WO2017220065A1 - Vernetzte hochstabile anionenaustauscherblendmembranen mit polyethylenglycolen als hydrophiler membranphase - Google Patents
Vernetzte hochstabile anionenaustauscherblendmembranen mit polyethylenglycolen als hydrophiler membranphase Download PDFInfo
- Publication number
- WO2017220065A1 WO2017220065A1 PCT/DE2017/000179 DE2017000179W WO2017220065A1 WO 2017220065 A1 WO2017220065 A1 WO 2017220065A1 DE 2017000179 W DE2017000179 W DE 2017000179W WO 2017220065 A1 WO2017220065 A1 WO 2017220065A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- groups
- halomethylated
- membrane
- room temperature
- Prior art date
Links
- URGLLJMGRBQWJG-UHFFFAOYSA-N CCc(c(F)c(c(-c(c(F)c(c(Oc(c(CBr)c1)c(CBr)cc1-c(cc1CBr)cc(CBr)c1OC)c1F)F)c1F)c1F)F)c1F Chemical compound CCc(c(F)c(c(-c(c(F)c(c(Oc(c(CBr)c1)c(CBr)cc1-c(cc1CBr)cc(CBr)c1OC)c1F)F)c1F)c1F)F)c1F URGLLJMGRBQWJG-UHFFFAOYSA-N 0.000 description 1
- HSFZYWJTEPDWER-UHFFFAOYSA-N CP(c1ccccc1)(S(S(SC)=O)(=O)=O)=O Chemical compound CP(c1ccccc1)(S(S(SC)=O)(=O)=O)=O HSFZYWJTEPDWER-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
- B01J41/13—Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/28—Polymers of vinyl aromatic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/28—Polymers of vinyl aromatic compounds
- B01D71/281—Polystyrene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/52—Polyethers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/52—Polyethers
- B01D71/521—Aliphatic polyethers
- B01D71/5211—Polyethylene glycol or polyethyleneoxide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/52—Polyethers
- B01D71/522—Aromatic polyethers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/52—Polyethers
- B01D71/522—Aromatic polyethers
- B01D71/5222—Polyetherketone, polyetheretherketone, or polyaryletherketone
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
- B01D71/68—Polysulfones; Polyethersulfones
-
- 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
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
- B01J41/14—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B13/00—Diaphragms; Spacing elements
- C25B13/04—Diaphragms; Spacing elements characterised by the material
- C25B13/08—Diaphragms; Spacing elements characterised by the material based on organic materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1025—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon and oxygen, e.g. polyethers, sulfonated polyetheretherketones [S-PEEK], sulfonated polysaccharides, sulfonated celluloses or sulfonated polyesters
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- 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]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- 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]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
- H01M8/184—Regeneration by electrochemical means
- H01M8/188—Regeneration by electrochemical means by recharging of redox couples containing fluids; Redox flow type batteries
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/42—Ion-exchange membranes
-
- 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
- C08J2325/00—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 at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
-
- 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
- C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2471/02—Polyalkylene oxides
-
- 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
- C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- 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
- C08J2481/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
- C08J2481/06—Polysulfones; Polyethersulfones
Definitions
- AEMs anion exchange membranes
- APEFCs alkaline polymer electrolyte fuel cells
- AEE alkaline polymer electrolyte electrolysis
- RFBs redox flow batteries
- RED Reverse electrodialysis
- MFCs microwave fuel cells
- DD diffusion dialysis
- a major advantage of using AEM in electrochemical conversion processes such as fuel cells or electrolysis is that when using AEMs for the electrocatalytic reactions at the electrodes no precious metal catalysts consisting of platinum group metals (PGM) are required, thus containing AEM Membrane electrode assemblies (MEAs) are significantly less expensive than cation exchange membrane (CEM) containing MEAs.
- PGM platinum group metals
- AEMs have the following major drawbacks compared to CEMs:
- Ion conductivity is significantly lower for most AEM types than for CEMs of comparable ion exchange capacity (IEC), in part because most of the AEMs have a hydrocarbon backbone that is significantly less hydrophobic than perfluorinated ones, for example Polymer backbone of perfluorinated membranes of the Nafion ® type, so that it comes in the AEM to a lower separation between ionic groups and polymer backbone, which leads to lower ionic conductivity because of the then lower local density of the anion exchange groups, especially for most AEM types the Festkationen merely attached to the polymer backbone via a CH 2 bridge [20].
- IEC ion exchange capacity
- AEM A monomer having aromatic groups
- polystyrene polystyrene
- polyphenylene ethers or other aromatic polyethers
- polyethersulfones polyether ketones o. ⁇ .
- the first step in the preparation of AEM is the synthesis of a polymer with halomethyl side groups.
- Halomethylation is achieved by (1) chloro- or bromomethylation with hydrogen, formaldehyde and a Lewis acid such as ZnCl 2 or AICI 3 (Blanc reaction [23,24]), or (2) bromination of the CH 3 side group of aromatic polymers with N-bromo-succinimide (NBS) by the well-Ziegler bromination reaction [25].
- the Blanc reaction is associated with the appearance of the highly carcinogenic by-product bis (chloromethyl) ether. For this reason, the Wohl-Ziegler reaction is now preferably used in the production of halomethylated aromatic polymers.
- Literature examples for the preparation of bromomethylated aromatic polymers by the Wohl-Ziegler reaction are the bromomethylation of polyphenylene oxide [26] or the bromomethylation of a methylated polyethersulfone [27].
