DE69510563T2 - Verfahren zum caronylieren von aethylen und in diesem gebrauchtes katalytisches system - Google Patents
Verfahren zum caronylieren von aethylen und in diesem gebrauchtes katalytisches systemInfo
- Publication number
- DE69510563T2 DE69510563T2 DE69510563T DE69510563T DE69510563T2 DE 69510563 T2 DE69510563 T2 DE 69510563T2 DE 69510563 T DE69510563 T DE 69510563T DE 69510563 T DE69510563 T DE 69510563T DE 69510563 T2 DE69510563 T2 DE 69510563T2
- Authority
- DE
- Germany
- Prior art keywords
- caronylating
- aethylene
- system used
- catalytic system
- catalyst system
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- 230000003197 catalytic effect Effects 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 230000006315 carbonylation Effects 0.000 abstract 1
- 238000005810 carbonylation reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229940078552 o-xylene Drugs 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
Classifications
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
- B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9425911.6A GB9425911D0 (en) | 1994-12-22 | 1994-12-22 | Process for the carbonylation of olefins and catalyst system for use therein |
| PCT/GB1995/003021 WO1996019434A1 (en) | 1994-12-22 | 1995-12-22 | Process for the carbonylation of ethylene and catalyst system for use therein |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69510563D1 DE69510563D1 (de) | 1999-08-05 |
| DE69510563T2 true DE69510563T2 (de) | 1999-11-25 |
Family
ID=10766369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69510563T Expired - Lifetime DE69510563T2 (de) | 1994-12-22 | 1995-12-22 | Verfahren zum caronylieren von aethylen und in diesem gebrauchtes katalytisches system |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6348621B1 (de) |
| EP (1) | EP0799180B1 (de) |
| JP (1) | JP3949716B2 (de) |
| KR (1) | KR100423212B1 (de) |
| CN (1) | CN1073546C (de) |
| AT (1) | ATE181725T1 (de) |
| AU (1) | AU701935B2 (de) |
| BR (1) | BR9510249A (de) |
| CA (1) | CA2207672C (de) |
| CZ (1) | CZ288904B6 (de) |
| DE (1) | DE69510563T2 (de) |
| DK (1) | DK0799180T3 (de) |
| ES (1) | ES2133837T3 (de) |
| GB (1) | GB9425911D0 (de) |
| HU (1) | HU215407B (de) |
| NZ (1) | NZ297842A (de) |
| TW (1) | TW318839B (de) |
| WO (1) | WO1996019434A1 (de) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9705699D0 (en) | 1997-03-19 | 1997-05-07 | Ici Plc | Process for the carbonylation of ethylene |
| US6489506B2 (en) | 1997-03-19 | 2002-12-03 | Lucite International Uk Limited | Process for the palladium and phosphine ligand catalyzed carbonylation of ethylene |
| GB9717059D0 (en) * | 1997-08-13 | 1997-10-15 | Ici Plc | Method of manufacturing phosphine compound |
| GB9722733D0 (en) * | 1997-10-29 | 1998-10-28 | Ici Plc | Production of esters |
| GB9800915D0 (en) * | 1998-01-17 | 1998-03-11 | Ici Plc | Production of alkyl esters |
| GB9805348D0 (en) * | 1998-03-16 | 1998-05-06 | Ici Plc | Compound |
| GB9918229D0 (en) † | 1999-08-04 | 1999-10-06 | Ici Plc | Improvements relating to metal-compound catalysed processes |
| US6743911B2 (en) † | 2000-03-14 | 2004-06-01 | Shell Oil Company | Process for the carbonylation of pentenenitrile |
| MY127358A (en) * | 2000-03-14 | 2006-11-30 | Shell Int Research | Process for the carbonylation of ethylenically unsaturated compounds |
| MY127093A (en) * | 2000-05-17 | 2006-11-30 | Lucite Int Uk Ltd | Bidentate ligands useful in catalyst systems |
| DE10048874A1 (de) | 2000-09-29 | 2002-04-11 | Basf Ag | Katalysatorsystem und Verfahren zur Carbonylierung |
| DE10106348A1 (de) | 2001-02-09 | 2002-08-14 | Basf Ag | Als Katalysator oder zur Herstellung eines Katalysatorsystems geeignete Verbindung |
| DE10228293A1 (de) | 2001-07-28 | 2003-02-13 | Basf Ag | Verfahren zur Herstellung von Dialkylketonen |
