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Synthesis and characterization of heat-resistant and soluble poly(amide-imide)s from unsymmetrical dicarboxylic acid containing 2-(triphenyl phosphoranylidene) moiety and various aromatic diamines

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Abstract

An unsymmetrical and non-coplaner heterocyclic phosphorus containing dicarboxylic acid monomer, (DCA-3) is successfully synthesized with high purity. A series of novel aromatic poly(amide-imide)s having ether or/sulphur or/fluorine or/phosphorus containing phenyl moieties in their backbone are then prepared via a direct phosphorylation polycondensation of synthesized dicarboxylic acid with various aromatic diamines. Chemical structures of DCA-3 as well as resulting polymers are confirmed by FT-IR, NMR spectroscopic techniques and elemental analysis. These polymers are readily soluble in a variety of aprotic polar solvents such as NMP, DMSO, DMAc and DMF, etc. UV spectra showed that all poy(amide-imide)s films exhibit high optical transparency. In addition, the glass transition temperatures (Tg) of these polymers were determined by differential scanning calorimetry and found in the range 271–346C. Furthermore, thermogravimetric analysis of these polymers showed good thermal stability, 10% weight loss at temperature in excess of 538C and char yield at 700C in nitrogen ranging from 68 to 79%. From wide-angle X-ray diffraction experiments, all polymers showed amorphous behaviour.

Phosphorus containing aromatic poly(amide-imide)s are prepared from a new kind of dicarboxylic acid, having 2-(triphenyl phosphoranylidene) pendent group, with various aromatic diamines by polycondensation method. The resulting poly(amide-imide)s exhibit good solubility in organic solvents, excellent thermal stability, high optical transparency, as well as low crystallinity and good film forming capability.

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Acknowledgements

The author (S. Agrawal) is grateful to Guru Gobind Singh Indraprastha University, New Delhi for providing financial support in the form of IPRF.

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Correspondence to ANUDEEP KUMAR NARULA.

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Supplementary Information

Supplementary information contains elementary data of polymer 5a, 5b, 5c and 5d. GPC data of polymer 5c, 1H-NMR spectra of polymer 5a, 5c and 5d and is available at www.ias.ac.in/chemsci.

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AGRAWAL, S., NARULA, A.K. Synthesis and characterization of heat-resistant and soluble poly(amide-imide)s from unsymmetrical dicarboxylic acid containing 2-(triphenyl phosphoranylidene) moiety and various aromatic diamines. J Chem Sci 127, 737–749 (2015). https://doi.org/10.1007/s12039-015-0830-1

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