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Cyanoacrylate

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Cyanoacrylate
Cyanoacrylate.png
General
Systematic name Cyanoacrylate(1−)
Other names

ethyl-2-cyanoacrylate
methyl 2-cyanoacrylate
Superglue
Krazy Glue
2-octyl cyanoacrylate
n-butyl-cyanoacrylate

Molecular formula

Methyl: C5H5NO2
Ethyl: C6H7NO2

SMILES

Methyl: N#CC(C(OC)=O)=C
Ethyl: N#CC(=C)C(=O)OCC

Molar mass

Molar mass::111.1 g/mol (Methyl)
Molar mass::125.13 g/mol (Ethyl)

Appearance Clear to Cloudy White
CAS number

CAS number::137-05-3 (Methyl)
CAS number::7085-85-0 (Ethyl)

Properties
Density

Density::1.1 (Methyl)
Density::1.06 (Ethyl)

Phase Liquid
Soluble in Acetone, Nitromethane,

or Methylene chloride

Melting point

Melting point::-40 °C (Methyl)
Melting point::-22 °C (Ethyl)

Boiling point

Boiling point::48°C Methyl (2.5-2.7 mm Hg)
Boiling point::54 °C Ethyl (3mm Hg)

Hazards
MSDS Methyl: Material safety data sheet

Ethyl: Material safety data sheet

Main hazards

Methyl: on contact will bond skin,
will bond eyelids together,
eye irritant, skin irritant.

Ethyl: Harmful if swallowed.
May be harmful if inhaled
or in contact with the skin

Flash point

Methyl: 79 °C
Ethyl: 75°C

RTECS number Methyl: AS7000000

Ethyl: UD3330050

Related compounds
Related compounds

Butyl cyanoacrylate
n-butyl cyanoacrylate
2-octyl cyanoacrylate
octyl cyanoacrylate

Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Cyanoacrylate also known as Superglue or Krazy glue by its common name, or methyl 2-cyanoacrylate or ethyl 2-cyanoacrylate. Cyanoacrylate is a common glue that adheres and cures quickly, especially when exposed to moisture. It is quite popular in many areas of study including the medical field, where it is starting to replace many old methods. What makes Cyanoacrylate so effective is its ability to polymerize quickly, providing a quick and very strong bond to almost any surface.

Properties

A tube of superglue that has been exposed to too much moisture and has hardened.

In addition to the properties listed in the table to the right, [1] [2] [3] [4] [5] [6] Cyanoacrylate is extremely reactive with water. It will form a very strong adhesive whenever exposed to water. This is why it is important to keep bottles of Cyanoacrylate tightly sealed and away from water or humidity. If a bottle is left with its lid open, it is likely to lose its adhesive abilities because the humidity in the air will cause it to harden. However, after it has dried, Cyanoacrylate is waterproof. Cyanoacrylate is an extremely fast acting adhesive that can be used in a wide range of ways. It is able to adhere quickly and can have added accelerators for an even faster reaction time, however it will lose some of its strength in its bond, but that is only a relatively small amount. A common accelerator used in Cyanoacrylate is toluidine. However, there are some ways in which a person can separate two objects that have been attached using Cyanoacrylate, one way is to put the objects in the freezer. The cold causes the Cyanoacrylate to become brittle and break apart. Another way to separate to objects adhered together is by using a solvent like Acetone, which is usually found in nail polish, other solvents include Nitromethane, or Methylene chloride. This means that a person could soak something in nail polish remover and it would cause the Cyanoacrylate bond to break apart. [1]

Manufacturing

Cyanoacrylate is formed by synthetic polymers, a molecule that is made up of even smaller molecules that stay together by bonding to each other. After one polymeric reaction has occurred often times, it is followed by many more, causing the glue to dry and harden quickly.

