Butyl rubber

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Butyl_rubber

 

Butyl rubber gloves

 

Butyl rubber, sometimes just called "butyl", is a synthetic rubber, a copolymer of isobutylene with isoprene. 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, but has two methyl groups substituted on every other carbon atom, rather than one. Polyisobutylene is a colorless to light yellow viscoelastic material. It is generally odorless and tasteless, though it may exhibit a slight characteristic odor. 

Butyl rubber has excellent impermeability, and the long polyisobutylene segments of its polymer chains give it good flex properties. Its formula is:

 

It can be made from the monomer 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, agricultural chemicals, fiber optic compounds, ball bladders, O-rings, caulks and sealants, cling film, electrical fluids, lubricants (2 stroke engine oil), paper and pulp, personal care products, pigment concentrates, for rubber and polymer modification, for protecting and sealing certain equipment for use in areas where chemical weapons are present, as a gasoline/diesel fuel additive, and chewing gum. 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 in 1825. Polyisobutylene (PIB) was first developed by the BASF unit of IG Farben in 1931 using a boron trifluoride catalyst at low temperatures and sold under the trade name Oppanol B [de]. 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 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 and styrene-butadiene rubber. Halobutyl is today the most important material for the inner linings of tubeless tires. Francis P. Baldwin received the 1979 Charles Goodyear Medal 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 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 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 spills as part of the commercial product Elastol. When added to crude oil it increases the oil's viscoelasticity 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, 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 and diesel fuel to resist buildup of deposits and engine knock.

Polyisobutylene is used in some formulations as a thickening agent.

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, netballs) to provide a tough, airtight inner compartment.

Damp proofing and roof repair

Butyl rubber sealant is used for damp proofing, rubber roof 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 agents 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) or certain solvents, it breaks down more slowly than comparable elastomers. It is therefore used to create seals in gas masks 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

Gumdrop chewing gum collecting bin

 

Most modern chewing gum uses food-grade butyl rubber as the central gum base, which contributes not only the gum's elasticity but an obstinate, 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 innerliner that holds the air in the tire.

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.

Chloroprene

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Chloroprene

 

Chloroprene

Names
IUPAC name 2-Chlorobuta-1,3-diene
Other names Chloroprene, 2-chloro-1,3-butadiene, Chlorobutadiene, β-Chloroprene
Identifiers
CAS Number	126-99-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:39481
ChEMBL	ChEMBL555660
ChemSpider	29102
ECHA InfoCard	100.004.381
KEGG	C19208
PubChem CID	31369
RTECS number	EL9625000
CompTox Dashboard (EPA)	DTXSID5020316
Properties
Chemical formula	C4H5Cl
Molar mass	88.5365 g/mol
Appearance	Colorless liquid
Odor	pungent, ether-like
Density	0.9598 g/cm3
Melting point	−130 °C (−202 °F; 143 K)
Boiling point	59.4 °C (138.9 °F; 332.5 K)
Solubility in water	0.026 g/100 mL
Solubility	soluble in alcohol, diethyl ether miscible in ethyl ether, acetone, benzene
Vapor pressure	188 mmHg (20 °C)
Refractive index (nD)	1.4583
Hazards
Main hazards	Highly flammable, irritant, toxic.
R-phrases (outdated)	R45, R11, R20/22, R36/37/38, R48/20
S-phrases (outdated)	S53, S45
NFPA 704 (fire diamond)	3 2 0
Flash point	−15.6 °C (3.9 °F; 257.5 K)
Explosive limits	1.9%–11.3%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	450 mg/kg (rat, oral)
LC50 (median concentration)	3207 ppm (rat, 4 hr)
LCLo (lowest published)	1052 ppm (rabbit, 8 hr) 350 ppm (cat, 8 hr)
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 25 ppm (90 mg/m3) [skin]
REL (Recommended)	Ca C 1 ppm (3.6 mg/m3) [15-minute]
IDLH (Immediate danger)	300 ppm
Related compounds
Related Dienes	Butadiene Isoprene
Related compounds	Vinyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chloroprene is the common name for 2-chlorobuta-1,3-diene (IUPAC name) with the chemical formula CH₂=CCl−CH=CH_2. Chloroprene is a colorless volatile liquid, almost exclusively used as a monomer for the production of the polymer polychloroprene, a type of synthetic rubber. Polychloroprene is better known as Neoprene, the trade name given by DuPont.

