JP7364585B2 - オレフィン重合のための二核助触媒としての高溶解性ビスホウ酸 - Google Patents
オレフィン重合のための二核助触媒としての高溶解性ビスホウ酸 Download PDFInfo
- Publication number
- JP7364585B2 JP7364585B2 JP2020551431A JP2020551431A JP7364585B2 JP 7364585 B2 JP7364585 B2 JP 7364585B2 JP 2020551431 A JP2020551431 A JP 2020551431A JP 2020551431 A JP2020551431 A JP 2020551431A JP 7364585 B2 JP7364585 B2 JP 7364585B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- cocatalyst
- independently
- 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.)
- Active
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 32
- 150000001336 alkenes Chemical class 0.000 title description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 11
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 59
- 239000005977 Ethylene Substances 0.000 claims description 59
- 239000003054 catalyst Substances 0.000 claims description 57
- 229920000642 polymer Polymers 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 39
- -1 n-octyl Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 239000004711 α-olefin Substances 0.000 claims description 17
- 150000001768 cations Chemical class 0.000 claims description 15
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003426 co-catalyst Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 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 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000002948 undecyl 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])[H] 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 13
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000012454 non-polar solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000003636 chemical group Chemical group 0.000 description 6
- 230000009977 dual effect Effects 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000004896 high resolution mass spectrometry Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000007614 solvation Methods 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 2
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 2
- 125000006313 (C5-C8) alkyl group Chemical group 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910000799 K alloy Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910000528 Na alloy Inorganic materials 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 description 2
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 239000003039 volatile agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- QPFMBZIOSGYJDE-QDNHWIQGSA-N 1,1,2,2-tetrachlorethane-d2 Chemical compound [2H]C(Cl)(Cl)C([2H])(Cl)Cl QPFMBZIOSGYJDE-QDNHWIQGSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FKFQAMBWSMTERU-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2-octylbenzene Chemical compound C(CCCCCCC)C1=C(C(C2=CC=CC=C2)(C2=CC=CC=C2)Cl)C=CC=C1 FKFQAMBWSMTERU-UHFFFAOYSA-N 0.000 description 1
