Journal of Science  and Technology of Composites

Journal of Science and Technology of Composites

The Effect of Amine and Phenolic Curing Agents on Curing Temperature of High Temperature Phthalonitrile Resin for Preparation of High Performance Carbon/ Phthalonitrile Composite

Document Type : Research Paper

Authors
1 Polymer Engineering, Malek Ashtar University of Technology, Tehran, Iran.
2 Polymer Chemistry, Malek Ashtar University of Technology, Tehran, Iran.
Abstract
In this work, Phthalonitrile resin based on bisphenol A was synthesized with a yield of 93% and a purity of 98.91%, and its structure was identified using various techniques. To investigate the effect of curing agent type on curing temperature and thermal property of resin, the synthesized resin was cured with two different curing agents including bisphenole A and methylene dianiline. It was observed that the amine curing agent, despite its lower weight percentage, has a more significant effect on accelerating the curing process. Finally, a composite of the synthesized phthalonitrile resin and carbon fibers was prepared with two resin contents, 32% and 41%, and its mechanical and thermal properties were evaluated. The results indicated that the composite with 32% resin content exhibited superior properties, with an interlaminar shear strength (ILSS) of 36.4 MPa and a modulus of 14.56 GPa. The thermal resistance of both resin and composite was assessed using the TGA technique, revealing that the pure resin has a char yield of 72%, while the composite with 32% resin content has a char yield of 87% at 800°C under a nitrogen atmosphere. Moreover, the TGA results demonstrated that the phthalonitrile / carbon fiber composites has approximately the same thermal stability at air and argon atomosphere, domenstrating excellent ability of this resin as a thermal barrier.
Keywords

