Synthesis and characterization of novel amino cellulose esters

Abstract

The homogeneous conversion of cellulose dissolved in N-methyl-2-pyrrolidone/LiCl and 1-N-butyl-3-methylimidazolium chloride with N-methyl-2-pyrrolidone, e-caprolactam, N-methyl-e-caprolactam, and N-methyl-2-piperidone in the presence of p-toluenesulphonic acid chloride was studied. Depending on the reaction conditions, novel cellulose esters with degree of substitution (DS) values ranging from 0.12 to 1.17 could be prepared. The structure of the amino group containing cellulose esters was elucidated by elemental analysis, FTIR- and NMR spectroscopy. NMR spectroscopy revealed an almost complete esterification of position 6 of the anhydroglucose unit at DS of 1. The conversion can be conducted between room temperature and 40 °C, while side-reactions became predominant at 60 °C. Starting with DS of 0.24, the samples were soluble both in water and dimethyl sulphoxide. The derivatives described are capable of forming polyelectrolyte complexes. The samples were stable at room temperature in aqueous solution at pH 2 and 7. Lower viscosities were found for samples with higher DS in aqueous solution at comparable molar mass.