Degradable polyurethanes containing thioaminal groups

Patent metadata

Field	Value
Publication number	US-2017349694-A1
Application number	US-201615170375-A
Country	US
Kind code	A1
Filing date	Jun 1, 2016
Priority date	Jun 1, 2016
Publication date	Dec 7, 2017
Grant date	—

Abstract

Embodiments of the disclosure generally provide compositions and methods related to oligomeric and polymeric urethane materials that contain hydrolyzable polythioaminal groups for use in biomedical applications.

First claim

What is claimed is:

1 . A method of producing a biodegradable urethane material comprising thioaminal groups, comprising:
forming a urethane oligomer or a urethane polymer with functional groups; reacting the functional groups with a sulfur compound to produce thiol groups; and heating and reacting the thiol groups with hexahydrotriazine compounds to produce a biodegradable urethane material comprising thioaminal groups.

2 . The method of claim 1 , wherein the functional groups are terminal groups.

3 . The method of claim 1 , wherein the functional groups are pendant groups.

4 . The method of claim 1 , wherein the functional groups are unsaturated carbon groups.

5 . The method of claim 4 , wherein the functional groups are alkene groups.

6 . The method of claim 1 , wherein the sulfur compound is dihydrogen sulfide.

7 . The method of claim 1 wherein the thiols groups are a reaction product of a Michael addition reaction.

8 . The method of claim 1 wherein the forming a urethane oligomer or a urethane polymer with functional groups, reacting the functional groups with a sulfur compound to produce thiol groups, and heating and reacting the thiol groups with hexahydrotriazine compounds to produce a biodegradable urethane material comprising thioaminal groups are performed in one reaction vessel.

9 . The method of claim 1 wherein the biodegradable urethane material comprising thioaminal groups is a reaction product of a sequential addition of some of the starting materials.

10 . The method of claim 1 wherein the biodegradable urethane material comprising thioaminal groups hydrolyzes in aqueous media.

11 . The method of claim 10 wherein the hydrolysis products of the biodegradable urethane material comprising thioaminal groups are non-toxic.

12 . A biocompatible polymer, comprising:
urethane groups and thioaminal groups, wherein the thioaminal groups hydrolyze.

13 . The biocompatible polymer of claim 12 , wherein the urethane groups have a repeat unit of at least 2 and less than 100.

14 . The biocompatible polymer of claim 12 , wherein the thioaminal groups have a repeat unit of at least 2 and less than 100

15 . The biocompatible polymer of claim 14 , further comprising at least one oligomeric or polymeric thioaminal terminal or end group.

16 . The biocompatible polymer of claim 15 , wherein the polymer is an “ABA” block copolymer, wherein A is a oligomeric or polymeric thioaminal group, and B is a urethane oligomer or polymer.

17 . The biocompatible polymer of claim 12 , wherein the polymer is a random copolymer.

18 . The biocompatible polymer of claim 12 , wherein the polymer is a dendritic polymer.

19 . The biocompatible polymer of claim 13 , wherein the oligomeric or polymeric urethane groups comprise at least one pendant thioaminal group.

20 . The biocompatible polymer of claim 19 , wherein the thioaminal group is a crosslinking group.

Assignees

• IBM

Inventors

• Boday Dylan J
• Garcia Jeannette M
• Hedrick James L
• Wojtecki Rudy J

Classifications

• C08G18/3876

  containing mercapto groups · CPC title

• C08G2230/00

  Compositions for preparing biodegradable polymers · CPC title

• C08G18/675

  Low-molecular-weight compounds · CPC title

• C08G18/87 Primary

  by sulfur · CPC title

• C08G18/735

  containing one isocyanate or isothiocyanate group linked to a primary carbon atom and at least one isocyanate or isothiocyanate group linked to a tertiary carbon atom · CPC title