Synthesis and characterization of four alkyl 2‐cyanoacrylate monomers and their precursors for use in latent fingerprint detection

Abstract

Four novel cyanoacrylates, 2-cyanoethyl 2-cyanoacrylate, 1-cyanoethyl 2-cyanoacrylate, trideuteromethyl 2-cyanoacrylate and pentadeuteroethyl 2-cyanoacrylate have been synthesized using a Diels-Alder protection/deprotection route involving anthracene. The common route for the synthesis of alkyl 2-cyanoacrylates was found to be unsatisfactory for the production of small quantities of the targeted cyanoacrylates, which have potential as reagents for the mid-infrared spectral imaging of fingerprints on difficult surfaces.• the use of acid catalysts for the condensation reaction between alkyl cyanoacetates and formaldehyde [35][36][37][38] • Diels-Alder protection and deprotection [39][40][41][42][43][44][45][46][47][48][49] • esterification of 2-cyanoacryloyl chloride with an alcohol or diol (for bis cyanoacrylates) 50

Polycyanoacrylates

“…To date, most of these routes have not been exploited on an industrial scale and have mainly been used for the synthesis of cyanoacrylates that are difficult or impossible to synthesize via the more common industrial Knoevenagel method. Reedy and colleagues (16), and separately Domb and co-workers (15) recently reported the synthesis of 2-cyanoethyl-2-cyanoacrylate for use as reagents for midinfrared spectral imaging of latent fingerprints on difficult surfaces. The authors report they failed to isolate the desired monomer via the standard Knoevenagel-depolymerization route, but succeeded using an anthracene adduct-esterification-deprotection route as illustrated in Figure 8.…”

“…It is caused by the migration of monomer vapor beyond the adhesive bond line which subsequently polymerizes to leave the characteristic chalky white deposits known as "blooming," as shown in Figure 3. In some applications, the high vapor pressure and blooming effect of cyanoacrylate monomers has been exploited to good advantage for the detection of latent fingerprints (15,16).…”

Breathable rubbery skin protectors: Design, synthesis, characterization, and properties of cyanoacrylated silicone rubber networks

“…9,10 The length of the silicone copolymer did not affect deprotection efficiency, and deprotection was ~92% in all systems.…”

“…In this molecule the SiH groups are sterically less encumbered than in the shorter one (see above) so that substitution by A/Allyl-CA groups increased to 58%, i.e., to [8][9][10] A/Allyl-CA adduct per copolymer.…”

Radical Polymerization of Alkyl 2-Cyanoacrylates

“…Colloidal nanoparticles derived from CAs have shown great promise in the field of drug and vaccine delivery [11,12,13,14,15,16]. CA is used in latent fingerprint development in forensic science, whereby CA vapors adheres to trace amino acids present in the fingerprint [17,18]. Due to its unsaturated ester group, allyl 2-cyanoacrylate has the ability to undergo crosslinking reactions at elevated temperatures, a feature that has found use in thermally resistant adhesives [5].…”