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Glycolysis of epoxide–amine hardened networks II—aminoether model compound

Abstract : The aim of this work was to understand the reactions that appear during glycolytic depolymerization of an epoxide-amine hardened thermoset. A model compound (product of condensation of phenylglycidyl ether to N,N'-dimethylethylenediamine) of the epoxy thermoset was synthesized to simplify the study. By reaction with 1,4-butanediol, a cleavage of the rho-O-C linkage occurs, leading to formation of phenol. A stagnation of the yield in phenol at about 20% was observed for the uncatalysed reaction. Different catalysts were checked (sodium methylate, titanium(IV) n-butoxide, lithium perchlorate and p-toluenesulfonic acid). The most efficient of them are p-toluenesulfonic acid (3 w/w%) and sodium methylate (30 w/w%). The disappearance of the initial model compound was also observed, even for a low yield in phenol. The different reaction products were separated and analysed by NMR spectroscopy. The results are in accordance with a reaction scheme based on two mechanisms of rho-O-C linkage cleavage.
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N. Destais-Orvoën, Geoffroy Durand, G. Tersac. Glycolysis of epoxide–amine hardened networks II—aminoether model compound. Acta Polymerica, Wiley-VCH Verlag, 2004, 45 (16), pp.5473-5482. ⟨10.1016/j.polymer.2004.06.010⟩. ⟨hal-01252372⟩



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