Bioderived epoxide triazine networks and methods of making the same

Patent metadata

Field	Value
Publication number	US-11548858-B2
Application number	US-202117324222-A
Country	US
Kind code	B2
Filing date	May 19, 2021
Priority date	May 19, 2020
Publication date	Jan 10, 2023
Grant date	Jan 10, 2023

Abstract

The present disclosure relates to a method that includes a first reacting of a first molecule and formaldehyde and/or a paraformaldehyde to form a triazine-containing intermediate and a second reacting of the triazine-containing intermediate with a second molecule having an epoxy group to form a triazine-containing product. As described herein, the triazine-containing product may be bioderived and biodegradable.

First claim

What is claimed is:

1. A method comprising:
a first reacting of a first molecule and formaldehyde or a paraformaldehyde to form a triazine-containing intermediate; and
a second reacting of the triazine-containing intermediate with a second molecule comprising an epoxy group to form a triazine-containing product, wherein:
the first molecule has a structure comprising

the triazine-containing intermediate has a structure comprising

the second molecule has a structure comprising

the triazine-containing product has a structure comprising

R 1 comprises at least one of a covalent bond or an alkyl having between 1 and 4 carbon atoms,
R 2 is derived from at least one of an amine group, an amide group, an ester group, or a carboxylic acid group,
R 3 comprises at least one of an alkoxy group, a hydroxyl group, an epoxide group, or a methylene group,
R 4 comprises at least one of an alkoxy group, a hydroxyl group, an epoxide group, or a methylene group, and
represents a covalent bond to a neighboring atom.

2. The method of claim 1 , wherein R 2 further comprises an alkyl group.

3. The method of claim 1 , wherein the structure of the triazine-containing product further comprises

4. The method of claim 3 , wherein the structure of the triazine-containing product further comprises

5. The method of claim 4 , wherein the structure of the triazine-containing product further comprises

6. The method of claim 1 , wherein:
the structure of the first molecule comprises

 and
the structure of the triazine-containing intermediate comprises

7. The method of claim 6 , further comprising:
a third reacting of the triazine-containing intermediate with a diamine, wherein:
the diamine has a structure comprising H 2 N—R—NH 2 ,
the third reacting transforms the triazine-containing intermediate to a structure comprising

 and
R comprises an alkyl group having between 1 and 10 carbon atoms.

8. The method of claim 7 , wherein the second reacting forms the triazine-containing product having a structure comprising

9. The method of claim 6 , further comprising:
a fourth reacting of the triazine-containing intermediate with a base, wherein:
the fourth reacting transforms the triazine-containing intermediate to a structure comprising

10. The method of claim 9 , wherein the second reacting forms the triazine-containing product having a structure comprising

11. The method of claim 1 , wherein at least one of the first molecule or the second molecule is bioderived.

12. The method of claim 1 , wherein the triazine-containing produce is biodegradable.

13. A composition comprising:
the structure

 wherein:
R 1 comprises at least one of a covalent bond or an alkane having between 1 and 4 carbon atoms,
R 2 comprises at least one of an amine group, an amide group, an ester group, or a carboxylic acid group,
R 3 comprises at least one of an alkoxy group, a hydroxyl group, an epoxide group, or a methylene group,
R 4 comprises at least one of an alkoxy group, a hydroxyl group, an epoxide group, or a methylene group, and
represents a covalent bond to a neighboring atom.

14. The composition of claim 13 , wherein:
the structure further comprises

15. The composition of claim 14 , wherein:
the structure further comprises

16. The composition of claim 15 , wherein:
the structure further comprises

17. The composition of claim 13 , wherein:
the structure comprises

 wherein:
R comprises an alkyl group having between 1 and 10 carbon atoms.

18. The composition of claim 13 , wherein:
the structure comprises

19. The composition of claim 13 , wherein at least a portion of the composition is bioderived.

20. The composition of claim 13 , wherein composition is biodegradable.

Assignees

• Alliance Sustainable Energy

Inventors

• Hoyt Caroline Bradshaw
• Rorrer Nicholas A
• Beckham Gregg Tyler

Classifications

• C07D251/04 Primary

  having no double bonds between ring members or between ring members and non-ring members · CPC title