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Home Science Chemistry. The Editors of Encyclopaedia Britannica Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree See Article History.

Alternative Titles: nylon 6,6, polyhexamethylene adipamide. Read More on This Topic. In October , DuPont announced the invention of the first wholly synthetic fibre ever produced.

Given the trade name Nylon Get exclusive access to content from our First Edition with your subscription. Subscribe today.

Learn More in these related Britannica articles:. Given the trade name Nylon which has now become a generic term , the material was actually polyhexamethylene adipamide, also known as nylon 6,6 for the presence of six carbon….

Nylon consists of long chains of carbon-based molecules, giving fibres of unprecedented strength and flexibility. It is formed by melting the component materials and extruding them; the strength of the fibre is greatly increased by stretching it when cold.

Although pure nylon has many flaws and is now rarely used, its derivatives have greatly influenced and contributed to society. From scientific discoveries relating to the production of plastics and polymerization, to economic impact during the depression and the changing of women's fashion, nylon was a revolutionary product.

Nylons are condensation polymers or copolymers , formed by reacting difunctional monomers containing equal parts of amine and carboxylic acid , so that amides are formed at both ends of each monomer in a process analogous to polypeptide biopolymers.

Most nylons are made from the reaction of a dicarboxylic acid with a diamine e. PA66 or a lactam or amino acid with itself e.

In the second case so called AA , the repeating unit corresponds to the single monomer. In common usage, the prefix "PA" polyamide or the name "Nylon" are used interchangeably and are equivalent in meaning.

The nomenclature used for nylon polymers was devised during the synthesis of the first simple aliphatic nylons and uses numbers to describe the number of carbons in each monomer unit, including the carbon s of the carboxylic acid s.

One number after "PA" or "Nylon" indicates a homopolymer which is monadic or based on one amino acid minus H 2 O as monomer:. Two numbers or sets of letters indicate a dyadic homopolymer formed from two monomers: one diamine and one dicarboxylic acid.

The first number indicates the number of carbons in the diamine. The two numbers should be separated by a comma for clarity, but the comma is often omitted.

To overcome this problem, a crystalline , solid "nylon salt " can be formed at room temperature , using an exact ratio of the acid and the base to neutralize each other.

The salt is crystallized to purify it and obtain the desired precise stoichiometry. The peptide bond within the caprolactam is broken with the exposed active groups on each side being incorporated into two new bonds as the monomer becomes part of the polymer backbone.

In general linear polymers are the most useful, but it is possible to introduce branches in nylon by the condensation of dicarboxylic acids with polyamines having three or more amino groups.

Two molecules of water are given off and the nylon is formed. Its properties are determined by the R and R' groups in the monomers.

In Kevlar, both R and R' are benzene rings. Industrial synthesis is usually done by heating the acids, amines or lactams to remove water, but in the laboratory, diacid chlorides can be reacted with diamines.

For example, a popular demonstration of interfacial polymerization the " nylon rope trick " is the synthesis of nylon 66 from adipoyl chloride and hexamethylene diamine.

Nylons can also be synthesized from dinitriles using acid catalysis. For example, this method is applicable for preparation of nylon 1,6 from adiponitrile , formaldehyde and water.

Nylon monomers are manufactured by a variety of routes, starting in most cases from crude oil but sometimes from biomass.

Those in current production are described below. Various diamine components can be used, which are derived from a variety of sources.

Most are petrochemicals , but bio-based materials are also being developed. Due to the large number of diamines, diacids and aminoacids that can be synthesized, many nylon polymers have been made experimentally and characterized to varying degrees.

A smaller number have been scaled up and offered commercially, and these are detailed below. Homopolymer polyamides derived from pairs of diamines and diacids or diacid derivatives.

Shown in the table below are polymers which are or have been offered commercially either as homopolymers or as a part of a copolymer.

It is easy to make mixtures of the monomers or sets of monomers used to make nylons to obtain copolymers. This lowers crystallinity and can therefore lower the melting point.

Most nylon polymers are miscible with each other allowing a range of blends to be made. The two polymers can react with one another by transamidation to form random copolymers.

According to this classification, PA66, for example, is an aliphatic semi-crystalline homopolyamide. All nylons are susceptible to hydrolysis , especially by strong acids , a reaction essentially the reverse of the synthetic reaction shown above.

The molecular weight of nylon products so attacked drops, and cracks form quickly at the affected zones. Lower members of the nylons such as nylon 6 are affected more than higher members such as nylon This means that nylon parts cannot be used in contact with sulfuric acid for example, such as the electrolyte used in lead—acid batteries.

