Carrie Brubaker Chemistry 30H June 2, 2000

The Chemistry of Superglue

From its use in model planes to passenger planes, SuperglueTM is possibly the most wellrecognized example of the glue compounds. Indeed, any person who has unknowingly glued his fingers together while using the product can acknowledge its remarkable (and insidious) adhesive properties. The curing process that facilitates these properties is a chain polymerization reaction. Although this process involves the contribution of fillers and stabilizers, the ingredient that gives Superglue its adhesive ability is methyl cyanoacrylate. This compound is just one member of a larger family of cyanoacrylates with the following basic structure:
C H2C C C O R O N

Contrary to popular understanding, Superglue does not air dry. In fact, cyanoacrylates in the compound cure (convert from liquid to solid) in the presence of weak bases such as water, alcohol, and blood. At normal conditions, a thin layer of water is present on almost all surfaces. This accounts for many unintended adhesions involving appendages and/or expensive tools! The curing process involves the anionic chain polymerization reaction, which occurs as follows: In the chain-initiating step, the weak base (X-) donates an electron pair to a cyanoacrylate monomer. The CH2 group is highly electropositive as a result of the electron-withdrawing properties of the cyanide and ester groups; therefore, the electron pair is attracted to this region. This attraction alters the carbon-carbon double bond to create bonding sites on both ends of the reactant group.
C N X C O R O O R C H2 C O C N

X-

H 2C

In this manner, the electron pair is passed on in chain propagation as each monomer alters the next. Bonds form between monomers, ultimately creating the powerfully adhesive polymer chains of cured Superglue.

C X C H2 C O R

N CH2 O O C

N C H2 C

O O

It is not surprising that with uses so varied, Superglue has a rich history. It begins during World War II, when cyanoacrylates were discovered in an attempt to produce optically clear gun sights. Tests with Superglue s main ingredient failed for obvious reasons; the compound stuck to all instruments. Approximately ten years later, researchers at Eastman Kodak rediscovered cyanoacrylates, and Kodak first marketed them in 1958. Superglue has been improved since that time with stabilizers and other supplementary ingredients that reinforce its adhesive strength. In recent years, that same adhesive strength has captured the attention of new fields. Research has shown that medical grade superglues such as 2-octylcyanoacrylate and 2butylcyanoacrylate are as successful as sutures in laceration repair. They have also shown to be effective in skin, bone, and cartilage grafts. Dentists use cyanoacrylates in dental cements and fillings, and paleontologists use them to reorganize fragile fossil specimens. Superglue has many fascinating applications, all facilitated by the anionic chain polymerization reaction.

Sources and References

Bound references: Bikales, N.M.; Mark, H.F.; Menges, G.; Overberger, C.G.: Encyclopedia of Polymer Science and Engineering, Second Edition. Volume 1, pp. 275-276, 290; Volume 2, pp. 17-20. John Wiley & Sons, Inc., 1985. Brown, W.H.; Foote, C.S.: Organic Chemistry, Second Edition. pp. 931-934. Saunders College Publishing, 1998. Web references: Chemfinder: www.chemfinder.com Loctite Corporation: www.loctite.com Journal of the American Academy of Pediatrics: www.pediatrics.org American Academy of Dermatology: www.aad.org Elmer s Products Inc.: www.elmers.com www.ethiconinc.com www.eff.org/pub/Publications/Bruce_Sterling/FSF_columns/fsf.07