JP2000515195A - オレフィンに対する重合法 - Google Patents
オレフィンに対する重合法Info
- Publication number
- JP2000515195A JP2000515195A JP10507183A JP50718398A JP2000515195A JP 2000515195 A JP2000515195 A JP 2000515195A JP 10507183 A JP10507183 A JP 10507183A JP 50718398 A JP50718398 A JP 50718398A JP 2000515195 A JP2000515195 A JP 2000515195A
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbyl
- independently
- compound
- olefin
- substituted
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 66
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 57
- 238000006116 polymerization reaction Methods 0.000 title description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 70
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract description 57
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 55
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 32
- -1 palladium [II] compound Chemical class 0.000 claims abstract description 31
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 29
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005977 Ethylene Substances 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 11
- 239000002184 metal Substances 0.000 claims abstract description 11
- 239000004711 α-olefin Substances 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 103
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 150000001450 anions Chemical class 0.000 claims description 23
- 125000003107 substituted aryl group Chemical group 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 150000002941 palladium compounds Chemical class 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052727 yttrium Inorganic materials 0.000 claims description 7
- 229910052718 tin Inorganic materials 0.000 claims description 6
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- 229910000071 diazene Inorganic materials 0.000 abstract description 4
- 150000007517 lewis acids Chemical class 0.000 abstract description 4
- 229920000098 polyolefin Polymers 0.000 abstract description 4
- 238000000465 moulding Methods 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 239000010408 film Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 229920000642 polymer Polymers 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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 17
- 238000003756 stirring Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 8
- 239000002168 alkylating agent Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000012018 catalyst precursor Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical class C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001676573 Minium Species 0.000 description 2
- 150000004703 alkoxides Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052878 cordierite Inorganic materials 0.000 description 2
