Coated porous polymeric membranes

Patent metadata

Field	Value
Publication number	US-11285443-B2
Application number	US-201716304900-A
Country	US
Kind code	B2
Filing date	May 26, 2017
Priority date	May 27, 2016
Publication date	Mar 29, 2022
Grant date	Mar 29, 2022

Abstract

The present disclosure provides a porous polymeric membrane that is coated with a cross-linked polymerized monomer. The coating on the porous polymeric membrane has a charge when it is immersed in an organic liquid. The coated porous polymeric membrane, a filter utilizing the membrane, and a method for treating an organic liquid used for photoresist with the coated porous polymeric membrane to remove metal contaminants from the organic liquid are disclosed.

First claim

What is claimed is:

1. A coated porous polymeric membrane comprising a porous polymeric membrane having a polymer coating on surfaces thereof, wherein the polymer coating is cross-linked and not grafted to the porous polymeric membrane surfaces and has a polymerized monomer comprising a positive charge in an organic liquid,
wherein the coating is cross-linked with a cross-linking agent selected from the group consisting of 1,6-hexanediol diacrylate, tetraethylene glycol diacrylate, 1,1,1-trimethylolpropane triacrylate, and combinations thereof and
wherein the porous polymeric membrane is a polyolefin membrane having a bubble point, measured from the pressure required to displace ethoxy-nonafluorobutane through pores of the porous polymeric membrane, in a range of 4-160 psi.

2. The porous membrane of claim 1 , wherein the monomer comprising the positive charge in the organic liquid is selected from a group consisting of 2-(dimethylamino)ethyl hydrochloride acrylate, [2-(acryloyloxy)ethyl]trimethylammonium chloride, 2-aminoethyl methacrylate hydrochloride, N-(3-aminopropyl) methacrylate hydrochloride, 2-(dimethylamino)ethyl methacrylate hydrochloride, [3-(methacryloylamino)propyl] trimethylammonium chloride solution, [2-(methacryloyloxy)ethyl]trimethylammonium chloride, acrylamidopropyl trimethylammonium chloride, 2-aminoethyl methacrylamide hydrochloride, N-(2-aminoethyl) methacrylamide hydrochloride, N-(3-aminopropyl)-methacrylamide hydrochloride, diallyldimethylammonium chloride, allylamine hydrochloride, vinyl imidazolium hydrochloride, vinyl pyridinium hydrochloride, and vinyl benzyl trimethyl ammonium chloride.

3. The porous membrane of claim 1 , wherein the monomer comprising the positive charge in the organic liquid comprises acrylamido propyl trimethylammonium chloride (APTAC).

4. The porous membrane of claim 1 , wherein the monomer comprising the positive charge in the organic liquid is a zwitterion.

5. A filtration device comprising: a first coated porous polymeric membrane comprising a first porous polymeric membrane having a polymer coating on surfaces thereof, wherein the polymer coating is cross-linked and not grafted to the first porous polymeric membrane surfaces and has a polymerized monomer with a positive charge in an organic liquid, and a second coated porous polymeric membrane comprising a second porous polymeric membrane having a polymer coating on surface thereof, wherein the polymer coating is cross-linked and not grafted to the second porous polymeric surfaces and has a polymerized monomer with a negative charge in the organic liquid,
wherein the coating is cross-linked with a cross-linking agent selected from the group consisting of 1,6-hexanediol diacrylate, tetraethylene glycol diacrylate, 1,1,1-trimethylolpropane triacrylate, and combinations thereof and
wherein the first porous polymeric membrane or the second porous polymeric membrane is a polyolefin membrane having a bubble point, measured from the pressure required to displace ethoxy-nonafluorobutane through pores of the porous polymeric membrane, in a range of 4-160 psi.

6. The filtration device of claim 5 , in which the monomer comprising the positive charge in the organic liquid is selected from a group consisting of 2-(dimethylamino)ethyl hydrochloride acrylate, [2-(acryloyloxy)ethyl]trimethylammonium chloride, 2-aminoethyl methacrylate hydrochloride, N-(3-aminopropyl) methacrylate hydrochloride, 2-(dimethylamino)ethyl methacrylate hydrochloride, [3-(methacryloylamino)propyl] trimethylammonium chloride solution, [2-(methacryloyloxy)ethyl]trimethylammonium chloride, acrylamidopropyl trimethylammonium chloride, 2-aminoethyl methacrylamide hydrochloride, N-(2-aminoethyl) methacrylamide hydrochloride, N-(3-aminopropyl)-methacrylamide hydrochloride, diallyldimethylammonium chloride, allylamine hydrochloride, vinyl imidazolium hydrochloride, vinyl pyridinium hydrochloride, and vinyl benzyl trimethyl ammonium chloride.

