JP2021519363A - 二核オレフィン重合活性化剤 - Google Patents
二核オレフィン重合活性化剤 Download PDFInfo
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- JP2021519363A JP2021519363A JP2020551576A JP2020551576A JP2021519363A JP 2021519363 A JP2021519363 A JP 2021519363A JP 2020551576 A JP2020551576 A JP 2020551576A JP 2020551576 A JP2020551576 A JP 2020551576A JP 2021519363 A JP2021519363 A JP 2021519363A
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- hydrocarbyl
- alkyl
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- 239000012190 activator Substances 0.000 title claims abstract description 96
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 title claims description 33
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000005977 Ethylene Substances 0.000 claims abstract description 45
- 150000001450 anions Chemical class 0.000 claims abstract description 43
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 229910052751 metal Inorganic materials 0.000 claims abstract description 40
- 239000002184 metal Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 33
- 150000001768 cations Chemical class 0.000 claims abstract description 32
- 230000003197 catalytic effect Effects 0.000 claims abstract description 30
- 239000004711 α-olefin Substances 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 25
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 6
- -1 or R 13 R 21 Chemical compound 0.000 claims description 134
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 229930195733 hydrocarbon Natural products 0.000 claims description 39
- 239000004215 Carbon black (E152) Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 37
- 239000003446 ligand Substances 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 238000012360 testing method Methods 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 239000002952 polymeric resin Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 229920003002 synthetic resin Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 10
- 238000010586 diagram Methods 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 description 60
- 239000000243 solution Substances 0.000 description 37
- 150000003254 radicals Chemical group 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 34
- 238000005481 NMR spectroscopy Methods 0.000 description 31
- 125000005842 heteroatom Chemical group 0.000 description 26
- YSRFHVJGXPIDGR-UHFFFAOYSA-N dimethylsilane titanium Chemical compound [Ti].C[SiH2]C YSRFHVJGXPIDGR-UHFFFAOYSA-N 0.000 description 25
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 20
- 150000002500 ions Chemical class 0.000 description 19
- 239000002904 solvent Substances 0.000 description 17
- 125000002947 alkylene group Chemical group 0.000 description 16
- 238000003756 stirring Methods 0.000 description 14
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000010828 elution Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003426 co-catalyst Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- 125000003636 chemical group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229930195734 saturated hydrocarbon Natural products 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- DVZWQGLVEOWFOU-UHFFFAOYSA-N C[Hf]C Chemical compound C[Hf]C DVZWQGLVEOWFOU-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 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 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- SRKKQWSERFMTOX-UHFFFAOYSA-N cyclopentane;titanium Chemical compound [Ti].[CH]1C=CC=C1 SRKKQWSERFMTOX-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000004474 heteroalkylene group Chemical group 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000003039 volatile agent Substances 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- DPSOUODMTOWXTB-UHFFFAOYSA-N CC1=C(C)C(C)([Ti])C(C)=C1C Chemical compound CC1=C(C)C(C)([Ti])C(C)=C1C DPSOUODMTOWXTB-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920006124 polyolefin elastomer Polymers 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 239000000178 monomer Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000047 product 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
