Synthesis and characterization of new polyamideimides with a highly flexible soft block

Abstract

Five new polyamideimides (PAI) were synthesized from five diacid chlorides with preformed imide rings and a telechelic α,ω-diamino-polyoxyethylene (Jeffamine JFA ED600). The diacid chloride monomers could be obtained in high yields (77–92%) from chlorinating the corresponding diacids which were obtained from the reaction of trimellitic anhydride with aromatic diamines (1,4-phenylene diamine; 2,2-bis(4-aminophenyl)methane; 2,2-bis(4-aminophenyl)propane; 4,4′-oxydianiline and 1,1-bis(4-aminophenyl)cyclohexane). The telechelic monomers were characterized by FTIR and 1H-NMR. After a few preliminary experiments aimed at optimizing the polymerization conditions for particularly poorly soluble diacid chlorides, five new PAI were synthesized with inherent viscosities in the range of 0.35–0.65 dL/g. Their characterization by transmission FTIR and by advanced NMR techniques, including heteronuclear 2D NMR, fully confirmed their chemical structure as shown by the complete assignments of their 1H and 13C-NMR spectra. Compared with other PAI described in the literature, these polymers proved to be much more sensitive towards polar organic solvents even showing significant solubilities in chloroform and tetrahydrofuran. These materials enabled the casting of transparent films which were very tough in the dry state. However, and as further evidenced by a DSC investigation, their phase separation is usually not sufficient to provide a very strong physical crosslinking by the aggregation of the polymer hard blocks. Consequently, their physical crosslinking would have to be significantly improved for preventing the material failure in highly solvating media and open the way for new performances in membrane separation systems. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 2873–2889, 1999