Antimicrobial compositions and methods

• US 20060147847A1
• Filed: 12/30/2004
• Published: 07/06/2006
• Est. Priority Date: 12/30/2004
• Status: Abandoned Application

• Current Assignee: Surmodics Incorporated
• Original Assignee: Surmodics Incorporated
• Inventors: Wen, Jie, Guire, Patrick E., Taton, Kristin S.
• Application Number:
  US11/027,036
• Publication Number:
  US 20060147847A1
• Time in Patent Office: Days
• US Class Current: 430/323
• CPC Class Codes: A01N 59/00 Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
• CPC Class Codes: A61L 15/46 Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
• CPC Class Codes: A61L 2300/106 Halogens or compounds thereof, e.g. iodine, chlorite
• CPC Class Codes: A61L 2300/404 Biocides, antimicrobial agents, antiseptic agents
• CPC Class Codes: A61L 2300/606 Coatings

Abstract

The invention provides polymeric reagents of a formula:
X_a—Y-Z_b wherein X is a latent reactive group, Y is a polymeric backbone, and Z is a melamine group. In some aspects of the above formula, a is in the range of 0.5 to 90 mole percent, and b is in the range of 10 to 99.5 mole percent. The latent reactive group can be a photoreactive group or a thermally-reactive group. Monomeric units for preparing the polymeric reagents are also described. Methods of using the polymeric reagents to provide modified surfaces are also described, as well as methods of providing biocidal surfaces and methods of treating habitats for halogen-sensitive microorganisms.

Claims

1. A polymeric reagent of a formula:

X_a—

Y-Z_b

wherein X is a latent reactive group, Y is a polymeric backbone, and Z is a melamine group.

2. The polymeric reagent according to claim 1 wherein the latent reactive group is a photoreactive group.

3. The polymeric reagent according to claim 2 wherein the photoreactive group is a photoreactive aryl ketone.

4. The polymeric reagent according to claim 3 wherein the photoreactive aryl ketone is selected from acetophenone, benzophenone, anthraquinone, anthrone, and anthrone-like heterocycles.

5. The polymeric reagent according to claim 1 wherein the latent reactive group is a thermally-reactive group.

6. The polymeric reagent according to claim 5 wherein the thermally-reactive group comprises a peroxide group.

7. The polymeric reagent according to claim 6 wherein the thermally-reactive group comprises a peroxyester group.

8. The polymeric reagent according to claim 7 wherein the thermally-reactive group comprises a group selected from benzyl, diphenylacetyl, phenylacetyl, benzoyl, phenylbenzyl, hydrocinnamoyl, mandelyl, phenacyl, phenethyl, thiophenacyl, triphenylmethyl, biphenylacetyl, biphenylethyl, or biphenylmethyl.

9. The polymeric reagent according to claim 1 wherein the polymeric backbone is selected from polystyrene, polyvinylchloride, polymethacrylates, polyvinylpyrrolidone and polyacrylamides.

10. The polymeric reagent according to claim 1 wherein the polymeric backbone is selected from polyester, polycarbonate, polyamide, polyether, polysulfone, polyurethane, polyimide, and polyvinyl backbones.

11. The polymeric reagent according to claim 1 wherein the polymeric backbone is formed from monomeric units having ethylenically unsaturated groups.

12. The polymeric reagent according to claim 1 wherein the polymeric backbone comprises methacrylamide, acrylamide, or vinylpyrrolidone monomeric units.

13. The polymeric reagent according to claim 12 wherein the polymeric backbone comprises methacrylamide.

14. A method for making a modified surface, the method comprising steps of:

a. providing a polymeric reagent composition, the polymeric reagent composition comprising a polymeric backbone, latent reactive groups bound to the polymeric backbone, and melamine groups bound to the polymeric backbone, to a surface, and

b. binding the polymeric reagent to the surface.

15. The method according to claim 14 further comprising the step of halogenating the melamine groups with a halogen.

16. The method according to claim 14 wherein the providing step comprises providing a polymeric reagent comprising a polymeric backbone selected from polyester, polycarbonate, polyamide, polyether, polysulfone, polyurethane, polyimide, and polyvinyl backbones.

