Ion-conducting membrane

Abstract

An anionic polymer conductive membrane, vinylbenzyl-R s Vinyl benzyl-R x and styrene. In some examples, R s is tetramethylimidazolium, and R s It is a positively charged amine. In some examples, vinylbenzyl-R s The total weight of the substrate is greater than 20% of the total weight of the membrane.

Description

Cross-reference of related applications

[0001] This application relates to and claims priority from U.S. Patent Application No. 18 / 453,011, filed on 21 August 2023, the title of which is “Ion Conducting Membrane”. The entire text of Application '011 is incorporated herein by reference. [Technical Field]

[0002] The field of this invention is electrochemistry. These devices, systems, compositions, and membranes can be used in fields such as the electrolysis of water and carbon dioxide, power generation by batteries and fuel cells, water purification, and carbon dioxide capture systems. [Background technology]

[0003] Chemical conversion processes using electrochemical cells have been known for many years. Typically, an electrochemical cell comprises an anode, a cathode, and an electrolyte. A catalyst can be placed in the anode, cathode, and / or electrolyte to facilitate the desired chemical reaction. During the operation, reactants or a solution containing reactants are supplied to the cell. The desired electrochemical reaction is then promoted by applying a voltage between the anode and the cathode. In the case of a water electrolysis device, hydrogen is generated on the cathode and oxygen on the anode.

[0004] Over the years, the use of a wide variety of ion-conducting membranes in these batteries has been explored. Some of these ion-conducting membranes are listed in the U.S. Patent Publication Nos. 9,012,345, 9,370,773, 9,464,359, 9,481,939, 9,580,824, 9,555,367, 9,815,021, 9,849,450, 9,943,841, 9,945,040, 9,957,624, 9,982,353, and 10,023,967. This is disclosed in Patent Nos. 10,047,446, 10,975,480, 10,147,974, 10,173,169, 10,396,329, 10,428,432, 10,724,142, 10,774,431 and U.S. Patent Application Nos. 15 / 922,883, 16 / 024,827, 16 / 552,952 and 16 / 429,868.

[0005] As disclosed in U.S. Patents 9,982,353 and 10,724,142, these membranes are particularly suitable for anion exchange membrane (AEM) water electrolysis devices. The membranes disclosed in Patents 9,982,353 and 10,724,142 were tested by passing a 1 M KOH solution through the anode and cathode.

[0006] In recent years, there has been growing interest in operating AEM water electrolysis systems using a "dry cathode" (where KOH solution is supplied to the anode but not to the cathode). Currently available membranes perform poorly in dry cathode configurations, which may be due to insufficient water transport. [Overview of the project] [Problems that the invention aims to solve]

[0007] The anion-conducting membrane disclosed herein has higher mechanical strength and improved water transport compared to the membranes disclosed in U.S. Patents 9,982,353 and 10,724,142. [Means for solving the problem]

[0008] In some preferred embodiments, the anion-conducting membrane comprises a polymer, the polymer being vinylbenzyl-R s Vinyl benzyl-R x and the reaction products of styrene, where, (a)R s It is a positively charged amine or phosphine, (b) Vinyl benzyl-R x The reaction product comprises benzyl-X and at least one of the following: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, and N-methyl-1-D-glucosamine, where X is a halogen. (c) Vinylbenzyl-R x and vinyl benzyl-Rs is a different chemical substance from (d) vinylbenzyl-R s the total weight of is at least 10% based on the weight of the polymer, and / or (e) vinylbenzyl-R x the total weight of is at least 1% based on the weight of the polymer.

[0009] In some preferred embodiments, the anion exchange membrane comprises a polymer, and the polymer comprises vinylbenzyl-R s , vinylbenzyl-R x and a reaction product of styrene, wherein (a) vinylbenzyl-R s comprises a reaction product of tetramethylimidazolium and benzyl chloride, (b) vinylbenzyl-R x comprises a reaction product of benzyl chloride and at least one compound selected from the group consisting of sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, and N-methyl-D-glucosamine, (c) vinylbenzyl-R s the total weight of is at least 20% based on the weight of the polymer, (d) vinylbenzyl-R x the total weight of is at least 10% based on the weight of the polymer, and / or (e) the total weight of styrene is at least 20% based on the weight of the polymer.

