Furanone copolymers
View Patent ↗The present disclosure provides copolymers including a first monomer including at least one phospholipid possessing at least one vinyl group and a second monomer including a furanone possessing vinyl and/or acrylate groups. Compositions, medical devices, and coatings including such copolymers are also provided.
1. An article comprising a coating comprising:
a first monomer comprising at least one vinyl phospholipid monomer; 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 or 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.
2. The article of claim 1 , wherein the article is selected from the group consisting of textiles, medical devices, and packaging materials.
3. The article of claim 1 , wherein the article comprises a textile formed of fibers made of components selected from the group consisting of natural fibers, synthetic fibers, blends of natural fibers, blends of synthetic fibers, and blends of natural fibers with synthetic fibers.
4. The article of claim 1 , wherein the article comprises a textile formed of fibers made of components selected from the group consisting of furanone copolymers, polyesters, polyamides, polyolefins, halogenated polymers, polyester/polyethers, polyurethanes, homopolymers thereof, copolymers thereof, and combinations thereof.
5. The article of claim 1 , wherein the article comprises a medical device selected from the group consisting of clips, fasteners, staples, sutures, pins, screws, prosthetic devices, wound dressings, bandages, drug delivery devices, anastomosis rings, surgical blades, contact lenses, intraocular lenses, surgical meshes, stents, grafts, catheters, stent/grafts, knotless wound closures, sealants, adhesives, tissue scaffolds, stapling devices, buttresses, lapbands, orthopedic hardware, pacers, pacemakers, and other implantable devices.
6. The article of claim 1 , wherein the article comprises a packaging material for a product selected from the group consisting of medical devices, pharmaceuticals, textiles, consumer goods, and foods.
7. The article of claim 1 , wherein the coating is applied as part of a solution including a solvent selected from the group consisting of alcohols, ketones, ethers, aldehydes, acetonitrile, acetic acid, methylene chloride, chloroform, and water.
8. The article of claim 1 , wherein the first monomer comprises a 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.
9. The article of claim 1 , wherein the first monomer is selected from the group consisting of 2-methacryloyloxyethyl phosphorylcholine, 2-acryloyloxyethyl phosphorylcholine and combinations thereof.
10. The article of claim 1 , wherein the second monomer comprises a vinyl furanone.
11. The article of claim 1 , wherein the article possesses from about 2 to about 8 moles of the second monomer per mole of the first monomer.
12. The article of claim 1 , wherein the coating further comprises at least one additional monomer selected from the group consisting of vinyl monomers, acrylate monomers, and combinations thereof.
13. The article of claim 1 , wherein the coating 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.
14. The article of claim 1 , wherein the coating further comprises a fatty acid component selected from the group consisting of fatty acids, fatty acid salts, and salts of fatty acid esters.
15. The article of claim 1 , wherein the coating further comprises a component selected from the group consisting of dyes, antimicrobial agents, growth factors, anti-inflammatory agents, and polymer drugs.
16. The article of claim 15 , wherein the antimicrobial agent is selected from the group consisting of antibiotics, antiseptics, disinfectants and combinations thereof.
17. The article of claim 15 , wherein the antimicrobial agent is selected from the group consisting of minocycline, rifampin, erythromycin, penicillin, nafcillin, cefazolin, imipenem, aztreonam, gentamicin, chloramphenicol, sulfamethoxazole, vancomycin, ciprofloxacin, fusidic acid, trimethoprim, metronidazole, clindamycin, mupirocin, amphotericin B, fluconazole, sulbactam, antimicrobial peptides, antimicrobial proteins, chemotherapeutic drugs, telomerase inhibitors, 5-furanones, mitoxanthone, hexachlorophene, chlorhexidine, cyclohexidine, iodine, povidone-iodine, p-chloro-m-xylenol, triclosan, nitrofurantoin, anitrofurazone, methenamine, glutaraldehyde, formaldehyde, alcohols, and combinations thereof.
18. The article of claim 15 , wherein the polymer drug is selected from the group consisting of polymeric antibiotics, polymeric antiseptics, and polymeric non-steroidal anti-inflammatory drugs.