New Highly Functionalised Starch Derivatives

Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, HunAoldstrc e 10, D-07743 Jena, Germany 

Abstract Pure, well soluble p-toluenesulfwiyl (tosyl) starch samples with a DSm range 

In contrast to the recent progress in cellulose chemistry, which is in particular stimulated by the use of non-aqueous cellulose solvents and regioselectively protected or activated derivatives, a fiilly satisfying solution to design high-perfonnance materials based on starch is still missing. Most of the starch derivatives, which are available commercially, have low degree 

Biorelated Polymers Sustainable Polymer Science and Technology Edited by Chiellini et al., Kluwer Academic/Plenum Publishers, 2001 

In this context our interest was focused on sulfonic acid esters of starch, derived fh)m the reaction of organic sulfonyl chloride (e.g. benzene, methane, or toluene sulfonyl chloride). These derivatives can be employed as partially protected and reactive intermediates. Up to now, especially the reaction of starch with p-toluenesulfonyl chloride in pyridine was studied, i.e. under heterogeneous reaction conditions, which may be accompanied by several side reactions. Alternatively, a homogeneous procedure was published using dimethyl sulfoxide as solvent for starch. However, the sulphur contents of the products were very low and an extensive degradation of the polymer occured . The extent of / toluenesulfonyIation of primary and secondary groups was determined by the iodination method. It was revealed that the reaction proceeds faster at 0-6 than at 0-2 and 0-2 

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Heinze, U., Haack, V. and Heinze, T. (2001) New Highly Functionalised Starch Derivatives, In Biorelated Polymers-Sustainable Polymer Science and Technology, E. Chiellini, H. Gil, G. Braunegg, J. Buchert, P. Gatenholm, and M. Van der Zee (eds.), Kluwer Academic/Plenum Publishers, pp. 20 -218. 

The increasing use of bioplastics has opened entirely new generations of materials with new performances in comparison with traditional plastics. The possibility offered by physically modified starch to create functionalised nanoparticles able to modify the properties of natural and synthetic mbbers and other synthetic polymers, the naturally high oxygen barrier of starch and its derivatives, and their high permeability to water vapour already offer a range of completely new solutions to the plastic industry. 

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