JP5605715B2 - 合成潤滑剤の製造方法 - Google Patents
合成潤滑剤の製造方法 Download PDFInfo
- Publication number
- JP5605715B2 JP5605715B2 JP2011500806A JP2011500806A JP5605715B2 JP 5605715 B2 JP5605715 B2 JP 5605715B2 JP 2011500806 A JP2011500806 A JP 2011500806A JP 2011500806 A JP2011500806 A JP 2011500806A JP 5605715 B2 JP5605715 B2 JP 5605715B2
- Authority
- JP
- Japan
- Prior art keywords
- olefin
- oligomerization
- alpha
- molecular weight
- catalyst
- 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 - Fee Related
Links
Classifications
-
- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
- C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
- C07C2/22—Metal halides; Complexes thereof with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
- C07C2/34—Metal-hydrocarbon complexes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
- C10G50/02—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1088—Olefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/10—Lubricating oil
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6982608P | 2008-03-18 | 2008-03-18 | |
| US61/069,826 | 2008-03-18 | ||
| PCT/US2009/001713 WO2009117110A2 (en) | 2008-03-18 | 2009-03-18 | Process for synthetic lubricant production |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011514381A JP2011514381A (ja) | 2011-05-06 |
| JP2011514381A5 JP2011514381A5 (https=) | 2013-07-04 |
| JP5605715B2 true JP5605715B2 (ja) | 2014-10-15 |
Family
ID=41089574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011500806A Expired - Fee Related JP5605715B2 (ja) | 2008-03-18 | 2009-03-18 | 合成潤滑剤の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8865959B2 (https=) |
| EP (1) | EP2265563B1 (https=) |
| JP (1) | JP5605715B2 (https=) |
| CN (2) | CN105925340A (https=) |
| CA (1) | CA2718879C (https=) |
| WO (1) | WO2009117110A2 (https=) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8748361B2 (en) | 2005-07-19 | 2014-06-10 | Exxonmobil Chemical Patents Inc. | Polyalpha-olefin compositions and processes to produce the same |
| WO2007011462A1 (en) | 2005-07-19 | 2007-01-25 | Exxonmobil Chemical Patents Inc. | Lubricants from mixed alpha-olefin feeds |
| US8921290B2 (en) | 2006-06-06 | 2014-12-30 | Exxonmobil Research And Engineering Company | Gear oil compositions |
| US8535514B2 (en) | 2006-06-06 | 2013-09-17 | Exxonmobil Research And Engineering Company | High viscosity metallocene catalyst PAO novel base stock lubricant blends |
| US8501675B2 (en) | 2006-06-06 | 2013-08-06 | Exxonmobil Research And Engineering Company | High viscosity novel base stock lubricant viscosity blends |
| US8299007B2 (en) | 2006-06-06 | 2012-10-30 | Exxonmobil Research And Engineering Company | Base stock lubricant blends |
| US8834705B2 (en) | 2006-06-06 | 2014-09-16 | Exxonmobil Research And Engineering Company | Gear oil compositions |
| US8624738B2 (en) * | 2008-03-17 | 2014-01-07 | Radar Corporation | Golf club apparatuses and methods |
| US8394746B2 (en) | 2008-08-22 | 2013-03-12 | Exxonmobil Research And Engineering Company | Low sulfur and low metal additive formulations for high performance industrial oils |
| US8247358B2 (en) | 2008-10-03 | 2012-08-21 | Exxonmobil Research And Engineering Company | HVI-PAO bi-modal lubricant compositions |
| EP2351722A1 (en) * | 2008-11-04 | 2011-08-03 | Idemitsu Kosan Co., Ltd. | Method for producing -olefin oligomer, -olefin oligomer, and lubricating oil composition |
| US8716201B2 (en) | 2009-10-02 | 2014-05-06 | Exxonmobil Research And Engineering Company | Alkylated naphtylene base stock lubricant formulations |
| CN102666806B (zh) | 2009-12-24 | 2015-09-16 | 埃克森美孚化学专利公司 | 用于生产新型合成基础油料的方法 |
| US8728999B2 (en) | 2010-02-01 | 2014-05-20 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
| US8642523B2 (en) | 2010-02-01 | 2014-02-04 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
| US8748362B2 (en) | 2010-02-01 | 2014-06-10 | Exxonmobile Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed gas engines by reducing the traction coefficient |
| US8598103B2 (en) | 2010-02-01 | 2013-12-03 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low, medium and high speed engines by reducing the traction coefficient |
| US8759267B2 (en) | 2010-02-01 | 2014-06-24 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
| KR20130103652A (ko) * | 2010-04-02 | 2013-09-24 | 이데미쓰 고산 가부시키가이샤 | 내연 기관용 윤활유 조성물 |
| US8703683B2 (en) * | 2010-04-23 | 2014-04-22 | Exxonmobil Research And Engineering Company | Poly (alkyl epdxides), process for making, and lubricant compositions having same |
| US8524968B2 (en) * | 2010-12-13 | 2013-09-03 | Chevron U.S.A. Inc. | Process to make base oil by oligomerizing low boiling olefins |
| US20140323665A1 (en) * | 2011-03-30 | 2014-10-30 | Exxonmobil Chemical Patents Inc. | Polyalphaolefins by Oligomerization and Isomerization |
| US9234151B2 (en) | 2011-10-10 | 2016-01-12 | Exxonmobil Research And Engineering Company | Lubricating compositions |
| US9422497B2 (en) | 2012-09-21 | 2016-08-23 | Exxonmobil Research And Engineering Company | Synthetic lubricant basestocks and methods of preparation thereof |
| US9266793B2 (en) | 2012-12-26 | 2016-02-23 | Chevron Phillips Chemical Company Lp | Acid-catalyzed olefin oligomerizations |
| US20140275664A1 (en) * | 2013-03-13 | 2014-09-18 | Chevron Phillips Chemical Company Lp | Processes for Preparing Low Viscosity Lubricants |
| US9963648B2 (en) * | 2013-06-28 | 2018-05-08 | Dow Global Technologies Llc | Process for the preparation of branched polyolefins for lubricant applications |
| US9708549B2 (en) * | 2013-12-18 | 2017-07-18 | Chevron Phillips Chemical Company Lp | Method for making polyalphaolefins using aluminum halide catalyzed oligomerization of olefins |
| US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
| EP3173462A1 (de) * | 2015-11-30 | 2017-05-31 | Fuchs Petrolub SE | Getriebeöl |
| US20170335217A1 (en) * | 2016-05-19 | 2017-11-23 | Chevron U.S.A. Inc. | Alkylation of metallocene-oligomer with isoalkane to make heavy base oil |
| US10093594B2 (en) | 2016-05-19 | 2018-10-09 | Chevron U.S.A. Inc. | High viscosity index lubricants by isoalkane alkylation |
| US10647626B2 (en) | 2016-07-12 | 2020-05-12 | Chevron Phillips Chemical Company Lp | Decene oligomers |
| CN106978245A (zh) * | 2017-04-14 | 2017-07-25 | 上海欧勒奋生物科技有限公司 | 一种pao60基础油制备的方法 |
| CN107057823B (zh) * | 2017-04-14 | 2020-08-04 | 安徽欧勒奋生物科技有限公司 | 一种pao40基础油高效制备的方法 |
| CN106867583B (zh) * | 2017-04-14 | 2019-03-05 | 安徽欧勒奋生物科技有限公司 | 一种高效制备pao50基础油的方法 |
| CN106957677A (zh) * | 2017-04-14 | 2017-07-18 | 上海欧勒奋生物科技有限公司 | 一种由高纯度线性α烯烃通过无水AlCl3合成低粘度PAO4的方法 |
