Synthesis and Characterization of Chitosan Linked by Methylene Bridge and Schiff Base of 4,4-Diaminodiphenyl Ether-Vanillin

Ahmad Fatoni; Poedji Loekitowati Hariani; Hermansyah Hermansyah; Aldes Lesbani

doi:10.22146/ijc.25866

Synthesis and Characterization of Chitosan Linked by Methylene Bridge and Schiff Base of 4,4-Diaminodiphenyl Ether-Vanillin

https://doi.org/10.22146/ijc.25866

Ahmad Fatoni^(1*), Poedji Loekitowati Hariani⁽²⁾, Hermansyah Hermansyah⁽³⁾, Aldes Lesbani⁽⁴⁾

(1) Bhakti Pertiwi School of Pharmacy Science Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sriwijaya University
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sriwijaya University
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sriwijaya University
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sriwijaya University
(*) Corresponding Author

Abstract

The synthesis chitosan-methylene bridge-Schiff base of 4,4-diaminodiphenyl ether-vanillin using casting method has been done. The aims of this research were modification chitosan with Schiff base of 4,4-diaminodiphenyl ether-vanillin, formaldehyde and its characterization using FTIR spectroscopy, SEM analysis, ¹H-NMR and X-Ray Diffraction analysis. The first step was a synthesis of modified chitosan between chitosan and Schiff base of 4,4-diaminodiphenyl ether-vanillin. The second step was chitosan modified Schiff base of 4,4-diaminodiphenyl ether-vanillin then reacted with formaldehyde through casting method. The result showed that chitosan can be modified with Schiff base of 4,4-diaminodiphenyl ether-vanillin and formaldehyde and this modified chitosan can be linked by methylene bridge (-NH-CH₂-NH-) and had azomethine group (-C=N-). The functional group of –C=N in modified chitosan before and after adding formaldehyde appeared at a constant wavenumber of 1597 cm^-1. The functional group C-N in methylene bridge detected at 1388 and 1496 cm^-1. The chitosan-Schiff base of 4,4-diaminodiphenyl ether-vanillin and Chitosan-methylene bridge-Schiff base of 4,4-diaminodiphenyl ether-vanillin had index crystalline (%)16.04 and 25.76, respectively. The chemical sift of signal proton azomethine group (-C=N-) in modified chitosan detected at 8.44–8.48 and 9.77 ppm. Proton from methylene bridge in modified chitosan appeared at 4.97–4.99 and 3.75 ppm. Surface morphology chitosan-methylene bridge-Schiff base of 4,4-diaminodiphenylether-vanillin had dense surfaces, mostly uniform and regular in shape.

Keywords

chitosan; methylene bridge; Schiff base

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DOI: https://doi.org/10.22146/ijc.25866