Water-mediated preparations of polymeric materials
A process is provided for preparing a polymeric material through a water-mediated polymerization process that includes combining an alcohol monomer and an aqueous solution in a vessel, adding an acid monomer to the vessel, removing water from the vessel and producing the polymeric material from the vessel, wherein the polymeric material comprises a polyester of the alcohol monomer and the acid monomer. The methods described herein are particularly suitable for polymerization of poly(glycerol sebacate).
1. A method of preparing a polymeric material, comprising the steps of:
combining an alcohol monomer and an aqueous liquid in a vessel;
adding an acid monomer to the vessel;
removing water from the vessel; and
producing the polymeric material from the vessel, wherein the polymeric material comprises a polyester of the alcohol monomer and the acid monomer.
2. The method of claim 1 , comprising the step of refluxing the alcohol monomer, the aqueous liquid, and the acid monomer in the vessel.
3. The method of claim 1 , wherein the alcohol monomer comprises glycerol.
4. The method of any one of the preceding claims, wherein the aqueous liquid comprises a water-soluble agent.
5. The method of claim 4 , wherein the water-soluble agent comprises a vitamin, an anti-inflammatory agent, a protein, a protease, an herbicide, an aquarium food source, a growth factor, a glycoprotein, a proteoglycan, an anti-mitotic agent, an antiplatelet agent, an anti-coagulant agent, an anti-thrombotic agent, a thrombolytic agent, an enzyme, a chemotherapeutic agent, an antibiotic agent, an immunological adjuvant, a scaffolding material, a processing agent, or a combination thereof.
6. The method of claim 1 , wherein the aqueous liquid is water.
7. The method of claim 1 , wherein the acid monomer comprises a diacid.
8. The method of claim 7 , wherein the diacid comprises a compound of the formula [HOOC(CH 2 ) n COOH], wherein n=1-30.
9. The method of claim 8 , wherein the diacid comprises malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, or a combination thereof.
10. The method of claim 8 , wherein the diacid is sebacic acid.
11. The method of claim 1 , wherein the step of combining the alcohol monomer and the aqueous liquid comprises heating the alcohol monomer and the aqueous solution to about 50-200° C.
12. The method of claim 1 , wherein the step of combining the alcohol monomer and the aqueous liquid comprises heating the alcohol monomer and the aqueous solution to about 90-110° C.
13. The method of claim 1 , wherein the step of combining the alcohol monomer and the aqueous liquid comprises heating the alcohol monomer and the aqueous solution for a period of about 5 minutes to about 240 minutes.
14. The method of claim 1 , wherein the step of removing the water comprises heating the vessel to about 50-200° C.
15. The method of claim 1 , comprising reacting the acid monomer and alcohol monomer at atmospheric pressure under an inert atmosphere for about 1 hour to about 48 hours.
16. The method of claim 15 , further comprising applying a sub-atmospheric pressure for about 1 hour to about 76 hours after the step of reacting at atmospheric pressure under an inert atmosphere.
17. The method of claim 1 , comprising producing the polymeric material by applying a sub-atmospheric pressure for about 1 hour to about 76 hours.
18. The method of claim 1 further comprising adding a co-monomer or a polymer to the vessel to form the polymeric material as a co-polymer.
19. The method of claim 18 , wherein the co-monomer comprises a diacid, lactic acid, caprolactone, or a combination thereof.
20. The method of claim 1 further comprising reacting the produced polymeric material to form a co-polymer.
21. The method of claim 20 , wherein the polymeric material is poly(glycerol sebacate) and the co-polymer is formed by reacting the poly(glycerol sebacate) with poly(lactic acid).
22. A method of preparing a polymeric material, comprising the steps of:
combining glycerol and water in a vessel;
adding sebacic acid to the vessel;
removing water from the vessel;
reacting the glycerol and sebacic acid in the vessel at atmospheric pressure and a temperature in the range of 50-200° C. in the presence of an inert gas for a period of about 1 hour to about 48 hours;
applying a sub-atmospheric pressure to the vessel for about 1 hour to about 76 hours after the step of reacting in the presence of an inert gas at atmospheric pressure, with a temperature in the vessel in the range of 50-200° C. thereby forming a polymeric material in the vessel.
23. The method of claim 22 , wherein the sub-atmospheric pressure is in the range of 5 Torr to 20 Torr.
24. The method of claim 22 , wherein the sub-atmospheric pressure is applied for about 24 hours to about 36 hours.
25. An article of manufacture prepared by the method of claim 1 .
26. A bioabsorbable polymeric material prepared by the process of claim 1 , comprising poly(glycerol sebacate).
27. The bioabsorbable polymeric material of claim 26 , wherein the bioabsorbable polymeric material has anti-microbial characteristics.