Synthesis and characterization of new polyimides containing pendent pentadecyl chains

Abstract

A new unsymmetrical aromatic diamine, viz., 4-pentadecylbenzene-1,3-diamine was synthesized through a series of reaction steps starting from 3-pentadecylphenol. 4-Pentadecylbenzene-1,3-diamine was employed to synthesize a series of new polyimides by one-step polycondensation in m-cresol with four commercially available aromatic dianhydrides, viz., 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA), 3,3′,4,4′-benzophenonetetracarboxylic dianhydride (BTDA), 4,4′-oxydiphthalic anhydride (ODPA) and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6-FDA). Inherent viscosities of resulting polyimides were in the range 0.33–0.67 dL/g and number average molecular weights were in the range 14,700–52,200 (GPC, polystyrene standard). Polyimides containing pendent pentadecyl chains were soluble in organic solvents such as chloroform, m-cresol, N, N-dimethylacetamide (DMAc), 1-methyl-2-pyrrolidinone (NMP), pyridine and nitrobenzene. Strong and flexible films of polyimides could be cast from their chloroform solutions. Polyimides exhibited glass transition temperature in the range 158–206 °C. The temperature at 10% wt. loss ( T 10), determined by TGA in nitrogen atmosphere, of polyimides was in the range 470–480 °C indicating good thermal stability.