CN109687004A - A kind of multipole ion cross-linking type anion-exchange membrane and preparation method thereof - Google Patents
A kind of multipole ion cross-linking type anion-exchange membrane and preparation method thereof Download PDFInfo
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- CN109687004A CN109687004A CN201811441042.3A CN201811441042A CN109687004A CN 109687004 A CN109687004 A CN 109687004A CN 201811441042 A CN201811441042 A CN 201811441042A CN 109687004 A CN109687004 A CN 109687004A
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- 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]
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- 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
- H01M8/1039—Polymeric electrolyte materials halogenated, e.g. sulfonated polyvinylidene fluorides
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- 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
- H01M8/1067—Polymeric electrolyte materials characterised by their physical properties, e.g. porosity, ionic conductivity or thickness
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- 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
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. insitu polymerisation or insitu crosslinking
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Abstract
A kind of multipole ion cross-linking type anion-exchange membrane and preparation method thereof, belongs to fuel cell field of membrane material.The present invention is grafted the monomer N- amide containing N and carbon-carbon double bond simultaneously first on polysulfones main chain, complete first step ionization, then VBC and ST copolymer is grafted by free radical polymerization, finally it is crosslinked again with TMHDA, second step ionization is completed, multipole ion cross-linking type anion-exchange membrane is made.The present invention increases the quantity of ionic group by multipole ion process, improves the conductivity of film；The introducing of crosslinking can inhibit the water absorption and swelling of film, enhance the dimensional stability of film while improving conductivity, improve the comprehensive performance of film on the whole.
Description
Technical field
The invention belongs to fuel cell field of membrane material, be related to a kind of multipole ion cross-linking type anion-exchange membrane and its
Preparation method.
Background technique
As energy and environmental problem grows in intensity, fuel cell is as a kind of cleaning, efficient energy conversion device, more
To be more concerned by people.And alkaline anion-exchange membrane fuel cell (AAEMFCs) has redox overpotential low, it can
Make catalyst using base metal, the low advantage of fuel permeability even more has become a hot topic of research.
Critical component of the anion-exchange membrane (AEMS) as AAEMFCs, its effect are to separate fuel and oxidant, with
And transmitting H-.It has direct influence to the performance of AAEMFCs, can should be met by the AEM of application claimed below:
(1) ionic conductivity wants high.Since that transmit in AAEMFCs is OH-, it is contemplated that the diffusion coefficient of OH- ratio H+
It is low, therefore so that AAEMFCs is worked normally it is necessary to guarantee that the conductivity of AEM cannot be too low.
(2) good heat resistance and alkaline resistance properties.In the work of AAEMFCs, film will be greater than 60 DEG C of alkaline item
It works long hours under part.Main polymer chain and cation group must have preferable alkali-resistant performance, just can guarantee battery
Normal operation.
(3) good dimensional stability and mechanical performance.Since film needs to operate for a long time under the high temperature conditions,
There is film preferable mechanical strength to be very important.
Currently, the significant challenge that researchers encounter be how balance film conductivity and dimensional stability the problem of.Cause
For film conductivity height along with the increase of film water absorption and swelling, just necessarily cause the dimensional stability of film to be deteriorated.For this purpose, researcher
Different trials has also been made, for example, on main chain be grafted polycation side chain, prepared film have good microfacies divide
From form, conductivity is improved, but dimensional stability is not fully up to expectations.
To solve the above-mentioned problems, this project passes through free radical polymerization grafting p-chloromethyl styrene (VBC) and styrene
(ST) then copolymer side chain is crosslinked again, be prepared for multipole ion cross-linking type anion-exchange membrane.The advantages of this film
It is on the one hand to increase the quantity of ionic group by multipole ion process, achievees the purpose that improve conductivity；Another party
Face, introducing crosslinked structure enhance the dimensional stability of film while improving conductivity, from the whole performance for improving film.
Summary of the invention
The present invention is prepared for a kind of multipole ion cross-linking type yin by the preparation method of the existing anion-exchange membrane of optimization
Amberplex.The film enhances the mechanical performance of film while improving conductivity, improves the property of film on the whole
Energy.
