The Effect of Curing Cycle on Interlaminar Shear Strength and Thermal Properties of Carbon Fiber Composite of High Temperature Maleimide-containing Phthalonitrile Dual-curing Resin

Hassan Fattahi; Milad Hatami; Mohammad Reza Ehsani; Mehrzad Mortezaei

doi:10.1007/s10118-026-3798-z

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The Effect of Curing Cycle on Interlaminar Shear Strength and Thermal Properties of Carbon Fiber Composite of High Temperature Maleimide-containing Phthalonitrile Dual-curing Resin

RESEARCH ARTICLE | Updated：2026-08-28

- The Effect of Curing Cycle on Interlaminar Shear Strength and Thermal Properties of Carbon Fiber Composite of High Temperature Maleimide-containing Phthalonitrile Dual-curing Resin
- The Effect of Curing Cycle on Interlaminar Shear Strength and Thermal Properties of Carbon Fiber Composite of High Temperature Maleimide-containing Phthalonitrile Dual-curing Resin
- Chinese Journal of Polymer Science 2026年44卷页码：1-14
- Affiliations：
  
  Department of Polymer Engineering, Composite Research Institute, Faculty of Materials and Manufacturing Technologies, Malek Ashtar University of ‎Technology, Tehran 1774-15875, Iran
- Author bio：
  
  fattahi@mut.ac.ir, hassan.fattahi@gmail.com
- Funds：
  
  The authors declare no interest conflict.The data are available from the corresponding author upon reasonable request.
- DOI：10.1007/s10118-026-3798-z
  中图分类号：
- 收稿：2026-05-17，
  
  录用：2026-06-30，
  
  网络首发：2026-08-28，
  
  纸质出版：2026-07
- Accepted：
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Fattahi, H.; Hatami, M.; Ehsani, M. R.; Mortezaei, M. The effect of curing cycle on interlaminar shear strength and thermal properties of carbon fiber composite of high temperature maleimide-containing phthalonitrile dual-curing resin. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-026-3798-z

Hassan Fattahi, Milad Hatami, Mohammad Reza Ehsani, et al. The Effect of Curing Cycle on Interlaminar Shear Strength and Thermal Properties of Carbon Fiber Composite of High Temperature Maleimide-containing Phthalonitrile Dual-curing Resin[J/OL]. Chinese Journal of Polymer Science, 2026, 441-14.
Fattahi, H.; Hatami, M.; Ehsani, M. R.; Mortezaei, M. The effect of curing cycle on interlaminar shear strength and thermal properties of carbon fiber composite of high temperature maleimide-containing phthalonitrile dual-curing resin. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-026-3798-z DOI：

Hassan Fattahi, Milad Hatami, Mohammad Reza Ehsani, et al. The Effect of Curing Cycle on Interlaminar Shear Strength and Thermal Properties of Carbon Fiber Composite of High Temperature Maleimide-containing Phthalonitrile Dual-curing Resin[J/OL]. Chinese Journal of Polymer Science, 2026, 441-14. DOI： 10.1007/s10118-026-3798-z.

摘要

Abstract

In this study

a phthalonitrile monomer containing a maleimide group (MPN) with a melting point of 106.8 °C was successfully synthesized. Differential scanning calorimetry (DSC) showed that the MPN resin can act as an autocatalyzed resin without any curing agent. The monomer was then cured using diallyl bisphenol A (DABA) as the curing agent. Based on the results of FTIR analysis

a suitable curing cycle was established. Given the dual-stage curing behavior of the monomer

three composite samples were fabricated using three different curing cycles to investigate the relationship between the polymer structure and final properties. Interlaminar shear strength (ILSS) tests showed that samples with approximately 95% curing degree for the phthalonitrile part of this resin exhibited an ILSS of approximately 37.5 MPa. Dynamic mechanical thermal analysis (DMTA) confirmed the formation of a thermally stable and rigid crosslinked network in the synthesized composite. The storage modulus (

′) exhibited relatively high values even at incomplete curing stages

maintaining significant stiffness up to approximately 100 °C

which highlights the early formation of a semi-crosslinked structure. Thermogravimetric analysis (TGA) revealed that the fabricated composite had good thermal resistance with

and

10%

of 484 and 584 °C

respectively

with a char yield of 84% at 900

°C.