[0010] In some embodiments, the total weight of vinylbenzyl-R x is at least 20% based on the weight of the polymer.

[0011] In some embodiments, the step of preparing the anion exchange membrane comprises exposing the anion exchange membrane to sodium ethoxide.

[0012] In some embodiments, vinylbenzyl-R xIt contains the reaction product of benzyl chloride and N-methyl-D-glucosamine.

[0013] In some examples, the anion conductive membrane is vinylbenzyl-R s Vinyl benzyl-R x1 Vinyl benzyl-R x2 and the reaction products of styrene, further, (a) Vinylbenzyl-R x1 It contains a reaction product of benzyl chloride with at least one of the following compounds: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, and N-methyl-D-glucosamine. (b) Vinyl benzyl-R x1 It contains the reaction product of benzyl chloride and ethoxy-sodium, (c) The polymer is vinylbenzyl-R x1 Contains at least 1%, (d) The polymer is vinylbenzyl-R x2 Contains at least 10% of it.

[0014] In some examples, the molecular weight of the polymer is between 1,000 and 10,000,000 in atomic units (AU).

[0015] In some embodiments, the thickness of the anion conductive film is between 10 and 300 micrometers.

[0016] In some examples, the film has an area resistivity of 0.1 ohms / square centimeter or less at 60°C and in a 1M KOH solution.

[0017] In some embodiments, a battery, fuel cell, electrolyzer, water purification system, or CO2 recovery system may include an anion conductive membrane as described in this disclosure.

[0018] In some preferred embodiments, vinylbenzyl-R sThese are benzyl-X (where X is a halogen), 1,2,2,6,6-pentamethylpiperidine, 1,2,2,5,5-pentamethylpyrrolidine, tetramethylimidazole, triethylamine, tripropylamine, trimethylamine, N-methylpiperidine, 1-ethylpiperidine, piperidine, 1,4'-bipiperidine, 1-methylpyrrolidine, 2,2,6,6-tetramethylpiperidine, pyrrolidine, 1-pyrrolidineethylamine, 2,3,5-trimethylpyridine, 2,4,6-trimethylpyridine, 2,6- Dimethylpyridine, 2,4-dimethylpyridine, 2,3,5-trimethylpyridine, 4-methyl-2-(1-pyrrolyl)pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, pyridine, 4,4'-bipyridine, 2,2'-bipyridine, tributylamine, N,N-diisopropylethylamine, triphenylamine, N,N-dimethylcyclohexylamine, N,N-dicyclohexylmethylamine, triphenylphosphine, 1,2-dimethylindole, indole, 1-methylindole, Xamethylenetetramine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine, 2,3-dimethylpyrazine, 3-methylpyridazine, 2-methylpyrazine, 2,3-diethylpyrazine, ethylpyrazine, pyrazine, 1-methylimidazole, pyrimidine, 4-methylpyrimidine, pyridazine, triazole, 3,5-dimethyl-1,2,4-triazole, 1,2-dimethylimidazole, 2,4,5-triphenylimidazole, 1-decyl-2-methylimidazole, 1-(2-hydroxyethyl The reaction product includes a reaction product with at least one of the following: imidazole, guanidine, tetramethylguanidine, dipiperidine, dipyridine, ethylenediamine, propylenediamine, N,N,N'-trimethylethylenediamine, ethylenediaminetetraacetic acid, alkyldiamine, other diamines, ethanolamine, triethanolamine, methylethanolamine, dimethylethanolamine, propanolamine, 3-butenylmagnesium, isobutylmagnesium bromide, cyclohexylmagnesium chloride, and amino acids.

[0019] In some preferred embodiments, vinylbenzyl-R s This includes the reaction product of tetramethylimidazolium and benzyl-X, where X is a halogen.

