UA75349C2 - A continuous method for hydrogenation of adinonitrile into amidocapronitrile and/or hexamethyldiamine - Google Patents
A continuous method for hydrogenation of adinonitrile into amidocapronitrile and/or hexamethyldiamine Download PDFInfo
- Publication number
- UA75349C2 UA75349C2 UA2002097275A UA2002097275A UA75349C2 UA 75349 C2 UA75349 C2 UA 75349C2 UA 2002097275 A UA2002097275 A UA 2002097275A UA 2002097275 A UA2002097275 A UA 2002097275A UA 75349 C2 UA75349 C2 UA 75349C2
- Authority
- UA
- Ukraine
- Prior art keywords
- catalyst
- hydrogenation
- solvent
- raney
- metal
- Prior art date
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 39
- 238000011437 continuous method Methods 0.000 title claims 2
- 239000003054 catalyst Substances 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000002904 solvent Substances 0.000 claims abstract description 28
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims abstract description 17
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000003750 conditioning effect Effects 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 7
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 25
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 20
- 150000007529 inorganic bases Chemical class 0.000 claims description 19
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 238000003860 storage Methods 0.000 claims description 15
- 239000012429 reaction media Substances 0.000 claims description 14
- 239000007868 Raney catalyst Substances 0.000 claims description 10
- 229910017052 cobalt Inorganic materials 0.000 claims description 10
- 239000010941 cobalt Substances 0.000 claims description 10
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 10
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 8
- 238000005275 alloying Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 239000006229 carbon black Substances 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 230000001143 conditioned effect Effects 0.000 claims description 3
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical group [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 238000012876 topography Methods 0.000 claims 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 150000004985 diamines Chemical class 0.000 abstract description 10
- 150000001412 amines Chemical group 0.000 abstract description 6
- 150000002825 nitriles Chemical group 0.000 abstract description 5
- -1 amine compound Chemical class 0.000 abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 3
- 239000011707 mineral Substances 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
- C07C209/48—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 nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0002997A FR2806081B1 (fr) | 2000-03-08 | 2000-03-08 | Procede d'hydrogenation de fonctions nitriles en fonctions amines |
| PCT/FR2001/000687 WO2001066511A1 (fr) | 2000-03-08 | 2001-03-07 | Procede d'hydrogenation de fonctions nitriles en fonctions amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75349C2 true UA75349C2 (en) | 2006-04-17 |
Family
