JP2019515997A - 混成担持メタロセン触媒及びこれを利用した加工性に優れたポリオレフィン樹脂 - Google Patents
混成担持メタロセン触媒及びこれを利用した加工性に優れたポリオレフィン樹脂 Download PDFInfo
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- JP2019515997A JP2019515997A JP2018556893A JP2018556893A JP2019515997A JP 2019515997 A JP2019515997 A JP 2019515997A JP 2018556893 A JP2018556893 A JP 2018556893A JP 2018556893 A JP2018556893 A JP 2018556893A JP 2019515997 A JP2019515997 A JP 2019515997A
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- 239000012968 metallocene catalyst Substances 0.000 title claims abstract description 74
- 229920005672 polyolefin resin Polymers 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- 238000004519 manufacturing process Methods 0.000 claims abstract description 38
- 238000009826 distribution Methods 0.000 claims abstract description 30
- 229920000098 polyolefin Polymers 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 157
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 77
- 239000000126 substance Substances 0.000 claims description 59
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 57
- -1 cationic Lewis acid Chemical class 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 33
- 150000004645 aluminates Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 26
- 229910052723 transition metal Inorganic materials 0.000 claims description 26
- 150000003624 transition metals Chemical class 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 22
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 20
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- 239000002904 solvent Substances 0.000 claims description 20
- 238000002844 melting Methods 0.000 claims description 18
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- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 14
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 14
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- 239000005977 Ethylene Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 230000000737 periodic effect Effects 0.000 claims description 13
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical compound OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 claims description 12
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 12
- GGSUCNLOZRCGPQ-UHFFFAOYSA-O diethyl(phenyl)azanium Chemical compound CC[NH+](CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-O 0.000 claims description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 10
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- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 10
- 239000004711 α-olefin Substances 0.000 claims description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 8
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 8
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 8
