Nylon

Template:Short description {{#invoke:other uses|otheruses}} Template:Use British English

Nylon 6 Nylon Nylon 6,6
Density	1.15 g/cm3
Electrical conductivity (σ)	10−12 S/m
Thermal conductivity	0.25 W/(m·K)
Melting point	463–624 K 190–350 °C 374–663 °F

Nylon is a family of synthetic polymers characterised by amide linkages, typically connecting aliphatic or semi-aromatic groups.

Nylons are generally brownish in color<ref>Template:Cite book</ref> and can possess a soft texture, with some varieties exhibiting a silk-like appearance.<ref>Template:Cite book</ref> As thermoplastics, nylons can be melt-processed into fibres, films, and diverse shapes.<ref name="Vogler">Template:Cite journal</ref><ref name="AOGHS" /><ref name="Kohan">Template:Cite book</ref>Template:Rp The properties of nylons are often modified by blending with a variety of additives.

Numerous types of nylon are available. One family, designated nylon-XY, is derived from diamines and dicarboxylic acids of carbon chain lengths X and Y, respectively. An important example is nylon-6,6 (Template:Chem2). Another family, designated nylon-Z, is derived from aminocarboxylic acids with carbon chain length Z. An example is nylon-[6].

Nylon polymers have extensive commercial applications, including uses in textiles and fibres (such as apparel, flooring and rubber reinforcement), molded components for automotive and electrical equipment, and films (mostly for food packaging).<ref name="BPF">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

History

File:Wallace Carothers, in the lab.jpg

Wallace Carothers

DuPont and the invention of nylon

Researchers at DuPont began developing cellulose-based fibres, culminating in the synthetic fibre rayon. DuPont's experience with rayon was an important precursor to its development and marketing of nylon.<ref name="Ndiaye">Template:Cite book</ref>Template:Rp

DuPont's invention of nylon spanned an eleven-year period, ranging from the initial research program in polymers in 1927 to its announcement in 1938, shortly before the opening of the 1939 New York World's Fair.<ref name=":1">Template:Cite book</ref> The project grew from a new organisational structure at DuPont, suggested by Charles Stine in 1927, in which the chemical department would be composed of several small research teams that would focus on "pioneering research" in chemistry and would "lead to practical applications".<ref name="Ndiaye" />Template:Rp Harvard instructor Wallace Hume Carothers was hired to direct the polymer research group. Initially he was allowed to focus on pure research, building on and testing the theories of German chemist Hermann Staudinger.<ref name="Kativa"/> He was very successful, as research he undertook greatly improved the knowledge of polymers and contributed to the science.<ref name="Meikle">Template:Cite book</ref>

Nylon was the first commercially successful synthetic thermoplastic polymer.<ref name="PlasticsCHF">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> DuPont began its research project in 1927.<ref name=":1" /> The first nylon, nylon 66, was synthesised on February 28, 1935, by Wallace Hume Carothers at DuPont's research facility at the DuPont Experimental Station.<ref name="ACS">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Carothers">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In response to Carothers' work, Paul Schlack at IG Farben developed nylon 6, a different molecule based on caprolactam, on January 29, 1938.<ref name="McIntyre">Template:Cite book</ref>Template:Rp<ref name="Travis">Template:Cite book</ref>

In the spring of 1930, Carothers and his team had already synthesised two new polymers. One was neoprene, a synthetic rubber greatly used during World War II.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The other was a white elastic but strong paste that would later become nylon. After these discoveries, Carothers' team was made to shift its research from a more pure research approach investigating general polymerisation to a more practically focused goal of finding "one chemical combination that would lend itself to industrial applications".<ref name="Ndiaye" />Template:Rp

It was not until the beginning of 1935 that a polymer called "polymer 6-6" was finally produced. Carothers' coworker, Washington University alumnus Julian W. Hill had used a cold drawing method to produce a polyester in 1930.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> This cold drawing method was later used by Carothers in 1935 to fully develop nylon.<ref>Template:Cite news</ref> The first example of nylon (nylon 6.6) was produced on February 28, 1935, at DuPont's research facility at the DuPont Experimental Station.<ref name=ACS/> It had all the desired properties of elasticity and strength. However, it also required a complex manufacturing process that would become the basis of industrial production in the future. DuPont obtained a patent for the polymer in September 1938,<ref name="US 2130523"/> and quickly achieved a monopoly of the fibre.<ref name="Meikle" /> Carothers died 16 months before the announcement of nylon, therefore he was never able to see his success.<ref name=":1" /> The name "Nylon" came from the a modification of norun (no run) into a unique name that could be used to market the product but was not trademarked.<ref name="Myers">Template:Cite book</ref>

