Oxygen Permeability and Biodegradability of Polyuronic Acids Prepared from Polysaccharides by TEMPO-Mediated Oxidation

Abstract

Polyuronic acids, i.e., amylouronic acid, cellouronic acid and chitouronic acid, were prepared from starch, cellulose and chitin, respectively, by the 2,2,6,6-tetramethylpiperidine-1-oxy radical (TEMPO)-mediated oxidation, and their gas-barrier properties and biodegradability were studied in consideration to use the polyuronic acids as flexible packaging films or coating materials. Cellouronic acid and amylouronic acid had excellent oxygen-barrier properties similar to that of poly(vinyl alcohol) (PVA), while chitouronic acid did not. The regular chemical structures of the former two polyuronic acids with no bulky substituents or adducts may have brought about such high oxygen-barrier levels. An oxidized product prepared form fine microcrystalline cellulose by the TEMPO-mediated oxidation was not completely dissolved in water, but became a paste. However, this paste also formed sufficiently smooth films by coating, and had good gas-barrier property. All polyuronic acids prepared were biodegradable; cellouronic acid and chitouronic acid had high degrees of biodegradability, while amylouronic acid had quite low value. These various characteristics are significant for end use of these new polyuronic acids as gas-barrier materials for biodegradable packaging.