membrane

Abstract

An anion exchange membrane obtainable by curing a curable composition, the curable composition comprising (a) a component (a) of formula (I); AR 1 -(CH2) n -N + (R a R b )-(CH2) n -AR 2 , X - Formula (I) and (b) component (b) of formula (II); AR 3 -(CH2) n -N + (R c R d )-LN + (R e R f )-(CH2) n -AR 4 , 2X - Formula (II), wherein n, L, X -、 R a , R b , R c , R d , R e and R f is as defined in claim 1; AR 1 , A.R. 2 , A.R. 3 and A.R. 4 each independently contain an aromatic group; and component (a) of formula (I) and component (b) of formula (II) each contain at least two curable ethylenically unsaturated groups.

Description

[Technical Field]

[0001] The present invention relates to ion exchange membranes, in particular anion exchange membranes (AEMs), their preparation process and their use. [Background technology]

[0002] Ion exchange membranes are used in electrodialysis, electrolysis, acid and base production, and many other processes. Typically, the transport of ions through a membrane occurs under the influence of a driving force, such as a potential gradient.

[0003] Some ion exchange membranes include a porous support, which provides mechanical strength. Such membranes are often called "composite membranes" because of the presence of both an ionic-charged polymer that discriminates against oppositely charged ions and a porous support that provides mechanical strength.

[0004] BPM is commonly used to generate acids and bases, for example in a process called bipolar electrodialysis (BPED). BPM has both a cationic or anion exchange layer (AEL) and an anionic or cation exchange layer (CEL), and therefore has both negatively and positively charged layers.

[0005] In the BPED process, acids and bases are generated at the boundary of the BPM by the water dissociation reaction (WDR). + and OH -The ions pass through the corresponding ion exchange layers toward the cathode and anode, respectively. The BPED process is carried out in a bipolar electrodialysis stack, which contains monopolar anion exchange and monopolar cation exchange membranes in addition to a bipolar membrane. In a bipolar electrodialysis stack, the monopolar cation and anion exchange membranes are responsible for selectively separating salt ions in the feed stream according to their charge. The salt anions then combine with H+ formed by the WDR to form acids, and the salt cations combine with OH- to form bases. For example, if NaCl is used in the feed stream, the monopolar membrane will separate Cl - From Na + By separating the two, NaOH and HCl are formed.

[0006] To generate high concentrations of acids and bases, it is important that the monopolar membrane has very high pH stability and durability (high pH stability and durability result in a long membrane life). High efficiency of the process for generating acids and bases is also desirable. This is due to the H + and OH - Ions reach the wrong channel and H + and OH - To prevent ions from recombining to form water and resulting in product loss, the membrane needs to have very high permselectivity. Especially for anion exchange membranes, it is difficult to achieve high proton blocking capacity at high concentrations due to the small size of protons. Summary of the Invention [Problem to be solved by the invention]

[0007] The object of the present invention is to provide an anion exchange membrane that is mechanically strong and has high permselectivity at very low pH values, which is achieved by controlling the swelling behavior. [Means for solving the problem]

[0008] According to a first aspect of the present invention, there is provided an anion exchange membrane obtainable by curing a curable composition, the curable composition comprising: (a) component (a) of formula (I); and AR 1 -(CH2) n -N + (R a R b )-(CH2) n -AR 2 , X - Formula (I) (b) component (b) of formula (II); AR 3 -(CH2) n -N + (R c R d )-LN + (R e R f )-(CH2) n -AR 4 , 2X - Formula (II) Including, During the ceremony, each n independently has a value of 1 or 2; L is a non-aromatic linking group; each X - are independently anions; AR 1 , A.R. 2 , A.R. 3 and A.R. 4 each independently comprises an aromatic group; (i)R a , R b , R c , R d , R e and R f each independently represents an optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 is an alkenyl group or a vinylbenzyl group; or (ii)R a and R btogether with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; or (iii)R a and R b one of which is optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 alkenyl or vinylbenzyl group, and R a and R b The other is the formula AR 1 -(CH2) n -N + together with the group: (iv)R a is the formula AR 1 -(CH2) n -N + together with the group R b is the formula N + -(CH2) n -AR 2 together with the group: (v)R c and R d together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring, and R e and R f each independently represents an optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 is an alkenyl group or a vinylbenzyl group; or (vi)R c and R d together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring, and R e and R f together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; or (vii)R c and R done of which is optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 alkenyl or vinylbenzyl group, and R c and R d The other is the formula AR 3 -(CH2) n -N + together with the group R e and R f each independently represents an optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 is an alkenyl group or a vinylbenzyl group; or (viii)R c and R d one of which is optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 alkenyl or vinylbenzyl group, and R c and R d The other is the formula AR 3 -(CH2) n -N + together with the group R e and R f together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; or (ix)R c and R d One of the two and R e and R f one of which is optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 alkenyl or vinylbenzyl group, and R c and R d The other is the formula AR 3 -(CH2) n -N + together with the group R e and R f The other is the formula N+ -(CH2) n -AR 4 together with the group: (x)R c and R d one of which is optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 alkenyl or vinylbenzyl group, and R c and R d is connected to L to form an optionally substituted ring, and R e and R f each independently represents an optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 an alkenyl group or a vinylbenzyl group; The anion exchange membrane is provided as described above, wherein component (a) of formula (I) and component (b) of formula (II) each contain at least two curable ethylenically unsaturated groups.

[0009] Preferably, the water uptake of the anion exchange membrane is 11 to 16.5%. Preferably, the anion exchange capacity of the anion exchange membrane is 0.7 to 1.0 meq / g dry membrane.

[0010] Preferably, the mole fraction of component (a) to component (b) is at least 0.60 and not more than 0.96, more preferably at least 0.65 and not more than 0.95, especially at least 0.65 and not more than 0.90, and more especially at least 0.70 and not more than 0.80.

[0011] In this document (including the claims), the verb "comprise" and its conjugations are used in their open-ended sense, meaning that items following the word are included, while items not specifically mentioned are not excluded. Additionally, reference to an element by the indefinite article "a" or "an" does not exclude the possibility that more than one of the element is present, unless the context clearly requires that one or only one element be present. Thus, the indefinite article "a" or "an" typically means "at least one." A vinylbenzyl group is a CH₂=CHC₆H₄CH₂*— group, where the asterisk denotes the point of attachment to the rest of the molecule.

[0012] Preferred curable ethylenically unsaturated groups are vinyl and allyl groups, most preferably vinyl groups. The vinyl group (CH=CH-) is non-acrylic, i.e., the vinyl group is not bonded to a (C=O)O- or (C=O)NH- group.

[0013] Curable ethylenically unsaturated groups can react with other curable ethylenically unsaturated groups to form covalent bonds therewith, for example, when heated and / or irradiated with light (e.g., ultraviolet light) or an electron beam.

[0014] Preferably, L is a non-aromatic linking group (e.g., an optionally interrupted C 2~7 Alkylene group or C 2~7 an alkelene group or an optionally substituted C5-C6-cycloalkylene group, wherein the optional interruptions are selected from oxygen, nitrogen and sulfur, or L is a group consisting of one of the positively charged nitrogen atoms and R c , R d , R e and R fExamples of L include ethylene (-CH2CH2-), propylene (-C3H6-), butylene (-C4H8-), 2,2-dimethylpropylene, methoxymethylene, diethylene ether (-CH2CH2-O-CH2CH2-), diethylene thioether (-CH2CH2-S-CH2CH2-), diallylpropylene, cyclopentylene, and cyclohexylene.

[0015] Preferably, both component (a) and component (b) contain at least two curable ethylenically unsaturated groups, more preferably two and only two curable ethylenically unsaturated groups. Preferably, the curable ethylenically unsaturated groups present in component (a) are AR 1 and / or A.R. 2 and component (b) is present in AR 3 and / or A.R. 4 In a preferred embodiment, AR 1 , A.R. 2 , A.R. 3 and A.R. 4 each contain one or only one curable ethylenically unsaturated group, and components (a) and (b) each have a total of two curable ethylenically unsaturated groups. The additional curable ethylenically unsaturated group (preferably a vinyl group) is a , R b , R c , R d , R e and R f may be present in one or more of:

[0016] The positively charged nitrogen atom (N + ) is a non-aromatic system, i.e., it is not part of an aromatic heterocycle. Preferably, the anion X - does not react with other components of the curable composition, i.e., X - is inactive. X -Preferred anions represented by X include hydroxide, fluoride, chloride, bromide, iodide, nitrate, thiocyanate, hexafluoroborate, methanesulfonate, trifluoromethanesulfonate, formate, and acetate. - is a chloride anion because it can provide a component of formula (I) with excellent solubility without dramatically increasing the molecular weight of component (a) of formula (I).

[0017] Preferably, each n independently has a value of 1. In a particularly preferred embodiment, in both Formula (I) and Formula (II), both n have a value of 1. In one embodiment, R a , R b , R c , R d , R e and R f each independently represents an optionally substituted C 1~3 alkyl groups (e.g., methyl, ethyl, propyl, or isopropyl), optionally substituted C 2~3 It is selected from an alkenyl group (for example -CH=CH2 or -CH2CH=CH2) and a vinylbenzyl group (CH2=CH-C6H6-).

[0018] In another embodiment, R a and R b , and / or R c and R d and / or R e and R f together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring, for example an optionally substituted pyrrolidinium, pyrrolinium, imidazolinium, piperidinium or morpholinium ring.

[0019] In another embodiment, R a and R b one of which is optionally substituted C1~3 alkyl group, optionally substituted C 2~3 alkenyl or vinylbenzyl group, and R a and R b The other is the formula AR 1 -(CH2) n -N + A group of formula (wherein AR 1 and n is as defined above) together form an optionally substituted 5- or 6-membered ring, for example an optionally substituted pyrrolidinium, pyrrolinium, piperidinium or morpholinium ring, in each case having an aromatic ring (e.g. a benzene ring) fused thereto (preferably with two or more, preferably one, curable ethylenically unsaturated group attached to the benzene ring).

[0020] In another embodiment, R a is the formula AR 1 -(CH2) n -N + A group of formula (wherein AR 1 and n is as defined above) together form an optionally substituted 5- or 6-membered ring, R b is the formula N + -(CH2) n -AR 2 A group of formula (wherein AR 2 and n is as defined above) together form an optionally substituted 5- or 6-membered ring.

[0021] In another embodiment, R c and R d and / or R e and R f One or both of the groups may be optionally substituted C 1~3 alkyl group, optionally substituted C 2~3 alkenyl or vinylbenzyl group, and R c and R d The other is the formula AR 3 -(CH2) n -N + A group of formula (wherein AR3 and n is as defined above) together form an optionally substituted 5- or 6-membered ring, for example an optionally substituted pyrrolidinium, pyrrolinium, piperidinium or morpholinium ring, in each case having an aromatic ring (e.g. a benzene ring) fused thereto (preferably with two or more, preferably one, curable ethylenically unsaturated group attached to the benzene ring), and / or R e and R f The other is the formula N + -(CH2) n -AR 4 A group of formula (wherein AR 4 and n is as defined above) together form an optionally substituted 5- or 6-membered ring.

[0022] Preferred optionally substituted 5- or 6-membered rings are as defined above (an example is a 6-azoniaspiro[5.5]undecylene ring in the case of component (a)). Preferred optional substituents are curable ethylenically unsaturated groups (as described above and are preferred).

[0023] Preferably, AR 1 , A.R. 2 , A.R. 3 and A.R. 4 Each independently contains a phenyl or styrenyl group. More preferably, AR 1 , A.R. 2 , A.R. 3 and A.R. 4 is a styrenyl group (i.e., a CH2=CH-C6H4- group).

[0024] In a preferred embodiment, component (a) is of formula (III):

[0025] [ka]

[0026] wherein R a, R b and X - is as defined above. Component (a) may optionally comprise one or more components (a) of formula (I) (more preferably formula (III)), such as AR 1 and / or A.R. 2 It may also comprise a mixture of isomers in which the curable unsaturated groups are present in different positions (eg, ortho, meta and / or para positions).

[0027] Examples of monomers that can be used as component (a) include the following compounds AXL-1 to AXL-14.

[0028] [ka]

[0029] [ka]

[0030] [ka]

[0031] In a preferred embodiment, component (b) is of formula (IV):

[0032] [ka]

[0033] wherein L, R c , R d , R e , R f and X - is as defined above. Component (b) may optionally comprise one or more components (b) of formula (II) (more preferably formula (IV)), such as AR 3 and / or A.R. 4It may also comprise a mixture of isomers in which the curable unsaturated groups are present in different positions (eg, ortho, meta and / or para positions).

[0034] Examples of monomers that can be used as component (b) include the following compounds AXL2-1 to AXL2-18.

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038] [ka]

[0039] In one embodiment, the anion exchange membrane according to the first aspect of the present invention contains at least 1 ppm of component (a), preferably at least 10 ppm of component (a), particularly at least 100 ppm of component (a) (typically as a result of incomplete curing when the membrane is formed), and at least 1 ppm of component (b), preferably at least 10 ppm of component (b), particularly at least 100 ppm of component (b). Preferably, the anion exchange membrane contains less than 20,000 ppm of component (a), more preferably less than 10,000 ppm of component (a), and less than 20,000 ppm of component (b), more preferably less than 10,000 ppm of component (b). The amount present in the anion exchange membrane can be determined by the method described on page 19 of WO2022 / 162083.

[0040] The curable composition preferably comprises 35 to 70 wt%, more preferably 40 to 70 wt%, in particular 40 to 65 wt%, more particularly 45 to 65 wt%, and most preferably 50 to 60 wt% of component (a), and preferably 3 to 40 wt%, more preferably 4 to 35 wt%, in particular 5 to 34 wt%, more particularly 5 to 30 wt%, and most preferably 15 to 30 wt% of component (b).

[0041] Optionally, the curable composition further comprises, as component (c), a monomer comprising a group having a cationic charge and one or only one curable ethylenically unsaturated group. Preferably, the curable composition does not comprise component (c), or the composition comprises a small amount of component (c), for example, the curable composition preferably comprises 0 to 10 wt % of component (c), more preferably 0 to 7 wt % of component (c).

[0042] In component (c), the group having a cationic charge is preferably a quaternary ammonium group. The one and only curable ethylenically unsaturated group present in component (c) is preferably a vinyl or allyl group, more preferably a vinyl group.

[0043] Component (c) may comprise one or more monomers containing a group bearing a cationic charge and one or only one curable ethylenically unsaturated group. In one embodiment, component (c) has the formula (SM), where R 1 , R 2 and R 3 each independently represents an alkyl group or an aryl group, or R 1 , R 2 and R 3 two or three of these, together with the positively charged nitrogen atom to which they are attached, form an optionally substituted 5- or 6-membered ring; n3 represents an integer of 1 to 3; X3 - represents an anion, preferably a chloride ion, a bromide ion, an iodide ion or a hydroxide ion.

[0044] [ka]

[0045] Examples of component (c) of formula (SM) include the following compounds:

[0046] [ka]

[0047] The above components can be prepared, for example, as described in US2016 / 177006. The curable composition optionally further comprises a radical initiator as component (d). Preferred radical initiators include thermal initiators, photoinitiators, and combinations thereof. The curable composition preferably comprises 0 to 10 wt % of the radical initiator, more preferably 0 to 3 wt % of the radical initiator. When the curable composition is cured using ultraviolet light, visible light, or thermally, the curable composition preferably comprises 0.001 to 2 wt %, particularly 0.005 to 1.5 wt %, of the radical initiator.

[0048] Examples of suitable thermal initiators that can be used as component (d) include 2,2'-azobis(2-methylpropionitrile) (AIBN), 4,4'-azobis(4-cyanovaleric acid), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), nitrile), dimethyl 2,2'-azobis(2-methylpropionate), 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide, 1-[(1-cyano-1-methylethyl)azo]formamide, 2,2'-azobis(N-butyl-2-methylpropionamide), 2,2'-azobis(N-cyclohexyl-2-methylpropionamide), 2,2'-azobis(2-methylpropionamide) 2,2'-Azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride, 2,2'-Azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride, 2,2'-Azobis[2-(2-imidazolin-2-yl)propane]disulfate dihydrate, 2,2'-Azobis[N-(2-carboxyethyl)-2-methylpropionamidine]hydrate, 2,2'-Azobis{2-[1-(2-hydroxyethyl)-2-imidazolin-2-yl]propane}dihydrate Examples of suitable azobis include 2,2'-azobis[2-(2-imidazolin-2-yl)propane], 2,2'-azobis(1-imino-1-pyrrolidino-2-ethylpropane) dihydrochloride, 2,2'-azobis{2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide}, and 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide].

[0049] Examples of suitable photoinitiators that may be included as component (d) in the curable composition include aromatic ketones, acylphosphine compounds, aromatic onium salt compounds, organic peroxides, thio compounds, hexaarylbiimidazole compounds, ketoxime ester compounds, boric acid compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds. Preferred examples of aromatic ketones, acylphosphine oxide compounds, and thio compounds include compounds having a benzophenone skeleton or thioxanthone skeleton described in "RADIATION CURING IN POLYMER SCIENCE AND TECHNOLOGY," pp. 77-117 (1993).More preferred examples thereof include alpha-thiobenzophenone compounds described in JP1972-6416B (JP 47-006416), benzoin ether compounds described in JP1972-3981B (JP 47-003981), alpha-substituted benzoin compounds described in JP1972-22326B (JP 47-022326), and alpha-substituted benzoin compounds described in JP1972-23664B (JP 47-022326). benzoin derivatives described in JP1982-30704A (JP 57-030704 A), aroylphosphonic acid esters described in JP1982-30704A (JP 57-030704 B), dialkoxybenzophenones described in JP1985-26483B (JP 60-026483 B), and benzoin derivatives described in JP1985-26403B (JP 60-026403 B) and JP1987-81345A (JP 62-081345 B). Benzoin ethers, alpha-aminobenzophenones described in JP1989-34242B (JP-B 01-034242), US4,318,791A, and EP0284561A1, p-di(dimethylaminobenzoyl)benzene described in JP1990-211452A (JP-A 02-211452), thio-substituted benzoin ethers described in JP1986-194062A (JP-A 61-194062), and the like. Examples of suitable initiators include substituted aromatic ketones, acylphosphine sulfides described in JP1990-9597B (JP Patent Publication No. 02-009597), acylphosphines described in JP1990-9596B (JP Patent Publication No. 02-009596), thioxanthones described in JP1988-61950B (JP Patent Publication No. 63-061950), and coumarins described in JP1984-42864B (JP Patent Publication No. 59-042864). In addition, photoinitiators described in JP2008-105379A and JP2009-114290A are also preferred. In addition, photoinitiators described in "Ultraviolet Curing System" by Kato Kiyomi, pages 65-148 (published by Research Center Co., Ltd. in 1989) can also be used.

