CN102365262B - 疏水单体、疏水衍生载体及其制备和使用方法 - Google Patents

疏水单体、疏水衍生载体及其制备和使用方法 Download PDF

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Publication number
CN102365262B
CN102365262B CN201080014204.0A CN201080014204A CN102365262B CN 102365262 B CN102365262 B CN 102365262B CN 201080014204 A CN201080014204 A CN 201080014204A CN 102365262 B CN102365262 B CN 102365262B
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Prior art keywords
hydrophobic
alkylaryl
aryl
alkyl
monomer
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Chinese (zh)
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CN102365262A (zh
Inventor
杰拉尔德·K·拉斯穆森
卡里·A·基普克
詹姆斯·I·亨布里
彼得·D·维克特
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Shuwanuo Intellectual Property Co
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3M Innovative Properties Co
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/282Porous sorbents
    • B01J20/285Porous sorbents based on polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/04Immunostimulants
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D15/00Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08Selective adsorption, e.g. chromatography
    • B01D15/10Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/20Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the sorbent material
    • B01D15/206Packing or coating
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D15/00Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08Selective adsorption, e.g. chromatography
    • B01D15/26Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/32Bonded phase chromatography
    • B01D15/325Reversed phase
    • B01D15/327Reversed phase with hydrophobic interaction
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D67/00Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002Organic membrane manufacture
    • B01D67/0006Organic membrane manufacture by chemical reactions
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D67/00Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0081After-treatment of organic or inorganic membranes
    • B01D67/0088Physical treatment with compounds, e.g. swelling, coating or impregnation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D67/00Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0081After-treatment of organic or inorganic membranes
    • B01D67/0093Chemical modification
    • B01D67/00931Chemical modification by introduction of specific groups after membrane formation, e.g. by grafting
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D69/00Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
    • B01D69/12Composite membranes; Ultra-thin membranes
    • B01D69/125In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D71/00Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06Organic material
    • B01D71/56Polyamides, e.g. polyester-amides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52Amides or imides
    • C08F20/54Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2323/00Details relating to membrane preparation
    • B01D2323/30Cross-linking
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D2325/00Details relating to properties of membranes
    • B01D2325/38Hydrophobic membranes

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Immunology (AREA)
  • Polymers & Plastics (AREA)
  • Transplantation (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
CN201080014204.0A 2009-03-31 2010-03-19 疏水单体、疏水衍生载体及其制备和使用方法 Active CN102365262B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US16513209P 2009-03-31 2009-03-31
US61/165,132 2009-03-31
PCT/US2010/027978 WO2010117598A2 (en) 2009-03-31 2010-03-19 Hydrophobic monomers, hydrophobically-derivatized supports, and methods of making and using the same

Publications (2)

Publication Number Publication Date
CN102365262A CN102365262A (zh) 2012-02-29
CN102365262B true CN102365262B (zh) 2014-09-17

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Country Status (6)

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US (3) US20120039920A1 (enExample)
EP (1) EP2414321B1 (enExample)
JP (1) JP5681166B2 (enExample)
CN (1) CN102365262B (enExample)
BR (1) BRPI1006782A2 (enExample)
WO (1) WO2010117598A2 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5767584B2 (ja) 2008-09-02 2015-08-19 ナトリックス セパレイションズ インコーポレーテッド クロマトグラフィー膜、それを含む装置及びその使用方法
EP2499192B1 (en) * 2009-11-13 2020-07-15 Merck Millipore Ltd. Hydrophobic interaction chromatography membranes
WO2012158896A2 (en) 2011-05-17 2012-11-22 Natrix Separations Inc. Layered tubular membranes for chromatography, and methods of use thereof
CN104812491B (zh) 2012-03-08 2018-06-19 生物辐射实验室股份有限公司 阴离子交换-疏水性混合模式
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
CN111818980B (zh) * 2018-03-08 2022-10-11 生物辐射实验室股份有限公司 阴离子交换-疏水混合模式色谱树脂
US11045773B2 (en) * 2018-08-31 2021-06-29 Pall Corporation Salt tolerant porous medium
EP3721998A1 (de) * 2019-04-10 2020-10-14 Philipps-Universität Marburg Verfahren zur erzeugung einer hydrophilen oberfläche auf ps/dvb copolymerpartikeln
CN114040815B (zh) 2019-09-05 2024-06-28 生物辐射实验室股份有限公司 阴离子交换-疏水混合模式色谱树脂
CN112552204A (zh) * 2019-09-25 2021-03-26 天津大学 丙烯酰-n-(2-硝基苄基)甘氨酰胺光敏单体及其制备方法
WO2022138975A1 (ja) * 2020-12-25 2022-06-30 東レ株式会社 複合半透膜
EP4581090A1 (en) 2022-08-29 2025-07-09 3M Innovative Properties Company Pressure sensitive adhesive compositions comprising polymerized amide monomers, articles, and methods
CN115894800A (zh) * 2022-10-18 2023-04-04 北京石油化工学院 一种高载量多模式层析介质及其制备方法和应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1108383A (en) * 1965-12-23 1968-04-03 Kodak Ltd Acrylic polymers and light sensitive materials containing them
US5274167A (en) * 1989-01-26 1993-12-28 Bayer Aktiengesellschaft Polymeriable optically active (meth) acrylic acid derivatives
WO1996024074A1 (en) * 1995-02-03 1996-08-08 Novartis Ag Crosslinked polymers
WO1996024644A1 (en) * 1995-02-10 1996-08-15 Minnesota Mining And Manufacturing Company Process for the production of an article coated with a crosslinked pressure sensitive adhesive
WO2001030872A1 (en) * 1999-10-28 2001-05-03 3M Innovative Properties Company Compositions and articles made therefrom

