EP3155674A2 - Système de matières combinatoire pour des membranes échangeuses d'ions et son utilisation dans des processus électrochimiques - Google Patents

Système de matières combinatoire pour des membranes échangeuses d'ions et son utilisation dans des processus électrochimiques

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Publication number
EP3155674A2
EP3155674A2 EP15763190.4A EP15763190A EP3155674A2 EP 3155674 A2 EP3155674 A2 EP 3155674A2 EP 15763190 A EP15763190 A EP 15763190A EP 3155674 A2 EP3155674 A2 EP 3155674A2
Authority
EP
European Patent Office
Prior art keywords
membrane
membranes
polymer
groups
pbi
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.)
Pending
Application number
EP15763190.4A
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German (de)
English (en)
Inventor
Jochen Kerres
Carlo Morandi
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.)
HAERING, THOMAS
Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart
Original Assignee
Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart
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Application filed by Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart filed Critical Institut fuer Chemische Verfahrenstechnik Universitaet Stuttgart
Publication of EP3155674A2 publication Critical patent/EP3155674A2/fr
Pending legal-status Critical Current

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    • 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
    • C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
    • C08J5/2262—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation containing fluorine
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
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    • B01D71/06—Organic material
    • B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
    • B01D71/62—Polycondensates having nitrogen-containing heterocyclic rings in the main chain
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    • C25B13/04—Diaphragms; Spacing elements characterised by the material
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    • H01M8/1027—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having carbon, oxygen and other atoms, e.g. sulfonated polyethersulfones [S-PES]
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    • H01M8/103—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having nitrogen, e.g. sulfonated polybenzimidazoles [S-PBI], polybenzimidazoles with phosphoric acid, sulfonated polyamides [S-PA] or sulfonated polyphosphazenes [S-PPh]
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    • H01M8/1018—Polymeric electrolyte materials
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    • H01M8/1032—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having sulfur, e.g. sulfonated-polyethersulfones [S-PES]
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    • H01M8/1034—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having phosphorus, e.g. sulfonated polyphosphazenes [S-PPh]
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    • H01M8/1086—After-treatment of the membrane other than by polymerisation
    • H01M8/1088—Chemical modification, e.g. sulfonation
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Definitions

  • Multi-use embranen (use as AEM, H 3 P0 4 -doped HT membranes, HT-HyS electrolysis membranes, membranes as separators for redox-flow batteries)
  • a halomethylated polymer with a basic polymer (eg PBI: F 6 PBI or PBIOO) in a dipolar aprotic solvent such as DMSO or DMAc, NM P, etc.
  • a dipolar aprotic solvent such as DMSO or DMAc, NM P, etc.
  • a halomethylated polymer with a PBI (preferably ABPBI, F 6 PBI or PBIOO) in DMAc, cooling to 0-5 ° C., addition of any tertiary amine (eg TEA, DABCO, ABCO), rapid homogenization and knife coating, Evaporation at 60-150 ° C, post-treatment in sulfuric acid (60-90% H 2 S0 4 ), washing the film -> covalently ionically cross-linked acid-base blend membrane
  • Phosphoric acid-doped polybenzimidazole (PBI) for use in fuel cells is the work of Savinell et al. back 1 .
  • the advantage of the PBI / H 3 P0 4 composite membranes is that instead of water, the phosphoric acid takes over the H + line 2 , which makes this type of membrane suitable for use at fuel cell operating temperatures between 100 and 200 ° C.
  • Disadvantage of this type of membrane is the possible bleeding of the phosphoric acid from the composite membrane when the fuel cell temperature drops below 100 ° C, and condensing product water from the membrane flours phosphoric acid 3 . The liberated phosphoric acid can then cause severe corrosion damage in the fuel cell system.
  • H 3 P0 4 -doped PBI membranes Another disadvantage of H 3 P0 4 -doped PBI membranes is the chemical degradation of the PBI in the fuel cell 4 .
