Hydrophobic and Hydrophilic Effects in a Mussel-Inspired Citrate-Based Adhesive.

ABSTRACT

The citrate-based tissue adhesive, synthesized by citric acid, diol, and dopamine, is a kind of mussel-inspired adhesive. The adhesion of mussel-inspired adhesive is not completely dependent on 3, 4-dihydroxyphenylalanine (Dopa) groups. The backbone structure of the adhesive also greatly affects the adhesion. In this study, to explore the effects of hydrophobicity and hydrophilicity of the backbone structure on adhesion, we prepared a series of citrate-based tissue adhesives (POEC-d) by changing the molar ratio of two diols, 1, 8-octanediol (O) and poly(ethylene oxide) (E), which formed hydrophobic segment units and hydrophilic segment units, respectively, in the molecule structure. The properties of cured adhesives showed that the adhesive with high E units had high swelling, rapid degradation, and low cohesion. In the adhesion strength measurement on the porcine skin, the adhesive with higher hydrophobicity was more likely to perform better. For the interfacial adhesion, hydrophilicity was conducive to the diffusion and penetration on the skin surface, but hydrophobic interaction showed a stronger effect to adhere with skin and hydrophobic association increased the adhesive concentration on the interface; for the bulk cohesion, hydrophobicity led to coacervation, promoting the Dopa-quinone coupling for cross-linking. In this amphipathic, citrate-based, soft-tissue adhesive system, when the feed ratio of hydrophilic segment was lower than 0.7, the coacervation could be formed through hydrophobic interaction, forming an efficient underwater adhesion system similar to that of mussels.