ID=8847881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002097275A UA75349C2 (en) | 2000-03-08 | 2001-07-03 | A continuous method for hydrogenation of adinonitrile into amidocapronitrile and/or hexamethyldiamine |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6790994B2 (xx) |
| EP (1) | EP1265845B1 (xx) |
| JP (1) | JP2003525924A (xx) |
| KR (1) | KR100586668B1 (xx) |
| CN (1) | CN1212306C (xx) |
| AR (1) | AR029487A1 (xx) |
| AT (1) | ATE344790T1 (xx) |
| AU (1) | AU2001239356A1 (xx) |
| BR (1) | BR0109261B1 (xx) |
| CA (1) | CA2403210A1 (xx) |
| DE (1) | DE60124378T2 (xx) |
| FR (1) | FR2806081B1 (xx) |
| IN (1) | IN211182B (xx) |
| MX (1) | MXPA02008765A (xx) |
| PL (1) | PL365069A1 (xx) |
| RU (1) | RU2242460C2 (xx) |
| SK (1) | SK12732002A3 (xx) |
| TW (1) | TWI259832B (xx) |
| UA (1) | UA75349C2 (xx) |
| WO (1) | WO2001066511A1 (xx) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101086508B1 (ko) * | 2003-01-31 | 2011-11-23 | 디에스엠 아이피 어셋츠 비.브이. | 나이트릴의 촉매 수소화 방법 |
| CA2624999A1 (en) * | 2005-09-15 | 2007-03-22 | Basf Se | Method for the hydrogenation of nitriles to form primary amines or amino nitriles and suitable catalysts for said process |
| FR2892118B1 (fr) | 2005-10-18 | 2010-12-10 | Rhodia Recherches & Tech | Procede de fabrication d'hexamethylene diamine et d'aminocapronitrile. |
| DE102005060488A1 (de) * | 2005-12-15 | 2007-06-28 | Basf Ag | Verfahren zur Hydrierung von Nitrilen zu primären Aminen oder Aminonitrilen und dafür geeignete Katalysatoren |
| KR101858297B1 (ko) † | 2011-04-15 | 2018-06-28 | 라디치 키미카 에스.피.에이. | 헥사메틸렌디아민을 제조하는 개선된 방법 |
| EA025555B1 (ru) | 2012-01-18 | 2017-01-30 | Ренновиа, Инк. | Способ получения гексаметилендиамина из 5-гидроксиметилфурфурола |
| CN107001197B (zh) | 2014-12-02 | 2021-06-25 | 阿彻丹尼尔斯米德兰公司 | 由hmf生产bhmf、bhmthf、hdo和hto的方法 |
| CN104888800B (zh) * | 2015-05-12 | 2018-04-27 | 常州鑫邦再生资源利用有限公司 | 一种复合金属的炭催化剂的制备方法 |
| TWI565686B (zh) * | 2015-11-26 | 2017-01-11 | 南亞塑膠工業股份有限公司 | 一種ｎ，ｎ’－雙（３－胺基丙基）－１，２－乙二胺的製備方法 |
| CN108686660B (zh) * | 2018-04-24 | 2020-06-26 | 浙江大学 | 一种用于异佛尔酮腈还原胺化合成异佛尔酮二胺的催化剂及其制备方法和应用 |
| CN111054432B (zh) * | 2019-12-16 | 2021-09-03 | 中国科学院大连化学物理研究所 | 用于制备己二胺的催化剂及其制备方法与应用 |
| WO2021191289A1 (en) | 2020-03-25 | 2021-09-30 | Basf Se | Process for the preparation of hexamethylenediamine by hydrogenation of adiponitrile in the presence of raney nickel and a basic co-catalyst |
| CN111995526A (zh) * | 2020-09-22 | 2020-11-27 | 江苏扬农化工集团有限公司 | 一种固定床加氢合成己二胺的方法 |
| CN115779956B (zh) * | 2022-12-07 | 2024-04-09 | 万华化学集团股份有限公司 | 一种己二腈加氢催化剂的制备方法与应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758296A (fr) * | 1969-11-07 | 1971-04-01 | Rhodiatoce | Procede de fabrication d'hexamethylenediamine |
| DE2238452A1 (de) * | 1972-08-04 | 1974-02-14 | Davy Ashmore Ag | Verfahren zur kontinuierlichen herstellung von hexamethylendiamin durch hydrierung von adiponitril |
| FR2619377B1 (fr) * | 1987-08-12 | 1989-12-08 | Rhone Poulenc Chimie | Procede de fabrication de la methyl-2 pentanediamine par hydrogenation du methyl-2 glutaronitrile |
| SG55029A1 (en) * | 1993-12-28 | 1998-12-21 | Rhone Poulenc Chimie | Catalyst for the hydrogenation of nitriles to amines preparation process thereof and hydrogenation process making use thereof |
