Polycyanoacrylates

Abstract

Alkyl 2‐cyanoacrylate monomers are commonly used as instant adhesives or “superglue,” mainly because of their unique ability to undergo rapid polymerization under ambient conditions on a wide range of surfaces. This article overviews the chemistry and physical properties of these materials, the most common methods of preparation, their mode(s) of polymerization, and typical performance properties. The main performance limitations of alkyl 2‐cyanoacrylate adhesives, such as poor hot strength and resistance to extreme environments (high heat and humidity) are explained in terms of the susceptibility of the polymer to degradation, and how the chemical structure of the polymer directly affects this degradation process. An overview is given of how the performance properties of cyanoacrylate adhesives are modified through the inclusion of various thickeners for viscosity modification, accelerators for cure acceleration, and recent advances in two component cyanoacrylate adhesives. The uses of polycyanoacrylates in medical adhesive applications and for the preparation of nanoparticles for drug delivery are briefly reviewed.

Skin Protectants Made of Curable Polymers: Effect of Application on Local Skin Temperature

“…Cyanoacrylate adhesives cure rapidly on skin surfaces (within 5–60 s). 6 The first generation of cyanoacrylate adhesives were based on lower alkyl (methyl) ester monomers and caused tissue toxicity. Research showed that the longer the hydrocarbon group at the –R position, the slower the rate of polymerization, the less heat released during polymerization, and the lower the histotoxicity.…”

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]. …”

“…β-Methoxyethyl- and β-ethoxyethyl 2-cyanoacrylate have lower vapor pressures compared to shorter chain CAs and are often used as low odor adhesives. Additionally, these adhesives avoid a phenomenon characteristic of their shorter chain counterparts, known as “blooming”, whereby polymerized monomer vapor is deposited as a fine chalky powder on the surface near an adhesive bond-line, and are sometimes referred to as “low-bloom” adhesives [4]. Phenylethyl 2-cyanoacrylate differs from the previously named CAs in that it is a solid and is utilized in industrial adhesive tapes and films [19].…”

“…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.…”