JP5023522B2 - 有機遷移金属化合物、それを用いたオレフィン重合用触媒およびポリオレフィンの製造方法 - Google Patents
有機遷移金属化合物、それを用いたオレフィン重合用触媒およびポリオレフィンの製造方法 Download PDFInfo
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- JP5023522B2 JP5023522B2 JP2006071437A JP2006071437A JP5023522B2 JP 5023522 B2 JP5023522 B2 JP 5023522B2 JP 2006071437 A JP2006071437 A JP 2006071437A JP 2006071437 A JP2006071437 A JP 2006071437A JP 5023522 B2 JP5023522 B2 JP 5023522B2
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- 229920000098 polyolefin Polymers 0.000 title claims abstract description 52
- 239000003054 catalyst Substances 0.000 title claims abstract description 39
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 28
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 238000006116 polymerization reaction Methods 0.000 title claims description 45
- 150000003623 transition metal compounds Chemical class 0.000 title claims description 37
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 12
- -1 oxy compound Chemical class 0.000 claims description 213
- 150000002430 hydrocarbons Chemical group 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000002734 clay mineral Substances 0.000 claims description 21
- 230000004913 activation Effects 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000002894 organic compounds Chemical class 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002879 Lewis base Substances 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000007527 lewis bases Chemical class 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000003426 co-catalyst Substances 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229910052798 chalcogen Inorganic materials 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052696 pnictogen Inorganic materials 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000000470 constituent Substances 0.000 abstract description 4
- 230000003213 activating effect Effects 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 150000002899 organoaluminium compounds Chemical class 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 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 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 229920002554 vinyl polymer Polymers 0.000 description 16
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 15
- 239000004698 Polyethylene Substances 0.000 description 14
- 229920000573 polyethylene Polymers 0.000 description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 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 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000004645 aluminates Chemical class 0.000 description 10
- 229910052809 inorganic oxide Inorganic materials 0.000 description 10
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 9
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GWLSZDSYQDPPGB-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] GWLSZDSYQDPPGB-UHFFFAOYSA-L 0.000 description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 6
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 5
- 125000005917 3-methylpentyl group Chemical group 0.000 description 5
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 0 CC1=C(*)C(*)=C(*)C1* Chemical compound CC1=C(*)C(*)=C(*)C1* 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XJONFIGVOQMBIP-UHFFFAOYSA-L Cl[Zr](Cl)C1C=CC=C1 Chemical compound Cl[Zr](Cl)C1C=CC=C1 XJONFIGVOQMBIP-UHFFFAOYSA-L 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- 239000012968 metallocene catalyst Substances 0.000 description 4
