JP5509484B2 - 添加剤及びそれを含む潤滑油組成物 - Google Patents
添加剤及びそれを含む潤滑油組成物 Download PDFInfo
- Publication number
- JP5509484B2 JP5509484B2 JP2010511349A JP2010511349A JP5509484B2 JP 5509484 B2 JP5509484 B2 JP 5509484B2 JP 2010511349 A JP2010511349 A JP 2010511349A JP 2010511349 A JP2010511349 A JP 2010511349A JP 5509484 B2 JP5509484 B2 JP 5509484B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- diphenylamine
- carbon atoms
- less
- oil
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen
- C09K15/18—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen containing an amine or imine moiety
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/019—Shear stability
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/071—Branched chain compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/073—Star shaped polymers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07109917.0 | 2007-06-08 | ||
| EP07109917 | 2007-06-08 | ||
| PCT/US2008/066026 WO2008154334A1 (en) | 2007-06-08 | 2008-06-06 | Additives and lubricating oil compositions containing same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010529141A JP2010529141A (ja) | 2010-08-26 |
| JP2010529141A5 JP2010529141A5 (enExample) | 2011-07-21 |
| JP5509484B2 true JP5509484B2 (ja) | 2014-06-04 |
Family
ID=38561951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010511349A Active JP5509484B2 (ja) | 2007-06-08 | 2008-06-06 | 添加剤及びそれを含む潤滑油組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8999903B2 (enExample) |
| EP (1) | EP2155657B1 (enExample) |
| JP (1) | JP5509484B2 (enExample) |
| CN (1) | CN101687766B (enExample) |
| CA (1) | CA2690200C (enExample) |
| WO (1) | WO2008154334A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120329694A1 (en) * | 2009-11-24 | 2012-12-27 | The Lubrizol Corporation | Lubricating Composition Containing Viscosity Modifier Combination |
| US20140187455A1 (en) * | 2012-12-28 | 2014-07-03 | Chevron Oronite LLC | Ultra-low saps lubricants for internal combustion engines |
| ES2620681T3 (es) * | 2014-12-04 | 2017-06-29 | Infineum International Limited | Lubricación de motores marinos |
| WO2016123548A1 (en) * | 2015-01-30 | 2016-08-04 | Basf Corporation | Combination of low/no ash oil and emission control catalysts for improved emission control durability and performance |
| WO2017011159A1 (en) | 2015-07-15 | 2017-01-19 | Chemtura Corporation | Diaryl amine antioxidants prepared from branched olefins |
| WO2020194125A1 (en) | 2019-03-22 | 2020-10-01 | Chevron Oronite Company Llc | Antioxidants with high mono-alkylated diphenylamine content |
| EP3851507B1 (en) * | 2020-01-15 | 2023-01-18 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
| EP4118170A1 (en) * | 2020-03-11 | 2023-01-18 | Chevron Oronite Company LLC | Lubricating oil compositions with improved oxidative performance comprising alkylated diphenylamine antioxidant and carboxylate detergents |
| KR20220148849A (ko) * | 2020-03-11 | 2022-11-07 | 셰브런 오로나이트 컴퍼니 엘엘씨 | 알킬화된 다이페닐아민 항산화제 및 설포네이트 세정제를 포함하는 개선된 산화 성능을 갖는 윤활유 조성물 |
| EP4225870A1 (en) * | 2020-10-08 | 2023-08-16 | ExxonMobil Chemical Patents Inc. | Heat transfer fluids comprising isomeric branched paraffin dimers derived from linear alpha olefins and use thereof |
| CN120574619A (zh) | 2020-11-17 | 2025-09-02 | 松原实业有限公司 | 性能提高的包含烷基化二苯胺的组合物 |
| CA3203263A1 (en) | 2020-12-23 | 2022-06-30 | Scott Capitosti | Benzazepine compounds as antioxidants for lubricant compositions |
| WO2022136384A1 (en) * | 2020-12-24 | 2022-06-30 | Infineum International Limited | Thermally responsive brush polymers having a copolymer backbone and copolymer arms |
| TW202311225A (zh) | 2021-06-25 | 2023-03-16 | 韓商松原產業股份有限公司 | O-烷基化位阻抗氧化劑 |
