Methyl -cyanoacrylate

The 2-cyanoacryhc esters have sharp, pungent odors and are lacrimators, even at very low concentrations. These esters can be irritating to the nose and throat at concentrations as low as 3 ppm eye irritation is observed at levels of 5 ppm (13). The TLV for methyl 2-cyanoacrylate is 2 ppm and the short-term exposure limit is 4 ppm (14). Good ventilation when using the adhesives is essential. 

Toxicology. Methyl 2-cyanoacrylate is an irritant of the eyes and nose and can induce occupational asthma. 

When methyl 2-cyanoacrylate was applied as an adhesive to rabbit or human eyes, some reports described corneal haze and inflammation other reports with highly purified material indicated less toxicity. Mistaken use in the eyes as eyedrops has caused immediate brief smarting and firm gluing of the eyelids together. Acetone on a swab can be used to unglue the lids and remove the glue from the cornea with minimal, if any, injury to the corneal epithelium. ... 

Methyl 2-cyanoacrylate was positive in the Ames test with and without activation by metabolic enzymes. ... 

The 2003 ACGIH threshold limit value-time-weighted average (TLV-TWA) for methyl 2-cyanoacrylate is 2 ppm (9.1mg/m ) with a short-term excursion limit (STEL) of 4 ppm (18mg/m ). 

ACGIH Methyl 2-cyanoacrylate. Documentation of the TLVs for Substances in Workroom Air, 6th ed, pp 965-966. Cincinnati, OH, American Conference of Governmental Hygienists, 1991... 

Rietveld ED, Garnaat MA, Seutter-Berlage E Bacterial mutagenicity of some methyl 2-cyanoacrylates and methyl 2-cyano-3-phenylacrylates. Mutat Res 188 97-104, 1987... 

With two stabilizing groups on the carbon radical, polymerization becomes even easier. A famous example is SuperGlue , which is methyl 2-cyanoacrylate. The monomer in the tube polymerizes on to any surface (wood, metal, plastic, fingers, eyelids, lips,...) catalysed by traces of moisture or air, and the bonds, once formed, are very difficult to break. The intermediate radical in this polymerization is stabilized by both CN and CC Me groups. 

Methyl 2 Cyanoacrylate (MCA) Ethyl 2 Cyanoacrylate (ECA). Occupational Safety and Health Administration. http //www.osha slc.gov/dts/sltc/methods/organic/orgo55/orgo55. html (accessed on October 6, 2005). 

Methyl-2-cyanoacrylate Formula CH2=C(CN)C00CH3 CAS 137-05-3 RTECS AS7000000 IDLH N.D. 

The compoimds listed in Table 10.11 have been found to photoinitiate the polymerization of neat ethyl or methyl 2-cyanoacrylate, CA, that readily polymerize by an anionic mechanism. Therefore, this has been taken as evidence for the occurrence of an anionic mechanism [57-59]. 

---