CN109265714A - A kind of preparation method of the cross-linking type anion-exchange membrane of low-water-content - Google Patents
A kind of preparation method of the cross-linking type anion-exchange membrane of low-water-content Download PDFInfo
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- CN109265714A CN109265714A CN201810704108.7A CN201810704108A CN109265714A CN 109265714 A CN109265714 A CN 109265714A CN 201810704108 A CN201810704108 A CN 201810704108A CN 109265714 A CN109265714 A CN 109265714A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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
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- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
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- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08J2371/12—Polyphenylene oxides
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Abstract
A kind of preparation method of the cross-linking type anion-exchange membrane of low-water-content, it include: (1) using bromomethylation polyphenylene oxide as basal lamina material, solvent 1-Methyl-2-Pyrrolidone is added into bromomethylation polyphenylene oxide solid, mechanical stirring is to being completely dissolved, quaternary ammonium reagent 1- vinyl imidazole, mechanical stirring to abundant reaction is added into the solution being completely dissolved again;(2) cross-linking reagent 1,6- ethanthiol and photoinitiator, stirring to formation homogeneous solution are added in the solution obtained to step (1);(3) on a glass by the homogeneous solution of step (2) acquisition, after scraping film-like on a glass using scraper, placement is irradiated in the UV lamp, carries out UV crosslinking, glass plate is heated to solvent after crosslinking to volatilize completely, to obtain cross-linking type anion-exchange membrane.The moisture content of film can be effectively reduced, to improve the swelling resistance and mechanical strength of film while anion-exchange membrane has high ion exchange volume in the present invention.
Description
Technical field
The invention belongs to anion exchange technical field of membrane, and in particular to a kind of cross-linking type yin with compared with low-water-content from
The preparation method of proton exchange.
Background technique
In recent years, amberplex was many important in membrane reactor battery, fuel cell, chlor-alkali manufacture, electrodialysis etc.
It has a wide range of applications in industrial process.Electrodialysis (ED) technology mature as one, other than its Technology Potential, due to
Its is at low cost, high-efficient, easy to operate and environmental-friendly and is widely used in water process.As the core of these processes, ion
Exchange membrane is by high polymer main chain, and exchangeable ion forms on electrically charged functional group and functional group.Amberplex is wanted
Reach for a long time, the requirement of efficient operation is not only wanted ion-selective permeability with higher and ionic conductivity, but also wanted
There are good mechanical performance, chemical stability and dimensional stability.
The key of the ion-selective permeability and ionic conductivity that improve amberplex is to improve the ion exchange of film
Capacity (IEC), but with the increase of IEC, film surface current potential can be enhanced to bring higher hydrophily.It will increase in this way
The moisture content of amberplex, making film that swelling easily occur leads to mechanical performance degradation, thus affects amberplex
Service life.Here ion exchange capacity and the swellbility of film there is " Tradeoff " relationship, this relationship one
Directly it is present in amberplex research and application process.So while guaranteeing that amberplex possesses higher IEC,
It is effectively reduced the moisture content of film, to guarantee the swelling resistance and mechanical strength of film.So preparing a kind of macroion
The exchange capacity and lower anion-exchange membrane of moisture content has great significance.Its research is conducive to anion-exchange membrane
It promotes and applies, is also beneficial to resource and preferably develop and uses.
Summary of the invention
For the above-mentioned problems in the prior art, the purpose of the present invention is to provide a kind of cross-linking type anion exchanges
The moisture content of film is effectively reduced while to guarantee that anion-exchange membrane has high ion exchange volume in the preparation method of film, from
And improve the swelling resistance and mechanical strength of film.
For achieving the above object, the present invention adopts the following technical scheme:
A kind of preparation method of cross-linking type amberplex, comprising:
(1) bromomethylation polyphenylene oxide (BPPO) is used as basal lamina material, solvent is added into bromomethylation polyphenylene oxide solid
1-Methyl-2-Pyrrolidone, mechanical stirring is to being completely dissolved, then quaternary ammonium reagent 1- ethylene is added into the solution being completely dissolved
Base imidazoles, mechanical stirring to abundant reaction;The wherein amount ratio of BPPO solid, 1-Methyl-2-Pyrrolidone, 1- vinyl imidazole
For 1-5g:1-15mL:0.1-1mL;
(2) cross-linking reagent 1,6- ethanthiol and photoinitiator, stirring to shape are added in the solution obtained to step (1)
At homogeneous solution;Wherein cross-linking reagent 1, the molar ratio of 6- ethanthiol and 1- vinyl imidazole are 0.1-1:1, photoinitiator with
The amount ratio of 1- vinyl imidazole is 0.01-0.1g:0.1-1mL;
(3) on a glass by the homogeneous solution of step (2) acquisition, after scraping film-like on a glass using scraper,
Placement is irradiated in the UV lamp, carries out UV crosslinking, glass plate is heated to solvent after crosslinking and is volatilized completely, to obtain
Cross-linking type anion-exchange membrane.
