SG42936A1 - Ferrocenyl diphosphines as ligands for homogeneous catalysts - Google Patents
Ferrocenyl diphosphines as ligands for homogeneous catalystsInfo
- Publication number
- SG42936A1 SG42936A1 SG1996001003A SG1996001003A SG42936A1 SG 42936 A1 SG42936 A1 SG 42936A1 SG 1996001003 A SG1996001003 A SG 1996001003A SG 1996001003 A SG1996001003 A SG 1996001003A SG 42936 A1 SG42936 A1 SG 42936A1
- Authority
- SG
- Singapore
- Prior art keywords
- ligands
- homogeneous catalysts
- diphosphines
- ferrocenyl
- ferrocenyl diphosphines
- Prior art date
Links
Classifications
-
- 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
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
-
- 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
- B01J31/2291—Olefins
-
- 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
-
- 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
- B01J31/24—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
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/2471—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- 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
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
-
- 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
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0202—Polynuclearity
- B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
-
- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0286—Complexes comprising ligands or other components characterized by their function
-
- 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
- B01J2531/822—Rhodium
-
- 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
- B01J2531/827—Iridium
-
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH106892 | 1992-04-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
SG42936A1 true SG42936A1 (en) | 1997-10-17 |
Family
ID=4201698
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SG1996001003A SG42936A1 (en) | 1992-04-02 | 1993-03-24 | Ferrocenyl diphosphines as ligands for homogeneous catalysts |
Country Status (6)
Country | Link |
---|---|
US (4) | US5371256A (ja) |
EP (1) | EP0564406B1 (ja) |
JP (1) | JP3320488B2 (ja) |
CA (1) | CA2093084C (ja) |
DE (1) | DE59309554D1 (ja) |
SG (1) | SG42936A1 (ja) |
Families Citing this family (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5171892A (en) * | 1991-07-02 | 1992-12-15 | E. I. Du Pont De Nemours And Company | Chiral phospholanes via chiral 1,4-diol cyclic sulfates |
EP0612758B1 (de) * | 1993-02-26 | 2003-04-09 | Syngenta Participations AG | Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
EP0646590B1 (de) * | 1993-10-01 | 1999-08-25 | Novartis AG | Mit Fluoralkyl substituierte Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
AU1575495A (en) | 1994-02-02 | 1995-08-21 | Ciba-Geigy Ag | Hydrogenation catalyst, process for the preparation thereof and hydrogenation process |
CN1117727C (zh) * | 1994-02-02 | 2003-08-13 | 辛根塔参与股份公司 | 亚胺的氢化方法 |
US5543559A (en) | 1994-07-07 | 1996-08-06 | Hoffman-La Roche Inc. | Process for the enantioselective hydrogenation of ketosiophorone derivatives |
US5563284A (en) * | 1994-09-09 | 1996-10-08 | Phillips Petroleum Company | Cyclopentadienyl-type ligands, metallocenes, catalyst systems, preparation, and use |
EP0729969B1 (de) * | 1995-02-24 | 2000-08-16 | Novartis AG | Silylierte Ferrocenyldiphosphine, an anorganische oder polymere organische Träger gebundene silylierte Ferrocenyldiphosphine sowie Metallkomplexe davon, ihre Herstellung und Verwendung |
