JP5498781B2 - 複素環式有機リガンドのハフニウム錯体 - Google Patents
複素環式有機リガンドのハフニウム錯体 Download PDFInfo
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- JP5498781B2 JP5498781B2 JP2009509569A JP2009509569A JP5498781B2 JP 5498781 B2 JP5498781 B2 JP 5498781B2 JP 2009509569 A JP2009509569 A JP 2009509569A JP 2009509569 A JP2009509569 A JP 2009509569A JP 5498781 B2 JP5498781 B2 JP 5498781B2
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- Prior art keywords
- phenyl
- methylethyl
- tri
- bis
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000623 heterocyclic group Chemical group 0.000 title claims description 7
- 150000002362 hafnium Chemical class 0.000 title description 3
- 239000013110 organic ligand Substances 0.000 title description 2
- -1 2-ethylbenzofuran-3-yl Chemical group 0.000 claims description 101
- 239000003054 catalyst Substances 0.000 claims description 101
- 238000000034 method Methods 0.000 claims description 92
- 239000000203 mixture Substances 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 239000003446 ligand Substances 0.000 claims description 41
- 238000006116 polymerization reaction Methods 0.000 claims description 40
- 229910052735 hafnium Inorganic materials 0.000 claims description 38
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 35
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 34
- 150000004696 coordination complex Chemical class 0.000 claims description 32
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 31
- 239000005977 Ethylene Substances 0.000 claims description 31
- 239000000047 product Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 150000001336 alkenes Chemical class 0.000 claims description 18
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 238000012644 addition polymerization Methods 0.000 claims description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 13
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 12
- 239000006227 byproduct Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- KJHYAEZMOHLVCH-UHFFFAOYSA-N 2-ethyl-1-benzofuran Chemical group C1=CC=C2OC(CC)=CC2=C1 KJHYAEZMOHLVCH-UHFFFAOYSA-N 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 7
- 159000000003 magnesium salts Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 5
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 claims description 4
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical class [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- 229920000642 polymer Polymers 0.000 description 58
- 230000008569 process Effects 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 229910052751 metal Inorganic materials 0.000 description 46
- 239000002184 metal Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 239000012190 activator Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000007983 Tris buffer Substances 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 150000002431 hydrogen Chemical class 0.000 description 13
