JP2002532584A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002532584A5 JP2002532584A5 JP2000588228A JP2000588228A JP2002532584A5 JP 2002532584 A5 JP2002532584 A5 JP 2002532584A5 JP 2000588228 A JP2000588228 A JP 2000588228A JP 2000588228 A JP2000588228 A JP 2000588228A JP 2002532584 A5 JP2002532584 A5 JP 2002532584A5
- Authority
- JP
- Japan
- Prior art keywords
- pentafluorophenyl
- borate
- pyrrolyl
- methyl
- bis
- 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.)
- Pending
Links
- -1 for example Chemical group 0.000 description 181
- BCGLJOUZEXZYCA-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl) 1H-pyrrol-2-yl borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=CC=CN1 BCGLJOUZEXZYCA-UHFFFAOYSA-N 0.000 description 63
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 40
- 229910052726 zirconium Inorganic materials 0.000 description 37
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 32
- 238000006116 polymerization reaction Methods 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 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 30
- 229910052799 carbon Inorganic materials 0.000 description 29
- 229910052739 hydrogen Inorganic materials 0.000 description 29
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 25
- UGHSGZIDZZRZKT-UHFFFAOYSA-N methane;zirconium Chemical compound C.[Zr] UGHSGZIDZZRZKT-UHFFFAOYSA-N 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 17
- 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 17
- 125000003118 aryl group Chemical group 0.000 description 15
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- VGHPFRSUUZDVPO-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)-(1H-pyrrol-2-yloxy)borinic acid Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1OB(O)OC1=CC=CN1 VGHPFRSUUZDVPO-UHFFFAOYSA-N 0.000 description 13
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 13
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000002904 solvent Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 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 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 9
- 239000012876 carrier material Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- GPHWCWIMKQJDGR-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl)-(1h-pyrrol-2-yl)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=CC=CN1 GPHWCWIMKQJDGR-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 8
- 239000002841 Lewis acid Substances 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical compound OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 150000004645 aluminates Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003623 transition metal compounds Chemical class 0.000 description 5
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 5
- 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 5
- 238000004607 11B NMR spectroscopy Methods 0.000 description 4
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 150000001721 carbon Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 4
- 229910052735 hafnium Inorganic materials 0.000 description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical class CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical class C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 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
- 239000002245 particle Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 238000006276 transfer reaction Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 3
- 238000005406 washing Methods 0.000 description 3
- HTGQCLJTWPSFNL-UHFFFAOYSA-N (2-methylphenoxy)boronic acid Chemical compound CC1=CC=CC=C1OB(O)O HTGQCLJTWPSFNL-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 2
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VAFGZWDYTDHMCR-UHFFFAOYSA-N 2H-cyclopenta[b]furan-5-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1=CC2=CCOC2=C1)C VAFGZWDYTDHMCR-UHFFFAOYSA-N 0.000 description 2