Nylon was first used commercially in a nylon-bristled toothbrush in 1938,<ref name="AOGHS"/><ref name="Nicholson">Template:Cite magazine</ref> followed more famously in women's stockings or "nylons" which were shown at the 1939 New York World's Fair and first sold commercially in 1940,<ref name="Wolfe2008">Template:Cite journal</ref> whereupon they became an instant commercial success with 64 million pairs sold during their first year on the market. During World War II, almost all nylon production was diverted to the military for use in parachutes and parachute cord. Wartime uses of nylon and other plastics greatly increased the market for the new materials.<ref name="Conflicts">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

The production of nylon required interdepartmental collaboration between three departments at DuPont: the Department of Chemical Research, the Ammonia Department, and the Department of Rayon.<ref>Template:Cite book</ref> Some of the key ingredients of nylon had to be produced using high pressure chemistry, the main area of expertise of the Ammonia Department. Nylon was considered a "godsend to the Ammonia Department",<ref name="Ndiaye" /> which had been in financial difficulties. The reactants of nylon soon constituted half of the Ammonia Department's sales and helped them come out of the period of the Great Depression by creating jobs and revenue at DuPont.<ref name="Ndiaye" />

DuPont's nylon project demonstrated the importance of chemical engineering in industry, helped create jobs, and furthered the advancement of chemical engineering techniques. In fact, it developed a chemical plant that provided 1800 jobs and used the latest technologies of the time, which are still used as a model for chemical plants today.<ref name="Ndiaye" /> The ability to acquire a large number of chemists and engineers quickly was a huge contribution to the success of DuPont's nylon project.<ref name="Ndiaye" />Template:Rp The first nylon plant was located at Seaford, Delaware, beginning commercial production on December 15, 1939. On October 26, 1995, the Seaford plant was designated a National Historic Chemical Landmark by the American Chemical Society.<ref name="Landmark">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Early marketing strategies

An important part of nylon's popularity stems from DuPont's marketing strategy. DuPont promoted the fibre to increase demand before the product was available to the general market. Nylon's commercial announcement occurred on October 27, 1938, at the final session of the Herald TribuneTemplate:'s yearly "Forum on Current Problems", on the site of the approaching New York City world's fair.<ref name="Kativa">Template:Cite journal</ref><ref name="Meikle" />Template:Rp The "first man-made organic textile fibre" which was derived from "coal, water and air" and promised to be "as strong as steel, as fine as the spider's web" was received enthusiastically by the audience, many of them middle-class women, and made the headlines of most newspapers.<ref name="Meikle" />Template:Rp Nylon was introduced as part of "The world of tomorrow" at the 1939 New York World's Fair<ref name="Blakinger">Template:Cite news</ref> and was featured at DuPont's "Wonder World of Chemistry" at the Golden Gate International Exposition in San Francisco in 1939.<ref name="Kativa"/><ref name="Sundberg">Template:Cite book</ref> Actual nylon stockings were not shipped to selected stores in the national market until May 15, 1940. However, a limited number were released for sale in Delaware before that.<ref name="Meikle" />Template:Rp The first public sale of nylon stockings occurred on October 24, 1939, in Wilmington, Delaware. 4,000 pairs of stockings were available, all of which were sold within three hours.<ref name="Kativa"/>

Another added bonus to the campaign was that it meant reducing silk imports from Japan, an argument that won over many wary customers. Nylon was even mentioned by President Roosevelt's cabinet, which addressed its "vast and interesting economic possibilities" five days after the material was formally announced.<ref name="Meikle" />

However, the early excitement over nylon also caused problems. It fueled unreasonable expectations that nylon would be better than silk, a miracle fabric as strong as steel that would last forever and never run.<ref name="Meikle" />Template:Rp<ref name="Wolfe2008"/> Realizing the danger of claims such as "New Hosiery Held Strong as Steel" and "No More Runs", DuPont scaled back the terms of the original announcement, especially those stating that nylon would possess the strength of steel.<ref name="Meikle" />

