CA2285964C - Living olefin polymerization processes - Google Patents
Living olefin polymerization processes Download PDFInfo
- Publication number
- CA2285964C CA2285964C CA002285964A CA2285964A CA2285964C CA 2285964 C CA2285964 C CA 2285964C CA 002285964 A CA002285964 A CA 002285964A CA 2285964 A CA2285964 A CA 2285964A CA 2285964 C CA2285964 C CA 2285964C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- group
- matter according
- atom
- matter
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract description 44
- 150000001336 alkenes Chemical class 0.000 title abstract description 42
- 238000006116 polymerization reaction Methods 0.000 title description 21
- 229910052751 metal Inorganic materials 0.000 claims abstract description 36
- 239000002184 metal Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims description 57
- 125000004429 atom Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 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 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 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 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 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 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
- 239000000178 monomer Substances 0.000 abstract description 51
- 239000003999 initiator Substances 0.000 abstract description 49
- 229920000642 polymer Polymers 0.000 abstract description 49
- 229920001400 block copolymer Polymers 0.000 abstract description 40
- 229920001519 homopolymer Polymers 0.000 abstract description 37
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- 238000000034 method Methods 0.000 abstract description 22
- 230000015572 biosynthetic process Effects 0.000 abstract description 19
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 17
- 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 69
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 47
- 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 29
- 241000894007 species Species 0.000 description 28
- 239000007787 solid Substances 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 19
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 18
- 229960004132 diethyl ether Drugs 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 239000012018 catalyst precursor Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 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
- 239000000725 suspension Substances 0.000 description 11
- -1 2,6-dimethylphenyl Chemical group 0.000 description 10
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 7
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 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
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 229910007928 ZrCl2 Inorganic materials 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
- 230000002194 synthesizing effect Effects 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 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
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-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
- 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
- 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
- 229910008067 ZrI2 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
- 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
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 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
- 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
- 238000012546 transfer Methods 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-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
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 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
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 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
- 101150113676 chr1 gene Proteins 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
- 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
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
- 229910052710 silicon Inorganic materials 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
- 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
