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FKM is a family of
fluorocarbon Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often has distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Fluorocarbons and their derivatives are commerci ...
-based
fluoroelastomer {{refimprove, date=June 2008 A fluoroelastomer is a fluorocarbon-based synthetic rubber. Fluroelastomers generally have wide chemical resistance. Composition Several compositions of fluoroelastomers exist including FKM (by ASTM D1418 standard, equi ...
materials defined by ASTM International standard D1418, and ISO standard 1629. It is commonly called fluorine rubber or fluoro-rubber. FKM is an abreveation of Fluorine Kautschuk Material. All FKMs contain
vinylidene Methylidenecarbene (systematically named λ2-ethene and dihydrido-1κ2''H''-dicarbon(''C''—''C'')) is an organic compound with the chemical formula (also written [] or ). It is a metastability, metastable proton tautomer of acetylene, which on ...
fluoride as a monomer. Originally developed by DuPont (1802–2017), DuPont (under the brand name Viton, now owned by Chemours), FKMs are today also produced by many companies, including:
Daikin is a Japanese multinational air conditioning manufacturing company headquartered in Osaka. It has operations in Japan, China, Australia, the United States, India, Southeast Asia, Europe, the Middle East, Latin America, and Africa. Daikin is th ...
(Dai-El), 3M (Dyneon),
Solvay S.A. Solvay is a Belgian multinational chemical company established in 1863, with its headquarters located in Neder-Over-Heembeek, Brussels, Belgium. In 2015, it realized €12.4 billion in revenues, €2.336 billion of EBITDA, 43% of its sales in ...
(Tecnoflon), HaloPolymer (Elaftor), Gujarat Fluorochemicals (Fluonox), and several Chinese manufacturers. Fluoroelastomers are more expensive than
neoprene Neoprene (also polychloroprene) is a family of synthetic rubbers that are produced by polymerization of chloroprene.Werner Obrecht, Jean-Pierre Lambert, Michael Happ, Christiane Oppenheimer-Stix, John Dunn and Ralf Krüger "Rubber, 4. Emulsion R ...
or
nitrile rubber Nitrile rubber, also known as nitrile butadiene rubber, NBR, Buna-N, and acrylonitrile butadiene rubber, is a synthetic rubber derived from acrylonitrile (ACN) and butadiene. Trade names include Perbunan, Nipol, Krynac and Europrene. This rubber is ...
elastomer An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus and high failure strain compared with other materials. The term, a portmanteau of ''elastic p ...
s. They provide additional heat and chemical resistance. FKMs can be divided into different classes on the basis of either their chemical composition, their
fluorine Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reacti ...
content, or their cross-linking mechanism.


Types

On the basis of their chemical composition FKMs can be divided into the following types: * Type-1 FKMs are composed of
vinylidene fluoride 1,1-Difluoroethylene, also known as vinylidene fluoride, is a hydrofluoroolefin. It is a flammable gas. Global production in 1999 was approximately 33,000 metric tons. It is primarily used in the production of fluoropolymers such as polyvinyliden ...
(VDF) and hexafluoropropylene (HFP). Copolymers are the standard type of FKMs showing a good overall performance. Their fluorine content is approximately 66 weight percent. * Type-2 FKMs are composed of VDF, HFP, and tetrafluoroethylene (TFE). Terpolymers have a higher fluorine content compared to copolymers (typically between 68 and 69 weight percent fluorine), which results in better chemical and heat resistance. Compression set and low temperature flexibility may be affected negatively. * Type-3 FKMs are composed of VDF, TFE, and perfluoromethylvinylether (PMVE). The addition of PMVE provides better low temperature flexibility compared to copolymers and terpolymers. Typically, the fluorine content of type-3 FKMs ranges from 62 to 68 weight percent. * Type-4 FKMs are composed of propylene, TFE, and VDF. While base resistance is increased in type-4 FKMs, their swelling properties, especially in hydrocarbons, are worsened. Typically, they have a fluorine content of about 67 weight percent. * Type-5 FKMs are composed of VDF, HFP, TFE, PMVE, and
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
. Known for base resistance and high-temperature resistance to
hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The unde ...
.


