New Polymer Syntheses Part 53. Novel Polyamides of Diarylidenecycloalkanone Containing Azo Groups in the Polymer Backbone: Synthesis and Characterization

A new interesting class of polyamides of diarylidenecycloalkanone containing azo groups in the polymer backbone 6 a-d was synthesized by a solution polycondensation reaction of bis 2-aminoarylidene monomers 3 a,b with 4,4′-azodibenzoyl dichlorides and 3,3′-azodibenzoyl dichlorides in NMP as a solvent, using anhydrous LiCl as a catalyst at room temperature. The model compounds 4, 5 were synthesized by the interaction of one mole of bis 2-aminoarylidene monomers 3 a,b with two moles of benzoyl chloride using anhydrous LiCl as a catalyst in NMP at room temperature. The resulting polymers were characterized by elemental and spectral analyses, besides solubility and viscometry measurements. The thermal properties of those polymers were evaluated by TGA, DTG and DTA measurements and correlated to their structural units. X–ray analysis of the polymers showed that polyamides based on para-azo linkage have a higher degree of crystallinity than those based on meta-azo linkage in the region 2θ = 5−60°. In addition, the morphological properties of selected examples were tested by SEM. Keywords: aromatic azo chromophoresazo polymerssynthesis Notes *Measured in DMSO, with C = 0.5 g/100 ml at 30°C. ++: Soluble at room temperature (RT). +: Partially soluble at (RT). −: Insoluble. *The values were determined by TGA at a heating rate of 10°C/min.