TW387908B - Highly soluble olefin polymerization catalyst activator - Google Patents
Highly soluble olefin polymerization catalyst activator Download PDFInfo
- Publication number
- TW387908B TW387908B TW086103868A TW86103868A TW387908B TW 387908 B TW387908 B TW 387908B TW 086103868 A TW086103868 A TW 086103868A TW 86103868 A TW86103868 A TW 86103868A TW 387908 B TW387908 B TW 387908B
- Authority
- TW
- Taiwan
- Prior art keywords
- bis
- catalyst activator
- group
- borate
- catalyst
- Prior art date
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- 239000012190 activator Substances 0.000 title claims abstract description 30
- 150000001336 alkenes Chemical class 0.000 title claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 6
- 239000002685 polymerization catalyst Substances 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims abstract description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 150000001450 anions Chemical class 0.000 claims abstract description 20
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims abstract description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 8
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 metal complex compound Chemical class 0.000 claims description 123
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- 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 claims description 29
- 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 claims description 28
- 238000011049 filling Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 235000015170 shellfish Nutrition 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000003760 tallow Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000004711 α-olefin Substances 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims description 5
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 claims description 4
- 238000007639 printing Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- VAUMWVVODNTNEA-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)methoxyboronic acid Chemical compound FC1=C(C(=C(C(=C1COB(O)O)F)F)F)F VAUMWVVODNTNEA-UHFFFAOYSA-N 0.000 claims 2
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 claims 2
- 101100229939 Mus musculus Gpsm1 gene Proteins 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 239000007848 Bronsted acid Substances 0.000 abstract description 4
- 150000001768 cations Chemical class 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 36
- 239000010936 titanium Substances 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 17
- 229910052719 titanium Inorganic materials 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 12
- 230000002079 cooperative effect Effects 0.000 description 12
- 239000003426 co-catalyst Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
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- GWAGOKMZTSJCBP-UHFFFAOYSA-N C[SiH](C)[Ti] Chemical compound C[SiH](C)[Ti] GWAGOKMZTSJCBP-UHFFFAOYSA-N 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- 229910052796 boron Inorganic materials 0.000 description 8
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- 229910052726 zirconium Inorganic materials 0.000 description 7
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 5
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- 239000000178 monomer Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910052702 rhenium Inorganic materials 0.000 description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 5
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 230000003287 optical effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WQIQNKQYEUMPBM-UHFFFAOYSA-N pentamethylcyclopentadiene Chemical compound CC1C(C)=C(C)C(C)=C1C WQIQNKQYEUMPBM-UHFFFAOYSA-N 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical class [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-O tert-butylammonium Chemical compound CC(C)(C)[NH3+] YBRBMKDOPFTVDT-UHFFFAOYSA-O 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- BNOPYGRAXZULSM-UHFFFAOYSA-N tri(tetradecyl)phosphane Chemical compound CCCCCCCCCCCCCCP(CCCCCCCCCCCCCC)CCCCCCCCCCCCCC BNOPYGRAXZULSM-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-O tridecylazanium Chemical compound CCCCCCCCCCCCC[NH3+] ABVVEAHYODGCLZ-UHFFFAOYSA-O 0.000 description 1