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 13
- 238000009826 distribution Methods 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- 239000010936 titanium Substances 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000010828 elution Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001994 activation Methods 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 230000001976 improved effect Effects 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 150000003624 transition metals Chemical class 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000011148 porous material Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- 229910052723 transition metal Inorganic materials 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000004913 activation Effects 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 125000005234 alkyl aluminium group Chemical group 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 230000000737 periodic effect Effects 0.000 description 7
- 239000002685 polymerization catalyst Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical group ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229920001038 ethylene copolymer Polymers 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
- 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 6
- 239000002245 particle Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-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
- 125000004429 atom Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 229910052720 vanadium Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
- PSOKQSNKTAQFKV-UHFFFAOYSA-N 3-bromo-2-ethyl-1-benzofuran Chemical compound C1=CC=C2C(Br)=C(CC)OC2=C1 PSOKQSNKTAQFKV-UHFFFAOYSA-N 0.000 description 4
- MECCSFDHAVAAAW-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yl-1,3,2-dioxaborolane Chemical compound CC(C)B1OC(C)(C)C(C)(C)O1 MECCSFDHAVAAAW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 4
- 229940063655 aluminum stearate Drugs 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 238000012685 gas phase polymerization Methods 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 125000000743 hydrocarbylene group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- 229920001580 isotactic polymer Polymers 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920005606 polypropylene copolymer Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 150000003623 transition metal compounds Chemical class 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- FXNGQGIWLUWGBV-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)-n-methylmethanamine Chemical compound CNCC1=NC=CN1 FXNGQGIWLUWGBV-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- OOQKVEBNEUBZHO-UHFFFAOYSA-K C(C(C)(C)C)(=O)[O-].C(C(C)(C)C)(=O)[O-].C(C(C)(C)C)(=O)[O-].CC1(C=CC=C1)[Zr+3] Chemical compound C(C(C)(C)C)(=O)[O-].C(C(C)(C)C)(=O)[O-].C(C(C)(C)C)(=O)[O-].CC1(C=CC=C1)[Zr+3] OOQKVEBNEUBZHO-UHFFFAOYSA-K 0.000 description 2
