Octyl cyanoacrylate

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Octyl cyanoacrylate
Skeletal formula
Space-filling model of the octyl cyanoacrylate molecule
Names
Preferred IUPAC name
Octyl 2-cyanoprop-2-enoate
Other names
Octyl 2-cyanopropenoate
Octyl 2-cyanoacrylate
Ocrylate
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.027.045
Properties
C12H19NO2
Molar mass 209.29 g·mol−1
Appearance Colorless liquid
Reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Octyl cyanoacrylate (OCA), a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. Its chief use is as the main component of medical cyanoacrylate glues.

In medical and veterinary applications, octyl cyanoacrylate, n-butyl cyanoacrylate and isobutyl cyanoacrylate are commonly used. They provide rapid wound closure,[1] are bacteriostatic, and their use is usually painless[citation needed]. Butyl esters provide a stronger bond, but the glue is rigid. The octyl ester, while providing weaker bond, is more flexible. Blends of octyl cyanoacrylate and n-butyl cyanoacrylate are available which offer both flexibility and a strong bond.

It polymerizes rapidly in presence of moisture.

Heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritating to lungs and eyes.

References[edit]

  1. ^ Singer, A. J.; McClain, S. A.; Katz, A. (2004). "A porcine epistaxis model: hemostatic effects of octylcyanoacrylate". Otolaryngology-Head and Neck Surgery. 130 (5): 553–557. doi:10.1016/j.otohns.2003.09.035. PMID 15138419. 

See also[edit]