DE102007039525A1 - Verfahren zum Metathese-Abbau von Nitrilkautschuk - Google Patents
Verfahren zum Metathese-Abbau von Nitrilkautschuk Download PDFInfo
- Publication number
- DE102007039525A1 DE102007039525A1 DE102007039525A DE102007039525A DE102007039525A1 DE 102007039525 A1 DE102007039525 A1 DE 102007039525A1 DE 102007039525 A DE102007039525 A DE 102007039525A DE 102007039525 A DE102007039525 A DE 102007039525A DE 102007039525 A1 DE102007039525 A1 DE 102007039525A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- general formula
- aryl
- catalyst
- alkoxy
- 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.)
- Withdrawn
Links
- TXRUBUGERHLKKJ-UHFFFAOYSA-N CC(N(C(C1c2ccccc2)c2ccccc2)SC)N1SC Chemical compound CC(N(C(C1c2ccccc2)c2ccccc2)SC)N1SC TXRUBUGERHLKKJ-UHFFFAOYSA-N 0.000 description 2
- POKQCCVKEUHHGT-UHFFFAOYSA-N CC(N(CC1)SC)N1SC Chemical compound CC(N(CC1)SC)N1SC POKQCCVKEUHHGT-UHFFFAOYSA-N 0.000 description 2
- BTFOHYMUDSJZTJ-UHFFFAOYSA-N CCCCC(C(CCCC)N(C1C)SC)N1SC Chemical compound CCCCC(C(CCCC)N(C1C)SC)N1SC BTFOHYMUDSJZTJ-UHFFFAOYSA-N 0.000 description 1
- LUKMXJJAJSYYSD-UHFFFAOYSA-N CCCCC(N(C1C)SC)=C(CCCC)N1SC Chemical compound CCCCC(N(C1C)SC)=C(CCCC)N1SC LUKMXJJAJSYYSD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/08—Depolymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
- C08L15/005—Hydrogenated nitrile rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007039525A DE102007039525A1 (de) | 2007-08-21 | 2007-08-21 | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
| DE502008000361T DE502008000361D1 (de) | 2007-08-21 | 2008-08-08 | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
| EP08162051A EP2030988B1 (de) | 2007-08-21 | 2008-08-08 | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
| AT08162051T ATE457320T1 (de) | 2007-08-21 | 2008-08-08 | Verfahren zum metathese-abbau von nitrilkautschuk |
| US12/193,816 US7875683B2 (en) | 2007-08-21 | 2008-08-19 | Process for the metathetic degradation of nitrile rubber |
| BRPI0822786-1A BRPI0822786A2 (pt) | 2007-08-21 | 2008-08-20 | processo para redução do peso molecular de borracha nitrìlica |
| MX2008010685A MX2008010685A (es) | 2007-08-21 | 2008-08-20 | Procedimiento para la degradacion por metatesis de caucho de nitrilo. |
| JP2008212062A JP5455337B2 (ja) | 2007-08-21 | 2008-08-20 | ニトリルゴムをメタセシス分解するための方法 |
| CN2008102101285A CN101372517B (zh) | 2007-08-21 | 2008-08-21 | 用于丁腈橡胶复分解降解的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007039525A DE102007039525A1 (de) | 2007-08-21 | 2007-08-21 | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102007039525A1 true DE102007039525A1 (de) | 2009-02-26 |
Family
ID=40225260
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102007039525A Withdrawn DE102007039525A1 (de) | 2007-08-21 | 2007-08-21 | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
| DE502008000361T Active DE502008000361D1 (de) | 2007-08-21 | 2008-08-08 | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502008000361T Active DE502008000361D1 (de) | 2007-08-21 | 2008-08-08 | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7875683B2 (https=) |
| EP (1) | EP2030988B1 (https=) |
| JP (1) | JP5455337B2 (https=) |
| CN (1) | CN101372517B (https=) |
| AT (1) | ATE457320T1 (https=) |
| BR (1) | BRPI0822786A2 (https=) |
| DE (2) | DE102007039525A1 (https=) |
| MX (1) | MX2008010685A (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2011002606A (es) | 2008-09-12 | 2011-06-24 | Lanxess Corp | Composiciones de hnbr con niveles de carga muy altos que tienen excelente capacidad de procesado y resistencia a fluidos agresivos. |
| EP2289620A1 (en) * | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Process for the preparation of hydrogenated nitrile rubber |
| CA2771242A1 (en) * | 2009-08-31 | 2011-03-03 | Lanxess Deutschland Gmbh | Vulcanizable polymer composition comprising a low molecular weight optionally hydrogenated nitrile rubber |
| EP2289621A1 (en) | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| EP2289622A1 (en) * | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Ruthenium based catalysts for the metathesis of nitrile rubbers |
| EP2289623A1 (en) * | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Metathesis of nitrile rubbers in the presence of transition metal catalysts |
| EP2418225A1 (de) | 2010-08-09 | 2012-02-15 | LANXESS Deutschland GmbH | Teilhydrierte Nitrilkautschuke |
| US8633280B2 (en) * | 2011-03-30 | 2014-01-21 | Zannan Scitech Co., Ltd | Methods of modifying polymers with highly active and selective metathesis catalysts |
| WO2013056461A1 (en) | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
| WO2013056463A1 (en) | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
| WO2013056400A1 (en) * | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
| WO2013056459A1 (en) | 2011-10-21 | 2013-04-25 | Lanxess Deutschland Gmbh | Catalyst compositions and their use for hydrogenation of nitrile rubber |
| CN104861095B (zh) * | 2014-02-26 | 2017-09-26 | 中国石油化工股份有限公司 | 一种降低聚合物分子量的方法 |
| CN104861093B (zh) * | 2014-02-26 | 2017-08-25 | 中国石油化工股份有限公司 | 一种降低聚合物分子量的方法 |
| CN104324752B (zh) * | 2014-08-18 | 2016-08-24 | 杭州师范大学 | 一种n-杂环卡宾铂配合物羧酸金属盐一体化催化剂及其制备方法 |
| FR3027601B1 (fr) * | 2014-10-23 | 2018-03-02 | Compagnie Generale Des Etablissements Michelin | Procede de fonctionnalisation d'un polydiene au moyen d'une faible teneur en catalyseur de metathese |
| TWI566835B (zh) | 2014-12-25 | 2017-01-21 | 財團法人工業技術研究院 | 烯烴複分解觸媒及低分子量丁腈橡膠之製備方法 |
| CN109867750B (zh) * | 2017-12-01 | 2024-08-06 | 中国石油化工股份有限公司 | 三元乙丙橡胶接枝共聚物及其制备方法 |
| KR102702569B1 (ko) * | 2017-12-08 | 2024-09-06 | 아란세오 도이치란드 게엠베하 | 루테늄 착물 촉매를 사용하여 니트릴 고무를 생성하기 위한 방법 |
| US11311868B2 (en) * | 2018-07-23 | 2022-04-26 | Arlanxeo Deutschland Gmbh | Use of catalysts for the metathesis of nitrile rubber |
| KR102536751B1 (ko) * | 2020-04-07 | 2023-05-24 | 주식회사 엘지화학 | 촉매 조성물, 이를 포함하는 세척액 조성물 및 이를 이용한 중합장치의 세척방법 |
Citations (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700637A (en) | 1970-05-08 | 1972-10-24 | Shell Oil Co | Diene-nitrile rubbers |
| DE2539132A1 (de) | 1975-09-03 | 1977-03-17 | Bayer Ag | Hydrierung von polymeren |
| US4464515A (en) | 1982-12-08 | 1984-08-07 | Polysar Limited | Polymer hydrogenation process |
| US4503196A (en) | 1982-12-08 | 1985-03-05 | Polysar Limited | Polymer hydrogenation process |
| EP0134023A1 (de) | 1983-08-19 | 1985-03-13 | Bayer Ag | Herstellung von hydrierten Nitrilkautschuken |
| DE3433392A1 (de) | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| DE3529252A1 (de) | 1985-08-16 | 1987-02-19 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3540918A1 (de) | 1985-11-19 | 1987-05-21 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3541689A1 (de) | 1985-11-26 | 1987-05-27 | Bayer Ag | Verfahren zur selektiven hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| EP0298386A2 (en) | 1987-07-06 | 1989-01-11 | University Of Waterloo | Polymer hydrogenation process |
| EP0419952A1 (de) | 1989-09-26 | 1991-04-03 | Bayer Ag | Verfahren zur Herstellung von hydriertem Nitrilkautschuk mässiger Viskosität |
| EP0471250A1 (de) | 1990-08-15 | 1992-02-19 | Bayer Ag | Hydrierte Butadien/Isopren/(Meth-)Acrylnitril-Copolymerisate |
| WO1996004289A1 (en) | 1992-04-03 | 1996-02-15 | California Institute Of Technology | High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof |
| WO1997006185A1 (en) | 1995-08-03 | 1997-02-20 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
| WO2000071554A2 (en) | 1999-05-24 | 2000-11-30 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| US20020107138A1 (en) | 2000-08-10 | 2002-08-08 | Hoveyda Amir H. | Recyclable metathesis catalysts |
| WO2002100941A1 (en) | 2001-06-12 | 2002-12-19 | Bayer Inc. | Low molecular weight hydrogenated nitrile rubber |
| WO2002100905A1 (en) | 2001-06-12 | 2002-12-19 | Bayer Inc. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| WO2003002613A1 (en) | 2001-06-29 | 2003-01-09 | Bayer Inc. | Low molecular weight nitrile rubber |
| WO2003011455A1 (en) | 2001-08-01 | 2003-02-13 | California Institute Of Technology | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
| WO2003087167A2 (en) | 2002-04-05 | 2003-10-23 | California Institute Of Technology | Cross-metathesis of olefins directly substituted with an electron-withdrawing group using transition metal carbene catalysts |
| US6683136B2 (en) | 2000-12-28 | 2004-01-27 | Bayer Inc. | Epoxidized soybean oil enhanced hydrogenation of nitrile copolymer |
| WO2004035596A1 (en) | 2002-10-15 | 2004-04-29 | Boehringer Ingelheim International Gmbh | Ruthenium complexes as (pre)catalysts for metathesis reactions |
| US20040127647A1 (en) | 2002-10-17 | 2004-07-01 | Ong Christopher M. | Polymer blends comprising low molecular weight nitrile rubber |
| US20040132891A1 (en) | 2002-12-05 | 2004-07-08 | Ong Christopher M. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| WO2004112951A2 (en) | 2003-06-19 | 2004-12-29 | University Of New Orleans Research & Technology Foundation, Inc. | Preparation of ruthenium-based olefin metathesis catalysts |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4812528A (en) * | 1987-07-06 | 1989-03-14 | University Of Waterloo | Polymer hydrogenation process |
| US6021533A (en) * | 1997-08-25 | 2000-02-08 | Hill-Rom, Inc. | Mattress apparatus having a siderail down sensor |
| US7329758B1 (en) * | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| US6610626B2 (en) * | 2000-09-05 | 2003-08-26 | Cymetech, Llp | Highly active metathesis catalysts generated in situ from inexpensive and air stable precursors |
| DE60109762T2 (de) * | 2000-10-20 | 2005-08-25 | Idemitsu Kosan Co. Ltd. | Flexibles polypropylenharz |
| CA2462005A1 (en) * | 2004-02-23 | 2005-08-23 | Bayer Inc. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| CA2462011A1 (en) * | 2004-02-23 | 2005-08-23 | Bayer Inc. | Process for the preparation of low molecular weight nitrile rubber |
| EP1757623A1 (en) * | 2005-07-14 | 2007-02-28 | Lanxess Inc. | Process for the preparation of low mooney nitrile terpolymers |
| ATE538139T1 (de) * | 2005-08-30 | 2012-01-15 | Lanxess Deutschland Gmbh | Verwendung von katalysatoren für den metatheseabbau von nitrilkautschuk |
| DE102005040939A1 (de) * | 2005-08-30 | 2007-03-01 | Lanxess Deutschland Gmbh | Neuer Katalysator für den Metatheseabbau von Nitrilkautschuk |
| DE102006008520A1 (de) * | 2006-02-22 | 2007-08-23 | Lanxess Deutschland Gmbh | Neue Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| DE102006008521A1 (de) * | 2006-02-22 | 2007-08-23 | Lanxess Deutschland Gmbh | Verwendung von Katalysatoren mit erhöhter Aktivität für die NBR-Metathese |
| DE102006040569A1 (de) * | 2006-08-30 | 2008-03-06 | Lanxess Deutschland Gmbh | Verfahren zum Metathese-Abbau von Nitrilkautschuken |
-
2007
- 2007-08-21 DE DE102007039525A patent/DE102007039525A1/de not_active Withdrawn
-
2008
- 2008-08-08 EP EP08162051A patent/EP2030988B1/de not_active Not-in-force
- 2008-08-08 AT AT08162051T patent/ATE457320T1/de active
- 2008-08-08 DE DE502008000361T patent/DE502008000361D1/de active Active
- 2008-08-19 US US12/193,816 patent/US7875683B2/en active Active
- 2008-08-20 BR BRPI0822786-1A patent/BRPI0822786A2/pt not_active IP Right Cessation
- 2008-08-20 JP JP2008212062A patent/JP5455337B2/ja not_active Expired - Fee Related
- 2008-08-20 MX MX2008010685A patent/MX2008010685A/es active IP Right Grant
- 2008-08-21 CN CN2008102101285A patent/CN101372517B/zh not_active Expired - Fee Related
Patent Citations (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700637A (en) | 1970-05-08 | 1972-10-24 | Shell Oil Co | Diene-nitrile rubbers |
| DE2539132A1 (de) | 1975-09-03 | 1977-03-17 | Bayer Ag | Hydrierung von polymeren |
| US4464515A (en) | 1982-12-08 | 1984-08-07 | Polysar Limited | Polymer hydrogenation process |
| US4503196A (en) | 1982-12-08 | 1985-03-05 | Polysar Limited | Polymer hydrogenation process |
| EP0134023A1 (de) | 1983-08-19 | 1985-03-13 | Bayer Ag | Herstellung von hydrierten Nitrilkautschuken |
| DE3433392A1 (de) | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| US4631315A (en) | 1984-09-12 | 1986-12-23 | Bayer Aktiengesellschaft | Hydrogenation of nitrile group-containing unsaturated polymers |
| DE3529252A1 (de) | 1985-08-16 | 1987-02-19 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3540918A1 (de) | 1985-11-19 | 1987-05-21 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3541689A1 (de) | 1985-11-26 | 1987-05-27 | Bayer Ag | Verfahren zur selektiven hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| EP0298386A2 (en) | 1987-07-06 | 1989-01-11 | University Of Waterloo | Polymer hydrogenation process |
| EP0419952A1 (de) | 1989-09-26 | 1991-04-03 | Bayer Ag | Verfahren zur Herstellung von hydriertem Nitrilkautschuk mässiger Viskosität |
| EP0471250A1 (de) | 1990-08-15 | 1992-02-19 | Bayer Ag | Hydrierte Butadien/Isopren/(Meth-)Acrylnitril-Copolymerisate |
| WO1996004289A1 (en) | 1992-04-03 | 1996-02-15 | California Institute Of Technology | High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof |
| WO1997006185A1 (en) | 1995-08-03 | 1997-02-20 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
| WO2000071554A2 (en) | 1999-05-24 | 2000-11-30 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| US20020107138A1 (en) | 2000-08-10 | 2002-08-08 | Hoveyda Amir H. | Recyclable metathesis catalysts |
| US6683136B2 (en) | 2000-12-28 | 2004-01-27 | Bayer Inc. | Epoxidized soybean oil enhanced hydrogenation of nitrile copolymer |
| WO2002100905A1 (en) | 2001-06-12 | 2002-12-19 | Bayer Inc. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| WO2002100941A1 (en) | 2001-06-12 | 2002-12-19 | Bayer Inc. | Low molecular weight hydrogenated nitrile rubber |
| WO2003002613A1 (en) | 2001-06-29 | 2003-01-09 | Bayer Inc. | Low molecular weight nitrile rubber |
| WO2003011455A1 (en) | 2001-08-01 | 2003-02-13 | California Institute Of Technology | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
| WO2003087167A2 (en) | 2002-04-05 | 2003-10-23 | California Institute Of Technology | Cross-metathesis of olefins directly substituted with an electron-withdrawing group using transition metal carbene catalysts |
| WO2004035596A1 (en) | 2002-10-15 | 2004-04-29 | Boehringer Ingelheim International Gmbh | Ruthenium complexes as (pre)catalysts for metathesis reactions |
| US20040127647A1 (en) | 2002-10-17 | 2004-07-01 | Ong Christopher M. | Polymer blends comprising low molecular weight nitrile rubber |
| US20040132891A1 (en) | 2002-12-05 | 2004-07-08 | Ong Christopher M. | Process for the preparation of low molecular weight hydrogenated nitrile rubber |
| WO2004112951A2 (en) | 2003-06-19 | 2004-12-29 | University Of New Orleans Research & Technology Foundation, Inc. | Preparation of ruthenium-based olefin metathesis catalysts |
Non-Patent Citations (15)
| Title |
|---|
| Angew Chem. Int. Ed. 2003, 42, 4592 |
| Angew. Chem. Int. Ed. 2002, 41, 4038 |
| Angew. Chem. Int. Ed. 2004, 43, 6161-6165 |
| Biomol. Chem. 2005, 3, 4139 |
| Chem. Eur. J 2004, 10, 777-784 |
| ChemBioChem 2003, 4, 1229-1231 |
| Eur. J. Org. Chem 2003, 963-966 |
| Hoveyda et al. |
| Inorganica Chimica Acta 359 (2006) 2910-2917 |
| J. Am. Chem. Soc. 1997, 119, 3887-3897 |
| J. Am. Chem. Soc. 1997, 119, 9130 |
| J. Org. Chem. 2003, 68, 202-2023 |
| J. Org. Chem. 2004, 69, 6894-96 |
| Organometallics 2001, 20, 5314 und Angew. Chem. Int. Ed. 2002, 41, 4038 |
| Synlett 2005, No4, 670-672 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5455337B2 (ja) | 2014-03-26 |
| CN101372517A (zh) | 2009-02-25 |
| ATE457320T1 (de) | 2010-02-15 |
| MX2008010685A (es) | 2009-03-05 |
| BRPI0822786A2 (pt) | 2012-01-17 |
| EP2030988A1 (de) | 2009-03-04 |
| US7875683B2 (en) | 2011-01-25 |
| US20090076227A1 (en) | 2009-03-19 |
| DE502008000361D1 (de) | 2010-03-25 |
| JP2009057555A (ja) | 2009-03-19 |
| EP2030988B1 (de) | 2010-02-10 |
| CN101372517B (zh) | 2012-10-10 |
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Effective date: 20110325 |