IL93109A - Process for preparation of 2, (2-bipyridyls) - Google Patents
Process for preparation of 2, (2-bipyridyls)Info
- Publication number
- IL93109A IL93109A IL9310990A IL9310990A IL93109A IL 93109 A IL93109 A IL 93109A IL 9310990 A IL9310990 A IL 9310990A IL 9310990 A IL9310990 A IL 9310990A IL 93109 A IL93109 A IL 93109A
- Authority
- IL
- Israel
- Prior art keywords
- catalyst
- reacting
- pyridine
- nickel
- additionally
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 114
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 107
- 238000006243 chemical reaction Methods 0.000 abstract description 58
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 57
- 238000000034 method Methods 0.000 abstract description 52
- 229910052759 nickel Inorganic materials 0.000 abstract description 38
- 230000008569 process Effects 0.000 abstract description 26
- 239000007788 liquid Substances 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 10
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- 238000013461 design Methods 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 description 112
- 239000002585 base Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 25
- 229910000564 Raney nickel Inorganic materials 0.000 description 21
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000908 ammonium hydroxide Substances 0.000 description 16
- 239000007868 Raney catalyst Substances 0.000 description 14
- 239000008188 pellet Substances 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 239000010935 stainless steel Substances 0.000 description 10
- 229910001220 stainless steel Inorganic materials 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 8
- 230000009849 deactivation Effects 0.000 description 8
- 230000007420 reactivation Effects 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 230000004913 activation Effects 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000975 co-precipitation Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000012421 spiking Methods 0.000 description 5
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N alpha-methylpyridine Natural products CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000282346 Meles meles Species 0.000 description 2
- 241001469893 Oxyzygonectes dovii Species 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- JLDSOYXADOWAKB-UHFFFAOYSA-N aluminium nitrate Chemical class [Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JLDSOYXADOWAKB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000004311 natamycin Substances 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006578 reductive coupling reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/299,789 US4966972A (en) | 1989-01-19 | 1989-01-19 | Process and catalyst for the preparation of 2,2'-bipyridyls |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL93109A true IL93109A (en) | 1994-04-12 |
Family
ID=23156313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9310990A IL93109A (en) | 1989-01-19 | 1990-01-18 | Process for preparation of 2, (2-bipyridyls) |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4966972A (pt) |
| EP (1) | EP0454731B1 (pt) |
| JP (1) | JP2828773B2 (pt) |
| KR (1) | KR930002274B1 (pt) |
| AT (1) | ATE135691T1 (pt) |
| AU (1) | AU626766B2 (pt) |
| BR (1) | BR9007042A (pt) |
| CA (1) | CA2008014C (pt) |
| DE (1) | DE69026073T2 (pt) |
| DK (1) | DK0454731T3 (pt) |
| ES (1) | ES2084020T3 (pt) |
| IL (1) | IL93109A (pt) |
| WO (1) | WO1990008139A1 (pt) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2882189A (en) * | 1988-02-05 | 1989-08-10 | Signode Corporation | Hot gas welding of thermoplastic material and transverse weld produced thereby |
| US5221747A (en) * | 1989-01-19 | 1993-06-22 | Reilly Industries, Inc. | Improved process and catalyst for the preparation of 2,2' bipyridyls |
| IE63524B1 (en) * | 1990-07-18 | 1995-05-03 | Reilly Ind Inc | Improved Processes and Catalysts for the Preparation of 2,2'-Bipyridyls |
| GR1002169B (en) * | 1995-03-29 | 1996-03-06 | Georgios Karathanos | Welding tape machine for the packing of objects. |
| JP3032980B1 (ja) * | 1999-06-14 | 2000-04-17 | 三協化学株式会社 | ２―ピリジルピリジン誘導体の製造方法 |
| JP3272326B2 (ja) * | 1999-06-14 | 2002-04-08 | 三協化学株式会社 | ２−ピリジルピリジン誘導体の製造方法 |
| CN105461620B (zh) * | 2015-11-23 | 2018-06-19 | 安徽千和新材料科技发展有限公司 | 一种2,2’-联吡啶的雷尼镍催化制备方法 |
| CN107935919B (zh) * | 2017-11-17 | 2019-09-03 | 南京红太阳生物化学有限责任公司 | 一种2,2’-联吡啶及其衍生物的制备方法 |
| CN108440392B (zh) * | 2018-04-19 | 2020-09-25 | 合肥工业大学 | 一种合成2，2’-联吡啶的连续化生产装置及生产方法 |
| CN110801841A (zh) * | 2019-11-27 | 2020-02-18 | 中国科学院大连化学物理研究所 | 一种用于合成吡啶偶联制2,2’-联吡啶的催化剂及其制备方法和应用 |
| GB2599981B (en) * | 2020-05-14 | 2023-06-14 | Johnson Matthey Plc | Catalyst for producing a substituted or unsubstituted pyridine |
| CN116948681B (zh) * | 2022-04-20 | 2025-04-01 | 中国石油化工股份有限公司 | 一种全馏分汽油加氢装置及方法 |
| CN114920687B (zh) * | 2022-05-25 | 2024-04-09 | 南京红太阳生物化学有限责任公司 | 一种4,4′-联吡啶的制备方法 |
| CN115010654A (zh) * | 2022-06-14 | 2022-09-06 | 南京红太阳生物化学有限责任公司 | 一种2,2’联吡啶绿色合成工艺 |
| CN115245841B (zh) * | 2022-08-22 | 2024-01-26 | 山东明化新材料有限公司 | 一种镍钴金属骨架催化剂在2,2’-联吡啶制备中的应用 |
| CN115430365B (zh) * | 2022-11-09 | 2023-03-03 | 北京弗莱明科技有限公司 | 一种利用近等温反应装置制备2,2’-联吡啶的方法 |
| CN116099218B (zh) * | 2023-03-07 | 2023-06-23 | 北京弗莱明科技有限公司 | 一种连续式制备α,α'-联氮杂苯的方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053846A (en) * | 1962-09-11 | Method for the manufacture of z | ||
| US2526718A (en) * | 1950-10-24 | Coating compositions | ||
| GB899015A (en) * | 1960-04-26 | 1962-06-20 | Ici Ltd | Preparation of catalyst |
| DE1156768B (de) * | 1960-12-17 | 1963-11-07 | Varta Ag | Verfahren zur Aktivierung metallischer Katalysatoren |
| GB1000656A (en) * | 1962-03-08 | 1965-08-11 | Ici Ltd | 2-2 dipyridyl and dialkyl derivatives thereof |
| GB981353A (en) * | 1962-07-03 | 1965-01-27 | Ici Ltd | Preparation of dipyridyls |
| GB1014076A (en) * | 1963-06-18 | 1965-12-22 | Ici Ltd | Dipyridyls |
| GB1060661A (en) * | 1963-09-12 | 1967-03-08 | Ici Ltd | Manufacture of bipyridyls |
| US3560404A (en) * | 1966-12-30 | 1971-02-02 | Varta Ag | Reactivating pyrophoric type catalysts in an organic solvent |
| GB1202711A (en) * | 1967-01-20 | 1970-08-19 | Ici Ltd | Catalyst regeneration process |
| GB1283693A (en) * | 1968-10-03 | 1972-08-02 | Ici Ltd | Preparation of 2,2'-bipyridyls |
| GB1377213A (en) * | 1971-05-03 | 1974-12-11 | Ici Ltd | Preparation of 2,2-bipyridyls |
| BE785802A (fr) * | 1971-07-15 | 1973-01-03 | Ici Ltd | Preparation de 2,2'-bipyridyles |
| US3822279A (en) * | 1971-07-15 | 1974-07-02 | Ici Ltd | Preparation of 2,2'-bipyridyls |
-
1989
- 1989-01-19 US US07/299,789 patent/US4966972A/en not_active Expired - Lifetime
-
1990
- 1990-01-16 KR KR1019900702059A patent/KR930002274B1/ko not_active Expired - Lifetime
- 1990-01-16 DK DK90902013.3T patent/DK0454731T3/da active
- 1990-01-16 ES ES90902013T patent/ES2084020T3/es not_active Expired - Lifetime
- 1990-01-16 AU AU49560/90A patent/AU626766B2/en not_active Expired
- 1990-01-16 JP JP2502285A patent/JP2828773B2/ja not_active Expired - Lifetime
- 1990-01-16 WO PCT/US1990/000295 patent/WO1990008139A1/en not_active Ceased
- 1990-01-16 EP EP90902013A patent/EP0454731B1/en not_active Expired - Lifetime
- 1990-01-16 DE DE69026073T patent/DE69026073T2/de not_active Expired - Lifetime
- 1990-01-16 BR BR909007042A patent/BR9007042A/pt not_active IP Right Cessation
- 1990-01-16 AT AT90902013T patent/ATE135691T1/de not_active IP Right Cessation
- 1990-01-18 CA CA002008014A patent/CA2008014C/en not_active Expired - Lifetime
- 1990-01-18 IL IL9310990A patent/IL93109A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU626766B2 (en) | 1992-08-06 |
| EP0454731A1 (en) | 1991-11-06 |
| DK0454731T3 (da) | 1996-06-24 |
| WO1990008139A1 (en) | 1990-07-26 |
| EP0454731B1 (en) | 1996-03-20 |
| BR9007042A (pt) | 1991-11-12 |
| KR910700235A (ko) | 1991-03-14 |
| CA2008014C (en) | 1999-05-11 |
| AU4956090A (en) | 1990-08-13 |
| ATE135691T1 (de) | 1996-04-15 |
| DE69026073T2 (de) | 1996-09-05 |
| DE69026073D1 (de) | 1996-04-25 |
| ES2084020T3 (es) | 1996-05-01 |
| US4966972A (en) | 1990-10-30 |
| JPH04504567A (ja) | 1992-08-13 |
| KR930002274B1 (ko) | 1993-03-27 |
| JP2828773B2 (ja) | 1998-11-25 |
| CA2008014A1 (en) | 1990-07-19 |
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