Polymers, fluorinated ionic polymer networks, and methods related thereto
Disclosed herein are materials and methods related to the removal of a polyfluorinated alkyl compound from water. The materials contain both fluorine and an ion, which materials can be used as a network to remove the polyfluorinated alkyl compound from water.
1. A method of removing a polyfluorinated alkyl compound from water, the method comprising absorbing the polyfluorinated alkyl compound from the water with a resin comprising a fluorinated ionic polymer network,
wherein the fluorinated ionic polymer network is a co-polymer made from a) a monomer comprising an ion generating moiety or a monomer comprising an ion; and b) a monomer comprising a fluorine having a structure:
wherein each X is individually CF 2 or O, wherein each Y is polymerizable group, wherein n is from 0-100, wherein o is from 0-100, and wherein each m is individually from 1-30.
2. The method of claim 1 , wherein the method further comprises the step of removing the fluorinated ionic polymer network comprising the absorbed polyfluorinated alkyl compound from the water.
3. The method of claim 2 , wherein the method further comprises the step of separating the absorbed polyfluorinated alkyl compound from the fluorinated ionic polymer network.
4. The method of claim 1 , wherein the fluorinated ionic polymer network is a fluorinated cationic polymer network.
5. The method of claim 1 , wherein the fluorinated ionic polymer network is a fluorinated anionic polymer network.
6. The method of claim 1 , wherein the fluorinated ionic polymer network is a fluorinated zwitterionic polymer network.
7. The method of claim 1 , wherein the fluorinated ionic polymer network is a co-polymer made from a monomer comprising fluorine and a monomer comprising an ion-generating moiety.
8. The method of claim 7 , wherein the ion-generating moiety is an amine, imidazole, benzimidazole, guanidinium, triazole, pyridine, diazine, triazine, thiol, thioether, phosphorane, or phosphine.
9. The method of claim 1 , wherein the fluorinated ionic polymer network comprises a quaternary ammonium or quaternary phosphonium.
10. The method of anyone of claim 1 , wherein the polymerizable group is acrylate, methacrylate, acrylamide, methacrylamide, vinylcarbonate, vinylcarbamate, vinyl ester, vinyl benzyl, vinyl halobenzyl, vinyl ether, epoxide, oxirane, hydroxyl, or isocyanate.
11. The method of claim 1 , wherein the fluorinated ionic polymer network is in the form of a particle having a mean average diameter from 5 nm to 10 cm.
12. The method of claim 1 , wherein the fluorinated ionic polymer network is a membrane or part of a membrane.
13. A method of removing a polyfluorinated alkyl compound from water, the method comprising absorbing the polyfluorinated alkyl compound from the water with a resin comprising a fluorinated ionic polymer network,
wherein the fluorinated ionic polymer network is a co-polymer made from a monomer comprising fluorine and a monomer comprising an ion,
wherein the monomer comprising fluorine has a structure:
wherein n is from 0-100 and o is from 0-100.
14. The method of claim 13 , wherein the monomer comprising an ion generating moiety has a structure:
wherein each R 1 group independently is H or C1-C3 alkyl.
15. The method of claim 13 , wherein the monomer comprising an ion generating moiety has a structure:
wherein each R 2 group independently is H, C1-C6 alkyl, C1-C6 fluoroalkyl, aryl, or fluoroaryl,
wherein p is from 0-11, and
wherein Y is a polymerizable group.
16. The method of claim 13 , wherein the monomer comprising an ion has a structure:
wherein each R 3 group independently is H, C1-C6 alkyl, C1-C6 fluoroalkyl, aryl, or fluoroaryl,
wherein p is from 0-11,
wherein Y is a polymerizable group, and
wherein Q is a counter-ion.
17. The method of claim 13 , wherein the monomer comprising an ion has a structure;
wherein each R 4 group independently is H, C1-C6 alkyl, C1-C6 fluoroalkyl, aryl, or fluoroaryl,
wherein each u is independently from 0-10,
wherein Y is a polymerizable group,
wherein Z is an anionic group or a polymerizable group, and
wherein Q is a counter-ion.