Reversible Covalent Immobilization of Cinnamaldehyde on Chitosan Films via Schiff Base Formation and Their Application in Active Food Packaging

Abstract

In this work, cinnamaldehyde was reversibly anchored to chitosan films via imino-covalent bonding. The Schiff base was synthesized in solid phase employing neutralized chitosan films immersed in acidified 95 % (v/v) ethanolic solution in which the aldehyde was dissolved. The substitution degree (%) of cinnamaldehyde to the amine group was close to 70 %. Attenuated total reflectance–Fourier transform infrared spectroscopy (ATR-FTIR) analysis revealed the formation of the chitosan-cinnamaldehyde Schiff base. The hydrolysis of the imino bond and subsequent release of cinnamaldehyde were studied after the films had been subjected to different combinations of temperature/time treatments simulating food preservation methods. The amount of aldehyde that remained covalently attached to the films was monitored by ATR-FTIR, and the substitution degree was determined by elemental analysis. Surface contact angle and colour parameters of cinnamaldehyde-imine-chitosan films and these films subjected to different treatments were also evaluated. The antimicrobial properties of chitosan-Schiff base films were tested in vitro against Staphylococcus aureus and Escherichia coli and in milk inoculated with Listeria monocytogenes. The antimicrobial activity varied depending on the treatment applied and consequently the degree of imino bond hydrolysis achieved and cinnamaldehyde released. Films of Schiff base-chitosan derivative subjected to different time/temperature treatments inhibited the growth of L. monocytogenes for 12 days under refrigeration conditions, which may extend the microbiological shelf life of such products. Sensory analysis of milk in contact with the films showed that a cinnamon smell does not cause any rejection among potential consumers. These novel films could be used in the design of antimicrobial food packaging and in various other technological areas where sustained-release systems are required.