High Molecular Weight Chitosan from Shrimp Shells: Synthesis of Para-Substituted Schiff Bases with Selective Leishmanicidal Activity and Application in CO₂/O₂-Selective Films

Penaeus sp. shells (shrimp) were used to extract chitosan using acid and basic treatments, which were characterized by IR spectroscopy, Raman spectroscopy, potentiometric titration, and elemental analysis. The degrees of deacetylation were determined to be 71.8%, 75.6%, 53.4%, and 68.6%, respectively. Likewise, viscosimetry measurements were carried out, determining an average molecular weight of chitosan 1 of 1521467.919 (g/mol). The obtained chitosan was used as a substrate in condensation reactions with 10 para-substituted benzaldehydes. The products obtained were characterized by IR, Raman, and ¹H-NMR spectroscopy, AE (Elemental Analysis), TGA (Thermogravimetric Analysis), and DSC (Differential Scanning Calorimetry). For the obtained polymers, biological assays of cytotoxicity using RAW macrophage cells and leishmanicidal activity on promastigotes of Leishmania mexicana were performed. The results show that the synthesized products do not present in vitro cytotoxicity, and that 1 (Chitosan) and 3i (Schiff Base) present leishmanicidal activity. Selected derivatives were incorporated into polyvinyl alcohol-based films and evaluated for surface topography and gas permeability. AFM revealed nanometric roughness patterns, while gas exchange studies demonstrated selective CO₂/O₂ permeability, supporting passive modified atmosphere formation in packaged carrots. Mechanical characterization revealed that the incorporation of Schiff base derivatives significantly influences tensile strength and flexibility, with certain films exhibiting enhanced elongation and mechanical performance compared to pure PVA, highlighting their potential for packaging applications. These findings confirm that chemical functionalization enhances the versatility of chitosan, allowing the design of tailored biopolymers. The synthesized derivatives show promising characteristics for the development of biodegradable films with potential applications in food packaging and antiparasitic material development.