- 150000003649 tritium Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
- C08F4/603—Component covered by group C08F4/60 with a metal or compound covered by group C08F4/44 other than an organo-aluminium compound
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/01—Additive used together with the catalyst, excluding compounds containing Al or B
-
- 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
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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
- 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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- 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
Description
經濟部中央梂準局貝工消费合作社印裝 A7 B7 五、發明説明（） 本發明係Μ於一催化劑之活化劑。較待別地是本發明 係期於一催化劑之活化劑特別適用於爲α-烯垤聚合反應 的溶掖聚合反應方法中。此一栝化劑特別利於用在一連鑲 的溶液聚合反應方法中，其中催化劑、催化劑活化劑、和 至少一可聚合的單髏連鑲加入一於溶液聚合反瞍狀況下的 反應器中，並且聚合產物連编從此反應中移出。 在此技已知话化齊格勒纳搭聚合作用催化劑，尤其是 包含具非定域鍵結Κ位體基之第4族金屬錯合物之催 化琍，藉由可轉移一質子之布倫斯特酸鹽Μ形成逭些第4 族金屬錯合物的陽離子衍生物。較佳的布倫斯特酸鹽爲含 有一非配位陰離子之化合物Μ能穩定，味H第4滅石屬陽 離子，尤其是四（五氟笨基）硼睃盥。此爲一棰離子活化 劑之布倫斯特酸鹽活化剤的例示，係掲露於專利US-A- | < 5,198,401，l!S-A-5，132,380, US-A-5, 470,927,和 US-Λ-5,153,157中的質子化的銨、卷幻、或縝盏。 由於逭些活化劑是完全離子化且其相對應之陰離子是 高度未配位，這樣的活化劑可非常有效的用來做烯垤的聚 合反應催化劑之活化劑。然而缺酤是由於其是離子性Η類 ，道種话化劑在脂肪族之硪氳化合物中棰為難溶並且僅能 少量溶解在芳香族之溶劑中》—般想要在脂肪族的碘氦化 合物溶劑中進行大部份的α -烯烴的聚合 反應r因為 此類溶劑和單體之相容性以及為了在聚合物產物中減少芳 香族碘氳化合物之含量。通常離子鹽活化剤以在芳番族溶 劑，如甲苯中的溶液形式加入此聚合反應過程。卽使使用 本紙張尺度逋用中國國家標準（CNS ) A4規格（210X297公釐） --------「^.------ΐτ------| (請先閲讀背面之注意事項再填寫本頁)；， 經濟部中央標準局負工消費合作社印裝 A7 _ B7 五、發明説明（2 )
I 少置的此種芳香族溶劑Μ達此目的也是不欲的，因爲它必 須Μ去揮發的步软中移除且由其他揮發性的成份中分離， 此方法會對任何商業製程增加相當成本與褀雑性。除此之 外，前述的離子共催化劑通常存在於一油性的、難於應付 的物質形式，而不易於處理及計量、或是準確地合併於反 應物中。 @此，預期是苔可提供一可用於溶液聚合反應的離子 性催化劑之栝化劑，其係使用脂肪族之溶劑，其包括缩合 的a-烯垤單體。此外欲提供一棰新式的離子性催化劑之 活化劑，其特別適用於連續的溶液聚合反應，其中該话化 劑特定量之控制添加是需要的。 本發明現提供了一催化劑的话化劑，其包含一能供给 一質子之布倫斯恃酸的陽離子，Μ及一惰性、相容、未配 位的陰離子，其特激在於在25¾下在己烷、環己院、或甲 基環己烷中之溶解度至少為5重量百分比，較佳至少7.5 重量百分比。除此之外本發明提供了一 cc烯烴之溶液聚合 反應方法，其包含至少一 σ-烯烴，選擇地在一惰性脂肪 族、脂瑁族或是芳香族的硪氫化合物存在下，與包含前述 催化劑活化劑的催化劑条統接觸。 使用前述的催化劑栝化劑，可得到改良的催化劑活性 。較特別地是可得到增加的催化劑效率及聚合反應速率， 待別是在溶液聚合反應狀況下，尤其是連續的溶液聚合作 用狀況下。 於此所有提到持定族群的元素是參考CRC press, Inc., 本紙張尺度逋用中國國家揉準（CNS ) A4規格（2丨OX297公釐） --------(政------IT------Q (請先閱讀背面之注意事項再填寫本頁)，， ， -5 - A7 B7 五、發明説明（3 ) 1989出版及掬有箸作描之元素遇期表。同時所有提及的元 素族或為示於該元素遇期表採用IUPAC条統之族编號所示 之族。 本發明之催化劑话化劑之進一步特激在於下列方式。 較桂的陰離子具有一單一配位錯合物*其包含有一承受電 荷之金羼或類金屬核心，於其上陰離子可平衡當兩棰成份 組合時所形成栝化催化劑（金屬陽離子）的電荷。同時， 該險離子必須有足夠的活性Μ被烯類、雙烯類及乙炔類未飽 和化合物或是中性路易士鹸如醚、胺、或丨胃等所取代。適 當的金屬包括（但非局限於）鋁、金、和白金。適當的准 金屬包括（但非局限於）硼、硫、和矽。包含具單一金旖 或准金屬原子的配位錯合物之陰離子的化合物，當然爲已 知且有許多，特別是在陰離子部份有單一硼原子的化合物 為商業上可Μ買的到。因此該單一硼原子的化合物是較好 的0 本發明的共催化劑可由下列的通式：+ 表示，其中： L-是一中性的路易士鹼； 經濟部中央梂準扃負工消费合作社印装 (請先閱讀背面之注意事項再填寫本頁)丨 α·-Η>*是一布倫斯特酸； Α-·是一未配位，具電荷d-的相容陰離子，且(1是從1 至3的整數。 具化學式Arf-之適當陰離子的例子包括如下式位阻遮 蔽的燹硼陰離子 本科叙通《|由WSJ搴揉舉4GNSa>A4.iJMM 秘#4、 經濟部中央標準局貝工消費合作社印裂 Λ7 B7 五、發明説明（4 ) . -, · — ·- — X1 / Ατ、Β、 /BAr、-CS2 其中： S是烷基、氟化烷基、芳香烴基或氟化芳香烴基（又 兩S基表示另外之氫），
Ar?是氟化芳香烴基，且 X1是氳或是鹵化物。 此雙硼陰離子掲露於專利US-A-5,447,895中。 A·*·陰離子額外的例子為具分子式[^1’》-(^’]--之陰離 子，其中： K是從1至3的整數； η’是從2至6的整數； η ’ -k = d ; Μ’是從元素週期表中第13族中遼出的元素；且 Q在每一狀況各自為選自氫化物、雙烷基醯胺基、鹵 化物、烷氧化物、芳香族氧化物、羰基、Μ及豳取代羰氳 ，該Q具最多至20_磺原子且條件為在不超過一次狀況下Q 爲鹵化物。 在一較佳也實施例中，d是1，亦即相對離子有箪一 負霣荷且其式為A·。在本發明中特別有用之含有硼的活化 共催化劑為以下列通式表示：[BQ’ *]-,其中： L·是一含有#、碕或磷的中性路易士鹼； B是在氧化態為3之硼；且 本紙張尺度適用中國國家標準（CNS ) A4規格（2丨0X297公楚） (锖先閲婧背面之注意事項再填寫本頁) 裝
，1T 經濟部中央標準局負工消費合作社印製 Λ7 B7 五、發明説明（5 ) Q’是一氟化的C丨·ae氳磺基群。 最好是(3¾每一狀況中氟化芳番基，尤其是一五氟苯 基。 一般而言，本發明中偁化劑话化劑在脂肪族化合物中 溶解度之增加是在布倫斯特酸L中併入一或多親油基如長 鏈烷基；長鍵烯基；或鹵基、烷氧基、胺基、矽烷基或鴯 烷基取代之長鋪烷基或烯基。此"長鋪”表示在每一基圃 中有10異50傾非氫原子，最好是不分支的形式。較好的此 L基含有1至3 C^-4。η-烷基有總數為12至100値碘原 子，最好能有2 烷基群及總數為21至90磺原子。 親油基的存在相信是讓活性劑較易溶解於脂肪族液體中， 因而改善催化劑活化性之效率。催化劑之活化劑可包含有 不同長度親油基之混合物。例如，一適當的栝化物是質子 化的銨鹽，其衍生自商業上可寅到的包含有兩値Cm、Cts 或Cie烷基和一甲基涯合物的畏鍵胺類。此胺類可得自 Witco Corp.之商標名 KemaiiiineTM T9701，Μ 及得自 Akzo-Nobel之商摞名Arneen™ M2HT。本發明共催化劑與先前所 無之已知共催化劑量相較在基於金屬錯合物的里以一較低 灌度使用，同時保持相等或改良的催化劑效率。 可用來做本發明中離子活化共催{b劑的硼化合物之例 示於下，但非局限於此，例如： 癸基二（甲基）銨四（五氣苯基）砸酸鹽， 十二基二（甲基）銨四（五氟苯基）硼睃發， +四基二（甲基）銨四（五氟苯基）硼酸鹽， 本紙張尺度適用中國國家標準（CNS > A4規格（210X297公釐） --------「裝-- ' I * * - V: (請先閲讀背扃/y隹填"本t
