Sustainable design of vanillin-based vitrimers using vinylogous urethane chemistry

Abstract

Research on bio-based covalent adaptable networks is popular nowadays in the search for an optimal implementation of thermoset materials and composites in a circular context. Herein, a vanillin derivative is...

Vitrimeric Epoxy-Amine Polyimine Networks Based on a Renewable Vanillin Derivative

“…Methods. 1 H NMR and 13 C NMR spectra were recorded on a Varian VNMR-S400 NMR spectrometer. DMSO-d 6 was used as a solvent.…”

“…1 H NMR (DMSO-d 6 , δ in ppm): 9.72 (s, 2H), 8.48 (s, 2H), 7.52 (d, 2H), 7.33 (dd, 2H), 7.28 (dd, 4H), 7.05 (dd, 4H), 6.89 (d, 2H), 3.85 (s, 6H). 13…”

“…In them, the bond exchange is produced in a concerted way, without any intermediate state, without losing the network integrity and always keeping the cross-linking density constant . Many organic reactions have been studied as a potential dynamic process in vitrimers such as transesterification, − disulfide metathesis, − transamination of vinylogous urethanes, , trans -thiocarbamoylation, , and imine exchange, − among others.…”

One-shot transformation of ordinary polyesters into vitrimers: decomposition-triggered cross-linking and assistance of dynamic covalent bonds

“…11,12 In addition to reprocessability, vitrimers can exhibit various useful functions, such as recyclability, healability, and strong adhesion. [13][14][15] In the most recent situation, the vitrimer concept has been applied to bio-based materials [16][17][18][19] and advanced technology, such as 3D printers, 20,21 strain sensors, 22 and functional coatings. 23 So far, versatile vitrimer designs with different polymer species and compatible bond exchange mechanisms have been reported.…”

Biobased, Creep-Resistant Covalent Adaptable Networks Based on β-Amino Ester Chemistry

“…As described above, the development of recyclable and reprocessable covalently cross-linked networks and the construction of polymers from renewable resources are both stimulated by the economic and environmental problems associated with traditional thermoset materials. Consequently, efforts to combine these two strategies in material design for sustainable thermosets were already carried out with a focus on epoxy matrices and accessible transamination-based chemistry systems. , A comprehensive overview of the state-of-the-art in combining reprocessable and renewable research strategies in the area of CANs is described in a recent review by Avérous and co-workers . Although several biobased CANs have been reported recently, it should be noted that these materials are often only partially biobased or involve (multi)­step derivatization of bioderived raw materials into functional building blocks, decreasing the overall sustainability.…”