- Phase-segregated AEMs with improved ionic conductivity are obtainable by the preparation of linear block copolymers from hydrophobic and ionic blocks [31] or by graft copolymers with an anion exchange group-containing grafting side chain [32] (example: grafting of vinylbenzyl chloride side chains onto e " irradiated ETFE, and quaternization of the chloromethylated side chains with trimethylamine [33]).
- a sterically hindered chemically stabilized cationic functional group is the tris (2,4,6-trimethoxyphenyl) phosphonium cation [40], which was attached to polyvinylbenzyl chloride graft chains after storage for 75 hours in IN NaOH at 60 ° C had no degradation.
- a positively charged bis (terpyridine) ruthenium (II) complex was attached to a norbornene polymer [41].
- the AEM thus prepared showed excellent stability in an alkaline environment: incorporation of the polymer in IN NaOH at room temperature showed no degradation even after half a year.
- AK ionically and covalently cross-linked AEM blends from bromomethylated PPO or a bromomethylated and partially fluorinated arylene main chain polymer and a partially fluorinated PBI (FePBI) as a mechanically and chemically stable matrix and a sulfonated polyethersulfone sPPSU added in excess [46].
- the halomethylated blend component was quaternized with N-methylmorpholine (NMM) to form the anion exchange group [47].
- AEMs were synthesized consisting of rigid / flexible semi-interpenetrating networks of triethylamine quaternized PPO and a polyethylene glycol network. It was found that this AEM has high ionic conductivity ( ⁇ 0 ⁇ - up to 80 mS / cm) and a high alkali stability (degradation of ionic conductivity between 25 and 30% within 30 days of storage in IM NaOH at 80 ° C) [52].
- polyethylene glycols were grafted onto chloromethylated SEBS polymers and the resulting copolymers were then quaternized with trimethylamine.
- the resulting AEMs showed very high mechanical and chemical stabilities in 2.5M KOH at 60 ° C (increasing the ionic conductivity during storage in the KOH from 20 to 24 mS / cm) and high ionic conductivities ( ⁇ 0 ⁇ - up to 52 mS / cm) to [53].
- anion-exchange blend membranes of the following blend components are present in anion-exchange blend membranes of the following blend components:
- x 0-12, for example chloromethylated polystyrene or bromomethylated polyphenylene oxide;
- sterically hindered tertiary nitrogen compounds are:
- halomethylated polymers 1, 2-dimethyl-4,5-diphenyl-1H-imidazoles
- Bromomethylated partially fluorinated aromatic polyether II a matrix polymer, for example, a basic polybenzimidazole;
- a matrix polymer for example, a basic polybenzimidazole;
- Examples of basic matrix polymers are:
- a sulfonated aryl polymer as an ionic macromolecular crosslinker (ionic crosslinking with the basic functional groups of the matrix polymer and with the anion exchange groups of the quaternized halomethylated polymer.
- sulfonated aryl polymers examples include sulfonation SFS001)
- sulfonated aromatic poly (phenylphosphine oxide) II optionally a sulfonated polymer as a covalent macromolecular crosslinker whose sulfinate groups undergo covalent crosslinking via the sulfinate-S-alkylation with the halomethyl groups of the halomethylated polymer.
- a covalent crosslinking reaction between a sulfonated aromatic poly (phenylphosphine oxide) II optionally a sulfonated polymer as a covalent macromolecular crosslinker whose sulfinate groups undergo covalent crosslinking via the sulfinate-S-alkylation with the halomethyl groups of the halomethylated polymer.
- the membrane properties such as conductivity and thermal and chemical stability, in particular stability in strongly alkaline solutions, such as aqueous potassium hydroxide solution or sodium hydroxide solution
- the sulfinate groups of the sulfinated polymer with epoxy or halomethyl end groups of the polyethylene glycol are capable of reaction, presumably under sulfinate S-alkylation of the sulfinate groups by the epoxide or halomethyl groups.
- the reaction of the sulfinate groups of the sulfinated polymer with the epoxide end groups of the polyethylene glycol are shown below:
- anion-exchange blend membranes AEBM
- polymeric blend components halomethylated polymer, matrix polymer (eg.
- Polybenzimidazole polyethylene glycol with epoxide or halomethyl end groups, optionally sulfonated polymer and / or sulfinated polymer) are together in a dipoiar-aprotic solvent or in a mixture of different dipoiar-aprotic solvents (examples: ⁇ , ⁇ -dimethylacetamide, N-methylpyrrolidinone, N-ethyl pyrrolidinone, dimethyl sulfoxide sulfolane).
- the polymer solutions are doctored or cast on a support (glass plate, metal plate, plastic film, etc.), and the solvent is evaporated in a circulating air dryer or a vacuum oven at temperatures between room temperature and 150 ° C.
- Polybenzimidazole polyethylene glycol with epoxide or halomethyl end groups, optionally sulfonated polymer and / or sulfinated polymer) are together in a dipoiar-aprotic solvent or in a mixture of different dipoiar-aprotic solvents (examples: ⁇ , ⁇ -dimethylacetamide, N-methylpyrrolidinone, N-ethyl pyrrolidinone, dimethyl sulfoxide sulfolane).
- the tertiary amine or the N-monoalkylated (benz) imidazole or N-monoalkylated pyrazole is added to the solution .