,1T .^Α, -8 - Λ7 ^^___B7 _____ 五、發明説明（6 ) " 十六基二（甲基）銨四（五氟苯基）硼酸鹽， 十八基二（甲基）铵四（五氟苯基）硼睃鹽， 二十基二（甲基）銨四（五氟苯基）硼酸鹽， 甲基二癸基銨四（五氟苯基）砸酸鹽， 甲基雙十二基銨四（五氟苯基）硼酸發， 甲基雙十四基銨四（五氟苯基）硼酸鹽， 甲基雙十六基铵四（五氟苯基）硼酸鹽， 甲基雙十八基銨四（五氟苯基）硼酸鹽， 甲基雙二+基銨四（五氟苯基）硼酸鹽* 三癸基銨四（五氟苯基）硼酸鹽， 三（十二基）銨四（五氟苯基）硼睃鹽， 三（十四基）銨四（五氟苯基）硼酸鹽， 三（十六基）銨四（五氟苯基）硼酸鹽， 三（+八基）銨四（五氟苯基）硼酸鹽* 三（二十基）铵四（五氟苯基）硼酸鹽， 癸基二丁基銨四（五氟苯基）硼酸鹽， 十二基二丁基銨四（五氟苯基）硼酸鹽， .經濟部中央標準局貝工消費合作社印製 十八基二丁基銨四（五氟苯基）硼酸鹽， Ν,Ν-雙十二烷基苯胺锚四（五氟苯基）硼酸鹽， Ν-甲基-Ν-+二烷基笨胺錤四（五氟苯基）硼酸S, Ν,Ν-二（十八基）（2,4,6-三甲基苯胺錨）四（五氣 笨基）硼酸鹽， 瓌己基二（十二基）妓四（五氟苯基）硼酸留[，和 甲基二（十二基）妓四（2.3,4,6-四氟笨基）硼酸鹽 本紙張尺度適用中國囷家揉準（CNS ) Α4規格（210X297公釐） A7 B7 五、發明説明（7 適當的相似地麻或辚取代鹽類，如 二癸基4^四（五氟苯基）硼酸鹽， (η-丁基）十二基絲i四（五氟苯基）硼酸豳，三癸基 鱗四（五氟苯基）珊睃锸， 二（十八基）甲基镔四（五氟苯基）硼酸鹽，和 三（十四基）鎩四（五氟苯基）硼酸鹽亦可被採用。 較佳的活化劑是二（十八基）甲基銨四（五氟苯基） 硼酸鹽和二（十八基）（η-丁基）銨四（五氟苯基）硼酸 鹽。 用於此的適當催化剤包括任何元素週期表3至10族中 的金屬化合物或錯合物能夠被本發明中銨鹽栝化劑活化而 做烯烴物揷入及聚合反應。 例子包括了具此化學式的第10族雙亞胺衍生物：
N、 CT-CT (Μ* Κ2Α'其中 Ν · Ν 是 Ar*-N ^N-Ar* 、Μ"是 Ni(Π )或 Pd(K > ; Κ是鹵基、磺氳基、或碘氫基氣； 經濟部中央標準局貝工消費合作社印装
Ar·是一個芳基族，特別是2,6雙異丙基苯基或苯胺族 » CT-CT是1,2乙烷二基、2,3-丁烷二基，或楚形成一値 融合瓌条統其中此二T群合起來形成一艏1,8-察二基.群； 以及 A·是一傾惰性未配位陰離子。 本紙張尺度適用中囷國家標準（CNS ) A4規格（210X297公釐） A7 ______B7 五、發明説明（8 ) 前述的催化劑掲S於M. Brookhart等人於J. Am. Chem Soc. 118,267-268(1996)和J. Am. Chem. Soc., 117,6414 -64 15 ( 1995)的文獻中，作為活性聚合反應催化劑特別是 用於ct-烯烴的聚合反睡，既可單獨使用或是和極性的共 單髌如乙烯基氣化物、烷基丙烯酸鹽和烷基甲基丙嫌酸鹽 0 額外的催化劑包拮了 3、4族或是鑭金厲在+2、+3或+4 正式氣化態的衍生物。較佳的化合物包括了金屬錯合物含 有1至3値；r-鍵结陰離子的或中性的配基群，其可為環狀 或非瓌狀非定域π -鍵结陰離子的配基群。這樣π -鍵結的 陰離子的配基群的例子有共轭或非共轭的、瓌狀或非環狀 的二烯烴基群、烯丙基群、硼化苯基群、和芳烴群。此用 詞"τι -鍵结“表示配基群和過渡性金屬Μ分享從部份非 定域；r-鍵來的霄子的方式鍵結。 在非定域；r-鍵結群中的每一錮原子可獨立為從下群 中的自由基所取代。此群包含有氳、鹵素、碘氳基、鹵硪 氳基、硪氫基取代之準金屬自由基其中準金屬是由元素遇 期表第14族中所選出，且這些碘氫基或碳氫基取代之準金 »自由基進一步為含有15或16族雑原子之基類所取代。包 含於"碳氪基”的有C, - a n直的和分叉的瓌烷基自由基， Ce-ae芳香族的自由基，烷基取代的芳香族自由基， 和(：，-91)芳基取代之垸基自由基。除此之外兩値或多値此 類自由基可合併形成一融合的環条統，包括部份或完全氳 化的融合瓌条統，或是它們可和金屬形成金屬環狀物。適
發明説明（9 ) 當的磷氫基取代之有機準金屬自由基包括單-、雙-、和三 -取代之14族元素的有機準金屬自由基其中每一個碳氳基 包含有1痼至20値磺原子。適當的磷氫基、取代有機準金 颶自由基的例子包含有三甲基矽烷基、三乙基矽烷基、乙 基雙甲基矽烷基、甲澤雙乙基矽烷基、三苯基δ|ι烷基、和 三甲基硌烷基群。 包含有15或16族雜原子基類的例子有胺、磷化氫、乙 醚或碇乙醚部份或從其而來的雙價衍生物，例如酿胺、磷 化物、和過渡性金屬或網条金屬鍵結的乙越或硫乙醚群、 Μ及和磺氫基群或含有磺筮基取代準金颶群鍵結的乙雄或 硫乙_群。 適當的陰離子、非定域；r -bond鍵結群例子包含有瓖 戊二烯基、茚基、笏基、四氫茚基、四氫笏基、八氳笏基 、戊二烯基、環己二烯基、二氳蒽基、六氫Μ基、+氫Μ 基群、和硼化苯基群，以及從其產生的硝氬基取代 或是Ct-u碳氫基取代矽烷基所取代的衍生物。較好的陰 離子非定域τί-键結群有瓌戊二烯基、五甲基環戊二烯基 、四甲基環戊二烯基、四甲矽烷基璟戊二烯基、茚基、 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 2,3-二甲基茚基、笏基、2-甲基茚基、2-甲基-4-苯基茚 基、四氫笏基、八氫笏基、和四氳茚基。 硼化苯是含硼類似苯的陰離子配基*它們先前所知描 述於 G_ Herberich 等人於 Organometallics, 14，1, 471-480 ( 1995)之文獻中。較诖的硼化苯具此化學式 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐〉 -12 - 五、發明説明（10 ) Λ7 Β7
經濟部中央標準局貝工消费合作社印製 其中R”是從包含有磺氳基、矽烷基、或碥烷基之群中選出 ，該R有最多到20傾非氫的葭子。在與這樣非定域；r -bond 鍵結群二價衍生物有關的錯合物中，一艏原子是Μ共價鍵 •结合或是雙價群和錯合物中另一原子產生共價鍵而形成一 橋狀的糸統。 —個適當棰類的催化劑是具此化學式的金屬錯合物： L<MXraX’nX%，或是由其而來的二聚物 其中： L是一個和Μ遽接的陰離子、非定域、π-鍵結群，包 含有最多至50値非氳原子，選择性地兩値L群可聯接一起 形成橋狀的結構，且進一步地L可選擇性地和X連接；Μ是 元素週期表第4族的金屬處於+2、+3或是+4正式氧化態； X是一値選擇性地、雙價取代物有最多至50艏非氳原 子可和L一起和Μ形成金屬環狀物； X’是一値選擇性的中性配基最多有20値非氳原子； t X”每一次出現是一傾單價、陰離子之物最多有40傾非 氫原子，選擇性地，兩傾X”群可共儐連接一起形成一個雙 價的雙陰離子之物有兩傾共價層和Μ鍵結，或是，選擇性 地兩艏X”群可共價連接形成一中性、共轭或是非共軛的雙 烯和ΜΜ π -鍵鍵結（Μ是處於+2的氣化態），或是進一步 選擇性地一豳或多餾X”和一豳或多Ι@Χ_可鍵結一起而形成 (請先閲讀背面之注·^項再填寫本頁) -裝. 本紙張尺度適用中國國家揉準（〇«)々4規格（2】0\297公釐） -13 ~ Λ7 Β7 五、發明説明（11 ) 一傾部份既和Μ共價連接又與路易士齡配位； 义是0 , 1或2 ί π是0或1 i η是從0至3的數宇ί Ρ是從0至3的整數：以及 的和等於Μ的正式氧化數，除了當2Χ”群一起形 成和Μ π -bond鍵結的中性共轭或非共轭雙烯，在此悚形 i + n之和等於Μ的正式氧化數。 較佳的錯合物包含了那些有一傾或兩傾L群的錯合物 。後者包含了那些錯合物有相連兩偁L群的橋群。較佳的 檐群有化學式UR·,)*其中Ε是矽、擁）、錫、或硪，每一催 値別出現是氫或是從矽烷基、碘氡基、磺氫基氧中的一傾 或是其中的结合，該R*有最多至30傾碘或矽原子，以及X 是從1至8。最好每一艇獨立出現的R_是甲基、乙基、丙 基、新丁基、苯基、甲氣基、乙氧基、或是苯氧基。 具有2値L群错合物的例子為具有此化學式的化合物 r3 R3
經濟部中央樣準局貝工消費合作社印裝 其中： Μ是结、结或給，最好锆或姶在+2或是+4正式氧化態 本紙張尺度適用中國國家標準（CNS 規格（2丨0X297公釐） 一 14 一 (請先閲讀背面之注意事項再填寫本頁} 五、發明説明（12 ) Λ7 B7 經濟部中央標準局貝工消費合作社印製 每一値別出現的R3是從包含有氫、硪氫基、矽烷基、蝻 烷基、氨基、鹵基Μ及其連接物的群中選出，該R3有最 多至20傾非氫的原子，或相鄰的R3群一起形成二儐的衍生 物（如磷氫雙基、矽垸雙基、或他烷雙基）而形成一艢融 合的環条統，以及 每一値獨立出現的X”是一魅陰離子配基群有最多40値 非氳的原子，或兩傕X”群一起形成一個雙價陰離子配基群 最多有40値非氫的原子或一起最一個有4至30値非氩原子 的雙烯和Μ形成一傾錯合物，其中Μ是在+2的正式氧化態， 且 Re、Ε和X前面已定義過。 前面的金屬錯合物特別適合用來配製有立體規則分子 結構的聚合物。在此容量最好錯合物有（：*的對稱性或有旋 光性、立體堅硬榷造。第一型的例子是擁有不同非定域π -鍵结条統的化合物，像是一悃瓌戊二烯基和一俚笏基。 類似的基於Ti(IV>和Zr(IV)的条统用來配製順聯烯垤聚合 物掲露於 Ewen 等人於 J. An. Chem. Soc. 110, 6255-6256 (1980)之文獻。旋光性檐造的例子包括消旋的雙茚基错合 物。類似基於TUIV)或Zr (IV)的糸統掲露於Wild等人於J. Organomet. Chem., 232, 233-47, U982)之文獻中用來 配製間規烯煙聚合物。 