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Cyanoacrylates are a family of strong fast-acting
adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advant ...
s with industrial, medical, and household uses. They are derived from
ethyl cyanoacrylate Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with low viscosity and a faint sweet smell in pure form. It is the main component of cyanoacrylate glues and can be encount ...
and related
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
s. The cyanoacrylate group in the monomer rapidly
polymer A polymer (; Greek '' poly-'', "many" + '' -mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
izes in the presence of water to form long, strong chains. They have some minor toxicity. Specific cyanoacrylates include methyl 2-cyanoacrylate (MCA), ethyl 2-cyanoacrylate (ECA, commonly sold under trade names such as "Super Glue" and "Krazy Glue", or
Toagosei is a Japanese chemical company, producing cyanoacrylate adhesives since 1963. Other chemical products of the company include high purity gases, soda and chlorine products, and instant glue, which is sold in Japan as Aron Alpha and marketed in t ...
), ''n''-butyl cyanoacrylate (n-BCA),
octyl cyanoacrylate Octyl cyanoacrylate (OCA), a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. Its chief use is as the main component of medical cyanoacrylate glues. In medical and ...
, and 2-octyl cyanoacrylate (used in medical, veterinary and first aid applications). Octyl cyanoacrylate was developed to address toxicity concerns and to reduce skin irritation and allergic response. Cyanoacrylate adhesives are sometimes known generically as instant glues, power glues or superglues. The abbreviation "CA" is commonly used for industrial grade cyanoacrylate.


Development

The original
patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an enabling disclosure of the invention."A ...
for cyanoacrylate was filed in 1947 by the
B.F. Goodrich Company The Goodrich Corporation, formerly the B.F. Goodrich Company, was an American manufacturing company based in Charlotte, North Carolina. Founded in Akron, Ohio in 1870 as Goodrich, Tew & Co. by Benjamin Goodrich, the company name was ch ...
as an outgrowth of a search for materials suitable for clear plastic gun sights for the war effort. In 1942, a team of scientists headed by
Harry Coover Harry Wesley Coover Jr. (March 6, 1917 – March 26, 2011) was the inventor of Eastman 910, commonly known as Super Glue. Life and career Coover was born in Newark, Delaware. He lived in Delaware until his teen years. During this time he was hi ...
Jr. stumbled upon a formulation that stuck to everything with which it came in contact. The team quickly rejected the substance for the wartime application, but in 1951, while working as researchers for
Eastman Kodak The Eastman Kodak Company (referred to simply as Kodak ) is an American public company that produces various products related to its historic basis in analogue photography. The company is headquartered in Rochester, New York, and is incorpor ...
, Coover and a colleague, Fred Joyner, rediscovered cyanoacrylates. The two realized the true commercial potential, and a form of the adhesive was first sold in 1958 under the title "Eastman #910" (later "Eastman 910"). During the 1960s, Eastman Kodak sold cyanoacrylate to
Loctite Loctite is an American brand of adhesives, sealants, surface treatments, and other industrial chemicals that include acrylic, anaerobic, cyanoacrylate, epoxy, hot melt, silicone, urethane, and UV/light curing technologies. Loctite product ...
, 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 the late 1970s it was believed to have exceeded Eastman Kodak's share in the
North America North America is a continent in the Northern Hemisphere and almost entirely within the Western Hemisphere. It is bordered to the north by the Arctic Ocean, to the east by the Atlantic Ocean, to the southeast by South America and th ...
n industrial cyanoacrylate market. National Starch and Chemical Company purchased Eastman Kodak's cyanoacrylate business and combined it with several acquisitions made throughout the 1970s forming Permabond. Other manufacturers of cyanoacrylate include LePage (a
Canadian Canadians (french: Canadiens) are people identified with the country of Canada. This connection may be residential, legal, historical or cultural. For most Canadians, many (or all) of these connections exist and are collectively the source of ...
company acquired by
Henkel AG & Co. KGaA, commonly known as Henkel, is a German multinational chemical and consumer goods company headquartered in Düsseldorf, Germany. It is active in both the consumer and industrial sectors. Founded in 1876, the DAX company is organ ...
in 1996), the Permabond Division of National Starch and Chemical, which was a subsidiary of
Unilever Unilever plc is a British multinational consumer goods company with headquarters in London, England. Unilever products include food, condiments, bottled water, baby food, soft drink, ice cream, instant coffee, cleaning agents, energy dri ...
. Together, Loctite, Eastman, and Permabond accounted for approximately 75% of the industrial cyanoacrylate market. Permabond continued to manufacture the original 910 formula.


