Chitosan films as pH-responsive sustained release systems of naturally occurring antifungal volatile compounds

Reversible imine bonds have been used as a strategy to develop pH-dependent antifungal systems based on grafting benzaldehyde and citral onto the surface of chitosan films. Formation of imine bonds was confirmed by ATR-FTIR and XPS. Aldehyde unit incorporation respect to glucosamine units of chitosan polymer was estimated by elemental analysis. The rate and extent of imine bond hydrolysis depended on the pH of the media and the chemical structure of the aldehyde. The release of the aldehydes was monitored by gas chromatography observing acidic media favours the release. Imine bond obtained from benzaldehyde was more prone to be hydrolysed than citral. Chitosan films grafted with benzaldehyde and triggered at acidic pH controlled in vitro growth of common fruit and vegetable spoilage and pathogenic fungi. The films developed could be applied in the design of food packages intended to prevent postharvest fungal spoilage. [Display omitted] •An in situ process was developed to covalently graft aldehydes to the surface of chitosan films.•Synthetized imine bonds act as reversible covalent linkers of citral and benzaldehyde.•Triggering aldehyde release from the films was achieved by pH-dependent hydrolysis of CN bonds.•Aldehyde chemical structure plays a major role on imine bond reversibility.