- ZMCAXKMVYONJBS-UHFFFAOYSA-N C1=CC=C2C([Li])=C(CC)OC2=C1 Chemical compound C1=CC=C2C([Li])=C(CC)OC2=C1 ZMCAXKMVYONJBS-UHFFFAOYSA-N 0.000 description 2
- 125000001853 C4-C20 hydrocarbyl group Chemical group 0.000 description 2
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- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- SCABQASLNUQUKD-UHFFFAOYSA-N silylium Chemical class [SiH3+] SCABQASLNUQUKD-UHFFFAOYSA-N 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 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 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- NVBHDPLKAHDQDC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)borane;2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1.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.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 NVBHDPLKAHDQDC-UHFFFAOYSA-N 0.000 description 1
- MDYARPNTSPYOED-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)borane;2-undecyl-4,5-dihydro-1h-imidazole Chemical compound CCCCCCCCCCCC1=NCCN1.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.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 MDYARPNTSPYOED-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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 System
- C07F5/02—Boron compounds
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/645—Component covered by group C08F4/64 with a metal or compound covered by group C08F4/44, not provided for in a single group of groups C08F4/642 - C08F4/643
-
- 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
Description
本出願は、2006年5月5日に出願された米国仮出願第60/798,108号の利益を主張する。
式中、Xは各出現で独立して、C4-20ヒドロカルビル、トリヒドロカルビルシリル又はトリヒドロカルビルシリルヒドロカルビル基であり;
Yは、水素をカウントせずに合計2〜50個の原子を有するC2-3ヒドロカルビレン架橋基又はその置換誘導体であり、−C−N=C−と共に5又は6員脂肪族又は芳香族環式又は多環式基を形成し;
Tは、1又はそれ以上の環を含有する脂環式又は芳香族基であり;
R1は各出現で独立して、水素、ハロゲン、又は1価、多原子アニオン性リガンドであり、或いは2又はそれ以上のR1基が共に結合されてそれにより多価縮合環系を形成し;
R2は各出現で独立して、水素、ハロゲン、又は1価、多原子アニオン性リガンドであり、或いは2又はそれ以上のR2基が共に結合されてそれにより多価縮合環系を形成し;
ただし、金属錯体が20℃(±1℃)にて少なくとも5パーセントの、さらに好ましくは少なくとも7パーセントの、なおさらに好ましくは少なくとも10パーセントの、最も好ましくは少なくとも12パーセントのメチルシクロヘキサン溶解度を有するという条件である。この点で最も好ましい錯体は、Xが各出現においてC4-20n−アルキルである錯体である。
式中、R1は各出現で独立して、フェニル環に結合された炭素が2級又は3級置換されたC3-12アルキル基であり、好ましくは各R1はイソプロピルであり;
R2は各出現で独立して、水素又はC1-12アルキル基であり、好ましくは少なくとも1のオルト−R2基が、フェニル環に結合された炭素が2級又は3級置換されるメチル又はC3-12アルキルであり;
R3は、水素、ハロ又はR1であり;
R4は、水素、1〜20個の炭素のアルキル、アリール、アラルキル、トリヒドロカルビルシリル、又はトリヒドロカルビルシリルメチルであり;及び
X及びTは、式(I)の化合物で先に定義した通りである。
式中、
R1は各出現で独立して、フェニル環に結合された炭素が2級又は3級置換されたC3-12アルキル基であり、さらに好ましくは、各R1はイソプロピルであり;
R2は各出現で独立して、水素又はC1-12アルキル基であり、さらに好ましくは少なくとも1のオルト−R2基が、フェニル環に結合された炭素が2級又は3級置換されたメチル又はC3-12アルキルであり;
R4は、メチル又はイソプロピルであり;
R5は、水素又はC1-6アルキル、最も好ましくはエチルであり;
R6は、水素、C1-6アルキル又はシクロアルキルであり、或いは2個のR6基が一緒になって縮合芳香族環を形成し、好ましくは2個のR6基は共にベンゾ置換基であり;