[0020] In some preferred embodiments, the molecular weight of the polymer is 1,000 to 10,000,000 in atomic units (AU), preferably 10,000 to 1,000,000 AU, and most preferably 25,000 to 250,000 AU.

[0021] In some preferred embodiments, the polymer composition is in the form of a film. The thickness of the film is preferably 10 to 300 micrometers.

[0022] In some preferred embodiments, the film has an area resistivity of 0.1 ohms / square centimeter or less in a 1 M KOH solution at 60°C. [Brief explanation of the drawing]

[0023] [Figure 1] This is a nuclear magnetic resonance spectrum. [Figure 2] This is another nuclear magnetic resonance spectrum. [Modes for carrying out the invention]

[0024] It should be understood that the aforementioned process is not limited to the specific methods, embodiments, and reagents described herein, for a person familiar with the art relating to this specification will recognize that these may be modified. It should also be understood that the terms used herein are used solely for the purpose of describing specific examples and are not intended to limit the scope of the process. Furthermore, it should be noted that the singular forms “one,” “one type,” and “the aforementioned” as used herein and in the appended claims include multiple references unless the context clearly indicates otherwise. For example, “linker” as used refers to one or more linkers known to a person skilled in the art, and their equivalents. Similarly, the phrase “and / or” is used to indicate that one or two of the aforementioned situations may occur, for example, A and / or B includes (A and B) and (A or B).

[0025] Unless otherwise defined, the technical and scientific terms used herein have the same meanings as those commonly understood by those skilled in the art in which this process pertains. Examples of this process, as well as various features and advantageous details thereof, are shown in the non-limiting examples and / or drawings, and are described in detail below. Features shown in the drawings are not necessarily drawn to scale, and as those skilled in the art will recognize, features of one example can be used in combination with those of another example, even if not explicitly stated herein.

[0026] Any numerical range described herein includes all values ​​from the lowest to the highest, with a unit increment of 1, provided that there is at least a 2-unit interval between any lower and highest value. For example, when numerical values ​​for component concentrations or process variables (e.g., dimensions, angle magnitudes, pressure, time, etc.) are described, if the range is, for example, 1 to 98, specifically 20 to 80, and more specifically 30 to 70, then it is intended that values ​​such as 15 to 85, 22 to 68, 43 to 51, and 30 to 32 be explicitly listed herein. For numbers less than 1, 1 unit is considered to be 0.0001, 0.001, 0.01, or 0.1, depending on the context. These are merely examples illustrating a specific intent, and all possible combinations of numbers between the lower and upper limits shall be treated in a similar manner.

[0027] Furthermore, a "Definitions" section is provided immediately afterward to clearly define specific terms related to the process. While specific methods, apparatus, and materials are described, any methods and materials similar to or equivalent to those described herein may be used to carry out or test the process. definition

[0028] As used herein, the term "polymer electrolyte membrane" refers to a cation exchange membrane containing multiple polymers having typically covalently bonded negatively charged groups, as well as an anion exchange membrane containing multiple polymers having typically covalently bonded positively charged groups. Typical cation exchange membranes include proton conduction membranes, such as the perfluorosulfonic acid polymer sold under the trade name NAFION® by DuPont, headquartered in Wilmington, Delaware.

[0029] As used herein, the term "anion exchange membrane electrolytic device" refers to an electrolytic device having an anion-conducting polymer electrolyte membrane separating the anode and cathode.

[0030] As used herein, the term "EMIM" refers to the 1-ethyl-3-methylimidazole cation.

[0031] The term "CV" refers to cyclic voltammetry.

[0032] The term "Millipore water" refers to water produced by a Millipore® filtration system with a resistivity of at least 18.2 megaohms-centimeters.