  • Some strategies have been implemented in the R & D of this type of membrane to reduce the degradation of PBI in fuel cell operation.
  • One strategy is the preparation of acid-base blend membranes from PBI and acidic polymers, wherein the acidic polymer takes on the role of an ionic crosslinker by proton transfer from the acidic polymer to the PBI-imidazole.
  • Acid-base blend membranes were researched and developed in the inventor's working group 5 and, in part, modified in collaboration with Q. Li's research group at the Danish Technical University (DTU) for medium-temperature membranes in an EU project.
  • DTU Danish Technical University
  • base-acid blend membranes were prepared from different PBIs such as PBIOO and F 6 PBI with phosphonated poly (pentafluorostyrene) 7 and doped with H 3 P0 4 8 .
  • the blend membranes had excellent chemical stabilities: one of the membranes (blend of 50 wt% PBIOO and 50 wt% PWN) showed a mass loss of only 2% even after 144 h in Fenton's reagent, whereas pure PBIOO after the same storage time in Fenton's reagent had a mass loss of 8%.
  • Another way to increase the chemical stability of PBI-type membranes is to prepare covalently cross-linked PBI membranes described by Q. Li et al. and other research groups.
  • the PBI can be crosslinked with a low molecular weight crosslinker such as bisphenol A bisepoxide 9 , divinyl sulfone 10 or a high molecular weight crosslinker such as chloromethylated PSU 11 or bromomethylated polyether ketone 12 .
  • a low molecular weight crosslinker such as bisphenol A bisepoxide 9 , divinyl sulfone 10 or a high molecular weight crosslinker such as chloromethylated PSU 11 or bromomethylated polyether ketone 12 .
  • Further attempts to increase the stability of PBI membranes relate to the preparation of nanoparticle-modified PBI membranes 13 , or the preparation of partially sulfonated PBI, which crosslinks intra- or intermolecularly ionically by proton transfer from the acidic group to the imidazole group 14 15 .
  • a variety of polymers are currently used as backbonead polymers for the production of novel AEMs, including ethylene-tetrafluoroethylene, polyetheretherketones, polyethersulfone, poly (ether sulfone ketone). , Polyethylene, polyphenylene oxide, polystyrene, polyvinyl acetate, poly (vinylbenzyl chloride), polyvinylidene fluoride.
  • Table 1 gives a comprehensive compilation of relevant non-commercial AEMs, which are also juxtaposed with the Tokuyama A201 benchmark membrane.
  • the corresponding IEC value is 1.7 meq-g -1 .
  • the benchmark membrane was characterized in the context of this invention under the same measuring conditions.
  • Covalently and / or ionically crosslinked PBI blend membranes which are prepared with halomethylated and optionally sulfonated and / or phosphonated polymers and tailored in terms of their properties, are described in the context of this invention based on the state of R & D.
  • the blend membranes are additionally crosslinked covalently, for example by adding a low and / or a macromolecular crosslinker.
  • the membranes can be used in electrochemical processes as low-temperature cation exchange membranes, low-temperature anion exchange membranes (temperature range without pressure up to 100 ° C.
  • redox flow batteries for example all-vanadium, iron-chromium, etc.
  • the anion exchange membranes consist of the following components: a) Any polybenzimidazole (PBI) as a matrix polymer, examples of which are as follows: Polyphenzimidazoles as ABPBI, PBI Celazol, p-PBI, F 6 PBI, SO 2 PBI, and PBIOO. Characteristic of the polybenzimidazoles used is the recurring occurrence of the benzimidazole unit in the main chain or side chain of the polymer.
  • PBI polybenzimidazole
  • alkyl halide (monohaloalkane, dihaloalkane, oligohaloalkane, monobenzyl halide, dibenzyl halide, tribenzyl halide, etc.), for example, diiodoalkane such as diiodopropane, diiodobutane, diiodopentane, diiodohexane, diiodoheptane, diiodooctane, diiodononane, diiododecane, etc.
