Solvent-less ionic liquid epoxy resin

Patent metadata

Field	Value
Publication number	US-2021363341-A1
Application number	US-202117227223-A
Country	US
Kind code	A1
Filing date	Apr 9, 2021
Priority date	Oct 25, 2016
Publication date	Nov 25, 2021
Grant date	—

Abstract

Solvent free epoxy system that includes: a hardener compound H comprising: a molecular structure (Y1—R1—Y2), wherein R1 is an ionic moiety Y1 is a nucleophilic group and Y2 nucleophilic group; and an ionic moiety A acting as a counter ion to R1; and an epoxy compound E comprising: a molecular structure (Z1—R2—Z2), wherein R2 is an ionic moiety, Z1 comprises an epoxide group, and Z2 comprises an epoxide group; and an ionic moiety B acting as a counter ion to R2. 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

1 - 30 . (canceled)

31 . A method of preparing a diamine imidazolium compound, 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 imazolium compound.

32 . The method of claim 31 , wherein the haloalkylamine is bromoethylamine.

33 . The method of claim 31 , wherein the triphenylmethyl halide is tritylchloride.

34 . The method of claim 31 , wherein reacting the haloalkylamine with the triphenylmethyl halide occurs in the presence of triethylamine and dichloromethane.

35 . The method of claim 31 , wherein the protected haloalkylamine is bromoethyltriphenylmethylamine.

36 . The method of claim 31 , wherein the alkylimidazole is 2-methylimidazole.

37 . The method of claim 31 , wherein reacting the protected haloalkylamine with the alkylimidazole occurs in the presence of sodium hydride and dimethylformamide.

38 . The method of claim 31 , wherein removing the triphenylmethyl from the bisubstituted alkylimidazole occurs in acidic media.

39 . The method of claim 31 , wherein neutralizing the halide derivative of the bisubstituted alkylimidazole occurs in basic media.

40 . The method of claim 31 , wherein the diamine imidazolium ionic liquid is 1,3-di(2′-aminoethylene)-2-methylimidazolium bromide.

41 . An ionic liquid comprising the diamine imidazolium compound of claim 31 .

42 . A method of synthesizing a hardener compound of an epoxy system, the method comprising:
reacting a trialkylamino-substituted tertiary amine with a dialkyl dicarbonate to yield a protected trialkylamino-substituted tertiary amine with alkyloxycarbonyl protecting groups; reacting the protected trialkylamino substituted tertiary amine with an alkyl halide to yield a protected trialkylamino substituted alkylated quaternary amine cation and a halide counterion; and removing the alkyloxycarbonyl protecting groups from the protected trialkylamino-substituted tertiary amine to yield a trialkylamino-substituted alkylated quaternary amine cation.

43 . The method of claim 42 , wherein the trialkylamino-substituted tertiary amine is N1-bis(2-aminoethyl)-1,2-ethanediamine.

44 . The method of claim 42 , wherein each alkyloxycarbonyl protecting group is di-tert-butyl dicarbonate.

45 . The method of claim 42 , wherein the alkyl halide is methyl iodide.

46 . The method of claim 42 , wherein reacting the trialkylamino-substituted tertiary amine with the dialky dicarbonate occurs in the presence of triethylamine and dimethyl carbonate.

47 . The method of claim 42 , wherein reacting the protected trialkylamino substituted tertiary amine with the alkyl halide occurs in the presence of acetonitrile.

48 . The method of claim 42 , wherein removing the alkyloxycarbonyl protecting groups from the protected trialkylamino substituted alkylated quaternary amine cation occurs in the presence of an acid and dioxane and neutralizing excess acid with a base to yield an ionic liquid.

49 . The method of claim 48 , further comprising metathesizing the ionic liquid in an aqueous solution of a fluorinated lithium alkylsulfonimide.

50 . The method of 42 , wherein the trialkylamino-substituted alkylated quaternary amine cation is i 2-amino-N, N-bis(2-aminoethyl)-N-methyl-ethanaminium.

Assignees

• Univ Arizona State

Inventors

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

Classifications

• Y02P70/50

  Manufacturing or production processes characterised by the final manufactured product · CPC title

• C08K5/19

  Quaternary ammonium compounds · CPC title

• C08G59/504

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

• C08G59/5073 Primary

  having two nitrogen atoms in the ring · CPC title

• C08K5/3435

  Piperidines · CPC title