[0033] As used herein, the term "imidazolium" refers to a positively charged ligand containing an imidazole group. This includes unsubstituted or substituted imidazoles. Specifically, it includes ligands in the following forms: [ka] (In the formula, R1-R5 are each independently selected from hydrogen, halides, linear alkyl groups, branched alkyl groups, cyclic alkyl groups, heteroalkyl groups, aryl groups, heteroaryl groups, alkylaryl groups, heteroalkylaryl groups, and polymers thereof, for example, vinylbenzyl copolymers as described herein are explicitly included.)

[0034] As used herein, the term "pyridine" refers to a positively charged ligand containing a pyridine group. This includes unsubstituted or substituted pyridines. Specifically, it includes ligands in the following forms: [ka] (R6-R in the formula 11 Each of these is independently selected from hydrogen, halides, linear alkyl groups, branched alkyl groups, cyclic alkyl groups, heteroalkyl groups, aryl groups, heteroaryl groups, alkylaryl groups, heteroalkylaryl groups, and polymers thereof, for example, vinylbenzyl copolymers as described herein are explicitly included.

[0035] As used herein, the term "phosphonium" refers to a positively charged ligand containing phosphorus, including substituted phosphorus. The ligand morphology is as follows: P + (R 12 R 13 R 14 R 15 ) (R in the formula 12 -R 15 Each of these is independently selected from hydrogen, halides, linear alkyl groups, branched alkyl groups, cyclic alkyl groups, heteroalkyl groups, aryl groups, heteroaryl groups, alkylaryl groups, heteroalkylaryl groups, and polymers thereof, for example, vinylbenzyl copolymers as described herein are explicitly included.

[0036] As used herein, the term “positively charged cyclic amine” refers to a positively charged ligand containing a cyclic amine. Specifically, this includes imidazolium, pyridinium, pyrazolium, pyrrolidinium, pyrrolium, pyrimidinium, piperidinium, indolium, triazinium, and polymers thereof, such as the vinylbenzyl copolymers described herein.

[0037] As used herein, the term "simple amine" refers to the following forms of substances: N(R 16 R 17 R 18 ) (R in the formula 16 , R 17 and R 18 Each of these is independently selected from hydrogen, linear alkyl groups, branched alkyl groups, cyclic alkyl groups, heteroalkyl groups, aryl groups, heteroaryl groups, alkylaryl groups, and heteroalkylaryl groups, but they are not polymers.

[0038] As used herein, the term "substituted ethylene" refers to monomers in the following forms: [ka] (In the formula, R1-R4 are each independently selected from hydrogen, a halide, a linear alkyl group, a branched alkyl group, a cyclic alkyl group, a heteroalkyl group, an aryl group, a heteroaryl group, an alkylaryl group, and a heteroalkylaryl group, and the polymer is included.)

[0039] As used herein, the term "TMIM" refers to tetramethylimidazole.

[0040] As used herein, the term "water purification system" refers to a device that removes unwanted components from water, and in the case of a membrane-based device, the device employs a membrane as a barrier to allow the passage of certain substances while blocking others.

[0041] As used herein, the term "battery" refers to a device that generates electrical energy through electrochemical reactions between substances stored inside the battery.

[0042] As used herein, the term "fuel cell" refers to a device that generates electrical energy through electrochemical reactions between substances supplied to the fuel cell from an external source.

[0043] As used herein, the term "electrolytic apparatus" refers to an electrochemical apparatus that uses electrical energy to convert substances into their constituent components. Taking a water electrolytic apparatus as an example, this apparatus uses electricity to convert water into hydrogen and oxygen.

[0044] As used herein, the term "CO2 recovery system" refers to a device capable of separating CO2 from a gaseous or liquid flow. Detailed description

[0045] The examples provided herein are for illustrative purposes only and do not constitute an exhaustive list of all possible embodiments, uses, or modifications relating to the electrochemical apparatus. Accordingly, various changes and modifications relating to the methods and systems of the present invention are obvious to those skilled in the art and do not depart from the scope of the invention. While the present invention is described with reference to specific embodiments, it should be understood that the invention for which protection is claimed should not be unduly limited to these specific embodiments. In practice, various modifications relating to embodiments of the present invention are obvious to those skilled in the chemical or related fields and are intended to be included within the scope of the appended claims.

