Exploiting β-amino ester chemistry to obtain methacrylate-based covalent adaptable networks

Ivaldi, Chiara; Laguzzi, Erica; Ospina, Viviana Maria; Antonioli, Diego; Chiarcos, Riccardo; Campo, Federica; Cuminetti, Nicola; De Buck, Janosc; Laus, Michele

doi:10.1016/j.polymer.2023.126636

Cited by 1 publication

(2 citation statements)

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“…In this context, it should be mentioned that the reversible aza-Michael reaction also plays a significant role in the self-healing mechanism. , As our CANs have been constructed using disulfide linkages and aza-Michael bonds, we may consider that the self-healing nature of our CAN films is not only due to the disulfide bond exchange but also due to the contribution of the reversible aza-Michael reaction. However, the reversible aza-Michael reaction generally occurs at high temperatures. , As we have used a maximum temperature of 120 °C, we may expect a negligible contribution of the reversible aza-Michael reaction during the self-healing process of our prepared CAN films.…”

Section: Resultsmentioning

confidence: 99%

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Fully Biobased Self-Healing and Recyclable Covalent Adaptable Networks Prepared via a Catalyst-Free Aza-Michael Reaction

Kashyap,

Borah,

Shivam Shailesh Kumar

et al. 2024

ACS Appl. Polym. Mater.

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In the present scenario, petroleum resource-based thermoset materials have become an environmental threat due to their permanent cross-linked structure that limits their recyclability. To overcome this problem, the development of covalent adaptable networks (CANs) containing dynamic covalent bonds has emerged in recent years that can be recycled under suitable conditions. However, the development of fully biobased as well as recyclable CANs following a green synthetic protocol is yet a great challenge and a dream toward a sustainable environment. With this goal, here, we report the development of fully biobased CAN films from acrylated castor oil (a low-cost vegetable oil derivative) and cystamine (a biobased diamine) via a catalyst-free aza-Michael reaction using disulfide linkage as the dynamic covalent bond. The CAN films show excellent thermoself-healing behavior and recyclability for at least 10 cycles while maintaining their material properties. In addition, the CAN films can be catalytically degraded, which can be further reprocessed to reconstruct the films. Furthermore, the CAN films are hydrophobic in nature, indicating that these biobased recyclable CAN films are useful for protective surface coating applications. Therefore, as a proof of concept, we further demonstrate the anticorrosive properties of a film having a maximum water contact angle of 102.4°, analyzed by a polarization method, electrochemical impedance, and a salt spray fog test under a corrosive environment. This work provides an economical as well as environmentally friendly route to develop multifunctional materials for a sustainable future.

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Section: Resultsmentioning

confidence: 99%

“…However, the reversible aza-Michael reaction generally occurs at high temperatures. 7,49 As we have used a maximum temperature of 120 °C, we may expect a negligible contribution of the reversible aza-Michael reaction during the self-healing process of our prepared CAN films.…”

Section: Swelling and Gel Content Studiesmentioning

confidence: 99%