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Sharavanan, K. ; Komber, H. ; Böhme, F.
Synthesis and Properties of Aliphatic Polyacetamidines

A series of aliphatic polyacetamidines (1) with the common structure [(CH2)mNC(CH3)NH]n was synthesized by the phenol-catalyzed melt polycondensation reaction of various aliphatic diamines with triethyl orthoacetate. The resulting polyacetamidines were characterized by 1H and 13C NMR spectroscopy. It could be shown that the NMR spectra are strongly influenced by the solvents used. In pyridine and CD3OD, prototropic tautomerism of the amidine group was observed. In pyridine this process is mainly caused by intermolecular proton exchange between two amidine groups whereas in CD3OD, proton exchange mainly proceeds via the solvent. The methyl residue on the amidine group revealed pronounced CH-acidity, which is apparent in a proton-deuteron exchange when CD3OD was used as a solvent. In CF3COOD, the respective amidinium salts were formed. It was found that the thermal stability of the polymers increased with increasing chain length of the aliphatic diamines. The shorter aliphatic diamines formed cyclic products with a defined structure.

Source
Macromolecular Chemistry and Physics 203

Pages
1852-1858

DOI
http://dx.doi.org/10.1002/1521-3935(200208)203:12<1852::AID-MACP1852>3.0.CO;2-5

Published
September 2002
 
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