CA2315179A1 - Components and catalysts for the polymerization of olefins - Google Patents
Components and catalysts for the polymerization of olefins Download PDFInfo
- Publication number
- CA2315179A1 CA2315179A1 CA002315179A CA2315179A CA2315179A1 CA 2315179 A1 CA2315179 A1 CA 2315179A1 CA 002315179 A CA002315179 A CA 002315179A CA 2315179 A CA2315179 A CA 2315179A CA 2315179 A1 CA2315179 A1 CA 2315179A1
- Authority
- CA
- Canada
- Prior art keywords
- diethyl
- malonate
- group
- catalyst
- cycloalkyl
- 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
- 239000003054 catalyst Substances 0.000 title claims abstract description 51
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 33
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 19
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 150000002690 malonic acid derivatives Chemical class 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 12
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- -1 hydrocarbyl radical Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 239000011949 solid catalyst Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000010936 titanium Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910003074 TiCl4 Inorganic materials 0.000 claims description 12
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000003377 silicon compounds Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003609 titanium compounds Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- UVGKQRAGAYVWQV-UHFFFAOYSA-N 2,3-dimethylbutan-2-yl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C(C)C UVGKQRAGAYVWQV-UHFFFAOYSA-N 0.000 claims description 2
- WWYDYZMNFQIYPT-UHFFFAOYSA-L 2-phenylpropanedioate Chemical compound [O-]C(=O)C(C([O-])=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-L 0.000 claims description 2
- 229910010062 TiCl3 Inorganic materials 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- IOMXYXJOPMOHHQ-UHFFFAOYSA-N bis(2-chloroethyl) 2-propan-2-ylpropanedioate Chemical compound ClCCOC(=O)C(C(C)C)C(=O)OCCCl IOMXYXJOPMOHHQ-UHFFFAOYSA-N 0.000 claims description 2
- IBBBCERBWSGIGK-UHFFFAOYSA-N bis(2-fluoroethyl) 2-ethylpropanedioate Chemical compound FCCOC(=O)C(CC)C(=O)OCCF IBBBCERBWSGIGK-UHFFFAOYSA-N 0.000 claims description 2
- OBRQWGHGPSOIBZ-UHFFFAOYSA-N bis(2-fluoroethyl) 2-propan-2-ylpropanedioate Chemical compound FCCOC(=O)C(C(C)C)C(=O)OCCF OBRQWGHGPSOIBZ-UHFFFAOYSA-N 0.000 claims description 2
- NGJVJQYLRRSLCM-UHFFFAOYSA-N bis[(4-chlorophenyl)methyl] 2-cyclohexyl-2-methylpropanedioate;bis(2-trimethylsilylethyl) 2-(2-methylpropyl)-2-propan-2-ylpropanedioate Chemical compound C[Si](C)(C)CCOC(=O)C(C(C)C)(CC(C)C)C(=O)OCC[Si](C)(C)C.C=1C=C(Cl)C=CC=1COC(=O)C(C(=O)OCC=1C=CC(Cl)=CC=1)(C)C1CCCCC1 NGJVJQYLRRSLCM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 claims description 2
- CCCNBSNGQZMDOB-UHFFFAOYSA-N diethyl 2-(1,1,1-trifluoropropan-2-ylidene)propanedioate Chemical compound CCOC(=O)C(=C(C)C(F)(F)F)C(=O)OCC CCCNBSNGQZMDOB-UHFFFAOYSA-N 0.000 claims description 2
- SDTMIUZTSZWABV-UHFFFAOYSA-N diethyl 2-(2-ethylpiperidin-1-yl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)N1CCCCC1CC SDTMIUZTSZWABV-UHFFFAOYSA-N 0.000 claims description 2