  • diiodoalkane such as diiodopropane, diiodobutane, diiodopentane, diiodohexane, diiodoheptane, diiodooctane, diiodononane, diiododecane, etc.
  • diiodoalkane such as diiodo
  • the anion exchange groups of the blend are in molar excess compared to the other functional groups such.
  • a dipolar aprotic solvent NM P, DMAc, DMF, DMSO, NEP, sulfolane, etc.
  • the chemical compound containing tertiary nitrogen may contain one, two or more tertiary nitrogen atoms.
  • the tertiary nitrogen compound may also be an oligomer (eg a polyvinylpyridine). Thereafter, the polymer solution is laced on a substrate, sprayed or poured and the solvent evaporated. Thereafter, the resulting membrane is aftertreated:
  • membranes consist of a molar excess of a polybenzimidazole, where the polybenzimidazole may be differentially crosslinked to limit its mineral acid or water uptake.
  • the membranes may consist of the following components: a) a polybenzimidazole (PBI) as matrix polymer (as example ABPBI, PBI Celazol, p-PBI, F 6 PBI, SO 2 PBI, PBIOO and other polybenzimidazoles)
  • alkyl halide (monohaloalkane, dihaloalkane, oligohaloalkane, monobenzyl halide, dibenzyl halide, tribenzyl halide, etc.), for example, diiodoalkane such as diiodopropane, diiodobutane, diiodopentane, diiodohexane, diiodoheptane, diiodooctane, diiodononane, diiododecane, etc.
  • diiodoalkane such as diiodopropane, diiodobutane, diiodopentane, diiodohexane, diiodoheptane, diiodooctane, diiodononane, diiododecane, etc.
  • Covalently cross-linked PBI blend membranes can consist of the components a), b), c), d) and optionally a polymeric sulfinate RSO 2 X, covalently-ionically cross-linked membranes additionally contain cation exchange polymers listed under e).
  • the membranes are doped with phosphoric acid or phosphonic acid.
  • the Phosphor Textre- / Phosphonklare mask by the concentration of the acid, by the bath temperature and by the residence time of the membrane in the mineral acid such.
  • B. phosphoric acid / PhosphonTalkrebad be controlled.
  • a covalently cross-linked PBI is obtained, for example, by: a) mixing the PBI with a halomethylated polymer, the halomethylated polymer reacting with one or both N atoms of the imidazole group of the PBI by alkylation ( Figure 1).
  • a covalently ionically crosslinked membrane is obtained by a) Before the evaporation of the solvent, a phosphonated and / or sulfonated polymer is added to the polymer mixture.
  • the membrane is placed in a solution containing tris (trimethylsilyl) phosphite.
  • part of the aromatic F is replaced by Phosphonklasilylester groups, which can be easily hydrolyzed by boiling with water to free phosphonic acid groups.
  • Nucleophilic replaceable aromatic F bonds can also be replaced by other functional groups, for example by thiol groups, which can be used in a further step after for crosslinking.
  • Acid-excess blend membranes for H 2 fuel cells, DMFC, PEM electrolysis, redox-flow batteries
  • a polybenzimidazole (PBI) as a matrix polymer (as example ABPBI, PBI Celazol, p-PBI, F 6 PBI, SO 2 PBI, PBIOO and other polybenzimidazoles)
  • alkyl halide optionally an alkyl halide (monohaloalkane, dihaloalkane, oligohaloalkane, monobenzyl halide, dibenzyl halide, tribenzyl halide, etc.), for example diiodoalkane such as diiodopropane, diiodobutane, diiodopentane, diiodohexane diiodoheptane, diiodooctane, diiodononane, diiododecane, etc.
  • diiodoalkane such as diiodopropane, diiodobutane, diiodopentane, diiodohexane diiodoheptane, diiodooctane, diiodononane, diiododecane, etc.