- the polymer solutions are doctored or cast on a support (glass plate, metal plate, plastic film, etc.), and the solvent is evaporated in a circulating air dryer or a vacuum oven at temperatures between room temperature and 150 ° C.
- Figure 1 shows the chloride conductivities of the membranes 2175 and 2176 in the temperature range between 30 and 90 ° C with a constant relative humidity of 90%.
- Figure 2 shows the chloride conductivity of the membrane 2176 before and after 10, 20 and 30 days of incorporation in IM KOH in a temperature range of 30 to 90 ° C and a relative humidity of 90%.
- Figure 3 shows the TGA curves of membranes 2175 and 2176 before and after 10 days treatment in IM KOH at 90 ° C
- Figure 4 shows the TGA curves of membrane 2176 before and after 10, 20 and 30 days treatment in IM KOH at 90 ° C
- Figure 5 shows the chloride conductivity of the membrane 2190A before and after 10 days storage in IM KOH in the temperature range 30-90 ° C at a relative humidity of 90%
- Figure 6 shows the TGA curves of membrane 2190A before and after 10 days of storage in IM KOH at 90 ° C
- Figure 7 shows the chloride conductivity of membrane 2215 before and after 10 days storage in IM KOH in the temperature range 30-90 ° C at a relative humidity of 90%
- Figure 8 shows the TGA curves of membrane 2215 before and after 10 days storage in IM KOH at 90 ° C
- Figure 9 shows the chloride conductivity of the membrane 2179B before and after 10 days storage in IM KOH in the temperature range 30-90 ° C at a relative humidity of 90%
- Figure 10 shows the chloride conductivity of membrane 2216 before and after 10 days storage in IM KOH in the temperature range 30-90 ° C at a relative humidity of 90%
- Figure 11 shows the chloride conductivity of the commercial anion exchange membrane Tokuyama A201 in the temperature range 30-80 ° C at a relative humidity of 90%
- membrane 2175 0.25 g of epoxide-terminated polyethylene glycol (molecular mass 500 daltons, ALDRICH product no. 475696) are added to this mixture after homogenization, in the case of membrane 2176 0.25 g of epoxide-terminated polyethylene glycol (Molecular mass 6000 daltons, ALDRICH product no. 731803).
- the polymer solutions are doctored on a glass plate. Thereafter, the solvent is evaporated in a convection oven at 130 ° C for a period of 2 hours. The polymer films are then removed under water and after-treated as follows: at 60 ° C for 24 hours in a 10% strength by weight solution of tetramethylimidazole in ethanol
- Membrane 2175 ion exchange capacity before / after KOH treatment * [meq OH ⁇ / g membrane]: 2.92 / 2.96
- Membrane 2176 ion exchange capacity before / after KOH treatment * [meq OH ⁇ / g membrane]:
- FIG. 2 shows the chloride conductivities of the membrane 2176 before and after 10, 20 and 30 days incorporation in IM KOH in the temperature range from 30 to 90 ° C.
- TGA curves of the 2176 were recorded before and after 10, 20 and 30 days of incorporation in KOH. These TGA curves are shown in Figure 4. From Figure 4, it can be seen that the TGA curves of all 4 samples are nearly congruent up to a temperature of about 430 ° C, from which one can conclude that the 2176 still shows no sign of significant degradation even after 30 days of incorporation into KOH which confirms the results of the conductivity tests.
- Application Example 2 AEM blend of PVBCI, PBIOO, a sulfonated polyethersulfone (SAC098, see description), tetramethylimidazole for quaternizing the PVBCI and an epoxide-terminated polyethylene glycol having a lower AEM content than in Application Example 1 but the same molar ratio between PBIOO and PEG -Diepoxid 6000 (Membrane MJK2190A)
- epoxide-terminated polyethylene glycol molecular mass 6000 daltons, ALDRICH product no. 731803
- the polymer solution is doctored onto a glass plate. Thereafter, the solvent is evaporated in a convection oven at 130 ° C for a period of 2 hours.
- the polymer film is then removed under water and after-treated as follows: at 60 ° C for 24 hours in a 10 wt% solution of tetramethylimidazole in ethanol
- Part of the membrane is placed in an aqueous IM KOH solution for a period of 10 days at a temperature of 90 ° C.
- the chloride conductivity was also determined in this membrane as a function of the temperature between 30 and 90 ° C at a relative humidity of 90%.
- the conductivity curves are shown in Figure 5.
- the conductivity of the 2190A membrane also increases during KOH treatment.
- TGA curves of the membrane were recorded before and after 10 days of KOH treatment.
- the TGA curves are shown in Figure 6. Even with this membrane, the TGA curves before and after 10 days of KOH treatment almost congruent, at least up to a temperature of about 350 ° C, what indicates that after 10 days of incorporation in IM KOH at 90 ° C, no significant degradation of the membranes has yet occurred.
- the solvent is evaporated in a convection oven at 140 ° C for a period of 2 hours.
- the polymer film is then removed under water and after-treated as follows: at 60 ° C for 24 hours in a 10 wt% solution of tetramethylimidazole in ethanol
- Part of the membrane is placed in an aqueous IM KOH solution for a period of 10 days at a temperature of 90 ° C *
- the chloride conductivity was also determined in this membrane as a function of the temperature between 30 and 90 ° C at a relative humidity of 90%.
- the conductivity curves are shown in Figure 7.