- HITFOSUOCSFDFG-UHFFFAOYSA-N diethyl 2-[(4-chlorophenyl)methyl]-2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)(C(C)C)CC1=CC=C(Cl)C=C1 HITFOSUOCSFDFG-UHFFFAOYSA-N 0.000 claims description 2
- KNUFXHRJTVSEPI-UHFFFAOYSA-N diethyl 2-[(4-chlorophenyl)methyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)CC1=CC=C(Cl)C=C1 KNUFXHRJTVSEPI-UHFFFAOYSA-N 0.000 claims description 2
- GNBIEAFILSNSFO-UHFFFAOYSA-N diethyl 2-benzyl-2-(1,1,1-trifluoropropan-2-yl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)(C(C)C(F)(F)F)CC1=CC=CC=C1 GNBIEAFILSNSFO-UHFFFAOYSA-N 0.000 claims description 2
- WTBWYYBKLWALEL-UHFFFAOYSA-N diethyl 2-methyl-2-(1,1,1-trifluoro-2-methylpropan-2-yl)propanedioate Chemical compound CCOC(=O)C(C)(C(C)(C)C(F)(F)F)C(=O)OCC WTBWYYBKLWALEL-UHFFFAOYSA-N 0.000 claims description 2
- OKHZKYVJDYFFDA-UHFFFAOYSA-N diethyl 2-methyl-2-(trimethylsilylmethyl)propanedioate Chemical compound CCOC(=O)C(C)(C[Si](C)(C)C)C(=O)OCC OKHZKYVJDYFFDA-UHFFFAOYSA-N 0.000 claims description 2
- FHGBSYITFWPWDM-UHFFFAOYSA-N diethyl 2-methyl-2-piperidin-2-ylpropanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)C1CCCCN1 FHGBSYITFWPWDM-UHFFFAOYSA-N 0.000 claims description 2
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 claims description 2
- NETBVGNWMHLXRP-UHFFFAOYSA-N tert-butyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C(C)(C)C NETBVGNWMHLXRP-UHFFFAOYSA-N 0.000 claims description 2
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims description 2
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 claims description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 2
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- NRIHFBVDRRUXTK-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane;dicyclopentyl(dimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1.C1CCCC1[Si](OC)(OC)C1CCCC1 NRIHFBVDRRUXTK-UHFFFAOYSA-N 0.000 claims 1
- WQMNKCNKYFTUIK-UHFFFAOYSA-N diethyl 2-(1,1,1-trifluoropropan-2-yl)propanedioate Chemical compound CCOC(=O)C(C(C)C(F)(F)F)C(=O)OCC WQMNKCNKYFTUIK-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 10
- 229920000642 polymer Polymers 0.000 abstract description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 10
- 150000002148 esters Chemical class 0.000 abstract description 7
- 239000008096 xylene Substances 0.000 abstract description 6
- 150000002691 malonic acids Chemical class 0.000 abstract description 4
- 238000012721 stereospecific polymerization Methods 0.000 abstract description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 8
- 235000011147 magnesium chloride Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JWCYDYZLEAQGJJ-UHFFFAOYSA-N dicyclopentyl(dimethoxy)silane Chemical compound C1CCCC1[Si](OC)(OC)C1CCCC1 JWCYDYZLEAQGJJ-UHFFFAOYSA-N 0.000 description 2
