CA2212668A1 - Supported chemical compound - Google Patents
Supported chemical compoundInfo
- Publication number
- CA2212668A1 CA2212668A1 CA002212668A CA2212668A CA2212668A1 CA 2212668 A1 CA2212668 A1 CA 2212668A1 CA 002212668 A CA002212668 A CA 002212668A CA 2212668 A CA2212668 A CA 2212668A CA 2212668 A1 CA2212668 A1 CA 2212668A1
- Authority
- CA
- Canada
- Prior art keywords
- dimethyl
- zirconium
- bis
- integer
- phenylindenyl
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- 230000000737 periodic effect Effects 0.000 claims abstract description 13
- 125000006850 spacer group Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 150000001768 cations Chemical class 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- -1 sulfonium cation Chemical class 0.000 claims description 146
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 11
- 150000003624 transition metals Chemical class 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 150000003623 transition metal compounds Chemical class 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 claims description 4
- 125000005517 carbenium group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 description 180
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 66
- 229910052735 hafnium Inorganic materials 0.000 description 57
- 229910052719 titanium Inorganic materials 0.000 description 53
- 239000010936 titanium Substances 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 28
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000725 suspension Substances 0.000 description 19
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 17
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 13
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 13
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 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 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 12
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 8
- 238000004293 19F NMR spectroscopy Methods 0.000 description 7
- 241000723368 Conium Species 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 229910000085 borane Inorganic materials 0.000 description 7
- 229910052681 coesite Inorganic materials 0.000 description 7
- 229910052906 cristobalite Inorganic materials 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- 229910052682 stishovite Inorganic materials 0.000 description 7
- 229910052905 tridymite Inorganic materials 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- VHOBAVSVXOKJLC-UHFFFAOYSA-N triethoxy-[(2,3,5,6-tetrafluorophenoxy)methyl]silane Chemical compound CCO[Si](OCC)(OCC)COC1=C(F)C(F)=CC(F)=C1F VHOBAVSVXOKJLC-UHFFFAOYSA-N 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- NPCGBGCBMXKWIH-UHFFFAOYSA-N chloro-bis(2,3,4,5,6-pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(Cl)C1=C(F)C(F)=C(F)C(F)=C1F NPCGBGCBMXKWIH-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910052706 scandium Inorganic materials 0.000 description 4
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910003849 O-Si Inorganic materials 0.000 description 3
- 229910003872 O—Si Inorganic materials 0.000 description 3
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 3
- 241000927721 Tritia Species 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 3
- XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 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
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- PBYIIRLNRCVTMQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorophenol Chemical compound OC1=C(F)C(F)=CC(F)=C1F PBYIIRLNRCVTMQ-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
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- 241000191368 Chlorobi Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000010499 C–H functionalization reaction Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- JLDSOYXADOWAKB-UHFFFAOYSA-N aluminium nitrate Chemical compound [Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JLDSOYXADOWAKB-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- RMVKLSURSIYQTI-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl)boron Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[B]C1=C(F)C(F)=C(F)C(F)=C1F RMVKLSURSIYQTI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- YNEOILNOYXEUJZ-UHFFFAOYSA-N chloro-dimethyl-(2,3,5,6-tetrafluorophenoxy)silane Chemical compound C[Si](C)(Cl)OC1=C(F)C(F)=CC(F)=C1F YNEOILNOYXEUJZ-UHFFFAOYSA-N 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001485 cycloalkadienyl group Chemical group 0.000 description 2
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 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
- 125000002347 octyl 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])[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 238000005406 washing Methods 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 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
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 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
- KUKRLSJNTMLPPK-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(C)C=CC1C2(C)C KUKRLSJNTMLPPK-UHFFFAOYSA-N 0.000 description 1
- LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 description 1
- 229910015845 BBr3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- GLVKGYRREXOCIB-UHFFFAOYSA-N Bornylene Natural products CC1CCC(C(C)(C)C)C=C1 GLVKGYRREXOCIB-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 compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXXFHLYRPHXLDJ-UHFFFAOYSA-N C1(C=CC=C1)C1(C2CCC(C2C(C=C1)(C)C)[Zr](C)C)C Chemical compound C1(C=CC=C1)C1(C2CCC(C2C(C=C1)(C)C)[Zr](C)C)C UXXFHLYRPHXLDJ-UHFFFAOYSA-N 0.000 description 1
- BZAMWJKSASXCKQ-UHFFFAOYSA-N C1=CC2=CC=CC=C2C1[Ti](C1C=CC2=CC=CC=C12)=[Si](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1=CC2=CC=CC=C2C1[Ti](C1C=CC2=CC=CC=C12)=[Si](C1=CC=CC=C1)C1=CC=CC=C1 BZAMWJKSASXCKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 description 1
- BKLRHFWSTMIIMQ-UHFFFAOYSA-N C[Si](=[Ti](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)C1=CC=CC=C1 Chemical compound C[Si](=[Ti](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)C1=CC=CC=C1 BKLRHFWSTMIIMQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07F5/02—Boron compounds
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- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- 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
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- 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
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- 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
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
-
- 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
- C08F4/65922—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 containing at least two cyclopentadienyl rings, fused or not
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catalysts (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19632558A DE19632558A1 (de) | 1996-08-13 | 1996-08-13 | Geträgerte chemische Verbindung |
| DE1996132557 DE19632557A1 (de) | 1996-08-13 | 1996-08-13 | Chemische Verbindung |
| DE19632558.7 | 1996-11-14 | ||
| DE1996147070 DE19647070A1 (de) | 1996-11-14 | 1996-11-14 | Geträgerte chemische Verbindung |
| DE19647070.6 | 1996-11-14 | ||
| DE19632557.9 | 1996-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2212668A1 true CA2212668A1 (en) | 1998-02-13 |
Family
ID=27216553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002212668A Abandoned CA2212668A1 (en) | 1996-08-13 | 1997-08-11 | Supported chemical compound |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6329313B1 (enExample) |
| EP (1) | EP0824112B1 (enExample) |
| JP (1) | JPH10158269A (enExample) |
| KR (1) | KR19980018651A (enExample) |
| CN (1) | CN1182093A (enExample) |
| AT (1) | ATE325821T1 (enExample) |
| AU (1) | AU3413397A (enExample) |
| BR (1) | BR9704354A (enExample) |
| CA (1) | CA2212668A1 (enExample) |
| DE (1) | DE59712644D1 (enExample) |
| NO (1) | NO973707L (enExample) |
| TW (1) | TW408138B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6228795B1 (en) | 1997-06-05 | 2001-05-08 | Exxon Chemical Patents, Inc. | Polymeric supported catalysts |
| US6255531B1 (en) | 1996-06-03 | 2001-07-03 | Targor Gmbh | Boron compounds and other compounds of group IIIa |
| US6391989B1 (en) | 1998-02-27 | 2002-05-21 | Basell Polypropylen Gmbh | Catalyst system, method for producing same and its use for the polymerization of olefins |
| US6476166B1 (en) | 1998-07-16 | 2002-11-05 | Univation Technologies, Llc | Aluminum-based lewis acid cocatalysts for olefin polymerization |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6341144B1 (en) * | 1996-09-20 | 2002-01-22 | At&T Corp. | Video coder providing implicit coefficient prediction and scan adaptation for image coding and intra coding of video |
| WO2000004059A1 (en) * | 1998-07-16 | 2000-01-27 | Exxon Chemical Patents Inc. | Supported lewis acid cocatalysts for olefin polymerization |
| JP2002524621A (ja) * | 1998-09-16 | 2002-08-06 | ザ ダウ ケミカル カンパニー | 機能化した触媒担体及び担持触媒系 |
| JP4864176B2 (ja) * | 1999-02-19 | 2012-02-01 | トータル・ペトロケミカルズ・リサーチ・フエリユイ | ポリオレフィン製造 |
| US6515086B1 (en) | 1999-02-19 | 2003-02-04 | Fina Research, S.A. | Polyolefin production |
| CN1590422A (zh) | 1999-12-23 | 2005-03-09 | 巴塞尔聚烯烃有限公司 | 过渡金属化合物，配体体系，催化剂体系及其在烯烃的聚合反应和共聚反应中的用途 |
| US7105690B2 (en) | 2000-05-31 | 2006-09-12 | Basell Polyolefine Gmbh | Method for producing transition metal compounds and their use for the polymerization of olefins |
| JP4491915B2 (ja) * | 2000-05-31 | 2010-06-30 | 住友化学株式会社 | メタロセン錯体を保存する方法 |
| FR2813079B1 (fr) * | 2000-08-18 | 2003-07-25 | Atofina | Ligands avec au moins un substituant fluorosilicone pour la preparation de metallocenes |
| AU2002227186A1 (en) * | 2000-11-06 | 2002-05-15 | Exxonmobil Chemical Patents Inc | Fluorinated zwitterionic cocatalyst activators for olefin polymerization |
| DE10057009A1 (de) | 2000-11-17 | 2002-05-29 | Celanese Ventures Gmbh | Non-Metallocene, Verfahren zur Herstellung von diesen und deren Verwendung zur Polymerisation von Olefinen |
| DE10130229A1 (de) | 2001-06-22 | 2003-01-02 | Celanese Ventures Gmbh | Non-Metallocene, Verfahren zur Herstellung von diesen und deren Verwendung zur Polymerisation von Olefinen |
| WO2003037937A1 (en) | 2001-10-18 | 2003-05-08 | The Dow Chemical Company | Diene functionalized catalyst supports and supported catalyst compositions |
| DE10208252A1 (de) | 2002-02-26 | 2003-09-04 | Celanese Ventures Gmbh | Konvalent fixierte Non-Metallocene, Verfahren zur Herstellung von diesen und deren Verwendung zur Polymerisation von Olefinen |
| DE10213191A1 (de) | 2002-03-23 | 2003-10-02 | Celanese Ventures Gmbh | Non-Metallocene, Verfahren zur Herstellung von diesen und deren Verwendung zur Polymerisation von Olefinen |
| BR0315341B1 (pt) | 2002-10-15 | 2014-02-18 | Adesivos compreendendo poliolefina. | |
| US7700707B2 (en) | 2002-10-15 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| US7223822B2 (en) | 2002-10-15 | 2007-05-29 | Exxonmobil Chemical Patents Inc. | Multiple catalyst and reactor system for olefin polymerization and polymers produced therefrom |
| US7550528B2 (en) | 2002-10-15 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Functionalized olefin polymers |
| US7541402B2 (en) | 2002-10-15 | 2009-06-02 | Exxonmobil Chemical Patents Inc. | Blend functionalized polyolefin adhesive |
| ES2427626T3 (es) | 2003-02-21 | 2013-10-31 | Styron Europe Gmbh | Procedimiento para homo- o copolimerización de olefinas conjugadas |
| US7217676B2 (en) * | 2004-01-16 | 2007-05-15 | Exxon Mobil Chemical Patents Inc. | Hydrophobization and silica for supported catalyst |
| US7456021B2 (en) * | 2004-01-16 | 2008-11-25 | Exxonmobil Chemical Patents Inc. | Analysis method |
| US7285608B2 (en) | 2004-04-21 | 2007-10-23 | Novolen Technology Holdings C.V. | Metallocene ligands, metallocene compounds and metallocene catalysts, their synthesis and their use for the polymerization of olefins |
| US8034886B2 (en) | 2005-11-04 | 2011-10-11 | Ticona Gmbh | Process for manufacturing high to ultra high molecular weight polymers using novel bridged metallocene catalysts |
| US7598329B2 (en) * | 2005-11-04 | 2009-10-06 | Ticona Gmbh | Process for manufacturing ultra high molecular weight polymers using novel bridged metallocene catalysts |
| JP5034371B2 (ja) * | 2006-02-10 | 2012-09-26 | 富士通株式会社 | Ｒｆｉｄタグの製造方法およびｒｆｉｄタグ |
| EP1847555A1 (en) * | 2006-04-18 | 2007-10-24 | Borealis Technology Oy | Multi-branched Polypropylene |
| EP2203486B9 (en) | 2007-10-25 | 2012-08-01 | Lummus Novolen Technology Gmbh | Racemoselective synthesis of ansa-metallocene compounds, ansa-metallocene compounds, catalysts comprising them, process for producing an olefin polymer by use of the catalysts, and olefin homo- and copolymers |
| EP2235071A2 (en) | 2007-10-25 | 2010-10-06 | Novolen Technology Holdings, C.V. | Metallocene compounds, catalysts comprising them, process for producing an olefin polymer by use of the catalysts, and olefin homo and copolymers |
| JP5598856B2 (ja) * | 2007-10-25 | 2014-10-01 | ルムス・ノボレン・テクノロジー・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | メタロセン化合物、それを含む触媒、その触媒を使用するオレフィンポリマーの製造プロセス、ならびにオレフィンホモポリマーおよびコポリマー |
| WO2009082546A2 (en) | 2007-12-18 | 2009-07-02 | Exxonmobil Chemical Patents Inc. | Polyethylene films and process for production thereof |
| US8507630B2 (en) * | 2008-03-07 | 2013-08-13 | National Institute Of Advanced Industrial Science And Technology | Organic inorganic composite material and utilization thereof |
| EP2915826B1 (en) | 2010-10-21 | 2024-02-28 | Univation Technologies, LLC | Polyethylene and process for production thereof |
| EP3774941B1 (en) | 2018-03-30 | 2022-11-02 | Dow Global Technologies LLC | Binuclear olefin polymerization activators |
| JP2021519362A (ja) | 2018-03-30 | 2021-08-10 | ダウ グローバル テクノロジーズ エルエルシー | オレフィン重合活性化剤 |
| JP7364585B2 (ja) | 2018-03-30 | 2023-10-18 | ダウ グローバル テクノロジーズ エルエルシー | 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 |
| US11447586B2 (en) | 2018-03-30 | 2022-09-20 | Dow Global Technologies Llc | Olefin polymerization activators |
| US11787880B2 (en) | 2018-03-30 | 2023-10-17 | Dow Global Technologies Llc | Highly soluble alkyl substituted carbenium borate as co-catalysts for olefin polymerizations |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2108861T3 (es) * | 1991-11-25 | 1998-01-01 | Exxon Chemical Patents Inc | Composiciones cataliticas polionicas de metales de transicion. |
| DE4207899A1 (de) * | 1992-03-12 | 1993-09-16 | Basf Ag | Feststoff, enthaltend chemisch gebundene metallalkylgruppen, und seine verwendung |
| EP0631589A1 (en) * | 1992-03-16 | 1995-01-04 | Exxon Chemical Patents Inc. | IONIC CATALYST FOR THE PRODUCTION OF POLY-$g(a)-OLEFINS OF CONTROLLED TACTICITY |
| US5347024A (en) | 1993-03-19 | 1994-09-13 | The Dow Chemical Company | Preparation of addition polymerization catalysts via Lewis acid mitigated metal center oxidation |
| US5502017A (en) | 1994-03-10 | 1996-03-26 | Northwestern University | Metallocene catalyst containing bulky organic group |
| US5447895A (en) | 1994-03-10 | 1995-09-05 | Northwestern University | Sterically shielded diboron-containing metallocene olefin polymerization catalysts |
| CA2195879C (en) * | 1994-08-03 | 2001-01-09 | John Flexer Walzer Jr. | Supported ionic catalyst composition |
| EP0710663A1 (en) * | 1994-11-01 | 1996-05-08 | Japan Polyolefins Co., Ltd. | Boron-containing compound, its polymer, catalyst comprising the polymer and metallocene compound, and process for producing polyolefin |
| GB9423606D0 (en) | 1994-11-23 | 1995-01-11 | Piers Warren E | Method of producing base free ziegler-natta olefin polymerizaton catalysts using a new, highly electrophilic borane reagent |
| US5939347A (en) * | 1995-01-25 | 1999-08-17 | W.R. Grace & Co. -Conn. | Supported catalytic activator |
| BR9604776A (pt) * | 1995-03-10 | 1998-06-23 | Dow Chemical Co | Componente de catalisador sustentado catalisador sustentado processo para preparar um componente de catalisador sustentado e um catalisador sustentado aduto de um composto organometálico processo de polimerizaçao por adiç o composto complexo e método para preparar um composto complexo |
| WO1996041808A1 (en) | 1995-06-08 | 1996-12-27 | Showa Denko K.K. | Ionic compounds and catalyst for olefin polymerization using the compounds |
| BR9611772A (pt) * | 1995-11-27 | 1999-02-23 | Dow Chemical Co | Suporte para uso na preparação de catalisadores para polimerizações por adição catalisador suportado e processo de polimerização por adição |
-
1997
- 1997-08-01 EP EP97113300A patent/EP0824112B1/de not_active Expired - Lifetime
- 1997-08-01 AT AT97113300T patent/ATE325821T1/de not_active IP Right Cessation
- 1997-08-01 DE DE59712644T patent/DE59712644D1/de not_active Expired - Fee Related
- 1997-08-11 CA CA002212668A patent/CA2212668A1/en not_active Abandoned
- 1997-08-11 TW TW086111464A patent/TW408138B/zh not_active IP Right Cessation
- 1997-08-12 CN CN97117378A patent/CN1182093A/zh active Pending
- 1997-08-12 US US08/907,938 patent/US6329313B1/en not_active Expired - Fee Related
- 1997-08-12 NO NO973707A patent/NO973707L/no not_active Application Discontinuation
- 1997-08-12 AU AU34133/97A patent/AU3413397A/en not_active Abandoned
- 1997-08-13 KR KR1019970038623A patent/KR19980018651A/ko not_active Withdrawn
- 1997-08-13 BR BR9704354A patent/BR9704354A/pt not_active Application Discontinuation
- 1997-08-13 JP JP9218716A patent/JPH10158269A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255531B1 (en) | 1996-06-03 | 2001-07-03 | Targor Gmbh | Boron compounds and other compounds of group IIIa |
| US6410665B1 (en) | 1996-06-03 | 2002-06-25 | Basell Polyolefine Gmbh | Chemical compound |
| US6228795B1 (en) | 1997-06-05 | 2001-05-08 | Exxon Chemical Patents, Inc. | Polymeric supported catalysts |
| US6391989B1 (en) | 1998-02-27 | 2002-05-21 | Basell Polypropylen Gmbh | Catalyst system, method for producing same and its use for the polymerization of olefins |
| US6476166B1 (en) | 1998-07-16 | 2002-11-05 | Univation Technologies, Llc | Aluminum-based lewis acid cocatalysts for olefin polymerization |
Also Published As
| Publication number | Publication date |
|---|---|
| NO973707L (no) | 1998-02-16 |
| BR9704354A (pt) | 1999-01-12 |
| NO973707D0 (no) | 1997-08-12 |
| KR19980018651A (ko) | 1998-06-05 |
| ATE325821T1 (de) | 2006-06-15 |
| CN1182093A (zh) | 1998-05-20 |
| US6329313B1 (en) | 2001-12-11 |
| EP0824112B1 (de) | 2006-05-10 |
| TW408138B (en) | 2000-10-11 |
| AU3413397A (en) | 1998-02-19 |
| EP0824112A1 (de) | 1998-02-18 |
| DE59712644D1 (de) | 2006-06-14 |
| JPH10158269A (ja) | 1998-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |