A new Schiff base epoxy oligomer resin: Synthesis, characterization, and thermal decomposition kinetics

Abstract

Oligo{2,2 0 -{1,4-phenylenebis[nitrilomethylylidene]}bis(6-methoxyphenol)} (OPNMMP) was synthesized from o-vanillin and p-phenylene diamine by oxidative polycondensation with NaOCl in an aqueous alkaline. Then, a new Schiff Base epoxy oligomer resin, OPNMMP-epichlorohydrine (EPC), was produced with EPC. The structures of the resulting compounds were confirmed by Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, 1 H-NMR, and 13 C-NMR. Further characterization processes were preformed by thermogravimetry (TG)-differential thermal analysis, gel permeation chromatography, and solubility testing. Also, the kinetics of the thermal decomposition of OPNMMP-EPC were investigated by thermogravimetric analysis. The TG curves showed that the thermal decomposition of OPNMMP-EPC occurred in one stage. The kinetic parameters related to the decomposition kinetics of OPNMMP-EPC were obtained from TG curves with the following methods: Friedman, Flynn-Wall-Ozawa, Kissinger, invariant kinetic parameter, and Coats-Redfern (CR), under an N 2 dynamic atmosphere and different heating rates (5, 10, 15, and 20 C/min). The mechanism function and pre-exponential factor were also determined by a master plots method. The apparent activation energies of the thermal decomposition were calculated from these methods for OPNMMP-EPC. The analysis of the results obtained by the CR and master plots methods showed that the decomposition mechanism of OPNMMP-EPC in N 2 was a deceleration-type mechanism.

Biobased Thermosetting Epoxy: Present and Future

“…Some research teams have already reported works on vanillin for epoxy synthesis and various applications. A Schiff base synthesized was used for metal ion chelation applications (Scheme ) …”

“…A Schiff base synthesized was used for metal ion chelation applications (Scheme 27). 133 Moreover, vanillin was used to synthesize biobased epoxy monomer by a chemoenzymatic process with Candida antartica lipase 134 (Scheme 28). In all cases, epoxy networks exhibited interesting thermal properties.…”

Renewable Epoxy Networks Derived from Lignin-Based Monomers: Effect of Cross-Linking Density

“…6,7 Because of the above-mentioned limitations associated with the use of bulk lignin, use of well characterized lignin-derived monomers for thermosets design is most appealing and has received extensive attention. Thermosets including epoxy resins, polybenzoxazines, vinyl ester resins and cyanate ester resins developed from lignin-derived building blocks like eugenol, 8,9 vanillin, 10,11 guaiacol 12 and creosol 13 have been reported. Improved reactivity of lignin-derived monomers rather than bulk lignin provides thermosets that exhibit more satisfactory mechanical and thermal properties.…”

Synthesis, characterization, and properties of silicone grafted epoxy/acrylonitrile butadiene styrene/graphene oxide nanocomposite with high adhesion strength and thermal stability

“…According to Kissinger's method and using Equation ( 8), the activation energy can be estimated by plotting Ln(β/ T p 2 ) versus 1/T p and fitting a straight line to the data points. [100,101] Slope of lines show E/R values. Calculation of activation energy through this method is shown in Figure S5.…”