Synthesis of an epoxy-based adhesive hydrogel from asymmetrically protected ethylenediamine

Summary

Poly[aminoethylbutyl ether] (poly-AEBE), a new adhesive hydrogel film bearing primary amine pendants, was synthesized. The key synthetic step, in the synthesis of poly-AEBE, involved a novel use of asymmetrically and reversibly protected ethylenediamine (ED). Initially silylated oligomeric-AEBE was prepared from the reaction of 1,4-butanediol diglycidyl ether with N,N-bis(trimethylsilyl)-ethylenediamine. Oligomer crosslinking was initiated by deprotection of the primary amine pendants with excess ethanol, yielding poly-AEBE. When adhered to glass and skin, films of poly-AEBE gave peel forces of 16.90±0.73 N and 1.05±0.15 N, respectively. In addition, poly-AEBE had a high water uptake (1840%) and an equilibrium water content of 94%. The residual water extractables were 3.3%. These results strongly support the potential use of poly-AEBE for adhesive hydrogels and affinity chromatography supports.