| JP3340439B2 (ja) * | 1993-12-28 | 2002-11-05 | ローヌ−プーラン シミ | ドーピングさせたラニーニッケル型の触媒の存在におけるニトリルの、アミンへの接触水素添加方法 |
| FR2738757B1 (fr) * | 1995-09-15 | 1997-10-31 | Rhone Poulenc Fibres | Nouveaux composes metalliques utilisables comme catalyseurs |
| US5898085A (en) * | 1997-03-28 | 1999-04-27 | E. I. Du Pont De Nemours And Company | Production of 1,3-diaminopentane by hydrogenation of 3-aminopentanenitrile |
| FR2773086B1 (fr) * | 1997-12-29 | 2000-02-11 | Rhone Poulenc Fibres | Procede de regeneration d'un catalyseur d'hydrogenation procede d'hydrogenation de composes comprenant des fonctions nitriles |
-
2000
- 2000-03-08 FR FR0002997A patent/FR2806081B1/fr not_active Expired - Fee Related
-
2001
- 2001-03-07 KR KR20027011780A patent/KR100586668B1/ko not_active IP Right Cessation
- 2001-03-07 AU AU2001239356A patent/AU2001239356A1/en not_active Abandoned
- 2001-03-07 CA CA002403210A patent/CA2403210A1/fr not_active Abandoned
- 2001-03-07 JP JP2001565331A patent/JP2003525924A/ja active Pending
- 2001-03-07 IN IN935DE2002 patent/IN211182B/en unknown
- 2001-03-07 AT AT01913956T patent/ATE344790T1/de not_active IP Right Cessation
- 2001-03-07 CN CNB018074987A patent/CN1212306C/zh not_active Expired - Fee Related
- 2001-03-07 WO PCT/FR2001/000687 patent/WO2001066511A1/fr active IP Right Grant
- 2001-03-07 SK SK1273-2002A patent/SK12732002A3/sk unknown
- 2001-03-07 EP EP01913956A patent/EP1265845B1/fr not_active Expired - Lifetime
- 2001-03-07 PL PL01365069A patent/PL365069A1/xx unknown
- 2001-03-07 MX MXPA02008765A patent/MXPA02008765A/es unknown
- 2001-03-07 US US10/220,821 patent/US6790994B2/en not_active Expired - Lifetime
- 2001-03-07 BR BRPI0109261-8B1A patent/BR0109261B1/pt not_active IP Right Cessation
- 2001-03-07 DE DE60124378T patent/DE60124378T2/de not_active Expired - Lifetime
- 2001-03-07 RU RU2002126613/04A patent/RU2242460C2/ru not_active IP Right Cessation
- 2001-03-08 AR ARP010101090A patent/AR029487A1/es not_active Application Discontinuation
- 2001-06-01 TW TW090105305A patent/TWI259832B/zh not_active IP Right Cessation
- 2001-07-03 UA UA2002097275A patent/UA75349C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2002DE00935A (xx) | 2005-01-21 |
| AR029487A1 (es) | 2003-07-02 |
| IN211182B (xx) | 2007-11-09 |
| SK12732002A3 (sk) | 2003-04-01 |
| RU2242460C2 (ru) | 2004-12-20 |
| WO2001066511A1 (fr) | 2001-09-13 |
| AU2001239356A1 (en) | 2001-09-17 |
| CN1420861A (zh) | 2003-05-28 |
| DE60124378T2 (de) | 2007-10-04 |
| PL365069A1 (en) | 2004-12-27 |
| FR2806081B1 (fr) | 2003-03-14 |
| KR100586668B1 (ko) | 2006-06-07 |
| MXPA02008765A (es) | 2003-04-14 |
| US6790994B2 (en) | 2004-09-14 |
| BR0109261B1 (pt) | 2013-11-19 |
| TWI259832B (en) | 2006-08-11 |
| JP2003525924A (ja) | 2003-09-02 |
| BR0109261A (pt) | 2003-06-03 |
| RU2002126613A (ru) | 2004-02-27 |
| DE60124378D1 (de) | 2006-12-21 |
| FR2806081A1 (fr) | 2001-09-14 |
| US20030144552A1 (en) | 2003-07-31 |
| ATE344790T1 (de) | 2006-11-15 |
| CA2403210A1 (fr) | 2001-09-13 |
| EP1265845A1 (fr) | 2002-12-18 |
| CN1212306C (zh) | 2005-07-27 |
| EP1265845B1 (fr) | 2006-11-08 |
| KR20020079992A (ko) | 2002-10-21 |
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