[0050] Particularly preferred photoinitiators include Norrish Type II photoinitiators having an absorption maximum at a wavelength greater than 380 nm when measured in one or more of water, ethanol, and toluene at a temperature of 23° C. Examples include photoinitiators derived from xanthenes, flavins, curcumins, porphyrins, anthraquinones, phenoxazines, camphorquinones, phenazines, acridines, phenothiazines, xantithones, thioxantithones, thioxanthenes, acridones, flavones, coumarins, fluorenones, quinolines, quinolones, naphthoquinones, quinolinones, arylmethanes, azos, benzophenones, carotenoids, cyanines, phthalocyanines, dipyrrines, squarines, stilbenes, styryls, triazines, or anthocyanins.

[0051] Optionally, the curable composition further comprises a monomer that does not contain a group with a cationic charge, and preferably further comprises a monomer that contains at least two curable ethylenically unsaturated groups as component (e).

[0052] Preferably, the curable composition contains 0 to 5 wt % of component (e), and more preferably, the curable composition does not contain component (e). The curable composition preferably further comprises a solvent as component (f). The solvent is preferably an inert solvent. The inert solvent does not react with any of the other components of the curable composition. In a preferred embodiment, component (f) comprises water and optionally an organic solvent, particularly when some or all of the organic solvent is water-miscible. Water is useful for dissolving components (a) and (b), and optionally also component (c), and the organic solvent is also useful for dissolving any organic components present in the curable composition.

[0053] Component (f) is useful for reducing the viscosity and / or surface tension of the curable composition. In a preferred embodiment, the curable composition comprises 10 to 40 wt %, especially 20 to 30 wt %, of component (f).

[0054] Examples of inert solvents that can be used as or in component (f) include water, alcohol-based solvents, ether-based solvents, amide-based solvents, ketone-based solvents, sulfoxide-based solvents, sulfone-based solvents, nitrile-based solvents, and organophosphorus-based solvents. Examples of alcohol-based solvents that can be used as or in (f) (especially in combination with water) include methanol, ethanol, isopropanol, n-propanol, n-butanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, and mixtures containing two or more thereof. Additionally, preferred inert organic solvents that can be used in (f) include dimethyl sulfoxide, dimethylimidazolidinone, sulfolane, N-methylpyrrolidone, dimethylformamide, acetonitrile, acetone, 1,4-dioxane, 1,3-dioxolane, tetramethylurea, hexamethylphosphoramide, hexamethylphosphorotriamide, pyridine, propionitrile, butanone, cyclohexanone, tetrahydrofuran, tetrahydropyran, 2-methyltetrahydrofuran, ethylene glycol diacetate, cyclopentyl methyl ether, methyl ethyl ketone, ethyl acetate, y-butyrolactone, and mixtures containing two or more thereof.

[0055] The curable composition may further comprise other ingredients such as inhibitors, wetting agents to improve coating properties, biocides, stabilizers, preferably in small amounts, for example 0-3 wt %.

[0056] The AEM preferably has a low water permeability so that (hydrate) ions can pass through the membrane, but (free) water molecules do not easily pass through the membrane. The water permeability of the AEM is preferably 1.10 -11 m 3 / m 2 Lower than s kPa, preferably 5.10 -12 m 3 / m 2 Lower than s kPa, especially 4.10 -12 m 3 / m 2 Lower than ·s·kPa.

[0057] The distance between the two cationic nitrogen atoms in component (b) is preferably at least 0.35 nm, which enhances the pH stability of the resulting film. Preferably, the distance between the two cationic nitrogen atoms in component (b) is less than 1.5 nm, because a short distance enhances the crosslinking density of the resulting film.

[0058] Preferably, components (a) and (b) each have a molecular weight of less than 600 Daltons, more preferably less than 550 Daltons. Higher molecular weights are expected to result in membranes with higher electrical resistance.

[0059] The molar fraction of the sum of components (a) and (b) relative to all curable compounds present in the curable composition is preferably at least 0.95. A high ratio of components (a) and (b) relative to all curable compounds present in the curable composition is preferred to obtain a membrane with high crosslink density and therefore high permselectivity. The molar fraction of components (a) and (b) relative to all curable compounds present in the curable composition is preferably at most 1.0. The molar fraction of the sum of components (a) and (b) relative to all curable compounds present in the curable composition can be calculated by dividing the sum of the molar amounts of components (a) and (b) by the sum of the molar amounts of all curable compounds present in the curable composition. Alternatively, the molar fraction can be determined by measuring the extractables from the anion exchange membrane, as described, for example, on page 19 of WO 2022 / 162083.

[0060] The permselectivity (PS) of the membranes of the invention for protons, as determined as described below (in a 0.05M to 4M HCl system), is preferably at least 50%, more preferably at least 60%.

[0061] The electrical resistance of the membrane of the present invention, as determined below (in 2M NaCl), is preferably 15 ohms / cm 2 less than, more preferably 12 ohms / cm 2 Less than 10 ohms / m 2 is less than.

[0062] Preferably, the anion exchange membrane according to the present invention has an ion exchange capacity (IEC) of at least 0.7 meq / g dry membrane, more preferably at least 0.8 meq / g dry membrane, as measured by the method described below. Such an IEC can provide an anion exchange membrane with low electrical resistance.

[0063] Preferably, the anion exchange membrane according to the present invention has an IEC of less than 1.00 meq / g dry membrane, more preferably less than 0.95 meq / g dry membrane, as measured by the method described below. Such an IEC can provide an anion exchange membrane that does not swell excessively and therefore retains excellent permselectivity during use.