T’は、酸素、硫黄、或いはC1-20ヒドロカルビル置換窒素又はリン基であり;
T”は、窒素又はリンであり;
Xは、式(I)に関して先に定義した通りであり、最も好ましくはXは、n−ブチル、n−オクチル又はn−ドデシルである。
A*+はカチオン、特にプロトン含有カチオンであり、好ましくは1又は2個のC10-40アルキル基を含有するトリヒドロカルビルアンモニウムカチオン、特にメチルジ(C14-20アルキル)アンモニウムカチオンであり、
R4は各出現で独立して、水素又は水素をカウントせずに原子30個までのハロ、ヒドロカルビル、ハロカルビル、ハロヒドロカルビル、シリルヒドロカルビル、或いはシリル(モノ、ジ及びトリ(ヒドロカルビル)シリルを含む)基、好ましくはC1-20アルキルであり、及び
J*は、トリス(ペンタフルオロフェニル)ボラン又はトリス(ペンタフルオロフェニル)アルマン)である。
ビス(トリス(ペンタフルオロフェニル)ボラン)イミダゾリド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−2−ウンデシルイミダゾリド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−2−ヘプタデシルイミダゾリド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−4,5−ビス(ウンデシル)イミダゾリド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−4,5−ビス(ヘプタデシル)イミダゾリド、
ビス(トリス(ペンタフルオロフェニル)ボラン)イミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−2−ウンデシルイミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−2−ヘプタデシルイミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−4,5−ビス(ウンデシル)イミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−4,5−ビス(ヘプタデシル)イミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−5,6−ジメチルベンズイミダゾリド、
ビス(トリス(ペンタフルオロフェニル)ボラン)−5,6−ビス(ウンデシル)ベンズイミダゾリド、
ビス(トリス(ペンタフルオロフェニル)アルマン)イミダゾリド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−2−ウンデシルイミダゾリド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−2−ヘプタデシルイミダゾリド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−4,5−ビス(ウンデシル)イミダゾリド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−4,5−ビス(ヘプタデシル)イミダゾリド、
ビス(トリス(ペンタフルオロフェニル)アルマン)イミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−2−ウンデシルイミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−2−ヘプタデシルイミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−4,5−ビス(ウンデシル)イミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−4,5−ビス(ヘプタデシル)イミダゾリニド、
ビス(トリス(ペンタフルオロフェニル)アルマン)−5,6−ジメチルベンズイミダゾリド、及び
ビス(トリス(ペンタフルオロフェニル)アルマン)−5,6−ビス(ウンデシル)ベンズイミダゾリド
の、メチルジ(C14-20アルキル)アンモニウム塩を含む。
金属錯体及び共触媒又はアクチベーターに加えて、改善された触媒性能又は他の利点を得るために、ある第3成分又はその混合物が触媒組成物又は反応混合物に添加されうることが考慮される。このような第3成分の例は、触媒不活性化を防止するために反応混合物中の汚染物質と反応するように設計されたスカベンジャーを含む。適切な第3成分はまた、触媒組成物で使用される金属錯体の1又はそれ以上の活性化を活性化又は補助しうる。
M(Q)x(OOCR)yによって表され、式中
Mは、1〜16族並びにランタニド及びアクチニド系列からの、好ましくは1〜7及び12〜16族からの、さらに好ましくは3〜7及び12〜14族からの、なおさらに好ましくは12族からの金属、最も好ましくはZnであり;
Qは、ハロゲン、水素、ヒドロキシド、或いは水素をカウントしない原子20個までのアルキル、アルコキシ、アリールオキシ、シロキシ、シラン、スルホナート又はシロキサン基であり;
Rは、1〜50個の炭素原子、好ましくは1〜20個の炭素原子を有し、場合により1又はそれ以上のヒドロキシ、アルコキシ、N,N−ジヒドロカルビルアミノ、又はハロ基によって置換されたヒドロカルビルラジカルであり、ただし、1回の出現においてRがヒドロキシ又はN,N−ジヒドロカルビルアミノ基、好ましくは金属Mにその非共有電子によって配位されているヒドロキシ基によって置換されるという条件であり;
xは、0〜3の整数であり;
yは、1〜4の整数である。
式中、
Mは、+2又は+4形式酸化状態のチタン、ジルコニウム又はハフニウム、好ましくはジルコニウム又はハフニウムであり;
R3は各出現において独立して、水素、ヒドロカルビル、シリル、ゲルミル、シアノ、ハロ及びその組合せからなる群より選択され、前記R3は最大20個の非水素原子を有し、又は隣接R3基は共に2価誘導体(すなわち、ヒドロカルバジイル、シラジイル、又はゲルマジイル基)を形成してそれにより縮合環形を形成し、
X”は各出現で独立して、最大40個の非水素原子のアニオン性リガンド基であり、或いは2個のX”基は、最大40個の非水素原子の2価アニオン性リガンド基を共に形成するか、又は共に、Mとπ錯体を形成する4〜30個の非水素原子を有するコンジュゲートジエンであり、ここでMは+2形式酸化状態にあり、
