Phospholipid Copolymers
The present disclosure provides copolymers including a first monomer including at least one phospholipid possessing at least one hydroxyl group and a second monomer including a cyclic monomer. Compositions, medical devices, and coatings including such copolymers are also provided.
1 . A method comprising:
contacting at least one cyclic monomer with an initiator comprising at least one phospholipid possessing at least one hydroxyl group;
polymerizing the at least one cyclic monomer; and
recovering a resulting copolymer.
2 . The method of claim 1 , wherein the at least one cyclic monomer comprises a lactone.
3 . The method of claim 1 , wherein the at least one cyclic monomer is selected from the group consisting of trimethylene carbonate, caprolactone, valerolactone, 1,4-dioxane-2-one, 1,5-dioxepan-2-one, glycolide, lactide, and combinations thereof.
4 . The method of claim 1 , wherein the at least one phospholipid possessing at least one hydroxyl group is selected from the group consisting of phosphorylcholine diols, phosphorylcholine polyols, phosphorylcholine macrodiols, and combinations thereof.
5 . The method of claim 1 , wherein the at least one phospholipid possessing at least one hydroxyl group comprises a phosphorylcholine polyol of the following formula:
wherein R 1 is a polyol possessing at least one hydroxyl group and y is a number from about 1 to about 10.
6 . The method of claim 1 , wherein the at least one phospholipid possessing at least one hydroxyl group comprises a phosphorylcholine macrodiol of the following formula:
wherein R 1 is a polyol possessing at least one hydroxyl group, R 3 is an alkyl group having from about 1 carbon atom to about 10 carbon atoms, x is a number from about 1 to about 1000, y is a number from about 1 to about 10, and z is a number from about 1 to about 1000.
7 . The method of claim 1 , further comprising contacting the at least one cyclic monomer and at least one phospholipid possessing at least one hydroxyl group with at least one additional monomer selected from the group consisting of polyethylene glycol, polypropylene glycol, polyethylene glycol-polypropylene glycol copolymers, vinyl monomers, silicones, and combinations thereof.
8 . A copolymer comprising:
at least one phospholipid comprising a phosphorylcholine polyol of the following formula:
wherein R 1 is a polyol possessing at least one hydroxyl group and y is a number from about 1 to about 10; and
at least one cyclic monomer.
9 . The copolymer of claim 8 , wherein the at least one cyclic monomer is selected from the group consisting of trimethylene carbonate, caprolactone, valerolactone, 1,4-dioxane-2-one, 1,5-dioxepan-2-one, glycolide, lactide, and combinations thereof.
10 . The copolymer of claim 8 , wherein the copolymer possesses the phospholipid in an amount of from about 5 percent by weight to about 95 percent by weight of the copolymer, and the cyclic monomer in an amount from about 5 percent by weight to about 95 percent by weight of the copolymer.
11 . The copolymer of claim 8 , further comprising at least one additional monomer selected from the group consisting of polyethylene glycol, polypropylene glycol, polyethylene glycol-polypropylene glycol copolymers, vinyl monomers, silicones, and combinations thereof.
12 . A medical device comprising the copolymer of claim 8 .
13 . The medical device of claim 12 , wherein the copolymer comprises a coating on at least a portion of the medical device.
14 . The medical device of claim 12 , wherein the medical device is selected from the group consisting of sutures, surgical meshes, anti-adhesion devices, 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, spacers, and pacemakers.
15 . A copolymer comprising:
at least one phospholipid comprising a phosphorylcholine macrodiol of the following formula:
wherein R 1 is a polyol possessing at least one hydroxyl group, R 3 is an alkyl group having from about 1 carbon atom to about 10 carbon atoms, x is a number from about 250 to about 750, y is a number from about 1 to about 10, and z is a number from about 250 to about 750, and
at least one cyclic monomer.
16 . The copolymer of claim 15 , wherein the at least one cyclic monomer is selected from the group consisting of trimethylene carbonate, caprolactone, valerolactone, 1,4-dioxane-2-one, 1,5-dioxepan-2-one, glycolide, lactide, and combinations thereof.
17 . The copolymer of claim 15 , wherein the copolymer possesses the phospholipid in an amount from about 5 percent by weight to about 95 percent by weight of the copolymer, and the cyclic monomer in an amount from about 5 percent by weight to about 95 percent by weight of the copolymer.
18 . The copolymer of claim 15 , further comprising at least one additional monomer selected from the group consisting of polyethylene glycol, polypropylene glycol, polyethylene glycol-polypropylene glycol copolymers, vinyl monomers, silicones, and combinations thereof.
19 . A medical device comprising the copolymer of claim 15 .
20 . The medical device of claim 19 , wherein the copolymer comprises a coating on at least a portion of the medical device.
21 . The medical device of claim 19 , wherein the medical device is selected from the group consisting of sutures, surgical meshes, anti-adhesion devices, 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, spacers, and pacemakers.