# US 9,873,116 B2 · Ion exchange membrane, method for manufacturing same, module, and device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,873,116 B2 - Document ID: US9873116B2 - Status: Granted - Kind: B2 - Application number: 15/413,432 - Filed: 2017-01-24 - Published: 2017-05-11 - Granted: 2018-01-23 - Earliest claimed: 2014-08-14 - Assignees: FUJIFILM Corporation - Applicants: Fujifilm Corporation - Inventors: Kuniyuki Kaminaga; Kazuomi Inoue - Web page: https://patentgrep.com/patent/US9873116B2 ## CPC - B01J 41/14: obtained by reactions only involving unsaturated carbon-to-carbon bonds - B01J 41/07: in the weakly basic form - B01J 47/12: characterised by the use of ion-exchange material in the form of ribbons, filaments, fibres or sheets, e.g. membranes (electrodialysis or electro-osmosis B01D61/42) - C08F 8/32: by reaction with amines - C08F 12/18: Chlorine - C08F 212/18: {Chlorine} - C08J 5/22: Films, membranes or diaphragms - C08J 5/2243: {obtained by introduction of active groups capable of ion-exchange into compounds of the type C08J5/2231} - C08J 2325/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen - C08J 2453/02: of vinyl aromatic monomers and conjugated dienes - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) ## Abstract An ion exchange membrane of the present invention contains a resin having an amino group and a constitutional unit represented by Formula 1, in which the number of amino groups per dry mass is 0.15 to 2.4 mmol/g. In Formula 1, L1 represents an alkylene group or an alkenylene group, Ra, Rb, Rc, and Rd each independently represent an alkyl group or an aryl group, Ra and Rb and/or Rc and Rd may form a ring by being bonded to each other, n1 and n2 each independently represent an integer of 1 to 10, and X1− and X2− each independently represent an organic or inorganic anion. ## Claims ### Claim 1 An ion exchange membrane comprising: a resin having an amino group and a constitutional unit represented by Formula 1, wherein the number of amino groups per dry mass is 0.15 to 2.4 mmol/g, in Formula 1, L1 represents an alkylene group or an alkenylene group, Ra, Rb, Rc, and Rd each independently represent an alkyl group or an aryl group, Ra and Rb and/or Rc and Rd may form a ring by being bonded to each other, n1 and n2 each independently represent an integer of 1 to 10, and X1− and X2− each independently represent an organic or inorganic anion. ### Claim 2 (depends on 1) The ion exchange membrane according to claim 1, wherein the resin has, as a structure having the amino group, a constitutional unit represented by the following Formula 2 in at least a portion of the resin, in Formula 2, L2 represents an alkylene group or an alkenylene group, Re, Rf, Rg, and Rh each independently represent an alkyl group or an aryl group, Re and Rf and/or Rg and Rh may form a ring by being bonded to each other, n3 represents an integer of 1 to 10, and X3− represents an organic or inorganic anion. ### Claim 3 (depends on 1) The ion exchange membrane according to claim 1, wherein Ra and Rb and/or Rc and Rd form a ring by being bonded to each other. ### Claim 4 (depends on 2) The ion exchange membrane according to claim 2, wherein Re and Rf and/or Rg and Rh form a ring by being bonded to each other. ### Claim 5 (depends on 1) The ion exchange membrane according to claim 1, wherein X1− and X2− each independently are a halide ion. ### Claim 6 (depends on 1) The ion exchange membrane according to claim 1, wherein the resin further has a cross-linked structure in addition to the constitutional unit represented by Formula 1. ### Claim 7 (depends on 6) The ion exchange membrane according to claim 6, wherein a content of the cross-linked structure other than the constitutional unit represented by Formula 1 is 0.05 to 0.5 mmol/g with respect to a total mass of the resin. ### Claim 8 (depends on 1) A method for manufacturing the ion exchange membrane according to claim 1, comprising: a membrane preparation step of preparing a membrane containing a resin having a constitutional unit represented by Formula 3; and a reaction step of reacting the membrane with an amine compound represented by Formula 4, in Formulae 3 and 4, n4 represents an integer of 1 to 10, X represents a leaving group, L3 represents an alkylene group or an alkenylene group, Ri, Rj, Rk, and Rm each independently represent an alkyl group or an aryl group, and Ri and Rj and/or Rk and Rm may form a ring by being bonded to each other. ### Claim 9 (depends on 8) The method for manufacturing the ion exchange membrane according to claim 8, wherein in the membrane preparation step, the resin having a constitutional unit represented by Formula 3 is formed by polymerizing a composition containing a compound represented by Formula 5 and a polymerization initiator, in Formula 5, n4 represents an integer of 1 to 10, and X represents a leaving group. ### Claim 10 (depends on 9) The method for manufacturing the ion exchange membrane according to claim 9, wherein the compound represented by Formula 5 is a liquid at 25° C. ### Claim 11 (depends on 9) The method for manufacturing the ion exchange membrane according to claim 9, wherein a content of the compound represented by Formula 5 in the composition is equal to or greater than 50% by weight. ### Claim 12 (depends on 9) The method for manufacturing the ion exchange membrane according to claim 9, wherein the composition does not contain an organic solvent, or a content of an organic solvent in the composition is greater than 0% by mass and equal to or less than 1% by mass. ### Claim 13 (depends on 8) The method for manufacturing the ion exchange membrane according to claim 8, wherein X is a halogen atom. ### Claim 14 (depends on 8) The method for manufacturing the ion exchange membrane according to claim 8, wherein in the reaction step, both of the constitutional unit represented by Formula 1 and the constitutional unit represented by Formula 2 are formed in the resin. ### Claim 15 (depends on 1) A module comprising: the ion exchange membrane according to claim 1. ### Claim 16 (depends on 1) A device comprising: the ion exchange membrane according to claim 1.