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Journal of Bioactive and Compatible Polymers
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Optimized Synthesis and Characterization of N-Triethyl Chitosan

M. R. Avadi

Faculty of Pharmacy Shahid Beheshti University of Medical Sciences Tehran, Iran and Hakim Pharmaceutical Company P.O. Box 11365-5465, Tehran, Iran

M. J. Zohuriaan-Mehr

Iran Polymer and Petrochemical Institute (IPPI) P.O. Box 14965-115, Tehran, Iran

P. Younessi

M. Amini

M. Rafiee Tehrani

A. Shafiee

Tehran University of Medical Sciences, Tehran, Iranashafiee{at}ams.ac.ir

Chitosan exhibits poor solubility at pH values above 6 which prevents its enhancing effects at drugs absorption of sites. In the present work, N-triethylated chitosan (TEC) was prepared based on a modified one-step process via a 22 factorial design to optimize the preparative conditions. TEC polymer with different degree of quaternization for pharmacological and pharmaceutical experiments was achieved. Ethyl iodide and sodium hydroxide concentrations were chosen as independent variables. The degree of deacetylation of the starting chitosan was predetermined by pH-metric titration, infrared, and NMR methods. TEC chloride was fully characterized using FTIR and 1H-NMR spectroscopies. Based on NMR calculations, a high degree of quaternization was achieved through the optimized one-step process. These highly N-triethylated chitosan chlorides were soluble in water at room temperature.

Key Words: chitosan • triethyl chitosan • modification • absorption enhancer • NMR • IR

Journal of Bioactive and Compatible Polymers, Vol. 18, No. 6, 469-479 (2003)
DOI: 10.1177/0883911503040432
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