History

Although it may have been discovered earlier, the chemistry of chloroprene was largely developed by DuPont during the early 1930s, specifically with the formation of neoprene in mind. The chemists Elmer K. Bolton, Wallace Carothers, Arnold Collins and Ira Williams are generally accredited with its development and commercialisation although the work was based upon that of Julius Arthur Nieuwland, with whom they collaborated.

Production

Chloroprene is produced in three steps from 1,3-butadiene: (i) chlorination, (ii) isomerization of part of the product stream, and (iii) dehydrochlorination of 3,4-dichlorobut-1-ene.

Chlorine adds to 1,3-butadiene to afford a mixture of 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene. The 1,4-dichloro isomer is subsequently isomerized to 3,4 isomer, which in turn is treated with base to induce dehydrochlorination to 2-chlorobuta-1,3-diene. This dehydrohalogenation entails loss of a hydrogen atom in the 3 position and the chlorine atom in the 4 position thereby forming a double bond between carbons 3 and 4. In 1983, approximately 2,000,000 kg was produced in this manner. The chief impurity in chloroprene prepared in this way is 1-chlorobuta-1,3-diene, which is usually separated by distillation. 

Acetylene process

Until the 1960s, chloroprene production was dominated by the "acetylene process," which was modeled after the original synthesis of vinylacetylene. In this process, acetylene is dimerized to give vinyl acetylene, which is then combined with hydrogen chloride to afford 4-chloro-1,2-butadiene (an allene derivative), which in the presence of copper(I) chloride, rearranges to the targeted 2-chlorobuta-1,3-diene.

This process is energy-intensive and has high investment costs. Furthermore, the intermediate vinyl acetylene is unstable. This "acetylene process" has been replaced by a process, which adds Cl₂ to one of the double bonds in 1,3-butadiene, and subsequent elimination produces HCl instead, as well as chloroprene.

Regulations

 

Transportation

Transportation of uninhibited chloroprene has been banned in the United States by the US Department of Transportation. Stabilized chloroprene is in hazard class 3 (flammable liquid). Its UN number is 1991 and is in packing group 1. 

Occupational health and safety

Hazards

GHS hazard pictograms that apply to chloroprene. From left: flammability; carcinogenicity, mutagenicity, reproductive toxicity, respiratory sensitization, target organ toxicity, or aspiration toxicity; irritant (skin and eye), skin sensitizer, respiratory tract irritant, hazardous to ozone layer, may have narcotic effects; aquatic toxicity; and acute toxicity (fatal or toxic).

 

As a way to visually communicate hazards associated with chloroprene exposure, the United Nations Globally Harmonized System of Classification and Labeling of Chemicals (GHS) has designated the following hazards for exposure to chloroprene: flammable, toxic, dangerous to the environment, health hazard and irritant. Chloroprene poses fire hazard (flash point -4 °F). OSHA identifies chloroprene as a category 2 flammable liquid and emphasizes that at least one portable fire extinguisher should be within 10 and no more than 25 feet away from the flammable liquid storage area. OSHA provides resources on addressing flammable liquids at industrial plants which is where the likely exposure to chloroprene exists (see external resources). As a vapor, chloroprene is heavier than air. 

According to the National Fire Protection Association's rating system, chloroprene is designated with a category 2 health hazard (temporary incapacitation or residual injury), a category 3 fire hazard (ignition under the presence of moderate heat), and a category 1 reactivity (unstable at high temperatures and pressures).

Chronic exposure to chloroprene may have the following symptoms: liver function abnormalities, disorders of the cardiovascular system, and depression of the immune system.

The Environmental Protection Agency(EPA) designated chloroprene as likely to be carcinogenic to humans based on evidence from studies that showed a statistically significant association between occupational chloroprene exposure and the risk of lung cancer. As early as 1975, NIOSH had identified the potential health hazards of chloroprene in their bulletin primarily citing two Russian cohort studies from those working with chloroprene in an occupational setting.

