New Epoxy Thermosets Derived from a Bisimidazolium Ionic Liquid Monomer: An Experimental and Modeling Investigation

Abstract

In this study, a novel polymerizable ionic liquid monomer (ILM) based on a bisimidazolium salt was first synthesized in order to substitute bisphenol A diglycidyl ether (DGEBA) as a starting material, avoiding the use of highly toxic and carcinogenic bisphenol A and epichlorohydrin products. From such a new epoxy monomer, an epoxy network was prepared from the copolymerization between the bisimidazolium salt and isophorone diamine (IPD). Subsequently, the properties of this novel ionic liquid based polymer network have been investigated in terms of polyaddition reaction kinetics as well as the architectureproperties, i.e., thermal stability, surface properties, and the mechanical performances. In addition, for the first time, molecular dynamics simulations were combined with experimental measurements in order to confirm the experimental data as well to be able to predict the physical behaviors from their architecture, molecular scale structuration, and thermomechanical properties of the resulting network. Finally, the substitution of DGEBA by this ILM led to a thermosetting polymer with high thermal stability (up to 450 °C), hydrophobic behavior (21 mJ m −2 ), and promising mechanical performances (1.7 GPa) including a shape memory behavior.

Molecular-Level Investigation of Cycloaliphatic Epoxidised Ionic Liquids as a New Generation of Monomers for Versatile Poly(Ionic Liquids)

“…We also predicted the coefficients of volumetric thermal expansions ( ) and the coefficients of linear thermal expansions ( ) for the glassy region (the region below T ) and amorphous region (the region above T ) for each system [ 21 ]. Our results indicate that the results in larger in the amorphous region (above T ) than that in the glassy region (below T ) for both systems.…”

“…Notwithstanding the fact that the design of epoxidised ILs is an elegant and efficient strategy to tailor new epoxy materials, the synthesis of monomers can be costly and laborious. Hence, the development of computational routines that are able to accurately predict the mechanical properties of materials can supply valuable insights for monomer designing [ 21 ]. Molecular dynamics (MD) simulations are a versatile tool to investigate materials at the molecular level.…”

A Review on Ionic Liquid Gas Separation Membranes

“…Furthermore, several hybrid urethane-imide PILs showed enhanced CO 2 sorption capacity in the CO 2 physisorption experiments [ 180 ]. Various attempts successfully yielded PILs incorporating polyepoxide building blocks [ 181 , 182 , 183 , 184 , 185 ]. Most of the research uniting PILs and epoxides focuses on PILs usage as catalysts for the fixation of CO 2 by cycloaddition to form cyclic carbonates [ 186 ].…”

Synthesis of new ionic liquid-grafted metal-oxo nanoclusters – Design of nanostructured hybrid organic-inorganic polymer networks

“…The anionic exchange of Cl − to NTf 2 was studied here because the later one is known to give materials with better thermal stability and higher T g [54,58]. The present study unfolds as following: first, the influence of non-modified POSS® Ph (POSS® Ph -triol) and IL-g-POSS® Ph on the polymerization of the epoxy prepolymer is described.…”