FI119430B - Katalysaattorikoostumus ja menetelmä olefiinin polymerointiin - Google Patents
Katalysaattorikoostumus ja menetelmä olefiinin polymerointiin Download PDFInfo
- Publication number
- FI119430B FI119430B FI971823A FI971823A FI119430B FI 119430 B FI119430 B FI 119430B FI 971823 A FI971823 A FI 971823A FI 971823 A FI971823 A FI 971823A FI 119430 B FI119430 B FI 119430B
- Authority
- FI
- Finland
- Prior art keywords
- group
- olefin
- catalyst composition
- eller
- transition metal
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 21
- 230000000379 polymerizing effect Effects 0.000 title description 3
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 64
- 150000003624 transition metals Chemical class 0.000 claims abstract description 62
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 36
- 239000003446 ligand Substances 0.000 claims abstract description 29
- 239000010936 titanium Substances 0.000 claims abstract description 22
- 230000000737 periodic effect Effects 0.000 claims abstract description 17
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 3
- -1 cyclic olefin Chemical class 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
- 239000005977 Ethylene Substances 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000004711 α-olefin Substances 0.000 claims description 12
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229920001971 elastomer Polymers 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 150000001993 dienes Chemical class 0.000 claims description 6
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 claims 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- 238000005452 bending Methods 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 239000003426 co-catalyst Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 238000001816 cooling Methods 0.000 description 17
- 239000010410 layer Substances 0.000 description 17
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 150000002902 organometallic compounds Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- UILZQFGKPHAAOU-ARJAWSKDSA-N (z)-2-bromobut-2-ene Chemical compound C\C=C(\C)Br UILZQFGKPHAAOU-ARJAWSKDSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229910010068 TiCl2 Inorganic materials 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- UXQAEOWCSOPBLF-UHFFFAOYSA-N 2,2,3,3-tetramethyloctane Chemical compound CCCCCC(C)(C)C(C)(C)C UXQAEOWCSOPBLF-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910010062 TiCl3 Inorganic materials 0.000 description 2
- NSMYRAHIJDSFIE-UHFFFAOYSA-L [Cl-].[Cl-].C(CCC)N(CCCC)CC[Ti+]C1C(=C(C(=C1C)C)C)C.C(CCC)N(CCCC)CC[Ti+]C1C(=C(C(=C1C)C)C)C Chemical compound [Cl-].[Cl-].C(CCC)N(CCCC)CC[Ti+]C1C(=C(C(=C1C)C)C)C.C(CCC)N(CCCC)CC[Ti+]C1C(=C(C(=C1C)C)C)C NSMYRAHIJDSFIE-UHFFFAOYSA-L 0.000 description 2
- WRAMVPJTSNTLPS-UHFFFAOYSA-L [Cl-].[Cl-].CN(C)CCC[Ti+]C1C(=C(C(=C1C)C)C)C.CN(C)CCC[Ti+]C1C(=C(C(=C1C)C)C)C Chemical compound [Cl-].[Cl-].CN(C)CCC[Ti+]C1C(=C(C(=C1C)C)C)C.CN(C)CCC[Ti+]C1C(=C(C(=C1C)C)C)C WRAMVPJTSNTLPS-UHFFFAOYSA-L 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- IZMJWGJGVGRWBW-UHFFFAOYSA-N ethyl 3-(dimethylamino)propanoate Chemical compound CCOC(=O)CCN(C)C IZMJWGJGVGRWBW-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
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- 125000003936 heterocyclopentadienyl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 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
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- 238000012360 testing method Methods 0.000 description 2
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- 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 1
- OGQVROWWFUXRST-FNORWQNLSA-N (3e)-hepta-1,3-diene Chemical compound CCC\C=C\C=C OGQVROWWFUXRST-FNORWQNLSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- VNPQQEYMXYCAEZ-UHFFFAOYSA-N 1,2,3,4-tetramethylcyclopenta-1,3-diene Chemical compound CC1=C(C)C(C)=C(C)C1 VNPQQEYMXYCAEZ-UHFFFAOYSA-N 0.000 description 1
