High-T sub(g) Thiol-Click Thermoset Networks via the Thiol-Maleimide Michael Addition

Thiol-click reactions lead to polymeric materials with a wide range of interesting mechanical, electrical, and optical properties. However, this reaction mechanism typically results in bulk materials with a low glass transition temperature (T sub(g)) due to rotational flexibility around the thioethe...

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Bibliographic Details
Published in:Macromolecular rapid communications. 2016-07, Vol.37 (13), p.1027-1032
Main Authors: Parker, Shelbi, Reit, Radu, Abitz, Haley, Ellson, Gregory, Yang, Kejia, Lund, Benjamin, Voit, Walter E
Format: Article
Language:English
Subjects:
Dynamical systems
Dynamics
High temperature
Homogeneity
Mechanical analysis
Networks
Reaction mechanisms
Thermosetting resins
Online Access:Get full text
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Summary:Thiol-click reactions lead to polymeric materials with a wide range of interesting mechanical, electrical, and optical properties. However, this reaction mechanism typically results in bulk materials with a low glass transition temperature (T sub(g)) due to rotational flexibility around the thioether linkages found in networks such as thiol-ene, thiol-epoxy, and thiol-acrylate systems. This report explores the thiol-maleimide reaction utilized for the first time as a solvent-free reaction system to synthesize high-T sub(g) thermosetting networks. Through thermomechanical characterization via dynamic mechanical analysis, the homogeneity and T sub(g)s of thiol-maleimide networks are compared to similarly structured thiol-ene and thiol-epoxy networks. While preliminary data show more heterogeneous networks for thiol-maleimide systems, bulk materials exhibit T sub(g)s 80 degree C higher than other thiol-click systems explored herein. Finally, hollow tubes are synthesized using each thiol-click reaction mechanism and employed in low- and high-temperature environments, demonstrating the ability to withstand a compressive radial 100 N deformation at 100 degree C wherein other thiol-click systems fail mechanically. The thiol-maleimide Michael addition is demonstrated as a reaction mechanism used to synthesize high-T sub(g) thiol-click thermosetting networks that exhibit T sub(g)s 80 degree C higher than similarly structured thiol-click systems. Hollow cylindrical samples of each composition are fabricated and loaded radially, showing the thiol-maleimide thermosets withstanding a 100 N load at elevated temperatures.
ISSN:1022-1336
1521-3927
DOI:10.1002/marc.201600033