Water treatment membrane and method for manufacturing same

Patent metadata

Field	Value
Publication number	US-11173455-B2
Application number	US-201816490012-A
Country	US
Kind code	B2
Filing date	Apr 18, 2018
Priority date	Apr 19, 2017
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

Provided is a water treatment membrane including: a porous support; and a polyamide active layer provided on the porous support, in which the polyamide active layer includes one or more units selected from among a unit of Chemical Formula 1:

a unit of Chemical Formula 2;

a unit of Chemical Formula 3;

and a unit of Chemical Formula 4;

and a manufacturing method thereof.

First claim

The invention claimed is:

1. A water treatment membrane, comprising:
a porous support; and
a polyamide active layer provided on the porous support,
wherein the polyamide active layer comprises a biguanidine compound including three or more nitrogen atoms, in which both ends of the biguanidine compound are bonded to the main chain of the polyamide active layer by forming a covalent bond with an amine-based compound or an acyl halide compound in the polyamide active layer resulting in one or more units selected from among a unit of the following Chemical Formula 1, a unit of the following Chemical Formula 2, a unit of the following Chemical Formula 3, and a unit of the following Chemical Formula 4:

wherein in Chemical Formulae 1 to 4:
U 1 and U 2 are the same as or different from each other, and are each independently a substituted or unsubstituted divalent aliphatic group, a substituted or unsubstituted divalent alicyclic group, or a substituted or unsubstituted divalent aromatic group,

U 3 is a substituted or unsubstituted trivalent aliphatic group, a substituted or unsubstituted trivalent alicyclic group, or a substituted or unsubstituted trivalent aromatic group;
A 1 to A 9 are the same as or different from each other, and are each independently any one of the following Chemical Formulae 5 to 7;
A 10 is any one of the following Chemical Formula 5 or 8;

wherein in Chemical Formulae 5 to 8:
V 1 and V 2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenylene group, and
V 3 is a substituted or unsubstituted trivalent benzene ring group; and
provided that one of A 1 to A 3 , one of A 4 and A 5 , one of A 6 and A 7 , and one of A 8 and A 9 is Chemical Formula 5.

2. The water treatment membrane of claim 1 , wherein the water treatment membrane exhibits a peak of a benzene ring between 6.8 ppm and 7.8 ppm as a result of 1 H-NMR analysis before and after the water treatment membrane is dissociated in an acid or a base.

3. The water treatment membrane of claim 1 , wherein an amount of one or more units selected from among the unit of Chemical Formula 1, the unit of Chemical Formula 2, the unit of Chemical Formula 3, and the unit of Chemical Formula 4 in the polyamide active layer is 0.01 wt % to 10 wt %.

4. The water treatment membrane of claim 1 , wherein the water treatment membrane exhibits peaks of a C═N bond and a N—C—N bond as a result of IR analysis before and after the water treatment membrane is dissociated in the acid or the base.

5. The water treatment membrane of claim 1 , wherein the water treatment membrane exhibits an m/z value of 277, 193, 178, 102, 85 or 60 as a result of MS analysis after the water treatment membrane is dissociated in the acid or the base.

6. A method for manufacturing the water treatment membrane of claim 1 , the method comprising:
preparing a porous support; and
forming a polyamide active layer on the porous support,
wherein the forming of the polyamide active layer comprises an interfacial polymerization using an aqueous solution comprising an amine-based compound and an organic solution comprising an acyl halide compound,
at least one of the aqueous solution comprising the amine-based compound and the organic solution comprising the acyl halide compound comprises one or more biguanidine compounds of the following Chemical Formula 9 or Chemical Formula 10, and
each end of the biguanidine compound separately forms a covalent bond with the amine-based compound or the acyl halide compound in the polyamide active layer thereby being covalently bonded to the main chain of the polyamide active layer:

wherein in Chemical 10:
U 4 is a substituted or unsubstituted divalent aliphatic group, a substituted or unsubstituted divalent alicyclic group, or a substituted or unsubstituted divalent aromatic group; and

T 1 to T 4 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a hydroxyl group, an acyl halide group, an isocyanate group, or a substituted or unsubstituted amine group.

7. The method of claim 6 , wherein the biguanidine compound is present in an amount of 0.01 wt % to 10 wt % in the aqueous solution comprising the amine-based compound or the organic solution comprising the acyl halide compound.

8. The method of claim 6 , wherein the amine-based compound is one or more selected from the group consisting of m-phenylenediamine, p-phenylenediamine, 1,3,6-benzenetriamine, 4-chloro-1,3-phenylenediamine, 3-chloro-1,4-phenylenediamine, and a mixture thereof.

9. The method of claim 6 , wherein the acyl halide compound is one or more selected from the group consisting of trimesolyl chloride, isophthaloyl chloride, terephthaloyl chloride, and a mixture thereof.

10. A water treatment module comprising the water treatment membrane of claim 1 .

Assignees

• Lg Chemical Ltd

Inventors

• Byun Eunkyoung
• Shin Chong Kyu
• Lee Youngju
• Jeon Hyungjoon

Classifications

• B01D69/1251 Primary

  by interfacial polymerisation · CPC title

• B01D69/1071

  Woven, non-woven or net mesh · CPC title

• B01D67/0006 Primary

  by chemical reactions (in-situ polymerisation, polycondensation, cross-linking or reaction for manufacturing composite membranes B01D69/125) · CPC title

• B01D61/025

  Reverse osmosis; Hyperfiltration · CPC title

• C02F1/44

  by dialysis, osmosis or reverse osmosis {(general membrane separation processes B01D61/00, membrane modules B01D63/00, electrodialysis C02F1/4693, combination of membrane modules and bioreactors C02F3/1268)} · CPC title