- BUAKPITZELZWNI-UHFFFAOYSA-N 1-chlorocyclohexene Chemical compound ClC1=CCCCC1 BUAKPITZELZWNI-UHFFFAOYSA-N 0.000 description 1
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- CVRYIGYZQFVSBC-UHFFFAOYSA-N 5-[2-(dibutylamino)ethyl]nona-2,7-dien-5-ol Chemical compound CCCCN(CCCC)CCC(O)(CC=CC)CC=CC CVRYIGYZQFVSBC-UHFFFAOYSA-N 0.000 description 1
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- ABNCGYCFZDYTQP-UHFFFAOYSA-L CC1=C(C)C(C)=C(C)C1[Ti](Cl)Cl Chemical compound CC1=C(C)C(C)=C(C)C1[Ti](Cl)Cl ABNCGYCFZDYTQP-UHFFFAOYSA-L 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 239000012459 cleaning agent Substances 0.000 description 1
- 239000012967 coordination catalyst Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 108700003601 dimethylglycine Proteins 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HEAMQYHBJQWOSS-UHFFFAOYSA-N ethene;oct-1-ene Chemical compound C=C.CCCCCCC=C HEAMQYHBJQWOSS-UHFFFAOYSA-N 0.000 description 1
- SVFAGVSFZREYAA-UHFFFAOYSA-N ethyl 3-(dibutylamino)propanoate Chemical compound CCCCN(CCCC)CCC(=O)OCC SVFAGVSFZREYAA-UHFFFAOYSA-N 0.000 description 1
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 230000003834 intracellular effect Effects 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
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- KSFKITHBJMMBKK-UHFFFAOYSA-N n,n-dimethyl-1-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)methanamine Chemical compound CN(C)CC1C(C)=C(C)C(C)=C1C KSFKITHBJMMBKK-UHFFFAOYSA-N 0.000 description 1
- SYAYMMQVHBRFQH-UHFFFAOYSA-N n,n-dimethyl-2-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)ethanamine Chemical compound CN(C)CCC1C(C)=C(C)C(C)=C1C SYAYMMQVHBRFQH-UHFFFAOYSA-N 0.000 description 1
- MBMVWDXQKAKMCL-UHFFFAOYSA-N n,n-dimethyl-3-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)propan-1-amine Chemical compound CN(C)CCCC1C(C)=C(C)C(C)=C1C MBMVWDXQKAKMCL-UHFFFAOYSA-N 0.000 description 1
- 229940078490 n,n-dimethylglycine Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- GCKZPELTJOBCOU-UHFFFAOYSA-N n-butyl-n-[2-(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)ethyl]butan-1-amine Chemical compound CCCCN(CCCC)CCC1C(C)=C(C)C(C)=C1C GCKZPELTJOBCOU-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical group CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920005638 polyethylene monopolymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ONQCKWIDZTZEJA-UHFFFAOYSA-N sodium;pentane Chemical compound [Na+].CCCC[CH2-] ONQCKWIDZTZEJA-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61908—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
- C08F4/61912—Component covered by group C08F4/60 containing a transition metal-carbon bond in combination with an organoaluminium compound
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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL9401800 | 1994-10-31 | ||
| NL9401800 | 1994-10-31 | ||
| PCT/NL1995/000372 WO1996013529A1 (en) | 1994-10-31 | 1995-10-27 | Catalyst composition and process for the polymerization of an olefin |
| NL9500372 | 1995-10-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI971823A0 FI971823A0 (fi) | 1997-04-29 |
| FI971823L FI971823L (fi) | 1997-06-27 |
| FI119430B true FI119430B (fi) | 2008-11-14 |
Family
ID=19864842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI971823A FI119430B (fi) | 1994-10-31 | 1997-04-29 | Katalysaattorikoostumus ja menetelmä olefiinin polymerointiin |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5986029A (de) |
| EP (1) | EP0789718B1 (de) |
| JP (1) | JPH10508055A (de) |
| CN (1) | CN1171794A (de) |
| AT (1) | ATE164858T1 (de) |
| AU (1) | AU3817595A (de) |
| BR (1) | BR9509457A (de) |
