JP5336368B2 - マクロ孔質カチオン交換樹脂を製造する方法 - Google Patents
マクロ孔質カチオン交換樹脂を製造する方法 Download PDFInfo
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- JP5336368B2 JP5336368B2 JP2009522920A JP2009522920A JP5336368B2 JP 5336368 B2 JP5336368 B2 JP 5336368B2 JP 2009522920 A JP2009522920 A JP 2009522920A JP 2009522920 A JP2009522920 A JP 2009522920A JP 5336368 B2 JP5336368 B2 JP 5336368B2
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- Prior art keywords
- cation exchange
- aqueous phase
- exchange resin
- monomer
- porogen
- 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
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/32—Polymerisation in water-in-oil emulsions
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- 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
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction, e.g. ion-exchange, ion-pair, ion-suppression or ion-exclusion
- B01D15/361—Ion-exchange
- B01D15/362—Cation-exchange
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- 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
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- 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
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/26—Cation exchangers for chromatographic processes
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/20—Aqueous medium with the aid of macromolecular dispersing agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/24—Homopolymers or copolymers of amides or imides
- C08J2333/26—Homopolymers or copolymers of acrylamide or methacrylamide
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Filtering Materials (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Peptides Or Proteins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/460,826 | 2006-07-28 | ||
| US11/460,826 US7674836B2 (en) | 2006-07-28 | 2006-07-28 | Method of making macroporous cation exchange resins |
| PCT/US2007/073571 WO2008014137A1 (en) | 2006-07-28 | 2007-07-16 | Method of making macroporous cation exchange resins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009544835A JP2009544835A (ja) | 2009-12-17 |
| JP2009544835A5 JP2009544835A5 (enExample) | 2010-09-02 |
| JP5336368B2 true JP5336368B2 (ja) | 2013-11-06 |
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Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7645312B2 (en) * | 2004-10-15 | 2010-01-12 | 3M Innovative Properties Company | Pleated multi-layer filter media and cartridge |
| US7674835B2 (en) * | 2005-12-21 | 2010-03-09 | 3M Innovative Properties Company | Method of making macroporous anion exchange resins |
| US7683100B2 (en) * | 2005-12-21 | 2010-03-23 | 3M Innovative Properties Company | Method of making macroporous cation exchange resins |
| US7674836B2 (en) * | 2006-07-28 | 2010-03-09 | 3M Innovative Properties Company | Method of making macroporous cation exchange resins |
| CN101910268B (zh) | 2007-11-09 | 2014-07-30 | 3M创新有限公司 | 多孔聚合物树脂 |
| EP2585541B1 (en) | 2010-06-25 | 2016-06-08 | 3M Innovative Properties Company | Semi-interpenetrating polymer network |
| WO2013077981A1 (en) | 2011-11-21 | 2013-05-30 | 3M Innovative Properties Company | Polymeric particles for storage and delivery of active agents |
| SG10201701224UA (en) * | 2012-03-12 | 2017-04-27 | Merck Patent Gmbh | Removal of protein aggregates from biopharmaceutical preparations in a flowthrough mode |
| CN104470606B (zh) * | 2012-05-31 | 2017-03-22 | 新加坡科技研究局 | 用带负电荷颗粒对多核苷酸的色谱纯化 |
