Chitosan
is a polysaccharide widely used as a structuring agent
in foods and other materials because of its positive charge (amino
groups). At present, however, it is difficult to form and stabilize
emulsions using chitosan due to its high hydrophilicity. In this study,
oil-in-water emulsions were prepared using a one-pot green-chemistry
method. The chitosan and aldehyde molecules were in situ interfacially conjugated during homogenization, which promoted the
adsorption of chitosan onto the oil droplet surfaces where they created
a protective coating. The universality of this method was verified
by using chitosan with different molecular weights and four kinds
of natural aldehydes [cinnamaldehyde (CA), citral (CT), citronella
(CN), and vanillin (VL)]. Chitosan with higher molecular weight facilitated
the formation of emulsions. By harnessing the dynamic covalent nature
of imine bonds, chitosan emulsions with an imine link display dynamic
behavior with acid-catalyzed hydrolysis. The aldehyde structure could
control the pH point of trigger for breakdown of emulsions, which
was 1.0, 3.0, 4.0, and 4.0 for CA emulsion, CT emulsion, CN emulsion,
and VL emulsion, respectively. At pH 6.5, aldehyde helped to decrease
the interfacial tension of chitosan to about 10 mN/m, while this value
would increase if the pH decreased by adding acid during the measurement.
Chemical kinetics studies indicated that the hydrophobicity and conjugation
effect of the aldehyde together determined the trigger points and
properties of the emulsion. Finally, we used the optimized emulsions
to encapsulate and control the release of curcumin. The gastric release
behavior of the curcumin depended on aldehyde structure: VL > CN
>
CT ≈ CA. Hence, a tailor-made trigger release emulsion system
can be achieved by rational selection and design of aldehyde structure
to control hydrophobicity and conjugation effect of aldehydes.