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N-sulfonyl urethanes to design polyurethane networks with temperature-controlled dynamicity

Stephan Maes (UGent) , Filip Van Lysebetten, Johan Winne (UGent) and Filip Du Prez (UGent)
(2023) MACROMOLECULES. 56(5). p.1934-1944
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Abstract
(Re)processing of cross-linked polyurethanes (PUs) is often energy intensive and inefficient since dissociation of urethane linkages at elevated temperatures generates highly reactive isocyanate moieties that can react with a wide range of nucleophiles. In this study, we first show with a small molecule study that the introduction of N-sulfonyl urethane bonds leads to dynamic covalent exchange reactions under much milder conditions compared to regular urethane groups. Then, these exchangeable N-sulfonyl urethane motifs have been introduced, in relatively small amounts (5, 10, and 20%), in a cross-linked PU matrix in an attempt to facilitate plastic flow at lower temperatures. Rheological analysis of the elastomeric dissociative networks revealed an interesting double relaxation behavior, even for temperatures between 150 and 100 degrees C, which could be described by a Maxwell model with two elements, which can be related to the activated and less activated urethane bonds. Finally, the (re)processability of these sulfonyl urethanes containing PUs was demonstrated through multiple cutting and hot pressing cycles and the corresponding materials showed a good retention of thermal properties.
Keywords
BLOCKED ISOCYANATES-III, COVALENT CHEMISTRY, POLYMER NETWORKS, REVERSIBILITY, POLYESTER, VITRIMER, BEHAVIOR, AGENTS, BONDS, ACID

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MLA
Maes, Stephan, et al. “N-Sulfonyl Urethanes to Design Polyurethane Networks with Temperature-Controlled Dynamicity.” MACROMOLECULES, vol. 56, no. 5, 2023, pp. 1934–44, doi:10.1021/acs.macromol.2c02456.
APA
Maes, S., Van Lysebetten, F., Winne, J., & Du Prez, F. (2023). N-sulfonyl urethanes to design polyurethane networks with temperature-controlled dynamicity. MACROMOLECULES, 56(5), 1934–1944. https://doi.org/10.1021/acs.macromol.2c02456
Chicago author-date
Maes, Stephan, Filip Van Lysebetten, Johan Winne, and Filip Du Prez. 2023. “N-Sulfonyl Urethanes to Design Polyurethane Networks with Temperature-Controlled Dynamicity.” MACROMOLECULES 56 (5): 1934–44. https://doi.org/10.1021/acs.macromol.2c02456.
Chicago author-date (all authors)
Maes, Stephan, Filip Van Lysebetten, Johan Winne, and Filip Du Prez. 2023. “N-Sulfonyl Urethanes to Design Polyurethane Networks with Temperature-Controlled Dynamicity.” MACROMOLECULES 56 (5): 1934–1944. doi:10.1021/acs.macromol.2c02456.
Vancouver
1.
Maes S, Van Lysebetten F, Winne J, Du Prez F. N-sulfonyl urethanes to design polyurethane networks with temperature-controlled dynamicity. MACROMOLECULES. 2023;56(5):1934–44.
IEEE
[1]
S. Maes, F. Van Lysebetten, J. Winne, and F. Du Prez, “N-sulfonyl urethanes to design polyurethane networks with temperature-controlled dynamicity,” MACROMOLECULES, vol. 56, no. 5, pp. 1934–1944, 2023.
@article{01H2ASGRGDWC9MP9RHTSM6BY94,
  abstract     = {{(Re)processing of cross-linked polyurethanes (PUs) is often energy intensive and inefficient since dissociation of urethane linkages at elevated temperatures generates highly reactive isocyanate moieties that can react with a wide range of nucleophiles. In this study, we first show with a small molecule study that the introduction of N-sulfonyl urethane bonds leads to dynamic covalent exchange reactions under much milder conditions compared to regular urethane groups. Then, these exchangeable N-sulfonyl urethane motifs have been introduced, in relatively small amounts (5, 10, and 20%), in a cross-linked PU matrix in an attempt to facilitate plastic flow at lower temperatures. Rheological analysis of the elastomeric dissociative networks revealed an interesting double relaxation behavior, even for temperatures between 150 and 100 degrees C, which could be described by a Maxwell model with two elements, which can be related to the activated and less activated urethane bonds. Finally, the (re)processability of these sulfonyl urethanes containing PUs was demonstrated through multiple cutting and hot pressing cycles and the corresponding materials showed a good retention of thermal properties.}},
  author       = {{Maes, Stephan and Van Lysebetten, Filip and Winne, Johan and Du Prez, Filip}},
  issn         = {{0024-9297}},
  journal      = {{MACROMOLECULES}},
  keywords     = {{BLOCKED ISOCYANATES-III,COVALENT CHEMISTRY,POLYMER NETWORKS,REVERSIBILITY,POLYESTER,VITRIMER,BEHAVIOR,AGENTS,BONDS,ACID}},
  language     = {{eng}},
  number       = {{5}},
  pages        = {{1934--1944}},
  title        = {{N-sulfonyl urethanes to design polyurethane networks with temperature-controlled dynamicity}},
  url          = {{http://doi.org/10.1021/acs.macromol.2c02456}},
  volume       = {{56}},
  year         = {{2023}},
}
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