- 230000007704 transition Effects 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
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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
-
- 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
-
- 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
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
-
- 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
-
- 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
- Y10S526/903—Monomer polymerized in presence of transition metal containing catalyst and hydrocarbon additive affecting polymer properties of catalyst activity
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Graft Or Block Polymers (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2610433A CA2610433C (en) | 1997-04-11 | 1998-04-09 | Living olefin polymerization processes |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/843,161 | 1997-04-11 | ||
| US08/843,161 US5889128A (en) | 1997-04-11 | 1997-04-11 | Living olefin polymerization processes |
| PCT/US1998/007466 WO1998046651A2 (en) | 1997-04-11 | 1998-04-09 | Living olefin polymerization processes |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2610433A Division CA2610433C (en) | 1997-04-11 | 1998-04-09 | Living olefin polymerization processes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285964A1 CA2285964A1 (en) | 1998-10-22 |
| CA2285964C true CA2285964C (en) | 2008-02-12 |
Family
ID=25289222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002285964A Expired - Lifetime CA2285964C (en) | 1997-04-11 | 1998-04-09 | Living olefin polymerization processes |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US5889128A (enExample) |
| EP (1) | EP0975579B1 (enExample) |
| JP (1) | JP2001520696A (enExample) |
| AU (1) | AU6970998A (enExample) |
| CA (1) | CA2285964C (enExample) |
| DE (1) | DE69810605T2 (enExample) |
| WO (1) | WO1998046651A2 (enExample) |
Families Citing this family (124)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5889128A (en) * | 1997-04-11 | 1999-03-30 | Massachusetts Institute Of Technology | Living olefin polymerization processes |
| US6271325B1 (en) | 1999-05-17 | 2001-08-07 | Univation Technologies, Llc | Method of polymerization |
| US6271315B1 (en) | 1999-06-17 | 2001-08-07 | Wisconsin Alumni Research Foundation | Methods for making multivalent arrays |
| US6291616B1 (en) | 1999-06-17 | 2001-09-18 | Wisconsin Alumni Research Foundation | Methods and reagents for capping ruthenium or osmium carbene-catalyzed ROMP products |
| US6333423B1 (en) * | 1999-09-10 | 2001-12-25 | Ramot University Authority For Applied Research And Industrial Development Ltd. | Ultra-high activity non-metallocene pre-catalyst and method for catalytic polymerization of alpha-olefin monomers |
| DE10002214C2 (de) | 1999-09-20 | 2001-09-13 | Solarlux Aluminium Sys Gmbh | Schiebedrehflügelsystem |
| WO2001026806A2 (en) * | 1999-10-12 | 2001-04-19 | Dow Global Technologies Inc. | Possibly dicationic non-metallocene group 4 metal complexes with anionic n, o or p ligands |
| US6300439B1 (en) * | 1999-11-08 | 2001-10-09 | Univation Technologies, Llc | Group 15 containing transition metal catalyst compounds, catalyst systems and their use in a polymerization process |
| US6380328B1 (en) | 1999-12-10 | 2002-04-30 | Univation Technologies, Llc | Catalyst systems and their use in a polymerization process |
| US6271323B1 (en) * | 1999-10-28 | 2001-08-07 | Univation Technologies, Llc | Mixed catalyst compounds, catalyst systems and their use in a polymerization process |
| US6274684B1 (en) * | 1999-10-22 | 2001-08-14 | Univation Technologies, Llc | Catalyst composition, method of polymerization, and polymer therefrom |
| US6265505B1 (en) * | 1999-11-18 | 2001-07-24 | Univation Technologies, Llc | Catalyst system and its use in a polymerization process |
| US6624107B2 (en) | 1999-10-22 | 2003-09-23 | Univation Technologies, Llc | Transition metal catalyst compounds having deuterium substituted ligand and catalyst systems thereof |
| US6417304B1 (en) | 1999-11-18 | 2002-07-09 | Univation Technologies, Llc | Method of polymerization and polymer produced therefrom |