Hazard determination

OSHA defines hazard determination as "the process of evaluating available scientific evidence in order to determine if a chemical is hazardous pursuant to the HCS." While chemical manufacturers and importers are required to conduct a hazard determination, other companies may voluntarily conduct a hazard determination to ensure worker health and safety. Under the hazard determination framework, any chemical that has a physical or health hazard is considered a hazardous chemical. Physical hazards include fire hazards, reactive hazards, and explosion hazards. Heath hazards include systemic effects and target organ effects. Chloroprene is on OSHA's list for substances that are regulated as toxic and hazardous.

In the European Union, the hazard-determination-equivalent is the Registration, Evaluation, Authorization, and Restriction of Chemicals (REACH) regulation enacted on June 1, 2007 by the European Chemicals Agency (ECHA). The goal of REACH is to "improve the protection of human health and the environment from the risks that can be posed by chemicals, while enhancing the competitiveness of the EU chemicals industry." If risks of chemicals are unmanageable, ECHA may ban its use. 

Hazard controls

Several epidemiological studies and toxicological reports provide evidence of chloroprene's capability to inflict occupational health and safety concerns. However, varying reviews of the degree to which chloroprene should be held responsible for health concerns highlight the criticality of sound scientific research. Nonetheless, health and safety practices should always be implemented in the workplace. Some of these occupational concerns include: cleaning equipment or unclogging pipes coated with chloroprene, inhaling chloroprene off-gas, chloroprene spontaneously reacting with other chemicals and chloroprene inducing a workplace fire. Upon the clogging of equipment associated with occupational chloroprene use, employers should ensure that their employees are wearing the proper PPE and set up administrative controls so that skin exposure to and inhalation of chloroprene is avoided. Only one fatality as a result of chloroprene intoxication has been recorded which was a result of cleaning a container used for chloroprene.

NIOSH Hierarchy of Controls

 

The primary occupational concern for chloroprene is limited to the facilities producing chloroprene and using chloroprene to produce the synthetic rubber, polychloroprene. NIOSH developed a list of actions to address specific workplace hazards. These actions are represented in their diagram of the "Hierarchy of Controls" shown below with the most effective steps at the top and the least effective at the bottom. 

The high vaporization potential and flammability of chloroprene has significant implications for handling and storage operations in the occupational setting. Chloroprene should be stored in closed containers in a cool, well-ventilated area with the temperature no higher than 50 degrees Fahrenheit. In addition, chloroprene has a high reactivity and should be stored away from oxidizing agents such as perchlorate, peroxides, permanganates, chlorates, nitrates, chlorine, bromine, and fluorine. All activities inducing a potential fire hazard should be avoided. For instance, smoking, having open flames or using sparking tools to open or close storage containers should be prohibited. It is also advised that grounded and bonded metal containers are used for the transport of chloroprene.

Occupational exposure limits

The official legal body that develops and enforces occupational exposure limits (OEL) in order to ensure workplace safety and health regulations is the Occupational Health and Safety Administration (OSHA) that works under the U.S. Department of Labor. OSHA's permissible exposure limits (PELs), a guideline for occupational exposures, were adopted from the 1968 threshold limit values (TLVs) of the American Conference of Governmental Industrial Hygienists (ACGIH). Each year, the ACGIH publish their TLV and BEI booklet that provides updated information on "occupational exposure guidelines for more than 700 chemical substances and physical agents." The scientific literature on certain chemical and physical exposures has evolved since 1968, therefore OSHA recognizes that their PELs may not guarantee worker health and safety. The National Institute for Occupational Health and Safety (NIOSH) under the U.S. Department of Health and Human Services compensates for the rigidity of the PEL by researching "all medical, biological, engineering, chemical, and trade information relevant to the hazard" and publishing recommended exposure limits (RELs) based on their research. Therefore, as a way to ensure worker safety and health, the following sections on safety guidelines and hazard control will consider the most recent occupational exposure limits from ACGIH's 2018 TLV and BEI booklet and NIOSH's REL.

