DE69826001T2 - Verfahren zur herstellung von copolymeren von ethylen and norbornen-typ monomeren mit cationischen palladium-katalysatoren - Google Patents
Verfahren zur herstellung von copolymeren von ethylen and norbornen-typ monomeren mit cationischen palladium-katalysatoren Download PDFInfo
- Publication number
- DE69826001T2 DE69826001T2 DE69826001T DE69826001T DE69826001T2 DE 69826001 T2 DE69826001 T2 DE 69826001T2 DE 69826001 T DE69826001 T DE 69826001T DE 69826001 T DE69826001 T DE 69826001T DE 69826001 T2 DE69826001 T2 DE 69826001T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- norbornene
- palladium
- ethylene
- branched
- 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 - Fee Related
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 107
- 239000005977 Ethylene Substances 0.000 title claims description 103
- 239000003054 catalyst Substances 0.000 title claims description 96
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims description 78
- 239000000178 monomer Substances 0.000 title claims description 67
- 229920001577 copolymer Polymers 0.000 title claims description 51
- 229910052763 palladium Inorganic materials 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 palladium halides Chemical class 0.000 claims description 88
- 239000003446 ligand Substances 0.000 claims description 60
- 150000001450 anions Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 10
- 125000002524 organometallic group Chemical group 0.000 claims description 10
- 150000002941 palladium compounds Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000011065 in-situ storage Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052727 yttrium Inorganic materials 0.000 claims description 9
- 125000002091 cationic group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003586 protic polar solvent Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 59
- 229920000642 polymer Polymers 0.000 description 51
- 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 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 22
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 229920001897 terpolymer Polymers 0.000 description 15
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RGGBKNFGPFEDRC-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enyl(triethoxy)silane Chemical compound C1CC2C=CC1([Si](OCC)(OCC)OCC)C2 RGGBKNFGPFEDRC-UHFFFAOYSA-N 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 10
- 239000003426 co-catalyst Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 8
- 239000002841 Lewis acid Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 229940050176 methyl chloride Drugs 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UAXNXOMKCGKNCI-UHFFFAOYSA-N 1-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 UAXNXOMKCGKNCI-UHFFFAOYSA-N 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000005234 alkyl aluminium group Chemical group 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 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 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 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 5
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 5
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 5
- LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 5
- 229920001038 ethylene copolymer Polymers 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000002879 Lewis base Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 150000007527 lewis bases Chemical class 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 150000002848 norbornenes Chemical class 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- ZOICEQJZAWJHSI-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)boron Chemical compound [B]C1=C(F)C(F)=C(F)C(F)=C1F ZOICEQJZAWJHSI-UHFFFAOYSA-N 0.000 description 3
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 229910018286 SbF 6 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000002940 palladium Chemical class 0.000 description 3
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 3
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920006029 tetra-polymer Polymers 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- 229910052716 thallium Inorganic materials 0.000 description 3
