JP2003529572A - 置換多環式シクロペンタジエン及びその製造方法 - Google Patents
置換多環式シクロペンタジエン及びその製造方法Info
- Publication number
- JP2003529572A JP2003529572A JP2001572442A JP2001572442A JP2003529572A JP 2003529572 A JP2003529572 A JP 2003529572A JP 2001572442 A JP2001572442 A JP 2001572442A JP 2001572442 A JP2001572442 A JP 2001572442A JP 2003529572 A JP2003529572 A JP 2003529572A
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- JP
- Japan
- Prior art keywords
- group
- formula
- metal
- compound
- carbon atoms
- 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.)
- Pending
Links
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 125000003367 polycyclic group Chemical group 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 9
- -1 Polycyclic cyclopentadiene compound Chemical class 0.000 claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 41
- 239000004711 α-olefin Substances 0.000 claims abstract description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000005977 Ethylene Substances 0.000 claims abstract description 26
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 13
- 150000003624 transition metals Chemical class 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 62
- 229910052751 metal Inorganic materials 0.000 claims description 50
- 239000002184 metal Substances 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 42
- 239000000047 product Substances 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 36
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 30
- 229910052782 aluminium Inorganic materials 0.000 claims description 22
- 239000000725 suspension Substances 0.000 claims description 21
- 239000011734 sodium Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 16
- 229910052726 zirconium Inorganic materials 0.000 claims description 15
- 150000001993 dienes Chemical class 0.000 claims description 14
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 13
- 230000000737 periodic effect Effects 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000000962 organic group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052733 gallium Inorganic materials 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 150000002902 organometallic compounds Chemical group 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- 229910052749 magnesium Chemical group 0.000 claims description 4
- 239000011777 magnesium Chemical group 0.000 claims description 4
- 150000002739 metals Chemical group 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 150000002602 lanthanoids Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 230000002547 anomalous effect Effects 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000007334 copolymerization reaction Methods 0.000 description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical class C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 7
- BIKNWJXRLLQCCI-UHFFFAOYSA-N 4,5-dihydro-3ah-cyclopenta[a]naphthalene Chemical compound C1=CC=C2C3=CC=CC3CCC2=C1 BIKNWJXRLLQCCI-UHFFFAOYSA-N 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 6
- OZZOQKKWIZTPKB-UHFFFAOYSA-N 6,8-dimethyl-3,3a,4,5-tetrahydrocyclopenta[a]naphthalen-2-one Chemical compound C1CC2CC(=O)C=C2C2=CC(C)=CC(C)=C21 OZZOQKKWIZTPKB-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- GCHBULYORREASW-UHFFFAOYSA-L [Cl-].[Cl-].C123C=CC=CC3=CCCC2=CC=C1[Zr+2]C1=CC=C2C11C=CC=CC1=CCC2 Chemical compound [Cl-].[Cl-].C123C=CC=CC3=CCCC2=CC=C1[Zr+2]C1=CC=C2C11C=CC=CC1=CCC2 GCHBULYORREASW-UHFFFAOYSA-L 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- DPNICLBGUUSDGM-UHFFFAOYSA-N 3a,4,5,6-tetrahydrobenzo[e]azulene Chemical compound C1CCC2C=CC=C2C2=CC=CC=C21 DPNICLBGUUSDGM-UHFFFAOYSA-N 0.000 description 5