[0064] Therefore, the anion exchange membrane according to the present invention preferably has an IEC of 0.7 to 1.0 meq / g dry membrane when measured by the method described below. Generally, it is preferable that PS is as high as possible and ER is as low as possible. It is generally known to those skilled in the art that there is a trade-off between PS and ER: a very high PS can be achieved at the expense of a higher ER, and if a low ER is desired, permselectivity must be sacrificed. The membranes of the present invention exhibit very high PS and acceptable ER. A suitable parameter for selecting a good membrane in a simple manner is to measure the water uptake (WU) of the membrane. The water uptake is preferably 11-16%, more preferably 12-16%.

[0065] However, the ion exchange capacity (IEC) has a significant impact on the swelling characteristics, and therefore the permselectivity, as well as the electrical resistance of the membrane. Therefore, a more accurate method for selecting a good membrane is based on both the water absorption and the ion exchange capacity, e.g., the product of the water absorption value and the ion exchange capacity value. Preferably, WU × IEC is 8.5 to 15.5, more preferably 9.0 to 15.0, and especially 9.2 to 14.7, where the water absorption is expressed as a percentage (%) and the ion exchange capacity is expressed as meq / g dry membrane. The water absorption and ion exchange capacity can be determined as described below in the experimental section.

[0066] The anion exchange membrane of the present invention preferably further comprises a porous support. Examples of usable porous supports include woven and nonwoven synthetic fabrics and extruded films. Examples include wet-laid and dry-laid nonwoven materials, spunbond and meltblown fabrics, and nanofiber webs made from, for example, polyethylene, polypropylene, polyacrylonitrile, polyvinyl chloride, polyphenylene sulfide, polyester, polyamide, polyaryletherketone, such as polyetheretherketone, and copolymers thereof. The porous support can also be a porous membrane, such as polysulfone, polyethersulfone, polyphenylene sulfone, polyphenylene sulfide, polyimide, polyetherimide, polyamide, polyamideimide, polyacrylonitrile, polycarbonate, polyacrylate, cellulose acetate, polypropylene, poly(4-methyl-1-pentene), polyvinylidene fluoride, polytetrafluoroethylene, polyhexafluoropropylene, and polychlorotrifluoroethylene membranes, and their derivatives.

[0067] The porous support preferably has an average thickness of 10 to 800 μm, more preferably 15 to 300 μm, especially 20 to 150 μm, and even more especially 30 to 130 μm, for example about 60 μm or about 100 μm.

[0068] The porous support preferably has a porosity of 30 to 95%, more preferably 55 to 75%, in which case (in the final membrane) the pores are filled with the anion exchange polymer obtained by curing the composition, i.e. the membrane preferably comprises 25 to 45 vol.% porous (unfilled) support material and 75 to 60 vol.% anion exchange polymer material (i.e. the cured composition according to the first aspect of the invention). The free volume of the porous support is determined by the thickness (m) and weight (g / m 2 ) and fiber density (g / m 3 ) data can be calculated.

[0069] The porosity of the support, before deposition, can be determined by a porometer, for example a Porolux™ 1000 from IB-FT GmbH, Germany.

[0070] If present, the porous support may be treated to modify its surface energy, for example to a value greater than 45 mN / m, preferably greater than 55 mN / m. Suitable treatments include corona discharge treatment, plasma glow discharge treatment, flame treatment, ultraviolet light irradiation treatment, chemical treatment, etc., for the purposes of improving the wettability of the porous support and the adhesion of the porous support to the anion exchange membrane.

[0071] Commercially available porous supports are available from a variety of sources, such as Freudenberg Filtration Technologies (Novatexx materials), Lydall Performance Materials, Celgard LLC, APorous Inc., SWM (Conwed Plastics, DelStar Technologies), Teijin, Hirose, Mitsubishi Paper Mills Ltd, and Sefar AG.

[0072] Preferably, the porous support is a porous polymeric support. Preferably, the porous support is a woven or nonwoven synthetic fabric or an extruded film that does not have covalently attached ionic groups.

[0073] Preferably, the anion exchange membrane of the present invention has an average thickness of 15 μm to 600 μm, more preferably 15 to 300 μm, particularly 20 μm to 200 μm, and more particularly 50 to 140 μm.

[0074] According to a second aspect of the present invention, there is provided a process for preparing an anion exchange membrane, the process comprising curing a curable composition as defined (and preferably as defined) in relation to the first aspect of the present invention.

[0075] The process according to the second aspect of the present invention preferably comprises: i. providing a porous support; ii. impregnating a porous support with a curable composition; and iii. Curing the curable composition and the curable composition is as defined above.

[0076] The curable composition can be cured by any suitable process, examples of which include thermal curing, photocuring, electron beam (EB) irradiation, gamma irradiation, and combinations of the foregoing.

[0077] Preferably, the process according to the second aspect of the present invention comprises a first curing step and a second curing step (dual curing). Dual curing is preferred because it increases the crosslink density of the resulting anion exchange membrane, which in turn improves the permselectivity.

[0078] In a preferred embodiment of the process according to the second aspect of the present invention, the curable composition is first cured by photocuring, for example by irradiating the curable composition with ultraviolet (UV) or visible light, or by gamma or electron beam radiation, thereby polymerizing the curable components present in the curable composition, and then by applying a second curing step. The second curing step preferably involves thermal curing, gamma irradiation, or EB irradiation of the product of the first curing step, and therefore preferably applies a different curing technique than the first curing step. If gamma or electron beam irradiation is used in the first curing step, a dose of 60 to 200 kGy, more preferably 80 to 150 kGy, is applied to the curable composition.

[0079] In one embodiment, the process according to the second aspect of the present invention comprises curing a curable composition to form an anion exchange membrane in a first curing step, winding the anion exchange membrane onto a core (optionally with an inert polymer foil), and then carrying out a second curing step on the wound product of the first curing step.

[0080] In a preferred embodiment, the first and second curing steps are each selected from: (i) UV curing (first curing step) followed by thermal curing (second curing step); (ii) UV curing followed by electron beam curing; and (iii) electron beam curing followed by thermal curing.

[0081] Component (d) may contain only one radical initiator or more than one radical initiator, for example a mixture of several photoinitiators (e.g., for a single cure) or a mixture of a photoinitiator and a thermal initiator (e.g., for a dual cure).

[0082] In one embodiment, the second curing step is carried out using gamma or electron beam (EB) irradiation. For the second curing step by gamma or EB irradiation, preferably a dose of 60 to 200 kGy is applied to the product of the first curing step, more preferably a dose of 80 to 150 kGy.

[0083] For the optional second curing step, heat curing is preferred. Heat curing is preferably carried out at a temperature of 50-100°C, more preferably 60-90°C. Heat curing is preferably carried out for 2-72 hours, e.g., about 3 hours for sheets, and 8-16 hours, e.g., about 10 hours for small rolls, and 24-72 hours for large rolls. Optionally, after the first curing step, a polymer foil is applied to the product of the first curing step before winding it onto a spool (this reduces oxygen inhibition, drying, and / or stacking of the product of the first curing step onto itself).

[0084] In a preferred process according to the second aspect of the present invention, the curable composition is continuously applied to a moving (preferably porous) substrate, preferably by a manufacturing unit comprising a curable composition application station, one or more irradiation sources for curing the curable composition, a film collection station, and means for moving the substrate from the curable composition application station to the irradiation sources and further to the film collection station.

[0085] The curable composition application station may be located at an upstream position relative to the irradiation source, which is located at an upstream position relative to the film collection station. Examples of coating techniques suitable for applying the curable composition to a substrate include slot die coating, slide coating, air knife coating, roller coating, screen printing, and immersion. Depending on the technique used and the desired final specifications, it may be desirable to remove excess coating from the substrate, for example, by roll-to-roll squeeze, roll-to-blade or blade-to-roll squeeze, blade-to-blade squeeze, or removal using a coating bar. Photocuring is preferably performed for the first curing step, preferably at 40 to 20,000 mJ / cm. 2 The irradiation is typically done at a wavelength of 300 nm to 800 nm, using a dose of 1000 ppm. In some cases, additional drying may be required, in which case temperatures of 40° C. to 200° C. may be employed. If gamma or EB curing is used, irradiation may be done under low-oxygen conditions, e.g., less than 200 ppm oxygen.

[0086] According to a third aspect of the present invention there is provided the use (method of use) of an anion exchange membrane according to the first aspect of the present invention for use in an electromembrane process, for example for the treatment of polar liquids (e.g. desalination), the production of acids and bases, or the generation or storage of electricity.

[0087] According to a fourth aspect of the present invention there is provided an electrodialysis or electrodialysis reversal device, a bipolar electrodialysis device, an electrodeionization module, a flow-through capacitor, a diffusion dialysis apparatus, a membrane distillation module, an electrolyzer, a redox flow battery, an acid-base flow battery or a fuel cell comprising one or more anion exchange membranes according to the first aspect of the present invention. [Example]

[0088] The invention will now be illustrated by the following non-limiting examples in which all parts and percentages are by weight unless otherwise specified.

[0089] Water absorption (WU) Water absorption (WU) was determined as follows: The membrane sample (at least 44 cm 2 The membranes (having a size of 1 / 4" x 1 / 4") were equilibrated in deionized water at room temperature for 24 hours and gently dried with a tissue to remove any hanging water droplets. Each sample was placed in a dry, open container, and the container containing the sample was dried at 80°C for 24 hours. After 24 hours, the container lid was closed and the container was allowed to cool to room temperature. The container containing the sample was weighed again, and the water absorption was calculated using equation (A). The weight of the membrane was determined by subtracting the weight of the empty container from the weight of the container containing the membrane sample. Water absorption (%) = (weight of wet film / weight of dry film × 100) - 100 Formula (A)

[0090] Permselectivity (PS) The permselectivity (PS) (%) (i.e., the selectivity of an anion exchange membrane for the passage of ions of opposite charge) was measured as follows: The anion exchange membrane to be tested was placed in a two-compartment system: one compartment was filled with a 0.05 M solution of HCl and the other compartment was filled with a 4 M solution of HCl, the two compartments being separated by the membrane under test.

[0091] setting: The capillary, as well as the Ag / AgCl reference electrode (Metrohm type 6.0750.100), contained 3 M KCl; Effective membrane area is 9.62cm 2 was; · The distance between the capillaries was approximately 15 mm; · The measured temperature was 21.0±0.2℃; Cole Parmer Masterflex console drives (77521-47) with easy load II model 77200-62 gear pumps were used in two compartments; The flow rate was controlled at a constant 500 ml / min using a Porter Instrument flow meter (type 150AV-B250-4RVS) and a Cole-Parmer flow meter (type G-30217-90); Prior to the measurement, the anion exchange membrane samples were equilibrated in 0.25 M HCl solution for 1 hour. After 20 minutes, the voltage was read from a standard VOM (multimeter).

[0092] The PS was calculated from the voltage readings using the Nernst equation. Preferably, the PS for HCl was at least 50%, more preferably at least 60%.

[0093] Ion Exchange Capacity (IEC) Prior to measurement, the membranes were converted to the chloride form by soaking the samples in 2 M NaCl solution for 1 hour. The 2 M NaCl solution was replaced once, and the samples were allowed to equilibrate for an additional 24 hours. The membrane samples were then rinsed with Milli-Q water, soaked in fresh Milli-Q water for 1 hour, and rinsed again with Milli-Q water.

[0094] A 2.0 cm diameter sample was punched out from the membrane sample with chloride counterion (12.57 cm 2 ), dried at 40°C for 24 hours, and weighed. The samples were then placed in 75 ml of Milli-Q® water for 24 hours to remove all non-counterions, followed by rinsing with Milli-Q® water. Each sample was then immersed in 10.00 ml of 0.1 M AgNO3 solution, and the solution was shaken with the sample for 24 hours. During shaking, AgCl salt precipitated, resulting in AgNO3. + - ions are Cl - As the -ions are removed, Cl - Ions are NO3 -The AgNO3 solution was completely exchanged with the ions. The samples were then removed from the AgNO3 solution and rinsed with a small amount of Milli-Q® water. The rinse water for each sample and the corresponding AgNO3 solution remaining after shaking the membrane sample were combined and titrated with a calibrated 0.1 M KBr solution, and the results were compared to the titration value of 10.00 ml of a blank solution of 0.1 M AgNO3 containing no membrane sample. The difference in titration results between the blank solution and each sample's test solution was correlated to the ion exchange capacity of the corresponding membrane using equation (I): IEC(meq / g dry membrane)=(YX)×0.1 / W Equation (I) where Y is the amount (in ml) of 0.1 M KBr used in the titration of the blank AgNO3 solution; X is the amount (in ml) of 0.1 M KBr used in titrating the AgNO3 solution in which the membrane sample was immersed, combined with the Milli-Q® water used to rinse the membrane sample after immersion in the AgNO3 solution; W is the dry weight of the membrane (in grams).

[0095] Porosity of the porous support The porosity of the porous support was calculated based on the thickness (m) and weight (g / m) provided by the supplier. 2 ) and fiber density (g / m 3 ) calculated from the data.

[0096] Electrical Resistivity (ER) ER (ohm cm) of the anion exchange membranes prepared in the examples 2 ) was measured by the method described by Dlugolecki et al., J. of Membrane Science 319 (2008) pp. 217-218, with the following modifications: The auxiliary membranes were CMX and AMX from Astom Co., Ltd., Japan; · The capillary, as well as the Ag / AgCl reference electrode (Metrohm type 6.0750.100) contained 3 M KCl; · The calibration liquid and the liquid in compartments 2, 3, 4 and 5 were 2.0 M NaCl solutions at 25°C; Effective membrane area is 9.62cm 2 was; · The distance between the capillaries was 5.0 mm; The measurement temperature was 25°C; · Cole-Parmer Masterflex console drives (77521-47) with Easyload II model 77200-62 gear pumps were used in all compartments; · The flow rate of each stream was 475 ml / min and was controlled by a Porter Instrument flow meter (type 150AV-B250-4RVS) and a Cole-Parmer flow meter (type G-30217-90); Prior to the measurements, the anion exchange membrane samples were equilibrated in a 0.5 M solution of NaCl at room temperature for at least 1 h.

[0097] The ER is preferably low, e.g., 15 ohm cm 2 less than, more preferably 10 ohm cm 2 is less than.

[0098] Determination of the distance between nitrogen atoms bearing cationic charges in component (b) The distance between the nitrogen atoms bearing the cationic charge in each component (b) was determined by simulation using the open-source Avogadro software version 1.2.0 (Marcus D Hanwell, Donald E Curtis, David C Lonie, Tim Vandermeersch, Eva Zurek, and Geoffrey R Hutchison; see "Avogadro: An advanced semantic chemical editor, visualization, and analysis platform," Journal of Cheminformatics 2012, 4:17). The structure of each component (b) was drawn in the software, and the optimal chemical structure was determined using an automatic optimization tool. The automatic optimization tool was run with the following settings: - Force Field: UFF - Steps per update: 4 - Algorithm: Molecular Dynamics (300K) - Atoms were neither fixed nor ignored.

[0099] Once the automatic optimization tool was finished (dE=0), the distance between the nitrogen atoms bearing the cationic charge was determined using the "click to measure" tool.

[0100] [Table 1]

[0101] General procedure for preparing AXL-1, 3, 4

[0102] [ka]

[0103] To a 40% solution (1 mmol) of the corresponding amine in PW containing 4-OH-TEMPO (0.1 g) was added dropwise CMS-14 (2.02 mmol) over 1 h. The mixture was then vigorously stirred for 2 h. Diethyl ether was added and the aqueous phase was extracted three times (3 x 200 mL). The product was isolated as a pale yellow solid from water by spray drying.

[0104] [Table 2]

[0105] General procedure for preparing AXL-9

[0106] [ka]

[0107] 5-Ethenyl-2,3-dihydro-1H-isoindole (1 mmol) was dissolved in chloroform (140 ml, 10 wt%) along with 4-OH-TEMPO (0.01 mmol). Potassium carbonate (2 mmol) was suspended in the mixture, and iodomethane (1.05 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour. Water was added to the reaction, and the organic layer was separated and then washed with saturated ammonium chloride (2 x 150 ml). The organic layer was placed in a reflux flask, and 1 mmol of CMS-14 was added dropwise. The mixture was gently warmed to 40 °C and stirred overnight. Upon completion, the product was filtered off and washed three times with diethyl ether. AXL-9 was obtained as a pale yellow solid in 65% yield.

[0108] General procedure for preparing AXL2-1 to 2-4

[0109] [ka]

[0110] To a 50% solution of the corresponding diamine (1 mmol) containing 4-OH-TEMPO (0.1 g) in ethyl acetate, CMS-14 (2.02 mmol) was added dropwise over 1 hour. The mixture was then vigorously stirred for 2 hours. The resulting precipitate was filtered, rinsed with additional ethyl acetate, and dried. The diammonium salt was isolated as a white solid. Table 3 below shows the structures of the crosslinkers prepared in this manner and their yields.

[0111] [Table 3]

[0112] Preparation of Examples 1 to 11 and Comparative Examples 1 to 4 The compositions shown in Table 4 below were prepared by sequentially mixing the stated amounts of solids (in wt%) into a mixture of water and n-propanol at a temperature of 40° C. Each of the compositions listed in Table 4 was applied to a porous support PS1 (26 g / m2 with a thickness of 80 μm and a porosity of 67.5%) using a 100 μm Mayer bar.2 Anion exchange membranes according to the first aspect of the present invention and comparative examples were prepared by applying a composition onto a PP / PE porous support (of which the composition is a PP / PE porous support) at room temperature (21°C), removing the excess using a 4 µm Meyer bar, and then curing the composition. UV curing was carried out by placing a sample of the support containing the composition on a conveyor equipped with a D bulb in a Light Hammer® 10 from Fusion UV Systems Inc. at 5 m / min and exposing the sample to UV light emitted from the D bulb at 50% power.

[0113] The UV-cured samples were covered with 60 μm polyethylene terephthalate (PET) foil (from Toray Industries, Inc.) without any surface treatment and placed in a metallized bag. The bag was evacuated and sealed. The bag containing the film was placed in a conventional oven, and the film was heat-cured at 90°C for 3 hours.

[0114] [Table 4]

[0115] [Table 5]

[0116] [Table 6]

Claims

1. An anion exchange membrane obtainable by curing a curable composition, the curable composition comprising: (a) component (a) of formula (I); and AR １ -(CH ２ ) ｎ -N ＋ (R ａ R ｂ )-(CH ２ ) ｎ -AR ２ 、X － Formula (I) (b) component (b) of formula (II); AR ３ -(CH ２ ) ｎ -N ＋ (R ｃ R ｄ )-L-N ＋ (R ｅ R ｆ )-(CH ２ ) ｎ -AR ４ 、2X － Formula (II) wherein each n independently has a value of 1 or 2; L is a non-aromatic linking group; each X － are independently anions; AR １ , A.R. ２ , A.R. ３ and A.R. ４ each independently comprises an aromatic group; (i) R ａ , R ｂ , R ｃ , R ｄ , R ｅ and R ｆ each independently represents an optionally substituted C １～３ alkyl group, optionally substituted C ２～３ is an alkenyl group or a vinylbenzyl group; or (ii) R ａ and R ｂ together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; or (iii) R ａ and R ｂ one of which is optionally substituted C １～３ alkyl group, optionally substituted C ２～３ alkenyl group or vinylbenzyl group, R ａ and R ｂ The other is of the formula AR １ - (CH ２ ) ｎ -N ＋ together with the group (iv) R ａ is the formula AR １ - (CH ２ ) ｎ -N ＋ together with the group R ｂ is the formula N ＋ - (CH ２ ) ｎ -AR ２ together with the group: (v) R ｃ and R ｄ together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring, and R ｅ and R ｆ each independently represents an optionally substituted C １～３ alkyl group, optionally substituted C ２～３ is an alkenyl group or a vinylbenzyl group; or (vi) R ｃ and R ｄ together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring, and R ｅ and R ｆ together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; or (vii) R ｃ and R ｄ one of which is optionally substituted C １～３ alkyl group, optionally substituted C ２～３ alkenyl group or vinylbenzyl group, R ｃ and R ｄ The other is of the formula AR ３ - (CH ２ ) ｎ -N ＋ together with the group R ｅ and R ｆ each independently represents an optionally substituted C １～３ alkyl group, optionally substituted C ２～３ is an alkenyl group or a vinylbenzyl group; or (viii) R ｃ and R ｄ one of which is optionally substituted C １～３ alkyl group, optionally substituted C ２～３ alkenyl group or vinylbenzyl group, R ｃ and R ｄ The other is of the formula AR ３ - (CH ２ ) ｎ -N ＋ together with the group R ｅ and R ｆ together with the positively charged nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; or (ix) R ｃ and R ｄ and R ｅ and R ｆ one of which is optionally substituted C １～３ alkyl group, optionally substituted C ２～３ alkenyl group or vinylbenzyl group, R ｃ and R ｄ The other is of the formula AR ３ - (CH ２ ) ｎ -N ＋ together with the group R ｅ and R ｆ The other is a compound of formula N ＋ - (CH ２ ) ｎ -AR ４ together with the group (x)R ｃ and R ｄ one of which is optionally substituted C １～３ alkyl group, optionally substituted C ２～３ alkenyl group or vinylbenzyl group, R ｃ and R ｄ is connected to L to form an optionally substituted ring, and R ｅ and R ｆ each independently represents an optionally substituted C １～３ alkyl group, optionally substituted C ２～３ an alkenyl group or a vinylbenzyl group; The anion exchange membrane, wherein component (a) of formula (I) and component (b) of formula (II) each contain at least two curable ethylenically unsaturated groups.

2. 2. The anion exchange membrane according to claim 1, wherein the water absorption is 11 to 16.5%.

3. 3. The anion exchange membrane according to claim 1, wherein the ion exchange capacity of the ion exchange membrane is 0.7 to 1.0 meq / g dry membrane.

4. 4. The anion exchange membrane according to claim 1, wherein the product of the water absorption value and the ion exchange capacity value is 8.5 to 15.5, the water absorption being expressed as a percentage (%), and the ion exchange capacity being expressed in meq / g of dry membrane.

5. The anion exchange membrane according to any one of claims 1 to 4, further comprising a porous support.

6. The anion exchange membrane according to any one of claims 1 to 5, wherein n has a value of 1 in formula (I) and formula (II).

7. AR １ , A.R. ２ , A.R. ３ and A.R. ４ The anion exchange membrane according to any one of claims 1 to 6, wherein each of

8. The anion exchange membrane according to any one of claims 1 to 7, wherein the curable ethylenically unsaturated group is a vinyl group.

9. The anion exchange membrane according to any one of claims 1 to 8, wherein the molar fraction of component (a) to component (b) in the curable composition is at least 0.60 and not more than 0.

96.

10. The anion exchange membrane according to any one of claims 1 to 9, wherein the curable composition comprises 35 to 70 wt% of component (a) and 3 to 40 wt% of component (b).

11. 11. The anion exchange membrane according to claim 1, wherein the components (a) and (b) each have a molecular weight of less than 600 Daltons.

12. The anion exchange membrane according to any one of claims 1 to 11, wherein L is a non-aromatic linking group containing 2 to 7 carbon atoms and, optionally, one or more atoms selected from oxygen, nitrogen, and sulfur.

13. AR in formula (I) １ and A.R. ２ and AR in formula (II) ３ and A.R. ４ The anion exchange membrane according to any one of claims 1 to 12, wherein each independently comprises a phenyl group or a styrenyl group.

14. The anion exchange membrane according to any one of claims 1 to 13, wherein the curable composition further comprises a radical initiator.

15. The anion exchange membrane according to any one of claims 1 to 14, wherein the curable composition further comprises a monomer that does not contain a group having a cationic charge.

16. The anion exchange membrane according to any one of claims 1 to 15, wherein the curable composition further comprises a solvent.

17. 17. The anion exchange membrane according to any one of claims 1 to 16, comprising at least 1 ppm of component (a) and at least 1 ppm of component (b).

18. A process for preparing an anion exchange membrane, comprising curing a curable composition as defined in any one of claims 1 to 17.

19. (i) providing a curable composition as defined in any one of claims 1 to 17; (ii) applying the curable composition onto a porous support to impregnate the porous support with at least a portion of the curable composition; and (iii) curing the curable composition 20. The process of claim 18, comprising:

20. 18. An electrodialysis device, a bipolar electrodialysis device, an electrolyzer, a redox flow battery, an acid-base flow battery or a fuel cell comprising one or more anion exchange membranes according to any one of claims 1 to 17.

21. Use of an anion exchange membrane according to any one of claims 1 to 17 for the treatment of polar liquids, for the production of acids and bases, or for the generation or storage of electricity.

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