Tailoring vinylogous urethane chemistry for the cross-linked polybutadiene: Wide freedom design, multiple recycling methods, good shape memory behavior

Li, Yong; Zhang, Changxu; Shi, Zixing; Yin, Jie; Tian, Ming

doi:10.1016/j.polymer.2018.06.042

Cited by 56 publications

(36 citation statements)

References 42 publications

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“…For that purpose, the transamination of vinylogous urethanes (VU), a relatively well-studied vitrimer chemistry both within and beyond our own research group, was selected as dynamic exchange reaction platform (Figure 1A). 5,[30][31][32][33][34][35][36] Additionally, in order to investigate the effects of the crosslinking density (interpreted as concentration), different molecular weights of macromolecular monomers were studied. Conveniently, the different polymer matrices could be obtained starting from a wide range of commercially available diols (Figure 1C, right panel) and a commercially available trifunctional amine.…”

Section: Introductionmentioning

confidence: 99%

Influence of the polymer matrix on the viscoelastic behaviour of vitrimers

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Influence of the polymer matrix on the viscoelastic behaviour of vitrimers

et al. 2020

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“…an addition/elimination pathway), meaning that first a new covalent bond needs to be formed before an already existing one can be broken. 4 Since their discovery in 2011, a wide variety of chemistries have been investigated for this purpose ranging from transesterification, [10][11][12][13][14][15][16][17][18][19] transalkylation of trialkylsulfonium salts, 20 boronic ester transesterification [21][22][23][24][25] to the vinylogous urethane transamination [26][27][28][29][30][31][32][33][34][35][36] and many more. [37][38][39][40][41][42][43][44] The vinylogous urethane (VU) chemistry was first introduced in vitrimer materials by our research group in 2015.…”

Section: Introductionmentioning

confidence: 99%

Polyaddition Synthesis Using Alkyne Esters for the Design of Vinylogous Urethane Vitrimers

et al. 2021

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Vitrimers are a subclass of covalent adaptable networks, which introduce reshapeability and recyclability in thermoset materials while maintaining a high degree of chemical resistance and dimensional stability. Vitrimer materials based on vinylogous urethane (VU) chemistry have drawn a lot of attention in this area. Classically, these are obtained by the polycondensation polymerization of acetoacetate and amine monomers. Unfortunately, this also releases water, often leading to porosity defects in the initially obtained non-reprocessed crosslinked materials. Here, we demonstrate that alkyne esters (AE) can be used as alternative building blocks for VU vitrimers by a polyaddition polymerization with amines, leading to water-free formulations and straightforward access to defect-free cured VU vitrimer materials.The bond formation and dynamic bond exchange was also studied by small molecule reactions, further rationalized by a computational (DFT) approach. The resulting water-free VU vitrimers display similar material properties compared to vitrimers based on acetoacetates, although also some differences are seen, which can be related to a minor amide-bond forming side reaction. Furthermore, using this novel AE approach, polyaddition curing of VU epoxy vitrimers can easily be prepared in a one-pot three-component method, combining AE, amine and epoxy monomers. This study shows that AE monomers can be used as an easy drop-in method to obtain processable epoxy materials with tunable viscoelastic properties, where the viscous flow behavior can in principle be fully tuned by varying the monomers' ratios and compositions.

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“…1). In fact, vinylogous urethanes are most commonly used for undergoing associative transamin-ation reactions to achieve fast processing, 27 reprocessability, 28 and multiple recycling 29 properties at a very high heat. However, in our study, this structure was used to synthesize a novel curing agent through this reaction to provide a basis for a toughened network instead of to provide dynamic performance.…”

Section: Polymer Chemistrymentioning

confidence: 99%