CA2411712C - Polycyclic, fused ring compounds, metal complexes and polymerization process - Google Patents
Polycyclic, fused ring compounds, metal complexes and polymerization process Download PDFInfo
- Publication number
- CA2411712C CA2411712C CA2411712A CA2411712A CA2411712C CA 2411712 C CA2411712 C CA 2411712C CA 2411712 A CA2411712 A CA 2411712A CA 2411712 A CA2411712 A CA 2411712A CA 2411712 C CA2411712 C CA 2411712C
- Authority
- CA
- Canada
- Prior art keywords
- hydrocarbyl
- substituted hydrocarbyl
- dimethyl
- group
- dihydrodibenzo
- 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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- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
- 239000002184 metal Chemical class 0.000 title claims abstract description 45
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 45
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 38
- 125000003367 polycyclic group Chemical group 0.000 title claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 41
- 125000004429 atom Chemical group 0.000 claims abstract description 40
- 239000003446 ligand Substances 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 32
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
- 150000001336 alkenes Chemical class 0.000 claims abstract description 21
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 112
- -1 hydrocarbyloxy Chemical group 0.000 claims description 103
- 239000000203 mixture Substances 0.000 claims description 58
- 239000003054 catalyst Substances 0.000 claims description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 230000003213 activating effect Effects 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 29
- 230000003647 oxidation Effects 0.000 claims description 25
- 238000007254 oxidation reaction Methods 0.000 claims description 25
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 230000007935 neutral effect Effects 0.000 claims description 21
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 150000004696 coordination complex Chemical class 0.000 claims description 16
- 150000004820 halides Chemical class 0.000 claims description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002879 Lewis base Substances 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001923 cyclic compounds Chemical class 0.000 claims description 10
- 150000007527 lewis bases Chemical class 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 125000000129 anionic group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 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 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 5
- 150000001993 dienes Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- WVJWYWLMNBSPDF-UHFFFAOYSA-N 4-nitro-N,N-dioctadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)C1=CC=C([N+]([O-])=O)C=C1 WVJWYWLMNBSPDF-UHFFFAOYSA-N 0.000 claims description 4
- GMHXCZMREGWHSW-UHFFFAOYSA-N N,N-dioctadecyl-4-(trifluoromethyl)aniline Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)C1=CC=C(C(F)(F)F)C=C1 GMHXCZMREGWHSW-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 238000012685 gas phase polymerization Methods 0.000 claims description 3
- WFJUDXWNVREHKE-UHFFFAOYSA-N 2,3,4,5,6-pentafluoro-N,N-dioctadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)C1=C(F)C(F)=C(F)C(F)=C1F WFJUDXWNVREHKE-UHFFFAOYSA-N 0.000 claims description 2
- NKCOXUPKACCMPR-UHFFFAOYSA-N 2,4,6-trifluoro-N,N-dioctadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)C1=C(F)C=C(F)C=C1F NKCOXUPKACCMPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- YWKBFXMDPRGXSX-UHFFFAOYSA-N N,2-dimethyl-N-[oxo(4-tetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2,5,7,9,11,14,16-octaenylmethyl)silyl]propan-2-amine 4-phenylbuta-1,3-dienylbenzene titanium(2+) Chemical compound [Ti+2].C=1C=CC=CC=1C=CC=CC1=CC=CC=C1.C1C2=CC=CC=C2C2=CC(C[Si](=O)N(C)C(C)(C)C)C=C2C2=CC=CC=C21 YWKBFXMDPRGXSX-UHFFFAOYSA-N 0.000 claims description 2
- ITHIGDMVZYJBDO-UHFFFAOYSA-N N-methyl-N-[oxo(3-tetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2,5,7,9,11,14,16-octaenylmethyl)silyl]cyclohexanamine penta-1,3-diene titanium(2+) Chemical compound [Ti+2].CC=CC=C.C12=CC=CC=C2CC2=CC=CC=C2C=2C1=CCC=2C[Si](=O)N(C)C1CCCCC1 ITHIGDMVZYJBDO-UHFFFAOYSA-N 0.000 claims description 2