| US6300438B1 (en) * | 1999-10-22 | 2001-10-09 | Univation Technolgies, Llc | Hafnium transition metal catalyst compounds, catalyst systems and their use in a polymerization process |
| BR0015241B1 (pt) * | 1999-10-22 | 2010-10-05 | processo para polimerização de olefina(s) na presença de uma sistema catalisador, sistemas catalisadores e uso de um composto catalisador. | |
| US6281306B1 (en) * | 1999-12-16 | 2001-08-28 | Univation Technologies, Llc | Method of polymerization |
| AU8149901A (en) * | 2000-03-21 | 2001-10-03 | Wisconsin Alummi Res Foundatio | Methods and reagents for regulation of cellular responses in biological systems |
| US20040248801A1 (en) * | 2000-03-21 | 2004-12-09 | Kiessling Laura L. | Methods and reagents for regulation of cellular responses in biological systems |
| JP5290488B2 (ja) | 2000-09-28 | 2013-09-18 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | 酸化物、ケイ酸塩及びリン酸塩の気相成長 |
| US6686490B1 (en) * | 2000-11-06 | 2004-02-03 | Ramot University Authority For Applied Research & Industrial Development Ltd. | Active non-metallocene pre-catalyst and method for tactic catalytic polymerization of alpha-olefin monomers |
| JP2002206007A (ja) * | 2000-11-08 | 2002-07-26 | National Institute Of Advanced Industrial & Technology | オレフィン系ブロック共重合体の製法 |
| US6656866B2 (en) * | 2000-12-04 | 2003-12-02 | Univation Technologies, Llc | Catalyst preparation method |
| US6518444B1 (en) | 2000-12-18 | 2003-02-11 | Univation Technologies, Llc | Preparation of polymerization catalysts |
| GB2374771B (en) * | 2000-12-29 | 2004-07-07 | Vtech Communications Ltd | Frame structure with diversity |
| GB0102440D0 (en) | 2001-01-31 | 2001-03-14 | Borealis Tech Oy | Catalyst |
| EP1392706B1 (en) * | 2001-05-10 | 2005-06-01 | Univation Technologies LLC | Olefin polymerization catalysts containing a pyrrole bisimine ligand |
| US7002049B2 (en) * | 2002-08-19 | 2006-02-21 | Eastman Chemical Company | Process for α,β-dihydroxyalkenes and derivatives |
| EP1620479B1 (en) | 2002-10-15 | 2013-07-24 | ExxonMobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| US6953764B2 (en) | 2003-05-02 | 2005-10-11 | Dow Global Technologies Inc. | High activity olefin polymerization catalyst and process |
| US7285606B2 (en) * | 2003-08-04 | 2007-10-23 | Dsm Ip Assets B.V. | Process for the preparation of a polyolefin |
| US7547751B2 (en) | 2003-08-04 | 2009-06-16 | Dsm Ip Assets B.V. | Process for the preparation of a polyolefin |
| EP1506974A1 (en) | 2003-08-04 | 2005-02-16 | DSM IP Assets B.V. | Process for the preparation of a metalloorganic compound comprising at least one imine ligand |
| US7250523B2 (en) * | 2003-10-22 | 2007-07-31 | Board Of Trustees Of Michigan State University | Imido-tethered carbenes of molybdenum for ring-opening metathesis polymerization and ring-closing metathesis |
| US6967184B2 (en) * | 2004-02-17 | 2005-11-22 | Univation Technologies, Llc | Fluoroalcohol leaving group for non-metallocene olefin polymerization catalysts |
| US7193017B2 (en) * | 2004-08-13 | 2007-03-20 | Univation Technologies, Llc | High strength biomodal polyethylene compositions |
| US8202940B2 (en) * | 2004-08-19 | 2012-06-19 | Univation Technologies, Llc | Bimodal polyethylene compositions for blow molding applications |
| US7868092B2 (en) * | 2005-06-14 | 2011-01-11 | Univation Technologies, Llc | Bimodal polyethylene compositions for blow molding applications |
| US7432328B2 (en) * | 2005-06-14 | 2008-10-07 | Univation Technologies, Llc | Enhanced ESCR bimodal HDPE for blow molding applications |
| EP1805226A1 (en) * | 2004-10-29 | 2007-07-11 | Exxonmobil Chemical Patents Inc. | Catalyst compound containing divalent tridentate ligand |
| US6987152B1 (en) | 2005-01-11 | 2006-01-17 | Univation Technologies, Llc | Feed purification at ambient temperature |
| WO2006078021A1 (ja) * | 2005-01-21 | 2006-07-27 | Riken | 三座配位子を含む金属錯体、およびそれを含む重合用触媒 |
| US7312279B2 (en) * | 2005-02-07 | 2007-12-25 | Univation Technologies, Llc | Polyethylene blend compositions |
| US7858702B2 (en) * | 2005-06-14 | 2010-12-28 | Univation Technologies, Llc | Enhanced ESCR bimodal HDPE for blow molding applications |
| US7947797B2 (en) | 2005-09-14 | 2011-05-24 | Univation Technologies, Llc | Method for operating a gas-phase reactor at or near maximum production rates while controlling polymer stickiness |
| US20070109911A1 (en) * | 2005-11-16 | 2007-05-17 | Neubauer Anthony C | High speed and direct driven rotating equipment for polyolefin manufacturing |
| EP1803747A1 (en) | 2005-12-30 | 2007-07-04 | Borealis Technology Oy | Surface-modified polymerization catalysts for the preparation of low-gel polyolefin films |
| US20070203504A1 (en) * | 2006-02-27 | 2007-08-30 | Blair Denny | Skin-marking devices and their use |
| TWI432456B (zh) * | 2006-10-03 | 2014-04-01 | Univation Tech Llc | 用於觸媒注射之泡騰噴嘴 |
| BRPI0717152B1 (pt) | 2006-10-03 | 2018-07-03 | Univation Technologies, Llc. | Método para polimerização de olefina e sistema de reação para polimerização de olefina |
| US7932397B2 (en) * | 2006-11-22 | 2011-04-26 | Massachusetts Institute Of Technology | Olefin metathesis catalysts and related methods |
| EP2112175A1 (en) | 2008-04-16 | 2009-10-28 | ExxonMobil Chemical Patents Inc. | Activator for metallocenes comprising one or more halogen substituted heterocyclic heteroatom containing ligand coordinated to an alumoxane |
| TW200936564A (en) * | 2007-11-15 | 2009-09-01 | Univation Tech Llc | Methods for the removal of impurities from polymerization feed streams |
| TW200936619A (en) | 2007-11-15 | 2009-09-01 | Univation Tech Llc | Polymerization catalysts, methods of making, methods of using, and polyolefin products made therefrom |
| BRPI0906685A2 (pt) | 2008-01-25 | 2016-10-11 | Massachusetts Inst Technology | catalisadores para reações de metátese incluindo metátese de olefina enantiosseletiva, e métodos relacionados |
| US7910760B2 (en) * | 2008-04-15 | 2011-03-22 | Exxonmobil Chemical Patents Inc. | Semi-rigid linked diamines, precursors therefor, and transition metal diamido complexes as catalysts for olefin polymerization processes |
| US8148481B2 (en) | 2008-12-18 | 2012-04-03 | Univation Technologies, Llc | Method for seed bed treatment for a polymerization reaction |
| US8222469B2 (en) * | 2009-07-15 | 2012-07-17 | Massachusetts Institute Of Technology | Catalysts and processes for the formation of terminal olefins by ethenolysis |
| US8158733B2 (en) * | 2009-07-22 | 2012-04-17 | Equistar Chemicals, Lp | Catalysts based on 2-(2-aryloxy)quinoline or 2-(2-aryloxy)dihydroquinoline ligands |
| US8153544B2 (en) * | 2009-07-22 | 2012-04-10 | Equistar Chemicals, Lp | Method for preparing non-metallocene catalysts |
| US7858718B1 (en) | 2009-07-22 | 2010-12-28 | Equistar Chemicals, Lp | Catalysts based on 2-aryl-8-anilinoquinoline ligands |
| EP2456796B1 (en) | 2009-07-23 | 2013-07-17 | Univation Technologies, LLC | Polymerization reaction system |
| US8362311B2 (en) | 2009-09-30 | 2013-01-29 | Massachusetts Institute Of Technology | Highly Z-selective olefins metathesis |
| WO2011078923A1 (en) | 2009-12-23 | 2011-06-30 | Univation Technologies, Llc | Methods for producing catalyst systems |
| WO2011097642A1 (en) | 2010-02-08 | 2011-08-11 | Trustees Of Boston College | Efficient methods for z- or cis-selective cross-metathesis |
| CN102803308B (zh) | 2010-02-18 | 2015-04-01 | 尤尼威蒂恩技术有限公司 | 用于操作聚合反应器的方法 |
| EP2539377B1 (en) | 2010-02-22 | 2018-09-05 | Univation Technologies, LLC | Catalyst systems and methods for using same to produce polyolefin products |
| EP2558531B1 (en) | 2010-04-13 | 2017-02-15 | Univation Technologies, LLC | Polymer blends and films made therefrom |
| US20120016092A1 (en) | 2010-07-14 | 2012-01-19 | Sandor Nagy | Catalysts based on quinoline precursors |
| BR112013000679A2 (pt) | 2010-07-16 | 2016-05-31 | Univation Tech Llc | sistemas e métodos para medir acúmulo de partícula em superfícies de reator |
| WO2012009215A1 (en) | 2010-07-16 | 2012-01-19 | Univation Technologies, Llc | Systems and methods for measuring static charge on particulates |
| WO2012015898A1 (en) | 2010-07-28 | 2012-02-02 | Univation Technologies, Llc | Systems and methods for measuring velocity of a particle/fluid mixture |
| WO2012074709A1 (en) | 2010-11-30 | 2012-06-07 | Univation Technologies, Llc | Processes for the polymerization of olefins with extracted metal carboxylate salts |
