Polycyanoacrylates

Abstract

Cyanoacrylates are important materials in the production of rapidly curing structural adhesives. The monomers are generally low viscosity liquids, which are prepared in a two‐step process by a base‐catalyzed condensation of paraformaldehyde and cyanoacetate, followed by thermally induced depolymerization of the resultant oligomer under acidic conditions. The monomers are highly reactive toward basic materials and undergo extremely rapid anionic polymerization on contact with catalytic amounts of even weakly nucleophilic compounds or species. The polymers are amorphous materials that are readily depolymerized at elevated temperatures. They are generally soluble in polar aprotic solvents, although polymer solutions are unstable in the presence of basic materials. Adhesives are by far the most important end use for cyanoacrylates and they are widely used for component assembly and repair. The adhesive products are characterized by high rates of curing, high adhesive strength, and good adhesion to a wide range of different materials. They are becoming increasingly important materials as tissue adhesives and sealants for various surgical procedures.

Radical Polymerization of Alkyl 2-Cyanoacrylates

“…Alkyl 2-cyanoacrylates or cyanoacrylates (CAs) are a family of vinyl monomers renowned for their high reactivity, instant adhesive properties, and wide-ranging applications [1,2,3,4,5,6]. Short chain CAs, like methyl- and ethyl 2-cyanoacrylate have found great utility as the major components of industrial and household instant adhesives or “super glues”, including those manufactured at Henkel under the Loctite brand (Table 1) [4,5,6].…”

“…Short chain CAs, like methyl- and ethyl 2-cyanoacrylate have found great utility as the major components of industrial and household instant adhesives or “super glues”, including those manufactured at Henkel under the Loctite brand (Table 1) [4,5,6]. …”

“…The general monomer chemistry, synthesis, modes of polymerization, and the physical characteristics of the resulting polymers, along with several toxicological evaluations, have been detailed in a number of reviews [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,20,21,22]. In this review, after a general overview of reactivity and properties, the focus is the radical polymerization of CAs, with the advantages over the more facile anionic pathway clearly outlined.…”

Controlled living anionic polymerization of cyanoacrylates by frustrated Lewis pair based initiators

“…The excellent adhesive properties of polycyanoacrylates (PCA) have enabled their widespread use for many household applications (Super Glue®), and, most recently for applications in medicine,12 surgery,13 ophthalmology,14 dentistry,15 tissue reconstruction,16 and for drug delivery,17 due to their biocompatibility and biodegradability. Various other applications for CAs include fingerprint detection for forensic applications, coating for lithographic printing plates, waveguides for optical sensors, photoresists and holographic recording media, which exploit their rapid polymerizability or the optical properties of their polymers 18. However their use as designer materials is scarce partly due to the difficulty of controlling their polymerization and copolymerization processes.…”

Investigation of the effects of structure-sensor interaction on piezoceramic transducers for structural health monitoring applications

“…Kotzev et al (1981 showed that at 150°C a total loss of ethyl-2-cyanoacrylate adhesive properties occurred ( (Kotzev et al, 1981), p1946). Woods (2001), (p647) documents that the poly-cyanoacrylate group of polymers "undergo retro-polymerisation reactions at temperatures in the vicinity of 140°C to 180°C".…”