Carbonate copolymers
View Patent ↗Copolymer compositions are provided which include a cyclic monomer and an aromatic cyclic carbonate. The copolymer may be produced, in embodiments, by a ring-opening polymerization reaction initiated by the aromatic cyclic carbonate. The resulting copolymer may be utilized in producing medical devices, drug delivery devices, and/or coatings for medical devices.
1. A method of forming a copolymer comprising:
heating at least one cyclic monomer in the presence of an aromatic cyclic carbonate selected from the group consisting of:
wherein R is an aromatic comprising benzene, Z comprises COO, n is a number from about 1 to about 30 and m is a number from about 1 to about 30;
allowing the at least one cyclic monomer and the aromatic cyclic carbonate to polymerize to form a copolymer; and
recovering the resulting copolymer.
2. The method of claim 1 , wherein the at least one cyclic monomer is selected from the group consisting of cyclic esters and cyclic carbonates.
3. The method of claim 1 , wherein the at least one cyclic monomer comprises a cyclic ester selected from the group consisting of glycolide, L(−)-lactide, D(+)-lactide, meso-lactide, p-dioxanone, 1,4-dioxan-2one, 1,5-dioxepan-2-one, epsilon-caprolactone, delta-valerolactone, gamma-butyrolactone, beta-propiolactone, and combinations thereof.
4. The method of claim 1 , wherein at least one cyclic monomer comprises a cyclic carbonate selected from the group consisting of ethylene carbonate, trimethylene carbonate, dimethyl trimethylene carbonate, 3-ethyl-3-hydroxymethyl trimethylene carbonate, propylene carbonate, trimethyloipropane monocarbonate, 4,6 dimethyl-1,3-propylene carbonate, 2,2-dimethyl trimethylene carbonate, and 1,3-dioxepan-2-one, and combinations thereof.
5. The method of claim 1 , wherein the heating comprises heating the cyclic monomer and aromatic cyclic carbonate to a temperature of from about 170° C. to about 185° C., for a period of time from about 4 hours to about 6 hours.
6. The method of claim 1 , wherein the heating comprises heating the cyclic monomer and aromatic cyclic carbonate to a temperature of from about 175° C. to about 180° C., for a period of time from about 4.25 hours to about 4.75 hours.
7. The method of claim 1 , further comprising heating the copolymer to a temperature from about 100° C. to about 120° C., for a period of time ranging from about 25 hours to about 35 hours.
8. The method of claim 1 , further comprising heating the copolymer to a temperature from about 107° C. to about 113° C., for a period of time ranging from about 28 hours to about 32 hours.
9. A copolymer produced by the method of claim 1 .
10. A copolymer produced by the method of claim 1 having the formula
wherein W is a derivative obtained from the cyclic monomer selected from the group consisting of esters and carbonates, A is an aromatic carbonate derivative obtained from the aromatic cyclic oligomeric carbonate, x is a number from about 1 to about 200, and y is a number from about 1 to about 200.
11. The copolymer of claim 10 , wherein W comprises from about 15% to about 75% by total weight of the copolymer, and A comprises from about 20% to about 75% by total weight of the copolymer.
12. A copolymer produced by the method of claim 1 having the formula
wherein W is a derivative obtained from the cyclic monomer selected from the group consisting of esters and carbonates, x is a number from about 1 to about 200, and y is a number from about 1 to about 200.
13. A copolymer produced by the method of claim 1 having the formula
wherein W is a derivative obtained from the cyclic monomer selected from the group consisting of esters and carbonates, x is a number from about 50 to about 150, and y is a number from about 50 to about 150.
14. A medical device comprising the copolymer produced by the method of claim 1 .
15. A drug delivery device comprising the copolymer produced by the method of claim 1 .
16. A coating for a medical device comprising the copolymer produced by the method of claim 1 .
17. A copolymer having the formula
wherein W is a derivative obtained from a cyclic monomer selected from the group consisting of cyclic esters and cyclic carbonates, x is a number from about 1 to about 200, y is a number from about 1 to about 200, and A is an aromatic carbonate derivative obtained from an aromatic cyclic oligomeric carbonate of formula
wherein R is an aromatic comprising benzene, Z comprises COO, and n is a number from about 1 to about 30.
18. The copolymer of claim 17 , wherein W is a derivative obtained from a cyclic monomer selected from the group consisting of glycolide, L(−)-lactide, D(+)-lactide, meso-lactide, p-dioxanone, 1,4-dioxan-2one, 1,5 -dioxepan-2-one, epsilon-caprolactone, delta-valerolactone, gamma-butyrolactone, beta-propiolactone, ethylene carbonate, trimethylene carbonate, dimethyl trimethylene carbonate, 3-ethyl-3-hydroxymethyl trimethylene carbonate, propylene carbonate, trimethyloipropane monocarbonate, 4,6 dimethyl- 1,3-propylene carbonate, 2,2-dimethyl trimethylene carbonate, and 1,3-dioxepan-2-one, and combinations thereof, and A is an aromatic carbonate derivative obtained from an aromatic cyclic carbonate selected from the group consisting of formula
wherein m is a number from about 1 to about 30.
19. The copolymer of claim 17 , wherein W comprises from about 15% to about 75% by total weight of the copolymer, and A comprises from about 20% to about 75% by total weight of the copolymer.