Construction of chiral polyesters from polycondensation of multifunctional monomer containing both flexible amino acid and rigid pendant groups with aromatic diols.
A number of chiral wholly aromatic polyesters (PEs) with phthalimido and flexible chiral unit in the backbone were prepared from a chiral synthesized diacid monomer, 5-(3-methyl-2-phthalimidylpentanoylamino)isophthalic acid (1), and various aromatic diols via the polyesterification reaction. The tosyl chloride/pyridine/N,N-dimethylformamide (DMF) system was used as a condensing agent. All of the these polymers having bulky phthalimido and amino acid functionalities in the side chain showed excellent solubility and readily dissolved in various solvents such as N-methyl-2-pyrrolidinone, N,N-dimethylacetamide and DMF. Since, these chiral polymers have natural amino acids in the polymer architecture, they are expected to be biodegradable and therefore may be classified under eco-friendly polymers. They had useful levels of thermal stability associated with excellent solubility. Thermogravimetric analysis (TGA) showed that the obtained PEs are rather thermally stable, 10% weight loss temperatures in excess of 317 degrees C, and char yields at 700 degrees C in the nitrogen atmosphere higher than 24%. The resulting polymers were obtained in good yields with inherent viscosities ranging between 0.22 and 0.56 dL/g and were characterized with FT-IR, 1H-NMR, elemental and TGA techniques.
Mallakpour
Shadpour
S
Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, 84156-83111, Isfahan, I R Iran. mallak@cc.iut.ac.ir
Khani
Marziyeh
M
D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D012995:Solubility; D013818:Thermogravimetry
D000596:Amino Acids; D011084:Polycyclic Aromatic Hydrocarbons; D011091:Polyesters; D011108:Polymers