Systems chemistry approach to polyhexahydrotriazine polymeric structures

Patent metadata

Field	Value
Publication number	US-10975201-B2
Application number	US-201816156606-A
Country	US
Kind code	B2
Filing date	Oct 10, 2018
Priority date	Nov 24, 2015
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

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 first compound that is a diamine;
a second compound that is an aldehyde;
a third compound having an α,β-unsaturated electron withdrawing moiety; and
a fourth compound that is a cross-linkable polymer.

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

3. The product of claim 1 , wherein the cross-linkable polymer is functionalized with at least one of cyanate, alkyne, epoxide, maleimide, or norbornene-2,3-dicarboximide.

4. The product of claim 1 , wherein the cross-linkable polymer is selected from the group consisting of:

wherein each instance of CZ′ is independently selected from a maleimide group, a norbornene-2,3-dicarboximide, a cyanate, an alkyne, and an epoxide, wherein the maleimide group, the norbornene-2,3-dicarboximide, the cyanate, the alkyne, and the epoxide are unsubstituted or substituted with alkyl or aryl, and wherein n is a positive integer.

5. The product of claim 4 , wherein the maleimide is

the norbornene-2,3-dicarboximide is

the cyanate is

the alkyne is

and the epoxide is

6. 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.

7. The product of claim 6 , wherein the ether is the aryl is

and the

alkyl is

8. The product of claim 6 , wherein R is an ether.

9. The product of claim 6 , wherein R is aryl.

10. The product of claim 6 , wherein R is alkyl.

11. 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.

12. The product of claim 11 , wherein the phosphine derivative is

the ether is

and the lactone is

13. The product of claim 1 , wherein the compound having an α,β-unsaturated electron withdrawing moiety is an acrylate that is 1,4-butanediol diacrylate or trimethylolpropane triacrylate.

14. The product of claim 1 , wherein the cross-linkable polymer is an epoxide that is a diglycidyl ether of a bisphenol.

15. The product of claim 1 , wherein the cross-linkable polymer is a compound with a backbone comprising aryl moieties.

16. The product of claim 1 , wherein the cross-linkable polymer is a compound comprising one or more functional moieties present at an α-terminus, a ω-terminus, and/or along a polymer backbone of the cross-linkable polymer.

Assignees

• IBM

Inventors

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

Classifications

• C08G73/1064

  containing sulfur · CPC title

• C08L79/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/1039

  comprising halogen-containing substituents · CPC title

• C08G73/065

  Preparatory processes · CPC title

• C08G73/0644 Primary

  Poly(1,3,5)triazines · CPC title