- 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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 239000006228 supernatant Substances 0.000 claims description 5
- HCIMXTXCDVBLOA-UHFFFAOYSA-N [4-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=C(C(F)(F)F)C=C1 HCIMXTXCDVBLOA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003426 co-catalyst Substances 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims description 4
- 238000012685 gas phase polymerization Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 4
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 claims description 4
- DQVXWCCLFKMJTQ-UHFFFAOYSA-N (4-methylphenoxy)boronic acid Chemical compound CC1=CC=C(OB(O)O)C=C1 DQVXWCCLFKMJTQ-UHFFFAOYSA-N 0.000 claims description 3
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 3
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- VOJDOIOUUAYUKD-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C(=C(C(=C1)C)C)C)C)C1C=CC2=C(C=CC=C12)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr+2](C1(C(=C(C(=C1)C)C)C)C)C1C=CC2=C(C=CC=C12)C1=CC=CC=C1 VOJDOIOUUAYUKD-UHFFFAOYSA-L 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052795 boron group element Inorganic materials 0.000 claims description 3
- 125000005626 carbonium group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 claims description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 3
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 claims description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims description 3
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 claims description 2
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- DNFMTFCPAWFGPK-UHFFFAOYSA-L [Cl-].[Cl-].CC1=C2C=CC(C2=CC=C1)C1(C=CC=C1)[Zr+2] Chemical compound [Cl-].[Cl-].CC1=C2C=CC(C2=CC=C1)C1(C=CC=C1)[Zr+2] DNFMTFCPAWFGPK-UHFFFAOYSA-L 0.000 claims description 2
- XFNJQHPCDTWSNM-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH](C)[Zr+2](C1C(=CC2=C(C=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C1(C(=C(C(=C1)C)C)C)C Chemical compound [Cl-].[Cl-].C[SiH](C)[Zr+2](C1C(=CC2=C(C=CC=C12)C1=CC=C(C=C1)C(C)(C)C)C)C1(C(=C(C(=C1)C)C)C)C XFNJQHPCDTWSNM-UHFFFAOYSA-L 0.000 claims description 2
- MYBJXSAXGLILJD-UHFFFAOYSA-N diethyl(methyl)alumane Chemical compound CC[Al](C)CC MYBJXSAXGLILJD-UHFFFAOYSA-N 0.000 claims description 2
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 claims description 2
- MWNKMBHGMZHEMM-UHFFFAOYSA-N dimethylalumanylium;ethanolate Chemical compound CCO[Al](C)C MWNKMBHGMZHEMM-UHFFFAOYSA-N 0.000 claims description 2
- SHGOGDWTZKFNSC-UHFFFAOYSA-N ethyl(dimethyl)alumane Chemical compound CC[Al](C)C SHGOGDWTZKFNSC-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- BQBCXNQILNPAPX-UHFFFAOYSA-N methoxy(dimethyl)alumane Chemical compound [O-]C.C[Al+]C BQBCXNQILNPAPX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 claims description 2
