A Modular and Practical Synthesis of Zwitterionic Hydrogels through Sequential Amine-Epoxy “Click” Chemistry and N-Alkylation Reaction

• Main Authors: Junki Oh, Kevin Injoe Jung, Hyun Wook Jung, Anzar Khan
• Format: Article
• Language: English
• Published: MDPI AG 2019-09-01
• Series: Polymers
• Subjects: amine-epoxy reaction; “click” chemistry; poly(β-hydroxyl amine)s; hydrogel synthesis; sequential reactions; “click” hydrogels; hydrogel patterning
• Online Access: https://www.mdpi.com/2073-4360/11/9/1491

In this work, the amine-epoxy “click” reaction is shown to be a valuable general tool in the synthesis of reactive hydrogels. The practicality of this reaction arises due to its catalyst-free nature, its operation in water, and commercial availability of a large variety of amine and epoxide molecules that can serve as hydrophilic network precursors. Therefore, hydrogels can be prepared in a modular fashion through a simple mixing of the precursors in water and used as produced (without requiring any post-synthesis purification step). The gelation behavior and final hydrogel properties depend upon the molecular weight of the precursors and can be changed as per the requirement. A post-synthesis modification through alkylation at the nitrogen atom of the newly formed β-hydroxyl amine linkages allows for functionalizing the hydrogels. For example, ring-opening reaction of cyclic sulfonic ester gives rise to surfaces with a zwitterionic character. Finally, the established gelation chemistry can be combined with soft lithography techniques such as micromolding in capillaries (MIMIC) to obtain hydrogel microstructures.