Monomers

In its liquid form, cyanoacrylate consists of
monomer In chemistry, a monomer ( ; '' mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification ...
s of cyanoacrylate ester molecules. Methyl 2-cyanoacrylate (CH2=C(C≡N)COOCH3) has a
molecular weight A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bio ...
of 111.1 g/mol, a flashpoint of , and a density of 1.1 g/mL. Ethyl 2-cyanoacrylate ((CH2=C(C≡N)COOCH2CH3)) has a molecular weight of 125 g/mol and a flashpoint of more than . To facilitate easy handling, a cyanoacrylate adhesive is frequently formulated with an ingredient such as
fumed silica Fumed silica (CAS_Registry_Number, CAS number 112945-52-5), also known as pyrogenic silica because it is produced in a flame, consists of microscopic droplets of amorphous silica fused into branched, chainlike, three-dimensional secondary partic ...
to make it more
viscous The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water. Viscosity quantifies the in ...
or gel-like. More recently, formulations are available with additives to increase
shear strength In engineering, shear strength is the strength of a material or component against the type of yield or structural failure when the material or component fails in shear. A shear load is a force that tends to produce a sliding failure on a materi ...
, creating a more impact resistant bond. Such additives may include
rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Thailand, Malaysia, and ...
, as in Loctite's "Ultra Gel", or others which are not specified. In general, the acryl groups rapidly undergo chain-growth polymerisation in the presence of water (specifically
hydroxide ion Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It ...
s), forming long, strong chains, joining the bonded surfaces together. Because the presence of moisture causes the glue to set, exposure to normal levels of
humidity Humidity is the concentration of water vapor present in the air. Water vapor, the gaseous state of water, is generally invisible to the human eye. Humidity indicates the likelihood for precipitation, dew, or fog to be present. Humidity dep ...
in the air causes a thin skin to start to form within seconds, which very greatly slows the reaction; hence, cyanoacrylates are applied as thin coats to ensure that the reaction proceeds rapidly for bonding. Cyanoacrylate adhesives have a short
shelf life Shelf life is the length of time that a commodity may be stored without becoming unfit for use, consumption, or sale. In other words, it might refer to whether a commodity should no longer be on a pantry shelf (unfit for use), or no longer on a ...
—about one year from manufacture if unopened, and one month once opened.


Uses


General properties

Cyanoacrylates are mainly used as adhesives. Thin layers bond effectively, thick layers much less so. They bond many substances, including human skin and tissues, natural fibres, cotton, wool, and leather. Cyanoacrylate glue has a low
shearing Sheep shearing is the process by which the woollen fleece of a sheep is cut off. The person who removes the sheep's wool is called a '' shearer''. Typically each adult sheep is shorn once each year (a sheep may be said to have been "shorn" o ...
strength, which has led to its use as a temporary adhesive in cases where the piece needs to be sheared off later. Common examples include mounting a workpiece to a sacrificial glue block on a
lathe A lathe () is a machine tool that rotates a workpiece about an axis of rotation to perform various operations such as cutting, sanding, knurling, drilling, deformation, facing, and turning, with tools that are applied to the workpiece ...
, and tightening pins and bolts. It is also used in conjunction with another slower, but more resilient, adhesive as a way of rapidly forming a joint, which then holds the pieces in the appropriate configuration until the second adhesive has set. Cyanoacrylate-based glue has a weak bond with smooth surfaces and as such easily gives to friction; a good example of this is the fact that cyanoacrylates may be removed from human skin by means of abrasives (e.g. sugar or sandpaper).


Electronics

Cyanoacrylates are used to assemble prototype
electronics The field of electronics is a branch of physics and electrical engineering that deals with the emission, behaviour and effects of electrons using electronic devices. Electronics uses active devices to control electron flow by amplification ...
(used in
wire wrap Wire wrap is an electronic component assembly technique that was invented to wire telephone crossbar switches, and later adapted to construct electronic circuit boards. Electronic components mounted on an insulating board are interconnected by ...
), flying
model aircraft A model aircraft is a small unmanned aircraft. Many are replicas of real aircraft. Model aircraft are divided into two basic groups: flying and non-flying. Non-flying models are also termed static, display, or shelf models. Aircraft manufactur ...
, and as retention dressings for nuts and bolts. Their effectiveness in bonding metal and general versatility have made them popular among
modeling A model is an informative representation of an object, person or system. The term originally denoted the plans of a building in late 16th-century English, and derived via French and Italian ultimately from Latin ''modulus'', a measure. Models c ...
and miniatures hobbyists.


Aquaria

Cyanoacrylate glue's ability to resist water has made it popular with marine aquarium hobbyists for fragmenting corals. The cut branches of
hard corals Scleractinia, also called stony corals or hard corals, are marine animals in the phylum Cnidaria that build themselves a hard skeleton. The individual animals are known as polyps and have a cylindrical body crowned by an oral disc in which a mo ...
, such as
Acropora ''Acropora'' is a genus of small polyp stony coral in the phylum Cnidaria. Some of its species are known as table coral, elkhorn coral, and staghorn coral. Over 149 species are described. ''Acropora'' species are some of the major reef corals r ...
, can be glued to a piece of live rock (harvested reef coral) or
Milliput {{Primary sources, date=December 2010 Milliput is a UK-based brand of epoxy putty used by modellers, and also for household and restoration applications. Created in 1968 by Jack and Lena Rickman, Milliput was initially marketed for use in DIY and ...
(epoxy putty) to allow the new fragment to grow out. It is safe to use directly in the tank, unlike
silicone A silicone or polysiloxane is a polymer made up of siloxane (−R2Si−O−SiR2−, where R = organic group). They are typically colorless oils or rubber-like substances. Silicones are used in sealants, adhesives, lubricants, medicine, cookin ...
which must be cured to be safe. However, as a class of adhesives, traditional cyanoacrylates are classified as having "weak" resistance to both moisture and heat although the inclusion of
phthalic anhydride Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commer ...
reportedly counteracts both of these characteristics. Cyanoacrylate glue is also used frequently in
aquascaping Aquascaping is the craft of arranging aquatic plants, as well as rocks, stones, cavework, or driftwood, in an aesthetically pleasing manner within an aquarium—in effect, gardening under water. Aquascape designs include a number of distinct styl ...
both freshwater and marine aquariums for the purpose of securing the
rhizomes In botany and dendrology, a rhizome (; , ) is a modified subterranean plant stem that sends out roots and shoots from its nodes. Rhizomes are also called creeping rootstalks or just rootstalks. Rhizomes develop from axillary buds and grow ...
of live plants to pieces of wood or stone.


Smooth surfaces

Most standard cyanoacrylate adhesives do not bond well with smooth
glass Glass is a non- crystalline, often transparent, amorphous solid that has widespread practical, technological, and decorative use in, for example, window panes, tableware, and optics. Glass is most often formed by rapid cooling (quenchin ...
, although they can be used as a quick, temporary bond prior to application of an epoxy or cyanoacrylate specifically formulated for use on glass. A mechanical adhesive bond may be formed around
glass fibre Glass fiber ( or glass fibre) is a material consisting of numerous extremely fine fibers of glass. Glassmakers throughout history have experimented with glass fibers, but mass manufacture of glass fiber was only made possible with the inventio ...
mat or tissue to reinforce joints or to fabricate small parts.


Filler

When added to baking soda (
sodium bicarbonate Sodium bicarbonate ( IUPAC name: sodium hydrogencarbonate), commonly known as baking soda or bicarbonate of soda, is a chemical compound with the formula NaHCO3. It is a salt composed of a sodium cation ( Na+) and a bicarbonate anion ( HCO3− ...
), cyanoacrylate glue forms a hard, lightweight adhesive filler. This works well with porous materials that do not work well with the adhesive alone. This method is sometimes used by aircraft modelers to assemble or repair
polystyrene Polystyrene (PS) is a synthetic polymer made from monomers of the Aromatic hydrocarbon, aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin pe ...
parts. It is also used to repair small nicks in the leading edge of wood
propeller A propeller (colloquially often called a screw if on a ship or an airscrew if on an aircraft) is a device with a rotating hub and radiating blades that are set at a pitch to form a helical spiral which, when rotated, exerts linear thrust upon ...
blades on light aircraft, although this technique is limited to use on aircraft registered in the "experimental" category (composite propellers can be repaired in a similar way using two-part epoxies). This technique can also be used to fill in the slots in the nut of a guitar so that new ones can be cut. The reaction between cyanoacrylate and baking soda is very exothermic (heat-producing) and also produces noxious vapors. One brand of cyanoacrylate, "SupaFix", uses
calcium oxide Calcium oxide (CaO), commonly known as quicklime or burnt lime, is a widely used chemical compound. It is a white, caustic, alkaline, crystalline solid at room temperature. The broadly used term "'' lime''" connotes calcium-containing inorganic ...
as a filler giving an even harder (mortar-like in texture) result that can be used to join hard materials and even repair cracked castings.