| JP2020524733A (ja) | 2017-06-22 | 2020-08-20 | エクソンモービル リサーチ アンド エンジニアリング カンパニーExxon Research And Engineering Company | メチルパラフィン含有炭化水素流体に基づく低粘度潤滑油 |
| US11021553B2 (en) | 2018-02-12 | 2021-06-01 | Exxonmobil Chemical Patents Inc. | Metallocene dimer selective catalysts and processes to produce poly alpha-olefin dimers |
| US11078308B2 (en) | 2018-02-12 | 2021-08-03 | Exxonmobil Chemical Patents Inc. | Processes to produce poly alpha-olefin trimers |
| US11084894B2 (en) | 2018-02-12 | 2021-08-10 | Exxonmobil Chemical Patents Inc. | Catalyst systems and processes for poly alpha-olefin having high vinylidene content |
| CN108947759A (zh) * | 2018-07-20 | 2018-12-07 | 山西潞安纳克碳化工有限公司 | 一种利用煤制烯烃制备烷基萘的方法 |
| CN112912357B (zh) | 2018-09-17 | 2024-06-04 | 埃克森美孚化学专利公司 | 聚α-烯烃三聚物的制备方法和制备设备 |
| EP3856879B1 (en) * | 2018-09-27 | 2026-03-25 | ExxonMobil Chemical Patents Inc. | Base stocks and oil compositions containing the same |
| KR102586499B1 (ko) * | 2018-10-26 | 2023-10-11 | 에스케이이노베이션 주식회사 | 고점도 윤활기유 제조 방법 |
| WO2020085833A1 (ko) * | 2018-10-26 | 2020-04-30 | 에스케이이노베이션 주식회사 | 저점도 윤활기유 제조방법 |
| CN109762631A (zh) * | 2018-12-29 | 2019-05-17 | 广州科卢斯流体科技有限公司 | 一种无灰型高性能真空泵油 |
| US12091380B2 (en) | 2019-08-09 | 2024-09-17 | Exxonmobil Chemical Patents Inc. | Processes for producing poly alpha olefins and apparatuses therefor |
| CN114450262B (zh) | 2019-08-09 | 2024-03-15 | 埃克森美孚化学专利公司 | 制备聚α-烯烃的方法及其分析方法和装置 |
| US11661465B2 (en) | 2019-10-28 | 2023-05-30 | Exxonmobil Chemical Patents Inc. | Dimer selective metallocene catalysts, non-aromatic hydrocarbon soluble activators, and processes to produce poly alpha-olefin oligmers therewith |
| US11370987B2 (en) * | 2020-04-14 | 2022-06-28 | Indian Oil Corporation Limited | Method of controlling kinematic viscosity of polyalphaolefin |
| US12522677B2 (en) | 2020-04-29 | 2026-01-13 | Exxonmobil Chemical Patents Inc. | Processes to produce poly alpha-olefins |
| KR102368349B1 (ko) * | 2020-05-04 | 2022-02-25 | 디엘케미칼 주식회사 | 적은 단쇄분지를 갖는 알파올레핀 올리고머 및 이의 제조방법 |
| CN115212922B (zh) | 2021-04-15 | 2024-11-26 | 中国石油天然气股份有限公司 | 一种α-烯烃聚合的催化剂组合物及其制备与应用 |
| WO2023017779A1 (ja) * | 2021-08-11 | 2023-02-16 | 出光興産株式会社 | α-オレフィンオリゴマー組成物の製造方法 |
| CN116554920A (zh) * | 2022-01-30 | 2023-08-08 | 中国石油天然气股份有限公司 | 一种润滑油基础油的制备方法 |
| US12043588B2 (en) | 2022-12-15 | 2024-07-23 | Chevron Phillips Chemical Company Lp | Solid oxide and chemically-treated solid oxide catalysts for the production of polyalphaolefins |
| CN121001982A (zh) | 2023-05-22 | 2025-11-21 | 埃克森美孚技术与工程公司 | 反应器中活化茂金属催化剂以提高pao生产中催化剂生产率的方法 |
| WO2025198839A1 (en) | 2024-03-19 | 2025-09-25 | ExxonMobil Technology and Engineering Company | Hybrid compositions from a type of lightly branched olefins |
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-
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| CA2718879A1 (en) | 2009-09-26 |
| CN105925340A (zh) | 2016-09-07 |
| US20090240012A1 (en) | 2009-09-24 |
| EP2265563B1 (en) | 2019-04-17 |
| EP2265563A4 (en) | 2013-07-17 |
| CN101977879A (zh) | 2011-02-16 |
| US8865959B2 (en) | 2014-10-21 |
| EP2265563A2 (en) | 2010-12-29 |
| WO2009117110A3 (en) | 2009-12-30 |
| CA2718879C (en) | 2015-02-17 |
| WO2009117110A2 (en) | 2009-09-24 |
| JP2011514381A (ja) | 2011-05-06 |
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