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gnin-based covalent adaptable networks (CANs): a potential
substitute for thermosets made of fossil fuels
Benedetto Tiz Davide ¹*, Vicente Filipa A.¹, Likozar Blaž ¹
1 Department of Catalysis and Chemical Reaction Engineering, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia,
Davide.Benedetto.Tiz@ki.si
* Corresponding author
Thermoset polymers offer high strength and durability; however, they display limited recyclability. In contrast,
thermoplastics are more flexible and have greater recyclability, but they may lack strength and durability.
Petroleum-based polymers are no longer acceptable given our current environmental crisis. Their main drawback
is not only their non-renewable character, but most importantly the detrimental impacts that their extraction
and processing have on the environment, including air and water pollution, habitat destruction, and climate
change. Thus, covalent adaptable networks (CANs) emerged as an interesting approach to develop reprocessable
thermosets (Kloxin et al., 2013). The combination of covalent and non-covalent bonds in CANs provides several
advantages. Covalent bonds provide strength and stability to the network structure, while non-covalent bonds
allow for dynamic, reversible changes in the network's properties. Using lignin and its building blocks to develop
bio-based CANs is an attractive option due to the lignin’s renewable and abundant character (Zhao et al., 2022).
This work focuses on the use of vanillin and syringaldehyde (two lignin derivatives) to develop lignin-based CANs.
The diversity of this work relies on the fact that imine (Lei et al., 2021) and acyl hydrazone bonds are built on
vanillin structure and incorporated in the final structure of thermosets, allowing its recyclability at the end of its
life.
Keywords: lignin, bio-based materials, vanillin, reversible bonds
Acknowledgment: The authors gratefully acknowledge receiving funding from Österreichische
Forschungsförderungsgesellschaft FFG within the THINK.WOOD.Innovation.Kooperative F&E Projekte program
[FFG-Nr. 893366], and financial as well as cooperative support from a wide range of industrial partners.
REFERENCES
Kloxin, C.J.; Bowman, C.N., 2013. Covalent Adaptable Networks: Smart, Reconfigurable and Responsive
Network Systems. Chem. Soc. Rev., 42, 7161–7173, doi:10.1039/C3CS60046G.
Zhao, X.-L.; Tian, P.-X.; Li, Y.-D.; Zeng, J.-B. 2022. Biobased Covalent Adaptable Networks: Towards Better
Sustainability of Thermosets. Green Chem., 24, 4363–4387, doi:10.1039/D2GC01325H.
Lei, Y.; Zhang, A.; Lin, Y., 2021. Interpenetrating covalent adaptable networks with enhanced mechanical
properties and facile reprocessability and recyclability. Polym. Chem., 12, 4052–4062, doi:10.1039/
D1PY00623A.
6 13–14 SEPTEMBER 2023 I IZOLA, SLOVENIA
substitute for thermosets made of fossil fuels
Benedetto Tiz Davide ¹*, Vicente Filipa A.¹, Likozar Blaž ¹
1 Department of Catalysis and Chemical Reaction Engineering, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia,
Davide.Benedetto.Tiz@ki.si
* Corresponding author
Thermoset polymers offer high strength and durability; however, they display limited recyclability. In contrast,
thermoplastics are more flexible and have greater recyclability, but they may lack strength and durability.
Petroleum-based polymers are no longer acceptable given our current environmental crisis. Their main drawback
is not only their non-renewable character, but most importantly the detrimental impacts that their extraction
and processing have on the environment, including air and water pollution, habitat destruction, and climate
change. Thus, covalent adaptable networks (CANs) emerged as an interesting approach to develop reprocessable
thermosets (Kloxin et al., 2013). The combination of covalent and non-covalent bonds in CANs provides several
advantages. Covalent bonds provide strength and stability to the network structure, while non-covalent bonds
allow for dynamic, reversible changes in the network's properties. Using lignin and its building blocks to develop
bio-based CANs is an attractive option due to the lignin’s renewable and abundant character (Zhao et al., 2022).
This work focuses on the use of vanillin and syringaldehyde (two lignin derivatives) to develop lignin-based CANs.
The diversity of this work relies on the fact that imine (Lei et al., 2021) and acyl hydrazone bonds are built on
vanillin structure and incorporated in the final structure of thermosets, allowing its recyclability at the end of its
life.
Keywords: lignin, bio-based materials, vanillin, reversible bonds
Acknowledgment: The authors gratefully acknowledge receiving funding from Österreichische
Forschungsförderungsgesellschaft FFG within the THINK.WOOD.Innovation.Kooperative F&E Projekte program
[FFG-Nr. 893366], and financial as well as cooperative support from a wide range of industrial partners.
REFERENCES
Kloxin, C.J.; Bowman, C.N., 2013. Covalent Adaptable Networks: Smart, Reconfigurable and Responsive
Network Systems. Chem. Soc. Rev., 42, 7161–7173, doi:10.1039/C3CS60046G.
Zhao, X.-L.; Tian, P.-X.; Li, Y.-D.; Zeng, J.-B. 2022. Biobased Covalent Adaptable Networks: Towards Better
Sustainability of Thermosets. Green Chem., 24, 4363–4387, doi:10.1039/D2GC01325H.
Lei, Y.; Zhang, A.; Lin, Y., 2021. Interpenetrating covalent adaptable networks with enhanced mechanical
properties and facile reprocessability and recyclability. Polym. Chem., 12, 4052–4062, doi:10.1039/
D1PY00623A.
6 13–14 SEPTEMBER 2023 I IZOLA, SLOVENIA