- PYLGJXLKFZZEBJ-UHFFFAOYSA-N tricyclopentylalumane Chemical compound C1CCCC1[Al](C1CCCC1)C1CCCC1 PYLGJXLKFZZEBJ-UHFFFAOYSA-N 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 claims description 2
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 claims description 2
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- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 claims description 2
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- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 claims description 2
- ZMPKTELQGVLZTD-UHFFFAOYSA-N tripropylborane Chemical compound CCCB(CCC)CCC ZMPKTELQGVLZTD-UHFFFAOYSA-N 0.000 claims description 2
- WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
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- NZDLIIBVQQCHBI-UHFFFAOYSA-L Cl[Zr]Cl.CC1=C[CH]C=C1 Chemical compound Cl[Zr]Cl.CC1=C[CH]C=C1 NZDLIIBVQQCHBI-UHFFFAOYSA-L 0.000 claims 1
- DZETZMSAJDMAKS-UHFFFAOYSA-L Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 Chemical compound Cl[Zr]Cl.[CH]1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 DZETZMSAJDMAKS-UHFFFAOYSA-L 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims 1
- GXZJUGGTMPCASB-UHFFFAOYSA-L [Cl-].[Cl-].C1(C=CC2=CC=CC=C12)C1(C(=C(C(=C1C)C)C)C)[Zr+2] Chemical compound [Cl-].[Cl-].C1(C=CC2=CC=CC=C12)C1(C(=C(C(=C1C)C)C)C)[Zr+2] GXZJUGGTMPCASB-UHFFFAOYSA-L 0.000 claims 1
- NSDVYNWCHDHIEY-UHFFFAOYSA-L [Cl-].[Cl-].CC=1C(C2=C3C(=CC=C2C=1)C=CC=C3)C1(C=CC=C1)[Zr+2] Chemical compound [Cl-].[Cl-].CC=1C(C2=C3C(=CC=C2C=1)C=CC=C3)C1(C=CC=C1)[Zr+2] NSDVYNWCHDHIEY-UHFFFAOYSA-L 0.000 claims 1
- 239000004411 aluminium Substances 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 claims 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
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- 229910007926 ZrCl Inorganic materials 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 20
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- 230000000704 physical effect Effects 0.000 description 11
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- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 8
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- 238000012545 processing Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- 150000003623 transition metal compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- RKICYRXUSNYDKO-UHFFFAOYSA-N 1h-indene;lithium Chemical compound [Li].C1=CC=C2CC=CC2=C1 RKICYRXUSNYDKO-UHFFFAOYSA-N 0.000 description 3
- WOMLTCOPRFPVBR-UHFFFAOYSA-N 7-phenyl-1h-indene Chemical compound C=12CC=CC2=CC=CC=1C1=CC=CC=C1 WOMLTCOPRFPVBR-UHFFFAOYSA-N 0.000 description 3
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- 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
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- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
