CA2440985A1 - Metal complexes containing acetylenic ligands, polymerization catalysts and addition polymerization process - Google Patents
Metal complexes containing acetylenic ligands, polymerization catalysts and addition polymerization process Download PDFInfo
- Publication number
- CA2440985A1 CA2440985A1 CA002440985A CA2440985A CA2440985A1 CA 2440985 A1 CA2440985 A1 CA 2440985A1 CA 002440985 A CA002440985 A CA 002440985A CA 2440985 A CA2440985 A CA 2440985A CA 2440985 A1 CA2440985 A1 CA 2440985A1
- Authority
- CA
- Canada
- Prior art keywords
- bis
- acetylene
- trimethylsilyl
- hydrocarbyl
- dimethylsilanamide titanium
- 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.)
- Abandoned
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 36
- 239000002184 metal Substances 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims description 37
- 239000003446 ligand Substances 0.000 title claims description 18
- 238000012644 addition polymerization Methods 0.000 title claims description 10
- 239000002685 polymerization catalyst Substances 0.000 title description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 23
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract 3
- -1 hydrocarbyloxy Chemical group 0.000 claims description 53
- 239000003054 catalyst Substances 0.000 claims description 50
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 45
- 239000000178 monomer Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 33
- 238000006116 polymerization reaction Methods 0.000 claims description 33
- 230000003213 activating effect Effects 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000004696 coordination complex Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 15
- 230000007935 neutral effect Effects 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000002879 Lewis base Substances 0.000 claims description 10
- 150000007527 lewis bases Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- OZLRXXUVWUZUKQ-UHFFFAOYSA-N titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C OZLRXXUVWUZUKQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- ICVKHBQMJWENEI-UHFFFAOYSA-N 3-[[[cyclohexyl(methyl)amino]-oxosilyl]methyl]-N,N-dimethyl-3H-inden-1-amine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C12=CC=CC=C2C(N(C)C)=CC1C[Si](=O)N(C)C1CCCCC1 ICVKHBQMJWENEI-UHFFFAOYSA-N 0.000 claims description 4
- HUEBRPHSLWDSOW-UHFFFAOYSA-N 3-[[[tert-butyl(methyl)amino]-oxosilyl]methyl]-N,N-dimethyl-3H-inden-1-amine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C1=CC=C2C(N(C)C)=CC(C[Si](=O)N(C)C(C)(C)C)C2=C1 HUEBRPHSLWDSOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 4
- 238000012685 gas phase polymerization Methods 0.000 claims description 4
- 125000003114 inden-1-yl group Chemical group [H]C1=C([H])C([H])(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- DSZAGXGWCYEVEF-UHFFFAOYSA-N C[Si](C#C[Si](C)(C)C)(C)C.[Ti+2].CC=1C(=C(C(C1)(C)C[Si](=O)N(C1CCCCC1)C)C)C Chemical group C[Si](C#C[Si](C)(C)C)(C)C.[Ti+2].CC=1C(=C(C(C1)(C)C[Si](=O)N(C1CCCCC1)C)C)C DSZAGXGWCYEVEF-UHFFFAOYSA-N 0.000 claims description 2
- WCQVRAXJXHXCKX-UHFFFAOYSA-N N,2-dimethyl-N-[(2-methyl-4-naphthalen-1-yl-1H-inden-1-yl)methyl-oxosilyl]propan-2-amine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C1=CC=C2C(C3=CC=CC4=C3C=C(C)C4C[Si](=O)N(C)C(C)(C)C)=CC=CC2=C1 WCQVRAXJXHXCKX-UHFFFAOYSA-N 0.000 claims description 2
- WPLAUTNZJRLJEM-UHFFFAOYSA-N N,2-dimethyl-N-[(2-methyl-4-phenyl-1H-inden-1-yl)methyl-oxosilyl]propan-2-amine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.CC(C)(C)N(C)[Si](=O)CC1C(C)=CC2=C1C=CC=C2C1=CC=CC=C1 WPLAUTNZJRLJEM-UHFFFAOYSA-N 0.000 claims description 2
- MDXOTIBDLDUBCG-UHFFFAOYSA-N N,2-dimethyl-N-[oxo(s-indacen-1-ylmethyl)silyl]propan-2-amine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C1=C2C=CC=C2C=C2C(C[Si](=O)N(C)C(C)(C)C)=CC=C21 MDXOTIBDLDUBCG-UHFFFAOYSA-N 0.000 claims description 2
- LFQKKUXYSATWGA-UHFFFAOYSA-N N-[1H-inden-1-ylmethyl(oxo)silyl]-N,2-dimethylpropan-2-amine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C1=CC=C2C(C[Si](=O)N(C)C(C)(C)C)C=CC2=C1 LFQKKUXYSATWGA-UHFFFAOYSA-N 0.000 claims description 2
- OPFWRPXXWSYYCF-UHFFFAOYSA-N N-[1H-inden-1-ylmethyl(oxo)silyl]-N-methylcyclohexanamine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C1=CC2=CC=CC=C2C1C[Si](=O)N(C)C1CCCCC1 OPFWRPXXWSYYCF-UHFFFAOYSA-N 0.000 claims description 2
- ZQFQMRDBLQNUOU-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 titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C1=C(C2=CC=CC=C2CC2=CC=CC=C22)C2=CC1C[Si](=O)N(C)C1CCCCC1 ZQFQMRDBLQNUOU-UHFFFAOYSA-N 0.000 claims description 2
- ARWPXWDYWZFKKY-UHFFFAOYSA-N N-methyl-N-[oxo(s-indacen-1-ylmethyl)silyl]cyclohexanamine titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C=1C=C2C=C3C=CC=C3C=C2C=1C[Si](=O)N(C)C1CCCCC1 ARWPXWDYWZFKKY-UHFFFAOYSA-N 0.000 claims description 2
- SAKRPKAURNGQPQ-UHFFFAOYSA-N [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.CC1=CC(C(=CC=C2)C=3C4=CC=CC=C4C=CC=3)=C2C1C[Si](=O)N(C)C1CCCCC1 Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.CC1=CC(C(=CC=C2)C=3C4=CC=CC=C4C=CC=3)=C2C1C[Si](=O)N(C)C1CCCCC1 SAKRPKAURNGQPQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- LDVJEFNTDAATDZ-UHFFFAOYSA-N C[Si](C#C[Si](C)(C)C)(C)C.[Ti+2].CC=1C(=C(C(C1)(C)C[Si](=O)N(C(C)(C)C)C)C)C Chemical group C[Si](C#C[Si](C)(C)C)(C)C.[Ti+2].CC=1C(=C(C(C1)(C)C[Si](=O)N(C(C)(C)C)C)C)C LDVJEFNTDAATDZ-UHFFFAOYSA-N 0.000 claims 1
