IP Library Granted Patent US 12,595,396
Granted Patent B2
US 12,595,396 · App. 17/356,201 · Granted Apr 7, 2026

Acid resistant filter media

Inventors: James Hamzik (North Billerica, MA); KwokShun Cheng (Nashua, NH); Jad A. Jaber (Westford, MA); Nicholas J. Filipancic (Medford, MA)
Assignee: Entegris, Inc.
C09D177/02B01D67/00931B01D69/02B01D69/10B01D69/1251B01D71/401B01D71/56B01D2239/0478B01D2325/36
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Quick Facts
Patent No.
US 12,595,396
App. No.
17/356,201
Granted
Apr 7, 2026
Kind
B2
Abstract

Provided are certain membranes useful in the filtration of liquids and removal of various contaminants therein. In certain aspects the membranes have as one component a polyamide such as Nylon 11 and/or Nylon 12. Also provided is methodology for manufacturing such membranes and their use in filtration and purification of liquids. Membranes of the disclosure thus prepared exhibit superior acid stability when compared to polyamide membranes prepared from Nylon 6 or Nylon 6,6.

Claims (21)

1 . A composite porous filter membrane comprising:

a porous hydrophobic polymeric filter media having a coating thereon which at least partially coats surfaces throughout the porous hydrophobic polymeric filter media,

wherein said coating is a polyamide polymer possessing a repeat unit structure of the formula —[(CH 2 ) x C(O)NH] n —, wherein x is an integer of from about 8 to 12, and n represents the number of repeat units in the polyamide polymer, and

wherein the composite porous filter membrane has the following characteristics:

(i) a surface energy of from greater than 30 to 100 dynes/cm;

(ii) an isopropanol flowtime of about 150 to about 20,000 seconds/500 mL, measured at 14.2 psi;

(iii) a bubble point of about 20 to about 200 psi, when measured using ethoxy-nonafluorobutane HFE 7200 at a temperature of about 22° C.;

(iv) a capacity to bind Ponceau S dye of between about 1 and about 30 μg/cm 2 and the capacity to bind methylene blue dye (MB DBC) of between about 1 and about 30 μg/cm 2 ; and

(v) after exposure of the composite porous filter membrane to a >96% formic acid solution for 24 hours and flushing of the composite porous filter membrane with de-ionized water until a stable pH is obtained, the composite porous filter membrane retaining the surface energy of from greater than 30 to 100 dynes/cm.

2 . The composite porous filter membrane of claim 1 , wherein the polyamide polymer is chosen from Nylon 11 and Nylon 12.

3 . The composite porous filter membrane of claim 1 , wherein the porous hydrophobic polymeric filter media is chosen from polyethylene, polypropylene, polycarbonate, poly (tetrafluoro ethylene), polyvinylidene fluoride, and polyarylsulfone.

4 . The composite porous filter membrane of claim 3 , wherein the porous hydrophobic polymeric filter media is chosen from ultrahigh molecular weight polyethylene and poly (tetrafluoro ethylene).

5 . The composite porous filter membrane of claim 1 , wherein the hydrophobic polymeric filter media having a coating thereon is coated with a free-radical reaction product of (i) at least one crosslinker and (ii) at least one monomer in the presence of a photo-initiator.

6 . The composite porous filter membrane of claim 5 , wherein each of the at least one crosslinker is chosen from methylene bis(acrylamide), tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, divinyl sulfone, divinyl benzene, 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, and ethylene glycol divinyl ether.

7 . The composite porous filter membrane of claim 5 ,

wherein each of the at least one monomer is chosen from 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, vinyl benzyl trimethyl ammonium chloride, and acrylamido propyl trimethylammonium chloride, 2-ethylacrylic acid, acrylic acid, 2-carboxy ethyl 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, 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 composite porous filter membrane of claim 5 , from 2-ethylacrylic acid, acrylic acid, 2-carboxy ethyl 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, 3-sulfopropyl methacrylate potassium salt, 2-acrylamido-2-methyl-1-propanesulfonic acid, 3-methacrylamido phenyl boronic acid, vinyl sulfonic acid, and vinyl phosphonic acid.

9 . The composite porous filter membrane of claim 5 , wherein each of the at least one monomer is chosen from acryl amide, N,N-dimethyl acrylamide, N-(hydroxyethyl)acrylamide, diacetone acrylamide, N-[tris(hydroxymethyl)methyl] acrylamide, N-(isobutoxymethyl)acrylamide, N-(3-methoxypropyl)acrylamide, 7-[4-(trifluoromethyl)coumarin] acrylamide, N-isopropyl acrylamide, 2-(dimethylamino)ethyl acrylate, 1,1,1,3,3,3-hexafluoroisopropyl acrylate, ethyl acrylate, 2-hydroxyethyl acrylate, butyl acrylate, ethylene glycol methyl ether acrylate, 4-hydroxybutyl acrylate, hydroxypropyl acrylate, 4-acetoxyphenethyl acrylate, benzyl acrylate, 1-vinyl-2-pyrrolidinone, vinyl acetate, ethyl vinyl ether, vinyl 4-tert-butylbenzoate, and phenyl vinyl sulfone.

10 . The composite porous filter membrane of claim 1 , wherein the composite membrane is grafted with pendant hydrophilic groups chosen from hydroxyl groups, amine groups, carboxylic groups, or combinations thereof; and pendant ionic groups that are different from the pendant hydrophilic groups.

11 . A method for removing an impurity from a liquid, which comprises contacting the liquid with the composite porous filter membrane of claim 1 .

12 . A filter comprising the composite porous filter membrane of claim 1 .

Assignments (3)
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.
To: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
Reel/Frame 060614/0980 →
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.; CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: TRUIST BANK, AS NOTES COLLATERAL AGENT
Reel/Frame 060613/0072 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2021
From: FILIPANCIC, NICHOLAS J.; HAMZIK, JAMES; CHENG, KWOK-SHUN; JABER, JAD A.
To: ENTEGRIS, INC.
Reel/Frame 056643/0156 →
Continuity (2)
Provisional Application 63043013 · Jun 23, 2020
Related Publication 20210395566A1 · Dec 23, 2021
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