- OOZQSVXPBCINJF-UHFFFAOYSA-N 1-bromo-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(Br)C=C1 OOZQSVXPBCINJF-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-RALIUCGRSA-N 1-chloro-2,3,4,5,6-pentadeuteriobenzene Chemical compound [2H]C1=C([2H])C([2H])=C(Cl)C([2H])=C1[2H] MVPPADPHJFYWMZ-RALIUCGRSA-N 0.000 description 1
- PRTLUGCYFALHIH-UHFFFAOYSA-N 1-tert-butyl-2-[chloro(diphenyl)methyl]benzene Chemical compound C(C)(C)(C)C1=C(C(C2=CC=CC=C2)(C2=CC=CC=C2)Cl)C=CC=C1 PRTLUGCYFALHIH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910019440 Mg(OH) Inorganic materials 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- JXBAVRIYDKLCOE-UHFFFAOYSA-N [C].[P] Chemical group [C].[P] JXBAVRIYDKLCOE-UHFFFAOYSA-N 0.000 description 1
- YCLSRHGKSJADJL-UHFFFAOYSA-N [Li+].B([O-])([O-])O.[Li+].B(O)(O)O Chemical compound [Li+].B([O-])([O-])O.[Li+].B(O)(O)O YCLSRHGKSJADJL-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- PREAJPIKNPDDON-APAIHEESSA-N dideuterio-[dichloro(deuterio)methyl]-lambda3-chlorane Chemical compound C(Cl([2H])[2H])(Cl)(Cl)[2H] PREAJPIKNPDDON-APAIHEESSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000630 rising effect Effects 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
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- 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
- C08F4/64003—Titanium, zirconium, hafnium or compounds thereof the metallic compound containing a multidentate ligand, i.e. a ligand capable of donating two or more pairs of electrons to form a coordinate or ionic bond
- C08F4/64006—Bidentate ligand
- C08F4/64041—Monoanionic ligand
- C08F4/64048—NO
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- C—CHEMISTRY; METALLURGY
- 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
- C07F5/02—Boron compounds
-
- 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
- C08F10/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F4/64003—Titanium, zirconium, hafnium or compounds thereof the metallic compound containing a multidentate ligand, i.e. a ligand capable of donating two or more pairs of electrons to form a coordinate or ionic bond
- C08F4/64082—Tridentate ligand
- C08F4/64141—Dianionic ligand
- C08F4/64144—NN(R)C
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
-
- 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
- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/03—Multinuclear procatalyst, i.e. containing two or more metals, being different or not
-
- 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
- C08F2420/00—Metallocene catalysts
- C08F2420/02—Cp or analog bridged to a non-Cp X anionic donor
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/03—Narrow molecular weight distribution, i.e. Mw/Mn < 3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/04—Broad molecular weight distribution, i.e. Mw/Mn > 6
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/09—Long chain branches
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/10—Short chain branches
-
- 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
- C08F4/52—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 selected from boron, aluminium, gallium, indium, thallium or rare earths
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
本出願は、2018年3月30日に出願された米国仮特許出願第62/650,437号に対する優先権を主張するものであり、その全体が参照により本明細書に組み込まれる。
先行する段落に記載される触媒系は、オレフィン、主にエチレンおよびプロピレンの重合に利用され、エチレン系ポリマーまたはプロピレン系ポリマーを形成する。いくつかの実施形態では、重合スキーム中に単一タイプのオレフィンまたはα-オレフィンのみが存在し、ホモポリマーを生成する。しかしながら、追加のα-オレフィンを重合手順に組み込んでもよい。追加のα-オレフィンコモノマーは、典型的には、20個以下の炭素原子を有する。例えば、α-オレフィンコモノマーは、3~10個の炭素原子、または3~8個の炭素原子を有し得る。例示的なα-オレフィンコモノマーとしては、プロピレン、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-ノネン、1-デセン、および4-メチル-1-ペンテンが挙げられるが、これらに限定されない。例えば、1つ以上のα-オレフィンコモノマーは、プロピレン、1-ブテン、1-ヘキセン、および1-オクテンからなる群から、または代替的に1-ヘキセンおよび1-オクテンからなる群から選択され得る。
トルエンでの重合手順:典型的な実験では、グローブボックスの内部で、150mLのガラス製圧力容器(使用前に120℃のオーブンで一晩乾燥)に、40mLの乾燥トルエンを充填した。大型磁気撹拌棒を圧力容器に加え、密閉して、グローブボックスから取り出し、高圧/高真空ラインに取り付けた。圧力容器をドライアイス/アセトン浴で-78℃まで冷却して脱気し、次いで外浴を使用して所望の反応温度で30分間加温および平衡化した。同時に、溶液を1.0気圧のエチレンで飽和した。測定された量のプロ触媒および助触媒を、グローブボックス内のバイアル(10mLのトルエン)中で混合して、10分間振とうすることにより、触媒的に活性な種を新たに生成した。次いで、触媒溶液をグローブボックスから取り出し、噴霧針を備える気密シリンジを使用して急速に撹拌している溶液に素早く注入した。代表的な重合実験におけるトルエン溶液の温度は、熱電対を使用して監視された。測定された時間間隔の後、5mLのMeOHを添加することにより重合をクエンチした。次いで、揮発性物質を真空下で除去することにより、溶液を約20mLに減らした。次いで、100mLの酸性化MeOH(MeOH中10%v/vのHCl)を添加し、ポリマーを数時間撹拌して、濾過し、メタノールで洗浄して、収集した。次いで、高真空下で80℃で一晩乾燥して、一定の重量にした。
エチレンおよび1-ヘキセンの共重合手順は、前述のエチレン単独重合手順と同様である。グローブボックスの内部で、350mLのガラス製圧力容器に、40mLの乾燥トルエンおよび10mLの1-ヘキセンを充填する。触媒の調製、重合フラスコへの注入、およびコポリマーの後処理のための手順は、前述の手順と同じである。
HT-GPC分析用の試料の実行は、IR分析に先行する。IR分析の場合、試料の堆積および1-オクテン取り込みの分析には、48ウェルのHTシリコンウエハを利用する。分析では、試料を160℃まで210分間以下加熱し、試料を再加熱して磁気GPC撹拌棒を取り外し、J-KEM Scientific加熱式ロボット振とう機においてガラス棒の撹拌棒を用いて振とうする。試料をTecan MiniPrepの75堆積ステーションを使用して加熱しながら堆積させ、1,2,4-トリクロロベンゼンを窒素パージ下で160℃でウエハの堆積ウェルから蒸発させる。1-オクテンの分析は、NEXUS 670 E.S.P.FT-IRを使用して、HTシリコンウエハ上で行う。
分子量データは、ハイブリッドのSymyx/Dow構築ロボット支援希釈高温度ゲル浸透クロマトグラフィー装置(Sym-RAD-GPC)における分析によって決定する。ポリマー試料を、300百万分率(ppm)のブチル化ヒドロキシルトルエン(BHT)によって安定化された10mg/mLの濃度で、1,2,4-トリクロロベンゼン(TCB)中に160℃で120分間加熱することによって溶解する。250μLアリコートの試料を注入する直前に、各試料を1mg/mLに希釈する。GPCは、160℃で2.0mL/分の流速で2つのPolymer Labs PLgelの10μmの混合-Bカラム(300×10mm)を備える。試料検出を、濃度モードでPolyChar IR4検出器を使用して行う。狭いポリスチレン(PS)標準の従来の較正を、この温度でTCB中のPSおよびPEについての既知のMark-Houwink係数を使用してホモポリエチレン(PE)に調整された見かけの単位を用いて利用する。
バッチ反応器重合は、2LのParrバッチ反応器内で行う。反応器を電気加熱マントルによって加熱し、冷却水を含有する内部蛇管冷却コイルによって冷却する。反応器および加熱/冷却システムの両方を、Camile(商標)TGプロセスコンピュータによって制御および監視する。反応器の底部をダンプ弁と嵌合し、これにより反応器の内容物を、触媒失活溶液(典型的には、5mLのIrgafos/Irganox/トルエン混合物)で事前に充填されたステンレス鋼ダンプポット内に出す。ポットおよびタンクの両方を窒素でパージして、ダンプポットを30ガロンのブローダウンタンクに通気する。重合または触媒組成に使用されるすべての溶媒は、溶媒精製カラムを通過させて、重合に影響を与え得るあらゆる不純物を除去する。1-オクテンおよびIsoparEは、A2アルミナを含有する第1のカラム、Q5を含有する第2のカラムの2つのカラムを通過させた。エチレンは、A204アルミナおよび4Åモレキュラーシーブを含有する第1のカラム、Q5反応物を含有する第2のカラムの2つのカラムを通過させた。移動のために使用した窒素ガスは、A204アルミナ、4Åモレキュラーシーブ、およびQ5を含有する単一のカラムを通過させる。
