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Cyanoacrylate (Molecule of the Month for March 2007)

Superglue, Krazy Glue, Dermabond, Traumaseal



Cyanoacrylate is the generic name for glues such as methyl-2-cyanoacrylate, which is typically sold under trademarks like Superglue and Krazy Glue, and 2-octyl cyanoacrylate or n-butyl-cyanoacrylate, which are used in medical glues such as Dermabond and Traumaseal. Cyanoacrylate adhesives are known as "instant adhesives".

Generally, cyanoacrylate is an acrylic resin which rapidly polymerises in the presence of water (specifically hydroxide ions), forming long, strong chains, joining the bonded surfaces together. Because the presence of moisture causes the glue to set, exposure to moisture in the air can cause a tube or bottle of glue to become unusable over time. Another important trait is that cyanoacrylate sets quickly, often in less than a minute. A normal bond reaches full strength in two hours and is waterproof. Accelerators such as toluidine trigger setting in two or three seconds, with some loss of strength.

Cyanoacrylate is a very strong adhesive, particularly when used to bond non-porous materials or those that contain minute traces of water. It is also very good at bonding body tissue, and while this can be a troublesome side effect during everyday use, it has been exploited for the benefit of suture-less surgery. Acetone, which is sometimes found in nail polish remover, is a commonly available solvent capable of softening cured cyanoacrylate. Nitromethane is also an excellent solvent.

Formal Chemical Name (IUPAC)
methyl 2-cyanoprop-2-enoate

References

http://en.wikipedia.org/wiki/Cyanoacrylate

http://www.supergluecorp.com/history.html

Picture of Cyanoacrylate

click on the picture above to interact
with the 3D model of the
Cyanoacrylate structure
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Picture of Cyanoacrylate

C5 H5 N O2



Update by Karl Harrison
(Molecule of the Month for March 2007 )