CA2292538A1 - Ethylene enhancement of processes for synthesis of high melting thermoplastic elastomeric .alpha.-olefin polymers (pre/epe effects) - Google Patents
Ethylene enhancement of processes for synthesis of high melting thermoplastic elastomeric .alpha.-olefin polymers (pre/epe effects) Download PDFInfo
- Publication number
- CA2292538A1 CA2292538A1 CA002292538A CA2292538A CA2292538A1 CA 2292538 A1 CA2292538 A1 CA 2292538A1 CA 002292538 A CA002292538 A CA 002292538A CA 2292538 A CA2292538 A CA 2292538A CA 2292538 A1 CA2292538 A1 CA 2292538A1
- Authority
- CA
- Canada
- Prior art keywords
- ethylene
- polymerization
- polymerization process
- metallocene
- elastomeric
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 140
- 239000005977 Ethylene Substances 0.000 title claims abstract description 140
- 238000000034 method Methods 0.000 title claims abstract description 50
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 19
- 230000000694 effects Effects 0.000 title claims description 55
- 238000002844 melting Methods 0.000 title claims description 28
- 230000008018 melting Effects 0.000 title claims description 28
- 229920001169 thermoplastic Polymers 0.000 title claims description 13
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 13
- 230000008569 process Effects 0.000 title abstract description 22
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 106
- 239000012968 metallocene catalyst Substances 0.000 claims abstract description 22
- 239000004711 α-olefin Substances 0.000 claims abstract description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 124
- 239000003054 catalyst Substances 0.000 claims description 123
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 74
- -1 1-methyl-2-phenylindenyl Chemical group 0.000 claims description 55
- 239000003446 ligand Substances 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 229920001577 copolymer Polymers 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 22
- 150000001336 alkenes Chemical class 0.000 claims description 20
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 230000000717 retained effect Effects 0.000 claims description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052723 transition metal Inorganic materials 0.000 claims description 15
- 150000003624 transition metals Chemical class 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229920001971 elastomer Polymers 0.000 claims description 11
- 239000000806 elastomer Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 8
- 229910052735 hafnium Inorganic materials 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 229910052768 actinide Inorganic materials 0.000 claims description 5
- 150000001255 actinides Chemical class 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- 150000002602 lanthanoids Chemical class 0.000 claims description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229920001198 elastomeric copolymer Polymers 0.000 claims 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims 1
- 238000003780 insertion Methods 0.000 abstract description 9
- 230000037431 insertion Effects 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 183
- 239000000243 solution Substances 0.000 description 137
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 95
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 87
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 48
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 47
- 239000007787 solid Substances 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 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 40
- 239000002904 solvent Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 31
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 28
- 229960004132 diethyl ether Drugs 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- 229920001155 polypropylene Polymers 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000004743 Polypropylene Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 238000011084 recovery Methods 0.000 description 19
- 101150041968 CDC13 gene Proteins 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 238000010348 incorporation Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910007932 ZrCl4 Inorganic materials 0.000 description 7
- 229920002725 thermoplastic elastomer Polymers 0.000 description 7
- BSBXLZYWGGAVHD-UHFFFAOYSA-N 2-phenyl-1h-indene Chemical compound C=1C2=CC=CC=C2CC=1C1=CC=CC=C1 BSBXLZYWGGAVHD-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 230000037048 polymerization activity Effects 0.000 description 5
- 238000013022 venting Methods 0.000 description 5
- SOKYZLBJLDLMTR-UHFFFAOYSA-N 1-methyl-2-phenyl-1h-indene Chemical compound C=1C2=CC=CC=C2C(C)C=1C1=CC=CC=C1 SOKYZLBJLDLMTR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910007928 ZrCl2 Inorganic materials 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000009021 linear effect Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001384 propylene homopolymer Polymers 0.000 description 4
- 229920005653 propylene-ethylene copolymer Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- MDFLZWDNYLIUMV-UHFFFAOYSA-N 1-phenyl-2,3-dihydroinden-1-ol Chemical compound C1CC2=CC=CC=C2C1(O)C1=CC=CC=C1 MDFLZWDNYLIUMV-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- BWRRWBIBNBVHQF-UHFFFAOYSA-N 4-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)butanoic acid Chemical compound O1C(CCCC(=O)O)=NC(C=2N=CC=CC=2)=N1 BWRRWBIBNBVHQF-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JEKOISATHYKFFC-UHFFFAOYSA-L [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 JEKOISATHYKFFC-UHFFFAOYSA-L 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- IDASTKMEQGPVRR-UHFFFAOYSA-N cyclopenta-1,3-diene;zirconium(2+) Chemical compound [Zr+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 IDASTKMEQGPVRR-UHFFFAOYSA-N 0.000 description 3