| US20250136889A1 (en) | 2023-10-27 | 2025-05-01 | Infineum International Limited | Lubricant Compositions Containing High C9 Disubstituted Diphenylamine Antioxidant Content |
| WO2025132964A1 (en) | 2023-12-20 | 2025-06-26 | Infineum International Limited | Lubricant compositions containing c8 disubstituted diphenylamine antioxidant |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1248643B (de) | 1959-03-30 | 1967-08-31 | The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) | Verfahren zur Herstellung von öllöslichen aeylierten Aminen |
| US3215707A (en) | 1960-06-07 | 1965-11-02 | Lubrizol Corp | Lubricant |
| US3231587A (en) | 1960-06-07 | 1966-01-25 | Lubrizol Corp | Process for the preparation of substituted succinic acid compounds |
| US3087936A (en) | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
| GB989409A (en) | 1962-08-24 | 1965-04-14 | Gen Electric | Organopolysiloxane compositions |
| US3185704A (en) | 1962-09-04 | 1965-05-25 | Exxon Research Engineering Co | Formamide of mono-alkenyl succinimide |
| US3284504A (en) * | 1963-03-01 | 1966-11-08 | Universal Oil Prod Co | O-alkylation of hydroxyarylamines |
| US3381022A (en) | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
| NL137371C (enExample) | 1963-08-02 | |||
| US3574576A (en) | 1965-08-23 | 1971-04-13 | Chevron Res | Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine |
| US3272746A (en) | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
| US3442808A (en) | 1966-11-01 | 1969-05-06 | Standard Oil Co | Lubricating oil additives |
| US3632511A (en) | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
| US3912764A (en) | 1972-09-29 | 1975-10-14 | Cooper Edwin Inc | Preparation of alkenyl succinic anhydrides |
| CA1048507A (en) | 1974-03-27 | 1979-02-13 | Jack Ryer | Additive useful in oleaginous compositions |
| US4110349A (en) | 1976-06-11 | 1978-08-29 | The Lubrizol Corporation | Two-step method for the alkenylation of maleic anhydride and related compounds |
| US4113639A (en) | 1976-11-11 | 1978-09-12 | Exxon Research & Engineering Co. | Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound |
| US4116876A (en) | 1977-01-28 | 1978-09-26 | Exxon Research & Engineering Co. | Borated oxazolines as varnish inhibiting dispersants in lubricating oils |
| US4234435A (en) | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
| GB2056482A (en) | 1979-08-13 | 1981-03-18 | Exxon Research Engineering Co | Lubricating oil compositions |
| US4686054A (en) | 1981-08-17 | 1987-08-11 | Exxon Research & Engineering Co. | Succinimide lubricating oil dispersant |
| EP0097118A3 (de) * | 1982-06-10 | 1984-07-25 | Ciba-Geigy Ag | Flüssige Antioxidantien für Schmierstoffe und Elastomere |
| US4579675A (en) | 1983-11-09 | 1986-04-01 | Texaco Inc. | N-substituted enaminones and oleaginous compositions containing same |
| US4612132A (en) | 1984-07-20 | 1986-09-16 | Chevron Research Company | Modified succinimides |
| EP0608962A1 (en) | 1985-03-14 | 1994-08-03 | The Lubrizol Corporation | High molecular weight nitrogen-containing condensates and fuels and lubricants containing same |
| CA1262721A (en) | 1985-07-11 | 1989-11-07 | Jacob Emert | Oil soluble dispersant additives useful in oleaginous compositions |
| US4663064A (en) | 1986-03-28 | 1987-05-05 | Texaco Inc. | Dibaisic acid lubricating oil dispersant and viton seal additives |
| US4963275A (en) | 1986-10-07 | 1990-10-16 | Exxon Chemical Patents Inc. | Dispersant additives derived from lactone modified amido-amine adducts |
| US4956107A (en) | 1987-11-30 | 1990-09-11 | Exxon Chemical Patents Inc. | Amide dispersant additives derived from amino-amines |
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| US4839071A (en) | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in lubricating oil compositions |
