Curable compositions and membranes

Patent metadata

Field	Value
Publication number	US-9309343-B2
Application number	US-201214233167-A
Country	US
Kind code	B2
Filing date	Jul 5, 2012
Priority date	Jul 19, 2011
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

A membrane obtainable from curing a composition comprising (i) a curable compound comprising at least two acrylic groups and a quaternary ammonium group; (ii) solvent; and optionally (iii) a curable compound having one ethylenically unsaturated group.

First claim

The invention claimed is:

1. A membrane obtained from curing a composition comprising:
(i) a curable compound comprising (a) at least two acrylamide groups; and (b) at least one quaternary ammonium group;
(ii) solvent;
and optionally (iii) a curable compound having one ethylenically unsaturated group.

2. The membrane according to claim 1 wherein the composition further comprises a radical initiator.

3. The membrane according to claim 1 wherein optional component (iii) is present.

4. The membrane according to claim 1 wherein component (ii) comprises water or a mixture comprising water and a water-miscible organic solvent.

5. The membrane according to claim 1 wherein the curable compound having one ethylenically unsaturated group further comprises a cationic group.

6. The membrane according to claim 1 wherein component (i) comprises a compound of the Formula (1):

wherein:
R 1 and R 2 are H;
R 3 and R 4 are each independently H or alkyl, or R 3 and R 4 together with the N atoms to which they are attached and Y form an optionally substituted 6- or 7-membered ring; and
Y is a linking group comprising an optionally substituted and optionally interrupted alkylene or arylene group;
provided that the compound of Formula (1) has at least one of 1, 2, 3 or 4 quaternary ammonium groups, wherein the at least one of 1, 2, 3 or 4 quaternary ammonium groups may be present as substituents and/or interruptions within the Y group or on the 6- or 7-membered ring formed by R 3 and R 4 together with the N atoms to which they are attached.

7. The membrane according to claim 1 comprising a structural unit of Formula (1′):

wherein:
R 1 and R 2 are H;
R 3 and R 4 are each independently H or alkyl, or R 3 and R 4 together with the N atoms to which they are attached and Y form an optionally substituted 6- or 7-membered ring; and
Y is a linking group comprising an optionally substituted and optionally interrupted alkylene or arylene group;
provided that the structural unit of Formula (1′) has at least one of 1, 2, 3 or 4 quaternary ammonium groups, wherein the at least one of 1, 2, 3 or 4 quaternary ammonium groups may be present as substituents and/or interruptions within the Y group or on the 6- or 7-membered ring formed by R 3 and R 4 together with the N atoms to which they are attached.

8. The membrane according to claim 1 wherein the composition further comprises a radical initiator, component (ii) comprises water or a mixture comprising water and a water-miscible organic solvent and optional component (iii) is present and further comprises a cationic group.

9. The membrane according to claim 1 wherein the molar fraction of curable compounds comprising at least two acrylamide groups and a quaternary ammonium group, relative to the total number of moles of curable compounds present in the composition, is at least 0.30.

10. The membrane according to claim 1 wherein the composition comprises:
(i) a curable compound comprising (a) at least two acrylamide groups; and (b) at least one quaternary ammonium group;
(ii) a solvent;
(iii) a curable compound having one ethylenically unsaturated group;
(iv) a curable compound comprising at least two acrylamide groups and being free from quaternary ammonium groups; and
(v) a radical initiator; and
wherein the composition comprises:
(a) 2 to 80 wt % of component (i), 15 to 70 wt % of component (ii), 1 to 70 wt % of component (iii), 0 to 40 wt % of component (iv); and 0 to 10 wt % of component (v); or
(b) 5 to 80 wt % of component (i), 20 to 45 wt % of component (ii), 0 to 60 wt % of component (iii), 0 to 30 wt % of component (iv); and 0.1 to 10 wt % of component (v).

11. An electrodialysis or reverse electrodialysis unit, a flow through capacitor device, an electrodeionization module, a continuous electrodeionization module, a fuel cell, a diffusion dialysis apparatus, a membrane distillation module or a membrane electrode assembly comprising one or more polymeric membranes according to claim 1 .

12. An electrodialysis or reverse electrodialysis unit, a flow through capacitor device, an electrodeionization module, a continuous electrodeionization module, a fuel cell, a diffusion dialysis apparatus, a membrane distillation module or a membrane electrode assembly comprising one or more polymeric membranes according to claim 7 .

13. A process for preparing a membrane comprising the following steps:
a) applying a composition to a support; and
b) curing the composition to form a membrane;
wherein the composition comprises (i) a curable compound comprising (a) at least two acrylamide groups; and (b) at least one quaternary ammonium group; (ii) solvent; and optionally (iii) a curable compound having one ethylenically unsaturated group; and
wherein the curing is performed by radical polymerisation using electromagnetic radiation.

14. The process according to claim 13 wherein the composition comprises:
(i) a curable compound comprising (a) at least two acrylamide groups; and (b) at least one quaternary ammonium group;
(ii) a solvent;
(iii) a curable compound having one ethylenically unsaturated group;
(iv) a curable compound comprising at least two acrylamide groups and being free from quaternary ammonium groups; and
(v) a radical initiator; and
wherein the composition comprises:
(a) 2 to 80 wt % of component (i), 15 to 70 wt % of component (ii), 1 to 70 wt % of component (iii), 0 to 40 wt % of component (iv); and 0 to 10 wt % of component (v); or
(b) 5 to 80 wt % of component (i), 20 to 45 wt % of component (ii), 0 to 60 wt % of component (iii), 0 to 30 wt % of component (iv); and 0.1 to 10 wt % of component (v).

15. The process according to claim 14 wherein the curing is performed using electron beam or UV radiation.

16. The process according to claim 13 wherein the curing is performed using electron beam or UV radiation.

17. The process according to claim 13 wherein the composition is applied continuously to a moving support by means of a manufacturing unit comprising a composition application station, an irradiation source for curing the composition, a membrane collecting station and a means for moving the support from the composition application station to the irradiation source and to the membrane collecting station.

18. The process according to claim 17 wherein the curable composition is applied to the support moving at a speed of over 5 m/min.

Assignees

• Van Berchum Bastiaan
• Van Baak Willem Johannes
• Hessing Jacko
• Fujifilm Mfg Europe Bv

Inventors

• Van Berchum Bastiaan
• Van Baak Willem Johannes
• Hessing Jacko

Classifications

• C08J2333/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• C08F20/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• B01D71/56

  Polyamides, e.g. polyester-amides · CPC title

• H01M2008/1095

  Fuel cells with polymeric electrolytes · CPC title

• B01D53/228

  characterised by specific membranes · CPC title