When being molded, nylon must be dried to prevent hydrolysis in the molding machine barrel since water at high temperatures can also degrade the polymer.

Berners-Lee calculates the average greenhouse gas footprint of nylon in manufacturing carpets at 5. This gives it almost the same carbon footprint as wool , but with greater durability and therefore a lower overall carbon footprint.

Data published by PlasticsEurope indicates for nylon 66 a greenhouse gas footprint of 6. In particular when cars are lightweight, significant savings in fuel consumption and CO 2 emissions are achieved.

Various nylons break down in fire and form hazardous smoke, and toxic fumes or ash, typically containing hydrogen cyanide.

Incinerating nylons to recover the high energy used to create them is usually expensive, so most nylons reach the garbage dumps, decaying slowly.

Much nylon resin is recycled directly in a closed loop at the injection molding machine, by grinding sprues and runners and mixing them with the virgin granules being consumed by the molding machine.

Nylon can be recycled but only a few companies do so. Above their melting temperatures , T m , thermoplastics like nylon are amorphous solids or viscous fluids in which the chains approximate random coils.

Below T m , amorphous regions alternate with regions which are lamellar crystals. The planar amide -CO-NH- groups are very polar , so nylon forms multiple hydrogen bonds among adjacent strands.

Because the nylon backbone is so regular and symmetrical, especially if all the amide bonds are in the trans configuration , nylons often have high crystallinity and make excellent fibers.

The amount of crystallinity depends on the details of formation, as well as on the kind of nylon. The three-dimensional disposition of each alkane hydrocarbon chain depends on rotations about the When extruded into fibers through pores in an industry spinneret , the individual polymer chains tend to align because of viscous flow.

If subjected to cold drawing afterwards, the fibers align further, increasing their crystallinity, and the material acquires additional tensile strength.

In practice, nylon fibers are most often drawn using heated rolls at high speeds. Block nylon tends to be less crystalline, except near the surfaces due to shearing stresses during formation.

Nylon is clear and colorless , or milky, but is easily dyed. Multistranded nylon cord and rope is slippery and tends to unravel. The ends can be melted and fused with a heat source such as a flame or electrode to prevent this.

Nylons are hygroscopic, and will absorb or desorb moisture as a function of the ambient humidity.

Variations in moisture content have several effects on the polymer. Firstly, the dimensions will change, but more importantly moisture acts as a plasticizer, lowering the glass transition temperature T g , and consequently the elastic modulus at temperatures below the T g [79].

When dry, polyamide is a good electrical insulator. However, polyamide is hygroscopic. The absorption of water will change some of the material's properties such as its electrical resistance.

Nylon is less absorbent than wool or cotton. On the other hand, nylon 6 is easy to dye, more readily fades; it has a higher impact resistance, a more rapid moisture absorption, greater elasticity and elastic recovery.

Nylon clothing tends to be less flammable than cotton and rayon, but nylon fibers may melt and stick to skin. Nylon was first used commercially in a nylon- bristled toothbrush in , [11] [12] followed more famously in women's stockings or " nylons " which were shown at the New York World's Fair and first sold commercially in Bill Pittendreigh , DuPont , and other individuals and corporations worked diligently during the first few months of World War II to find a way to replace Asian silk and hemp with nylon in parachutes.

It was also used to make tires , tents , ropes , ponchos , and other military supplies. It was even used in the production of a high-grade paper for U.

After the war, because of shortages of both silk and nylon, nylon parachute material was sometimes repurposed to make dresses. Nylon 6 and 66 fibers are used in carpet manufacture.

Nylon is one kind of fibers used in tire cord. Herman E. Schroeder pioneered application of nylon in tires. Nylon resins are widely used in the automobile industry especially in the engine compartment.

Molded nylon is used in hair combs and mechanical parts such as machine screws , gears , gaskets, and other low- to medium-stress components previously cast in metal.

Type 6,6 Nylon is the most common commercial grade of nylon, and Nylon 6 is the most common commercial grade of molded nylon. Nylon can be used as the matrix material in composite materials , with reinforcing fibers like glass or carbon fiber; such a composite has a higher density than pure nylon.

Nylon was used to make the stock of the Remington Nylon 66 rifle. Nylon resins are used as a component of food packaging films where an oxygen barrier is needed.

Nylon has been used for meat wrappings and sausage sheaths. Nylon filaments are primarily used in brushes especially toothbrushes [11] and string trimmers.

They are also used as monofilaments in fishing line. Nylon and are the most used polymers for filaments. Its various properties also make it very useful as a material in additive manufacturing ; specifically as a filament in consumer and professional grade fused deposition modeling 3D printers.

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