EP1989146A1 - Polymere grave moleculairement, son procede de fabrication et procede de traitement selectif de composes difficilement degradables et/ou toxiques dans des liquides - Google Patents

Polymere grave moleculairement, son procede de fabrication et procede de traitement selectif de composes difficilement degradables et/ou toxiques dans des liquides

Info

Publication number
EP1989146A1
EP1989146A1 EP07722869A EP07722869A EP1989146A1 EP 1989146 A1 EP1989146 A1 EP 1989146A1 EP 07722869 A EP07722869 A EP 07722869A EP 07722869 A EP07722869 A EP 07722869A EP 1989146 A1 EP1989146 A1 EP 1989146A1
Authority
EP
European Patent Office
Prior art keywords
acid
molecularly imprinted
polymer
imprinted polymer
acids
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.)
Withdrawn
Application number
EP07722869A
Other languages
German (de)
English (en)
Inventor
Ute Steinfeld
Barbara Palm
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Korea Institute of Science and Technology Europe Forschungs GmbH
Original Assignee
Korea Institute of Science and Technology Europe Forschungs GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Korea Institute of Science and Technology Europe Forschungs GmbH filed Critical Korea Institute of Science and Technology Europe Forschungs GmbH
Publication of EP1989146A1 publication Critical patent/EP1989146A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • 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
    • B01J20/26—Synthetic macromolecular compounds
    • 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
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/268—Polymers created by use of a template, e.g. molecularly imprinted polymers
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/30—Treatment of water, waste water, or sewage by irradiation
    • C02F1/32—Treatment of water, waste water, or sewage by irradiation with ultraviolet light
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/72—Treatment of water, waste water, or sewage by oxidation
    • C02F1/725—Treatment of water, waste water, or sewage by oxidation by catalytic oxidation
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
    • C02F2103/06—Contaminated groundwater or leachate
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2305/00—Use of specific compounds during water treatment
    • C02F2305/10—Photocatalysts