In order to reach above-mentioned technical purpose, the technical scheme is that
A kind of multipole ion cross-linking type anion-exchange membrane, the film are the polysulfones to be grafted N- amide
For main chain, VBC is grafted by free radical polymerization and is copolymerized ST side chain, introduce N, N, N between the VBC of side chain, N- tetramethyl oneself two
Amine (TMHDA) completes crosslinking, and finally obtained main chain is polysulfones, and side chain is VBC and ST copolymer, and crosslinking agent is the multistage of TMHDA
Change cross-linking type anion-exchange membrane.
The structural formula of the multipole ion cross-linking type anion-exchange membrane are as follows:
Wherein, n represents the number of repetitive unit on polysulfones main chain.
In a kind of preparation method of multipole ion cross-linking type anion-exchange membrane, it is grafted simultaneously on polysulfones main chain first
Monomer N- amide containing N and carbon-carbon double bond is completed first step ionization, is then grafted by free radical polymerization
VBC and ST copolymer, is finally crosslinked with TMHDA again, complete second step ionization, be made multipole ion cross-linking type yin from
Proton exchange.Specifically includes the following steps:
The first step synthesizes graft N-amide polysulfones main chain (N-PSF)
Firstly, at room temperature, CMPSF being added in N-Methyl pyrrolidone (NMP) and obtains reaction solution, concentration
For 0.05g/L-0.1g/L.Secondly, N- amide monomer is added in reaction solution, 3-5 is reacted at 30-50 DEG C
It, the solution after reaction, which is slowly poured into ethyl acetate, to be precipitated, and the white solid being settled out is washed with ethyl acetate repeatedly, often
It is secondary at least to wash 6 hours；The molar ratio of the CMPSF and N- amide is 1:8-1:10.Finally, by product
It is dried at room temperature for 48 hours, obtains beige solid.
Second step, the polymer (N-PSF-VBC) of synthesis grafting VBC and ST side chain
Firstly, at room temperature, the N-PSF that the first step synthesizes is added in solvent NMP, concentration is obtained after stirring is
The solution of 0.05g/L-0.1g/L adds VBC and ST monomer, carries out vacuum-high pure nitrogen circulate operation (at least three three times
It is secondary) remove reaction system in oxygen and water.Secondly, rapidly initiator A IBN is added to instead under high pure nitrogen protection
It answers in device, maintains the temperature at 50-80 DEG C of reaction 12-36 hours.Finally, the solution after reaction is slowly dripped to acetic acid with dropper
It in ethyl ester, is allowed to precipitate, be washed repeatedly with ethyl acetate, at least 6 hours every time, wash away the homopolymer of VBC and ST, after centrifugation,
It is dried at room temperature for obtaining within 48 hours yellow particle shape solid.
The molar ratio of the VBC and ST are that the molar ratio of 2:1, VBC and N-PSF are 6:1-12:1, initiator A IBN's
The ratio of quality and system gross mass is 1:100.
Third step is crosslinked film forming procedure
Firstly, at room temperature, the N-PSF-VBC that second step synthesizes is added in dimethyl sulfoxide (DMSO),
Concentration is 0.07g/L-0.1g/L.Secondly, crosslinking agent TMHDA is added, stirs 5- at 50-70 DEG C by after the centrifugation of above-mentioned solution
10 minutes, after solution viscosity increase, plastic film mulch liquid is transferred on smooth glass plate, after being dried 24-36 hours at 50-70 DEG C
Obtain dense film.The molar ratio of the TMHDA and N-PSF-VBC are 2:1.Finally, film is taken after solvent volatilizees completely
It descends and is immersed in 24-36 hours (room temperature) completion ion exchanges in 1MNaOH solution.And with the deionized water repeated flushing boiled
Immersion makes film surface reach neutrality to obtain multipole ion cross-linking type anion-exchange membrane.
The synthesis process of the multipole ion cross-linking type anion-exchange membrane illustrates route are as follows:
The invention has the benefit that (1) increases the quantity of ionic group by multipole ion process, film is improved
Conductivity；(2) introducing being crosslinked can inhibit the water absorption and swelling of film, enhance the dimensionally stable of film while improving conductivity
Property, the comprehensive performance of film is improved on the whole.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of multipole ion cross-linking type film
Fig. 2 is the FT-IR spectrogram of N-PSF and N-PSF-VBC
Fig. 3 is the mode of appearance figure of 1 multipole ion cross-linking type anion-exchange membrane of case study on implementation.