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 4
- 239000003643 water by type Substances 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
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 description 3
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SFPQWMKUAVIGIX-UHFFFAOYSA-N C1=CC=C2C([Ti])C=CC2=C1 Chemical compound C1=CC=C2C([Ti])C=CC2=C1 SFPQWMKUAVIGIX-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000002596 correlated effect Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 229910052735 hafnium Inorganic materials 0.000 description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 125000000743 hydrocarbylene group Chemical group 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- 229920005672 polyolefin resin Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000000923 (C1-C30) 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
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- NSFAOGQJJNSYAS-UHFFFAOYSA-N C(CCCCCCCCCC)C=1[N-]C=CN=1.[Na+] Chemical compound C(CCCCCCCCCC)C=1[N-]C=CN=1.[Na+] NSFAOGQJJNSYAS-UHFFFAOYSA-N 0.000 description 2
- ODMWVMRTMJXBPA-UHFFFAOYSA-N C1C=CC=C2C([Ti])CCC21 Chemical compound C1C=CC=C2C([Ti])CCC21 ODMWVMRTMJXBPA-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000007527 lewis bases Chemical class 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- YZERDTREOUSUHF-UHFFFAOYSA-N pentafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1F YZERDTREOUSUHF-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
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- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- QYXGWHHFSHVZON-UHFFFAOYSA-N tert-butylazanide dimethyl-(2-methyl-1H-inden-1-yl)silane 4-phenylbuta-1,3-dienylbenzene titanium(2+) Chemical compound C1(=CC=CC=C1)C=CC=CC1=CC=CC=C1.[Ti+2].CC=1C(C2=CC=CC=C2C1)[SiH](C)C.C(C)(C)(C)[NH-].C(C)(C)(C)[NH-] QYXGWHHFSHVZON-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- LGWZGBCKVDSYPH-UHFFFAOYSA-N triacontane Chemical compound [CH2]CCCCCCCCCCCCCCCCCCCCCCCCCCCCC LGWZGBCKVDSYPH-UHFFFAOYSA-N 0.000 description 1
- OLTHARGIAFTREU-UHFFFAOYSA-N triacontane Natural products CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000012795 verification Methods 0.000 description 1
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Abstract
Description
本出願は、2018年3月30日出願の米国仮特許出願第62/650,423号の利益を主張し、参照によりその全体が本明細書に組み込まれる。
絶縁媒体は、可能な限り効率的であるべきである。電気損失は、電場の存在下で、媒体が絶縁する効率を低下させる。抵抗は、電力または電気損失に逆相関するので、抵抗は、交流(AC)システムと直流(DC)システムとの両方で可能な限り高くする必要がある。
触媒系としては、プロ触媒を挙げることができる。プロ触媒は、式(I)のアニオンおよび対カチオンを有する二種金属活性化剤に錯体を接触させるか、または金属活性化剤と錯体を組み合わせることによって、触媒的に活性になることができる。プロ触媒は、チタン(Ti)金属−配位子錯体、ジルコニウム(Zr)金属−配位子錯体、またはハフニウム(Hf)金属−配位子錯体などの、第IV属金属(CASに従った第IVB族、またはIUPAC命名規則に従った第4族)−配位子錯体から選択することができる。限定を意図するものではないが、プロ触媒の例は、次の参考文献に見出すことができる:US8372927、WO2010/022228、WO2011/102989、US6953764、US6900321、WO2017/173080、US7650930、US6777509、WO99/41294、US6869904、WO2007/136496。これらの参考文献は、その全体が参照により本明細書に組み込まれる。
前の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る。いくつかの実施形態では、重合スキーム中に単一種類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つ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、4−メチル−1−ペンテン、5−エチリデン−2−ノルボルネン、および5−ビニル−2−ノルボルネンが挙げられるが、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。
バッチ式反応器の実験は、1ガロンの連続撹拌槽反応器で実施した。Isopar−E炭化水素溶媒、水素、および適切な量のオクテンコモノマーを反応器に充填した後、特定の温度に加熱し、エチレンと共に450psiに加圧した。反応器が圧力下にあるときに、プロ触媒、二種金属活性化剤錯体、溶媒、およびトリエチルアルミニウム捕捉剤を含む、活性化触媒溶液を添加することによって、重合を開始した。反応器の温度および圧力を維持しながら、重合を10分間進行させた。反応が完了した後、ポリマーを収集し、真空オーブンで一晩乾燥させた後分析した。
未希釈の1−オクテン(11mL)を、撹拌棒を備えた40mLバイアルに添加した。それ自体が磁気撹拌プレート上に位置するポリウレタン絶縁ブロックに、バイアルを置いた。撹拌溶液に活性化剤を添加した。次いで、触媒溶液を添加した。バイアルをすぐにセプタムスクリューキャップの蓋でキャップし、プローブの先端が1−オクテン溶液に浸るように温度計プローブをバイアルに挿入した。温度計プローブをデジタルレコーダに接続して、時間および温度を5秒間隔で記録した。バイアルの撹拌を継続し、10分間監視した。
市販の結晶化溶出分別装置(CEF)(Polymer Char、Spain)を使用して、高温熱勾配相互作用クロマトグラフィー(TGIC)測定を実施した(Cong,et al.,Macromolecules,2011,44(8),3062−3072)。HYPERCARBカラム(100×4.6mm、部品#35005〜104646、Thermo Scientific)を分離に使用した。27ミクロンのガラスビーズ(カタログ#GL01918/20〜27μm、MO−SCI Specialty Products,LLC(Rolla,MO,USA))を充填した「8cm×0.48cm(内径3/16インチ)」のステンレス鋼カラムを、IR検出器の前、CEF機器のトップオーブンに設置した。実験パラメータは次のとおりである:トップオーブン/輸送ライン/針温度150℃、溶解温度160℃、溶解撹拌設定2、試料充填容量0.400mL、ポンプ安定化時間15秒、洗浄カラムのポンプ流量0.500mL/分、カラム充填のポンプ流量0.300mL/分、安定化温度150℃、安定化時間(カラム充填前)3.0分、安定化時間(カラム充填後)1.0分、SF(可溶性画分)時間3.0分、150℃〜30℃の冷却速度3.00℃/分、冷却プロセス中の流量0.01mL/分、30℃〜160℃の加熱速度2.00℃/分、等温時間160℃で10分間、溶出流量0.500mL/分、および注入ループサイズ140マイクロリットル。
ポリマー試料と同じ実験条件下で、溶媒ブランク(純粋溶媒注入)を実施した。ポリマー試料のデータ処理は、較正の加熱速度から計算した、各検出器チャネルの溶媒ブランクの減算、較正プロセスで説明されている温度外挿、較正プロセスから決定した遅延容量を用いた温度の補正、および溶出温度軸の30℃〜160℃の範囲への調節を含む。
すべての溶媒および試薬を、商業的供給源から入手し、別段の記載がない限り、受け取ったまま使用した。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中で行われた実験に使用された溶媒は、活性化4Åモレキュラーシーブ上での貯蔵によってさらに乾燥させる。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させる。NMRスペクトルは、Bruker Avance III HD 400MHz NMR、Varian400−MR、または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実施する。LC−MS分離は、XBridge C18 3.5μm 2.1×50mmカラムで、イオン化剤として0.1%ギ酸を含む、5:95〜100:0のアセトニトリルおよび水の勾配を使用して実施する。HRMS分析は、エレクトロスプレーイオン化を備えたAgilent 6230 TOF質量分析計と組み合わせたZorbax Eclipse Plus C18 1.8μm 2.1×50mmカラムを備えたAgilent 1290 Infinity LCを使用して実施する。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)。標準物質として、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(TMS、δスケール)からの低磁場をppm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、標準物質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)からの低磁場としてppmで報告する。
Claims (15)
- オレフィンを重合するプロセスであって、触媒系の存在下で、エチレンと(C3−C40)アルファ−オレフィンコモノマーとを接触させて、ポリマー樹脂を生成することを含み、前記触媒系が、プロ触媒と、二種金属活性化剤錯体とを含み、前記二種金属活性化剤錯体が、アニオンおよび対カチオンを含み、前記アニオンが、式(I)に従った構造を有し、
各Mが独立して、アルミニウム、ホウ素、またはガリウムであり、
Lが、少なくとも2つのルイス塩基性部位を有する種から選択され、
各Qが独立して、単座配位子であり、
nが、0、1、または2であり、nが0であるとき、QnのQが存在せず、
xが、0、1、または2であり、xが0であるとき、QxのQが存在せず、
各Rが独立して、式(II)を有するラジカル、および式(III)を有するラジカルからなる群から選択され、
各R11、R12、R13、R21、R22、R23、R24、およびR25が独立して、(C1−C40)アルキル、(C6−C40)アリール、−H、−NRN 2、−ORC、−SRC、またはハロゲンから選択され、Rが式(II)に従ったラジカルであるとき、R11、R12、またはR13のうちの少なくとも1つが、過ハロゲン化(C1−C40)アルキル、過ハロゲン化(C6−C40)アリール、または−Fであり、Rが、式(III)に従ったラジカルであるとき、R21、R22、R23、R24、およびR25のうちの少なくとも1つが、過ハロゲン化(C1−C40)アルキル、過ハロゲン化(C6−C40)アリール、または−Fであり、
任意選択的に、nが0または1であるとき、式(I)の2つのR基が、共有結合しており、
各RNまたはRCが独立して、(C1−C30)ヒドロカルビル、または−Hである、プロセス。 - Lが、(C1−C20)ヘテロ炭化水素アニオン、−OC(O)RL、−S(O)3RL、−P(O)3RL、−NRL 2、−ORL、−SRL、またはハロゲン化物から選択され、式中、RLが、−H、(C1−C30)ヒドロカルビル、ハロゲン置換(C1−C30)ヒドロカルビルである、請求項1に記載のプロセス。
- Lが、−OC(O)RLであり、RLが、−C6F5である、請求項2に記載のプロセス。
- Lが、−OC(O)RLであり、RLが、−CH3である、請求項2に記載のプロセス。
- 各Mがアルミニウムであるとき、Lが、(C1−C20)ヘテロ炭化水素アニオン、−OC(O)RL、−S(O)3RL、−P(O)3RL、−NRL 2、−ORL、または−SRLから選択され、式中、RLが、−H、(C1−C30)ヒドロカルビル、またはハロゲン置換(C1−C30)ヒドロカルビルである、請求項1に記載のプロセス。
- R1が、−C(C11H23)−であり、R2が、−C(H)−であり、R3が、−Hである、請求項6に記載のプロセス。
- Lが−、−OS(O)2CF3である、請求項1または2に記載のプロセス。
- 各Rが、式(II)を有するラジカルであり、Yが、炭素であり、R11、R12、およびR13が、フッ素である、請求項1〜8のいずれか一項に記載のプロセス。
- 前記対カチオンが、+1の形式電荷を有する、請求項1〜9のいずれか一項に記載のプロセス。
- 前記対カチオンが、+N(H)RN 3であり、式中、各RNが、(C1−C20)アルキル、または(C6−C20)アリールから選択される、請求項1〜10のいずれか一項に記載の重合プロセス。
- 前記対カチオンが、+N(H)RN 3であり、式中、少なくとも2つのRNが、(C10−C20)アルキルから選択される、請求項11に記載の重合プロセス。
- 前記対カチオンが、+C(C6H5)3である、請求項9に記載の重合プロセス。
- 前記対カチオンが、+C(C6H4RC)3であり、式中、RCが、(C1−C20)アルキルである、請求項9に記載の重合プロセス。
- 高沸点完全飽和炭化水素1リットルあたり、200マイクロモルの濃度の二種金属活性化剤錯体および20ミリモルの水を有する、高沸点完全飽和炭化水素溶液中の前記二種金属活性化剤錯体が、炭化水素導電率試験によって測定すると、0.1以下の誘電正接パーセントを有する、請求項1〜14のいずれか一項に記載の重合プロセス。
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