- the chloride conductivity after lOd storage in IM KOH at 90 ° C is higher than before.
- TGA curves of the membrane were recorded before and after 10 days of KOH treatment. The TGA curves are shown in Figure 8.
- the TGA curves before and after 10 days KOH treatment almost congruent, at least up to a temperature of about 350 ° C, indicating that after 10 days of incorporation in IM KOH at 90 ° C, no significant Degradation of the membranes has taken place.
- Comparative Example 1 AEM blend of PVBCI, PBIOO, a sulfonated polyethersulfone (SAC098, see description), tetramethylimidazole for quaternization of the PVBCI with the same calculated IEC as the membranes MJK2175 and MJK2176, but without PEG diglycidyl ether (membrane 2179B)
- the polymer solutions are doctored on a glass plate. Thereafter, the solvent is evaporated in a convection oven at 140 ° C for a period of 2 hours.
- the polymer films are then dissolved in water and after-treated as follows: at 60 ° C for 24 hours in a 10 wt% solution of tetramethylimidazole in ethanol
- Parts of the membranes are placed in an aqueous IM KOH solution for a period of 10 days at a temperature of 90 ° C *
- Water uptake is significantly lower than at 2175 and 2176. This can be explained by the lower hydrophilicity of the control membrane.
- the impedance of the 2179B was higher in conductivity measurement at room temperature and in 0.5N NaCl as at 2175 and 2176 after the KOH treatment, the impedance of the 2179B again became function of the temperature at a relative humidity of 90 % measured.
- the conductivity curve of the 2179B under these conditions is shown in Figure 9.
- the chloride conductivity is much lower than that of the 2175 and 2176 containing a PEG phase, and the impedance after the KOH treatment is significantly lower than before.
- the solvent is evaporated in a convection oven at 140 ° C for a period of 2 hours.
- the polymer film is then removed under water and after-treated as follows: at 60 ° C for 24 hours in a 10 wt% solution of tetramethylimidazole in ethanol
- Portions of the membranes are placed in an aqueous IM KOH solution for a period of 10 days at a temperature of 90 ° C
- the cr conductivity at room temperature in 0.5N NaCl is significantly lower than in the case of the membrane 2215 according to the invention. This shows the positive influence that the addition of a hydrophilic PEG phase has to the membrane.
- the water uptake is significantly lower than at 2215. This can be explained by the lower hydrophilicity of the control membrane. Since the Cl " conductivity of the 2216 was higher at the room temperature and 0.5N NaCl than at 2215 after the KOH treatment, the impedance of the 2215 again became 90% relative to the temperature at a relative humidity of 90%. The conductivity curve of the 2215 under these conditions is shown in Figure 10.
- Comparative Example 3 Commercial anion exchange membrane A201 (development code A006) of the manufacturer Tokuyama
- This membrane is company secret.
- the anion exchange group of this membrane is the trimethylammonium group. But it is obviously a cross-linked membrane because the extraction of the membrane gave a gel content of 95%.
- this membrane is company secret. But it is obviously a cross-linked membrane, as the extraction of the membrane gave a gel content of 93.3%.
- the chloride conductivity of this membrane is substantially lower than that of most of the membranes of this invention listed as examples, which u. A. is also because this membrane is fabric reinforced.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Electrochemistry (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Metallurgy (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Fuel Cell (AREA)
- Cell Separators (AREA)
- Conductive Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019520195A JP2019522887A (ja) | 2016-06-22 | 2017-06-22 | 親水性膜相としてポリエチレングリコールを用いた架橋高安定アニオン交換ブレンド膜 |
