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Polyaddition synthesis using alkyne esters for the design of vinylogous urethane vitrimers

Yann Spiesschaert, Jens Danneels, Niels Van Herck, Marc Guerre, Guillaume Acke (UGent) , Johan Winne (UGent) and Filip Du Prez (UGent)
(2021) MACROMOLECULES. 54(17). p.7931-7942
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Abstract
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 cross-linked 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, by use of 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.
Keywords
COVALENT ADAPTABLE NETWORKS, POLYMER NETWORKS, TRANSESTERIFICATION, CHEMISTRY, TEMPERATURE, POTENT

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Citation

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MLA
Spiesschaert, Yann, et al. “Polyaddition Synthesis Using Alkyne Esters for the Design of Vinylogous Urethane Vitrimers.” MACROMOLECULES, vol. 54, no. 17, 2021, pp. 7931–42, doi:10.1021/acs.macromol.1c01049.
APA
Spiesschaert, Y., Danneels, J., Van Herck, N., Guerre, M., Acke, G., Winne, J., & Du Prez, F. (2021). Polyaddition synthesis using alkyne esters for the design of vinylogous urethane vitrimers. MACROMOLECULES, 54(17), 7931–7942. https://doi.org/10.1021/acs.macromol.1c01049
Chicago author-date
Spiesschaert, Yann, Jens Danneels, Niels Van Herck, Marc Guerre, Guillaume Acke, Johan Winne, and Filip Du Prez. 2021. “Polyaddition Synthesis Using Alkyne Esters for the Design of Vinylogous Urethane Vitrimers.” MACROMOLECULES 54 (17): 7931–42. https://doi.org/10.1021/acs.macromol.1c01049.
Chicago author-date (all authors)
Spiesschaert, Yann, Jens Danneels, Niels Van Herck, Marc Guerre, Guillaume Acke, Johan Winne, and Filip Du Prez. 2021. “Polyaddition Synthesis Using Alkyne Esters for the Design of Vinylogous Urethane Vitrimers.” MACROMOLECULES 54 (17): 7931–7942. doi:10.1021/acs.macromol.1c01049.
Vancouver
1.
Spiesschaert Y, Danneels J, Van Herck N, Guerre M, Acke G, Winne J, et al. Polyaddition synthesis using alkyne esters for the design of vinylogous urethane vitrimers. MACROMOLECULES. 2021;54(17):7931–42.
IEEE
[1]
Y. Spiesschaert et al., “Polyaddition synthesis using alkyne esters for the design of vinylogous urethane vitrimers,” MACROMOLECULES, vol. 54, no. 17, pp. 7931–7942, 2021.
@article{8738967,
  abstract     = {{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 cross-linked 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, by use of 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.}},
  author       = {{Spiesschaert, Yann and Danneels, Jens and Van Herck, Niels and Guerre, Marc and Acke, Guillaume and Winne, Johan and Du Prez, Filip}},
  issn         = {{0024-9297}},
  journal      = {{MACROMOLECULES}},
  keywords     = {{COVALENT ADAPTABLE NETWORKS,POLYMER NETWORKS,TRANSESTERIFICATION,CHEMISTRY,TEMPERATURE,POTENT}},
  language     = {{eng}},
  number       = {{17}},
  pages        = {{7931--7942}},
  title        = {{Polyaddition synthesis using alkyne esters for the design of vinylogous urethane vitrimers}},
  url          = {{http://doi.org/10.1021/acs.macromol.1c01049}},
  volume       = {{54}},
  year         = {{2021}},
}
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