Fabrication of biodegradable poly(ester-amide)s based on tyrosine natural amino acid |
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Authors: | Email author" target="_blank">Amir?AbdolmalekiEmail author Email author" target="_blank">Shadpour?MallakpourEmail author Sedigheh?Borandeh Mohammad?R?Sabzalian |
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Institution: | (1) Department of Chemistry, Isfahan University of Technology, 84156-83111 Isfahan, Iran;(2) Nanotechnology and Advanced Materials Institute, Isfahan University of Technology, 84156-83111 Isfahan, Iran;(3) Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, 84156-83111 Isfahan, Iran;(4) Department of Agronomy and Plant Breeding, College of Agriculture, Isfahan University of Technology, 84156-83111 Isfahan, Iran |
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Abstract: | N,N′-Bis2-(methyl-3-(4-hydroxyphenyl)propanoate)]isophthaldiamide (5), a novel diol monomer containing chiral group, was prepared by the reaction of S-tyrosine methyl ester (3) with isophthaloyl dichloride (4a). A new family of optically active and potentially biodegradable poly(ester-amide)s (PEAs) based on tyrosine amino acid were
prepared by the polycondensation reaction of diol monomer 5 with several aromatic diacid chlorides. The resulting new polymers were obtained in good yields with inherent viscosities
ranging between 0.25 and 0.42 dL/g and are soluble in polar aprotic solvents. They showed good thermal stability and high
optical purity. The synthetic compounds were characterized and studied by FT-IR, 1H-NMR, specific rotation, elemental and thermogravimetric analysis (TGA) techniques and typical ones by 13C-NMR, differential scanning calorimetry (DSC), X-ray diffraction (XRD), and field emission scanning electron microscopy (FE-SEM)
analysis. Soil burial test of the diphenolic monomer 5, and obtained PEA6a, and soil enzymatic assay showed that the synthesized diol and its polymer are biologically active and probably biodegradable
in soil environment. |
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