具有兩傾π-鍵結群的橋配基的例子爲：（二甲基矽 烷基-雙（瓌戊二烯基）），（二甲基矽烷基-雙（甲基環 本紙張尺度適用中國國家標準（CNS ) Α4規格（21 OX297公釐） _ 15 - (請先閲讀背面之注意事項再填寫本頁) -裝· 、1Τ Α7 Β7 經濟部中央標準局貝工消费合作杜印製 五、發明説明（13) 戊二烯基）），（二甲基矽烷基-雙（乙基環戊二烯基） )，（雙甲基矽烷基-雙（t-丁基環戊二烯基）），（二 甲基矽烷基-雙（四甲基瓖戊二烯基）），（雙甲基矽烷 基-二（喆基）），（二甲基矽烷基-雙（四氫茚基））， (二甲基矽烷基-雙（笏基）），（二甲基矽垸基-雙（四 氫笏基）），（二甲基矽烷基-雙（2-甲基-4-苯基茚基） )，（二甲基矽烷基-雙（2-甲基茚基）），（二甲基矽 烷基-瓖戊二烯基-¾基），（二甲基矽烷基-環戊二烯基-八氳喆基），（二甲基矽烷基-環戊二稀基-四氫茚基）， (1,1,2,2,-四甲基-1,2-雙矽烷基-雙-環戊二烯基），（ 1,2-雙（環戊二烯基）乙烷），和（異丙基喆-環戊二烯 基-¾基）。 較佳的X”群從氦化物、磺氫基、矽烷基、碥烷基、鹵 氳联基、鹵矽烷基、矽烷基磺氫基和氨基硪氬基中選出。 . 或兩傾Γ群一起形成一値共轭二烯的二價衍生物或是另外 它們可一起形成一中性鍵結共轭二烯。最好的 的磺氫基群。 另一類別用於本發明的金屬錯合物具前述化學式 LiMXmX、X”P，或由其而來的雙聚物，其中X是一籲雙價的 取代物有最多至50魅非氫的原子且和L—起和Μ形成一金屬 環狀物。 較佳的二價X取代物包含有最多30豳非氫的原子的群 ，其中至少一脑原子是氧、硫、硼或是元素週期表中14族 的一員且直接和非定域π-鍵結群聯接，以及另一從氮、 (請先閱讀背面之注意事項再填寫本頁) '装· 订 4· 本紙張尺度適用中國國家標準（CNS〉Α4規格（2丨〇><297公釐） 經濟部中央標準局負工消費合作社印装 Λ7 B7_____ 五、發明説明（14 ) 磷、氧或硫中遴出的不同葭子和Μ共價鍵結。 依本發明所用的一個較佳的4族金屬錯合物的類別具 此化學式： R3
R3 R3 其中： Μ是钛或锆，最好是钛在+2、+3、或是+4正式氧化態 每一掏立出現的R9是從包含有氫、磺氳基、矽烷基、 褚烷基、氛基、囱基及其連接物的群中選出來的，該R3有 最多至20翻非氫的原子，或相鄰的V群一起形成一催二價 的衍生物（那是一鏟碳氳二基、雙矽烷基或祕烷二基群） 而形成一融合的環系統， 每一傾X”是一値鹵基、碩氳基、碳氳基氧或矽烷基群 ，該群最多有20豳非氳的原子，或兩値X”群一起形成一個 中性的Ce-3e共轭二烯或一値雙價衍生物； Y是-〇-、-S-、-NR*-、-PR*-;以及 Z是 SiR、' CR%、SiR·»、cR"aCR"a、CR_ = CR*、 CR'SiR%、或GeR"a，其中R*如前面所定義。 可用於本發明的4族金屬錯合物的例子包括有： 環戊二烯基钛三甲華， 本紙張尺度適用中國國家橾率（CNS ) A4規格（210X297公釐〉 --------(；柴------ir------ (請先閱讀背面之注意事項再填寫本頁)，. -17 - 經濟部中央標準局貝工消費合作社印袋 Λ 7 Β7 五、發明説明（15 ) 環戊二烯基呔三乙基， 瓌戊二烯基钛三異丙基， 瓌戊二烯基钛三苯基， 環戊二烯基钛三苯甲基， 環戊二烯基钛-2,4-二甲基戊二烯基， 環戊二烯基钛-2,4-二甲基戊二烯基•兰乙瞵， 瓌戊二烯基钛-2,4-二乙基戊二烯基•三甲膦， 瓌戊二烯基I太雙甲基氧化物， 瓌戊二烯基钛二甲基氯化物， 五甲基環戊二烯基钛三甲基， 茚基钛三甲基， 茚基钛三乙基， 茚基钛三丙基， 訪基钛三苯基， 四氫茚基钛三苯甲基， 五甲基環戊二烯基钛三異丙基， 五甲基琿戊二烯基钛三苯甲基， 五甲基環戊二烯基钛二甲基甲氧化物， 五甲基環戊二烯基钛二甲基氣化物， 二U β-2,4-雙甲基戊二烯基）钛， 二U--2,4-雙甲基戊二烯基）钛•三甲膦， 二（ηβ_2,4-雙甲基戊二烯基）钛·三乙膦* 八氫笏基钛三甲基， 四氫茚基钛三甲基， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐） --------------1Τ----- (請先閱讀背面之注意事項再填寫本頁)， A7 B7 五、發明説明（16 ) 經濟部中央樣準局貝工消費合作杜印掣 四氫笏基钛三甲基，. (第三-丁醯胺基）（1,1-二甲基-2,3,4,9,10,-n -1,4,5 ,6,7,8-六氫禁基）二甲基矽烷钛二甲基* (第三-丁醯胺基）（1, 1,2,3-四甲基-2,3,4,9,10,-〇-1,4,5,6,7,8-六氲萘基）二甲基矽烷钛二甲基， (第三-丁醯胺基）（四甲基-η β-環戊二烯基）二甲基矽 烷钛二苯甲基， (第三-丁醯肢基）（四甲基-r?e-琛戊二烯基）二甲基矽 烷钛二甲基， (第三-丁醯胺基）（四甲基-η β-環戊二烯基）~1,2_二 乙烯基钛雙甲基， (第三-丁醯胺基）（四甲基-η β-茚基）二甲基矽烷I太二 甲基， (第三-丁醯胺基）（四甲基-η β-環戊二烯基）二甲基矽 烷钛（麗>2-(二甲基氡）苯甲基， (第三-丁醢胺基）（四甲基-τ?β-琢戊二烯基）二甲基矽 烷钛（Β )烯丙基， (第三-丁班胺基）（四甲基-η 烷钛U )2,4-雙甲基戊二烯基， (第三-丁醯胺基）（四甲基-rj 烷钛U >1,4-雙苯基-1,3-雙丁烯， (第三-丁醯胺基）（四甲基-η β-環戊二烯基）二甲基矽 烷钛U )1,3戊二烯，· (第三-丁酪胺基）（2-甲基訪基）二甲基矽烷軚（I )2,4 -己二烯， (第三-丁酿胺基）（2-甲基喆基）二甲基矽烷钛（IV >2,3 -二甲基-1,3-丁 二烯， (第三-丁越胺基）（2-甲基茚基）二甲基矽烷钛（W )異 瓌戊二烯基）二甲基矽 瓌戊二烯基）二甲基矽 --------(装-- (請先閲讀背面之注意事項再填寫本頁) 訂 MJ. A4規格（21 OX297公釐 19 - A7 _ _B7 五、發明説明（17) 丙烯， (第三-丁酿胺基）（2-甲基喆基）二甲基矽烷钛〇V)l,3 -丁二烯， (第三-丁醯胺基）（2,3-二甲基茚基）二甲基矽烷钛（w ) 2.3- 二甲基-1,3-丁 二烯， (第三-丁醯胺基）（2,3-二甲基茚基）二甲基矽烷钛（IV〉 異丙烯， (第三-丁醯肢基）（2,3-二甲基訪基）二甲基矽烷钛（IV) 一 03 甘 一中；S， (第三-丁醯胺基）（2,3-二甲基訪基）二甲基矽烷钛（IV ) 1.3- 丁二烯， (第三-丁酿胺基）（2, 3-二甲基茚基）二甲基矽烷钛U ) 1.4- 雙苯基-1,3-丁二嫌， (第三-丁醯胺基）（2-甲基茚基）二甲基矽烷钛（I ) 1,3 -戊二烯， (第三-丁醯胺基）（2-甲基茆基）二甲基矽烷钛（W)二 甲基， 經濟部中央標準局員工消費合作社印製 --------(装-- (請先閱讀背面之注意事項再填寫本頁} 4, (第三-丁醯胺基）（2-甲基茚基）二甲基矽烷钛（IV)二 笨甲基， (第三-丁醯胺基）（2-甲基-4-苯基茚基）二甲基矽烷鈦 (H )1,4-二笨甲基-1,3-丁二烯， (第三-丁醯胺基）（2-甲基-4-苯基茚基）二甲基矽烷钛 (H ) 1，3-戊二烯， (第三-丁醯胺基）（2-甲基-4-苯基訪基）二甲基矽烷钛 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -20 - 經濟部中失標準局員工消費合作社印裝 A7 B7__ 五、發明説明（18 ) < Π )2,4-己二烯， (第三-丁醯胺基）（四甲基-D β-瓌戊二烯基）二甲基-矽烷钛（IV ) 1·3-丁二烯， (第三-丁酿胺基）（四甲基-rj 頊戊二烯基）二甲基 矽烷鈦（1V>2,3-二甲基-1,3-丁二烯， (第三-丁酿胺基）（四甲基-rr β_瓌戊二烯基）二甲基 矽烷钛（IV〉異戊二烯， (第三-丁醯胺基）（四甲基-Τ7 瓖戊二烯基)二甲基 矽烷钛（Π )1,4-二苯甲基-1,3-丁二烯， (第三-丁醯胺基）（四甲基-r? β-環戊二烯基）二甲基 矽烷钛< I〉2,4-己二烯， (第三-丁醯胺基）（四甲基-η β-瓖戊二烯基）二甲基 矽烷钛U )3-甲基-1,3-«二烯， (第三-丁醯胺基）（2,4-二甲基戊二烯-3-基）二甲基矽 院钱二甲基， (第三-丁躔胺基）（6,6-二甲基瓌己二烯基）二甲基矽烷 钛二甲基， (第三-丁醯胺基）（1.卜二甲基-2,3,4,9, 10-η -1,4,5, 6.7.8- 六氫萘-4-基-〉二甲基矽烷呔二甲基， (第三-丁醯胺基）（1,1,2,3-四甲基-2· 3,4,9,10-τϊ -1, 4.5.6.7.8- 六氳萘-4-基）二甲基矽烷钛二甲基， (第三-丁醯胺基）（四甲基-π β-琛戊二烯基甲基苯基矽 烷呔（IV )二甲基， (第三-丁醣胺基）（四甲基-ηβ-環戊二烯基甲基苯基矽 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐> --------(-1-- (請先閱讀背面之注意事項再填寫本頁) 、1Τ
