Synthesis of biodegradable chiral poly(ester-imide)s derived from valine-, leucine- and tyrosine-containing monomers |
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Authors: | Mallakpour Shadpour Asadi Parvin Sabzalian Mohammad R |
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Institution: | (1) Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran;(2) Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran;(3) College of Agriculture, Department of Agronomy and Plant Breeding, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran |
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Abstract: | The present demand for a drastic reduction in environmental pollution is extended to qualitative change in the approach to
development of biodegradable polymers. The aim of this article is to focus on the synthesis of biodegradable optically active
poly(ester-imide)s (PEI)s, which compose of different amino acids in the main chain as well as in the side chain. These polymers
were synthesized by polycondensation of diacid monomers such as 5-(2-phthalimidyl-3-methyl butanoylamino) isophthalic acid
(1), 5-(4-methyl-2-phthalimidyl pentanoylamino)isophthalic acid (2) with N,N′-(pyromellitoyl)-bis-l-tyrosine dimethyl ester (3) as a phenolic diol. The direct polycondensation reaction was carried out in a system of tosyl
chloride, pyridine and N,N-dimethylformamide as a condensing agent under conventional heating conditions. The optically active PEIs were obtained in
good yield and moderate inherent viscosity. The synthesized polymers were characterized by means of FT-IR, 1H-NMR, elemental and thermo gravimetric analysis techniques. In addition, in vitro toxicity and soil burial test were employed
for assessing the sensitivity of these compounds to microbial degradation. To this purpose, biodegradability behavior of the
monomers and polymers were investigated in culture media and soil condition. The results of this study revealed that synthesized
monomers and their derived polymers are biologically active and probably microbiologically biodegradable. |
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