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910000271 hectorite Inorganic materials 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000723368 Conium Species 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- BZCATATVNHLONE-UHFFFAOYSA-L [Cl-].[Cl-].C[SiH]=[Zr+2](C1C=CC=C1)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C[SiH]=[Zr+2](C1C=CC=C1)C1C=CC=C1 BZCATATVNHLONE-UHFFFAOYSA-L 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- MMCPOSDMTGQNKG-UJZMCJRSSA-N aniline;hydrochloride Chemical compound Cl.N[14C]1=[14CH][14CH]=[14CH][14CH]=[14CH]1 MMCPOSDMTGQNKG-UJZMCJRSSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical class [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 2
- RMKNCYHVESPYFD-UHFFFAOYSA-N decan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCC[NH3+] RMKNCYHVESPYFD-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- PFKRTWCFCOUBHS-UHFFFAOYSA-N dimethyl(octadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH+](C)C PFKRTWCFCOUBHS-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-O dimethyloxidanium Chemical compound C[OH+]C LCGLNKUTAGEVQW-UHFFFAOYSA-O 0.000 description 2
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000012685 gas phase polymerization Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- SRUKOJDGOUUFRB-UHFFFAOYSA-N heptylazanium;chloride Chemical compound Cl.CCCCCCCN SRUKOJDGOUUFRB-UHFFFAOYSA-N 0.000 description 2
- ZWGTVKDEOPDFGW-UHFFFAOYSA-N hexadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[NH3+] ZWGTVKDEOPDFGW-UHFFFAOYSA-N 0.000 description 2
- XKDUZXVNQOZCFC-UHFFFAOYSA-N hexan-1-amine;hydron;chloride Chemical compound Cl.CCCCCCN XKDUZXVNQOZCFC-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 description 1
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- UCKITPBQPGXDHV-UHFFFAOYSA-N 7-methylocta-1,6-diene Chemical compound CC(C)=CCCCC=C UCKITPBQPGXDHV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- RCJWAJVCYGCCRO-UHFFFAOYSA-N 9h-fluoren-2-amine;hydrochloride Chemical compound Cl.C1=CC=C2C3=CC=C(N)C=C3CC2=C1 RCJWAJVCYGCCRO-UHFFFAOYSA-N 0.000 description 1
- QSHDQOIPIUYASJ-UHFFFAOYSA-N 9h-fluoren-3-amine;hydrochloride Chemical compound Cl.C1=CC=C2C3=CC(N)=CC=C3CC2=C1 QSHDQOIPIUYASJ-UHFFFAOYSA-N 0.000 description 1
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- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- CYRZCJKJBPNTEN-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] CYRZCJKJBPNTEN-UHFFFAOYSA-L 0.000 description 1
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- KIBZLYZADIDXHT-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] KIBZLYZADIDXHT-UHFFFAOYSA-L 0.000 description 1
- DPJHEBCVMZUITG-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] DPJHEBCVMZUITG-UHFFFAOYSA-L 0.000 description 1
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- YSCXNHRLPBJEAS-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] YSCXNHRLPBJEAS-UHFFFAOYSA-L 0.000 description 1
- FGFLHJLVJJBPMO-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr](C1C=CC=C1)C1C=CC=C1 Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr](C1C=CC=C1)C1C=CC=C1 FGFLHJLVJJBPMO-UHFFFAOYSA-N 0.000 description 1
- GLLJHZUYQXNROK-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] GLLJHZUYQXNROK-UHFFFAOYSA-L 0.000 description 1
- NGAKMRPIGWHLJL-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] NGAKMRPIGWHLJL-UHFFFAOYSA-L 0.000 description 1
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- FTBULAFTAZPWQC-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] FTBULAFTAZPWQC-UHFFFAOYSA-L 0.000 description 1
- JAJGWGFBGVNZMG-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCC[SiH]=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC[SiH]=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] JAJGWGFBGVNZMG-UHFFFAOYSA-L 0.000 description 1
- RWQPCATWUNZTMP-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] RWQPCATWUNZTMP-UHFFFAOYSA-L 0.000 description 1
- DSLZLHZYPLAISD-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] DSLZLHZYPLAISD-UHFFFAOYSA-L 0.000 description 1
- PMZKOYOBPPSYMC-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCC[Si](CCCCCCCCCCCCCCCCCCCCC)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] PMZKOYOBPPSYMC-UHFFFAOYSA-L 0.000 description 1