| US20030105348A1 (en) | 2001-11-19 | 2003-06-05 | Bunel Emilio E. | Process for making 5-cyanovaleric acid, adipic acid or dimethyl adipate |
| ATE552907T1 (de) * | 2002-02-19 | 2012-04-15 | Lucite Int Uk Ltd | Verfahren zur carbonylierung ethylenisch ungesättigter verbindungen und zugehöriger katalysator |
| TWI301481B (en) | 2002-08-10 | 2008-10-01 | Lucite Int Uk Ltd | A catalyst system |
| GB0218613D0 (en) * | 2002-08-10 | 2002-09-18 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds |
| GB0228018D0 (en) * | 2002-11-30 | 2003-01-08 | Lucite Int Uk Ltd | Carbonylation of ester |
| PL213201B1 (pl) | 2002-09-12 | 2013-01-31 | Lucite Int Uk Ltd | Zwiazek nadajacy sie w szczególnosci do katalizowania reakcji karbonylowania nienasyconych zwiazków, sposób wytwarzania tych zwiazków, kompozycja zawierajaca takie zwiazki, sposób karbonylowania etylenowo nienasyconych zwiazków z zastosowaniem tych zwiazków, a takze ich zastosowanie |
| WO2005003070A1 (en) * | 2003-07-03 | 2005-01-13 | Lucite International Uk Limited | Process for the hydroformylation of ethylenically unsaturated compounds |
| GB0315536D0 (en) * | 2003-07-03 | 2003-08-06 | Lucite Int Uk Ltd | Process for the hydroformylation of ethylenically unsaturated compounds |
| GB0403592D0 (en) * | 2004-02-18 | 2004-03-24 | Lucite Int Uk Ltd | A catalyst system |
| US7265242B2 (en) | 2004-02-26 | 2007-09-04 | Shell Oil Company | Process for the carbonylation of ethylenically or acetylenically unsaturated compounds |
| GB0411951D0 (en) * | 2004-05-28 | 2004-06-30 | Lucite Int Uk Ltd | Carbonylation of ester |
| GB0516556D0 (en) | 2005-08-12 | 2005-09-21 | Lucite Int Uk Ltd | Improved catalyst system |
| EA025600B1 (ru) | 2005-11-17 | 2017-01-30 | ЛУСАЙТ ИНТЕРНЕЙШНЛ Ю Кей ЛИМИТЕД | Способ карбонилирования этиленненасыщенных соединений, каталитическая система и бидентатный лиганд |
| GB0607494D0 (en) * | 2006-04-13 | 2006-05-24 | Lucite Int Uk Ltd | Metal complexes |
| EP2097429B1 (de) * | 2006-12-02 | 2019-03-06 | Lucite International UK Limited | Neue carbonilierungsliganden und ihre verwendung bei der carbonilierung von ethylenisch ungesättigten verbindungen |
| GB0625518D0 (en) * | 2006-12-21 | 2007-01-31 | Lucite Int Uk Ltd | Carbonylation of conjugated dienes |
| GB0713624D0 (en) * | 2007-07-13 | 2007-08-22 | Lucite Int Uk Ltd | Improved solvent for catalyst system |
| GB0812297D0 (en) * | 2008-07-04 | 2008-08-13 | Lucite Int Uk Ltd | Novel carbonylation ligand sand thier use of in the carbonylation of ethylenically unsaturated compounds |
| JP5918695B2 (ja) * | 2009-09-03 | 2016-05-18 | テクニカル・ユニヴァーシティ・オブ・デンマーク | 双性イオンおよび／または酸官能化イオン性液体を含むパラジウム触媒系 |
| GB0921875D0 (en) | 2009-12-15 | 2010-01-27 | Lucite Int Uk Ltd | A continuous process for the carbonylation of ethylene |
| GB0921876D0 (en) | 2009-12-15 | 2010-01-27 | Lucite Int Uk Ltd | Improved carbonylation process |
| GB0922255D0 (en) | 2009-12-21 | 2010-02-03 | Lucite Int Uk Ltd | Method of producing acrylic and methacrylic acid |
| GB201000078D0 (en) * | 2010-01-05 | 2010-02-17 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands |
| DE102010002809A1 (de) | 2010-03-12 | 2011-11-17 | Evonik Degussa Gmbh | Verfahren zur Herstellung von linearen alpha,omega-Dicarbonsäurediestern |
| MY179932A (en) | 2010-11-24 | 2020-11-19 | Lucite Int Uk Ltd | A process for the production of methacrylic acid and its derivatives and polymers produced therefrom |
| MX340192B (es) | 2011-02-09 | 2016-06-30 | Lucite Int Uk Ltd | Un proceso para la produccion de acido (met)acrilico y derivados y polimeros producidos a partir del mismo. |
| GB201122054D0 (en) | 2011-12-21 | 2012-02-01 | Lucite Int Uk Ltd | A continuous process for the carbonylation of ethylene |
| WO2013107902A1 (en) | 2012-01-20 | 2013-07-25 | Dsm Ip Assets B.V. | Process for the separation of a dissolved catalyst system from an alkoxycarbonylation reaction mixture |
