALXVXZHYIIWQP-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-1h-isochromene Chemical compound C1OCCC2CCCCC21 LALXVXZHYIIWQP-UHFFFAOYSA-N 0.000 claims 1
YKCNBNDWSATCJL-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hepta-2,5-diene Chemical compound C1=CC2C=CC1O2 YKCNBNDWSATCJL-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 64
238000006116 polymerization reaction Methods 0.000 description 49
238000005481 NMR spectroscopy Methods 0.000 description 46
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
239000000463 material Substances 0.000 description 40
238000006243 chemical reaction Methods 0.000 description 33
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239000000243 solution Substances 0.000 description 30
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 24
125000004435 hydrogen atom Chemical class [H]* 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
239000002904 solvent Substances 0.000 description 21
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229910052707 ruthenium Inorganic materials 0.000 description 19
239000007787 solid Substances 0.000 description 19
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230000015572 biosynthetic process Effects 0.000 description 17
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 17
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 16
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 16
238000003786 synthesis reaction Methods 0.000 description 16
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 15
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 14
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229910052782 aluminium Inorganic materials 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
239000002516 radical scavenger Substances 0.000 description 13
229910052723 transition metal Inorganic materials 0.000 description 13
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 12
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239000003446 ligand Substances 0.000 description 12
CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 12
239000000523 sample Substances 0.000 description 12
239000000126 substance Substances 0.000 description 12
239000012876 carrier material Substances 0.000 description 11
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150000001768 cations Chemical class 0.000 description 10
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238000010438 heat treatment Methods 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002002 slurry Substances 0.000 description 10
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 9
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229920002521 macromolecule Polymers 0.000 description 9
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GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 9
150000003624 transition metals Chemical class 0.000 description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
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239000000654 additive Substances 0.000 description 8
239000002585 base Substances 0.000 description 8
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
230000000694 effects Effects 0.000 description 8
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QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 8
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 8
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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238000000113 differential scanning calorimetry Methods 0.000 description 6
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230000004913 activation Effects 0.000 description 5
125000000129 anionic group Chemical group 0.000 description 5
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238000001035 drying Methods 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
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150000008282 halocarbons Chemical group 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229910052809 inorganic oxide Inorganic materials 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000012968 metallocene catalyst Substances 0.000 description 5
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238000002360 preparation method Methods 0.000 description 5
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238000001228 spectrum Methods 0.000 description 5
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239000004215 Carbon black (E152) Substances 0.000 description 4
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SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
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125000003545 alkoxy group Chemical group 0.000 description 4
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239000001273 butane Substances 0.000 description 4
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SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
WQIQNKQYEUMPBM-UHFFFAOYSA-N pentamethylcyclopentadiene Chemical compound CC1C(C)=C(C)C(C)=C1C WQIQNKQYEUMPBM-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
OSWUTXHGHGEDGK-UHFFFAOYSA-N phthalate;tributylazanium Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O.CCCC[NH+](CCCC)CCCC.CCCC[NH+](CCCC)CCCC OSWUTXHGHGEDGK-UHFFFAOYSA-N 0.000 description 1
239000012041 precatalyst Substances 0.000 description 1
238000011045 prefiltration Methods 0.000 description 1
ZTILHLWDFSMCLZ-UHFFFAOYSA-N prop-2-enylhydrazine Chemical compound NNCC=C ZTILHLWDFSMCLZ-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
230000005588 protonation Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011002 quantification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007670 refining Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000001542 size-exclusion chromatography Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229910052600 sulfate mineral Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000010558 suspension polymerization method Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical group SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
KUUVQVSHGLHAKZ-UHFFFAOYSA-N thionine Chemical compound C=1C=CC=CSC=CC=1 KUUVQVSHGLHAKZ-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
HSNQNPCNYIJJHT-ISLYRVAYSA-N trans-octadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCC HSNQNPCNYIJJHT-ISLYRVAYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
WCZKTXKOKMXREO-UHFFFAOYSA-N triethylsulfanium Chemical compound CC[S+](CC)CC WCZKTXKOKMXREO-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-O tris(2-methylphenyl)phosphanium Chemical compound CC1=CC=CC=C1[PH+](C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-O 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003754 zirconium Chemical class 0.000 description 1
229910001928 zirconium oxide Inorganic materials 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/14—Monomers containing five or more carbon atoms
- 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
- C08F210/14—Monomers containing five or more carbon atoms
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

