2,3-Dialdehyde celluloses were prepared by homogeneous periodate oxidation in an aqueous solution of methylol cellulose. Since methylol cellulose stays dissolved in water for a certain time before decomposing gradually into regenerated cellulose, the oxidation reaction progressed homogeneously throughout the period. The resulting dialdehyde cellulose achieved an oxidation level of over 90 % in as little as 12 h. Reducing the dialdehyde celluloses with NaBH4 resulted in water-soluble dialcohol celluloses, which have an open-ring structure at the C2–C3 position. The dialcohol celluloses were characterized using nuclear magnetic resonance spectrometry, Fourier transform infrared spectroscopy, and differential scanning calorimetry. The Tg of the products decreased with increasing oxidation levels. The products might be processable, and unique tensile properties were obtained by cutting the C2–C3 bonds in the glucopyranose rings. The dialcohol celluloses prepared using a cast method yielded clear and transparent films which showed unique mechanical properties by tensile tests depending on the values of oxidation level.
This is a preview of subscription content, log in to check access.
W.K. acknowledges a Grant from the Jacob Wallenberg Research Foundation. Domsjö Fabriker AB, Sweden, is acknowledged for providing the pulp samples.
Cantley M, Hough L, Pittet AO (1963) The non-malapradian oxidation of carbohydrates and related compounds by periodate. J Chem Soc 2527–2535. doi: 10.1039/JR9630002527
Casu B, Meille V, Naggi A, Su P, Torri G, Zoppetti G (1982) Structure and conformation of polyalcohols and polyacids obtained from periodate oxyamylose and oxycellulose. Carbohydr Res 2:283–287. doi:10.1016/0144-8617(82)90032-7Google Scholar
Casu B, Naggi A, Torri G, Allegra G, Meille V, Cosani A, Terbojevich M (1985) Stereoregular acyclic polyalcohols and polyacetates from cellulose and amylase. Macromolecules 18:2762–2767. doi:10.1021/ma00154a068CrossRefGoogle Scholar
Potthast A, Schiehser S, Rosenau T, Kostic M (2009) Oxidative modifications of cellulose in the periodate system: reduction and beta-elimination reactions. Holzforschung 63:12–17. doi:10.1515/HF.2009.108CrossRefGoogle Scholar
Swenson HA (1975) Proceedings of the 8th cellulose conference. J Polymer Sci CGoogle Scholar