| DE (1) | DE69502028T2 (de) |
| ES (1) | ES2116776T3 (de) |
| FI (1) | FI119430B (de) |
| NO (1) | NO971843L (de) |
| RU (1) | RU2135522C1 (de) |
| WO (1) | WO1996013529A1 (de) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6030917A (en) | 1996-07-23 | 2000-02-29 | Symyx Technologies, Inc. | Combinatorial synthesis and analysis of organometallic compounds and catalysts |
| US6440745B1 (en) | 1994-10-18 | 2002-08-27 | Symyx Technologies | Combinatorial synthesis and screening of organometallic compounds and catalysts |
| US6419881B1 (en) | 1994-10-18 | 2002-07-16 | Symyx Technologies, Inc. | Combinatorial arrays of organometallic compounds and catalysts |
| ES2124054T3 (es) * | 1995-06-12 | 1999-01-16 | Targor Gmbh | Compuesto de metal de transicion. |
| US5962714A (en) * | 1995-10-02 | 1999-10-05 | Mccullough; Laughlin Gerard | Monocyclopentadienyl transition metal catalyst and olefin polymerization process |
| AU2411697A (en) * | 1996-05-03 | 1997-11-26 | Dsm N.V. | Process for the production of polymers containing cyclic olefins |
| AU2412597A (en) * | 1996-05-03 | 1997-11-26 | Dsm N.V. | Inverted polyolefin copolymers |
| TW370537B (en) * | 1996-05-03 | 1999-09-21 | Dsm Nv | Process for the preparation of an ethylene/α-olefin copolymer |
| AU2653097A (en) * | 1996-05-03 | 1997-11-26 | Dsm N.V. | Process for the production of functional polyolefins |
| EA199800975A1 (ru) * | 1996-05-03 | 1999-04-29 | Дсм Н.В. | СПОСОБ ПОЛУЧЕНИЯ ТЕРПОЛИМЕРА ЭТИЛЕНА, α-ОЛЕФИНА И ДИЕНА |
| NL1003016C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Gesubstitueerde pentadieenverbinding. |
| BR9709144A (pt) * | 1996-05-03 | 1999-08-03 | Dsm Nv | Processo para co-polimerização de uma olefina e um monômero aromático vinílico |
| NL1003014C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met tertiaire groepen gesubstitueerde cyclopentadieenverbinding. |
| US6124488A (en) * | 1996-05-03 | 2000-09-26 | Dsm N.V. | Cyclopentadiene compound substituted with branched alkyl groups |
| NL1003004C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met onderling verschillende groepen gesubstitueerde cyclopentadieen- verbinding. |
| NL1003007C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met vertakte alkylgroepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003006C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met vertakte alkylgroepen gesubstitueerde cyclopentadieenverbinding. |
| NL1003008C2 (nl) * | 1996-05-03 | 1997-11-06 | Dsm Nv | Met een heteroatoom-bevattende groep gesubstitueerde cyclopentadieen- verbinding. |
| US6117811A (en) * | 1996-05-03 | 2000-09-12 | Dsm N.V. | Cyclopentadiene compound substituted with linear groups |
| EA199800979A1 (ru) * | 1996-05-03 | 1999-04-29 | Дсм Н.В. | Каталитическая композиция на носителе и способ полимеризации олефиновых мономеров |
| BR9708971A (pt) * | 1996-05-03 | 1999-08-03 | Dsm Nv | Processo para a polimerização de alfa-olefinas |
| WO1997042237A1 (en) * | 1996-05-03 | 1997-11-13 | Dsm N.V. | A process for making polyolefins having broad molecular weight distributions |
| EP0901497B1 (de) * | 1996-05-14 | 2001-01-10 | The Dow Chemical Company | Yttrium enthaltend metallkomplexe und verfahren zur polymerisation von olefinen |
| CA2260003A1 (en) * | 1996-07-30 | 1998-02-05 | Studiengesellschaft Kohle Mbh | Catalysts containing organochromium compounds and their use for polymerising alkenes |
| ES2224266T3 (es) | 1996-08-08 | 2005-03-01 | Dow Global Technologies Inc. | Copmplejos metalicos que contienen ciclopentadienilo sustituido en la posicion 3 con un heteroatomo y procedimiento de polimerizacion de olefinas. |
| US6271322B1 (en) | 1996-10-02 | 2001-08-07 | Mccullough Laughlin Gerard | Monocyclopentadienyl transition metal catalyst and olefin polymerization process |
