Compound for fouling resistance, membrane for fouling resistance, and method of preparing membrane for fouling resistance

Patent metadata

Field	Value
Publication number	US-10220355-B2
Application number	US-201415103120-A
Country	US
Kind code	B2
Filing date	Dec 8, 2014
Priority date	Dec 9, 2013
Publication date	Mar 5, 2019
Grant date	Mar 5, 2019

Abstract

A fouling resistant and antibiotic copolymer including a first structural unit and a second structural unit is disclosed.

First claim

The invention claimed is:

1. A fouling resistant and antibiotic copolymer, comprising
a first structural unit represented by the following Chemical Formula 1 and a second structural unit represented by the following Chemical Formula 2:

wherein, in the above Chemical Formulae 1 and 2,
R 1 to R 3 and R 5 to R 7 are independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 heterocycloalkyl group, a substituted or unsubstituted C5 to C20 heteroaryl group, a substituted or unsubstituted C2 to C20 alkylaryl group, or a substituted or unsubstituted C2 to C30 arylalkyl group,
L 1 and L 2 are a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C5 to C20 arylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C1 to C20 heterocycloalkylene group, a substituted or unsubstituted C1 to C30 heteroarylene group, a substituted or unsubstituted C2 to C20 alkylarylene group, a substituted or unsubstituted C2 to C20 arylalkylene group, or a combination thereof linked to each other,
X 1 is a single bond, —O—, —NH—, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C5 to C20 arylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C1 to C20 heterocycloalkylene group, a substituted or unsubstituted C1 to C20 heteroarylene group, a substituted or unsubstituted C2 to C20 alkylarylene group, a substituted or unsubstituted C2 to C20 arylalkylene group, or a combination thereof linked to each other,
R 4 is independently a C1 to C30 alkyl group, a C5 to C30 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C30 alkoxy group, a C1 to C30 fluoroalkyl group, a C5 to C30 alkenyl group having at least one double bond, or a C5 to C30 alkynyl group having at least one triple bond, provided that at least one thereof is a saturated or unsaturated hydrocarbon group having a carbon number of 4 or more,
R 8 is independently —OH, —COOH, —NH 2 , —SH, —SO 3 H, —F, —Cl, —Br, —I, a C1 to C10 alkyl group, a C2 to C10 alkenyl group, a C3 to C20 cycloalkyl group, a C2 to C20 heterocycloalkyl group, a C6 to C20 aryl group, a C2 to C20 heteroaryl group, a C1 to C10 alkoxy group, or a C1 to C10 fluoroalkyl group, provided at least two thereof are OH groups,
m is an integer of 1 to 5, and
n is an integer of 2 to 5.

2. The copolymer of claim 1 , wherein, in the above Chemical Formula 1, R 1 to R 3 are hydrogen or a C1 to C4 alkyl group, L 1 is a substituted or unsubstituted C1 to C10 alkylene group, R 4 is a C4 to C30 alkyl group or a C4 to C30 alkenyl group including 1 to 5 double bonds, and m is 1 or 2.

3. The copolymer of claim 1 , wherein, in the above Chemical Formula 2, R 8 to R 7 are hydrogen or a C1 to C4 alkyl group, L 2 is a substituted or unsubstituted C1 to C10 alkylene group, X 1 is —O—, —NH—, or a C1 to C20 alkylene group, R 8 is —OH, and n is 2.

4. The copolymer of claim 1 , wherein the above Chemical Formula 1 is represented by the following Chemical Formula 3:

wherein, in the above Chemical Formula 3, R 4 is independently a C4 to C30 alkyl group or a C4 to C30 alkenyl group including 1 to 5 double bonds in each repeating unit.

5. The copolymer of claim 1 , wherein the above Chemical Formula 2 is represented by the following Chemical Formula 4:

6. The copolymer of claim 1 , which is represented by the following Chemical Formula 5:

wherein, in the above Chemical Formula 5,
R 1 to R 8 , L 1 , L 2 , X 1 , m, and n are the same as defined in the Chemical Formulae 1 and 2,
x and y indicate each mole fraction of the structural unit represented by the above Chemical Formula 1 and the structural unit represented by the above Chemical Formula 2, 0<x≤0.5, and 0.5≤y<1.

7. The copolymer of claim 6 , wherein x and y are in the ranges of 0.1≤x≤0.4, and 0.6≤y≤0.9.

8. The copolymer of claim 6 , wherein x and y are in the ranges of 0.2≤x≤0.3 and 0.7≤y≤0.8.

9. The copolymer of claim 1 , which has a number average molecular weight of about 3000 to about 100,000.

10. The copolymer of claim 1 , which is represented by the following Chemical Formula 6:

wherein, in the above Chemical Formula 6,
0.1≤x≤0.4, 0.6≤y≤0.9, and R 4 is independently a C10 to C20 alkyl group or a C10 to C20 alkenyl group including 1 to 5 double bonds in each repeating unit.

11. A fouling resistant and antibiotic membrane comprising the copolymer of claim 1 .

12. The fouling resistant and antibiotic membrane of claim 11 , which comprises a surface layer comprising the copolymer on an inner layer comprising at least one selected from a polyacrylate-based compound, a polymethacrylate-based compound, a polystyrene-based compound, a polycarbonate-based compound, a polyethylene terephthalate-based compound, a polyimide-based compound, a polybenzimidazole-based compound, a polybenzthiazole-based compound, a polybenzoxazole-based compound, a polyepoxy-based resin compound, a polyolefin-based compound, a polyphenylene vinylene compound, a polyamide-based compound, a polyacrylonitrile-based compound, a polysulfone-based compound, a cellulose-based compound, polyvinylidene fluoride (PVDF), polytetrafluoroethylene (PTFE), and a polyvinyl chloride (PVC) compound.

13. The fouling resistant and antibiotic membrane of claim 12 , wherein the inner layer is a single membrane formed of a homogeneous material, or a hybrid membrane including a plurality of layers formed of heterogeneous materials.

14. The fouling resistant and antibiotic membrane of claim 12 , wherein the surface layer is manufactured by coating a solution including the copolymer on the surface of the inner layer.

15. The fouling resistant and antibiotic membrane of claim 12 , wherein the surface layer has a thickness of about 0.01 μm to about 100 μm.

16. The fouling resistant and antibiotic membrane of claim 12 , wherein the inner layer comprises polysulfone.

17. A separation membrane for water treatment comprising the fouling resistant and antibiotic membrane of claim 11 .

18. A water treatment device comprising the separation membrane for water treatment of claim 17 .

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kang Hyo
• Han Sung Soo

Classifications

• C08F220/58

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} · CPC title

• B01D2325/36

  Hydrophilic membranes · CPC title

• C08F120/30

  containing aromatic rings in the alcohol moiety · CPC title

• B01D69/02

  characterised by their properties · CPC title

• B01D71/76 Primary

  Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 (rubbers in general B01D71/24) · CPC title