ES2105503T3 - Procedimiento para la produccion de 1,4-ciclohexanodimetanol. - Google Patents
Procedimiento para la produccion de 1,4-ciclohexanodimetanol.Info
- Publication number
- ES2105503T3 ES2105503T3 ES94300072T ES94300072T ES2105503T3 ES 2105503 T3 ES2105503 T3 ES 2105503T3 ES 94300072 T ES94300072 T ES 94300072T ES 94300072 T ES94300072 T ES 94300072T ES 2105503 T3 ES2105503 T3 ES 2105503T3
- Authority
- ES
- Spain
- Prior art keywords
- dialkyl
- cyclohexanedicarboxylate
- feed
- contg
- cyclohexanedimethanol
- 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
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 abstract 10
- 239000003054 catalyst Substances 0.000 abstract 8
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 abstract 7
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 238000005984 hydrogenation reaction Methods 0.000 abstract 4
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000012544 monitoring process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/27—Polyhydroxylic alcohols containing saturated rings
- C07C31/272—Monocyclic
- C07C31/276—Monocyclic with a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
Abstract
SE DESCRIBE UN PROCESO CONTINUO PARA LA PRODUCCION DE 1,4CICLOHEXANODIMETANO QUE TIENE UNA RELACION DESEADA O PREDETERMINADA DE TRANS-:CIS-ISOMERO POR HIDROGENACION CATALITICA DE UN 1,4CICLOHEXANODICARBOXILATO DE DIALQUILO EN PRESENCIA DE UN CATALIZADOR DE HIDROGENACION DE ESTE, CUYO PROCESO ES CAPAZ DE SER ACTIVO DURANTE UN PERIODO EXTENSO DE TIEMPO DURANTE EL CUAL EL CATALIZADOR DE HIDROGENACION DISMINUYE LA ACTIVIDAD CATALITICA, CONSISTIENDO DICHO PROCESO EN: A) PREVER UNA ZONA DE HIDROGENACION QUE CONTIENEN UNA CARGA DE CATALIZADOR DE HIDROGENACION GRANULAR CAPAZ DE CATALIZAR LA HIDROGENACION DE ESTERES; DETERMINAR UNA ACTIVIDAD DE REFERENCIA (RA) DEL CATALIZADOR DE HIDROGENACION GRANULAR MIDIENDO LA EXTENSION DE CONVERSION DE 1,4CICLOHEXANODICARBOXILATO DE DIALQUILO A 1,4-CILOHEXANODEIMETANOL AL PASO DE UNA MEZCLA DE REACCION QUE COMPRENDE EL 1,4CICLOHEXANODICARBOXILATO DE DIALQUILO Y UN GAS QUE CONTIENE HIDROGENO A TRAVES DEL CATALIZADOR DE HIDROGENACION GRANULAR A UNA TEMPERATURA Y PRESION DE ALIMENTACION PRESELECCIONADAS, UNA VELOCIDAD DE ALIMENTACION DE 1,4-CICLOHEXANODICARBOXILATO DE DIALQUILO PRESELECCIONADA Y UNA RELACION MOLAR GAS QUE CONTIENEN HIDROGENO:1,4-CICLOHEXANODICARBOXILATO PRESELECCIONADA; C) DETERMINAR UN TIEMPO DE RESIDENCIA EFECTIVO (ERT) PARA PONER EN CONTACTO LA MEZCLA DE REACCION A TEMPERATURA DE ALIMENTACION Y PRESION DE ALIMENTACION CON EL CATALIZADOR DE HIDROGENACION GRANULAR EN LA ACTIVIDAD DE REFERENCIA DE ESTE QUE PRODUCE 1,4-CILOHEXANODIMETANOL QUE TIENE LA RELACION TRANS-:CIS_ISOMRO; D) FORMAR UNA CORRIENTE DE ALIMENTACION VAPOROSA QUE COMPRENDE 1,4-CILOHEXANODICARBOXILATO DE DIALQUILO Y UN GAS QUE CONTIENEN HIDROGENO QUE TIENE UNA RELACION MOLAR DE GAS QUE CONTIENE HIDROGENO:1,4CICLOHEXANODICARBOXILATO DE DIALQUILO; E) ALIMENTAR LA CORRIENTE DE ALIMENTACION VAPOROSA EN LA ZONA DE HIDROGENACION A UNA TEMPERATURA SUSTANCIALMENTE CONSTANTE DE APROXIMADAMENTE 150 (GRADOS) C A APROXIMADAMENTE 350 (GRADOS) C