Ethyl cyanoacetate is mixed together with formaldehyde in a glass-lined kettle with revolving blades. As the two chemicals mixed condensation is produced, after any water in the mixture has evaporated off C.A. (another way to refer to Cyanoacrylate) polymer is left. The kettle now has to be heated to around 305 degrees Fahrenheit so that the polymer will go through thermal cracking, releasing reactive monomers. These monomers will reattach when the glue is actually used. The monomers being less heavy than the polymers evaporate upward quickly and are transferred into another kettle through a pipe. As they are traveling through the pipe, the monomers pass through multiple cooling coils which cause them to change phases from gases to liquids. If the manufacturer wants a truly good product, he or she may put it through one or more additional rounds of distillation. The now liquid monomers are Cyanoacrylate glue, but they must now have chemicals added to it to keep it form curing to soon. These chemicals are referred to as free radical inhibitors their job is simple to keep the Cyanoacrylate from becoming hard before it is actually meant to be used. Along with the free radical inhibitors, base scavengers are added to the monomers. These function just like the free radical inhibitors, they both will separate out impurities that would cause the glue to prematurely cure or harden. After these are added the producer of the glue can add anything that he wants to add to the glue, they can add something that will cause the glue to have a thicker viscosity. It really all just depends on what the consumer is buying the glue for. Now the glue is ready to be packaged, however it must be packaged using albeit humidity-free, techniques. This is because when exposed to moisture the glue will harden. Also it can not be packaged in just anything because it may react with it so it usually is put in plastic or aluminum tubes. The whole process would have fallen apart however if any of the chemicals, equipment, or even if one step was changed. Because of the chance of polymerization, this would cause all the glue to harden destroying an entire kettle of Cyanoacrylate. [7]

Uses

Skin closed with DuraBond (medical superglue) after surgery.

Cyanoacrylate has many different uses including many home uses like model airplanes or simple repairs. Many times Cyanoacrylate or super glue is used to hold together the pieces of a model airplane; it can also help fix a broken object like a broken figurine. This is one of the reasons that Cyanoacrylate is so popular with hobbyists. Also it is used by some people to repair shoes even ballerinas slippers. The nice thing about Cyanoacrylate is it is waterproof this means that after the couple of minutes it takes to dry you can place a glued object in water. This is extremely helpful for people with marine aquariums, they are able to glue their plants and other decorations in the tank or onto each other, and they will stay because the glue is waterproof. Also Cyanoacrylate can be used along with baking soda to fill larger porous cracks, for example you can fill a crack in foam with baking soda and then put some super glue in it. The super glue will go a long way in the crack because of the baking soda, filling in the crack. [2] An extremely helpful use of Cyanoacrylate actually involves fingerprinting. If a forensic technician is trying to remove a fingerprint from something smooth like glass they can use Cyanoacrylate. How they do that is first they heat Cyanoacrylate until it begins to produce fumes, these fumes are then attracted to the ridges of the fingerprint, and bond with them. The bonds form a white kind of polymer, the fingerprint is then recorded. [8] Cyanoacrylate also has a place next to the scalpel and suture on a surgeon’s instrument table. It is being used more and more because of many factors; it does not leave as much scaring as stitches do but will still hold the skin together. Also it does not allow germs or bacteria in because it is not penetrating the skin like a suture does. Cyanoacrylate is a lot easier to use, a suture takes much longer then it takes to use cyanoacrylate to close a wound. This time saved also means money saved because a person is not in surgery as long. [9]

History

Cyanoacrylate was first discovered by Dr. Harry Coover who worked for the Kodak Research Laboratories. He was working on a clear plastic that could be used for gun sights, instead of discovering that however he found Cyanoacrylate which he passed over because it was too sticky. Coover later came back to the glue with Dr. Fred Joyner in 1951. The two men had been trying to create a heat-resistant acrylate polymer for jet canopies, again Coover stumbled upon Cyanoacrylate. As the two men tested a thin piece of ethyl Cyanoacrylate in their prism, this stuck the two pieces together destroying their prism. Coover did not try to make a profit off of Cyanoacrylate until 1958 when he sold it under the name the Eastman compound #910, the name later changed to superglue. [10]

References

  1. 1.0 1.1 Cyanoacrylate Spectrum, WikiDoc, last modified 18:30, 3 August 2010.
  2. 2.0 2.1 Cyanoacrylate Unknown Author, Wikipedia, last modified on 16 February 2011 at 10:42.
  3. Methyl cyanoacrylate Unknown Author, Wikipedia, last modified on 31 January 2011 at 07:28.
  4. Ethyl cyanoacrylate Unknown Author, Wikipedia, last modified on 3 February 2011 at 13:55.
  5. Methyl-2-cyanoacrylate Kenneth Barbalace, Environmental Chemistry, Accessed on-line: 2/16/2011.
  6. ETHYL 2-CYANOACRYLATE Unknown Author, International Labor Organizatoin, partly updated in April 2005.
  7. Super Glue Unknown Author, How Products Are Made, Accessed; February 17, 2011.
  8. The Cyanoacrylate Fuming Method Eric W. Brown, Published in NU-ENG 1990, Accessed: February 16, 2011.
  9. New Process of Obtaining Cyanoacrylate Monomers and Cyanoacrylate Nanoparticles European University, Tynax Inc, Accessed: February 17, 2011.
  10. The History of Adhesives and Glue Mary Bellis, About.com, Accessed: February 17, 2011.