IP Library Granted Patent US 11,548,858
Granted Patent B2
US 11,548,858 · App. 17/324,222 · Granted Jan 10, 2023

Bioderived epoxide triazine networks and methods of making the same

Inventors: Caroline Bradshaw Hoyt (Denver, CO); Nicholas A. Rorrer (Golden, CO); Gregg Tyler Beckham (Golden, CO)
Assignee: Alliance for Sustainable Energy, LLC
C07D251/04
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Quick Facts
Patent No.
US 11,548,858
App. No.
17/324,222
Granted
Jan 10, 2023
Kind
B2
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.

Claims (55)

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.

Assignments (3)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
CONFIRMATORY LICENSE Recorded Jun 10, 2021
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 056497/0091 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2021
From: HOYT, CAROLINE BRADSHAW; BECKHAM, GREGG TYLER; RORRER, NICHOLAS A.
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 056455/0059 →