Forensics

Cyanoacrylate is used as a
forensic Forensic science, also known as criminalistics, is the application of science to criminal and civil laws, mainly—on the criminal side—during criminal investigation, as governed by the legal standards of admissible evidence and criminal p ...
tool to capture latent fingerprints on non-porous surfaces like glass,
plastic Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adapta ...
, etc. Cyanoacrylate is warmed to produce fumes that 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.


Woodworking

Thin cyanoacrylate glue has application in
woodworking Woodworking is the skill of making items from wood, and includes cabinet making (cabinetry and furniture), wood carving, joinery, carpentry, and woodturning. History Along with stone, clay and animal parts, wood was one of the first mate ...
. It can be used as a fast-drying, glossy finish. An oil, such as
boiled linseed oil Linseed oil, also known as flaxseed oil or flax oil (in its edible form), is a colourless to yellowish oil obtained from the dried, ripened seeds of the flax plant (''Linum usitatissimum''). The oil is obtained by pressing, sometimes followed by ...
, may be used to control the rate at which the cyanoacrylate cures. Cyanoacrylate glue is also used in combination with
sawdust Sawdust (or wood dust) is a by-product or waste product of woodworking operations such as sawing, sanding, milling, planing, and routing. It is composed of small chippings of wood. These operations can be performed by woodworking machine ...
(from a saw or sanding) to fill voids and cracks. These repair methods are used on piano soundboards, wood instruments, and wood furniture. Cyanoacrylate glue is also used in the finishing of pen blanks (wooden blanks for turning pens) that have been turned on a lathe by applying multiple thin layers to build up a hard, clear finish that can then be sanded and polished to a glossy finish.


