Butyl Rubber
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Butyl rubber, sometimes just called butyl, is a
synthetic rubber A synthetic rubber is an artificial elastomer. They are polymers synthesized from petroleum byproducts. About of rubber is produced annually in the United States, and of that amount two thirds are synthetic. Synthetic rubber, just like natural ru ...
, 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 som ...
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. Product ...
with
isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers ar ...
. The abbreviation IIR stands for isobutylene isoprene rubber. Polyisobutylene, also known as "PIB" or polyisobutene, (C4H8)n, is the homopolymer 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 Propene, propylene. Polypropylene belongs to the group of polyolefin ...
, 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 (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...
s substituted on every other
carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
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 Viscosity, viscous and Elasticity (physics), elastic characteristics when undergoing deformation (engineering), deformation. Viscous mate ...
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 () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...
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 A monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or two- or three-dimensional network in a process called polymerization. Classification Chemis ...
isobutylene (CH2=C(CH3)2) only via cationic addition polymerization. A synthetic rubber, or
elastomer An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus (E) and high failure strain compared with other materials. The term, a portmanteau of ''ela ...
, 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 advantage ...
, agricultural chemicals,
fiber optic An optical fiber, or optical fibre, is a flexible glass or plastic fiber that can transmit light from one end to the other. Such fibers find wide usage in fiber-optic communications, where they permit transmission over longer distances and at ...
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 (geometry), cross-section, designed to be seated in a groove and compressed during assembl ...
s,
caulk Caulk (also known as caulking and calking) is a material used to Seal (mechanical), seal Joint (building), joints or seams against leakage in various structures and piping. The oldest form of caulk consisted of fibrous materials driven into ...
s and sealants, cling film, electrical fluids,
lubricants A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces ...
(2 stroke engine oil), paper and pulp, personal care products,
pigment A pigment is a powder used to add or alter color or change visual appearance. Pigments are completely or nearly solubility, insoluble and reactivity (chemistry), chemically unreactive in water or another medium; in contrast, dyes are colored sub ...
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 ( North American English) or petrol ( Commonwealth English) is a petrochemical product characterized as a transparent, yellowish, and flammable liquid normally used as a fuel for spark-ignited internal combustion engines. When for ...
/ 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 tex ...
. 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 chemist and physicist who contributed to the study of electrochemistry and electromagnetism. His main discoveries include the principles underlying electromagnetic inducti ...
in 1825. Polyisobutylene (PIB) was first developed by the
BASF BASF SE (), an initialism of its original name , is a European Multinational corporation, multinational company and the List of largest chemical producers, largest chemical producer in the world. Its headquarters are located in Ludwigshafen, Ge ...
unit of
IG Farben I. G. Farbenindustrie AG, commonly known as IG Farben, was a German Chemical industry, chemical and Pharmaceutical industry, pharmaceutical conglomerate (company), conglomerate. It was formed on December 2, 1925 from a merger of six chemical co ...
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 and Robert M. Thomas, at
Standard Oil Standard Oil Company was a Trust (business), corporate trust in the petroleum industry that existed from 1882 to 1911. The origins of the trust lay in the operations of the Standard Oil of Ohio, Standard Oil Company (Ohio), which had been founde ...
of New Jersey's Linden, N.J., laboratory. Today, the majority of the global supply of butyl rubber is produced by two companies,
ExxonMobil Exxon Mobil Corporation ( ) is an American multinational List of oil exploration and production companies, oil and gas corporation headquartered in Spring, Texas, a suburb of Houston. Founded as the Successors of Standard Oil, largest direct s ...
(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 Sarnia is a city in Lambton County, Ontario, Canada. It had a Canada 2021 Census, 2021 population of 72,047, and is the largest city on Lake Huron. Sarnia is located on the eastern bank of the junction between the Upper and Lower Great Lakes, ...
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,
halogen The halogens () are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the radioactive elements astatine (At) and tennessine (Ts), though some authors would ...
ated 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. Types of polyisoprene ...
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 ...
rubber. Halobutyl is today the most important material for the inner linings of tubeless tires. Francis P. Baldwin received the 1979
Charles Goodyear Medal The Charles Goodyear Medal is the highest honor conferred by the American Chemical Society#Organization, American Chemical Society, Rubber Division. Established in 1941, the award is named after Charles Goodyear, the discoverer of vulcanization, ...
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 Marine pollution occurs when substances used or spread by humans, such as industrial waste, industrial, agricultural pollution, agricultural, and municipal solid waste, residential waste; particle (ecology), particles; noise; excess carbon dioxi ...
'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 . 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 polymers. Str ...
to make polyisobutenylsuccinic anhydride (PIBSA), which can then be converted into polyisobutenylsuccinimides (PIBSI) by reacting it with various ethyleneamines. 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 Machining is a manufacturing process where a desired shape or part is created using the controlled removal of material, most often metal, from a larger piece of raw material by cutting. Machining is a form of subtractive manufacturing, which util ...
results in a significant reduction in the generation of oil mist and thus reduces the operator's inhalation of oil mist. It is also used to clean up waterborne
oil spill An oil spill is the release of a liquid petroleum hydrocarbon into the environment, especially the marine ecosystem, due to human activity, and is a form of pollution. The term is usually given to marine oil spills, where oil is released into th ...
s as part of the commercial product Elastol. When added to
crude oil Petroleum, also known as crude oil or simply oil, is a naturally occurring, yellowish-black liquid chemical mixture found in geological formations, consisting mainly of hydrocarbons. The term ''petroleum'' refers both to naturally occurring u ...
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 both shear flow and strain lin ...
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 A detergent is a surfactant or a mixture of surfactants with Cleanliness, cleansing properties when in Concentration, dilute Solution (chemistry), solutions. There are a large variety of detergents. A common family is the alkylbenzene sulfonate ...
properties. When added to
diesel fuel Diesel fuel, also called diesel oil, heavy oil (historically) or simply diesel, 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 re ...
, 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 ( North American English) or petrol ( Commonwealth English) is a petrochemical product characterized as a transparent, yellowish, and flammable liquid normally used as a fuel for spark-ignited internal combustion engines. When for ...
and diesel fuel to resist buildup of deposits and
engine knock In Spark-ignition engine, spark-ignition internal combustion engines, knocking (also knock, detonation, spark knock, pinging or pinking) occurs when combustion of some of the air-fuel ratio, air/fuel mixture in the cylinder does not result from ...
. Polyisobutylene is used in some formulations as a thickening agent.