A table of occupational exposure limits (OELs) from various jurisdictions follows. In general, the OELs range from 0.55 ppm to 25 ppm.

Occupational Exposure Limits for Chloroprene

In the ACGIH's 2018 TLV and BEI booklet, chloroprene was designated with a skin and an A2 notation. The skin notation designation is based on animal and human research that have shown chloroprene's ability to be absorbed by the skin. An A2 designation by the ACGIH means that the substance is a suspected human carcinogen with support from human data that are accepted as adequate in quality but may not be enough to declare an A1 (known human carcinogen) designation. Additionally, the TLV basis for these designations are due to scientific studies that show an association between chloroprene exposure and lung cancer, upper respiratory tract (URT) and eye irritation.

Public health implications

Since chloroprene usage is limited to those facilities producing Neoprene, the occupational health risks are isolated to those facilities. However, insufficient control of chloroprene emissions may extend the health and safety concerns of chloroprene beyond the facility and into the surrounding areas. Chloroprene release is predominately as an air pollutant, but other feasible fates and transport of chloroprene in the environment are discussed below.

In the fourteenth edition of the National Institute of Health report on carcinogens, the half-life time differences between chloroprene in air, water and soil were highlighted. In the air, chloroprene “reacts with photo-chemically generated hydroxyl radicals” and has a half-life of 18 hours. The smaller amounts that are removed by reaction with ozone have a half-life of 10 days. In streams, chloroprene is stated to volatilize quickly with a half-life of 3 hours. However, in bigger bodies of water such as a lake, the half-life of chloroprene is 4 days. Similar to its reaction with water, chloroprene on soil was cited to volatilize from the surface. However, the report remarked that chloroprene holds the potential to leach into groundwater supplies. Due to its volatility and extreme reactivity, the threat of chloroprene exists predominantly as an air pollutant and is not expected to bioaccumulate or persist in the environment according to the U.S EPA Toxicological Review of Chloroprene. However, the Centers for Disease Control and Prevention (CDC) states that chloroprene does, in fact, have the potential to persist in the environment. Nonetheless, the primary route of exposure for animals and humans is inhalation, but can be absorbed through the skin or indigestion.

In December 2015, the EPA released its 2011 National Air Toxic Assessment to help state and local agencies prioritize the required steps in identifying and mitigating sources of air pollution. In this report, it was measured that chloroprene was being released from Denka Performance Elastomer's Pontchartrain facility located in LaPlace, Louisiana. EPA worked with the Louisiana Department of Environmental Quality, DuPont and the nonprofit organization Louisiana Environmental Action Network to institute monitoring of chloroprene pollution near the facility and in the surrounding neighborhood. Air monitoring is ongoing.

Neoprene

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Neoprene

 

A neck seal, wrist seal, manual vent, inflator, zip and fabric of a neoprene dry suit. Here the soft thin rubber-like seal material at neck and wrists is made from non-foam neoprene for elasticity; the blue area is a thin blue knit fabric laminated onto spongy foamed neoprene for insulation.

 

Chemical structure of the repeating unit of polychloroprene

Neoprene (also polychloroprene or pc-rubber) is a family of synthetic rubbers that are produced by polymerization of chloroprene. Neoprene exhibits good chemical stability and maintains flexibility over a wide temperature range. Neoprene is sold either as solid rubber or in latex form and is used in a wide variety of applications, such as laptop sleeves, orthopaedic braces (wrist, knee, etc.), electrical insulation, liquid and sheet applied elastomeric membranes or flashings, and automotive fan belts.

Production

Neoprene is produced by free-radical polymerization of chloroprene. In commercial production, this polymer is prepared by free radical emulsion polymerization. Polymerization is initiated using potassium persulfate. Bifunctional nucleophiles, metal oxides (e.g. zinc oxide), and thioureas are used to crosslink individual polymer strands.

