IP Library Granted Patent US 11,643,551
Granted Patent B2
US 11,643,551 · App. 16/642,053 · Granted May 9, 2023

Synthetic membrane composition comprising a polyurethane and a polyoxazoline

Inventors: Jennifer Al-Rashid (Exton, PA); Jacob Riffey (Exton, PA); Chad Sugiyama (Exton, PA); John Zupancich (Exton, PA)
Assignee: DSM IP ASSETS B.V.
C08L75/08A61B5/14532A61B5/14735B01D67/0011B01D67/0095B01D69/02B01D71/54B01D71/58C08G18/244C08G18/283C08G18/2825C08G18/4808C08G18/4833C08G18/4854C08G18/6674C08G18/73C08G18/755C08G18/758C08J5/18C12Q1/00A61B5/14546B01D2323/12B01D2325/34B01D2325/36C08J2375/08C08J2475/04C08L2203/16C08L2205/025
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,643,551
App. No.
16/642,053
Granted
May 9, 2023
Kind
B2
Abstract

Disclosed are compositions that may be useful for forming synthetic membranes, methods of forming membranes therefrom, and membranes. In an embodiment, a membrane comprises a free hydrophilic polymer comprising a polyoxazoline, and a polyurethane, the polyurethane comprising a backbone comprising the reaction product of a diisocyanate, a polymeric aliphatic 5 diol, and optionally a chain extender.

Claims (29)

1. A composition for forming a membrane comprising from 90 to 99.5 wt %, based on the total weight of the composition, of a solvent and from 0.5 to 10 wt %, based on the total weight of the composition, of a polymer mixture, the polymer mixture comprising from 60 to 99.5 wt %, based on the total weight of the polymer mixture, of a polyurethane and from 0.5 to 40 wt %, based on the total weight of the polymer mixture, of a free hydrophilic polymer comprising a polyoxazoline,

wherein the polyurethane comprises a backbone comprising the reaction product of a diisocyanate, a polymeric aliphatic diol, and optionally a chain extender, and

wherein the free hydrophilic polymer is a hydrophilic polymer that is not bound to the polyurethane by covalent bonds.

2. A membrane comprising:

a. a free hydrophilic polymer comprising a polyoxazoline, and

b. a polyurethane, the polyurethane comprising a backbone comprising a reaction product of a diisocyanate, a polymeric aliphatic diol, and optionally a chain extender,

wherein the free hydrophilic polymer is a hydrophilic polymer that is not bound to the polyurethane by covalent bonds.

3. The membrane according to claim 2 , wherein the membrane comprises from 90 to 99 wt %, based on the total weight of the membrane, of the polyurethane, and from 1.0 to 10 wt %, based on the total weight of the membrane, of the free hydrophilic polymer.

4. The membrane according to claim 2 , wherein the free hydrophilic polymer comprises poly(2-methyl-2-oxazoline) or poly(2-ethyl-2-oxazoline).

5. The membrane according to claim 2 , wherein the free hydrophilic polymer consists of poly(2-methyl-2-oxazoline), poly(2-ethyl-2-oxazoline), copolymers thereof, or a mixture thereof.

6. The membrane according to claim 2 , wherein the free hydrophilic polymer has a number average molecular weight of at least 100,000 g/mol and at most 1,000,000 g/mol.

7. The membrane according to claim 2 , wherein the polyurethane comprises an endgroup and the endgroup is present in an amount of at least 0.1 wt % and at most 3 wt %, based on the total weight of the polyurethane.

8. The membrane according to claim 2 , wherein the polymeric aliphatic diol comprises a polysiloxane diol or a random or block copolymer diol comprising a polysiloxane.

9. The membrane according to claim 2 , wherein the polyurethane comprises a C 2 -C 16 fluoroalkyl or a C 2 -C 16 fluoroalkyl ether.