- KRQBFAFGLLFSGW-UHFFFAOYSA-L N-methyl-N-[oxo(3-tetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2,5,7,9,11,14,16-octaenylmethyl)silyl]cyclohexanamine titanium(4+) dichloride Chemical compound [Cl-].[Cl-].[Ti+4].C12=CC=CC=C2CC2=CC=CC=C2C=2C1=CCC=2C[Si](=O)N(C)C1CCCCC1 KRQBFAFGLLFSGW-UHFFFAOYSA-L 0.000 claims description 2
- ASXBPROXZUQYBG-UHFFFAOYSA-N N-methyl-N-[oxo(4-tetracyclo[12.4.0.02,6.07,12]octadeca-1(18),2,5,7,9,11,14,16-octaenylmethyl)silyl]cyclohexanamine 4-phenylbuta-1,3-dienylbenzene titanium(2+) Chemical compound [Ti+2].C=1C=CC=CC=1C=CC=CC1=CC=CC=C1.C1=C(C2=CC=CC=C2CC2=CC=CC=C22)C2=CC1C[Si](=O)N(C)C1CCCCC1 ASXBPROXZUQYBG-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- RBUPWCCCYMXZET-UHFFFAOYSA-L [Cl-].[Cl-].[Ti+4].C1=C(C2=CC=CC=C2CC2=CC=CC=C22)C2=CC1C[Si](=O)N(C)C1CCCCC1 Chemical compound [Cl-].[Cl-].[Ti+4].C1=C(C2=CC=CC=C2CC2=CC=CC=C22)C2=CC1C[Si](=O)N(C)C1CCCCC1 RBUPWCCCYMXZET-UHFFFAOYSA-L 0.000 claims description 2
- FQVAVYDYXCJFKX-UHFFFAOYSA-L [Cl-].[Cl-].[Ti+4].C1C2=CC=CC=C2C2=CC(C[Si](=O)N(C)C(C)(C)C)C=C2C2=CC=CC=C21 Chemical compound [Cl-].[Cl-].[Ti+4].C1C2=CC=CC=C2C2=CC(C[Si](=O)N(C)C(C)(C)C)C=C2C2=CC=CC=C21 FQVAVYDYXCJFKX-UHFFFAOYSA-L 0.000 claims description 2
- SZVCTQJKQRBYQT-UHFFFAOYSA-N [Ti+2].C=1C=CC=CC=1C=CC=CC1=CC=CC=C1.C12=CC=CC=C2CC2=CC=CC=C2C=2C1=CCC=2C[Si](=O)N(C)C1CCCCC1 Chemical compound [Ti+2].C=1C=CC=CC=1C=CC=CC1=CC=CC=C1.C12=CC=CC=C2CC2=CC=CC=C2C=2C1=CCC=2C[Si](=O)N(C)C1CCCCC1 SZVCTQJKQRBYQT-UHFFFAOYSA-N 0.000 claims description 2
- SYYMETDPRQLVFE-UHFFFAOYSA-N [Ti+2].C=1C=CC=CC=1C=CC=CC1=CC=CC=C1.C1C2=CC=CC=C2C2=C(C[Si](=O)N(C)C(C)(C)C)CC=C2C2=CC=CC=C21 Chemical compound [Ti+2].C=1C=CC=CC=1C=CC=CC1=CC=CC=C1.C1C2=CC=CC=C2C2=C(C[Si](=O)N(C)C(C)(C)C)CC=C2C2=CC=CC=C21 SYYMETDPRQLVFE-UHFFFAOYSA-N 0.000 claims description 2
- SPPNFMHAQMHCKJ-UHFFFAOYSA-N [Ti+2].CC=CC=C.C1=C(C2=CC=CC=C2CC2=CC=CC=C22)C2=CC1C[Si](=O)N(C)C1CCCCC1 Chemical compound [Ti+2].CC=CC=C.C1=C(C2=CC=CC=C2CC2=CC=CC=C22)C2=CC1C[Si](=O)N(C)C1CCCCC1 SPPNFMHAQMHCKJ-UHFFFAOYSA-N 0.000 claims description 2
- RLIGXPYOLZDHGO-UHFFFAOYSA-N [Ti+2].CC=CC=C.C1C2=CC=CC=C2C2=C(C[Si](=O)N(C)C(C)(C)C)CC=C2C2=CC=CC=C21 Chemical compound [Ti+2].CC=CC=C.C1C2=CC=CC=C2C2=C(C[Si](=O)N(C)C(C)(C)C)CC=C2C2=CC=CC=C21 RLIGXPYOLZDHGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- DSGBCNOCBIBUCQ-UHFFFAOYSA-L [Cl-].[Cl-].[Ti+4].C1C2=CC=CC=C2C2=C(C[Si](=O)N(C)C(C)(C)C)CC=C2C2=CC=CC=C21 Chemical compound [Cl-].[Cl-].[Ti+4].C1C2=CC=CC=C2C2=C(C[Si](=O)N(C)C(C)(C)C)CC=C2C2=CC=CC=C21 DSGBCNOCBIBUCQ-UHFFFAOYSA-L 0.000 claims 1
- POUDSGSEUKWIDN-UHFFFAOYSA-N [Ti+2].CC=CC=C.C1C2=CC=CC=C2C2=CC(C[Si](=O)N(C)C(C)(C)C)C=C2C2=CC=CC=C21 Chemical compound [Ti+2].CC=CC=C.C1C2=CC=CC=C2C2=CC(C[Si](=O)N(C)C(C)(C)C)C=C2C2=CC=CC=C21 POUDSGSEUKWIDN-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 239000002685 polymerization catalyst Substances 0.000 abstract description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 36
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 34
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 33
- 239000005977 Ethylene Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 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 32
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 150000001450 anions Chemical class 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 150000002431 hydrogen Chemical class 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 239000003638 chemical reducing agent Substances 0.000 description 11
- 239000003085 diluting agent Substances 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 6
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical class C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- JDEDKRLRGDEWKM-UHFFFAOYSA-N n,n-dioctadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)C1=CC=CC=C1 JDEDKRLRGDEWKM-UHFFFAOYSA-N 0.000 description 6
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- 239000007848 Bronsted acid Substances 0.000 description 4
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 4