- LKCNBWOMZOFEGO-UHFFFAOYSA-N 2H-cyclopenta[b]thiophen-5-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1=CC2=CCSC2=C1)C LKCNBWOMZOFEGO-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FOJJREBLHNCKQL-UHFFFAOYSA-N BBBBBCBBB Chemical compound BBBBBCBBB FOJJREBLHNCKQL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- DTPVPZKOLQISTJ-UHFFFAOYSA-N C1(C=CC=C1)[Zr](C1C=CC=C1)C1C=CC=C1 Chemical compound C1(C=CC=C1)[Zr](C1C=CC=C1)C1C=CC=C1 DTPVPZKOLQISTJ-UHFFFAOYSA-N 0.000 description 2
- VLOOGSDCMKSQPK-UHFFFAOYSA-N C1=CC=C2C([Zr])C(C)=CC2=C1 Chemical compound C1=CC=C2C([Zr])C(C)=CC2=C1 VLOOGSDCMKSQPK-UHFFFAOYSA-N 0.000 description 2
- PNVXYOCEPXYKGG-UHFFFAOYSA-N CC1(C=CC=C1)[Zr](C1(C)C=CC=C1)C1(C)C=CC=C1 Chemical compound CC1(C=CC=C1)[Zr](C1(C)C=CC=C1)C1(C)C=CC=C1 PNVXYOCEPXYKGG-UHFFFAOYSA-N 0.000 description 2
- LAIDHGZHKKHYNQ-UHFFFAOYSA-N CC1=C(C=CC(=C1)C1=CC=CC2=CC=CC=C12)C=1C(C2=CC=CC=C2C1)[Zr] Chemical compound CC1=C(C=CC(=C1)C1=CC=CC2=CC=CC=C12)C=1C(C2=CC=CC=C2C1)[Zr] LAIDHGZHKKHYNQ-UHFFFAOYSA-N 0.000 description 2
- YSZQYEXXRQLKJI-UHFFFAOYSA-N CC1=Cc2c(cccc2-c2ccccc2)C1[Zr] Chemical compound CC1=Cc2c(cccc2-c2ccccc2)C1[Zr] YSZQYEXXRQLKJI-UHFFFAOYSA-N 0.000 description 2
- JYNZGZAAMRTCNI-UHFFFAOYSA-N CCC1=Cc2c(cccc2-c2ccccc2)C1[Zr] Chemical compound CCC1=Cc2c(cccc2-c2ccccc2)C1[Zr] JYNZGZAAMRTCNI-UHFFFAOYSA-N 0.000 description 2
- VGPDUAWWCXXJSJ-UHFFFAOYSA-N CCCCC1(C=CC=C1)[Zr](C1(CCCC)C=CC=C1)C1(CCCC)C=CC=C1 Chemical compound CCCCC1(C=CC=C1)[Zr](C1(CCCC)C=CC=C1)C1(CCCC)C=CC=C1 VGPDUAWWCXXJSJ-UHFFFAOYSA-N 0.000 description 2
- VWERTVYAPCQBMT-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)C)C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)C)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)C)C1C(=CC2=C(C=CC=C12)C1=CC=CC2=CC=CC=C12)C)C1=CC=CC=C1 VWERTVYAPCQBMT-UHFFFAOYSA-N 0.000 description 2
- UGVVIPAIDGTTNN-UHFFFAOYSA-N C[Zr]C Chemical compound C[Zr]C UGVVIPAIDGTTNN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 2
- VAZKROOLPOKMTJ-UHFFFAOYSA-N cyclopenta[b]pyrrol-5-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1=CC2=CC=NC2=C1)C VAZKROOLPOKMTJ-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- PXPVIOAGNBJCBG-UHFFFAOYSA-N dimethyl-[(1-phenyl-2H-cyclopenta[b]pyrrol-5-yl)methylidene]silane Chemical compound C[Si](=CC=1C=C2N(CC=C2C=1)C1=CC=CC=C1)C PXPVIOAGNBJCBG-UHFFFAOYSA-N 0.000 description 2
- YNIAZEDCCPGOTJ-UHFFFAOYSA-N dimethyl-[(5-methyl-1-phenyl-2H-cyclopenta[b]pyrrol-2-yl)methylidene]silane Chemical compound C[Si](=CC1N(C2=CC(=CC2=C1)C)C1=CC=CC=C1)C YNIAZEDCCPGOTJ-UHFFFAOYSA-N 0.000 description 2
- UOKWFSNVSIMQSB-UHFFFAOYSA-N dimethyl-[(5-methyl-2H-cyclopenta[b]thiophen-2-yl)methylidene]silane Chemical compound C[Si](=CC1C=C2C=C(C=C2S1)C)C UOKWFSNVSIMQSB-UHFFFAOYSA-N 0.000 description 2
- GDZRSSPGIXTSJF-UHFFFAOYSA-N dimethyl-[(5-methylcyclopenta[b]pyrrol-2-yl)methylidene]silane Chemical compound C[Si](=CC1=NC2=CC(=CC2=C1)C)C GDZRSSPGIXTSJF-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- AGOOAFIKKUZTEB-UHFFFAOYSA-N tris(3,5-difluorophenyl)borane Chemical compound FC1=CC(F)=CC(B(C=2C=C(F)C=C(F)C=2)C=2C=C(F)C=C(F)C=2)=C1 AGOOAFIKKUZTEB-UHFFFAOYSA-N 0.000 description 2
- LKWLQPNRJQQVEB-UHFFFAOYSA-N (2,3-dimethylphenoxy)boronic acid Chemical compound CC1=CC=CC(OB(O)O)=C1C LKWLQPNRJQQVEB-UHFFFAOYSA-N 0.000 description 1
- PHBVXHIVWULVNF-UHFFFAOYSA-N (4-fluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(F)C=C1 PHBVXHIVWULVNF-UHFFFAOYSA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- 238000004229 14N NMR spectroscopy Methods 0.000 description 1
- MWFLBUXIVJTNRA-UHFFFAOYSA-N 1H-cyclopenta[c]furan-5-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1=CC2=COCC2=C1)C MWFLBUXIVJTNRA-UHFFFAOYSA-N 0.000 description 1
