[en] In this work, we synthesized and investigated three fully biobased benzoxazine matrices containing exchangeable ester bonds for natural fiber composites. The thermoset properties were investigated and the transesterification behavior was assessed. The obtained polymers show high tunability. Using isosorbide as the starting building block, the thermoset exhibits a glass transition of 130 °C, a tensile modulus of 2.5 GPa, and thermal stability leading to degradation occurring after 270 °C with 31% char at 800 °C. All formulations stress relax under catalyst-free conditions within minutes with properties recovery superior to 80%. Finally, flax composites were manufactured. We highlight strong affinities between the matrices and the fibers through high mechanical performances with a modulus over 30 GPa and stress at break of 400 MPa in the longitudinal direction. 5 GPa modulus and 47 MPa stress at break were found in the transverse direction. Excellent fire retardancy properties, with self-extinguishment and UL-94 V1 classification were obtained for the isosorbide-based/flax composite. The obtained composites were able to be welded with comparable results to glued ones, paving the way to processable laminates and stable cured prepreg perfectly suited for transportation-engineered applications.
Disciplines :
Chemistry
Author, co-author :
Seychal, Guillem ; Université de Mons - UMONS > Faculté des Sciences > Service des Matériaux Polymères et Composites
Van Renterghem, Louis; Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons, Mons, Belgium
Ocando, Connie; Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons, Mons, Belgium
Bonnaud, Leila ; Université de Mons - UMONS > Unités externes > Materia Nova ASBL ; Materia Nova asbl, Parc Initialis, Mons, Belgium
Raquez, Jean-Marie ; Université de Mons - UMONS > Faculté des Sciences > Service des Matériaux Polymères et Composites
Language :
English
Title :
Towards sustainable reprocessable structural composites: Benzoxazines as biobased matrices for natural fibers
H2020 - 955700 - NIPU - SYNTHESIS, CHARACTERIZATION, STRUCTURE AND PROPERTIES OF NOVEL NONISOCYANATE POLYURETHANES
Funders :
Union Européenne
Funding text :
The authors wish to thank the Wallonia-Brussels Federation, Wallonia, and the European Community for general support in the frame of European Union's Horizon 2020 research and innovation program under the Marie Skłodowska-Curie grant agreement No. 955700 (NIPU-EJD project) and the Concerted Research Action program (ARC 2020 - PROCOMAG project). L.B. also want to thank the INTERREG V FWVL program (ATHENS project) and PIT AERO (WINGS project). JMR is a Senior FRS-FNRS Research Associate.The authors wish to thank the Wallonia-Brussels Federation, Wallonia, and the European Community for general support in the frame of European Union’s Horizon 2020 research and innovation program under the Marie Skłodowska-Curie grant agreement No. 955700 (NIPU-EJD project) and the Concerted Research Action program (ARC 2020 - PROCOMAG project). L.B. also want to thank the INTERREG V FWVL program (ATHENS project) and PIT AERO (WINGS project). JMR is a Senior FRS-FNRS Research Associate.
Machado, Irlaine, Shaer, Cecilia, Hurdle, Kalan, Calado, Veronica, Ishida, Hatsuo, Towards the development of green flame retardancy by polybenzoxazines. Prog Polym Sci, 121, 2021, 101435.
Ao, Xiang, Vázquez-López, Antonio, Mocerino, Davide, González, Carlos, Wang, De-Yi, Flame retardancy and fire mechanical properties for natural fiber/polymer composite: A review. Composites B, 268, 2024, 111069.
Shi, Xiao-Hui, Li, Xue-Lin, Li, Ying-Ming, Li, Zhi, Wang, De-Yi, Flame-retardant strategy and mechanism of fiber reinforced polymeric composite: A review. Composites B, 233, 2022, 109663.
Wei, Zhibiao, Ji, Chao, Yu, Tao, Li, Yan, Liu, Xiaoqing, The unique wick effect and combustion behavior of flax fiber reinforced composites: Experiment and simulation. Composites B, 265, 2023, 110954.
Perrin, Henri, Vaudemont, Régis, Del Frari, Doriane, Verge, Pierre, Puchot, Laura, Bodaghi, Masoud, On the cyclic delamination-healing capacity of vitrimer-based composite laminates. Composites A, 177, 2024, 107899.
Bonnaud, Leïla, Chollet, Benjamin, Dumas, Ludovic, Peru, Aurélien A.M., Flourat, Amandine L., Allais, Florent, Dubois, Philippe, High-performance bio-based benzoxazines from enzymatic synthesis of diphenols. Macromol Chem Phys, 220(1), 2019, 1800312.
Samyn, Fabienne, Murariu, Oltea, Bonnaud, Leila, Duquesne, Sophie, Preparation and flame retardancy of flax fabric/polybenzoxazine laminates. Fire Mater 45:3 (2021), 366–378.
Dumas, Ludovic, Bonnaud, Leïla, Olivier, Marjorie, Poorteman, Marc, Dubois, Philippe, High performance bio-based benzoxazine networks from resorcinol and hydroquinone. Eur Polym J 75 (2016), 486–494.
