Bio-based cross-linked polyitaconamides synthesized through a Michael ene-amine addition and bulk polycondensation

A simple method is established to synthesize bio-based cross-linked polyitaconamides (cPITAs) through a Michael ene-amine addition and bulk polycondensation. A tetraester, i.e. tetramethyl piperazine-N,N′-bis(2-methylene butanedioate) (TMPB), was synthesized through a Michael addition of dimethyl itaconate and piperazine at 90 °C. Bulk polycondensation of TMPB with butanediamine or hexamethylenediamine was conducted at 130–170 °C under atmospheric pressure, and several cPITAs with tunable properties were prepared. The Michael addition and the polycondensation were monitored by FT-IR and ¹H NMR spectra. The cPITA films were characterized by DSC, WAXS, TGA, dynamic mechanical analysis, and tensile test. cPITAs exhibited T_g ranging from 58 to 72 °C, tensile strength up to 85 MPa, and strain at break from 9% to 17%.