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Synthesis and thermal evaluation of novel mono- and bis-adamantylated resorcinol-based phthalonitrile resins with enhanced solubility

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Abstract

Phthalonitrile (PN) resins are high-temperature-resistant thermosetting polymers which find applications in military as well as aerospace owing to their outstanding performance. At present, most of the PN resins are melt-processed and cured at high temperature via resin transfer moulding owing to their poor solubility in common organic solvents. In the present, embodiment efforts have been made to change the PN resin backbone with adamantane as potential functionality. Mono- and novel bis-adamantylated resorcinols 1a and 1b have been synthesized via Amberlyst-15 solid acid resin-catalysed Friedel–Crafts alkylation reaction, as precursor material for the synthesis of novel phthalonitrile (PN) resin monomers 2a and 2b, respectively. The study includes structural and thermal characterization of resin monomers 2a and 2b along with their solubility in common organic solvents. These resins when cured to their thermosets have demonstrated thermal stability ~ 723 K (5% mass loss) with no glass transition temperature (Tg) up to 673 K. The resin monomers show very good solubility in industry-friendly organic solvents like acetone, ethyl acetate, methyl ethyl ketone and methyl isobutyl ketone.

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Acknowledgements

The authors are highly thankful to Mr. Ram Prakash for his valuable suggestions in drafting the manuscript. The authors are also thankful to director DMSRDE, for providing necessary support to carry out work.

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  1. The Defence Materials and Stores Research Development Establishment, G.T. Road, Kanpur, 208013, India

    Ajit Shankar Singh, S. K. Shukla, Preeti Mishra & A. K. Pandey

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  1. Ajit Shankar Singh
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Singh, A.S., Shukla, S.K., Mishra, P. et al. Synthesis and thermal evaluation of novel mono- and bis-adamantylated resorcinol-based phthalonitrile resins with enhanced solubility. J Therm Anal Calorim 147, 6665–6677 (2022). https://doi.org/10.1007/s10973-021-10991-0

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