Structure property relationships of biobased n-alkyl bisferulate epoxy resins†
In this work, a series of bio-based chemically recyclable epoxy resins were synthesized from n-alkyl bisferulate esters that do not activate human estrogen receptor alpha (ERα). Viscosities of corresponding glycidyl ether n-alkyl bisferulate resins, determined by steady shear rheology, range from 12–9.4 Pa s. Activation energies of flow range from 83–96 kJ mol−1 and are similar to the diglycidyl ether bisphenol A (DGEBA). Thermomechanical properties of diglycidyl ether n-alkyl bisferulate resins cured with isophorone diamine were governed by the length of α,ω-diols that link glycidyl ether ferulate units. That is, the glassy phase modulus and alpha transition temperatures range from 3400–2400 MPa (at 25 °C) and 40–53 °C (peak of E′′), respectively. Furthermore, the onset of thermal degradation (Td5%) varied from 331–300 °C. Chemical recycling of cured epoxy resins was performed by static immersion in 10 w/w sodium hydroxide aqueous solutions at 60 °C. Times required for complete conversion of cured resins to water-soluble degradation products was also α,ω-diol length dependent and varied from 5 to 65 h. Thus, diglycidyl ether of n-alkyl bisferulate resins provides a viable biobased alternative to BPA epoxy resins as well as the option of chemical degradability and recovery of fillers in composite applications.