- BYQFBFWERHXONI-UHFFFAOYSA-N diethyl 2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(C)C)C(=O)OCC BYQFBFWERHXONI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- RZAFMLDBKOEORQ-UHFFFAOYSA-N C(C)C(C(C)C)(C(C(=O)O)(C(=O)O)CC(C)C)CC.C(CC(=O)O)(=O)O Chemical compound C(C)C(C(C)C)(C(C(=O)O)(C(=O)O)CC(C)C)CC.C(CC(=O)O)(=O)O RZAFMLDBKOEORQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 238000006653 Ziegler-Natta catalysis Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 description 1
- NZAVQESSPMUTLE-UHFFFAOYSA-N diethyl 2-(1,1,1-trifluoro-2-methylpropan-2-yl)propanedioate Chemical compound CCOC(=O)C(C(C)(C)C(F)(F)F)C(=O)OCC NZAVQESSPMUTLE-UHFFFAOYSA-N 0.000 description 1
- ZEOGFXACYDZIKN-UHFFFAOYSA-N diethyl 2-(trimethylsilylmethyl)propanedioate Chemical compound CCOC(=O)C(C[Si](C)(C)C)C(=O)OCC ZEOGFXACYDZIKN-UHFFFAOYSA-N 0.000 description 1
- AIGAJLAWBNKHFS-UHFFFAOYSA-N diethyl 2-benzyl-2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)(C(C)C)CC1=CC=CC=C1 AIGAJLAWBNKHFS-UHFFFAOYSA-N 0.000 description 1
- RPNFNBGRHCUORR-UHFFFAOYSA-N diethyl 2-butylpropanedioate Chemical compound CCCCC(C(=O)OCC)C(=O)OCC RPNFNBGRHCUORR-UHFFFAOYSA-N 0.000 description 1
- VICRZZUITQGKDF-UHFFFAOYSA-N diethyl 2-methyl-2-(1,1,1-trifluoropropan-2-yl)propanedioate Chemical compound CCOC(=O)C(C)(C(C)C(F)(F)F)C(=O)OCC VICRZZUITQGKDF-UHFFFAOYSA-N 0.000 description 1
- NQSVPQIOJRYMGQ-UHFFFAOYSA-N diethyl 2-methyl-2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C)(C(C)C)C(=O)OCC NQSVPQIOJRYMGQ-UHFFFAOYSA-N 0.000 description 1
- WEISAZNMMVPNTH-UHFFFAOYSA-N diethyl 2-propan-2-ylidenepropanedioate Chemical compound CCOC(=O)C(=C(C)C)C(=O)OCC WEISAZNMMVPNTH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000000386 donor Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- 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
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98203733 | 1998-11-04 | ||
| EP98203733.5 | 1998-11-04 | ||
| PCT/EP1999/008018 WO2000026259A1 (en) | 1998-11-04 | 1999-10-22 | Components and catalysts for the polymerization of olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2315179A1 true CA2315179A1 (en) | 2000-05-11 |
Family
ID=8234301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002315179A Abandoned CA2315179A1 (en) | 1998-11-04 | 1999-10-22 | Components and catalysts for the polymerization of olefins |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US6605562B1 (enExample) |
| EP (1) | EP1042372B1 (enExample) |
| JP (1) | JP2002528606A (enExample) |
| KR (1) | KR20010033872A (enExample) |
| CN (1) | CN1146585C (enExample) |
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| CN100338018C (zh) | 2004-10-29 | 2007-09-19 | 中国石油化工股份有限公司 | 一种环戊酯类化合物及其合成方法和应用 |
| JP5340916B2 (ja) * | 2007-03-30 | 2013-11-13 | 東邦チタニウム株式会社 | オレフィン類重合用固体触媒成分、重合用触媒およびこれを用いたオレフィン類重合体の製造方法 |
| CN101735346B (zh) | 2008-11-07 | 2012-05-30 | 中国石油天然气股份有限公司 | 一种丙烯均聚和共聚的催化剂及其制备方法和应用 |
| US8088872B2 (en) | 2008-11-25 | 2012-01-03 | Dow Global Technologies Llc | Procatalyst composition including silyl ester internal donor and method |
| CN102292358B (zh) * | 2008-11-25 | 2014-04-30 | 联合碳化化学及塑料技术有限责任公司 | 包含具有甲硅烷基酯的多内给体的前催化剂组合物和方法 |
| US8383540B2 (en) | 2010-12-21 | 2013-02-26 | Dow Global Technologies Llc | Catalyst composition with halo-malonate internal electron donor and polymer from same |
