JP5501962B2 - アルミニウムフェノキシド化合物を用いた安定化ポリマーの製造方法。 - Google Patents
アルミニウムフェノキシド化合物を用いた安定化ポリマーの製造方法。 Download PDFInfo
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- JP5501962B2 JP5501962B2 JP2010515833A JP2010515833A JP5501962B2 JP 5501962 B2 JP5501962 B2 JP 5501962B2 JP 2010515833 A JP2010515833 A JP 2010515833A JP 2010515833 A JP2010515833 A JP 2010515833A JP 5501962 B2 JP5501962 B2 JP 5501962B2
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- -1 aluminum phenoxide compound Chemical class 0.000 title claims description 231
- 229920000642 polymer Polymers 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 239000005977 Ethylene Substances 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000004711 α-olefin Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002480 mineral oil Substances 0.000 claims description 6
- 235000010446 mineral oil Nutrition 0.000 claims description 6
- 239000011954 Ziegler–Natta catalyst Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000002002 slurry Substances 0.000 claims description 5
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004079 stearyl 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])[H] 0.000 claims description 4
- 125000002960 margaryl 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])[H] 0.000 claims description 3
- 125000000913 palmityl 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])[H] 0.000 claims description 3
- 239000002685 polymerization catalyst Substances 0.000 claims description 3
- 229920001384 propylene homopolymer Polymers 0.000 claims description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 229920010524 Syndiotactic polystyrene Polymers 0.000 claims description 2
- 238000012662 bulk polymerization Methods 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 2
- 238000012685 gas phase polymerization Methods 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 229920001083 polybutene Polymers 0.000 claims description 2
- 229920005638 polyethylene monopolymer Polymers 0.000 claims description 2
- 229920005606 polypropylene copolymer Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 30
- 150000003623 transition metal compounds Chemical class 0.000 description 30
- 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 25
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 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 19
- 150000002430 hydrocarbons Chemical class 0.000 description 19
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 18