- YJPRSAQSMGYBGL-UHFFFAOYSA-N 1H-cyclopenta[c]thiophen-5-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1=CC2=CSCC2=C1)C YJPRSAQSMGYBGL-UHFFFAOYSA-N 0.000 description 1
- CYAQLQLZZYVOSR-UHFFFAOYSA-N 1H-pyrrol-2-yloxyboronic acid Chemical compound OB(O)OC1=CC=CN1 CYAQLQLZZYVOSR-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical class C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- BKWNZVQQIYSORG-UHFFFAOYSA-N 3-ethylbicyclo[2.2.1]hepta-1,3-diene Chemical compound C1CC2=CC(CC)=C1C2 BKWNZVQQIYSORG-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- XYZWMVYYUIMRIZ-UHFFFAOYSA-N 4-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Br)C=C1 XYZWMVYYUIMRIZ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KFRIPBOVARWFNK-UHFFFAOYSA-N C(C)(C)=[Zr](C1=CC=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 Chemical compound C(C)(C)=[Zr](C1=CC=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 KFRIPBOVARWFNK-UHFFFAOYSA-N 0.000 description 1
- MOBNLAWYKFVFSS-UHFFFAOYSA-N C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr](C1=CC=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)=[Zr](C1=CC=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 MOBNLAWYKFVFSS-UHFFFAOYSA-N 0.000 description 1
- VNWLMDDJAZMGMC-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C Chemical compound C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C VNWLMDDJAZMGMC-UHFFFAOYSA-N 0.000 description 1
- FCAWXAVZZZNKIC-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C(C)C)C)C1C(=CC2=C(C=CC=C12)C(C)C)C)C Chemical compound C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C(C)C)C)C1C(=CC2=C(C=CC=C12)C(C)C)C)C FCAWXAVZZZNKIC-UHFFFAOYSA-N 0.000 description 1
- JNDHVVVMHLIAFY-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)C Chemical compound C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)C JNDHVVVMHLIAFY-UHFFFAOYSA-N 0.000 description 1
- DNEICPOIDFHHJM-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=CC(=CC=C12)CC(C)C)C)C1C(=CC2=CC(=CC=C12)CC(C)C)C)C Chemical compound C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=CC(=CC=C12)CC(C)C)C)C1C(=CC2=CC(=CC=C12)CC(C)C)C)C DNEICPOIDFHHJM-UHFFFAOYSA-N 0.000 description 1
- KDBOJLGGPMELSV-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C Chemical compound C1(=CC=CC=C1)[Si](=[Zr](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C)C KDBOJLGGPMELSV-UHFFFAOYSA-N 0.000 description 1
- CPNALZXLUFBDPN-UHFFFAOYSA-N C=C.C1=CC2=CC=CC=C2C1[Zr]C1C2=CC=CC=C2C=C1 Chemical compound C=C.C1=CC2=CC=CC=C2C1[Zr]C1C2=CC=CC=C2C=C1 CPNALZXLUFBDPN-UHFFFAOYSA-N 0.000 description 1
- IZLYCAWDIGDJAK-UHFFFAOYSA-N CC(C(C1=CC=C2)[Zr](C3C4=CC=CC(C5=CC6=CC=CC=C6C=C5)=C4C=C3C)=[Si](C)C3=CC=CC=C3)=CC1=C2C1=CC2=CC=CC=C2C=C1 Chemical compound CC(C(C1=CC=C2)[Zr](C3C4=CC=CC(C5=CC6=CC=CC=C6C=C5)=C4C=C3C)=[Si](C)C3=CC=CC=C3)=CC1=C2C1=CC2=CC=CC=C2C=C1 IZLYCAWDIGDJAK-UHFFFAOYSA-N 0.000 description 1
- MPCANJLCGGUXJG-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC1[Zr](C1=CC=CC2=C1CC1=CC=CC=C21)=[Si](C)C Chemical compound CC(C)(C)C(C=C1)=CC1[Zr](C1=CC=CC2=C1CC1=CC=CC=C21)=[Si](C)C MPCANJLCGGUXJG-UHFFFAOYSA-N 0.000 description 1
- RTAQCQOZRWKSTQ-UHFFFAOYSA-N CC(C)C[Mg]CC(C)C Chemical compound CC(C)C[Mg]CC(C)C RTAQCQOZRWKSTQ-UHFFFAOYSA-N 0.000 description 1
- JPVJJKXZXMZGCK-UHFFFAOYSA-N CC(C)[Zr](C1C2=C(C=CC=C3)C3=CC=C2C=C1C)(C1C2=C(C=CC=C3)C3=CC=C2C=C1C)=[SiH2] Chemical compound CC(C)[Zr](C1C2=C(C=CC=C3)C3=CC=C2C=C1C)(C1C2=C(C=CC=C3)C3=CC=C2C=C1C)=[SiH2] JPVJJKXZXMZGCK-UHFFFAOYSA-N 0.000 description 1
- XLMURYKHYGVLGO-UHFFFAOYSA-N CC(C)[Zr](C1C2=CC(C)=CC(C)=C2C=C1C)(C1C2=CC(C)=CC(C)=C2C=C1C)=[SiH2] Chemical compound CC(C)[Zr](C1C2=CC(C)=CC(C)=C2C=C1C)(C1C2=CC(C)=CC(C)=C2C=C1C)=[SiH2] XLMURYKHYGVLGO-UHFFFAOYSA-N 0.000 description 1