| EP2646481B1 (en) | 2010-11-30 | 2015-04-22 | Univation Technologies, LLC | Catalyst composition having improved flow characteristics and methods of making and using the same |
| BR112013014992B1 (pt) | 2010-12-17 | 2020-12-29 | Univation Technologies, Llc | sistemas e métodos para recuperar hidrocarbonetos de um produto gasoso da purga de poliolefina |
| RU2598023C2 (ru) | 2011-05-13 | 2016-09-20 | Юнивейшн Текнолоджиз, Ллк | Полученные распылительной сушкой каталитические композиции и способы полимеризации, в которых они применяются |
| US8546500B2 (en) | 2011-05-27 | 2013-10-01 | Massachusetts Institute Of Technology | Complexes for use in metathesis reactions |
| WO2012167171A2 (en) | 2011-06-03 | 2012-12-06 | Massachusetts Institute Of Technology | Z-selective ring-closing metathesis reactions |
| WO2013028283A1 (en) | 2011-08-19 | 2013-02-28 | Univation Technologies, Llc | Catalyst systems and methods for using same to produce polyolefin products |
| US9234060B2 (en) | 2011-11-08 | 2016-01-12 | Univation Technologies, Llc | Methods of preparing a catalyst system |
| WO2013070602A1 (en) | 2011-11-08 | 2013-05-16 | Univation Technologies, Llc | Methods for producing polyolefins with catalyst systems |
| US9650453B2 (en) | 2012-12-28 | 2017-05-16 | Univation Technologies, Llc | Methods of integrating aluminoxane production into catalyst production |
| ES2918582T3 (es) | 2012-12-28 | 2022-07-19 | Univation Tech Llc | Catalizador soportado con fluidez mejorada |
| CA2897456C (en) | 2013-01-14 | 2021-08-31 | Univation Technologies, Llc | Methods for preparing catalyst systems with increased productivity |
| WO2014120494A1 (en) | 2013-01-30 | 2014-08-07 | Univation Technologies, Llc | Processes for making catalyst compositions having improved flow |
| KR102113899B1 (ko) | 2013-02-07 | 2020-05-21 | 유니베이션 테크놀로지즈, 엘엘씨 | 폴리올레핀의 제조 |
| EP2970526B1 (en) | 2013-03-15 | 2017-08-09 | Univation Technologies, LLC | Ligands for catalysts |
| WO2014149360A1 (en) | 2013-03-15 | 2014-09-25 | Univation Technologies, Llc | Multiple catalyst system comprising metallocenes and tridentate nitrogen based ligand complexes for olefin polymerisation |
| ES2667196T3 (es) | 2013-03-15 | 2018-05-10 | Univation Technologies, Llc | Ligandos tridentados basados en nitrógeno para catalizadores de la polimerización de olefinas |
| US9604893B2 (en) | 2013-06-05 | 2017-03-28 | Univation Technologies, Llc | Protecting phenol groups |
| CN103408577B (zh) * | 2013-08-13 | 2016-02-24 | 中国科学院化学研究所 | 基于芳基二胺的胺基硅烷化合物及其制备方法 |
| WO2015153082A1 (en) | 2014-04-02 | 2015-10-08 | Univation Technologies, Llc | Continuity compositions and methods of making and using the same |
| WO2015195188A1 (en) | 2014-06-16 | 2015-12-23 | Univation Technologies, Llc | Methods of modifying the melt flow ratio and/or swell of polyethylene resins |
| WO2015195189A1 (en) | 2014-06-16 | 2015-12-23 | Univation Technologies, Llc | Polyethylene resins |
| WO2016094870A1 (en) | 2014-12-12 | 2016-06-16 | Exxonmobil Chemical Patents Inc. | Olefin polymerization catalyst system comprising mesoporous organosilica support |
| CA2964385C (en) | 2014-12-12 | 2021-06-01 | Exxonmobil Research And Engineering Company | Aromatic hydrogenation catalysts and uses thereof |
| WO2016145179A1 (en) | 2015-03-10 | 2016-09-15 | Univation Technologies, Llc | Spray dried catalyst compositions, methods for preparation and use in olefin polymerization processes |
| CN107531827B (zh) | 2015-04-17 | 2021-04-23 | 尤尼威蒂恩技术有限责任公司 | 用于烯烃聚合的方法和系统 |
| CN107531839B (zh) | 2015-04-24 | 2021-05-25 | 尤尼威蒂恩技术有限责任公司 | 用于操作聚合反应器的方法 |
| SG11201708626SA (en) | 2015-04-27 | 2017-11-29 | Univation Tech Llc | Supported catalyst compositions having improved flow properties and preparation thereof |
| US10414887B2 (en) | 2015-10-02 | 2019-09-17 | Exxonmobil Chemical Patents Inc. | Supported catalyst systems and methods of using same |
| WO2018022263A1 (en) | 2016-07-29 | 2018-02-01 | Exxonmobil Chemical Patents Inc. | Polymerization processes using high molecular weight polyhydric quenching agents |
| WO2018048472A1 (en) | 2016-09-09 | 2018-03-15 | Exxonmobil Chemical Patents Inc. | Pilot plant scale semi-condensing operation |
| WO2018075243A1 (en) | 2016-10-19 | 2018-04-26 | Exxonmobil Chemical Patents Inc. | Supported catalyst systems and methods of using same |
| WO2018118258A1 (en) | 2016-12-20 | 2018-06-28 | Exxonmobil Chemical Patents Inc. | Methods for controlling start up conditions in polymerization processes |
| CN110191902B (zh) | 2017-02-13 | 2022-08-09 | 尤尼威蒂恩技术有限责任公司 | 双峰聚乙烯树脂 |
| CN112055719B (zh) | 2018-05-02 | 2022-11-25 | 埃克森美孚化学专利公司 | 从中试装置放大到较大生产设施的方法 |
| WO2019217173A1 (en) | 2018-05-02 | 2019-11-14 | Exxonmobil Chemical Patents Inc. | Methods for scale-up from a pilot plant to a larger production facility |
| WO2020028059A1 (en) | 2018-07-31 | 2020-02-06 | Dow Global Technologies Llc | Polyethylene formulations for large part blow molding applications |
| ES2967059T3 (es) | 2018-11-06 | 2024-04-25 | Dow Global Technologies Llc | Precatalizadores no metaloceno solubles en alcanos |
| JP7590961B2 (ja) | 2018-11-06 | 2024-11-27 | ダウ グローバル テクノロジーズ エルエルシー | アルカン可溶性非メタロセンプレ触媒を使用してオレフィンを重合する方法 |
| EP3877392B1 (en) | 2018-11-06 | 2023-11-15 | Dow Global Technologies LLC | Alkane-soluble non-metallocene precatalysts |
| KR102139882B1 (ko) | 2019-03-12 | 2020-07-31 | 대림산업 주식회사 | 폴리올레핀 수지 제조를 위한 신규한 메탈로센 촉매 화합물 또는 이의 제조방법 |
| CN115667329B (zh) | 2020-05-29 | 2025-06-06 | 尤尼威蒂恩技术有限责任公司 | 用于挤出吹塑转筒应用的具有改善的模量的单反应器双峰聚乙烯 |
| US20230303737A1 (en) | 2020-08-05 | 2023-09-28 | Dow Global Technologies Llc | Thermoplastic compositions comprising bimodal polyethylene and articles manufactured therefrom |
| JP2023538501A (ja) | 2020-08-05 | 2023-09-08 | ダウ グローバル テクノロジーズ エルエルシー | 再生ポリマーを含む熱可塑性組成物及びそれから製造される物品 |
| EP4330294A1 (en) | 2021-04-30 | 2024-03-06 | ExxonMobil Chemical Patents Inc. | Processes for transitioning between different polymerization catalysts in a polymerization reactor |
| US20240376236A1 (en) | 2021-10-21 | 2024-11-14 | Univation Technologies, Llc | Bimodal poly(ethylene-co-1-alkene) copolymer and blow-molded intermediate bulk containers made therefrom |
| EP4587514A1 (en) | 2022-10-11 | 2025-07-23 | Dow Global Technologies LLC | Bimodal hdpe and polyethylene blend containing virgin and recycled hdpe materials |
| EP4587513A1 (en) | 2022-10-11 | 2025-07-23 | Dow Global Technologies LLC | Polyethylene blends containing virgin and recycled hdpe materials |
| CN120202060A (zh) | 2022-12-12 | 2025-06-24 | 尤尼威蒂恩技术有限责任公司 | 减少聚烯烃颗粒的摩擦生电和/或反应器结垢 |
| WO2024263748A1 (en) | 2023-06-23 | 2024-12-26 | Univation Technologies, Llc | Single reactor-made bimodal high-density polyethylene copolymer and methods and articles |
| WO2025034361A1 (en) | 2023-08-10 | 2025-02-13 | Dow Global Technologies Llc | Multimodal polyethylene compositions |
| WO2025101264A1 (en) | 2023-11-09 | 2025-05-15 | Dow Global Technologies Llc | Multimodal polyethylene compositions |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4882406A (en) * | 1983-06-15 | 1989-11-21 | Exxon Research & Engineering Company | Nodular copolymers formed of alpha-olefin copolymers coupled by non-conjugated dienes |
| US4959436A (en) | 1983-06-15 | 1990-09-25 | Exxon Research And Engineering Co. | Narrow MWD alpha-olefin copolymers |
| US4480075A (en) * | 1983-06-24 | 1984-10-30 | Shell Oil Company | Block copolymers of Ziegler-Natta polymerized and anionically polymerized monomers |
| JPH0612089B2 (ja) * | 1984-10-15 | 1994-02-16 | 本田技研工業株式会社 | 内燃エンジンのアイドル回転数フィードバック制御方法 |
| US4681956A (en) | 1985-09-25 | 1987-07-21 | Massachusetts Institute Of Technology | Catalyst composition for effecting metathesis of olefins |
| US4791180A (en) | 1985-12-12 | 1988-12-13 | Exxon Chemical Patents Inc. | New polymerization catalyst |
| US4752597A (en) | 1985-12-12 | 1988-06-21 | Exxon Chemical Patents Inc. | New polymerization catalyst |
| US5391629A (en) * | 1987-01-30 | 1995-02-21 | Exxon Chemical Patents Inc. | Block copolymers from ionic catalysts |
| US5621126A (en) | 1987-01-30 | 1997-04-15 | Exxon Chemical Patents Inc. | Monocyclopentadienyl metal compounds for ethylene-α-olefin-copolymer production catalysts |
| US5384299A (en) | 1987-01-30 | 1995-01-24 | Exxon Chemical Patents Inc. | Ionic metallocene catalyst compositions |
