Antimicrobial materials and coatings
View Patent ↗An antimicrobial material is provided for use in forming textiles, medical devices, packaging materials, and the like, or coatings thereon. In some embodiments, the antimicrobial material may be utilized for bulk modification of an article. The antimicrobial material includes a furanone possessing vinyl and/or acrylate functional groups, optionally in combination with another monomer possessing vinyl and/or acrylate groups.
1. A method comprising:
providing an article;
contacting the article with a first monomer comprising at least one vinyl or acrylate group in combination with a second monomer of formula:
wherein R 2 , R 3 and R 4 are independently or all H or halogen,
R 1 is a moiety selected from the group consisting of H, halogen, formyl, carboxyl, cyano, ester, amide, alkyl, alkoxy, oxoalkyl, alkenyl, alkynyl, aryl and arylalkyl,
at least one of R 1 , R 2 , R 3 and R 4 are substituted with a moiety selected from the group consisting of vinyl moieties and acrylate moieties; and
polymerizing the first monomer and the second monomer wherein the first monomer is selected from the group consisting of 2-methacryloyloxyethyl phosphorylcholine, 2-acryloyloxyethyl phosphorylcholine, and combinations thereof.
2. The method of claim 1 , wherein the first monomer and the second monomer are in a solution comprising at least one solvent selected from the group consisting of liquid vinyl monomers, water, organic solvents, and combinations thereof.
3. The method of claim 1 , wherein the second monomer comprises a vinyl furanone.
4. The method of claim 1 , wherein polymerizing the first monomer and the second monomer occurs in situ.
5. The method of claim 1 , wherein polymerizing the first monomer and the second monomer occurs in the presence of an initiator selected from the group consisting of photoinitiators, chemical initiators, and combinations thereof.
6. The method of claim 1 , wherein polymerizing the first monomer and the second monomer further comprises the application of at least one energy source selected from the group consisting of gamma radiation, e-beam radiation, ultraviolet light, pulsed laser ablation deposition, plasma energy, positron, and combinations thereof.
7. The method of claim 1 , wherein polymerizing the first monomer and the second monomer forms a polymer on or within the article.
8. The method of claim 1 , wherein the article is selected from the group consisting of sutures, surgical meshes, contact lenses, intraocular lenses, staples, clips, buttresses, lapbands, catheters, bandages, stents, grafts, stent/grafts, knotless wound closures, sealants, adhesives, tissue scaffolds, pins, screws, orthopedic hardware, pacers, and pacemakers.
9. A method comprising:
contacting an article with a solution comprising a first monomer comprising at least one phosphorylcholine possessing at least one vinyl group of the formula:
wherein x is from about 1 to about 10 and y is from about 1 to about 10 and a second monomer of formula
wherein R 2 , R 3 and R 4 are independently or all H or halogen; and
R 1 is a moiety selected from the group consisting of H, halogen, formyl, carboxyl, cyano, ester, amide, alkyl, alkoxy, oxoalkyl, alkenyl, alkynyl, aryl and arylalkyl,
wherein at least one of R 1 , R 2 , R 3 and R 4 are substituted with a moiety selected from the group consisting of vinyl moieties and acrylate moieties; and
polymerizing the first monomer and the second monomer.
10. The method of claim 9 , wherein the solution comprises at least one solvent selected from the group consisting of liquid vinyl monomers, water, organic solvents, and combinations thereof.
11. The method of claim 9 , wherein the first monomer is selected from the group consisting of 2-methacryloyloxyethyl phosphorylcholine, 2-acryloyloxyethyl phosphorylcholine and combinations thereof.
12. The method of claim 9 , wherein the second monomer comprises a vinyl furanone.
13. The method of claim 9 , wherein the polymerization occurs in situ.
14. The method of claim 9 , wherein the solution further comprises at least one additional monomer selected from the group consisting of vinyl monomers and acrylate monomers.
15. The method of claim 9 , wherein the solution further comprises at least one additional monomer selected from the group consisting of vinyl functional quaternary amines, hydroxyethyl methacrylate, n-vinyl pyrrolidone, sodium acrylate, bis-acrylate, styrene sulfonic acid, butyl acrylate, sulfopropyl acrylate, sulfopropyl methacylate, acrylamide, diacrylamide, methacrylic acid, acrylic acid, polyethylene glycol acrylates, polyethylene glycol/polypropylene glycol acrylates, silicone acrylates, and combinations thereof.
16. The method of claim 9 , wherein polymerizing the first monomer and the second monomer occurs in the presence of an initiator selected from the group consisting of photoinitiators, chemical initiators, and combinations thereof.
17. The method of claim 9 , wherein polymerizing the first monomer and the second monomer further comprises the application of at least one energy source selected from the group consisting of gamma radiation, e-beam radiation, ultraviolet light, pulsed laser ablation deposition, plasma energy, positron, and combinations thereof.
18. The method of claim 9 , wherein polymerizing the first monomer and the second monomer forms a polymer on or within the article.
19. The method of claim 9 , wherein the article is selected from the group consisting of sutures, surgical meshes, contact lenses, intraocular lenses, staples, clips, buttresses, lapbands, catheters, bandages, stents, grafts, stent/grafts, knotless wound closures, sealants, adhesives, tissue scaffolds, pins, screws, orthopedic hardware, pacers, and pacemakers.