KR102510436B1 - 분지형 폴리올레핀의 제조 방법 - Google Patents
분지형 폴리올레핀의 제조 방법 Download PDFInfo
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- KR102510436B1 KR102510436B1 KR1020177020264A KR20177020264A KR102510436B1 KR 102510436 B1 KR102510436 B1 KR 102510436B1 KR 1020177020264 A KR1020177020264 A KR 1020177020264A KR 20177020264 A KR20177020264 A KR 20177020264A KR 102510436 B1 KR102510436 B1 KR 102510436B1
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- KR
- South Korea
- Prior art keywords
- hydrocarbyl
- group
- metal
- bis
- aluminum
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000098 polyolefin Polymers 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 61
- 230000008569 process Effects 0.000 title abstract description 36
- 229910052751 metal Inorganic materials 0.000 claims abstract description 186
- 239000002184 metal Substances 0.000 claims abstract description 179
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 158
- 150000001336 alkenes Chemical class 0.000 claims abstract description 60
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 55
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000000178 monomer Substances 0.000 claims abstract description 39
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 35
- -1 ethyl (3-buten-1-yl) Chemical group 0.000 claims description 187
- 239000003054 catalyst Substances 0.000 claims description 90
- 229910052782 aluminium Inorganic materials 0.000 claims description 47
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 47
- 239000012685 metal catalyst precursor Substances 0.000 claims description 46
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 239000011701 zinc Substances 0.000 claims description 32
- 229910052725 zinc Inorganic materials 0.000 claims description 30
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 29
- 229910052796 boron Inorganic materials 0.000 claims description 29
- 229910052735 hafnium Inorganic materials 0.000 claims description 26
- 239000011777 magnesium Substances 0.000 claims description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
- 239000012018 catalyst precursor Substances 0.000 claims description 25
- 239000003426 co-catalyst Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 230000000737 periodic effect Effects 0.000 claims description 23
- 229910052733 gallium Inorganic materials 0.000 claims description 22
- 229910052749 magnesium Inorganic materials 0.000 claims description 22
- 239000004711 α-olefin Substances 0.000 claims description 22
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 21
- 239000011575 calcium Substances 0.000 claims description 20
- 229910052726 zirconium Inorganic materials 0.000 claims description 20
- 229910052791 calcium Inorganic materials 0.000 claims description 17
- 150000004678 hydrides Chemical class 0.000 claims description 17
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052804 chromium Inorganic materials 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 15
- 238000010791 quenching Methods 0.000 claims description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 14
- 230000000171 quenching effect Effects 0.000 claims description 14
- 229910052719 titanium Inorganic materials 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 229910010277 boron hydride Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910007926 ZrCl Inorganic materials 0.000 claims description 9
- 229910000085 borane Inorganic materials 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 8
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-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
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 7
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 6
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 claims description 6
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 6
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 6
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 claims description 6
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 6
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 claims description 6
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims description 6
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 6
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 5
- 229910052763 palladium Inorganic materials 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 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 150000003754 zirconium Chemical class 0.000 claims description 4
- 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 3
- 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
- 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 3
- ZMVFRPYKRCLPGS-UHFFFAOYSA-N C(C)[Zn]CCCCCCC=C Chemical compound C(C)[Zn]CCCCCCC=C ZMVFRPYKRCLPGS-UHFFFAOYSA-N 0.000 claims description 3
