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High Performance Polymers
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Synthesis and Characterization of Organosoluble Optically Active Poly(ester-imide)s Derived from Trimellitic Anhydride, L-Methionine and Bisphenols

Shadpour Mallakpour

Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, I.R. Iran, mallak{at}cc.iut.ac.ir

Shahrzad Meratian

Organic Polymer Chemistry Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, I.R. Iran

The reaction of thionyl chloride in pyridine as a condensing agent was used for the direct polycondensation of N-trimellitylimido-L-methionine (4) with various aromatic diols such as bisphenol A (5a), phenolphthalein (5b), 1,5-naphthalendiol (5c), 2,6-dihydroxytoluene (5d), hydroquinone (5e), biphenyl-2,2'-diol (5f), 1,4-dihydroxyanthraquinone (5g). This reaction leads to the formation of novel optically active poly(ester-imide)s (PEI)s. The resulting PEIs were obtained in good yields and exhibited low to moderate inherent viscosities ranging from 0.15 to 0.40 dL g-1. All of the PEIs showed good solubility and readily dissolved in solvents such as N-methyl-2-pyrrolidinone (NMP), N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), pyridine and tetrahydrofuran. Thermogravimetric analysis showed that PEI 6b was stable, with 10% weight loss recorded above 370oC in nitrogen. All of the above polymers were characterized by FTIR, specific rotation, and representative PEIs were also characterized by 1 H NMR, elemental analysis, and thermogravimetric analysis. The structural characterization and physical properties of these new optically active PEIs are reported.

Key Words: Organosoluble • thionyl chloride/pyridine condensing agent • trimellitic anhydride • poly(ester-imide)s • optically active polymers • thermally stable polymers

This version was published on February 1, 2008

High Performance Polymers, Vol. 20, No. 1, 3-18 (2008)
DOI: 10.1177/0954008307078385


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