AJ -21 - 經濟部中央橾準局貝工消費合作社印製 Λ7 Β7 五、發明説明（19) 烷钛（I )1,4-二苯基-1,3-丁二烯， 1-(笫三-丁醯胺基）-2-(四甲基-T) β_瓌戊二烯基）乙 烷二基钛（IV )二甲基，和 1-(第三-丁醯胺基> -2-(四甲基-r? β-環戊二烯基）乙 烷二基钛U) 1,4-二苯基-1,3-丁二烯。 有兩但L群的錯合物包栝橋接錯合物在内而通用於本 .發明的包含有： 雙（瓌戊二烯基）锆二甲基， 雙（琛戊二烯基）锆二苯甲基， 雙（琿戊二烯基）锆甲基苯甲基， 雙（頊戊二烯基）鉻甲基苯基， 雙（環戊二烯基）锆二苯基， 雙（琢戊二烯基）钛烯丙基， 雙（環戊二烯基）结甲基甲氧化物， 雙（環戊二烯基）結甲基氮化物， 雙（五甲基瓖戊二烯基）锆二甲基， 雙（五甲基環戊二烯基）钛二甲基， «(訪基）锆二甲基* 茚基笏基锆二甲基， 雙（茚基）结甲基（2-(二甲基氨基）苯甲基）， 雙（茚基）鉻甲基三甲基矽烷基， 雙（四氳茚基）锆甲基三甲基矽烷基， 雙（五甲基環戊二烯基）錯甲基苯甲基， 雙（五甲基環戊二烯基）锆二笨甲基， 本紙張尺度適用中國固家標準（CNS ) Α4規格（210Χ297公釐） --------(I------II------^乂 (請先閲讀背面之注意事項再填寫本頁)，， ： 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（20 ) 雙（五甲基環戊二烯基）结甲基甲氧化物， 雙（五甲基環戊二烯基）锆甲基氣化物， 雙（甲基乙基瓌戊二烯基）锆二甲基， 雙（丁基環戊二烯基）锆二苯甲基， 雙U-丁基環戊二烯基）锆二甲基， 雙（乙基四甲基環戊二烯基）锆二甲基， 雙（甲基丙基瓌戊二烯基）錶二苯甲基， 雙（三甲基矽烷基環戊二烯基）锆二苯甲基， 二甲基矽烷基-雙（環戊二烯基）锆二甲基， 二甲基矽烷基-雙（四甲基環戊二烯基）钛（1δ)烯丙基， 二甲基矽烷基-雙（t-丁基環戊二烯基）锆氣化物， 二甲基矽烷基-雙（η-丁基環戊二烯基）鍤氯化物， (亞甲基-雙（四甲基環戊二烯基）钛U) 2-(二甲基氨 基）笨甲基， (亞甲基-雙（η-丁基環戊二烯基）I太U)2-(二甲基氨 基）苯甲基， 二甲基矽烷基-雙（茚基）锆苯甲基氣化物， 二甲基矽烷基-雙（2-甲基喆基）锆二甲基， 二甲基矽烷基-雙（2-甲基-4-苯基茚基）锆二甲基* 二甲基矽烷基-雙（2-甲基茆基）锆-1,4-二苯基-1,3-丁 二烯， 二甲基矽烷基-雙（2-甲基-4-苯基茚基）锆U)l,4-二苯 基-1,3-丁二拥， 二甲基矽烷基-雙（四氫茚基）锆（S)l,4-二苯基-1,3-丁 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -----;---(&------tl------{乂 (請先閱讀背面之注意事項再填寫本頁)： ： -23 - Λ7 Β7 五、發明説明（21) 二烯， 二甲基矽烷基-雙（笏基）鍺甲基氣牝物， 二甲基矽烷基-¾ (四氳笏基）锆雙（三甲基矽烷基）》 (異丙塞an (瓖戊二烯基> (笏基）锆二苯甲基，和 二甲基矽烷基（四甲基琛戊二烯基）（¾基）锆二甲基。 其他偁化剤，特別是含有其他4群金屬的催化劑，當 然對於熟知此技蓊者是非常淸楚的。 本發明的共催化劑可和下列化合物一起使用，包括一 有1至10健硪在每一钿硪氫基群的三（磺氫基）鋁化合物 ，一低聚合的或高聚合的铝氧烷化合物，一镝二（硪氬基 )(碘氬基氧）鋁化合物有1至20餹磺原子在每一齒碘氳 基或硝氳基氧群，或是前面化合物的混合物，如想要的話 。埴些鋁化合物是用它們的功能來清除從聚合反應混合物 來的雑質如氧、水及醛類等。 鲤濟部中央標準局貝工消費合作社印袋 (請先閱讀背面之注意事項再填寫本頁)： 適當的二（硪氫基）（碘氳基氧）鋁化合物具化學式 TSAIOT1*，其中T1是C3-e次级或三级烷基，最好是異丙基、 異丁基、或第三-丁基；以及T*是Cl8-ae烷芳基自由基或 芳烷基自由基，最好是2,6-二（第三-丁基）-4-甲基苯基 ，2,6-二（第三-丁基）-4-甲基甲苯基，2,6-二U-丁基 )-4-甲基苯基，或4- (3’，5’-二第三-丁基甲苯基）-2,6 -二第三-丁基苯基。 較好的鋁化合物包括了 C·-·三烷基鋁化合物，特別是 那些其中烷基是乙基、丙基、異丙基、η-丁基、異丁基、 戊基、新戊基、或異戊基》二垸基（芳基氧）鋁化合物含 本紙張尺度適用中國國家揉準（〇^)六4規格（2丨0父297公浼） -24 - 經濟部中央榡準局貝工消費合作.社印装 Λ7 Β7 五、發明説明（22) 有1至6饈联在烷基群以及6至18海磺在芳基群（尤其是 (3,5-二（t-丁基）4-甲基苯基氧）二異丁基鋁），甲基 耝氧烷修正的甲基鋁氧烷Μ及二異丁基鋁氧烷。鋁化合物 和金屬錯合物的其耳比值較好是從1: 10,000至1,000: 1 ，比較更好是從1: 5,000至100: 1，最好是從1: 100至100 :1 〇 所有的催化劑/共催化劑其耳比值較好範圍是從1: 10 是10 : 1，比較更好是從1 : 5至1 ί 1，最好是從1 *· 1.5至1 :1»如果想要的話本發明的活化共催化劑亦可被使用。 適當的添加可聚合單賭包括乙烯未飽和箪饅、乙炔化 合物、共轭或非共轭二烯物、和多烯物。較好的單賸包括 烯垤類，例如alpha-烯烴類有2至20,000磺原子，較好是 2至20僱，更好是2至8值硪原子Μ及兩傾或更多傾逭樣 alpha-烯烴物的結合。特別適當的alpha-烯垤物包括，例 如，乙烯、丙烯、卜丁烯、1-戊烯、4-甲基-卜丁烯、卜 己烯、1-庚烯、：[-辛烯、1-壬烯、卜癸烯、1-11烯、1-12 烯、1-13烯、1-14烯、W5烯、或是它們的结合，K及在 聚合反應形成的長辣乙烯基終结的低聚合或聚合物產 物*逋有特定加入反應混合物中用來產生相對長鍊分支聚 合物產物的烯烴物。較好的α-烯烴物是丙烯、 卜丁烯、4-甲基卜戊烯、1-己烯、1-辛烯、或是乙烯Μ 及或是丙烯與一餡或多傾道樣烯烴物的結合。其他較佳的 單腰包括苯乙烯、鹵基或烷基取代的苯乙烯、四氧乙烯、 乙烯基環丁烯、1,4-己二烯、二環戊二烯、亞乙基原冰石 本紙張尺度適用中國國家椟芈（〇阳）六4規格（2丨0><297公1) -----；---^ 裝 II (請先聞讀背面之注意事項再填寫本頁) 訂 -25 - A7 _____B7 五、發明説明（23) 烯、和1,7-辛二烯。前述單體的混合物亦可被使用。 一般而言，這聚合物反脯可在Ziegler-Natta或Kaminsky-Sinn式的聚合物反應等先前技醯中為人熟知的狀況下完成 。懸浮、溶液、漿、氣相、或高K，不管是使用於整批或 連績的形式或是其他生成狀態，如果想要都可使用。這些 熟知的聚合反應遇程描寫於W0 88/02009、U.S.專利號碼 5,084,534、 5,405,922、 4.588,790、 5,032,652、 4,543,399 、4.564,647、4.522,987中Μ及其他地方。較佳的聚合反 應溫度是從0-250t：，較佳的聚合反應歷力是從大氣壓至 3000大氣壓》 然而本發明特別值得注葱的優勢是當催化劑条统用於 溶液聚合反應，最好是一鶴連绩的溶液聚合反應過程 ，在有腊肪族或脂瓌族液體稀惲劑存在的情形下，逭用詞 "連續聚合反應”表示至少聚合反應的產物連鋇被從反應 生成物中移走，例如像是將部份反應混合物除揮發。較好 是在聚合反應過程中一摘或多館反應物能被連纗加入聚合 物化貉合物。邃當的脂肪族或脂瓌族液體稀釋劑的例子包 括有直鍊和分辣碘氲物像是異丁烷、丁烷、戊垸、己烷、 經濟部中央標準局貝工消费合作社印裝 --------(裝-- (請先閲讀背面之注意事項再填寫本頁) 庚烷、辛烷、以及其混合物；脗琛族碘氫物如瓌己烷、琛 庚烷、甲基琢己烷、甲基瓖庚烷、Μ及其混合物；以及遇 氟硪氳物如過氟烷類及類似物。適當的稀釋劑也包 含了芳香族的硝篋物（持別是和芳番族的α-烯垤物如苯 乙烯或環烷基取代之苯乙烯使用）有甲苯、乙苯、雙甲苯 ，Μ及掖醭嫌垤物（可當單《或共單體）包括乙烯、丙烯 本紙張尺度適用中國國家榇準（CNS ) Α4規格（210Χ297公f ) -26 - 經濟部中央梯準局頁工消費合作社印裝 Λ7 ______B7 五、發明説明（24) 、丁二烯、琛戊烯、卜己烯、3-甲基-卜戊烯、4-甲基-卜 戊烯、1,4-己二烯、1-辛烯、卜癸烯、笨乙烯、二乙烯基 苯、乙烯基甲苯（包括所有異檐物自身或混合）、Μ及類 似物。前逑化合物的混合物也適合。 在大部份的聚合物反應中催化劑：可聚合反應化合物 的其耳比值所用的是從10 〃 ·· 1至101 : 1，較好是從10-〃 :1至10·β : 1。 本發明的催化劑条統亦可與另相串聯或並聯的反應器 中的至少一《額外的均勻或非均勻聚合作用漼化劑結合使 用，Μ配裂具有所想要性質的聚合物混合物。逭樣遇程的 例掲露於W0 94/00500，相當於U.S.编號07/904,700。一 傾比較特定的過程掲露於共同應用U.S.编號08Λ0958 »存 楢於1993年1月29日。 分子量控制劑可和本共催化劑結合使用。如此的分子 Μ控制劑包括有氳、三烷基鋁化合物或是其他知暁的辣傳 送爾。一項使用本共催化劑的特別好處是其能力（依反睡 狀況）可以極大改良的催化劑效率產生狹窄分子量分佈的 α-烯垤物均一聚合物與共聚合物。較好的聚合物具Mw/Hn 小於2.5,更好是小於2.3。逭樣窄的分子量分佈聚合物由 於其改良的抗拉強度是非常想要的。 要知道本發明在缺少任何沒有待定掲S的成份之愴況 下是可操作的。下列提供的例子是為了進一步閜釋本發明 而非僅限於此。除非陳述到相反的，所有部份及百分比濃 本纸張尺度適用中國國家椟準（CNS ) A4規格（210X297公釐） --------(I------1T------ (請先閱讀背面之注意事項再填寫本頁)： 二 27 經濟部中央標準局負工消費合作社印裝 A7 B7 五、發明説明（25) 度都以重量為底來表示。 例1 二（+八基）甲基銨四（五輟苯基）硼酸鹽之配製 ((Ci.HarJ^NiMeJH'BCCeF,,)^) 二（+八基）甲基銨氢化物（（CieH37)aN(Me>lTCl·〉 0.50克的二（十八基）甲基銨（（CltlH3T)aN(Me)) (Aldrich Chemical)溶於50毫升的己烷中。HC1在Eta〇中 (1M, Aldrich, 1.17毫升）Μ針筒加入，而立刻產生白色 沈澱。此混合物經攪拌數小時，然後經過一傾中等孔隙 <10-15徹米）的搪瓷過嫌。殘留在搪瓷上的固賭經由額外 的己烷沖洗，然後在搪瓷上乾燥且最後置於真空狀態下。 約有0.56g像白色固醴狀的產物可得到。 配製A ) 在乾煉箱中，0.50完的LiB(CsFe>«和0.38g的 <CieH3T)aNMe>H*Cl·在一傾小瓶中混合成固體狀。此瓶被 從乾燦箱中移走且加入30毫升的蒸餾水。此UB(C,Fe) «呈 溶解狀，但此氳氣酸銨懸浮於液賭®上。此混合物置於機 械振動器上一小時。在這段時間，此氫氣酸銨缓慢消失且 為一黏在瓶壁上的黏稠白色沈澱所取代。在一小時結尾， 混合物被倒入一分離瀰斗中且加入20毫升的飽和硝酸納溶 液。此層被分離且丢寨液體層。此有機層以20毫升Ha〇冲 洗，以破酸鎂乾燥之，且經由一値小的Sc hi enl{管過濾。 此揮發性的物質然後於真空下移除而留下一個淡棕色的黏 油。此Schlenlc管然後被放置於乾燥箱且此油溶解於環己