| EP3052556B1 (en) * | 2013-10-03 | 2021-01-20 | 3M Innovative Properties Company | Ligand-functionalized substrates with enhanced binding capacity |
| EP3509729A1 (en) | 2016-09-09 | 2019-07-17 | 3M Innovative Properties Company | Functionalized copolymers and use thereof |
| EP3510041B1 (en) * | 2016-09-09 | 2023-05-31 | 3M Innovative Properties Company | Processes for separating aggregated proteins from monomeric proteins in a biological solution |
| US10927228B2 (en) | 2017-11-16 | 2021-02-23 | 3M Innovative Properties Company | Polymer matrix composites comprising intumescent particles and methods of making the same |
| CN111447993A (zh) | 2017-11-16 | 2020-07-24 | 3M创新有限公司 | 包含官能化颗粒的聚合物基质复合材料及其制备方法 |
| US10836873B2 (en) | 2017-11-16 | 2020-11-17 | 3M Innovative Properties Company | Polymer matrix composites comprising thermally insulating particles and methods of making the same |
| US10913834B2 (en) | 2017-11-16 | 2021-02-09 | 3M Innovative Properties Company | Polymer matrix composites comprising indicator particles and methods of making the same |
| US11732104B2 (en) | 2017-11-16 | 2023-08-22 | 3M Innovative Properties Company | Polymer matrix composites comprising dielectric particles and methods of making the same |
| WO2019097449A1 (en) | 2017-11-16 | 2019-05-23 | 3M Innovative Properties Company | Method of making polymer matrix composites |
| CN108043463B (zh) * | 2017-11-27 | 2020-10-16 | 天津工业大学 | 一种用于二氧化碳资源化的高性能催化剂及其制备方法 |
| WO2019111157A1 (en) * | 2017-12-04 | 2019-06-13 | King Abdullah University Of Science And Technology | Methods of making porous membranes |
| CN115443266B (zh) | 2020-04-14 | 2024-05-17 | 舒万诺知识产权公司 | 用于生物材料捕集的单体、聚合物和制品 |
| CN112588272B (zh) * | 2020-11-23 | 2023-01-24 | 扬州工业职业技术学院 | 一种黄酮类物质吸附剂及其制备方法 |
| CN115487875A (zh) * | 2022-10-17 | 2022-12-20 | 蚌埠市天星树脂有限责任公司 | 一种改性酸性阳离子交换树脂及其用途 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527300A (en) | 1948-03-18 | 1950-10-24 | American Cyanamid Co | Copolymers of unsaturated sulfonic acids and polyunsaturated compounds |
| US3058594A (en) | 1960-06-06 | 1962-10-16 | Purolator Products Inc | Pleated paper filter |
| CS171962B1 (enExample) | 1974-02-01 | 1976-11-29 | ||
| CS177507B1 (enExample) | 1974-02-12 | 1977-07-29 | ||
| US3929741A (en) | 1974-07-16 | 1975-12-30 | Datascope Corp | Hydrophilic acrylamido polymers |
| US4071508A (en) | 1975-02-11 | 1978-01-31 | Plastomedical Sciences, Inc. | Anionic hydrogels based on hydroxyalkyl acrylates and methacrylates |
| US4134815A (en) | 1976-05-31 | 1979-01-16 | Ici Australia Limited | Amphoteric composite resins and method of preparing same by polymerization of a two-phase dispersion of monomers |
| US4153661A (en) | 1977-08-25 | 1979-05-08 | Minnesota Mining And Manufacturing Company | Method of making polytetrafluoroethylene composite sheet |
| JPS54100489A (en) | 1978-01-26 | 1979-08-08 | Asahi Chem Ind Co Ltd | New basic crosslinked copolymer and its preparation |
| US4157418A (en) | 1978-02-08 | 1979-06-05 | Minnesota Mining And Manufacturing Company | Acrylic functional aminocarboxylic acids and derivatives as components of pressure sensitive adhesives |
| FR2482112B1 (fr) | 1980-05-09 | 1985-06-07 | Pharmindustrie | Nouveaux copolymeres hydrophiles a base de n-(tris (hydroxymethyl) methyl) acrylamide, procedes pour leur preparation, gels aqueux desdits copolymeres et leur utilisation comme echangeurs d'ions |