Specific embodiment
The preparation method of this alkaline anion-exchange membrane is further illustrated below by way of specific implementation case.
Case study on implementation 1:
The first step, the synthesis of N-PSF
Firstly, at room temperature, 2gCMPSF is added in 40mlN- methyl pyrrolidone (NMP), concentration is
0.05g/L；Secondly, being 1:8 by 3.5mlN- amide according to the molar ratio of CMPSF and N- amide
Monomer is added in reaction solution, is reacted 5 days at 30 DEG C, and the solution after reaction, which is slowly poured into ethyl acetate, to be precipitated, precipitating
White solid out is washed with ethyl acetate repeatedly, is at least washed 6 hours every time；Finally, it is small that product is dried at room temperature for 48
When, obtain beige solid.
Second step, the synthesis of N-PSF-VBC
Firstly, at room temperature, the 2gN-PSF that the first step synthesizes is added in 40mlNMP, concentration 0.05g/
L proportionally sequentially adds 1.13mlVBC and 0.46mlST, carries out vacuum-high pure nitrogen circulate operation (at least three times) three times
Remove the oxygen and water in reaction system；Secondly, rapidly initiator 0.026gAIBN is added under high pure nitrogen protection
In reactor, maintains the temperature at 50 DEG C and react 36 hours；Finally, the solution after reaction is slowly dripped to ethyl acetate with dropper
In, it is allowed to precipitate, be washed repeatedly with ethyl acetate, at least 6 hours every time, the homopolymer of VBC and ST are washed away, after centrifugation, in room
Obtain yellow particle shape solid within temperature lower dry 48 hours.The molar ratio of the VBC and ST are mole of 2:1, VBC and N-PSF
Than for 6:1, the quality of initiator A IBN and the ratio of system gross mass are 1:100.
Third step is crosslinked film forming procedure
Firstly, at room temperature, the 0.2gN-PSF-VBC that second step synthesizes is added to 4ml dimethyl sulfoxide
(DMSO) in, concentration 0.05g/L.Secondly, 0.318ml crosslinking agent TMHDA is added, at 60 DEG C for after the centrifugation of above-mentioned solution
Plastic film mulch liquid is transferred on smooth glass plate, after drying 24 hours at 60 DEG C by lower stirring 5 minutes after solution viscosity increase
Obtain dense film.The molar ratio of the TMHDA and N-PSF-VBC are 2:1.Finally, film is taken after solvent volatilizees completely
It descends and is immersed in 36 hours (room temperature) completion ion exchanges in 1MNaOH solution.And it is soaked with the deionized water repeated flushing boiled
Steeping, which makes film surface reach neutrality, obtains multipole ion cross-linking type anion-exchange membrane.The water absorption rate of obtained film is
64.35%, swelling ratio 27.04%, conductivity is 28.67mScm at 30 DEG C-1。
Case study on implementation 2:
The first step, the synthesis of N-PSF
Firstly, at room temperature, 2gCMPSF is added in 30mlN- methyl pyrrolidone (NMP), concentration is
0.067g/L；Secondly, being 1:9 by 3.93mlN- methyl diallyl according to the molar ratio of CMPSF and N- amide
Amine monomers are added in reaction solution, are reacted 4 days at 45 DEG C, and the solution after reaction, which is slowly poured into ethyl acetate, to be precipitated, and are sunk
The white solid to form sediment out is washed with ethyl acetate repeatedly, is at least washed 6 hours every time；Finally, product is dried at room temperature for 48
Hour, obtain beige solid.