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- C08F4/65925—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 non-bridged
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Abstract
Description
([4,5-benzoindenyl(tetramethylcyclopentadienyl)] ZrCl2)であり得るが、これに限定されるものではない。
また、上記第2メタロセン化合物は、例えば、ジメチルシリル{テトラメチルシクロペンタジエニル} {2 - メチル - 4 - (4 -タート- ブチルフェニル)インデニル} ジルコニウムジクロライド(dimethylsilyl {tetramethylcyclopentadienyl} {2-methyl-4-(4-tert-buthylphenyl)indeny l} ZrCl2)、ジメチルシリル(テトラメチルシクロペンタジエニル)(2-メチル - 4-フェニルインデニル)ジルコニウムジクロライド(dimethylsilyl(tetracyclopentadienyl)(2-methyl-4-phenylindenyl)ZrCl2)、ジメチルシリル(テトラメチルシクロペンタジエニル)(4-フェニルインデニル)ジルコニウムジクロライド(dimethylsilyl(tetramethylcyclopentadienyl )(4-phenylindenyl)ZrCl2)であり得るが、これらに制限されるものではない。
NaH(60wt%in mineral oil、4.42g、1.1eq)をTHF(80ml)に分散させた溶液にdiethyl 2-methylmalonate(17.5g、1eq)を-30℃でゆっくり添加した後、1時間攪拌する。 THF(10ml)に溶かした2-Bromobenzyl bromide(26.36g、1.05eq)を0℃で1時間かけて 添加し、12時間還流攪拌する。濾過し、溶媒を乾燥させて黄色のオイルDiethyl 2-(2-bromobenzyl)-2-methylmalonate 34g(99%)を得る。
第1メタロセン化合物の製造例2の化合物0.031 g、第2メタロセン化合物の製造例 5化合物0.070 gを使用したことを除いては、製造例9と同じ方法で製造した。
Claims (18)
- 下記化学式1で表される少なくとも1種以上の第1メタロセン化合物、下記化学式2で表される少なくとも1種以上の第2のメタロセン化合物、下記化学式3乃至化学式6で表される化合物群から選択された少なくとも1種以上の助触媒化合物と担体を含み、前記担体は、シリカを含み、平均粒度が10乃至250ミクロンであり、微細気孔容積は、0.1乃至10 cc / gであり、比表面積は、1乃至1000 m2 / gであり、ヒドロキシ基濃度は、0.1乃至5 mmol / gであることを特徴とする混成担持メタロセン触媒:
- 第1項において、前記第1メタロセン化合物は、[4-メチルインデニル(シクロペンタジエニル)] ジルコニウムジクロライド、[インデニル(テトラメチルシクロペンタジエニル)]ジルコニウムジクロライド、[2-メチルインデニル(テトラメチルシクロペンタジエニル)]ジルコニウムジクロライド、[2-メチルベンゾインデニル(シクロペンタジエニル)]ジルコニウムジクロライド及び[4,5-ベンゾインデニル(テトラメチルシクロペンタジエニル)]ジルコニウムジクロリドからなる群から選択された少なくともいずれか1種以上を含むことを特徴とする混成担持メタロセン触媒。
- 第1項において、前記第2メタロセン化合物は、ジメチルシリル{テトラメチルシクロペンタジエニル} {2-メチル-4-(4-タート - ブチルフェニル)インデニル}ジルコニウムジクロライド、ジメチルシリル(テトラメチルシクロペンタジエニル)(2-メチル-4-フェニルインデニル)ジルコニウムジクロライド及びジメチルシリル(テトラメチルシクロペンタジエニル)(4-フェニルインデニル)ジルコニウムジクロライドからなる群から選択された少なくともいずれか一つ以上を含むことを特徴とする混成担持メタロセン触媒。
- 第1項において、メチルアルミノキサン、エチルアルミノキサン、イソブチルアルミノキサン、及びブチルアルミノキサンからなる群から選択された少なくともいずれか一つ以上を含むことを特徴とする混成担持メタロセン触媒。
- 第1項において、前記化学式4で表される助触媒化合物は、トリメチルアルミニウム、トリエチルアルミニウム、トリイソブチルアルミニウム、トリプロピルアルミニウム、トリブチルアルミニウム、ジメチルクロロアルミニウム、トリイソプロピルアルミニウム、トリシクロペンチルアルミニウム、トリペンチルアルミニウム、トリイソペンチルアルミニウム、トリヘキシルアルミニウム、トリオクチルアルミニウム、エチルジメチルアルミニウム、メチルジエチルアルミニウム、トリフェニルアルミニウム、トリ-p-トリルアルミニウム、ジメチルアルミニウムメトキシド、ジメチルアルミニウムエトキシド、トリメチルボロン、トリエチルボロン、トリイソブチルボロン、トリプロピルボロン、トリブチルボロン及びトリ ペンタフルオロフェニルボロン群から選択された少なくともいずれか一つ以上を含むことを特徴とする混成担持メタロセン触媒。
- 第1項において、前記化学式5又は6で表される助触媒化合物は、メチルジオクタテシルアンモニウムテトラキス(ペンタフルオロフェニル)ボレート、トリメチルアンモニウムテトラキス(フェニル)ボレート、トリエチルアンモニウムテトラキス(フェニル)ボレート、トリプロピルアンモニウムテトラキス(フェニル)ボレート、トリブチルアンモニウムテトラキス(フェニル)ボレート、トリメチルアンモニウムテトラキス(p-トリル)ボレート、トリプロピルアンモニウムテトラキス(p-トリル)ボレート、トリメチルアンモニウムテトラキス(o、p-ジメチルフェニル)ボレート、トリエチルアンモニウムテトララキス(o、p-ジメチルフェニル)ボレート、トリメチルアンモニウムテトラキス(p-トリフルオロメチルフェニル)ボレート、トリブチルアンモニウムテトラキス(p-トリフルオロメチルフェニル)ボレート、 ツリーブチルアンモニウムテトラキス(ペンタフルオロフェニル)ボレート、ジエチルアンモニウムテトラキス(ペンタフルオロフェニル)ボレート、トリフェニルホスホニウムテトラキス(フェニル)ボレート、トリメチルホスホニウムテトラキス(フェニル)ボレート、N、 