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 150000001639 boron compounds Chemical class 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 229920001155 polypropylene Polymers 0.000 description 16
- 239000004743 Polypropylene Substances 0.000 description 13
- 150000001450 anions Chemical group 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 239000012968 metallocene catalyst Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000000087 stabilizing effect Effects 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 125000004437 phosphorous atom Chemical group 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 150000008282 halocarbons Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 239000013557 residual solvent Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 230000006641 stabilisation Effects 0.000 description 6
- 238000011105 stabilization Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 5
- 239000007848 Bronsted acid Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- HFKJQIJFRMRSKM-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFKJQIJFRMRSKM-UHFFFAOYSA-N 0.000 description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 150000001767 cationic compounds Chemical class 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 4
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 150000002892 organic cations Chemical class 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- 239000002879 Lewis base Substances 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- ZRTWIJKGTUGZJY-UHFFFAOYSA-N 3,4,5-trifluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1 ZRTWIJKGTUGZJY-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical class C1(=CC=CC1)* 0.000 description 2
- RFUDQCRVCDXBGK-UHFFFAOYSA-L dichloro(propyl)alumane Chemical compound [Cl-].[Cl-].CCC[Al+2] RFUDQCRVCDXBGK-UHFFFAOYSA-L 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003609 titanium compounds Chemical class 0.000 description 2
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 2
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- DJXJARQPGKYVNA-UHFFFAOYSA-N trifluoromethanolate Chemical compound [O-]C(F)(F)F DJXJARQPGKYVNA-UHFFFAOYSA-N 0.000 description 2
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- BSHDALZPYCORND-UHFFFAOYSA-L [Cl-].[Cl-].CC=1C(=C(C(C=1)(C)[Ti+2]C1C=CC2=CC=CC=C12)C)C Chemical compound [Cl-].[Cl-].CC=1C(=C(C(C=1)(C)[Ti+2]C1C=CC2=CC=CC=C12)C)C BSHDALZPYCORND-UHFFFAOYSA-L 0.000 description 1
- CHIHJSQOMGQVCV-UHFFFAOYSA-L [Cl-].[Cl-].CC=1C(C=CC=1)(CC)[Hf+2] Chemical compound [Cl-].[Cl-].CC=1C(C=CC=1)(CC)[Hf+2] CHIHJSQOMGQVCV-UHFFFAOYSA-L 0.000 description 1