Family Cites Families (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2701809A (en) * 1951-01-09 1955-02-08 Plaut Herman Nu-caylamido fatty acid compounds
US3452182A (en) 1964-07-24 1969-06-24 Polaroid Corp Photographic products and processes
NL6509157A (enExample) 1964-07-24 1966-01-25
JPS4514031Y1 (enExample) 1968-07-16 1970-06-15
US3850646A (en) * 1970-03-24 1974-11-26 H Wagner Light sensitive photographic element
US3721565A (en) 1971-07-06 1973-03-20 Polaroid Corp Polymeric binders for photographic emulsions
US3713834A (en) 1971-07-06 1973-01-30 Polaroid Corp Polymeric binders for photographic emulsions
SE420838B (sv) * 1975-12-12 1981-11-02 Pharmacia Fine Chemicals Ab Dextranderivatgel i partikelform for separationsendamal
US4304705A (en) 1980-01-02 1981-12-08 Minnesota Mining And Manufacturing Company Radiation-curable polymers containing pendant unsaturated peptide groups derived from azlactone polymers
US4395524A (en) 1981-04-10 1983-07-26 Rohm And Haas Company Acrylamide copolymer thickener for aqueous systems
US4451619A (en) 1982-09-30 1984-05-29 Minnesota Mining And Manufacturing Company Method of hydrophilizing or hydrophobizing polymers
US4521580A (en) 1982-12-29 1985-06-04 Exxon Research & Engineering Co. Microemulsion process for producing acrylamide-alkyl acrylamide copolymers
US4528348A (en) 1982-12-29 1985-07-09 Exxon Research & Engineering Company Micellar process for the production of acrylamide-alkyl acrylamide copolymers
US4520182A (en) 1982-12-29 1985-05-28 Exxon Research & Engineering Co. Acrylamide-alkylacrylamide copolymers
IL78169A0 (en) * 1986-03-17 1986-07-31 Weizmann Kiryat Membrane Prod Novel membranes and process for making them
US4730028A (en) 1986-03-28 1988-03-08 Exxon Research And Engineering Company Process for preparing hydrophobically associating terpolymers containing sulfonate functionality
US5336742A (en) 1987-03-13 1994-08-09 Minnesota Mining And Manufacturing Company Polymeric supports
US4871824A (en) 1987-03-13 1989-10-03 Minnesota Mining And Manufacturing Company Variably crosslinked polymeric supports
DE3811042A1 (de) * 1988-03-31 1989-10-19 Merck Patent Gmbh Ionenaustauscher
US5094960A (en) * 1988-10-07 1992-03-10 New York Blood Center, Inc. Removal of process chemicals from labile biological mixtures by hydrophobic interaction chromatography
US4981935A (en) 1988-12-29 1991-01-01 Exxon Research And Engineering Company Hydrophobically associating polymers containing dimethyl acrylamide functionality
US5030352A (en) 1990-01-25 1991-07-09 Purdue Research Foundation Coated media for chromatography
US5993935A (en) * 1991-10-11 1999-11-30 3M Innovative Properties Company Covalently reactive particles incorporated in a continous porous matrix
US5344701A (en) 1992-06-09 1994-09-06 Minnesota Mining And Manufacturing Company Porous supports having azlactone-functional surfaces
DE4228135A1 (de) * 1992-08-25 1994-03-03 Bayer Ag Polymerisierbare Dipeptide, Synthese, Polymerisation und Verwendung der Polymere zur chromatographischen Enantiomerentrennung
US5641403A (en) * 1993-07-16 1997-06-24 Merck Patent Gesellschaft Mit Beschrankter Haftung Separating materials for hydrophobic chromatography
DE4333821A1 (de) * 1993-10-04 1995-04-06 Merck Patent Gmbh Ionenaustauscher
DE4334353A1 (de) * 1993-10-08 1995-04-13 Merck Patent Gmbh Verfahren und Träger für die Gelpermeationschromatographie
US5429746A (en) 1994-02-22 1995-07-04 Smith Kline Beecham Corporation Antibody purification
US5503933A (en) 1994-02-25 1996-04-02 Purdue Research Foundation Covalently bonded coatings
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
US5641870A (en) 1995-04-20 1997-06-24 Genentech, Inc. Low pH hydrophobic interaction chromatography for antibody purification
JP4344863B2 (ja) * 1995-07-28 2009-10-14 スリーエム カンパニー 発色団光架橋化合物としてのアクリルアミド誘導体
US5714632A (en) 1995-11-13 1998-02-03 Minnesota Mining And Manufacturing Company Azlactone-based surfactants
SE9702427D0 (sv) 1997-06-25 1997-06-25 Pharmacia Biotech Ab Coated polymer article
US6479300B1 (en) * 1999-03-15 2002-11-12 Millipore Corporation Metal loaded ligand bound membranes for metal ion affinity chromatography
US6689854B2 (en) 2001-08-23 2004-02-10 3M Innovative Properties Company Water and oil repellent masonry treatments
US6992217B2 (en) * 2002-12-11 2006-01-31 3M Innovative Properties Company Ring-opened azlactone initiators for atom transfer radical polymerization
US7332546B2 (en) 2004-10-01 2008-02-19 3M Innovative Properties Company Ring-opened azlactone telechelic polymer
US7304112B2 (en) 2004-10-01 2007-12-04 3M Innovative Properties Company Azlactone telechelic polymer
EP1968792B1 (en) * 2005-12-30 2013-12-11 3M Innovative Properties Company Functionalized substrates
EP2043767B1 (en) * 2006-07-14 2020-03-25 Wisconsin Alumni Research Foundation Adsorptive membranes for trapping viruses
JP6062630B2 (ja) * 2008-06-26 2017-01-18 スリーエム イノベイティブ プロパティズ カンパニー グラフト化鎖を伴う固体支持体