The present invention does not have particular/special requirement for photoinitiator, such as 2- benzyl -2- dimethylamino -1- (4- morpholinyl phenyl) fourth
Ketone, Irgacure-2959 etc. are suitable for the present invention, and those skilled in the art can select according to actual needs.
Further, in step (1), BPPO solid, 1-Methyl-2-Pyrrolidone, 1- vinyl imidazole amount ratio be 2g:
10mL:0.4mL.
Further, in step (1), reaction temperature be 25-50 DEG C (preferably 45 DEG C), the reaction time be 1-24h (preferably
24h)。
Further, in step (2), cross-linking reagent 1,6- ethanthiol and the molar ratio of 1- vinyl imidazole are preferably 0.2-
0.4。
Further, in step (2), the preferred 0.05g:0.4mL of amount ratio of photoinitiator and 1- vinyl imidazole.
Further, in step (3), scraper thickness used by knifing is 550-650 μm (preferably 600um), ultraviolet lamp light wave
A length of 100-400nm (preferably 345nm), ultraviolet lamp irradiation time are 10-60min (preferably 30min), heating temperature 50-100
DEG C (preferably 60 DEG C), heating time are 10-15 hours (preferably 12 hours).
Compared with prior art, beneficial effects of the present invention are as follows:
In the present invention, by 1- vinyl imidazole and 1,6- ethanthiol carries out UV crosslinking, and preparation possesses three-dimensional netted
The anion-exchange membrane of structure has while guaranteeing that anion-exchange membrane has higher ion exchange capacity and conductivity
Effect reduces the moisture content of film, the anti-swelling and the mechanical strength during utilization for ensureing anion-exchange membrane.While such
For industrializing very big directive significance from now on, preparation process is simple for the preparation of type anion-exchange membrane, to solve ion
Existing " Tradeoff " relationship provides preferable solution between exchange capacity and the swellbility of film, has industrialized latent
Energy.
Detailed description of the invention
Fig. 1 is anion-exchange membrane preparation process schematic diagram in the present invention;
Fig. 2 is the atomic force microscope phasor of anion-exchange membrane in the present invention;
Fig. 3 is the ion exchange capacity of anion-exchange membrane;
Fig. 4 (a) (b) varies with temperature figure for the moisture content of anion-exchange membrane, swellbility;(a) anion-exchange membrane
Moisture content, (b) swellbility of anion-exchange membrane;
Fig. 5 is the mechanical strength figure of anion-exchange membrane;
Fig. 6 is the hydroxyl conductivity of anion-exchange membrane;
Fig. 7 is the schematic diagram of electrodialysis desalination device and process;
In Fig. 8, (a) is the conductivity variations figure of light room and dense room feed liquid, (b) is the removal efficiency figure of salt;
In Fig. 9, (a) and (b) is respectively current efficiency and energy consumption figure.
Specific embodiment
The preferred embodiment of the present invention is described in detail below, so that contents of the present invention feature is easy to by this field
In researcher understand, to make more full and accurate define to protection scope of the present invention.
Bromomethylation polyphenylene oxide that embodiment uses, 1,6- ethanthiol, 1- vinyl imidazole and trimethylamine structural formula
It is as follows:
Embodiment 1
(1) (production of Shandong Tian Wei company, bromomethylation degree is the 1- methyl -2- pyrrolidines for 55%) being dissolved in 10mL to 2gBPPO
In ketone, magnetic agitation is completely dissolved to obtain amber transparent solution up to BPPO, obtains BPPO solution.
(2) the 1- vinyl imidazole (Shanghai Mike woods company production, 97%) of 0.4mL is added dropwise into BPPO solution, 45
At DEG C, magnetic agitation is reacted for 24 hours, obtains the quaternary ammoniated BPPO solution of 1- vinyl imidazole.
