Composite polyamide membrane derived from carboxylic acid containing acyl halide monomer

Patent metadata

Field	Value
Publication number	US-9289729-B2
Application number	US-201313844839-A
Country	US
Kind code	B2
Filing date	Mar 16, 2013
Priority date	Mar 16, 2013
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

A method for making a composite polyamide membrane comprising the step of applying polyfunctional amine and acid halide monomers to a surface of a porous support and interfacially polymerizing the monomers to form a thin film polyamide layer. The method further includes the step of conducting the interfacial polymerization in the presence of: a carboxylic acid monomer comprising an aliphatic or aromatic moiety substituted with single carboxylic acid functional group and at least one acyl halide functional group, and a tri-hydrocarbyl compound.

First claim

The invention claimed is:

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 acid 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 applying a coating solution to the surface of the porous support comprising:
i) a hydrocarbon solvent:
ii) greater than 0.01 weight percent of an additional monomer comprising a carboxylic acid monomer comprising an aliphatic or aromatic moiety substituted with single carboxylic acid functional group and at least one acyl halide functional group and comprising equal to or less than 30 carbon atoms, and
iii) a tri-hydrocarbyl phosphate compound represented by Formula (I):

wherein R 1 , R 2 and R 3 are independently selected from hydrogen and hydrocarbyl groups comprising from 1 to 10 carbon atoms, with the proviso that no more than one of R 1 , R 2 and R 3 are hydrogen,
wherein the interfacial polymerization is conducted in the presence of the carboxylic acid monomer and tri-hydrocarbyl phosphate compound.

2. The method of claim 1 wherein the coating solution further comprises the polyfunctional acyl halide monomer.

3. The method of claim 2 wherein the coating solution further comprises the polyfunctional acyl halide monomer.

4. The method of claim 2 wherein the carboxylic acid monomer and tri-hydrocarbyl phosphate compound are provided in the coating solution in a molar ratio of from 1:1000 to 2:1.

5. The method of claim 2 wherein the carboxylic acid monomer and tri-hydrocarbyl phosphate compound are provided in the coating solution in a molar ratio of from 1:100 to 1:1.

6. The method of claim 1 wherein the carboxylic acid monomer is present in the coating solution at a concentration greater than its solubility limit in the hydrocarbon solvent but less than its solubility limit in the coating solution.

7. The method of claim 1 wherein the carboxylic acid monomer is present in the coating solution at a concentration greater than 0.02 weight percent.

8. The method of claim 1 wherein the carboxylic acid monomer is a mono-hydrolyzed analog of the polyfunctional monomer.

9. The method of claim 1 wherein the carboxylic acid monomer is formed in-situ within a coating solution prepared by combining water with the polyfunctional acyl halide monomer, tri-hydrocarbyl phosphate compound and a hydrocarbon solvent.

10. The method of claim 9 wherein the coating solution comprises:
i) water at a concentration of less than 1 wt %,
ii) the polyfunctional acyl halide monomer at a concentration of less than 10 wt % and
iii) the tri-hydrocarbyl phosphate compound at a concentration of less than 10 wt %.

11. The method of claim 9 wherein the coating solution comprises:
i) water at a concentration of less than 0.5 wt %,
ii) the polyfunctional acyl halide monomer at a concentration of less than 5 wt %, and
iii) the tri-hydrocarbyl phosphate compound at a concentration of less than 5 wt %.

12. The method of claim 9 wherein the coating solution comprises the polyfunctional acyl halide monomer at a molar ratio with water from 1:2 to 100:1.

13. The method of claim 9 wherein the coating solution comprises the tri-hydrocarbyl phosphate compound at a molar ratio with the polyfunctional acyl halide monomer of 100:1 to 1:1000.

14. The method of claim 9 wherein the coating solutions comprises at least 80 v/v % of the hydrocarbon solvent.

Assignees

• Dow Global Technologies Llc

Inventors

• Roy Abhishek
• Jons Steven D
• Koob Joseph D
• Peery Martin H
• Qiu Xiaohua Sam
• Rosenberg Steven
• Tomlinson Ian A

Classifications

• B01D69/125

  In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction · CPC title

• B01D71/56 Primary

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

• B01D69/10

  Supported membranes; Membrane supports · CPC title

• B01D69/107

  Organic support material · CPC title

• B01D69/1251

  by interfacial polymerisation · CPC title