7. The filtration device of claim 5 , in which the monomer comprising the negative charge in the organic liquid is selected from a group consisting of 2-ethylacrylic acid, acrylic acid, 2-carboxyethyl acrylate, 3-sulfopropyl acrylate potassium salt, 2-propyl acrylic acid, 2-(trifluoromethyl)acrylic acid, methacrylic acid, 2-methyl-2-propene-1-sulfonic acid sodium salt, mono-2-(methacryloyloxy)ethyl maleate, and 3-sulfopropyl methacrylate potassium salt, 2-acrylamido-2-methyl-1-propanesulfonic acid, 3-methacrylamido phenyl boronic acid, vinyl sulfonic acid, and vinyl phosphonic acid.

8. The porous membrane of claim 1 , wherein said coating further comprises polymerized monomers with negative charges.

9. The porous membrane of claim 8 , wherein the monomer with a positive charge is selected from a group consisting of 2-(dimethylamino)ethyl hydrochloride acrylate, [2-(acryloyloxy)ethyl]trimethylammonium chloride, 2-aminoethyl methacrylate hydrochloride, N-(3-aminopropyl) methacrylate hydrochloride, 2-(dimethylamino)ethyl methacrylate hydrochloride, [3-(methacryloylamino)propyl]trimethylammonium chloride solution, [2-(methacryloyloxy)ethyl]trimethylammonium chloride, acrylamidopropyl trimethylammonium chloride, 2-aminoethyl methacrylamide hydrochloride, N-(2-aminoethyl) methacrylamide hydrochloride, N-(3-aminopropyl)-methacrylamide hydrochloride, diallyldimethylammonium chloride, allylamine hydrochloride, vinyl imidazolium hydrochloride, vinyl pyridinium hydrochloride, and vinyl benzyl trimethyl ammonium chloride.

10. The porous membrane of claim 8 , wherein the monomer with a negative charge is selected from a group consisting of 2-ethylacrylic acid, acrylic acid, 2-carboxyethyl acrylate, 3-sulfopropyl acrylate potassium salt, 2-propyl acrylic acid, 2-(trifluoromethyl)acrylic acid, methacrylic acid, 2-methyl-2-propene-1-sulfonic acid sodium salt, mono-2-(methacryloyloxy)ethyl maleate, and 3-sulfopropyl methacrylate potassium salt, 2-acrylamido-2-methyl-1-propanesulfonic acid, 3-methacrylamido phenyl boronic acid, vinyl sulfonic acid, and vinyl phosphonic acid.

11. The porous polymeric membrane of claim 1 , wherein the polyolefin membrane is an ultra-high molecular weight polyethylene membrane.

12. The porous membrane of claim 1 , wherein the monomer comprising the positive charge in the organic liquid is selected from a group consisting of 2-(dimethylamino)ethyl hydrochloride acrylate, [2-(acryloyloxy)ethyl]trimethylammonium chloride, 2-aminoethyl methacrylate hydrochloride, N-(3-aminopropyl) methacrylate hydrochloride, 2-(dimethylamino)ethyl methacrylate hydrochloride, [3-(methacryloylamino)propyl] trimethylammonium chloride solution, [2-(methacryloyloxy)ethyl]trimethylammonium chloride, acrylamidopropyl trimethylammonium chloride, diallyldimethylammonium chloride, allylamine hydrochloride, vinyl imidazolium hydrochloride, vinyl pyridinium hydrochloride, and vinyl benzyl trimethyl ammonium chloride.

13. The filtration device of claim 5 , wherein the monomer comprising the positive charge in the organic liquid is selected from a group consisting of 2-(dimethylamino)ethyl hydrochloride acrylate, [2-(acryloyloxy)ethyl]trimethylammonium chloride, 2-aminoethyl methacrylate hydrochloride, N-(3-aminopropyl) methacrylate hydrochloride, 2-(dimethylamino)ethyl methacrylate hydrochloride, [3-(methacryloylamino)propyl] trimethylammonium chloride solution, [2-(methacryloyloxy)ethyl]trimethylammonium chloride, acrylamidopropyl trimethylammonium chloride, diallyldimethylammonium chloride, allylamine hydrochloride, vinyl imidazolium hydrochloride, vinyl pyridinium hydrochloride, and vinyl benzyl trimethyl ammonium chloride.

Assignees

• Entegris Inc

Inventors

• Jaber Jad Ali
• Ly Saksatha
• Hamzik James
• Kohyama Testu

Classifications

• B01D71/261

  Polyethylene · CPC title

• B01D67/0088 Primary

  Physical treatment with compounds, e.g. swelling, coating or impregnation · CPC title

• B01J47/12

  characterised by the use of ion-exchange material in the form of ribbons, filaments, fibres or sheets, e.g. membranes (electrodialysis or electro-osmosis B01D61/42) · CPC title

• C08J2333/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• B01J20/3282

  Crosslinked polymers · CPC title