17. The method according to claim 14 wherein the providing step comprises providing a polymeric reagent comprising a polymeric backbone formed from monomeric units having ethylenically unsaturated groups.

18. The method according to claim 14 wherein the providing step comprises providing a polymeric backbone that comprises methacrylamide, acrylamide, or vinylpyrrolidone monomeric units.

19. The method according to claim 18 wherein the providing step comprises providing a polymeric reagent wherein the polymeric backbone comprises methacrylamide.

20. The method according to claim 14 wherein the providing step comprises providing a polymeric reagent wherein the latent reactive groups comprise photoreactive groups.

21. The method according to claim 20 wherein the providing step comprises providing a polymeric reagent comprising aryl ketones.

22. The method according to claim 21 wherein the providing step comprises providing a polymeric reagent comprising aryl ketones selected from acetophenone, benzophenone, anthraquinone, anthrone, and anthrone-like heterocycles.

23. The method according to claim 20 wherein the binding step comprises providing energy of a suitable wavelength.

24. The method according to claim 14 wherein the providing step comprises providing a polymeric reagent wherein the latent reactive groups comprise thermally-reactive groups.

25. The method according the claim 24 wherein the providing step comprises providing a polymeric reagent wherein the thermally-reactive groups comprise a peroxide group.

26. The method according to claim 25 wherein the providing step comprises providing a polymeric reagent wherein the thermally-reactive group comprises a peroxyester group.

27. The method according to claim 26 wherein the providing step comprises providing a polymeric reagent wherein the thermally-reactive group comprises a group selected from benzyl, diphenylacetyl, phenylacetyl, benzoyl, phenylbenzyl, hydrocinnamoyl, mandelyl, phenacyl, phenethyl, thiophenacyl, triphenylmethyl, biphenylacetyl, biphenylethyl, or biphenylmethyl.

28. The method according to claim 24 wherein the binding step comprises providing heat to the surface in a temperature sufficient to bind the polymeric reagent to the surface.

29. The method according to claim 14 wherein the surface is provided in a form of medical water supply lines.

30. The method according to claim 29 wherein the surface comprises a material selected from polystyrene, polyvinyl chloride, polyurethane, silicon, polypropylene, polyethylene, and metal.

31. The method according to claim 15 wherein the halogenating step comprises contacting the polymeric reagent composition with sodium hypochlorite.

32. A polymer-coupled support comprising:

a. a polymeric reagent composition of a formula

X_a—

Y—

Z_b

wherein X is a latent reactive group, Y is a polymeric backbone, and Z is a melamine group; and

b. a support, wherein the polymeric reagent is bound to the support.

33. The polymer-coupled support according to claim 32 wherein the latent reactive group is a photoreactive group.

34. The polymer-coupled support according to claim 33 wherein the photoreactive group is a photoreactive aryl ketone.

35. The polymer-coupled support according to claim 32 wherein the latent reactive group is a thermally-reactive group.

36. The polymeric reagent according to claim 35 wherein the thermally-reactive group comprises a peroxide group.

37. A halamine-modified surface comprising a polymeric reagent composition bound to a surface, the polymeric reagent having a formula

X_a—

Y-Z_b,

wherein X is a latent reactive group that is selected to bind the polymeric reagent to the surface, Y is a polymeric backbone, and Z is melamine containing halogen atoms at one or more amine groups pendent from the melamine.

38. A method for treating a habitat for halogen-sensitive microorganisms comprising contacting the habitat with an antimicrobial amount of a polymeric reagent having a formula

X_a—

Y-Z_b,

wherein X is a latent reactive group that is selected to bind the polymeric reagent to a surface within the habitat, Y is a polymeric backbone, and Z is melamine containing halogen atoms at one or more amine groups pendent from the melamine.

39. The method according to claim 38 further comprising providing a source of free halogen to the polymeric reagent on a periodic basis.

40. The method according to claim 38 wherein the microorganisms are selected from bacteria, fungi, molds, protozoa, viruses, and algae.

41. A monomeric unit having the formula:

wherein n is 2 to 4.