Synthesis of Benzene Tetracarboxamide Polyamine and Its Effect on Epoxy Resin Properties

Abstract

Epoxy resins have found various industrial applications in high-performance thermosetting resins, high-performance composites, electronic-packaging materials, adhesives, protective coatings, etc., due to their outstanding performance, including high toughness, high-temperature performance, chemical and environmental resistance, versatile processability and adhesive properties. However, cured epoxy resins are very brittle, which limits their applications. In this work, we attempted to enhance the toughness of cured epoxy resins by introducing benzene tetracarboxamide polyamine (BTCP), synthesized from pyromellitic dianhydride (PMDA) and diamines in N-methyl-2-pyrrolidone (NMP) solvent. During this reaction, increased viscosity and formation of amic acid could be confirmed. The chemical reactions were monitored and evidenced using 1 H-NMR spectroscopy, FT-IR spectroscopy, water gel-phase chromatography (GPC) analysis, amine value determination and acid value determination. We also studied the effect of additives on thermomechanical properties using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), dynamical mechanical analysis (DMA), thermomechanical analysis (TMA) and by measuring mechanical properties. The BTCP-containing epoxy resin exhibited high mechanical strength and adhesion strength proportional to the amount of BTCP. Furthermore, field-emission scanning electron microscopy images were obtained for examining the cross-sectional morphology changes of the epoxy resin specimens with varying amounts of BTCP.

VOC-free tricomponent reaction platform for epoxy network formation mediated by a recyclable ionic liquid

“…7 However, the molecules used for this task are usually limited to a handful and predominated by nitrogen compounds such as polyamines, polyamides, and polycarbamides. 8,9 Consequently, even the efforts to obtain bio-based alternatives to crosslinkers are highly focused on this class of compounds. 10 A more sustainable alternative to this issue is the use of crosslinkers based on functional groups such as carboxylates and alcohols, as they are amongst the most abundant groups in nature.…”

“…7 However, the molecules used for this task are usually limited to a handful and predominated by nitrogen compounds such as polyamines, polyamides, and polycarbamides. 8,9 Consequently, even the efforts to obtain bio-based alternatives to crosslinkers are highly focused on this class of compounds. 10…”

Synthesis of Tri‐Aryl Methane Epoxy Resin Isomers and Their Cure with Aromatic Amines

“…It also had a higher creep displacement attributed to increased chain mobility in the glassy state. Yu et al (2018) combined a rigid carboxamide structure with flexible aliphatic ethers to synthesize an amine, which when cured with an epoxy resin reported improvements in tensile strength, failure strain, and impact strength without any commensurate deterioration in flexural strength. Varley et al (2019) synthesized highly aromatic ether‐linked epoxy monomers and amines, exploring the impact of substitution patterns on the properties and processability .…”

Novel functionalized isocyanate groups polyhedral oligomeric silsesquioxanes/epoxy composites with advanced thermal and moisture resistance properties

“…26 Further the FT-IR spectrogram demonstrates that γ-aminopropylphenyl triethoxysilane reacted with 3OH-POSS to form caged Ph 7 POSS-NH 2 , and the disappearance of the stretching vibration peak of Si OH can be seen from the FT-IR spectrum, while the stretching vibration peak of NH 2 appeared at 3304 cm À1 . 27 In the FT-IR spectrum of MP, the characteristic absorption peak of N C O appears at 2264 cm À1 , which can be seen that MDI combines with Ph 7 POSS-NH 2 . 28 Meanwhile when the nitrogen atom is attached to Each peak position has a good attribution, and the integrated area of each peak is consistent with the theoretical value, which indicates that MP was successfully synthesized.…”