Medical and veterinary

Cyanoacrylate glue was in veterinary use for mending bone, hide, and tortoise shell by the early 1970s or before.
Harry Coover Harry Wesley Coover Jr. (March 6, 1917 – March 26, 2011) was the inventor of Eastman 910, commonly known as Super Glue. Life and career Coover was born in Newark, Delaware. He lived in Delaware until his teen years. During this time he was hi ...
said in 1966 that a cyanoacrylate spray was used in the
Vietnam War The Vietnam War (also known by #Names, other names) was a conflict in Vietnam, Laos, and Cambodia from 1 November 1955 to the fall of Saigon on 30 April 1975. It was the second of the Indochina Wars and was officially fought between North Vie ...
to reduce bleeding in wounded soldiers until they could be taken to a hospital. ''n''-Butyl cyanoacrylate has been used medically since the 1970s. In the US, due to its potential to irritate the skin, the U.S. Food and Drug Administration (FDA) did not approve its use as a medical adhesive until 1998 with Dermabond (2-octyl cyanoacrylate). A 1986 independent study suggests that cyanoacrylate can be safer and more functional for wound closure than traditional
suturing A surgical suture, also known as a stitch or stitches, is a medical device used to hold body tissues together and approximate wound edges after an injury or surgery. Application generally involves using a needle with an attached length of thre ...
(stitches). The adhesive is superior in terms of time required to close wounds, the incidence of
infection An infection is the invasion of tissues by pathogens, their multiplication, and the reaction of host tissues to the infectious agent and the toxins they produce. An infectious disease, also known as a transmissible disease or communicable di ...
(suture canals through the skin's epidermal, dermal, and subcutaneous fat layers introduce additional routes of contamination), and finally cosmetic appearance. Some
rock climbers Rock climbing is a sport in which participants climb up, across, or down natural rock formations. The goal is to reach the summit of a formation or the endpoint of a usually pre-defined route without falling. Rock climbing is a physically an ...
use cyanoacrylate to repair damage to the skin on their fingertips. Similarly, stringed-instrument players can form protective finger caps (typically, when they lose their
callus A callus is an area of thickened and sometimes hardened skin that forms as a response to repeated friction, pressure, or other irritation. Since repeated contact is required, calluses are most often found on the feet and hands, but they may o ...
es due to inactivity or accidents) with cyanoacrylates. While the glue is not very toxic and wears off quickly with shed skin, applying large quantities of glue and its fumes directly to the skin can cause
chemical burn A chemical burn occurs when living tissue is exposed to a corrosive substance (such as a strong acid, base or oxidizer) or a cytotoxic agent (such as mustard gas, lewisite or arsine). Chemical burns follow standard burn classification and may c ...
s. While standard "superglue" is 100% ethyl 2-cyanoacrylate, many custom formulations (e.g.'','' 91% ECA, 9%
poly(methyl methacrylate) Poly(methyl methacrylate) (PMMA) belongs to a group of materials called engineering plastics. It is a transparent thermoplastic. PMMA is also known as acrylic, acrylic glass, as well as by the trade names and brands Crylux, Plexiglas, Acrylit ...
, <0.5%
hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''pa ...
, and a small amount of organic
sulfonic acid In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula , where R is an organic alkyl or aryl group and the group a sulfonyl hydroxide. As a substituent, it is k ...
, and variations on the compound ''n''-butyl cyanoacrylate for medical applications) have come to be used for specific applications. There are three cyanoacrylate compounds currently available as topical skin adhesives. 2-Octyl cyanoacrylate is marketed as Dermabond, SurgiSeal, and more recently LiquiBand Exceed. ''n''-Butyl cyanoacrylate is marketed as Histoacryl, Indermil, GluStitch, GluSeal, PeriAcryl, and LiquiBand. The compound ethyl 2-cyanoacrylate is available as Epiglu. The ester substituent has several effects upon the biocompatibility of the adhesive. Longer side chains result in higher flexibility of the cured adhesive allowing a better match for the flexibility of skin, and can result in a slower release of formaldehyde after curing. Alkoxy-ethyl substituents have also been investigated and have shown some promise as a medical adhesive.


Archery

Cyanoacrylate is used in
archery Archery is the sport, practice, or skill of using a bow to shoot arrows.Paterson ''Encyclopaedia of Archery'' p. 17 The word comes from the Latin ''arcus'', meaning bow. Historically, archery has been used for hunting and combat. In ...
to glue
fletching Fletching is the fin-shaped aerodynamic stabilization device attached on arrows, bolts, darts, or javelins, and are typically made from light semi-flexible materials such as feathers or bark. Each piece of such fin is a fletch, also known as a ...
to arrow shafts. Some special fletching glues are primarily cyanoacrylate repackaged in special fletching glue kits. Such tubes often have a long, thin metal nozzle for improved precision in applying the glue to the base of the fletching and to ensure secure bonding to the arrow shaft.


Cosmetics

Cyanoacrylate is used in the cosmetology and beauty industry as an eyelash extension glue, or a "nail glue" for some artificial nail enhancements such as nail tips and nail wraps, and is sometimes mistaken for
eye drops Eye drops or eyedrops are liquid drops applied directly to the surface of the eye usually in small amounts such as a single drop or a few drops. Eye drops usually contain saline to match the salinity of the eye. Drops containing only saline ...
causing accidental injury (
chemical eye injury Chemical eye injury are due to either an acidic or alkali substance getting in the eye. Alkalis are typically worse than acidic burns. Mild burns will produce conjunctivitis while more severe burns may cause the cornea to turn white. Litmus paper ...
).


Safety issues


Skin injuries

Cyanoacrylate adhesives may adhere to body parts, and injuries may occur when parts of the skin are torn off. Without force, however, the glue will spontaneously separate from the skin in time (up to four days). Separation can be accelerated by applying
vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or f ...
near, on, and around the glue. In the case of glued eyelids, especially if it has contacted the eyeball, a doctor should be consulted.