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1108383A (en) * 1965-12-23 1968-04-03 Kodak Ltd Acrylic polymers and light sensitive materials containing them
US5274167A (en) * 1989-01-26 1993-12-28 Bayer Aktiengesellschaft Polymeriable optically active (meth) acrylic acid derivatives
WO1996024074A1 (en) * 1995-02-03 1996-08-08 Novartis Ag Crosslinked polymers
WO1996024644A1 (en) * 1995-02-10 1996-08-15 Minnesota Mining And Manufacturing Company Process for the production of an article coated with a crosslinked pressure sensitive adhesive
WO2001030872A1 (en) * 1999-10-28 2001-05-03 3M Innovative Properties Company Compositions and articles made therefrom

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Estimation of Molecular Environment for Amino Acids in Proteins by Monolayer Behaviors of the Amino Acid Derivative Polymers on a Water Surface;Makoto Ide et al.;《Langmuir》;20010323;第17卷(第8期);第2493-2496页 *
THE SYNTHESIS OF VINYL PEPTIDE MONOMERS;Lloyd D. Taylor et al.;《JOURNAL OF POLYMER SCIENCE, POLYMER LETTERS EDITION》;19691231;第7卷(第8期);第597-603页 *

Also Published As

Publication number Publication date
EP2414321A2 (en) 2012-02-08
EP2414321A4 (en) 2012-10-24
US10807069B2 (en) 2020-10-20
WO2010117598A3 (en) 2011-01-13
US20160325268A1 (en) 2016-11-10
JP2012522112A (ja) 2012-09-20
WO2010117598A2 (en) 2010-10-14
CN102365262A (zh) 2012-02-29
US20120039920A1 (en) 2012-02-16
JP5681166B2 (ja) 2015-03-04
US20200406231A1 (en) 2020-12-31
BRPI1006782A2 (pt) 2016-03-15
EP2414321B1 (en) 2020-02-12

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