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Development of a Novel Hydrophilic, Biocompatible Adhesive

The synthesis of two novel hydrogel adhesive films, poly(butoxy- Entprol) and poly(butoxy/ethylene-Entprol) was accomplished by crosslinking either epoxy end-capped oligomeric-butoxy-Entprol or epoxy end-capped oligo meric-butoxy/ethylene-Entprol with 5-10 mole% diethylenetriamine. The two oligomers with Mn 1700 to 5000 were obtained in a 78-87% yield, by the reac tion of one equivalent of N,N'-bis(2-hydroxypropyl)ethylenediamine with either one equivalent of 1,4-butanediol diglycidyl ether or one equivalent of a 1:1 mole ratio mixture of 1,2,7,8-diepoxyoctane and 1,4-butanediol diglycidyl ether. Peel adhesion to glass for poly(BE) and poly(BEE) gave peel forces of 12.02 and 13.61 N, respectively, as compared to five acrylate adhesives, ranging from 4.90-11.56 N. Poly(BE) had superior adhesion to skin (3.45 N) compared to poly(BEE) (0.97 N) and the acrylate-based adhesives (0.79-2.64 N). In addition, fully hydrated poly(BE) and poly(BEE) have both a high water uptake (971% and 630%, respectively) and equilibrium water content (90% and 86%, respec tively). Both films lose adhesion with progressive hydration. These hydrogels actively support the growth of 3T3 fibroblasts and SCC-13 epithelial cells. These results strongly support the potential of these films as single-layered adhesive hydrogel dressings.