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Chitosan and naproxen salts: preparation and characterization

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Abstract

Chitosan (CTS) and naproxen (NAP) salts were prepared using different reaction parameters such as time, molar ratio and temperature. The salt was also synthesized from chitosan crosslinked with epichlorohydrin (EP). The starting reagents and salts were characterized by spectroscopic (1H NMR and FTIR) and thermoanalytical (TG/DTG/DTA, DSC and TG-FTIR) techniques. Under dry air atmosphere, the CTS TG/DTG curve showed three mass loss events, one resulting from dehydration and the other two referring to the decomposition and burning of the carbonized material, with a residue of 5.95% at 1000 °C. Under the same conditions, the DTA curve exhibited an endothermic dehydration peak and an exothermic decomposition peak. TG/DTG curve of NAP shows two stages of mass loss, the first related to the drug decomposition and the other of burning the carbonized material. The DTA curve showed an endothermic peak at 156.7 °C (melting), in addition to other endo and exothermic peaks attributed to evaporation, decomposition and burning of the carbonized material. The TG/DTG/DTA curves of naproxen salts with non-crosslinked (CN) and crosslinked (CEPN) chitosan showed profiles similar to those of CTS; however, the mass loss events were observed at different temperature intervals, suggesting an interaction between CTS and NAP. The DSC curves of CNs and CEPNs showed salt formation, as the endothermic peak characteristic of NAP melt was not observed. These data are supported by spectroscopic techniques (FTIR and 1H NMR). In experiments involving TG-FTIR, the release of gases was observed: CO, CO2, CH3CONH2, CH3COOH, NH3 and CH4.

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Funding

Fundação de Amparo à Pesquisa do Estado de São Paulo,Conselho Nacional de Desenvolvimento Científico e Tecnológico.

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  1. Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador São-carlense, 400, São Carlos, SP, 13566-590, Brazil

    R. S. Medeiros, A. P. G. Ferreira & E. T. G. Cavalheiro

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Contributions

RSM Conceptualization; Data curation; Formal analysis; Investigation; Methodology; Validation; Visualization; Roles/Writing-original draft; Writing-review & editing. APGF Conceptualization; Data curation; Formal analysis; Funding acquisition; Investigation; Methodology; Project administration; Supervision; Validation; Visualization; Roles/Writing-original draft; Writing-review & editing. ETGC Conceptualization; Data curation; Formal analysis; Funding acquisition; Project administration; Resources; Supervision; Validation; Visualization; Roles/Writing-original draft; Writing-review & editing.

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Correspondence to E. T. G. Cavalheiro.

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Medeiros, R.S., Ferreira, A.P.G. & Cavalheiro, E.T.G. Chitosan and naproxen salts: preparation and characterization. J Therm Anal Calorim 148, 177–190 (2023). https://doi.org/10.1007/s10973-022-11626-8

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