Recyclable, Strong Thermosets and Organogels via Paraformaldehyde Condensation with Diamines

Recyclable, Strong Thermosets and Organogels via Paraformaldehyde Condensation with Diamines

Nitrogen-based thermoset polymers have many industrial applications (for example, in composites), but are difficult to recycle or rework. We report a simple one-pot, low-temperature polycondensation between paraformaldehyde and 4,4′-oxydianiline (ODA) that forms hemiaminal dynamic covalent networks...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) Vol. 344; no. 6185; pp. 732 - 735
Main Authors: García, Jeannette M., Jones, Gavin O., Virwani, Kumar, McCloskey, Bryan D., Boday, Dylan J., ter Huurne, Gijs M., Horn, Hans W., Coady, Daniel J., Bintaleb, Abdulmalik M., Alabdulrahman, Abdullah M. S., Alsewailem, Fares, Almegren, Hamid A. A., Hedrick, James L.
Format: Journal Article
Language:English
Published: United States American Association for the Advancement of Science 16-05-2014
The American Association for the Advancement of Science
Subjects:
Carbon nanotubes
Condensation
Diamines
Glaciers
Infrared radiation
Materials
Materials science
Monomers
Polymers
Recycling
Solvents
Youngs modulus
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Summary:Nitrogen-based thermoset polymers have many industrial applications (for example, in composites), but are difficult to recycle or rework. We report a simple one-pot, low-temperature polycondensation between paraformaldehyde and 4,4′-oxydianiline (ODA) that forms hemiaminal dynamic covalent networks (HDCNs), which can further cyclize at high temperatures, producing poly(hexahydrotriazine)s (PHTs). Both materials are strong thermosetting polymers, and the PHTs exhibited very high Young's moduli (up to ∼14.0 gigapascals and up to 20 gigapascals when reinforced with surface-treated carbon nanotubes), excellent solvent resistance, and resistance to environmental stress cracking. However, both HDCNs and PHTs could be digested at low pH (<2) to recover the bisaniline monomers. By simply using different diamine monomers, the HDCN- and PHT-forming reactions afford extremely versatile materials platforms. For example, when poly(ethylene glycol) (PEG) diamine monomers were used to form HDCNs, elastic organogels formed that exhibited self-healing properties.
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ISSN:0036-8075
1095-9203
DOI:10.1126/science.1251484