Wazeer, Adil, Das, Apurba, Abeykoon, Chamil, Sinha, Arijit, Karmakar, Amit, Composites for electric vehicles and automotive sector: A review. Green Energy Intell Transp, 2022, 100043.
Van, Amy, Chiou, Kevin, Ishida, Hatsuo, Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring. Polymer 55:6 (2014), 1443–1451.
Wen, Zhibin, Bonnaud, Leïla, Mincheva, Rosica, Dubois, Philippe, Raquez, Jean-Marie, Development of low-viscosity and high-performance biobased monobenzoxazine from tyrosol and furfurylamine. Materials, 14(2), 2021, 440.
Zhao, Wenqian, Hao, Boran, Lu, Yin, Zhang, Kan, Thermal latent and low-temperature polymerization of a bio-benzoxazine resin from natural renewable chrysin and furfurylamine. Eur Polym J, 166, 2022, 111041.
Ramdani, Noureddine, Derradji, Mehdi, Mokhnache, El Oualid, Natural fiber reinforced polybenzoxazine composites: A review. Mater Today Commun, 31, 2022, 103645.
Pisupati, Anurag, Bonnaud, Leila, Deléglise-Lagardère, Mylène, Park, Chung Hae, Influence of environmental conditions on the mechanical properties of flax fiber reinforced thermoset composites. Appl Compos Mater 28:3 (2021), 633–649.
Lyu, Ya, Ishida, Hatsuo, Natural-sourced benzoxazine resins, homopolymers, blends and composites: A review of their synthesis, manufacturing and applications. Prog Polym Sci, 99, 2019, 101168.
Liu, Xue, Liu, Jincong, Lei, Dengwei, Zhao, Guang-Rong, Modular metabolic engineering for production of phloretic acid, phloretin and phlorizin in Escherichia coli. Chem Eng Sci, 247, 2022, 116931.
Wang, Meng Wei, Jeng, Ru Jong, Lin, Ching Hsuan, Study on the ring-opening polymerization of benzoxazine through multisubstituted polybenzoxazine precursors. Macromolecules 48:3 (2015), 530–535.
Altuna, Facundo I., Hoppe, Cristina E., Williams, Roberto J.J., Epoxy vitrimers with a covalently bonded tertiary amine as catalyst of the transesterification reaction. Eur Polym J 113 (2019), 297–304.
Lim, Jacob Song Kiat, Gan, Chee Lip, Hu, Xiao Matthew, Unraveling the mechanistic origins of epoxy degradation in acids. ACS Omega 4:6 (2019), 10799–10808.
Cadu, Thomas, Berges, Michael, Sicot, Olivier, Person, Véronique, Piezel, Benoit, Van Schoors, Laetitia, et al. What are the key parameters to produce a high-grade bio-based composite? Application to flax/epoxy UD laminates produced by thermocompression. Composites B 150 (2018), 36–46.
Le Gall, Maelenn, Davies, Peter, Martin, Nicolas, Baley, Christophe, Recommended flax fibre density values for composite property predictions. Ind Crops Prod 114 (2018), 52–58.
Kudoh, Ryoichi, Sudo, Atsushi, Endo, Takeshi, A highly reactive benzoxazine monomer, 1-(2-hydroxyethyl)-1,3-benzoxazine: Activation of benzoxazine by neighboring group participation of hydroxyl group. Macromolecules 43:3 (2010), 1185–1187.
Kiskan, Baris, Koz, Banu, Yagci, Yusuf, Synthesis and characterization of fluid 1,3-benzoxazine monomers and their thermally activated curing. J Polym Sci A 47:24 (2009), 6955–6961.
Advani, S.G., Hsiao, K.-T., 1 - Introduction to composites and manufacturing processes. Advani, Suresh G., Hsiao, Kuang-Ting, (eds.) Manufacturing techniques for polymer matrix composites Woodhead publishing series in composites science and engineering, 2012, Woodhead Publishing, 1–12.
Shah, Darshil U., Developing plant fibre composites for structural applications by optimising composite parameters: A critical review. J Mater Sci 48:18 (2013), 6083–6107.
Liu, Yuqi, Yuan, Li, Liang, Guozheng, Gu, Aijuan, Developing thermally resistant and strong biobased resin from benzoxazine synthesized using green solvents. Eur Polym J, 173, 2022, 111320.
Yee Low, Hong, Ishida, Hatsuo, Structural effects of phenols on the thermal and thermo-oxidative degradation of polybenzoxazines. Polymer 40:15 (1999), 4365–4376.
Adjaoud, Antoine, Trejo-Machin, Acerina, Puchot, Laura, Verge, Pierre, Polybenzoxazines: A sustainable platform for the design of fast responsive and catalyst-free vitrimers based on trans-esterification exchanges. Polym Chem 12:22 (2021), 3276–3289.
Jeannin, Thomas, Gabrion, Xavier, Ramasso, Emmanuel, Placet, Vincent, About the fatigue endurance of unidirectional flax-epoxy composite laminates. Composites B 165 (2019), 690–701.
Allagui, Sami, Mahi, Abderrahim, Rebiere, Jean-Luc, Beyaoui, Moez, Bouguecha, Anas, Haddar, Mohamed, Effect of recycling cycles on the mechanical and damping properties of flax fibre reinforced elium composite: Experimental and numerical studies. J. Renewable Materials 9:4 (2021), 695–721 Publisher: Tech Science Press.
Witthayolankowit, Kuntawit, Rakkijakan, Thanya, Ayub, Rabia, Kumaniaev, Ivan, Pourchet, Sylvie, Boni, Gilles, et al. Use of a fully biobased and non-reprotoxic epoxy polymer and woven hemp fabric to prepare environmentally friendly composite materials with excellent physical properties. Composites B, 258, 2023, 110692.
Trejo-Machin, Acerina, Puchot, Laura, Verge, Pierre, A cardanol-based polybenzoxazine vitrimer: Recycling, reshaping and reversible adhesion. Polym Chem 11:44 (2020), 7026–7034.
Di Mauro, Chiara, Malburet, Samuel, Graillot, Alain, Mija, Alice, Recyclable, repairable, and reshapable (3R) thermoset materials with shape memory properties from bio-based epoxidized vegetable oils. ACS Appl Bio Mater 3:11 (2020), 8094–8104.
Memon, Hafeezullah, Liu, Haiyang, Rashid, Muhammad A., Chen, Li, Jiang, Qiuran, Zhang, Liying, et al. Vanillin-based epoxy vitrimer with high performance and closed-loop recyclability. Macromolecules 53:2 (2020), 621–630.
Krishnakumar, Balaji, Sanka, R.V.S. Prasanna, Binder, Wolfgang H., Parthasarthy, Vijay, Rana, Sravendra, Karak, Niranjan, Vitrimers: Associative dynamic covalent adaptive networks in thermoset polymers. Chem Eng J, 385, 2020, 123820.
Pickering, K.L., Efendy, M.G. Aruan, Le, T.M., A review of recent developments in natural fibre composites and their mechanical performance. Composites A 83 (2016), 98–112.
Madsen, Bo, Thygesen, Anders, Lilholt, Hans, Plant fibre composites – Porosity and stiffness. Compos Sci Technol 69:7–8 (2009), 1057–1069.
Hallak Panzera, Tulio, Jeannin, Thomas, Gabrion, Xavier, Placet, Vincent, Remillat, Chrystel, Farrow, Ian, et al. Static, fatigue and impact behaviour of an autoclaved flax fibre reinforced composite for aerospace engineering. Composites B, 197, 2020, 108049.
Seychal, Guillem, Ramasso, Emmanuel, Le Moal, Patrice, Bourbon, Gilles, Gabrion, Xavier, Placet, Vincent, Towards in-situ acoustic emission-based health monitoring in bio-based composites structures: Does embedment of sensors affect the mechanical behaviour of flax/epoxy laminates?. Composites B, 2022, 109787.
Zhandarov, Serge, Mäder, Edith, Characterization of fiber/matrix interface strength: Applicability of different tests, approaches and parameters. Compos Sci Technol 65:1 (2005), 149–160.
Liang, Shaoxiong, Gning, Papa-Birame, Guillaumat, Laurent, Quasi-static behaviour and damage assessment of flax/epoxy composites. Mater Des 67 (2015), 344–353.
Baley, Christophe, Perrot, Yves, Busnel, Frederic, Guezenoc, Herve, Davies, Peter, Transverse tensile behaviour of unidirectional plies reinforced with flax fibres. Mater Lett, 2006, 4.
Saha, Prosenjit, Manna, Suvendu, Sen, Ramkrishna, Roy, Debasis, Adhikari, Basudam, Durability of lignocellulosic fibers treated with vegetable oil–phenolic resin. Carbohydr Polymers 87:2 (2012), 1628–1636.
Saba, N., Jawaid, M., Alothman, Othman Y., Paridah, M.T., A review on dynamic mechanical properties of natural fibre reinforced polymer composites. Constr Build Mater 106 (2016), 149–159.
Vinu Kumar, S M, Senthil Kumar, K L, Siddhi Jailani, H, Rajamurugan, G, Mechanical, DMA and sound acoustic behaviour of flax woven fabric reinforced epoxy composites. Mater Res Express, 7(8), 2020, 085302.
Kabir, M.M., Wang, H., Lau, K.T., Cardona, F., Chemical treatments on plant-based natural fibre reinforced polymer composites: An overview. Composites B 43:7 (2012), 2883–2892.
Mauldin, Timothy C., Zammarano, Mauro, Gilman, Jeffrey W., Shields, John R., Boday, Dylan J., Synthesis and characterization of isosorbide-based polyphosphonates as biobased flame-retardants. Polym Chem, 5(17), 2014, 5139.
Siniscalco, David, Arnould, Olivier, Bourmaud, Alain, Le Duigou, Antoine, Baley, Christophe, Monitoring temperature effects on flax cell-wall mechanical properties within a composite material using AFM. Polym Test 69 (2018), 91–99.