| JPS57158209A (en) | 1981-03-25 | 1982-09-30 | Kao Corp | Production of bead-form highly water-absorbing polymer |
| US4565663A (en) | 1981-06-26 | 1986-01-21 | Minnesota Mining And Manufacturing Company | Method for making water-swellable composite sheet |
| US4439545A (en) | 1981-11-19 | 1984-03-27 | Societe D "Expansion Scientifique "Expansia" | Acrylic copolymers of N-acryloylpolymethyleneimines or N-acryloyldialkylamides, N,N'-acryloyldiaminoalcanes and N-acryloylaminoacids (or esters) their preparation and use as cation exchangers |
| US4552939A (en) | 1983-12-19 | 1985-11-12 | Exxon Research And Engineering Co. | Preparation of sulfonated copolymers by suspension copolymerization |
| US4833198A (en) | 1985-07-22 | 1989-05-23 | The Dow Chemical Company | Suspending agent for the suspension polymerization of water-soluble monomers |
| US5336742A (en) | 1987-03-13 | 1994-08-09 | Minnesota Mining And Manufacturing Company | Polymeric supports |
| US4842739A (en) | 1987-08-20 | 1989-06-27 | Minnesota Mining And Manufacturing Company | High surface area filter cartridge |
| US4810381A (en) | 1987-12-28 | 1989-03-07 | Minnesota Mining And Manufacturing Company | Composite chromatographic article |
| US4971736A (en) | 1987-12-28 | 1990-11-20 | Minnesota Mining And Manufacturing Company | Method of preparing composite chromatographic article |
| US6323249B1 (en) | 1988-09-26 | 2001-11-27 | Purolite International, Ltd. | Macroporous resins having large pores but with high crush strength |
| US4957943A (en) | 1988-10-14 | 1990-09-18 | Minnesota Mining And Manufacturing Company | Particle-filled microporous materials |
| US5264125A (en) | 1989-09-08 | 1993-11-23 | Ionics' Incorporated | Process for manufacturing continuous supported ion selective membranes using non-polymerizable high boiling point solvents |
| US5171808A (en) | 1990-06-11 | 1992-12-15 | American Cyanamid Company | Cross-linked anionic and amphoteric polymeric microparticles |
| US5037858A (en) | 1990-06-21 | 1991-08-06 | Ionics, Incorporated | Anion selective polymers prepared from concentrated solutions of N,N'-methylenebisacrylamide |
| US5104729A (en) | 1990-08-20 | 1992-04-14 | Monsanto Company | Process for surface modifying a support membrane and product produced |
| US5993935A (en) | 1991-10-11 | 1999-11-30 | 3M Innovative Properties Company | Covalently reactive particles incorporated in a continous porous matrix |
| JP3301628B2 (ja) | 1992-03-06 | 2002-07-15 | 日立化成工業株式会社 | りん酸基を有する陽イオン交換樹脂及びその製造法 |
| JP3112682B2 (ja) * | 1992-06-19 | 2000-11-27 | セプラコア インコーポレーテッド | 表面処理および安定化した多孔質支持体,その製造法ならびに使用法 |
| US5906734A (en) * | 1992-06-19 | 1999-05-25 | Biosepra Inc. | Passivated porous polymer supports and methods for the preparation and use of same |
| JPH06228215A (ja) | 1993-02-03 | 1994-08-16 | Dainippon Ink & Chem Inc | 感温性多孔質重合体の製造方法 |
| JPH06228216A (ja) | 1993-02-03 | 1994-08-16 | Dainippon Ink & Chem Inc | pH応答性多孔質重合体の製造方法 |
| US5468847A (en) | 1994-03-10 | 1995-11-21 | Minnesota Mining And Manufacturing Company | Method of isolating and purifying a biomacromolecule |
| US5561097A (en) | 1994-04-28 | 1996-10-01 | Minnesota Mining And Manufacturing Company | Method of controlling density of ligand coupled onto supports and products produced therefrom |
| AUPM587094A0 (en) * | 1994-05-25 | 1994-06-16 | Poseidon Scientific Instruments Pty Ltd | Microwave loop oscillators |
