Self-integrating hydrogels and methods for making the same

Patent metadata

Field	Value
Publication number	US-10513587-B2
Application number	US-201715720430-A
Country	US
Kind code	B2
Filing date	Sep 29, 2017
Priority date	Apr 2, 2015
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

A self-integrating hydrogel includes a water-soluble polymer. The water-soluble polymer includes a repeating unit having at least one functional group that includes an oxygen atom, a sulfur atom, or a nitrogen atom, and a pendant chain covalently attached to the oxygen atom, the sulfur atom, or the nitrogen atom of the at least one functional group of the repeating unit. The pendant chain includes ureido-pyrimidinone.

First claim

What is claimed is:

1. A self-integrating hydrogel, consisting of
a water-soluble polymer, including:
a repeating unit containing at least one glucose unit; and
a pendant chain covalently attached to an oxygen atom of some of the repeating units, the pendant chain including ureido-pyrimidinone, wherein a density of substitution of the ureido-pyrimidinone is 8.1 or less.

2. The self-integrating hydrogel as defined in claim 1 wherein the hydrogel does not have a core-shell structure.

3. The self-integrating hydrogel as defined in claim 1 wherein the water-soluble polymer is a modified dextran.

4. The self-integrating hydrogel as defined in claim 1 wherein the water-soluble polymer is a modified cellulose and the repeating unit includes two β(1→4) linked D-glucose units.

5. The self-integrating hydrogel as defined in claim 1 wherein the pendant chain includes an isocyanate that links the ureido-pyrimidinone to the oxygen atom of the some of the repeating units.

6. The self-integrating hydrogel as defined in claim 1 wherein the pendant chain includes an activated ester, an epoxy group, or an acyl chloride group that links the ureido-pyrimidinone to the oxygen atom of the some of the repeating units.

7. A method for making the self-integrating hydrogel as defined in claim 1 , the method comprising grafting a ureido-pyrimidinone-isocyanate to a hydroxyl group of some repeating units of a backbone of the water soluble polymer, each repeating unit containing the at least one glucose unit, thereby forming the pendant chain including the ureido-pyrimidinone-isocyanate.

8. The method as defined in claim 7 , further comprising forming the ureido-pyrimidinone-isocyanate by reacting an isocyanate with 2-amino-4-hydroxy-6-methylpyrimidine.

9. The method as defined in claim 8 , further comprising:
dissolving water soluble polymer in a first solvent to form a first solution;
dissolving the ureido-pyrimidinone-isocyanate in a second solvent to form a second solution;
mixing at least some of the first solution with the second solution to form a mixture;
adding a catalyst to the mixture under stirring;
curing the mixture at a predetermined temperature for a predetermined time to form the self-integrating hydrogel; and
exposing the self-integrating hydrogel to a solvent exchange process.

10. The method as defined in claim 7 , further comprising controlling the density of substitution of ureido-pyrimidinone by changing a feed ratio of the ureido-pyrimidinone-isocyanate to the water-soluble polymer.

Assignees

• Univ Michigan Regents

Inventors

• Ma Peter X
• Hou Sen

Classifications

• C08J2301/02

  Cellulose; Modified cellulose · CPC title

• C08J2305/08

  Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof · CPC title

• C08J2305/02

  Dextran; Derivatives thereof · CPC title

• C08F271/02

  on to polymers of monomers containing heterocyclic nitrogen · CPC title

• C08B37/003

  Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof · CPC title