Butyl rubber
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Butyl rubber, sometimes just called "butyl", is a synthetic rubber, a
copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...
of
isobutylene Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Producti ...
with isoprene. The abbreviation IIR stands for isobutylene isoprene rubber. Polyisobutylene, also known as "PIB" or polyisobutene, (C4H8)n, is the
homopolymer 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 an ...
of isobutylene, or 2-methyl-1-propene, on which butyl rubber is based. Butyl rubber is produced by polymerization of about 98% of isobutylene with about 2% of isoprene. Structurally, polyisobutylene resembles
polypropylene Polypropylene (PP), also known as polypropene, is a thermoplastic polymer used in a wide variety of applications. It is produced via chain-growth polymerization from the monomer propylene. Polypropylene belongs to the group of polyolefins a ...
, but has two
methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ma ...
s substituted on every other
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 mak ...
atom, rather than one. Polyisobutylene is a colorless to light yellow
viscoelastic In materials science and continuum mechanics, viscoelasticity is the property of materials that exhibit both viscous and elastic characteristics when undergoing deformation. Viscous materials, like water, resist shear flow and strain linearly ...
material. It is generally odorless and tasteless, though it may exhibit a slight characteristic odor.


Properties

Butyl rubber has excellent impermeability to gas diffusion, and the long polyisobutylene segments of its
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 ...
chains give it good flex properties. The formula for PIB is: –(–CH2–C(CH3)2–)n– The formula for IIR is: It can be made from the
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 ...
isobutylene (CH2=C(CH3)2) only via cationic addition polymerization. A synthetic rubber, or elastomer, butyl rubber is impermeable to air and used in many applications requiring an airtight rubber. Polyisobutylene and butyl rubber are used in the manufacture of
adhesives 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 ...
, agricultural chemicals,
fiber optic An optical fiber, or optical fibre in Commonwealth English, is a flexible, transparent fiber made by drawing glass (silica) or plastic to a diameter slightly thicker than that of a human hair. Optical fibers are used most often as a means t ...
compounds, ball bladders,
O-ring An O-ring, also known as a packing or a toric joint, is a mechanical gasket in the shape of a torus; it is a loop of elastomer with a round cross-section, designed to be seated in a groove and compressed during assembly between two or more par ...
s,
caulk Caulk or, less frequently, caulking is a material used to seal joints or seams against leakage in various structures and piping. The oldest form of caulk consisted of fibrous materials driven into the wedge-shaped seams between boards on ...
s and sealants, cling film, electrical fluids, lubricants (2 stroke engine oil), paper and pulp, personal care products,
pigment A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compou ...
concentrates, for rubber and polymer modification, for protecting and sealing certain equipment for use in areas where chemical weapons are present, as a
gasoline Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organi ...
/ diesel fuel additive, and
chewing gum Chewing gum is a soft, cohesive substance designed to be chewed without being swallowed. Modern chewing gum is composed of gum base, sweeteners, softeners/ plasticizers, flavors, colors, and, typically, a hard or powdered polyol coating. Its t ...
. The first major application of butyl rubber was tire inner tubes. This remains an important segment of its market even today.