- BAJBOYFXNHJDPD-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCC[Si](C(C)C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCC[Si](C(C)C)=[Zr+2](C1C=CC=C1)C1C=CC=C1.[Cl-].[Cl-] BAJBOYFXNHJDPD-UHFFFAOYSA-L 0.000 description 1
- IUHGBHAJYPCGDB-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C(C=C1C2=CC=CC=C2)(C(C2=CC=CC=C2)=C1C1=CC=CC=C1)C1=CC=CC=C1)C(C=C1C2=CC=CC=C2)(C(C2=CC=CC=C2)=C1C1=CC=CC=C1)C1=CC=CC=C1.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C(C=C1C2=CC=CC=C2)(C(C2=CC=CC=C2)=C1C1=CC=CC=C1)C1=CC=CC=C1)C(C=C1C2=CC=CC=C2)(C(C2=CC=CC=C2)=C1C1=CC=CC=C1)C1=CC=CC=C1.[Cl-].[Cl-] IUHGBHAJYPCGDB-UHFFFAOYSA-L 0.000 description 1
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- DTDXOJRZALNCNX-UHFFFAOYSA-L CCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1=CC=CC2=C1CC1=CC=CC=C21)C1=CC=CC2=C1CC1=CC=CC=C21.[Cl-].[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCC[Si](C)=[Zr+2](C1=CC=CC2=C1CC1=CC=CC=C21)C1=CC=CC2=C1CC1=CC=CC=C21.[Cl-].[Cl-] DTDXOJRZALNCNX-UHFFFAOYSA-L 0.000 description 1
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- 238000011088 calibration curve Methods 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ASWRLCJWTCTHCL-UHFFFAOYSA-N cyclohexyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)C1CCCCC1 ASWRLCJWTCTHCL-UHFFFAOYSA-N 0.000 description 1
- KNGAVTDYYJIGHA-UHFFFAOYSA-N cyclohexyl(methyl)azanium;chloride Chemical compound [Cl-].C[NH2+]C1CCCCC1 KNGAVTDYYJIGHA-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- BDVSONRJQWXMHG-UHFFFAOYSA-N cyclopentylazanium;chloride Chemical compound Cl.NC1CCCC1 BDVSONRJQWXMHG-UHFFFAOYSA-N 0.000 description 1
- OPFLTAIGKDNPHR-UHFFFAOYSA-N di(cyclopenta-1,3-dien-1-yl)-docosyl-methylsilane Chemical compound CCCCCCCCCCCCCCCCCCCCCC[Si](C)(C1=CC=CC1)C2=CC=CC2 OPFLTAIGKDNPHR-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- XJNNFXAJDSSMBZ-UHFFFAOYSA-N dichloro-docosyl-methylsilane Chemical compound CCCCCCCCCCCCCCCCCCCCCC[Si](C)(Cl)Cl XJNNFXAJDSSMBZ-UHFFFAOYSA-N 0.000 description 1
- 229910001649 dickite Inorganic materials 0.000 description 1
- JQRYDCPSJSWQGZ-UHFFFAOYSA-N didecylazanium;chloride Chemical compound Cl.CCCCCCCCCCNCCCCCCCCCC JQRYDCPSJSWQGZ-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- DETPPCCUWRJLKU-UHFFFAOYSA-N diethylsulfanium bromide Chemical compound [Br-].CC[SH+]CC DETPPCCUWRJLKU-UHFFFAOYSA-N 0.000 description 1
- ZWTUDXRRWXKNAV-UHFFFAOYSA-N diethylsulfanium fluoride Chemical compound [F-].CC[SH+]CC ZWTUDXRRWXKNAV-UHFFFAOYSA-N 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 1
- VXKJCYOFOIIBHH-UHFFFAOYSA-N dimethyl(tetradecyl)azanium;chloride Chemical compound Cl.CCCCCCCCCCCCCCN(C)C VXKJCYOFOIIBHH-UHFFFAOYSA-N 0.000 description 1
- KVLJKZLFLIJDCM-UHFFFAOYSA-N dimethyl-(2-methylphenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1C KVLJKZLFLIJDCM-UHFFFAOYSA-N 0.000 description 1
- MSWANEMFQROHCW-UHFFFAOYSA-N dimethyl-(4-methylphenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=C(C)C=C1 MSWANEMFQROHCW-UHFFFAOYSA-N 0.000 description 1
- TUTOKIOKAWTABR-UHFFFAOYSA-N dimethylalumane Chemical compound C[AlH]C TUTOKIOKAWTABR-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- GVXYYRZMASRTPS-UHFFFAOYSA-N dimethylsulfanium chloride Chemical compound [Cl-].C[SH+]C GVXYYRZMASRTPS-UHFFFAOYSA-N 0.000 description 1
- TWFQJFPTTMIETC-UHFFFAOYSA-N dodecan-1-amine;hydron;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH3+] TWFQJFPTTMIETC-UHFFFAOYSA-N 0.000 description 1
- PGQAXGHQYGXVDC-UHFFFAOYSA-N dodecyl(dimethyl)azanium;chloride Chemical compound Cl.CCCCCCCCCCCCN(C)C PGQAXGHQYGXVDC-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002363 hafnium compounds Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical class Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- ADALIFAVBBCNGP-UHFFFAOYSA-N heptadecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCC[NH3+] ADALIFAVBBCNGP-UHFFFAOYSA-N 0.000 description 1
