Mixed 3-mono-O-alkyl cellulose: synthesis, structure characterization and thermal properties

Abstract

The 3-mono-O-alkyl cellulose samples bearing two different ether moieties, namely methyl/ethyl, methyl/n-propyl, and ethyl/n-propyl were synthesized applying protecting group technique. The NMR spectra of the peracetylated products revealed the regioselectivity of the alkylation as well as the degree of substitution of both alkyl moieties. The number average degree of polymerization (DPn) monitored by size exclusion chromatography decreases from DPn 117 (Avicel PH-101, starting material) to DPn 34 (sample 4f) due to the multi-step synthesis. It could be demonstrated that the lower critical solution temperature (LCST) is influenced by the degree of substitution of both alkyl groups. For example, LCST values between 33 and 58 °C were measured for aqueous solutions of 3-mono-O-ethyl/n-propyl cellulose. On the contrary, the thermal behavior of a physical mixture of 3-mono-O-ethyl- and 3-mono-O-n-propyl cellulose, e.g., was controlled by the derivative with the lowest LCST.