Use of eugenol and rosin as feedstocks for biobased epoxy resins and study of curing and performance properties

• Published in: Polymer international 2014-04, Vol.63 (4), p.760-765
• Main Authors: Qin, Jianglei, Liu, Hongzhi, Zhang, Pei, Wolcott, Michael, Zhang, Jinwen
• Format: Article
• Language: English
• Subjects: Anhydrides; Applied sciences; bioepoxy; Bisphenol A; Catalysts; Chemical industry; Chemical properties; Curing; Curing agents; curing kinetics; Differential scanning calorimetry; Dynamic mechanical properties; Dynamic stability; Epoxy resins; Eugenol; Exact sciences and technology; Fourier transforms; Intermediates; Maleopimaric acid; Mechanical analysis; Mechanical properties; NMR; Nuclear magnetic resonance; Organic chemistry; Polymer industry, paints, wood; Polymers; Properties and testing; Rosin; Stability analysis; Technology of polymers; Thermal stability; Thermogravimetric analysis; Thermomechanical properties
• ISSN: 0959-8103; 1097-0126
• DOI: 10.1002/pi.4588

In this study, an epoxy based on eugenol and an anhydride curing agent based on rosin were prepared. Curing of the eugenol epoxy with a commercial anhydride curing agent and with the rosin‐derived anhydride curing agent was studied. For comparison, a commercial bisphenol A type epoxy, DER353, was also selected in the curing study. The syntheses of the eugenol epoxy and rosin anhydride were investigated and the chemical structures of the products and intermediates were characterized using 1H NMR and Fourier transform infrared spectroscopies. Non‐isothermal curing of the eugenol epoxy with hexahydrophthalic anhydride and the rosin‐derived maleopimaric acid was studied using differential scanning calorimetry. Thermomechanical properties and thermal stability of the cured epoxy resins were evaluated using dynamic mechanical analysis and thermogravimetric analysis, respectively. Addition of 2‐ethyl‐4‐methylimidazole as catalyst greatly decreased the curing temperature and promoted the completion of cure reactions. The results suggest that the eugenol epoxy and the bisphenol A type epoxy have similar reactivity, dynamic mechanical properties and thermal stability. © 2013 Society of Chemical Industry Eugenol and rosin are potential feedstocks for epoxy resins and the resulting biobased epoxy resins exhibit very comparable performance with respect to that of their petrochemical counterparts.