Composite polyamide membrane derived from monomer including amine-reactive and phosphorous-containing functional groups
A method for making a composite polyamide membrane comprising the steps of applying a polyfunctional amine monomer and polyfunctional acyl halide monomer to a surface of the porous support and interfacially polymerizing the monomers to form a thin film polyamide layer, wherein the method is includes at least one of the following steps: i) conducting the interfacial polymerization in the presence of a monomer comprising at least one phosphorous-containing functional group or salt thereof and an at least one amine-reactive functional group; and/or ii) applying such a monomer to the thin film polyamide layer.
1. A method for making a composite polyamide membrane comprising a porous support and a thin film polyamide layer, wherein the method comprises the step of applying a polyfunctional amine monomer and polyfunctional acyl halide monomer to a surface of the porous support and interfacially polymerizing the monomers to form a thin film polyamide layer, wherein the method is characterized by including at least one of the following steps:
i) conducting the interfacial polymerization in the presence of a monomer comprising: a hydrocarbon moiety, at least one phosphorous-containing functional group or salt thereof and at least one amine-reactive-functional group selected from acyl halide and epoxy; and
ii) applying a monomer comprising: a hydrocarbon moiety, at least one phosphorous containing-functional group or salt thereof and at least one amine-reactive functional group selected from acyl halide and epoxy to the thin film polyamide layer.
2. The method of claim 1 wherein the amine-reactive functional groups is an acyl halide.
3. The method of claim 1 wherein the phosphorous-containing functional group is represented by Formula (III):
wherein A and A′ are independently selected from: amine, alkoxy, aryoxy, halogen, hydrogen and hydroxyl, and Y is a linking group selected from: a chemical bond, oxygen, sulfur, alkyl and amine.
4. The method of claim 3 wherein A and A′ are independently selected from: halogen and hydroxyl.
5. The method of claim 3 wherein Y is selected from oxygen, an alkyl and a chemical bond.
6. The method of claim 1 wherein the hydrocarbon moiety comprises an acyclic or cyclic group comprising from 1 to 9 carbon atoms.
7. The method of claim 1 wherein the hydrocarbon moiety comprises a benzene ring.
8. The method of claim 1 wherein the monomer comprising a phosphorous-containing functional group or salt thereof and an amine-reactive functional group is represented by at least one of Formula (V) and Formula (VIa):
wherein A and A′ are independently selected from: amine, alkoxy, aryoxy, halogen, hydrogen and hydroxyl, and Y is a linking group selected from: a chemical bond, oxygen, sulfur, alkyl and amine, and Z is an amine-reactive functional group selected from: acyl halide and epoxy.
9. The method of claim 1 wherein the monomer comprising a phosphorous-containing functional group or salt thereof and an amine-reactive functional group is represented by (Vc):
wherein X and X′ are independently selected from halogens, A and A′ are independently selected from amine, alkoxy, aryoxy, halogen, hydrogen and hydroxyl, and Y is a linking group selected from: a chemical bond, oxygen, sulfur, alkyl and amine.
10. The method of claim 1 wherein the step of applying the polyfunctional monomers to the surface of the porous support comprises applying a polar solution comprising the polyfunctional amine monomer and a non-polar solution comprising the polyfunctional acyl halide monomer; and wherein the non-polar solution further comprises the monomer comprising a phosphorous-containing functional group or salt thereof and an amine-reactive functional group.
11. The method of claim 10 wherein the non-polar solution comprises at least 0.001 weight/volume of the monomer comprising a phosphorous-containing functional group or salt thereof and an amine-reactive functional group.