Definitions

  • the present invention relates to a molecularly imprinted polymer and a production process therefor and to a process for selectively treating sparingly degradable and / or toxic compounds in liquids using the molecularly imprinted polymers.
  • Such polymers and processes will be needed to selectively remove and / or degrade biologically degradable pollutants or toxic compounds, for example, from effluents.
  • AOP Advanced Oxidation Processes
  • Claim 5 solved. Advantageous developments of Polymers according to the invention, the preparation process according to the invention and the treatment process according to the invention are given in the respective dependent claims.
  • the method according to the invention for the selective treatment of compounds has several individual steps, which will be explained in more detail below. First, the inclusion of the compound, ie a substance or a specific group of substances from the liquid, such as water or wastewater, in a molecularly imprinted polymer, as described for example in claim 1.
  • the specific or selective uptake of the target molecule and similar compounds in the solution takes place on the one hand via the molecular shape, on the other by defined molecular recognition mechanisms or specific binding interactions (such as ionic interactions or salt bridges, hydrogen bonds, hydrophobic interactions and others)
  • specific binding interactions such as ionic interactions or salt bridges, hydrogen bonds, hydrophobic interactions and others
  • bonding groups on the Kavticians- surfaces, It can be the inclusion of the respective scaffle or the relevant substance group rniccels adsorption (attachment) on the surface as well as by absorption (storage) inside the material (in the further course is therefore generally of “sorption "or” sorb “spoken).
  • the target compounds are liberated or desorbed as preferred compounds or their degradation products with suitable solvents or solvent mixtures.
  • suitable solvents or solvent mixtures water, all imaginable aqueous solutions and organic solvents can be used, even in mixtures with one another and with water or else with dissolved organic or inorganic compounds.
  • AOP advanced oxidation processes
  • a further improvement results when materials or substances are used which have a catalytically active reaction-accelerating effect. These can be used in addition or else coupled to the polymer, for example. Coupling with the AOPs is also possible, but only the activation energy for the formation of certain oxidation products can be reduced. It is also possible to control the reaction by means of such materials or substances in such a way that biodegradable products are already formed by partial oxidation and that thus the oxidizing agent or oxidation process of the AOP can be used more effectively.
  • the washing step for removing the foreign substances taken up and / or the release of the substance or compound (compound) which has been taken up in preference can be avoided or omitted.
  • MGP molecularly imprinted polymer
  • the reagents required for the AOP can be directly: injected into the polymer material or passed through. Direct coupling with catalysts is also possible.
  • the selectively to be treated compound is already degraded directly in the polymer and then the degradation products with suitable
  • Solvents or solvent mixtures as described above removed from the polymer again or sorbierc.
  • catalytically active center is incorporated into the structure of the molecularly imprinted polymer (MIP) and thus serves as an artificial enzyme analogue.
  • MIP molecularly imprinted polymer
  • the catalytic activity of the polymers can by the correct organization of the catalytic groups in the molecularly imprinted binding sites is achieved.
  • catalytic groups may serve structures which generate hydroxyl radicals and / or other oxygen-containing oxidants.
  • TSAs TSA which stabilizes the transition state of the particular degradation reaction and increases the rate of product formation and / or controls product formation either directly or indirectly.
  • Typical degradation reactions may be, for example: hydrolysis of esters, amides, ethers; Ring cleavage, aromatic substitution and other reactions whose transition states can be used as transition state analogues in the manufacturing processes.
  • Coenzyi Ti analogs or coordinating compounds to catalytically assist the reactions.
  • Other catalytic centers can also be used.
  • the predetermined selected and relevant hardly degradable or toxic compounds or classes of compounds are specifically taken up from the liquid, whereby an extension of the operating time of the selective filter component (polymer) is made possible.
  • the relevant pollutants in contrast to the use with activated carbon, can also be degraded later or at the same time to less harmful products, e.g. by an AOP integrated into the polymer or by separation downstream of the polymer.
  • the process according to the invention makes it possible to flexibly use individually tailored molecularly imprinted polymers for a large number of different critical pollutants.
  • the molecularly imprinted polymers used in this way can be regenerated and reused. It is also possible, instead of degrading the hardly degradable compound, to recover them from the polymer, especially in the case of rare compounds.
  • the process can be used to treat liquid media such as water or wastewater that is contaminated or contaminated with special pollutants. Examples include, among other areas:
  • Industrial wastewater such as Process waste water of the chemical or pharmaceutical industry or the pulp and paper industry, municipal wastewater,
  • the method is suitable for the treatment of waste water with a high AOX content.
  • the process can be used in the sewage treatment plant as a replacement for activated carbon or the use of ultrafiltranion as final cleaning.
  • ⁇ from a complex formation of the target molecule (template, print molecule) dissolved in a suitable solvent (porogen) or its molecular units or functional groups with the so-called functional monomer (polymerizable unit which interacts with the print molecule) via specific interactions .
  • a suitable solvent prorogen
  • the functional monomer polymerizable unit which interacts with the print molecule
  • the cross-linker unit having two or more linkages with the functional monomers
  • the subject of the present invention is the use in connection with environmental fluid media, e.g. Water or wastewater, and with: the selective removal and degradation of ingredients of these liquid media.
  • environmental fluid media e.g. Water or wastewater
