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Cyanoacrylate

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Chemical structure of methyl cyanoacrylate
File:Super Glue tube.jpg
A tube of The Original Super Glue.

Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate (commonly sold under trade names like SuperGlue and Krazy Glue), and n-butyl cyanoacrylate (used in the veterinary glues Vetbond and LiquiVet and skin glues like Indermil and Histoacryl). 2-octyl cyanoacrylate is a medical grade glue encountered under various trade names; e.g., LiquiBand, SurgiSeal, FloraSeal, Dermabond, Orabase and Nexaband. Cyanoacrylate adhesives are sometimes known as "instant glues". The abbreviation "CA" is commonly used for industrial grades.

Uses

Cyanoacrylate is a tenacious 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 bothersome (or even dangerous) side effect during everyday use, it has been exploited for the benefit of suture-less surgery.

Cyanoacrylate glue has a low shearing strength, which has also led to its use as a temporary adhesive in cases where the piece can easily be sheared off at a later time. Common examples include mounting a workpiece to a sacrificial glue block on a lathe,[citation needed] and tightening pins and bolts.

Cyanoacrylates are used to assemble prototype electronics (see wire wrap), flying model aircraft, and as retention dressings for nuts and bolts. Their effectiveness in bonding metal and general versatility have also made them popular amongst modeling and miniatures hobbyists.[citation needed] They are used to re-harden the boxes and shanks of ballerinas' pointe shoes as well.

Cyanoacrylate glue's ability to resist water has made it popular with marine aquarium hobbyists for fragging corals. The cut branches of hard corals such as Acropora can be glued to a piece of live rock (harvested reef coral) or Milliput (epoxy putty) to allow the new frag to grow out.[citation needed] In fact, it is actually safe to use directly in the tank, unlike silicone, which must be cured to be safe.[citation needed]

Standard cyanoacrylate adhesive does not bond well to smooth glass, although there are special formulations which are more suitable. A mechanical adhesive bond may be formed around glass fibre mat or tissue to reinforce joints or to fabricate small parts.

When added to baking soda (sodium bicarbonate), cyanoacrylate glue forms a hard, lightweight filler/adhesive (baking soda is first used to fill a gap then the adhesive is dropped onto the baking soda). This works well with porous materials that the glue doesn't work well with alone. This method is sometimes used by aircraft modelers to assemble or repair polystyrene foam parts[citation needed]. It is also used to repair small nicks in the leading edge of composite propeller blades on light aircraft. Note that the reaction between cyanoacrylate and baking soda is very exothermic (heat producing) and also produces noxious vapors. See Reaction with cotton below.

Cyanoacrylate is used as a forensic tool to capture latent fingerprints on non-porous surfaces like glass, plastic, etc.[1] Cyanoacrylate is warmed to produce fumes which react with the invisible fingerprint residues and atmospheric moisture to form a white polymer (polycyanoacrylate) on the fingerprint ridges. The ridges can then be recorded. The developed fingerprints are, on most surfaces (except on white plastic or similar), visible to the naked eye. Invisible or poorly visible prints can be further enhanced by applying a luminescent or non-luminescent stain.

Thin CA glue is also used as a wood finish, particularly among woodturners.[citation needed] It can give a fast drying, glossy finish to wood.

Some rock climbers use cyanoacrylate to repair damage to the skin on their fingertips. Similarly, stringed-instrument players can form protective finger caps (in addition to calluses) with cyanoacrylates.[citation needed]

Superglue was in veterinary use for mending bone, hide, and tortoise shell by at least the early 1970s.[citation needed] The inventor of cyanoacrylates, Harry Coover, said in 1966 that a superglue spray was used in the Vietnam War to retard bleeding in wounded soldiers until they could be brought to a hospital. As it can irritate the skin, the U.S. Food and Drug Administration did not approve superglue's civilian medical use until 1998 when a variant called 2-octyl-cyanoacrylate was developed.[citation needed]

Some glues are 100% ethyl cyanoacrylate,[citation needed] but other glues may be have a mixed composition (e.g., 91% ECA, 9% poly(methyl methacrylate), <0.5% hydroquinone, and a small amount of organic sulfonic acid).[2]

Properties

In its liquid form, cyanoacrylate consists of monomers of cyanoacrylate molecules. Methyl-2-cyanoacrylate (CH2=C(CN)COOCH3 or C5H5NO2) has a molecular weight equal to 111.1, a flashpoint of 79 °C, and 1.1 times the density of water.[citation needed] Ethyl-2-cyanoacrylate (C6H7NO2) has a molecular weight equal to 125 and a flashpoint of >75°C. To facilitate easy handling, a cyanoacrylate adhesive is frequently formulated with an ingredient such as fumed silica to make it more viscous or gel-like.

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. To prevent an opened container of glue from setting before use, it must be stored in an airtight jar or bottle with a package of silica gel.

Polymerization of methyl-2-cyanoacrylate

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.[citation needed]

Acetone, which is commonly found in nail polish remover, is a widely available solvent capable of softening cured cyanoacrylate. Nitromethane is also an excellent solvent. Dimethyl sulfoxide can be used as solvent too. Methylene chloride is the most effective solvent, but is toxic. Gamma-butyrolactone is also effective at removing cured cyanoacrylate, and has low toxicity.

