Solvent-less ionic liquid epoxy resin

Patent metadata

Field	Value
Publication number	US-11976162-B2
Application number	US-202017431961-A
Country	US
Kind code	B2
Filing date	Feb 18, 2020
Priority date	Feb 18, 2019
Publication date	May 7, 2024
Grant date	May 7, 2024

Abstract

Solvent free epoxy systems are disclosed that can include a hardener compound H comprising: a molecular structure (R 1 —(Y 1 )n), wherein R 1 is an ionic moiety, Y 1 is a nucleophilic group, n is a between 2 and 10; and an ionic moiety A acting as a counter ion to R 1 ; and an epoxy compound E comprising: a molecular structure (R 2 —Z 1 )n), wherein R 2 is an ionic moiety, Z 1 comprises an epoxide group, n is a between 2 and 10, and an ionic moiety B acting as a counter ion to R 2 . In embodiments, the epoxy compound E and/or the hardener H is comprised in a solvent-less ionic liquid. The systems can further include accelerators, crosslinkers, plasticizers, inhibitors, ionic hydrophobic and/or super-hydrophobic compounds, ionic hydrophilic compounds, ionic transitional hydrophobic/hydrophilic compounds, biological active compounds, and/or plasticizer compounds. Polymers made from the disclosed epoxy systems and their methods of use are described.

First claim

What is claimed is:

1. An epoxy system, comprising:
a hardener compound H comprising a structure represented by R 1 -(Y) n and an ionic moiety A, wherein:
R 1 is an ionic moiety comprising a 2-methyl substituted imidazolium,
Y is a nucleophilic group,
n is an integer between 2 and 10 inclusive, and

A is a counter ion to R 1 ; and
an epoxy compound E comprising a structure represented by R 2 -(Z) p and an ionic moiety B, wherein:
R 2 is an ionic moiety,
Z comprises an epoxide group,
p is an integer between 2 and 10 inclusive, and

B is a counter ion to R 2 ,
wherein the hardener compound H and the epoxy compound E are configured to form a polymer when mixed.

2. The epoxy system of claim 1 , wherein the epoxy compound E is a solvent-less ionic liquid.

3. The epoxy system of claim 1 , wherein the hardener compound H is a solvent-less ionic liquid.

4. The epoxy system of claim 1 , wherein the structure represented by R 1 -(Y) n is 1,3,5-tris[1-(2′-aminoethyl)-2-methyl-1H-imidazol-3-iummethylenelbenzene.

5. The epoxy system of claim 1 , wherein the structure represented by R 1 -(Y) n is tetrakis[1-(2′-aminoethyl)-2-methyl-1H-imidazol-3-iummethyl]methane.

6. The epoxy system of claim 1 , further comprising one or more of an accelerator, a crosslinker, a plasticizer, and an inhibitor.

7. The epoxy system of claim 1 , further comprising one or more of the following additives:
an ionic hydrophobic compound;
a super-hydrophobic compound;
an ionic hydrophilic compound;
an ionic transitional hydrophobic/hydrophilic compound;
a biological active liquid compound; and
a plasticizer compound;
wherein the one or more additives are released as an ionic liquid upon polymerization of the hardener compound H and the epoxy compound E.

8. The epoxy system of claim 1 , further comprising a plasticizer compound, wherein the plasticizer compound has zero volatility.

9. The epoxy system of claim 1 , wherein the polymer comprises a plurality of polymeric chains, each polymeric chain having stable electrical charges along its length.

10. The epoxy system of claim 1 , wherein the polymer is porous.

11. The epoxy system of claim 1 , wherein the structure represented by R 1 -(Y) n is 1,3-di(2′-aminoethylene)-2-methylimidazolium.

12. The epoxy system of claim 1 , wherein R 1 and R 2 have the same charge.

13. A filtration membrane, a solid electrolyte, or an exchange membrane comprising the polymer of claim 1 .

14. A polymer produced by the polymerization of the epoxy system of claim 1 .

15. The polymer of claim 14 , wherein the polymer is a solid electrolyte.

16. An electronic component comprising the polymer of claim 15 .

17. The electronic component of claim 16 , wherein electronic component is a battery, a capacitor, a piezoelectric material, or an electro-actuator.

18. An epoxy system comprising:
a hardener compound H comprising a cation of 2-amino-N,N-bis( 2-aminoethyl)-N-methyl-ethanaminium and a counterion A; and
an epoxy compound E comprising a structure represented by R 2 -(Z) p and an ionic moiety B, wherein:
R 2 is an ionic moiety,
Z comprises an epoxide group,
p is an integer between 2 and 10 inclusive; and
B is a counter ion to R 2 ; and

wherein the hardener compound H and the epoxy compound E are configured to form a polymer when mixed.

19. An epoxy system comprising:
a hardener compound H comprising a cation having the following structure and a counterion A

and
an epoxy compound E comprising a structure represented by R 2 -(Z) p and an ionic moiety B, wherein:
R 2 is an ionic moiety,
Z comprises an epoxide group,
p is an integer between 2 and 10 inclusive; and
B is a counter ion to R 2 ; and

wherein the hardener compound H and the epoxy compound E are configured to form a polymer when mixed.

20. An epoxy system comprising:
a hardener compound H comprising a cation having the following structure and a counterion A

and
an epoxy compound E comprising a structure represented by R 2 -(Z) p and an ionic moiety B, wherein:
R 2 is an ionic moiety,
Z comprises an epoxide group,
p is an integer between 2 and 10 inclusive; and
B is a counter ion to R 2 ; and

wherein the hardener compound H and the epoxy compound E are configured to form a polymer when mixed.

Assignees

• Univ Arizona State

Inventors

• Friesen Cody
• Bautista-Martinez Jose Antonio
• Goncharenko Mykhaylo
• Johnson Paul

Classifications

• C08G59/5073 Primary

  having two nitrogen atoms in the ring · CPC title

• C08G59/022

  characterised by the preparation process or apparatus used · CPC title

• C08G59/245

  aromatic · CPC title

• C08G59/304

  containing phosphorus · CPC title

• C08G59/4064

  sulfur containing compounds (C08G59/4021, C08G59/4028 take precedence) · CPC title