Second step, the synthesis of N-PSF-VBC
Firstly, at room temperature, the 2gN-PSF that the first step synthesizes is added in 30mlNMP, concentration is
0.067g/L, proportionally sequentially adds 3.4mlVBC and 1.38mlST, carries out three times that vacuum-high pure nitrogen circulate operation is (extremely
The oxygen and water in reaction system are removed less three times)；Secondly, under high pure nitrogen protection, rapidly by initiator
0.069gAIBN is added in reactor, is maintained the temperature at 65 DEG C and is reacted 24 hours；Finally, by the solution dropper after reaction
It slowly drips in ethyl acetate, is allowed to precipitate, be washed repeatedly with ethyl acetate, at least 6 hours every time, wash away the equal of VBC and ST
Polymers after centrifugation, is dried at room temperature for obtaining within 48 hours yellow particle shape solid.The molar ratio of the VBC and ST are 2:1,
The molar ratio of VBC and N-PSF is 9:1, and the quality of initiator A IBN and the ratio of system gross mass are 1:100.
Third step is crosslinked film forming procedure
Firstly, at room temperature, the 0.2gN-PSF-VBC that second step synthesizes is added to 3ml dimethyl sulfoxide
(DMSO) in, concentration 0.08g/L.Secondly, 0.376ml crosslinking agent TMHDA is added, at 60 DEG C for after the centrifugation of above-mentioned solution
Plastic film mulch liquid is transferred on smooth glass plate, after drying 24 hours at 60 DEG C by lower stirring 5 minutes after solution viscosity increase
Obtain dense film.The molar ratio of the TMHDA and N-PSF-VBC are 2:1.Finally, film is taken after solvent volatilizees completely
It descends and is immersed in 36 hours (room temperature) completion ion exchanges in 1MNaOH solution.And it is soaked with the deionized water repeated flushing boiled
Steeping, which makes film surface reach neutrality, obtains multipole ion cross-linking type anion-exchange membrane.The water absorption rate of obtained film is
62.79%, swelling ratio 28.10%, conductivity is 30.34mScm at 30 DEG C-1。
Case study on implementation 3:
The first step, the synthesis of N-PSF
Firstly, at room temperature, 2gCMPSF is added in 30mlN- methyl pyrrolidone (NMP), concentration is
0.1g/L；Secondly, being 1:10 by 4.37mlN- methyl diallyl according to the molar ratio of CMPSF and N- amide
Amine monomers are added in reaction solution, are reacted 3 days at 50 DEG C, and the solution after reaction, which is slowly poured into ethyl acetate, to be precipitated, and are sunk
The white solid to form sediment out is washed with ethyl acetate repeatedly, is at least washed 6 hours every time；Finally, product is dried at room temperature for 48
Hour, obtain beige solid.
Second step, the synthesis of N-PSF-VBC
Firstly, at room temperature, the 2gN-PSF that the first step synthesizes is added in 20mlNMP, concentration 0.1g/
L proportionally sequentially adds 4.53mlVBC and 1.84mlST, carries out vacuum-high pure nitrogen circulate operation (at least three times) three times
Remove the oxygen and water in reaction system；Secondly, rapidly initiator 0.084gAIBN is added under high pure nitrogen protection
In reactor, maintains the temperature at 80 DEG C and react 12 hours；Finally, the solution after reaction is slowly dripped to ethyl acetate with dropper
In, it is allowed to precipitate, be washed repeatedly with ethyl acetate, at least 6 hours every time, the homopolymer of VBC and ST are washed away, after centrifugation, in room
Obtain yellow particle shape solid within temperature lower dry 48 hours.The molar ratio of the VBC and ST are mole of 2:1, VBC and N-PSF
Than for 12:1, the quality of initiator A IBN and the ratio of system gross mass are 1:100.
