Synthesis and degradation of poly (alkyl α‐cyanoacrylates)

Abstract

In order to study structure‐tissue reactivity relationships and ultimately develop a less necrotizing adhesive, this laboratory undertook a study of the synthesis and degradation of the homologous series of α‐cyanoacrylate monomers and polymers. A method for synthesizing high purity cyanoacrylates and some of their chemical and physical properties and presented. In vitro kinetics studies under heterotgeneous and homogeneous conditions indicate that cyanoacrylate polymers degrade by hydrolytic scission of the polymer chain. The products resulting from such a scission are formaldehyde (positively identified by derivative formation) and ultimately and alkyl cyanoacetate. As the homologous series is ascended, the rate of degradation under neutral conditions decreases. In homogeneous solutions, under alkaline conditions, the ràte of degradation is considerably higher than under neutral conditions and the rates obtained with the methyl to the butyl derivative are of the same order. Aproposed mechanism of degradation is presented. Medical evaluation has indicated that as the homologous series is ascended, the greater the tissue tolerance to the monomers and polymers. The relevance of the results of the in vitro studies to this medical finding is presented.