Synthesis and properties of a novel bismaleimide resin containing 1,3,4‐oxadiazole moiety and the blend systems thereof with epoxy resin

Abstract

A new bismaleimide monomer, 2‐((4‐maleimidophenoxy)methyl)‐5‐(4‐maleimidophenyl)‐1,3,4‐oxadiazole (Mioxd), was designed and synthesized. The chemical structure of the monomer was confirmed by means of Fourier transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (1H NMR) spectroscopy and elemental analysis, and its thermal properties were characterized using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Mioxd as a reactive modifier was blended with epoxy resin based on bisphenol A diglycidyl ether (DGEBA) in weight ratio of 5, 10, and 15%, using 4,4′‐diaminodiphenyl sulfone (DDS) as hardener. The effect of Mioxd addition on the cure behavior and thermal properties of the blend resins was studied by DSC, TGA, and dynamic mechanical analysis (DMA). DSC investigations showed that the main exothermic peak temperature (Tp) of the blend systems did not obviously shift with increasing Mioxd content whereas a new shoulder appeared and gradually grew on the high temperature side of the exothermic peak. The results of DMA measurements exhibited the glassy storage modulus (G') and glass transition temperatures (Tg) increased as the Mioxd content was increased, the cured blends investigated were miscible and no phase separation occurred. Further, the thermal decomposition temperature first decreased and then increased, but the char yield at 600°C increased with an increase in Mioxd content. POLYM. ENG. SCI., 2011. © 2011 Society of Plastics Engineers

Synthesis and characterization of asymmetric bismaleimide oligomers with improved processability and thermal/mechanical properties

“…They are employed as base resins in advanced composites and printed circuit boards due to their high performance‐to‐cost ratio and relatively high temperature resistance. A consideration of both performance and cost has made BMI resins the leading contenders in the field of advanced thermosetting polymers .…”

“…They are employed as base resins in advanced composites and printed circuit boards due to their high performance-to-cost ratio and relatively high temperature resistance. A consideration of both performance and cost has made BMI resins the leading contenders in the field of advanced thermosetting polymers [1][2][3][4]. BMI oligomers are low-molecular-weight versions that are terminated by two maleimide functional groups, often containing multiple aromatic moieties in order to enhance their processability and cured properties.…”

Properties of bismaleimide resin modified with polyrotaxane as a stress relaxation material

“…While these investigations demonstrated an increased toughness of the cured resin, the mechanical properties were often degraded. Another approach is to incorporate the 1,3,4‐oxadiazole ring with a highly rigid and symmetrical molecular structure into the BMI structure . While BMI containing 1,3,4‐oxadiazole has shown an improvement in toughness, the high melting temperatures lead to unfavourable processability properties for these materials.…”

Soluble asymmetric bismaleimide with low molten viscosity and its high glass transition temperature polymer

“…Based on the structure–properties relationships, the unsymmetrical chemical structure can hinder the ordered packing or crystallization of the molecules, hence improve the solubility of the monomers. Recently, Chen synthesized three asymmetric bismaleimide monomers containing 1,3,4‐oxadiazole group 8, which are soluble in acetone and tetrahydrofuran. However, the melting points of the three BMI monomers are higher than 200 °C and close to the onset curing temperatures, which means the processing temperature window is very narrow for the molten resins.…”