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We present the synthesis of polymers by means of self-condensation of ethyl 3-aminophenyl acetate, using HCl as catalyst at high temperature and reduced pressure. This polymer was fractionated by successive precipitation from mixtures of methanol/diethylether of different polarity, yielding three polymeric fractions: Poly A, Poly B and Poly C. Likewise, under the same conditions, 3- aminophenyl acetic acid yields only one polymeric fraction, Poly D. These polymers were characterized by elemental analysis, IR and, in some cases, by  1 H-NMR and X-Ray Photoelectron Spectroscopy (XPS). The obtained results show that polymers can be classified as hybrid materials, because in the backbone, they contain simultaneously the amide and imine groups and, at the end of the chain, they have amine and carboxylic acid functions. High solubility of some of these polymers in DMF or methanol has permitted the determination of viscosities and the preparation of films. Poly B and Poly C films exhibit amorphous morphology; and Poly D display spherullitic-type semi-crystallization pattern. The polymers can absorb solvents and they can swell up forming large-sized gels in DMF and methanol. Besides these polymers have high thermal stability that reaches a weight loss of 11.60% at 353 °C.

Synthesis, characterization and properties of polymers containing simultaneously the imine and amide moieties.