Coated porous polymeric membranes

Patent metadata

Field	Value
Publication number	US-11731085-B2
Application number	US-202117522159-A
Country	US
Kind code	B2
Filing date	Nov 9, 2021
Priority date	May 27, 2016
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

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 method of removing metal contaminants from an organic liquid used for photoresist, the method comprising:
passing the organic liquid through a first coated porous polymeric membrane comprising a first porous polymeric membrane having a first polymer coating on surfaces thereof, wherein the first polymer coating is crosslinked and not grafted to the first porous polymeric membrane surfaces and comprises a first polymerized monomer comprising a positive charge in the organic liquid, and wherein the first polymer coating is crosslinked 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
removing a portion of the metal contaminants from the organic liquid, wherein the organic liquid used for photoresist has a lower concentration of the metal contaminants after passing through the first coated porous polymeric membrane.

2. The method of claim 1 , wherein the first porous polymeric membrane is a polyolefin membrane having a bubble point, measured from the pressure required to displace ethoxy-nonafluorobutane through pores of the first porous polymeric membrane, in a range of 4-160 psi.

3. The method of claim 1 , wherein the first polymerized monomer with a 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.

4. The method of claim 1 , wherein the first polymerized monomer with a positive charge in the organic liquid comprises acrylamido propyl trimethylammonium chloride (APTAC).

5. The method of claim 1 , wherein the first polymer coating further comprises a second polymerized monomer with a negative charge in the organic liquid, wherein the second polymerized monomer with a negative charge is selected from the 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.

6. The method of claim 1 , wherein the first polymerized monomer comprising a positive charge is a zwitterion.

7. The method of claim 1 , wherein the organic liquid comprises one or more solvents selected from the group consisting of methyl-amyl ketone, ethyl-3-ethoxypropionate, propylene glycol methyletheracetate, methanol, ethyl lactate, methyl isobutyl carbinol, N-butyl acetate, methyl-2-hydroxyisobutyrate, cyclohexanone, and propylene glycol methyl ether.

8. The method of claim 1 , wherein the metal contaminants removed from the organic liquid are selected from the group consisting of Al, Ca, Cr, Cu, Fe, Pb, Mg, Mn, Ni, K, Na, Sn, Ti, and Zn.

9. The method of claim 1 , wherein the method further comprises:
after passing the organic liquid through the first coated porous polymeric membrane, passing the organic liquid through a second coated porous polymeric membrane comprising a second porous polymeric membrane having a second polymer coating on surfaces thereof, wherein the second polymer coating is crosslinked and not grafted to the second porous polymeric membrane surfaces and comprises a second polymerized monomer with a negative charge; and
removing a portion of remaining metal contaminants from the organic liquid.

10. The method of claim 1 , wherein the first polymer coating further comprises a second polymerized monomer comprising a negative charge in the organic liquid.

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

• B01D71/82

  characterised by the presence of specified groups, e.g. introduced by chemical after-treatment · CPC title

• B01J20/3208

  Polymeric carriers, supports or substrates · CPC title

• B01J20/3282

  Crosslinked polymers · CPC title