Wound Adhesive from Cyanoacrylate: Synthesis and Characterization

Abstract

Abstract. 1-octyl cyanoacryalte is a main component of medical cyanoacrylate glues. As it rapidly polymerizes with water as an initiator, there are practical difficulties in designing simple synthetic routes. Any synthetic routes that evolve free nucleophilic products cannot, therefore be successful. Its synthesis too has not been reported in the open literature so far. Synthetic methods, which involve esterification of cyanoacetic acid with a chosen alcohol, polymerization by knoevenagel condensation and subsequent depolymerization, are applied to the synthesis of lower membered alkyl cyanoacryaltes in which the alkyl groups carry less than 8 carbons. We have synthesized 1-octyl cyanoacetate by a usual method involving p-toluene sulphonic acid as the catalyst. Its conversion to poly (1-octyl cyanoacrylate) is effected with 1, 3, 5-trioxane in a solvent free route, although paraformaldehyde has been suggested in few patents. Its FTIR spectrum confirmed its functional groups: Its -OH stretching yielded a broad band around 3400 cm -1 . Its depolymerization to high yield of 1-octyl cyano acrylate is under progress: during depolymerization p-toluene sulphonic acid, hydroquinone and phosphorous pentoxide are tried. We have avoided high temperature pyrolysis, as it is verified to degrade long alkyl chain.