Polyester based degradable materials and implantable biomedical articles formed therefrom
View Patent ↗A method of making an aliphatic polyester prepolymer, comprising: reacting, alone or in combination with other reactants, a diol with at least a first diacid (or a diester of the first diacid) to produce an aliphatic polyester prepolymer. The first diacid is preferably a trans-beta-hydromuconic acid (HMA). In some embodiments, the diol contains at least one ether linkage. In some embodiments the diol is further reacted with at a second diacid, or a diester of the second diacid, wherein the second diacid is different from the first diacid. Prepolymers produced from such processes and articles formed therefrom are also described.
1. A method of making an article comprising a thermoset elastomeric polymer, said method comprising:
forming an aliphatic polyester prepolymer into said article, and then
thermally crosslinking said prepolymer to produce said article;
wherein said aliphatic polyester prepolymer is produced by the process comprising reacting a diol or polyol with at least a first diacid, or a diester of said first diacid, to produce said aliphatic polyester prepolymer; wherein said first diacid is a trans-beta-hydromuconic acid (HMA); said prepolymer further comprising a crosslinking agent;
wherein said thermoset elastomeric polymer completely degrades within six months when immersed in phosphate buffered saline solution at 37° C.;
and wherein said article has a Young's modulus of 0.02 MPa to 20 MPa.
2. The method of claim 1 , wherein said diol or polyol contains at least one ether linkage.
3. The method of claim 1 , wherein said diol or polyol is further reacted with at a second diacid, or a diester of said second diacid, wherein said second diacid is different from said first diacid.
4. The method of claim 1 , said prepolymer selected from the group consisting of:
poly(diethylene glycol hydromuconoate);
poly(triethylene glycol hydromuconoate);
poly(tetraethylene glycol hydromuconoate); and
poly(diethylene glycol hydromuconoate-co-diethylene glycol adipate).
5. The method of claim 1 , wherein said prepolymer is liquid at a temperature of 25° C.
6. The method of claim 1 , wherein said prepolymer is amorphous at a temperature of 25° C.
7. The method of claim 1 , said prepolymer further comprising a polymerization initiator.
8. The method of claim 1 , said prepolymer further comprising an active agent.
9. The method of claim 1 , wherein said article is a biomedical implant.
10. The method of claim 1 , wherein said article is a drug depot.
11. The method of claim 1 , wherein said article is a drug eluting stent.
12. The method of claim 1 , wherein said article is a tissue engineering scaffold.
13. A method of making an article comprising a thermoset elastomeric polymer, said method comprising:
forming an aliphatic polyester prepolymer into said article, and then
thermally crosslinking said prepolymer to produce said article; wherein:
said aliphatic polyester prepolymer is produced by the process comprising reacting a diol with at least a first diacid, or a diester of said first diacid, to produce said aliphatic polyester prepolymer; wherein said first diacid is a trans-beta-hydromuconic acid (HMA), said prepolymer further comprising a crosslinking agent;
said diol is a polyol selected from the group consisting of poly(ethylene glycol) and poly(propylene glycol);
said prepolymer is liquid and amorphous at a temperature of 25° C.;
said thermoset elastomeric polymer completely degrades within six months when immersed in phosphate buffered saline solution at 37° C.; and
said article has a Young's modulus of 0.02 MPa to 20 MPa.