  • the acidic groups are in molar excess, so that these membranes are cation-conductive.
  • the blend membranes are covalently-ionically crosslinked when they the components a), b) c) and optionally d) and e).
  • Membranes are claimed which, depending on the proportion of the respective main blend components, can be used in various electrochemical processes.
  • the tabular overview lists the main membrane types and their respective fields of application.
  • the membranes according to the invention have excellent mechanical and chemical stability and, at the same time, excellent ionic conductivities.
  • Table 1 shows the values of comparative membranes from the prior art.
  • the membranes are laced on glass plates for the sake of simplicity.
  • the membranes may also be applied to other substrates and substrates, e.g. on foils or metal strips to be produced from roll to roll or in suspended dryers.
  • the membranes can also be deposited on substrates without them necessarily having to be removed from them again.
  • An example is graphite felts, nonwovens, fabrics or porous materials, such as films with pores or felts. All listed aftertreatments then take place with the substrate on which the membrane was deposited or was formed after removal of the solvent. In this case, the membrane no longer separates from the carrier material, which is wanted.
  • the solvent is removed. This happens here by evaporation at 140 ° C.
  • the solvent will also evaporate at lower or higher temperatures, e.g. in the temperature range from 30 ° C to 180 ° C.
  • Example 1 HTPEM from PBI, halomethylated polymer (covalently crosslinked) (membrane MJK 1885)
  • Example 2 HTPEM of PBI, Halomethylated Polymer, Tertiary Amine, Sulfonated Polymer (Covalently-Ionically Crosslinked) (MJK-1959)
  • Example 3 AEM from PBI, halomethylated polymer, tertiary amine, sulfonated polymer (covalently ionically crosslinked] (membrane MJK-1932)
  • 0.5 g of F 6 PBI are mixed as a 5% solution in DMAc with 0.5 g of PPOBr as 5% solution in DMAc and 0.107 g of the sulfonated polymer sPPSU and 1.08 ml of the tertiary amine N-methylmorpholine (polymeric blend components see Figure 10).
  • a membrane is straightened from this solution on a glass plate, and the solvent is removed in a convection oven at 140 ° C. Thereafter, the membrane is dissolved under water and post-treated as follows: 48 hours 10% HCl at 90 ° C, then 48 hours DI water at 60 ° C. By reaction of a small part of the CH 2 Br groups with the imidazole NH under alkylation, covalent cross-linking bridges are formed. Thereafter, the membrane is characterized as follows:
  • Thickness 105 ⁇
  • Example 4 CEM of Sulfonated Polymer, PBI, Halomethylated Polymer, Tertiary Amine (Covalently-Ionically Crosslinked) (Membrane MJK-1957)
  • 0.12 g of F 6 PBI are mixed as a 5% solution in DMAc with 0.12 g of PARBrl as a 5% solution in DMAc and 2 g of the sulfonated polymer sPPSU and 0.195 g of 1-ethyl-2-methylimidazole (see Polymer Blend Components Figure 12).
  • a membrane is straightened from this solution on a glass plate, and the solvent is removed in a convection oven at 140 ° C. Thereafter, the membrane is dissolved under water and post-treated as follows: 48 hours 10% HCl at 90 ° C, then 48 hours DI water at 60 ° C.
  • reaction of a small part of the CH 2 Br groups with the imidazole NH under alkylation covalent cross-linking bridges are formed.