DE112017003141.9T DE112017003141A5 (de) | 2016-06-22 | 2017-06-22 | Vernetzte hochstabile Anionenaustauscherblendmembranen mit Polyethylenglycolen als hydrophiler Membranphase |
EP17767982.6A EP3478750A1 (de) | 2016-06-22 | 2017-06-22 | Vernetzte hochstabile anionenaustauscherblendmembranen mit polyethylenglycolen als hydrophiler membranphase |
US16/312,975 US11278879B2 (en) | 2016-06-22 | 2017-06-22 | Cross-linked high stable anion exchange blend membranes with polyethyleneglycols as hydrophilic membrane phase |
AU2017280451A AU2017280451A1 (en) | 2016-06-22 | 2017-06-22 | Cross-linked high stable anion exchange blend membranes with polyethyleneglycols as hydrophilic membrane phase |
US17/700,325 US20220212183A1 (en) | 2016-06-22 | 2022-03-21 | Cross-linked high stable anion exchange blend membranes with polyethyleneglycols as hydrophilic membrane phase |
JP2022107354A JP2022160413A (ja) | 2016-06-22 | 2022-07-01 | 親水性膜相としてポリエチレングリコールを用いた架橋高安定アニオン交換ブレンド膜 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102016007815.4 | 2016-06-22 | ||
DE102016007815.4A DE102016007815A1 (de) | 2016-06-22 | 2016-06-22 | Vernetzte hochstabile Anionenaustauscherblendmembranen mit Polyethylenglycolen als hydrophiler Membranphase |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/312,975 A-371-Of-International US11278879B2 (en) | 2016-06-22 | 2017-06-22 | Cross-linked high stable anion exchange blend membranes with polyethyleneglycols as hydrophilic membrane phase |
US17/700,325 Continuation US20220212183A1 (en) | 2016-06-22 | 2022-03-21 | Cross-linked high stable anion exchange blend membranes with polyethyleneglycols as hydrophilic membrane phase |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2017220065A1 true WO2017220065A1 (de) | 2017-12-28 |
Family
ID=59886976
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/DE2017/000179 WO2017220065A1 (de) | 2016-06-22 | 2017-06-22 | Vernetzte hochstabile anionenaustauscherblendmembranen mit polyethylenglycolen als hydrophiler membranphase |
Country Status (6)
Country | Link |
---|---|
US (2) | US11278879B2 (de) |
EP (1) | EP3478750A1 (de) |
JP (2) | JP2019522887A (de) |
AU (1) | AU2017280451A1 (de) |
DE (2) | DE102016007815A1 (de) |
WO (1) | WO2017220065A1 (de) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109316979A (zh) * | 2018-11-02 | 2019-02-12 | 绿邦膜分离技术(江苏)有限公司 | 一种高致密性聚苯乙烯系阳离子交换膜的连续制备方法 |
CN109701400A (zh) * | 2019-03-11 | 2019-05-03 | 福州大学 | 一种基于聚醚砜的多孔阴离子交换膜的制备方法 |
CN110280149A (zh) * | 2019-07-02 | 2019-09-27 | 中国科学院宁波材料技术与工程研究所 | 超亲水聚合物微孔膜、其制备方法及应用 |
CN110560181A (zh) * | 2019-09-04 | 2019-12-13 | 中国科学技术大学先进技术研究院 | 一种阴离子交换膜的制备方法 |
CN111303436A (zh) * | 2020-03-06 | 2020-06-19 | 珠海冠宇电池有限公司 | 一种聚烯烃-g-超支化聚苯并咪唑接枝共聚物及其制备方法与应用 |
CN114144453A (zh) * | 2019-07-22 | 2022-03-04 | 赢创运营有限公司 | 聚合物阴离子传导膜 |
CN114456393A (zh) * | 2022-01-19 | 2022-05-10 | 武汉理工大学 | 一种sebs接枝聚苯醚阴离子交换膜的制备方法 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102016007815A1 (de) * | 2016-06-22 | 2017-12-28 | Universität Stuttgart | Vernetzte hochstabile Anionenaustauscherblendmembranen mit Polyethylenglycolen als hydrophiler Membranphase |
CN110550788A (zh) * | 2019-09-12 | 2019-12-10 | 欧润吉生态环保(浙江)有限公司 | 一种零排放水处理装置 |
CN111040156B (zh) * | 2019-11-28 | 2022-05-31 | 李南文 | 一种耐溶剂且高尺寸稳定性的交联型聚酰亚胺薄膜 |
CN111359453A (zh) * | 2020-03-21 | 2020-07-03 | 山东科技大学 | 一种掺杂咪唑类离子液体/改性壳聚糖均相阴离子交换膜及其制备方法 |
CN112316988A (zh) * | 2020-10-23 | 2021-02-05 | 天津市大陆制氢设备有限公司 | 一种高效的阴离子交换膜及其制备方法 |
CN113041850A (zh) * | 2021-04-07 | 2021-06-29 | 福州大学 | 一种用于扩散渗析的多孔交联阴离子交换膜的制备方法 |
CN113600026B (zh) * | 2021-09-09 | 2022-07-22 | 浙江工业大学 | 一种基于聚乙烯醇抗污染交联型阴离子交换膜的制备方法 |
DE102022120196A1 (de) | 2022-08-10 | 2024-02-15 | Forschungszentrum Jülich GmbH | Seitenkettenfunktionalisierte Polystyrole als Membranmaterialien für alkalische Wasserelektrolyseure, Brennstoffzellen und Flow-Batterien |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102014009170A1 (de) | 2014-06-12 | 2015-12-17 | Universität Stuttgart | Kombinatorisches Materialsystem für Ionenaustauschermembranen und dessen Verwendung in elektrochemischen Prozessen |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009081841A1 (ja) * | 2007-12-21 | 2009-07-02 | Tokuyama Corporation | 固体高分子型燃料電池用隔膜、及び隔膜-触媒電極接合体 |