I 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） (諳先閲讀背面之注項再填寫本頁) 裝· 訂 -28 - 經濟部中央標準局負工消費合作社印袋 Α7 Β7 五、發明説明（26 ) 烷。此溶液Μ—量瓶配置成10亳升。由置稱此Schlenk管 的重量於移走產物及環己烷之前後，產物的重量決定為 0.80g。假設（CieH,T),N(Me)H*B(C*Fe)4-的分子置是 1216.08 g/B〇l，此溶液計算得到的濃度是0.066M，10.3 重量百分比。 配躲B) 在乾燥箱中，0.50克的LiB<C«Fe)*和0.42g的 ((：1,11〃>,—6)11*(：1-在一小瓶於25毫升的甲苯中漿化。此 瓶從乾播箱中移開且加入20毫升的蒸皤水。此瓶置於一振 動器且完全癀動一小時。在此時間結束，加入20毫升飽和 硪酸納溶液且此混合物傳送至一分離漏斗。此層被分離而 將水溶液層抛«。此有機層M20毫升飽和碘醢納沖洗後再 以20毫升H，0沖洗，Μ硫酸镁乾燥且過濾。此揮發物真空 下移除而留下0.71克的淡棕色油。此瓶置於乾燥箱中且此 油溶解於10毫升的混合烷類（Isopar™ Ε，可從Exxon Cheaicals Inc.得到）而得到0.0075M，9.0重蚤百分比的 溶液灌度，然後進一步稀惲至最後溶液濃度0.0075M。 配製C ) 在乾煉箱中，0.50克的LiBKiF*〉《和〇.42g的 ((^,Η3Τ>·Ν(Μβ>Η·(：1-於20毫升的環己烷中漿化。此混合 物加熱至回滾達1.5小時。加熱後不久此溶篏變澄清。在 回流時間终止，此溶液被冷郤至室溫且用矽薄土遇濾辅肋 <CelUe~ )經由一中孔徑（10-15β«Ο搪瓷漏斗過濾。此溶 液傳送至一4盎司的瓶中且從乾燥箱移走，以気氣短暫嗅 本紙張尺度適用中國圏家標率（CNS ) Α4規格（2丨0><297公釐） --------「^.------ίτ------(广 (請先閲讀背面之注項再填寫本頁)二 : -29 - 經濟部中央揉準局WC工消費合作社印製 Λ 7 __Β7 五、發明説明（27 ) 射然後放回乾燥箱中。一份溶液被移走且Μ重最分析置其 濃度；所得到溶濃度值爲0.022Μ * 3.4重童百分比。 聚合作用 一加侖的抿拌反應器中加入Isopar’M Ε溶劑、卜辛烯 和5毫其的氫。此反應器加熱至1301C且Μ乙烯跑和至450 psig (3.1MPa)。催化劑組成於乾燥箱中配製，Μ針简一 起注入2,5毫其耳（t-丁基醯胺）二甲基（ηβ-四甲基瓌 戊二烯基）钛3-戊二烯）催化劑、二（十八基） 甲基銨四脑（五氟苯基）硼酸鹽共催化劑（Κ先前的配裂 A)、 Β)或C)中之一來配製），以及選擇性地的第三 個成份（三異丁基鋁修正的甲基鋁氧垸（ΜΜΑ0)，三異丁基 鋁（TIBΑ〉，或（2,6-二（t-丁基）-4-甲基苯氧基〉二（i-丁基） 鋁（D丨BAL-B0T))。此混合物由針筒傳送至一添加環路且注 入反應器約超過4分鐘。此聚合.反應讓其進行10分鐘 同時注入乙烯Μ保持450 psig (3.1 MPa)的壓力。此聚合 物溶液可以從反應傳送至玻瑰鍋中，接箸再於真空壚内充 分乾燥，或是被丢_掉。當聚合物被分離且乾燥的情形下 *催化劑的效率可以計算為每克钛多少公斤聚合物。當聚 合物沒有保存下來的倩形*造效率可Μ計箕為每克钛多少 公斤乙烯在反應中消耗掉。聚合反應的詳倩示於表1。 本紙張尺度適用中國國家標準（CNS ) Α4规格（2〗ΟΧ297公1 ) --------「I------ΐτ------Ρ (請先閱讀背面之注意Ϋ項再填寫本頁)： ： -30 - Λ7 B7 五、發明説明（28 ) 表 1 次數共催化劑 第3成份 溶劑辛烯 效率 (撤其耳） （撤其耳）《克）（克）（公斤克Ti> 1 A 2.5 MMAO 25 1426 138 0.8 2 A 3.75 ” 1423 132 1.0 3 A 3.15 rt 1415 138 0.9 4 A 5.0 tt 1410 136 1.0 5 A 1.5 ” ” 1433 137 0.5 6 A 3.75 無 0 1432 130 0.5 7 A ” MMAO 25 1462 137 0.6 8 A，， TIBA 25 1459 133 0.7 9 A " DIBAL-BOT 25 1470 130 0.9 10 B " *» 50 1427 139 1.5 11 C ” rt tt 1420 140 0.9 雙（氫化牛脂烷基）甲基銨四（五氟苯基）砸酸鹽 ((C,,-aaH,T-4e)*N* (Me)HB' (CeF,,)^) 經濟部中央標準局負工消费合作社印製 --------「裝— (請先閱讀背面之注意事項再填寫本頁) 例1的合成步思，配製C之過程大都被重覆除了玆鹽 是從雙（氫化-牛脂烷基）甲基胺（一種三烷基胺含有從 牛脂衍生而來的。*-^烷基群混合物，可從Witco Corporation 或 Akzo Nobel 得到） 製逭而來。
配剪A 雙（氣化-牛脂烷基）甲基胺（KEMAMINE® T-9701從 Witco Corporation取得；此胺之分子量從供應商報導的 本紙張尺度適用中國國家橾準（CMS ) A4規格（210X297公釐） -31 - 經濟部中央標準局貝工消費合作社印策 Λ7 B7 五、發明説明（29) ” Total Amine Value"計算出來為 513.8。（5.65 克，11.0 毫其耳）溶解於50毫升己烷。HC1在乙醚中的溶液（1M， 13.75毫升）以針茼加入之，產生白色沈澱。此混合物被抿 拌30分鐘，然後用一孔徑10-5撤米的玻璃搪瓷過濾。殘餘 的固體Μ己烷沖洗並在真空下乾燥。 在乾燥箱中*前面得到的1.20克的胺氳氣酸鹽（2. 18 毫其耳 >和1.57克的1^8(0^9)«(2.29毫其耳）在己烷中混 合並在25Ό後拌2小時。在此時間結束時，琿己烷被加入 (10-15毫升）且此溶液被用一孔徑10-15撤米的玻璃搪瓷 過濾並被覆蓋Μ矽蒱土過濾輔助物（Celite—)。此溶液濃 度Μ重量分析方法測得為6.3重董百分比。
配剪R 雙（氫化-牛脂烷基）甲基胺（ARMEEN® Μ2ΗΤ從Akzo Nobel得到；此胺之分子量依據供應商提供的分析證明為 521.〖）（5.00克，9.6毫其耳>溶於50毫升己烷中。HC1在乙 醚的溶液Μ針筒加入，產生白色沈澱。此混合物以手搖幌 10分鐘，然後用一孔徑10-15微米的玻璃搪瓷過濾。白色 殘餘的固體用己烷沖洗並在真空下乾燥。 在乾煉箱中，前面得到的2.00克的胺氳氣酸鹽（3.59 毫其耳）和2.58克Li β)4(3.77毫其耳）混合成固體。 環己烷<30毫升）被加入且此混合物被攪拌2小時。在此结 束時，此混合物波Μ一孔徑10-15撖米覆蓋者Celite〃過 濂輔助物的玻璃搪瓷遇疏而得到一清晰淡棕色的溶液。此 溶液漉度經重力测量為10.3重量百分比。 本紙張尺度適用中國國家標準（CNS)A4規格（210X 297公釐） ---------(裝-- (請先閱讀背面之注意事項再填寫本頁) 訂 -32 - 經濟部中央標準局貝工消费合作社印製 Λ7 _______B7 五、發明説明（30 ) 配靱C ( Μ畤庙半1[氣彳h物級） 雙（氫化-牛脂烷基）甲基胺（ARMEEN® M2HT，l.Og ，1.92毫其耳）溶於25¾升甲基瓌己烷中。HC丨水溶液（1M ，1.92毫升）Μ針筒加入之。此混合物被攪拌30分鐘》然 後加入20毫升LiB(CeFe)*U.32克，1.92毫其耳）溶於水的 溶液。此混合物再被JS拌另30分撞。然後其被倒入一分離 漏斗中且加入50毫升的跑和氯化納水溶液。此層被分雔且 將水層丢薄。此有機層Μ碕酸鎂乾燥過夜。此混合物然後 Μ —孔徑10-15撤米的玻璃搪瓷過液而得到一清晰的淡棕 色溶液。此溶液被傳送至一瓶内，撤底地Μ氮氣喷射之且 放置於乾燦箱中。此溶液濃度Μ重力方法测量為17.5重量 百分比。 配H:大最 甲基環己烷（1200毫升）加入於一 2升的圓拉瓶中。當 抿拌時，雙（氫化-牛脂垸基）甲基銨（ARMEEN® Μ2ΗΤ， l〇4g，磨成顆粒狀）被加入此瓶且攪拌至完全溶解。HC1 水溶液（1M，200¾升）被加入此瓶中，且此混合物被搜拌 30分瘇。一掴白色沈锻物立邸形成。在時間结束時， LiB(C8Peh ♦ Eta〇 · 3LiCl (Mw = 887.3 ; 177.4g>被加入此 瓶中。此溶液開姶呈乳狀白色。此瓶配著一6英吋的管柱 覆以一蒸蹓裝置且此混合物被加熱（140Ό外腌溫度）。 乙®和甲基瓌己烷的混合物由此瓶中蒸皤而出。此二柑的 溶液此時只是稍徹混濁。此混合物讓其冷卻至室溫，且將 其置於4升的分離瀰斗中。此水溶液1被移走且丢薄之， 本紙張尺度適用中國國家鱗（CNS } Α4· ( 210X297公釐) -----；---Μ ^------?1------^ (請先閱讀背面之注項再填寫本頁)： ： -33 - 經濟部中央樣準局貝工消費合作社印製 A7 B7 五、發明説明（31 ) 且此有機層Μ H *〇清洗兩次並再將水溶液屬丢_。此生成 溶液分爲兩莽份以估計兩値工作過程。這呰丨丨》0跑和的甲 基琢己烷溶液置得有0.48重置百分比的二乙基秘（EU0〉。 工作步驟b 13X分子篩技術 此溶液（600毫升傳送至一値1升的瓶中，徹底用赛 氣噴射，且傳送至乾燥箱中。