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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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Citation

Please use this url to cite or link to this publication:

MLA
Houck, Hannes et al. “Tunable Blocking Agents for Temperature-controlled Triazolinedione-based Cross-linking Reactions.” MACROMOLECULES 51.8 (2018): 3156–3164. Print.
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.
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): 3156–3164.
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.
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://dx.doi.org/10.1021/acs.macromol.7b02526},
  volume       = {51},
  year         = {2018},
}

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