Self-wetting porous membranes (II)
Disclosed is a self-wetting porous membrane comprising an aromatic hydrophobic polymer such as polysulfone and a wetting agent comprising a copolymer of formula A-B or A-B-A, wherein A is a hydrophilic segment comprising a polymerized monomer of the formula (I): CH 2 ═C(R 1 )(R 2 ), wherein R 1 and R 2 are as described herein, and B is polyethersulfone, wherein segments B and A are linked through an oxygen atom. Also disclosed is a method of preparing a self-wetting membrane comprising casting a solution containing an aromatic hydrophobic polymer and the wetting agent, followed by subjecting the cast solution to phase inversion. The self-wetting porous membrane finds use in hemodialysis, microfiltration, and ultrafiltration.
1. A self-wetting porous membrane comprising an aromatic hydrophobic polymer and a wetting agent comprising a copolymer of formula A-B or A-B-A,
wherein A is a hydrophilic segment comprising a polymerized monomer or mixture of monomers, wherein the monomer is of the formula (I):
CH 2 ═C(R 1 )(R 2 ) (I),
wherein R 1 is hydrogen or alkyl, and R 2 is selected from pyrrolidinonyl, imidazolyl, N-methylimidazolyl, formylamino, formylaminoalkyl, alkylcarbonyloxy, and aminocarbonylalkyl substituted with a zwitterionic group,
and B is polyethersulfone, wherein segments B and A are linked through an oxygen atom;
wherein the copolymer has an end group selected from 2-methylpropionitrile, benzoate, laurate, t-butyloxy, and cumyloxy.
2. The self-wetting porous membrane of claim 1 , wherein R 1 is hydrogen or methyl, and R 2 is selected from pyrrolidinonyl, imidazolyl, N-methylimidazolyl, formylamino, formylaminomethyl, methylcarbonyloxy, and aminocarbonylpropyl substituted with a zwitterionic group.
3. The self-wetting porous membrane of claim 1 , wherein the monomer of A is selected from 1-vinylpyrrolid-2-one, N-[3-(dimethylamino)propyl]methacrylamide, vinyl acetate, 1-vinylimidazole, 1-vinyl-3-methylimidazole, N-vinylformamide, N-allylformamide, and 3-(methacrylamidopropyl)dimethyl(3-sulfopropyl)ammonium inner salt.
4. The self-wetting porous membrane of claim 1 , wherein the aromatic hydrophobic polymer is selected from polysulfone, polyethersulfone, polyphenylene ether, polyphenylene ether sulfone, polyphenylene oxide, polycarbonate, poly(phthalazinone ether sulfone ketone), polyether ketone, polyether ether ketone, polyether ketone ketone, polyimide, polyetherimide, and polyamide-imide.
5. The self-wetting porous membrane of claim 1 , wherein the aromatic hydrophobic polymer is polysulfone or polyethersulfone.
6. The self-wetting porous membrane of claim 1 , wherein the wetting agent is a copolymer of the formula A-B-A and is represented by formula (Ia):
or the wetting agent is a copolymer of the formula A-B and is represented by formula (Ib):
wherein A′ is a polymeric segment of the hydrophilic monomer, T is an end group selected from 2-methylpropionitrile, benzoate, laurate, t-butyloxy, and cumyloxy, Y is chloro or fluoro, m 1 or m 2 is from about 5 to about 80, and n is from about 20 to about 200.
7. The self-wetting porous membrane of claim 1 , wherein the copolymer is of the formula:
wherein m 1 or m 2 is from about 5 to about 80 and n is from about 20 to about 200.
8. A method of preparing a self-wetting porous membrane comprising:
(i) casting a solution comprising a solvent, an aromatic hydrophobic polymer, and a copolymer of formula A-B or A-B-A, wherein A is a hydrophilic segment comprising a polymerized monomer or mixture of monomers, wherein the monomer is of the formula (I):
CH 2 ═C(R 1 )(R 2 ) (I),
wherein R 1 is hydrogen or alkyl, and R 2 is selected from pyrrolidinonyl, imidazolyl, N-methylimidazolyl, formylamino, formylaminoalkyl, alkylcarbonyloxy, and aminocarbonylalkyl substituted with a zwitterionic group, and
wherein the copolymer has an end group selected from 2-methylpropionitrile, benzoate, laurate, t-butyloxy, and cumyloxy,
and B is polyethersulfone, wherein segments B and A are linked through an oxygen atom, to a desired shape;
(ii) subjecting the cast solution to phase inversion to form the self-wetting porous membrane; and
(iii) optionally rinsing the self-wetting porous membrane with water.
9. The method of claim 8 , wherein R 1 is hydrogen or methyl, and R 2 is selected from pyrrolidinonyl, imidazolyl, N-methylimidazolyl, formylamino, formylaminomethyl, methylcarbonyloxy, and aminocarbonylpropyl substituted with a zwitterionic group.
10. The method of claim 8 , wherein the monomer of A is selected from 1-vinylpyrrolid-2-one, N-[3-(dimethylamino)propyl]methacrylamide, vinyl acetate, 1-vinylimidazole, 1-vinyl-3-methylimidazole, N-vinylformamide, and N-allylformamide, and 3-(methacrylamidopropyl)dimethyl(3-sulfopropyl)ammonium inner salt.
11. The method of claim 8 , wherein the aromatic hydrophobic polymeric segment B is polyethersulfone.
12. The method of claim 8 , wherein the aromatic hydrophobic polymer is selected from polysulfone, polyethersulfone, polyphenylene ether, polyphenylene ether sulfone, polyphenylene oxide, polycarbonate, poly(phthalazinone ether sulfone ketone), polyether ketone, polyether ether ketone, polyether ketone ketone, polyimide, polyetherimide, and polyamide-imide.
13. The method of claim 8 , wherein the aromatic hydrophobic polymer is polysulfone or polyethersulfone.
14. The method of claim 8 , wherein the copolymer of formula A-B-A is of the formula (Ia):
and the copolymer of formula A-B is of the formula (Ib):
wherein A′ is a polymeric segment of the hydrophilic monomer, T is an end group selected from 2-methylpropionitrile, benzoate, laurate, t-butyloxy, and cumyloxy, Y is chloro or fluoro, m 1 or m 2 is from about 5 to about 80, and n is from about 20 to about 200.
15. The method of claim 8 , wherein the copolymer is of the formula:
wherein m 1 or m 2 is from about 5 to about 80 and n is from about 20 to about 200.
16. A self-wetting porous membrane prepared by the method of claim 8 .
17. A method of filtering a fluid, the method comprising passing the fluid through the self-wetting porous membrane of claim 1 .