WO2009019012A3 - Immobilisation of chelating groups for immobilised metal ion chromatography (imac) - Google Patents
Immobilisation of chelating groups for immobilised metal ion chromatography (imac) Download PDFInfo
- Publication number
- WO2009019012A3 WO2009019012A3 PCT/EP2008/006485 EP2008006485W WO2009019012A3 WO 2009019012 A3 WO2009019012 A3 WO 2009019012A3 EP 2008006485 W EP2008006485 W EP 2008006485W WO 2009019012 A3 WO2009019012 A3 WO 2009019012A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- immobilisation
- imac
- metal ion
- ion chromatography
- chelating groups
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/22—Affinity chromatography or related techniques based upon selective absorption processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
- B01D15/3804—Affinity chromatography
- B01D15/3828—Ligand exchange chromatography, e.g. complexation, chelation or metal interaction chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
- B01J20/28009—Magnetic properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J20/289—Phases chemically bonded to a substrate, e.g. to silica or to polymers bonded via a spacer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
- B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
- B01J20/3219—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond involving a particular spacer or linking group, e.g. for attaching an active group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3248—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such
- B01J20/3251—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulphur
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3265—Non-macromolecular compounds with an organic functional group containing a metal, e.g. a metal affinity ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/13—Labelling of peptides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/52—Sorbents specially adapted for preparative chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Peptides Or Proteins (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008801057565A CN101808731B (en) | 2007-08-06 | 2008-08-06 | Immobilisation of chelating groups for immobilised metal ion chromatography (IMAC) |
CA2695586A CA2695586C (en) | 2007-08-06 | 2008-08-06 | Immobilisation of chelating groups for immobilised metal ion chromatography (imac) |
US12/672,345 US9073971B2 (en) | 2007-08-06 | 2008-08-06 | Immobilization of chelating groups for immobilized metal ion chromatography (IMAC) |
EP14173856.7A EP2826555B1 (en) | 2007-08-06 | 2008-08-06 | Use of immobilized chelator for purification of recombinant polypeptides by immobilized metal ion chromatography |
ES08785398T ES2524786T5 (en) | 2007-08-06 | 2008-08-06 | Use of immobilized chelators for purification of recombinant proteins by immobilized metal ion chromatography and recombinant protein purification method |
JP2010519377A JP5629208B2 (en) | 2007-08-06 | 2008-08-06 | Immobilization of chelating groups for immobilized metal ion chromatography (IMAC) |
EP08785398.2A EP2183049B2 (en) | 2007-08-06 | 2008-08-06 | Use of immobilized chelator for purification of recombinant proteins by immobilized metal ion chromatography and method of purifying recombinant proteins |
HK10109243.4A HK1142843A1 (en) | 2007-08-06 | 2010-09-28 | Immobilisation of chelating groups for immobilised metal ion chromatography(imac) |
US14/723,770 US9675960B2 (en) | 2007-08-06 | 2015-05-28 | Immobilization of chelating groups for immobilized metal ion chromatography (IMAC) |
US15/491,048 US10538552B2 (en) | 2007-08-06 | 2017-04-19 | Immobilisation of chelating groups for immobilised metal ion chromatography (IMAC) |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US95414407P | 2007-08-06 | 2007-08-06 | |
US60/954,144 | 2007-08-06 | ||
EP07015389A EP2022561A1 (en) | 2007-08-06 | 2007-08-06 | Immobilisation of chelating groups for immobilised metal ion chromatography (IMAC) |
EP07015389.5 | 2007-08-06 | ||
EP08012686 | 2008-07-14 | ||
EP08012686.5 | 2008-07-14 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/672,345 A-371-Of-International US9073971B2 (en) | 2007-08-06 | 2008-08-06 | Immobilization of chelating groups for immobilized metal ion chromatography (IMAC) |
