New organosoluble aromatic poly(esterimide)s containing pendent pentadecyl chains

Abstract

A new diimide dicarboxylic acid, namely 2,2′-(4-pentadecyl-1,3-phenylene)bis(1,3-dioxoisoindoline-5-carboxylic acid), containing preformed imide rings and pentadecyl chain, was synthesized by the reaction of 4-pentadecylbenzene-1,3-diamine with trimellitic anhydride. A series of new aromatic poly(esterimide)s (PEIs) was synthesized using diphenylchlorophosphate-activated direct polycondensation of 2,2′-(4-pentadecyl-1,3-phenylene)bis(1,3-dioxoisoindoline-5-carboxylic acid), with five commercially available bisphenols, namely 4,4′-isopropylidenediphenol (I), 4,4′-(hexafluoroisopropylidene)diphenol (II), 4,4′-oxydiphenol (III), 4,4′-biphenol (IV), and 4,4′-(9-fluorenylidene)diphenol (V) in the presence of pyridine and lithium chloride. Inherent viscosities of PEIs were in the range 0.54–0.83 dL g−1 in chloroform (CHCl3) at 30 ± 0.1°C. PEIs containing pendent pentadecyl chains were soluble in organic solvents such as CHCl3, m-cresol, N, N-dimethylacetamide, 1-methyl-2-pyrrolidinone, pyridine, and nitrobenzene. Tough, transparent, and flexible films of PEIs could be cast from their CHCl3 solutions. PEIs exhibited glass transition temperature in the range 145–198°C. The temperature at 10% weight loss of PEIs, determined by thermogravimetric analysis under the nitrogen atmosphere, was in the range of 450–470°C indicating good thermal stability.