R*は各出現で独立して、C1-4アルキル又はフェニルであり、及び
Eは各出現で独立して、炭素又はケイ素であり、
xは、1〜8の整数である。
式中、
Mは、+2、+3又は+4形式酸化状態のチタン、ジルコニウム又はハフニウムであり;
R3は各出現において独立して、水素、ヒドロカルビル、シリル、ゲルミル、シアノ、ハロ及びその組合せからなる群より選択され、前記R3は最大20個の非水素原子を有し、又は隣接R3基は共に2価誘導体(すなわち、ヒドロカルバジイル、シラジイル、又はゲルマジイル基)を形成してそれにより縮合環形を形成し、
各X”は、ハロ、ヒドロカルビル、ヒドロカルビルオキシ、ヒドロカルビルアミノ、又はシリル基であり、前記基は最大20個の非水素原子を有するか、あるいは2個のX”基は共に中性C5-30コンジュゲートジエン又はその2価誘導体を形成し;
Yは、−O−、−S−、−NR*−、−PR*−であり;
Zは、SiR* 2、CR* 2、SiR* 2SiR* 2、CR* 2CR* 2、CR*=CR*、CR* 2SiR* 2、又はGeR* 2であり、ここでR*は先に定義した通りであり、及び
nは、0〜3の整数である。
式中、M’は、元素周期律表の4、5又は6族からの金属、好ましくはチタン、ジルコニウム又はハフニウム、最も好ましくはジルコニウム又はハフニウムであり;
L’は、M’に配位された、そしてTが存在するときにはTに結合された置換又は非置換π−結合リガンドであり、好ましくはL’は、1〜20個の炭素原子を有する1又はそれ以上のヒドロカルビル置換基を場合により備えたシクロアルカジエニルリガンド、又はその縮合環誘導体、例えばシクロペンタジエニル、インデニル又はフルオレニルリガンドであり;
各Q’は、−O−、−NR’−、−CR’2−及び−S−からなる群より独立して選択され、好ましくは酸素であり;
Y’は、C又はSのどちらか、好ましくは炭素であり;
Z’は、−OR’、−NR’2、−CR’3、−SR’、−SiR’3、−PR’2、−H、及び置換又は非置換アリール基からなる群より選択され、ただし、Qが−NR’−であるときに、そこでZは、−OR’、−NR’2、−SR’、−SiR’3、−PR’2及び−Hからなる群より選択され、好ましくはZは、−OR’、−CR’3及び−NR’2からなる群より選択されるという条件であり;
n’は、1又は2、好ましくは1であり;
A’は、nが2であるときに1価アニオン性基であり、又はA’は、nが1であるときに2価アニオン性基であり、好ましくはA’は、カルバメート、ヒドロキシカルボキシラート、又はQ’、Y’及びZ’の組合せによって記載される他のヘテロアリール部分であり;
各R’は独立して、炭素、ケイ素、窒素、酸素、及び/又はリンを含有する基であり、1又はそれ以上のR’基はL’置換基にも結合でき、好ましくはR’は、1〜20個の炭素原子を含有する炭化水素基、最も好ましくはアルキル、シクロアルキル、又はアリール基であり;
Tは、炭素又は(複数の)ヘテロ原子によって場合により置換される1〜10個の炭素原子を含有するアルキレン及びアリーレン基、ゲルマニウム、ケイ素及びアルキルホスフィンからなる群より選択される架橋基であり;
mは、2〜7、好ましくは2〜6、最も好ましくは2又は3である。
本発明の工程によって製造されたポリマーは、多種多様の製品及び最終使用用途で使用されうる。本発明の工程によって製造されたポリマーは、高密度ポリエチレン、低密度ポリエチレン、直鎖低密度ポリエチレン(エチレン/α−オレフィンコポリマー)、ポリプロピレン、プロピレン及びエチレンのコポリマー、並びにエチレン/プロピレン/ジエンターポリマーを含む。特に好ましいポリマーは、65パーセント又はそれ以上の、好ましくは85パーセント又はそれ以上の重合プロピレン及び実質的にアイソタクチックプロピレンセグメントを含有するプロピレン/エチレン又はプロピレン/エチレン/ジエンインターポリマーである。
式中、Kpp=1.90×10-4、app=0.725及びKps=1.26×10-4、aps=0.702。
本発明の次の具体的な実施形態及びその組合せは特に望ましく、添付請求項の詳細な開示を与えるために本明細書によって記載されている。
Yは、水素をカウントせずに合計2〜50個の原子を有するC2-3ヒドロカルビレン架橋基又はその置換誘導体であり、−C−N=C−と共に5又は6員脂肪族又は芳香族環式又は多環式基を形成し;
Tは、1又はそれ以上の環を含有する脂環式又は芳香族基であり;
R1は各出現で独立して、水素、ハロゲン、又は1価、多原子アニオン性リガンドであり、或いは2又はそれ以上のR1基が共に結合されてそれにより多価縮合環系を形成し;
R2は各出現で独立して、水素、ハロゲン、又は1価、多原子アニオン性リガンドであり、或いは2又はそれ以上のR2基が共に結合されてそれにより多価縮合環系を形成し;
ただし、金属錯体が20℃(±1℃)にて少なくとも5パーセントの、さらに好ましくは少なくとも7パーセントの、なおさらに好ましくは少なくとも10パーセントの、最も好ましくは少なくとも12パーセントのメチルシクロヘキサン溶解度を有するという条件である)
に相当する金属錯体。
R1は各出現で独立して、フェニル環に結合された炭素が2級又は3級置換されたC3-12アルキル基であり、好ましくは各R1はイソプロピルであり;
R2は各出現で独立して、水素又はC1-12アルキル基であり、好ましくは少なくとも1のオルト−R2基が、フェニル環に結合された炭素が2級又は3級置換されるメチル又はC3-12アルキルであり;
R3は、水素、ハロ又はR1であり;
R4は、水素、1〜20個の炭素のアルキル、アリール、アラルキル、トリヒドロカルビルシリル、又はトリヒドロカルビルシリルメチルであり;
X及びTは、式(I)の化合物で先に定義した通りである)
に相当する、実施形態1に記載の金属錯体。
R1は各出現で独立して、フェニル環に結合された炭素が2級又は3級置換されたC3-12アルキル基であり、さらに好ましくは各R1はイソプロピルであり;
R2は各出現で独立して、水素又はC1-12アルキル基であり、さらに好ましくは少なくとも1のオルト−R2基が、フェニル環に結合された炭素が2級又は3級置換されるメチル又はC3-12アルキルであり;
R4は、メチル又はイソプロピルであり;
R5は、水素又はC1-6アルキル、最も好ましくはエチルであり;
R6は、水素、C1-6アルキル又はシクロアルキルであり、或いは2個のR6基が一緒になって縮合芳香族環を形成し、好ましくは2個のR6基は共にベンゾ置換基であり;