  • Relevant here is the selection and modification of the functional monomers or of a mixture of functional monomers, cross-linkers or a mixture of crosslinkers, porogen or porogen mixtures and of radical initiators and suitable catalytic groups for particular target molecules or target molecule groups or their Derivatives and the preparation of a suitable washing and purification protocol for newly prepared polymers.
  • the invention relates in addition to the production of novel functional monomers, by the inventive method for the selective treatment of liquids with recording, washing, desorption and degradation step with the materials and reagents or technologies used, if necessary, the method can all listed
  • Typical functional monomers used may be: Carboxylic acids, such as acrylic acid, methacrylic acid, Triflu- or methacrylic acid, vinyl benzoic acid, itaconic acid, and their amides;
  • Sulfonic acids such as acrylamidomethylpropanesulfonic acid
  • heteroaromatic or weak bases such as substituted or unsubstituted vinylpyridines, vinylpyrimidines, vinylpyrazoles, vinylimidazoles, vinyltriazines, vinylpurines, -indoles, -quinolines, -acridines, -phenanthridines, bis (acrylamido) pyridine;
  • aliphatic or aromatic vinyl derivatives such as substituted or unsubstituted styrenes, vinylnaphthalenes, vinylnaphthalenecarboxylic acids, vinylnaphthols, vinylanthracenes, vinylanthracenecarboxylic acids, vinylphenanthrenes, vinylphenanthrenecarboxylic acids, and similar fused aromatics, vinylbenzamidine; Acryloylamino-benzamidine, (amidinoalkyl) -styrene, where the alkyl may be methyl, ethyl or propyl, N-acryloyl- (amidinoalkyl) -aniline, vinyl derivatives with chelating groups, such as iminodiacetic acid, ethylenediamine tetraacetic acid, inter alia, for complexing metal ions , Silanes, as well as mixtures of such monomers. Other functional monomers can also be used.
  • crosslinker (unity mic two or more linkage possibilities with the functional monomers) can serve:
  • Bis (acryloyl) alkanes ethane, propane and butane being suitable as aikans
  • Systems based on acrylic acid or methacrylic acid such as, for example, ethylene glycol dimethacrylate (EDMA) and trimethylolpropane trimethacrylate (TRIM);
  • PTRA Pentaerythritol triacrylate
  • PETEA pentaerythritol tetraacrylate
  • Crosslinkers containing functional groups e.g. Acrylamide units which are linked to the amide nitrogens by means of aliphatic (methylene-a.a.), aromatic (phenylene and the like) or heteroaromatic (pyridinyl and the like) spacers.
  • Other cross-linkers can also be used, for example also cross-linkers that are stable against UV light or ozone.
  • solvents of different dielectric constants can be used, the parameters such as different swelling properties of the polymer, different morphologies of the polymer with different structures and pore diameters / porosity or influence different inductive strengths of noncovalent interactions, in particular aliphatic or alicyclic hydrocarbons such as hexane, heptane or cyclohexane,
  • aromatic hydrocarbons such as toluene
  • halogenated hydrocarbons such as chloroform, dichloromethane or 1,2-dichloro-anhane
  • short-chain alcohols such as methanol, ethanol, propanol; Ether, acetonitrile, tetrahydrofuran, ethyl acetate, acetone, dimethylformamide, dioxane, dimethyl sulfoxide;
  • UV initiators 2,2'-azobisisobutyronitrile (AIBN), 2,2'-azobis (2,4-dimethyl valeronicril) (ADVN) and others can be used, including the use of UV light possible.
  • AIBN 2,2'-azobisisobutyronitrile
  • ADVN 2,2'-azobis (2,4-dimethyl valeronicril)
  • others can be used, including the use of UV light possible.
  • the molecularly imprinted polymers can be present in the following forms after the production process:
  • the polymer can be introduced into a separation column or into a filter device made of plastic, glass, stainless steel or other materials; or bonded to thin films, surfaces of different materials or polymer membranes or else itself can be used as a membrane.
  • the particles can be freely floating in the liquid phase.
  • Other devices for receiving the polymer can be used.
  • reactor shape can also vary.
  • Water can be passed through both the separation column, filter device, membrane, etc., and also be conducted past the sorbent material almost in parallel. Other methods can also be used.
  • Fig. 1 shown. This table represents the relevant substances used for the preparation of the molecularly imprinted polymers.
  • the individual components were mixed together in 50 ml test tubes with ice cooling, purged with nitrogen for 5 min, sealed with parafilm and left at 60 ° C. for 19 h.
  • the polymer blocks were crushed until particles with a particle size ⁇ 250 microns are formed; then triturated four times with 50 ml of acetone and filtered through a 20 micron sieve.
  • FIG. 2 now shows the proportion of sorbed (in%) and concentration of clofibric acid remaining in the aqueous phase (in mol / l) after one or two sorption reactions per 300 mg of the molecularly imprinted polymer in MIP 1 treated wastewater 10 ml landfill leachate with the addition of 1.2 * 10 "4 M clofibric acid, 300 mg MIP 1 was added to this effluent to be treated and stirred for 30 minutes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Hydrology & Water Resources (AREA)
  • Water Treatment By Sorption (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Biological Treatment Of Waste Water (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un polymère gravé moléculairement ainsi qu'un procédé de fabrication de ce polymère et un procédé de traitement sélectif de composés difficilement dégradables et/ou toxiques dans des liquides par utilisation du polymère gravé moléculairement. Le polymère et le procédé sont utiles pour éliminer et/ou réduire les polluants biologiques, difficilement dégradables ou les composés toxiques, par exemple dans des eaux usées. L'invention concerne donc un polymère gravé moléculairement utile pour le traitement sélectif d'au moins un composé difficilement dégradable et/ou toxique avec un réseau polymérique constitué de monomères comportant des cavités d'une taille prédéterminée, les cavités étant disposées à intervalles prédéterminés et présentant des sites et/ou motifs de liaison spécifiques aux composés difficilement dégradables et/ou toxiques.
EP07722869A 2006-02-20 2007-02-20 Polymere grave moleculairement, son procede de fabrication et procede de traitement selectif de composes difficilement degradables et/ou toxiques dans des liquides Withdrawn EP1989146A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006007796A DE102006007796B3 (de) 2006-02-20 2006-02-20 Verfahren zur selektiven Behandlung von schwer abbaubaren und/oder toxischen Verbindungen in Abwasser oder Wasser
PCT/EP2007/001455 WO2007096135A1 (fr) 2006-02-20 2007-02-20 Polymere grave moleculairement, son procede de fabrication et procede de traitement selectif de composes difficilement degradables et/ou toxiques dans des liquides