Low temperatures cause cured cyanoacrylate to become brittle. Cyanoacrylate's bonds can be weakened (allowing disassembly) by placing a glued object in a household freezer for several hours. Opened containers of cyanoacrylate glue can also be delayed from prematurely setting by storing the containers in the household refrigerator.

Discovery

Cyanoacrylates were invented in 1942 by Dr. Harry Coover and Fred Joyner of Kodak Laboratories during experiments to make a special extra-clear plastic suitable for gun sights.[3] Although not appropriate for the gun sights, they did find that cyanoacrylates would quickly glue together many materials with great strength. Seeing possibilities for a new adhesive, Kodak developed "Eastman #910" (later "Eastman 910") a few years later as the first true "super glue."

During the 1960s, Eastman Kodak sold cyanoacrylate to Loctite, which in turn repackaged and distributed it under a different brand name "Loctite Quick Set 404." In 1971, Loctite developed its own manufacturing technology and introduced its own line of cyanoacrylate, called Super Bonder. Loctite quickly gained market share and by late 1970s it was believed to have exceeded Eastman Kodak's share in the North American industrial cyanoacrylate market. Other manufacturers of cyanoacrylate included Permabond Division of National Starch and Chemical, Inc., which was a subsidiary of Unilever. Together, Loctite, Eastman and Permabond accounted for approximately 75% of the industrial cyanoacrylate market.[4]

Reaction with cotton

Applying cyanoacrylate to materials made of cotton or wool (such as cotton swabs, cotton balls, and certain yarns or fabrics) results in a powerful, rapid exothermic reaction. The heat released may cause minor burns, and if enough cyanoacrylate is used, the reaction is capable of igniting the cotton product, as well as releasing irritating vapor in the form of white smoke.[5]

Material Safety Data Sheets for cyanoacrylate instruct users not to wear cotton or wool clothing, especially cotton gloves, when applying or handling cyanoacrylates.[6]

Toxicity

The fumes from CA are a vaporized form of the cyanoacrylate monomer that irritate sensitive membranes in the eyes, nose and throat. They are immediately polymerized by the moisture in the membranes and become inert. These risks can be minimized by using CA in well ventilated areas. About 5% of the population can become sensitized to CA fumes after repeated exposure, resulting in flu-like symptoms.[7] It may also act as a skin irritant and may cause an allergic skin reaction. The ACGIH assign a Threshold Limit Value exposure limit of 200 parts per billion. On rare occasions, inhalation may trigger asthma. There is no singular measurement of toxicity for all cyanoacrylate adhesives as there is a wide variety of adhesives that contain various cyanoacrylate formulations.

The United States National Toxicology Program and the United Kingdom Health and Safety Executive have concluded that the use of ethyl cyanoacrylate is safe and that additional study is unnecessary.[8] 2-octyl cyanoacrylate degrades much more slowly due to its longer organic backbone which slows the degradation of the adhesive enough to remain below the threshold of tissue toxicity. Due to the toxicity issues of ethyl cyanoacrylate, the use of 2-octyl cyanoacrylate for sutures is preferred.

See also

References

Specific references:

  1. ^ Eric W. Brown "The Cyanoacrylate Fuming Method"
  2. ^ Safety data for ethyl cyanoacrylate from the Physical and Theoretical Chemistry Laboratory of Oxford University
  3. ^ "Inventor of the Week Archive". Lemelson-MIT Program. September 2004. Retrieved 13 February 2010.
  4. ^ HBS, “Loctite Corporation: Industrial Product Group,” July 15, 1991, p.3
  5. ^ Spontaneous Combustion ! - How To Video from metacafe.com
  6. ^ "Material Safety Data Sheet" (PDF). accumetricinc.com. Retrieved 2008-06-09.
  7. ^ CA PLUS Adhesives, Inc. FAQ
  8. ^ Methyl Cyanoacrylate and Ethyl Cyanoacrylate from inchem.org

General references:

  • Fernandez, Tania (Dr) and Bliskovsky, Val (Dr). "Cyanoacrylate Technology: Stay Glued", Pharmbiz.com, 2 January 2003.
  • Hayes, Sharon Caskey. "Discovery of Super Glue helped land Coover in National Inventors Hall of Fame", Kingsport Times-News, July 11, 2004.
  • Jueneman, F, "Stick it to um", Industrial Research & Development, August 1981, p. 19.
  • Perry LC: An evaluation of acute incisional strength with Traumaseal surgical tissue adhesive wound closure. Dimensional Analysis Systems Inc.
  • Quinn, J., & Kissack, J., "Tissue Adhesives for Laceration Repair During Sporting Events", Clinical Journal of Sports Medicine, Vol. 4 No. 4, 1994, p. 245.
  • Schwade, Nathan D. "Wound Adhesives, 2-Octyl Cyanoacrylate", eMedicine article, 10 April 2002.
  • Vinters HV, Galil KA, Lundie MJ, Kaufmann JC: The histotoxicity of cyanoacrylates. A selective review. Neuroradiology 1985; 27(4): 279–91.
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