TW101108460A 2011-03-25 2012-03-13 以乙烯基為終端之高級烯烴的聚合物及其製造方法 TWI460193B (zh)

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US13/072,288 US8426659B2 (en)	2011-03-25	2011-03-25	Vinyl terminated higher olefin polymers and methods to produce thereof
EP11167033		2011-05-23

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TWI460193B true TWI460193B (zh)	2014-11-11

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EP (1)	EP2688924A4 (fr)
JP (1)	JP5826913B2 (fr)
CN (1)	CN103443139B (fr)
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WO (1)	WO2012134721A2 (fr)

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KR101757370B1 (ko)	2015-06-01	2017-07-12	주식회사 엘지화학	1-옥텐 조성물
EP3387046B1 (fr) *	2015-12-09	2019-12-25	SABIC Global Technologies B.V.	Procédé de préparation de copolymères greffés à base de polyoléfine fonctionnalisée comprenant un premier bloc de polyoléfine ramifié à chaîne courte et une ou plusieurs chaînes latérales de polymères
US10882932B2 (en)	2016-10-05	2021-01-05	Exxonmobil Chemical Patents Inc.	Sterically hindered metallocenes, synthesis and use
CN109790240A (zh) *	2016-10-05	2019-05-21	埃克森美孚化学专利公司	空间位阻金属茂、合成和用途
WO2019094132A1 (fr) *	2017-11-13	2019-05-16	Exxonmobil Chemical Patents Inc.	Compositions de polyéthylène et articles fabriqués à partir de celles-ci
CN112912357B (zh) *	2018-09-17	2024-06-04	埃克森美孚化学专利公司	聚α-烯烃三聚物的制备方法和制备设备
US11661465B2 (en) *	2019-10-28	2023-05-30	Exxonmobil Chemical Patents Inc.	Dimer selective metallocene catalysts, non-aromatic hydrocarbon soluble activators, and processes to produce poly alpha-olefin oligmers therewith
CN116194494B (zh) *	2020-09-30	2025-04-08	博里利斯股份公司	改善性能特征的乙烯-辛烯共聚物
JP2025075105A (ja) *	2022-03-30	2025-05-15	三井化学株式会社	オレフィン重合体の製造方法

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- 2012-03-05 CN CN201280015024.3A patent/CN103443139B/zh not_active Expired - Fee Related
- 2012-03-05 EP EP12764747.7A patent/EP2688924A4/fr not_active Ceased
- 2012-03-05 JP JP2014501094A patent/JP5826913B2/ja not_active Expired - Fee Related
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CN103443139A (zh)	2013-12-11
TW201300431A (zh)	2013-01-01
EP2688924A4 (fr)	2015-02-25
EP2688924A2 (fr)	2014-01-29
WO2012134721A3 (fr)	2012-11-29
JP2014511912A (ja)	2014-05-19
JP5826913B2 (ja)	2015-12-02
WO2012134721A2 (fr)	2012-10-04
CN103443139B (zh)	2016-10-12

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2022-08-11	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
TWI460193B (zh)	2014-11-11	以乙烯基為終端之高級烯烴的聚合物及其製造方法
TWI549972B (zh)	2016-09-21	帶有乙烯基終端之高級烯烴共聚物及其製法
US8426659B2 (en)	2013-04-23	Vinyl terminated higher olefin polymers and methods to produce thereof
US8841397B2 (en)	2014-09-23	Vinyl terminated higher olefin polymers and methods to produce thereof
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US8816027B2 (en)	2014-08-26	Catalysts and methods of use thereof to produce vinyl terminated polymers
US8658556B2 (en)	2014-02-25	Catalyst systems comprising multiple non-coordinating anion activators and methods for polymerization therewith
US11059918B2 (en)	2021-07-13	Metallocene catalyst compositions and polymerization process therewith
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CN104428326A (zh)	2015-03-18	乙烯基封端聚合物及其制造方法
CN103596686B (zh)	2015-08-12	包含多种非配位阴离子化活化剂的催化剂体系以及使用其的聚合方法
CN103443144B (zh)	2016-07-06	乙烯基封端的高级烯烃共聚物及其制造方法
EP4665774A1 (fr)	2025-12-24	Composés de catalyseur métallocène ayant des substituants ferrocényle
WO2025080492A1 (fr)	2025-04-17	Composés catalyseurs métallocènes pour la production de polyoléfines