T’は、酸素、硫黄、或いはC1-20ヒドロカルビル置換窒素又はリン基であり、
T”は、窒素又はリンであり;
Xは、式(I)に関して先に定義した通りであり、最も好ましくはXは、n−ブチル、n−オクチル又はn−ドデシルである)
に相当する、実施形態2に記載の金属錯体。
続いての4〜20個の炭素を有するヒドロカルビル、トリヒドロカルビルシリル又はトリヒドロカルビルシリルヒドロカルビル基のマグネシウムブロミド又はマグネシウムクロライド誘導体との反応と、生じたアルキル化生成物の回収とによる、実施形態1に記載の有機複素環式リガンドのハフニウム錯体の調製のための工程において、改善(improvement)が脂肪族又は脂環式炭化水素液体を使用してアルキル化の不溶性マグシウム副生成物からアルキル化生成物を抽出するステップと、金属錯体を回収するステップとを含む工程。
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,4,6−トリ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)、
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,6−ジ(l−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)、
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,4,6−トリ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−オクチル)、又は
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,6−ジ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−オクチル)である、実施形態8に記載の工程。
前記工程が、式、
得られたボラートエステル生成物を回収するステップと、
を含み、式中、
RWはC1-4アルキルであり;
RXは、C1-10ヒドロカルビル又はハロヒドロカルビルであり;及び
RYは各出現で独立して、C1-10ヒドロカルビル、ハロヒドロカルビル又はトリアルキルシリルヒドロカルビルであるか、或いは2RY基は共に最大20個の炭素の2価ヒドロカルビレンである、工程。
3−リチオ−2−エチルベンゾフランを形成するために−75℃未満の温度にて3−ブロモ−2−エチルベンゾフランにn−ブチルリチウムを接触させるステップと、
−75℃未満の温度にて3−リチオ−2−エチルベンゾフランに式、
得られた環式ボロナートエステルを回収するステップと、
を含む、工程。
2−リチオ化誘導体を形成するために10℃未満の、好ましくは0℃未満の、最も好ましくは−25℃未満の温度にて式、
生じた生成物を分離するステップと、−75℃未満の温度にてほぼ等モル量の生成物をジメチルホルムアミドと接触させるステップと、
得られた生成物を回収するステップと、を含み、式中、
RSはC1-4アルキルであり、及び
RTは、ハロ又はC1-4アルキルである、工程。
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,4,6−トリ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3,4−ジイル−κ−C4)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)
1H NMR(CDCl3)δ1.2(d,12H)、1.5(t,3H),3.0(七重線,2H),3.15(q,2H)4.2(s,3H),7.2(m,3H),7.35(m,2H),7.6(d,2H),7.85(d,2H)。
GC/MS 413(M+),398,370,227,211,186,170,155,144,128,115,103。
1H NMR(CDCl3)δ0.5(bs,3H),0.7(bs,3H),0.95(d,6H),1.25(d,6H),1.3−1.4(m,12H))1.6(t,3H),2.75(七重線,1H),2.9(七重線,1H),3.0(s,3H),3.1(七重線,2H),3.25(七重線,1H),3.35(q,2H),3.8(bs,1H),5.1(s,1H),5.7(s,1H),6.9(s,1H),6.95−7.1(m,3H),7.2(m,2H),7.45(dd,2H),7.75(dd,2H)ppm。
GC/MS 617(M+),442,425,399,281,227,162,120。
1H NMR(C6D6):δ7.62(d,J=8Hz,1H),7.42(d,J=8Hz,1H),7.25−7.00(多重線,6H),6.93(d,J=2Hz,1H),6.22(s,1H),5.84(s,1H)、3.95(七重線,J=7Hz、1H),3.71(七重線,J=7Hz,1H),3.60(七重線,J=7Hz,1H),2.89(七重線,J=7Hz,1H),2.85(q,J=8Hz,2H),2.72(七重線,J=7Hz,1H),2.32(s,3H),2.0−0.8(多重線,アルキル鎖プロトン),1.55(d,J=7Hz,3H),1.54(d,J=7Hz,3H),1.41(d,J=7Hz,3H),1.40(d,J=7Hz,3H),1.18(d,J=7Hz,3H),1.17(d,J=7Hz,3H),1.05(d,J=7Hz,3H),0.90(t,J=7Hz,9H),0.76(t,J=7Hz,3H),0.72(d,J=7Hz,3H),0.52(d,J=7Hz,3H),0.20,(d,J=7Hz,3H)。
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,6−ジ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル−κ−C4)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)
1H NMR(C6D6):δ7.61(d,J=8Hz,1H),7.43(d,J=8Hz,1H),7.25−7.05(多重線,7H),6.94(dd,J=2,7Hz,1H),6.22(s,1H),5.84(s,1H),3.96(七重線,J=7Hz,1H),3.75(七重線,J=7Hz,1H),3.59(七重線,J=7Hz,1H),2.86(多重線,3H),2.26(s,3H),2.0−1.15(多重線,アルキル鎖メチレンプロトン),1.55(d,J=7Hz,3H),1.51(d,J=7Hz,3H),1.41(t,J=7Hz,3H),1.02(d,J=7Hz,3H),0.91(t,J=7Hz,9H),0.75(d,J=7Hz,3H),0.72(d,J=7Hz,3H),0.71(d,J=7Hz,3H),0.52(d,J=7Hz,3H),0.27(d,J=7Hz,3H)。
