A tube of Super glue

Cyanoacrylate is the generic name for substances such as ethyl-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 sometimes known as "instant adhesives". The acronym "CA" is quite commonly used for industrial grades. Image File history File linksMetadata Download high resolution version (1424x576, 167 KB) A tube of super glue Source: Taken by User:Omegatron using a Canon Powershot SD110 File links The following pages link to this file: Cyanoacrylate Metadata This file contains additional information, probably added from the digital camera or... Image File history File linksMetadata Download high resolution version (1424x576, 167 KB) A tube of super glue Source: Taken by User:Omegatron using a Canon Powershot SD110 File links The following pages link to this file: Cyanoacrylate Metadata This file contains additional information, probably added from the digital camera or... Look up glue in Wiktionary, the free dictionary. ... For the chemical substances known as medicines, see medication. ...

History

Cyanoacrylate was discovered by Harry Coover at Eastman Kodak during World War II when searching for a way to make plastic gun-sight lenses. It did not solve this problem, since it stuck to all the apparatus used to handle it. It was first marketed to industry as well as consumers in February 1955 as a product called "Flash Glue" which is still available today and now owned by Gary Shipko, president of Super Glue International, a United States based firm. It was patented in 1956 and developed into Eastman 910 adhesive in 1958. The new glue was demonstrated in 1959 on the television show I've Got a Secret when the host Garry Moore was lifted into the air by two steel plates held together with a drop of Eastman 910. Cyanoacrylates are now a family of adhesives based on similar chemistry. Harry Coover (b. ... Eastman Kodak Company (NYSE: EK) is an American multinational public company which produces photographic materials and equipment. ... Combatants Allied powers: China France Great Britain Soviet Union United States and others Axis powers: Germany Italy Japan and others Commanders Chiang Kai-shek Charles de Gaulle Winston Churchill Joseph Stalin Franklin Roosevelt Adolf Hitler Benito Mussolini Hideki Tōjō Casualties Military dead: 17,000,000 Civilian dead: 33,000... Ive Got a Secret (abbreviated as IGAS) was a weekly panel game show produced by Mark Goodson and Bill Todman for CBS television and was created by Allan Sherman as essentially a knockoff of Whats My Line?. The original version of the show premiered in June 19, 1952... Garry Moore smoking as he often did while hosting Ive Got A Secret Garry Moore (January 31, 1915 – November 28, 1993) was born in Baltimore, Maryland as Thomas Garrison Morfit. ... For the band, see Adhesive (band). ...

Uses

General 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. For the band, see Adhesive (band). ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... For other uses, see Suture (disambiguation). ... “Surgeon” redirects here. ...

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 and also tightening pins and bolts. For other uses, see Lathe (disambiguation). ...

Cyanoacrylates are often 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. They are used to re-harden the boxes and shanks of ballerinas' pointe shoes as well. This article is about the engineering discipline. ... This article deals with electronics manufacturing and prototyping techniques, see Wire wrap jewellery for the jewellery related topic Wire wrap is a technique for constructing small numbers of complex electronics. ... A Die Cast Boeing 747-800 static model. ... A nut is a type of hardware fastener with a threaded hole. ... Screws come in a variety of shapes and sizes for different purposes. ... A scale model of the Tower of London. ... 15mm British Camel Corps and Heliograph Team from Peter Pig A miniature figure -- also known as a miniature or just a mini -- is a small figurine commonly used in role playing games (RPGs) such as Dungeons & Dragons. ... A pair of pointe shoes. ...

One non-adhesive use for cyanoacrylate is as a forensic tool.^[1] Fumes from warmed CA can develop latent fingerprints on smooth surfaces like glass, plastic, etc. The invisible fingerprint residues react with the CA fumes and atmospheric moisture to form a white polymer (polycyanoacrylate) on the fingerprint ridges and can then be recorded. The developed fingerprints are, on most surfaces (except on white plastic or similar), visible to the naked eye. Non-visible or poorly visible prints can be furthermore enhanced by applying a luminescent or non-luminescent stain. This technique was shown in the films Beverly Hills Cop II and National Treasure, and frequently features in the television series CSI: Crime Scene Investigation and its spin-offs. “Beverly Hills Cop II” redirects here. ... This article is about the film. ... CSI: Crime Scene Investigation is a popular Alliance Atlantis/CBS police procedural television series, running since October 2000, about a team of forensic scientists. ...

Thin CA glue is also used as a wood finish, particularly among woodturners. Its fast drying time and glossy finish make it ideal for small applications which generally look best when glossy (such as pens), although it is messy and somewhat expensive. A common mistake made by novice users is to use an accelerator, which can cloud and thus ruin the finish. This article or section is not written in the formal tone expected of an encyclopedia article. ...

Some climbers use glue to prevent damage to the skin on their fingertips.