关键词

Keywords

references

Liu, J.; Wang, S.; Peng, Y.; Zhu, J.; Zhao, W.; Liu, X.Advances in sustainable thermosetting resins: from renewable feedstock to high performance and recyclability. Prog. Polym. Sci. 2021 , 113 , 101353..

[Huang, X.; Peng, S.; Zheng, L.; Zhuo, D.; Wu, L.; Weng, Z. 3D printing of high viscosity UV-curable resin for highly stretchable and resilient elastomer. Adv. Mater . 2023 , 35 , 2304430..

Sun, X.; Wang, S.; Dong, S.; Chen, X.; Dong, X.; Wang, Y.; Jian, X.; Liu, C. Synthesis and degradation mechanisms of Schiff-base-containing phthalonitrile resins: thermal stability and bond reconfiguration. Polym. Degrad. Stab. 2026 , 246 , 111945..

Gacal, B.; Cianga, L.; Agag, T.; Takeichi, T.; Yagci, Y. Synthesis and characterization of maleimide (co)polymers with pendant benzoxazine groups by photoinduced radical polymerization and their thermal curing. J. Polym. Sci. Part A: Polym. Chem. 2007 , 45 , 2774−2786..

Sirotin, I. S.; Sarychev, I. A.; Vorobyeva, V. V.; Kuzmich, A. A.; Bornosuz, N. V.; Onuchin, D. V.; Gorbunova, I. Y.; Kireev, V. V. Synthesis of phosphazene-containing, bisphenol A-based benzoxazines and properties of corresponding polybenzoxazines. Polymers 2020 , 12 , 1225..

Xu, M.; Lei, Y.; Ren, D.; Chen, L.; Li, K.; Liu, X. Thermal stability of allyl-functional phthalonitriles-containing benzoxazine/bismaleimide copolymers and their improved mechanical properties. Polymers 2018 , 10 , 596..

[Jahani, M.; Fatahi, H.; Mortezaeei, M. Effect of aromatic amine structure as a curing agent on molecular packing and mechanical properties of cured epoxy resin. Iran. J. Polym. Sci. Technol . 2019 , 32 , 267–276 (in Persian)..

Hajebi, S.; Payamani, M.; Fattahi, H.; Mortezaei, M.; Jalilolghadr, S. Dual-curing epoxy thermosets: Design, curing, properties and applications. Polym. Rev. 2025 , 65 , 250−280..

Pouladvand, A. R.; Mortezaei, M.; Fattahi, H.; Amiri Amraei, I. A novel custom-tailored epoxy prepreg formulation based on epoxy-amine dual-curable systems. Compos. Part A Appl. Sci. Manuf. 2020 , 132 , 105852..

Nechausov, S. S.; Bulgakov, B. A.; Solopchenko, A. V.; Serdan, A. A.; Kalugin, D. I.; Lyalin, A.; Kepman, A. V.; Malakho, A. P. Thermosetting matrices for composite materials based on allyl/propargyl substituted novolac resins. J. Polym. Res. 2016 , 23 , 114..

Augustine, D.; Mathew, D.; Nair, C. P. R. One component propargyl phthalonitrile novolac: synthesis and characterization. Eur. Polym. J. 2015 , 71 , 389−400..

Nechausov, S.; Bulgakov, B.; Kalugin, D.; Babkin, A.; Kepman, A.; Malakho, A.; Avdeev, V. Carbon fabric reinforced addition-cure phenolic resins based on propargyl and allyl ether functional novolac produced by vacuum infusion. Eurasian Chem.-Technol. J. 2020 , 22 , 99−106..

Bulgakov, B.; Babkin, A.; Makarenko, I.; Tikhonov, N.; Kalugin, D.; Kepman, A.; Malakho, A.; Avdeev, V. Ni(II) and Cu(II) based catalysts for propargylated novolac resins curing: Activity study and curing process simulation. Eur. Polym. J. 2015 , 73 , 247−258..

Dirlikov, S. K. Propargyl-terminated resins—a hydrophobic substitute for epoxy resins. High Perform. Polym. 1990 , 2 , 67−77..

Bulgakov, B.; Kalugin, D.; Babkin, A.; Makarenko, I.; Malakho, A.; Kepman, A.; Avdeev, V.; Garadja, N.; Rogozin, A. Propargylated novolac resins for fibre-reinforced plastics: processing aspects. Can. J. Chem. Eng. 2016 , 94 , 46−52..

[Hamerton, I. High-performance thermoset-thermoset polymer blends: A review of the chemistry of cyanate ester–bismaleimide blends. High Perform. Polym . 1996 , 8 , 83–95..

Bauer, J.; Bauer, M. Curing of cyanates with primary amines. Macromol. Chem. Phys. 2001 , 202 , 2213−2220..

Uhlig, C.; Kahle, O.; Schäfer, O.; Ewald, D.; Oswaldbauer, H.; Bauer, J.; Bauer, M. Blends of tri-block copolymers and addition curing resins: Influence of block copolymer–resin compatibility on toughness and matrix properties on toughenability. React. Funct. Polym. 2019 , 142 , 159−182..

[Ahmadi, M.; Fattahi, H.; Mortezaei, M.; Mirbagheri, S. M. J. High temperature cyanate ester/carbon fiber compos ite with high ILSS based on synthesized 2,2′-bis(4-cyanatophenyl) propane resin. J. Sci. Technol. Compos . 2024 , 11 , 2419–2428 (in Persian)..

Iredale, R. J.; Ward, C.; Hamerton, I. Modern advances in bismaleimide resin technology: a 21st century perspective on the chemistry of addition polyimides. Prog. Polym. Sci. 2017 , 69 , 1−21..

Dolci, E.; Froidevaux, V.; Joly-Duhamel, C.; Auvergne, R.; Boutevin, B.; Caillol, S. Maleimides as a building block for the synthesis of high performance polymers. Polym. Rev. 2016 , 56 , 512−556..

Evsyukov, S.; Klomp-de Boer, R.; Stenzenberger, H. D.; Pohlmann, T.; ter Wiel, M. A new m-xylylene bismaleimide-based high performance resin for vacuum-assisted infusion and resin transfer molding. J. Compos. Mater. 2019 , 53 , 3063−3072..

[Payamani, M.; Fattahi, H.; Mortezaei, M. Synthesis and characterization of 4,4′-bis(maleimido)diphenylmethane resin and evaluation of its curing behavior in blending with epoxy. Iran. J. Polym. Sci. Technol . 2022 , 35 , 339–352 (in Persian)..

Keller, T. M. Phthalonitrile-based high temperature resin. J. Polym. Sci. Part A: Polym. Chem. 1988 , 26 , 3199−3212..

Keller, T. M. Synthesis and polymerization of multiple aromatic ether phthalonitriles. Chem. Mater. 1994 , 6 , 302−305..

Timoshkin, I. A.; Aleshkevich, V. V.; Afanas’eva, E. S.; Bulgakov, B. A.; Babkin, A. V.; Kepman, A. V.; Avdeev, V. V. Heat-resistant carbon fiber reinforced plastics based on a copolymer of bisphthalonitriles and bisbenzonitrile. Polym. Sci. Ser. C 2020 , 62 , 172−182..

Wang, G.; Han, Y.; Guo, Y.; Sun, J.; Wang, S.; Zhou, H.; Zhao, T. Phthalonitrile terminated fluorene based copolymer with outstanding thermal and mechanical properties. Eur. Polym. J. 2019 , 113 , 1−11..

Ye, J.; Li, Q.; Zhang, S.; Liu, X. Melamine modified phthalonitrile resins: Synthesis, polymerization and properties. Polymer 2022 , 256 , 125156..

Chen, M.; He, X.; Lv, J.; Tan, W.; Wang, Y.; Hu, J.; Zeng, K.; Yang, G. A new bio-based thermosetting with amorphous state, sub-zero softening point and high curing efficiency. Polymer 2023 , 264 , 125518..

Ma, A.; Rong, J.; Li, D.; Chen, X.; Yu, X.; Zhang, Q. Thermal stability and curing mechanism of self-catalytic bio-based phthalonitrile resins. Polymer 2025 , 336 , 128916..

Xu, F.; Sha, Z.; Zhuo, L.; Chang, W.; Sun, B.; Wang, C. H.; Gu, B.; Zhang, J. Improving thermal stability and mechanical properties of high temperature carbon fibre phthalonitrile resin composites via nano-CuO modified matrices. Compos. Part A Appl. Sci. Manuf. 2025 , 197 , 109035..

Li, Q.; Zhang, S.; Ye, J.; Liu, X. Multiple catalytic polymerization of phthalonitrile resin bearing benzoxazine moiety: greatly reduced curing temperature. Eur. Polym. J. 2022 , 180 , 111472..

Lv, J.; Hong, J.; Liang, B.; Zhao, E.; Zeng, K.; Chen, M.; Hu, J.; Yang, G. Study of the curing kinetics of melamine/phthalonitrile resin system. Thermochim. Acta 2020 , 683 , 178442..

Gao, C.; Gu, H.; Du, A.; Zhou, H.; Pan, D.; Naik, N.; Guo, Z. Polyaniline facilitated curing of phthalonitrile resin with enhanced processibility and mechanical property. Polymer 2021 , 219 , 123533..

Sastri, S. B.; Keller, T. M. Phthalonitrile cure reaction with aromatic diamines. J. Polym. Sci. Part A Polym. Chem. 1998 , 36 , 1885−1890..

Badshah, A.; Kessler, M. R.; Heng, Z.; Hasan, A. Synthesis and characterization of phthalonitrile resins from ortho-linked aromatic and heterocyclic monomers. Polym. Int. 2014 , 63 , 465−469..

Laskoski, M.; Neal, A.; Schear, M. B.; Keller, T. M.; Ricks-Laskoski, H. L.; Saab, A. P. Oligomeric aliphatic–aromatic ether containing phthalonitrile resins. J. Polym. Sci. Part A Polym. Chem. 2015 , 53 , 2186−2191..

Zeng, K.; Hong, H.; Zhou, S.; Wu, D.; Miao, P.; Huang, Z.; Yang, G. A new soluble aramide with pendant phthalonitrile units and polymer property enhancement by nitrile cure reactions. Polymer 2009 , 50 , 5002−5006..

Kirmani, M. H.; Ramachandran, J.; Arias-Monje, P. J.; Gulgunje, P.; Kumar, S. The effects of processing and carbon nanotube type on the impact strength of aerospace-grade bismaleimide based nanocomposites. Polym. Eng. Sci. 2022 , 62 , 1187−1196..

Lan, K.; Deng, Y.; Huang, A.; Li, S. Q.; Liu, G.; Xie, H. L. Highly-performance polyimide as an efficient photothermal material for solar-driven water evaporation. Polymer 2022 , 256 , 125177..

Jiao, Y.; Yuan, L.; Liang, G.; Gu, A. Dispersing carbon nanotubes in the unfavorable phase of an immiscible reverse-phase blend with Haake instrument to fabricate high-k nanocomposites with extremely low dielectric loss and percolation threshold. Chem. Eng. J. 2016 , 285 , 650−659..

Lyu, J.; Ji, B.; Wu, N.; Liao, W.; Yin, C.; Bai, S.; Xing, S. The effect of substituent group in allyl benzoxazine on the thermal, mechanical and dielectric properties of modified bismaleimide. React. Funct. Polym. 2023 , 191 , 105673..

Xie, H.; Chen, S.; Qu, B.; Liu, X.; Li, W.; Wang, R.; Hou, L.; Zhuo, D. Preparation of silicone-bismaleimide photosensitiveresin and its application in 3D printing. J. Sci. Adv. Mater. Devices 2026 , 11 , 101099..

Jiang, M.; Xu, M.; Jia, K.; Liu, X. Copolymerization of self-catalyzed phthalonitrile with bismaleimide toward high-temperature-resistant polymers with improved processability. High Perform. Polym. 2016 , 28 , 895−907..

Zhang, B.; Liu, F.; Chen, S.; Huang, L.; Zhong, Y.; Fan, W.; Li, J. Fluorine bismaleimide resin with outstanding piezoelectric characteristics for structure-function integrated composites. Chem. Eng. J. 2025 , 503 , 158506..

Zhu, X.; Yin, S.; Liu, L.; Yi, W.; Luo, G.; Zhao, Z.; Chen, W. Effects of temperature on mechanical properties and impact resistance of carbon fiber/bismaleimide resin composites. J. Mater. Res. Technol. 2025 , 34 , 2553−2569..

Kaliavaradhan, K.; Muthusamy, S. Synthesis and characterization of various phenylene diamine-based bismaleimide-containing phthalonitrile resins. Polym. Bull. 2016 , 73 , 1921−1938..

Nechausov, S. S.; Aleksanova, A. A.; Morozov, O. S.; Bulgakov, B. A.; Babkin, A. V.; Kepman, A. V. Low-melting phthalonitrile monomers containing maleimide group: synthesis, dual-c uring behavior, thermal and mechanical properties. React. Funct. Polym. 2021 , 164 , 104932..

[ASTM: D2344/D2344M-00e1. Standard test method for short-beam strength of polymer matrix composite materials and their laminates.

[Liu, Z.; Liu, Y.; Peng, W.; Lu, Z.; Liang, B.; Liu, Y.; Li, C.; Hu, J.; Zeng, K.; Yang, G. New model phthalonitrile resin system based on self-promoted curing reaction for exploring the mechanism of radical promoted-polymerization effect. J. Appl. Polym. Sci. 2019 , 136 , 48134.

Torrecillas, R.; Regnier, N.; Mortaigne, B. Thermal degradation of bismaleimide and bisnadimide networks—products of thermal degradation and type of crosslinking points. Polym. Degrad. Stab. 1996 , 51 , 307−318..

Liu, C.; Li, S.; Yuan, Z.; Xue, S.; Sun, M.; Zhang, X.; Li, J.; Xue, G.; Bai, X.; Liu, W.; Zhang, B. Low-melting maleimide-containing phthalonitrile resins: synthesis, curing behavior, and thermal performance. Polymer 2024 , 315 , 127821..

Xu, M.; Ren, D.; Chen, L.; Li, K.; Liu, X. Understanding of the polymerization mechanism of the phthalonitrile-based resins containing benzoxazine and their thermal stability. Polymer 2018 , 143 , 28−39..

Wang, G.; Guo, Y.; Han, Y.; Li, Z.; Ding, J.; Jiang, H.; Zhou, H.; Zhao, T. Enhanced properties of phthalonitrile resins reinforced by novel phthalonitrile-terminated polyaryl ether nitrile containing fluorene group. High Perform. Polym. 2020 , 32 , 3−11..

Wu, Z.; Wang, S.; Zong, L.; Li, N.; Wang, J.; Jian, X. Novel phthalonitrile-based composites with excellent processing, thermal, and mechanical properties. High Perform. Polym. 2018 , 30 , 720−730..

Hu, J.; Hu, Y.; Deng, S. F.; Zhou, J. L.; Jiang, N.; Zhu, Y.; Sun, M. Synthesis and properties of a novel silicon-containing phthalonitrile resin and its quartz-fiber-reinforced composites. High Perform. Polym. 2020 , 32 , 1112−1121..

Poliakova, D. I.; Morozov, O. S.; Nechausov, S. S.; Afanaseva, E. A.; Bulgakov, B. A.; Babkin, A. V.; Kepman, A. V.; Avdeev, V. V. Fast curing phthalonitrile modified novolac resin: synthesis, curing study and preparation of carbon and glass fiber composites. React. Funct. Polym. 2022 , 181 , 105450..

[Mirbagheri, S. M. J.; Fattahi, H.; Mortezaei, M.; Ahmadi, M. The effect of amine and phenolic curing agents on curing temperature of high temperature phthalonitrile resin for preparation of high performance carbon/phthalonitrile composite. J. Sci. Technol. Compos . 2025 , 11 , 2569–2579 (in Persian)..

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