JP7115852B2 - 一又は複数の末端官能化された分岐を有するポリオレフィンの調製方法 - Google Patents
一又は複数の末端官能化された分岐を有するポリオレフィンの調製方法 Download PDFInfo
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- JP7115852B2 JP7115852B2 JP2017533759A JP2017533759A JP7115852B2 JP 7115852 B2 JP7115852 B2 JP 7115852B2 JP 2017533759 A JP2017533759 A JP 2017533759A JP 2017533759 A JP2017533759 A JP 2017533759A JP 7115852 B2 JP7115852 B2 JP 7115852B2
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- hydrocarbyl
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- bis
- polyolefin
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- 229920000098 polyolefin Polymers 0.000 title claims description 163
- 238000000034 method Methods 0.000 title claims description 76
- 229910052751 metal Inorganic materials 0.000 claims description 208
- 239000002184 metal Substances 0.000 claims description 202
- -1 ethylene, propylene, 1-butene Chemical group 0.000 claims description 167
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 167
- 239000003054 catalyst Substances 0.000 claims description 94
- 239000003795 chemical substances by application Substances 0.000 claims description 62
- 150000001336 alkenes Chemical class 0.000 claims description 53
- 239000012986 chain transfer agent Substances 0.000 claims description 51
- 239000007800 oxidant agent Substances 0.000 claims description 51
- 239000012685 metal catalyst precursor Substances 0.000 claims description 49
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 46
- 230000008569 process Effects 0.000 claims description 39
- 150000002739 metals Chemical class 0.000 claims description 38
- 238000010791 quenching Methods 0.000 claims description 37
- 230000000171 quenching effect Effects 0.000 claims description 37
- 229910052782 aluminium Inorganic materials 0.000 claims description 36
- 150000004678 hydrides Chemical class 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 239000011701 zinc Substances 0.000 claims description 27
- 229910052725 zinc Inorganic materials 0.000 claims description 25
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052726 zirconium Inorganic materials 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 9
- 229910007926 ZrCl Inorganic materials 0.000 claims description 9
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 8
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 claims description 8
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-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
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 8
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 150000002118 epoxides Chemical class 0.000 claims description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 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 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 4
- 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 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 claims description 4
- 229940069096 dodecene Drugs 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 4
- QBLGPUPHRFDAMT-UHFFFAOYSA-N C(C)[Zn]CCC=C Chemical compound C(C)[Zn]CCC=C QBLGPUPHRFDAMT-UHFFFAOYSA-N 0.000 claims description 3
- ZMVFRPYKRCLPGS-UHFFFAOYSA-N C(C)[Zn]CCCCCCC=C Chemical compound C(C)[Zn]CCCCCCC=C ZMVFRPYKRCLPGS-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
- FJMJPZLXUXRLLD-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2]([SiH](C)C)C1C2=CC=CC=C2C=C1 Chemical group [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2]([SiH](C)C)C1C2=CC=CC=C2C=C1 FJMJPZLXUXRLLD-UHFFFAOYSA-L 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 64
- 229910052799 carbon Inorganic materials 0.000 description 60
- 229920000642 polymer Polymers 0.000 description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 49
- 238000012546 transfer Methods 0.000 description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 37
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 36
- 229910052727 yttrium Inorganic materials 0.000 description 33
- 229910052760 oxygen Inorganic materials 0.000 description 29
- 229910052735 hafnium Inorganic materials 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 22
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 22
- 238000007254 oxidation reaction Methods 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
- 239000011575 calcium Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 21
- 230000003647 oxidation Effects 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 20
- 125000005842 heteroatom Chemical group 0.000 description 20
- 239000003446 ligand Substances 0.000 description 20
- 150000001408 amides Chemical class 0.000 description 19
- 230000000737 periodic effect Effects 0.000 description 19
