Abstract
In the present embodiment, bisphthalonitrile resin has been cured using synthesized novel bisphenyl nitrile-containing benzoxazine (NBZ) vis-a-vis traditional curing agents such as 4-(3′aminophenoxy)diphenyl sulphone (m-DDS) and amino-functionalized phthalonitrile (APN) to study the curing efficacy coupled with processing window and mechanism of curing. It has been established by FT-IR and DSC that NBZ molecules cure the bisphthalonitrile resin matrix by formation of free phenolic groups which act as nucleophile triggering the curing reaction through nitrile–nitrile addition polymerization reaction. Additionally, it has been seen that NBZ-catalyzed phthalonitrile resin curing system showed better processing window in comparison to m-DDS- and APN-catalyzed system. Considering the end-user applications, the NBZ- and m-DDS-cured resins have also been studied for their TG, DMA, water uptake, thermo-oxidative and dielectric properties.
Similar content being viewed by others
References
Keller TM (1988) Phthalonitrile based high temperature resin. J Polym Sci Part A Polym Chem 26:3199–3212
Sastri SB, Armistead JP, Keller TM (1996) Phthalonitrile-carbon fiber composite. Polym Compos 17:816–822
Dominguez DD, Jones HN, Keller TM (2004) The effect of curing additive on mechanical properties of phthalonitrile-carbon fiber composites. Polym Compos 25:554–561
Sumner MJ, Sankarapardian M, McGrath JE, Riffle JS, Sorathia U (2002) Flame retardant novolac-bisphthalonitrile structural thermosets. Polymer 43:5069–5076
Keller TM, Dominguez DD (2005) High temperature resorcinol based phthalonitrile polymers. Polymer 46:4614–4618
Laskoski M, Dominguez DD, Keller TM (2007) Synthesis and properties of aromatic ether phosphine oxide containing oligomeric phthalonitrile resins with improved oxidative stability. Polymer 48:6234–6240
Dominguez DD, Keller TM (2007) Properties of phthalonitrile monomer blends and thermosetting phthalonitrile copolymers. Polymer 48:91–97
Sumner MJ, Weyers RY, Rosario AC, Riffle JS, Sorathia U (2004) Synthesis and characterization of vinyl ester networks containing phthalonitrile moieties. Polymer 45:5099–6106
Yang Y, Min Z, Yi L (2007) A novel addition curable novolac bearing phthalonitrile groups: synthesis, characterization and thermal properties. Polym Bull 59:185–194
Laskoski M, Dominguez DD, Keller TM (2005) Synthesis and properties of bisphenol A based phthalonitrile resins. J Polym Sci Part A Polym Chem 43:4136–4143
Sastri SB, Keller TM (1998) Phthalonitrile cure reaction with aromatic diamines. J Poly Sci Part A Polym Chem 36:1885–1890
Sastri SB, Keller TM (1998) Phthalonitrile polymers: cure behaviour and properties. J Poly Sci Part A Polym Chem 37:1885–1890
Li WT, Zua F, Liu XB (2009) Study of catalytic effect of ammonium molybdate on bisphthalonitrile resins curing reaction with aromatic amines. Chin Chem Lett 20:348–351
Zeng K, Zhoo K, Tang WR, Tang Y, Zhoo HF, Liu T, Wang YP, Zhou HB, Yang G (2007) Synthesis and curing of a novel amino containing phthalonitrile derivative. Chin Chem Lett 18:523–526
Zang K, Zhou K, Hong H, Zhou H, Wang Y, Miao P, Yang G (2009) Studies on self promoted cure behaviour of hydroxy-containing phthalonitrile model compounds. Euro Polym J 45:1328–1335
Agag T, Takeichi T (2001) Novel benzoxazine monomers containing p-phenyl propargyl ether. Polymerization of monomers and properties of polybenzoxazines. Macromolecules 34:7257–7263
Velez-Herrera P, Doyama K, Hiroshi Abe, Ishida H (2008) Synthesis and characterization of highly fluorinated polymer with the benzoxazine moiety in the main chain. Macromolecules 41:9704–9714
Ghosh NN, Kiskan B, Yagci Y (2007) Polybenzoxazines-new high performance thermosetting resins: synthesis and properties. Progr Polym Sci 32:1344–1391
Men W, Lu Z (2007) Synthesis and characterization of 4,4′-diaminophenyl methane based benzoxazine and their polymers. J Appl Polym Sci 106:2769–2774
Brunovska Z, Lyon R, Ishida H (2000) Thermal properties of phthalonitrile functional polybenzoxazines. Thermochem Acta 357–358:195–203
Agag T, Takeichi T (2006) Preparation, characterization and polymerization of maleimidobenzoxazine monomers as a novel class of thermosetting resins. J Appl Polym Sci 44:1424–1435
Kim HJ, Brunovska Z, Ishida H (1999) Synthesis and thermal characterization of polybenzoxazines based on acetylene-functional monomers. Polymer 40:6565–6573
Chernykh A, Agag T, Ishida H (2009) Effect of polymerizing diacetylene groups on the lowering of polymerization temperature of benzoxazine groups in the highly thermally stable main-chain-type polybenzoxazines. Macromolecules 42:5121–5127
Brunovska Z, Ishida H (1999) Thermal study on the copolymers of phthalonitrile and phenylnitrile-functional benzoxazines. J Appl Polym Sci 73:2937–2949
Cao GP, Chen WJ, Liu XB (2008) Synthesis and thermal properties of the thermosetting resin based on cyano functionalized benzoxazine. Polym Degrad Stab 93:739–744
Sheng H, Peng X, Guo H, Yu X, Naito K, Qu X, Zhang Q (2014) Synthesis of high performance bisphthalonitrile resins cured with self-catalyzed 4-aminophenoxy phthalonitrile. Thermochim Acta 577:17–24
Van Krevelan DW (1990) Properties of polymers. Elsevier, New York, p 649
Gou H, Chen Z, Zhang J, Yang X, Zhao R, Liu X (2012) Self-promoted curing phthalonitrile with high glass transition temperature for advanced composites. J Polym Res 19:9918–9926
Augustine D, Mathew D, Nair CPR (2015) One component propargyl phthalonitrile novolac: synthesis and characterization. Eur Polym J 71:389–400
Acknowledgements
Authors are also thankful to Mr. Ram Prakash for his valuable suggestions in drafting of manuscript.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Singh, A.S., Shukla, S.K., Pandey, A.K. et al. Synthesis and evaluation of catalytic curing behavior of novel nitrile-functionalized benzoxazine for phthalonitrile resins. Polym. Bull. 75, 3781–3800 (2018). https://doi.org/10.1007/s00289-017-2235-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-017-2235-4