| KR102293168B1 (ko) | 2013-09-30 | 2021-08-24 | 다우 글로벌 테크놀로지스 엘엘씨 | 알킬 알카노에이트의 기상 제조 |
| CN106458831A (zh) | 2014-06-24 | 2017-02-22 | 陶氏环球技术有限责任公司 | 用于制造低voc聚结助剂的方法 |
| WO2017135897A1 (en) * | 2016-02-02 | 2017-08-10 | Agency For Science, Technology And Research | A catalyst for the carbonylation of alkenes |
| EP3272730B1 (de) | 2016-07-19 | 2019-01-02 | Evonik Degussa GmbH | Verfahren zur alkoxycarbonylierung von ethern |
| KR20210133296A (ko) | 2019-03-12 | 2021-11-05 | 미쯔비시 케미컬 주식회사 | 촉매, 촉매의 제조 방법, 그리고 불포화 카르복실산 및/또는 불포화 카르복실산에스테르의 제조 방법 |
| CN111087306B (zh) | 2019-12-27 | 2021-08-03 | 南京诚志清洁能源有限公司 | 芳基双齿膦配体组合催化制备有机羧酸酯的方法 |
| CN113912646B (zh) * | 2021-11-18 | 2024-05-17 | 浙江新化化工股份有限公司 | 一种双齿膦配体的制备方法 |
| WO2023117754A1 (de) | 2021-12-23 | 2023-06-29 | Röhm Gmbh | Verfahren zur herstellung von alkylmethacrylaten mit verbesserter ausbeute und verminderten emissionen flüchtiger organischer verbindungen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4269781A (en) * | 1980-02-08 | 1981-05-26 | Celanese Corporation | Dimeric carbonylation of 1,3-butadiene |
| KR880007426A (ko) * | 1986-12-24 | 1988-08-27 | 오노 알버어스 | 팔라듐 촉매를 사용한 올레핀형 불포화 화합물의 카르보닐화 방법 |
| US4960949A (en) * | 1988-12-22 | 1990-10-02 | Eastman Kodak Company | Low pressure rhodium catalyzed hydroformylation of olefins |
| ES2077337T3 (es) * | 1991-01-15 | 1995-11-16 | Shell Int Research | Procedimiento para la carbonilacion de olefinas. |
| CN1036915C (zh) * | 1992-04-08 | 1998-01-07 | 国际壳牌研究有限公司 | 用钯/膦催化剂进行的羰基化方法 |
-
1994
- 1994-12-22 GB GBGB9425911.6A patent/GB9425911D0/en active Pending
-
1995
- 1995-12-22 ES ES95941792T patent/ES2133837T3/es not_active Expired - Lifetime
- 1995-12-22 HU HU9702202A patent/HU215407B/hu not_active IP Right Cessation
- 1995-12-22 EP EP95941792A patent/EP0799180B1/de not_active Expired - Lifetime
- 1995-12-22 AT AT95941792T patent/ATE181725T1/de active
- 1995-12-22 NZ NZ297842A patent/NZ297842A/xx not_active IP Right Cessation
- 1995-12-22 DE DE69510563T patent/DE69510563T2/de not_active Expired - Lifetime
- 1995-12-22 JP JP51961196A patent/JP3949716B2/ja not_active Expired - Lifetime
- 1995-12-22 CN CN95197050A patent/CN1073546C/zh not_active Expired - Lifetime
- 1995-12-22 AU AU43095/96A patent/AU701935B2/en not_active Expired
- 1995-12-22 US US08/860,159 patent/US6348621B1/en not_active Expired - Lifetime
- 1995-12-22 DK DK95941792T patent/DK0799180T3/da active
- 1995-12-22 CZ CZ19971932A patent/CZ288904B6/cs not_active IP Right Cessation
- 1995-12-22 WO PCT/GB1995/003021 patent/WO1996019434A1/en not_active Application Discontinuation
- 1995-12-22 KR KR1019970704200A patent/KR100423212B1/ko active
- 1995-12-22 CA CA002207672A patent/CA2207672C/en not_active Expired - Lifetime
- 1995-12-22 BR BR9510249A patent/BR9510249A/pt not_active IP Right Cessation
-
1996
- 1996-01-04 TW TW85100056A patent/TW318839B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| AU4309596A (en) | 1996-07-10 |
| AU701935B2 (en) | 1999-02-11 |
| ATE181725T1 (de) | 1999-07-15 |
| NZ297842A (en) | 2000-01-28 |
| JP3949716B2 (ja) | 2007-07-25 |
| CA2207672A1 (en) | 1996-06-27 |
| DK0799180T3 (da) | 2000-01-31 |
| CZ288904B6 (cs) | 2001-09-12 |
| CA2207672C (en) | 2006-10-10 |
| DE69510563D1 (de) | 1999-08-05 |
| US6348621B1 (en) | 2002-02-19 |
| EP0799180A1 (de) | 1997-10-08 |
| KR100423212B1 (ko) | 2004-05-20 |
| HU215407B (hu) | 1998-12-28 |
| CN1073546C (zh) | 2001-10-24 |
| JPH10511034A (ja) | 1998-10-27 |
| GB9425911D0 (en) | 1995-02-22 |
| WO1996019434A1 (en) | 1996-06-27 |
| CN1171098A (zh) | 1998-01-21 |
| KR987000251A (en) | 1998-03-30 |
| BR9510249A (pt) | 1997-11-04 |
| TW318839B (en) | 1997-11-01 |
| ES2133837T3 (es) | 1999-09-16 |
| HUT77016A (hu) | 1998-03-02 |
| CZ193297A3 (cs) | 1998-02-18 |
| EP0799180B1 (de) | 1999-06-30 |
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