Names | |
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Preferred IUPAC name Octyl 2-cyanoprop-2-enoate | |
Other names Octyl 2-cyanopropenoate Octyl 2-cyanoacrylate Ocrylate | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.027.045 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C12H19NO2 | |
Molar mass | 209.289 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.0±0.1 g/cm3 |
Boiling point | 297.6±23.0 °C |
Reacts | |
Hazards | |
Flash point | 137.2±9.4 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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 veterinary applications, OCA, n-butyl cyanoacrylate (n-BCA) and isobutyl cyanoacrylate (ICA) are commonly used. They provide rapid wound closure, [1] are bacteriostatic, and their use is usually painless.[ citation needed ] Butyl esters provide a stronger bond, but the glue is rigid. The octyl ester, while providing weaker bond, is more flexible. Blends of OCA and n-BCA are available which offer both flexibility and a strong bond.
It polymerizes rapidly in presence of moisture.
Heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritating to the lungs and eyes.
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.
In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
Cyanoacrylates are a family of strong fast-acting adhesives with industrial, medical, and household uses. They are derived from ethyl cyanoacrylate and related esters. The cyanoacrylate group in the monomer rapidly polymerizes in the presence of water to form long, strong chains.
Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.
A plasticizer is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.
Benzyl butyl phthalate (BBP) is an organic compound historically used a plasticizer, but which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and n-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB.
Hot-melt adhesive (HMA), also known as hot glue, is a form of thermoplastic adhesive that is commonly sold as solid cylindrical sticks of various diameters designed to be applied using a hot glue gun. The gun uses a continuous-duty heating element to melt the plastic glue, which the user pushes through the gun either with a mechanical trigger mechanism on the gun, or with direct finger pressure. The glue squeezed out of the heated nozzle is initially hot enough to burn and even blister skin. The glue is sticky when hot, and solidifies in a few seconds to one minute. Hot-melt adhesives can also be applied by dipping or spraying, and are popular with hobbyists and crafters both for affixing and as an inexpensive alternative to resin casting.
Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-acrylic 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 encountered under many trade names. It is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. ECA polymerizes rapidly in presence of moisture.
Harry Wesley Coover Jr. was the inventor of Eastman 910, commonly known as Super Glue.
An acrylate polymer is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity.
Wood glue is an adhesive used to tightly bond pieces of wood together. Many substances have been used as glues. Traditionally animal proteins like casein from milk or collagen from animal hides and bones were boiled down to make early glues. They worked by solidifying as they dried. Later, glues were made from plant starches like flour or potato starch. When combined with water and heated, the starch gelatinizes and forms a sticky paste as it dries. Plant-based glues were common for books and paper products, though they can break down more easily over time compared to animal-based glues. Examples of modern wood glues include polyvinyl acetate (PVA) and epoxy resins. Some resins used in producing composite wood products may contain formaldehyde. As of 2021, “the wood panel industry uses almost 95% of synthetic petroleum-derived thermosetting adhesives, mainly based on urea, phenol, and melamine, among others”.
Elmer's Products, Inc. or simply Elmer's, is an American-based company that has a line of adhesive, craft, home repair, and office supply products. It is best known as the manufacturer of Elmer's Glue-All, a popular PVA-based synthetic glue, in addition to other brands including Krazy Glue, ProBond and CraftBond adhesives, and X-Acto cutting tools.
Liquid bandage is a topical skin treatment for minor wounds which binds to the skin to form a protective polymeric layer that keeps dirt and germs out and moisture in.
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 thread. There are numerous types of suture which differ by needle shape and size as well as thread material and characteristics. Selection of surgical suture should be determined by the characteristics and location of the wound or the specific body tissues being approximated.
Wound closure strips are porous surgical tape strips which can be used to close small wounds. They are applied across the laceration in a manner which pulls the skin on either side of the wound together. Wound closure strips may be used instead of sutures (stitches) in some injuries, because they lessen scarring and are easier to care for.
Methyl cyanoacrylate is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.
n-Butyl cyanoacrylate, a cyanoacrylate ester, is a butyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various trade names, e.g. Cutseal, MediBond, MediCryl, PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand, Histoacryl, IFABond, CutisSeal and others. The generic international nonproprietary name (INN) for NBCA is enbucrilate.
Isobutyl cyanoacrylate is an isomer of butyl cyanoacrylate. It is used in medical procedures either to close incisions and lacerations without the use of sutures, or as an adjunct to strengthen the suturing. This use is possible because it is a bactericidal liquid monomer which, in the presence of small amounts of moisture, rapidly polymerizes to form a strong adhesive.
2-Octyl cyanoacrylate is a cyanoacrylate ester typically used as a wound closure adhesive. It is closely related to octyl cyanoacrylate. The use of 2-octyl cyanoacrylate was approved in 1998; offered as an alternative to stitches, sutures, and or adhesive strips.
Chemence is a speciality chemical and medical device manufacturer which products include cyanoacrylate adhesives, anaerobic adhesives, impregnation sealants, adhesive activators, epoxy resins, UV adhesives, photopolymer resins, custom printer ink cartridges, Gas pipe sealants, and soak off nail polishes. Chemence is a supplier of photopolymer and commercial printers to the flexographic industry in the US and Europe, as well as the primary sealant supplier to British Gas, and a primary supplier of private-label adhesives to companies including Tesco, 3M, Bostik, and Bondo. The company's catalogue of patents includes processes, packaging devices, and chemical combinations.