[0046] Example 1: Preparation of alternative film The objective of Example 1 is to provide a variety of alternative membranes applicable to water and carbon dioxide electrolysis, batteries, fuel cell power generation, and water purification.

[0047] Typically, the film synthesis procedure in Example 1 is based on the procedure described in U.S. Patent No. 9,370,773, but with the addition of steps 5 and 6.

[0048] Step 1: Styrene (Sigma Aldrich, Saint Louis, MO) was washed twice with an equal volume of 7.5% aqueous sodium hydroxide solution to prepare inhibitor-free styrene. Then, to ensure neutralization, the inhibitor-free styrene was washed four times with an equal volume of water and then dried over anhydrous magnesium sulfate. The t-butylcatechol (TBC) inhibitor in vinyl benzyl chloride (VBC) was extracted and removed with a 0.5% potassium hydroxide solution until a colorless extract was obtained. The extract was washed with water until neutral and then dried over anhydrous magnesium sulfate.

[0049] Step 2: Next, the polymer (vinylbenzyl chloride-co-styrene) was synthesized. In a water-jacketed reactor at 60-65°C under a nitrogen atmosphere, a solution of inhibitor-free styrene (Sigma-Aldrich) (440 g) and vinylbenzyl chloride (Dupont) (360 g) was heated with 2 liters of chlorobenzene (Sigma-Aldrich) for 12-18 hours using AIBN (a,a'-azobisisobutyronitrile, Sigma-Aldrich) (8 g) as an initiator. The resulting copolymer was precipitated in ethanol and dried under vacuum.

[0050] Step 3: The copolymer sample obtained in Step 2 was dissolved in 1-methoxy-2-propanol (Sigma Aldrich) to form a solution with a polymer weight content of 27-32%.

[0051] Step 4: The solution from Step 3 was heated to 60°C, tetramethylimidazole was added, and the solution was stirred for 48 hours. Nuclear magnetic resonance (NMR) analysis showed that approximately 40% of the vinylbenzyl chloride (VBC) remained unreacted at this time. Figure 1 shows the NMR spectrum after Step 4.

[0052] Step 5: 5 mL of the solution from Step 4 was added to a series of 20 mL vials. One of the following amines was added to each vial: triethylamine, tripropylamine, ethanolamine, 3-(dimethylamino)-1-propylamine, hexylamine, 1-methylpiperidine, 1-piperidineethanol, 1-benzylimidazole, 4-(dimethylamino)pyridine, N-methyl-D-glucosamine, or decylamine (all purchased from Sigma Aldrich). The vials were heated to 45°C in a shaking water bath and maintained for 48 hours.

[0053] Step 6: A second set of vials, identical to those in Step 5, was prepared. The vials were cooled to room temperature, and 2.4 mL of 21% ethoxysodium (also known as sodium ethoxide) (C2H5ONa) (Sigma Aldrich) ethanol solution was added to each vial. An additional 2 mL of 21% ethoxysodium ethanol solution was added to the vials containing the solutions from Step 4. In each case, the vials were placed in a shaking water bath for 5-10 minutes. NMR analysis showed that the amount of unreacted VBC remaining at this time was less than 1%. Figure 2 shows the NMR spectrum after Step 5.

[0054] Step 7: We attempted to prepare films by directly casting each of the solutions prepared in Steps 5 and 6 onto a polyethylene terephthalate (PET) substrate. The thickness of the solution on the substrate was controlled using a squeegee-adjustable casting machine (MTI, Richmond, California). The films were then dried in a 60°C oven for 120–150 minutes. Each resulting film was immersed overnight in a 1 mole KOH solution and then washed with deionized water (DI water). At this point, the film thickness was between 40 and 100 micrometers.

[0055] Next, the water permeability of each membrane was measured using the following procedure.

