Solvent-less ionic liquid epoxy resin

Patent metadata

Field	Value
Publication number	US-11859077-B2
Application number	US-202117227223-A
Country	US
Kind code	B2
Filing date	Apr 9, 2021
Priority date	Oct 25, 2016
Publication date	Jan 2, 2024
Grant date	Jan 2, 2024

Abstract

Solvent free epoxy system that includes: a hardener compound H comprising: a molecular structure (Y 1 —R 1 —Y 2 ), wherein R 1 is an ionic moiety Y 1 is a nucleophilic group and Y 2 nucleophilic group; and an ionic moiety A acting as a counter ion to R 1 ; and an epoxy compound E comprising: a molecular structure (Z 1 —R 2 —Z 2 ), wherein R 2 is an ionic moiety, Z 1 comprises an epoxide group, and Z 2 comprises an epoxide group; 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 used.

First claim

What is claimed is:

1. A method of preparing a diamine imidazolium halide, the method comprising:
reacting a haloalkylamine with a triphenylmethyl halide to yield a protected haloalkylamine, wherein the haloalkylamine is a primary amine and the protected haloalkylamine is a secondary amine;
reacting the protected haloalkylamine with an alkylimidazole to yield a bisubstituted alkylimidazole;
removing the triphenylmethyl from the bisubstituted alkylimidazole to yield a halide derivative of the bisubstituted alkylimidazole; and
neutralizing the halide derivative of the bisubstituted alkylimidazole to yield the diamine imidazolium halide,
wherein:
the haloalkylamine is bromoethylamine,
the triphenylmethyl halide is tritylchloride,
the protected haloalkylamine is bromoethyltriphenylmethylamine;
the alkylimidazole is 2-methylimidazole, and
the diamine imidazolium halide is 1,3-di(2′-aminoethylene)-2-methylimidazolium bromide.

2. The method of claim 1 , wherein reacting the haloalkylamine with the triphenylmethyl halide occurs in the presence of triethylamine and dichloromethane.

3. The method of claim 1 , wherein reacting the protected haloalkylamine with the alkylimidazole occurs in the presence of sodium hydride and dimethylformamide.

4. The method of claim 1 , wherein removing the triphenylmethyl from the bisubstituted alkylimidazole occurs in acidic media.

5. The method of claim 1 , wherein neutralizing the halide derivative of the bisubstituted alkylimidazole occurs in basic media.

6. An ionic liquid comprising the diamine imidazolium halide of claim 1 .

7. The method of claim 1 , wherein the 1,3-di(2′-aminoethylene)-2-methylimidazolium bromide is a hardener compound of an ionic liquid epoxy system.

8. The method of claim 7 , wherein the 1,3-di(2′-aminoethylene)-2-methylimidazolium bromide is configured to react with an ionic epoxy compound of the ionic liquid epoxy system.

9. The method of claim 8 , wherein the ionic epoxy compound comprises: a molecular structure (Z 1 —R 2 —Z 2 ), where R 2 is an ionic moiety, Z 1 comprises an epoxide group, and Z 2 comprises an epoxide group; and an ionic moiety B acting as a counter ion to R 2 .

10. A method comprising:
preparing 1,3-di(2′-aminoethylene)-2-methylimidazolium bromide according to the method of claim 9 ;
preparing the ionic liquid epoxy system with the 1,3-di(2′-aminoethylene)-2-methylimidazolium bromide as a hardener compound; and
reacting the 1,3-di(2′-aminoethylene)-2-methylimidazolium bromide with the ionic epoxy compound to yield a polymer.

11. The method of claim 10 , wherein the polymer is suitable as a component of a battery.

Assignees

• Univ Arizona State

Inventors

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

Classifications

• C08L63/00 Primary

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08G59/245

  aromatic · CPC title

• C08G59/302

  containing sulfur · CPC title

• C08G59/304

  containing phosphorus · CPC title

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title