| US6720186B1 (en) | 1998-04-03 | 2004-04-13 | Symyx Technologies, Inc. | Method of research for creating and testing novel catalysts, reactions and polymers |
| EP0839835B1 (de) * | 1996-10-30 | 2000-02-16 | Repsol Quimica S.A. | Organometallische Katalysatoren für die Polymerisation und die Copolymerisation von Alpha-Olefinen |
| EP0919571A1 (de) * | 1997-12-01 | 1999-06-02 | Dsm N.V. | Katalysatorzusammensetzung enthaltend einen Komplex eines reduzierten Ubergangsmetalls und einen Co-Kalalysator |
| US6489261B1 (en) | 1997-12-01 | 2002-12-03 | Dsm N.V. | Catalyst composition comprising a reduced transition metal complex and a cocatalyst |
| US6362294B1 (en) | 1997-12-11 | 2002-03-26 | Exxon Mobil Chemical Patents Inc. | Reduced oxidation state transition metal compounds useful as olefin polymerization catalysts |
| DE19757524A1 (de) | 1997-12-23 | 1999-06-24 | Bayer Ag | eta-Komplex-Verbindungen |
| DE19809159A1 (de) | 1998-03-04 | 1999-09-09 | Bayer Ag | Metallorganische Verbindungen |
| DE19812881A1 (de) | 1998-03-24 | 1999-10-07 | Bayer Ag | Neue dendrimere Verbindungen, ein Verfahren zu deren Herstellung sowie deren Verwendung als Katalysatoren |
| US6100414A (en) * | 1998-04-02 | 2000-08-08 | Eastman Chemical Company | Cyclopentadienyl transition metal compounds useful as polymerization catalysts |
| KR100586118B1 (ko) | 1998-05-01 | 2006-06-02 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 올레핀 중합반응을 위한 삼좌 리간드-함유 금속 촉매 착체 |
| DE19837739A1 (de) | 1998-08-20 | 2000-02-24 | Bayer Ag | Katalysatorsystem auf Basis von Fulven-Cyclopentadienyl-Metallkomplexen |
| DE19837734C1 (de) | 1998-08-20 | 1999-12-23 | Bayer Ag | Verfahren zur Herstellung von Katalysatoren auf Basis von Fulven-Metallkomplexen |
| US6403773B1 (en) | 1998-09-30 | 2002-06-11 | Exxon Mobil Chemical Patents Inc. | Cationic group 3 catalyst system |
| US6465385B1 (en) | 1999-02-12 | 2002-10-15 | Sunoco, Inc. (R&M) | Zwitterionic polymerization catalyst |
| JP2000283243A (ja) * | 1999-03-29 | 2000-10-13 | Bando Chem Ind Ltd | 伝動ベルト |
| JP2002543208A (ja) | 1999-04-29 | 2002-12-17 | ザ ダウ ケミカル カンパニー | ビス（ｎ、ｎ−ジヒドロカルビルアミノ）置換シクロペンタジエン及びそれらの金属錯体 |
| DE60001557T2 (de) | 1999-05-13 | 2004-01-08 | Dow Global Technologies, Inc., Midland | Metallkomplexe mit heteroatom-enthaltende brücke für olefinpolymerisationsverfahren |
| DE60001558T2 (de) | 1999-05-13 | 2004-01-08 | Dow Global Technologies, Inc., Midland | Di- und tri-heteroatom-substituierte metall-indenylkomplexe |
| DE60020968T2 (de) | 1999-06-04 | 2006-05-11 | Dow Global Technologies, Inc., Midland | Borsubstituierte cyclopentadiene und metallkomplexe dieser liganden |
| US6437161B1 (en) | 1999-08-13 | 2002-08-20 | Basf Aktiengesellschaft | Monocyclopentadienyl complexes of chromium, molybdenum or tungsten |
| US6239062B1 (en) | 1999-09-02 | 2001-05-29 | Equistar Chemicals, L.P. | Olefin polymerization catalysts containing indolyl-amido ligands |
| ATE299898T1 (de) * | 1999-10-22 | 2005-08-15 | Univation Tech Llc | Katalysatorsysteme und deren verwendung in einem polymerisationsverfahren |
| US6825295B2 (en) | 1999-12-10 | 2004-11-30 | Dow Global Technologies Inc. | Alkaryl-substituted group 4 metal complexes, catalysts and olefin polymerization process |
| US6723675B1 (en) | 2000-05-25 | 2004-04-20 | Univation Technologies, Llc | Catalyst for the production of olefin polymers |
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| SG99905A1 (en) | 2000-06-21 | 2003-11-27 | Sumitomo Chemical Co | Transition metal compound, catalyst for addition polymerization, and process for producing addition polymer |
| GB0020613D0 (en) | 2000-08-21 | 2000-10-11 | Borealis Tech Oy | Catalysts |
| MXPA03003389A (es) | 2000-10-19 | 2004-01-26 | Exxonmobil Chem Patents Inc | Sistema catalizador del grupo 3 cationico. |
| KR20030082543A (ko) | 2000-10-25 | 2003-10-22 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 양이온성 촉매 시스템 |