此溶液讓其經過一管柱（1 吋直徑、6时高）含有13X分子豳。這樣減少Eta〇的程度 從0.48重董百分tb至0.28重畺百分比。這物質然後被攪拌 於13X分子筛（2〇g>上4小時。EU0的程度再測量為0.19重 童百分tb灌度。此混合物於是攪拌過夜，導致一値更低 EU0程度至40 ppm。此混合物於是用一値配備有孔徑10-15撤米玻瑀搪瓷的瀰斗過濾而得到一清晰的溶液（這分子 篩以頟外的甲基環己烷沖洗）。此濃度以重量分析测得之 值為16.7重童百分比。 工作步驟b 真空技術 此溶液（600毫升）傳送至一瓶中且加入35克硫酸鎂 。這混合物被價拌5分鐘*然後經過一個配備有孔徑10-15 撒米的玻璃搪瓷的湄斗過濾至第二傾1升的瓶中。此清晰 溶液以氮氣徹底嘖射，然後傳送至乾燥箱内。此揮發性物 質在真空狀態下移走而留下一値清楚的淡黃色油。這油再 溶解於乾的去氣的甲基環己烷中且其濃度以重力分析方法 測置（23.5重量百分比）。以氣體色層法（GC)分析顯示此 溶液含有<20 ppm的EtiO。 聚合反應 本紙張尺度適用中國國家標準（CNS ) ( 210X297公釐〉 --------「袭------ΐτ------^ (請先閱讀背面之注意事項再填寫本頁)，， -34 - 經濟部中央標準局貝工消费合作社印製 387908 at _____B7 五、發明説明（32 ) 例1的聚合反應狀態大部份被重覆以前面的牛脂胺盥 衍生物為活化劑而各種過渡性金屬錯合物爲催化劑。結果 包含於表2中。 表 2 次數 催化劑 (撖其耳） 共催化劑 (拥tM耳） 第3成份 (撤其耳） 溶劑 (克） 辛烯 效 率 (克）（公斤Ceiu/克Ti) 12 A(1.5) A (2.25) DIBAL-B0T (15) 1461 135 1.35 13 A(1.5) B(2.25) DIBAL-B0T (15) 1461 137 1.35 14 Α(1·5) C(2.25) DIBAL-B0T (15) 1453 139 1.90 15 Β(〇_5) C(0.75) DIBAL-B0T ⑸ 1444 137 3.29 16 Α(0.5) C(0.75) DIBAL-B0T (5) 1462 140 4.02 17 Β(0·5) C(0.75) DIBAL-B0T ⑸ 1456 137 2.51 18 C(0.5) C(0.75> DIBAL-B0T (5) 1450 138 2.77 A=(t-丁基酿胺基)二甲基（η β-四甲基瓌戊二烯基浪（π 4-1，3-戊二稀) Β=(異丙基酿胺基Μ二甲基Μη β-2,3,4,6-四甲基?δ基)鈦二甲基 C=(t-丁基醯胺基 >(二甲基）（^*-2,3,4,6-四甲基茚基)钛二甲基 Μ 3 二（去氳牛脂烷基〉甲基銨甲基）三（五氟笨基）苯基硼酸鹽 ((Ct ·- *e) aN(Me)H*B<CeHe) (C*Fe) 3)之配製 例2的合成步驟大童被重覆除了那硼酸鹽是甲基三（' 五氟苯基）硼醴鹽的娌播。 聚合作用 一掴一加侖的携拌反應器中加入1440毫升的Isopar·" E 溶液、126g的卜辛烯、和氫（約25毫升於35Apsi * 0.24Δ MPa)。此反應器加熱至13〇υ且跑和以乙烯至450 psig 本紙張尺度適用中國國家標準（CNS ) A4祕（210X297公釐) ----------"'装------訂------^ .- -- (請先閱讀背面之注意事項再填寫本頁} : 「 -35 - 387908 Λ7 B7 五、發明説明（33 ) (3.1 MPa)。催化劑組成配製於乾燥箱中Μ混合（t-丁基醯 胺基）二甲基（n a-四甲基環戊二烯基）钛（η «-1,3-戊二烯） 催化劑、二（去氫牛脂烷基）甲基鞍）三（五氟苯基）苯 基硼酸鹽和（三異丁基鋁修正甲基鋁氣烷（ΜΜΑ0) —起而成 得到B/Ti原子比例1.5/1以及Al/Titb 10/1。此混合物接箸 傳送至添加環路並注入於反應器。聚合反應讓其進行 10分撞同時加入乙烯Μ維持歴力在450 psU(3.1 MPa>。 此聚合物溶液從反應器傳送至一悃玻璃鍋中且在120C下 於真空爐內乾燥16小時。效率是0.6《公斤·聚合物/克钛金 屬）〇 例4 二（二十二基）甲基銨四（五氟苯基）硼酸鹽 (Ca,H*„)a(GH,)NHB(C6F9)* 經濟部中央標準局貝工消费合作社印褽 (請先閲讀背面之注意事項再填寫本頁) (C"H«e), (CH3)NHB(CsFe)* (ARMEEN® M2HE從 Akzo Nobel得到）（3.87克，5.97毫其耳）溶於40ml己烷中，HC1 水溶液（1M，5.97毫升）以針简加入，導致形成白色沈澱。 此混合物置於一機械搌動器且剌烈拫動30分鐘，然後加入 一値在30寒升水和20毫升戊烷混合物中的LiB(CBFeh(4.30g ，6.27毫其耳）於其中。這混合物再被拫動另30分鐘。其 接箸被倒入一分撞湄斗且此水溶液層被移除。此有機層以 < 30毫升的飽和氣化納水溶液沖洗兩次 > 接箸以水沖洗兩次 。此有機層Μ硫酸鎂乾燥。此有機層然後過濾經過一餹玻 璃搪瓷（10-15撤米）而得到一清晰的淡棕色溶液。這溶液 傳送至一瓶子，徹底Μ氮氣喷射，且放置於乾燥箱。己烷 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐） -36 - 3§1祕 ： ._ _ 丨丨_ 五、發明说明（34) 在真空下移除而得到固體殘餘物。此殘餘物毫升戊烷 磨碎而得到一淡棕色固體。此固體再溶解於35-40毫升丨sopar E之中，且此溶掖濃度以重力測置為18.0重董百分比。 聚合作用 大量重覆例1中的聚合反醮狀況用1444克混合的烷類 溶劑、124克卜辛烯共單醴、1·〇撤其耳（t-丁基酿胺基） 二甲基（rje-四甲基瓌戊二烯基）钛（n4-l,3-戊二烯）催 化劑、1.0撤其耳二（二十二基）甲基敍四（五截苯基） 硼酸鹽共催化劑和10撤其耳甲基鋁氣烷而導致形成乙燔/ 卜丁烯共聚物有3.2kg聚合物/克钛的效率。 ：--------^d------IT------^ • - 〆 (請先聞讀背面之注^^項再填寫本頁)Γ ? 經濟部中央標準局貝工消費合作杜印褽 本紙張尺度通用中國國家梯準（CNS > A4说格（210X297公釐） -37 -
Claims (1)
- SST908 A8B8C8D8 六、申請專利範圍 專利範圍修正本修正 補見_妗1丨/1^ -ft : 告本 經 濟 部 智 慧 財 產 局 貝 工 消 费 合 作 杜 印 製 修正日期：88年11月 其係由下列通式所表示：[L*_ H]+A-，其中：L*為一有機胺，該有機胺包含從】至3 個Cww之烷基，且具有從12至1〇〇個總碳數；以及 A—為一未配位的硼酸鹽陰離子， 該活化劑之特徵在於在25。〇下，其於己烷、環己 烷或是甲基環己烷争之溶解度至少為5重量百分比。 2.如申請專利範圍第丨項之催化劑活化劑，其中該未配 位陰離子是四（五氟笨基）硼酸鹽。 3·如申請專利範圍第1項之催化劑活化劑 2 個 C10_40 烷基且含有21至90個總碳數 4_如申請專利範圍第2項之催化劑活化劑 2個C丨a，烷基且含有21至90個總碳數。 5·如申請專利範圍第4項之催化劑活化劑’其係為二（十 八基）甲基銨四（五氟苯基）硼酸鹽，或是二（去氫_牛脂 烷基）甲基銨四（五氟苯基）硼酸鹽。 —種聚合反應方法，其包含在從〇至25(rc之溫度與 從1個大氣壓至1〇〇個大氣壓之壓力下，使至少一或 數個α-烯烴與一包含一第4族金屬錯化合物及一催化 劑活化劑之催化劑系統接觸，其特徵在於該催化劑活 化劑係為_如申諝專利範圍第1至5項中任一項之催 化劑活化劑β 7. 如申請專利範圍第6項之方法其為一溶液聚合反應。 8. 如申請專利範圍第7項之方法，其為迷續式的。 其申1/包含 其中1/包含 6. 本紙張尺度國國家棬準規格⑽χ 297 4-- —-—η衣--------訂---------線^ (請先閱讀背面之注意Ϋ項再填寫本頁) •38· SST908 A8B8C8D8 六、申請專利範圍 專利範圍修正本修正 補見_妗1丨/1^ -ft : 告本 經 濟 部 智 慧 財 產 局 貝 工 消 费 合 作 杜 印 製 修正日期：88年11月 其係由下列通式所表示：[L*_ H]+A-，其中：L*為一有機胺，該有機胺包含從】至3 個Cww之烷基，且具有從12至1〇〇個總碳數；以及 A—為一未配位的硼酸鹽陰離子， 該活化劑之特徵在於在25。〇下，其於己烷、環己 烷或是甲基環己烷争之溶解度至少為5重量百分比。 2.如申請專利範圍第丨項之催化劑活化劑，其中該未配 位陰離子是四（五氟笨基）硼酸鹽。 3·如申請專利範圍第1項之催化劑活化劑 2 個 C10_40 烷基且含有21至90個總碳數 4_如申請專利範圍第2項之催化劑活化劑 2個C丨a，烷基且含有21至90個總碳數。 5·如申請專利範圍第4項之催化劑活化劑’其係為二（十 八基）甲基銨四（五氟苯基）硼酸鹽，或是二（去氫_牛脂 烷基）甲基銨四（五氟苯基）硼酸鹽。 —種聚合反應方法，其包含在從〇至25(rc之溫度與 從1個大氣壓至1〇〇個大氣壓之壓力下，使至少一或 數個α-烯烴與一包含一第4族金屬錯化合物及一催化 劑活化劑之催化劑系統接觸，其特徵在於該催化劑活 化劑係為_如申諝專利範圍第1至5項中任一項之催 化劑活化劑β 7. 如申請專利範圍第6項之方法其為一溶液聚合反應。 8. 如申請專利範圍第7項之方法，其為迷續式的。 其申1/包含 其中1/包含 6. 本紙張尺度國國家棬準規格⑽χ 297 4-- —-—η衣--------訂---------線^ (請先閱讀背面之注意Ϋ項再填寫本頁) •38·