- HXHXUOYNZWHFLT-UHFFFAOYSA-N C(CCCC=C)[Al](CCCCC=C)CCCCC=C Chemical compound C(CCCC=C)[Al](CCCCC=C)CCCCC=C HXHXUOYNZWHFLT-UHFFFAOYSA-N 0.000 claims description 3
- VHNNPTGLWYHNHE-UHFFFAOYSA-N C1=CC2=CC=CC=C2C1[Zr]C1C2=CC=CC=C2C=C1 Chemical compound C1=CC2=CC=CC=C2C1[Zr]C1C2=CC=CC=C2C=C1 VHNNPTGLWYHNHE-UHFFFAOYSA-N 0.000 claims description 3
- HEMYFEFGZYYQSU-UHFFFAOYSA-N C=CCCCCCC[Zn]CCCCCCC=C Chemical compound C=CCCCCCC[Zn]CCCCCCC=C HEMYFEFGZYYQSU-UHFFFAOYSA-N 0.000 claims description 3
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 3
- 229940069096 dodecene Drugs 0.000 claims description 3
- 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 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 3
- KYOZLPKCURERER-UHFFFAOYSA-N tris(but-3-enyl)alumane Chemical compound C=CCC[Al](CCC=C)CCC=C KYOZLPKCURERER-UHFFFAOYSA-N 0.000 claims description 3
- RRWJQXJVEHEZJR-UHFFFAOYSA-N tris(oct-7-enyl)alumane Chemical compound C=CCCCCCC[Al](CCCCCCC=C)CCCCCCC=C RRWJQXJVEHEZJR-UHFFFAOYSA-N 0.000 claims description 3
- 229910000051 zinc hydride Inorganic materials 0.000 claims description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 2
- ZXDAZVCFYFCCLZ-UHFFFAOYSA-N C=CCCCC[Zn]CCCCC=C Chemical compound C=CCCCC[Zn]CCCCC=C ZXDAZVCFYFCCLZ-UHFFFAOYSA-N 0.000 claims description 2
- PHUYKZNPNVDCIC-UHFFFAOYSA-N CC[Zn]CCCCC=C Chemical compound CC[Zn]CCCCC=C PHUYKZNPNVDCIC-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- ZULTYUIALNTCSA-UHFFFAOYSA-N zinc hydride Chemical compound [ZnH2] ZULTYUIALNTCSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910012375 magnesium hydride Inorganic materials 0.000 claims 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 61
- 229920000642 polymer Polymers 0.000 description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
- 239000000047 product Substances 0.000 description 35
- 238000012546 transfer Methods 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 125000003118 aryl group Chemical group 0.000 description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 21
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 20
- 239000003446 ligand Substances 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
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 18
- 239000011651 chromium Substances 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 15
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 229910052698 phosphorus Inorganic materials 0.000 description 15
- 239000010936 titanium Substances 0.000 description 15
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 13
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 13
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 125000003368 amide group Chemical group 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 11
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 11
- 229910052727 yttrium Inorganic materials 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
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 230000000670 limiting effect Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229910052723 transition metal Inorganic materials 0.000 description 9
- 150000003624 transition metals Chemical class 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 238000001542 size-exclusion chromatography Methods 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 229910010068 TiCl2 Inorganic materials 0.000 description 7
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 7
- 125000005234 alkyl aluminium group Chemical group 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical group 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 229920002521 macromolecule Polymers 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- ZCBSOTLLNBJIEK-UHFFFAOYSA-N silane titanium Chemical compound [SiH4].[Ti] ZCBSOTLLNBJIEK-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001424 substituent group Chemical group 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
- LCCYHJHSEYKZED-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Ni] Chemical compound C1(=CC=CC=C1)C1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Ni] LCCYHJHSEYKZED-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 229910021554 Chromium(II) chloride Inorganic materials 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
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 229910052740 iodine 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
- 229920001684 low density polyethylene Polymers 0.000 description 5
- 239000004702 low-density polyethylene Substances 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- LLDZJTIZVZFNCM-UHFFFAOYSA-J 3-[18-(2-carboxyethyl)-8,13-diethyl-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid;dichlorotin(2+) Chemical compound [H+].[H+].[Cl-].[Cl-].[Sn+4].[N-]1C(C=C2C(=C(C)C(=CC=3C(=C(C)C(=C4)N=3)CC)[N-]2)CCC([O-])=O)=C(CCC([O-])=O)C(C)=C1C=C1C(C)=C(CC)C4=N1 LLDZJTIZVZFNCM-UHFFFAOYSA-J 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- 239000004305 biphenyl Chemical group 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- 150000001639 boron compounds Chemical class 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
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- WBQLICPIMKTKKK-UHFFFAOYSA-L n,n'-bis[2,6-di(propan-2-yl)phenyl]ethane-1,2-diimine;dibromonickel Chemical compound Br[Ni]Br.CC(C)C1=CC=CC(C(C)C)=C1N=CC=NC1=C(C(C)C)C=CC=C1C(C)C WBQLICPIMKTKKK-UHFFFAOYSA-L 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
- 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 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 239000012005 post-metallocene catalyst Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- SCABQASLNUQUKD-UHFFFAOYSA-N silylium Chemical compound [SiH3+] SCABQASLNUQUKD-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- VSEOIQRHQSIHRZ-UHFFFAOYSA-L titanium(4+);dichloride Chemical compound Cl[Ti+2]Cl VSEOIQRHQSIHRZ-UHFFFAOYSA-L 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 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
- 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
- 238000013022 venting Methods 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- QMBQEXOLIRBNPN-UHFFFAOYSA-L zirconocene dichloride Chemical compound [Cl-].[Cl-].[Zr+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 QMBQEXOLIRBNPN-UHFFFAOYSA-L 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
Landscapes
- 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 |
|---|---|---|---|
| EP14200125.4A EP3037438A1 (en) | 2014-12-23 | 2014-12-23 | Process for the preparation of a branched polyolefin |
| EP14200125.4 | 2014-12-23 | ||
| PCT/EP2015/081203 WO2016102690A1 (en) | 2014-12-23 | 2015-12-23 | Process for the preparation of a branched polyolefin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20170108958A KR20170108958A (ko) | 2017-09-27 |
| KR102510436B1 true KR102510436B1 (ko) | 2023-03-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020177020264A Active KR102510436B1 (ko) | 2014-12-23 | 2015-12-23 | 분지형 폴리올레핀의 제조 방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10450388B2 (enExample) |
| EP (2) | EP3037438A1 (enExample) |
| JP (1) | JP6770960B2 (enExample) |
| KR (1) | KR102510436B1 (enExample) |
| CN (1) | CN107207660B (enExample) |
| SA (1) | SA517381805B1 (enExample) |
| WO (1) | WO2016102690A1 (enExample) |
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| CN108137748B (zh) * | 2015-07-23 | 2021-05-04 | Sabic环球技术有限责任公司 | 用于制备具有一个或多个侧官能团的聚烯烃的方法 |
| 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 |
| CN107922528B (zh) * | 2015-08-31 | 2020-11-03 | 埃克森美孚化学专利公司 | 通过使用乙烯基转移剂生产的聚合物 |
| US9982067B2 (en) | 2015-09-24 | 2018-05-29 | Exxonmobil Chemical Patents Inc. | Polymerization process using pyridyldiamido compounds supported on organoaluminum treated layered silicate supports |
| 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 |
| 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 |
| US10927196B2 (en) | 2016-06-30 | 2021-02-23 | Exxonmobil Chemical Patents Inc. | Long chain branched polypropylene via polymerization with aluminum vinyl transfer agent |
| 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 |
| 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 |
| 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 |
| CN111491955A (zh) | 2017-12-22 | 2020-08-04 | Sabic环球技术有限责任公司 | 制备半结晶官能化烯烃共聚物的方法 |
| WO2019122455A1 (en) | 2017-12-22 | 2019-06-27 | Sabic Global Technologies B.V. | Process for preparation of amorphous functionalized olefin copolymer |
| KR102320012B1 (ko) * | 2018-01-12 | 2021-11-02 | 주식회사 엘지화학 | 리간드 화합물, 전이금속 화합물 및 이를 포함하는 촉매 조성물 |
| 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 |
| 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。 |
| CN118742438A (zh) * | 2022-02-23 | 2024-10-01 | 希悦尔公司 | 散装乳酪阻隔袋 |
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2015
- 2015-12-23 JP JP2017533760A patent/JP6770960B2/ja active Active
- 2015-12-23 US US15/537,926 patent/US10450388B2/en active Active
- 2015-12-23 EP EP15816486.3A patent/EP3237460A1/en active Pending
- 2015-12-23 CN CN201580075828.6A patent/CN107207660B/zh active Active
- 2015-12-23 WO PCT/EP2015/081203 patent/WO2016102690A1/en not_active Ceased
- 2015-12-23 KR KR1020177020264A patent/KR102510436B1/ko active Active
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2017
- 2017-06-22 SA SA517381805A patent/SA517381805B1/ar unknown
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| WO2016102690A1 (en) | 2016-06-30 |
| EP3237460A1 (en) | 2017-11-01 |
| US20170355786A1 (en) | 2017-12-14 |
| CN107207660B (zh) | 2020-02-14 |
| CN107207660A (zh) | 2017-09-26 |
| SA517381805B1 (ar) | 2021-01-14 |
| EP3037438A1 (en) | 2016-06-29 |
| KR20170108958A (ko) | 2017-09-27 |
| JP2018500431A (ja) | 2018-01-11 |
| JP6770960B2 (ja) | 2020-10-21 |
| US10450388B2 (en) | 2019-10-22 |
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