- ABWAEOGELQZXCF-UHFFFAOYSA-N CC(C)[Zr](C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)(C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)=[SiH2] Chemical compound CC(C)[Zr](C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)(C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)=[SiH2] ABWAEOGELQZXCF-UHFFFAOYSA-N 0.000 description 1
- NYPSHJVOBAYDPM-UHFFFAOYSA-N CC(C)[Zr](C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1C)(C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1C)=[SiH2] Chemical compound CC(C)[Zr](C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1C)(C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1C)=[SiH2] NYPSHJVOBAYDPM-UHFFFAOYSA-N 0.000 description 1
- CXAWFMBYKQQJDB-UHFFFAOYSA-N CC(C)[Zr](C1C2=CC=CC=C2C=C1C)(C1C2=CC=CC=C2C=C1C)=[SiH2] Chemical compound CC(C)[Zr](C1C2=CC=CC=C2C=C1C)(C1C2=CC=CC=C2C=C1C)=[SiH2] CXAWFMBYKQQJDB-UHFFFAOYSA-N 0.000 description 1
- AVRQGYWXJCADIP-UHFFFAOYSA-N CC(C1=CC=CC=C1)=[Zr](C1C=CC=C1)C1=CC=CC2=C1CC1=CC=CC=C21 Chemical compound CC(C1=CC=CC=C1)=[Zr](C1C=CC=C1)C1=CC=CC2=C1CC1=CC=CC=C21 AVRQGYWXJCADIP-UHFFFAOYSA-N 0.000 description 1
- QUPHEHKVVIHWPV-UHFFFAOYSA-N CC(C1=CC=CC=C1)[Zr](C1C2=C(C=CC=C3)C3=CC=C2C=C1C)(C1C2=C(C=CC=C3)C3=CC=C2C=C1C)=[SiH2] Chemical compound CC(C1=CC=CC=C1)[Zr](C1C2=C(C=CC=C3)C3=CC=C2C=C1C)(C1C2=C(C=CC=C3)C3=CC=C2C=C1C)=[SiH2] QUPHEHKVVIHWPV-UHFFFAOYSA-N 0.000 description 1
- TWATUDXVTDTFDM-UHFFFAOYSA-N CC(C1=CC=CC=C1)[Zr](C1C2=CC(C)=CC(C)=C2C=C1C)(C1C2=CC(C)=CC(C)=C2C=C1C)=[SiH2] Chemical compound CC(C1=CC=CC=C1)[Zr](C1C2=CC(C)=CC(C)=C2C=C1C)(C1C2=CC(C)=CC(C)=C2C=C1C)=[SiH2] TWATUDXVTDTFDM-UHFFFAOYSA-N 0.000 description 1
- HORSKBBYAADFIB-UHFFFAOYSA-N CC(C1=CC=CC=C1)[Zr](C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)(C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)=[SiH2] Chemical compound CC(C1=CC=CC=C1)[Zr](C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)(C1C2=CC=CC(C3=CC=CC4=CC=CC=C34)=C2C=C1C)=[SiH2] HORSKBBYAADFIB-UHFFFAOYSA-N 0.000 description 1
- PWKBOACLWALVMP-UHFFFAOYSA-N CC(C1=CC=CC=C1)[Zr](C1C2=CC=CC=C2C=C1C)(C1C2=CC=CC=C2C=C1C)=[SiH2] Chemical compound CC(C1=CC=CC=C1)[Zr](C1C2=CC=CC=C2C=C1C)(C1C2=CC=CC=C2C=C1C)=[SiH2] PWKBOACLWALVMP-UHFFFAOYSA-N 0.000 description 1
- NCSHNSSCXBJNOY-UHFFFAOYSA-N CC([Zr](C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)(C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)=[SiH2])C1=CC=CC=C1 Chemical compound CC([Zr](C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)(C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)=[SiH2])C1=CC=CC=C1 NCSHNSSCXBJNOY-UHFFFAOYSA-N 0.000 description 1
- ZNIKHDUVCVBPSM-UHFFFAOYSA-N CC([Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)(C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)=[SiH2])C1=CC=CC=C1 Chemical compound CC([Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)(C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)C)=[SiH2])C1=CC=CC=C1 ZNIKHDUVCVBPSM-UHFFFAOYSA-N 0.000 description 1
- QYCKAFBVVSSHAU-UHFFFAOYSA-N CC1(C=CC=C1)[Zr](C)C1(C)C=CC=C1 Chemical compound CC1(C=CC=C1)[Zr](C)C1(C)C=CC=C1 QYCKAFBVVSSHAU-UHFFFAOYSA-N 0.000 description 1
- ULPLZIBFOBHKHG-UHFFFAOYSA-N CC1=C2C(=CCO2)C=C1 Chemical compound CC1=C2C(=CCO2)C=C1 ULPLZIBFOBHKHG-UHFFFAOYSA-N 0.000 description 1
- GDDMNJLTBQQLAK-UHFFFAOYSA-N CC1=CC2=C(C(CC3=CC=C4)C5=C3C4=CC=C5)C=CC=C2C1[Zr](C1C2=CC=CC(C(CC3=CC=C4)C5=C3C4=CC=C5)=C2C=C1C)=[Si](C)C1=CC=CC=C1 Chemical compound CC1=CC2=C(C(CC3=CC=C4)C5=C3C4=CC=C5)C=CC=C2C1[Zr](C1C2=CC=CC(C(CC3=CC=C4)C5=C3C4=CC=C5)=C2C=C1C)=[Si](C)C1=CC=CC=C1 GDDMNJLTBQQLAK-UHFFFAOYSA-N 0.000 description 1
- GLVAUWBGOFAFOS-UHFFFAOYSA-N CC1=CC2=C(C)C=CC(C)=C2C1[Zr](C1C2=C(C)C=CC(C)=C2C=C1C)=[Si](C)C1=CC=CC=C1 Chemical compound CC1=CC2=C(C)C=CC(C)=C2C1[Zr](C1C2=C(C)C=CC(C)=C2C=C1C)=[Si](C)C1=CC=CC=C1 GLVAUWBGOFAFOS-UHFFFAOYSA-N 0.000 description 1
- CGJXGEUOYVPNFI-UHFFFAOYSA-N CC1=CC2=CC(C)=C(C)C=C2C1[Zr](C1C2=CC(C)=C(C)C=C2C=C1C)=[Si](C)C1=CC=CC=C1 Chemical compound CC1=CC2=CC(C)=C(C)C=C2C1[Zr](C1C2=CC(C)=C(C)C=C2C=C1C)=[Si](C)C1=CC=CC=C1 CGJXGEUOYVPNFI-UHFFFAOYSA-N 0.000 description 1
- SYZNTZDBHZCZBG-UHFFFAOYSA-N CC1=CC2=CC=C(C=CC=C3)C3=C2C1[Zr](C)C1C2=C(C=CC=C3)C3=CC=C2C=C1C Chemical compound CC1=CC2=CC=C(C=CC=C3)C3=C2C1[Zr](C)C1C2=C(C=CC=C3)C3=CC=C2C=C1C SYZNTZDBHZCZBG-UHFFFAOYSA-N 0.000 description 1
- GSVVOWUDMHSUNI-UHFFFAOYSA-N CC1=Cc2c(cccc2-c2ccccc2)C1[Zr]1(CC1)C1C(C)=Cc2c1cccc2-c1ccccc1 Chemical compound CC1=Cc2c(cccc2-c2ccccc2)C1[Zr]1(CC1)C1C(C)=Cc2c1cccc2-c1ccccc1 GSVVOWUDMHSUNI-UHFFFAOYSA-N 0.000 description 1
- VTWSVYRNNUORMT-UHFFFAOYSA-N CC1=Cc2ccccc2C1[Zr]1(CC1)C1C(C)=Cc2ccccc12 Chemical compound CC1=Cc2ccccc2C1[Zr]1(CC1)C1C(C)=Cc2ccccc12 VTWSVYRNNUORMT-UHFFFAOYSA-N 0.000 description 1
- SCDZMQTXRGZYJJ-UHFFFAOYSA-N CCC1=C(C=C(C)C2[Zr](C3C4=CC=CC(CC)=C4C=C3C)=[Si](C)C3=CC=CC=C3)C2=CC=C1 Chemical compound CCC1=C(C=C(C)C2[Zr](C3C4=CC=CC(CC)=C4C=C3C)=[Si](C)C3=CC=CC=C3)C2=CC=C1 SCDZMQTXRGZYJJ-UHFFFAOYSA-N 0.000 description 1
- YFFVZVVORFKCBS-UHFFFAOYSA-N CCC1=CC2=C(CC)C=CC=C2C1[Zr](C(C)C)(C1C2=CC=CC(CC)=C2C=C1CC)=[SiH2] Chemical compound CCC1=CC2=C(CC)C=CC=C2C1[Zr](C(C)C)(C1C2=CC=CC(CC)=C2C=C1CC)=[SiH2] YFFVZVVORFKCBS-UHFFFAOYSA-N 0.000 description 1
- AEENIGKQBYFUEL-UHFFFAOYSA-N CCCCC1(C=CC=C1)[Zr](C)C1(CCCC)C=CC=C1 Chemical compound CCCCC1(C=CC=C1)[Zr](C)C1(CCCC)C=CC=C1 AEENIGKQBYFUEL-UHFFFAOYSA-N 0.000 description 1
- NSKVFTJEKYEULC-UHFFFAOYSA-N CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O Chemical compound CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O NSKVFTJEKYEULC-UHFFFAOYSA-N 0.000 description 1
- NZBAXDDBOGVSII-UHFFFAOYSA-N CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O Chemical compound CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O NZBAXDDBOGVSII-UHFFFAOYSA-N 0.000 description 1
- WWQQTQQJSUTWJO-UHFFFAOYSA-N CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O Chemical compound CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O.OB(O)O WWQQTQQJSUTWJO-UHFFFAOYSA-N 0.000 description 1
- OKUJQNLYGXPVKV-UHFFFAOYSA-N CN(C)C.CN(C)C.OB(O)OC1=CC=CC=C1 Chemical compound CN(C)C.CN(C)C.OB(O)OC1=CC=CC=C1 OKUJQNLYGXPVKV-UHFFFAOYSA-N 0.000 description 1
- NKTVJGOOYQZLRX-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C1C(=CC2=C(C=C(C=C12)C(C)C)C(C)C)C)C NKTVJGOOYQZLRX-UHFFFAOYSA-N 0.000 description 1
- BPAXINOSKHVFOD-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C)C)C)C1C(=CC2=C(C=C(C=C12)C)C)C)C Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C)C)C)C1C(=CC2=C(C=C(C=C12)C)C)C)C BPAXINOSKHVFOD-UHFFFAOYSA-N 0.000 description 1
- GYOLTFVQUDUPFC-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C)C)C)C1C(=CC2=C(C=C(C=C12)C)C)C)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=C(C=C12)C)C)C)C1C(=CC2=C(C=C(C=C12)C)C)C)C1=CC=CC=C1 GYOLTFVQUDUPFC-UHFFFAOYSA-N 0.000 description 1
- USZOGQRPDZNGIK-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC(=C12)C)C)C)C1C(=CC2=C(C=CC(=C12)C)C)C)C Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC(=C12)C)C)C)C1C(=CC2=C(C=CC(=C12)C)C)C)C USZOGQRPDZNGIK-UHFFFAOYSA-N 0.000 description 1
- CROVPFYDPOJOIR-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C(C)(C)C)C)C1C(=CC2=C(C=CC=C12)C(C)(C)C)C)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C(C)(C)C)C)C1C(=CC2=C(C=CC=C12)C(C)(C)C)C)C1=CC=CC=C1 CROVPFYDPOJOIR-UHFFFAOYSA-N 0.000 description 1
- REUDQDYGMQYNDG-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C)C)C1C(=CC2=C(C=CC=C12)C)C)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C)C)C1C(=CC2=C(C=CC=C12)C)C)C1=CC=CC=C1 REUDQDYGMQYNDG-UHFFFAOYSA-N 0.000 description 1
- XNLRYGYUUAUHGC-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)CC)C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)CC)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)CC)C1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)CC)C1=CC=CC=C1 XNLRYGYUUAUHGC-UHFFFAOYSA-N 0.000 description 1
- GZPFUFLSVKECIZ-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)CC)CC)C1C(=CC2=C(C=CC=C12)CC)CC)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=C(C=CC=C12)CC)CC)C1C(=CC2=C(C=CC=C12)CC)CC)C1=CC=CC=C1 GZPFUFLSVKECIZ-UHFFFAOYSA-N 0.000 description 1
- QHDGOQZSUZVJDU-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC(=C(C=C12)C)C)C)C1C(=CC2=CC(=C(C=C12)C)C)C)C Chemical compound C[Si](=[Zr](C1C(=CC2=CC(=C(C=C12)C)C)C)C1C(=CC2=CC(=C(C=C12)C)C)C)C QHDGOQZSUZVJDU-UHFFFAOYSA-N 0.000 description 1
- PJHCUXMHYXMYKT-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C Chemical compound C[Si](=[Zr](C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C PJHCUXMHYXMYKT-UHFFFAOYSA-N 0.000 description 1
- WBFASBWSNXWIFZ-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C1C(=CC2=CC(=CC=C12)C(C)(C)C)C)C1=CC=CC=C1 WBFASBWSNXWIFZ-UHFFFAOYSA-N 0.000 description 1
- PAYYBMZFQCXCRH-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC(=CC=C12)CC(C)C)C)C1C(=CC2=CC(=CC=C12)CC(C)C)C)C Chemical compound C[Si](=[Zr](C1C(=CC2=CC(=CC=C12)CC(C)C)C)C1C(=CC2=CC(=CC=C12)CC(C)C)C)C PAYYBMZFQCXCRH-UHFFFAOYSA-N 0.000 description 1
- PJCQLMXHSNHPLZ-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)C)C3C(=CC1=CC=C2C(=C31)C=CC=C2)C)C2=CC=CC=C2 Chemical compound C[Si](=[Zr](C1C(=CC2=CC=C3C(=C12)C=CC=C3)C)C3C(=CC1=CC=C2C(=C31)C=CC=C2)C)C2=CC=CC=C2 PJCQLMXHSNHPLZ-UHFFFAOYSA-N 0.000 description 1
- GWHQKWUMBYZKRT-UHFFFAOYSA-N C[Si](=[Zr](C1C(=CC2=CC=CC=C12)CC)C1C(=CC2=CC=CC=C12)CC)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C(=CC2=CC=CC=C12)CC)C1C(=CC2=CC=CC=C12)CC)C1=CC=CC=C1 GWHQKWUMBYZKRT-UHFFFAOYSA-N 0.000 description 1
- CZFNEECNJGSIRF-UHFFFAOYSA-N C[Si](=[Zr](C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12)C1=CC=CC=C1 Chemical compound C[Si](=[Zr](C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12)C1=CC=CC=C1 CZFNEECNJGSIRF-UHFFFAOYSA-N 0.000 description 1
- NFQXVSSXTLAYQC-UHFFFAOYSA-N C[Si](C1=CC=CC=C1)=[Zr](C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1)C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1 Chemical compound C[Si](C1=CC=CC=C1)=[Zr](C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1)C1C2=CC=CC(C3=CC=CC=C3)=C2C=C1 NFQXVSSXTLAYQC-UHFFFAOYSA-N 0.000 description 1
- GVBSSQOXLHKEIP-UHFFFAOYSA-N C[Zr](C1(C)C(C)=C(C)C(C)=C1C)C1(C)C(C)=C(C)C(C)=C1C Chemical compound C[Zr](C1(C)C(C)=C(C)C(C)=C1C)C1(C)C(C)=C(C)C(C)=C1C GVBSSQOXLHKEIP-UHFFFAOYSA-N 0.000 description 1
- DGFXGNPHXNJLFT-UHFFFAOYSA-N C[Zr](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C Chemical compound C[Zr](C1C(=CC2=CC=CC=C12)C)C1C(=CC2=CC=CC=C12)C DGFXGNPHXNJLFT-UHFFFAOYSA-N 0.000 description 1
- KBVFEDDBPKIWDE-UHFFFAOYSA-N C[Zr](C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12 Chemical compound C[Zr](C1C=CC2=CC=CC=C12)C1C=CC2=CC=CC=C12 KBVFEDDBPKIWDE-UHFFFAOYSA-N 0.000 description 1
- MSVMXTWPQBFQQF-UHFFFAOYSA-N C[Zr](C1C=CC=C1)C1C=CC=C1 Chemical compound C[Zr](C1C=CC=C1)C1C=CC=C1 MSVMXTWPQBFQQF-UHFFFAOYSA-N 0.000 description 1
- 238000010499 C–H functionalization reaction Methods 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- UVSSPWOKVSKHCU-UHFFFAOYSA-N [2-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=CC=C1C(F)(F)F UVSSPWOKVSKHCU-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- PBZHFLGIROVUPM-UHFFFAOYSA-N cyclopenta[c]pyrrol-5-ylmethylidene(dimethyl)silane Chemical compound C[Si](=CC1=CC2=CN=CC2=C1)C PBZHFLGIROVUPM-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- JVCISIKHAZUSCH-UHFFFAOYSA-N dichloro(pyrrolidin-1-yl)borane Chemical compound ClB(Cl)N1CCCC1 JVCISIKHAZUSCH-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-O diethyl(phenyl)azanium Chemical compound CC[NH+](CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-O 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- IAAKXIPQVRCQAY-UHFFFAOYSA-N difluoro-(2,3,4,5,6-pentafluorophenyl)borane Chemical compound FB(F)C1=C(F)C(F)=C(F)C(F)=C1F IAAKXIPQVRCQAY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MKMUUVUYHMGIFI-UHFFFAOYSA-N dimethyl-[(2-phenyl-1H-cyclopenta[c]pyrrol-5-yl)methylidene]silane Chemical compound C[Si](=CC1=CC2=CN(CC2=C1)C1=CC=CC=C1)C MKMUUVUYHMGIFI-UHFFFAOYSA-N 0.000 description 1