- ZOQSUCDFCNSPFH-UHFFFAOYSA-L [Cl-].[Cl-].CCC1=CC=CC1(C)[Ti++]C1(C)C=CC=C1CC Chemical compound [Cl-].[Cl-].CCC1=CC=CC1(C)[Ti++]C1(C)C=CC=C1CC ZOQSUCDFCNSPFH-UHFFFAOYSA-L 0.000 description 1
- DCBUEAHDPHOBMR-UHFFFAOYSA-L [Cl-].[Cl-].CCCCC1=CC=CC1(C)[Ti++]C1(C)C=CC=C1CCCC Chemical compound [Cl-].[Cl-].CCCCC1=CC=CC1(C)[Ti++]C1(C)C=CC=C1CCCC DCBUEAHDPHOBMR-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- PCGYNXNSBCFBSU-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl)-phenylborane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=CC=CC=C1 PCGYNXNSBCFBSU-UHFFFAOYSA-N 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- QQHRHLXGCZWTDK-UHFFFAOYSA-L butylaluminum(2+);dibromide Chemical compound [Br-].[Br-].CCCC[Al+2] QQHRHLXGCZWTDK-UHFFFAOYSA-L 0.000 description 1
- CZQIDPLTQBOKMO-UHFFFAOYSA-L butylcyclopentane;dichlorotitanium Chemical compound Cl[Ti]Cl.CCCC[C]1[CH][CH][CH][CH]1.CCCC[C]1[CH][CH][CH][CH]1 CZQIDPLTQBOKMO-UHFFFAOYSA-L 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- DFGSACBYSGUJDZ-UHFFFAOYSA-M chloro(dihexyl)alumane Chemical compound [Cl-].CCCCCC[Al+]CCCCCC DFGSACBYSGUJDZ-UHFFFAOYSA-M 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- CYKLGTUKGYURDP-UHFFFAOYSA-L copper;hydrogen sulfate;hydroxide Chemical compound O.[Cu+2].[O-]S([O-])(=O)=O CYKLGTUKGYURDP-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- VJRUISVXILMZSL-UHFFFAOYSA-M dibutylalumanylium;chloride Chemical compound CCCC[Al](Cl)CCCC VJRUISVXILMZSL-UHFFFAOYSA-M 0.000 description 1
- QEHKWLKYFXJVLL-UHFFFAOYSA-N dichloro(dimethoxy)silane Chemical compound CO[Si](Cl)(Cl)OC QEHKWLKYFXJVLL-UHFFFAOYSA-N 0.000 description 1
- YQZMEUFOYRWASB-UHFFFAOYSA-L dichlorotitanium;ethylcyclopentane Chemical compound Cl[Ti]Cl.CC[C]1[CH][CH][CH][CH]1.CC[C]1[CH][CH][CH][CH]1 YQZMEUFOYRWASB-UHFFFAOYSA-L 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-O diethyl(phenyl)azanium Chemical compound CC[NH+](CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-O 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
- CPDVHGLWIFENDJ-UHFFFAOYSA-N dihexylalumane Chemical compound C(CCCCC)[AlH]CCCCCC CPDVHGLWIFENDJ-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- XOCWTYIVWYOSGQ-UHFFFAOYSA-N dipropylalumane Chemical compound C(CC)[AlH]CCC XOCWTYIVWYOSGQ-UHFFFAOYSA-N 0.000 description 1
- PTOQCUYVGKZAFS-UHFFFAOYSA-N ethenylcycloheptane Chemical compound C=CC1CCCCCC1 PTOQCUYVGKZAFS-UHFFFAOYSA-N 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 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 1
