Linear Dendritic Block Copolymers as Promising Biomaterials for the Manufacturing of Soft Tissue Adhesive Patches Using Visible Light Initiated Thiol–Ene Coupling Chemistry

Abstract

A library of dendritic–linear–dendritic (DLD) materials comprising linear poly(ethylene glycol) and hyperbranched dendritic blocks based on 2,2‐bis(hydroxymethyl) propionic acid is successfully synthesized and postfunctionalized with peripheral allyl groups. Reactive DLDs with pseudo‐generations of 3 to 6 (G3‐G6) are isolated in large scale allowing their thorough evaluation as important components for the development of biomedical adhesives. Due to their branched nature and inherent degradable ester‐bonds, promising biomaterial resins are accomplished with suitable viscosity, eliminating the excessive use of co‐solvents. By utilizing benign high‐energy visible light initiated thiol–ene coupling chemistry, DLDs together with tris[2‐(3‐mercaptopropionyloxy)ethyl] isocyanurate and surgical mesh enable the fabrication of soft tissue adhesive patches (STAPs) within a total irradiation time of 30 s. The STAPs display the ability to create good adhesion to wet soft tissue and encouraging results in cytotoxicity tests. All crosslinked materials are also found to degrade after being stored in human blood plasma and phosphate buffered saline. The proposed benign methodology coupled with the promising features of the crosslinked materials is herein envisioned as a soft tissue adhesive with properties that do not exist in currently available tissue adhesives.