Systems chemistry approach to polyhexahydrotriazine polymeric structures

Patent metadata

Field	Value
Publication number	US-10118993-B2
Application number	US-201715460785-A
Country	US
Kind code	B2
Filing date	Mar 16, 2017
Priority date	Nov 24, 2015
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

In some embodiments, a product, such as a thermoset, has a polyhexahydrotriazine and a self-polymerized cross-linkable polymer. In some embodiments, a product is the reaction product of a diamine, an aldehyde, and a compound having an α,β-unsaturated electron withdrawing moiety.

First claim

What is claimed is:

1. A product that is the reaction product of:
a diamine;
an aldehyde; and
a compound having an α,β-unsaturated electron withdrawing moiety.

2. The product of claim 1 , wherein the aldehyde is paraformaldehyde.

3. The product of claim 1 , wherein the compound having an α,β-unsaturated electron withdrawing moiety is

wherein R is selected from the group consisting of ether, aryl, and alkyl.

4. The product of claim 3 , wherein the ether is

the aryl is

and the alkyl is

5. The product of claim 1 , wherein the diamine is of the structure: NH 2 —X—NH 2 , wherein X is selected from the group consisting of a phosphine derivative, an ether, and a lactone.

6. The product of claim 5 , wherein the phosphine derivative is

the ether is

and the lactone is

7. The product of claim 1 , wherein the product comprises a polyhexahydrotriazine including the structure:

wherein each instance of X is independently a phosphine derivative, ether, or lactone.

8. The product of claim 7 , wherein the product further comprises: the structure

wherein R is selected from the group consisting of an ether, an aryl group, and an alkyl group, wherein X is selected from the group consisting of a phosphine, an ether, and a lactone, and wherein n is a positive integer.

9. The composition of claim 8 , wherein R is selected from the group consisting of ether of structure

aryl of structure

and alkyl of structure:

10. The composition of claim 9 , wherein n is a positive integer from between about 2 to about 500.

11. The composition of claim 8 , wherein R is ether.

12. The composition of claim 8 , wherein R is aryl.

13. The composition of claim 8 , wherein R is alkyl.

14. The product of claim 7 , wherein the product further comprises: the structure

wherein R is selected from the group consisting of ether, aryl, and alkyl, and wherein n is a positive integer.

15. The composition of claim 14 , wherein R is selected from the group consisting of ether of structure

aryl of structure

and alkyl of structure:

16. The composition of claim 15 , wherein n is a positive integer from between about 2 to about 500.

17. The composition of claim 14 , wherein R is ether.

18. The composition of claim 14 , wherein R is aryl.

19. The composition of claim 14 , wherein R is alkyl.

20. The product of claim 1 , wherein the product comprises: the structure

wherein R is selected from the group consisting of an ether, an aryl group, and an alkyl group, wherein X is selected from the group consisting of a phosphine, an ether, and a lactone, and wherein n is a positive integer.

Assignees

• IBM

Inventors

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

Classifications

• C08G73/0644 Primary

  Poly(1,3,5)triazines · CPC title

• H05K999/99

  Electricity · mapped topic

• C08G73/1039

  comprising halogen-containing substituents · CPC title

• C08G73/1067

  Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound · CPC title

• C07D207/452

  with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom · CPC title