- 230000005595 deprotonation Effects 0.000 description 3
- 238000010537 deprotonation reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000007514 turning Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- AWEIZPJLIGMMLJ-UHFFFAOYSA-N 2-(3,5-ditert-butylphenyl)-1h-indene Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=2CC3=CC=CC=C3C=2)=C1 AWEIZPJLIGMMLJ-UHFFFAOYSA-N 0.000 description 2
- IOIQJBOQKBUDNH-UHFFFAOYSA-N 2-(4-methylphenyl)-1h-indene Chemical compound C1=CC(C)=CC=C1C1=CC2=CC=CC=C2C1 IOIQJBOQKBUDNH-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 229910003865 HfCl4 Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910007930 ZrCl3 Inorganic materials 0.000 description 2
- ZGARTXQPRARGDR-UHFFFAOYSA-L [Cl-].[Cl-].C1(C=CC=C1)[Zr+2]C1C(=CC2=CC=CC=C12)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C1(C=CC=C1)[Zr+2]C1C(=CC2=CC=CC=C12)C1=CC=CC=C1 ZGARTXQPRARGDR-UHFFFAOYSA-L 0.000 description 2
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- MAKZRXHPNSQVHZ-UHFFFAOYSA-L [Cl-].[Cl-].CC1C(=C([Zr++]C2=C(C(C)c3ccccc23)c2ccccc2)c2ccccc12)c1ccccc1 Chemical compound [Cl-].[Cl-].CC1C(=C([Zr++]C2=C(C(C)c3ccccc23)c2ccccc2)c2ccccc12)c1ccccc1 MAKZRXHPNSQVHZ-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
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- 150000001450 anions Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-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
- 150000002363 hafnium compounds Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 230000009022 nonlinear effect Effects 0.000 description 2
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 229920006124 polyolefin elastomer Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
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- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
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Classifications
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- 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
- 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
- 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
- C08F4/639—Component covered by group C08F4/62 containing a transition metal-carbon bond
- C08F4/63912—Component covered by group C08F4/62 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
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5433597P | 1997-06-14 | 1997-06-14 | |
| US5039397P | 1997-06-19 | 1997-06-19 | |
| US5010597P | 1997-06-20 | 1997-06-20 | |
| US7105098P | 1998-01-09 | 1998-01-09 | |
| PCT/US1998/012077 WO1998057996A1 (en) | 1997-06-14 | 1998-06-12 | ETHYLENE ENHANCEMENT OF PROCESSES FOR SYNTHESIS OF HIGH MELTING THERMOPLASTIC ELASTOMERIC α-OLEFIN POLYMERS (PRE/EPE EFFECTS) |
| US60/071,050 | 1998-06-12 | ||
| US60/050,393 | 1998-06-12 | ||
| US09/097,234 | 1998-06-12 | ||
| US60/050,105 | 1998-06-12 | ||
| US09/097,234 US6160064A (en) | 1997-06-14 | 1998-06-12 | Ethylene enhancement of processes for synthesis of high melting theromoplastic elastomeric α-olefin polymers (PRE/EPE effects) |
| US60/054,335 | 1998-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2292538A1 true CA2292538A1 (en) | 1998-12-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002292538A Abandoned CA2292538A1 (en) | 1997-06-14 | 1998-06-12 | Ethylene enhancement of processes for synthesis of high melting thermoplastic elastomeric .alpha.-olefin polymers (pre/epe effects) |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US6160064A (enExample) |
| EP (1) | EP0991675A4 (enExample) |
| JP (1) | JP2002505707A (enExample) |
| AU (1) | AU8066498A (enExample) |
| CA (1) | CA2292538A1 (enExample) |
| WO (1) | WO1998057996A1 (enExample) |
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| AU2111599A (en) * | 1998-01-09 | 1999-07-26 | Board Of Trustees Of The Leland Stanford Junior University | High-melting polyolefin copolymer elastomers, catalysts and methods of synthesis |
| US6380341B1 (en) * | 1998-01-09 | 2002-04-30 | The Board Of Trustees Of Leland Stanford Jr. University | Ethylene copolymers with narrow composition distribution and high melting temperatures, and methods of production thereof |
| US6479685B2 (en) * | 1998-01-09 | 2002-11-12 | The Board Of Trustees Of The Leland Standard Junior University | Metallocene catalysts for synthesis of high-melting polyolefin copolymer elastomers |
| US6518378B2 (en) * | 1998-01-09 | 2003-02-11 | The Board Of Trustees Of The Leland Stanford Junior University | High-melting polyolefin copolymer elastomers, catalysts and methods of synthesis |
| US6479424B1 (en) * | 1998-12-14 | 2002-11-12 | Bp Corporation North America Inc. | Fluxional catalysts and related ligands containing bulky substituents |
-
1998
- 1998-06-12 CA CA002292538A patent/CA2292538A1/en not_active Abandoned
- 1998-06-12 AU AU80664/98A patent/AU8066498A/en not_active Abandoned
- 1998-06-12 US US09/097,234 patent/US6160064A/en not_active Expired - Lifetime
- 1998-06-12 JP JP50456699A patent/JP2002505707A/ja not_active Ceased
- 1998-06-12 EP EP98928995A patent/EP0991675A4/en not_active Withdrawn
- 1998-06-12 WO PCT/US1998/012077 patent/WO1998057996A1/en not_active Ceased
-
2000
- 2000-09-25 US US09/669,411 patent/US6559262B1/en not_active Expired - Lifetime
-
2003
- 2003-03-18 US US10/392,088 patent/US6960550B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU8066498A (en) | 1999-01-04 |
| EP0991675A1 (en) | 2000-04-12 |
| WO1998057996A1 (en) | 1998-12-23 |
| EP0991675A4 (en) | 2002-07-03 |
| JP2002505707A (ja) | 2002-02-19 |
| US20030195308A1 (en) | 2003-10-16 |
| US6559262B1 (en) | 2003-05-06 |
| US6960550B2 (en) | 2005-11-01 |
| US6160064A (en) | 2000-12-12 |
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| EEER | Examination request | ||
| FZDE | Discontinued |