Water‐Soluble AmphiphilicO‐(Carboxymethyl)cellulose Derivatives – Synthesis and Properties

Abstract

AbstractSummary:Water‐soluble, partially hydrophobized derivatives ofO‐(carboxymethyl)cellulose (CMC) were prepared by esterification of CMC in its ‘gel suspension’ form. The classical esterification method (A) using stearoyl chloride/pyridine as well as two unconventional methods based on reaction with mixed anhydrides (B) and transesterification with vinyl laurate (C) respectively, were compared in terms of the structural, molecular and performance properties of the obtained derivatives. The classical esterification and method B yielded water‐soluble simple fatty acid esters, whereas mixed acetic‐fatty acid esters were obtained by method C. In all cases, molecular degradation of CMC was observed.1H and13C NMR spectroscopy of the acetyl‐lauroyl derivatives of CMC with a degree of esterificationDSEof 0.20 indicated a prevalence of the lauroyl groups (DSAc:DSLa = 0.03:0.17). Most of the water‐soluble derivatives exhibited excellent emulsifying efficiency. They represent polysaccharide‐based surfactants with effective anti‐redeposition properties as well as good washing power. Suitable derivatives can be prepared under mild reaction conditions by both unconventional methods which implies that they have potential as substitutes for the expensive and invasive conventional method.Preparation of CMC derivatives.magnified imagePreparation of CMC derivatives.