A non-bisphenol-A epoxy resin with high Tg derived from the bio-based protocatechuic Acid:Synthesis and properties

• Published in: Polymer (Guilford) Vol. 195; p. 122443
• Main Authors: Chen, Xingrong, Hou, Jiaren, Gu, Qun, Wang, Qinhong, Gao, Junfei, Sun, Jing, Fang, Qiang
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 08.05.2020; Elsevier BV
• Subjects: Acids; Biotransformation; Bisphenol A; Chemical synthesis; Crosslinking; Curing; Epichlorohydrin; Epoxy resins; Glass transition temperature; Protocatechuic acid; Rapid prototyping; Reaction kinetics; Thermal expansion; Thermal stability; Transition temperatures; Protocatechuic acid; Epoxy resins; Thermal stability
• ISSN: 0032-3861; 1873-2291
• DOI: 10.1016/j.polymer.2020.122443

A new bio-based non-bisphenol-A epoxy (PA-EP) resin was synthesized by one-pot reaction between protocatechuic acid (PA) and epichlorohydrin. This resin was cured by 4,4′-diaminodiphenyl methane (DDM) to give a cross-linked network showing a glass transition temperature (Tg) of more than 250 °C, which was much higher than that of a cured commercial bisphenol-A epoxy resin (DGEBA) (189 °C). The cured PA-EP resin also displayed the coefficient of thermal expansion (CTE) of 66 ppm/°C, which was lower than 72 ppm/°C of cured DGEBA resin. The curing kinetics of PA-EP/DDM system was also investigated, indicating that the curing process was a pseudo first order reaction (n = 0.94) and the activation energy was about 54.17 kJ/mol. Because protocatechuic acid is produced through the bio-transformation of glucose, this contribution may provide a new method for the preparation of non-bisphenol-A high-performance epoxy resins, as well as give a new way for the conversion of the bio-based protocatechuic acid. [Display omitted] Synopsis:A new non-bisphenol-A epoxy (PA-EP) based on a bio-based protocatechuic acid was reported, which was cured to give a cross-linked network, exhibiting Tg of more than 250 °C and CTE of 66 ppm/°C, which are much outstanding than those of a commercial bisphenol-A epoxy resin (DGEBA). •A high-performance epoxy resin derived from a bio-based protocatechuic acid.•The cured resin exhibits Tg of more than 250 °C and CTE of 66 ppm/°C.•These properties are better than these of commercial phenolic and epoxy resins.