JP6770960B2 - 分岐ポリオレフィンの調製方法 - Google Patents
分岐ポリオレフィンの調製方法 Download PDFInfo
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- JP6770960B2 JP6770960B2 JP2017533760A JP2017533760A JP6770960B2 JP 6770960 B2 JP6770960 B2 JP 6770960B2 JP 2017533760 A JP2017533760 A JP 2017533760A JP 2017533760 A JP2017533760 A JP 2017533760A JP 6770960 B2 JP6770960 B2 JP 6770960B2
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- group
- hydrocarbyl
- metal
- bis
- aluminum
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- 229920000098 polyolefin Polymers 0.000 title claims description 78
- 238000000034 method Methods 0.000 title claims description 72
- -1 hydrocarbyl zinc Chemical compound 0.000 claims description 185
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 155
- 229910052751 metal Inorganic materials 0.000 claims description 155
- 239000002184 metal Substances 0.000 claims description 148
- 239000003054 catalyst Substances 0.000 claims description 91
- 150000001336 alkenes Chemical class 0.000 claims description 62
- 229910052782 aluminium Inorganic materials 0.000 claims description 51
- 239000012986 chain transfer agent Substances 0.000 claims description 50
- 239000003795 chemical substances by application Substances 0.000 claims description 50
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 50
- 239000000178 monomer Substances 0.000 claims description 42
- 239000012685 metal catalyst precursor Substances 0.000 claims description 41
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 39
- 239000011701 zinc Substances 0.000 claims description 37
- 238000006116 polymerization reaction Methods 0.000 claims description 36
- 229910052725 zinc Inorganic materials 0.000 claims description 35
- 229910052726 zirconium Inorganic materials 0.000 claims description 20
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 18
- 238000010791 quenching Methods 0.000 claims description 16
- 230000000171 quenching effect Effects 0.000 claims description 16
- 230000003197 catalytic effect Effects 0.000 claims description 15
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 13
- 229910007926 ZrCl Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 11
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims description 11
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 10
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 9
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 9
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 claims description 8
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 8
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 claims description 8
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims description 8
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 claims description 8
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims description 8
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims description 8
- 239000003426 co-catalyst Substances 0.000 claims description 8
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 8
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 8
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 7
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- IQEPEDROVHGOAR-UHFFFAOYSA-N C(C(C)C)[Al](CCC=C)CC(C)C Chemical compound C(C(C)C)[Al](CCC=C)CC(C)C IQEPEDROVHGOAR-UHFFFAOYSA-N 0.000 claims description 5
- FJMJPZLXUXRLLD-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2]([SiH](C)C)C1C2=CC=CC=C2C=C1 Chemical compound [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2]([SiH](C)C)C1C2=CC=CC=C2C=C1 FJMJPZLXUXRLLD-UHFFFAOYSA-L 0.000 claims description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 5
- 229940069096 dodecene Drugs 0.000 claims description 4
- 238000007306 functionalization reaction Methods 0.000 claims description 4
- DYSCYJQZDQCNEG-UHFFFAOYSA-N hex-5-enyl-bis(2-methylpropyl)alumane Chemical compound C(C(C)C)[Al](CCCCC=C)CC(C)C DYSCYJQZDQCNEG-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- KLAWFKRMCIXRFS-UHFFFAOYSA-N 5-ethenylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C=C)CC1C=C2 KLAWFKRMCIXRFS-UHFFFAOYSA-N 0.000 claims description 3
- QBLGPUPHRFDAMT-UHFFFAOYSA-N C(C)[Zn]CCC=C Chemical compound C(C)[Zn]CCC=C QBLGPUPHRFDAMT-UHFFFAOYSA-N 0.000 claims description 3
- PHUYKZNPNVDCIC-UHFFFAOYSA-N CC[Zn]CCCCC=C Chemical compound CC[Zn]CCCCC=C PHUYKZNPNVDCIC-UHFFFAOYSA-N 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims 1
- IMZDBFZGBFMQGD-UHFFFAOYSA-N C(CCCCCC=C)[Zn] Chemical compound C(CCCCCC=C)[Zn] IMZDBFZGBFMQGD-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 56
- 229910052757 nitrogen Inorganic materials 0.000 description 52
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 37
- 239000000047 product Substances 0.000 description 34
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 32
- 238000012546 transfer Methods 0.000 description 30
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 26
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
- 239000012018 catalyst precursor Substances 0.000 description 23
- 229910052735 hafnium Inorganic materials 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 229910052733 gallium Inorganic materials 0.000 description 22
