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Oligomeric poly(imide-amides)s containing side 1,8-naphthalimidyl groups: synthesis and characterization

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Abstract

Poly(imide-amide)s (PIAs) were synthesized from isophthalic acids, which have in position 5 a bulky group like 1,8-naphthalimidyl bonded to amino acids as flexible spacers, and the diamine bis(4-aminophenyl)diphenylsilane, which provides a polar group in the main chain. Glycine, l-alanine, l-phenylalanine, l-valine and p-aminobenzoic acid were used as amino acids. Polymers were obtained according to the Yamazaki method and characterized by elemental analysis, optical activity, IR and 1H, 13C and 29Si NMR spectroscopy. PIAs were soluble in aprotic polar solvents but not in common organic solvents, and obtained with low η inh values, which was an indicative of low molecular weights species, probably of oligomeric nature. According to the polymeric structure, the only difference between PIAs is the structure of the amino acid residue, and in this sense it was possible to see an increase of the T g values when the volume of the amino acid residue also increased, due to the lower possibility of internal mobility of the side chains. The higher Tg value was obtained with the PIA-e, which includes an aromatic ring as a side chain, derived from p-aminobenzoic acid. PIAs, in spite of the good TDT values obtained, were not thermally stable in the sense that the 10 % of weight lost was obtained at lower temperature than 400 °C, with the exception of PIA-e derived from p-aminobenzoic acid. However, there was an increase of the TDT values when the volume of the amino acid residue increases. The PIAs do not show good UV–vis transparence probably due to the low free volume of those including an aliphatic amino acid residue.

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Acknowledgments

Authors acknowledge “Fondo Nacional de Investigación Científica y Tecnológica”, FONDECYT, through Project 1100015.

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Authors and Affiliations

  1. Facultad de Química, Pontificia Universidad Católica de Chile, P.O. Box 306, Santiago, Chile

    L. H. Tagle, C. A. Terraza, A. Tundidor-Camba & F. A. Lara

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  1. L. H. Tagle
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  2. C. A. Terraza
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  3. A. Tundidor-Camba
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  4. F. A. Lara
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Correspondence to L. H. Tagle.

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Tagle, L.H., Terraza, C.A., Tundidor-Camba, A. et al. Oligomeric poly(imide-amides)s containing side 1,8-naphthalimidyl groups: synthesis and characterization. Polym. Bull. 71, 1031–1042 (2014). https://doi.org/10.1007/s00289-014-1109-2

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  • DOI: https://doi.org/10.1007/s00289-014-1109-2

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