Neoprenes

Neoprene, or polychloroprene, is a synthetic rubber discovered by the Du Pont Company in 1931. It is an organic polymer composed of carbon, hydrogen, and chlorine in the ratio of 55 5 40. Its relatively high chlorine content was responsible for the early recognized resistance of the polymer to burning. Practical use of this property was not developed until procedures for making foam structures from neoprene latex were developed in the 1940 s. The U.S. Navy adapted the material to make neoprene foam mattresses that reduced the fire hazards in the crews quarters of naval vessels. For many years neoprene has been the only material to meet Navy specifications for this application. 

Polychloroprene begins to release hydrogen chloride (HCl) on heating to 430°F (221 C). The evolution of other gases, including carbon monoxide (CO) and carbon dioxide (CO2), and visible smoke continues as the temperature increases to 700°F (371°C). By the time this 

In the early 1980 s a neoprene-type foam (VONAR) made by Du Pont was developed specifically for use as a comfort cushioning material for critical applications where low flammabUity was required, such as in transport aircraft seat cushions. This material is designed for use over flame-retardant polymethane foam and is believed to provide 50 seconds more of evacuation time in the event of a post-crash fire. VONAR has a density of 10.66 Ib/ft , compared to 7-8 Ib/ft for standard neoprene foam, and 1.2-2 Ib/ft for polyurethane foam (5). 

Natural rubber is a polymer of isoprene, a conjugated diene. Synthetic rubbers called neoprenes are produced by the polymerization of chloroprene, a synthetic conjugated diene. Neoprene is used in many commercial products, from industrial hoses to wet suits for scuba diving and surfing. 

Terpenes have two or more isoprene units as their common structural feature. They can have different degrees of unsaturation and a variety of functional groups. Terpenes are classified according to the number of isoprene units they contain. 

Sesquiterpenes contain three isoprene units. (The prefix sesqui means one and a half. ) 

Farnesol contains three isoprene units joined head to tail. Dashed lines indicate where the three units are joined. 

Many terpenes contain one or more rings—carvone, for example— and we can also divide them into isoprene units. 

---

Ethyne is the starting point for the manufacture of a wide range of chemicals, amongst which the most important are acrylonitrile, vinyl chloride, vinyl acetate, ethanal, ethanoic acid, tri- and perchloro-ethylene, neoprene and polyvinyl alcohol. Processes such as vinylation, ethinylation, carbonylation, oligomerization and Reppe processes offer the possibility of producing various organic chemicals cheaply. Used in oxy-acetylene welding. 

The synthetic fiber industry as we know it began m 1928 when E I Du Pont de Nemours Company lured Professor Wallace H Carothers from Harvard University to direct their research department In a few years Carothers and his associates had pro duced nylon the first synthetic fiber and neoprene a rubber substitute Synthetic fibers and elastomers are both products of important contemporary industries with an economic influence far beyond anything imaginable m the middle 1920s... 

The hydrocarbon shown called vmylacetylene is used in the syn neoprene a synthetic rubber Identify the orbital overlaps involved in How many cr bonds are there in vmylacetylene How many... 

As the demand for rubber increased so did the chemical industry s efforts to prepare a synthetic sub stitute One of the first elastomers (a synthetic poly mer that possesses elasticity) to find a commercial niche was neoprene discovered by chemists at Du Pont in 1931 Neoprene is produced by free radical polymerization of 2 chloro 1 3 butadiene and has the greatest variety of applications of any elastomer Some uses include electrical insulation conveyer belts hoses and weather balloons... 

Chloro 1 3 butadiene (chloroprene) is the monomer from which the elastomer neoprene IS prepared 2 Chloro 1 3 butadiene is the thermodynamically controlled product formed by addi tion of hydrogen chloride to vinylacetylene (H2C=CHC=CH) The principal product under conditions of kinetic control is the allenic chlonde 4 chloro 1 2 butadiene Suggest a mechanism to account for the formation of each product... 

In most cases the sample bottle has a wide mouth, making it easy to fill and remove the sample. A narrow-mouth sample bottle is used when exposing the sample to the container cap or to the outside environment is undesirable. Unless exposure to plastic is a problem, caps for sample bottles are manufactured from polyethylene. When polyethylene must be avoided, the container cap includes an inert interior liner of neoprene or Teflon. 

Polymers of chloroprene (structure [XII]) are called neoprene and copolymers of butadiene and styrene are called SBR, an acronym for styrene-butadiene rubber. Both are used for many of the same applications as natural rubber. Chloroprene displays the same assortment of possible isomers as isoprene the extra combinations afforded by copolymer composition and structure in SBR offsets the fact that structures [XIIll and [XIV] are identical for butadiene. 

Using cuprous chloride as catalyst, hydrogen chloride adds to acetylene, giving 2-chloro-1,3-butadiene [126-99-8], chloroprene, C H Cl, the monomer for neoprene mbber. 

The synthesis in 1928 of polychloroprene or Neoprene, which has found much use in high strength elastomeric adhesives. 

Fluorine, the most reactive element known, is a dangerous material but may be handled safely using proper precautions. In any situation where an operator may come into contact with low pressure fluorine, safety glasses, a neoprene coat, boots, and clean neoprene gloves should be worn to afford overall body protection. This protection is effective against both fluorine and the hydrofluoric acid which may form from reaction of moisture in the air. 

In unalloyed steel containers formamide discolors slowly during shipment and storage. Both copper and brass are also subject to corrosion, particularly in the presence of water. Lead is less readily attacked. Aluminum and stainless steel are resistant to attack by formamide and should be used for shipping and storage containers where the color of the product is important or when metallic impurities must be minimized. Formamide attacks natural mbber but not neoprene. As a result of the solvent action of formamide, most protective paints and finishes are unsatisfactory when in contact with formamide. Therefore, formamide is best shipped in containers made of stainless steel or in dmms made of, or coated with, polyethylene. Formamide supphed by BASF is packed in Lupolen dmms (230 kg) or Lupolen canisters (60 kg) both in continental Europe and overseas. 

Other Uses. Large quantities of hydrocarbon resins are used in mastics, caulks, and sealants (qv). Polymers for these adhesive products include neoprene, butyl mbber, polyisoprene, NR, SBR, polyisobutylene, acryHcs, polyesters, polyamides, amorphous polypropylene, and block copolymers. These adhesives may be solvent or water-borne and usually contain inorganic fillers. 

At one time, the only commercial route to 2-chloro-1,3-butadiene (chloroprene), the monomer for neoprene, was from acetylene (see Elastomers, synthetic). In the United States, Du Pont operated two plants in which acetylene was dimeri2ed to vinylacetylene with a cuprous chloride catalyst and the vinyl-acetylene reacted with hydrogen chloride to give 2-chloro-1,3-butadiene. This process was replaced in 1970 with a butadiene-based process in which butadiene is chlorinated and dehydrochlorinated to yield the desired product (see Chlorocarbonsandchlorohydrocarbons). 

Plastics and Elastomers. Common plastics and elastomers (qv) show exceUent resistance to hydrochloric acid within the temperature limits of the materials. Soft natural mbber compounds have been used for many years as liners for concentrated hydrochloric acid storage tanks up to a temperature of 60°C (see Rubber, natural). SemUiard mbber is used as linings in pipe and equipment at temperatures up to 70°C and hard mbber is used for pipes up to 50°C and pressures up to 345 kPa (50 psig). When contaminants are present, synthetic elastomers such as neoprene, nitrile, butyl. 

Elastomeric materials, which provide relatively low practical static deflections and have relatively high natural frequencies, are used only to isolate higher frequencies. The volume compressibiUty of elastomeric materials is relatively low, therefore the shape of the elastomeric isolator must be taken into account, and space must be provided for lateral expansion. Because of their inherent resistance to chemical and environmental deterioration, neoprene and other synthetic materials often can be used in severe environments where natural materials would deteriorate. 

Fig. 8. Vibration isolators (a) single-spring mount with base plate (b) neoprene mount (c) spring and neoprene hanger and (d) neoprene waffle pad.

Lead sesquioxide is used as an oxidation catalyst for carbon monoxide ia exhaust gases (44,45) (see Exhaust control), as a catalyst for the preparation of lactams (46) (see Antibiotics, P-lactams), ia the manufacture of high purity diamonds (47) (see Carbon, diamond-natural), ia fireproofing compositions for poly(ethylene terephthalate) plastics (48), ia radiation detectors for x-rays and nuclear particles (49), and ia vulcanization accelerators for neoprene mbber (50). 

Extreme caution must be taken to prevent the possibility of fire when using flammable removers. Extra care must be taken when stripping on location to secure the area of ignition sources. When used on lacquer finishes, the dissolved finish and remover combined are extremely flammable. Natural mbber, neoprene, or other gloves suitable for use with the remover formula must be worn. The effect of skin contact with the remover is limited because there is immediate irritation and discomfort. Canister respirators are available for most petroleum and oxygenate remover solvents. Symptoms of long-term overexposure should be compared to symptoms of the major ingredients in the formula. 

---