Polyarylene polymer

Abstract

A polyarylene polymer containing sulfonic acid ester functional groups in powder form can be obtained, and this can be converted into a polyarylene polymer containing sulfonic acid functional groups by a heat treatment process.

Claims

1. A polyarylene polymer, the repeating unit of which is - Repeating unit of equation (1): 【Chemistry 1】 (In the formula, R １ (These are C1-C20 alkoxy groups); - Repeating unit of equation (2): 【Chemistry 2】 (In the formula, R ２ (wherein is -C(O)Ar, and Ar is a C6-C20 aryl group which may be substituted with at least one selected from the group consisting of a fluorine atom, a cyano group, a C1-C20 alkoxy group and a C6-C20 aryloxy group); and -Optionally, the repeating unit of equation (3): 【Transformation 3】 (In the formula, A is either H or CN.) It consists of, A polyarylene polymer characterized by being in powder form.

2. The polyarylene polymer according to claim 1, wherein the powder is an aggregate of solid particles having an average particle size in the range of 50 microns to 20 mm.

3. The polyarylene polymer according to claim 1 or 2, wherein the amount of repeating units of formula (1) is 0.1 to 90.0 mol%, 5.0 to 70.0 mol%, 10.0 to 65.0 mol%, and further 25.0 to 60.0 mol%, and 35.0 to 65.0 mol%, relative to the total amount of repeating units in the polyarylene polymer.

4. A polyarylene polymer according to any one of claims 1 to 3, comprising 20.0 to 65.0 mol% of repeating units of formula (1), 10.0 to 80.0 mol% of repeating units of formula (2), and 1.0 to 50.0 mol% of repeating units of formula (3).

5. R １ The polyarylene polymer according to any one of claims 1 to 4, wherein is 2,2-dimethylpropoxy.

6. The polyarylene polymer according to any one of claims 1 to 5, wherein in formula (2), Ar is phenyl.

7. An article comprising the polyarylene polymer according to any one of claims 1 to 6.

8. The article according to claim 7, which is a film.

9. A process for converting sulfonic acid ester groups in a polyarylene polymer according to any one of claims 1 to 6 to sulfonic acid groups, A process comprising heating the polyarylene polymer to a temperature of 100°C to 200°C.

10. The process according to claim 9, wherein the polyarylene polymer powder is dissolved in a solvent and subjected to a heat treatment step at a temperature of 100 to 160°C, preferably 130 to 160°C.

11. A process for producing a film containing a polyarylene polymer, wherein the repeating unit is the repeating unit of formula (4): 【Chemistry 4】 It essentially consists of repeating units of formula (2) and optionally repeating units of formula (3), wherein the repeating units of formulas (2) and (3) are as described in any one of claims 1 to 6; The process is a step of dissolving the polyarylene polymer according to any one of claims 1 to 6 in an organic solvent to obtain a solution; and i) A step of heating the solution to a temperature of 100 to 200°C to convert the sulfonic acid ester groups to sulfonic acid groups, casting the solution to form a film, and drying it; or ii) A process comprising the steps of casting the solution to form a film, heating the cast film to a temperature of 100 to 200°C to convert sulfonic acid ester groups to sulfonic acid groups, and optionally drying the film.

12. A process for producing a film containing a polyarylene polymer, wherein the repeating units essentially consist of repeating units of formula (4), repeating units of formula (2), and optionally repeating units of formula (3), wherein the repeating units of formula (2) and (3) are as described in any one of claims 1 to 6; 【Transformation 5】 A process comprising the step of heating the film according to claim 8 to a temperature of 100 to 200°C to convert sulfonic acid ester groups to sulfonic acid groups.

13. A process for producing a film containing a polyarylene polymer, wherein the repeating units essentially consist of repeating units of formula (4), repeating units of formula (2), and optionally repeating units of formula (3), wherein the repeating units of formula (2) and (3) are as described in any one of claims 1 to 6; 【Transformation 6】 A process comprising the steps of providing a solution of a polyarylene polymer according to any one of claims 1 to 6 in a solvent, heating the solution at a temperature of 100 to 200°C to convert sulfonic acid ester groups to sulfonic acid groups, recovering the polymer containing sulfonic acid groups, forming a solution in a polar organic solvent, and casting and drying the solution.

14. The process according to any one of claims 10, 11, or 13, wherein the solvent is selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, or N-methyl-2-pyrrolidone.

15. The process according to any one of claims 9 to 14, wherein the step of heating the polyarylene polymer is performed for 0.1 to 20.0 hours, preferably 1.0 to 15.0 hours, and more preferably 1.0 to 10.0 hours.

16. A film containing a polyarylene polymer, wherein the repeating unit is of formula (4), 【Transformation 7】 A film comprising essentially repeating units of formula (2) and optionally repeating units of formula (3), wherein the repeating units of formula (2) and (3) are as described in any one of claims 1 to 6, and the polymer has an ion exchange capacity of 2.43 to 4.00 meq / g.

17. An electrochemical device, a filtration device, or a gas separation device comprising the film described in claim 16.

18. Use of the film according to claim 16 as a polymer electrolyte membrane in an electrochemical device, or as a membrane in a microfiltration, ultrafiltration, or reverse osmosis device, or a gas separation device.

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