- 239000004711 α-olefin 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 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000012018 catalyst precursor Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 125000004122 cyclic group Chemical group 0.000 description 16
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- 239000011777 magnesium Substances 0.000 description 16
- 229910052717 sulfur Inorganic materials 0.000 description 16
- 239000010936 titanium Substances 0.000 description 16
- 229910052733 gallium Inorganic materials 0.000 description 15
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 14
- 150000002367 halogens Chemical class 0.000 description 14
- 229910052719 titanium Inorganic materials 0.000 description 14
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 14
- 229910052796 boron Inorganic materials 0.000 description 13
- 239000011651 chromium Substances 0.000 description 13
- 238000007334 copolymerization reaction Methods 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 13
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000004698 Polyethylene Substances 0.000 description 12
- 229910052804 chromium Inorganic materials 0.000 description 12
- 239000003426 co-catalyst Substances 0.000 description 12
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 12
- 229910052749 magnesium Inorganic materials 0.000 description 12
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 12
- 238000010626 work up procedure Methods 0.000 description 12
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 229910010068 TiCl2 Inorganic materials 0.000 description 11
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- 238000007306 functionalization reaction Methods 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
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- 229910010277 boron hydride Inorganic materials 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 238000001542 size-exclusion chromatography Methods 0.000 description 10
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- 150000003624 transition metals Chemical class 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
- 150000004703 alkoxides Chemical class 0.000 description 9
- 125000005234 alkyl aluminium group Chemical group 0.000 description 9
- 230000000670 limiting effect Effects 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 9
- ZCBSOTLLNBJIEK-UHFFFAOYSA-N silane titanium Chemical compound [SiH4].[Ti] ZCBSOTLLNBJIEK-UHFFFAOYSA-N 0.000 description 9
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- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 8
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- 238000012711 chain transfer polymerization Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 8
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- 238000006460 hydrolysis reaction Methods 0.000 description 7
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- 125000001424 substituent group Chemical group 0.000 description 7
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- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 6
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 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 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
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- 238000005481 NMR spectroscopy Methods 0.000 description 5
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 125000003158 alcohol group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
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- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 5
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
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- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
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- 229940071182 stannate Drugs 0.000 description 4
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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Images
Classifications
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
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- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (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 |
|---|---|---|---|
| EP14200124.7 | 2014-12-23 | ||
| EP14200124.7A EP3037437A1 (en) | 2014-12-23 | 2014-12-23 | Process for the preparation of a polyolefin having one or multiple end-functionalized branches. |
| PCT/EP2015/081207 WO2016102694A1 (en) | 2014-12-23 | 2015-12-23 | Process for the preparation of a polyolefin having one or multiple end-functionalized branches |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018500430A JP2018500430A (ja) | 2018-01-11 |
| JP2018500430A5 JP2018500430A5 (enExample) | 2018-11-22 |
| JP7115852B2 true JP7115852B2 (ja) | 2022-08-09 |
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| US (1) | US10465018B2 (enExample) |
| EP (2) | EP3037437A1 (enExample) |
| JP (1) | JP7115852B2 (enExample) |
| KR (1) | KR102470347B1 (enExample) |
| CN (1) | CN107223138B (enExample) |
| SA (1) | SA517381806B1 (enExample) |
| WO (1) | WO2016102694A1 (enExample) |
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| JP6866346B2 (ja) * | 2015-07-23 | 2021-04-28 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | 一又は複数の懸垂官能基を有するポリオレフィンの調製方法 |
| WO2017039994A1 (en) | 2015-08-31 | 2017-03-09 | Exxonmobil Chemical Patents Inc. | Aluminum alkyls with pendant olefins on clays |
| 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 |
| JP2018525507A (ja) * | 2015-08-31 | 2018-09-06 | エクソンモービル・ケミカル・パテンツ・インク | ビニル連鎖移動剤の使用によって製造されたポリマー |
| WO2017039995A1 (en) * | 2015-08-31 | 2017-03-09 | Exxonmobil Chemical Patents Inc. | Aluminum alkyls with pendant olefins for polyolefin reactions |
| EP3387047B1 (en) | 2015-12-09 | 2020-01-01 | 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 |
| 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 |
| WO2018160278A1 (en) * | 2017-03-01 | 2018-09-07 | Exxonmobil Chemical Patents Inc. | Branched ethylene copolymers produced via use of vinyl transfer agents and processes for production thereof |
| EP3728351A1 (en) * | 2017-12-22 | 2020-10-28 | SABIC Global Technologies B.V. | Process for preparation of ethylene and propylene ionomer |
| SG11202005532YA (en) | 2017-12-29 | 2020-07-29 | Dow Global Technologies Llc | Capped dual-headed organoaluminum compositions |
| CN109467660B (zh) * | 2018-10-06 | 2021-03-02 | 天津大学 | 利用链穿梭方法合成聚(乙烯-r-降冰片烯/乙烯)多嵌段共聚物 |
| BR112021012845A2 (pt) * | 2018-12-28 | 2021-09-28 | Dow Global Technologies Llc | Composição curável, e, artigo |
| WO2020140064A1 (en) * | 2018-12-28 | 2020-07-02 | 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 |
| US12195563B2 (en) * | 2020-12-29 | 2025-01-14 | Exxonmobil Chemical Patents Inc. | Polyolefin-based ionomers and production thereof |
| CN117083307A (zh) * | 2021-04-30 | 2023-11-17 | 陶氏环球技术有限责任公司 | 磺酰卤封端的聚乙烯的合成 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001278928A (ja) | 2000-01-25 | 2001-10-10 | Mitsui Chemicals Inc | フィルムおよびシート |
| JP2005307113A (ja) | 2004-04-26 | 2005-11-04 | National Institute Of Advanced Industrial & Technology | 極性基含有共重合体及びその製造方法 |
| JP2007262338A (ja) | 2006-03-29 | 2007-10-11 | Japan Polypropylene Corp | 極性基を有すプロピレン系共重合体又はその組成物を用いた塗装用成形品 |
| WO2013182290A1 (en) | 2012-06-04 | 2013-12-12 | Sasol Olefins & Surfactants Gmbh | Amidinate and guanidinate complexes, their use as chain transfer polymerization catalysts and long chain alcohols obtained by such process |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5106806A (en) | 1990-10-18 | 1992-04-21 | Shell Oil Company | Olefin polymerization catalyst |
| US5077357A (en) | 1990-10-22 | 1991-12-31 | Shell Oil Company | Olefin polymerization catalyst |
| CA1141093A (en) | 1979-05-17 | 1983-02-08 | Brian L. Goodall | Olefin polymerization catalyst compositions and a process for the polymerization of olefins employing such compositions |
| JPS61151202A (ja) * | 1984-12-26 | 1986-07-09 | Toa Nenryo Kogyo Kk | プロピレン重合体の製造法 |
| IT1227259B (it) | 1988-09-30 | 1991-03-28 | Himont Inc | Catalizzatori per la polimerizzazione di olefine. |
| US5556820A (en) | 1989-12-28 | 1996-09-17 | Idemitsu Petrochemical Co., Ltd. | Catalyst component for olefin polymerization and process for producing polyolefins |
| US5374696A (en) | 1992-03-26 | 1994-12-20 | The Dow Chemical Company | Addition polymerization process using stabilized reduced metal catalysts |
| NL9201970A (nl) | 1992-11-11 | 1994-06-01 | Dsm Nv | Indenylverbindingen en katalysatorcomponenten voor de polymerisatie van olefinen. |
| US5468819A (en) * | 1993-11-16 | 1995-11-21 | The B.F. Goodrich Company | Process for making polymers containing a norbornene repeating unit by addition polymerization using an organo (nickel or palladium) complex |
| US5472785A (en) * | 1994-04-12 | 1995-12-05 | Minnesota Mining And Manufacturing Company | Reactive wax-containing moisture curable hot melt composition |
| JP3719727B2 (ja) * | 1994-10-13 | 2005-11-24 | 三井化学株式会社 | 末端に官能基を有するポリオレフィンの製造方法 |
| ES2116776T3 (es) | 1994-10-31 | 1998-07-16 | Dsm Nv | Composicion catalitica y procedimiento para la polimerizacion de una olefina. |
| WO1996032426A1 (en) | 1995-04-10 | 1996-10-17 | Dsm N.V. | Method for the preparation of a catalyst suitable for the polymerisation of an olefine |
| US5756416A (en) * | 1995-11-28 | 1998-05-26 | Union Carbide Chemicals & Plastics Technology Corporation | Catalyst composition having improved comonomer reactivity |
| BR9708971A (pt) | 1996-05-03 | 1999-08-03 | Dsm Nv | Processo para a polimerização de alfa-olefinas |
| AU2653097A (en) | 1996-05-03 | 1997-11-26 | Dsm N.V. | Process for the production of functional polyolefins |
