The Chemistry of Superglue

Introduction

Super glue is a glue that sets very quickly, and forms a strong bond.

Super glue is made of repeating monomers of Cyanoacrylate. Cyanoacrylate is made of carbon, oxygen, hydrogen, and nitrogen. Before superglue is polymerised, it has double bonds that can be stolen if exposed to anions, this initiates the chain reaction that bonds super glue. Superglue is a great tool to bind something together. I chose Superglue because I thought it would be interesting to see how it works. I have used superglue to fix many things, from coffee cups to lamps. Although it is an easy tool to use, most people never think about what makes it work.

Composition of ...The only ingredient in super glue is cyanoacrylate. The container can be made from different plastics, as long as it is airtight.

Main Chemicals, Compounds, Components

Cyanoacrylate, or C5H5NO2 is the main chemical in superglue. Cyanoacetate, formaldehyde, and nitrogen are all used to manufacture super glue. Cyanoacrylate is superglue. It is liquid until it is exposed to moisture, then it becomes solid.

Chemistry's Role

The Chemistry of how superglue works is interesting. Super Glue cures quickly and strongly because even trace amounts of hydroxyl ions (OH-) in water can start a chain polymerization reaction. This means that all the separated molecules of cyanoacrylate called monomers link together into long chains, called polymers. This causes the cyanoacrylate to solidify, because the monomers can’t slide past each other. This polymerization is possible because the anion’s (usually hydroxyl’s) electronegativity breaks a double bond in cyanoacrylates monomer structure. Hydroxyl (OH-) is found in the humidity in the air, so once cyanoacrylate is exposed to air, superglue immediately begins to cure. Once one cyanoacrylate monomer’s double bond is broken, it causes each monomer of cyanoacrylate to want to form a bond with the cyanoacrylate polymer structure. When cyanoacrylate polymerizes, the cyanoacrylate sticks together on an atomic level, and it becomes solid. Super Glue solidifies in all the microscopic crevices of an object that it moved into when it was a liquid, and it can form chemical bonds with any anions in the object. That is why superglue sticks things together so quickly.

Background Research

Dr. Harry Coover invented superglue in 1949. He was trying to make a plastic to form gun sights. He gave up on cyanoacrylate because it was too sticky. In 1951, he realized cyanoacrylates potential as a commercial adhesive. Super Glue, or cyanoacrylate is manufactured in factories. To make superglue, cyanoacetate is put in an airtight kettle and mixed with formaldehyde. Water is given off when the cyanoacetate and formaldehyde react, and the kettle is heated to evaporate this water. After the water is evaporated, cyanoacetate remains, but it is solid (in polymer form.) Any air in the kettle is replaced with nitrogen because nitrogen will not polymerize the cyanoacrylate. Then, the mixture is heated to over 300 degrees fahrenheit, it becomes liquid (polymers split into monomers) and any remaining water is evaporated and separated, leaving liquid cyanoacetate, also known as superglue. Chemistry was used in the invention of superglue, and it is necessary in all parts of manufacturing superglue.

Resources

http://home.howstuffworks.com/question695.htm

    • Super glue is cyanoacrylate
    • Cyanoacrylate is C5H5NO2
    • Hydroxyl ions are in water, and trigger anionic polymerization in superglue

https://en.wikipedia.org/wiki/Anionic_addition_polymerization

    • Explains polymerization, monomers, and polymers

http://www.ems.psu.edu/sites/default/files/u5/students/Martin%20Antensteiner%20Paper_Third.pdf

    • Explains how cyanoacrylate has monomers, and polymerizes, and how double bond is involved.

http://www.supergluecorp.com/blog/2015/09/01/how-does-super-glue-work/

    • Explains how humidity contains hydroxyl anions that cause polymerization.

http://www.chm.bris.ac.uk/motm/superglue/superglueh.htm

    • Explains Dr. Harry Coover’s relation to superglue
    • Detailed description of super glue’s polymerization process.

http://www.supergluecorp.com/?q=history.html

    • Explains Dr. Harry Coover’s relation to superglue

http://www.madehow.com/Volume-1/Super-Glue.html

    • Explains how super glue is manufactured

About the Author

Connor Scoles is a junior at BIllings Senior High School. Connor enjoys camping, fishing, and skiing.