Hydrogels from dynamic covalent networks

Patent metadata

Field	Value
Publication number	US-10696791-B2
Application number	US-201715621854-A
Country	US
Kind code	B2
Filing date	Jun 13, 2017
Priority date	Nov 11, 2015
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

A polymer is described herein that includes a plurality of N-J-N or N—C—S repeating units, wherein each J is independently a carbon atom, an alkyl group, or an aryl group; a plurality of hydrophilic groups bonded with the repeating units; and a plurality of hydrophobic groups bonded with the hydrophilic groups and the repeating units. Such polymers may be made into hydrogels by exposure to water, and the hydrogels may be used as delivery vehicles for various payloads.

First claim

What is claimed is:

1. A method of forming a polymer, comprising:
reacting a hydrophobic component with a hydrophilic component to form a polymer having hydrophobic sections and hydrophilic sections, the polymer having a general structure selected from the group consisting of

wherein:
each instance of R 1 is independently aryl, polyester, or polyamide,
each instance of R 6 is independently a group having hydrophilic components,
each instance of R 2 and R 5 is independently an organic or hetero-organic group,
each instance of R 3 is independently an electron-deficient organic or hetero-organic group,
each instance of R 7 is a trivalent organic or hetero-organic group,
each instance of X is independently a hydrophobic group, and
each instance of n is a positive integer, and wavy bonds in a structure signify covalent bonds to other atoms, and
at least one of the hydrophilic component or the hydrophobic component comprises a thioaminal or a polythioaminal, the polythioaminal having repeated S—C—N—C—S linkages or repeated S—C—N—R 3 —N—C—S linkages.

2. The method of claim 1 , wherein the hydrophobic component is a monothiol.

3. The method of claim 2 , wherein the hydrophobic component is a theranostic agent.

4. The method of claim 3 , wherein the hydrophobic component is selected from the group consisting of

wherein G is any carbon-bondable substituent.

5. A method of forming a polymer, comprising:
reacting a hydrophobic component with a hydrophilic component to form a polymer having hydrophobic sections and hydrophilic sections, the polymer having a general structure selected from the group consisting of

wherein:
each instance of R 1 is independently aryl, polyester, or polyamide,
each instance of R 6 is independently a group having hydrophilic components,
each instance of R 2 and R 5 is independently an organic or hetero-organic group,
each instance of R 3 is independently an electron-deficient organic or hetero-organic group,
each instance of R 7 is a trivalent organic or hetero-organic group,
each instance of X is independently a hydrophobic group,
each instance of n is a positive integer,
wavy bonds in a structure signify covalent bonds to other atoms, and
at least one of the hydrophilic component or the hydrophobic component comprises a hexahydrotriazine, a polyhexahydrotriazine, a thioaminal, or a polythioaminal, the polythioaminal having repeated S—C—N—C—S linkages or repeated S—C—N—R 3 —N—C—S linkages.

6. The method of claim 5 , wherein the hydrophobic component is a monothiol.

7. The method of claim 6 , wherein the hydrophobic component is a theranostic agent.

8. The method of claim 7 , wherein the hydrophobic component is selected from the group consisting of

wherein G is any carbon-bondable substituent.

9. A method of forming a polymer, comprising:
reacting a hydrophobic component with a hydrophilic component to form a polymer having hydrophobic sections and hydrophilic sections, the polymer having a general structure selected from the group consisting of

wherein:
each instance of R 1 is independently aryl, polyester, or polyamide,
each instance of R 6 is independently a group having hydrophilic components,
each instance of R 2 and R 5 is independently an organic or hetero-organic group,
each instance of R 3 is independently an electron-deficient organic or hetero-organic group,
each instance of R 7 is a trivalent organic or hetero-organic group,
each instance of X is independently a hydrophobic group,
each instance of n is a positive integer,
wavy bonds in a structure signify covalent bonds to other atoms,
the hydrophilic component comprises a hexahydrotriazine, a polyhexahydrotriazine, a thioaminal, or a polythioaminal, the polythioaminal having repeated S—C—N—C—S linkages or repeated S—C—N—R 3 —N—C—S linkages, and
the hydrophobic component is a monothiol.

10. The method of claim 9 , wherein the monothiol is selected from the group consisting of

wherein G is any carbon-bondable substituent.

Assignees

• IBM

Inventors

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

Classifications

• C08G81/00 Primary

  Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42}) · CPC title

• C08G73/0253

  Polyamines containing sulfur in the main chain · CPC title

• C08G73/0638

  with at least three nitrogen atoms in the ring · CPC title

• A61K47/6903

  the form being semi-solid, e.g. an ointment, a gel, a hydrogel or a solidifying gel · CPC title

• A61K47/59

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes · CPC title