History

Isobutylene was discovered by
Michael Faraday Michael Faraday (; 22 September 1791 – 25 August 1867) was an English scientist who contributed to the study of electromagnetism and electrochemistry. His main discoveries include the principles underlying electromagnetic inducti ...
in 1825. Polyisobutylene (PIB) was first developed by the
BASF BASF SE () is a German multinational chemical company and the largest chemical producer in the world. Its headquarters is located in Ludwigshafen, Germany. The BASF Group comprises subsidiaries and joint ventures in more than 80 countries ...
unit of IG Farben in 1931 using a boron trifluoride catalyst at low temperatures and sold under the trade name . PIB remains a core business for BASF to this day. It was later developed into butyl rubber in 1937, by researchers
William J. Sparks William Joseph Sparks (February 26, 1905 – October 23, 1976) was a chemist at Exxon. As an inventor, his most important contribution was the development of butyl rubber. Sparks served as president of the American Chemical Society in 1966 and ...
and Robert M. Thomas, at Standard Oil of New Jersey's Linden, N.J., laboratory. Today, the majority of the global supply of butyl rubber is produced by two companies, ExxonMobil (one of the descendants of Standard Oil) and Polymer Corporation, a Canadian federal crown corporation established in 1942 to produce artificial rubber to substitute for overseas supply cut off by World War II. It was renamed Polysar in 1976 and the rubber component became a subsidiary, Polysar Rubber Corp. The company was privatized in 1988 with its sale to NOVA Corp which, in turn, sold Polysar Rubber in 1990 to Bayer AG of Germany. In 2005 Bayer AG spun off chemical divisions, including most of the Sarnia site, creating LANXESS AG, also of Germany. PIB homopolymers of high molecular weight (100,000–400,000 or more) are polyolefin elastomers: tough extensible rubber-like materials over a wide temperature range; with low density (0.913–0.920), low permeability and excellent electrical properties. In the 1950s and 1960s, halogenated butyl rubber (halobutyl) was developed, in its chlorinated (chlorobutyl) and brominated (bromobutyl) variants, providing significantly higher curing rates and allowing covulcanization with other rubbers such as
natural 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 ...
and
styrene-butadiene Styrene-butadiene or styrene-butadiene rubber (SBR) describe families of synthetic rubbers derived from styrene and butadiene (the version developed by Goodyear is called Neolite). These materials have good abrasion resistance and good aging st ...
rubber. Halobutyl is today the most important material for the inner linings of
tubeless tires Tubeless tires ( also spelled as tubeless tyres in Commonwealth English) are pneumatic tires that do not require a separate inner tube. Unlike pneumatic tires which use a separate inner tube, tubeless tires have continuous ribs molded integral ...
. Francis P. Baldwin received the 1979
Charles Goodyear Medal The Charles Goodyear Medal is the highest honor conferred by the American Chemical Society, Rubber Division. Established in 1941, the award is named after Charles Goodyear, the discoverer of vulcanization, and consists of a gold medal, a framed ...
for the many patents he held for these developments. In the spring of 2013 two incidents of PIB contamination in the English Channel, believed to be connected, were described as the worst UK marine pollution 'for decades'. The RSPB estimated over 2,600 seabirds were killed by the chemical and hundreds more were rescued and decontaminated.


Uses


Fuel and lubricant additive

Polyisobutylene can be reacted with
maleic anhydride Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and pol ...
to make polyisobutenylsuccinic anhydride (PIBSA), which can then be converted into polyisobutenylsuccinimides (PIBSI) by reacting it with various
ethyleneamines Ethyleneamines are a class of amine compounds containing ethylene (-CH2CH2-) linkages between amine groups. These compounds are generally colorless, low-viscosity liquids with a fishy amine odor. They are primarily used as building block chemicals ...
. When used as an additive in lubricating oils and motor fuels, they can have a substantial effect on the properties of the oil or fuel. Polyisobutylene added in small amounts to the lubricating oils used in machining results in a significant reduction in the generation of oil mist and thus reduces the operator's inhalation of
oil mist Oil mist refers to oil droplets suspended in the air in the size range 1~10 μm. Formation of Oil Mist Oil mist may form when high pressure fuel oil, lubricating oil, hydraulic oil, or other oil is sprayed through a narrow crack, or when l ...
. It is also used to clean up waterborne oil spills as part of the commercial product Elastol. When added to crude oil it increases the oil's
viscoelasticity In materials science and continuum mechanics, viscoelasticity is the property of materials that exhibit both viscous and elastic characteristics when undergoing deformation. Viscous materials, like water, resist shear flow and strain linearl ...
when pulled, causing the oil to resist breakup when it is vacuumed from the surface of the water. As a fuel additive, polyisobutylene has detergent properties. When added to
diesel fuel Diesel fuel , also called diesel oil, is any liquid fuel specifically designed for use in a diesel engine, a type of internal combustion engine in which fuel ignition takes place without a spark as a result of compression of the inlet air and ...
, it resists fouling of fuel injectors, leading to reduced hydrocarbon and particulate emissions. It is blended with other detergents and additives to make a "detergent package" that is added to
gasoline Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organi ...
and diesel fuel to resist buildup of deposits and
engine knock In spark ignition internal combustion engines, knocking (also knock, detonation, spark knock, pinging or pinking) occurs when combustion of some of the air/fuel mixture in the cylinder does not result from propagation of the flame front ignite ...
. Polyisobutylene is used in some formulations as a
thickening agent A thickening agent or thickener is a substance which can increase the viscosity of a liquid without substantially changing its other properties. Edible thickeners are commonly used to thicken sauces, soups, and puddings without altering the ...
.