| US5196491A (en) * | 1988-11-25 | 1993-03-23 | E. I. Du Pont De Nemours And Company | Living cationic polymerization of alkyl vinyl ethers |
| US5026798A (en) | 1989-09-13 | 1991-06-25 | Exxon Chemical Patents Inc. | Process for producing crystalline poly-α-olefins with a monocyclopentadienyl transition metal catalyst system |
| US5504169A (en) | 1989-09-13 | 1996-04-02 | Exxon Chemical Patents Inc. | Process for producing amorphous poly-α-olefins with a monocyclopentadienyl transition metal catalyst system |
| CA2075035A1 (en) * | 1990-02-09 | 1991-08-10 | Howard W. Turner | Block copolymers from ionic catalysts |
| US5079205A (en) | 1990-07-13 | 1992-01-07 | Exxon Chemical Patents Inc. | Group ivb, vb and vib metal hydrocarbyloxides, with alumoxane for olefin polymerization |
| EP0569388B1 (en) * | 1990-12-27 | 1996-03-13 | Exxon Chemical Patents Inc. | An amido transition metal compound and a catalyst system for the production of isotactic polypropylene |
| ES2127199T3 (es) * | 1991-02-27 | 1999-04-16 | Ticona Gmbh | Proceso para la preparacion de (co)polimeros de cicloolefinas con distribucion estrecha de pesos moleculares. |
| US5399626A (en) * | 1991-04-29 | 1995-03-21 | Shell Oil Company | Viscous conjugated diene block copolymers |
| ES2108861T3 (es) * | 1991-11-25 | 1998-01-01 | Exxon Chemical Patents Inc | Composiciones cataliticas polionicas de metales de transicion. |
| DE69220675T2 (de) | 1991-12-13 | 1997-10-23 | Exxon Chemical Patents, Inc., Baytown, Tex. | ETHYLEN/HöHERE ALPHA-OLEFINCOPOLYMERE |
| US5281368A (en) * | 1992-03-31 | 1994-01-25 | Exxon Chemical Patents Inc. | Norbornene polymerization initiators and process for preparing same |
| JP2888639B2 (ja) | 1992-04-20 | 1999-05-10 | エクソン・ケミカル・パテンツ・インク | エチレン／分枝鎖オレフィンのコポリマー |
| CA2139356C (en) | 1992-07-01 | 2001-02-06 | Donna J. Crowther | Transition metal olefin polymerization catalysts |
| US5635573A (en) | 1992-12-01 | 1997-06-03 | Exxon Chemical Patents Inc. | Method for preparing alpha-olefin/cycloolefin copolymers |
| DE59402624D1 (de) * | 1993-02-12 | 1997-06-12 | Hoechst Ag | Verfahren zur Herstellung von Cycloolefincopolymeren |
| US5438102A (en) * | 1993-06-24 | 1995-08-01 | Mobil Oil Corporation | Solid elastomeric block copolymers |
| EP0654476B1 (de) * | 1993-11-24 | 2001-01-24 | TARGOR GmbH | Metallocene, Verfahren zu ihrer Herstellung und ihrer Verwendung als Katalysatoren |
| DE4344689A1 (de) * | 1993-12-27 | 1995-06-29 | Hoechst Ag | Metallocenverbindung |
| DE4344688A1 (de) * | 1993-12-27 | 1995-06-29 | Hoechst Ag | Metallocenverbindung |
| US5489651A (en) * | 1994-02-14 | 1996-02-06 | The Regents Of The University Of California | Polymerization using bimetallic bis-lanthanoid initiators |
| DE4422157A1 (de) * | 1994-06-24 | 1996-01-04 | Hoechst Ag | Verfahren zur Herstellung von Cycloolefincopolymeren |
| US5476915A (en) * | 1994-06-29 | 1995-12-19 | The Regents Of The University Of California | Method for controlled synthesis of polymers |
| JPH0881415A (ja) * | 1994-07-12 | 1996-03-26 | Ube Ind Ltd | アルケンカルボン酸エステルの製造方法 |
| DE4425408A1 (de) * | 1994-07-13 | 1996-01-18 | Hoechst Ag | Cycloolefinpolymere |
| US5621428A (en) * | 1994-12-12 | 1997-04-15 | Auravision Corporation | Automatic alignment of video window on a multimedia screen |
| EP0763553B1 (en) | 1995-02-07 | 1999-05-06 | Mitsui Chemicals, Inc. | Process for preparing olefin polymer |
| US5789474A (en) * | 1995-09-28 | 1998-08-04 | Arizona Chemical Company | Additive composition and method for increasing the upper service temperature of adhesives |
| DE69711718T2 (de) * | 1996-05-02 | 2002-10-17 | Centre National De La Recherche Scientifique, Paris | Neue verbindungen, die ein element der gruppe 13 enthalten, das mit einem mono- oder dianionischen dreizähnigen liganden gebunden ist, ein verfahren zu ihrer herstellung und ihre anwendung als polymerisationskatalysatoren |
| US5763556A (en) | 1996-05-21 | 1998-06-09 | Exxon Chemical Patents Inc. | Copolymers of ethylene and geminally disubstituted olefins |
| US6255419B1 (en) | 1997-02-07 | 2001-07-03 | Mitsui Chemicals, Inc. | Olefin polymerization catalyst and process for producing olefin polymers |