Publications (1)

Publication Number Publication Date
EP1989146A1 true EP1989146A1 (fr) 2008-11-12

Family

ID=37963849

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07722869A Withdrawn EP1989146A1 (fr) 2006-02-20 2007-02-20 Polymere grave moleculairement, son procede de fabrication et procede de traitement selectif de composes difficilement degradables et/ou toxiques dans des liquides

Country Status (6)

Country Link
US (1) US20100036188A1 (fr)
EP (1) EP1989146A1 (fr)
JP (1) JP2009529066A (fr)
KR (1) KR20080110590A (fr)
DE (1) DE102006007796B3 (fr)
WO (1) WO2007096135A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010100708A (ja) * 2008-10-22 2010-05-06 Mukogawa Gakuin 分子インプリントポリマーおよびその製造方法
JP2013501108A (ja) * 2009-08-05 2013-01-10 モナシュ ユニバーシティ 分子インプリントポリマー、それらを製造するための方法およびそれらの使用
PE20161381A1 (es) * 2009-08-27 2016-12-28 Alltech Inc Adsorbentes sinteticos de micotoxina y metodos para elaborarlos y utilizarlos
JP2011062594A (ja) * 2009-09-15 2011-03-31 Nagoya Institute Of Technology インジウム吸着材とその製造方法、及びインジウム吸着方法
CN101816923B (zh) * 2010-04-07 2012-09-05 东北林业大学 一种金属离子吸附剂的制备方法
GB201206190D0 (en) * 2012-04-05 2012-05-23 Health Prot Agency Decontaminant product and method
US9248439B2 (en) * 2012-07-06 2016-02-02 Empire Technology Development Llc Molecularly imprinted catalysts and methods of making and using the same
DE102013203484A1 (de) 2013-03-01 2014-09-04 Henkel Ag & Co. Kgaa Farbschützende Waschmittel
JP2016141665A (ja) * 2015-02-04 2016-08-08 オルテック インコーポレイテッド アフラトキシン鋳型、分子インプリントポリマー、ならびにその作製法および使用法
CN106746345A (zh) * 2017-01-04 2017-05-31 安徽国星生物化学有限公司 一种吡啶生产废水的处理方法
CN107986387B (zh) * 2017-12-14 2023-09-22 长安大学 基于磁性分子印迹的超声辅助选择性光催化方法及其装置
CN109180864B (zh) * 2018-07-18 2021-05-18 江苏全给净化科技有限公司 用于净化水中磺胺类药物的分子印迹聚合物材料及应用
CN109179814B (zh) * 2018-11-26 2024-06-14 南京紫江工程科技有限公司 一种组合高级氧化处理污水的方法
CN110523398B (zh) * 2019-09-11 2021-08-06 山东大学 一种碳纳米片层负载TiO2分子印迹材料及其制备方法和应用
CN116554486B (zh) * 2023-05-23 2024-05-17 合肥普力先进材料科技有限公司 一种三叶草型高选择性吸附钴离子的吸附剂及其制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4575539A (en) * 1985-06-03 1986-03-11 E. R. Squibb & Sons, Inc. Drug delivery systems including novel interpenetrating polymer networks and method
US5942444A (en) * 1997-01-27 1999-08-24 Biocode, Inc. Marking of products to establish identity, source and fate
WO1998038222A2 (fr) * 1997-02-27 1998-09-03 Universität Karlsruhe (Th) Formes modifiees de cyclodextrine a canaux moleculaires, procedes pour leur preparation ainsi que leur utilisation
US6783686B2 (en) * 2001-06-25 2004-08-31 Anna Madeleine Leone Method for removing the gasoline additive MTBE from water using molecularly imprinted polymers
JP2006137805A (ja) * 2004-11-10 2006-06-01 Tohoku Univ 対象化合物を捕捉することができるモレキュラーインプリンテッドポリマー、その調製方法、およびモレキュラーインプリンテッドポリマーにより対象試料中の対象化合物を捕捉する方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007096135A1 *

Also Published As

Publication number Publication date
KR20080110590A (ko) 2008-12-18
WO2007096135A1 (fr) 2007-08-30
JP2009529066A (ja) 2009-08-13
DE102006007796B3 (de) 2008-01-10
US20100036188A1 (en) 2010-02-11

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