溶解度試験は室温(22.5±2.5℃)で行う。選択した温度を、機器のすべての関連する部分で一定に保つ。バイアルに、30mgの助触媒(試料)および1.0mLの溶媒を入れる。助触媒と溶媒の懸濁液を、周囲温度で30分間撹拌する。次いで、混合物を、風袋引きしたバイアルにシリンジフィルターを介して濾過し、溶液を測量する(Xgの溶液)。次に、溶媒を高真空下で完全に除去し、バイアルを再度測量する(Ygの試料)。「ρ溶媒」は、g/mL単位での溶媒の密度である。溶媒中の助触媒の溶解度は、mg/mLの単位で測定した。溶媒中の助触媒の溶解度を、以下のように計算した。
実施例1:n-オクチルトリチルアルコールの合成
すべての溶媒および試薬は商業的供給源から入手し、特に記載がない限り、受領したままの状態で使用する。無水トルエン、ヘキサン、テトラヒドロフラン、およびジエチルエーテルを、活性アルミナ、および場合によってはQ-5反応物質を通過させることによって精製する。窒素充填グローブボックス内で行われた実験に使用された溶媒を、活性化4Åモレキュラーシーブ上での保存によってさらに乾燥する。感湿反応用ガラス器具を、使用前に一晩オーブン内で乾燥する。NMRスペクトルを、Varian 400-MRおよびVNMRS-500分光計で記録する。LC-MS分析は、Waters 2424 ELS検出器、Waters 2998 PDA検出器、およびWaters 3100 ESI質量検出器と組み合わせたWaters e2695分離モジュールを使用して行う。LC-MS分離は、XBridge C18 3.5μm 2.1×50mmカラムで、5:95~100:0のアセトニトリルおよび水勾配(イオン化剤として0.1%ギ酸を有する)を使用して行う。HRMS分析は、エレクトロスプレーイオン化を備えるAgilent 6230 TOF質量分析計と組み合わせたZorbax Eclipse Plus C18 1.8μm 2.1×50mmカラムを備えるAgilent 1290 Infinity LCを使用して行う。1H NMRデータは、次のように報告する:化学シフト(多重度(br=幅広線、s=1重線、d=2重線、t=3重線、q=4重線、p=5重線、sex=6重線、sept=7重線、およびm=多重線)、積分値、および帰属)。基準物質として重水素化溶媒中の残留プロトンを使用して、1H NMRデータの化学シフトをテトラメチルシラン内部より低磁場のppm(TMS、δスケール)で報告する。13C NMRデータは、1Hデカップリングを用いて決定し、化学シフトは、基準として重水素化溶媒中の残留炭素を使用して、テトラメチルシラン(TMS、δスケール)からの低磁場(ppm)として報告する。
Claims (9)
- 触媒系であって、
プロ触媒と、
非ハロゲン化溶媒中に溶解された助触媒と、を含み、前記助触媒が、
以下の式を有する非配位性ホウ酸ジアニオンと、
2つのカチオンと、を含み、各カチオンが独立して、式(I)または式(II)に
従うカチオンから選択され、
式中、
各R1、R2、R3、R4、およびR5が独立して、-H、-F、-Cl、置換
もしくは非置換(C4-C40)アルキル、置換もしくは非置換(C4-C40)アルケ
ニル、または置換もしくは非置換(C4-C40)シクロアルキルから選択され、前記置
換(C4-C40)アルキルおよび置換(C4-C40)シクロアルキルが、1つ以上の
RSで置換され、各RSが、(C1-C20)アルキルまたはハロゲンから選択されるが
、
ただし、R1、R2、R3、R4、またはR5のうちの少なくとも1つが、置換
もしくは非置換(C4-C30)アルキル、または置換もしくは非置換(C4-C40)
シクロアルキルから選択されることを条件とし、
各R6およびR7が独立して、(C4-C30)アルキルから選択され、R8が
独立して、(C1-C20)アルキルまたは(C6-C18)アリールのいずれかから選
択される、触媒系。 - 各R1が独立して、(C4-C30)アルキルである、請求項1に記載の触媒系。
- 各R2、R3、R4、およびR5が、-Hである、請求項1又は2に記載の触媒系。
- 各R1が独立して、n-ブチル、tert-ブチル、1-ペンチル、1-ヘキシル、
ヘプチル、n-オクチル、tert-オクチル、ノニル、デシル、ウンデシル、またはドデシルから選択される、請求項1~3のいずれか一項に記載の触媒系。 - 各R1が独立して、直鎖(C4-C30)アルキル、または直鎖もしくは分岐(C5
-C30)アルキルから選択される、請求項1~4のいずれか一項に記載の触媒系。 - 各R1、R2、R3、R4、またはR5が、任意に置換された[C40]アルキルで
あり、前記置換[C 40 ]アルキルが、1つ以上のR S で置換され、各R S が独立して、(C 1 -C 20 )アルキルまたはハロゲンから選択される、請求項1に記載の触媒系。 - エチレン系ポリマーを生成するための重合プロセスであって、前記プロセスが、エチ
レンおよび任意に1つ以上のα-オレフィンを、触媒系の存在下で重合することを含み、
前記触媒系が、非ハロゲン化非プロトン性炭化水素溶媒中に溶解されたプロ触媒および助
触媒を含み、前記助触媒が、
以下の式を有する非配位性ホウ酸ジアニオンと、
2つのカチオンと、を含み、各カチオンが式(I)または式(II)に従い、
式中、
各R1、R2、R3、R4、およびR5が独立して、-H、F、Cl、置換もしくは非置換(C4-C40)アルキル、置換もしくは非置換(C4-C40)アルケニル、または置換もしくは非置換(C4-C40)シクロアルキルから選択され、前記置換(C4-C40)アルキルおよび置換(C4-C40)シクロアルキルが、1つ以上のRSで置換され、各RSが、(C1-C20)アルキルまたはハロゲンから選択されるが、
ただし、R1、R2、R3、R4、またはR5のうちの少なくとも1つが、置換もしくは非置換(C4-C30)アルキル、または置換もしくは非置換(C4-C40)シクロアルキルから選択されることを条件とし、各R6およびR7が独立して、(C4-C30)アルキルから選択され、R8が独立して、(C1-C20)アルキルまたは(C6-C18)アリールのいずれかから選択される、重合プロセス。 - 各R1が独立して、tert-ブチル、n-ブチル、tert-オクチル、またはn-オクチルである、請求項7に記載のプロセス。