Third step is crosslinked film forming procedure
Firstly, at room temperature, the 0.2gN-PSF-VBC that second step synthesizes is added to 2ml dimethyl sulfoxide
(DMSO) in, concentration 0.1g/L；Secondly, 0.411ml crosslinking agent TMHDA is added, at 60 DEG C for after the centrifugation of above-mentioned solution
Plastic film mulch liquid is transferred on smooth glass plate, after drying 24 hours at 60 DEG C by lower stirring 5 minutes after solution viscosity increase
Obtain dense film.The molar ratio of the TMHDA and N-PSF-VBC are 2:1；Finally, film is removed after solvent volatilizees completely
And it is immersed in 36 hours (room temperature) completion ion exchanges in 1MNaOH solution.And it is impregnated with the deionized water repeated flushing boiled
So that film surface is reached neutrality and obtains multipole ion cross-linking type anion-exchange membrane.The water absorption rate of obtained film is 63.47%,
Swelling ratio is that conductivity is 27.25mScm at 29.05,30 DEG C-1。
Claims (6)
1. a kind of multipole ion cross-linking type anion-exchange membrane, which is characterized in that the anion-exchange membrane is to be grafted
The polysulfones of N- amide is main chain, is grafted VBC by free radical polymerization and is copolymerized ST side chain, between the VBC of side chain
By introducing N, N, N, N- 4-methyl hexamethylene diamine completes crosslinking, and finally obtained main chain is polysulfones, and side chain is VBC and ST copolymer,
Crosslinking agent is the multipolarity cross-linking type anion-exchange membrane of TMHDA；The multipole ion cross-linking type anion-exchange membrane
Structural formula are as follows:
Wherein, n represents the number of repetitive unit on polysulfones main chain.
2. a kind of preparation method of multipole ion cross-linking type anion-exchange membrane, it is characterised in that following steps:
The first step synthesizes graft N-amide polysulfones main chain N-PSF
Firstly, at room temperature, CMPSF being added in N-Methyl pyrrolidone NMP and obtains reaction solution；Secondly, by N- first
Base Diallylamine monomers are added in reaction solution, are reacted 3-5 days at 30-50 DEG C, the solution after reaction is added drop-wise to acetic acid second
Precipitated in ester, be filtered, washed, dry after obtain product；The molar ratio of the CMPSF and N- amide is 1:8-
1:10；
Second step, the polymer (N-PSF-VBC) of synthesis grafting VBC and ST side chain
Firstly, at room temperature, the N-PSF that the first step synthesizes is added in solvent NMP, reaction solution is obtained after stirring, then
VBC and ST monomer is added, carries out oxygen and water in vacuum-high pure nitrogen circulate operation removing reaction system；Secondly, high-purity
Under nitrogen protection, by initiator A IBN be added reactor in, and 50-80 DEG C reaction 12-36 hours；Finally, by after reaction
Solution is added drop-wise in ethyl acetate and precipitates, and is washed repeatedly with ethyl acetate after filtering, washes away the homopolymer of VBC and ST, after centrifugation,
Drying at room temperature obtains yellow particle shape solid；The molar ratio of the VBC and ST are that the molar ratio of 2:1, VBC and N-PSF are 6:
The quality of 1-12:1, initiator A IBN and the ratio of system gross mass are 1:100；
Third step is crosslinked film forming procedure
Firstly, at room temperature, the N-PSF-VBC that second step synthesizes being added in dimethyl sulfoxide DMSO and is reacted
Liquid；Secondly, crosslinking agent TMHDA is added, is stirred 5-10 minutes at 50-70 DEG C, increases to solution viscosity by after the centrifugation of above-mentioned solution
After big, plastic film mulch liquid be transferred on smooth glass plate, obtain dense film after drying 24-36 hours at 50-70 DEG C；Finally, will
Film, which is removed and is immersed in NaOH solution, completes ion exchange, and so that film surface is reached neutrality with deionized water flushing immersion and obtain
Multipole ion cross-linking type anion-exchange membrane；The molar ratio of the TMHDA and N-PSF-VBC are 2:1.
3. a kind of preparation method of multipole ion cross-linking type anion-exchange membrane according to claim 2, feature exist
In reaction solution concentration described in the first step is 0.05g/L-0.1g/L.
4. a kind of preparation method of multipole ion cross-linking type anion-exchange membrane according to claim 2 or 3, feature
It is, reaction solution concentration described in second step is 0.05g/L-0.1g/L.
5. a kind of preparation method of multipole ion cross-linking type anion-exchange membrane according to claim 2 or 3, feature
It is, reaction solution concentration described in second step is 0.07g/L-0.1g/L.
6. a kind of preparation method of multipole ion cross-linking type anion-exchange membrane according to claim 4, feature exist
In reaction solution concentration described in second step is 0.07g/L-0.1g/L.
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| CN112751067A (en) * | 2021-01-04 | 2021-05-04 | 西北工业大学 | Cross-linked anion exchange membrane and preparation method and application thereof |
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