CA2509074C - A catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers - Google Patents
A catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers Download PDFInfo
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- CA2509074C CA2509074C CA002509074A CA2509074A CA2509074C CA 2509074 C CA2509074 C CA 2509074C CA 002509074 A CA002509074 A CA 002509074A CA 2509074 A CA2509074 A CA 2509074A CA 2509074 C CA2509074 C CA 2509074C
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- 239000000178 monomer Substances 0.000 title claims abstract description 163
- 229920000642 polymer Polymers 0.000 title claims abstract description 95
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 125000002091 cationic group Chemical group 0.000 claims abstract description 172
- 238000000034 method Methods 0.000 claims abstract description 72
- 229910052751 metal Inorganic materials 0.000 claims description 424
- 239000002184 metal Substances 0.000 claims description 424
- 239000003446 ligand Substances 0.000 claims description 269
- -1 cyclic olefin Chemical class 0.000 claims description 164
- 239000002243 precursor Substances 0.000 claims description 163
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 123
- 239000011572 manganese Substances 0.000 claims description 78
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 71
- 239000011651 chromium Substances 0.000 claims description 62
- 229910017052 cobalt Inorganic materials 0.000 claims description 60
- 239000010941 cobalt Substances 0.000 claims description 60
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 60
- 229910052742 iron Inorganic materials 0.000 claims description 60
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 58
- 229910052804 chromium Inorganic materials 0.000 claims description 58
- 150000001336 alkenes Chemical class 0.000 claims description 54
- 229910052703 rhodium Inorganic materials 0.000 claims description 52
- 239000010948 rhodium Substances 0.000 claims description 52
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 52
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 51
- 229910052748 manganese Inorganic materials 0.000 claims description 51
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 50
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 47
- 229910052802 copper Inorganic materials 0.000 claims description 47
- 239000010949 copper Substances 0.000 claims description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 44
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 40
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 37
- 229910052707 ruthenium Inorganic materials 0.000 claims description 37
- 239000012190 activator Substances 0.000 claims description 35
- 150000001450 anions Chemical class 0.000 claims description 27
- 229910052763 palladium Inorganic materials 0.000 claims description 21
- 229910052759 nickel Inorganic materials 0.000 claims description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 abstract description 38
- 125000004429 atom Chemical group 0.000 description 279
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 86
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 125000003118 aryl group Chemical group 0.000 description 49
- 125000000217 alkyl group Chemical group 0.000 description 41
- 150000003254 radicals Chemical class 0.000 description 40
- 125000001424 substituent group Chemical group 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 30
- 239000005977 Ethylene Substances 0.000 description 30
- 229910052739 hydrogen Inorganic materials 0.000 description 30
- 239000001257 hydrogen Substances 0.000 description 30
- 229920001577 copolymer Polymers 0.000 description 29
- 150000002367 halogens Chemical class 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 26
- 229910052736 halogen Inorganic materials 0.000 description 26
- 239000003054 catalyst Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 23
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 125000000753 cycloalkyl group Chemical group 0.000 description 21
- 239000002245 particle Substances 0.000 description 21
- 238000010168 coupling process Methods 0.000 description 20
- 238000005859 coupling reaction Methods 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 19
- 125000004122 cyclic group Chemical group 0.000 description 19
- 238000005227 gel permeation chromatography Methods 0.000 description 19
- 150000002430 hydrocarbons Chemical class 0.000 description 19
- 150000002431 hydrogen Chemical class 0.000 description 19
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- 239000003085 diluting agent Substances 0.000 description 16
- 230000007935 neutral effect Effects 0.000 description 16
- 125000003710 aryl alkyl group Chemical group 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 239000011521 glass Substances 0.000 description 14
- 125000001188 haloalkyl group Chemical group 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 229920001519 homopolymer Polymers 0.000 description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
- 229910052805 deuterium Inorganic materials 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 11
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Chemical group 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000005060 rubber Substances 0.000 description 9
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 210000002966 serum Anatomy 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 150000003568 thioethers Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 238000012644 addition polymerization Methods 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 150000002466 imines Chemical class 0.000 description 7
- 238000003780 insertion Methods 0.000 description 7
- 230000037431 insertion Effects 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- 150000003573 thiols Chemical class 0.000 description 7
- 229910052723 transition metal Inorganic materials 0.000 description 7
- 150000003624 transition metals Chemical class 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 150000004645 aluminates Chemical class 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 150000001718 carbodiimides Chemical class 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 6
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical compound OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 description 6
- 125000002524 organometallic group Chemical group 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 125000000262 haloalkenyl group Chemical group 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 125000002577 pseudohalo group Chemical group 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000105 evaporative light scattering detection Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
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- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 150000003003 phosphines Chemical class 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052710 silicon Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- JFNLZVQOOSMTJK-ULUSZKPHSA-N (4r)-bicyclo[2.2.1]hept-2-ene Chemical compound C1C2CC[C@H]1C=C2 JFNLZVQOOSMTJK-ULUSZKPHSA-N 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000000746 allylic group Chemical group 0.000 description 3
- 229920005603 alternating copolymer Polymers 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001975 deuterium Chemical group 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- MBADAMTZLHTHEG-UHFFFAOYSA-N triethoxysilylarsane Chemical compound CCO[Si]([AsH2])(OCC)OCC MBADAMTZLHTHEG-UHFFFAOYSA-N 0.000 description 1
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- RLAHVFHMDPTRKL-UHFFFAOYSA-N tris(2,4,4,6,6-pentamethylheptyl)alumane Chemical compound CC(C)(C)CC(C)(C)CC(C)C[Al](CC(C)CC(C)(C)CC(C)(C)C)CC(C)CC(C)(C)CC(C)(C)C RLAHVFHMDPTRKL-UHFFFAOYSA-N 0.000 description 1
- XZIKSWMNFLIAQP-UHFFFAOYSA-N tris(2,4,4-trimethylpentyl)alumane Chemical compound CC(C)(C)CC(C)C[Al](CC(C)CC(C)(C)C)CC(C)CC(C)(C)C XZIKSWMNFLIAQP-UHFFFAOYSA-N 0.000 description 1
- MTSCGCDHTLJJCY-UHFFFAOYSA-N tris(2-butyloctyl)alumane Chemical compound CCCCCCC(CCCC)C[Al](CC(CCCC)CCCCCC)CC(CCCC)CCCCCC MTSCGCDHTLJJCY-UHFFFAOYSA-N 0.000 description 1
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- ZYMOVZXNTDGPED-UHFFFAOYSA-N tris(2-hexyldecyl)alumane Chemical compound CCCCCCCCC(CCCCCC)C[Al](CC(CCCCCC)CCCCCCCC)CC(CCCCCC)CCCCCCCC ZYMOVZXNTDGPED-UHFFFAOYSA-N 0.000 description 1
- YFDAMRSZJLWUSQ-UHFFFAOYSA-N tris(2-methylphenyl)borane Chemical compound CC1=CC=CC=C1B(C=1C(=CC=CC=1)C)C1=CC=CC=C1C YFDAMRSZJLWUSQ-UHFFFAOYSA-N 0.000 description 1
- LKNHGIFPRLUGEG-UHFFFAOYSA-N tris(3,4,5-trifluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC(B(C=2C=C(F)C(F)=C(F)C=2)C=2C=C(F)C(F)=C(F)C=2)=C1 LKNHGIFPRLUGEG-UHFFFAOYSA-N 0.000 description 1
- OHSAEOPCBBOWPU-UHFFFAOYSA-N tris(3,5-dimethylphenyl)borane Chemical compound CC1=CC(C)=CC(B(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 OHSAEOPCBBOWPU-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- OUMZKMRZMVDEOF-UHFFFAOYSA-N tris(trimethylsilyl)phosphane Chemical compound C[Si](C)(C)P([Si](C)(C)C)[Si](C)(C)C OUMZKMRZMVDEOF-UHFFFAOYSA-N 0.000 description 1
- SPSNIEJUWOBGEO-UHFFFAOYSA-N tris[2-(trifluoromethyl)phenyl]phosphane Chemical compound FC(F)(F)C1=CC=CC=C1P(C=1C(=CC=CC=1)C(F)(F)F)C1=CC=CC=C1C(F)(F)F SPSNIEJUWOBGEO-UHFFFAOYSA-N 0.000 description 1
- OSMBUUFIZBTSNO-UHFFFAOYSA-N tris[4-(fluoromethyl)phenyl]borane Chemical compound C1=CC(CF)=CC=C1B(C=1C=CC(CF)=CC=1)C1=CC=C(CF)C=C1 OSMBUUFIZBTSNO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
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- B—PERFORMING OPERATIONS; TRANSPORTING
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| WO2008120912A1 (en) * | 2007-03-30 | 2008-10-09 | Lg Chem, Ltd. | Copolymer comprising alkene, acrylate and unsaturated organic acid, and method for preparing the same |
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| CN108003094B (zh) * | 2017-11-22 | 2020-04-17 | 中国科学技术大学 | 配体、其制备方法、镍配合物、其制备方法及其应用 |
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|---|---|---|---|---|
| SU432769A1 (ru) | 1970-07-13 | 1974-12-15 | Способ получения линейных полимеров | |
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| DE102004025938A1 (de) * | 2004-05-27 | 2005-12-22 | Bayer Ag | Dinukleare Übergangsmetallkomplexe |
-
2005
- 2005-05-27 US US11/139,874 patent/US7172986B2/en not_active Expired - Fee Related
- 2005-06-02 CA CA002509074A patent/CA2509074C/en not_active Expired - Fee Related
- 2005-06-02 TW TW094118119A patent/TWI318987B/zh not_active IP Right Cessation
- 2005-06-04 EP EP05253453A patent/EP1607413A1/en not_active Withdrawn
- 2005-06-13 JP JP2005171927A patent/JP4620530B2/ja not_active Expired - Fee Related
- 2005-06-13 KR KR1020050050317A patent/KR101160556B1/ko not_active Expired - Fee Related
- 2005-06-14 CN CNB2005100789507A patent/CN1331895C/zh not_active Expired - Fee Related
-
2009
- 2009-02-16 JP JP2009033235A patent/JP2009108332A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1715300A (zh) | 2006-01-04 |
| JP4620530B2 (ja) | 2011-01-26 |
| JP2009108332A (ja) | 2009-05-21 |
| TWI318987B (en) | 2010-01-01 |
| US20050277569A1 (en) | 2005-12-15 |
| CA2509074A1 (en) | 2005-12-14 |
| TW200604228A (en) | 2006-02-01 |
| JP2006009003A (ja) | 2006-01-12 |
| CN1331895C (zh) | 2007-08-15 |
| EP1607413A1 (en) | 2005-12-21 |
| KR101160556B1 (ko) | 2012-06-26 |
| KR20060049580A (ko) | 2006-05-19 |
| US7172986B2 (en) | 2007-02-06 |
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