Radical Polymerization of Alkyl 2-Cyanoacrylates

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.

In situpolymerization process: an essential design tool for lithium polymer batteries

“…486 In cyanoacrylates, the strong electron-withdrawing nitrile moiety is covalently linked to the unsaturated α-carbon atom of the acrylate group. 487 Therefore, the β-carbon becomes highly electrophilic, resulting in high- reactivity for cyanoacrylate monomers. Unlike the free-radical polymerization pathway in the presence of an external initiator and energy source, anionic polymerization is energy efficient and can be carried out even at ambient temperature.…”

Leakage‐Proof Electrolyte Chemistry for a High‐Performance Lithium–Sulfur Battery

“…It is speculated that the sharp weight increase origins from the fast polymerization of the residual ECA monomers catalyzed by the moisture from ambient air. [6,7,10] To verify this,I R spectra of the leakage-proof electrolyte before and after exposed to ambient air are compared. As shown in Figure S7e,after exposed to ambient air,the intensity of the peak at 1600 cm À1 decreases while the intensity of the peak at 1744 cm À1 increases substantially,w hich means that the ethenolate motif decreases while the carbonyl (C=O) of the Poly(ECA) segment increases,c onfirming the speculation of further polymerization.…”

“…[6] Polymerization of ECAi si nitiated by anions in the absence of water and ambient air, what is called anionic polymerization. [7] On the basis of this mechanism, LPSCl with strong nucleophilicity as well as high Li + fraction neutralized by anions of PS 4 3À ,S 2À , and Cl À is av ery promising choice to initiate ECA polymerization, [8] in which the anions are bonded to poly(ECA) segments while Li + is attracted around by coulombic force to make ECA conductive.The detailed preparation process and the reaction mechanism between LPSCl and ECAc an be found in the Supporting Information. Ther eaction products are defined as LPSCl-grafted poly(ECA),i .e., LgP,f or convenience.…”

Biomaterials in Gastroenterology: A Critical Overview

“…It was the Eastman Kodak Co. (Rochester, NY, USA) that launched them as adhesives in industrial and medical markets [85]. There is vast literature on cyanoacrylate polymers and their medical applications, as summarized in some recommended reviews [86,87,88,89,90,91]. Proposed in the late 1950s, the cyanoacrylate glues have been soon employed by surgeons for creating sutureless wound seals, and early pioneering work has been carried out in vascular surgery [92,93], ophthalmic surgery [94,95], and surgery of the GI tract [96,97].…”