| DE10236112B4 (de) * | 2001-08-13 | 2017-01-26 | Bando Chemical Industries, Ltd. | Kraftübertragungsriemen und Verfahren zu dessen Herstellung |
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| DE60137638D1 (de) | 2001-12-19 | 2009-03-26 | Borealis Tech Oy | Herstellung von geträgerten Katalysatoren für die Olefinpolymerisation |
| EP1323747A1 (de) | 2001-12-19 | 2003-07-02 | Borealis Technology Oy | Herstellung von Katalysatoren für die Olefinpolymerisation |
| US6703338B2 (en) * | 2002-06-28 | 2004-03-09 | Univation Technologies, Llc | Polymerization catalyst activators, method of preparing, and their use in polymerization processes |
| US20060089253A1 (en) * | 2002-08-13 | 2006-04-27 | Shahram Mihan | Monocyclopentadienyl complexes |
| ATE364047T1 (de) | 2002-08-22 | 2007-06-15 | Basell Polyolefine Gmbh | Monocyclopentadienylkomplexe |
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| DE3836059A1 (de) * | 1988-10-22 | 1990-05-03 | Hoechst Ag | Verfahren zur herstellung eines ethylen-propylen-copolymers |
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| US5374696A (en) * | 1992-03-26 | 1994-12-20 | The Dow Chemical Company | Addition polymerization process using stabilized reduced metal catalysts |
| GB9300934D0 (en) * | 1993-01-19 | 1993-03-10 | Bp Chem Int Ltd | Metallocene complexes |
| EP0722466B1 (de) * | 1993-10-08 | 1997-07-09 | The Dow Chemical Company | Verfahren zur herstellung von syndiotaktischen vinylaromatischen polymeren unter verwendung von reduzierten metallkationischen katalysatoren |
| CA2180558A1 (en) * | 1994-01-18 | 1995-07-20 | Thomas H. Newman | Process for preparation of reduced metal titanium complexes |
| US5512693A (en) * | 1994-12-07 | 1996-04-30 | The Dow Chemical Company | Preparation of titanium (II) or zirconium (II) complexes |
| US5747406A (en) * | 1997-01-10 | 1998-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Catalyst composition for the production of olefin polymers |
| US5780698A (en) * | 1997-03-31 | 1998-07-14 | Chevron Chemical Company | Olefin oligomerization catalyst and process employing and preparing same |
-
1995
- 1995-10-27 EP EP95936129A patent/EP0789718B1/de not_active Expired - Lifetime
- 1995-10-27 RU RU97108581A patent/RU2135522C1/ru active
- 1995-10-27 BR BR9509457A patent/BR9509457A/pt not_active Application Discontinuation
- 1995-10-27 JP JP8514470A patent/JPH10508055A/ja active Pending
- 1995-10-27 WO PCT/NL1995/000372 patent/WO1996013529A1/en not_active Ceased
- 1995-10-27 CN CN95197148A patent/CN1171794A/zh active Pending
- 1995-10-27 DE DE69502028T patent/DE69502028T2/de not_active Expired - Lifetime
- 1995-10-27 AT AT95936129T patent/ATE164858T1/de not_active IP Right Cessation
- 1995-10-27 ES ES95936129T patent/ES2116776T3/es not_active Expired - Lifetime
- 1995-10-27 AU AU38175/95A patent/AU3817595A/en not_active Abandoned
-
1997
- 1997-04-22 NO NO971843A patent/NO971843L/no not_active Application Discontinuation
- 1997-04-29 FI FI971823A patent/FI119430B/fi not_active IP Right Cessation
- 1997-04-30 US US08/841,672 patent/US5986029A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RU2135522C1 (ru) | 1999-08-27 |
| FI971823A0 (fi) | 1997-04-29 |
| NO971843D0 (no) | 1997-04-22 |
| US5986029A (en) | 1999-11-16 |
| EP0789718B1 (de) | 1998-04-08 |
| FI971823L (fi) | 1997-06-27 |
| BR9509457A (pt) | 1998-01-06 |
| NO971843L (no) | 1997-06-26 |
| MX9703254A (es) | 1997-10-31 |
| DE69502028T2 (de) | 1998-12-10 |
| CN1171794A (zh) | 1998-01-28 |
| DE69502028D1 (de) | 1998-05-14 |
| ES2116776T3 (es) | 1998-07-16 |
| AU3817595A (en) | 1996-05-23 |
| ATE164858T1 (de) | 1998-04-15 |
| EP0789718A1 (de) | 1997-08-20 |
| JPH10508055A (ja) | 1998-08-04 |
| WO1996013529A1 (en) | 1996-05-09 |
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