Antimicrobial polyurethane materials and methods of forming and using same

Patent metadata

Field	Value
Publication number	US-9949484-B2
Application number	US-201314398393-A
Country	US
Kind code	B2
Filing date	May 1, 2013
Priority date	May 1, 2012
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

Antimicrobial quaternized polyurethane materials and methods of forming and using the materials are disclosed. The quaternized polyurethane antimicrobial materials may be synthesized from one or more diisocyanates and one or more diols or triols. The quaternized polyurethane materials may be stand alone or coated onto other surfaces, such as medical devices, table tops, air/water filters, or the like to provided desired antimicrobial devices and surfaces.

First claim

The invention claimed is:

1. An antimicrobial compound, wherein the compound comprises quaternized polyurethane comprising an end group comprising a quaternary compound, and wherein the quaternized polyurethane has a general structure of:

wherein I ranges from about 20 to about 200, m is 2 or 3 and n is 6-22.

2. The antimicrobial compound of claim 1 , wherein the quaternized polyurethane is synthesized from one or more diisocyanates and one or more compounds selected from the group of one or more diols comprising an amine group and one or more triols comprising an amine group.

3. The antimicrobial compound of claim 2 , wherein one or more diisocyanates are selected from one or more of the group consisting of isophorone diisocyanate, 1,4-phenylene diisocyanate, 1,3-phenylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, 2,4,6-trimethyl-1,3-phenylene diisocyanate, tetramethylene diisocyanate, octamethylene diisocyanate, 1,3-bis(1-isocyanato-1-methylethyl) benzene, 4,4′-methylenebis(phenyl isocyanate), 3,3′-dimethyloxy-4,4′-bisphenylene diisocyanate, 1,8 diisocyanateoctane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, and 3,3′-dimethoxy-4,4′-biphenylene diisocyanate.

4. The antimicrobial compound of claim 2 , wherein one or more diols are selected from the group consisting of serinol, 3-dimethylaminopropane-1,2-diol, 2-amino-2-methyl-1,3-propanediol, 2-amino-1,1-propanediol, 2-aminobutane-1,4-diol, 2-amino-1,2-propanediol, 2-amino-1,6-hexanediol, 2,5-diamino-1,6-hexanediol, 2-amino-1,7-heptanediol, 2-amino-1,5-pentanediol, 2-amino-2-ethyl-1,3-propanediol, 2,3-diamino-1,4-butanediol, 2,4-diamino-1,5-pentanediol, 2-amino-1,3-octanediol, 4-amino-3,5-heptanediol, 4-amino-1,3-hexanediol, 2-amino-2-isopropyl-1,3-propanediol, 4-amino-1,3-heptanediol, 2-amino-1,2,4-trideoxypentitol, and 2,4-diamino-1,6-hexanediol.

5. The antimicrobial compound of claim 2 , wherein one or more triols include an amine group.

6. The antimicrobial compound of claim 2 , wherein the one or more diols comprising an amine group and one or more triols comprising an amine group are initially protected by a protecting group.

7. The antimicrobial compound of claim 1 , wherein the compound comprises nanoparticles having an average diameter of about 25 nm to about 300 nm.

8. The antimicrobial compound of claim 1 , wherein the compound comprises nanofibers having an average diameter of about 150 nm to about 300 nm.

9. The antimicrobial compound of claim 1 , wherein the antimicrobial material compound comprises an aqueous suspension.

10. The antimicrobial compound of claim 1 , wherein n ranges from about 6 to about 12.

11. The antimicrobial compound of claim 1 , wherein the antimicrobial material compound comprises a solution.

12. The antimicrobial compound of claim 11 , wherein the solution comprises an organic solvent.

13. The antimicrobial compound of claim 12 , wherein the solvent comprises a compound selected from the group consisting of tetrahydrofuran, methanol, chloroform, butanol, and dimethylformamide.

14. A device comprising the quaternized polyurethane of claim 1 .

15. The device of claim 14 comprising a filter.

16. The device of claim 14 comprising a medical device.

17. The device of claim 14 comprising a plurality of layers of quaternized polyurethane.

18. A method of forming the quaternized polyurethane of claim 1 , the method comprising the steps of:
dissolving a one or more diols or triols, the diols or triols having an amine group protected with a protecting group, in a solvent to form a solution;
adding one or more diisocyanates to the solution;
polymerizing the solution to form the polyurethane;
precipitating the polyurethane;
removing protecting group; and
forming the quaternized polyurethane.

19. The method of claim 18 , wherein the polymerizing step is performed in a nitrogen environment.

20. The method of any claim 18 , further comprising the step of forming nanoparticles.

21. The method of any claim 18 , further comprising the step of forming nanofibers.

22. The method of claim 21 , further comprising the step of weaving the nanofibers.

23. An antimicrobial Quat-n-PU material, having the general formula of:

wherein I ranges from about 20 to about 200, m is 2 or 3, n is 6-22 and wherein a molecular weight of the antimicrobial Quat-n-PU material ranges from about 5,000 to about 50,000 Da.

24. The antimicrobial Quat-n-PU material of claim 23 , wherein the material exhibits antiviral behavior against enveloped viruses.

25. The antimicrobial Quat-n-PU material of claim 23 , wherein the material is antibacterial.

26. A device formed from the antimicrobial Quat-n-PU material of claim 23 .

27. The antimicrobial compound of claim 1 , wherein I ranges from about 25 to 140.

28. The antimicrobial compound of claim 23 , wherein I ranges from about 25 to 140.

29. The antimicrobial compound of claim 1 , wherein n is about 6.

30. The antimicrobial compound of claim 1 , wherein n is about 12.

31. The antimicrobial compound of claim 23 , wherein n is about 6.

32. The antimicrobial compound of claim 23 , wherein n is about 12.

Assignees

• Univ Colorado Regents

Inventors

• Park Daewon

Classifications

• A61L27/18

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C08G18/833

  by nitrogen containing compounds (by azo compounds C08G18/85) · CPC title

• A61L2300/404

  Biocides, antimicrobial agents, antiseptic agents · CPC title

• C08G2340/00

  Filter material · CPC title

• A61L31/16

  Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)} · CPC title