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Structure property relationships of biobased n-alkyl bisferulate epoxy resins

Abstract : In this work, a series of bio-based chemically recyclable epoxy resins were synthesized from n-alkyl bis-ferulate esters that do not activate human estrogen receptor alpha (ERa). 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 alpha,omega-diols that link glycidyl ether ferulate units. That is, the glassy phase modulus and alpha transition temperatures range from 3400-2400 MPa (at 25 degrees C) and 40-53 degrees C (peak of E''), respectively. Furthermore, the onset of thermal degradation (T-d5%) varied from 331-300 degrees C. Chemical recycling of cured epoxy resins was performed by static immersion in 10 w/w sodium hydroxide aqueous solutions at 60 degrees C. Times required for complete conversion of cured resins to water-soluble degradation products was also alpha,omega-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.
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Submitted on : Thursday, June 1, 2017 - 8:08:29 PM
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Anthony Maiorana, Armando F. Reano, Robert Centore, Marina Grimaldi, Patrick Balaguer, et al.. Structure property relationships of biobased n-alkyl bisferulate epoxy resins. Green Chemistry, Royal Society of Chemistry, 2016, 18 (18), pp.4961-4973. ⟨10.1039/c6gc01308b⟩. ⟨hal-01531705⟩



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