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. A copolymer 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 copolymer 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.
3. The copolymer of claim 1 , wherein the first monomer is selected from the group consisting of 2-methacryloyloxyethyl phosphorylcholine, 2-acryloyloxyethyl phosphorylcholine and combinations thereof.
4. The copolymer of claim 1 , wherein the second monomer comprises a vinyl furanone.
5. The copolymer of claim 1 , wherein the copolymer possesses a molar ratio of first monomer to second monomer of from about 1:10 to about 10:1.
6. The copolymer of claim 1 , further comprising at least one additional monomer selected from the group consisting of vinyl monomers, acrylate monomers, and combinations thereof.
7. The copolymer of claim 1 , further comprising 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.
8. A copolymer comprising:
a first monomer comprising 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, and a furanone 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.
9. The copolymer of claim 8 , wherein the first monomer is selected from the group consisting of 2-methacryloyloxyethyl phosphorylcholine, 2-acryloyloxyethyl phosphorylcholine and combinations thereof.
10. The copolymer of claim 8 , wherein the second monomer comprises a vinyl furanone.
11. The copolymer of claim 8 wherein the molar ratio of phosphorylcholine to furanone is from about 1:10 to about 10:1.
12. The copolymer of claim 8 , further comprising at least one additional monomer selected from the group consisting of vinyl monomers, acrylate monomers, and combinations thereof.
13. The copolymer of claim 8 , further comprising 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. An article 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.
15. The article of claim 14 , 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.
16. The article of claim 14 , wherein the first monomer is selected from the group consisting of 2-methacryloyloxyethyl phosphorylcholine, 2-acryloyloxyethyl phosphorylcholine and combinations thereof.
17. The article of claim 14 , wherein the second monomer comprises a vinyl furanone.
18. The article of claim 14 , wherein the article possesses from about 2 to about 8 moles of the second monomer per mole of the first monomer.
19. The article of claim 14 , 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.
20. The article of claim 14 , further comprising at least one additional monomer selected from the group consisting of vinyl monomers, acrylate monomers, and combinations thereof.
21. The article of claim 14 , further comprising 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.