- 各R2、R3、R4、およびR5が、-Hである、請求項7又は8に記載のプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862650437P | 2018-03-30 | 2018-03-30 | |
US62/650,437 | 2018-03-30 | ||
PCT/US2019/024599 WO2019191440A1 (en) | 2018-03-30 | 2019-03-28 | Highly soluble bis-borate as binuclear co-catalysts for olefin polymerizations |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021519357A JP2021519357A (ja) | 2021-08-10 |
JP7364585B2 true JP7364585B2 (ja) | 2023-10-18 |
Family
ID=66286978
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020551431A Active JP7364585B2 (ja) | 2018-03-30 | 2019-03-28 | オレフィン重合のための二核助触媒としての高溶解性ビスホウ酸 |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP3774934A1 (ja) |
JP (1) | JP7364585B2 (ja) |
KR (1) | KR20200141452A (ja) |
CN (1) | CN112041351B (ja) |
BR (1) | BR112020019339A2 (ja) |
SG (1) | SG11202008654WA (ja) |
WO (1) | WO2019191440A1 (ja) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002348336A (ja) | 2001-05-28 | 2002-12-04 | Idemitsu Petrochem Co Ltd | オレフィン系重合体、その製造方法及び該重合体を含む熱可塑性樹脂組成物 |
JP2002348343A (ja) | 2001-05-28 | 2002-12-04 | Idemitsu Petrochem Co Ltd | オレフィン系重合体、その製造方法及び該重合体を含む熱可塑性樹脂組成物 |
JP2009126902A (ja) | 2007-11-21 | 2009-06-11 | Nippon Polyethylene Kk | オレフィン重合用触媒及びそれを用いたオレフィンの重合方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3189175B2 (ja) * | 1993-07-02 | 2001-07-16 | 出光興産株式会社 | 芳香族ビニル化合物共重合体の製造方法 |
ATE194629T1 (de) | 1996-03-27 | 2000-07-15 | Dow Chemical Co | Hochlösliches aktivierungsmittel für olefinpolymerisationskatalysator |
DE59703850D1 (de) * | 1996-08-13 | 2001-07-26 | Basell Polyolefine Gmbh | Geträgertes Katalysatorsystem, Verfahren zu seiner Herstellung und seine Verwendung zur Polymerisation von Olefinen |
DE19703478A1 (de) * | 1997-01-31 | 1998-08-06 | Hoechst Ag | Verfahren zur Herstellung eines Matallocen-Katalysatorsystems |
CA2387874A1 (en) * | 1999-10-22 | 2001-05-03 | Exxon Chemical Patents, Inc. | Carbenium cationic complexes suitable for polymerization catalysts |
WO2003010171A1 (en) * | 2001-07-23 | 2003-02-06 | Dow Global Technologies, Inc. | Salt of lewis acid/acid adducts and catalyst activators therefrom |
AU2005224259B2 (en) | 2004-03-17 | 2010-09-09 | Dow Global Technologies Inc. | Catalyst composition comprising shuttling agent for ethylene multi-block copolymer formation |
WO2011021805A2 (ko) * | 2009-08-18 | 2011-02-24 | 주식회사 엘지화학 | 신규한 화합물, 이를 포함하는 촉매 조성물 및 이를 이용한 고리형 올레핀계 중합체의 제조방법 |
EP2722345B1 (en) * | 2012-10-18 | 2018-12-05 | Borealis AG | Catalyst for the polymerisation of olefins |
MX2015016913A (es) | 2013-06-28 | 2016-04-04 | Dow Global Technologies Llc | Oligomeros hiper-ramificados a base de etileno. |
-
2019
- 2019-03-28 CN CN201980022077.XA patent/CN112041351B/zh active Active