Also, DuPont executives marketing nylon as a revolutionary man-made material did not at first realise that some consumers experienced a sense of unease and distrust, even fear, towards synthetic fabrics.<ref name="Meikle" />Template:Rp A particularly damaging news story, drawing on DuPont's 1938 patent for the new polymer, suggested that one method of producing nylon might be to use cadaverine (pentamethylenediamine),Template:Efn a chemical extracted from corpses. Although scientists asserted that cadaverine was also extracted by heating coal, the public often refused to listen. A woman confronted one of the lead scientists at DuPont and refused to accept that the rumour was not true.<ref name="Meikle" />Template:Rp

DuPont changed its campaign strategy, emphasizing that nylon was made from "coal, air and water", and started focusing on the personal and aesthetic aspects of nylon, rather than its intrinsic qualities.<ref name="Meikle" />Template:Rp Nylon was thus domesticated,<ref name="Meikle"/>Template:Rp and attention shifted to the material and consumer aspect of the fibre with slogans like "If it's nylon, it's prettier, and oh! How fast it dries!".<ref name="Ndiaye" />Template:Rp

Production of nylon fabric

File:NMA.0028271, Fashion Photo by Erik Liljeroth 1954.jpg

Nylon stockings being inspected in Malmö, Sweden, in 1954

After nylon's nationwide release in 1940, its production ramped up significantly. In that year alone, 1300 tons of the fabric were produced, marking a remarkable start for this innovative material.[8]: 100  The demand for nylon surged, particularly for nylon stockings, which became an instant sensation. During their first year on the market, an astounding 64 million pairs of nylon stockings were sold, reflecting the fabric's rapid integration into daily life and fashion.[8]: 101  Such was the success of nylon that in 1941, just a year after its launch, a second plant was opened in Martinsville, Virginia, to meet the growing demand and ensure a steady supply of this popular fabric. This expansion underscored the profound impact nylon had on the textile industry and its rapid rise to prominence as a versatile and sought-after material.<ref name=":0">Template:Cite book</ref>

File:Particolare di calza di nylon.jpg

Close-up photograph of the knitted nylon fabric used in stockings

File:Nylon fibre SEM.tif

Nylon fibres visualised using scanning electron microscopy

While nylon was marketed as the durable and indestructible material of the people, it was sold at about one-and-a-half times the price of silk stockings ($4.27 per pound of nylon versus $2.79 per pound of silk).<ref name="Ndiaye" />Template:Rp Sales of nylon stockings were strong in part due to changes in women's fashion. As Lauren Olds explains: "by 1939 [hemlines] had inched back up to the knee, closing the decade just as it started off". The shorter skirts were accompanied by a demand for stockings that offered fuller coverage without the use of garters to hold them up.<ref name="Olds">Template:Cite journal</ref>

However, as of February 11, 1942, nylon production was redirected from being a consumer material to one used by the military.<ref name="Kativa" /> DuPont's production of nylon stockings and other lingerie stopped, and most manufactured nylon was used to make parachutes and tents for World War II.<ref name="Krier">Template:Cite news</ref> Although nylon stockings already made before the war could be purchased, they were generally sold on the black market for as high as $20.<ref name=":0" />

Once the war ended, the return of nylon was awaited with great anticipation. Although DuPont projected yearly production of 360 million pairs of stockings, there were delays in converting back to consumer rather than wartime production.<ref name="Kativa" /> In 1946, the demand for nylon stockings could not be satisfied, which led to the nylon riots. In one instance, an estimated 40,000 people lined up in Pittsburgh to buy 13,000 pairs of nylons.<ref name="Wolfe2008"/> In the meantime, women cut up nylon tents and parachutes left from the war in order to make blouses and wedding dresses.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite journal</ref> Between the end of the war and 1952, production of stockings and lingerie used 80% of the world's nylon. DuPont put focus on catering to the civilian demand, and continually expanded its production.