Explosives

Polyisobutylene is often used by the
explosives An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An exp ...
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 rectangular court by two teams of seven players. The primary objective is to shoot a ball through the defender's goal ring while preventing the opposing team from shooting through their own. It is one of a ...
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, 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 tempera ...
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 EPDM rubber (ethylene propylene diene monomer rubber) is a type of synthetic rubber that is used in many applications. EPDM is an M-Class rubber under ASTM standard D-1418; the ''M'' class comprises elastomers with a saturated polyethylene chai ...
). 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 agents and
decontamination Decontamination (sometimes abbreviated as decon, dcon, or decontam) is the process of removing contaminants on an object or area, including chemicals, micro-organisms, and/or radioactive substances. This may be achieved by chemical reaction, dis ...
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 chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
) 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 piece of personal protective equipment 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 ...
and other protective clothing.


Pharmaceutical stoppers

Butyl and bromobutyl rubber are commonly used for manufacturing rubber stoppers used for sealing medicine vials and bottles.


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 tex ...
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

Because of their superior resistance to gas
diffusion Diffusion is the net movement of anything (for example, atoms, ions, molecules, energy) generally from a region of higher concentration to a region of lower concentration. Diffusion is driven by a gradient in Gibbs free energy or chemical p ...
, butyl rubber and halogenated rubber are used for the innerliner inside pneumatic tubeless tires, and for the inner tube in older 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