Biodegradable Elastomers

Patent metadata

Field	Value
Publication number	US-2019091377-A1
Application number	US-201816206937-A
Country	US
Kind code	A1
Filing date	Nov 30, 2018
Priority date	Jan 12, 2006
Publication date	Mar 28, 2019
Grant date	—

Abstract

The present inventions in various aspects provide elastic biodegradable polymers. In various embodiments, the polymers are formed by the reaction of a multifunctional alcohol or ether and a difunctional or higher order acid to form a pre-polymer, which is cross-linked to form the elastic biodegradable polymer. In preferred embodiments, the cross-linking is performed by functionalization of one or more OR groups on the pre-polymer backbone with vinyl, followed by photopolymerization to form the elastic biodegradable polymer composition or material. Preferably, acrylate is used to add one or more vinyls to the backbone of the pre-polymer to form an acrylated pre-polymer. In various embodiments, acrylated pre-polymers are co-polymerized with one or more acrylated co-polymers.

First claim

What is claimed is:

1 . An elastomeric composition comprising a cross-linked polyester, the cross-linked polyester comprising:
a polymeric unit of the general formula (-A-B—) n cross-linked between at least a portion of the A components of the polyester, at least a portion of the cross-links forming a dioic acid ester; wherein, A represents a substituted or unsubstituted ester, B represents a substituted or unsubstituted acid ester comprising at least two acid ester functionalities; and n represents an integer greater than 1.

2 . The composition of claim 1 , wherein the cross-linked polyester comprises a portion that can be represented by the general formula (I)

wherein m, n, p, q, and v each independently represent an integer greater than 1.

3 . The composition of claim 2 , wherein p=8, q=8 and v=4.

4 . The composition of claim 1 , wherein the average ratio of the number of cross-links to the number of (-A-B—) n , polymeric units is less than about 0.4.

5 . The composition of claim 1 , wherein the average ratio of the number of cross-links to the number of (-A-B—) n , polymeric units is greater than about 0.5.

6 . The composition of claim 1 , wherein the at least a portion of the cross-links forming a dioic acid ester comprise one or more substituted or unsubstituted alkylester functionalities.

7 . The composition of claim 1 , wherein the at least a portion of the cross-links forming a dioic acid ester comprise one or more substituted or unsubstituted carbonic acid alkylester functionalities.

8 . The composition of claim 1 , wherein the cross-linked polyester comprises
a polymeric unit of the general formula (-A-B—) n cross-linked to a substituted or unsubstituted alkane through at least a portion of the A components of the polyester, at least a portion of the cross-links forming an acid ester; wherein, A represents a substituted or unsubstituted ester, B represents a substituted or unsubstituted acid ester comprising at least two acid ester functionalities; and n represents an integer greater than 1.

9 . A biodegradable material formed from the composition of claim 1 , the material having a tensile Young's modulus less than about 1.5 MPa when measured according to ASTM standard D412-98a.

10 . A biodegradable material formed from the composition of claim 1 , the material having a tensile Young's modulus greater than about 0.05 MPa and an elongation of greater than about 45%, both when measured according to ASTM standard D412-98a.

11 . A biodegradable material formed from the composition of claim 1 , the material having a Young's modulus in the range between about 0.4 MPa and about 0.55 MPa when measured according to ASTM standard D412-98a.

12 . A biodegradable material formed from the composition of claim 1 , the material having a maximum elongation greater than about 170%.

13 . A biodegradable material formed from the composition of claim 1 , wherein the biodegradable material is one or more of non-toxic to humans, biocompatible and bioabsorbable.

14 . An elastomeric composition comprising a cross-linked polyester, the cross-linked polyester comprising:
a polymeric unit of the general formula (-A-B—) n cross-linked between at least a portion of the A components of the polyester, the cross-link forming a link comprising at least a portion of the general formula -(D) k -C—; wherein A represents a substituted or unsubstituted ester, B represents a substituted or unsubstituted acid ester comprising at least two acid ester functionalities; C represents a substituted or unsubstituted dioic acid ester; D represents one or more of a substituted or unsubstituted ester; n represents an integer greater than 1; and k represents an integer greater than 0.

15 . The composition of claim 14 , wherein the cross-linked polyester comprises at least a portion that can be represented by the general formula (II)

wherein m, n, p, q, and v each independently represent an integer greater than 1, and k represents an integer greater than 0.

16 . The composition of claim 15 , wherein p=8, q=8 and v=4.

17 . The composition of claim 14 , wherein the average ratio of the number of cross-links to the number of (-A-B—) n , polymeric units is less than about 0.4.

18 . The composition of claim 14 , wherein the average ratio of the number of cross-links to the number of (-A-B—) n polymeric units is greater than about 0.5.

19 . The composition of claim 14 , wherein the cross-linked polyester comprises
a polymeric unit of the general formula (-A-B—) n cross-linked to a substituted or unsubstituted alkane through at least a portion of the A components of the polyester, at least a portion of the cross-links forming an acid ester; wherein, A represents a substituted or unsubstituted ester, B represents a substituted or unsubstituted acid ester comprising at least two acid ester functionalities; and n represents an integer greater than 1.

20 . A biodegradable material formed from the composition of claim 14 , the material having a tensile Young's modulus less than about 17 MPa when measured according to ASTM standard D412-98a.

21 . A biodegradable material formed from the composition of claim 14 , the material having a tensile Young's modulus greater than about 0.6 MPa and an elongation of greater than about 20%, both when measured according to ASTM standard D412-98a.

22 . A biodegradable material formed from the composition of claim 14 , the material having a tensile Young's modulus greater than about 0.25 MPa when measured according to ASTM standard D412-98a and a swelling in water of greater than about 1%.

23 . A biodegradable material formed from the composition of claim 14 , the material having a tensile Young's modulus greater than about 0.25 MPa when measured according to ASTM standard D412-98a and a swelling in water of greater than about 40%.

24 . A biodegradable material formed from the composition of claim 14 , the material having a Young's modulus in the range between about 0.4 MPa and about 0.55 MPa when measured according to ASTM standard D412-98a.

25 . A biodegradable material formed from the composition of claim 14 , the material having a maximum elongation greater than about 60%.

26 . A biodegradable material formed from the composition of claim 14 , wherein the biodegradable material is one or more of: non-toxic to humans, biocompatible and bioabsorbable.

27 . An elastomeric biodegradable material formed from a cross-linked polyester, the elastomeric biodegradable material having a degradation rate that is substantially non-monotonic as a function of overall cross-link density.

28 . The elastomeric biodegradable material of claim 27 , wherein the cross-linked elastomeric polyester comprises:
a polymeric unit of the general formula (-A-B—) n cross-linked between at least a portion of the A components of the polyester, the cross-link forming a link comprising at least a portion of the general formula -(D) k -C—; wherein A represents a substituted or unsubstituted ester, B represents a substituted or unsubstituted acid ester comprising at least two acid ester functionalities

Assignees

• Massachusetts Inst Technology

Inventors

• Bettinger Christopher J
• Bruggeman Joost P
• Ferreira Lino Da Silva
• Karp Jeffrey M
• Langer Robert S
• Nijst Christiaan
• Zumbuehl Andreas
• Burdick Jason
• Kim Sonia J

Classifications

• C08J2367/07

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• A61L27/18

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61L27/58

  Materials at least partially resorbable by the body · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C08G63/6854

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title