Toxicity

The fumes from cyanoacrylate are a vaporized form of the cyanoacrylate monomer that irritate the sensitive
mucous membrane A mucous membrane or mucosa is a membrane that lines various cavities in the body of an organism and covers the surface of internal organs. It consists of one or more layers of epithelial cells overlying a layer of loose connective tissue. It i ...
s of the
respiratory tract The respiratory tract is the subdivision of the respiratory system involved with the process of respiration in mammals. The respiratory tract is lined with respiratory epithelium as respiratory mucosa. Air is breathed in through the nose to ...
(nose, throat, and lungs) and the eyes. They are immediately polymerized by the moisture in the membranes and become inert. These risks can be minimized by using cyanoacrylate in well-ventilated areas. About 5% of the population can become sensitized to cyanoacrylate fumes after repeated exposure, resulting in
flu-like symptoms Influenza-like illness (ILI), also known as flu-like syndrome or flu-like symptoms, is a medical diagnosis of possible influenza or other illness causing a set of common symptoms. These include fever, shivering, chills, malaise, dry cough, loss ...
. Cyanoacrylate may also be a skin irritant, causing an allergic skin reaction. The
American Conference of Governmental Industrial Hygienists The American Conference of Governmental Industrial Hygienists (ACGIH) is a professional association of industrial hygienists and practitioners of related professions, with headquarters in Cincinnati, Ohio. One of its goals is to advance worker pr ...
(ACGIH) assign a threshold limit value exposure limit of 200
parts per billion In science and engineering, the parts-per notation is a set of pseudo-units to describe small values of miscellaneous dimensionless quantities, e.g. mole fraction or mass fraction. Since these fractions are quantity-per-quantity measures, th ...
. On rare occasions, inhalation may trigger
asthma Asthma is a long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wheezing, co ...
. There is no singular measurement of toxicity for all cyanoacrylate adhesives because of the large number of adhesives that contain various cyanoacrylate formulations. The United Kingdom's
Health and Safety Executive The Health and Safety Executive (HSE) is a UK government agency responsible for the encouragement, regulation and enforcement of workplace health, safety and welfare, and for research into occupational risks in Great Britain. It is a non-depar ...
and the United States
National Toxicology Program The National Toxicology Program (NTP) is an inter-agency program run by the United States Department of Health and Human Services to coordinate, evaluate, and report on toxicology within public agencies. The National Toxicology Program is headqua ...
have concluded that the use of ethyl cyanoacrylate is safe and that additional study is unnecessary. The compound 2-octyl cyanoacrylate degrades much more slowly due to its longer organic backbone (series of covalently bonded
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ...
molecules) and the adhesive does not reach the threshold of tissue toxicity. Due to the toxicity issues of ethyl cyanoacrylate, the use of 2-octyl cyanoacrylate for sutures is preferred.


Reaction with cotton, wool, and other fibrous materials

Applying cyanoacrylate to some natural materials such as
cotton Cotton is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure cellulose, and can contain minor pe ...
(
jeans Jeans are a type of pants or trousers made from denim or dungaree cloth. Often the term "jeans" refers to a particular style of trousers, called "blue jeans", with copper-riveted pockets which were invented by Jacob W. Davis in 1871 and pa ...
,
cotton swab Cotton is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus ''Gossypium'' in the mallow family Malvaceae. The fiber is almost pure cellulose, and can contain minor perc ...
s,
cotton ball Cotton pads are pads made of cotton which are used for medical or cosmetic purposes. For medical purposes, cotton pads are used to stop or prevent bleeding from minor punctures such as injections or venipuncture. They may be secured in place wi ...
s, and certain
yarn Yarn is a long continuous length of interlocked fibres, used in sewing, crocheting, knitting, weaving, embroidery, ropemaking, and the production of textiles. Thread is a type of yarn intended for sewing by hand or machine. Modern manu ...
s or fabrics), or
leather Leather is a strong, flexible and durable material obtained from the tanning, or chemical treatment, of animal skins and hides to prevent decay. The most common leathers come from cattle, sheep, goats, equine animals, buffalo, pigs and hog ...
or
wool Wool is the textile fibre obtained from sheep and other mammals, especially goats, rabbits, and camelids. The term may also refer to inorganic materials, such as mineral wool and glass wool, that have properties similar to animal wool. ...
results in a powerful, rapid,
exothermic In thermodynamics, an exothermic process () is a thermodynamic process or reaction that releases energy from the system to its surroundings, usually in the form of heat, but also in a form of light (e.g. a spark, flame, or flash), electricity ...
reaction. This reaction also occurs with
fiberglass Fiberglass ( American English) or fibreglass (Commonwealth English) is a common type of fiber-reinforced plastic using glass fiber. The fibers may be randomly arranged, flattened into a sheet called a chopped strand mat, or woven into glass cl ...
and
carbon fiber Carbon fiber-reinforced polymers (American English), carbon-fibre-reinforced polymers (Commonwealth English), carbon-fiber-reinforced plastics, carbon-fiber reinforced-thermoplastic (CFRP, CRP, CFRTP), also known as carbon fiber, carbon compo ...
. The heat released may cause serious burns or release irritating white smoke. Material safety data sheets for cyanoacrylate instruct users not to wear cotton (jeans) or wool clothing, especially cotton gloves, when applying or handling cyanoacrylates.