[0056] Step 8: Each film is made of Dioxide Materials® 25cm 2 It was installed between the anode and cathode of the electrolytic device hardware, with a polyether ether ketone (PEEK) mesh as the support.

[0057] Step 9: 1 mole of KOH was circulated through the anode of the battery hardware while simultaneously supplying 1 L / min of dry nitrogen gas to the cathode. The electrolytic device hardware was heated to 60°C and then equilibrated.

[0058] Step 10: The gas discharged from the electrolyzer was introduced into a cold trap and cooled with dry ice for 20 minutes. The cold trap was then weighed, and the weight of the condensed water inside the trap was calculated as the difference between the initial weight of the flask and the weight when condensed water was attached. The results are shown in Table 1.

[0059] [Table 1]

[0060] The results in Table 1 demonstrate that a film with a water electrical conductivity 20% or more higher than the film prepared in Example 1 can be prepared. This provides sufficient additional permeability, making it possible to apply the film to a water electrolysis apparatus having a dry cathode. In all examples, the water electrical conductivity of the film was improved by adding ethoxysodium in step 6 compared to a similar film that did not undergo step 6.

[0061] The data in Table 1 yielded some surprising results. While the films in Examples 3, 5, 6, 7, and 8 were too soft to use, adding sodium ethoxide to the solution before casting resulted in films with sufficient strength.

[0062] When the solution in Step 6 was left overnight, it gelled. This suggests that the sodium ethoxide solution was not simply reacting with unreacted chlorine in the membrane. Conversely, the sodium ethoxide catalyzed membrane crosslinking in some way. Until now, there had been no known instances of sodium ethoxide or related compounds catalyzing membrane crosslinking.

[0063] Furthermore, we also tested membranes prepared using the procedures described in Li et al.'s "A Novel Polymerizable Imidazolium Salt-Based Anion Exchange Membrane for Alkaline Fuel Cell Applications," Journal of Materials Chemistry 21 (2011), pp. 11340-11346, and Lin et al.'s "Alkali-Stable C2-Substituted Imidazolium-Based Anion Exchange Membrane," Materials Chemistry 25 (2013), p. 1858. The polymers prepared using these procedures did not exhibit high mechanical strength.

[0064] Example 2: Changing the concentration The data in Example 1 were obtained under conditions where VBC accounted for 43-46% of the total weight of the copolymer prepared in Step 2. However, according to U.S. Patent No. 9,370,773, useful polymers can be prepared using copolymers containing 10, 20, 30, 40, 40, 60, 70, 80, or 90% (each ±5%) of VBC by weight. Similarly, the data in Example 1 were obtained when 58-62% of the VBC in the copolymer reacted with TMIM in Step 4. By changing the reaction time, 1, 5, 10, 20, 30, 40, 50, or 60% (each ±5%) of VBC can be used to react with TMIM in Step 4.

[0065] Furthermore, the results revealed that when dimethylformamide was used instead of 1-methoxy-2-propanol in step 3, at least 70%, at least 80%, at least 90%, or at least 95% (each value ±5%) of VBC could be reacted with TMIM. The resulting polymer may contain all or at least part styrene in the range of approximately 10, 20, 30, 40, 50, 60, 70, or 80% by weight, and vinylbenzyl-R in the range of approximately 10, 20, 30, 40, 50, 60, 70, 80, or 90% by weight. s Vinylbenzyl-R may contain all or at least a portion of it, and / or in the range of about 1, 5, 10, 20, 30, 40, 50, 60, 70% by weight. x It may contain all or at least a portion of it.

[0066] The above embodiments are illustrative and do not constitute a detailed list of all possible embodiments, uses, or modifications of the electrochemical apparatus. Therefore, various changes and modifications to the methods and systems according to the present invention will be obvious to those skilled in the art and will not depart from the scope and spirit of the invention. While the invention has been described in conjunction with specific embodiments, it should be understood that the invention for which protection is claimed should not be unduly limited to these specific embodiments. In practice, various changes to embodiments of the invention will be obvious to those skilled in the chemical or related fields and are intended to fall within the scope of the appended claims.