重合はコンピュータ制御され、撹拌されている、ジャケット付き1.8Lステンレス鋼オートクレーブ溶液バッチリアクタで実施する。リアクタの底に大型オリフィス底排出弁が装着されていて、リアクタの内容を6Lステンレス鋼容器に排出する。容器を30ガロン排出タンクへ排出させて、容器及びタンクの両方を窒素でパージする。重合又は触媒補給に使用する全ての化学薬品は精製カラムを通過させて、いずれの不純物も除去する。プロピレン及び溶媒を2個のカラムに通過させて、第1のカラムはアルミナを含有し、第2のカラムは精製反応物質(Englehardt Corporationから入手可能なQ5(商標))を含有している。窒素及び水素ガスを、Q5(商標)反応物質を含有する1個のカラムに通過させる。
Claims (6)
- ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,4,6−トリ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)、
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,6−ジ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)、
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,4,6−トリ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−オクチル)、又は
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,6−ジ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−オクチル)である、金属錯体。 - 100ppm未満のマグネシウム塩副生成物を含有する、請求項1に記載の金属錯体。
- HfCl4と、式、
(式中、Tは2−エチルベンゾフランであり;R1はイソプロピルであり;R2は各出現で独立して、水素またはフェニル環に結合された炭素が2級置換されるC 3 アルキルであり;R 3 は水素であり;さらにR 4 はメチルである)に相当する複素環式化合物のリチオ化誘導体との化合、
続いての4〜20個の炭素を有するヒドロカルビル基のマグネシウムブロミド又はマグネシウムクロライド誘導体との反応と、生じたアルキル化生成物の回収とによる、
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,4,6−トリ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)、
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,6−ジ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−ブチル)、
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,4,6−トリ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−オクチル)、又は
ハフニウム,[N−[2,6−ビス(1−メチルエチル)フェニル]−α−[2,6−ジ(1−メチルエチル)フェニル]−5−(2−エチルベンゾフラン−3−イル)−2−(N’−メチル)イミダゾール−2−イル)メタンアミナート(2−)−κN1,κN2]トリ(n−オクチル)から選択される、有機複素環式リガンドのハフニウム錯体の調製方法において、
改善が脂肪族又は脂環式炭化水素液体を使用してアルキル化の不溶性マグシウム副生成物からアルキル化生成物を抽出するステップと、金属錯体を回収するステップとを含む方法。 - 1又はそれ以上のオレフィンモノマーが重合条件下で触媒組成物と接触される付加重合の方法であって、触媒組成物が請求項1に記載の金属錯体及び共触媒を含むことを特徴とする、付加重合方法。
- 溶液重合工程である、請求項4に記載の方法。
- プロピレン及びエチレンが共重合され、或いはプロピレン、エチレン、及び1−オクテン、4−メチル−1−ペンテン、ブタジエン、ノルボルネン、エチリデンノルボルネン、1,4−ヘキサジエン、1,5−ヘキサジエン、ノルボルナジエン、及び1−ブテンからなる群より選択される1又はそれ以上のモノマーが、100〜150℃の温度、100kPa〜10MPaの圧力、及び25〜500kPaの水素分圧にて共重合される、請求項5に記載の方法。
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EP (1) | EP2021381B1 (ja) |
JP (2) | JP5498781B2 (ja) |
KR (3) | KR101476581B1 (ja) |
CN (1) | CN101479299B (ja) |
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CA (1) | CA2651314A1 (ja) |
ES (1) | ES2560247T3 (ja) |
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WO (1) | WO2007130242A2 (ja) |
Families Citing this family (4)
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US7858817B2 (en) * | 2008-03-10 | 2010-12-28 | Exxonmobil Chemical Patents Inc. | Metallocene-substituted pyridyl amines, their metal complexes, and processes for production and use thereof |