- WRBYIIJMCRHQCQ-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 titanium(2+) trimethyl(2-trimethylsilylethynyl)silane Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.C1C2=CC=CC=C2C2=CC(C[Si](=O)N(C)C(C)(C)C)C=C2C2=CC=CC=C21 WRBYIIJMCRHQCQ-UHFFFAOYSA-N 0.000 claims 1
- HAZIRYKMBVATEY-UHFFFAOYSA-N [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1C[Si](=O)N(C)C1CCCCC1 Chemical group [Ti+2].C[Si](C)(C)C#C[Si](C)(C)C.CC1=CC(C(=CC=C2)C=3C=CC=CC=3)=C2C1C[Si](=O)N(C)C1CCCCC1 HAZIRYKMBVATEY-UHFFFAOYSA-N 0.000 claims 1
- 101150068906 snr-6 gene Proteins 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 35
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 33
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 31
- 239000005977 Ethylene Substances 0.000 description 31
- 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 31
- 229920000642 polymer Polymers 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 22
- 150000001450 anions Chemical class 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 17
- 150000001336 alkenes Chemical class 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 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 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000003085 diluting agent Substances 0.000 description 10
- 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 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000047 product 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
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 6
- 229910052796 boron Inorganic materials 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
- 150000007517 lewis acids Chemical class 0.000 description 6
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical class C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical class [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 150000002738 metalloids Chemical group 0.000 description 3
- JDEDKRLRGDEWKM-UHFFFAOYSA-N n,n-dioctadecylaniline Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)C1=CC=CC=C1 JDEDKRLRGDEWKM-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- KCMTVIZYKDBFFS-UHFFFAOYSA-N n-hexadecyl-n-methylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCC KCMTVIZYKDBFFS-UHFFFAOYSA-N 0.000 description 3
- KUFYUMSBZMUWAN-UHFFFAOYSA-N n-methyl-n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCC KUFYUMSBZMUWAN-UHFFFAOYSA-N 0.000 description 3
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- SCABQASLNUQUKD-UHFFFAOYSA-N silylium Chemical compound [SiH3+] SCABQASLNUQUKD-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 2
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical class C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 2
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- 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
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Classifications
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- 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
- 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
- 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
- C08F10/02—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
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—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
- 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
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- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27710501P | 2001-03-19 | 2001-03-19 | |
| US60/277,105 | 2001-03-19 | ||
| PCT/US2002/003702 WO2002074779A1 (en) | 2001-03-19 | 2002-02-08 | Metal complexes containing acetylenic ligands, polymerization catalysts and addition polymerization process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2440985A1 true CA2440985A1 (en) | 2002-09-26 |
Family
ID=23059427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002440985A Abandoned CA2440985A1 (en) | 2001-03-19 | 2002-02-08 | Metal complexes containing acetylenic ligands, polymerization catalysts and addition polymerization process |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6872844B2 (enExample) |
| EP (1) | EP1373281B1 (enExample) |
| JP (1) | JP2004530664A (enExample) |
| CA (1) | CA2440985A1 (enExample) |
| DE (1) | DE60205597T2 (enExample) |
| WO (1) | WO2002074779A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003049856A1 (en) * | 2001-12-05 | 2003-06-19 | Exxonmobil Chemical Patents Inc. | Bulky borate activators |
| US6703338B2 (en) | 2002-06-28 | 2004-03-09 | Univation Technologies, Llc | Polymerization catalyst activators, method of preparing, and their use in polymerization processes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9407034A (pt) * | 1993-06-24 | 1996-03-19 | Dow Chemical Co | Complexos de titânio ( I) ou zircônio (II) e catalisadores de polimerização por adição dos mesmos |
-
2002
- 2002-02-08 CA CA002440985A patent/CA2440985A1/en not_active Abandoned
- 2002-02-08 WO PCT/US2002/003702 patent/WO2002074779A1/en not_active Ceased
- 2002-02-08 US US10/468,531 patent/US6872844B2/en not_active Expired - Fee Related
- 2002-02-08 EP EP02703354A patent/EP1373281B1/en not_active Expired - Lifetime
- 2002-02-08 JP JP2002573788A patent/JP2004530664A/ja not_active Abandoned
- 2002-02-08 DE DE60205597T patent/DE60205597T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60205597D1 (de) | 2005-09-22 |
| EP1373281A1 (en) | 2004-01-02 |
| JP2004530664A (ja) | 2004-10-07 |
| WO2002074779A1 (en) | 2002-09-26 |
| DE60205597T2 (de) | 2006-05-18 |
| EP1373281B1 (en) | 2005-08-17 |
| US20040082769A1 (en) | 2004-04-29 |
| US6872844B2 (en) | 2005-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |