Photoresponsive hexahydrotriazine polymers

Patent metadata

Field	Value
Publication number	US-9828467-B2
Application number	US-201615016610-A
Country	US
Kind code	B2
Filing date	Feb 5, 2016
Priority date	Feb 5, 2016
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

This disclosure describes new compositions and methods related to photoresponsive poly(hexahydrotriazines) and related polymers.

First claim

What is claimed is:

1. A polyhexahydrotriazine (PHT), comprising:
a plurality of trivalent hexahydrotriazine groups having the structure

and
a plurality of phenyl groups having the structure

wherein each wavy bond site of a given hexahydrotriazine group is covalently linked at a respective wavy bond site of a phenyl group, and each wavy bond site of a given phenyl group is covalently linked at a respective wavy bond site of a hexahydrotriazine group, and wherein at least one of A, B, C, D, and E is a photoreactive group, and wherein at least one of A, B, C, D, or E is a bridging group between at least two hexahydrotriazine groups.

2. The PHT of claim 1 , wherein at least one of A, B, C, D, and E absorbs ultraviolet radiation.

3. The PHT of claim 2 , wherein at least one of A, B, C, D, and E comprises a reaction product of ultraviolet radiation absorption.

4. The PHT of claim 3 , wherein the reaction product is a product of a photoreversible reaction.

5. The PHT of claim 3 , wherein the reaction product comprises a cyclic carbon group.

6. The PHT of claim 5 , wherein the reaction product comprises a cycloaliphatic carbon group.

7. The PHT of claim 5 , wherein the cyclic carbon group is the reaction product of a [2π+2π] cycloaddition reaction.

8. The PHT of claim 5 , wherein the cyclic carbon group is the reaction product of a [4π+4π] cycloaddition reaction.

9. The PHT of claim 6 , wherein cycloaliphatic carbon group comprises a cyclobutane group.

10. The PHT of claim 9 , wherein the cyclobutane group is a photoreaction product of at least two carbon-carbon double bonds.

11. The PHT of claim 10 , wherein the carbon-carbon double bonds are resonance stabilized.

12. The PHT of claim 3 , wherein at least one of A, B, C, D, and E comprises a carbon-carbon double bond.

13. The PHT of claim 12 , wherein at least one carbon-carbon double bond is resonance stabilized.

14. The PHT of claim 3 , wherein the reaction product includes at least one conjugated carbon-carbon double bond from a photo-cleavage reaction.

15. The PHT of claim 14 , wherein the at least one conjugated carbon-carbon double bond is a reaction product of a cyclobutane photo-cleavage reaction.

Assignees

• IBM

Inventors

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

Classifications

• C08G73/0644 Primary

  Poly(1,3,5)triazines · CPC title

• C08G73/065

  Preparatory processes · CPC title

• C08G12/08

  aromatic · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title