Medical uses

The use of cyanoacrylate glues in medicine was considered fairly early on. Eastman Kodak and Ethicon began studying whether the glues could be used to hold human tissue together after surgery. In 1964, Eastman submitted an application to use cyanoacrylate glues to seal wounds to the United States Food and Drug Administration (FDA). Soon afterward Dr. Harry Coover's glue did find use in Vietnam—reportedly in 1966, cyanoacrylates were tested on-site by a specially trained surgical team, with impressive results. In an interview with Dr. Coover by the Kingsport Times-News, Coover said that the compound demonstrated an excellent capacity to stop bleeding, and during the Vietnam War, he developed disposable cyanoacrylate sprays for use in the battlefield. For the chemical substances known as medicines, see medication. ... Eastman Kodak Company (NYSE: EK) is an American multinational public company which produces photographic materials and equipment. ... Ethicon can refer to two distinct subsidiares of Johnson & Johnson: [1], a manufacturer of surgical sutures and wound closure devices that was founded in 1949 Ethicon Endo-Surgery, Inc. ... The United States Food and Drug Administration is the government agency responsible for regulating food, dietary supplements, drugs, cosmetics, medical devices, biologics and blood products in the United States. ... Combatants Republic of Vietnam United States Republic of Korea Thailand Australia New Zealand The Philippines National Front for the Liberation of South Vietnam Democratic Republic of Vietnam People’s Republic of China Democratic Peoples Republic of Korea Strength US 1,000,000 South Korea 300,000 Australia 48,000...

The original Eastman formula was not FDA approved for medical use, however, because of a tendency to cause skin irritation and to generate heat. In 1998 the FDA approved 2-octyl cyanoacrylate for use in closing wounds and surgical incisions. Closure Medical has developed medical cyanoacrylates such as Dermabond, Soothe-N-Seal and Band-Aid Liquid Adhesive Bandage.

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. Ethyl-2-cyanoacrylate (C₆H₇NO₂) has a molecular weight equal to 125 and a flashpoint of >75°C. A monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer [1]. // Examples of monomers are hydrocarbons such as the alkene and arene homologous series. ... The flashpoint of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... H2O and HOH redirect here. ...

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. The acryl group is one of the functional groups sorted in the chemical class of acryl where one of four hydrogen atoms in ethene is replaced with a different functional group. ... This article does not cite any references or sources. ... A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ... Hydroxide is a polyatomic ion consisting of oxygen and hydrogen: OH− It has a charge of −1. ... This article is about the electrically charged particle. ... Beads of silica gel Silica gel is a granular, porous form of silica made synthetically from sodium silicate. ...

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. It has been suggested that Para-Toluidine be merged into this article or section. ...

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. Methylene chloride is the most effective but is toxic. Gamma-butyrolactone is also effective at removing superglue, and has low toxicity. The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Flash point 35 °C R/S statement R: S: RTECS number PA9800000 Related compounds Related nitro compounds nitroethane Related compounds methyl nitrite methyl nitrate Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references Nitromethane is an organic... Dichloromethane or Methylene chloride is a chemical compound widely used as a solvent for organic materials. ... gamma-Butyrolactone, also known as GBL, butyrolactone, 1,4-lactone, 4-butyrolactone, 4-hydroxybutyric acid lactone, and gamma-hydroxybutyric acid lactone, is a hygroscopic colorless oily liquid with a weak characteristic odor and is soluble in water. ...

Low temperatures cause cyanoacrylate to become brittle. Cyanoacrylate's bonds can be weakened (allowing disassembly) by placing a glued object in a household freezer for several hours.

If applied to cotton, cyanoacrylate undergoes an exothermic reaction rapid enough to cause minor burns if spilled on clothing. In thermodynamics, the word exothermic describes a process or reaction that releases energy in the form of heat. ...

Polymerization of methyl-2-cyanoacrylate

Image File history File links Download high resolution version (907x135, 12 KB) Summary Polymerization of methyl-2-cyanoacrylate Licensing This image is licensed under the Creative Commons Attribution License v. ... Image File history File links Download high resolution version (907x135, 12 KB) Summary Polymerization of methyl-2-cyanoacrylate Licensing This image is licensed under the Creative Commons Attribution License v. ...

Toxicity

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Cyanoacrylates bond skin and eyes in seconds. The 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.^[2] 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 these toxicity issues, 2-octyl-cyanoacrylate is used for sutures. Image File history File links Question_book-3. ...

Cyanoacrylates give off vapor which is irritating to eyes, mucous membranes and respiratory system. ACGIH assign a Threshold Limit Value exposure limit of 0.2 parts per million. On rare occasions inhalation may trigger asthma. There are a wide variety of adhesives of which different cyanoacrylate formulations may be a component. It is wisest to obtain and consult a manufacturers material safety data sheet for a product in order to consider the specific hazards associated with exposure. The mucous membranes (or mucosa) are linings of ectodermic origin, covered in epithelium, that line various body cavities and internal organs. ... The American Conference of Governmental Industrial Hygienists (ACGIH) community of professionals advance worker safety and health through education and the development and dissemination of scientific and technical knowledge. ... The Threshold Limit Value (TLV) of a chemical substance defines the reasonable level to which a worker can be exposed without adverse health effects. ... Parts per million (ppm) is a measure of concentration that is used where low levels of concentration are significant. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ...

External links

• Was Super Glue invented to seal battle wounds in Vietnam? (from The Straight Dope)
• Cyanoacrylate Toxicity

Cecil Adams is the pen name of the author of The Straight Dope since 1973, a popular question and answer column published in The Chicago Reader, syndicated in thirty newspapers in the United States and Canada, and available online. ...

Patent

U.S. Patent 2,768,109  Alcohol-Catalyzed α-Cyanoacrylate Adhesive Compositions, filed June 1954, issued October 1956

References

1. ^ Eric W. Brown "The Cyanoacrylate Fuming Method"
2. ^ http://www.inchem.org/documents/cicads/cicads/cicad36.htm#11.1

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