  • Example 5 AEM from sulfonated polymer, PBI, halomethylated polymer, tertiary amine (covalently-ionically crosslinked)
  • a membrane is straightened from this solution on a glass plate, and the solvent is removed in a convection oven at 140 ° C. Thereafter, the membrane is dissolved under water and post-treated as follows: 48 hours 10% HCl at 90 ° C, then 48 hours DI water at 60 ° C. By reaction of a small part of the CH 2 Br groups with the imidazole NH under alkylation, covalent cross-linking bridges are formed. Thereafter, the membrane is characterized as follows:
  • Example 6 AEM from sulfonated polymer, F 6 PBI, halomethylated / partially fluorinated polymer, tertiary mono- and diamine (covalently-ionically crosslinked)
  • a membrane is poured from this solution onto a Petri dish, and the solvent in a convection oven at 80 ° C withdrawn. Subsequently, the membrane is dissolved under water and aftertreated as follows: 48 hours in a mixture of 50/50 DABCO / EtOH at 80 ° C, then 48 hours in demineralized water at 90 ° C.
  • covalent cross-linking bridges are formed. The diamine further covalently cross-links the membrane.
  • Figure 14 shows the degree of crosslinking as a function of the SAC content in the polymer solution for NMM-DABCO quaternized membranes from PAK18r-60-F 6 PBI.
  • Example 7 AEMs of PBIOO, Halomethylated Polymer, Alkylimidazole (Covalently Crosslinked)
  • a membrane is poured in each case from the polymer solution onto a Petri dish, and the solvent is removed in a circulating air drying oven at 80.degree. Subsequently, the membranes are removed under water and rinsed for 48 hours in deionized water at 90 ° C.
  • covalent cross-linking bridges are formed.
  • Figure 15 shows the comparison of the chloride conductivities (1 M NaCl, RT) of the alkylimidazole quaternized PPO-PBIOO membranes and the commercial Tokuyama membrane A201 (development code A006).
  • Example 8 AEMs of (sulfonated polymer,) F 6 PBI, halomethylated polymer, tertiary mono- and diamine (covalently and / or ionically crosslinked (Figure 17)
  • a membrane is poured from the solution onto a Petri dish, and the solvent in a convection oven at 80 ° C withdrawn.
  • the membrane is then removed under water and after-treated as follows: 48 hours in TMEDA (1 d RT, ld 50 ° C), then 48 hours in deionized water at 90 ° C.
  • a membrane is poured from the solution onto a Petri dish, and the solvent in a convection oven at 80 ° C withdrawn.
  • the membrane is then dissolved under water and after-treated as follows: 48 hours in TMEDA (1 d RT, id 50 ° C, then 48 hours in demineralized water at 60 ° C.)
  • IEC value mmol / g: k. A. k. A.
  • Example 9 AEMs of sulfonated polymer F 6 PBI, halomethylated polymer, tertiary mono- and diamine (covalently ionically crosslinked) -> 44, 45, 46
  • 0.2025 g of F 6 PBI is added as a 5% solution in DMAc with 0.2025 g of PPOBr as a 5% solution in DMAc and, depending on the membrane, with 0.02025 g of SAC (44-PPO-50-F6PBI-SAC-5 -NMM-DABCO), 0.0405 g SAC (45-PPO-50-F6PBI-SAC-10-NMM-DABCO) or 0.06075 g SAC (46-PPO-50-F6PBI-SAC-15-NMM-DABCO ) as a 5% solution in DMAc and 0.59 ml of the tertiary monoamine N-methylmorpholine mixed (ionic-covalently cross-linked acid-base blends)
  • Example 10 AEMs of sulfonated polymer FePBI, halomethylated polymer, tertiary monoamine [covalently ionic crosslinked] -> 71, 72, 73, 74, 75
  • 0.2025 g of F 6 PBI are dissolved as a 5% solution in DMAc with 0.2025 g of PPOBr as a 5% solution in DMAc and, depending on the membrane, with 0.02025 g of SAC (71-PPO-50-F6PBI-SAC-5).
  • a membrane is poured from the solution onto a Petri dish, and the solvent in a convection oven at 80 ° C withdrawn.
  • the membrane is then removed under water and after-treated as follows: 48 hours in 15% NMM in EtOH (1 d RT, 1 d 50 ° C), then 48 hours in demineralized water at 90 ° C.