DE69603466T2 (de) * | 1995-04-11 | 1999-11-18 | Novartis Ag | Dihalogenierte ferrocene und verfahren zu deren herstellung |
ATE209190T1 (de) * | 1995-05-23 | 2001-12-15 | Lonza Ag | Verfahren zur herstellung von optisch aktiven 2- piperazincarbonsäurederivaten |
EP1125930A1 (de) * | 1995-05-23 | 2001-08-22 | Lonza Ag | Optisch aktive 2-Piperazincarbonsäurederivate und Verfahren zu ihrer Herstellung |
UA51652C2 (uk) * | 1995-06-08 | 2002-12-16 | Новартіс Аг | Спосіб гідрування імінів |
JPH11508903A (ja) * | 1995-07-11 | 1999-08-03 | ロンザ アーゲー | 光学活性1−(p−メトキシベンジル)−1,2,3,4,5,6,7,8−オクタヒドロイソキノリンの製造方法 |
HRP960302A2 (en) * | 1995-07-26 | 1998-04-30 | Ciba Geigy Ag | Process for the hydrogenation of imines |
TW330194B (en) * | 1995-07-27 | 1998-04-21 | Novartis Ag | Process for the hydrogenation of imines |
US6008393A (en) * | 1995-07-27 | 1999-12-28 | Novartis Ag | Iridium-diphospine complexes and process for the hydrogenation of imines |
JP3915015B2 (ja) | 1995-08-22 | 2007-05-16 | 味の素株式会社 | 光学活性2−ヒドロキシ−4−アリール酪酸またはそのエステルの製造方法 |
ES2147889T3 (es) * | 1996-01-19 | 2000-10-01 | Lonza Ag | Metodo para preparar 3-hidroxiquinuclidinol opticamente activo. |
DE59711086D1 (de) * | 1996-03-21 | 2004-01-22 | Lonza Ag | Verfahren zur Herstellung von Arylamiden Heteroaromatischer Carbonsäuren |
SK283920B6 (sk) | 1996-03-28 | 2004-05-04 | Lonza Ag | Spôsob výroby arylamidov heteroaromatických karboxylových kyselín |
CA2201218C (en) * | 1996-04-23 | 2004-09-28 | Rudolf Fuchs | Process for the preparation of optically active piperazine-2-carboxylic acid derivatives |
US5900484A (en) * | 1996-09-18 | 1999-05-04 | Lonza Ag | Process for the preparation of arylamides of heteroaromatic carboxylic acids |
ES2143816T3 (es) * | 1996-05-09 | 2000-05-16 | Lonza Ag | Procedimiento para la preparacion de arilamidas de acidos carboxilicos heteroaromaticos. |
WO1998001457A1 (en) * | 1996-07-10 | 1998-01-15 | Novartis Ag | Functionalized ferrocenyldiphosphines, a process for their preparation and their use |
CA2209392C (en) * | 1996-07-23 | 2007-02-20 | Yves Bessard | Process for preparing pyridinecarboxylic esters |
WO1998015565A1 (en) * | 1996-10-07 | 1998-04-16 | Novartis Ag | Chiral ferrocenyls |
US6214763B1 (en) * | 1997-05-20 | 2001-04-10 | Firmenich Sa | Ruthenium catalysts and their use in the asymmetric hydrogenation of weakly coordinating substrates |
WO1999001453A1 (en) * | 1997-07-02 | 1999-01-14 | F. Hoffmann-La Roche Ag | A process for the manufacture of optically active chromanylpyridine derivatives |
DE59807829D1 (de) * | 1997-10-14 | 2003-05-15 | Lonza Ag | Zweikernige Iridium(I)-phosphinkomplexe und ihre Verwendung als Katalysator in der asymmetrischen Hydroaminierung von Olefinen |
EP0967015B1 (de) * | 1998-06-19 | 2005-01-12 | Degussa AG | Verwendung von Ferrocenylliganden zur katalytischen enantioselektiven Hydrierung |
EP0965574B1 (de) | 1998-06-19 | 2004-10-13 | Degussa AG | Verfahren zur enantioselektiven Hydrierung |
EP0974590A1 (en) * | 1998-07-13 | 2000-01-26 | F. Hoffmann-La Roche Ag | Process for the preparation of chiral lactones by asymetrical hydrogenation |
US6222039B1 (en) | 1998-07-13 | 2001-04-24 | Hoffman-La Roche Inc. | Process for the preparation of chiral lactones |
CA2347146A1 (en) * | 1998-11-05 | 2000-05-18 | Chirotech Technology Limited | Chiral ligands for asymmetric catalysis |
DE19952348A1 (de) * | 1998-12-19 | 2000-06-21 | Degussa | Liganden und Komplexe zur enantioselektiven Hydrierung |
US6258979B1 (en) * | 1999-11-22 | 2001-07-10 | Henri Kagan | Chiral ferrocene phosphines active in asymmetric catalysis |