JP5959046B2 (ja) * | 2012-03-07 | 2016-08-02 | 国立研究開発法人日本原子力研究開発機構 | アニオン伝導電解質膜およびその製造方法 |
EP3106476A4 (de) * | 2014-02-14 | 2017-07-12 | Tokuyama Corporation | Teilweise quaternisiertes styrol-basiertes copolymer, ionenleitfähigkeitsvermittler, katalytische elektrodenschicht, membran-/elektrodenanordnung und verfahren zur herstellung davon, gasdiffusionselektrode und verfahren zur herstellung davon sowie brennstoffzelle mit anionenaustauschmembrane |
DE102016007815A1 (de) * | 2016-06-22 | 2017-12-28 | Universität Stuttgart | Vernetzte hochstabile Anionenaustauscherblendmembranen mit Polyethylenglycolen als hydrophiler Membranphase |
-
2016
- 2016-06-22 DE DE102016007815.4A patent/DE102016007815A1/de not_active Withdrawn
-
2017
- 2017-06-22 EP EP17767982.6A patent/EP3478750A1/de active Pending
- 2017-06-22 DE DE112017003141.9T patent/DE112017003141A5/de not_active Withdrawn
- 2017-06-22 JP JP2019520195A patent/JP2019522887A/ja active Pending
- 2017-06-22 WO PCT/DE2017/000179 patent/WO2017220065A1/de unknown
- 2017-06-22 AU AU2017280451A patent/AU2017280451A1/en not_active Abandoned
- 2017-06-22 US US16/312,975 patent/US11278879B2/en active Active
-
2022
- 2022-03-21 US US17/700,325 patent/US20220212183A1/en active Pending
- 2022-07-01 JP JP2022107354A patent/JP2022160413A/ja active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102014009170A1 (de) | 2014-06-12 | 2015-12-17 | Universität Stuttgart | Kombinatorisches Materialsystem für Ionenaustauschermembranen und dessen Verwendung in elektrochemischen Prozessen |
Non-Patent Citations (54)
Title |
---|
A. G. WRIGHT; S. HOLDCROFT, ACS MACRO LETT., vol. 3, 2014, pages 44 |
A. KATZFUSS; S. POYNTON; J. VARCOE; V. GOGEL; U. STORR; J. KERRES, J. MEMB. SEI., vol. 465, 2014, pages 129 |
A. KATZFUSS; V. GOGEL; L. JÖRISSEN; J. KERRES, J. MEMB. SEI., vol. 131, 2013, pages 425 - 426 |
A. WOHL, BER. DT. CHEM. GES., vol. 52, 1919, pages 51 |
B. BAUER; H. STRATHMANN; F. EFFENBERGER, DESALINATION, vol. 79, 1990, pages 125 |
B. E. LOGAN; M. ELIMELECH, NATURE, vol. 488, 2012, pages 313 |
B. SCHWENZER; J. ZHANG; S. KIM; L. LI; Z. YANG, CHEMSUSCHEM, vol. 4, 2011, pages 1388 |
C. G. MORANDI; R. PEACH; H. M. KRIEG; J. KERRES, J. MATER. CHEM. A, vol. 3, 2015, pages 1110 |
C. G. MORANDI; R. PEACH; H. M. KRIEG; J. KERRES, J. MEMB. SEI., vol. 476, 2015, pages 256 |
C. H. ZHAO; Y. GONG; Q. L. LIU; Q. G. ZHANG; A. M. ZHU, INT. J. HYDROGEN ENERGY, vol. 37, 2012, pages 11383 |
C. YANG; S. WANG; W. MA; S. ZHAO; Z. XU; G. SUN, J. MATER. CHEM. A, vol. 4, 2016, pages 3886 |
CARLO GOTTARDO MORANDI ET AL: "Novel imidazolium-functionalized anion-exchange polymer PBI blend membranes", JOURNAL OF MEMBRANE SCIENCE, vol. 476, 2 December 2014 (2014-12-02), NL, pages 256 - 263, XP055422725, ISSN: 0376-7388, DOI: 10.1016/j.memsci.2014.11.049 * |
CONGRONG YANG ET AL: "Highly stable poly(ethylene glycol)-grafted alkaline anion exchange membranes", JOURNAL OF MATERIALS CHEMISTRY A: MATERIALS FOR ENERGY AND SUSTAINABILITY, vol. 4, no. 10, 4 February 2016 (2016-02-04), GB, pages 3886 - 3892, XP055423046, ISSN: 2050-7488, DOI: 10.1039/C6TA00200E * |
D. S. KIM; A. LABOURIAU; M. D. GUIVER; Y. S. KIM, CHEM. MATER., vol. 23, 2011, pages 3795 |
D. S. KIM; C. H. FUJIMOTO; M. R. HIBBS; A. LABOURIAU; Y. K. CHOE; Y. S. KIM, MACROMOLECULES, vol. 46, 2013, pages 7826 |
F. ZHANG; H. ZHANG; C. QU, J. MATER. CHEM., vol. 21, 2011, pages 12744 |
G. L. BLANC, BULL. SOC. CHIM. FRANCE, vol. 33, 1923, pages 313 |
G. MERLE; M. WESSLING; K. NIJMEIJER, J. MEMBR. SEI., vol. 377, 2011, pages 1 |
G. Z. RAMON; B. J. FEINBERG; E. M. V. HOEK, ENERGY ENVIRON. SEI., vol. 4, 2011, pages 4423 |
