Mixed
chitin esters, that is, chitin benzoate stearates, exhibiting
thermoplasticity, were synthesized by the acylation of chitin using
benzoyl and stearoyl chlorides in the presence of pyridine and N,N-dimethyl-4-aminopyridine for 1 h + 24 h at 100 °C
in an ionic liquid, 1-allyl-3-methylimidazolium bromide. IR and 1H NMR spectroscopic analyses confirmed the formation of the
desired chitin benzoate stearates. Powder X-ray diffraction analysis
of the products indicated that the crystalline structures of the chitin
main-chains and stearoyl side-chains were strongly affected by the
benzoyl/stearoyl substituent ratios. Introducing a small number of
benzoyl groups, in addition to a large ratio of stearoyl groups, contributed
to disrupting the intrinsic chitin crystals and enabling the chitin
main chains and stearoyl side chains to form regularly controlled
layered and parallel arrays, respectively. The resulting products
exhibited meting points, associated with regular stearoyl packings,
and formed melt-pressed films during the melt-pressing process. These
results suggest that chitin benzoate stearates with appropriate benzoyl/stearoyl
substituent ratios exhibit thermoplasticity.