Introduction of nylon blends

As pure nylon hosiery was sold in a wider market, problems became apparent. Nylon stockings were found to be fragile, in the sense that the thread often tended to unravel lengthwise, creating 'runs'.<ref name="Ndiaye" />Template:Rp People also reported that pure nylon textiles could be uncomfortable due to nylon's lack of absorbency.<ref>Template:Cite book</ref> Moisture stayed inside the fabric near the skin under hot or moist conditions instead of being "wicked" away.<ref>Template:Cite journal</ref> Nylon fabric could also be itchy and tended to cling and sometimes spark as a result of static electrical charge built up by friction.<ref name="Mendelson">Template:Cite book</ref><ref name="Shaeffer">Template:Cite book</ref> Also, under some conditions, nylon could degrade, perforating or shredding stockings.<ref name="Meikle"/>Template:Rp Scientists explained this as acid hydrolysis resulting from air pollution, attributing it to London smog in 1952, as well as poor air quality in New York and Los Angeles.<ref name="Cheremisinoff">Template:Cite book</ref><ref name="Stern">Template:Cite book</ref><ref name="Garte">Template:Cite book</ref><ref>Template:Cite journal</ref>

The solution found to problems with pure nylon fabric was to blend nylon with other existing fibres or polymers such as cotton, polyester, and spandex. This led to the development of a wide array of blended fabrics. The new nylon blends retained the desirable properties of nylon (elasticity, durability, ability to be dyed) and kept clothes prices low and affordable.<ref name="Krier" />Template:Rp As of 1950, the New York Quartermaster Procurement Agency (NYQMPA), which developed and tested textiles for the Army and Navy, had committed to developing a wool-nylon blend. They were not the only ones to introduce blends of both natural and synthetic fibres. America's Textile Reporter referred to 1951 as the "Year of the blending of the fibres".<ref name="Haggard">Template:Cite journal</ref> Fabric blends included mixes like "Bunara" (wool-rabbit-nylon) and "Casmet" (wool-nylon-fur).<ref name="Handley"/> In Britain, in November 1951, the inaugural address of the 198th session of the Royal Society for the Encouragement of Arts, Manufactures and Commerce focused on the blending of textiles.<ref name="GOODALE">Template:Cite journal</ref>

DuPont's Fabric Development Department cleverly targeted French fashion designers, supplying them with fabric samples. In 1955, designers such as Coco Chanel, Jean Patou, and Christian Dior showed gowns created with DuPont fibres, and fashion photographer Horst P. Horst was hired to document their use of DuPont fabrics.<ref name="Wolfe2008"/> American Fabrics credited blends with providing "creative possibilities and new ideas for fashions which had been hitherto undreamed of."<ref name="Handley">Template:Cite book</ref>

Etymology

DuPont went through an extensive process to generate names for its new product.<ref name="Meikle" />Template:Rp In 1940, John W. Eckelberry of DuPont stated that the letters "nyl" were arbitrary, and the "on" was copied from the suffixes of other fibres such as cotton and rayon. A later publication by DuPont (Context, vol. 7, no. 2, 1978) explained that the name was originally intended to be "No-Run" ("run" meaning "unravel") but was modified to avoid making such an unjustified claim. Since the products were not really run-proof, the vowels were swapped to produce "nuron", which was changed to "nilon" "to make it sound less like a nerve tonic". For clarity in pronunciation, the "i" was changed to "y".<ref name="Wolfe2008" /><ref>Template:Cite book</ref>

A persistent urban legend exists that the name is derived from "New York" and "London"; however, no organisation in London was ever involved in the research and production of nylon.<ref>Template:Cite book</ref>

Longer-term popularity

Nylon’s popularity soared in the 1940s and 1950s due to its durability and sheerness. In the 1970s, it became more popular due to its flexibility and price.

