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Biobased Epoxy Resin by Electrochemical Modification of Tall Oil Fatty Acids
journal contribution
posted on 2019-05-23, 00:00 authored by Goswinus
H. M. de Kruijff, Thorsten Goschler, Lukasz Derwich, Nicole Beiser, Oliver M. Türk, Siegfried R. WaldvogelA biobased
epoxy resin was prepared from tall oil fatty acids (TOFAs),
a byproduct of the pulping industry. As free carboxylic acids compromise
resin stability, TOFA was subjected to non-Kolbe decarboxylation to
give alkenes upon loss of CO2. Thereby, the degree of unsaturation
is significantly increased. This electrosynthetic protocol using an
undivided cell setup and inexpensive graphite electrodes in a galvanostatic
operation mode was scaled to a 1.5 L reactor, making use of electric
current as a green and waste-free reagent. Simple, cost-efficient
epoxidation using oxone subsequently gives an epoxy resin of low viscosity.
Curing with anhydrides yields thermoset materials. Dynamic mechanical
analyses and tensile and flexural tests were conducted to determine
the effect of different curing agents on the thermomechanical properties.
For methyl tetrahydrophthalic anhydride (MTHPA) and methyl-5-norbornene-2,3-dicarboxylic
anhydride (MNA), good mechanical properties were observed, whereas
dodecenyl succinic anhydride (DDSA) resulted in a brittle material
with low Tg.
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MTHPAelectrosynthetic protocolmethyl tetrahydrophthalic anhydrideBiobased Epoxy Resindodecenyl succinic anhydridegraphite electrodesMNAwaste-free reagentTOFAanhydrides yields thermoset materialsCO 2T gcell setupgalvanostatic operation modeTall Oil Fatty AcidsDDSAthermomechanical propertiescarboxylic acids compromise resin stabilitynon-Kolbe decarboxylationmethyl -5-norbornene anhydride1.5 L reactorElectrochemical Modification
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