| KR101868664B1 (ko) * | 2011-07-06 | 2018-06-18 | 도호 티타늄 가부시키가이샤 | 올레핀류 중합용 고체 촉매 성분, 올레핀류 중합용 촉매 및 올레핀류 중합체의 제조 방법 |
| EP2679609A1 (en) | 2012-06-28 | 2014-01-01 | Lummus Novolen Technology Gmbh | Sterically demanding dialkoxydialkylsilanes as external donors for ziegler catalysts for the polymerization of propylene |
| CN104513328B (zh) * | 2013-09-30 | 2017-09-29 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组合物及其应用 |
| TWI639626B (zh) | 2013-09-30 | 2018-11-01 | 中國石油化工科技開發有限公司 | Catalyst composition for olefin polymerization and application thereof |
| CN104558290B (zh) * | 2013-10-28 | 2018-11-02 | 中国石油化工股份有限公司 | 一种用于烯烃聚合催化剂组分和催化剂 |
| CN104558292B (zh) * | 2013-10-28 | 2017-05-31 | 中国石油化工股份有限公司 | 一种用于烯烃聚合催化剂制备方法 |
| CN104610056B (zh) * | 2013-11-01 | 2017-04-26 | 中国石油化工股份有限公司 | 一种化合物、含所述化合物的催化剂固体组分及催化剂 |
| CN105566534B (zh) * | 2014-10-13 | 2018-03-02 | 中国石油化工股份有限公司 | 一种烯烃聚合物及其制造方法 |
| US9593184B2 (en) | 2014-10-28 | 2017-03-14 | Formosa Plastics Corporation, Usa | Oxalic acid diamides as modifiers for polyolefin catalysts |
| RS64114B1 (sr) | 2015-10-23 | 2023-04-28 | Navitor Pharm Inc | Modulatori interakcije sestrin-gator2 i nјihova upotreba |
| US9777084B2 (en) * | 2016-02-19 | 2017-10-03 | Formosa Plastics Corporation, Usa | Catalyst system for olefin polymerization and method for producing olefin polymer |
| US11427660B2 (en) | 2016-08-17 | 2022-08-30 | Formosa Plastics Corporation, Usa | Organosilicon compounds as electron donors for olefin polymerization catalysts and methods of making and using same |
| US9815920B1 (en) | 2016-10-14 | 2017-11-14 | Formosa Plastics Corporation, Usa | Olefin polymerization catalyst components and process for the production of olefin polymers therewith |
| JP6914348B2 (ja) | 2017-03-06 | 2021-08-04 | ダブリュー・アール・グレース・アンド・カンパニー−コーンＷ Ｒ Ｇｒａｃｅ ＆ Ｃｏ−Ｃｏｎｎ | オレフィン重合のためのチーグラー−ナッタ触媒調製用の電子供与体及び触媒系 |
| EP4556069A3 (en) | 2017-04-26 | 2025-08-13 | Navitor Pharmaceuticals, Inc. | Modulators of sestrin-gator2 interaction and uses thereof |
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| US10124324B1 (en) | 2017-05-09 | 2018-11-13 | Formosa Plastics Corporation, Usa | Olefin polymerization catalyst components and process for the production of olefin polymers therewith |
| JP7644002B2 (ja) | 2018-10-24 | 2025-03-11 | ナビター ファーマシューティカルズ， インコーポレイテッド | 多形化合物およびその使用 |
| CN113179643B (zh) * | 2019-01-09 | 2024-07-05 | 巴塞尔聚烯烃意大利有限公司 | 用于烯烃聚合的催化剂组分 |
| CN114786660A (zh) | 2019-11-01 | 2022-07-22 | 纳维托制药有限公司 | 使用mtorc1调节剂的治疗方法 |
| ES1320681Y (es) | 2021-10-15 | 2025-10-24 | Skechers Usa Inc Ii | Zapato |
| CN116041577B (zh) | 2021-10-28 | 2024-12-06 | 中国石油化工股份有限公司 | 烯烃聚合催化剂组分、催化剂体系及应用和烯烃聚合方法 |
| US20250066513A1 (en) | 2023-08-23 | 2025-02-27 | Formosa Plastics Corporation, U.S.A. | Catalyst System For Enhanced Stereo-Specificity Of Olefin Polymerization |
| US20250066514A1 (en) | 2023-08-24 | 2025-02-27 | Formosa Plastics Corporation, U.S.A. | Catalysts component and process for the production of polypropylene having high melt flow rate with high isotacticity |