In spite of oil shortages in the 1970s, consumption of nylon textiles continued to grow by 7.5% per year between the 1960s and 1980s.<ref name="Wilson">Template:Cite book</ref> Overall production of synthetic fibres, however, dropped from 63% of the worlds textile production in 1965, to 45% of the world's textile production in early 1970s.<ref name="Wilson" /> The appeal of "new" technologies wore off, and nylon fabric "was going out of style in the 1970s".<ref name="Ndiaye" /> Also, consumers became concerned about environmental costs throughout the production cycle: obtaining the raw materials (oil), energy use during production, waste produced during creation of the fibre, and eventual waste disposal of materials that were not biodegradable.<ref name="Wilson" /> Synthetic fibres have not dominated the market since the 1950s and 1960s. Template:As of, the worldwide production of nylon is estimated at 8.9 million tons.<ref name="Businesswire">Template:Cite news</ref>

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 polymerisation, to economic impact during the depression and the changing of women's fashion, nylon was a revolutionary product.<ref name="Wolfe2008" /> The Lunar Flag Assembly, the first flag planted on the moon in a symbolic gesture of celebration, was made of nylon. The flag itself cost $5.50 but had to have a specially designed flagpole with a horizontal bar so that it would appear to "fly".<ref name="Welsh">Template:Cite news</ref><ref name="Platoff">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> One historian describes nylon as "an object of desire", comparing the invention to Coca-Cola in the eyes of 20th century consumers.<ref name="Ndiaye" />

Chemistry

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).<ref>Template:Cite book</ref><ref>Template:Cite book</ref> Subsequent use of cyclic and aromatic monomers required the use of letters or sets of letters. One number after "PA" or "Nylon" indicates a homopolymer which is monadic or based on one amino acid (minus H₂O) as monomer:

PA 6 or Nylon 6: [NH−(CH₂)₅−CO]_n made from ε-caprolactam.

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.

PA or Nylon 6,10 (or 610): [NH−(CH₂)₆−NH−CO−(CH₂)₈−CO]_n made from hexamethylenediamine and sebacic acid;

For copolymers the comonomers or pairs of comonomers are separated by slashes:

PA 6/66: [NH−(CH₂)₆−NH−CO−(CH₂)₄−CO]_n−[NH−(CH₂)₅−CO]_m made from caprolactam, hexamethylenediamine and adipic acid;

PA 66/610: [NH−(CH₂)₆−NH−CO−(CH₂)₄−CO]_n−[NH−(CH₂)₆−NH−CO−(CH₂)₈−CO]_m made from hexamethylenediamine, adipic acid and sebacic acid.

The term polyphthalamide (abbreviated to PPA) is used when 60% or more moles of the carboxylic acid portion of the repeating unit in the polymer chain is composed of a combination of terephthalic acid (TPA) and isophthalic acid (IPA).

Types

Nylon 66 and related heteropolymers

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}}

Nylon 66 and related polyamides are condensation polymers forms from equal parts of diamine and dicarboxylic acids.<ref name="Ratner">Template:Cite book</ref> In the first case, the "repeating unit" has the ABAB structure, as also seen in many polyesters and polyurethanes. Since each monomer in this copolymer has the same reactive group on both ends, the direction of the amide bond reverses between each monomer, unlike natural polyamide proteins, which have overall directionality: C terminal → N terminal. In the second case (so called AA), the repeating unit corresponds to the single monomer.<ref name="McIntyre"/>Template:Rp<ref name="Denby">Template:Cite book</ref>

Wallace Carothers at DuPont patented nylon 66.<ref name="US 2130523">Template:Cite patent</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In the case of nylons that involve reaction of a diamine and a dicarboxylic acid, it is difficult to get the proportions exactly correct, and deviations can lead to chain termination at molecular weights less than a desirable 10,000 daltons. To overcome this problem, a crystalline, solid "nylon salt" can be formed at room temperature, using an exact 1:1 ratio of the acid and the base to neutralise each other. The salt is crystallised to purify it and obtain the desired precise stoichiometry. Heated to Template:Cvt, the salt reacts to form nylon polymer with the production of water.

Nylon 510, made from pentamethylene diamine and sebacic acid, was included in the Carothers patent to nylon 66<ref name="US 2130523" /> Nylon 610 is produced similarly using hexamethylene diamine. These materials are more expensive because of the relatively high cost of sebacic acid. Owing to the high hydrocarbon content, nylon 610 is more hydrophobic and finds applications suited for this property, such as bristles.<ref>Template:Cite book</ref>