- JOPQZCZKKFHRNT-UHFFFAOYSA-N heptan-2-amine;hydrochloride Chemical compound Cl.CCCCCC(C)N JOPQZCZKKFHRNT-UHFFFAOYSA-N 0.000 description 1
- AZNMTKYRAKUZOC-UHFFFAOYSA-N heptan-3-ylazanium;chloride Chemical compound Cl.CCCCC(N)CC AZNMTKYRAKUZOC-UHFFFAOYSA-N 0.000 description 1
- URXQDXAVUYKSCK-UHFFFAOYSA-N hexadecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[NH+](C)C URXQDXAVUYKSCK-UHFFFAOYSA-N 0.000 description 1
- DZZKHRZZALRSLB-UHFFFAOYSA-N hexylaluminum Chemical compound CCCCCC[Al] DZZKHRZZALRSLB-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- GCZDACZURJFILX-UHFFFAOYSA-N hydron;2,2,6,6-tetramethylpiperidine;chloride Chemical compound Cl.CC1(C)CCCC(C)(C)N1 GCZDACZURJFILX-UHFFFAOYSA-N 0.000 description 1
- DLDIDQIZPBIVNQ-UHFFFAOYSA-N hydron;2-methylpropan-2-amine;chloride Chemical compound Cl.CC(C)(C)N DLDIDQIZPBIVNQ-UHFFFAOYSA-N 0.000 description 1
- VQYJLACQFYZHCO-UHFFFAOYSA-N hydron;4-methoxyaniline;chloride Chemical compound [Cl-].COC1=CC=C([NH3+])C=C1 VQYJLACQFYZHCO-UHFFFAOYSA-N 0.000 description 1
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
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- DNMZJIGSDQVGSA-UHFFFAOYSA-N methoxymethane;hydrochloride Chemical compound Cl.COC DNMZJIGSDQVGSA-UHFFFAOYSA-N 0.000 description 1
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- SQBLJTGBJPNTCF-UHFFFAOYSA-N methylsulfanylmethane;hydrofluoride Chemical compound F.CSC SQBLJTGBJPNTCF-UHFFFAOYSA-N 0.000 description 1
- VLYLVPWRADZEDL-UHFFFAOYSA-N methylsulfanylmethane;hydroiodide Chemical compound [I-].C[SH+]C VLYLVPWRADZEDL-UHFFFAOYSA-N 0.000 description 1
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- 239000000178 monomer Substances 0.000 description 1
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- 238000000465 moulding Methods 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- BFDDMZKDAIOGFP-UHFFFAOYSA-N n,n-dimethyloctan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCC[NH+](C)C BFDDMZKDAIOGFP-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- BXOXWGNIYYQESH-UHFFFAOYSA-N n-methylhexan-1-amine;hydrochloride Chemical compound Cl.CCCCCCNC BXOXWGNIYYQESH-UHFFFAOYSA-N 0.000 description 1
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- DCEXISJPIKBSAD-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine;hydrochloride Chemical compound Cl.CC(C)NC1CCCCC1 DCEXISJPIKBSAD-UHFFFAOYSA-N 0.000 description 1
- SISUCHKDQBFGEI-UHFFFAOYSA-N n-tert-butylcyclohexanamine;hydrochloride Chemical compound Cl.CC(C)(C)NC1CCCCC1 SISUCHKDQBFGEI-UHFFFAOYSA-N 0.000 description 1
- FOKKJVHTXPJHEN-UHFFFAOYSA-N naphthalen-1-ylazanium;chloride Chemical compound Cl.C1=CC=C2C(N)=CC=CC2=C1 FOKKJVHTXPJHEN-UHFFFAOYSA-N 0.000 description 1
- QKGIPGSKJBOHSL-UHFFFAOYSA-N naphthalen-2-amine;hydrochloride Chemical compound [Cl-].C1=CC=CC2=CC([NH3+])=CC=C21 QKGIPGSKJBOHSL-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- AXTDZHQPXGKMIB-UHFFFAOYSA-N octan-2-amine;hydrochloride Chemical compound [Cl-].CCCCCCC(C)[NH3+] AXTDZHQPXGKMIB-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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
- 239000003960 organic solvent Substances 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- SMPAPEKFGLKOIC-UHFFFAOYSA-N oxolane;hydrochloride Chemical compound Cl.C1CCOC1 SMPAPEKFGLKOIC-UHFFFAOYSA-N 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JRCNNGRDCFZVPA-UHFFFAOYSA-N pentadecylazanium;chloride Chemical compound Cl.CCCCCCCCCCCCCCCN JRCNNGRDCFZVPA-UHFFFAOYSA-N 0.000 description 1
- FZFZFCIODKYFEV-UHFFFAOYSA-N pentan-1-amine;hydrochloride Chemical compound Cl.CCCCCN FZFZFCIODKYFEV-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- UWAAFUVSRWSVSK-UHFFFAOYSA-N phenoxybenzene;hydrochloride Chemical compound Cl.C=1C=CC=CC=1OC1=CC=CC=C1 UWAAFUVSRWSVSK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001954 samarium oxide Inorganic materials 0.000 description 1