| US6248837B1 (en) * | 1996-07-15 | 2001-06-19 | The Penn State Research Foundation | Process for preparing polyolefin diblock copolymers involving borane chain transfer reaction in transition metal-mediated olefin polymerization |
| US6208151B1 (en) * | 1997-12-23 | 2001-03-27 | Texas Instruments Incorporated | Method and apparatus for measurement of microscopic electrical characteristics |
| JP2002503732A (ja) * | 1998-02-11 | 2002-02-05 | ザ ダウ ケミカル カンパニー | 改良されたオレフィン重合方法 |
| KR100280373B1 (ko) * | 1998-09-18 | 2001-02-01 | 김충섭 | 메탈로센 촉매에 의한 관능성 말단기를 갖는 폴리에틸렌의 제조방법 |
| DE60018870T2 (de) | 1999-01-22 | 2006-04-13 | Mitsui Chemicals, Inc. | Verfahren zur herstellung eines olefinpolymers und olefinpolymer |
| US6342622B1 (en) | 1999-06-11 | 2002-01-29 | Dsm B.V. | Indenyl compounds for the polymerization of olefins |
| EP1086961A1 (en) | 1999-09-27 | 2001-03-28 | Dsm N.V. | Process for the preparation of a catalyst component for the polymerisation of an olefin |
| BR0204687B1 (pt) | 2001-03-30 | 2012-12-11 | componente de catalisador sólido para a polimerização de olefinas, catalisador para a polimerização de olefinas, e, copolìmero em bloco de propileno. | |
| US7087686B2 (en) | 2001-08-06 | 2006-08-08 | Bp Chemicals Limited | Chain growth reaction process |
| JP3891905B2 (ja) * | 2002-08-28 | 2007-03-14 | 日本ポリプロ株式会社 | 末端ビニル基含有プロピレン−アルケニルアルミニウム共重合体の製造方法および共重合体 |
| US20060287449A1 (en) | 2003-03-10 | 2006-12-21 | Koichi Miyamoto | Ultrahigh-molecular ethylene polymer |
| EP2357203B1 (en) | 2004-03-17 | 2017-05-24 | Dow Global Technologies LLC | Catalyst composition comprising shuttling agent for higher olefin multi-block copolymer formation |
| ATE416233T1 (de) | 2004-07-30 | 2008-12-15 | Saudi Basic Ind Corp | Hochtransparente propylencopolymerzusammensetzungen |
| RU2008110052A (ru) * | 2005-09-15 | 2009-09-20 | Дау Глобал Текнолоджиз Инк. (Us) | Олефиновые блок-сополимеры, получаемые каталитически с использованием полимеризуемого челночного агента |
| BRPI0711891B1 (pt) | 2006-05-24 | 2018-05-02 | Saudi Basic Industries Corporation | Processo para a preparação de um componente catalisador para a polimerização de propileno |
| BR112012001942B1 (pt) | 2009-07-29 | 2019-10-22 | Dow Global Technologies Llc | agente de permuta de cadeia multifuncional, processo para preparar um agente de permuta de cadeia multifuncional, processo para preparar uma composição multifuncional, composição multifuncional, processo para preparar um agente de permuta de cadeia multifuncional contendo poli-radical poliolefina, poliolefina telequélica, processo para preparar uma poliolefina com funcionalidade terminal e separador de bateria |
| KR102001440B1 (ko) | 2011-12-12 | 2019-07-18 | 사우디 베이식 인더스트리즈 코포레이션 | 촉매 시스템의 존재 하에 2형식 폴리에틸렌을 생산하는 방법 |
| EP2882810B1 (en) | 2012-08-03 | 2018-01-17 | ExxonMobil Chemical Patents Inc. | Catalysts comprising salan ligands |
| WO2014022010A2 (en) | 2012-08-03 | 2014-02-06 | Exxonmobil Chemical Patents Inc. | Non-symmetric catalysts comprising salan ligands |
| EP2880097B1 (en) | 2012-08-03 | 2023-10-18 | ExxonMobil Chemical Patents Inc. | Process to prepare a vinyl terminated polyethylene with long chain branching |
-
2014
- 2014-12-23 EP EP14200124.7A patent/EP3037437A1/en not_active Withdrawn
-
2015
- 2015-12-23 CN CN201580075823.3A patent/CN107223138B/zh active Active
- 2015-12-23 US US15/537,933 patent/US10465018B2/en active Active
- 2015-12-23 KR KR1020177020265A patent/KR102470347B1/ko active Active
- 2015-12-23 WO PCT/EP2015/081207 patent/WO2016102694A1/en not_active Ceased
- 2015-12-23 JP JP2017533759A patent/JP7115852B2/ja active Active
- 2015-12-23 EP EP15823164.7A patent/EP3237461A1/en active Pending
-
2017
- 2017-06-22 SA SA517381806A patent/SA517381806B1/ar unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001278928A (ja) | 2000-01-25 | 2001-10-10 | Mitsui Chemicals Inc | フィルムおよびシート |
| JP2005307113A (ja) | 2004-04-26 | 2005-11-04 | National Institute Of Advanced Industrial & Technology | 極性基含有共重合体及びその製造方法 |
| JP2007262338A (ja) | 2006-03-29 | 2007-10-11 | Japan Polypropylene Corp | 極性基を有すプロピレン系共重合体又はその組成物を用いた塗装用成形品 |
| WO2013182290A1 (en) | 2012-06-04 | 2013-12-12 | Sasol Olefins & Surfactants Gmbh | Amidinate and guanidinate complexes, their use as chain transfer polymerization catalysts and long chain alcohols obtained by such process |
Also Published As
| Publication number | Publication date |
|---|---|
| US20170355787A1 (en) | 2017-12-14 |
| CN107223138B (zh) | 2020-10-23 |
| JP2018500430A (ja) | 2018-01-11 |
| US10465018B2 (en) | 2019-11-05 |
| EP3237461A1 (en) | 2017-11-01 |
| KR102470347B1 (ko) | 2022-11-23 |
| KR20170108959A (ko) | 2017-09-27 |
| CN107223138A (zh) | 2017-09-29 |
| SA517381806B1 (ar) | 2021-01-14 |
| EP3037437A1 (en) | 2016-06-29 |
| WO2016102694A1 (en) | 2016-06-30 |
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