Cross-linking mechanisms

There are three established cross-linking mechanisms used in the curing process of FKMs. *
Diamine A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to primary diamines, as those are the most reactive. In terms of quantities p ...
cross-linking using a blocked diamine. In the presence of basic (alkaline) media, VDF is vulnerable to
dehydrofluorination In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halid ...
, which enables the addition of the diamine to the polymer chain. Typically,
magnesium oxide Magnesium oxide ( Mg O), or magnesia, is a white hygroscopic solid mineral that occurs naturally as periclase and is a source of magnesium (see also oxide). It has an empirical formula of MgO and consists of a lattice of Mg2+ ions and O2− ions ...
is used to neutralize the resulting
hydrofluoric acid Hydrofluoric acid is a Solution (chemistry), solution of hydrogen fluoride (HF) in water. Solutions of HF are colourless, acidic and highly Corrosive substance, corrosive. It is used to make most fluorine-containing compounds; examples include th ...
and rearrange into magnesium fluoride and water. Although rarely used today, diamine curing provides superior rubber-to-metal bonding properties as compared with other cross-linking mechanisms. The diamine's capability to be hydrated makes the diamine cross-link vulnerable in aqueous media. * Ionic cross-linking ( dihydroxy cross-linking) was the next step in curing FKMs. This is today the most common cross-linking chemistry used for FKMs. It provides superior heat resistance, improved hydrolytic stability and better compression set than diamine curing. In contrast to diamine curing, the ionic mechanism is not an addition mechanism but an aromatic nucleophilic substitution. Dihydroxy aromatic compounds are used as the cross-linking agent, and
quaternary The Quaternary ( ) is the current and most recent of the three periods of the Cenozoic Era in the geologic time scale of the International Commission on Stratigraphy (ICS). It follows the Neogene Period and spans from 2.58 million years ...
phosphonium salts are typically used to accelerate the curing process. * Peroxide cross-linking was originally developed for type 3 FKMs containing PMVE as diamine and bisphenolic cross-linking systems can lead to cleavage in a polymer backbone chain containing PMVE. While diamine and bisphenolic cross-linking are
ionic reaction Ionic bonding is a type of chemical bonding that involves the Coulomb's law, electrostatic attraction between oppositely charged ions, or between two atoms with sharply different electronegativities, and is the primary interaction occurring in ion ...
s, peroxide cross-linking is a free-radical mechanism. Though peroxide cross-links are not as thermally stable as bisphenolic cross-links, they normally are the system of choice in aqueous media and nonaqueous
electrolyte An electrolyte is a medium containing ions that is electrically conducting through the movement of those ions, but not conducting electrons. This includes most soluble salts, acids, and bases dissolved in a polar solvent, such as water. Upon dis ...
media.


Properties

Fluoroelastomers provide excellent high temperature (up to 500°F or 260°C) and aggressive fluids resistance when compared with other elastomers, while combining the most effective stability to many sorts of chemicals and fluids such as oil,
diesel Diesel may refer to: * Diesel engine, an internal combustion engine where ignition is caused by compression * Diesel fuel, a liquid fuel used in diesel engines * Diesel locomotive, a railway locomotive in which the prime mover is a diesel engin ...
, ethanol mix or body fluid. The performance of fluoroelastomers in aggressive chemicals depends on the nature of the base polymer and the compounding ingredients used for molding the final products (e.g. o-rings). Some formulations are generally compatible with hydrocarbons, but incompatible with
ketones In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bon ...
such as acetone and
methyl ethyl ketone Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nat ...
, ester solvents such as ethyl acetate, amines, and organic acids such as
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
. They can be easily distinguished from many other elastomers because of their high density of over 1800 kg/m3, significantly higher than most types of rubber.


Applications

Because of their outstanding performance they find use in a number of sectors, including the following: * Chemical process and petroleum refining, where they are used for seals, pumps, gaskets and so on, due to their resistance to chemicals; * Analysis and process instruments: separators, diaphragms, cylindrical fittings, hoops, gaskets, etc. * Semiconductor manufacturing; * Food and pharmaceutical, because of their low degradation, also in contact with fluids; * Aviation and aerospace: high operating temperatures and high altitudes require superior heat and low-temperature resistance. They are suitable for the production of wearables, due to low wear and discoloration even during prolonged lifetimes in contact with skin oils and frequent exposure to light, while guaranteeing high comfort and stain resistance; The automotive industry represents their main application sector, where constant reach for higher efficiencies push manufacturers towards high-performing materials. An example are FKM o-rings used as an upgrade to the original neoprene seals on Corvair pushrod tubes that deteriorated under the high heat produced by the engine, allowing oil leakage. FKM tubing or lined hoses are commonly recommended in automotive and other transportation fuel applications when high concentrations of biodiesel are required. Studies indicate that types B and F (FKM- GBL-S and FKM-GF-S) are more resistant to acidic biodiesel. (This is because biodiesel fuel is unstable and oxidizing.) FKM O-rings have been used safely for some time in SCUBA diving by divers using gas blends referred to as nitrox. FKMs are used because they have a lower probability of catching fire, even with the increased percentages of oxygen found in nitrox. They are also less susceptible to decay under increased oxygen conditions. While these materials have a wide range of applications, their cost is prohibitive when compared to other types of elastomers, meaning that their adoption must be justified by the need for outstanding performance (as in the aerospace sector) and is inadvisable for low-cost products. FKM/butyl gloves are highly impermeable to many strong organic solvents that would destroy or permeate commonly used gloves (such as those made with
nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...
s).


Precautions

At high temperatures or in a fire, fluoroelastomers decompose and may release
hydrogen fluoride Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock i ...
. Any residue must be handled using protective equipment.


See also

* Magnesium/Teflon/Viton


References

* * Overview of different types and their applications.


Weblinks


Properties of Elastomers - Chemical Resitancelist
(PDF; 0,6 MB)
Designing with Fluoroelastomers
(PDF; 0,8 MB)


See also

*
FFKM FFKMs (by ASTM 1418 standard) (equivalent to FFPMs by ISO/DIN 1629 standard) are perfluoroelastomeric compounds containing an even higher amount of fluorine than FKM fluoroelastomers. They have improved resistance to high temperatures and chemic ...
, perfluoro-elastomers * FEPM, tetrafluoro ethylene/propylene elastomers {{DEFAULTSORT:FKM Organofluorides Elastomers Materials science Fluoropolymers