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Tunable blocking agents for temperature-controlled triazolinedione-based cross-linking reactions

(2018) MACROMOLECULES. 51(8). p.3156-3164
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Abstract
The remarkable reactivity of triazolinediones (TADs) toward olefin-type substrates marks them as highly attractive click reagents, in particular for polymer modification and cross-linking. Critically, their ultrafast reaction rates result in handling issues and a rather limited shelf life whereas a particular concern for polymer material applications is homogeneous network formation. Herein, we introduce 2phenylindoles as highly promising blocking agents for TADs, giving bench-stable reagents at ambient temperature from which the initial TADs can be released upon heating. A set of 11 indoles with varying substitution patterns was synthesized, leading to a precise control for the temperature of deblocking within a broad range 100 degrees C. The established indole TAD platform was next applied to bivalent TAD reagents to enable on-demand TAD-based cross-linking reactions of a diene-containing polyurethane (M-n = 12.5 kDa). Fine-tuning of the curing temperatures, down to 50 degrees C, was evidenced via rheological measurements.
Keywords
CLICK CHEMISTRY, OLEFIN REACTIONS, ISOCYANATE, POLYURETHANE, SYSTEMS, DESIGN, ENE, ULTRAFAST, NETWORKS

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MLA
Houck, Hannes, et al. “Tunable Blocking Agents for Temperature-Controlled Triazolinedione-Based Cross-Linking Reactions.” MACROMOLECULES, vol. 51, no. 8, 2018, pp. 3156–64, doi:10.1021/acs.macromol.7b02526.
APA
Houck, H., De Bruycker, K., Barner-Kowollik, C., Winne, J., & Du Prez, F. (2018). Tunable blocking agents for temperature-controlled triazolinedione-based cross-linking reactions. MACROMOLECULES, 51(8), 3156–3164. https://doi.org/10.1021/acs.macromol.7b02526
Chicago author-date
Houck, Hannes, Kevin De Bruycker, Christopher Barner-Kowollik, Johan Winne, and Filip Du Prez. 2018. “Tunable Blocking Agents for Temperature-Controlled Triazolinedione-Based Cross-Linking Reactions.” MACROMOLECULES 51 (8): 3156–64. https://doi.org/10.1021/acs.macromol.7b02526.
Chicago author-date (all authors)
Houck, Hannes, Kevin De Bruycker, Christopher Barner-Kowollik, Johan Winne, and Filip Du Prez. 2018. “Tunable Blocking Agents for Temperature-Controlled Triazolinedione-Based Cross-Linking Reactions.” MACROMOLECULES 51 (8): 3156–3164. doi:10.1021/acs.macromol.7b02526.
Vancouver
1.
Houck H, De Bruycker K, Barner-Kowollik C, Winne J, Du Prez F. Tunable blocking agents for temperature-controlled triazolinedione-based cross-linking reactions. MACROMOLECULES. 2018;51(8):3156–64.
IEEE
[1]
H. Houck, K. De Bruycker, C. Barner-Kowollik, J. Winne, and F. Du Prez, “Tunable blocking agents for temperature-controlled triazolinedione-based cross-linking reactions,” MACROMOLECULES, vol. 51, no. 8, pp. 3156–3164, 2018.
@article{8599659,
  abstract     = {{The remarkable reactivity of triazolinediones (TADs) toward olefin-type substrates marks them as highly attractive click reagents, in particular for polymer modification and cross-linking. Critically, their ultrafast reaction rates result in handling issues and a rather limited shelf life whereas a particular concern for polymer material applications is homogeneous network formation. Herein, we introduce 2phenylindoles as highly promising blocking agents for TADs, giving bench-stable reagents at ambient temperature from which the initial TADs can be released upon heating. A set of 11 indoles with varying substitution patterns was synthesized, leading to a precise control for the temperature of deblocking within a broad range 100 degrees C. The established indole TAD platform was next applied to bivalent TAD reagents to enable on-demand TAD-based cross-linking reactions of a diene-containing polyurethane (M-n = 12.5 kDa). Fine-tuning of the curing temperatures, down to 50 degrees C, was evidenced via rheological measurements.}},
  author       = {{Houck, Hannes and De Bruycker, Kevin and Barner-Kowollik, Christopher and Winne, Johan and Du Prez, Filip}},
  issn         = {{0024-9297}},
  journal      = {{MACROMOLECULES}},
  keywords     = {{CLICK CHEMISTRY,OLEFIN REACTIONS,ISOCYANATE,POLYURETHANE,SYSTEMS,DESIGN,ENE,ULTRAFAST,NETWORKS}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{3156--3164}},
  title        = {{Tunable blocking agents for temperature-controlled triazolinedione-based cross-linking reactions}},
  url          = {{http://doi.org/10.1021/acs.macromol.7b02526}},
  volume       = {{51}},
  year         = {{2018}},
}

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