Commercial heteropolymer polyamides

	1,4-diamino­butane	1,5-diamino­pentane	MPMD	HMD	MXDA	Nonane­diamine	Decane­diamine	Dodecane­diamine	Bis­(para-amino­cyclohexyl)­methane	Trimethyl­hexamethylene­diamine
Adipic acid	46		D6	66	MXD6
Sebacic acid	410	510		610			1010
Dodecanedioic acid				612				1212	PACM12
Terephthalic acid	4T		DT	6T		9T	10T	12T		TMDT
Isophthalic acid			DI	6I

Examples of these polymers that are or were commercially available:

• PA46 DSM Stanyl<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• PA410 DSM Ecopaxx<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• PA4T DSM Four Tii<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• PA66 DuPont Zytel<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

Nylon 6 and related homopolymers

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}}

These polymers are made from a lactam or amino acid. The synthetic route using lactams (cyclic amides) was developed by Paul Schlack at IG Farben, leading to nylon 6, or polycaprolactam—formed by a ring-opening polymerisation. 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.

The Template:Cvt melting point of nylon 6 is lower than the Template:Cvt melting point of nylon 66.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Homopolymer nylons are derived from one monomer.

Monomer	Polymer
Caprolactam	6
11-aminoundecanoic acid	11
ω-aminolauric acid	12

Examples of these polymers that are or were commercially available:

• PA6 Lanxess Durethan B<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• PA11 Arkema Rilsan<ref name="Arkema">{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• PA12 Evonik Vestamid L<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

Nylon 1,6

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}}

Nylons can also be synthesised from dinitriles using acid catalysis. For example, this method is applicable for preparation of nylon 1,6 from adiponitrile, formaldehyde and water.<ref>Template:Cite journal</ref> Additionally, nylons can be synthesised from diols and dinitriles using this method as well.<ref>Template:Cite journal</ref>

Copolymers

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.

Some copolymers that have been or are commercially available are listed below:

• PA6/66 DuPont Zytel<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• PA6/6T BASF Ultramid T (6/6T copolymer)<ref name="Kutz"/>
• PA6I/6T DuPont Selar PA<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• PA66/6T DuPont Zytel HTN<ref name="Kutz">Template:Cite book</ref>
• PA12/MACMI EMS Grilamid TR<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

Blends

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.<ref>Template:Cite journal</ref>

Crystallinity

According to their crystallinity, polyamides can be:

• semi-crystalline:
  • high crystallinity: PA46 and PA66;
  • low crystallinity: PAMXD6 made from m-xylylenediamine and adipic acid;
• amorphous: PA6I made from hexamethylenediamine and isophthalic acid.

According to this classification, PA66, for example, is an aliphatic semi-crystalline homopolyamide.

Environmental impact

File:Amide hydrolysis.svg

The general chemical reaction involving hydrolysis of an amide to form a carboxylic acid and an amine

All nylons are susceptible to hydrolysis, especially by strong acids, a reaction essentially the reverse of their synthesis. 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 12. 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.<ref name="Reltek">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The reaction is shown above.

The average greenhouse gas footprint of nylon in manufacturing carpets is estimated at 5.43 kg CO₂ equivalent per kg, when produced in Europe. This gives it almost the same carbon footprint as wool, but with greater durability and therefore a lower overall carbon footprint.<ref name="Berners-Lee">Template:Cite book</ref>

Data published by PlasticsEurope indicates for nylon 66 a greenhouse gas footprint of 6.4 kg CO₂ equivalent per kg, and an energy consumption of 138 kJ/kg.<ref>Template:Cite book</ref> When considering the environmental impact of nylon, it is important to consider the use phase.

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.Template:Efn Discarded nylon fabric takes 30–40 years to decompose.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Nylon used in discarded fishing gear such as fishing nets is a contributor to debris in the ocean.<ref name="chhabra">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Nylon is a robust polymer and lends itself well to recycling. 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.<ref name="Boydell">Template:Cite journal</ref>

Because of the expense and difficulties of the nylon recycling process, few companies utilise it while most favor using cheaper, newly made plastics for their products instead.<ref name="chhabra"/> US clothing company Patagonia has products containing recycled nylon and in the mid-2010s invested in Bureo, a company that recycles nylon from used fishing nets to use in sunglasses and skateboards.<ref name="chhabra"/> The Italian company Aquafil also has demonstrated recycling fishing nets lost in the ocean into apparel.<ref>Template:Cite journal</ref> Vanden Recycling recycles nylon and other polyamides (PA) and has operations in the UK, Australia, Hong Kong, the UAE, Turkey and Finland.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Nylon is the most popular fibre type in the residential carpet industry today.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The US EPA estimates that 9.2% of carpet fibre, backing and padding was recycled in 2018, 17.8% was incinerated in waste-to-energy facilities, and 73% was discarded in landfills.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Some of the world's largest carpet and rug companies are promoting "cradle to cradle"—the re-use of non-virgin materials including ones not historically recycled—as the industry's pathway forward.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Properties

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.<ref>Valerie Menzer's Nylon 66 Webpage. Arizona University</ref> The amorphous regions contribute elasticity, and the crystalline regions contribute strength and rigidity. 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 fibres. The amount of crystallinity depends on the details of formation, as well as on the kind of nylon.

File:Nylon-3D-h bond.png

Hydrogen bonding in Nylon 66 (in mauve)

Nylon 66 can have multiple parallel strands aligned with their neighboring peptide bonds at coordinated separations of exactly six and four carbons for considerable lengths, so the carbonyl oxygens and amide hydrogens can line up to form interchain hydrogen bonds repeatedly, without interruption (see the figure opposite). Nylon 510 can have coordinated runs of five and eight carbons. Thus parallel (but not antiparallel) strands can participate in extended, unbroken, multi-chain β-pleated sheets, a strong and tough supermolecular structure similar to that found in natural silk fibroin and the β-keratins in feathers. (Proteins have only an amino acid α-carbon separating sequential -CO-NH- groups.) Nylon 6 will form uninterrupted H-bonded sheets with mixed directionalities, but the β-sheet wrinkling is somewhat different. The three-dimensional disposition of each alkane hydrocarbon chain depends on rotations about the 109.47° tetrahedral bonds of singly bonded carbon atoms.

When extruded into fibres through pores in an industry spinneret, the individual polymer chains tend to align because of viscous flow. If subjected to cold drawing afterwards, the fibres align further, increasing their crystallinity, and the material acquires additional tensile strength. In practice, nylon fibres are most often drawn using heated rolls at high speeds.<ref name=Campbell>Template:Cite book</ref>

Block nylon tends to be less crystalline, except near the surfaces due to shearing stresses during formation. Nylon is clear and colourless, 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 plasticiser, lowering the glass transition temperature (T_g), and consequently the elastic modulus at temperatures below the T_g<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

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.

The characteristic features of nylon 66 include:

• Pleats and creases can be heat-set at higher temperatures
• More compact molecular structure
• Better weathering properties; better sunlight resistance
• Softer "Hand"
• High melting point (Template:Cvt)
• Superior colourfastness
• Excellent abrasion resistance

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.

• Variation of luster: nylon has the ability to be very lustrous, semi-lustrous, or dull.
• Durability: its high tenacity fibres are used for seatbelts, tire cords, ballistic cloth, and other uses.
• High elongation
• Excellent abrasion resistance
• Highly resilient (nylon fabrics are heat-set)
• Paved the way for easy-care garments
• High resistance to insects, fungi, animals, as well as molds, mildew, rot, and many chemicals
• Used in carpets and nylon stockings
• Melts instead of burning
• Used in many military applications
• Good specific strength
• Transparent to infrared light (−12 dB)<ref>Template:Cite journal</ref>Template:Clarify

Nylon clothing tends to be less flammable than cotton and rayon, but nylon fibres may melt and stick to skin.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Phillips">Template:Cite book</ref>

Uses

Nylon was first used commercially in a nylon-bristled toothbrush in 1938,<ref name="AOGHS"/><ref name="Nicholson"/> followed more famously in women's stockings or "nylons" which were shown at the 1939 New York World's Fair and first sold commercially in 1940.<ref name="Wolfe2008"/> Its use increased dramatically during World War II, when the need for fabrics increased dramatically.