[0067] All disclosures of references and publications cited herein are incorporated herein by reference in the same manner as if each reference and publication were incorporated by reference individually.

[0068] Especially 9,012,345, 9,370,773, 9,464,359, 9,481,939, 9,580,824, 9,555,367, 9,815,021, 9,849,450, 9,943,841, 9,945,040, 9,957,624, 9,982,353, 10,023,967, 10,047,446, 10, The contents of patents 975,480, 10,147,974, 10,173,169, 10,396,329, 10,428,432, 10,724,142, and 10,774,431 and applications 15 / 922,883, 16 / 024,827, 16 / 552,952, and 16 / 429,868 are incorporated herein by reference in their entirety.

[0069] While specific elements, examples, and applications of the present invention have been shown and described, it should be understood that the present invention is not limited thereto. This is because those skilled in the art can make various modifications without departing from the scope of this disclosure, particularly in view of the teachings given above.

Claims

1. Vinylbenzyl-R ｓ Vinyl benzyl-R ｘ In an anion-conducting film containing a polymer including a reaction product of styrene, (a) The vinyl benzyl-R ｓ It contains the reaction product of tetramethylimidazolium and benzyl chloride. (b) The vinyl benzyl-R ｘ It contains a reaction product of benzyl chloride with at least one of the following compounds: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, and N-methyl-D-glucosamine. (c) The vinyl benzyl-R ｓ The total weight of the polymer is at least 20% of the weight of the polymer. (d) The vinyl benzyl-R ｘ The total weight of the polymer is at least 10% of the weight of the polymer, and (e) An anion-conducting membrane in which the total weight of the styrene is at least 20% of the weight of the polymer.

2. Vinylbenzyl-R ｘ The anion-conducting membrane according to claim 1, wherein the total weight of the polymer is at least 20% of the weight of the polymer.

3. The anion-conducting membrane according to claim 1, wherein the preparation step of the anion-conducting membrane includes exposing the anion-conducting membrane to sodium ethoxide.

4. Vinylbenzyl-R ｘ The anion-conducting membrane according to claim 1, comprising a reaction product of benzyl chloride and N-methyl-D-glucosamine.

5. The anion conductive membrane includes the vinylbenzyl-R ｓ , vinylbenzyl-R ｘ１ , vinylbenzyl-R Ｘ２ and a reaction product of the styrene, and further (a) The vinyl benzyl-R ｘ１ It contains a reaction product of benzyl chloride with at least one of the following compounds: sodium ethoxide, tripropylamine, triethylamine, benzimidazole, 1-piperidineethanol, dimethylaminopyridine, 1-methylpyrrolidine, methylpiperidine, and N-methyl-D-glucosamine. (b) The vinyl benzyl-R ｘ１ It contains the reaction product of benzyl chloride and ethoxy-sodium, (c) The polymer is the vinylbenzyl-R ｘ１ It contains at least 1% of and (d) The polymer is the vinylbenzyl-R ｘ２ The anion conductive film according to claim 1, comprising at least 10% of the above.

6. The anion-conducting membrane according to claim 1, wherein the molecular weight of the polymer is between 1,000 and 10,000,000 in atomic units (A.U.).

7. The anion conductive film according to claim 1, wherein the thickness of the anion conductive film is 10 to 300 micrometers.

8. The anion conductive membrane according to claim 1, wherein the anion conductive membrane has an area resistivity of 0.1 ohms / square centimeter or less in a 1 M KOH solution at 60°C.

9. A battery, fuel cell, electrolytic device, water purification system, or carbon dioxide recovery system comprising the anion conductive membrane described in claim 1.

10. Anion-conducting membrane.

11. Method for operating an anion-conducting membrane.

12. An electrolytic device containing an anion-conducting membrane.

13. A fuel cell containing an anion-conducting membrane.

14. A water purification system that includes an anion-conducting membrane.

15. A carbon dioxide capture system including an anion-conducting membrane.

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