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ZDMNAVSJDAXTBD-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)alumane 2-undecyl-4,5-dihydro-1H-imidazole Chemical compound CCCCCCCCCCCC1=NCCN1.FC1=C(F)C(F)=C(F)C(F)=C1[Al](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F.FC1=C(F)C(F)=C(F)C(F)=C1[Al](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F ZDMNAVSJDAXTBD-UHFFFAOYSA-N 0.000 description 1
- QEPDENOFSCCDEA-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)alumane;2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1.FC1=C(F)C(F)=C(F)C(F)=C1[Al](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F.FC1=C(F)C(F)=C(F)C(F)=C1[Al](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QEPDENOFSCCDEA-UHFFFAOYSA-N 0.000 description 1
- NVBHDPLKAHDQDC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)borane;2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1.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.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 NVBHDPLKAHDQDC-UHFFFAOYSA-N 0.000 description 1
- MDYARPNTSPYOED-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)borane;2-undecyl-4,5-dihydro-1h-imidazole Chemical compound CCCCCCCCCCCC1=NCCN1.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.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 MDYARPNTSPYOED-UHFFFAOYSA-N 0.000 description 1
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical group C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
- C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
-
- 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
- C08F2420/00—Metallocene catalysts
- C08F2420/02—Cp or analog bridged to a non-Cp X anionic donor
-
- 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
- C08F2420/00—Metallocene catalysts
- C08F2420/05—Cp or analog where at least one of the carbon atoms of the coordinating ring is replaced by a heteroatom
-
- 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21545600P | 2000-06-30 | 2000-06-30 | |
| US60/215,456 | 2000-06-30 | ||
| PCT/US2001/018808 WO2002002577A1 (en) | 2000-06-30 | 2001-06-12 | Polycyclic, fused ring compounds, metal complexes and polymerization process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2411712A1 CA2411712A1 (en) | 2002-01-10 |
| CA2411712C true CA2411712C (en) | 2011-01-25 |
Family
ID=22803050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2411712A Expired - Fee Related CA2411712C (en) | 2000-06-30 | 2001-06-12 | Polycyclic, fused ring compounds, metal complexes and polymerization process |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6613921B2 (enExample) |
| EP (1) | EP1299405B1 (enExample) |
| JP (1) | JP4964389B2 (enExample) |
| KR (1) | KR20030013479A (enExample) |
| AT (1) | ATE431353T1 (enExample) |
| AU (1) | AU2001275462A1 (enExample) |
| CA (1) | CA2411712C (enExample) |
| DE (1) | DE60138708D1 (enExample) |
| WO (1) | WO2002002577A1 (enExample) |
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-
2001
- 2001-06-12 CA CA2411712A patent/CA2411712C/en not_active Expired - Fee Related
- 2001-06-12 JP JP2002507829A patent/JP4964389B2/ja not_active Expired - Lifetime
- 2001-06-12 AU AU2001275462A patent/AU2001275462A1/en not_active Abandoned
- 2001-06-12 WO PCT/US2001/018808 patent/WO2002002577A1/en not_active Ceased
- 2001-06-12 EP EP01942174A patent/EP1299405B1/en not_active Expired - Lifetime
- 2001-06-12 KR KR1020027018046A patent/KR20030013479A/ko not_active Ceased
- 2001-06-12 US US09/879,463 patent/US6613921B2/en not_active Expired - Lifetime
- 2001-06-12 AT AT01942174T patent/ATE431353T1/de not_active IP Right Cessation
- 2001-06-12 DE DE60138708T patent/DE60138708D1/de not_active Expired - Lifetime
-
2003
- 2003-05-13 US US10/437,161 patent/US6800701B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE60138708D1 (de) | 2009-06-25 |
| WO2002002577A1 (en) | 2002-01-10 |
| JP4964389B2 (ja) | 2012-06-27 |
| US20030216529A1 (en) | 2003-11-20 |
| JP2004505019A (ja) | 2004-02-19 |
| KR20030013479A (ko) | 2003-02-14 |
| US6800701B2 (en) | 2004-10-05 |
| ATE431353T1 (de) | 2009-05-15 |
| US6613921B2 (en) | 2003-09-02 |
| CA2411712A1 (en) | 2002-01-10 |
| AU2001275462A1 (en) | 2002-01-14 |
| US20020062011A1 (en) | 2002-05-23 |
| EP1299405A1 (en) | 2003-04-09 |
| EP1299405B1 (en) | 2009-05-13 |
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