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 150000002848 norbornenes Chemical class 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 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 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 230000003335 steric effect Effects 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002352 surface water Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- LKAQFOKMMXWRRQ-UHFFFAOYSA-N 2-chloro-4,6-dimethylaniline Chemical compound CC1=CC(C)=C(N)C(Cl)=C1 LKAQFOKMMXWRRQ-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 1
- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000272534 Struthio camelus Species 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- BVFIWUYGGUULFF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene;5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2CCC1C=C2.C1C2C(C)CC1C=C2 BVFIWUYGGUULFF-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JUOOLZKBVJRIAM-UHFFFAOYSA-N n-chloro-4-methoxyaniline Chemical compound COC1=CC=C(NCl)C=C1 JUOOLZKBVJRIAM-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.約−100℃〜約+200℃の温度において、(I)のNi[II]また はPd[II]錯体、 ニッケルまたはパラジウム化合物にヒドロカルビル基を移すことのできる金属含 有ヒドロカルビル化化合物、及びB(C6F5)3,AlCl3,AlBr3,Al( OTf)3,及び(R13R14R15C)Yからなる群から選択される化合物(II )を、オレフィンと接触させることを含んでなる、但し、 該オレフィンがエチレン、式R17CH=CH2またはR17CH=CHR17のオ レフィン、シクロブテン、シクロペンテン、及びノルボルネンからなる群から選 択され、 R2及びR5が、両R2及びR5においてイミノ窒素原子に直接結合する炭素原子 に結合した炭素原子の少なくとも1つがそれに結合するいずれの水素原子も有さ ないという条件下に、それぞれ独立にアリールまたは置換アリールであり、 R3及びR4がそれぞれ独立に水素、ヒドロカルビル、置換ヒドロカルビルであ り、或いはR3及びR4が一緒になってヒドロカルビレンまたは置換ヒドロカルビ レンであって炭素環式環を形成し、 R13、R14及びR15はそれぞれ独立にアリールまたは置換アリールであり、 各R17が、該オレフィン中のオレフィン結合が第4級炭素原子または少なくと も2つの飽和炭素原子によっていずれか他のオレフィン結合または芳香族環から 隔離されているという条件下に、独立にヒドロカルビルまたは置換ヒドロカルビ ルであり、そして Yが弱く配位するアニオンである、 該オレフィンの重合法。 2.(I)を含むNi[II]またはPd[II]塩 を、ニッケルまたはパラジウム化合物にヒドロカルビル基を移すことのできる金 属含有ヒドロカルビル化化合物、及び随時B(C6F5)3,AlCl3,AlBr3 ,Al(OTf)3,及び(R13R14R15C) Yからなる群から選択される化 合物(II)と共に、オレフィンと接触させることを含んでなる、但し、 該Ni[II]またはPd[II]塩がNi(O2CR7)2,Ni[R8COC H=C(O)R8]2,NiX2,L1L2NiX2,Ni(OR18)2,Pd(O2C R9)2, Pd[R10COCH=C(O)R10]2,PdX2,L1L2PdX2, 及びPd(OR19)2からなる群から選択され、 該オレフィンがエチレン、式R17CH=CH2またはR17CH=CHR17のオ レフィン、シクロブテン、シクロペンテン、及びノルボルネンからなる群から選 択され、 R2及びR5が、両R2及びR5においてイミノ窒素原子に直接結合する 炭素原子に結合した炭素原子の少なくとも1つがそれに結合するいずれの水素原 子も有さない条件下に、それぞれ独立にアリールまたは置換アリールであり、 R3及びR4がそれぞれ独立に水素、ヒドロカルビル、置換ヒドロカルビルであ り、或いはR3及びR4は一緒になってヒドロカルビレンまたは置換ヒドロカルビ レンであって炭素環式環を形成し、 R13、R14及びR15がそれぞれ独立にアリールまたは置換アリールであり、 各R17が、該オレフィン中のオレフィン結合が第4級炭素原子または少なくと も2つの飽和炭素原子によっていずれか他のオレフィン結合または芳香族環から 隔離されているという条件下に、独立にヒドロカルビルまたは置換ヒドロカルビ ルであり、そして 各R18及びR19が独立にヒドロカルビル、置換ヒドロカルビル、またはR21S O3 -であり、 各R7、R8、R9及びR10が独立に炭素数1〜20のヒドロカルビルまたは置 換ヒドロカルビルであり、 各Xが独立にハロゲンまたはR21SO3 -であり、 各R21が独立にアリール、置換アリールまたはパーフルオロアルキルであり、 L1及びL2が、独立に(I)で置換されうる配位子または一緒になって(I) で置換されうる2価の配位子であり、そして Yが弱く配位するアニオンである、なお 該ヒドロカルビル化化合物がアルミニウム原子に結合した1つまたはそれ以上 のハロゲン原子を含むアルキルアルミニウム化合物或いは(R20 AlO)q以外であるとき、(II)が存在しなければならない、ここにR20 がアルキルでありそしてqは正の整数である、 該オレフィンの重合法。 3.該オレフィンがエチレンである、請求の範囲1または2の方法。 4.該オレフィンがノルボルネンである、請求の範囲1または2の方法。 5.該オレフィンがシクロペンテンである、請求の範囲1または2の方法。 6.該オレフィンが線状α−オレフィンである、請求の範囲1または2の方法 。 