- 229940075630 samarium oxide Drugs 0.000 description 1
- FKTOIHSPIPYAPE-UHFFFAOYSA-N samarium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Sm+3].[Sm+3] FKTOIHSPIPYAPE-UHFFFAOYSA-N 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 229910000269 smectite group Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
- 229910003452 thorium oxide Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
- XDRDMVYFQARLNH-UHFFFAOYSA-N tridecan-1-amine;hydrochloride Chemical compound Cl.CCCCCCCCCCCCCN XDRDMVYFQARLNH-UHFFFAOYSA-N 0.000 description 1
- GPQCSCQDQNXQSV-UHFFFAOYSA-N tridodecylazanium;chloride Chemical compound Cl.CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC GPQCSCQDQNXQSV-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- XOKPOPWYLRKXEA-UHFFFAOYSA-N trihexylazanium;chloride Chemical compound Cl.CCCCCCN(CCCCCC)CCCCCC XOKPOPWYLRKXEA-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- GZQXROYFQLBBPK-UHFFFAOYSA-N tris(2,3,5,6-tetrafluorophenyl)borane Chemical compound FC1=CC(F)=C(F)C(B(C=2C(=C(F)C=C(F)C=2F)F)C=2C(=C(F)C=C(F)C=2F)F)=C1F GZQXROYFQLBBPK-UHFFFAOYSA-N 0.000 description 1
- BIPFTJPEICZJRX-UHFFFAOYSA-N tris(2-methylphenyl)phosphane;hydrochloride Chemical compound Cl.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C BIPFTJPEICZJRX-UHFFFAOYSA-N 0.000 description 1
- SOZKFVWXFXBGSR-UHFFFAOYSA-N tris(3,4,5-trifluorophenyl)alumane Chemical compound FC1=C(F)C(F)=CC([Al](C=2C=C(F)C(F)=C(F)C=2)C=2C=C(F)C(F)=C(F)C=2)=C1 SOZKFVWXFXBGSR-UHFFFAOYSA-N 0.000 description 1
- LKNHGIFPRLUGEG-UHFFFAOYSA-N tris(3,4,5-trifluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC(B(C=2C=C(F)C(F)=C(F)C=2)C=2C=C(F)C(F)=C(F)C=2)=C1 LKNHGIFPRLUGEG-UHFFFAOYSA-N 0.000 description 1
- MILOMCIWZLGIEE-UHFFFAOYSA-N tris(4-methylphenyl)phosphane;hydrochloride Chemical compound [Cl-].C1=CC(C)=CC=C1[PH+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MILOMCIWZLGIEE-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
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
ジヘンイコシルシランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ドコシル)(ヘンイコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(トリコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(テトラコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ペンタコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ヘキサコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ヘプタコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(オクタコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ノナコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(トリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ヘントリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ドトリアコンチル)(ヘンイコシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(トリトリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(テトラトリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ペンタトリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ヘキサトリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ヘプタトリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(オクタトリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(ノナトリアコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(テトラコンチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(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、(ヘンイコシル)(メチル)シランジイルビス(2,4‐ジ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、(ヘンイコシル)(メチル)シランジイルビス(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、(ヘンイコシル)(メチル)シランジイルビス(テトラフェニルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(テトラヒドロインデニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(オクタヒドロフルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(インデニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(2−メチルインデニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(フルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(2,7−ジメチルフルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(2,7−ジ−tert−ブチルフルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(トリメチルシリルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(トリエチルシリルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(フェニルジメチルシリルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイルビス(ジフェニルメチルシリルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(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、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(2,4‐ジメチル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、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(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、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(テトラフェニルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(テトラヒドロインデニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(オクタヒドロフルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(インデニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(2−メチルインデニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(フルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(2,7−ジメチルフルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(2,7−ジ−tert−ブチルフルオレニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(トリメチルシリルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(トリエチルシリルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(フェニルジメチルシリルシクロペンタジエニル)ジルコニウムジクロライド、(ヘンイコシル)(メチル)シランジイル(シクロペンタジエニル)(ジフェニルメチルシリルシクロペンタジエニル)ジルコニウムジクロライド等のジクロロ体および、上記遷移金属化合物の金属に結合しているクロロ原子を炭化水素基、アルコキシ基等に変えた有機遷移金属化合物を例示することができる。また、上記遷移金属化合物と同等の構造を有し、中心金属がチタン原子に置き換わったチタニウム化合物、ハフニウム原子に置き換わったハフニウム化合物を例示することができる。ただし、本発明の(a)有機遷移金属化合物は、上記の例示化合物に限定されるものではなく、請求項記載の要件を満たす全ての化合物を包含するものである。
一般式(5)中、[R4R5 y−1M2H]はカチオンであり、Hはプロトンであり、M2は周期表の第15族または第16族から選ばれる元素であり、R4は炭素数1〜30の炭化水素基であり、R5は各々独立して水素原子または炭素数1〜30の炭化水素基であり、yは、M2が第15族元素の時y=3であり、M2が第16族元素の時y=2であり、[A]はアニオンであり、例えばフッ素イオン、塩素イオン、臭素イオン、ヨウ素イオン、硫酸イオン、硝酸イオン、リン酸イオン、過塩素酸イオン、シュウ酸イオン、クエン酸イオン、コハク酸イオン、テトラフルオロホウ酸イオンまたはヘキサフルオロリン酸イオンを用いることができるが、これらに限定されるものではない。さらに、aおよびbは電荷が釣り合うように選ばれた整数である。
[CL2 m][B(Ar)4] (9)
[D][B(Ar)4] (10)
B(Ar)3 (11)
(ここで、Hはプロトンであり、Bはホウ素原子またはアルミニウム原子である。L1はルイス塩基、L2はルイス塩基またはシクロペンタジエニル基である。Cはリチウム、鉄または銀から選ばれる金属の陽イオンであり、Dはカルボニウムカチオンまたはトロピニウムカチオンである。Arは炭素数6〜20のハロゲン置換アリール基である。mは0〜2の整数である。)
有機遷移金属化合物とイオン対を形成することができる化合物とは、該有機遷移金属化合物と作用もしくは反応することにより有機遷移金属化合物をカチオンに変換させることで、イオン性の錯体を形成することが可能な化合物のことを示している。さらに、これら化合物は該有機遷移金属化合物をカチオン性の化合物にした後、生成したカチオン種に対して弱く配位または相互作用するものの、該有機遷移金属カチオンとは反応しない対アニオンを提供する化合物である。
(R7)3Al (12)
(R7は各々同一でも異なっていてもよく、水素原子、ハロゲン原子、アミド基、アルコキシド基または炭化水素基を示し、そのうち少なくとも1つは炭化水素基である。)
で表される化合物を挙げることができる。
Y=X×(Mn/14000) (13)
(ただし、XはFT−IRで測定された末端ビニル基を有するポリオレフィンの主鎖メチレン炭素1000個あたりのビニル末端数、Mnは数平均分子量。)
で表されるYが0.35以上1以下であることを特徴とする。Yは、ポリオレフィンに存在するビニル末端の割合を表しており、Y値が大きいほど、ポリオレフィン中にビニル末端の数が多いことを示している。本発明で得られるポリオレフィンは、Y値が大きく、長鎖分岐を有するポリオレフィンを製造するために使用するポリオレフィンとして適したY値を示している。なお、オレフィン重合体のビニル末端数は、1H−NMR、13C−NMRまたはFT−IR等で求められることは、当該技術者には広く知られており、例えば、FT−IRでは、ビニル末端(CH=CH2)は908cm−1の吸収により、その存在および量が確認できる。
[「(ドコシル)(メチル)シランジイルビス(シクロペンタジエン)」の合成]
窒素気流下、−78℃に冷却したシクロペンタジエン(3.45g,52.2mmol)のTHF(150ml)溶液に、n−BuLiのヘキサン溶液(1.58mol/57.4mmol)をゆっくり滴下した。室温まで自然昇温し、終夜撹拌した後、再度−78℃まで冷却し、(ドコシル)(メチル)ジクロロシラン(5.53g,13.1mmol)のTHF溶液(30ml)をゆっくり加えた。この反応液を室温まで自然昇温し、終夜撹拌した後、希塩酸でクエンチした。酢酸エチルで抽出し、飽和食塩水で洗浄後、無水硫酸マグネシウムで乾燥し、溶媒留去を行った。得られた残渣をヘキサンに溶解させ、濾過カラムを行い、白色の固体(4.65g,9.6mmol)を得た。
[遷移金属化合物「(ドコシル)(メチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド」の合成]
窒素気流下、−78℃に冷却した(ドコシル)(メチル)シランジイルビス(シクロペンタジエン)(4.65g,9.6mmol)のTHF(200ml)溶液に、n−BuLiのヘキサン溶液(1.58mol/l,21mmol)をゆっくり滴下した。室温まで自然昇温し、終夜撹拌した後、再度−33℃まで冷却し、四塩化ジルコニウム(2.24g,9.6mmol)のTHF‐トルエン懸濁液(THF(30ml)‐トルエン(10ml))を加えた。この懸濁液を室温まで自然昇温し、終夜撹拌した後、減圧下で溶媒を留去した。残渣を塩化メチレンで抽出し、セライトを用いて不溶物を濾過後、得られた溶液を減圧下で濃縮したところ淡黄色の固体が析出してきた。この淡黄色の固体を濾取し、ヘキサンで洗浄したところ、乳白色の固体(1.82g,2.8mmol)を得た。
マススペクトル(EI‐MS、m/z):642(M+・).
