ZA200302284B - Catalyst system for high-cis polybutadiene. - Google Patents
Catalyst system for high-cis polybutadiene. Download PDFInfo
- Publication number
- ZA200302284B ZA200302284B ZA200302284A ZA200302284A ZA200302284B ZA 200302284 B ZA200302284 B ZA 200302284B ZA 200302284 A ZA200302284 A ZA 200302284A ZA 200302284 A ZA200302284 A ZA 200302284A ZA 200302284 B ZA200302284 B ZA 200302284B
- Authority
- ZA
- South Africa
- Prior art keywords
- catalyst system
- alkyl
- ternary
- aluminum
- amount
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims description 41
- 239000005063 High cis polybutadiene Substances 0.000 title claims description 7
- -1 alkyl aluminum chloride compound Chemical class 0.000 claims description 28
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 17
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 229910017052 cobalt Inorganic materials 0.000 claims description 15
- 239000010941 cobalt Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000001868 cobalt Chemical class 0.000 claims description 14
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 12
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- KDMCQAXHWIEEDE-UHFFFAOYSA-L cobalt(2+);7,7-dimethyloctanoate Chemical compound [Co+2].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O KDMCQAXHWIEEDE-UHFFFAOYSA-L 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 5
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
- OPAGOSHJYNFXGD-UHFFFAOYSA-L cobalt(2+) 2,2-dimethyloctanoate Chemical compound [Co+2].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O OPAGOSHJYNFXGD-UHFFFAOYSA-L 0.000 description 2
- HWVKIRQMNIWOLT-UHFFFAOYSA-L cobalt(2+);octanoate Chemical compound [Co+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HWVKIRQMNIWOLT-UHFFFAOYSA-L 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- UIUSXTVZPVPHOU-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol cobalt Chemical compound N(CCO)(CCO)CCO.[Co] UIUSXTVZPVPHOU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229920000231 antioxidant polymer Polymers 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- FCEOGYWNOSBEPV-FDGPNNRMSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FCEOGYWNOSBEPV-FDGPNNRMSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- QRQUTSPLBBZERR-UHFFFAOYSA-M dioctylalumanylium;chloride Chemical compound CCCCCCCC[Al](Cl)CCCCCCCC QRQUTSPLBBZERR-UHFFFAOYSA-M 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- BBDZBXWEYMXNTN-UHFFFAOYSA-M ethyl(octyl)alumanylium;chloride Chemical compound [Cl-].CCCCCCCC[Al+]CC BBDZBXWEYMXNTN-UHFFFAOYSA-M 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/26—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of manganese, iron group metals or platinum group metals
-
- 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/06—Butadiene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23983700P | 2000-10-12 | 2000-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302284B true ZA200302284B (en) | 2004-03-24 |
Family
ID=22903940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302284A ZA200302284B (en) | 2000-10-12 | 2003-03-24 | Catalyst system for high-cis polybutadiene. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6887956B2 (es) |
| EP (1) | EP1325040B1 (es) |
| JP (1) | JP2004511589A (es) |
| KR (1) | KR20030040528A (es) |
| CN (1) | CN1468263A (es) |
| AU (1) | AU2001296505A1 (es) |
| BR (1) | BR0114663A (es) |
| CA (1) | CA2425441A1 (es) |
| DE (1) | DE60141341D1 (es) |
| MX (1) | MXPA03003252A (es) |
| RO (1) | RO121273B1 (es) |
| RU (1) | RU2003113209A (es) |
| TW (1) | TWI287548B (es) |
| WO (1) | WO2002030997A2 (es) |
| ZA (1) | ZA200302284B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003102041A1 (en) * | 2002-05-31 | 2003-12-11 | Dow Global Technologies Inc. | A two-step butadiene polymerization process for manufacturing high-cis 1,4-ploybutadiene |
| EP2507270A1 (en) * | 2009-12-02 | 2012-10-10 | Styron Europe GmbH | Catalyst systems for rubber polymerizations |
| EP2523978A2 (en) * | 2010-01-15 | 2012-11-21 | Reliance Industries Limited | High-cis polybutadiene rubber in benign solvents and process for preparation thereof |
| US8893725B2 (en) | 2011-01-28 | 2014-11-25 | R. J. Reynolds Tobacco Company | Polymeric materials derived from tobacco |
| US9000107B2 (en) | 2011-01-31 | 2015-04-07 | Bridgestone Corporation | Process for producing polydienes |
| KR101986201B1 (ko) | 2011-05-09 | 2019-06-07 | 가부시키가이샤 브리지스톤 | 고-cis 폴리디엔 제조방법 |
| CN108409973A (zh) * | 2017-12-27 | 2018-08-17 | 管燕 | 一种用于折叠盆的橡胶及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135725A (en) * | 1957-05-31 | 1964-06-02 | Goodrich Gulf Chem Inc | Process of polymerizing conjugated diolefins with a cobalt salt-hydrocarbyl aluminumcompound catalyst |
| US3336280A (en) | 1960-10-14 | 1967-08-15 | Phillips Petroleum Co | Process for production of rubbery polymers |
| US5280081A (en) * | 1991-06-05 | 1994-01-18 | The B. F. Goodrich Company | Highly hydrogenated nonfunctional or functional terminated conjugated diene polymers |
| US5397851A (en) | 1993-11-09 | 1995-03-14 | Polysar Rubber Corporation | Process for cis-1,4-polybutadiene production with reduced gel formation |
| EP0770631B1 (en) | 1995-10-18 | 2000-06-21 | The Dow Chemical Company | Manufacturing process for high cis poly(butadiene) |
| EP0816398B1 (en) * | 1996-06-28 | 2002-08-14 | Ube Industries, Ltd. | Process for producing polybutadiene |
| US5733835A (en) | 1996-08-05 | 1998-03-31 | The Goodyear Tire & Rubber Company | Cobalt containing catalyst system |
| JP3680516B2 (ja) | 1997-09-12 | 2005-08-10 | 宇部興産株式会社 | 共役ジエン重合用触媒及び共役ジエン重合体の製造方法 |
| CA2246608A1 (en) | 1998-09-04 | 2000-03-04 | Bayer Inc. | Gel reduction in high cis-1,4 polybutadiene production process |
| US6235849B1 (en) | 1999-02-05 | 2001-05-22 | The B. F. Goodrich Company | Method of preparing norbornene sulfonamide polymers |
-
2001
- 2001-10-02 BR BR0114663-7A patent/BR0114663A/pt not_active IP Right Cessation
- 2001-10-02 CN CNA018170250A patent/CN1468263A/zh active Pending
- 2001-10-02 DE DE60141341T patent/DE60141341D1/de not_active Expired - Lifetime
- 2001-10-02 AU AU2001296505A patent/AU2001296505A1/en not_active Abandoned
- 2001-10-02 RU RU2003113209/04A patent/RU2003113209A/ru not_active Application Discontinuation
- 2001-10-02 WO PCT/US2001/030855 patent/WO2002030997A2/en active Application Filing
- 2001-10-02 MX MXPA03003252A patent/MXPA03003252A/es unknown
- 2001-10-02 EP EP01977379A patent/EP1325040B1/en not_active Expired - Lifetime
- 2001-10-02 CA CA002425441A patent/CA2425441A1/en not_active Abandoned
- 2001-10-02 JP JP2002534380A patent/JP2004511589A/ja active Pending
- 2001-10-02 KR KR10-2003-7005049A patent/KR20030040528A/ko not_active Application Discontinuation
- 2001-10-02 RO ROA200300320A patent/RO121273B1/ro unknown
- 2001-10-02 US US10/398,875 patent/US6887956B2/en not_active Expired - Fee Related
- 2001-10-11 TW TW090125111A patent/TWI287548B/zh not_active IP Right Cessation
-
2003
- 2003-03-24 ZA ZA200302284A patent/ZA200302284B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2425441A1 (en) | 2002-04-18 |
| MXPA03003252A (es) | 2003-09-10 |
| US6887956B2 (en) | 2005-05-03 |
| CN1468263A (zh) | 2004-01-14 |
| KR20030040528A (ko) | 2003-05-22 |
| EP1325040A2 (en) | 2003-07-09 |
| WO2002030997A2 (en) | 2002-04-18 |
| BR0114663A (pt) | 2004-01-13 |
| DE60141341D1 (de) | 2010-04-01 |
| JP2004511589A (ja) | 2004-04-15 |
| TWI287548B (en) | 2007-10-01 |
| AU2001296505A1 (en) | 2002-04-22 |
| RO121273B1 (ro) | 2007-02-28 |
| WO2002030997A3 (en) | 2002-07-18 |
| RU2003113209A (ru) | 2004-11-10 |
| US20040029722A1 (en) | 2004-02-12 |
| EP1325040B1 (en) | 2010-02-17 |
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