7.ランダムまたはブロック共重合体が製造される、請求の範囲1または2の 方法。 8.該ヒドロカルビル化化合物が MXmR6 n [式中、MはLi、Mg、Zn[II]、AlまたはSn[IV]であり、 各XはF、Cl、Br、I、またはOR12であり、 各R6は独立に炭素数1〜20のヒドロカルビルであり、 mは0或いは1またはそれ以上の整数であり、 nは1またはそれ以上の整数であり、 m+nはMの荷数であり、そして R12は炭素数1〜20のヒドロカルビルである] である、請求の範囲1または2の方法。 9.YがBAF、BF4、B(C6F5)4、SbF6またはPF6である、 請求の範囲1または2の方法。 10.R2、R3、R4及びR5が以下の通りである 請求の範囲1または2の方法。 11.該温度が約25〜約100℃である、請求の範囲1または2の方法。 12.(II)が(C6F5)3Bである、請求の範囲1または2の方 法。 13.該錯体が [式中、MはNiまたはPdであり、 T1及びT2はそれぞれ独立にハロゲン、R7CO2、R8COCH=C(O) R8、またはOR18であり、 R2及びR5は、両R2及びR5においてイミノ窒素原子に直接結合する炭素原 子に結合した炭素原子の少なくとも1つがそれに結合するいずれの水素原子も有 さないという条件下に、それぞれ独立にアリールまたは置換アリールであり、 R3及びR4はそれぞれ独立に水素、ヒドロカルビル、置換ヒドロカルビルで あり、或いはR3及びR4は一緒になってヒドロカルビレンまたは置換ヒドロカル ビレンであって炭素環式環を形成し、 各R18は独立にヒドロカルビルであり、そして 各R7及びR8は独立にヒドロカルビルまたは炭素数1〜20の置換ヒドロカ ルビルである] である、請求の範囲1の方法。 14.(II):PdまたはNiのモル比が約0.5〜約10であり、ヒドロ カルビル化化合物:PdまたはNiのモル比が約0.5〜約20である、請求の 範囲1の方法。 15.(II)が存在する場合、(II):PdまたはNiのモル比 が約0.5〜約10であり、ヒドロカルビル化化合物:PdまたはNiのモル比 が好ましくは約0.5〜約20であり、そして (II)が存在しない場合、ヒドロカルビル化化合物:PdまたはNiの該モル 比が約0.5〜約200である、 請求の範囲1の方法。 16.T1及びT2が塩素または臭素である、請求の範囲1の方法。 17.該ヒドロカルビル化化合物が MXmR6 n [式中、MはLi、Mg、Zn[II]、AlまたはSn[IV]であり、 各XはF、Cl、Br、I、またはOR12であり、 各R6は独立に炭素数1〜20のヒドロカルビルであり、 mは0或いは1またはそれ以上の整数であり、 nは1またはそれ以上の整数であり、 m+nはMの荷数であり、そして R12は炭素数1〜20のヒドロカルビルである] であり、そして 該温度が約25〜約100℃であり、そして (II)が(C6F5)3Bである、 請求の範囲1、2または13の方法。 18.該ヒドロカルビル化化合物が MXmR6 n [式中、MはLi、Mg、Zn[II]、AlまたはSn[IV]であり、 各XはF、Cl、Br、I、またはOR12であり、 各R6は独立に炭素数1〜20のヒドロカルビルであり、 mは0或いは1またはそれ以上の整数であり、 nは1またはそれ以上の整数であり、 m+nはMの荷数であり、そして R12は炭素数1〜20のヒドロカルビルである] であり、 該温度が約25〜約100℃であり、そして (II)が(C6F5)3Bであり、そして 該オレフィンがエチレン、ノルボルネン、シクロペンテン、または線状α−オ レフィンの1つまたはそれ以上である、 請求の範囲1、2または13の方法。 19.式 [式中、各Xは独立にハロゲン、R7CO2,R8COCH=C(O)R8,また はOR18であり、各R18は独立にヒドロカルビルであり、そしてR7,R8は炭素 数1〜20のヒドロカルビルまたは置換ヒドロカルビルである] の化合物。 20.Xの双方が塩素または臭素である、請求の範囲19の化合物。 21.式 の化合物。 22.各R18及びR19が独立にヒドロカルビルであり、各R7、R8、R9及び R10が独立にヒドロカルビルであり、そして各Xが独立に塩素または臭素である 、請求の範囲2の方法。
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US2229596P | 1996-07-23 | 1996-07-23 | |
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US2279696P | 1996-07-30 | 1996-07-30 | |
US60/022,796 | 1996-07-30 | ||
PCT/US1997/012801 WO1998003559A1 (en) | 1996-07-23 | 1997-07-21 | Polymerization processes for olefins |
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Also Published As
Publication number | Publication date |
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KR20000067989A (ko) | 2000-11-25 |
CN1226256A (zh) | 1999-08-18 |
EA199900152A1 (ru) | 1999-08-26 |
KR100469185B1 (ko) | 2005-01-31 |
DE69730838T2 (de) | 2006-02-16 |
CA2259582A1 (en) | 1998-01-29 |
EP0914354A1 (en) | 1999-05-12 |
EP0914354B1 (en) | 2004-09-22 |
US6002034A (en) | 1999-12-14 |
US5852145A (en) | 1998-12-22 |
DE69730838D1 (de) | 2004-10-28 |
ATE277091T1 (de) | 2004-10-15 |
AU3961797A (en) | 1998-02-10 |
WO1998003559A1 (en) | 1998-01-29 |
BR9710881A (pt) | 1999-09-08 |
IL127865A0 (en) | 1999-10-28 |
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