Polyaniline-based chlorine resistant hydrophilic filtration membranes

Patent metadata

Field	Value
Publication number	US-10532328-B2
Application number	US-201515302361-A
Country	US
Kind code	B2
Filing date	Apr 7, 2015
Priority date	Apr 8, 2014
Publication date	Jan 14, 2020
Grant date	Jan 14, 2020

Abstract

In one aspect, the invention relates to chlorine-resistant filtration membranes comprising n-alkyl substituted polyaniline derivatives for use in, for example, water purification, and methods for making and using same. 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 filtration membrane comprising

a polymer comprising a structure represented by formula I:

wherein each Z is independently selected from hydrogen and

wherein n is an integer selected from 1, 2, and 3;
wherein p is independently 0, 0.5, or 1;
wherein q is independently 0, 0.5, or 1;
wherein, for each x, p+q=1;
wherein each of R 1a , R 1b , R 1c , and R 1d is independently selected from hydrogen, halogen, —CN, —SR 20 , —OR 21 , —NR 22a R 22b , —NR 22a R 22b H + , —SO 2 R 23 , —(C═O)R 24 , and C1-C3 alkyl substituted with 0, 1, 2, or 3 groups selected from halogen, —CN, —SR 20 , —OR 21 , —NR 22a R 22b , —SO 2 R 23 , and —(C═O)R 24 ;
wherein each of R 2a and R 2b is independently selected from hydrogen, halogen, —CN, —SR 30 , —OR 31 , —NR 32a R 32b , —NR 32a R 32b H + , —SO 2 R 33 , —(C═O)R 34 , and C1-C3 alkyl substituted with 0, 1, 2, or 3 groups selected from halogen, —CN, —SR 30 , —OR 31 , —NR 32a R 32b , —SO 2 R 33 , and —(C═O)R 34 ;
wherein each of R 3a , R 3b , and R 3c is independently selected from hydrogen, halogen, —CN, —SR 40 , —OR 41 , —NR 42a R 42b H + , —NR 42a R 42b H + , —SO 2 R 43 , and —(C═O)R 44 ;
wherein each of R 20 , R 21 , R 22a , R 22b , R 30 , R 31 , R 32a , R 32b , R 40 , R 41 , R 42a , and R 42b , when present, is independently selected from hydrogen, C1-C3 alkyl, C1-C3 monohaloalkyl, and C1-C3 polyhaloalkyl;
wherein each of R 23 and R 24 , when present, is independently selected from —O − , —OR 25 , C1-C3 alkyl, C1-C3 monohaloalkyl, C1-C3 polyhaloalkyl, and —NR 26a R 26b ;
wherein each of R 25 , R 26a , and R 26b , when present, is independently selected from hydrogen, C1-C3 alkyl, C1-C3 monohaloalkyl, and C1-C3 polyhaloalkyl;
wherein each of R 33 and R 34 , when present, is independently selected from —O − , —OR 35 , C1-C3 alkyl, C1-C3 monohaloalkyl, C1-C3 polyhaloalkyl, and —NR 36a R 36b ;
wherein each of R 35 , R 36a , and R 36b , when present, is independently selected from hydrogen, C1-C3 alkyl, C1-C3 monohaloalkyl, and C1-C3 polyhaloalkyl;
wherein each of R 43 and R 44 , when present, is independently selected from —O − , —OR 45 , C1-C3 alkyl, C1-C3 monohaloalkyl, C1-C3 polyhaloalkyl, and —NR 46a R 46b ;
wherein each of R 45 , R 46a , and R 46b , when present, is selected from hydrogen, C1-C3 alkyl, C1-C3 monohaloalkyl, and C1-C3 polyhaloalkyl; and
wherein at least one Z is a structure represented by a formula:

2. The membrane of claim 1 , wherein the membrane further comprises a support structure.

3. The membrane of claim 1 , wherein the membrane further comprises a second polymer selected from polysulfone, sulfonated polysulfone, polyethersulfone, sulfonated polyethersulfone, polyaniline, polyaniline co-polymers, polyacrylonitrile, polyurethane, cellulose acetate, polyvinylidene fluoride, polytetrafluoroethylene, polyvinyl fluoride, polyvinylidene fluoride, polytrifluoroethylene, polyperfluoroalkyl vinyl ether, polyhexafluoropropylene, cellulose acetate, polyurethane, cellulose acetate, and polyurethane, or a mixture thereof.

4. The membrane of claim 1 , wherein the membrane further comprises polysulfone.

5. The membrane of claim 1 , wherein the polymer is present in an amount from about 0.1 wt % to about 35 wt %.

6. The filtration membrane of claim 1 , wherein each of R 1a , R 1b , R 1c , and R 1d is hydrogen.

7. The filtration membrane of claim 1 , wherein each Z is a structure represented by a formula:

and at least one Z is a structure represented by a formula

8. A filtration membrane comprising a polymer formed by polymerizing a compound having a structure represented by formula II:

wherein each of R 1a , R 1b , R 1c , and R 1d is independently selected from hydrogen, halogen, —CN, —SR 20 , —OR 21 , —NR 22a R 22b , —NR 22a R 22b H + , —SO 2 R 23 , —(C═O)R 24 , and C1-C3 alkyl substituted with 0, 1, 2, or 3 groups selected from halogen, —CN, —SR 20 , —OR 21 , —NR 22a R 22b , —SO 2 R 23 , and —(C═O)R 24 ;
wherein each of R 20 , R 21 , R 22a and R 22b , when present, is independently selected from hydrogen, C1-C3 alkyl, C1-C3 monohaloalkyl, and C1-C3 polyhaloalkyl;
wherein each of R 23 and R 24 , when present, is independently selected from —O − , —OR 25 , C1-C3 alkyl, C1-C3 monohaloalkyl, C1-C3 polyhaloalkyl, and —NR 26a R 26b ; and
wherein each of R 25 , R 26a , and R 26b , when present, is independently selected from hydrogen, C1-C3 alkyl, C1-C3 monohaloalkyl, and C1-C3 polyhaloalkyl.

9. The membrane of claim 8 , wherein the membrane further comprises a support structure.

10. The membrane of claim 8 , wherein the membrane further comprises a second polymer selected from polysulfone, sulfonated polysulfone, polyethersulfone, sulfonated polyethersulfone, polyaniline, polyaniline co-polymers, polyacrylonitrile, polyurethane, cellulose acetate, polyvinylidene fluoride, polytetrafluoroethylene, polyvinyl fluoride, polyvinylidene fluoride, polytrifluoroethylene, polyperfluoroalkyl vinyl ether, polyhexafluoropropylene, cellulose acetate, polyurethane, cellulose acetate, and polyurethane, or a mixture thereof.

11. The membrane of claim 8 , wherein the membrane further comprises polysulfone.

12. The membrane of claim 8 , wherein the polymer is present in an amount from about 0.1 wt % to about 35 wt %.

13. The membrane of claim 8 , wherein the compound is

Assignees

• Univ California

Inventors

• Hoek Eric M V
• Kaner Richard B
• Huang Xinwei
• Mcverry Brian T
• Mahendra Shaily

Classifications

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G73/0266

  Polyanilines or derivatives thereof · CPC title

• C02F1/441

  by reverse osmosis · CPC title

• B01D71/68

  Polysulfones; Polyethersulfones · CPC title

• B01D69/02

  characterised by their properties · CPC title