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 150000003623 transition metal compounds Chemical class 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- XYZWMVYYUIMRIZ-UHFFFAOYSA-N 4-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Br)C=C1 XYZWMVYYUIMRIZ-UHFFFAOYSA-N 0.000 description 2
- HHKDWDAAEFGBAC-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enyl(triethoxy)silane Chemical compound C1C2C([Si](OCC)(OCC)OCC)CC1C=C2 HHKDWDAAEFGBAC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 150000008648 triflates Chemical class 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-O triphenylazanium Chemical compound C1=CC=CC=C1[NH+](C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-O 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
-
- 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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87653897A | 1997-06-09 | 1997-06-09 | |
| US876538 | 1997-06-09 | ||
| PCT/US1998/012022 WO1998056839A1 (en) | 1997-06-09 | 1998-06-09 | Method for the preparation of copolymers of ethylene/norbornene-type monomers with cationic palladium catalysts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69826001D1 DE69826001D1 (de) | 2004-10-07 |
| DE69826001T2 true DE69826001T2 (de) | 2005-09-08 |
Family
ID=25367960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69826001T Expired - Fee Related DE69826001T2 (de) | 1997-06-09 | 1998-06-09 | Verfahren zur herstellung von copolymeren von ethylen and norbornen-typ monomeren mit cationischen palladium-katalysatoren |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6265506B1 (enExample) |
| EP (1) | EP0988331B1 (enExample) |
| JP (1) | JP2002504172A (enExample) |
| AU (1) | AU8065298A (enExample) |
| DE (1) | DE69826001T2 (enExample) |
| WO (1) | WO1998056839A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6103658A (en) * | 1997-03-10 | 2000-08-15 | Eastman Chemical Company | Olefin polymerization catalysts containing group 8-10 transition metals, processes employing such catalysts and polymers obtained therefrom |
| US6200925B1 (en) | 1997-03-13 | 2001-03-13 | Eastman Chemical Company | Catalyst compositions for the polymerization of olefins |
| US6245871B1 (en) | 1997-04-18 | 2001-06-12 | Eastman Chemical Company | Group 8-10 transition metal olefin polymerization catalysts |
| US6174976B1 (en) | 1998-02-24 | 2001-01-16 | Eastman Chemical Company | Neutral nickel complexes for olefin polymerization |
| CA2338847A1 (en) * | 1998-07-27 | 2000-02-10 | Basell Technology Company B.V. | A polymerization process |
| US6117959A (en) | 1998-09-02 | 2000-09-12 | Eastman Chemical Company | Polyolefin catalysts |
| AU6291999A (en) * | 1998-10-05 | 2000-04-26 | B.F. Goodrich Company, The | Catalyst and methods for polymerizing cycloolefins |
| US6620896B1 (en) | 1999-02-23 | 2003-09-16 | Eastman Chemical Company | Mixed olefin polymerization catalysts, processes employing such catalysts, and polymers obtained therefrom |
| GB9918635D0 (en) | 1999-08-06 | 1999-10-13 | Bp Chem Int Ltd | Polymerisation process |
| US6350837B1 (en) | 2000-06-09 | 2002-02-26 | Eastman Chemical Company | Copolymerization of norbornene and functional norbornene monomers |
| JP2002088029A (ja) | 2000-09-07 | 2002-03-27 | Takasago Internatl Corp | 芳香族アミン類の製造方法 |
| DE10118633A1 (de) * | 2001-04-12 | 2002-10-17 | Basf Ag | Verfahren zur übergangsmetallkatalysierten Herstellung von wässrigen Dispersionen enthaltend Polyolefine oder vinylaromatische Polymere |
| JP5093949B2 (ja) * | 2001-09-13 | 2012-12-12 | 三井化学株式会社 | α−オレフィン・環状オレフィン共重合体およびその製造方法 |
| US20030130452A1 (en) * | 2001-10-12 | 2003-07-10 | Johnson Lynda Kaye | Copolymers of ethylene with various norbornene derivatives |
| DE10297606T5 (de) * | 2001-12-28 | 2004-12-09 | Mitsui Chemicals, Inc. | Silicium-enthaltendes Olefin-Copolymer, vernetzbare Kautschukzusammensetzung desselben und Verwendungen desselben |
| US7674847B2 (en) * | 2003-02-21 | 2010-03-09 | Promerus Llc | Vinyl addition polycyclic olefin polymers prepared with non-olefinic chain transfer agents and uses thereof |
| JP4203739B2 (ja) * | 2003-08-20 | 2009-01-07 | Ｊｓｒ株式会社 | 環状オレフィン系付加重合体の製造方法 |
| KR101214355B1 (ko) * | 2003-08-20 | 2012-12-20 | 제이에스알 가부시끼가이샤 | 환상 올레핀계 부가 중합체의 제조 방법 |