Y QUE ES SUPERIOR AL PUNTO DE ROCIODE LA CORRIENTE DE ALIMENTACION Y A UNA PRESION SUSTANCIALMENTE CONSTANTE EN LA GAMA DE APROXIMADAMENTE 150 PSI (APROXIMADAMENTE 10. BARES) A APROXIMADAMENTE 2000 PSI (APROXIMADAMENTE 37.90 BARES) A UNA VELOCIDAD QUE CORRESPONDE A UN TIEMPO DE RESIDENCIA ACTUAL (ART) DE LA CORRIENTE DE ALIMENTACION EN CONTACTO CON EL CATALIZADOR QUE PRODUCE 1,4CICLOHEXANODIMETANOL DE LA RELACION DESEADA DE TRANS:CIS-ISOMERO: F) RECUPERAR DE LA ZONA DE HIDROGENACION UNA CORRIENTE DE PRODUCTO QUE CONTIENE 1,4CICLOHEXANODIMETANO: G) MONITORIZAR LA ACTIVIDAD ACTUAL (A) DEL CATALIZADOR DE HIDROGENACION GRANULAR CON EL PASO DEL TIEMPO MIDIENDO LA EXTENSION DE CONVERSION DE 1,4CICLOHEXANODICARBOXILATO DE DIALQUILO A 1,4-CICLOHEXANODIMETANOL BAJO LAS CONDICIONES OPERATIVAS ACTUALES DE TEMPERATURA DE ALIMENTACION Y PRESION DE ALIMENTACION, VELOCIDAD DE ALIMENTACION DE 1,4CICLOHEXANODICARBOXILATO DE DIALQUILO, RELACION MOLAR DE GAS QUE CONTIENE HIDROGENO:1,4CICLOHEXANODICARBOXIALTO DE DIALQUILO, H) AJUSTAR AL MENOS UNA CONDICION DE ALIMENTACION DE LA CORRIENTE DE ALIMENTACION VAPOROSA A LA ZONA DE HIDROGENACION ELEGIDA A PARTIR DE (I) LA VELOCIDAD DE ALIMENTACION DE 1,4-CICLOHEXANODICARBOXILATO DE DIALQUILO Y (II) LA RELACION MOLAR DE GAS QUE CONTIENEN HIDROGENO:CICLOHEXANODICARBOXILATO DE DIALQUILO MIENTRAS SE MANTIENEN LA CORRIENTE DE ALIMENTACION POR ENCIMA DE SU PUNTO DE ROCIO PARA OBTENER UN TIEMPO DE RESIDENCIA ACTUAL (ART) DE LA CORRIENTE DE ALIMENTACION VAPOROSA EN CONTACTO CON EL CATALIZADOR QUE CORRESPONDE AL TIEMPO DE RESIDENCIA EFECTIVA (ERT) REQUERIDO PARA OBTENER 1,4-CICLOHEXANODIMETANOL QUE TIENE LA RELACION DESEADA DE TRANS-:CIS-ISOMERO DE ACUERDO CON LA RELACION:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939324752A GB9324752D0 (en) | 1993-12-02 | 1993-12-02 | Process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2105503T3 true ES2105503T3 (es) | 1997-10-16 |
Family
ID=10746030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES94300072T Expired - Lifetime ES2105503T3 (es) | 1993-12-02 | 1994-01-06 | Procedimiento para la produccion de 1,4-ciclohexanodimetanol. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5395987A (es) |
| EP (1) | EP0656337B1 (es) |
| JP (1) | JP4153049B2 (es) |
| KR (1) | KR100279316B1 (es) |
| CN (1) | CN1060152C (es) |
| AT (1) | ATE156112T1 (es) |
| AU (1) | AU674460B2 (es) |
| BR (1) | BR9404846A (es) |
| DE (1) | DE69404612T2 (es) |
| ES (1) | ES2105503T3 (es) |
| GB (1) | GB9324752D0 (es) |
| HK (1) | HK1001727A1 (es) |
| MY (1) | MY121943A (es) |
| SG (1) | SG47898A1 (es) |
| TW (1) | TW279850B (es) |
| ZA (1) | ZA948638B (es) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9324823D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324783D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| GB9324785D0 (en) * | 1993-12-02 | 1994-01-19 | Davy Mckee London | Process |
| CN1073511C (zh) * | 1994-10-05 | 2001-10-24 | 罗姆股份有限公司 | 一种发光二极管印刷头 |
| WO2000058248A1 (en) * | 1999-03-25 | 2000-10-05 | Eastman Chemical Company | Process for producing 1,4-cyclohexanedimethanol with enhanced cis-isomer content |
