ES2211808T3 - Compuestos puenteados de bis(indenil)metaloceno. - Google Patents
Compuestos puenteados de bis(indenil)metaloceno.Info
- Publication number
- ES2211808T3 ES2211808T3 ES01937633T ES01937633T ES2211808T3 ES 2211808 T3 ES2211808 T3 ES 2211808T3 ES 01937633 T ES01937633 T ES 01937633T ES 01937633 T ES01937633 T ES 01937633T ES 2211808 T3 ES2211808 T3 ES 2211808T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- rac
- silafluorendiyl
- indenyl
- zirconium
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 97
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 45
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000004429 atom Chemical group 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 21
- 125000005018 aryl alkenyl group Chemical group 0.000 claims abstract description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 13
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 12
- 150000001993 dienes Chemical class 0.000 claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 8
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 7
- 229910052718 tin Inorganic materials 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims abstract description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 4
- 229910052758 niobium Inorganic materials 0.000 claims abstract description 4
- 229910052715 tantalum Inorganic materials 0.000 claims abstract description 4
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 4
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 229910052804 chromium Inorganic materials 0.000 claims abstract 2
- -1 ethylene, propylene, 1-butene Chemical class 0.000 claims description 485
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 79
- 230000003197 catalytic effect Effects 0.000 claims description 29
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 22
- 230000003213 activating effect Effects 0.000 claims description 20
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 239000010703 silicon Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 239000010936 titanium Substances 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000011733 molybdenum Chemical group 0.000 claims description 3
- 239000010955 niobium Chemical group 0.000 claims description 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical group [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical group [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Chemical group 0.000 claims description 3
- 239000010937 tungsten Chemical group 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical group [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims 1
- 239000011651 chromium Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 10
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 42
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- 239000002904 solvent Substances 0.000 description 24
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 22
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 13
- 150000001450 anions Chemical class 0.000 description 12
- 229920001155 polypropylene Polymers 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000011148 porous material Substances 0.000 description 10
- OCTIQWBTLNVDFV-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-2-propan-2-yl-1h-indene Chemical compound C1C(C(C)C)=CC2=C1C=CC=C2C1=CC(C)=CC(C)=C1 OCTIQWBTLNVDFV-UHFFFAOYSA-N 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 229910052744 lithium Inorganic materials 0.000 description 9
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 7