Property	Value
Appearance
Hardness, Shore A	40–95
Tensile failure stress, ultimate	500–3000 PSI
Elongation after fracture in %	≥ 600% maximum
Density	Can be compounded around 1.23 g/cm3

History

Neoprene was invented by DuPont scientists on April 17, 1930, after Dr Elmer K. Bolton of DuPont attended a lecture by Fr Julius Arthur Nieuwland, a professor of chemistry at the University of Notre Dame. Nieuwland's research was focused on acetylene chemistry and during the course of his work he produced divinyl acetylene, a jelly that firms into an elastic compound similar to rubber when passed over sulfur dichloride. After DuPont purchased the patent rights from the university, Wallace Carothers of DuPont took over commercial development of Nieuwland's discovery in collaboration with Nieuwland himself and DuPont chemists Arnold Collins, Ira Williams and James Kirby. Collins focused on monovinyl acetylene and allowed it to react with hydrogen chloride gas, manufacturing chloroprene.

DuPont first marketed the compound in 1931 under the trade name DuPrene, but its commercial possibilities were limited by the original manufacturing process, which left the product with a foul odor. A new process was developed, which eliminated the odor-causing byproducts and halved production costs, and the company began selling the material to manufacturers of finished end-products. To prevent shoddy manufacturers from harming the product's reputation, the trademark DuPrene was restricted to apply only to the material sold by DuPont. Since the company itself did not manufacture any DuPrene-containing end products, the trademark was dropped in 1937 and replaced with a generic name, neoprene, in an attempt "to signify that the material is an ingredient, not a finished consumer product". DuPont then worked extensively to generate demand for its product, implementing a marketing strategy that included publishing its own technical journal, which extensively publicized neoprene's uses as well as advertising other companies' neoprene-based products. By 1939, sales of neoprene were generating profits over $300,000 for the company (equivalent to $5,514,115 in 2019).

Applications

General

Two styles of well-worn Xtratuf boots made with neoprene

 

Neoprene resists degradation more than natural or synthetic rubber. This relative inertness makes it well suited for demanding applications such as gaskets, hoses, and corrosion-resistant coatings. It can be used as a base for adhesives, noise isolation in power transformer installations, and as padding in external metal cases to protect the contents while allowing a snug fit. It resists burning better than exclusively hydrocarbon based rubbers, resulting in its appearance in weather stripping for fire doors and in combat related attire such as gloves and face masks. Because of its tolerance of extreme conditions, neoprene is used to line landfills. Neoprene's burn point is around 260 °C (500 °F).

In its native state, neoprene is a very pliable rubber-like material with insulating properties similar to rubber or other solid plastics. 

Neoprene foam is used in many applications and is produced in either closed-cell or open-cell form. The closed-cell form is waterproof, less compressible and more expensive. The open-cell form can be breathable. It is manufactured by foaming the rubber with nitrogen gas, where the tiny enclosed and separated gas bubbles can also serve as insulation. Nitrogen gas is most commonly used for the foaming of Neoprene foam due to its inertness, flame resistance, and large range of processing temperatures.

Civil engineering

Neoprene is used as a load bearing base, usually between two prefabricated reinforced concrete elements or steel plates as well to evenly guide force from one element to another.

Aquatics

Neoprene is a popular material in making protective clothing for aquatic activities. Foamed neoprene is commonly used to make fly fishing waders and wetsuits, as it provides excellent insulation against cold. The foam is quite buoyant, and divers compensate for this by wearing weights. Thick wet suits made at the extreme end of their cold water protection are usually made of 7 mm thick neoprene.^{[citation needed]} Since foam neoprene contains gas pockets, the material compresses under water pressure, getting thinner at greater depths; a 7 mm neoprene wet suit offers much less exposure protection under 100 feet of water than at the surface. A recent advance in neoprene for wet suits is the "super-flex" variety, which mixes spandex into the neoprene for greater flexibility.

Neoprene waders are usually about 5 mm thick, and in the medium price range as compared to cheaper materials such as nylon and more expensive waterproof fabrics made with breathable membranes. 

Competitive swimming wetsuits are made of the most expanded foam; they have to be very flexible to allow the swimmer unrestricted movement. The downside is that they are quite fragile.

Home accessories

Recently, neoprene has become a favorite material for lifestyle and other home accessories including laptop sleeves, tablet holders, remote controls, mouse pads, and cycling chamois. In this market, it sometimes competes with LRPu (low-resilience polyurethane), which is a sturdier (more impact-resistant) but less-used material.