Subjects


[1]  Hsissou, R., Seghiri, R., Benzekri, Z., Hilali, M., Rafik, M. and Elharfi, A., “Polymer composite materials: A comprehensive review,” Composite structures, Vol. 262, pp. 113640, 2021.
[2]  Fattahi, H., Amani, M., Mosaei Oskoei, Y. and Arsalani, N., “Novel thermal stable polymeric nanocomposite based on poly (ethyl vinyl ether‐alt‐maleic anhydride) and organo‐modified montmorillonite,” Polymer Composites, Vol. 39, pp. 3889-3895, 2018.
[3]  Rahimi Pishbijari, M., Eskandari Jam, J. and Heydari Beni, M., “Design and Develpoment of Polymer Based Composite in Order to Minimize the RCS,” Journal of Science and Technology of Composites, Vol. 7, pp. 1047-1056, 2020.
[4]  Singh, A. S., Das, V., Chopra, S., Pandey, A. K. and Namburi, E. P., “High Temperature Resistant Thermosetting Resin Materials,” Novel Defence Functional and Engineering Materials, Vol. 1, pp. 37-71, 2024.
 [5] Liaw, D.J., Wang, K.L., Huang, Y.C., Lee, K.R., Lai, J.Y. and Ha, C. S., “Advanced polyimide materials: Syntheses, physical properties and applications,” Progress in Polymer Science, Vol. 37, pp. 907-974, 2012.
[6]  Payamani, M., Fattahi, H. and Mortezaei, M., “Synthesis and Characterization of 4, 4'-Bis (maleimido) diphenylmethane Resin and Evaluation of Its Curing Behavior in Blending with Epoxy,” Iranian Journal of Polymer Science and Technology, Vol. 35, pp. 339-352, 2022.
[7]  Iyer, N. P. and Arunkumar, N., “Review on Fiber reinforced/modified Bismaleimide resin composites for Aircraft Structure Application,” in IOP Conference Series: Materials Science and Engineering, Vol. 923, pp. 1205, 2020.
[8]  Ahmadi, M., Fattahi, H., Mortezaei, M., Mirbagheri, S. M. J., “High temperature cyanate ester/carbon fiber composite with high ILSS based on synthesized 2,2'-bis (4-cyanatophenyl) propane resin,” In Persian, Journal of Science and Technology of Composites, Vol. 11, pp. 2419-2428, 2024.
[9]  Goyal, S. and Cochran, E. W., “Cyanate ester composites to improve thermal performance: a review,” Polymer International, Vol. 71, pp. 583-589, 2022.
[10] Lochab, B., Monisha, M., Amarnath, N., Sharma, P., Mukherjee, S. and Ishida, H., “Review on the accelerated and low-temperature polymerization of benzoxazine resins: addition polymerizable sustainable polymers,” Polymers, Vol. 13, pp. 1260, 2021.
[11] Lyu, Y. and Ishida, H., “Natural-sourced benzoxazine resins, homopolymers, blends and composites: A review of their synthesis, manufacturing and applications,” Progress in Polymer Science, Vol. 99, pp. 101168, 2019.
[12] Bulgakov, B., Morozov, O., Timoshkin, I., Babkin, A. and Kepman, A., “Bisphthalonitrile-based thermosets as heat-resistant matrices for fiber reinforced plastics,” Polymer Science, Series C, Vol. 63, pp. 64-101, 2021.
[13] Hajebi, S., Payamani, M., Fattahi, H., Mortezaei, M. and Jalilolghadr, S., “Dual-Curing Epoxy Thermosets: Design, Curing, Properties and Applications,” Polymer Reviews, pp. 1-31, 2024.
[14] Pouladvand, A. R., Mortezaei, M., Fattahi, H. and Amraei, I. A., “A novel custom-tailored epoxy prepreg formulation based on epoxy-amine dual-curable systems,” Composites Part A: Applied Science and Manufacturing, Vol. 132, pp. 105852, 2020.
[15] Sahraei,             S. and Ahangaran, F., “A review on anti-corrosion self-healing epoxy coatings,” Journal of Science and Technology of Composites, Vol. 9, pp. 2046-2062, 2022.
[16] Asim, M., Saba, N., Jawaid, M., Nasir, M., Pervaiz, M. and Alothman, O. Y., “A review on phenolic resin and its composites,” Current Analytical Chemistry, Vol. 14, pp. 185-197, 2018.
[17] Knop, A. and Pilato, L. A., “Phenolic resins: chemistry, applications and performance. Springer Science & Business Media,” 2013.
[18] Faraji, M.  and Esfandeh, M., “Improvement of delamination resistance of glass-phenolic composites through matrix toughening mechanism using poly (vinyl butyral),” Journal of Science and Technology of Composites, Vol. 5, pp. 521-528, 2019.
[19] Derradji, M., Jun, W. and Wenbin, L., “Phthalonitrile resins and composites: properties and applications.,” William Andrew, 2018.
[20] Gu H., “An overview of high-performance phthalonitrile resins: fabrication and electronic applications,” Journal of Materials Chemistry C, Vol. 10, pp. 2925-2937, 2022.
[21] Derradji, M., Zegaoui, A., Medjahed, A., Liu, W. and Henniche, A., “Hybrid phthalonitrile‐based materials with advanced mechanical and nuclear shielding performances,” Polymer Composites, Vol. 41, pp. 134-141, 2020.
[22] Sastri, S. B., Armistead, J. P. and Keller, T. M., “Phthalonitrile‐carbon fiber composites,” Polymer Composites, Vol. 17, pp. 816-822, 1996.
