Composite membrane and method of making the same

Patent metadata

Field	Value
Publication number	US-12485388-B2
Application number	US-202117915533-A
Country	US
Kind code	B2
Filing date	Apr 1, 2021
Priority date	Apr 2, 2020
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

The present invention relates to a method for producing a composite membrane, the method comprising impregnating a surface of a porous membrane substrate with an aqueous suspension comprising a mixture of at least one polyamine and at least one phospholipid; and contacting the impregnated surface with an organic phase containing a monomer to thereby deposit a polyamide layer on the impregnated surface. The present invention also relates to a composite membrane comprising at least one porous membrane substrate having nano-sized or micro-sized pores; and at least a polyamide layer disposed on a surface of the porous membrane substrate, the polyamide layer comprising at least one phospholipid dispersed therein, and wherein the polyamide layer is an interfacial polymerization product.

First claim

The invention claimed is:

1 . A composite membrane comprising:
a) at least one porous membrane substrate having nano-sized or micro-sized pores, and b) at least a polyamide layer disposed on a surface of the porous membrane substrate, the polyamide layer comprising at least one phospholipid dispersed therein, and wherein the polyamide layer is an interfacial polymerization product; wherein the polyamide layer does not comprise aquaporins; and wherein the polyamide layer is a fully aromatic polyamide layer comprising leaf-like features with an apparent height of between 200 nm to 4,000 nm.

2 . The composite membrane of claim 1 , wherein the polyamide layer is formed via interfacial polymerization which comprises first impregnating the surface of the porous membrane substrate with an aqueous phase comprising at least one polyamine and the phospholipid;
rinsing the surface of the impregnated porous membrane substrate with an organic solvent; and contacting the impregnated porous membrane with an organic phase containing a monomer comprising at least one crosslinking group to thereby result in the formation of the polyamide layer.

3 . The composite membrane of claim 1 , wherein the phospholipid is provided in a molar concentration of from about 10 μM to about 10 mM in the aqueous phase; preferably from about 50 μM to about 4 mM.

4 . The composite membrane of claim 1 , wherein the phospholipid has a formula (I):

wherein R 1 represents a saturated or an unsaturated aliphatic group having 14 to 24 carbon atoms; and
wherein R 2 represents a saturated or an unsaturated aliphatic group having 14 to 24 carbon atoms; and
wherein R 3 is:

5 . The composite membrane of claim 2 , wherein the polyamine comprises at least two amine groups, wherein said amine groups are independently primary amine or secondary amine groups.

6 . The composite membrane of claim 2 , wherein the organic phase comprises the monomer comprising at least one crosslinking group in a concentration of from about 0.00001 wt. % to about 2 wt. %; preferably from about 0.001 wt. % to 1 wt. %.

7 . The composite membrane of claim 1 , wherein the porous membrane substrate comprises polyethersulfone, polyetherimide, polysulfone, polyacrylonitrile, polyimide, polyvinylidene fluoride, polypropylene, poly(tetrafluoroethylene), or co-polymers thereof.

8 . The composite membrane of claim 1 , wherein the polyamide layer does not comprise a transmembrane protein or analogues thereof.

9 . A hollow fiber membrane or a flat-sheet membrane comprising the composite membrane of claim 1 .

10 . The composite membrane of claim 4 , wherein the phospholipid is selected from the group consisting of: 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) (DOPG), L-α-phosphatidylcholine (egg PC), 1,2-ditetradecanoyl-sn-glycero-3-phosphocholine (DMPC), 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (POPC), 1,2-dilauroyl-sn-glycero-3-phosphocholine (DLPC), 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), 1,2-dilauroyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) (DLPG), 1,2-dimyristoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) (DMPG), 1,2-dipalmitoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) (DPPG), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (sodium salt) (POPG), 1,2-dimyristoyl-sn-glycero-3-phospho-L-serine (sodium salt) (DMPS), 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine (sodium salt) (DPPS), 1,2-distearoyl-sn-glycero-3-phospho-L-serine (sodium salt) (DSPS), 1,2-dioleoyl-sn-glycero-3-phospho-L-serine (sodium salt) (DOPS), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (sodium salt) (POPS), 1,2-dilauroyl-sn-glycero-3-phosphate (sodium salt) (DLPA), 1,2-dimyristoyl-sn-glycero-3-phosphate (sodium salt) (DMPA), 1,2-dipalmitoyl-sn-glycero-3-phosphate (sodium salt) (DPPA), 1,2-distearoyl-sn-glycero-3-phosphate (sodium salt) (DSPA), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphate (sodium salt) (POPA), 1,2-dilauroyl-sn-glycero-3-phosphoethanolamine (DLPE), 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine (DMPE), 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE), 1,2-distearoyl-sn-glycero-3-phosphoethanolamine (DSPE), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), E. coli lipid extract, soy lipid extract, yeast lipid extract, 1-palmitoyl-2-(dipyrrometheneboron difluoride) undecanoyl-sn-glycero-3-phosphocholine, 1,2-dioleoyl-sn-glycero-3-phospho-(1′-myo-inositol) (ammonium salt) (DOPI), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoinositol (ammonium salt) (POPI), 1,2-dipalmitoyl-sn-glycero-3-phospho-(1′-myo-inositol) (ammonium salt) (DPPI), 1,1′, 2,2′-tetraoleoyl cardiolipin (TOCL), 1,2-dioleoyl-sn-glycero-3-phosphoethanol (DOPEt), 1,2-dioleoyl-sn-glycero-3-phosphoethanol (DOPEt) (18:0 diethyl PC), or combinations thereof; or wherein the phospholipid is selected from the group consisting of: 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-Dioleoyl-snglycero-3-phospho-rac-(1-glycerol) (DOPG), L-α-phosphatidylcholine (egg PC), 1,2-ditetradecanoyl-sn-glycero-3-phosphocholine (DMPC), 2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (POPC), and mixtures thereof.

11 . The composite membrane of claim 5 , wherein the polyamine is selected from the group consisting of: m-phenylenediamine (MPD), m-phenylenediamine-4-methyl, 1,3-cyclohexanebis(methylamine), o-phenylenediamine (OPD), piperazine, p-phenylenediamine (PPD), 1,1′-biphenyl-4,4′-diamine (benzidine), polyethyleneimine, and mixtures thereof.

12 . The composite membrane of claim 2 , wherein the monomer comprising at least one crosslinking group is selected from the group consisting of trimesoyl chloride (1,3,5-benzenetricarbonyl trichloride), terephthalic acid chloride, isophthalic acid chloride, biphenyl dicarboxylic acid chloride, naphthalene dicarboxylic acid dichloride, biphenyl-4,4′-disulfonyl chloride, 1,3,6-naphthalenetrisulfonyl chloride, and mixtures thereof.

13 . The composite membrane of claim 2 , wherein the organic phase further comprises an organic solvent which is unreactive with the monomer comprising at least one crosslinking group.

Assignees

• Univ Nanyang Tech
• H2Mo Tech Pte Ltd

Inventors

• Wang Rong
• Li Qing
• Li Ye
• Chen Yunfeng
• Wang Yining
• Zhang Lizhi

Classifications

• B01D2323/46

  Impregnation · CPC title

• B01D2323/40

  in-situ membrane formation · CPC title

• B01D2323/30

  Cross-linking · CPC title

• B01D2323/12

  Specific ratios of components used · CPC title

• B01D71/56

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