Structure property relationships of biobased n-alkyl bisferulate epoxy resins. Issue 18 (8th June 2016)

• Record Type: Journal Article
• Authors: Maiorana, Anthony; Reano, Armando F.; Centore, Robert; Grimaldi, Marina; Balaguer, Patrick; Allais, Florent; Gross, Richard A.
• Is Part Of: Green chemistry. Volume 18:Issue 18(2016)
• Page Start: 4961
• Page End: 4973
• Publication Date: 2016-06-08
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c6gc01308b
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : 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). Abstract : 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 ( T d5% ) 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.