Tyrosinase-catalysed Grafting of Food-grade Gallates to Chitosan : Surface Properties of Novel Functional Coatings

Plasma-activated biaxially oriented polypropylene (BOPP) films and paper substrate have been coated with functional chitosan solutions. Plasma treatment increased the amount of surface peroxide groups and carboxyl groups on the BOPP films. As a result of plasma activation, the surface energy increased from 30 to 50 dynes/cm. The enzyme tyrosinase catalysed the grafting of octyl gallate and dodecyl gallate to amino groups of chitosan polysaccharide. Resulting coatings exhibited strong antimicrobial activity against Gram-positive Staphylococcus aureus and Gram-negative Listeria innocua. After 24 h of incubation, a total reduction in both bacteria cell numbers varied between >4.9 and 1.4 logarithmic units. Grafted dodecyl gallate and octyl gallate at pH 6 were found to have the lowest reduction values of <3 logarithmic units for S. aureus, while 1.4 logarithmic reduction value was obtained for grafted dodecyl gallate at pH 6 against L. innocua. Chitosan coatings were also effective barrier layers against oxygen transmission although the transmission rates clearly increased in high-humidity conditions. In dry conditions, however, the transmission rate of 2 cm3/(m2 · 24 h) was obtained with chitosan-coated BOPP. Coatings did not have any effects on water vapour transmission. Both gallates were successfully grafted at pH 6. As increased flocculation and colour formation indicated, the tyrosinase-catalysed grafting was more powerful with octyl gallate. Dodecyl gallate containing chitosan coatings was more hydrophobic as compared to octyl gallate. Total migration of substances into 95% ethanol was ≥5 mg/dm2, thus materials may be exploitable in packaging purposes in direct contact with certain foodstuffs. Copyright © 2008 John Wiley & Sons, Ltd.