  • Table 8 lists the compositions of various AEM blends, and Table 9 lists some of their properties.
  • the membranes are due to their excellent properties, conductivity and

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Abstract

L'invention concerne un procédé de fabrication de membranes mixtes réticulées de façon covalente et/ou ionique, à partir d'un polymère halométhylé, d'un polymère contenant des groupes N-basiques tertiaires, de préférence polybenzimidazole, et éventuellement d'un polymère contenant des groupes échangeurs de cations tels que des groupes acide sulfonique ou acide phosphonique. Les membranes peuvent être réalisées sur mesure en ce qui concerne leurs propriétés et peuvent par exemple être employées comme membranes échangeuses de cations ou membranes échangeuses d'anions dans des piles à combustible basse température ou des électrolyses basse température, ou dans des batteries redox, ou peuvent être employées, lorsqu'elles sont dopées avec des conducteurs de protons tels que l'acide phosphorique ou l'acide phosphonique, dans des piles à combustible moyenne température ou des électrolyses moyenne température.
EP15763190.4A 2014-06-12 2015-06-12 Système de matières combinatoire pour des membranes échangeuses d'ions et son utilisation dans des processus électrochimiques Pending EP3155674A2 (fr)

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DE102014009170.8A DE102014009170A1 (de) 2014-06-12 2014-06-12 Kombinatorisches Materialsystem für Ionenaustauschermembranen und dessen Verwendung in elektrochemischen Prozessen
PCT/DE2015/000294 WO2015188806A2 (fr) 2014-06-12 2015-06-12 Système de matières combinatoire pour des membranes échangeuses d'ions et son utilisation dans des processus électrochimiques

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DE102016007815A1 (de) 2016-06-22 2017-12-28 Universität Stuttgart Vernetzte hochstabile Anionenaustauscherblendmembranen mit Polyethylenglycolen als hydrophiler Membranphase
WO2019169064A1 (fr) * 2018-02-28 2019-09-06 Johnson Ip Holding, Llc Procédé de liaison de membranes dopées à l'acide
CN108479436B (zh) * 2018-04-10 2021-06-08 合肥工业大学 一种侧链型均相阴离子交换膜及其制备方法
CN108878740B (zh) * 2018-07-03 2020-04-07 大连理工大学 一种非离子型侧链修饰聚苯并咪唑膜及其制备方法
KR20210122231A (ko) * 2018-11-26 2021-10-08 렌슬러 폴리테크닉 인스티튜트 인산 음이온-사차 암모늄 이온 쌍 배위 고분자 막
CN109742428B (zh) * 2019-01-28 2021-07-23 太原理工大学 一种基于n-螺环季铵盐聚合物的共混阴离子交换膜
CN109904500B (zh) * 2019-02-25 2020-11-24 四川大学 一种侧链型磺化聚砜/聚乙烯醇质子交换膜及其制备方法
CN112952167A (zh) * 2019-12-10 2021-06-11 中国科学院大连化学物理研究所 一种酸碱交联离子传导膜在液流电池中的应用
CN111454475B (zh) * 2020-03-24 2022-05-31 深圳市燃气集团股份有限公司 一种氢燃料电池用质子交换膜材料及其制备方法与应用
CN113527684B (zh) * 2020-04-21 2023-11-03 武汉理工大学 一种基于接枝聚苯并咪唑作为质子导体的氧还原催化层及其制备方法
KR102358626B1 (ko) * 2020-06-11 2022-02-07 한국과학기술연구원 복합 이온 교환 멤브레인, 이의 제조방법 및 이의 용도
CN111682248A (zh) * 2020-06-29 2020-09-18 香港科技大学 一种具有高质子电导率和离子选择性的pbi膜活化处理方法
CN113078341A (zh) * 2021-03-30 2021-07-06 长春工业大学 一种聚醚醚酮/阳离子型金属有机框架交联膜及其制备方法
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