IP Library Granted Patent US 12,453,942
Granted Patent B2
US 12,453,942 · App. 17/738,518 · Granted Oct 28, 2025

Porous poly (cyclic olefin) membranes

Inventors: Sina Bonyadi (Billerica, MA); Pushkara Rao Varanasi (Poughkeepsie, NY); Zhifeng Li (Acton, MA); Carrie Lynn Frazee (Bedford, MA); Larry F. Rhodes (Akron, OH); Leah Langsdorf (Akron, OH)
Assignees: ENTEGRIS, INC.; PROMERUS, LLC
B01D71/44B01D67/0013B01D69/02B01D2325/02B01D2325/04
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Quick Facts
Patent No.
US 12,453,942
App. No.
17/738,518
Granted
Oct 28, 2025
Kind
B2
Abstract

The disclosure provides certain porous membranes comprised of cyclic polyolefin polymers, such as poly(norbornene)s. In one embodiment, a poly(norbornene) polymer is dissolved in tetrahydrofuran, cast into a film and subjected to solvent induced phase separation to provide a porous filter membrane (i.e., film).

Claims (28)

1. A porous membrane comprising:

a poly (cyclic olefin) copolymer according to:

wherein n and m represent the number of repeat units of each type, p is 0 or 1, and R is chosen from:

(i) a C 1 -C 10 alkyl group; and

(ii) a C 1 -C 10 alkyl group substituted one to three times with a group chosen from halo, nitro, C 1 -C 4 alkoxy, cyano, amine, sulfonamide, sulfonic acid, trifluoromethanesulfonamido, phosphonic acid, carboxyl, hydroxyl, and salts thereof;

the porous membrane having a thickness of about 40 μm to about 300 μm and a mean pore size of about 10 nm to about 100 nm, and

wherein the porous membrane exhibits an isopropanol flow time in a range from about 200 seconds/500 ml to about 50,000 seconds/500 ml when measured at 14.2 psi and at a temperature of about 21° C.

2. The porous membrane of claim 1 , wherein the porous membrane has a bubble point of about 5 psi to about 250 psi, when measured using ethoxynonafluorobutane HFE 7200 at a temperature of about 22° C.

3. The porous membrane of claim 1 , wherein the porous membrane exhibits an isopropanol flow time in a range from about 200 second/500 ml to about 8,000 seconds/500 ml when measured at 14.2 psi and at a temperature of about 21° C.

4. The porous membrane of claim 1 , wherein the porous membrane has a bubble point of about 5 psi to about 180 psi, when measured using ethoxynonafluorobutane HFE 7200 at a temperature of about 22° C.

5. The porous membrane of claim 1 wherein R is a C 1 -C 10 alkyl group.

6. A porous membrane comprising:

a poly (cyclic olefin) copolymer according to:

wherein n and m represent the number of repeat units of each type, p is 0 or 1, and Ris chosen from:

(i) a C 1 -C 10 alkyl group;

(ii) a C 1 -C 10 alkyl group substituted one to three times with a group chosen from halo, nitro, C 1 -C 4 alkoxy, cyano, amine, sulfonamide, sulfonic acid, trifluoromethanesulfonamido, phosphonic acid, carboxyl, hydroxyl, and salts thereof;

the porous membrane having a thickness of about 40 μm to about 300 μm,

wherein the porous membrane exhibits an isopropanol flow time in a range from about 200 seconds/500 ml to about 50,000 seconds/500 ml when measured at 14.2 psi and at a temperature of about 21° C., and wherein the porous membrane has a bubble point of about 5 psi to about 250 psi, when measured using ethoxynonafluorobutane HFE 7200 at a temperature of about 22° C.

7. The porous membrane of claim 6 , wherein the porous membrane exhibits an isopropanol flow time in a range from about 200 second/500 ml to about 8,000 seconds/500 ml when measured at 14.2 psi and at a temperature of about 21° C.

8. The porous membrane of claim 6 , wherein the porous membrane has a bubble point of about 5 psi to about 180 psi, when measured using ethoxynonafluorobutane HFE 7200 at a temperature of about 22° C.

9. The porous membrane of claim 6 wherein R is a C 1 -C 10 alkyl group.

10. The porous membrane of claim 6 , wherein the porous membrane has a bubble point of about 5 psi to about 180 psi, when measured using ethoxynonafluorobutane HFE 7200 at a temperature of about 22° C.

11. A composite filter comprising:

a first filter material and a second filter material, an output facing surface of the first filter material in contact with an input facing surface of the second filter material,

wherein the first filter material comprises the porous membrane of claim 1 , and wherein the second filter material is different from the first filter material.

12. A composite filter comprising:

a first filter material and a second filter material, an output facing surface of the first filter material in contact with an input facing surface of the second filter material,

wherein the first filter material comprises the porous membrane of claim 6 , and wherein the second filter material is different from the first filter material.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2023
From: LANGSDORF, LEAH; RHODES, LARRY F.
To: PROMERUS, LLC
Reel/Frame 064218/0282 →
SECURITY INTEREST Recorded Jun 2, 2023
From: ENTEGRIS, INC.; CMC MATERIALS LLC
To: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
Reel/Frame 063857/0199 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2023
From: BONYADI, SINA; VARANASI, PUSHKARA RAO; LI, ZHIFENG; FRAZEE, CARRIE LYNN
To: ENTEGRIS, INC.
Reel/Frame 062483/0366 →
Continuity (2)
Provisional Application 63185855 · May 7, 2021
Related Publication 20220362720A1 · Nov 17, 2022
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