- VMLUVDHAXSZZSR-UHFFFAOYSA-L hexylaluminum(2+);dichloride Chemical compound CCCCCC[Al](Cl)Cl VMLUVDHAXSZZSR-UHFFFAOYSA-L 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- YSTQWZZQKCCBAY-UHFFFAOYSA-L methylaluminum(2+);dichloride Chemical compound C[Al](Cl)Cl YSTQWZZQKCCBAY-UHFFFAOYSA-L 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 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
- NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940054334 silver cation Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- NPHLURKGGOFSPO-UHFFFAOYSA-N tris(2,3,4,5-tetrafluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC(B(C=2C(=C(F)C(F)=C(F)C=2)F)C=2C(=C(F)C(F)=C(F)C=2)F)=C1F NPHLURKGGOFSPO-UHFFFAOYSA-N 0.000 description 1
- BMKAZNZYKFHZCV-UHFFFAOYSA-N tris(2,3,4-trifluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC=C1B(C=1C(=C(F)C(F)=CC=1)F)C1=CC=C(F)C(F)=C1F BMKAZNZYKFHZCV-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
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
-
- 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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Toxicology (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
上記重合触媒として、チーグラー・ナッタ触媒を用いる安定化ポリマーの製造方法を提供するものである。
先ず、上記一般式(I)で表される、本発明のアルミニウムフェノキシド化合物について説明する。
t/n<1.3であると、重合触媒の活性を低下させたり、十分な安定化効果が得られなかったりする。
例えば、上記化合物1と有機アルミニウムを反応させる場合について説明すると、本発明のアルミニウムフェノキシド化合物は、化合物1とトリメチルアルミニウムやジエチルクロロアルミニウム等の有機アルミニウムとを、アルミニウム原子のモル数が化合物1のモル数の1.3倍以上になる比率で、不活性ガス雰囲気下、ヘキサン、ヘプタン又はミネラルオイル等の脂肪族系溶媒中で混合するか、溶媒を用いずに混合することで製造することができる。特に、ヘキサン及び/又はヘプタンを溶媒として用いて製造するか、溶媒を用いずに製造することが、残存溶媒量の少ない重合体が得られるので好ましい。
以下、本発明の製造方法をプロピレン重合体の製造に適用した場合について詳述する。
プロピレンと共重合するα-オレフィンとしては、1−ブテン、1−ペンテン、1−ヘキセン、1−ヘプテン1−オクテン、1−ヘキサデセン、1−エイコセン等の直鎖状のオレフィン;3−メチル−1−ブテン、3−メチル−1−ペンテン、1−エチル−1−ペンテン、4−メチル−1−ペンテン、4−メチル−1−ヘキセン、4,4−ジメチル−1−ヘキセン、4,4−ジメチル−1−ペンテン、4−エチル−1−ヘキセン、3−エチル−1−ヘキセン、アリルナフタレン、アリルノルボルナン、スチレン、ジメチルスチレン類、ビニルナフタレン類、アリルトルエン類、アリルベンゼン、ビニルシクロヘキサン、ビニルシクロペンタン、ビニルシクロヘプタン、アリルトリアルキルシラン類等の分岐構造を有するオレフィン等を用いることができる。これらポリマーの中では、特に、安定化効果が大きく、相溶性に優れる等の観点から、エチレン、1−ブテンが特に好ましく用いられる。
下記(i)の遷移金属化合物と、下記(ii)の遷移金属化合物とからなるメタロセン触媒が挙げられる。
(i):シクロペンタジエン形アニオン骨格を有する基を2個有し、且つ、このシクロペンタジエン形アニオン骨格を有する基が直接又は架橋基を介して互いに結合しており、中心金属がハフニウムである遷移金属化合物。
(ii):置換基を持つシクロペンタジエン形アニオン骨格を有する基を2個有し、且つ、このシクロペンタジエン形アニオン骨格を有する基が互いに結合しておらず、中心金属がジルコニウムである遷移金属化合物
以下、このメタロセン触媒を具体的に説明する。
(L2)2Hf(X1)2 [1]
(式中、L2はシクロペンタジエン形アニオン骨格を有する基であり、2つのL2は同じでも異なっていてもよく、2つのL2は直接又は炭素原子、ケイ素原子、窒素原子、酸素原子、硫黄原子若しくはリン原子を含有する残基を介して連結される。X1はハロゲン原子、炭化水素基又は炭化水素オキシ基を表す。)
上記一般式[1]における2つのL2は、直接又は炭素原子、ケイ素原子、窒素原子、酸素原子、硫黄原子又はリン原子を含有する残基を介して連結される。かかる残基については既に説明した通りであり、上記一般式[1]で表される遷移金属化合物として好ましくは、2つのL2が炭素原子、ケイ素原子、窒素原子、酸素原子、硫黄原子又はリン原子を含有する残基を介して連結されている遷移金属化合物である。
これらのアルキル基はいずれも、フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子で置換されていてもよい。ハロゲン原子で置換された炭素原子数1〜10のアルキル基としては、例えば、フルオロメチル基、トリフルオロメチル基、クロロメチル基、トリクロロメチル基、フルオロエチル基、ペンタフルオロエチル基、パーフルオロプロピル基、パーフルオロブチル基、パーフルオロヘキシル基、パーフルオロオクチル基、パークロロプロピル基、パークロロブチル基、パーブロモプロピル基等が挙げられる。また、これらのアルキル基はいずれも、メトキシ基、エトキシ基等のアルコキシ基、フェノキシ基等のアリールオキシ基又はベンジルオキシ基等のアラルキルオキシ基等で一部が置換されていてもよい。
これらのアラルキル基はいずれも、フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子、メトキシ基、エトキシ基等のアルコキシ基、フェノキシ基等のアリールオキシ基又はベンジルオキシ基等のアラルキルオキシ基等で一部が置換されていてもよい。
(L3)2(M2)(X2)2 [2]
(式中、M2はチタン原子又はジルコニウム原子であり、L3は置換基を持つシクロペンタジエン形アニオン骨格を有する基であり、二つのL3は架橋されていない。X2はハロゲン原子、炭化水素基又は炭化水素オキシ基を表す。)
即ち、本発明で用いられるメタロセン触媒としては、上記遷移金属化合物からなるメタロセン触媒(A)と、下記成分(B)及び/又は下記成分(C)とを接触させて得られるメタロセン触媒が好ましい。
下記(B1)〜(B3)から選ばれる1種以上のアルミニウム化合物
(B1):下記一般式で表される有機アルミニウム化合物
(E1)aAlZ3-a
(B2):下記一般式で表される構造を有する環状のアルミノキサン
{−Al(E2)−O−}b
(B3):下記一般式で表される構造を有する線状のアルミノキサン
(E3){−Al(E3)−O−}cAl(E3)2
(式中、E1、E2及びE3は、それぞれ、炭化水素基であり、全てのE1、全てのE2及び全てのE3は同じであっても異なっていても良い。Zは水素原子又はハロゲン原子を表し、全てのZは同じであっても異なっていても良い。aは0<a≦3を満足する数を、bは2以上の整数を、cは1以上の整数を表す。)
<成分(C)>
下記(C1)〜(C3)から選ばれる1種以上のホウ素化合物
(C1):下記一般式で表されるホウ素化合物
BQ1Q2Q3
(C2):下記一般式で表されるホウ素化合物
G+(BQ1Q2Q3Q4)-
(C3):下記一般式で表されるホウ素化合物
(L−H)+(BQ1Q2Q3Q4)-
(式中、Bは3価の原子価状態のホウ素原子であり、Q1〜Q4はハロゲン原子、炭化水素基、ハロゲン化炭化水素基、置換シリル基、アルコキシ基又は2置換アミノ基であり、それらは同じであっても異なっていても良い。G+は無機又は有機のカチオンであり、Lは中性ルイス塩基であり、(L−H)+はブレンステッド酸である。)
以下、かかる(B)成分及び(C)成分についてさらに詳しく説明する。
下記(B1)〜(B3)から選ばれる1種以上のアルミニウム化合物
(B1):下記一般式で表される有機アルミニウム化合物
(E1)aAlZ3-a
(B2):下記一般式で表される構造を有する環状のアルミノキサン
{−Al(E2)−O−}b
(B3):下記一般式で表される構造を有する線状のアルミノキサン
(E3){−Al(E3)−O−}cAl(E3)2
(式中、E1、E2、及びE3は、それぞれ炭化水素基であり、全てのE1、全てのE2及び全てのE3は同じであっても異なっていても良い。Zは水素原子又はハロゲン原子を表し、全てのZは同じであっても異なっていても良い。aは0<a≦3を満足する数を、bは2以上の整数を、cは1以上の整数を表す。)
E1、E2、又はE3で表される炭化水素基としては、炭素数1〜8の炭化水素基が好ましく、アルキル基がより好ましい。
(C1):下記一般式で表されるホウ素化合物
BQ1Q2Q3
(C2):下記一般式で表されるホウ素化合物
G+(BQ1Q2Q3Q4)-
(C3):下記一般式で表されるホウ素化合物
(L−H)+(BQ1Q2Q3Q4)-
(式中、Bは3価の原子価状態のホウ素原子であり、Q1〜Q4はハロゲン原子、炭化水素基、ハロゲン化炭化水素基、置換シリル基、アルコキシ基又は2置換アミノ基であり、それらは同じであっても異なっていても良い。G+は無機又は有機のカチオンであり、Lは中性ルイス塩基であり、(L−H)+はブレンステッド酸である。)
(a):下記一般式[3]で表される化合物
Zn(L1)2 [3]
(b):下記一般式[4]で表される化合物
R1OH [4]
(c):下記一般式[5]で表される化合物
H2O [5]
(上記一般式[3]及び[4]において、L1は炭化水素基を表し、L1は互いに同じであっても異なっていても良い。R1はハロゲン化炭化水素基を表す。)
ヘプタン50ml中で表1記載の配合を2時間攪拌し、アルミニウムフェノキシド化合物を製造した。得られた化合物の一部を80℃で減圧して脱ヘプタンし、得られた固体について、1H−NMRにより活性水素の残存有無を確認した。尚、活性水素の残存有無の確認は、5.1〜5.5ppmをN−Hに帰属するピーク、5.0〜5.1ppmをO−Hに帰属するピークとして行った。これらの結果を表1に示す。
ミネラルオイル50ml中で表2に記載の配合を2時間攪拌し、アルミニウムフェノキシド化合物を製造した。得られた化合物の一部を80℃で減圧して脱ミネラルオイルし、得られた固体の活性水素の残存有無を、実施例1と同様にして確認した。これらの結果を表2に示す。
アルゴン雰囲気下、表3記載の配合をミキサーで2時間混合し、アルミニウムフェノキシド化合物を製造した。得られた化合物の活性水素の残存有無を、実施例1と同様にして確認した。これらの結果を表3に示す。
トルエン50ml中で表4記載の配合を2時間攪拌し、アルミニウムフェノキシド化合物を製造した。得られた化合物の一部を80℃で減圧して脱トルエンし、得られた固体の活性水素の残存有無を、実施例1と同様にして確認した。これらの結果を表4に示す。
