Neue Polyamide aus niedermolekularen Kohlenhydraten: Darstellung und Polykondensation von Monomerbausteinen aus Saccharose, D-Glucose, D-Fructose, D-Galactose und Isomaltulose

The aim of the work was the development of efficient reaction sequences for the transformation of cheap low molecular carbohydrates into polyamide-monomers. The resulting polyamides should show hydrophilicity and biodegradability. Starting from sucrose two protected 6,6'-diamino-sucroses were prepared via bromination in the 6- and 6'- positions, subsequent substitution to the 6,6'-diazido-sucrose followed by permethylation and perpivaloylation, respectively. Their polycondensation with terephthaloyl chloride as well as with aliphatic dicarboxylic acid dichlorides delivered a preparative access to a novel type of sucrose-containing polyamides. Sucrose-6,6'-dicarboxylic acid, obtained from a technical oxidation process, was transformed into hydroxylated and O-protected polyamide-monomers of the dicarboxylic acid- and diamino-type. D-galactose was modified through oxidation and subsequent reductive amination into a new tetrahydroxy derivative of hexamethylendiamine. The monomer was polycondensed with adipoyl chloride to form a hydroxylated analogue of nylon 6.6. By a four step synthesis the lactone of the glucopyranosyl-arabinonic acid (GPA-lactone) was transformed into a stereoregular polyamide of the perlon-type. Starting from enzymaticly produced D-glucuronic acid it was possible to obtain a hydroxylated counter part of the industrial relevant caprolactame. The acid induced melt condensation of two molecules 5-hydroxymethyl-furfural (HMF), which could be produced in an industrial scale, led to the bis-HMF-ether. Its further derivatization provided a diamino- and two dicarboxylic acid-monomers. The polycondensation of these furanic monomers with aromatic as well as with aliphatic diamines and with one another furnished polyamides of high molecular weight. Some of them were totally build up from regrowing resources.SIGLEAvailable from: http://elib.tu-darmstadt.de/diss/000115/ / FIZ - Fachinformationszzentrum Karlsruhe / TIB - Technische InformationsbibliothekDEGerman