| US20250109218A1 (en) | 2023-09-29 | 2025-04-03 | Formosa Plastics Corporation, U.S.A. | Method for preparing catalyst component for polymerization of polyolefin without the use of internal electron donors |
| US20250115687A1 (en) | 2023-10-06 | 2025-04-10 | Formosa Plastics Corporation, U.S.A. | Production method for solid catalyst component for polymerizing olefins, and catalyst for polymerizaing olefins |
| US20250115686A1 (en) | 2023-10-09 | 2025-04-10 | Formosa Plastics Corporation, U.S.A. | Olefin polymerization catalyst components containing silane and process for the production of polypropylene having high isotacticity at high melt flow rate |
| US20250297039A1 (en) | 2024-03-19 | 2025-09-25 | Formosa Plastics Corporation, U.S.A. | Olefin polymerization catalyst components containing diglycidylester components and its use for the production of polypropylene having high isotacticity at high melt flow rate |
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-
1999
- 1999-10-22 HU HU0104266A patent/HUP0104266A2/hu unknown
- 1999-10-22 AT AT99950770T patent/ATE271072T1/de not_active IP Right Cessation
- 1999-10-22 WO PCT/EP1999/008018 patent/WO2000026259A1/en not_active Ceased
- 1999-10-22 BR BR9907140-1A patent/BR9907140A/pt unknown
- 1999-10-22 US US09/582,600 patent/US6605562B1/en not_active Expired - Fee Related
- 1999-10-22 KR KR1020007007440A patent/KR20010033872A/ko not_active Withdrawn
- 1999-10-22 AU AU63420/99A patent/AU6342099A/en not_active Abandoned
- 1999-10-22 JP JP2000579645A patent/JP2002528606A/ja active Pending
- 1999-10-22 CA CA002315179A patent/CA2315179A1/en not_active Abandoned
- 1999-10-22 CN CNB998036331A patent/CN1146585C/zh not_active Expired - Fee Related
- 1999-10-22 IL IL13676199A patent/IL136761A0/xx unknown
- 1999-10-22 ES ES99950770T patent/ES2224704T3/es not_active Expired - Lifetime
- 1999-10-22 DE DE69918662T patent/DE69918662T2/de not_active Expired - Fee Related
- 1999-10-22 EP EP99950770A patent/EP1042372B1/en not_active Expired - Lifetime
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2003
- 2003-06-06 US US10/455,899 patent/US6689850B2/en not_active Expired - Fee Related
- 2003-06-06 US US10/455,898 patent/US6699814B2/en not_active Expired - Fee Related
- 2003-06-06 US US10/455,900 patent/US20030207755A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE69918662D1 (de) | 2004-08-19 |
| KR20010033872A (ko) | 2001-04-25 |
| BR9907140A (pt) | 2000-10-17 |
| EP1042372B1 (en) | 2004-07-14 |
| WO2000026259A1 (en) | 2000-05-11 |
| US20030207754A1 (en) | 2003-11-06 |
| AU6342099A (en) | 2000-05-22 |
| ES2224704T3 (es) | 2005-03-01 |
| CN1146585C (zh) | 2004-04-21 |
| EP1042372A1 (en) | 2000-10-11 |
| US20030207755A1 (en) | 2003-11-06 |
| ATE271072T1 (de) | 2004-07-15 |
| US6699814B2 (en) | 2004-03-02 |
| IL136761A0 (en) | 2001-06-14 |
| CN1292800A (zh) | 2001-04-25 |
| US6605562B1 (en) | 2003-08-12 |
| HUP0104266A2 (hu) | 2002-03-28 |
| US6689850B2 (en) | 2004-02-10 |
| JP2002528606A (ja) | 2002-09-03 |
| US20030199388A1 (en) | 2003-10-23 |
| DE69918662T2 (de) | 2005-08-11 |
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