Polyurethane based medical articles

Patent metadata

Field	Value
Publication number	US-12370291-B2
Application number	US-202217680657-A
Country	US
Kind code	B2
Filing date	Feb 25, 2022
Priority date	Feb 25, 2021
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

Medical articles formed from a polyurethane-based resin including an ionically-charged modifier provide enhanced properties. The polyurethane-based resin is a reaction product of ingredients comprising: a diisocyanate; a diol chain extender; a polyglycol; and an anionic modifier incorporated into a backbone, as a side chain, or both of the polyurethane-based resin. Exemplary anionic modifier includes 2,2-bis(hydroxymethyl)butyric acid (BHMBA) and/or bis-1,4-((2-hydroxypropoxy)-2-propoxy)-butane sulfonate sodium salt (SULFADIOL®-7Q). Medical articles herein either have inherent antimicrobial and/or anti-fouling characteristics or can easily bond cationic active agents to provide desirable material properties, including antimicrobial, anti-fouling, and/or radiopacity.

First claim

What is claimed is:

1. A medical article formed from a polyurethane-based resin, which is a reaction product of ingredients consisting essentially of:
4,4′-diphenylmethane diisocyanate (MDI) as a diisocyanate;
1,4-butanediol as a diol chain extender;
a polytetramethylene ether glycol as a polyglycol; and
an anionic modifier incorporated into a backbone, as a side chain, or both of the polyurethane-based resin formed by the diisocyanate, the polyglycol, and the diol chain extender, wherein the anionic modifier comprises bis-1,4-((2-hydroxypropoxy)-2-propoxy)-butane sulfonate sodium salt,
the polyurethane-based resin having a hard segment content in a range of from 25% to 75% by weight of the overall resin composition and a soft segment content of the resin is in a range of from 75% to 25% by weight of the overall resin composition.

2. The medical article of claim 1 , which is effective to reduce thrombus formation and/or bacterial biofilm formation.

3. The medical article of claim 2 , which is effective to reduce thrombus formation and/or bacterial biofilm formation due to ionic repulsion of bacteria, protein, and blood components.

4. The medical article of claim 1 , wherein the anionic modifier is present in an amount of greater than or equal to 0.01 weight percent of the overall composition of the polyurethane-based resin.

5. The medical article of claim 1 , wherein the anionic modifier is present in an amount of less than or equal to 75 weight percent of the overall composition of the polyurethane-based resin.

6. The medical article of claim 1 , wherein the polyurethane-based resin is bound to a cationic agent through ionic bonding.

7. The medical article of claim 6 , wherein the ionic bonding is achieved by a technique comprising a solution imbibing technique or a bulk mixing technique.

8. The medical article of claim 7 , wherein the bulk mixing technique comprises a thermal compounding technique and a solvent mixing technique.

9. The medical article of claim 7 , wherein the solution imbibing technique comprises: de-protonating a portion of the anionic modifier, and soaking the polyurethane-based resin in a solution of the cationic agent.

10. The medical article of claim 9 , wherein the solution imbibing technique further comprises: swelling the polyurethane-based resin before the de-protonating of the portion of the anionic modifier, and rinsing the polyurethane-based resin before the soaking of the polyurethane-based resin in a solution of the cationic agent.

11. The medical article of claim 6 , wherein the cationic agent comprises one or more of: an antimicrobial agent, a lubricating agent, a radiopaque agent, and an antithrombotic agent.

12. The medical article of claim 11 comprising the antimicrobial agent, antithrombotic agent, or a combination thereof, which is effective to provide antimicrobial and/or anti-fouling activity.

13. The medical article of claim 12 , which is effective to actively provide enhanced surface properties, the enhanced surface properties comprising antimicrobial and/or anti-fouling activity.

14. The medical article of claim 11 , wherein the cationic agent comprises one or more of: chlorhexidine acetate, chlorhexidine gluconate, silver sulfadiazine, benzalkonium chloride, cetylpyridinium chloride, a cationic quaternary ammonium and guanidine-containing biocide, a cationic antimicrobial polymer, an antimicrobial peptide or peptide-mimics, and an antifouling phospholipid or phospholipid-mimics.

15. The medical article of claim 11 comprising the radiopaque agent comprising barium cations, bismuth cations, or a combination thereof, which is effective to provide medical article radiopacity.

16. The medical article of claim 1 , wherein the ingredients of the reaction product further comprise: a low-surface energy modifying oligomer incorporated into a backbone, as a side chain, or both of the polyurethane-based resin formed by the diisocyanate, the polyglycol, the anionic modifier, and the diol chain extender, the low-surface energy modifying oligomer comprising a diol-containing perfluoropolyether and/or a monofunctional polysiloxane.

17. The medical article of claim 16 , wherein the modifying oligomer has an alcohol (C—OH) moiety and a functional moiety.

18. The medical article of claim 17 , wherein the functional moiety comprises a fluoroether, a silicone, or a combination thereof.

19. The medical article of claim 16 , wherein the low-surface energy modifying oligomer is present in an amount ranging from about 0.1 to about 10 weight percent of the overall composition of the polyurethane-based resin.

Assignees

• Becton Dickinson Co

Inventors

• Bai He
• Zhang Hua
• Weimer Marc W
• Freasier James

Classifications

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title

• A61L2300/42

  Anti-thrombotic agents, anticoagulants, anti-platelet agents · CPC title

• C08G18/831

  by oxygen-containing compounds inclusive of carbonic acid halogenides, carboxylic acid halogenides and epoxy halides (by aldehydes C08G18/84, by peroxides C08G18/86) · CPC title

• C08G18/6674

  with compounds of group C08G18/3203 · CPC title

• C08G18/3206

  aliphatic · CPC title