Materials were designed based on cross-linked dynamic covalent bonds’ inherent self-healing ability. A dynamic network of imine-primary amine bonds prepared by PEO diamine and benzyl-trialdehyde shows malleability under stress by dynamic mechanical analysis (DMA). The disappearance of aldehyde C=O peak and appearance of imine C=N peak in IR spectrum have further confirmed the cross-linked network. H-NMR kinetics demonstrate the driving force of the self-healing process is due to imine and primary amine bond exchange. Solvent polarity affects the rate of bond exchange shown in both H-NMR and DMA. Samples made with polar aprotic solvents show fastest dynamic bond exchange compared to polar protic and non-polar solvents. Through the dynamic bonds, the damaged sample was able to be reattached and healed over time. Organic gels have been shown to successfully exhibit malleability and are capable of self-healing based on dynamic exchange of imine and primary amine bonds.

Malleable and self-healing polymer networks based on dynamic imine bond

249th National Meeting (2015)

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