Synthesis and characterization of novel water-soluble 6-deoxy-6-(2-amino-2-(hydroxymethyl)propane-1,3-diol)cellulose derivatives

Abstract

Amino celluloses are semisynthetic polysaccharide derivatives that are functionalized with amino groups. This class of bio-based polymers has a number of interesting properties for advanced applications such as potential antimicrobial activity and pronounced surface affinity towards various materials. Herein, the synthesis of a novel type of 6-deoxy-6-amino cellulose derivatives with a polar and highly branched substituent (2-amino-2-(hydroxymethyl)propane-1,3-diol/TRIS) is described for the first time. Fundamental principles for the synthesis by nucleophilic displacement of tosylated intermediates are highlighted, thus, providing access to materials with well-defined molecular structures. TRIS-functionalized cellulose derivatives with degrees of substitution (DS) of up to 0.5 were obtained. The solubility and rheological properties of the products showed a strong dependence on the pH value. Due to the unique structural features of the substituent, TRIS amino cellulose derivatives possess a high application potential. Keywords: Amino celluloses, Water soluble polysaccharide derivatives, 2-Amino-2-(hydroxymethyl)propane-1,3-diol, Nucleophilic displacement, NMR spectroscopy