- PTEGFVQBIPDXFA-UHFFFAOYSA-N 4-(3,5-ditert-butylphenyl)-2-methyl-1h-indene Chemical compound C1C(C)=CC2=C1C=CC=C2C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 PTEGFVQBIPDXFA-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZJHMRPBTRSQNPI-UHFFFAOYSA-N benzo[b][1]benzosilole Chemical compound C1=CC=C2[Si]C3=CC=CC=C3C2=C1 ZJHMRPBTRSQNPI-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 5
- IQURIBNOAPIFPZ-UHFFFAOYSA-N 5,5-dichlorobenzo[b][1]benzosilole Chemical compound C1=CC=C2[Si](Cl)(Cl)C3=CC=CC=C3C2=C1 IQURIBNOAPIFPZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- 229910007926 ZrCl Inorganic materials 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 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
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 229910007928 ZrCl2 Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- QWJRBTRSAZACSX-UHFFFAOYSA-N 4-chloro-2-methyl-1h-indene Chemical compound C1=CC=C(Cl)C2=C1CC(C)=C2 QWJRBTRSAZACSX-UHFFFAOYSA-N 0.000 description 2
- VDFIGYCUOGDOPV-UHFFFAOYSA-N 4-chloro-2-propan-2-yl-1h-indene Chemical compound C1=CC=C(Cl)C2=C1CC(C(C)C)=C2 VDFIGYCUOGDOPV-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
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- DDUAXFBYKYDFJT-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C=C(C=1)C(C)(C)C)[Mg] Chemical compound C(C)(C)(C)C=1C=C(C=C(C=1)C(C)(C)C)[Mg] DDUAXFBYKYDFJT-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 150000004678 hydrides Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229920001580 isotactic polymer Polymers 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002195 soluble material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000007704 transition Effects 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
- 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 2
- 239000003643 water by type Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZJDMXYIFGDPIN-UHFFFAOYSA-N 1-(4-naphthalen-1-ylbuta-1,3-dienyl)naphthalene Chemical compound C1=CC=C2C(C=CC=CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 AZJDMXYIFGDPIN-UHFFFAOYSA-N 0.000 description 1
- WTHBQEAHMCCGFM-UHFFFAOYSA-N 1-methyl-2-[4-(2-methylphenyl)buta-1,3-dienyl]benzene Chemical compound CC1=CC=CC=C1C=CC=CC1=CC=CC=C1C WTHBQEAHMCCGFM-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VSYZXASVWVQEMR-UHFFFAOYSA-N 2-methylbuta-1,3-dienylalumane Chemical compound CC(=C[AlH2])C=C VSYZXASVWVQEMR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RREAVEQOCKXSHQ-UHFFFAOYSA-N 2h-inden-2-ide Chemical compound C1=CC=C2[CH-]C=CC2=C1 RREAVEQOCKXSHQ-UHFFFAOYSA-N 0.000 description 1
- RLKASFXMXUOUFQ-UHFFFAOYSA-N 4-bromo-2-methyl-1h-indene Chemical compound C1=CC=C(Br)C2=C1CC(C)=C2 RLKASFXMXUOUFQ-UHFFFAOYSA-N 0.000 description 1
- QLKINISCYVCLTE-UHFFFAOYSA-N 6-phenylhexa-2,4-dienylbenzene Chemical compound C=1C=CC=CC=1CC=CC=CCC1=CC=CC=C1 QLKINISCYVCLTE-UHFFFAOYSA-N 0.000 description 1
- KFCMUZONUPOPAC-UHFFFAOYSA-N C1=CC=C2[SiH2]C3=CC=CC=C3C2=C1 Chemical compound C1=CC=C2[SiH2]C3=CC=CC=C3C2=C1 KFCMUZONUPOPAC-UHFFFAOYSA-N 0.000 description 1
- GPSLEIDMOQAVFA-UHFFFAOYSA-N CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)OC(C(F)=C(C(F)=C1F)F)=C1F Chemical compound CCCCN(CCCC)CCCC.CCCCN(CCCC)CCCC.OB(O)OC(C(F)=C(C(F)=C1F)F)=C1F GPSLEIDMOQAVFA-UHFFFAOYSA-N 0.000 description 1
- UGVVIPAIDGTTNN-UHFFFAOYSA-N C[Zr]C Chemical compound C[Zr]C UGVVIPAIDGTTNN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910003902 SiCl 4 Inorganic materials 0.000 description 1
- BCRJHHFLBOQAMG-YNRRLODASA-N [(1e,3e)-penta-1,3-dienyl]benzene Chemical compound C\C=C\C=C\C1=CC=CC=C1 BCRJHHFLBOQAMG-YNRRLODASA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Chemical class 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002469 indenes Chemical class 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 229910001504 inorganic chloride Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- UWIBIDGHIMGNRC-UHFFFAOYSA-M magnesium;1,3-dimethylbenzene-5-ide;bromide Chemical compound [Mg+2].[Br-].CC1=C[C-]=CC(C)=C1 UWIBIDGHIMGNRC-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 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 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 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 1
- 239000011236 particulate material Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis 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
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- KTDRTOYQXRJJTE-FIFLTTCUSA-N trimethyl-[(1e,3e)-4-trimethylsilylbuta-1,3-dienyl]silane Chemical compound C[Si](C)(C)\C=C\C=C\[Si](C)(C)C KTDRTOYQXRJJTE-FIFLTTCUSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US619749 | 1990-11-29 | ||
| US21545900P | 2000-06-30 | 2000-06-30 | |
| US21559700P | 2000-06-30 | 2000-06-30 | |
| US215459P | 2000-06-30 | ||
| US215597P | 2000-06-30 | ||
| US09/619,757 US6380334B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US620613 | 2000-07-19 | ||
| US620341 | 2000-07-19 | ||
| US620046 | 2000-07-19 | ||
| US620359 | 2000-07-19 | ||
| US619751 | 2000-07-19 | ||
| US09/619,764 US6376409B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US09/620,303 US6414095B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US09/620,198 US6380330B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US620303 | 2000-07-19 | ||
| US619757 | 2000-07-19 | ||
| US09/620,341 US6380123B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US619764 | 2000-07-19 | ||
| US09/620,302 US6376411B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US09/619,749 US6376407B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US619750 | 2000-07-19 | ||
| US620302 | 2000-07-19 | ||
| US620198 | 2000-07-19 | ||
| US09/619,750 US6380120B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US09/620,359 US6376413B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US09/619,751 US6380121B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US09/620,046 US6380122B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
| US09/620,613 US6380331B1 (en) | 2000-06-30 | 2000-07-19 | Metallocene compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2211808T3 true ES2211808T3 (es) | 2004-07-16 |
Family
ID=27585093
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01937633T Expired - Lifetime ES2211808T3 (es) | 2000-06-30 | 2001-05-21 | Compuestos puenteados de bis(indenil)metaloceno. |
| ES03027480T Expired - Lifetime ES2247473T3 (es) | 2000-06-30 | 2001-05-21 | Composiciones de bis-indenil-metaloceno puenteadas. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03027480T Expired - Lifetime ES2247473T3 (es) | 2000-06-30 | 2001-05-21 | Composiciones de bis-indenil-metaloceno puenteadas. |
Country Status (6)
| Country | Link |
|---|---|
| EP (2) | EP1411058B1 (https=) |
| JP (1) | JP2004502698A (https=) |
| AT (2) | ATE260289T1 (https=) |
| DE (2) | DE60102156T8 (https=) |
| ES (2) | ES2211808T3 (https=) |
| WO (1) | WO2002002575A1 (https=) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7122498B2 (en) | 2000-06-30 | 2006-10-17 | Exxonmobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
| JP2005522406A (ja) * | 2001-06-29 | 2005-07-28 | エクソンモービル・ケミカル・パテンツ・インク | メタロセン及び該メタロセン由来の触媒組成物 |
| DE10158656A1 (de) | 2001-11-30 | 2003-06-26 | Basell Polyolefine Gmbh | Organoübergangsmetallverbindung, Biscyclopentadienylligandsystem, Katalysatorsystem und Verfahren zur Herstellung von Polyolefinen |
| DE60306147T2 (de) * | 2002-04-23 | 2007-04-19 | Dow Global Technologies, Inc., Midland | Alkarylsubstituierte komplexe von gruppe-4-metallen, katalysatoren und verfahren zur polymerisierung von olefinen |
| US7569647B2 (en) | 2002-10-10 | 2009-08-04 | Basell Polyolefine Gmbh | Process for the copolymerization of ethylene |
| JP4590037B2 (ja) * | 2003-09-30 | 2010-12-01 | 日本ポリプロ株式会社 | オレフィン重合用触媒成分、α−オレフィン重合用触媒及びα−オレフィン重合体の製造方法 |
| JP2008509277A (ja) * | 2004-08-09 | 2008-03-27 | ダウ グローバル テクノロジーズ インコーポレイティド | ポリマーの製造のための担持ビス（ヒドロキシアリールアリールオキシ）触媒 |
| US20090017710A1 (en) * | 2006-02-02 | 2009-01-15 | Basell Polyolefine Gmbh | Propylene Melt Blown Resins, Propylene Melt Blown Resin Fibers and Non-Woven Fabric Made From the Same, and Methods of Making the Same |
| TW200932770A (en) | 2007-10-22 | 2009-08-01 | Univation Tech Llc | Metallocene catalysts and their use in polymerization processes |
| WO2011058089A1 (en) | 2009-11-13 | 2011-05-19 | Borealis Ag | Process for producing a polymerization catalyst |
| ES2424958T3 (es) | 2009-11-13 | 2013-10-10 | Borealis Ag | Proceso para polimerización de olefinas |
| US8603933B2 (en) | 2009-11-13 | 2013-12-10 | Borealis Ag | Process for recovering a transition metal compound |
| EP2322568B1 (en) | 2009-11-13 | 2013-05-15 | Borealis AG | Process for producing an olefin polymerization catalyst |
| EP2330136B1 (en) | 2009-12-07 | 2013-08-28 | Borealis AG | Process for the preparation of an unsupported, solid metallocene catalyst system and its use in polymerization of olefins |
| PT2495037T (pt) | 2011-03-02 | 2020-09-15 | Borealis Ag | Montagem de reator de alto rendimento para a polimerização de olefinas |
| EP2495038B1 (en) | 2011-03-02 | 2020-09-02 | Borealis AG | A process for the production polymers |
| EP2532687A3 (en) | 2011-06-10 | 2013-04-10 | Borealis AG | Bridged Metallocene Catalysts |
| EP2535372B1 (en) | 2011-06-15 | 2016-09-14 | Borealis AG | In-situ reactor blend of a Ziegler-Natta catalysed, nucleated polypropylene and a metallocene catalysed polypropylene |
| EP2890490B1 (en) | 2012-08-29 | 2020-05-06 | Borealis AG | Reactor assembly and method for polymerization of olefins |
| EP2914638A4 (en) * | 2012-10-31 | 2016-07-27 | Exxonmobil Chem Patents Inc | PROPYLENE COPOLYMER COMPOSITIONS AND METHODS OF MAKING THE SAME |
| EP2745926A1 (en) | 2012-12-21 | 2014-06-25 | Borealis AG | Gas phase polymerization and reactor assembly comprising a fluidized bed reactor and an external moving bed reactor |
| EP2746289B1 (en) | 2012-12-21 | 2017-09-27 | Borealis AG | Catalysts |
| EP2746301B1 (en) | 2012-12-21 | 2018-05-30 | Borealis AG | Catalyst |
| JP6193398B2 (ja) | 2012-12-21 | 2017-09-06 | ボレアリス エージー | 触媒 |
| EP2745927A1 (en) | 2012-12-21 | 2014-06-25 | Borealis AG | Fluidized bed reactor with internal moving bed reaction unit |
| ES2703344T3 (es) | 2013-07-17 | 2019-03-08 | Exxonmobil Chemical Patents Inc | Metalocenos y composiciones catalíticas derivadas de ellos |
| US9938364B2 (en) | 2013-07-17 | 2018-04-10 | Exxonmobil Chemical Patents Inc. | Substituted metallocene catalysts |
| US9834628B2 (en) | 2013-07-17 | 2017-12-05 | Exxonmobil Chemical Patents Inc. | Cyclopropyl substituted metallocene catalysts |
| EP3022238B1 (en) | 2013-07-17 | 2017-09-20 | ExxonMobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
| JP2016531978A (ja) | 2013-07-17 | 2016-10-13 | エクソンモービル ケミカル パテンツ インコーポレイテッド | 置換メタロセン触媒 |
| EP3848401A1 (en) | 2013-07-17 | 2021-07-14 | ExxonMobil Chemical Patents Inc. | Isotactic propylene polymers |
| EP3083649A4 (en) * | 2013-12-19 | 2016-10-26 | Exxonmobil Chem Patents Inc | BRIDGED TO (INDENYL) TRANSFER METAL COMPLEXES, MANUFACTURE AND USE THEREOF |
| US9944665B2 (en) | 2013-12-19 | 2018-04-17 | Exxonmobil Chemical Patents Inc. | Bridged bis(indenyl) transitional metal complexes, production, and use thereof |
| US9963522B2 (en) | 2014-03-20 | 2018-05-08 | Japan Polypropylene Corporation | Metallocene complex and method for producing olefin polymer |
| JP6201853B2 (ja) * | 2014-03-25 | 2017-09-27 | 日本ポリプロ株式会社 | メタロセン錯体及びオレフィン重合体の製造方法 |
| ES2635519T3 (es) | 2014-11-21 | 2017-10-04 | Borealis Ag | Procedimiento para producir gránulos de copolímeros blandos |
| US11292156B2 (en) | 2014-12-08 | 2022-04-05 | Borealis Ag | Process for producing pellets of copolymers of propylene |
| US10570219B2 (en) | 2015-06-05 | 2020-02-25 | Exxonmobil Chemical Patents Inc. | Production of heterophasic polymers in gas or slurry phase |
| US10280235B2 (en) | 2015-06-05 | 2019-05-07 | Exxonmobil Chemical Patents Inc. | Catalyst system containing high surface area supports and sequential polymerization to produce heterophasic polymers |
| US10280233B2 (en) | 2015-06-05 | 2019-05-07 | Exxonmobil Chemical Patents Inc. | Catalyst systems and methods of making and using the same |
| WO2016196334A1 (en) | 2015-06-05 | 2016-12-08 | Exxonmobil Chemical Patents Inc. | Single reactor production of polymers in gas or slurry phase |
| WO2016196331A1 (en) | 2015-06-05 | 2016-12-08 | Exxonmobil Chemical Patents Inc. | Supported metallocene catalyst systems for polymerization |
| US9809664B2 (en) | 2015-06-05 | 2017-11-07 | Exxonmobil Chemical Patents Inc. | Bimodal propylene polymers and sequential polymerization |
| US10329360B2 (en) | 2015-06-05 | 2019-06-25 | Exxonmobil Chemical Patents Inc. | Catalyst system comprising supported alumoxane and unsupported alumoxane particles |
| US10294316B2 (en) | 2015-06-05 | 2019-05-21 | Exxonmobil Chemical Patents Inc. | Silica supports with high aluminoxane loading capability |
| EP3124567A1 (en) | 2015-07-30 | 2017-02-01 | Borealis AG | Polypropylene based hot-melt adhesive composition |
| EP3178853B1 (en) | 2015-12-07 | 2018-07-25 | Borealis AG | Process for polymerising alpha-olefin monomers |
| JP6613987B2 (ja) * | 2016-03-28 | 2019-12-04 | 日本ポリプロ株式会社 | メタロセン錯体、オレフィン重合用触媒、およびオレフィン重合体の製造方法 |
| EP3243622B1 (en) | 2016-05-13 | 2020-09-09 | Borealis AG | Process for hydraulic conveying of polyolefin pellets |
| US11059918B2 (en) | 2016-05-27 | 2021-07-13 | Exxonmobil Chemical Patents Inc. | Metallocene catalyst compositions and polymerization process therewith |
| EP3608364A1 (en) | 2018-08-06 | 2020-02-12 | Borealis AG | Multimodal propylene random copolymer based composition suitable as hot melt adhesive composition |
| US20210277290A1 (en) | 2018-08-06 | 2021-09-09 | Borealis Ag | Propylene random copolymer based hot melt adhesive composition |
| ES2986685T3 (es) | 2018-11-30 | 2024-11-12 | Borealis Ag | Proceso de lavado |
| US12606657B2 (en) | 2019-08-22 | 2026-04-21 | Exxonmobil Chemical Patents Inc. | Isotactic propylene homopolymers and copolymers produced with C1 symmetric metallocene catalysts |
| US11472828B2 (en) | 2019-10-11 | 2022-10-18 | Exxonmobil Chemical Patents Inc. | Indacene based metallocene catalysts useful in the production of propylene polymers |
| EP4247825A1 (en) | 2020-11-23 | 2023-09-27 | ExxonMobil Chemical Patents Inc. | Metallocene polypropylene prepared using aromatic solvent-free supports |
| EP4144435A1 (en) | 2021-09-01 | 2023-03-08 | Borealis AG | Gas phase polymerization process with improved gas recycling |
| WO2023034889A1 (en) | 2021-09-02 | 2023-03-09 | Exxonmobil Chemical Patents Inc. | C1 symmetric metallocene catalysts tailored for production of vinyl-terminated polypropylene oligomers and macromonomers |
| JP2025526711A (ja) | 2022-08-09 | 2025-08-15 | エクソンモービル ケミカル パテンツ インコーポレイテッド | ジフェニルシラン架橋ｃ１対称触媒及びそれから製造するポリマー |
| EP4389776A1 (en) | 2022-12-20 | 2024-06-26 | Borealis AG | Process |
| EP4389783A1 (en) | 2022-12-20 | 2024-06-26 | Borealis AG | Catalyst transition process |
| KR20250126808A (ko) | 2022-12-23 | 2025-08-25 | 보레알리스 아게 | 폴리프로필렌 단독중합체 또는 공중합체의 제조방법 |
| CN120380036A (zh) | 2022-12-23 | 2025-07-25 | 北欧化工股份公司 | 高流动性聚丙烯均聚物的制造方法 |
| CN120380039A (zh) | 2022-12-23 | 2025-07-25 | 北欧化工股份公司 | 聚丙烯共聚物的生产方法 |
| EP4716625A1 (en) | 2023-05-23 | 2026-04-01 | Borealis GmbH | Process for producing pellets of polyolefins, and pellets so produced |
| WO2025003435A1 (en) | 2023-06-30 | 2025-01-02 | Borealis Ag | Process |
| WO2025219537A1 (en) | 2024-04-18 | 2025-10-23 | Borealis Gmbh | Process for propylene polymerization with optimized prepolymerization conditions |
| WO2025219533A1 (en) | 2024-04-18 | 2025-10-23 | Borealis Gmbh | Process for the preparation of a propylene homopolymer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW294669B (https=) * | 1992-06-27 | 1997-01-01 | Hoechst Ag |
-
2001
- 2001-05-21 AT AT01937633T patent/ATE260289T1/de not_active IP Right Cessation
- 2001-05-21 EP EP03027480A patent/EP1411058B1/en not_active Expired - Lifetime
- 2001-05-21 WO PCT/US2001/016425 patent/WO2002002575A1/en not_active Ceased
- 2001-05-21 EP EP01937633A patent/EP1294733B1/en not_active Expired - Lifetime
- 2001-05-21 JP JP2002507827A patent/JP2004502698A/ja active Pending
- 2001-05-21 DE DE60102156T patent/DE60102156T8/de active Active
- 2001-05-21 DE DE60114896T patent/DE60114896T8/de active Active
- 2001-05-21 ES ES01937633T patent/ES2211808T3/es not_active Expired - Lifetime
- 2001-05-21 AT AT03027480T patent/ATE309259T1/de not_active IP Right Cessation
- 2001-05-21 ES ES03027480T patent/ES2247473T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60102156T2 (de) | 2004-12-09 |
| DE60102156T8 (de) | 2005-06-23 |
| EP1294733A1 (en) | 2003-03-26 |
| DE60102156D1 (de) | 2004-04-01 |
| EP1411058B1 (en) | 2005-11-09 |
| JP2004502698A (ja) | 2004-01-29 |
| EP1294733B1 (en) | 2004-02-25 |
| EP1411058A1 (en) | 2004-04-21 |
| DE60114896D1 (de) | 2005-12-15 |
| WO2002002575A1 (en) | 2002-01-10 |
| DE60114896T2 (de) | 2006-07-27 |
| ATE260289T1 (de) | 2004-03-15 |
| DE60114896T8 (de) | 2007-04-26 |
| ES2247473T3 (es) | 2006-03-01 |
| ATE309259T1 (de) | 2005-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2211808T3 (es) | Compuestos puenteados de bis(indenil)metaloceno. | |
| US6888017B2 (en) | Metallocene compositions | |
| US6376410B1 (en) | Metallocene compositions | |
| CN1332966C (zh) | 桥接双(茚基)金属茂化合物 | |
| US6376627B1 (en) | Metallocene compositions | |
| US6399723B1 (en) | Metallocene compositions | |
| US6376412B1 (en) | Metallocene compositions | |
| US6380120B1 (en) | Metallocene compositions | |
| US6376409B1 (en) | Metallocene compositions | |
| US6380331B1 (en) | Metallocene compositions | |
| US6376407B1 (en) | Metallocene compositions | |
| EP0520732B1 (en) | Homogeneous olefin polymerization catalyst by ligand abstraction with lewis acids | |
| JP4119843B2 (ja) | メタロセン類、及びそれらから誘導される触媒組成物 | |
| ES2638094T3 (es) | Catalizadores de polimerización para producir polímeros con bajos niveles de ramificación de cadena larga | |
| ES2203714T3 (es) | Sistema de catalizador soportado, procedimiento para su produccion y su utilizacion para la polimerizacion de olefinas. | |
| US6894179B2 (en) | Metallocene compositions | |
| US6380334B1 (en) | Metallocene compositions | |
| US6380121B1 (en) | Metallocene compositions | |
| US6380123B1 (en) | Metallocene compositions | |
| US6376411B1 (en) | Metallocene compositions | |
| WO2001070395A2 (en) | Polymerization catalysts comprising an open eta-5 ligand | |
| US6380124B1 (en) | Metallocene compositions | |
| US6380330B1 (en) | Metallocene compositions | |
| US6376408B1 (en) | Metallocene compositions | |
| EP0705283B1 (en) | PROCESS FOR PRODUCING AMORPHOUS POLY-$g(a)-OLEFINS WITH A MONOCYCLOPENTADIENYL TRANSITION METAL CATALYST SYSTEM |