ATE312111T1 (de) | 2000-07-03 | 2005-12-15 | Solvias Ag | Ferrocenyl-diphosphane und ihre verwendung |
GB0120167D0 (en) * | 2001-08-17 | 2001-10-10 | Chirotech Technology Ltd | Asymmetric hydrogenation |
US20040186314A1 (en) * | 2001-08-17 | 2004-09-23 | Malan Christophe Guillaume | Process for the preparation of enantiomerically enriched n-acyl-beta-amino acid derivatives by enantioselective hydrogenation of the corresponding (z)-enamides |
AR043515A1 (es) * | 2003-03-19 | 2005-08-03 | Merck & Co Inc | Procedimiento para preparar derivados quirales beta aminoacidos mediante hidrogenacion asimetrica |
TW200602293A (en) * | 2004-04-05 | 2006-01-16 | Merck & Co Inc | Process for the preparation of enantiomerically enriched beta amino acid derivatives |
CN101175565B (zh) | 2005-04-08 | 2011-11-09 | 帝斯曼知识产权资产管理有限公司 | 内酯的制造 |
WO2006108636A1 (en) | 2005-04-15 | 2006-10-19 | Dsm Ip Assets B.V. | Manufacture of thiolactones |
DE102005052588A1 (de) * | 2005-11-02 | 2007-05-10 | Grünenthal GmbH | Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse |
JP2009530403A (ja) * | 2006-03-21 | 2009-08-27 | イエール・ユニバーシテイ | 芳香族化合物とアンモニアまたは金属アミドとの反応からのアリールアミンの合成法 |
EP2098511A1 (en) | 2008-03-07 | 2009-09-09 | Solvias AG | Process for preparing compounds containing a hydronaphtalene structure with an unsymmetrically substituted benzene ring |
EP2202236A1 (en) | 2008-12-23 | 2010-06-30 | Solvias AG | Chiral ligands |
US8450496B2 (en) * | 2009-03-24 | 2013-05-28 | Hoffman-La Roche Inc. | Process for the preparation of propionic acid derivatives |
GB201320869D0 (en) | 2013-11-26 | 2014-01-08 | Johnson Matthey Plc | Process |
CN112824423B (zh) * | 2019-11-21 | 2023-01-13 | 中国科学院大连化学物理研究所 | 一种手性二茂铁膦-吲哚氨基膦配体及其制备方法和应用 |
EP4222133A1 (en) | 2020-09-29 | 2023-08-09 | Eastman Chemical Company | Propylene hydroformylation processes using bisphosphine ligands as catalysts |
US20230382937A1 (en) | 2020-09-30 | 2023-11-30 | Eastman Chemical Company | Processes of preparing ferrocene ligand mixtures suitable for propylene hydroformylation |
WO2022072184A1 (en) | 2020-09-30 | 2022-04-07 | Eastman Chemical Company | Use of highly isoselective, thermally stable ferrocene catalysts for propylene hydroformylation |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5011995A (en) * | 1987-07-28 | 1991-04-30 | Ciba-Geigy Corporation | Process for the preparation of optically active secondary amines |
-
1993
- 1993-03-24 SG SG1996001003A patent/SG42936A1/en unknown
- 1993-03-24 DE DE59309554T patent/DE59309554D1/de not_active Expired - Lifetime
- 1993-03-24 EP EP93810212A patent/EP0564406B1/de not_active Expired - Lifetime
- 1993-03-26 US US08/037,783 patent/US5371256A/en not_active Ceased
- 1993-03-31 CA CA002093084A patent/CA2093084C/en not_active Expired - Lifetime
- 1993-03-31 JP JP07311593A patent/JP3320488B2/ja not_active Expired - Lifetime
-
1994
- 1994-08-17 US US08/292,150 patent/US5463097A/en not_active Expired - Lifetime
-
1995
- 1995-06-02 US US08/459,435 patent/US5563309A/en not_active Expired - Lifetime
-
2000
- 2000-05-18 US US09/572,931 patent/USRE37344E1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE59309554D1 (de) | 1999-06-10 |
USRE37344E1 (en) | 2001-08-28 |
JPH0641171A (ja) | 1994-02-15 |
EP0564406B1 (de) | 1999-05-06 |
US5371256A (en) | 1994-12-06 |
CA2093084C (en) | 2005-08-09 |
JP3320488B2 (ja) | 2002-09-03 |
CA2093084A1 (en) | 1993-10-03 |
US5563309A (en) | 1996-10-08 |
US5463097A (en) | 1995-10-31 |
EP0564406A1 (de) | 1993-10-06 |
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