J. CHENG; G. YANG; K. ZHANG; G. HE; J. JIA; H. YU; F. GAI; L. LI; C. HAO; F. ZHANG, J. MEMB. SEI., vol. 501, 2016, pages 100 |
J. PAN; L. ZHU; J. HAN; M. A. HICKNER, CHEM. MATER., vol. 27, 2015, pages 6689 |
J. R. VARCOE; P. ATANASSOV; D. R. DEKEL; A. M. HERRING; M. A. HICKNER; P. A. KOHL; A. R. KUCERNAK; W. E. MUSTAIN; K. NIJMEIJER; K., ENERGY ENVIRON. SEI., vol. 7, 2014, pages 3135 |
J. SANDEAUX; R. SANDEAUX; C. GAVACH, J. MEMB. SEI., vol. 59, 1991, pages 265 |
J. VARCOE; R. C. T. SLADE, FUEL CELLS, vol. 5, 2005, pages 187 |
J. WANG; S. LI; S. ZHANG, MACROMOLECULES, vol. 43, 2010, pages 3890 |
J. X. LEONG; W. R. W. DAUD; M. GHASEMI; K. B. LIEW; M. ISMAIL, RENEWABLE SUSTAINABLE ENERGY REV., 2013, pages 575 |
JING PAN ET AL: "Mechanically Tough and Chemically Stable Anion Exchange Membranes from Rigid-Flexible Semi-Interpenetrating Networks", CHEMISTRY OF MATERIALS, vol. 27, no. 19, 28 September 2015 (2015-09-28), US, pages 6689 - 6698, XP055423043, ISSN: 0897-4756, DOI: 10.1021/acs.chemmater.5b02557 * |
K. EMMANUEL; C. CHENG; B. ERIGENE; A. N. MONDAL; M. M. HOSSAIN; M. I. KHAN; N. U. AFSAR; G. LIANG; L. WU; T. XU, J. MEMB. SEI., vol. 497, 2016, pages 209 |
K. MIYATAKE; H. ZHOU; M. WATANABE, J. POLYM. SEI., PART A: POLYM. CHEM., vol. 43, 2005, pages 1741 |
M. A. HICKNER; A. M. HERRING; E. B. COUGHLIN, J. POLYM. SEI., PART B: POLYM. PHYS., vol. 51, 2013, pages 1727 |
M. R. HIBBS; M. A. HICKNER; T. M. ALAM; S. K. MCLNTYRE; C. H. FUJIMOTO; C. J. CORNELIUS, CHEM. MATER., vol. 20, 2008, pages 2566 |
M. SKYLLAS-KAZACOS; M. H. CHAKRABARTI; S. A. HAJIMOLANA; F. S. MJALLI; M. SALEEM, J. ELECTROCHEM. SOC., vol. 158, 2011, pages R55 |
N.T.REBEK; Y.LIAND; D.M.KNAUSS, J. POLYM.SCI., PARTB: POLYM. PHYS., vol. 51, 2013, pages 1770 |
O. D. THOMAS; K. J. W. Y. SOO; T. J. PECKHAM; M. P. KULKARNI; S. HOLDCROFT, J. AM. CHEM. SOC., vol. 134, 2012, pages 10753 |
P. ZSCHOCKE; D. QUELLMALZ, J. MEMB. SEI., vol. 22, 1985, pages 325 |
R. C. T. SLADE; J. R. VARCOE, FUEL CELLS, vol. 5, 2005, pages 187 |
S. A. NUNEZ; M. A. HICKNER, ACS MACRO LETT.,, vol. 2, 2013, pages 49 |
S. D. POYNTON; J. R. VARCOE, SOLID STATE LONICS, vol. 277, 2015, pages 38 |
S. KLIBER; J. A. WISNIEWSKI, DESAL. WATER TREATM., vol. 35, 2011, pages 158 |
S. MARINI; P. SALVI; P. NELLI; R. PESENTI; M. VILLA; M. BERRETTONI; G. ZANGARI; Y. KIROS, ELECTROCHIM. ACTA, vol. 82, 2012, pages 384 |
S. MAURYA; S. H. SHIN; M. K. KIM; S. H. YUN; S. H. MOON, J. MEMB. SEI., vol. 443, 2013, pages 28 |
T. SATA, J. MEMB. SEI., vol. 167, 2000, pages 1 |
T. SATA; K. MINE; K. MATSUSAKI, J. COLLOID INTERFACE SEI., vol. 202, 1998, pages 348 |
T. SATA; T. YAMAGUCHI; K. MATSUSAKI, J. PHYS. CHEM., vol. 99, 1995, pages 12875 |
T. SATA; Y. YAMANE; K. MATSUSAKI, J. POLYM. CHEM. PART A: POLYM. CHEM., vol. 36, 1998, pages 49 |
T. XU, J. MEMBR. SEI., vol. 263, 2005, pages 1 |
V. B. OLIVERIA; M. SIMOES; L. F. MELO; A. M. F. R. PINTO, BIOCHEM. ENG. J., vol. 73, 2013, pages 53 |
W. GELLET; J. SCHUMACHER; M. KESMEZ; D. LE; S. D. MINTEER, J. ELECTROCHEM. SOC., vol. 157, 2010, pages B557 |
W. WANG; Q. LUO; B. LI; X. WEI; L. LI; Z. YANG, ADV. FUNCT. MATER., vol. 23, 2013, pages 970 |
X. LIN; J. R. VARCOE; S. D. POYNTON; X. LIANG; A. L. ONG; J. RAN; Y. LI; T. XU, J. MATER. CHEM. A, vol. 1, 2013, pages 7262 |
Y. A. ELABD; M. A. HICKNER, MACROMOLECULES, vol. 44, 2011, pages 1 |
Y. HE; L. WU; J. PAN; Y. ZHU; X. GE; Z. YANG; J. RAN; T. XU, J. MEMB. SEI., vol. 504, 2016, pages 47 |
Y. LIU; J. WANG; Y. YANG; T. M. BRENNER; S. SEIFERT; Y. YAN; M. W. LIBERATORE; A. M. HERRING, J. PHYS. CHEM. C, vol. 118, 2014, pages 15136 |
Y. ZHA; M. L. DISABB-MILLER; Z. D. JOHNSON; M. A. HICKNER; G. N. TEW, J. AM. CHEM. SOC., vol. 134, 2012, pages 4493 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109316979A (zh) * | 2018-11-02 | 2019-02-12 | 绿邦膜分离技术(江苏)有限公司 | 一种高致密性聚苯乙烯系阳离子交换膜的连续制备方法 |
CN109701400A (zh) * | 2019-03-11 | 2019-05-03 | 福州大学 | 一种基于聚醚砜的多孔阴离子交换膜的制备方法 |
CN110280149A (zh) * | 2019-07-02 | 2019-09-27 | 中国科学院宁波材料技术与工程研究所 | 超亲水聚合物微孔膜、其制备方法及应用 |
