Synthesis of Soluble and Thermally Stable Polyamides from Diamine Containing (quinolin-8-yloxy) Aniline Pendant Group

A novel diamine monomer having pendant 4-(quinolin-S-yloxy) aniline group was successfully synthesized via aromatic substitution reaction of 8-quinolinol With p-fluoronitrobenzene followed by Pd/C catalyzed hydrazine reduction, amidation reaction between 4-(quinoline-8-yloxy) aniline and 3,5-dinitrobenzoylcholoride followed by Pd/C catalyzed hydrazine reduction. The diamine monomer was fully characterized by using FTIR, H-1-NMR, C-13-NMR, and elemental analysis. The diamine monomer was polymerized with various aromatic and aliphatic dicarboxylic acids to obtain the corresponding polyamides. The polyamides had inherent viscosity in the range of 0.30-0.41 dL/g and exhibited excellent Solubility in the polar aprotic solvents such as DMAc, NMP, N,N-dimethylformamide, Pyridine, and DMSO. The glass transition temperatures (T,,) of the polymers are high (up to 313 degrees C) and the decomposition temperatures (T) range between 200 and 370 degrees C, depending on the diacids residue in the polymers backbone. (C) 2009 Wiley Periodicals, Inc. J Appl Polym Sci 116: 64-71, 2010