US14/723,770 Division US9675960B2 (en) | 2007-08-06 | 2015-05-28 | Immobilization of chelating groups for immobilized metal ion chromatography (IMAC) |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2009019012A2 WO2009019012A2 (en) | 2009-02-12 |
WO2009019012A3 true WO2009019012A3 (en) | 2009-05-07 |
Family
ID=39870668
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2008/006485 WO2009019012A2 (en) | 2007-08-06 | 2008-08-06 | Immobilisation of chelating groups for immobilised metal ion chromatography (imac) |
Country Status (8)
Country | Link |
---|---|
US (3) | US9073971B2 (en) |
EP (2) | EP2826555B1 (en) |
JP (2) | JP5629208B2 (en) |
CN (2) | CN101808731B (en) |
CA (2) | CA2695586C (en) |
ES (2) | ES2832541T3 (en) |
HK (2) | HK1142843A1 (en) |
WO (1) | WO2009019012A2 (en) |
Families Citing this family (19)
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---|---|---|---|---|
JP2011173822A (en) * | 2010-02-24 | 2011-09-08 | National Institute For Materials Science | Metal complex array, method for producing the same and material |
CN102161757B (en) * | 2011-03-08 | 2015-07-01 | 上海树脂厂有限公司 | Special resin for vanadium extraction and preparation method thereof |
CN103157440B (en) * | 2011-12-19 | 2016-07-06 | 华东理工大学 | The material of heavy metal and method in a kind of adsorption aqueous solution |
HU230585B1 (en) * | 2012-05-30 | 2017-01-30 | Budapesti Műszaki és Gazdaságtudományi Egyetem | Carriers complexed with lanthanide metal ions capable for peptid absorption and isolation |
CN104525131A (en) * | 2015-01-05 | 2015-04-22 | 福州大学 | CDTA modified magnetic nano-adsorbent and preparation method and application thereof |
ITUA20163876A1 (en) * | 2016-05-27 | 2017-11-27 | Univ Del Salento | BIORECECTOR FOR METALLIC IONS. |
CN106000326B (en) * | 2016-06-14 | 2018-11-02 | 常州天地人和生物科技有限公司 | A kind of super metals tolerant chelates the preparation and application of affine filler |
GB201616758D0 (en) * | 2016-10-03 | 2016-11-16 | Ge Healthcare Bio Sciences Ab | Novel chromatography media |
CN107652352B (en) * | 2017-10-31 | 2021-02-26 | 苏州博进生物技术有限公司 | Affinity chromatography medium for purifying histidine-tagged protein |
CN109280204A (en) * | 2018-08-22 | 2019-01-29 | 泉州三欣新材料科技有限公司 | A kind of agarose aquogel microballoon and its preparation method and application |
CN113164915A (en) | 2018-11-28 | 2021-07-23 | 库贝生物科技有限公司 | Solid phase chelator material, method for the production thereof and use thereof for the purification of proteins |
CN109663384B (en) * | 2018-12-27 | 2021-05-11 | 苏州赛分科技有限公司 | IMAC (IMAC) filler based on NTA (nitrilotriacetic acid), preparation method and application thereof |
CN113646634A (en) | 2019-03-29 | 2021-11-12 | 豪夫迈·罗氏有限公司 | Transition metal chelate beads |
CN109967035A (en) * | 2019-04-30 | 2019-07-05 | 湘潭大学 | A kind of EGTA modified magnetic carbon adsorbent and preparation method thereof and its application method |
CN112156499A (en) * | 2020-09-22 | 2021-01-01 | 上海碧云天生物技术有限公司 | Metal chelating chromatography filler and preparation method thereof |
CN112812030B (en) * | 2020-12-31 | 2023-05-16 | 三棵树(上海)新材料研究有限公司 | Synthesis method of branched polyamide epoxy curing agent based on ethylenediamine tetraacetic acid |
CN113351191B (en) * | 2021-05-10 | 2023-12-01 | 翌圣生物科技(上海)有限公司 | Novel IMAC chromatographic medium of multidentate ligand and preparation method thereof |
CN114797804B (en) * | 2022-03-29 | 2023-08-04 | 翌圣生物科技(上海)股份有限公司 | NTA chromatographic medium with long connecting arm and preparation method thereof |
CN117946306B (en) * | 2024-03-26 | 2024-06-07 | 江苏海普功能材料有限公司 | Diketoxime resin, preparation method thereof and nickel removal method of lithium battery recovery liquid |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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GB2067203A (en) * | 1979-12-22 | 1981-07-22 | Ceskoslovenska Akademie Ved | Polymeric chelating agents |
US4423158A (en) * | 1983-01-27 | 1983-12-27 | Gelinnovation Handelsaktiebolag | Ion adsorbent for metals having a coordination number greater than two |
GB2183238A (en) * | 1985-11-11 | 1987-06-03 | Ceskoslovenska Akademie Ved | Silane reagents containing a complexon grouping and inorganic materials modified with these reagents |
WO1992017403A1 (en) * | 1991-04-05 | 1992-10-15 | Brigham Young University | Support bonded polyalkylene-polyamine-poly(carboxylic acid) and extraction of metal ions therewith |
