.alpha.-substituted acrylic acid esters

Abstract

.alpha.-Substituted acrylic acid esters, their polymers and adhesives therefrom, and methods of synthesizing these compounds. The compounds of the invention are useful as intermediates in the synthesis of isocyanato esters and can be polymerized to form an effective, non-toxic adhesive. The method of the invention encompasses utilizing the adhesive composition in biomedical applications, such as joining live animal tissue. Other adhesive applications are contemplated for living tissue and inanimate objects. The compounds are also used as monomers which can be polymerized, used in conjunction with other monomers as adhesive compositions, cross-linking agents, dye acceptor additives to vinylic polymers and useful chemical intermediates. The method of the invention encompasses synthesizing the aformentioned monomers and intermediates. Methyl .alpha.-(ethoxycarbonamido)acrylate is synthesized from either DL-serine or methyl pyruvate. For use as an intermediate, silyl substitution of the compound is accomplished by reacting the ester with trimethylchlorosilane. This .alpha.-substituted silated ester is used as an intermediate in the preparation of methyl .alpha.-isocyanatoacrylate, which can be polymerized with N-vinyl-2-pyrrolidone to produce a desirable adhesive. Analagous procedures, starting with L-ethyl serine and L-benzyl serine, respectively, are followed to arrive at the corresponding ethyl and benzyl esters.