- QIVPRXLVRZVXFY-UHFFFAOYSA-L [Cl-].[Cl-].CC1=C2CCC3=C(C2=CC(=C1)C)C(C=C3)[Zr+2]C3C=CC1=C3C3=CC(=CC(=C3CC1)C)C Chemical compound [Cl-].[Cl-].CC1=C2CCC3=C(C2=CC(=C1)C)C(C=C3)[Zr+2]C3C=CC1=C3C3=CC(=CC(=C3CC1)C)C QIVPRXLVRZVXFY-UHFFFAOYSA-L 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910003002 lithium salt Inorganic materials 0.000 description 5
- 159000000002 lithium salts Chemical class 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 5
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910007926 ZrCl Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002085 enols Chemical class 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- DOKKVPGOHCOXLC-UHFFFAOYSA-N ethyl 1-oxo-3,4-dihydro-2h-naphthalene-2-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)CCC2=C1 DOKKVPGOHCOXLC-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000008040 ionic compounds Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- KWHUHTFXMNQHAA-UHFFFAOYSA-N 6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CCCCC2=CC=CC=C12 KWHUHTFXMNQHAA-UHFFFAOYSA-N 0.000 description 3
- OCUWHDQQWWNFMS-UHFFFAOYSA-N 6,8-dimethyl-4,5-dihydro-3ah-cyclopenta[a]naphthalene Chemical compound C1CC2C=CC=C2C2=CC(C)=CC(C)=C21 OCUWHDQQWWNFMS-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- LHNMGYHIXMIZDE-UHFFFAOYSA-N ethyl 1-oxo-2-prop-2-ynyl-3,4-dihydronaphthalene-2-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)(CC#C)CCC2=C1 LHNMGYHIXMIZDE-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910000474 mercury oxide Inorganic materials 0.000 description 3
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- RJUCIROUEDJQIB-GQCTYLIASA-N (6e)-octa-1,6-diene Chemical compound C\C=C\CCCC=C RJUCIROUEDJQIB-GQCTYLIASA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- DBRSOGDNSUYZCR-UHFFFAOYSA-N 3,3a,4,5-tetrahydrocyclopenta[a]naphthalen-2-one Chemical compound C1=CC=C2C3=CC(=O)CC3CCC2=C1 DBRSOGDNSUYZCR-UHFFFAOYSA-N 0.000 description 2
- FUDNBFMOXDUIIE-UHFFFAOYSA-N 3,7-dimethylocta-1,6-diene Chemical compound C=CC(C)CCC=C(C)C FUDNBFMOXDUIIE-UHFFFAOYSA-N 0.000 description 2
- UYJCNOMEGPDXMV-UHFFFAOYSA-N 5,7-dimethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(C)=CC(C)=C21 UYJCNOMEGPDXMV-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000012312 sodium hydride Substances 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
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- 230000001502 supplementing effect Effects 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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Classifications
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/122—Metal aryl or alkyl compounds
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- 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
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
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- 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
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
-
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/12—Olefin polymerisation or copolymerisation
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
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- 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
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- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
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- 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
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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
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| PCT/EP2001/003127 WO2001074745A1 (en) | 2000-03-31 | 2001-03-20 | Substituted polycyclic cyclopentadienes and method for their preparation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004505019A (ja) * | 2000-06-30 | 2004-02-19 | ダウ グローバル テクノロジーズ インコーポレーテッド | 多環式、縮合環化合物、金属錯体及び重合方法 |
| WO2020171073A1 (ja) * | 2019-02-19 | 2020-08-27 | 株式会社 三和化学研究所 | ベンゾアゼピン誘導体の製造方法及びその中間体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2261292B1 (en) | 2002-10-15 | 2014-07-23 | ExxonMobil Chemical Patents Inc. | Polyolefin adhesive compositions |
| US7550528B2 (en) | 2002-10-15 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Functionalized olefin polymers |
| US7223822B2 (en) | 2002-10-15 | 2007-05-29 | Exxonmobil Chemical Patents Inc. | Multiple catalyst and reactor system for olefin polymerization and polymers produced therefrom |
| US7541402B2 (en) | 2002-10-15 | 2009-06-02 | Exxonmobil Chemical Patents Inc. | Blend functionalized polyolefin adhesive |
| WO2010077163A1 (en) * | 2008-12-30 | 2010-07-08 | Gosudarstvennoe Uchebno-Nauchnoe Uchrezhdenie Khimichesky Fakultet Moskovskogo Gosudarstvennogo Universiteta Im. M.V.Lomonosova | Synthesis of substituted tetrahydroindenyl complexes, metallocenes produced therefrom and use of the metallocenes in polymerisation processes |
| CN111132988B (zh) * | 2017-09-28 | 2023-06-20 | 尤尼威蒂恩技术有限责任公司 | 环状有机化合物和茂金属的合成 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06340684A (ja) * | 1990-11-12 | 1994-12-13 | Hoechst Ag | 2−置換インデニル誘導体のリガンドを含有するメタロセン、その製造方法およびその使用方法 |
| JPH0841088A (ja) * | 1994-03-22 | 1996-02-13 | Pcd Polymere Gmbh | メタロセン及びそれらをオレフィン重合に使用する方法 |
| JPH09501184A (ja) * | 1994-04-06 | 1997-02-04 | モンテル テクノロジー カンパニー ビーブイ | メタロセン化合物及びオレフィンの重合用触媒への使用 |
| JPH0967326A (ja) * | 1995-03-03 | 1997-03-11 | Roussel Uclaf | 新規な三環式誘導体、それらの製造法、光学活性又はラセミ形のコルヒチン及びチオコルヒチン並びにそれらの類似体又は誘導体の製造への使用並びに中間体 |
| JPH10158288A (ja) * | 1996-10-31 | 1998-06-16 | Hoechst Ag | 部分的に水素化されたπリガンドを含有するメタロセン |
| JPH10231314A (ja) * | 1996-12-19 | 1998-09-02 | Enichem Spa | メタロセン、それらの製造およびアルファ−オレフィンの重合におけるそれらの使用 |
| JP2001133886A (ja) * | 1999-08-26 | 2001-05-18 | Kuraray Co Ltd | 背面投射形スクリーン用プラスチックシート |
| JP2002530286A (ja) * | 1998-11-18 | 2002-09-17 | モンテル テクノロジー カンパニー ビーブイ | オレフィン重合触媒としてのビス(テトラヒドロ−インデニル)メタロセン |
-
2000
- 2000-03-31 IT IT2000MI000680A patent/IT1318436B1/it active
-
2001
- 2001-03-20 ES ES01913894T patent/ES2234819T3/es not_active Expired - Lifetime
- 2001-03-20 KR KR1020027011762A patent/KR100862128B1/ko not_active Expired - Fee Related
- 2001-03-20 CA CA2404549A patent/CA2404549C/en not_active Expired - Lifetime
- 2001-03-20 WO PCT/EP2001/003127 patent/WO2001074745A1/en not_active Ceased
- 2001-03-20 AT AT01913894T patent/ATE286496T1/de active
- 2001-03-20 DE DE60108231T patent/DE60108231T2/de not_active Expired - Lifetime
- 2001-03-20 US US10/240,279 patent/US6844478B2/en not_active Expired - Lifetime
- 2001-03-20 JP JP2001572442A patent/JP2003529572A/ja active Pending
- 2001-03-20 EP EP01913894A patent/EP1268375B1/en not_active Expired - Lifetime
- 2001-03-20 MX MXPA02009374A patent/MXPA02009374A/es active IP Right Grant
- 2001-03-20 AU AU2001239308A patent/AU2001239308A1/en not_active Abandoned
- 2001-03-28 MY MYPI20011448A patent/MY126014A/en unknown
- 2001-03-29 AR ARP010101493A patent/AR029503A1/es unknown
- 2001-04-16 TW TW090109058A patent/TWI222964B/zh not_active IP Right Cessation
-
2004
- 2004-11-12 US US10/986,188 patent/US6930158B2/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06340684A (ja) * | 1990-11-12 | 1994-12-13 | Hoechst Ag | 2−置換インデニル誘導体のリガンドを含有するメタロセン、その製造方法およびその使用方法 |
| JPH0841088A (ja) * | 1994-03-22 | 1996-02-13 | Pcd Polymere Gmbh | メタロセン及びそれらをオレフィン重合に使用する方法 |
| JPH09501184A (ja) * | 1994-04-06 | 1997-02-04 | モンテル テクノロジー カンパニー ビーブイ | メタロセン化合物及びオレフィンの重合用触媒への使用 |
| JPH0967326A (ja) * | 1995-03-03 | 1997-03-11 | Roussel Uclaf | 新規な三環式誘導体、それらの製造法、光学活性又はラセミ形のコルヒチン及びチオコルヒチン並びにそれらの類似体又は誘導体の製造への使用並びに中間体 |
| JPH10158288A (ja) * | 1996-10-31 | 1998-06-16 | Hoechst Ag | 部分的に水素化されたπリガンドを含有するメタロセン |
| JPH10231314A (ja) * | 1996-12-19 | 1998-09-02 | Enichem Spa | メタロセン、それらの製造およびアルファ−オレフィンの重合におけるそれらの使用 |
| JP2002530286A (ja) * | 1998-11-18 | 2002-09-17 | モンテル テクノロジー カンパニー ビーブイ | オレフィン重合触媒としてのビス(テトラヒドロ−インデニル)メタロセン |
| JP2001133886A (ja) * | 1999-08-26 | 2001-05-18 | Kuraray Co Ltd | 背面投射形スクリーン用プラスチックシート |
Non-Patent Citations (4)
| Title |
|---|
| JPN6011003206, KONDO,T. et al, "1−exo− and 1−endo(Trimethylsilyl)−2,3−ferrocenoindene. Preparation and methanolysis in the presence", Journal of Organometallic Chemistry, 1973, Vol.61, p.347−54 * |
| JPN6011003208, CAIS,M. et al, "Organometallic studies. XVII. A novel approach to the synthesis of the benzopentalene system", Journal of the American Chemical Society, 1965, Vol.87, No.24, p.5607−14 * |
| JPN6011003211, ALVAREZ,M. et al, "Using the National Cancer Institute Anticancer Drug Screen to assess the effect of MRP expression on", Molecular Pharmacology, 1998, Vol.54, No.5, p.802−814 * |
| JPN6011003214, RIED,W. et al, "Reactions with cyclopentadienones. XXVII. Reduction of substituted cyclopentadienones using the li", Justus Liebigs Annalen der Chemie, 1971, Vol.750, p.91−6 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004505019A (ja) * | 2000-06-30 | 2004-02-19 | ダウ グローバル テクノロジーズ インコーポレーテッド | 多環式、縮合環化合物、金属錯体及び重合方法 |
| WO2020171073A1 (ja) * | 2019-02-19 | 2020-08-27 | 株式会社 三和化学研究所 | ベンゾアゼピン誘導体の製造方法及びその中間体 |
Also Published As
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| AU2001239308A1 (en) | 2001-10-15 |
| DE60108231D1 (de) | 2005-02-10 |
| ITMI20000680A1 (it) | 2001-10-01 |
| EP1268375A1 (en) | 2003-01-02 |
| EP1268375B1 (en) | 2005-01-05 |
| CA2404549C (en) | 2013-06-04 |
| KR100862128B1 (ko) | 2008-10-09 |
| AR029503A1 (es) | 2003-07-02 |
| ATE286496T1 (de) | 2005-01-15 |
| US20050096439A1 (en) | 2005-05-05 |
| US20030166800A1 (en) | 2003-09-04 |
| CA2404549A1 (en) | 2001-10-11 |
| TWI222964B (en) | 2004-11-01 |
| WO2001074745A1 (en) | 2001-10-11 |
| DE60108231T2 (de) | 2005-12-15 |
| ES2234819T3 (es) | 2005-07-01 |
| US6930158B2 (en) | 2005-08-16 |
| MXPA02009374A (es) | 2004-05-14 |
| MY126014A (en) | 2006-09-29 |
| KR20020081413A (ko) | 2002-10-26 |
| IT1318436B1 (it) | 2003-08-25 |
| US6844478B2 (en) | 2005-01-18 |
| ITMI20000680A0 (it) | 2000-03-31 |
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