10. The membrane according to claim 2 , wherein the polymeric aliphatic diol comprises a polysiloxane diol, a polycarbonate diol, a poly(tetramethylene oxide) diol, or a mixture thereof.

11. The membrane according to claim 2 , wherein the polymeric aliphatic diol comprises a polysiloxane diol and one or more of a polycarbonate diol and a poly(tetramethylene oxide) diol.

12. The membrane according to claim 2 , wherein the polyurethane is devoid of a hydrophilic polymer moiety.

13. The membrane according to claim 2 , wherein the polyurethane backbone comprises a polysiloxane and the polyurethane comprises an average of from 0.25 to 3 endgroups per molecule comprising a C 2 -C 16 fluoroalkyl or a C 2 -C 16 fluoroalkyl ether.

14. The composition according to claim 1 , wherein the solvent comprises 40 wt % or more of tetrahydrofuran (THF), methyl-tetrahydrofuran (methyl-THF), or a mixture thereof, and methanol, ethanol, isobutanol, propanol, methyl ethyl ketone, or a mixture thereof at an amount of from 1 to 60 wt %, based on the total amount of solvent in the composition.

15. The composition according to claim 1 , wherein the solvent comprises at least 40 wt % of THF, and methanol, ethanol, or a mixture thereof at an amount of from 1 to 60 wt %, based on the total amount of solvent in the composition.

16. The composition according to claim 1 , wherein the solvent comprises at least 70 wt % of THF, and propanol, isobutanol, methyl-THF, or methyl ethyl ketone, or a mixture thereof, at an amount of from 1 to 30 wt %, based on the total amount of solvent in the composition.

17. The composition according to claim 1 , wherein the free hydrophilic polymer is present in an amount of from 5 to 40 wt %, based on the total combined weight of the polyurethane and the free hydrophilic polymer.

18. A membrane formed from a composition comprising from 90 to 99.5 wt %, based on the total weight of the composition, of a solvent and from 0.5 to 10 wt %, based on the total weight of the composition, of a polymer mixture, the polymer mixture comprising:

a. from 60 to 99.5 wt %, based on the total weight of the polymer mixture, of a polyurethane, and

b. from 0.5 to 40 wt %, based on the total weight of the polymer mixture, of a free hydrophilic polymer comprising a polyoxazoline,

wherein the polyurethane comprises a backbone comprising the reaction product of a diisocyanate, a polymeric aliphatic diol, and optionally a chain extender, and

wherein the free hydrophilic polymer is a hydrophilic polymer that is not bound to the polyurethane by covalent bonds.

19. The membrane according to claim 18 , wherein the membrane has a residual solvent content of less than 50 ppm after drying the membrane under nitrogen for 24 hours followed by drying in a convection oven at 50° C. for one hour.

20. A sensor comprising the membrane according to claim 2 , wherein the sensor is configured to detect glucose, lactic acid, glutamate, pyruvate, choline, acetylcholine, nitric oxide, sodium, potassium, calcium, chloride, bicarbonate, urea, creatine, or dopamine in the blood stream or another bodily fluid.

Assignments (2)
CHANGE OF ASSIGNEE ADDRESS Recorded Sep 12, 2025
From: DSM IP ASSETS B.V.
To: DSM IP ASSETS B.V.
Reel/Frame 072873/0389 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2024
From: AL-RASHID, JENNIFER; RIFFEY, JACOB; ZUPANCICH, JOHN; SUGIYAMA, CHAD
To: DSM IP ASSETS B.V.
Reel/Frame 068347/0465 →
Priority Claims (3)
WO 17191475 · Sep 15, 2017 · international
WO 17191476 · Sep 15, 2017 · international
WO 17191477 · Sep 15, 2017 · international
Continuity (4)
Provisional Application 62550922 · Aug 28, 2017
Provisional Application 62550937 · Aug 28, 2017
Provisional Application 62550929 · Aug 28, 2017
Related Publication 20210070989A1 · Mar 11, 2021