Synthesis and properties of lignin epoxide

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Virginia Polytechnic Institute and State University

A lignin epoxide resin was synthesized and characterized.

The epoxidation reaction was studied by reacting hydroxypropylated guaiacol (a lignin-like model compound) and epichlorohydrin using a catalyst system of potassium hydroxide and a phase transfer catalyst in toluene. The parameters studied were different epichlorohydrin level and temperature. The reaction was followed by HPLC and the structure of the product was identified with IR, ¹H and ¹³C NMR spectroscopy.

The lignin epoxide was synthesized by reacting hydroxyalkylated (hydroxypropyl and hydroxybutyl) lignin with epichlorohydrin using the reaction conditions defined by the model compound studies. The reaction was studied at different epichlorohydrin level and at elevated and room temperature. The epoxy content of the lignin epoxide was determined by titration with HBr and its structure was identified with IR, ¹H and ¹³C NMR spectroscopy.

Lignin epoxides were cured by crosslinking with a diamine and with phthalic anhydride. An amine-terminated rubber was added as toughening agent. Sol fraction and swelling behavior, stress-strain behavior and dynamic mechanical behavior of the cured lignin epoxides were studied in relation to cure conditions.