IP Library Granted Patent US 9,127,108
Granted Patent B2
US 9,127,108 · App. 13/441,052 · Granted Sep 8, 2015

Method for making polymer, and associated polymer, membrane and electrode

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Quick Facts
Patent No.
US 9,127,108
App. No.
13/441,052
Granted
Sep 8, 2015
Kind
B2
Abstract

A method is provided, comprising: copolymerizing a monomer comprising at least two amide groups, a monomer of formula (a) and a sulfonic acid or salt monomer, wherein R 1 is CH 3 or H. A polymer made by the method, a membrane and an electrode comprising the polymer are provided.

Claims (30)

1. A method comprising: copolymerizing a monomer comprising at least two amide groups, a monomer of formula (a)

and a sulfonic acid or salt monomer, wherein R 1 is CH 3 or H, wherein the monomer comprising at least two amide groups is selected from carbonyldiamine and a compound of formula (c)

wherein R 3 is NH, aliphatic radical or ether unit.

2. The method of claim 1 , wherein the sulfonic acid or salt monomer is of formula (b):

wherein

R 2 is CH 3 or H; X is NH or O and Y is alkyl.

3. The method of claim 2 , wherein the sulfonic acid or salt monomer is 2-acrylamido-2-methylpropane sulfonic acid.

4. The method of claim 1 , wherein the sulfonic acid or salt monomer is 2-acrylamido-2-methylpropanesulfonic acid, styrene sulfonic acid, sulfoalkyl (meth)-acrylates, sulfoalkyl itaconates, with a C 1 to C 6 alkyl radical, or vinylsulfonic acid and ammonium, alkali metal or alkaline earth metal salts thereof.

5. The method of claim 1 , wherein the sulfonic acid or salt monomer is 2-acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, p-styrenesulfonic acid, sulfopropyl acrylate, sulfopropyl itaconate or vinylsulfonic acid and ammonium, sodium, potassium and calcium salts thereof.

6. The method of claim 1 , wherein the monomer of formula (a) is N-methylolacrylamide (N-(hydroxymethyl) acrylamide, NMA), N-methylolmethacrylamide (NMMA), N-(isobutoxymethyl)-acrylamide (IBMA), N-(isobutoxymethyl)-methacrylamide or N-(n-butoxymethyl)-acrylamide (NBMA).

7. The method of claim 1 , wherein the monomer comprising at least two amide groups is selected from biuret and succinamide.

8. The method of claim 1 , additionally comprising copolymerizing in the presence of a free radical initiator.

9. The method of claim 8 , wherein the free radical initiator comprises ammonium or potassium persulphate, 2,2′-(azobis(2-methylpropionamidine) dihydrocloride, hydrogen peroxide, or potassium, sodium or ammonium peroxodiphosphate.

10. A polymer prepared by a method comprising: copolymerizing a monomer comprising at least two amide groups, a monomer of formula (a)

and a sulfonic acid or salt monomer, wherein R 1 is CH 3 or H, the monomer comprising at least two amide groups is selected from carbonyldiamine and a compound of formula (c)

wherein R 3 is NH, aliphatic radical or ether unit.

11. A membrane comprising the polymer prepared by: copolymerizing a monomer comprising at least two amide groups, a monomer of formula (a)

and a sulfonic acid or salt monomer, wherein R 1 is CH 3 or H, wherein the monomer comprising at least two amide groups is selected from carbonyldiamine and a compound of formula (c)

wherein R 3 is NH, aliphatic radical or ether unit.

12. An electrode comprising the membrane comprising a polymer prepared by: copolymerizing a monomer comprising at least two amide groups, a monomer of formula (a)

and a sulfonic acid or salt monomer, wherein R 1 is CH 3 or H, wherein the monomer comprising at least two amide groups is selected from carbonyldiamine and a compound of formula (c)

wherein R 3 is NH, aliphatic radical or either unit.

13. The electrode of claim 12 wherein the sulfonic acid or salt monomer is of formula (b):

wherein

R 2 is CH 3 or H; X is NH or O and Y is alkyl.

14. The electrode of claim 13 , wherein the sulfonic acid or salt monomer is 2-acrylamido-2-methylpropane sulfonic acid.

15. The electrode of claim 12 , wherein the sulfonic acid or salt monomer is 2-acrylamido-2-methylpropanesulfonic acid, styrene sulfonic acid, sulfoalkyl (meth)-acrylates, sulfoalkyl itaconates, with a C 1 to C 6 alkyl radical, or vinylsulfonic acid and ammonium, alkali metal or alkaline earth metal salts thereof.

16. The electrode of claim 12 , wherein the sulfonic acid or salt monomer is 2-acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, p-styrenesulfonic acid, sulfopropyl acrylate, sulfopropyl itaconate or vinylsulfonic acid and ammonium, sodium, potassium and calcium salts thereof.

17. The electrode of claim 12 , wherein the monomer of formula (a) is N-methylolacrylamide (N-(hydroxymethyl) acrylamide, NMA), N-methylolmethacrylamide (NMMA), N-(isobutoxymethyl)-acrylamide (IBMA), N-(isobutoxymethyl)-methacrylamide or N-(n-butoxymethyl)-acrylamide (NBMA).

18. The electrode of claim 12 , wherein the copolymerizing is in the presence of a free radical initiator.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2018
From: GENERAL ELECTRIC COMPANY
To: BL TECHNOLOGIES, INC.
Reel/Frame 047502/0065 →