CN114144453A (zh) * | 2019-07-22 | 2022-03-04 | 赢创运营有限公司 | 聚合物阴离子传导膜 |
CN110560181A (zh) * | 2019-09-04 | 2019-12-13 | 中国科学技术大学先进技术研究院 | 一种阴离子交换膜的制备方法 |
CN110560181B (zh) * | 2019-09-04 | 2022-08-02 | 中国科学技术大学先进技术研究院 | 一种阴离子交换膜的制备方法 |
CN111303436A (zh) * | 2020-03-06 | 2020-06-19 | 珠海冠宇电池有限公司 | 一种聚烯烃-g-超支化聚苯并咪唑接枝共聚物及其制备方法与应用 |
CN114456393A (zh) * | 2022-01-19 | 2022-05-10 | 武汉理工大学 | 一种sebs接枝聚苯醚阴离子交换膜的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2019522887A (ja) | 2019-08-15 |
JP2022160413A (ja) | 2022-10-19 |
DE112017003141A5 (de) | 2019-03-07 |
US20200023348A1 (en) | 2020-01-23 |
EP3478750A1 (de) | 2019-05-08 |
US20220212183A1 (en) | 2022-07-07 |
US11278879B2 (en) | 2022-03-22 |
DE102016007815A1 (de) | 2017-12-28 |
AU2017280451A1 (en) | 2019-02-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2017220065A1 (de) | Vernetzte hochstabile anionenaustauscherblendmembranen mit polyethylenglycolen als hydrophiler membranphase | |
Boaretti et al. | Mechanically stable nanofibrous sPEEK/Aquivion® composite membranes for fuel cell applications | |
EP3155674A2 (de) | Kombinatorisches materialsystem für ionenaustauschermembranen und dessen verwendung in elektrochemischen prozessen | |
Niu et al. | Pendent piperidinium-functionalized blend anion exchange membrane for fuel cell application | |
JP2020059862A (ja) | 新規ポリマー及びその製造方法 | |
Morandi et al. | Novel morpholinium-functionalized anion-exchange PBI–polymer blends | |
Mabrouk et al. | Ion exchange membranes based upon crosslinked sulfonated polyethersulfone for electrochemical applications | |
Morandi et al. | Novel imidazolium-functionalized anion-exchange polymer PBI blend membranes | |
Xu et al. | Modification of poly (aryl ether ketone) using imidazolium groups as both pendants and bridging joints for anion exchange membranes | |
EP1076676A2 (de) | Engineering-ionomerblends und engineering-ionomerblendmembranen | |
EP1971635A1 (de) | Protonenleitende polymermembran | |
CN113801352B (zh) | 一种阴离子交换膜及其制备方法和应用 | |
CA3066028A1 (en) | Crosslinked highly stable anion-exchange blend membranes with polyethyleneglycols as the hydrophilic membrane phase | |
EP4061879A1 (de) | Kationenaustauscher- und anionenaustauscherpolymere und -(blend)membranen aus hochfluorierte aromatische gruppen enthaltenden polymeren mittels nucleophiler substitution | |
KR101888935B1 (ko) | 방사선 가교에 의한 양이온교환레진/양이온교환고분자 복합막 및 이의 제조 방법 | |
CN114759238B (zh) | 一种星型交联碱性聚电解质及其制备方法 | |
DE10019732A1 (de) | Säure-Base-Polymermembranen | |
KR101728772B1 (ko) | 음이온전도성 전해질막, 상기 음이온전도성 전해질막 제조방법 및 상기 전해질막을 포함하는 에너지 저장 장치 및 수처리장치 | |
Son et al. | Preparation and characterization of chitosan membranes cross-linked using poly (2, 6-dimethyl-1, 4-phenylene oxide) polymer and chitosan | |
KR102105662B1 (ko) | 술폰화 폴리페닐렌설파이드 전해질막 및 그 제조방법 | |
Yang et al. | High-Performance Monovalent Selective Cation Exchange Membranes with Ionically Cross-Linkable Side Chains: Effect of the Acidic Groups | |
DE102021003228A1 (de) | Neuartige phosphonierte nichtfluorierte und teilfluorierte Arylpolymere aus sulfonierten Arylpolymeren und neuartige polymere Perfluorphosphonsäuren aus polymeren Perfluorsulfonsäuren, deren Herstellungsverfahren und Anwendung in Elektromembrananwendungen | |
Boaretti et al. | fuel cell applications, Journal of Membrane Science | |
KR101640095B1 (ko) | 음이온전도성 전해질막 및 상기 전해질막을 포함하는 에너지 저장 장치 및 수처리장치 | |
CN114551918A (zh) | 一种复合膜及其制备方法、应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 17767982 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2019520195 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2017767982 Country of ref document: EP Effective date: 20190122 |
|
ENP | Entry into the national phase |
Ref document number: 2017280451 Country of ref document: AU Date of ref document: 20170622 Kind code of ref document: A |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: R225 Ref document number: 112017003141 Country of ref document: DE |