1.固体Ti触媒の調製
無水塩化マグネシウム4.76g(50mmol)、デカン25ml及び2−エチルヘキシルアルコール23.4ml(150mmol)を130℃で2時間加熱反応を行い均一溶液とした後、この溶液中に無水フタル酸1.11g(7.5mmol)を添加し、130℃にて更に1時間撹拌反応を行い、無水フタル酸を該均一溶液に溶解させる。このようにして得られた均一溶液を室温に冷却した後、−20℃に保持された四塩化チタン200ml(1.8mol)中に1時間に渡って全量滴下装入する。装入終了後、この混合液の温度を4時間かけて110℃に昇温し、110℃に達したところでジイソブチルフタレート2.68ml(12.5mmol)を添加し、これより2時間同温度にて撹拌下保持する。2時間の反応終了後熱ろ過にて固体部を採取し、この固体部を200mlの四塩化チタンにて再懸濁させた後、再び110℃で2時間、加熱反応を行う。反応終了後、再び熱ろ過にて固体部を採取し、110℃デカン及びヘキサンにて、洗液中に遊離のチタン化合物が検出されなくなるまで充分洗浄する。以上の製造方法にて合成された固体Ti触媒成分はヘプタンスラリーとして保存するが、このうち一部を触媒組成を調べる目的で乾燥する。この様にして得られた固体Ti触媒成分の組成は、チタン2.6重量%、塩素56.0重量%、マグネシウム17.0重量%及びイソブチルフタレート20.9重量%であった。
窒素置換した1000mlオートクレーブにヘプタン600mlを加えた。トリエチルアルミニウム(1.8mmol)、表5記載のアルミニウムフェノキシド化合物(18mmol)加え、23℃で5分間攪拌した。ジシクロペンチルジメトキシシラン(0.18mmol)、固体Ti触媒16mgを順次加えた。オートクレーブ内をプロピレン雰囲気に置換し、プロピレンで1kgf/cm2Gの圧力をかけ、35℃で10分間プレ重合した。プロピレンをパージした後、水素150ml(標準状態換算)をオートクレーブ系内に導入し、昇温を開始するとともにプロピレンを導入し、6kgf/cm2Gの圧力をかけ、70℃で1時間重合を行なった。その後、冷却(40℃まで)を開始すると共に系内のプロピレンをパージし窒素にて置換し、次いでエタノール5mLを加え触媒を失活させると共に完全に重合を停止させた。得られたポリプロピレンパウダーを含むヘプタンスラリーに対して、50℃で減圧して脱溶媒を行ない、真空中、40℃でポリマーを5時間乾燥することにより、ポリプロピレンパウダーを得た。得られたポリプロピレンの収量及び重量平均分子量を表5に示す。
得られたポリプロピレン1gをo−ジクロロベンゼン100gに溶解してガスクロマトグラフで、ポリプロピレン中のヘプタン、ミネラルオイル及びトルエンの残存量を測定した。
これに対し、実施例4−1〜4−6のようにアルミニウム化合物の過剰率が40%当量以上(t/n=1.4又は1.8)である、本発明のアルミニウムフェノキシド化合物を添加した場合、アルミニウムフェノキシド化合物を添加しない参考例1−1と同等のポリプロピレンの収量が得られた。
従って、トルエンのような芳香族系溶媒を用いて製造したアルミニウムフェノキシド化合物は、重合そのものへ影響を与える。また、衛生性の観点から重合物の品質を低下させる。
Claims (4)
- ミネラルオイルを溶媒として用いるか、溶媒を用いずに製造された下記一般式(I)で表されるアルミニウムフェノキシド化合物を、重合前又は重合中に、触媒系又は重合系に添加する安定化ポリマーの製造方法であって、
上記重合触媒として、チーグラー・ナッタ触媒を用いる安定化ポリマーの製造方法。
- 上記一般式(I)におけるAが、エチル基である請求項1記載の安定化ポリマーの製造方法。
- 重合方法が、スラリー重合、バルク重合、気相重合、超臨界重合、溶液重合及びこれらの組合せの何れかである請求項1又は2記載の安定化ポリマーの製造方法。
- 製造されるポリマーが、プロピレン単独重合体、プロピレンとエチレン及び/又はα−オレフィンの共重合体、ポリエチレン単独重合体、エチレンとα−オレフィンの共重合体、ポリブテン単独重合体、ブテンとエチレン及び/又はα−オレフィンの共重合体、ポリ4−メチル−1−ペンテン、シクロオレフィンポリマー、又は、シンジオタクチックポリスチレンである請求項1〜3の何れか1項に記載の安定化ポリマーの製造方法。
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US20130331515A1 (en) * | 2011-03-02 | 2013-12-12 | Adeka Corporation | Process of producing laminate film and resin composition for coating members |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0253804A (ja) * | 1988-06-30 | 1990-02-22 | Ciba Geigy Ag | 熱安定性オレフィンポリマーの製造方法 |
JPH05271335A (ja) * | 1991-12-13 | 1993-10-19 | Himont Inc | 安定化したポリオレフィンの製造方法およびそれにより得られる生成物 |
JPH08208731A (ja) * | 1994-11-03 | 1996-08-13 | Ciba Geigy Ag | 安定化オレフィンポリマーの製造方法 |
JP2005206625A (ja) * | 2004-01-20 | 2005-08-04 | Asahi Denka Kogyo Kk | 安定化されたポリマーの製造方法 |
JP2005255953A (ja) * | 2004-03-15 | 2005-09-22 | Asahi Denka Kogyo Kk | 安定化されたポリマーの製造方法 |