- 239000004711 α-olefin Substances 0.000 description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 21
- 150000004678 hydrides Chemical class 0.000 description 21
- 230000000737 periodic effect Effects 0.000 description 21
- 239000011575 calcium Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 19
- 239000011777 magnesium Substances 0.000 description 19
- 229910052698 phosphorus Inorganic materials 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229910052791 calcium Inorganic materials 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 17
- 239000010936 titanium Substances 0.000 description 17
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 16
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 16
- 239000003446 ligand Substances 0.000 description 16
- 229910052749 magnesium Inorganic materials 0.000 description 15
- 125000004122 cyclic group Chemical group 0.000 description 14
- 229910052719 titanium Inorganic materials 0.000 description 14
- 239000011651 chromium Substances 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052804 chromium Inorganic materials 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 11
- 229910052796 boron Inorganic materials 0.000 description 11
- 229910010277 boron hydride Inorganic materials 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 10
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 238000001542 size-exclusion chromatography Methods 0.000 description 10
- 229910052727 yttrium Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 9
- 239000004698 Polyethylene Substances 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 229910052723 transition metal Inorganic materials 0.000 description 9
- 150000003624 transition metals Chemical class 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 230000000670 limiting effect Effects 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000005234 alkyl aluminium group Chemical group 0.000 description 6
- 238000012711 chain transfer polymerization Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229920002521 macromolecule Polymers 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910052718 tin Inorganic materials 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000001639 boron compounds Chemical class 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WNVPEOIVJPBPAN-UHFFFAOYSA-L [Cl-].[Cl-].C1=CCCC2C(C(C)(C)C(C)(C)C(C3([Zr+2])C)(C)C)(C)C3=C(CC=3C4=CC=CC=3)C4=C21 Chemical compound [Cl-].[Cl-].C1=CCCC2C(C(C)(C)C(C)(C)C(C3([Zr+2])C)(C)C)(C)C3=C(CC=3C4=CC=CC=3)C4=C21 WNVPEOIVJPBPAN-UHFFFAOYSA-L 0.000 description 4
- NDJMNNSJDIFFTH-UHFFFAOYSA-L [Cl-].[Cl-].CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr+2]([SiH](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1[Zr+2]([SiH](C)C)C1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 NDJMNNSJDIFFTH-UHFFFAOYSA-L 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- GMDSGSPTIDDIAZ-UHFFFAOYSA-N bis(2-methylpropyl)-oct-7-enylalumane Chemical compound CC(C)C[Al](CC(C)C)CCCCCCC=C GMDSGSPTIDDIAZ-UHFFFAOYSA-N 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- LRVUGEZGBKPRRZ-UHFFFAOYSA-L oxygen(2-);zirconium(4+);dichloride Chemical compound [O-2].[Cl-].[Cl-].[Zr+4] LRVUGEZGBKPRRZ-UHFFFAOYSA-L 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000007613 slurry method Methods 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006276 transfer reaction Methods 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tri-tert-butylphosphine Substances CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- 150000003754 zirconium Chemical class 0.000 description 4
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 3
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
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- ITKSXDXOEYKPIA-UHFFFAOYSA-N bis(trimethylsilyl)azanide;ethylaluminum(2+) Chemical compound CC[Al+2].C[Si](C)(C)[N-][Si](C)(C)C.C[Si](C)(C)[N-][Si](C)(C)C ITKSXDXOEYKPIA-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- PFEXTKFWFAKZQG-UHFFFAOYSA-N dipentylazanide;2-methylpropylaluminum(2+) Chemical compound CC(C)C[Al+2].CCCCC[N-]CCCCC.CCCCC[N-]CCCCC PFEXTKFWFAKZQG-UHFFFAOYSA-N 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001622 two pulse phase modulation pulse sequence Methods 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- DWTTZBARDOXEAM-UHFFFAOYSA-N zearalenone Chemical compound O=C1OC(C)CCCC(O)CCCCCC2=CC(O)=CC(O)=C21 DWTTZBARDOXEAM-UHFFFAOYSA-N 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- BYYXHWABFVUKLO-UHFFFAOYSA-N zinc;2-methylpropane Chemical compound [Zn+2].C[C-](C)C.C[C-](C)C BYYXHWABFVUKLO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—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
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP 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
- 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
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
-
- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/09—Long chain branches
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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)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14200125.4 | 2014-12-23 | ||
