Synthesis and Characterization of New Organosoluble Poly(Amide-Imide)s with Good Thermal Properties Containing Photosensitive and Bicyclo Segments in the Main Chain

Four new organosoluble poly(amide-imide)s (PAIs) (8a-d) with good inherent viscosities containing a photosensitive group and bicyclo segment were synthesized, from the direct polycondensation reaction of N,N'-bis(4-carboxyphenyl)bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic diimide 3 with four aromatic diamines (7a-d) containing a photosensitive group, by two different methods, i.e., direct polycondensation in a medium consisting of N-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride (CaCl(2))/pyridine (Py) and direct polycondensation in a tosyl chloride (TsCl)/pyridine (Py)/N,N-dimethylformamide (DMF) system. Dicarboxylic acid 3 was prepared by reaction of bicyclo[2,2,2] oct-7-ene-2,3,5,6-tetra carboxylic dianhydride 1 with p-aminobenzoic acid 2 in a mixture of acetic acid and pyridine (3:2). All of the above polymers were fully characterized by (1)H-NMR, FT-IR, elemental analysis, inherent viscosity, solubility tests, UV-Vis spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and derivative of thermaogravimetric (DTG). The resulting PAIs 8a-d have showed admirable good inherent viscosities, thermal stability and solubility. (C) Koninklijke Brill NV, Leiden, 2011