| US7087687B2 (en) * | 2003-08-21 | 2006-08-08 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| US7199074B2 (en) * | 2004-06-14 | 2007-04-03 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| US7172986B2 (en) * | 2004-06-14 | 2007-02-06 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| KR100733923B1 (ko) * | 2004-07-07 | 2007-07-02 | 주식회사 엘지화학 | 극성 작용기를 갖는 고리형 올레핀 중합체 제조용 촉매시스템, 이를 이용한 중합체 제조방법과 이 방법에 의해제조된 올레핀 중합체 및 상기 중합체를 포함하는 광학이방성 필름 |
| EP1930349B1 (en) * | 2005-09-27 | 2014-01-15 | Scivax Corporation | Resin for thermal imprint |
| US7727705B2 (en) * | 2007-02-23 | 2010-06-01 | Fujifilm Electronic Materials, U.S.A., Inc. | High etch resistant underlayer compositions for multilayer lithographic processes |
| JP2011073974A (ja) * | 2009-09-29 | 2011-04-14 | Sumitomo Bakelite Co Ltd | ノルボルネン誘導体およびその製造方法 |
| JP5738097B2 (ja) * | 2010-09-10 | 2015-06-17 | 昭和電工株式会社 | ノルボルネン系重合体の製造方法 |
| EP3190120B1 (en) * | 2012-05-11 | 2021-11-17 | The University Of Tokyo | Catalyst for synthesizing polyolefins |
| CN109081882B (zh) * | 2017-06-13 | 2020-12-18 | 中国石油化工股份有限公司 | 环烯烃共聚物及其制备方法 |
| JP7132087B2 (ja) * | 2017-11-29 | 2022-09-06 | 日本ポリエチレン株式会社 | オレフィン共重合体、及びその製造方法 |
| CN113121940B (zh) * | 2019-12-31 | 2022-12-30 | 广东生益科技股份有限公司 | 一种热固性树脂组合物及使用其的预浸料、层压板和印制线路板 |
| CN118434781B (zh) * | 2021-12-23 | 2025-05-06 | 宝理塑料株式会社 | 环烯烃共聚物的制造方法 |
| CN116925273A (zh) * | 2022-03-31 | 2023-10-24 | 中国石油化工股份有限公司 | 制备极性乙烯共聚物的反应体系及应用、极性乙烯共聚物及其聚合方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277036A (en) | 1962-09-10 | 1966-10-04 | Union Carbide Corp | Crosslinked copolymers of ethylene and derivatives of bicyclo[2.2.1]hept-2-ene |
| US3320222A (en) | 1963-10-28 | 1967-05-16 | Monsanto Co | Copolymers of ethylene and 2-hydroxymethyl-5-norbornene |
| US3494897A (en) | 1963-12-05 | 1970-02-10 | Union Carbide Corp | Ethylene/bicyclo(2.2.1)hept-2-ene copolymers |
| FR2087213A5 (enExample) | 1970-05-11 | 1971-12-31 | Aquitaine Petrole | |
| JPS60133042A (ja) | 1983-12-20 | 1985-07-16 | Nippon Petrochem Co Ltd | 電気絶縁用樹脂組成物 |
| CA1278899C (en) | 1985-05-24 | 1991-01-08 | Mitsui Chemicals, Inc. | Random copolymer, and process for production thereof |
| US5091506A (en) | 1989-10-11 | 1992-02-25 | Shell Oil Compnay | Polymerization of carbon monoxide/norbornene with p bidentate ligand |
| WO1992006123A1 (fr) | 1990-10-05 | 1992-04-16 | Idemitsu Kosan Co., Ltd. | Procede de production de polymere de cycloolefine et de copolymere de cycloolefine et composition et moulage prepares a partir de ces composes |
| US5837787A (en) | 1993-01-19 | 1998-11-17 | Exxon Chemical Patents, Inc. | Process for producing elastic thermoplastic α-olefin/cyclic olefin copolymers |
| AU729324B2 (en) | 1995-01-24 | 2001-02-01 | E.I. Du Pont De Nemours And Company | Alpha-olefins and olefin polymers and processes therefor |
| DE59605823D1 (de) * | 1995-05-22 | 2000-10-05 | Basf Ag | Verfahren zur herstellung von polymeren aus olefinisch ungesättigten monomeren |
| US5705503A (en) * | 1995-05-25 | 1998-01-06 | Goodall; Brian Leslie | Addition polymers of polycycloolefins containing functional substituents |
| US6169152B1 (en) * | 1996-07-05 | 2001-01-02 | Jsr Corporation | Olefin polymerization catalyst comprising transition metal compound containing a cyclic ligand having at least two nitrogen atoms in its main chain skeleton |
| ATE277091T1 (de) * | 1996-07-23 | 2004-10-15 | Du Pont | Polymerisationsverfahren für olefinen |
-
1998
- 1998-06-09 EP EP98928977A patent/EP0988331B1/en not_active Expired - Lifetime
- 1998-06-09 DE DE69826001T patent/DE69826001T2/de not_active Expired - Fee Related
- 1998-06-09 AU AU80652/98A patent/AU8065298A/en not_active Abandoned
- 1998-06-09 WO PCT/US1998/012022 patent/WO1998056839A1/en not_active Ceased
- 1998-06-09 JP JP50315499A patent/JP2002504172A/ja not_active Ceased
- 1998-06-09 US US09/094,349 patent/US6265506B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HK1026048A1 (en) | 2000-12-01 |
| DE69826001D1 (de) | 2004-10-07 |
| JP2002504172A (ja) | 2002-02-05 |
| WO1998056839A1 (en) | 1998-12-17 |
| EP0988331B1 (en) | 2004-09-01 |
| US6265506B1 (en) | 2001-07-24 |
| EP0988331A1 (en) | 2000-03-29 |
| AU8065298A (en) | 1998-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |