Poly(orthoester) polymers, and methods of making and using same

• US 8,133,968 B2
• Filed: 12/14/2010
• Issued: 03/13/2012
• Est. Priority Date: 06/29/2006
• Status: Expired due to Fees

• Current Assignee: Medtronic Incorporated (Medtronic Plc)
• Original Assignee: Medtronic Incorporated (Medtronic Plc)
• Inventors: Alkatout, Julie A., Benz, Michael Eric, Sparer, Randall V.
• Primary Examiner(s): Heincer, Liam
• Application Number:
  US12/968,004
• Publication Number:
  US 20110082275A1
• Time in Patent Office: 455 Days
• Field of Search: 528/425, 528/392, 528/406
• US Class Current: 528/425
• CPC Class Codes: C08G 63/664 derived from hydroxy carboxylic acids
• CPC Class Codes: C08G 64/183 containing polyether sequences
• CPC Class Codes: C08G 65/34 from hydroxy compounds or their metallic derivatives C08G65/26 takes precedence

Abstract

Poly(orthoester) polymers, and methods of making and using such poly(orthoester) polymers are provided. The poly(orthoester) polymers can be useful for applications including, for example, medical devices and pharmaceutical compositions. In a preferred embodiment, the poly(orthoester) polymers are biodegradable.

Claims

1. A method of preparing a polymer, the method comprising:

combining components comprising;

at least one hydroxy-containing compound of the formula (Formula I)

HO-A-OH; and

at least one orthoester of the formula (Formula II)

2. The method of claim 1 wherein the components further comprise at least one diol different than at least one hydroxy-containing compound of the formula (Formula I).

3. The method of claim 1 wherein combining components further comprises combining a solvent that forms an azeotrope with R¹⁴OH.

4. The method of claim 3 wherein removing byproducts comprises removing byproducts under azeotropic conditions.

5. The method of claim 1 wherein combining components further comprises combining a polymerization agent.

6. The method of claim 5 wherein the polymerization agent comprises a Lewis acid or a Brø

nsted-Lowry acid.

7. The method of claim 6 wherein the Brø

nsted-Lowry acid is selected from the group consisting of hydrochloric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, camphorsulfonic acid, and combinations thereof.

8. The method of claim 6 wherein the Lewis acid comprises an element selected from the group consisting of Al, Fe, B, Zn, Sb, Ti, Cu, Sn, Si, and combinations thereof.

9. The method of claim 5 wherein the polymerization agent comprises an organometallic compound or a metal salt.

10. The method of claim 9 wherein the metal salt is selected from the group consisting of metal halides, metal pseudohalides, metal sulfonates, metal carboxylates, metal carbonates, and combinations thereof.

11. The method of claim 10 wherein the metal salt comprises a metal selected from the group consisting of Zn, Cs, and combinations thereof.

12. The method of claim 5 wherein the polymerization agent comprises a plurality of sites for initiating polymerization.

13. The method of claim 1 wherein combining components further comprises combining an additional polymerizable compound selected from the group consisting of ketene acetals, monofunctional orthoesters, polyfunctional orthoesters, imagable compounds, compounds having latent reactive sites, and combinations thereof.

14. The method of claim 13 wherein the additional polymerizable compound is an orthoester different than the at least one orthoester.

15. The method of claim 1 wherein the polymer can be further reacted as a soft segment of a segmented polymer selected from the group consisting of polyurethanes, polyethylenes, polycarbonates, polyureas, and combinations thereof.

16. The method of claim 1 wherein conditions effective to polymerize comprise combining at least a portion of the components without adding a solvent.

17. The method of claim 1 wherein conditions effective to polymerize comprise combining at least a portion of the components in a dry organic solvent.

18. The method of claim 1 wherein conditions effective to polymerize comprise combining at least a portion of the components under an inert atmosphere.