Membrane and associated method
View Patent ↗Provided is a fluorine substituted oligomeric or polymeric ester including the reaction product of a fluorine substituted acrylate or a fluorine substituted methacrylate; an unsaturated anhydride; and an alkyl acrylate or an alkyl methacrylate. Also provided is a method of making the composition.
1. A membrane comprising a coating, the coating comprising:
a terpolymer having the structure of formula (I)
wherein R1 comprises an alkyl radical; R2 comprises of a formula CF 3 (CF 2 )p(CH 2 )q—wherein “p” is an integer in a range of from 1 to about 21, and “q” is an integer in a range of from 1 to about 10; R3 and R4 are separately hydrogen or a short chain alkyl; and
“m” is an integer greater than 1, “n” is an integer greater than about 2 to about 20,000, and “o” is an integer greater than about 2.
2. The membrane as defined in claim 1 , wherein R1 is an alkyl radical having from C1 to about C10 carbon atoms.
3. The membrane as defined in claim 2 , wherein R1 is butyl.
4. The membrane as defined in claim 1 , wherein R2 is fully substituted with fluorine.
5. The membrane as defined in claim 1 , wherein R2 is an alkyl radical having from C1 to about C10 carbon atoms.
6. The membrane as defined in claim 5 , wherein R2 is an alkyl chain having more than about C5 carbon atoms.
7. The membrane as defined in claim 1 , wherein R2 is a linear chain.
8. The membrane as defined in claim 1 , wherein “m”, “n”, and “o” represent mole proportions of 1:2:2 respectively.
9. The membrane as defined in claim 1 , wherein the coating further comprises a curing agent.
10. The membrane as defined in claim 9 , wherein the coating is cross-linked to form a hydrophilic coated membrane.
11. The membrane as defined in claim 10 , wherein the coated membrane is re-wettable in the absence of alcohol after at least one wet/dry cycle.
12. The membrane as defined in claim 10 , wherein the coated membrane has a flow rate of water that is greater than about 1 mL/min-cm at 27 inches Hg pressure differential after 10 wet/dry cycles at room temperature.
13. The membrane as defined in claim 1 , wherein the membrane comprises one or both of polyvinylidene fluoride or polytetrafluoroethylene.
14. The membrane as defined in claim 1 , wherein the base membrane comprises one or more of polyethylene, polyolefin, polyamide, polyester, polysulfone, polyether, polyacrylic, polymethacrylic, polystyrene, polyurethane, polypropylene, polyphenelene sulfone, polyphenylene oxide, or cellulosic polymer.
15. A membrane comprising a coating, wherein the coating comprises a reaction product of:
a fluorine substituted acrylate or a fluorine substituted methacrylate;
an unsaturated anhydride comprising itaconic anhydride or maleic anhydride; and
an alkyl acrylate or an alkyl methacrylate.
16. The membrane as defined in claim 15 , wherein the itaconic anhydride is present in an amount in a range of greater than about 20 mole percent.
17. The membrane as defined in claim 15 , wherein the fluorine substituted acrylate is present in an amount in a range of greater than about 20 mole percent.
18. The membrane as defined in claim 15 , wherein the fluorine substituted acrylate comprises 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl acrylate.
19. The membrane as defined in claim 17 , wherein the itaconic anhydride is present in an amount of about 25 mole percent.
20. The membrane as defined in claim 17 , wherein the fluorine substituted acrylate is present in an amount of about 25 mole percent.
21. The membrane as defined in claim 15 , wherein the alkyl acrylate is present in an amount in a range of greater than about 35 mole percent.
22. The membrane as defined in claim 21 , wherein the alkyl acrylate is present in an amount of about 50 mole percent.
23. The membrane as defined in claim 15 , wherein the alkyl acrylate comprises butyl acrylate.
24. The membrane as defined in claim 15 , further comprising residual amounts of an azo-based free radical polymerization initiator.
25. The membrane as defined in claim 15 , wherein the coating further comprises a polyfunctional cross-linking agent.
26. The membrane as defined in claim 25 , wherein the cross-linking agent comprises a polyfunctional amine.
27. The membrane as defined in claim 26 , wherein the polyfunctional amine comprises one or both of 2,2′-(ethylenedioxy) diethylamine or hexamethylenediamine.
28. The membrane as defined in claim 27 , wherein:
the fluorine substituted acrylate consists essentially of 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl acrylate;
the unsaturated anhydride consists essentially of itaconic anhydride; and
the alkyl acrylate consists essentially of butyl acrylate.
29. The membrane as defined in claim 25 , wherein the coating is cross-linked with the polyfunctional cross-linking agent to form a coated membrane.
30. The membrane as defined in claim 29 , wherein the coated membrane has a flow rate of water that is greater than about 1 mL/min-cm at 27 inches Hg pressure differential after 10 wet/dry cycles at room temperature.
31. A method, comprising:
reacting a fluorine substituted acrylate or a fluorine substituted methacrylate; an unsaturated anhydride comprising itaconic anhydride or maleic anhydride; an alkyl acrylate or an alkyl methacrylate; and an initiator in a solvent to form a terpolymer; and
reacting the terpolymer and a polyfunctional cross-linking agent to form a coating on a membrane.
32. The method as defined in claim 31 , further comprising wherein the cross-linking agent comprises one or both of 2,2′-(ethylenedioxy)diethylamine or hexamethylenediamine.
33. The method as defined in claim 31 , wherein reacting comprises curing the terpolymer to form a cross-linked hydrophilic coating.
34. The method as defined in claim 33 , wherein curing comprises generating a network of hydrophilic functionality such as carboxylic acid groups and inter/intramolecular ammonium-carboxylate ion pairs to impart hydrophilicity.
35. The method as defined in claim 31 , wherein the membrane is water permeable.