Polymer glass transition temperature manipulation via z/e hydrazone photoswitching

Patent metadata

Field	Value
Publication number	US-12435166-B2
Application number	US-202418638853-A
Country	US
Kind code	B2
Filing date	Apr 18, 2024
Priority date	Sep 13, 2019
Publication date	Oct 7, 2025
Grant date	Oct 7, 2025

Abstract

In an embodiment, the present disclosure pertains to a method of changing the glass transition temperature of a polymer. In some embodiments, the polymer includes at least one hydrazone-containing compound. In general, the methods of the present disclosure include one or more of the following steps of: (1) applying light to the polymer; and (2) thereby changing the glass transition temperature of the polymer. In another embodiment, the present disclosure pertains to a polymer having a light-adjustable glass transition temperature. In some embodiments, the polymer includes at least one hydrazone-containing compound.

First claim

What is claimed is:

1. A method of forming a polymer comprising a light-adjustable glass transition temperature (T g ), said method comprising:
covalently linking at least one hydrazone-containing compound to a polymer, wherein the hydrazone-containing compound linked to the polymer comprises:

 or combinations thereof,
wherein at least one of Y and R 1 comprises the polymer, and
wherein Y, R 1 and R 2 are each independently selected from the group consisting of H, alkyl groups, alkenyl groups, alkoxy groups, aryl groups, ketone groups, amine groups, amide groups, carboxyl groups, carboxylic acid groups, ester groups, thiol groups, sulfoxide groups, alcohol groups, alkyne groups, azide groups, CH 2 CH 3 , C(CH 3 ) 3 , (CH 2 ) 5 CH 3 , (CH 2 ) 7 CH 3 , (CH 2 ) 9 CH3, (CH 2 ) 11 CH 3 , (CH 2 ) 1-20 CH 3 , t-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl and combinations thereof.

2. The method of claim 1 , wherein the covalent linking comprises polymerization of monomers to the polymer in the presence of the at least one hydrazone-containing compound to form the hydrazone-containing compound linked to the polymer.

3. The method of claim 2 , wherein one or more of the monomers comprise one or more functional groups operable to facilitate the polymerization.

4. The method of claim 3 , wherein the one or more functional groups comprise an acrylate group.

5. The method of claim 3 , wherein the one or more functional groups comprise a methacrylate group.

6. The method of claim 1 , wherein the polymer is selected from the group consisting of polyethylene, polypropylene, polystyrene, poly(vinyl chloride), polyisobutylene, poly(methyl acrylate), poly(methyl methacrylate), polytetrafluoroethylene, poly(acrylic acid), polyacrylamide, polyacrylonitrile, poly(hydroxyethyl methacrylate), poly(hydroxyethyl acrylate), and combinations thereof.

7. The method of claim 1 , wherein the at least one hydrazone-containing compound is part of a side chain of the polymer.

8. The method of claim 1 , wherein Y comprises the polymer.

9. The method of claim 1 , wherein R 1 comprises the polymer.

10. The method of claim 1 , wherein Y and R 1 comprise the polymer.

11. The method of claim 1 , wherein Y and R 1 are each independently selected from the group consisting of:

wherein n is an integer of more than 1.

12. The method of claim 1 , wherein the at least one hydrazone-containing compound linked to the polymer is selected from the group consisting of:

and combinations thereof, wherein n is an integer of more than 1.

13. The method of claim 1 , wherein applied light increases the glass transition temperature (T g ) of the polymer, wherein the increase in T g occurs through photo-isomerization, and wherein the hydrazone in the at least one hydrazone-containing compound transitions from a Z state to an E state upon photoisomerization.

Assignees

• Dartmouth College

Inventors

• Abrahamian Ivan
• Yang Sirun
• Jeliazkov Laura L
• Harris Jared D

Classifications

• C08F20/60

  containing nitrogen in addition to the carbonamido nitrogen · CPC title

• C08F218/22

  Esters containing nitrogen · CPC title

• C08F212/26

  Nitrogen · CPC title

• C08F120/60

  containing nitrogen in addition to the carbonamido nitrogen · CPC title

• C08F220/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title