- DGUIDBYKNGVRCS-UHFFFAOYSA-N dimethyl-[(5-methyl-2H-cyclopenta[b]furan-2-yl)methylidene]silane Chemical compound C[Si](=CC1OC2=CC(=CC2=C1)C)C DGUIDBYKNGVRCS-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- OTRXCHZIIFVNRW-UHFFFAOYSA-N fluoro-bis(2,3,4,5,6-pentafluorophenyl)borane Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1B(F)C1=C(F)C(F)=C(F)C(F)=C1F OTRXCHZIIFVNRW-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GOYZJQHIHVWIRY-UHFFFAOYSA-N lithium;1,2-dihydropyrrol-2-ide Chemical compound [Li+].C=1C=[C-]NC=1 GOYZJQHIHVWIRY-UHFFFAOYSA-N 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- QJAIOCKFIORVFU-UHFFFAOYSA-N n,n-dimethyl-4-nitroaniline Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=C1 QJAIOCKFIORVFU-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- NEMUVWSQFWIZKP-UHFFFAOYSA-N n-methyl-n-trichlorosilylmethanamine Chemical compound CN(C)[Si](Cl)(Cl)Cl NEMUVWSQFWIZKP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical group [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-O triethylphosphanium Chemical compound CC[PH+](CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-O 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GIIXTFIYICRGMZ-UHFFFAOYSA-N tris(2,3-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C GIIXTFIYICRGMZ-UHFFFAOYSA-N 0.000 description 1
- YFDAMRSZJLWUSQ-UHFFFAOYSA-N tris(2-methylphenyl)borane Chemical compound CC1=CC=CC=C1B(C=1C(=CC=CC=1)C)C1=CC=CC=C1C YFDAMRSZJLWUSQ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- OHSAEOPCBBOWPU-UHFFFAOYSA-N tris(3,5-dimethylphenyl)borane Chemical compound CC1=CC(C)=CC(B(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 OHSAEOPCBBOWPU-UHFFFAOYSA-N 0.000 description 1
- YPVVTWIAXFPZLS-UHFFFAOYSA-N tris(4-fluorophenyl)borane Chemical compound C1=CC(F)=CC=C1B(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 YPVVTWIAXFPZLS-UHFFFAOYSA-N 0.000 description 1
- OSMBUUFIZBTSNO-UHFFFAOYSA-N tris[4-(fluoromethyl)phenyl]borane Chemical compound C1=CC(CF)=CC=C1B(C=1C=CC(CF)=CC=1)C1=CC=C(CF)C=C1 OSMBUUFIZBTSNO-UHFFFAOYSA-N 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998157377 DE19857377A1 (de) | 1998-12-12 | 1998-12-12 | Übergangsmetallverbindung |
| DE19857377.4 | 1998-12-12 | ||
| DE19903306A DE19903306A1 (de) | 1999-01-28 | 1999-01-28 | Organometallverbindung, Katalysatorsystem enthaltend diese Organometallverbindung und seine Verwendung |
| DE19903306.4 | 1999-01-28 | ||
| PCT/EP1999/009682 WO2000035973A1 (de) | 1998-12-12 | 1999-12-09 | Zwitterionische neutrale borenthaltende übergangsmetallverbindung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002532584A JP2002532584A (ja) | 2002-10-02 |
| JP2002532584A5 true JP2002532584A5 (enExample) | 2007-02-01 |
Family
ID=26050725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000588228A Pending JP2002532584A (ja) | 1998-12-12 | 1999-12-09 | 遷移金属化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6486277B1 (enExample) |
| EP (1) | EP1054914B1 (enExample) |
| JP (1) | JP2002532584A (enExample) |
| AT (1) | ATE260945T1 (enExample) |
| DE (1) | DE59908742D1 (enExample) |
| ES (1) | ES2217859T3 (enExample) |
| WO (1) | WO2000035973A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001232855A1 (en) | 2000-01-21 | 2001-07-31 | U.S. Borax Inc. | Nonaborate compositions and their preparation |
| CA2423246A1 (en) * | 2000-09-26 | 2002-04-04 | Bp Chemicals Limited | Supported catalyst systems |
| DE10114345A1 (de) | 2001-03-23 | 2002-09-26 | Bayer Ag | Katalysator mit einer Donor-Akzeptor-Wechselwirkung |
| DE60202524T2 (de) | 2001-05-21 | 2005-06-30 | Basell Polyolefine Gmbh | Katalysatorsystem für die polymerisierung von olefinen |
| US6841504B2 (en) * | 2002-01-28 | 2005-01-11 | Univation Technologies, Llc | Polymerization catalyst activator and its use in a polymerization process |
| US6703338B2 (en) | 2002-06-28 | 2004-03-09 | Univation Technologies, Llc | Polymerization catalyst activators, method of preparing, and their use in polymerization processes |
| WO2004037841A1 (ja) * | 2002-10-25 | 2004-05-06 | Japan Polyethylene Corporation | 新規な遷移金属化合物、オレフィン重合用触媒およびポリオレフィンの製造方法 |
| US8058200B2 (en) * | 2007-05-17 | 2011-11-15 | Chevron Phillips Chemical Company, L.P. | Catalysts for olefin polymerization |
| CN109824737B (zh) * | 2019-03-20 | 2021-03-05 | 上海应用技术大学 | 一种半夹心铱配合物及其制备和应用 |
| CN110016061B (zh) * | 2019-04-10 | 2021-02-26 | 上海应用技术大学 | 含碳硼烷基苯并咪唑结构的钌配合物及其制备方法与应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5384299A (en) * | 1987-01-30 | 1995-01-24 | Exxon Chemical Patents Inc. | Ionic metallocene catalyst compositions |
| DE4420456A1 (de) * | 1994-06-13 | 1995-12-14 | Hoechst Ag | Übergangsmetallverbindung |
| US5541349A (en) * | 1994-09-12 | 1996-07-30 | The Dow Chemical Company | Metal complexes containing partially delocalized II-bound groups and addition polymerization catalysts therefrom |
| US6174974B1 (en) * | 1996-07-05 | 2001-01-16 | Bayer Aktiengesellschaft | Method for producing thermoplastic elastomers |
-
1999
- 1999-12-09 EP EP99962247A patent/EP1054914B1/de not_active Expired - Lifetime
- 1999-12-09 JP JP2000588228A patent/JP2002532584A/ja active Pending
- 1999-12-09 AT AT99962247T patent/ATE260945T1/de not_active IP Right Cessation
- 1999-12-09 ES ES99962247T patent/ES2217859T3/es not_active Expired - Lifetime
- 1999-12-09 DE DE59908742T patent/DE59908742D1/de not_active Expired - Fee Related
- 1999-12-09 WO PCT/EP1999/009682 patent/WO2000035973A1/de not_active Ceased
- 1999-12-09 US US09/622,205 patent/US6486277B1/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6627764B1 (en) | Transition metal compound, ligand system, catalyst system and its use for the polymerization of olefins | |
| US6949614B1 (en) | Catalyst system | |
| US5776851A (en) | Metallocenes, process for their preparation and their use as catalysts | |
| US6350830B1 (en) | Catalyst system, method for the production thereof and its use for the polymerization of olefins | |
| US6271164B1 (en) | Supported catalyst system, process for its production and its use in polymerizing olefins | |
| US6469114B1 (en) | Metallocene compound and polymerization catalyst comprising heterocyclic group | |
| JPH06100579A (ja) | アリール置換インデニル誘導体をリガンドとして含んだメタロセン | |
| JP4150439B2 (ja) | メタロセン触媒システムを製造するための方法 | |
| JP2002530416A (ja) | モノアリールオキシ−アンサ−メタロセン | |
| US5792819A (en) | Process for the preparation of an olefin polymer | |
| US6365763B1 (en) | Method for producing metallocenes | |
| JPH08231573A (ja) | メタロセン化合物及び触媒成分としてのその使用 | |
| JP2002516358A (ja) | 触媒組成物およびプロピレン重合のためのその使用 | |
| US6486277B1 (en) | Zwitterionic transition metal compound which contains boron | |
| US6177526B1 (en) | Supported catalyst system, process for its preparation and its use for the polymerization of olefins | |
| JP2002532584A5 (enExample) | ||
| US6319874B1 (en) | Method for producing metallocenes | |
| US20040072975A1 (en) | Salt-like chemical compound, its preparation and its use in catalyst systems for preparing polyolefins | |
| JP2001011089A (ja) | 遷移金属化合物、触媒組成物、その製造方法及びオレフィン重合用としての使用 | |
| JPH08193092A (ja) | メタロセン化合物 | |
| US6002032A (en) | Transition metal compound | |
| JP3850048B2 (ja) | 有機遷移金属化合物およびそれを用いたポリオレフィンの製造方法 | |
| JP4166086B2 (ja) | 非メタロセン、その製造法及びそのオレフィンの重合への使用法 | |
| JP2004530653A (ja) | 非メタロセン、その製造方法およびオレフィンの重合での使用 | |
| JP4445044B2 (ja) | 担持触媒系、その調製法およびオレフィン重合用としてのその使用 |