JP2006052241A (ja) * | 2004-08-09 | 2006-02-23 | Asahi Denka Kogyo Kk | 安定化ポリマーの製造方法 |
JP2006282985A (ja) * | 2005-03-11 | 2006-10-19 | Adeka Corp | 安定化されたポリマーの製造方法 |
Family Cites Families (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4938986B1 (ja) | 1970-10-02 | 1974-10-22 | ||
CH543546A (fr) | 1971-03-23 | 1973-10-31 | Solvay | Système catalytique de polymérisation des alpha-oléfines |
AR206852A1 (es) | 1975-03-10 | 1976-08-23 | Union Carbide Corp | Procedimiento para preparar polimeros de etileno de densidad baja y media en un reactor de lecho fluido |
JPS595604B2 (ja) | 1980-03-18 | 1984-02-06 | 旭化成株式会社 | 斜板式アキシャルプランジャ型油圧作動装置 |
JPS595602B2 (ja) | 1979-12-04 | 1984-02-06 | 旭化成株式会社 | オレフインの重合用触媒 |
US4330433A (en) * | 1980-02-27 | 1982-05-18 | Exxon Research & Engineering Co. | Titanium trihalide catalyst and process for its production |
JPS5950242B2 (ja) | 1980-02-29 | 1984-12-07 | 旭化成株式会社 | オレフイン重合用高活性触媒 |
JPS5766865A (en) | 1980-10-14 | 1982-04-23 | Kenma Shizai Kogyo Kk | Rotary grindstone reinforcing glass cloth |
US4364839A (en) * | 1980-12-31 | 1982-12-21 | Phillips Petroleum Company | Catalyst comprising chromium on silica/phosphate support |
US4444963A (en) * | 1980-12-31 | 1984-04-24 | Phillips Petroleum Company | Polymerization process using catalysts comprising chromium on silica/phosphate support |
DE3110774A1 (de) | 1981-03-19 | 1982-10-14 | Daimler-Benz Ag, 7000 Stuttgart | "verfahren zur ermittlung von wartungs- und pflegedienstintervallen" |
JPS585310A (ja) | 1981-07-03 | 1983-01-12 | Mitsubishi Petrochem Co Ltd | オレフイン重合用触媒成分 |
JPS5823806A (ja) | 1981-08-04 | 1983-02-12 | Chisso Corp | α−オレフイン重合体を製造する方法 |
JPS5883006A (ja) | 1981-11-13 | 1983-05-18 | Mitsui Petrochem Ind Ltd | オレフインの重合方法 |
JPS58157808A (ja) | 1982-03-16 | 1983-09-20 | Ube Ind Ltd | α−オレフインの重合方法 |
JPS59196346A (ja) | 1983-04-21 | 1984-11-07 | Asahi Chem Ind Co Ltd | ポリエチレン樹脂組成物 |
JPS6036547A (ja) | 1983-08-09 | 1985-02-25 | Asahi Chem Ind Co Ltd | ポリエチレン系の組成物 |
JPS6147280A (ja) | 1984-08-13 | 1986-03-07 | Oki Electric Ind Co Ltd | 通帳記帳機 |
JPS61218606A (ja) | 1985-03-25 | 1986-09-29 | Sumitomo Chem Co Ltd | α−オレフイン重合体の製造法 |
FR2604439B1 (fr) | 1986-09-26 | 1989-07-28 | Solvay | Solide catalytique utilisable pour la polymerisation stereospecifique des alpha-olefines, procede pour le preparer et procede pour polymeriser des alpha-olefines en sa presence |
JPS63256541A (ja) | 1987-04-15 | 1988-10-24 | Nabeya:Kk | ガラス成形用型およびそれを用いたガラス製品の成形方法 |
US5032632A (en) * | 1990-05-15 | 1991-07-16 | E. I. Du Pont De Nemours And Company | Oxidation-resistant ethylene vinyl alcohol polymer compositions |