実施例2
[成分(b)(変性粘土鉱物)の調製]
水350mlにエタノール150mlと37%濃塩酸8.3mlを加えた後、得られた溶液にN,N−ジメチル−n−オクタデシルアミン29.8g(0.1mol)を添加し、60℃に加熱することによって、N,N−ジメチル−n−オクタデシルアミン塩酸塩溶液を調製した。この溶液にヘクトライト100gを加えた。この懸濁液を60℃で3時間撹拌し、上澄み液を除去した後、60℃の水1lで洗浄した。その後、60℃、10−3torrで24時間乾燥し、ジェットミルで粉砕することによって、平均粒径5.2μmの変性ヘクトライトを得た。
[触媒調製]
上記[成分(b)(変性粘土鉱物)の調製]で得た変性ヘクトライト2.1gに、ヘキサン5.2mlを添加し、60℃で1時間攪拌することによって、成分(b)のヘキサン懸濁液を調製した。一方、実施例1で得た(ドコシル)(メチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド59.9mg(93mmol)に、n−ヘキサン2.6mlとトリイソブチルアルミニウムのヘキサン溶液(20wt%)12.4mlを添加し、室温で30分間攪拌することによって、成分(a)と成分(c)の接触生成物を得た。前記成分(b)のヘキサン懸濁液全量に、上記成分(a)と成分(c)の接触生成物5.1mlを添加し、60℃で3時間攪拌して、成分(a)と成分(b)と成分(c)の接触生成物を得た。得られた接触生成物をトリイソブチルアルミニウムのヘキサン溶液(1wt%)20mlで2回洗浄し、さらにトリイソブチルアルミニウムのヘキサン溶液(5wt%)を添加し全量20mlの触媒スラリーを調製した。この触媒スラリー1mlをヘキサン7mlで希釈し、触媒スラリー(0.5μmolZr/ml)を得た。
[ポリエチレンの製造]
2lのオートクレーブに、ヘキサンを1200mlとトリイソブチルアルミニウムのヘキサン溶液(0.34mol/l)1.0mlを導入し、オートクレーブの内温を85℃に昇温した。次に、上記[触媒調製]で調製した触媒スラリー2.0ml(Zr:1μmolに相当する)を添加し、エチレンを分圧が1.2MPaになるまで導入して重合を開始した。重合中、エチレン分圧が1.2MPaに保たれるように、エチレンを連続的に導入した。また、重合温度を85℃に制御した。重合開始90分後に、オートクレーブの内圧を0MPaまで脱圧した後、オートクレーブの内容物をろ過し、得られたポリエチレンを12時間乾燥した。結果として、39.9gのポリエチレンを得た。得られたポリマーのMFRは86.2g/10分であった。また、GPCより求めた重量平均分子量(Mw)は3.4×104であり、分子量分布(Mw/Mn)は2.6であった。また、FT−IR測定により得られたビニル末端数は0.42個/1000Cであり、ビニル末端数から求められるYは0.39であった。
[ポリエチレンの製造]
2lのオートクレーブにトルエンを500ml加え、これにメチルアルミノキサン(東ソー・アクゾ(株)製、分子量1121)をアルミニウム原子換算で20mmolおよび実施例1で得た(ドコシル)(メチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライドを3.22mg(5μmol)加えた。その後、エチレンを分圧が1.2MPaになるまで導入して重合を開始した。重合中、エチレン分圧が1.2MPaに保たれるように、エチレンを連続的に導入した。また、重合温度を85℃に制御した。90分間エチレンの重合を行い、35.2gのポリエチレンを得た。得られたポリマーのMFRは85g/10分であった。
[ポリエチレンの製造]
2lのオートクレーブにトルエンを500ml加え、次にトリイソブチルアルミニウム 0.25mmolを加え、10分間攪拌した。この溶液に、実施例1で得た(ドコシル)(メチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド0.64mg(1μmol)のトルエン溶液(10ml)を加え、この混合物を20分間攪拌した。これに公知の方法で合成したトリス(ペンタフルオロフェニル)ホウ素5.12mg(10μmol)を10mlのトルエン溶液にして挿入した。その後、エチレンを分圧が1.2MPaになるまで導入して重合を開始した。重合中、エチレン分圧が1.2MPaに保たれるように、エチレンを連続的に導入した。また、重合温度を85℃に制御した。90分間エチレンの重合を行い、32.8gのポリエチレンを得た。得られたポリマーのMFRは83.3g/10分であった。
[触媒調製]
(ドコシル)(メチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライドの代わりにジメチルシランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド27.9mg(80μmol)を用いたこと以外、実施例2と同様に触媒を調製した。
[ポリエチレンの製造]
触媒スラリーとして、上記[触媒調製]で調製した触媒スラリー2ml(Zr:1μmolに相当する)を用いたこと以外、実施例2と同様に重合した。結果として、170.0gのポリエチレンを得た。得られたポリマーのMFRは78.0g/10分であった。また、GPCより求めた重量平均分子量(Mw)は4.2×104であり、分子量分布(Mw/Mn)は3.2であった。また、FT−IR測定により得られたビニル末端数は0.33個/1000Cであり、ビニル末端数から求められるYは0.30であった。
[触媒調製]
(ドコシル)(メチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライドの代わりにジ(n−ヘキシル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド41.1mg(84μmol)を用いたこと以外、実施例2と同様に触媒を調製した。
[ポリエチレンの製造]
触媒スラリーとして、上記[触媒調製]で調製した触媒スラリー2ml(Zr:1μmolに相当する)を用いたこと以外、実施例2と同様に重合した。結果として、59.0gのポリエチレンを得た。得られたポリマーのMFRは49.8g/10分であった。また、GPCより求めた重量平均分子量(Mw)は4.3×104であり、分子量分布(Mw/Mn)は3.0であった。また、FT−IR測定により得られたビニル末端数は0.34個/1000Cであり、ビニル末端数から求められるYは0.34であった。
[触媒調製]
(ドコシル)(メチル)シランジイルビス(シクロペンタジエニル)ジルコニウムジクロライドの代わりにメチルシランジイルビス(シクロペンタジエニル)ジルコニウムジクロライド26.8mg(80μmol)を用いたこと以外、実施例2と同様に触媒を調製した。
[ポリエチレンの製造]
触媒スラリーとして、上記[触媒調製]で調製した触媒スラリー2ml(Zr:1μmolに相当する)を用いたこと以外、実施例2と同様に重合した。結果として、191.4gのポリエチレンを得た。得られたポリマーのMFRは65.2g/10分であった。また、GPCより求めた重量平均分子量(Mw)は3.6×104であり、分子量分布(Mw/Mn)は2.8であった。また、FT−IR測定により得られたビニル末端数は0.26個/1000Cであり、ビニル末端数から求められるYは0.24であった。
Claims (7)
- 下記一般式(1)
で表されるM1に配位する配位子であり、R1は炭素数1〜40の炭化水素基であり、R2は炭素数21〜40の炭化水素基であり、Qは炭素原子、ケイ素原子、ゲルマニウム原子または錫原子で表され、Cp1とCp2を架橋するように作用している。]
で表される(a)有機遷移金属化合物。 - 請求項1に記載の(a)有機遷移金属化合物及び(b)活性化助触媒からなることを特徴とするオレフィン重合用触媒。
- 請求項1に記載の(a)有機遷移金属化合物、(b)活性化助触媒及び(c)有機アルミニウム化合物からなることを特徴とするオレフィン重合用触媒。
- 成分(b)活性化助触媒が下記一般式(5)
[R4R5 y−1M2H]a[A]b (5)
(式中、[R4R5 y−1M2H]はカチオンであり、Hはプロトンであり、M2は周期表の第15族または第16族から選ばれる元素であり、R4は炭素数1〜30の炭化水素基であり、R5は各々独立して水素原子または炭素数1〜30の炭化水素基であり、yは、M2が第15族元素の時y=3であり、M2が第16族元素の時y=2であり、[A]はアニオンであり、aおよびbは電荷が釣り合うように選ばれた整数である。)
で表される有機化合物で処理された、変性粘土鉱物であることを特徴とする請求項2又は3に記載のオレフィン重合用触媒。 - 成分(b)活性化助触媒が下記一般式(8)ないし(11)
[HL1][B(Ar)4] (8)
[CL2 m][B(Ar)4] (9)
[D][B(Ar)4] (10)
B(Ar)3 (11)
(式中、Hはプロトンであり、Bはホウ素原子またはアルミニウム原子である。L1はルイス塩基、L2はルイス塩基またはシクロペンタジエニル基である。Cはリチウム、鉄または銀から選ばれる金属の陽イオンであり、Dはカルボニウムカチオンまたはトロピニウムカチオンである。Arは炭素数6〜20のハロゲン置換アリール基である。mは0〜2の整数である。)で表される、有機遷移金属化合物とイオン対を形成することができる化合物であることを特徴とする請求項2又は3に記載のオレフィン重合用触媒。 - 請求項2ないし6に記載のオレフィン重合用触媒を用いてオレフィン重合を行うことを特徴とするポリオレフィンの製造方法。
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US8802797B2 (en) | 2008-06-20 | 2014-08-12 | Exxonmobil Chemical Patents Inc. | Vinyl-terminated macromonomer oligomerization |
US8372930B2 (en) | 2008-06-20 | 2013-02-12 | Exxonmobil Chemical Patents Inc. | High vinyl terminated propylene based oligomers |
US8399725B2 (en) | 2008-06-20 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Functionalized high vinyl terminated propylene based oligomers |
US8283419B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Olefin functionalization by metathesis reaction |
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US8841397B2 (en) | 2011-03-25 | 2014-09-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
US8501894B2 (en) | 2011-03-25 | 2013-08-06 | Exxonmobil Chemical Patents Inc. | Hydrosilyation of vinyl macromers with metallocenes |
US8785562B2 (en) | 2011-03-25 | 2014-07-22 | Exxonmobil Chemical Patents Inc. | Amphiphilic block polymers prepared by alkene metathesis |
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US8835563B2 (en) | 2011-03-25 | 2014-09-16 | Exxonmobil Chemical Patents Inc. | Block copolymers from silylated vinyl terminated macromers |
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