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 said 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 said second diacid, wherein said second diacid is different from said 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 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).
2. The method of claim 1 , wherein said diol contains at least one ether linkage.
3. The method of claim 1 , wherein said diol 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 , wherein said diol is a polyol.
5. The method of claim 1 , wherein said diol is a polyol selected from the group consisting of poly(ethylene glycol) and poly(propylene glycol).
6. 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).
7. The method of claim 1 , wherein said prepolymer is liquid at a temperature of 25° C.
8. The method of claim 1 , wherein said prepolymer is amorphous at a temperature of 25° C.
9. The method of claim 1 , said prepolymer further comprising a polymerization initiator.
10. The method of claim 1 , said prepolymer further comprising a crosslinking agent.
11. The method of claim 1 , said prepolymer further comprising an active agent.
12. The method of claim 1 , wherein said article has a Young's modulus of not less than 0.02 MPa.
13. The method of claim 1 , wherein said article is a biomedical implant.
14. The method of claim 1 , wherein said article is a drug depot.
15. The method of claim 1 , wherein said article is a drug eluting stent.
16. The method of claim 1 , wherein said article is a tissue engineering scaffold.
17. 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 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.; and
said article has a Young's modulus of not less than 0.02 MPa.