[23] Lobanova, M., “Effect of post‐curing temperature on the retention of mechanical strength of phthalonitrile thermosets and composites after a long‐term thermal oxidative aging,” Polymer Composites, Vol. 44, pp. 8330-8343, 2023.
[24] Boghozian, T., Stackpoole, M. M. and Gasch, M., “Cyanate Ester and Phthalonitrile Impregnated Carbon Ablative TPS,” in High Temperature Polymeric Laminate Workshop, 2016.
[25] Aleshkevich, V. V., Bulgakov, B. A., Lipatov, Y. V., Babkin, A. V. and Kepman, A. V., “High performance carbon–carbon composites obtained by a two-step process from phthalonitrile matrix composites,” Mendeleev Communications, Vol. 32, pp. 327-330, 2022.
[26] Dominguez, D. D., Jones, H. N. and Keller, T. M., “The effect of curing additive on the mechanical properties of phthalonitrile‐carbon fiber composites,” Polymer composites, Vol. 25, pp. 554-561, 2004.
[27] Bulgakov, B., “Phthalonitrile-carbon fiber composites produced by vacuum infusion process,” Journal of Composite Materials, Vol. 5,  pp. 4157-4164, 2017.
[28] Bulgakov, B. A., Babkin, A. V., Kepman, A. V. and Avdeev, V. V., “Advanced Phthalonitrile Resin Systems for Vacuum Processing,” SAMPE 2020| Virtual Series, 2020.
[29] Chen, Z., Guo, H., Tang, H., Yang, X., Xu, M. and Liu, X., “Preparation and properties of bisphenol A‐based bis‐phthalonitrile composite laminates,” Journal of Applied Polymer Science, Vol. 129, pp. 2621-2628, 2013.
[30] Luo, Y., Xu, M., Pan, H., Jia, K. and Liu, X., “Effect of ortho‐diallyl bisphenol A on the processability of phthalonitrile‐based resin and their fiber‐reinforced laminates,” Polymer Engineering & Science, Vol. 56, pp. 150-157, 2016.
[31] Sun, B.G., “Enhanced mechanical properties at 400° C of carbon fabric reinforced phthalonitrile composites by high temperature postcure,” Composites Part B: Engineering, Vol. 166, pp. 681-687, 2019.
[32] Keller, T. M., Price, T. R. and Griffith, J. R., “Synthesis of phthalonitriles by nitro displacement, ” Synthesis, Vol. 1980, pp. 613-613, .1980
 [33]        Jia, Y., “Catalytic polymerization of phthalonitrile resins by carborane with enhanced thermal oxidation resistance: Experimental and molecular simulation,” Polymers, Vol. 14, no. 1, p. 219, 2022.
[34] Keller, TM, “Polyphthalocyanine resins.,” United States Patent, 1980.
[35] Ting, R., Keller, T., Price, T. and Poranski Jr, C., “Characterization of the cure of diether-linked phthalonitrile resins,” ACS Symposium Series, 1982.
[36] Keller, T. M. and Price, T. R., “Amine-cured bisphenol-linked phthalonitrile resins,” Journal of Macromolecular Science—Chemistry, Vol. 18, pp. 931-937, 1982.
[37] Sastri, S. B. and Keller, T. M., “Phthalonitrile cure reaction with aromatic diamines,” Journal of Polymer Science Part A: Polymer Chemistry, Vol. 36,  pp. 1885-1890, 1998.
[38]           Jahani, M., Fattahi, H. and Mortezaei, M., “Effect of Aromatic Amine Structure as a Curing Agent on Molecular Packing and Mechanical Properties of Cured Epoxy Resin,” Iranian Journal of Polymer Science and Technology, Vol. 32, 2019.
[39] Keller, T. M., “Amino phenyl containing curing agent for high performance phthalonitrile resin,” Google Patents, 1991.
[40] Wolfgang, J. D., Dysart, J. L. and Laskoski, M., “Improved cure kinetics of phthalonitrile resins using dicyanamide‐based ionic liquids,” Journal of Applied Polymer Science, Vol. 140, pp. 53534, .2023
[41] Modirrousta, M., Fattahi, H., Mortezaei, M. and Jahani, M., “Curing kinetics effect on thermo-mechanical properties of an epoxy resin cured by imidazolium-based ionic liquid,” Iranian Polymer Journal, pp. 1-16, 2024.
[42] Yu, X. Y., Naito, K., Kang, C., Qu, X.W. and Zhang, Q. X., “Synthesis and properties of a high‐temperature naphthyl‐based phthalonitrile polymer,” Macromolecular Chemistry and Physics, Vol. 214, pp. 361-369, 2013.
[43] Pavia, D. L., Lampman, G. M., Kriz, G. S. and Vyvyan, J. A., “Introduction to spectroscopy,” Cengage learning, 2014.
[44] Augustine, D., Mathew, D. and Nair, C. R., “Phenol‐containing phthalonitrile polymers–synthesis, cure characteristics and laminate properties,” Polymer international, Vol. 62, pp. 1068-1076, 2013.
[45] Augustine, D., Mathew, D. and Reghunadhan Nair, C., “End‐functionalized thermoplastic‐toughened phthalonitrile composites: influence on cure reaction and mechanical and thermal properties,” Polymer International, Vol. 64, pp. 146-153, 2015.
[46] Yang, X., “Understanding the Thermal Degradation Mechanism of High-Temperature-Resistant Phthalonitrile Foam at Macroscopic and Molecular Levels,” Polymers, Vol. 15, pp. 3947, 2023.
[47] Liang B., “TG-MS-FTIR study on pyrolysis behavior of phthalonitrile resin,” Polymer Degradation and Stability, Vol. 169, pp. 108954, 2019.