IP Library Granted Patent US 9,649,597
Granted Patent B2
US 9,649,597 · App. 14/197,204 · Granted May 16, 2017

Polyamide water-treatment separation membrane with improved antifouling properties and manufacturing method thereof

Inventors: Phill Lee (Daejeon, KR); Jae-Hong Kim (Daejeon, KR); Chong-Kyu Shin (Daejeon, KR); Joung-Eun Yoo (Daejeon, KR); Seung-Pyo Jeong (Daejeon, KR); Young-Ju Lee (Daejeon, KR); Young-Hoon Ko (Daejeon, KR); Hye-Jin Kwon (Daejeon, KR)
Assignee: LG CHEM, LTD.
B01D61/025B01D67/0088B01D67/0093B01D69/12B01D71/32B01D71/56B01D71/80C02F1/441B01D71/52B01D2325/28C02F1/44
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Quick Facts
Patent No.
US 9,649,597
App. No.
14/197,204
Granted
May 16, 2017
Kind
B2
Abstract

A water-treatment separation membrane with good antifouling properties includes a support having pores, a polyamide layer formed on the support, and a passivation layer comprising specific materials formed on the polyamide layer.

Claims (33)

1. A water-treatment separation membrane comprising:

a support having pores;

a polyamide layer formed on the support; and

a passivation layer formed on the polyamide layer, the passivation layer including a compound represented by following formula (I),

L 1 -A-L 2 -B-L 3 ,  [Formula I]

in which L 1 is an amine, a haloalkyl, a haloalkenyl, a haloalkynyl, a hydroxyl, a ketone, an aldehyde, an acyl halide, a carbonate, an ester, an ether, an imine, an azide, a nitrile, a thiocyanate, a thione, a thial, a phosphate, an epoxide, an acryloyl amine or a thiol,

A includes one or more C1-6 alkylene unit, one or more C1-6 alkylene oxide unit or a combination thereof,

L 2 is at least one selected from the group consisting of following formulae (II) to (V),

B is an unsubstituted C 1-20 alkylene, aryl alkylene, alkylene oxide, alkenylene, aryl alkenylene or alkenylene oxide or a substituted C 1-20 alkylene, aryl alkylene, alkylene oxide, alkenylene, aryl alkenylene or alkenylene oxide in which the alkylene, the aryl alkylene, the alkylene oxide, the alkenylene, the aryl alkenylene or the alkenylene oxide is substituted with at least one selected from a group consisting of a halogen, a sulfonyl, an amine, a hydroxyl and a ketone, and

L 3 is —CF 3 or —F.

2. The water-treatment separation membrane of claim 1 , wherein A is at least one selected from a group consisting of the following formulae (VI) to (XII):

3. The water-treatment separation membrane of claim 1 , wherein B is at least one selected from a group consisting of following compounds, in which n is 1 to 10 and m is 0 to 10:

4. The water-treatment separation membrane of claim 1 , wherein the compound represented by formula (I) is selected from a group consisting of following compounds:

in which each of x, y and z is an integer from 0 to 70, x+y+z is an integer from 1 to 70, and q is an integer from 1 to 150.

5. The water-treatment separation membrane of claim 1 , wherein the compound represented by formula (I) is grafted to the polyamide layer.

6. A method of forming a water-treatment separation membrane, the method comprising:

providing a support having pores and a polyamide layer formed thereon; and

forming a passivation layer including a compound represented by following formula (I) on the polyamide layer,

L 1 -A-L 2 -B-L 3 ,  [Formula I]

in which L 1 is an amine, a haloalkyl, a haloalkenyl, a haloalkynyl, a hydroxyl, a ketone, an aldehyde, an acyl halide, a carbonate, an ester, an ether, an imine, an azide, a nitrile, a thiocyanate, a thione, a thial, a phosphate, an epoxide, an acryloyl amine or a thiol,

A includes one or more C 1-6 alkylene unit, one or more C 1-6 alkylene oxide unit or a combination thereof,

L 2 is at least one selected from the group consisting of following formulae (II) to (V),

B is an unsubstituted C 1-20 alkylene, aryl alkylene, alkylene oxide, alkenylene, aryl alkenylene or alkenylene oxide or a substituted C 1-20 alkylene, aryl alkylene, alkylene oxide, alkenylene, aryl alkenylene or alkenylene oxide in which the alkylene, the aryl alkylene, the alkylene oxide, the alkenylene, the aryl alkenylene or the alkenylene oxide is substituted with at least one selected from a group consisting of a halogen, a sulfonyl, an amine, a hydroxyl and a ketone, and

L 3 is —CF 3 or —F.

7. The method of claim 6 , wherein forming the passivation layer comprises impregnating the support including the polyamide layer formed thereon with an aqueous solution including the compound represented by formula (I).

8. The method of claim 6 , wherein forming the water treatment separation membrane comprises exposing the support to an aqueous solution including the compound represented by formula (I), and the aqueous solution includes 0.01 to 10 wt % of the compound represented by formula (I).

9. The method of claim 6 , wherein A is at least one selected from a group consisting of the following formulae (VI) to (XII):

10. The method of claim 6 , wherein B is at least one selected from a group consisting of following compounds, in which n is an integer from 1 to 10 and m is an integer from 0 to 10:

11. The method of claim 6 , wherein the compound represented by formula (I) is selected from a group consisting of following compounds:

in which each of x, y and z is an integer from 0 to 70, x+y+z is an integer from 1 to 70, and q is an integer from 1 to 150.

12. The method of claim 6 , wherein the compound represented by formula (I) is grafted to the polyamide layer.

13. A water-treatment module comprising the water-treatment separation membrane according to claim 1 .

14. A water-treatment apparatus comprising the water-treatment module of claim 13 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2025
From: LG CHEM, LTD.
To: NANOH2O CO., LTD.
Reel/Frame 073784/0326 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2017
From: YOO, JOUNG-EUN; JEONG, SEUNG-PYO
To: LG CHEM, LTD.
Reel/Frame 041788/0992 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2015
From: LEE, PHILL; KIM, JAE-HONG; SHIN, CHONG-KYU; LEE, YOUNG-JU; LEE, YOUNG-HOON; KWON, HYE-JIN
To: LG CHEM, LTD.
Reel/Frame 034771/0015 →
Priority Claims (2)
KR 10-2012-0124487 · Nov 5, 2012 · national
KR 10-2013-0108427 · Sep 10, 2013 · national
Continuity (2)
Continuation In Part PCTKR2013008183 · Sep 10, 2013
Related Publication 20140183128A1 · Jul 3, 2014