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Issue 18, 2016
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Structure property relationships of biobased n-alkyl bisferulate epoxy resins

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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 (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.

Graphical abstract: Structure property relationships of biobased n-alkyl bisferulate epoxy resins

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Supplementary files

Article information


Submitted
11 May 2016
Accepted
01 Jun 2016
First published
02 Jun 2016

Green Chem., 2016,18, 4961-4973
Article type
Paper

Structure property relationships of biobased n-alkyl bisferulate epoxy resins

A. Maiorana, A. F. Reano, R. Centore, M. Grimaldi, P. Balaguer, F. Allais and R. A. Gross, Green Chem., 2016, 18, 4961
DOI: 10.1039/C6GC01308B

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