Bioinspired chemistry is an important new area of study to expand the functionality of modern synthetic materials. In particular, synthetic polymers are applicable to various science fields using bioinspired chemistries. This talk will discuss a new class of polymers using a bioinspired adhesive concept that uses strong adhesion functionality referred to as catechol groups in 3,4-dihydroxy-L-phenylalanine (DOPA) that is found in many marine organisms’ adhesive proteins, such as those in mussels and polychaete. The new bioinspired adhesive is a glucose-based bioadhesive, poly(2-methacrylamido glucopyranose-co-N-methacryloyl-3,4-dihydroxyl-l-phenylalanine-co-8-azidooctyl methacrylate) [poly(MG-co-MDOPA-co-AOM)], that has been synthesized by thermally-initiated free radical polymerization. The new bioadhesive is composed of three modules: a hydrophilic glycopolymer segment, a mussels-inspired catechol segment, and a crosslinking azide segment. Poly(ethylene glycol) (PEG)-based crosslinker, (1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl PEG (BCN-PEG) was synthesized separately. Bulk adhesion properties of the terpolymer were enhanced by covalent bond forming crosslinking via strain-promoted azide-alkyne cycloaddition (SPAAC). The control of adhesion was studied under various crosslinker concentrations, crosslinking durations, and crosslinker lengths. Even without crosslinking, the new terpolymer adhesive demonstrated 20-fold higher adhesion strength (115 kPa) compared to a commercial rubber cement (5.8 kPa). The most significant factor to control for adhesion was crosslinker length. Crosslinking with the long crosslinker (PEG repeating units: 134) did not enhance adhesion strength. However, the short crosslinker (repeating units: 43) showed significant improvement in work of adhesion (150% higher than uncrosslinked).

Synthesis of bioinspired polymeric adhesives for precise control of properties via well-defined crosslinking chemistry

2019 Spring National Meeting

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