Music

The Rhodes piano used hammer tips made of neoprene in its electric pianos, after changing from felt hammers around 1970.

Neoprene is also used for speaker cones and drum practice pads.

Hydroponic gardening

Hydroponic and aerated gardening systems make use of small neoprene inserts to hold plants in place while propagating cuttings or using net cups. Inserts are relatively small, ranging in size from 1.5 to 5 inches (4 to 13 cm). Neoprene is a good choice for supporting plants because of its flexibility and softness, allowing plants to be held securely in place without the chance of causing damage to the stem. Neoprene root covers also help block out light from entering the rooting chamber of hydroponic systems, allowing for better root growth and helping to deter the growth of algae.

Other

Neoprene is used for Halloween masks and masks used for face protection, for insulating CPU sockets, to make waterproof automotive seat covers, in liquid and sheet-applied elastomeric roof membranes or flashings, and in a neoprene-spandex mixture for manufacture of wheelchair positioning harnesses.

Because of its chemical resistance and overall durability, neoprene is sometimes used in the manufacture of dishwashing gloves, especially as an alternative to latex.

In fashion, neoprene has been used by designers such as Gareth Pugh, Balenciaga, Rick Owens, Lanvin and Vera Wang. This trend, promoted by street style bloggers such as Jim Joquico of Fashion Chameleon, gained traction and trickled down to mainstream fashion around 2014.

A woman wearing neoprene leggings

 

Precautions

Some people are allergic to neoprene while others can get dermatitis from thiourea residues left from its production. The most common accelerator in the vulcanization of polychloroprene is ethylene thiourea (ETU), which has been classified as reprotoxic. The European rubber industry project called SafeRubber focused on alternatives to the use of ETU.

Isoprene

From Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Isoprene

 

Isoprene

Names
Preferred IUPAC name 2-Methylbuta-1,3-diene
Other names 2-Methyl-1,3-butadiene Isoprene
Identifiers
CAS Number	78-79-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:35194
ChemSpider	6309
ECHA InfoCard	100.001.040
KEGG	C16521
PubChem CID	6557
UNII	0A62964IBU
CompTox Dashboard (EPA)	DTXSID2020761
Properties
Chemical formula	C5H8
Molar mass	68.12 g/mol
Density	0.681 g/cm3
Melting point	−143.95 °C (−227.11 °F; 129.20 K)
Boiling point	34.067 °C (93.321 °F; 307.217 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isoprene, or 2-methyl-1,3-butadiene, is a common organic compound with the formula CH₂=C(CH₃)−CH=CH₂. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber. C. G. Williams named the compound in 1860 after obtaining it from thermal decomposition (pyrolysis) of natural rubber; he correctly deduced the empirical formula C₅H₈.

Natural occurrences

Isoprene is produced and emitted by many species of trees (major producers are oaks, poplars, eucalyptus, and some legumes). Yearly production of isoprene emissions by vegetation is around 600 million metric tons, half from tropical broadleaf trees and the remainder primarily from shrubs. This is about equivalent to methane emissions and accounts for around one-third of all hydrocarbons released into the atmosphere. 

Plants

Isoprene is made through the methyl-erythritol 4-phosphate pathway (MEP pathway, also called the non-mevalonate pathway) in the chloroplasts of plants. One of the two end products of MEP pathway, dimethylallyl pyrophosphate (DMAPP), is cleaved by the enzyme isoprene synthase to form isoprene and diphosphate. Therefore, inhibitors that block the MEP pathway, such as fosmidomycin, also block isoprene formation. Isoprene emission increases dramatically with temperature and maximizes at around 40 °C. This has led to the hypothesis that isoprene may protect plants against heat stress (thermotolerance hypothesis, see below). Emission of isoprene is also observed in some bacteria and this is thought to come from non-enzymatic degradations from DMAPP. 

Regulation

Isoprene emission in plants is controlled both by the availability of the substrate (DMAPP) and by enzyme (isoprene synthase) activity. In particular, light, CO₂ and O₂ dependencies of isoprene emission are controlled by substrate availability, whereas temperature dependency of isoprene emission is regulated both by substrate level and enzyme activity. 

