CA2610433C - Procedes de polymerisation vivante d'olefines - Google Patents

Procedes de polymerisation vivante d'olefines Download PDF

Info

Publication number: CA2610433C
Authority: CA; Canada
Prior art keywords: group; atom; metal; bond; initiator
Prior art date: 1997-04-11
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

Application number

CA2610433A

Other languages

English (en)

Other versions

CA2610433A1 (fr

Inventor

Richard R. Schrock

Robert Baumann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Massachusetts Institute of Technology

Original Assignee

Massachusetts Institute of Technology

Priority date (The priority date 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 date listed.)

1997-04-11

Filing date

1998-04-09

Publication date

2011-11-29

1997-04-11 Priority claimed from US08/843,161 external-priority patent/US5889128A/en

1998-04-09 Application filed by Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology

1998-10-22 Publication of CA2610433A1 publication Critical patent/CA2610433A1/fr

2011-11-29 Application granted granted Critical

2011-11-29 Publication of CA2610433C publication Critical patent/CA2610433C/fr

2018-04-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000006116 polymerization reaction Methods 0.000 title claims description 25
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 45
150000001336 alkenes Chemical class 0.000 title abstract description 43
239000003999 initiator Substances 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 65
229920000642 polymer Polymers 0.000 claims abstract description 57
229920001519 homopolymer Polymers 0.000 claims abstract description 53
239000000178 monomer Substances 0.000 claims abstract description 53
229910052751 metal Inorganic materials 0.000 claims abstract description 49
239000002184 metal Substances 0.000 claims abstract description 48
229920001400 block copolymer Polymers 0.000 claims abstract description 46
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 29
125000004429 atom Chemical group 0.000 claims description 54
229910052799 carbon Inorganic materials 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 24
239000002904 solvent Substances 0.000 claims description 20
239000012018 catalyst precursor Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 13
229920001577 copolymer Polymers 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
229930195733 hydrocarbon Natural products 0.000 claims description 9
150000002430 hydrocarbons Chemical class 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
229910052735 hafnium Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052719 titanium Inorganic materials 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229910052726 zirconium Inorganic materials 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 26
230000015572 biosynthetic process Effects 0.000 abstract description 19
238000003786 synthesis reaction Methods 0.000 abstract description 11
239000003446 ligand Substances 0.000 abstract description 10
230000008569 process Effects 0.000 abstract description 8
238000010550 living polymerization reaction Methods 0.000 abstract description 6
125000000129 anionic group Chemical group 0.000 abstract description 4
230000008901 benefit Effects 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 64
239000000243 solution Substances 0.000 description 47
241000894007 species Species 0.000 description 46
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 23
238000005160 1H NMR spectroscopy Methods 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 17
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 17
229960004132 diethyl ether Drugs 0.000 description 17
239000000047 product Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
QARVLSVVCXYDNA-RALIUCGRSA-N 1-bromo-2,3,4,5,6-pentadeuteriobenzene Chemical compound [2H]C1=C([2H])C([2H])=C(Br)C([2H])=C1[2H] QARVLSVVCXYDNA-RALIUCGRSA-N 0.000 description 12
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
-1 2,6-dimethylphenyl Chemical group 0.000 description 11
239000000725 suspension Substances 0.000 description 11
239000013078 crystal Substances 0.000 description 10
239000003039 volatile agent Substances 0.000 description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 8
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
230000002194 synthesizing effect Effects 0.000 description 6
229910052723 transition metal Inorganic materials 0.000 description 6
150000003624 transition metals Chemical class 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000003780 insertion Methods 0.000 description 5
230000037431 insertion Effects 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
101100297420 Homarus americanus phc-1 gene Proteins 0.000 description 4
239000004698 Polyethylene Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
238000005227 gel permeation chromatography Methods 0.000 description 4
229920000573 polyethylene Polymers 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000010936 titanium Substances 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
DWCMDRNGBIZOQL-UHFFFAOYSA-N dimethylazanide;zirconium(4+) Chemical compound [Zr+4].C[N-]C.C[N-]C.C[N-]C.C[N-]C DWCMDRNGBIZOQL-UHFFFAOYSA-N 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
230000000977 initiatory effect Effects 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
229920005604 random copolymer Polymers 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
238000004293 19F NMR spectroscopy Methods 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 description 2
101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910010068 TiCl2 Inorganic materials 0.000 description 2
239000012190 activator Substances 0.000 description 2
230000004075 alteration Effects 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000000149 argon plasma sintering Methods 0.000 description 2
101150113676 chr1 gene Proteins 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000006872 improvement Effects 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
230000001902 propagating effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 2
238000012546 transfer Methods 0.000 description 2
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
KHOITXIGCFIULA-UHFFFAOYSA-N Alophen Chemical compound C1=CC(OC(=O)C)=CC=C1C(C=1N=CC=CC=1)C1=CC=C(OC(C)=O)C=C1 KHOITXIGCFIULA-UHFFFAOYSA-N 0.000 description 1
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
239000004215 Carbon black (E152) Chemical group 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
238000004639 Schlenk technique Methods 0.000 description 1
241000287219 Serinus canaria Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229910008067 ZrI2 Inorganic materials 0.000 description 1
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
229910052768 actinide Inorganic materials 0.000 description 1
150000001255 actinides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
238000010539 anionic addition polymerization reaction Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000013626 chemical specie Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000011903 deuterated solvents‎ Substances 0.000 description 1
125000004431 deuterium atom Chemical group 0.000 description 1
AASUFOVSZUIILF-UHFFFAOYSA-N diphenylmethanone;sodium Chemical compound [Na].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 AASUFOVSZUIILF-UHFFFAOYSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
229920006343 melt-processible rubber Polymers 0.000 description 1
150000004681 metal hydrides Chemical group 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000008450 motivation Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012827 research and development Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000003860 storage Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