US5104841A (en) | 1991-04-22 | 1992-04-14 | Phillips Petroleum Company | Olefin polymerization catalysts and processes |
US5137997A (en) | 1991-04-22 | 1992-08-11 | Phillips Petroleum Company | Olefin polymerization catalysts and processes |
CA2121461C (en) | 1991-11-04 | 2001-08-28 | Pamela R. Auburn | Olefin polymerization using an aluminoxane/chromium catalyst |
JPH0925313A (ja) | 1995-07-10 | 1997-01-28 | Showa Denko Kk | エチレン系重合体の製造方法 |
JP2878991B2 (ja) | 1995-07-10 | 1999-04-05 | 昭和電工株式会社 | エチレン系重合体の製造方法 |
JPH0925314A (ja) | 1995-07-10 | 1997-01-28 | Showa Denko Kk | エチレン系重合体の製造方法 |
JPH11302465A (ja) | 1998-02-17 | 1999-11-02 | Showa Denko Kk | ポリエチレン樹脂組成物 |
JP4540902B2 (ja) | 2001-09-28 | 2010-09-08 | ローランド株式会社 | 電子楽器 |
WO2004013149A1 (en) | 2002-08-02 | 2004-02-12 | Dow Global Technologies Inc. | Group 4 metal complexes containing 4-aryl-substituted, tricyclic indenyl derivatives |
JP2006316145A (ja) | 2005-05-11 | 2006-11-24 | Mitsui Chemicals Inc | ビニル基含有αオレフィン系重合体とその製法 |
-
2009
- 2009-05-25 US US12/993,006 patent/US20110065876A1/en not_active Abandoned
- 2009-05-25 EP EP09758234A patent/EP2281825A4/en not_active Withdrawn
- 2009-05-25 CN CN2009801182381A patent/CN102036998A/zh active Pending
- 2009-05-25 WO PCT/JP2009/059533 patent/WO2009147967A1/ja active Application Filing
- 2009-05-25 JP JP2010515833A patent/JP5501962B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0253804A (ja) * | 1988-06-30 | 1990-02-22 | Ciba Geigy Ag | 熱安定性オレフィンポリマーの製造方法 |
JPH05271335A (ja) * | 1991-12-13 | 1993-10-19 | Himont Inc | 安定化したポリオレフィンの製造方法およびそれにより得られる生成物 |
JPH08208731A (ja) * | 1994-11-03 | 1996-08-13 | Ciba Geigy Ag | 安定化オレフィンポリマーの製造方法 |
JP2005206625A (ja) * | 2004-01-20 | 2005-08-04 | Asahi Denka Kogyo Kk | 安定化されたポリマーの製造方法 |
JP2005255953A (ja) * | 2004-03-15 | 2005-09-22 | Asahi Denka Kogyo Kk | 安定化されたポリマーの製造方法 |
JP2006052241A (ja) * | 2004-08-09 | 2006-02-23 | Asahi Denka Kogyo Kk | 安定化ポリマーの製造方法 |
JP2006282985A (ja) * | 2005-03-11 | 2006-10-19 | Adeka Corp | 安定化されたポリマーの製造方法 |
Non-Patent Citations (2)
Title |
---|
JPN6013039193; Journal of Applied Polymer Science 99(4), 2006, p.1350-1358 * |
JPN6013039194; Studies in Surface Science and Catalysis , 2006, p.13-18 * |
Also Published As
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EP2281825A4 (en) | 2012-02-22 |
CN102036998A (zh) | 2011-04-27 |
WO2009147967A1 (ja) | 2009-12-10 |
EP2281825A1 (en) | 2011-02-09 |
US20110065876A1 (en) | 2011-03-17 |
JPWO2009147967A1 (ja) | 2011-10-27 |
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