Solvents and debonders

Acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscibl ...
, commonly found as a fraction of
nail polish remover Nail polish (also known as nail varnish or nail enamel) is a lacquer that can be applied to the human fingernail or toenails to decorate and protect the nail plates. The formula has been revised repeatedly to enhance its decorative properties ...
(or at hardware stores in pure form), is a widely available solvent capable of softening cured cyanoacrylate. Other solvents include
nitromethane Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in ...
,
dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majo ...
,
dimethyl sulfoxide Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds a ...
, and
methylene chloride Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...
. Another viable solvent for removing cured cyanoacrylate is ''gamma''-butyrolactone. Commercial debonders are also available, many based on
propylene carbonate Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol. This colorless and odorless liquid is useful as a polar, aprotic solvent. Propylene carbonat ...
.


Shelf life

Cyanoacrylate adhesives have a short shelf life. Date-stamped containers help to ensure that the adhesive is still viable. One manufacturer supplies the following information and advice:
When kept unopened in a cool, dry location such as a refrigerator at a temperature of about 55 °F (13 °C), the shelf life of cyanoacrylate will be extended from about one year from manufacture to at least 15 months. If the adhesive is to be used within six months, it is not necessary to refrigerate it. Cyanoacrylates are moisture-sensitive, and moving from a cool to a hot location will create condensation; after removing from the refrigerator, it is best to let the adhesive reach room temperature before opening. After opening, it should be used within 30 days. Open containers should not be refrigerated.
Another manufacturer says that the maximum shelf life of 12 months is obtained for some of their cyanoacrylates if the original containers are stored at . User forums and some manufacturers say that an almost unlimited shelf life is attainable by storing unopened at , the typical temperature of a domestic
freezer A refrigerator, colloquially fridge, is a commercial and home appliance consisting of a thermally insulated compartment and a heat pump (mechanical, electronic or chemical) that transfers heat from its inside to its external environment so th ...
, and allowing the contents to reach room temperature before use. Opening a container while chilled may cause moisture from the air to condense in the container; however, reports from hobbyists suggest that storing cyanoacrylate in a freezer can preserve opened cyanoacrylate indefinitely. As cyanoacrylates age, they polymerize, become thicker, and cure more slowly. They can be thinned with a cyanoacrylate of the same chemical composition with lower
viscosity The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water. Viscosity quantifies the int ...
. Storing cyanoacrylates below will nearly stop the polymerization process and prevent aging.


References


Further reading

* derma+flex QS 510k Letter: http://www.accessdata.fda.gov/cdrh_docs/pdf10/K101276.pdf * LiquiBand 510k Letter: http://www.accessdata.fda.gov/cdrh_docs/pdf8/K083531.pdf * * * * * * *


External links


Was Super Glue invented to seal battle wounds in Vietnam?
(from
The Straight Dope "The Straight Dope" was a question-and-answer newspaper column written under the pseudonym Cecil Adams. Contributions were made by multiple authors, and it was illustrated (also pseudonymously) by Slug Signorino. It was first published in 1973 in ...
)
Cyanoacrylate Toxicity



Safety in the Home: Super Glue
-
Queensland Health Queensland Health is the name of the overall public health service in the state of Queensland, Australia. Like all other states and territories in Australia, the Queensland Government provides low- or no-cost primary, secondary, and tertiary ...

Cyanoacrylate Technical Data Sheet
* ''Alcohol-Catalyzed α-Cyanoacrylate Adhesive Compositions'', filed June 1954, issued October 1956.
3M Activators, Primers and Debonder

Application note on measuring cure kinetics of cyanoacrylate glues
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