Explosives

Polyisobutylene is often used by the explosives industry as a binding agent in plastic explosives such as C-4. Polyisobutylene binder is used because it makes the explosive more insensitive to premature detonation as well as making it easier to handle and mold.


Speakers and audio equipment

Butyl rubber is generally used in speakers, specifically the surrounds. It was used as a replacement for foam surrounds because the foam would deteriorate. The majority of modern speakers use butyl rubber, while most vintage speakers use foam.


Sporting equipment

Butyl rubber is used for the bladders in sporting balls (e.g. Rugby balls, footballs, basketballs,
netball Netball is a ball sport played on a court by two teams of seven players. It is among a rare number of sports which have been created exclusively for female competitors. The sport is played on indoor and outdoor netball courts and is specifical ...
s) and to make bicycle inner tubes to provide a tough, airtight inner compartment.


Damp proofing and roof repair

Butyl rubber sealant is used for
damp proofing Damp proofing in construction is a type of moisture control applied to building walls and floors to prevent moisture from passing into the interior spaces. Dampness problems are among the most frequent problems encountered in residences. ''Damp p ...
, rubber
roof A roof ( : roofs or rooves) is the top covering of a building, including all materials and constructions necessary to support it on the walls of the building or on uprights, providing protection against rain, snow, sunlight, extremes of te ...
repair and for maintenance of roof membranes (especially around the edges). It is important to have the roof membrane fixed, as a lot of fixtures (e.g., air conditioner vents, plumbing, and other pipes) can considerably loosen it. Rubber roofing typically refers to a specific type of roofing materials that are made of ethylene propylene diene monomers ( EPDM rubber). It is crucial to the integrity of such roofs to avoid using harsh abrasive materials and petroleum-based solvents for their maintenance. Polyester fabric laminated to butyl rubber binder provides a single-sided waterproof tape that can be used on metal, PVC, and cement joints. It is used for repairing and waterproofing metal roofs.


Gas masks and chemical agent protection

Butyl rubber is one of the most robust elastomers when subjected to
chemical warfare agent A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...
s and decontamination materials. It is a harder and less porous material than other elastomers, such as natural rubber or silicone, but still has enough elasticity to form an airtight seal. While butyl rubber will break down when exposed to agents such as NH3 (
ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...
) or certain solvents, it breaks down more slowly than comparable elastomers. It is therefore used to create seals in
gas masks A gas mask is a mask used to protect the wearer from inhaling airborne pollutants and toxic gases. The mask forms a sealed cover over the nose and mouth, but may also cover the eyes and other vulnerable soft tissues of the face. Most gas mask ...
and other protective clothing.


Pharmaceutical stoppers

Butyl and bromobutyl rubber are commonly used for manufacturing rubber stoppers used for sealing medicine
vials A vial (also known as a phial or flacon) is a small glass or plastic vessel or bottle, often used to store medication as liquids, powders or capsules. They can also be used as scientific sample vessels; for instance, in autosampler devices i ...
and
bottles A bottle is a narrow-necked container made of an impermeable material (such as glass, plastic or aluminium) in various shapes and sizes that stores and transports liquids. Its mouth, at the bottling line, can be sealed with an internal stop ...
.


Chewing gum

Most modern
chewing gum Chewing gum is a soft, cohesive substance designed to be chewed without being swallowed. Modern chewing gum is composed of gum base, sweeteners, softeners/ plasticizers, flavors, colors, and, typically, a hard or powdered polyol coating. Its t ...
uses food-grade butyl rubber as the central gum base, which contributes not only the gum's elasticity but also gives it a stubborn, sticky quality which has led some municipalities to propose taxation to cover costs of its removal. Recycled chewing gum has also been used as a source of recovered polyisobutylene. Amongst other products, this base rubber has been manufactured into coffee cups and 'Gumdrop' gum-collecting bins. When filled, the collecting bins and their contents are shredded together and recycled again.


Tires

Butyl rubber and halogenated rubber are used for the
inner tube An inner tube is an inflatable ring that forms the interior of some pneumatic tires. The tube is inflated with a valve stem, and fits inside of the casing of the tire. The inflated inner tube provides structural support and suspension, while the ...
that holds air inside most tires.


Insulating windows

Polyisobutylene is used as the primary seal in an insulating glass unit for commercial and residential construction providing the air and moisture seal for the unit.


Notes


External links


Brief overview of PolyisobutyleneAdditional information
for various polyisobutylene (PIB) grades {{Motor fuel Elastomers Fuel additives Organic polymers Thickening agents