| US6919489B1 (en) | 2004-03-03 | 2005-07-19 | Eastman Chemical Company | Process for a cyclohexanedimethanol using raney metal catalysts |
| US7538060B2 (en) * | 2007-02-14 | 2009-05-26 | Eastman Chemical Company | Palladium-copper chromite hydrogenation catalysts |
| US20080194398A1 (en) * | 2007-02-14 | 2008-08-14 | Eastman Chemical Company | Ruthenium-copper chromite hydrogenation catalysts |
| US20090142981A1 (en) | 2007-12-03 | 2009-06-04 | Velsicol Chemical Corporation | Novel Compositions Comprising Structural Isomers Of 1,4-Cyclohexanedimethanol Dibenzoate and Polymer Compositions Containing Same |
| KR101099127B1 (ko) * | 2008-10-16 | 2011-12-26 | 한화케미칼 주식회사 | 60%이상의 시스 디(c4-c20)알킬 시클로헥산-1,4-디카르복실레이트의 제조방법 |
| US8420869B2 (en) | 2010-12-09 | 2013-04-16 | Eastman Chemical Company | Process for the preparation of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US8394997B2 (en) | 2010-12-09 | 2013-03-12 | Eastman Chemical Company | Process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US8410317B2 (en) * | 2011-07-29 | 2013-04-02 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol |
| US8410318B2 (en) * | 2011-07-29 | 2013-04-02 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
| US8766017B2 (en) * | 2011-07-29 | 2014-07-01 | Eastman Chemical Company | Integrated process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
| US8877984B2 (en) | 2011-07-29 | 2014-11-04 | Eastman Chemical Company | Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid |
| JP6051980B2 (ja) * | 2013-03-14 | 2016-12-27 | 三菱化学株式会社 | 1,4−シクロヘキサンジメタノールの製造方法 |
| KR102056291B1 (ko) | 2013-06-28 | 2019-12-16 | 에스케이케미칼 주식회사 | 1,4-시클로헥산 디메탄올의 제조방법 |
| US9115155B1 (en) | 2014-03-20 | 2015-08-25 | Eastman Chemical Company | Low-pressure synthesis of cyclohexanedimethanol and derivatives |
| CN105620953B (zh) * | 2014-11-03 | 2018-08-10 | 内蒙古大唐国际克什克腾煤制天然气有限责任公司 | 一种促进储罐内部热扩散的系统和方法 |
| KR102413118B1 (ko) | 2015-11-02 | 2022-06-24 | 에스케이케미칼 주식회사 | 1,4-사이클로헥산디메탄올의 제조 부산물의 처리 방법 |
| CN106748704A (zh) * | 2016-11-14 | 2017-05-31 | 中海油天津化工研究设计院有限公司 | 一种联产1,4‑环己烷二甲醇和环己基‑1,4‑二甲醛的方法 |
| US10329235B2 (en) | 2017-08-31 | 2019-06-25 | ClearWaterBay CHDM Technology Limited | System and method for producing 1,4-cyclohexanedimethanol and 1,4- cyclohexanedicarboxylic acid from terephthalic acid |
| KR102188755B1 (ko) | 2017-12-22 | 2020-12-08 | 한화솔루션 주식회사 | 높은 트랜스 함량을 갖는 사이클로헥산 디메탄올 제조방법 및 이에 의해 제조된 사이클로헥산 디메탄올 |
| CN110152565A (zh) * | 2018-06-15 | 2019-08-23 | 宁波浙铁江宁化工有限公司 | 一种可调节的反应器及该反应器生产催化剂的制备方法 |
| CN114436771B (zh) * | 2020-10-20 | 2024-06-28 | 中国石油化工股份有限公司 | 一种制备环己烷二甲醇的方法 |
| CN115007075B (zh) * | 2021-04-30 | 2024-06-21 | 青岛京润石化工程有限公司 | 一种双反应段的催化剂连续循环反应实验装置 |
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| US2105664A (en) * | 1930-04-17 | 1938-01-18 | Du Pont | Catalytic hydrogenation of hydroaromatic carboxylic acids and their esters |
| US2137407A (en) * | 1931-05-11 | 1938-11-22 | Du Pont | Catalytic hydrogenation process |
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| US2755317A (en) * | 1952-11-10 | 1956-07-17 | Universal Oil Prod Co | Hydrogenation of benzene to cyclohexane |
| US2818393A (en) * | 1953-05-05 | 1957-12-31 | Kellogg M W Co | Method of preparing a catalyst |
| US2830095A (en) * | 1953-05-07 | 1958-04-08 | Olin Mathieson | Production of ethylene chlorohydrin |
| BE592181A (es) * | 1955-12-22 | |||
| US2884450A (en) * | 1956-04-20 | 1959-04-28 | Du Pont | Hydrogenation of unsaturated dilactones to 1,8-octanedioic acids and 1,8-octanediolswith copper chromite catalysts |
| US2917549A (en) * | 1958-01-07 | 1959-12-15 | Eastman Kodak Co | Preparation of trans-1,4-cyclohexanedimethanol |
| NL132671C (es) * | 1960-02-09 | |||
| DE1144703B (de) * | 1960-10-06 | 1963-03-07 | Eastman Kodak Co | Verfahren zur Herstellung von Alkoholen durch katalytische Hydrierung von Estern |
| FR1276722A (fr) * | 1960-10-11 | 1961-11-24 | Eastman Kodak Co | Procédé de préparation d'un catalyseur en vue de la réduction des esters en alcools |
| NL292315A (es) * | 1962-05-05 | |||
| CH438269A (it) * | 1963-05-10 | 1967-06-30 | Snam Spa | Processo di idrogenazione di composti acetilenici miscibili con acqua a composti etilenici |
| US3334149A (en) * | 1964-07-21 | 1967-08-01 | Eastman Kodak Co | Plural stage hydrogenation of dialkyl terephthalate using palladium and then copper chromite |
| US4052467A (en) * | 1967-11-08 | 1977-10-04 | Phillips Petroleum Company | Catalytic reduction of aldehydes to alcohols |
| GB1454440A (en) * | 1974-10-03 | 1976-11-03 | Ucb Sa | Process for the production of butane-1,4-diol from but-2-ene- 1,4-dioic acid |
| GB1464263A (en) * | 1974-12-03 | 1977-02-09 | Ucb Sa | Production of butane-1,4-diol |
| US4032458A (en) * | 1975-08-08 | 1977-06-28 | Petro-Tex Chemical Corporation | Production of 1,4-butanediol |
| US4172961A (en) * | 1975-08-08 | 1979-10-30 | Denka Chemical Corporation | Production of 1,4-butanediol |
| DE2719867A1 (de) * | 1977-05-04 | 1978-11-09 | Bayer Ag | Verfahren zur herstellung von butandiol-1,4 |
| DE2845905C3 (de) * | 1978-10-21 | 1983-05-26 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen Herstellung von Butandiol-1,4 |
| DE3106819A1 (de) * | 1981-02-24 | 1982-09-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,4-butandiol |
| IT1190783B (it) * | 1981-04-29 | 1988-02-24 | Davy Mckee Oil & Chem | Processo per l'idrogenolisi di esteri di acidi carbossilici |
| GB8331793D0 (en) * | 1983-11-29 | 1984-01-04 | Davy Mckee Ltd | Process |
| EP0204730A1 (en) * | 1984-11-21 | 1986-12-17 | DAVY McKEE (LONDON) LIMITED | Process for the production of butane-1,4-diol |
| GB8514002D0 (en) * | 1985-06-04 | 1985-07-10 | Davy Mckee Ltd | Process |
| GB8514001D0 (en) * | 1985-06-04 | 1985-07-10 | Davy Mckee Ltd | Process |
| US4652685A (en) * | 1985-11-15 | 1987-03-24 | General Electric Company | Hydrogenation of lactones to glycols |
| DE3610698A1 (de) * | 1986-03-29 | 1987-10-01 | Henkel Kgaa | Katalysator und verfahren zur katalytischen hydrierung von fettsaeuremethylestern im festbett |
| WO1988000937A1 (en) * | 1986-08-01 | 1988-02-11 | Davy Mckee (London) Limited | Process for the co-production of butane-1,4-diol and gamma-butyrolactone |
| GB8717989D0 (en) * | 1987-07-29 | 1987-09-03 | Davy Mckee Ltd | Catalyst |
| US4837368A (en) * | 1988-02-01 | 1989-06-06 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds and supported catalysts therefor |
| EP0397650B1 (en) * | 1987-08-03 | 1993-10-27 | Eastman Chemical Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds and catalysts therefor |
| US4999090A (en) * | 1988-04-10 | 1991-03-12 | Towa Chemical Industry Co., Ltd. | Process for preparing trans-1,4-cyclohexanedimethanol and powder of the same |
| DE3823457A1 (de) * | 1988-07-11 | 1990-01-18 | Henkel Kgaa | Verfahren zum hydrieren von fettsaeureestern, fetten, fettsaeuren und vorrichtung zum durchfuehren des verfahrens |
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| DE3843956A1 (de) * | 1988-12-24 | 1990-06-28 | Huels Chemische Werke Ag | Verfahren zur herstellung von aliphatischen und cycloaliphatischen diolen durch katalytische hydrierung von dicarbonsaeureestern |
| US5124435A (en) * | 1988-12-28 | 1992-06-23 | Mitsubishi Rayon Co., Ltd. | Polyester copolymer from terephthalic acid glycol and cycloaliphatic diol |
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| GB8917862D0 (en) * | 1989-08-04 | 1989-09-20 | Davy Mckee London | Process |
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-
1993
- 1993-12-02 GB GB939324752A patent/GB9324752D0/en active Pending
- 1993-12-30 US US08/175,502 patent/US5395987A/en not_active Expired - Lifetime
- 1993-12-31 TW TW082111213A patent/TW279850B/zh not_active IP Right Cessation
-
1994
- 1994-01-06 DE DE69404612T patent/DE69404612T2/de not_active Expired - Lifetime
- 1994-01-06 ES ES94300072T patent/ES2105503T3/es not_active Expired - Lifetime
- 1994-01-06 EP EP94300072A patent/EP0656337B1/en not_active Expired - Lifetime
- 1994-01-06 AT AT94300072T patent/ATE156112T1/de not_active IP Right Cessation
- 1994-01-06 SG SG1996005105A patent/SG47898A1/en unknown
- 1994-01-06 KR KR1019940000127A patent/KR100279316B1/ko not_active Expired - Lifetime
- 1994-01-10 JP JP00080394A patent/JP4153049B2/ja not_active Expired - Lifetime
- 1994-11-02 ZA ZA948638A patent/ZA948638B/xx unknown
- 1994-11-10 MY MYPI94002995A patent/MY121943A/en unknown
- 1994-12-01 AU AU79145/94A patent/AU674460B2/en not_active Ceased
- 1994-12-02 BR BR9404846A patent/BR9404846A/pt not_active IP Right Cessation
- 1994-12-02 CN CN94112836A patent/CN1060152C/zh not_active Expired - Lifetime
-
1998
- 1998-01-27 HK HK98100725A patent/HK1001727A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU7914594A (en) | 1995-06-08 |
| CN1060152C (zh) | 2001-01-03 |
| EP0656337A1 (en) | 1995-06-07 |
| CN1112102A (zh) | 1995-11-22 |
| DE69404612D1 (de) | 1997-09-04 |
| KR950017892A (ko) | 1995-07-20 |
| KR100279316B1 (ko) | 2001-02-01 |
| EP0656337B1 (en) | 1997-07-30 |
| BR9404846A (pt) | 1995-08-01 |
| US5395987A (en) | 1995-03-07 |
| DE69404612T2 (de) | 1998-01-15 |
| JP4153049B2 (ja) | 2008-09-17 |
| ATE156112T1 (de) | 1997-08-15 |
| GB9324752D0 (en) | 1994-01-19 |
| AU674460B2 (en) | 1996-12-19 |
| TW279850B (en) | 1996-07-01 |
| MY121943A (en) | 2006-03-31 |
| ZA948638B (en) | 1995-07-07 |
| SG47898A1 (en) | 1998-04-17 |
| HK1001727A1 (en) | 1998-07-03 |
| JPH07196559A (ja) | 1995-08-01 |
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