Fibres

File:The worn out nylon stockings in this barrel full of salvaged stockings will be reprocessed and made into parachutes... - NARA - 196427.jpg

These worn out nylon stockings will be reprocessed and made into parachutes for army fliers Template:Circa

File:Blue nylon ball gown 2007.154.jpg

Blue nylon fabric ball gown by Emma Domb, Science History Institute

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.S. currency. At the outset of the war, cotton accounted for more than 80% of all fibres used and manufactured, and wool fibres accounted for nearly all of the rest. By August 1945, manufactured fibres had taken a market share of 25%, at the expense of cotton. After the war, because of shortages of both silk and nylon, nylon parachute material was sometimes repurposed to make dresses.<ref>Template:Cite journal</ref>

Nylon 6 and 66 fibres are used in carpet manufacture.

Nylon is one kind of fibre used in tire cord. Herman E. Schroeder pioneered application of nylon in tires.

Molds and resins

Nylon resins are widely used in the automobile industry especially in the engine compartment.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Kohan"/>Template:Rp

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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=Youssef>Template:Cite book</ref> Engineering-grade nylon is processed by extrusion, casting, and injection molding. Type 6,6 Nylon 101 is the most common commercial grade of nylon, and Nylon 6 is the most common commercial grade of molded nylon.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Difference">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> For use in tools such as spudgers, nylon is available in glass-filled variants which increase structural and impact strength and rigidity, and molybdenum disulfide-filled variants which increase lubricity. Nylon can be used as the matrix material in composite materials, with reinforcing fibres like glass or carbon fibre; such a composite has a higher density than pure nylon.<ref name=PerformanceComposites>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Such thermoplastic composites (25% to 30% glass fibre) are frequently used in car components next to the engine, such as intake manifolds, where the good heat resistance of such materials makes them feasible competitors to metals.<ref name=Page2000>Template:Cite book</ref>

Nylon was used to make the stock of the Remington Nylon 66 rifle.<ref name=Field1971>Template:Cite journal</ref> The frame of the modern Glock pistol is made of a nylon composite.<ref name=Glock2013>Template:Cite book</ref>

Food packaging

Nylon resins are used as a component of food packaging films where an oxygen barrier is needed.<ref name="BPF"/> Some of the terpolymers based upon nylon are used every day in packaging. Nylon has been used for meat wrappings and sausage sheaths.<ref name=Colbert2013>Template:Cite book</ref> The high temperature resistance of nylon makes it useful for oven bags.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Filaments

Nylon filaments are primarily used in brushes especially toothbrushes<ref name="AOGHS">Template:Cite news</ref> and string trimmers. They are also used as monofilaments in fishing line. Nylon 610 and 612 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.

Other forms

Nylon resins can be extruded into rods, tubes, and sheets.<ref name="Kohan"/>Template:Rp

Nylon powders are used to powder coat metals. Nylon 11 and nylon 12 are the most widely used.<ref name="Kohan"/>Template:Rp

In the mid-1940s, classical guitarist Andrés Segovia mentioned the shortage of good guitar strings in the United States, particularly his favorite Pirastro catgut strings, to a number of foreign diplomats at a party, including General Lindeman of the British Embassy. A month later, the General presented Segovia with some nylon strings which he had obtained via some members of the DuPont family. Segovia found that although the strings produced a clear sound, they had a faint metallic timbre which he hoped could be eliminated.<ref name=Guitar>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Nylon strings were first tried on stage by Olga Coelho in New York in January 1944.<ref name="Bellow">Template:Cite book</ref> In 1946, Segovia and string maker Albert Augustine were introduced by their mutual friend Vladimir Bobri, editor of Guitar Review. On the basis of Segovia's interest and Augustine's past experiments, they decided to pursue the development of nylon strings. DuPont, skeptical of the idea, agreed to supply the nylon if Augustine would endeavor to develop and produce the actual strings. After three years of development, Augustine demonstrated a nylon first string whose quality impressed guitarists, including Segovia, in addition to DuPont.<ref name=Guitar/> Wound strings, however, were more problematic. Eventually, however, after experimenting with various types of metal and smoothing and polishing techniques, Augustine was also able to produce high quality nylon wound strings.<ref name=Guitar/>

See also

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Further reading

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External links

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• Polyamide Nylon Plastic
• Joseph X. Labovsky Collection of Nylon Photographs and Ephemera Science History Institute Digital Collections. (High-resolution scans of nylon-related photographs and ephemera collected by Joseph X. Labovsky, a lab assistant to Wallace Carothers, during the early stages of nylon development and production at DuPont).