Abstract
Cyanoacrylates (CAs) are well-known fast-setting adhesives, which are sold as liquids in the presence of stabilizers. Rapid anionic polymerization on exposure to surface moisture is responsible for instant adhesion. The more difficult, but synthetically more useful radical polymerization is only possible under acidic conditions. Recommendations on the handling of CAs and the resulting polymers are provided herein. In this review article, after a general description of monomer and polymer properties, radical homo- and copolymerization studies are described, along with an overview of nanoparticle preparations. A summary of our recently reported radical polymerization of CAs, using reversible addition-fragmentation chain transfer (RAFT) polymerization, is provided.
Highlights
Commercial CAs will often contain radical inhibitors, such as hydroquinone, catechol, p-methoxyphenol, butylated hydroxyanisole, and related phenolic compounds to suppress radical polymerization, which can be triggered with high temperatures or UV-light
Initiation takes place in two steps, as is normal in radical polymerization; the first involves the thermal homolysis of the initiator to give a pair of radicals
After 21 h, poly(ethyl 2-cyanoacrylate) was isolated by precipitation into hexane at greater than 70% conversion, polymer formation via anionic polymerization cannot be ruled out since no anionic inhibitor was employed
Summary
The stability of the propagnating species -is in stark contrast to other common monomers like styrenics or (meth)acrylates, for example, wCharebroexy, laitne the case of organolithium-initiated anionic polymerizations, the introduction of trace aAmnioonunts of air or moisture terminates polymer growth by reacting with the active chain-end anions or the (often organometallic) initiator. With the latter conventional anionic polymerizations stringent experimental conditions, including inert atmospheres and glove boxes are a requirement [33,34].
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