N-ジエチルアニリニウムテトラキス(フェニル)ボレート、N、N-ジメチルアニリニウムテトラキス(ペンタフルオロフェニル)ボレート、N、N-ジエチルアニリニウムテトラキス(ペンタフルオロフェニル)ボレート、トリフェニルカーボニウムテトラキス(p-トリフルオロメチルフェニル)ボレート、トリフェニルカーボニウムテトラキス(ペンタフルオロフェニル)ボレート、トリメチルアンモニウムテトラキス(フェニル)アルミネート、トリエチルアンモニウムテトラキス(フェニル)アルミネート、トリプロピルアンモニウムテトラキス(フェニル)アルミネート、トリブチルアンモニウムテトラキス(フェニル)アルミネート、トリメチルアンモニウムテトラキス(p-トリル)アルミネート、トリプロピルアンモニウムテトラキス(p-トリル)アルミネート、トリエチルアンモニウムテトラキス(o、p-ジメチルフェニル)アルミネート、トリブチルアンモニウムテトラキス(p-トリフルオロメチルフェニル)アルミネート、トリメチルアンモニウムテトラキス(p-トリフルオロメチルフェニル)アルミネート、トリブチルアンモニウムテトラキス(ペンタフルオロフェニル)アルミネート、N、N-ジエチルアニリニウムテトラキス(フェニル)アルミネート、N、N-ジエチルアニリニウムテトラキス(フェニル)アルミネート、N、N-ジエチルアニリニウムテトラキス(ペンタフルオロフェニル)アルミネート、ジエチルアンモニウムテトラキス(ペンタフルオロフェニル)アルルミネート、トリフェニルホスホニウムテトラキス(フェニル)アルミネート、トリメチルホスホニウムテトラキス(フェニル)アルミネート、トリエチルアンモニウムテトラキス(フェニル)アルミネート及びトリブチルアンモニウムテトラキス(フェニル)アルミネートから成る群から選択された少なくともいずれか一つ以上を含むことを特徴とする混成担持メタロセン触媒。
- 第1項において、前記第1メタロセン化合物の遷移金属と前記第2メタロセン化合物の転移金属の総質量と前記担体の質量比は、1:10乃至1:1000であり、前記第1メタロセン化合物の前記第2のメタロセン化合物の質量比は1:100乃至100:1であることを特徴とする混成担持メタロセン触媒。
- 第1項において、前記化学式3及び4で表される助触媒化合物の前記担体の質量比は1:100乃至100:1であり、前記化学式5及び6に表される助触媒化合物の前記担体の質量比は、1:20乃至20:1であることを特徴とする混成担持メタロセン触媒。
- 第1項乃至第10項のいずれか1項の規定による混成担持メタロセン触媒の存在下にオレフィン単量体が重合によって製造され、 密度が、0.910乃至0.960 g / cm3であり、分子量分布は、3乃至5の単峰性分子量分布を有し、MI2(溶融指数)は、0.1乃至100 g / 10minであり、MI21 / MI2(溶融流動性)は、20乃至40であることを特徴とする加工性に優れたポリオレフィン樹脂。
- 第11項において、前記ポリオレフィン樹脂は、エチレンホモ重合体又はエチレン - α-オレフィン共重合体を含むことを特徴とする加工性に優れたポリオレフィン樹脂。
- 第11項において、前記オレフィン単量体は、プロピレン、1-ブテン、1-ペンテン、3-メチル-1-ブテン、1-ヘキセン、4-メチル-1-ペンテン、3-メチル-1-ペンテン、1-ヘプテン、1-オクテン、及び1-デセンからなる群から選択された少なくとも1種以上を含むことを特徴とする加工性に優れたポリオレフィン樹脂。
- 下記化学式1で表される少なくとも1種以上の第1メタロセン化合物、下記の化学式2で表される少なくとも1種以上の第2のメタロセン化合物及び少なくとも1種以上の助触媒化合物を準備する段階、それぞれ用意された前記第1メタロセン化合物、第2メタロセン化合物と、前記助触媒化合物を0乃至100℃で5分乃至4時間を攪拌して触媒混合物を製造する段階、担体及び溶媒が存在する反応器に、前記触媒の混合物を添加して0乃至10 0℃で3分乃至48時間攪拌して、第1項から第10項のいずれか一項の規定による混成担持メタロセン触媒の組成物を製造する段階を含み、前記第1メタロセン化合物及び第2メタロセン化合物は、それぞれ独立して中心金属の濃度が1 * 10-5乃至9* 10-5 mol / lであることを特徴とする混成担持メタロセン触媒の製造方法。
R1乃至R5が結合しているシクロペンタジエンとR6乃至R10が結合しているシクロペンタジエンは、 互に同一構造または異なる構造であり、各シクロペンタジエンは、接続されていないため、非架橋構造の化合物を形成し、
- 第14項において、 前記助触媒化合物は、下記化学式3乃至化学式6で表される化合物群から選択された少なくとも1種以上を含むことを特徴とする混成担持メタロセン触媒の製造方法。
- 第14項において、前記担持された触媒組成物を沈殿反応させて上澄み液を分離する段階、分離された上澄み液を除去し、残った触媒組成物沈殿を溶媒で洗浄する段階、洗浄された触媒組成物沈殿を20乃至200℃で1時間乃至48時間真空乾燥する段階をさらに含むことを特徴とする混成担持メタロセン触媒の製造方法。
- オートクレーブ反応器又は気相重合反応器に、第14項の規定による混成担持メタロセン触媒の製造方法で製造された混成担持メタロセン触媒とオレフィン単量体を投入して、温度は0乃至120℃、圧力は1乃至150バーの環境でポリオレフィンに重合する段階を含むことを特徴とする加工性の優れたポリオレフィン樹脂製造方法。
- 第17項において、前記オレフィン単量体は、プロピレン、1-ブテン、1-ペンテン、3-メチル-1-ブテン、1-ヘキセン、4-メチル-1-ペンテン、3-メチル-1-ペンテン、1-ヘプテン、1-オクテン、及び1-デセンからなる群から選択された少なくともいずれか一つ以上を含むことを特徴とするポリオレフィン樹脂製造方法。
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KR101725004B1 (ko) | 2017-04-18 |
US20190263942A1 (en) | 2019-08-29 |
EP3450467A1 (en) | 2019-03-06 |
JP6804559B2 (ja) | 2020-12-23 |
CN109415450A (zh) | 2019-03-01 |
WO2017188602A1 (ko) | 2017-11-02 |
EP3450467A4 (en) | 2020-01-15 |
US11248067B2 (en) | 2022-02-15 |
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