EP2989130B1 (en) | 2013-04-23 | 2019-05-15 | ExxonMobil Chemical Patents Inc. | Pyridyldiamide metal catalysts and processes to produce polyolefins |
CN112533964B (zh) | 2018-07-31 | 2024-03-12 | 陶氏环球技术有限责任公司 | 双齿唑基氨基金属-配体络合物和烯烃聚合催化剂 |
CN111185241B (zh) * | 2020-03-09 | 2022-08-02 | 邯郸学院 | 一种金属催化剂及其制备方法与应用 |
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US5045557A (en) * | 1987-03-20 | 1991-09-03 | Schering Agrochemicals Ltd. | Imidazable fungicides and use thereof |
GB9110636D0 (en) * | 1991-05-16 | 1991-07-03 | Glaxo Group Ltd | Chemical compounds |
US6103657A (en) * | 1997-07-02 | 2000-08-15 | Union Carbide Chemicals & Plastics Technology Corporation | Catalyst for the production of olefin polymers |
CA2274994A1 (en) * | 1998-06-18 | 1999-12-18 | Lonza Ag | Process for the preparation of formylimidazoles |
US6713577B2 (en) * | 2000-11-07 | 2004-03-30 | Symyx Technologies, Inc. | Substituted pyridyl amine catalysts and processes for polymerizing and polymers |
EP1343838B1 (de) | 2000-12-13 | 2005-04-06 | Crompton Vinyl Additives GmbH | Stabilisatorsystem zur stabilisierung halogenhaltiger polymere |
US6960635B2 (en) * | 2001-11-06 | 2005-11-01 | Dow Global Technologies Inc. | Isotactic propylene copolymers, their preparation and use |
CA2485093A1 (en) * | 2002-05-02 | 2003-11-13 | Neurogen Corporation | Substituted imidazole derivatives: gabaa receptor ligands |
US7276603B2 (en) * | 2003-05-02 | 2007-10-02 | Wyeth | Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use |
US7387980B2 (en) * | 2004-09-22 | 2008-06-17 | Symyx Technologies, Inc. | Methods of using heterocycle-amine ligands, compositions, complexes, and catalysts |
US7256296B2 (en) * | 2004-09-22 | 2007-08-14 | Symyx Technologies, Inc. | Heterocycle-amine ligands, compositions, complexes, and catalysts |
US20090186996A1 (en) * | 2006-05-05 | 2009-07-23 | Boone Harold W | Hafnium complexes of carbazolyl substituted imidazole ligands |
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KR20140006108A (ko) | 2014-01-15 |
US20130085284A1 (en) | 2013-04-04 |
CN101479299A (zh) | 2009-07-08 |
US20090069567A1 (en) | 2009-03-12 |
JP2009536200A (ja) | 2009-10-08 |
KR20140004804A (ko) | 2014-01-13 |
US8362265B2 (en) | 2013-01-29 |
US20130102789A1 (en) | 2013-04-25 |
KR101476581B1 (ko) | 2014-12-24 |
CN101479299B (zh) | 2012-08-15 |
RU2008147894A (ru) | 2010-06-10 |
JP2013139456A (ja) | 2013-07-18 |
WO2007130242A3 (en) | 2008-01-31 |
KR101476582B1 (ko) | 2014-12-24 |
BRPI0710329A2 (pt) | 2011-08-09 |
KR101397289B1 (ko) | 2014-05-22 |
KR20090009947A (ko) | 2009-01-23 |
US20130102795A1 (en) | 2013-04-25 |
EP2021381B1 (en) | 2015-12-23 |
ES2560247T3 (es) | 2016-02-18 |
JP5775104B2 (ja) | 2015-09-09 |
US8580976B2 (en) | 2013-11-12 |
WO2007130242A2 (en) | 2007-11-15 |
CA2651314A1 (en) | 2007-11-15 |
EP2021381A2 (en) | 2009-02-11 |
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