(3) into quaternary ammoniated BPPO solution, be added 0.204mL 1,6- ethanthiol (Shanghai Aladdin company production,
95%) (Shanghai Aladdin company is raw with photoinitiator 2- benzyl -2- dimethylamino -1- (4- morpholinyl phenyl) butanone of 0.05g
Produce), magnetic agitation to solution is uniformly mixed.On a glass by homogeneous solution, it is spread on a glass using 600 μm of scrapers
It after membranaceous, be placed under the ultraviolet light of 345nm wavelength and irradiate 30min, carry out UV crosslinking.After crosslinking, by glass plate
It is placed on heating 12h on 60 DEG C of panel heater to volatilize completely to solvent, obtains cross-linking type anion-exchange membrane BPPO-Im0.2.
Preparation process schematic diagram is as shown in Figure 1.
It can be seen that the addition of crosslinking substance so that the phase separation degree of film increases from the atomic force microscope phasor of Fig. 2,
The successful progress of proved response.
Embodiment 2
The dosage of crosslinking agent 16- ethanthiol in examples detailed above 1 is changed to 0.136mL, other steps are constant, handed over
Connection type anion-exchange membrane BPPO-Im0.3.
Embodiment 3
By crosslinking agent 1 in examples detailed above 1, the dosage of 6- ethanthiol is changed to 0.272mL, other steps are constant, it is handed over
Connection type anion-exchange membrane BPPO-Im0.4.
Comparative example
(1) (production of Shandong Tian Wei company, bromomethylation degree is the 1- methyl -2- pyrrolidines for 55%) being dissolved in 10mL to 2gBPPO
In ketone, magnetic agitation is completely dissolved to obtain amber transparent solution up to BPPO, obtains BPPO solution.
(2) trimethylamine ethanol solution (Ann Kyrgyzstan company production, 33wt%) of 0.3mL is added dropwise into BPPO solution, 25
At DEG C, magnetic agitation reacts 6h, obtains with the quaternary ammoniated BPPO solution of trimethylamine.The solution that reaction is completed is poured on glass plate
On, 12h, which is heated, on 60 DEG C of panel heater volatilizees completely to solvent.Obtain uncrosslinked anion-exchange membrane BPPO-TMA
As a comparison case.
Embodiment 4: the IEC test of film
After membrane sample prepared in the above embodiments is dried completely, quality is weighed.Then membrane sample is respectively put into 20mL's
In 0.5MNaCl solution for 24 hours, the commutative group of film is replaced into Cl-.It then takes the film out, is cleaned for several times with deionized water,
Wash away the chloride ion of film surface.Then membrane sample is placed in the 0.05M metabisulfite solution of 10mL and is impregnated for 24 hours, by commutative base
Group Cl-It cements out completely, then measures Chlorine in Solution ion concentration with potentiometric titration.By the IEC that film is calculated.
Experimental result as shown in figure 3, the BPPO-TMA of the IEC of cross-linking type amberplex and uncrosslinked film, business yin from
Proton exchange AEM-TypeII (Japanese Fujifilm company) is essentially identical, partially also exceeds, has reached application level.
Embodiment 5: the moisture content of anion-exchange membrane, swellbility test
After membrane sample prepared in the above embodiments is dried completely, diaphragm quality is weighed, and measure diaphragm length, then
Membrane sample is soaked in the deionized water of different temperatures (20,40,60,80 DEG C).It takes out afterwards for 24 hours, using filter paper by diaphragm watch
The water in face is cleaned, and weighs the quality of wet film piece again, and measures the length of wet film piece.The aqueous of membrane sample is obtained by calculation
Rate and swellbility.
Experimental result as shown in figure 4, cross-linking type anion-exchange membrane moisture content and swellbility be all significantly lower than it is uncrosslinked
Anion-exchange membrane BPPO-TMA.In the case where guaranteeing that IEC is essentially identical, reach the anti-swelling for reducing moisture content and improving film
The purpose of performance.
Embodiment 6: the Measuring Mechanical Properties of film
Anion-exchange membrane is cut into the membrane sample of 1cm × 10cm, with tensile strength tester come to anion exchange
The mechanical strength of film is measured.
Experimental result as shown in figure 5, the tensile strength of cross-linking type anion-exchange membrane is apparently higher than uncrosslinked membrane sample,
Anion-exchange membrane in the available invention has better mechanical strength.Be conducive to application in practice.
Embodiment 7: the hydroxyl conductivity test of film
Anion-exchange membrane is cut into the membrane sample of 1cm × 4cm, is put into 1MNaOH solution and impregnates 48h at 60 DEG C.
