Syntheses of High-Performance Biopolyamides Derived from Itaconic Acid and Their Environmental Corrosion

Abstract

A new synthetic route for high-performance biopolyamides with a rigid N-substituted pyrrolidone ring was developed from the biomonomer itaconic acid (IA), which was mass-produced by the fermentation of Aspergillus terreus. We used salt-type monomers composed of diacidic IA and diamines. These salts thermally converted into polyamides in the presence of sodium dihydrogen phosphate through the aza-Michael addition, followed by intramolecular cyclization to create a pyrrolidone ring in the polymer main chain. Polyamides with molecular weights ranging over 28 000 showed T g values over 87 °C, which were higher than conventional polyamides (around 57 °C). The Young's modulus and mechanical strength of these polyamides also showed high values of 430−2800 MPa and 90−165 MPa, respectively. In addition, the polyamides became soluble in water by ring-opening reaction of the pyrrolidone, which led to environmental corrosion by landfill or ultraviolet irradiation.

Synthesis of biorenewable and water-degradable polylactam esters from itaconic acid

“…Compare this hydrolysis behavior to that of polylactam amides reported by Kaneko et al, 42 which resemble PEPC (Fig. Compare this hydrolysis behavior to that of polylactam amides reported by Kaneko et al, 42 which resemble PEPC (Fig.…”

“…† Electronic supplementary information (ESI) available: Synthetic details, complete polymer characterization data, and polymer degradation data. [38][39][40][41] While polyamides from itaconic acid containing the pyrrolidone ring system have been reported, 42 it appears that polyesters containing this lactam are novel. 24 Herein, we have focused on the 2-pyrrolidone ring system to function as the hard component of a repeating hard/soft motif.…”

Bio-polyamides based on renewable raw materials

“…The polyamides with different chain lengths between amide groups (ratio of methylene and amide groups) show different hydrogen bond densities and thus different water absorption. In general, the longer carbon chain results in higher impact strength, higher solvent resistance, and lower water absorption [16,17]. These characteristics bring possibilities to design novel biobased materials with specially tailored properties.…”

Itaconic acid used as a versatile building block for the synthesis of renewable resource‐based resins and polyesters for future prospective: a review

“…Ali et al . synthesized high‐performance biopolyamides from IA by the fermentation of Aspergillus terreus .…”