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Graft Or Block Polymers (AREA)

CA2610433A 1997-04-11 1998-04-09 Procedes de polymerisation vivante d'olefines Expired - Lifetime CA2610433C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/843,161 US5889128A (en)	1997-04-11	1997-04-11	Living olefin polymerization processes
US08/843,161		1997-04-11
CA002285964A CA2285964C (fr)	1997-04-11	1998-04-09	Procedes de polymerisation vivante d'olefines

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002285964A Division CA2285964C (fr)	1997-04-11	1998-04-09	Procedes de polymerisation vivante d'olefines

Publications (2)

Publication Number	Publication Date
CA2610433A1 CA2610433A1 (fr)	1998-10-22
CA2610433C true CA2610433C (fr)	2011-11-29

Family

ID=39182068

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2610433A Expired - Lifetime CA2610433C (fr)	1997-04-11	1998-04-09	Procedes de polymerisation vivante d'olefines

Country Status (1)

Country	Link
CA (1)	CA2610433C (fr)

1998
- 1998-04-09 CA CA2610433A patent/CA2610433C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2610433A1 (fr)	1998-10-22

Legal Events

Date	Code	Title	Description
2007-11-20	EEER	Examination request
2018-06-11	MKEX	Expiry	Effective date: 20180409

Publication	Publication Date	Title
CA2285964C (fr)	2008-02-12	Procedes de polymerisation vivante d'olefines
US5447895A (en)	1995-09-05	Sterically shielded diboron-containing metallocene olefin polymerization catalysts
US6596827B2 (en)	2003-07-22	Method for catalytic polymerization of alpha-olefin monomers using an ultra-high activity non-metallocene pre-catalyst
Bott et al.	2003	Monocyclopentadienyl phenoxy-imine and phenoxy-amine complexes of titanium and zirconium and their application as catalysts for 1-alkene polymerisation
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CA2469111A1 (fr)	2003-06-26	Compositions de catalyseurs imino-amide pour la polymerisation des olefines
US6825296B2 (en)	2004-11-30	Catalyst component for olefin polymerization
WO2001019512A1 (fr)	2001-03-22	Complexes d'hydrocarbyl phosphinimine/cyclopentadienyl du groupe 4 et leur utilisation dans la polymerisation des olefines
US8519070B2 (en)	2013-08-27	Post-metallocene complexes based on bis(naphthoxy)pyridine and bis(naphthoxy)thiophene ligands for the polymerisation of ethylene and alpha-olefins
WO2000018808A1 (fr)	2000-04-06	Systeme catalytique cationique du groupe 3
van der Ende et al.	2019	Ti (IV) Complexes with Bidentate O‐Chelating N‐Heterocyclic Carbenes for Use in the Homopolymerization of Ethylene and Its Copolymerization with Cyclic Olefins
US8598284B2 (en)	2013-12-03	Oxygen-bridged bimetallic complex and polymerization process
Hannant et al.	2006	The synthesis of new weakly coordinating diborate anions: anion stability as a function of linker structure and steric bulk
Jutzi et al.	1996	Mixed Bent Sandwich Titanium Complexes with the [2‐(Diisopropylamino) ethyl] cyclopentadienyl Ligand—Catalysts for the Polymerization of Ethylene and the Dehydrocoupling of Phenylsilane
KR100440480B1 (ko)	2004-07-14	폴리올레핀 제조용 촉매 및 이를 이용한 폴리올레핀의제조방법
Yu et al.	2010	Zirconium enolatoimine complexes in olefin polymerization
Schrock et al.	1998	Living olefin polymerization processes
KR100834889B1 (ko)	2008-06-03	전이금속 화합물, 프로필렌 중합용 촉매, 및 상기 촉매를이용한 프로필렌 중합체의 제조방법
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EP1379561B1 (fr)	2006-06-14	Procede de polymerisation d'olefines en utilisant des complexes de metal de transition
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