Universal scalable and cost-effective surface modifications

Patent metadata

Field	Value
Publication number	US-9662617-B2
Application number	US-201414768887-A
Country	US
Kind code	B2
Filing date	Feb 21, 2014
Priority date	Feb 21, 2013
Publication date	May 30, 2017
Grant date	May 30, 2017

Abstract

Disclosed are fouling resistant filtration membranes comprising a polymeric thin-film membrane comprising a surface. Also disclosed are methods of modifying thin-film filtration membranes, thereby improving, for example, the anti-fouling properties of the membranes. Also disclosed are methods of purifying water using the disclosed membranes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

First claim

What is claimed is:

1. A fouling resistant filtration membrane comprising a polymeric thin-film membrane comprising a surface, wherein the surface is modified with at least one residue of a compound having a structure represented by a formula:

wherein A is selected from —C(═O)— and —(SO 2 )—;
wherein L is selected from —OQ, —O − , —N + R 3 HQ and —NR 3 Q;
wherein Q is selected from hydrogen, a hydrophilic polymer, and a structure represented by a formula:

wherein Z is selected from —CR 6a R 6b —, —C(═O)—, —C(═NH)—, and —C(═NH)NR 7 —;
wherein m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;
wherein each of R 1a and R 1b is independently selected from hydrogen and halogen;
wherein each of R 2a and R 2b is halogen;
wherein R 3 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 4a and R 4b , when present, is independently selected from hydrogen,
halogen, —CN, —OH, —NR 8a R 8b , —NR 8a R 8b H + , C1-C4 alkyl, C1-C4 monohaloalkyl, C1-C4 polyhaloalkyl, —SO 3 − , —SO 3 R 9 , —CO 2 − , and —CO 2 R 9 ;
wherein each of R 5a , R 5b , and R 5c is independently selected from hydrogen, halogen, —CN, —OH, —NR 10a R 10b , —NR 10a R 10b H + , C1-C4 alkyl, C1-C4 monohaloalkyl, C1-C4 polyhaloalkyl, —SO 3 − , —SO 3 R 11 , —CO 2 − , and —CO 2 R 11 ;
wherein each of R 6a and R 6b , when present, is independently selected from hydrogen, halogen, —CN, —OH, —NR 12a R 12b , —NR 12a R 12b H + , C1-C4 alkyl, C1-C4 monohaloalkyl, C1-C4 polyhaloalkyl, —SO 3 − , —SO 3 R 13 , —CO 2 − , and —CO 2 R 13 ;
wherein R 7 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 8a and R 8b , when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein R 9 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 10a and R 10b when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein R 11 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 12a and R 12b , when present, is independently selected from hydrogen and C1-C4 alkyl; and
wherein R 13 , when present, is selected from hydrogen and C1-C4 alkyl.

2. The membrane of claim 1 , wherein the membrane comprises at least one polyamide.

3. The membrane of claim 1 , wherein L is —O − .

4. The membrane of claim 1 , wherein L is selected from —OQ and —NR 3 Q.

5. The membrane of claim 1 , wherein Q is hydrogen.

6. The membrane of claim 1 , wherein Q is a hydrophilic polymer.

7. The membrane of claim 6 , wherein the hydrophilic polymer comprises at least one moiety selected from poly(ethylene glycol), poly(ethyleneimine) and polyaniline, or a mixture thereof.

8. The membrane of claim 1 , wherein Q has a structure represented by a formula:

9. The membrane of claim 1 , wherein Q has a structure selected from:

10. The membrane of claim 1 , wherein Z is selected from —CH 2 and —C(═NH)NH—.

11. The membrane of claim 1 , wherein m is 0.

12. The membrane of claim 1 , wherein each of R 1a and R 1b is hydrogen.

13. The membrane of claim 1 , wherein each of R 1a and R 1b is halogen.

14. The membrane of claim 1 , wherein R 1a is halogen and R 1b is hydrogen.

15. The membrane of claim 1 , wherein the halogen is selected from —F and —Cl.

16. The membrane of claim 1 , wherein the halogen is —F.

17. The membrane of claim 1 , wherein R 5a is —CO 2 − , R 5b is —NH 3 + , and R 5c is hydrogen.

18. The membrane of claim 1 , wherein R 5a is —CO 2 − , and each of R 5b and R 5c is hydrogen.

19. The membrane of claim 1 , wherein R 5a is —NH 3 + , and each of R 5b and R 5c is hydrogen.

20. A method of modifying a thin-film membrane comprising a surface, the method comprising the step of bonding the surface with at least one residue of a compound having a structure represented by a formula:

wherein A is selected from —C(═O)— and —(SO 2 )—;
wherein L is selected from —OQ, —O − , —N + R 3 HQ and —NR 3 Q;
wherein Q is selected from hydrogen, a hydrophilic polymer, and a structure represented by a formula:

wherein Z is selected from —CR 6a R 6b —, —C(═NH)—, and —C(═NH)NR 7 —;
wherein m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;
wherein each of R 1a and R 1b is independently selected from hydrogen and halogen;
wherein each of R 2a and R 2b is halogen;
wherein R 3 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 4a and R 4b , when present, is independently selected from hydrogen, halogen, —CN, —OH, —NR 8a R 8b , —NR 8a R 8b H + , C1-C4 alkyl, C1-C4 monohaloalkyl, C1-C4 polyhaloalkyl, —SO 3 − , —SO 3 R 9 , —CO 2 − , and —CO 2 R 9 ;
wherein each of R 5a , R 5b , and R 5c is independently selected from hydrogen, halogen, —CN, —OH, —NR 10a R 10b , —NR 10a R 10b H + , C1-C4 alkyl, C1-C4 monohaloalkyl, C1-C4 polyhaloalkyl, —SO 3 − , —SO 3 R 11 , —CO 2 − , and —CO 2 R 11 ;
wherein each of R 6a and R 6b , when present, is independently selected from hydrogen, halogen, —CN, —OH, —NR 12a R 12b , —NR 12a R 12b H + , C1-C4 alkyl, C1-C4 monohaloalkyl, C1-C4 polyhaloalkyl, —SO 3 − , —SO 3 R 13 , —CO 2 − , and —CO 2 R 13 ;
wherein R 7 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 8a and R 8b , when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein R 9 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 10a and R 10b , when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein R 11 , when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R 11a and R 12b , when present, is independently selected from hydrogen and C1-C4 alkyl; and
wherein R 13 , when present, is selected from hydrogen and C1-C4 alkyl.

21. The method of claim 20 , wherein the surface comprises at least one —NH— and/or —C═C— residue.

22. The method of claim 20 , further comprising activating the azide, thereby forming a singlet nitrene.

23. A method of purifying water, the method comprising:
(a) providing the membrane of claim 1 , the membrane having a first face and a second face;
(b) contacting the first face of the membrane with a first solution of a first volume having a first salt concentration at a first pressure; and
(c) contacting the second face of the membrane with a second solution of a second volume having a second salt concentration at a second pressure;
wherein the first solution is in fluid communication with the second solution through the membrane,
wherein the first salt concentration is higher than the

Assignees

• Univ California

Inventors

• Hoek Eric M V
• Kaner Richard B
• Mcverry Brian T

Classifications

• B01D69/08

  Hollow fibre membranes (manufacture of hollow fibres D01D5/24, D01F1/08) · CPC title

• B01D2325/48

  Antimicrobial properties · CPC title

• B01D71/56

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

• B01D67/0088

  Physical treatment with compounds, e.g. swelling, coating or impregnation · CPC title

• B01D61/025

  Reverse osmosis; Hyperfiltration · CPC title