The creation of underwater adhesives inspired by marine mussels is important for bonding in wet environments, including several biomedical and industrial applications. Mussel adhesive proteins contain pendant catechol groups in the form of the amino acid 3,4-dihydroxy-phenylalanine (DOPA). Thus, several biomimetic adhesives have focused upon inclusion of catechol chemistry. Such a functional group can be considered a subtype of phenols. More broadly, polyphenols are often plant-derived chemicals with two or more phenolic groups. Antioxidant activity, adsorption on universal substrates, and biocompatibility have generated interest in these compounds. Many polyphenols include gallol groups (i.e., trihydroxyphenyl) in their chemical structure. In order to provide a potential alternative to catechol chemistry, gallic acid (GA) was chosen for a functional compound to modify styrenic copolymers. Here we present the synthesis, reactivity and adhesive characteristics of a simple biomimetic polymer, poly[(3,4,5-trihydroxystyrene)-<i>co</i>-styrene]. Pendent gallol groups (3,4,5-trihydroxy-styrene) are distributed throughout a polymer backbone. Several polymer derivatives were prepared, each with a different gallol content. Bonding characteristics of the adhesives was examined in both dry and underwater. Both the surface bonding and bulk cohesion were studied. This report builds upon prior efforts in which our lab and others are developing new polymeric materials on the basis of the principles learned from the nature.

Mussel-inspired gallol polymers: Design and generation of biomimetic adhesives

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ACS Fall 2022

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