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| US6130302A (en) | 1996-08-19 | 2000-10-10 | Northwestern University | Synthesis and use of (polyfluoroaryl)fluoroanions of aluminum, gallium and indium |
| US6262200B1 (en) | 1996-08-19 | 2001-07-17 | Northwestern University | (Polyfluoroaryl)fluoroanions of aluminum, gallium, and indium of enhanced utility, uses thereof, and products based thereon |
| AU747745B2 (en) | 1997-08-15 | 2002-05-23 | Dow Chemical Company, The | Films produced from substantially linear homogeneous olefin polymer compositions |
| WO2000001766A1 (en) | 1998-07-01 | 2000-01-13 | Exxon Chemical Patents Inc. | Elastic blends comprising crystalline polymer and crystallizable polymers of propylene |
| US6974878B2 (en) * | 2001-03-21 | 2005-12-13 | Symyx Technologies, Inc. | Catalyst ligands, catalytic metal complexes and processes using same |
| US6316663B1 (en) | 1998-09-02 | 2001-11-13 | Symyx Technologies, Inc. | Catalyst ligands, catalytic metal complexes and processes using and methods of making the same |
| US6521793B1 (en) | 1998-10-08 | 2003-02-18 | Symyx Technologies, Inc. | Catalyst ligands, catalytic metal complexes and processes using same |
| US6475946B1 (en) | 1999-10-22 | 2002-11-05 | Exxonmobil Chemical Patents Inc. | Olefin polymerization catalysis with aryl substituted carbenium cationic complexes |
| US6476164B1 (en) | 1999-10-22 | 2002-11-05 | Exxonmobil Chemical Patents Inc. | Carbenium cationic complexes suitable for polymerization catalysts |
| US6169208B1 (en) | 1999-12-03 | 2001-01-02 | Albemarle Corporation | Process for producing a magnesium di[tetrakis(Faryl)borate] and products therefrom |
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1997
- 1997-03-14 ES ES97915130T patent/ES2147985T3/es not_active Expired - Lifetime
- 1997-03-14 EP EP97915130A patent/EP0889912B1/en not_active Expired - Lifetime
- 1997-03-14 BR BR9708232A patent/BR9708232A/pt not_active IP Right Cessation
- 1997-03-14 US US08/818,530 patent/US5919983A/en not_active Expired - Lifetime
- 1997-03-14 CN CN97193268A patent/CN1120849C/zh not_active Expired - Lifetime
- 1997-03-14 AU AU22149/97A patent/AU2214997A/en not_active Abandoned
- 1997-03-14 JP JP53446297A patent/JP3990458B2/ja not_active Expired - Lifetime
- 1997-03-14 DE DE69702506T patent/DE69702506T2/de not_active Expired - Lifetime
- 1997-03-14 KR KR10-1998-0707648A patent/KR100437238B1/ko active IP Right Grant
- 1997-03-14 RU RU98119439/04A patent/RU2178422C2/ru not_active IP Right Cessation
- 1997-03-14 WO PCT/US1997/004234 patent/WO1997035893A1/en active IP Right Grant
- 1997-03-14 CA CA002245839A patent/CA2245839C/en not_active Expired - Lifetime
- 1997-03-14 AT AT97915130T patent/ATE194629T1/de not_active IP Right Cessation
- 1997-03-26 AR ARP970101236A patent/AR006420A1/es active IP Right Grant
- 1997-03-26 TW TW086103868A patent/TW387908B/zh not_active IP Right Cessation
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- 1997-03-27 ID IDP971040A patent/ID18470A/id unknown
- 1997-05-31 SA SA97180101A patent/SA97180101B1/ar unknown
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1998
- 1998-09-25 NO NO19984466A patent/NO323319B1/no not_active IP Right Cessation
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| AR006420A1 (es) | 1999-08-25 |
| EP0889912B1 (en) | 2000-07-12 |
| ES2147985T3 (es) | 2000-10-01 |
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| NO984466D0 (no) | 1998-09-25 |
| US5919983A (en) | 1999-07-06 |
| AU2214997A (en) | 1997-10-17 |
| US6121185A (en) | 2000-09-19 |
| KR20000005028A (ko) | 2000-01-25 |
| DE69702506T2 (de) | 2001-03-08 |
| CA2245839A1 (en) | 1997-10-02 |
| EP0889912A1 (en) | 1999-01-13 |
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| RU2178422C2 (ru) | 2002-01-20 |
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| ID18470A (id) | 1998-04-09 |
| SA97180101B1 (ar) | 2006-04-25 |
| KR100437238B1 (ko) | 2004-08-16 |
| BR9708232A (pt) | 1999-08-03 |
| WO1997035893A1 (en) | 1997-10-02 |
| CA2245839C (en) | 2005-06-14 |
| JP3990458B2 (ja) | 2007-10-10 |
| CN1214699A (zh) | 1999-04-21 |
| ATE194629T1 (de) | 2000-07-15 |
| NO984466L (no) | 1998-09-25 |
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