US20050272116A1 (en) * | 2004-06-04 | 2005-12-08 | Clemson University | Polymer substrate for recombinant protein purification and environmental remediation |
WO2005120700A2 (en) * | 2004-06-14 | 2005-12-22 | Novo Nordisk A/S | Peptide purification by means of hard metal ion affinity chromatography |
EP1767631A1 (en) * | 2005-09-26 | 2007-03-28 | NExtTec GmbH | A method for isolating RNA |
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CS256456B1 (en) * | 1985-11-11 | 1988-04-15 | Jaroslav Kahovec | Silane agents containing chemically bonded complex grouping |
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US6670159B1 (en) | 1997-12-31 | 2003-12-30 | Pierce Biotechnology, Inc. | Preparing monomeric metal ion chelator containing diacetyl glycine group linked to proteinaceous molecule |
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-
2008
- 2008-08-06 CN CN2008801057565A patent/CN101808731B/en active Active
- 2008-08-06 CN CN201310445701.1A patent/CN103586092B/en active Active
- 2008-08-06 JP JP2010519377A patent/JP5629208B2/en active Active
- 2008-08-06 EP EP14173856.7A patent/EP2826555B1/en active Active
- 2008-08-06 ES ES14173856T patent/ES2832541T3/en active Active
- 2008-08-06 ES ES08785398T patent/ES2524786T5/en active Active
- 2008-08-06 CA CA2695586A patent/CA2695586C/en active Active
- 2008-08-06 EP EP08785398.2A patent/EP2183049B2/en active Active
- 2008-08-06 US US12/672,345 patent/US9073971B2/en active Active
- 2008-08-06 CA CA2934502A patent/CA2934502C/en active Active
- 2008-08-06 WO PCT/EP2008/006485 patent/WO2009019012A2/en active Application Filing
-
2010
- 2010-09-28 HK HK10109243.4A patent/HK1142843A1/en unknown
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2014
- 2014-04-28 HK HK14104054.9A patent/HK1190978A1/en unknown
- 2014-08-13 JP JP2014164613A patent/JP6063907B2/en active Active
-
2015
- 2015-05-28 US US14/723,770 patent/US9675960B2/en active Active
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2017
- 2017-04-19 US US15/491,048 patent/US10538552B2/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2067203A (en) * | 1979-12-22 | 1981-07-22 | Ceskoslovenska Akademie Ved | Polymeric chelating agents |
US4423158A (en) * | 1983-01-27 | 1983-12-27 | Gelinnovation Handelsaktiebolag | Ion adsorbent for metals having a coordination number greater than two |
GB2183238A (en) * | 1985-11-11 | 1987-06-03 | Ceskoslovenska Akademie Ved | Silane reagents containing a complexon grouping and inorganic materials modified with these reagents |
WO1992017403A1 (en) * | 1991-04-05 | 1992-10-15 | Brigham Young University | Support bonded polyalkylene-polyamine-poly(carboxylic acid) and extraction of metal ions therewith |
US20050272116A1 (en) * | 2004-06-04 | 2005-12-08 | Clemson University | Polymer substrate for recombinant protein purification and environmental remediation |
WO2005120700A2 (en) * | 2004-06-14 | 2005-12-22 | Novo Nordisk A/S | Peptide purification by means of hard metal ion affinity chromatography |
EP1767631A1 (en) * | 2005-09-26 | 2007-03-28 | NExtTec GmbH | A method for isolating RNA |
Non-Patent Citations (1)
Title |
---|
S. GOVENDER: "A pluronic-coupled metal-chelating ligand for membrane affinity chromatography", JOURNAL OF MEMBRANE SCIENCE, vol. 279, 2006, pages 120 - 128, XP002502187 * |
Also Published As
Publication number | Publication date |
---|---|
EP2183049B2 (en) | 2019-03-13 |
CA2695586C (en) | 2016-09-06 |
EP2826555A3 (en) | 2016-01-27 |
WO2009019012A2 (en) | 2009-02-12 |
CN103586092A (en) | 2014-02-19 |
HK1142843A1 (en) | 2010-12-17 |
ES2524786T3 (en) | 2014-12-12 |
JP6063907B2 (en) | 2017-01-18 |
HK1190978A1 (en) | 2014-07-18 |
US9073971B2 (en) | 2015-07-07 |
CN103586092B (en) | 2016-06-08 |
ES2524786T5 (en) | 2019-06-19 |
CN101808731B (en) | 2013-10-23 |
EP2183049B1 (en) | 2014-09-17 |
CA2934502A1 (en) | 2009-02-12 |
JP2010535725A (en) | 2010-11-25 |
JP5629208B2 (en) | 2014-11-19 |
ES2832541T3 (en) | 2021-06-10 |
EP2826555B1 (en) | 2020-09-23 |
US10538552B2 (en) | 2020-01-21 |
CA2934502C (en) | 2020-03-24 |
US20150283536A1 (en) | 2015-10-08 |
CN101808731A (en) | 2010-08-18 |
US20170218013A1 (en) | 2017-08-03 |
US9675960B2 (en) | 2017-06-13 |
EP2183049A2 (en) | 2010-05-12 |
EP2826555A2 (en) | 2015-01-21 |
CA2695586A1 (en) | 2009-02-12 |
JP2015028026A (en) | 2015-02-12 |
US20110071274A1 (en) | 2011-03-24 |
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