| EP14200125.4A EP3037438A1 (en) | 2014-12-23 | 2014-12-23 | Process for the preparation of a branched polyolefin |
| PCT/EP2015/081203 WO2016102690A1 (en) | 2014-12-23 | 2015-12-23 | Process for the preparation of a branched polyolefin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018500431A JP2018500431A (ja) | 2018-01-11 |
| JP2018500431A5 JP2018500431A5 (https=) | 2018-11-22 |
| JP6770960B2 true JP6770960B2 (ja) | 2020-10-21 |
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|---|---|---|---|
| JP2017533760A Active JP6770960B2 (ja) | 2014-12-23 | 2015-12-23 | 分岐ポリオレフィンの調製方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10450388B2 (https=) |
| EP (2) | EP3037438A1 (https=) |
| JP (1) | JP6770960B2 (https=) |
| KR (1) | KR102510436B1 (https=) |
| CN (1) | CN107207660B (https=) |
| SA (1) | SA517381805B1 (https=) |
| WO (1) | WO2016102690A1 (https=) |
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| US20180251585A1 (en) * | 2015-07-23 | 2018-09-06 | Sabic Global Technologies B.V. | Process for the preparation of a polyolefin having one or multiple pending functionalities |
| US10618988B2 (en) | 2015-08-31 | 2020-04-14 | Exxonmobil Chemical Patents Inc. | Branched propylene polymers produced via use of vinyl transfer agents and processes for production thereof |
| EP3344666A4 (en) * | 2015-08-31 | 2019-07-31 | ExxonMobil Chemical Patents Inc. | POLYMERS PRODUCED BY VINYL TRANSFER AGENTS |
| US9982067B2 (en) | 2015-09-24 | 2018-05-29 | Exxonmobil Chemical Patents Inc. | Polymerization process using pyridyldiamido compounds supported on organoaluminum treated layered silicate supports |
| US10717826B2 (en) | 2015-12-09 | 2020-07-21 | Sabic Global Technologies B.V. | Process for the preparation of polyolefin-based graft copolymers comprising a first long chain branched polyolefin block and one or multiple polymer side chains |
| US10927196B2 (en) | 2016-06-30 | 2021-02-23 | Exxonmobil Chemical Patents Inc. | Long chain branched polypropylene via polymerization with aluminum vinyl transfer agent |
| US10562987B2 (en) | 2016-06-30 | 2020-02-18 | Exxonmobil Chemical Patents Inc. | Polymers produced via use of quinolinyldiamido transition metal complexes and vinyl transfer agents |
| WO2018160277A1 (en) * | 2017-02-28 | 2018-09-07 | Exxonmobil Chemical Patents Inc. | Branched propylene polymers produced via use of vinyl transfer agents and processes for production thereof |
| WO2018160276A1 (en) * | 2017-02-28 | 2018-09-07 | Exxonmobil Chemical Patents Inc. | Polymers produced via use of quinolinyldiamido transition metal complexes and vinyl transfer agents |
| US10626200B2 (en) | 2017-02-28 | 2020-04-21 | Exxonmobil Chemical Patents Inc. | Branched EPDM polymers produced via use of vinyl transfer agents and processes for production thereof |
| US10676551B2 (en) | 2017-03-01 | 2020-06-09 | Exxonmobil Chemical Patents Inc. | Branched ethylene copolymers produced via use of vinyl transfer agents and processes for production thereof |
| WO2019122455A1 (en) | 2017-12-22 | 2019-06-27 | Sabic Global Technologies B.V. | Process for preparation of amorphous functionalized olefin copolymer |
| WO2019122457A1 (en) | 2017-12-22 | 2019-06-27 | Sabic Global Technologies B.V. | Process for preparation of ethylene and propylene ionomer |
| KR102320012B1 (ko) * | 2018-01-12 | 2021-11-02 | 주식회사 엘지화학 | 리간드 화합물, 전이금속 화합물 및 이를 포함하는 촉매 조성물 |
| US12098160B2 (en) * | 2018-12-28 | 2024-09-24 | Dow Global Technologies Llc | Organometallic chain transfer agents |
| CN111116811B (zh) * | 2020-01-03 | 2022-07-05 | 天津大学 | 一种1-丁烯/降冰片烯共聚物及其制备方法 |
| WO2022029213A1 (en) * | 2020-08-06 | 2022-02-10 | Total Research & Technology Feluy | Process for preparing ethylene polymers having long chain branches |
| JP7697239B2 (ja) * | 2021-03-22 | 2025-06-24 | 日本ポリエチレン株式会社 | エチレン重合用触媒の製造方法および前記エチレン重合用触媒を含むエチレン重合体またはエチレンとα－オレフィンとの共重合体の製造方法。 |
| WO2023163962A1 (en) * | 2022-02-23 | 2023-08-31 | Sealed Air Corporation (Us) | Bulk cheese barrier bag |
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-
2014
- 2014-12-23 EP EP14200125.4A patent/EP3037438A1/en not_active Withdrawn
-
2015
- 2015-12-23 CN CN201580075828.6A patent/CN107207660B/zh active Active
- 2015-12-23 EP EP15816486.3A patent/EP3237460A1/en active Pending
- 2015-12-23 KR KR1020177020264A patent/KR102510436B1/ko active Active
- 2015-12-23 JP JP2017533760A patent/JP6770960B2/ja active Active
- 2015-12-23 WO PCT/EP2015/081203 patent/WO2016102690A1/en not_active Ceased
- 2015-12-23 US US15/537,926 patent/US10450388B2/en active Active
-
2017
- 2017-06-22 SA SA517381805A patent/SA517381805B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3037438A1 (en) | 2016-06-29 |
| US10450388B2 (en) | 2019-10-22 |
| SA517381805B1 (ar) | 2021-01-14 |
| CN107207660A (zh) | 2017-09-26 |
| EP3237460A1 (en) | 2017-11-01 |
| WO2016102690A1 (en) | 2016-06-30 |
| CN107207660B (zh) | 2020-02-14 |
| KR102510436B1 (ko) | 2023-03-14 |
| JP2018500431A (ja) | 2018-01-11 |
| KR20170108958A (ko) | 2017-09-27 |
| US20170355786A1 (en) | 2017-12-14 |
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