| FR2722097B1 (fr) | 1994-07-11 | 1997-05-16 | Oreal | Composition cosmetique et/ou dermatologique gelifiee, riche en solvant et contenant des particules creuses, ses application |
| US5906747A (en) * | 1995-11-13 | 1999-05-25 | Biosepra Inc. | Separation of molecules from dilute solutions using composite chromatography media having high dynamic sorptive capacity at high flow rates |
| US6059975A (en) | 1997-09-02 | 2000-05-09 | Lockheed Martin Energy Research Corporation | Bifunctional anion-exchange resins with improved selectivity and exchange kinetics |
| DE19907023A1 (de) | 1999-02-19 | 2000-08-24 | Bayer Ag | Verfahren zur Isolierung von Nucleinsäuren |
| US6423666B1 (en) | 1999-10-05 | 2002-07-23 | Bio-Rad Laboratories, Inc. | Large-pore chromatographic beads prepared by suspension polymerization |
| DE19959264A1 (de) | 1999-12-03 | 2001-07-12 | Elipsa Gmbh | Templat-geprägte Kompositmaterialien mit hoher Bindungsspezifität und Selektivität, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10009982A1 (de) * | 2000-03-03 | 2001-09-06 | Qiagen Gmbh | Polymere Anionenaustauscher und deren Verwendung in chromatographischen Verfahren |
| AU2001281906A1 (en) | 2000-06-27 | 2002-01-08 | Bia Separations D.O.O. | A chromatography material and a process of manufacturing that material |
| DE10033583A1 (de) | 2000-07-11 | 2002-01-24 | Bayer Ag | Superparamagnetische Perlpolymerisate |
| JP2004517980A (ja) | 2000-09-21 | 2004-06-17 | ローム アンド ハース カンパニー | 極性モノマーと多価カチオンとに関わる方法および組成物 |
| US6783838B2 (en) | 2001-04-30 | 2004-08-31 | 3M Innovative Properties Company | Coated film laminate having an ionic surface |
| FR2824734B1 (fr) | 2001-05-16 | 2003-06-27 | Oreal | Composition pulverulente pour la decoloration des fibres keratiniques humaines |
| US6756462B2 (en) | 2001-07-03 | 2004-06-29 | Rohm And Haas Company | Method for preparation of anion exchange resins |
| FI20011575A0 (fi) | 2001-07-26 | 2001-07-26 | Fortum Oyj | Polttoainekomponentit ja niiden selektiiviset valmistusmenetelmät |
| US7098253B2 (en) | 2004-05-20 | 2006-08-29 | 3M Innovative Properties Company | Macroporous ion exchange resins |
| KR20070057266A (ko) * | 2004-10-01 | 2007-06-04 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 복합 여과 제품 |
| US7683100B2 (en) * | 2005-12-21 | 2010-03-23 | 3M Innovative Properties Company | Method of making macroporous cation exchange resins |
| US7674835B2 (en) * | 2005-12-21 | 2010-03-09 | 3M Innovative Properties Company | Method of making macroporous anion exchange resins |
| US7674836B2 (en) * | 2006-07-28 | 2010-03-09 | 3M Innovative Properties Company | Method of making macroporous cation exchange resins |
-
2006
- 2006-07-28 US US11/460,826 patent/US7674836B2/en active Active
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2007
- 2007-07-16 EP EP07812958.2A patent/EP2046877B1/en not_active Not-in-force
- 2007-07-16 WO PCT/US2007/073571 patent/WO2008014137A1/en not_active Ceased
- 2007-07-16 JP JP2009522920A patent/JP5336368B2/ja not_active Expired - Fee Related
-
2010
- 2010-01-20 US US12/690,334 patent/US8349906B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008014137A1 (en) | 2008-01-31 |
| JP2009544835A (ja) | 2009-12-17 |
| US7674836B2 (en) | 2010-03-09 |
| US8349906B2 (en) | 2013-01-08 |
| US20080027153A1 (en) | 2008-01-31 |
| US20100116739A1 (en) | 2010-05-13 |
| EP2046877A1 (en) | 2009-04-15 |
| EP2046877B1 (en) | 2016-02-17 |
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