- 2019-03-28 JP JP2020551431A patent/JP7364585B2/ja active Active
- 2019-03-28 EP EP19719682.7A patent/EP3774934A1/en active Pending
- 2019-03-28 BR BR112020019339-9A patent/BR112020019339A2/pt active IP Right Grant
- 2019-03-28 SG SG11202008654WA patent/SG11202008654WA/en unknown
- 2019-03-28 WO PCT/US2019/024599 patent/WO2019191440A1/en active Application Filing
- 2019-03-28 KR KR1020207029422A patent/KR20200141452A/ko not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002348336A (ja) | 2001-05-28 | 2002-12-04 | Idemitsu Petrochem Co Ltd | オレフィン系重合体、その製造方法及び該重合体を含む熱可塑性樹脂組成物 |
JP2002348343A (ja) | 2001-05-28 | 2002-12-04 | Idemitsu Petrochem Co Ltd | オレフィン系重合体、その製造方法及び該重合体を含む熱可塑性樹脂組成物 |
JP2009126902A (ja) | 2007-11-21 | 2009-06-11 | Nippon Polyethylene Kk | オレフィン重合用触媒及びそれを用いたオレフィンの重合方法 |
Also Published As
Publication number | Publication date |
---|---|
US20210108005A1 (en) | 2021-04-15 |
CN112041351A (zh) | 2020-12-04 |
BR112020019339A2 (pt) | 2021-01-05 |
JP2021519357A (ja) | 2021-08-10 |
SG11202008654WA (en) | 2020-10-29 |
KR20200141452A (ko) | 2020-12-18 |
CN112041351B (zh) | 2023-12-29 |
WO2019191440A1 (en) | 2019-10-03 |
EP3774934A1 (en) | 2021-02-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2020515677A (ja) | オレフィン重合用のゲルマニウム架橋ビス−ビフェニル−フェノキシ触媒 | |
JP7495880B2 (ja) | オレフィン重合のための助触媒としての高溶解性アルキル置換ホウ酸カルベニウム | |
JP7293206B2 (ja) | 溶解性を改善させるために金属上に2つのメチレントリアルキルシリコン配位子を有するビスフェニルフェノキシポリオレフィン触媒 | |
JP7053589B2 (ja) | チオ尿素第4族遷移金属触媒および重合系 | |
JP7364585B2 (ja) | オレフィン重合のための二核助触媒としての高溶解性ビスホウ酸 | |
CN115038725B (zh) | 包括iii族和镧系元素双-苯基-苯氧基金属-配体络合物以及链转移剂的聚合方法 | |
JP7221948B2 (ja) | 溶解性を改善させるために金属上にメチレントリアルキルシリコン配位子を有するビスフェニルフェノキシポリオレフィン触媒 | |
JP7208981B2 (ja) | 溶解度を改善するために金属上にアルコキシ-またはアミド-配位子を有するビス-フェニル-フェノキシポリオレフィン触媒 | |
US12037440B2 (en) | Highly soluble bis-borate as binuclear co-catalysts for olefin polymerization | |
JP7051827B2 (ja) | チオグアニジン第iv族遷移金属触媒および重合系 | |
CN114364706A (zh) | 用于与链转移剂进行烯烃聚合的双齿联芳基苯氧基第iv族过渡金属催化剂 | |
JP7443328B2 (ja) | 二座アゾリルアミド金属-配位子錯体およびオレフィン重合触媒 | |
JP2023534663A (ja) | ビス-フェニルフェノキシ金属-配位子錯体のためのヒドロカルビル修飾メチルアルミノオキサン共触媒 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20201124 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20201120 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20210127 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220315 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20230224 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230314 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20230614 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230621 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20230912 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20231005 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7364585 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |