CA2262377A1 - Complexes metalliques contenant du cyclopentadienyle a substitution d'heteroatome en position 2 et procede de polymerisation d'olefine - Google Patents
Complexes metalliques contenant du cyclopentadienyle a substitution d'heteroatome en position 2 et procede de polymerisation d'olefine Download PDFInfo
- Publication number
- CA2262377A1 CA2262377A1 CA002262377A CA2262377A CA2262377A1 CA 2262377 A1 CA2262377 A1 CA 2262377A1 CA 002262377 A CA002262377 A CA 002262377A CA 2262377 A CA2262377 A CA 2262377A CA 2262377 A1 CA2262377 A1 CA 2262377A1
- Authority
- CA
- Canada
- Prior art keywords
- inden
- metal complex
- dimethyl
- hydrocarbyl
- dimethylethyl
- 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
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 73
- 239000002184 metal Substances 0.000 title claims abstract description 73
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 34
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 title claims abstract description 17
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 title claims description 64
- 239000003054 catalyst Substances 0.000 claims abstract description 96
- 239000003446 ligand Substances 0.000 claims abstract description 59
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 21
- -1 hydrocarbylsulfido Chemical group 0.000 claims description 202
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 98
- 238000000034 method Methods 0.000 claims description 94
- 150000004696 coordination complex Chemical class 0.000 claims description 64
- 230000008569 process Effects 0.000 claims description 57
- 239000000243 solution Substances 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 53
- 229920000642 polymer Polymers 0.000 claims description 48
- 125000004429 atom Chemical group 0.000 claims description 45
- 239000007789 gas Substances 0.000 claims description 38
- 150000001993 dienes Chemical class 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 229910052782 aluminium Inorganic materials 0.000 claims description 31
- 239000005977 Ethylene Substances 0.000 claims description 30
- 230000003647 oxidation Effects 0.000 claims description 30
- 238000007254 oxidation reaction Methods 0.000 claims description 30
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 29
- 230000003213 activating effect Effects 0.000 claims description 28
- 125000004122 cyclic group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229920000098 polyolefin Polymers 0.000 claims description 15
- 230000007935 neutral effect Effects 0.000 claims description 13
- 125000000129 anionic group Chemical group 0.000 claims description 12
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims description 12
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 239000002002 slurry Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
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- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 10
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 10
- 238000000638 solvent extraction Methods 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
- 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 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 8
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Chemical group CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- 239000002879 Lewis base Substances 0.000 claims description 7
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 7
- 150000002602 lanthanoids Chemical class 0.000 claims description 7
- 150000007527 lewis bases Chemical class 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 229910052768 actinide Inorganic materials 0.000 claims description 6
- 150000001255 actinides Chemical class 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical group C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 159000000003 magnesium salts Chemical class 0.000 claims description 3
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 125000005394 methallyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 150000005839 radical cations Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract description 11
- 229920006158 high molecular weight polymer Polymers 0.000 abstract description 3
- 239000010936 titanium Substances 0.000 description 166
- 229910052719 titanium Inorganic materials 0.000 description 159
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 138
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 126
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- 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 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000178 monomer Substances 0.000 description 45
- 239000000047 product Substances 0.000 description 44
- 238000002360 preparation method Methods 0.000 description 39
- 239000002904 solvent Substances 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 230000002829 reductive effect Effects 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 150000001450 anions Chemical class 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
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- 239000013078 crystal Substances 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 229920002943 EPDM rubber Polymers 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 125000003963 dichloro group Chemical group Cl* 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- 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 14
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
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- 150000002081 enamines Chemical class 0.000 description 11
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 150000001768 cations Chemical class 0.000 description 10
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
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- 238000006467 substitution reaction Methods 0.000 description 8
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 7
- 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 7
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- 125000002524 organometallic group Chemical group 0.000 description 7
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- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 6
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- 238000004364 calculation method Methods 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- CXKQHHJKHZXXPZ-UHFFFAOYSA-N triethylsilanylium Chemical compound CC[Si+](CC)CC CXKQHHJKHZXXPZ-UHFFFAOYSA-N 0.000 description 1
- VOYMPSZBODLRKS-UHFFFAOYSA-N trimethylsilanylium Chemical compound C[Si+](C)C VOYMPSZBODLRKS-UHFFFAOYSA-N 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- 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
-
- 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
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)
Abstract
L'invention concerne des ligands contenant du cyclopentadiényle à hétéroatome substitué, des complexes métalliques contenant lesdits ligands et des systèmes de catalyse à base de composants de catalyse qui comprennent lesdits complexes métalliques. Les complexes métalliques contiennent une liaison hétéroatome-Cp ou une liaison cyclique hétéroatome-Cp en position 2 du Cp. Dans les complexes métalliques préférés, le ligand est un groupe indényle à hétéroatome substitué en position 2. Les systèmes de catalyse pour la polymérisation de l'oléfine peuvent être utilisés à des températures élevées, sont très actifs et permettent de produire un polymère à masse moléculaire élevée.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2376896P | 1996-08-08 | 1996-08-08 | |
US60/023,768 | 1996-08-08 | ||
PCT/US1997/013171 WO1998006728A1 (fr) | 1996-08-08 | 1997-07-28 | Complexes metalliques contenant du cyclopentadienyle a substitution d'heteroatome en position 2 et procede de polymerisation d'olefine |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2262377A1 true CA2262377A1 (fr) | 1998-02-19 |
Family
ID=21817090
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002262377A Abandoned CA2262377A1 (fr) | 1996-08-08 | 1997-07-28 | Complexes metalliques contenant du cyclopentadienyle a substitution d'heteroatome en position 2 et procede de polymerisation d'olefine |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP1021454A1 (fr) |
JP (1) | JP2000516608A (fr) |
KR (1) | KR20000029853A (fr) |
CN (1) | CN1231668A (fr) |
AR (1) | AR009034A1 (fr) |
AU (1) | AU716659B2 (fr) |
BR (1) | BR9711115A (fr) |
CA (1) | CA2262377A1 (fr) |
CO (1) | CO4870709A1 (fr) |
CZ (1) | CZ42499A3 (fr) |
HU (1) | HUP9904148A3 (fr) |
ID (1) | ID18005A (fr) |
NO (1) | NO990546L (fr) |
NZ (1) | NZ333877A (fr) |
PL (1) | PL331526A1 (fr) |
RU (1) | RU2196776C2 (fr) |
SA (1) | SA97180735B1 (fr) |
SK (1) | SK15299A3 (fr) |
TR (1) | TR199900589T2 (fr) |
WO (1) | WO1998006728A1 (fr) |
ZA (2) | ZA976999B (fr) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI971565A (fi) * | 1997-04-14 | 1998-10-15 | Borealis As | Olefiinien polymerointiin tarkoitettujen katalysaattorisysteemien substituoituja metalloseeniyhdisteitä, niiden välituotteet ja valmistusmenetelmä |
DE19809159A1 (de) * | 1998-03-04 | 1999-09-09 | Bayer Ag | Metallorganische Verbindungen |
US6326493B1 (en) * | 1999-01-25 | 2001-12-04 | Chisso Corporation | Metallocene compounds, processes for the preparation thereof, catalyst components for olefin polymerization, and processes for the production of olefin polymers |
CA2365229A1 (fr) | 1999-04-29 | 2000-11-09 | Dow Global Technologies Inc. | Cyclopentadienes bis(n,n-dihydrocarbylamino)- substitues et complexes metalliques associes |
AU3764600A (en) | 1999-05-13 | 2000-12-05 | Dow Chemical Company, The | Di- and tri-heteroatom substituted indenyl metal complexes |
US6646071B1 (en) | 1999-05-13 | 2003-11-11 | The Dow Chemical Company | Metal complexes containing bridging heteroatom for olefin-polymerization-process |
DE60020968T2 (de) | 1999-06-04 | 2006-05-11 | Dow Global Technologies, Inc., Midland | Borsubstituierte cyclopentadiene und metallkomplexe dieser liganden |
US6825295B2 (en) | 1999-12-10 | 2004-11-30 | Dow Global Technologies Inc. | Alkaryl-substituted group 4 metal complexes, catalysts and olefin polymerization process |
EP1253158A1 (fr) * | 1999-12-10 | 2002-10-30 | Dow Global Technologies Inc. | Complexes métalliques du groupe 4 substitués, catalyseurs et procédé de polymérisation d'oléfines |
ES2379243T3 (es) * | 1999-12-10 | 2012-04-24 | Dow Global Technologies Llc | Complejos de metal del grupo 4 sustituidos, catalizadores y procedimiento de polimerización de olefinas |
BR0105177A (pt) | 2000-01-18 | 2002-01-15 | Basell Technology Co Bv | Processo para produzir homopolìmeros ou copolìmeros substancialmente amorfos de propileno |
WO2001053362A1 (fr) * | 2000-01-19 | 2001-07-26 | Borealis Technology Oy | Catalyseurs metallocenes comprenant un (des) groupe(s) cyclopentadienyle(s) siloxy substitue monocyclique(s) destines a la polymerisation d'olefines |
GB0001232D0 (en) * | 2000-01-19 | 2000-03-08 | Borealis Polymers Oy | Polymerisation catalysts |
JP4062929B2 (ja) | 2002-02-08 | 2008-03-19 | 住友化学株式会社 | 遷移金属錯体、配位子、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 |
ATE403684T1 (de) * | 2002-03-14 | 2008-08-15 | Dow Global Technologies Inc | Metallkomplexe mit substituierten indenylliganden und polymerisationsverfahren |
US6927264B2 (en) | 2003-05-28 | 2005-08-09 | Dow Global Technologies Inc. | Metal complexes and polymerization process using same |
MY158186A (en) | 2009-07-28 | 2016-09-15 | Univation Tech Llc | Polymerization process using a supported constrained geometry catalyst |
JP5579859B2 (ja) * | 2010-09-15 | 2014-08-27 | 株式会社日本触媒 | 熱潜在性重合開始剤として用い得る組成物 |
CN102101897B (zh) * | 2010-12-24 | 2013-02-06 | 上海化工研究院 | 侧链含杂环的茂金属催化剂及其在烯烃聚合中的应用 |
CN108794675B (zh) | 2014-03-21 | 2020-12-29 | 埃克森美孚化学专利公司 | 乙烯丙烯共聚物的制备方法 |
JP6739435B2 (ja) | 2015-01-06 | 2020-08-12 | エスシージー ケミカルズ カンパニー,リミテッド | SiO2−層状複水酸化物ミクロスフェアおよびその作製方法 |
KR102010630B1 (ko) * | 2016-01-20 | 2019-08-13 | 한화토탈 주식회사 | 올레핀 중합촉매 및 이를 이용한 올레핀 중합방법 |
GB201608384D0 (en) | 2016-05-12 | 2016-06-29 | Scg Chemicals Co Ltd | Unsymmetrical metallocene catalysts and uses thereof |
CN110612313A (zh) * | 2017-03-23 | 2019-12-24 | 埃克森美孚化学专利公司 | 催化剂体系及其制备和使用方法 |
KR102643986B1 (ko) | 2017-09-29 | 2024-03-07 | 사빅 에스케이 넥슬렌 컴퍼니 피티이 엘티디 | 신규한 인덴계 전이금속 화합물, 이를 포함하는 전이금속 촉매 조성물, 및 이를 이용한 에틸렌 단독중합체 또는 에틸렌과 α-올레핀의 공중합체의 제조방법 |
KR20200105409A (ko) | 2019-02-28 | 2020-09-07 | 사빅 에스케이 넥슬렌 컴퍼니 피티이 엘티디 | 신규한 테트라아릴보레이트 화합물, 이를 포함하는 촉매 조성물, 및 이를 이용한 에틸렌 단독중합체 또는 에틸렌과 α-올레핀의 공중합체의 제조방법 |
WO2020174346A1 (fr) | 2019-02-28 | 2020-09-03 | 사빅 에스케이 넥슬렌 컴퍼니 피티이 엘티디 | Nouveau composé de tétraarylborate, composition de catalyseur le contenant, et procédé de préparation d'homopolymères ou de copolymères d'éthylène et d'alpha-oléfine l'utilisant |
JP7118500B2 (ja) | 2019-09-27 | 2022-08-16 | エルジー・ケム・リミテッド | 混成担持触媒およびそれを用いたポリオレフィンの製造方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5096867A (en) * | 1990-06-04 | 1992-03-17 | Exxon Chemical Patents Inc. | Monocyclopentadienyl transition metal olefin polymerization catalysts |
NZ235032A (en) * | 1989-08-31 | 1993-04-28 | Dow Chemical Co | Constrained geometry complexes of titanium, zirconium or hafnium comprising a substituted cyclopentadiene ligand; use as olefin polymerisation catalyst component |
ATE198207T1 (de) * | 1992-08-03 | 2001-01-15 | Targor Gmbh | Verfahren zur herstellung eines olefinpolymers unter verwendung spezieller metallocene |
DE4406964A1 (de) * | 1994-03-03 | 1995-09-07 | Basf Ag | Geträgerte Metalloxenkomplexe mit heterofunktionellen Gruppen am Cyclopentadienylsystem als Katalysatorsysteme |
DE4406963A1 (de) * | 1994-03-03 | 1995-09-07 | Basf Ag | Metallocenkomplexe mit heterofunktionellen Gruppen am Cyclopentadienylsystem |
-
1997
- 1997-07-28 HU HU9904148A patent/HUP9904148A3/hu unknown
- 1997-07-28 CA CA002262377A patent/CA2262377A1/fr not_active Abandoned
- 1997-07-28 PL PL97331526A patent/PL331526A1/xx unknown
- 1997-07-28 RU RU99104650/04A patent/RU2196776C2/ru not_active IP Right Cessation
- 1997-07-28 JP JP10509760A patent/JP2000516608A/ja active Pending
- 1997-07-28 CN CN97198208A patent/CN1231668A/zh active Pending
- 1997-07-28 SK SK152-99A patent/SK15299A3/sk not_active Application Discontinuation
- 1997-07-28 TR TR1999/00589T patent/TR199900589T2/xx unknown
- 1997-07-28 EP EP97937033A patent/EP1021454A1/fr not_active Withdrawn
- 1997-07-28 NZ NZ333877A patent/NZ333877A/xx unknown
- 1997-07-28 WO PCT/US1997/013171 patent/WO1998006728A1/fr not_active Application Discontinuation
- 1997-07-28 KR KR1019997001015A patent/KR20000029853A/ko not_active Application Discontinuation
- 1997-07-28 AU AU39647/97A patent/AU716659B2/en not_active Ceased
- 1997-07-28 CZ CZ99424A patent/CZ42499A3/cs unknown
- 1997-07-28 BR BR9711115A patent/BR9711115A/pt not_active IP Right Cessation
- 1997-08-06 ZA ZA976999A patent/ZA976999B/xx unknown
- 1997-08-06 ZA ZA976998A patent/ZA976998B/xx unknown
- 1997-08-07 ID IDP972749A patent/ID18005A/id unknown
- 1997-08-08 CO CO97045592A patent/CO4870709A1/es unknown
- 1997-08-08 AR ARP970103616A patent/AR009034A1/es not_active Application Discontinuation
- 1997-12-24 SA SA97180735A patent/SA97180735B1/ar unknown
-
1999
- 1999-02-05 NO NO990546A patent/NO990546L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
ID18005A (id) | 1998-02-19 |
PL331526A1 (en) | 1999-07-19 |
CO4870709A1 (es) | 1999-12-27 |
EP1021454A1 (fr) | 2000-07-26 |
TR199900589T2 (xx) | 1999-07-21 |
CN1231668A (zh) | 1999-10-13 |
NO990546L (no) | 1999-03-29 |
BR9711115A (pt) | 1999-08-17 |
ZA976999B (en) | 1999-02-08 |
AU716659B2 (en) | 2000-03-02 |
HUP9904148A3 (en) | 2003-03-28 |
KR20000029853A (ko) | 2000-05-25 |
AR009034A1 (es) | 2000-03-08 |
NZ333877A (en) | 2000-08-25 |
AU3964797A (en) | 1998-03-06 |
ZA976998B (en) | 1999-02-08 |
SA97180735B1 (ar) | 2006-10-08 |
RU2196776C2 (ru) | 2003-01-20 |
NO990546D0 (no) | 1999-02-05 |
CZ42499A3 (cs) | 1999-07-14 |
HUP9904148A2 (hu) | 2000-03-28 |
SK15299A3 (en) | 2000-03-13 |
WO1998006728A1 (fr) | 1998-02-19 |
JP2000516608A (ja) | 2000-12-12 |
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