SynopsisI n order to study structure-tissue reactivity relationships arid ultimately develop a less necrotizing adhesive, this laboratory undertook a study of the synthesis and degradation of the homologous series of a-cyanoacrylate monomers and polymers. A method for synthesizing high purity cyanoacrylates and some of their chemical and physical properties are presented. In vitro kinetics studies under heterogeneous 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 an alkyl cyanoacetate. As the homologous series is ascended, the rate of degradation under neutral conditions decreases. In homogeneous solution, under alkaline conditions, the rate 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. A proposed 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.

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In an effort to obtain tissue adhesive monomem which would wet and spread on tissue substrates and be rapidly biodegradable, the branched esters of alkyl a-cyanoacrylates, as well as a 9.5-5 wt.-% mixture of n-heptyl and methyl a-cyanoacrylate, were studied. The data indicate that alkyl a-cyanoacrylates having branched alkoxy groups appear to be promising in this regard.

Considers reactions and the synthesis of organic isocyanates, polyisocyanates, fibers, foams, elastomers, adhesives, isocyanate generators, and plastics.

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