It is cleaned repeatedly after taking-up with deionized water, removes the hydroxide ion of film surface remnants.Then it is measured by electrochemical workstation
The impedance of anion-exchange membrane at different temperatures, so that the hydroxyl conductivity of film be calculated.
Experimental result as shown in fig. 6, BPPO-Im0.2,0.3 anion-exchange membrane have very high hydroxyl conductivity,
Illustrate that cross-linking type anion-exchange membrane has good ion-selective permeability and good alkaline stability.Meet anion friendship
Change the demand that film uses under various circumstances.
Embodiment 8: desalting performance test
As shown in fig. 7, the schematic diagram of electrodialysis desalination device and process.Electrode solution is 0.3MNa2SO4Solution, 0.5MNaCl
Solution is placed in anion-exchange membrane two sides as feed liquid, and anode membrane uses the CEM-TypeI of Fujifilm company of Japan.Every ten minutes
Measure and record the conductivity of light room and dense room feed liquid and the voltage at device both ends respectively by conductivity meter.By subsequent
Related calculating, obtain the related desalting performance such as NaCl removal efficiency, current efficiency, energy consumption, and with commercial anionic exchange membrane
AEM-Type II makes comparisons.
Experimental result is as shown in Figure 8, Figure 9, and the desalting performance of cross linking membrane is compared with commercial anionic exchange membrane, from the de- of salt
Except rate, current efficiency and energy consumption angle are seen, all slightly advantage, the anion-exchange membrane prepared in this way can be in electrodialysis
It is applied in the process.
Claims (9)
1. a kind of preparation method of cross-linking type amberplex, comprising:
(1) using bromomethylation polyphenylene oxide as basal lamina material, solvent 1- methyl -2- pyrrole is added into bromomethylation polyphenylene oxide solid
Pyrrolidone, mechanical stirring is to being completely dissolved, then quaternary ammonium reagent 1- vinyl imidazole is added into the solution being completely dissolved, mechanical
Stirring is reacted to abundant;The wherein amount ratio of bromomethylation polyphenylene oxide solid, 1-Methyl-2-Pyrrolidone, 1- vinyl imidazole
For 1-5g:1-15mL:0.1-1mL;
(2) cross-linking reagent 1,6- ethanthiol and photoinitiator are added in the solution obtained to step (1), stirring is equal to being formed
Even solution;The molar ratio of wherein cross-linking reagent 1,6- ethanthiol and 1- vinyl imidazole is 0.1-1:1, photoinitiator and 1- second
The amount ratio of alkenyl imidazoles is 0.01-0.1g:0.1-1mL;
(3) homogeneous solution for obtaining step (2) on a glass, after scraping film-like on a glass using scraper, is placed
It irradiates in the UV lamp, carries out UV crosslinking, glass plate is heated to solvent after crosslinking and is volatilized completely, to be crosslinked
Type anion-exchange membrane.
2. preparation method as described in claim 1, it is characterised in that: in step (1), reaction temperature is 25-50 DEG C, when reaction
Between be 1-24h.
3. preparation method as claimed in claim 2, it is characterised in that: in step (1), BPPO solid, 1- methyl -2- pyrrolidines
Ketone, 1- vinyl imidazole amount ratio be 2g:10mL:0.4mL.
4. preparation method as claimed in claim 3, it is characterised in that: in step (1), reaction temperature is 45 DEG C, the reaction time
For for 24 hours.
5. the preparation method as described in one of Claims 1 to 4, it is characterised in that: in step (1), the photoinitiator is
2- benzyl -2- dimethylamino -1- (4- morpholinyl phenyl) butanone or Irgacure-2959.
6. the preparation method as described in one of Claims 1 to 4, it is characterised in that: in step (2), cross-linking reagent 1,6- oneself two
The molar ratio of mercaptan and 1- vinyl imidazole is 0.2-0.4.
7. preparation method as claimed in claim 6, it is characterised in that: in step (2), photoinitiator and 1- vinyl imidazole
Amount ratio is 0.05g:0.4mL.
8. the preparation method as described in one of Claims 1 to 4, it is characterised in that: in step (3), scraper used by knifing
Thickness is 550-650 μm, a length of 100-400nm of ultraviolet lamp light wave, and ultraviolet lamp irradiation time is 10-60min, heating temperature 50-
100 DEG C, heating time is 10-15 hours.
9. preparation method as claimed in claim 8, it is characterised in that: in step (3), ultraviolet lamp light wave a length of 345nm is ultraviolet
The light irradiation time is 30min.
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