| CA2251471A1 (en) | 1997-02-07 | 1998-08-13 | Mitsui Chemicals, Incorporated | Olefin polymerization catalyst and process for the production of olefin polymers |
| US5889128A (en) | 1997-04-11 | 1999-03-30 | Massachusetts Institute Of Technology | Living olefin polymerization processes |
| US6271325B1 (en) | 1999-05-17 | 2001-08-07 | Univation Technologies, Llc | Method of polymerization |
-
1997
- 1997-04-11 US US08/843,161 patent/US5889128A/en not_active Expired - Lifetime
-
1998
- 1998-04-09 WO PCT/US1998/007466 patent/WO1998046651A2/en not_active Ceased
- 1998-04-09 CA CA002285964A patent/CA2285964C/en not_active Expired - Lifetime
- 1998-04-09 AU AU69709/98A patent/AU6970998A/en not_active Abandoned
- 1998-04-09 DE DE69810605T patent/DE69810605T2/de not_active Expired - Lifetime
- 1998-04-09 JP JP54419898A patent/JP2001520696A/ja not_active Ceased
- 1998-04-09 EP EP98915559A patent/EP0975579B1/en not_active Expired - Lifetime
-
1999
- 1999-03-04 US US09/307,241 patent/US6316555B1/en not_active Expired - Lifetime
-
2001
- 2001-08-23 US US09/935,775 patent/US6610806B2/en not_active Expired - Lifetime
-
2003
- 2003-08-22 US US10/646,355 patent/US20040138324A1/en not_active Abandoned
-
2004
- 2004-12-03 US US11/004,038 patent/US7135544B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0975579B1 (en) | 2003-01-08 |
| CA2285964A1 (en) | 1998-10-22 |
| DE69810605D1 (de) | 2003-02-13 |
| US20050187345A1 (en) | 2005-08-25 |
| AU6970998A (en) | 1998-11-11 |
| EP0975579A2 (en) | 2000-02-02 |
| US6316555B1 (en) | 2001-11-13 |
| US6610806B2 (en) | 2003-08-26 |
| US7135544B2 (en) | 2006-11-14 |
| JP2001520696A (ja) | 2001-10-30 |
| US20020111442A1 (en) | 2002-08-15 |
| WO1998046651A2 (en) | 1998-10-22 |
| US20040138324A1 (en) | 2004-07-15 |
| WO1998046651A3 (en) | 1999-03-25 |
| US5889128A (en) | 1999-03-30 |
| DE69810605T2 (de) | 2003-05-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2285964C (en) | Living olefin polymerization processes | |
| US5447895A (en) | Sterically shielded diboron-containing metallocene olefin polymerization catalysts | |
| CA2024899C (en) | Olefin polymerization catalysts | |
| EP2582710B1 (en) | Salalen ligands and organometallic complexes | |
| US6596827B2 (en) | Method for catalytic polymerization of alpha-olefin monomers using an ultra-high activity non-metallocene pre-catalyst | |
| EP3421506A1 (en) | Metallocene supported catalyst and method for producing polypropylene using same | |
| EP2739655B1 (en) | Catalysts for preparing ultra high molecular weight polyethylene (uhmwpe) | |
| CA2469111A1 (en) | Imino-amide catalyst compositions for the polymerization of olefins | |
| CN111943973B (zh) | 一类苯氧基亚胺配体骨架的双金属配合物、制备方法及应用 | |
| US7214749B2 (en) | Catalyst system for high activity and stereoselectivity in the homopolymerization and copolymerization of olefins | |
| WO2000018808A1 (en) | Cationic group 3 catalyst system | |
| JP2004513193A (ja) | オレフィン重合のためのフッ素化両性助触媒活性剤 | |
| US8598284B2 (en) | Oxygen-bridged bimetallic complex and polymerization process | |
| CA2610433C (en) | Living olefin polymerization processes | |
| Jutzi et al. | Mixed Bent Sandwich Titanium Complexes with the [2‐(Diisopropylamino) ethyl] cyclopentadienyl Ligand—Catalysts for the Polymerization of Ethylene and the Dehydrocoupling of Phenylsilane | |
| KR20190078516A (ko) | 메탈로센 담지 촉매 및 이를 이용한 폴리프로필렌의 제조 방법 | |
| Yu et al. | Zirconium enolatoimine complexes in olefin polymerization | |
| US6696532B2 (en) | Phosphinimine methanide transition metal catalysts | |
| Schrock et al. | Living olefin polymerization processes | |
| EP1101774A1 (en) | Multi-metallic metallocene catalysts for polymerization of styrene and method of polymerization using the same | |
| EP1379561B1 (en) | Olefin polymerization process using transition metal complexes | |
| US20230303597A1 (en) | Metal-ligand complex, catalyst composition for preparing ethylene-based polymer containing the same, and preparation method of ethylene -based polymer using the same | |
| CN120081878A (zh) | 多核茂金属配合物及其制备方法、催化剂组合物及其应用 | |
| CN117700585A (zh) | 用于制备乙烯共聚改性的聚（4-甲基-1-戊烯）的主催化剂及其应用 | |
| EP0896592A1 (en) | Cyclopentadiene compound with a non-coordinating anion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20180409 |