Other organisms

Isoprene is the most abundant hydrocarbon measurable in the breath of humans.^[5][6] The estimated production rate of isoprene in the human body is 0.15 µmol/(kg·h), equivalent to approximately 17 mg/day for a person weighing 70 kg. Isoprene is common in low concentrations in many foods. 

Chemical structure of cis-polyisoprene, the main constituent of natural rubber

 

Biological roles

Isoprene emission appears to be a mechanism that trees use to combat abiotic stresses. In particular, isoprene has been shown to protect against moderate heat stress (around 40 °C). It may also protect plants against large fluctuations in leaf temperature. Isoprene is incorporated into and helps stabilize cell membranes in response to heat stress. 

Isoprene also confers resistance to reactive oxygen species. The amount of isoprene released from isoprene-emitting vegetation depends on leaf mass, leaf area, light (particularly photosynthetic photon flux density, or PPFD) and leaf temperature. Thus, during the night, little isoprene is emitted from tree leaves, whereas daytime emissions are expected to be substantial during hot and sunny days, up to 25 μg/(g dry-leaf-weight)/hour in many oak species.

Isoprenoids

The isoprene skeleton can be found in naturally occurring compounds called terpenes (also known as isoprenoids), but these compounds do not arise from isoprene itself. Instead, the precursor to isoprene units in biological systems is dimethylallyl pyrophosphate (DMAPP) and its isomer isopentenyl pyrophosphate (IPP). The plural 'isoprenes' is sometimes used to refer to terpenes in general. 

Examples of isoprenoids include carotene, phytol, retinol (vitamin A), tocopherol (vitamin E), dolichols, and squalene. Heme A has an isoprenoid tail, and lanosterol, the sterol precursor in animals, is derived from squalene and hence from isoprene. The functional isoprene units in biological systems are dimethylallyl pyrophosphate (DMAPP) and its isomer isopentenyl pyrophosphate (IPP), which are used in the biosynthesis of naturally occurring isoprenoids such as carotenoids, quinones, lanosterol derivatives (e.g. steroids) and the prenyl chains of certain compounds (e.g. phytol chain of chlorophyll). Isoprenes are used in the cell membrane monolayer of many Archaea, filling the space between the diglycerol tetraether head groups. This is thought to add structural resistance to harsh environments in which many Archaea are found. 

Similarly, natural rubber is composed of linear polyisoprene chains of very high molecular weight and other natural molecules.

Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP) and squalene shown. Some intermediates are omitted.

 

Impact on aerosols

After release, isoprene is converted by short-lived free radicals (like the hydroxyl radical) and to a lesser extent by ozone into various species, such as aldehydes, hydroperoxides, organic nitrates, and epoxides, which mix into water droplets and help create aerosols and haze.

While most experts acknowledge that isoprene emission affects aerosol formation, whether isoprene increases or decreases aerosol formation is debated. A second major effect of isoprene on the atmosphere is that in the presence of nitric oxides (NO_x) it contributes to the formation of tropospheric (lower atmosphere) ozone, which is one of the leading air pollutants in many countries. Isoprene itself is not normally regarded as a pollutant, as it is a natural plant product. Formation of tropospheric ozone is only possible in presence of high levels of NO_x, which comes almost exclusively from industrial activities. Isoprene can have the opposite effect and quench ozone formation under low levels of NO_x. 

Industrial production

Isoprene is most readily available industrially as a byproduct of the thermal cracking of naphtha or oil, as a side product in the production of ethylene. About 800,000 metric tons are produced annually. About 95% of isoprene production is used to produce cis-1,4-polyisoprene—a synthetic version of natural rubber.

Natural rubber consists mainly of poly-cis-isoprene with a molecular mass of 100,000 to 1,000,000 g/mol. Typically natural rubber contains a few percent of other materials, such as proteins, fatty acids, resins, and inorganic materials. Some natural rubber sources, called gutta percha, are composed of trans-1,4-polyisoprene, a structural isomer that has similar, but not identical, properties.