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| US5026495A (en) | 1987-11-19 | 1991-06-25 | Exxon Chemical Patents Inc. | Oil soluble dispersant additives useful in oleaginous compositions |
| US5229022A (en) | 1988-08-01 | 1993-07-20 | Exxon Chemical Patents Inc. | Ethylene alpha-olefin polymer substituted mono- and dicarboxylic acid dispersant additives (PT-920) |
| US4952739A (en) | 1988-10-26 | 1990-08-28 | Exxon Chemical Patents Inc. | Organo-Al-chloride catalyzed poly-n-butenes process |
| CA2008258C (en) | 1989-01-30 | 2001-09-11 | Jacob Emert | Oil soluble dispersant additives modified with monoepoxy monounsaturated compounds |
| JP2587296B2 (ja) * | 1989-09-08 | 1997-03-05 | 日本石油株式会社 | 潤滑油組成物 |
| US5214211A (en) | 1991-12-12 | 1993-05-25 | Uop | Alkylation of diarylamines with olefins using rare earth modified pillared clays |
| US5259906A (en) | 1992-04-20 | 1993-11-09 | Wallace Computer Services, Inc. | Method of making and using a combined shipping label product information device |
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| CA2110654C (en) | 1992-12-17 | 2006-03-21 | Albert Rossi | Dilute process for the polymerization of ethylene/alpha-olefin copolymer using metallocene catalyst systems |
| IL107927A0 (en) | 1992-12-17 | 1994-04-12 | Exxon Chemical Patents Inc | Oil soluble ethylene/1-butene copolymers and lubricating oils containing the same |
| US5356552A (en) | 1993-03-09 | 1994-10-18 | Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc. | Chlorine-free lubricating oils having modified high molecular weight succinimides |
| US5334321A (en) | 1993-03-09 | 1994-08-02 | Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc. | Modified high molecular weight succinimides |
| US5750787A (en) * | 1995-09-13 | 1998-05-12 | B. F. Goodrich Company | Liquid alkylated diphenylamine antioxidant |
| US5821205A (en) | 1995-12-01 | 1998-10-13 | Chevron Chemical Company | Polyalkylene succinimides and post-treated derivatives thereof |
| US5716912A (en) | 1996-04-09 | 1998-02-10 | Chevron Chemical Company | Polyalkylene succinimides and post-treated derivatives thereof |
| SG65759A1 (en) | 1997-06-06 | 1999-06-22 | Ciba Sc Holding Ag | Nonylated diphenylamines |
| JPH1150081A (ja) * | 1997-08-06 | 1999-02-23 | Nippon Oil Co Ltd | 潤滑油組成物 |
| US5861363A (en) | 1998-01-29 | 1999-01-19 | Chevron Chemical Company Llc | Polyalkylene succinimide composition useful in internal combustion engines |
| US7189875B2 (en) | 2003-04-04 | 2007-03-13 | Crompton Corporation | Diphenylamine alkylated with olefin mixtures containing fractions with varying degrees of activity |
| WO2006130498A1 (en) | 2005-06-02 | 2006-12-07 | Albemarle Corporation | Improved process for synthesizing alkylated arylamines |
| US7145038B1 (en) * | 2005-12-14 | 2006-12-05 | Chemtura Corporation | Alkylation of a diphenylamine compound in ionic liquid |
-
2008
- 2008-06-06 JP JP2010511349A patent/JP5509484B2/ja active Active
- 2008-06-06 CA CA2690200A patent/CA2690200C/en active Active
- 2008-06-06 US US12/602,204 patent/US8999903B2/en active Active
- 2008-06-06 CN CN200880019358.1A patent/CN101687766B/zh active Active
- 2008-06-06 EP EP08770270.0A patent/EP2155657B1/en active Active
- 2008-06-06 WO PCT/US2008/066026 patent/WO2008154334A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN101687766A (zh) | 2010-03-31 |
| US20100173811A1 (en) | 2010-07-08 |
| US8999903B2 (en) | 2015-04-07 |
| EP2155657B1 (en) | 2017-05-03 |
| WO2008154334A1 (en) | 2008-12-18 |
| CN101687766B (zh) | 2014-04-16 |
| CA2690200C (en) | 2014-09-30 |
| EP2155657A1 (en) | 2010-02-24 |
| JP2010529141A (ja) | 2010-08-26 |
| CA2690200A1 (en) | 2008-12-18 |
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