Nylon 1

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Nylon is a generic designation for a family of synthetic polymers composed of polyamides (repeating units linked by amide links).[a][1][2] Nylon is a thermoplastic silky material,[3] generally made from petroleum,[4] that can be melt-processed into fibers, films, or shapes.[5]:2 Nylon polymers can be mixed with a wide variety of additives to achieve many different property variations. Nylon polymers have found significant commercial applications in fabric and fibers (apparel, flooring and rubber reinforcement), in shapes (molded parts for cars, electrical equipment, etc.), and in films (mostly for food packaging).[6]
Nylon was the first commercially successful synthetic thermoplastic polymer.[7] DuPont began its research project in 1927.[8] The first example of nylon, (nylon 66), was synthesized using diamines on February 28, 1935 by Wallace Hume Carothers at DuPont's research facility at the DuPont Experimental Station.[9][10] In response to Carothers' work, Paul Schlack at IG Farben developed nylon 6, a different molecule based on caprolactam, on January 29, 1938.[11]:10[12]
Nylon was first used commercially in a nylon-bristled toothbrush in 1938,[4][13] 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,[14] 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.[15]
DuPont, founded by Éleuthère Irénée du Pont, first produced gunpowder and later cellulose-based paints. Following WWI, DuPont produced synthetic ammonia and other chemicals. DuPont began experimenting with the development of cellulose based fibers, eventually producing the synthetic fiber rayon. DuPont's experience with rayon was an important precursor to its development and marketing of nylon.[16]:8,64,236
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.[8] The project grew from a new organizational 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".[16]:92 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.[17] He was very successful, as research he undertook greatly improved the knowledge of polymers and contributed to science.[18]
In the spring of 1930, Carothers and his team had already synthesized two new polymers. One was neoprene, a synthetic rubber greatly used during World War II.[19] 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 polymerization to a more practically-focused goal of finding "one chemical combination that would lend itself to industrial applications".[16]:94
It wasn't 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.[20] This cold drawing method was later used by Carothers in 1935 to fully develop nylon.[21] The first example of nylon (nylon 6,6) was produced on February 28, 1935, at DuPont's research facility at the DuPont Experimental Station.[9] 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,[22] and quickly achieved a monopoly of the fiber.[18] Carothers died 16 months before the announcement of nylon, therefore he was never able to see his success.[8]
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. 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”,[16] 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.[16]
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.[16] The ability to acquire a large number of chemists and engineers quickly was a huge contribution to the success of DuPont's nylon project.[16]:100–101 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.[23]
An important part of nylon's popularity stems from DuPont's marketing strategy. DuPont promoted the fiber 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 Tribune's yearly "Forum on Current Problems", on the site of the approaching New York City world's fair.[17][18]:141 The "first man-made organic textile fiber" 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.[18]:141 Nylon was introduced as part of "The world of tomorrow" at the 1939 New York World's Fair[24] and was featured at DuPont's "Wonder World of Chemistry" at the Golden Gate International Exposition in San Francisco in 1939.[17][25] 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.[18]:145–146 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.[17]
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.[18]
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.[18]:145–147[14] 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.[18]
Also, DuPont executives marketing nylon as a revolutionary man-made material did not at first realize that some consumers experienced a sense of unease and distrust, even fear, towards synthetic fabrics.[18]:126–128 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),[b] 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.[18]:146–147
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.[18]:146–147 Nylon was thus domesticated,[18]:151–152 and attention shifted to the material and consumer aspect of the fiber with slogans like "If it's nylon, it's prettier, and oh! How fast it dries!".[16]:2
After nylon's nationwide release in 1940, production was increased. 1300 tons of the fabric were produced during 1940.[16]:100 During their first year on the market, 64 million pairs of nylon stockings were sold.[16]:101 In 1941, a second plant was opened in Martinsville, Virginia due to the success of the fabric.[26]
While nylon was marketed as the durable and indestructible material of the people, it was sold at almost twice the price of silk stockings ($4.27 per pound of nylon versus $2.79 per pound of silk).[16]:101 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.[27]
However, as of February 11, 1942, nylon production was redirected from being a consumer material to one used by the military.[17] 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.[28] Although nylon stockings already made before the war could be purchased, they were generally sold on the black market for as high as $20.[26]
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.[17] 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.[14] In the meantime, women cut up nylon tents and parachutes left from the war in order to make blouses and wedding dresses.[29][30] Between the end of the war and 1952, production of stockings and lingerie used 80% of the world's nylon. DuPont put a lot of focus on catering to the civilian demand, and continually expanded its production.
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'.[16]:101 People also reported that pure nylon textiles could be uncomfortable due to nylon's lack of absorbency.[31] Moisture stayed inside the fabric near the skin under hot or moist conditions instead of being "wicked" away.[32] Nylon fabric could also be itchy, and tended to cling and sometimes spark as a result of static electrical charge built up by friction.[33][34] Also, under some conditions stockings could decompose[18] turning back into nylon's original components of air, coal, and water. Scientists explained this as a result of air pollution, attributing it to London smog in 1952, as well as poor air quality in New York and Los Angeles.[35][36][37]
The solution found to problems with pure nylon fabric was to blend nylon with other existing fibers 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.[28]:2 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 fibers. America's Textile Reporter referred to 1951 as the "Year of the blending of the fibers".[38] Fabric blends included mixes like "Bunara" (wool-rabbit-nylon) and "Casmet" (wool-nylon-fur).[39] 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.[40]
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 fibers, and fashion photographer Horst P. Horst was hired to document their use of DuPont fabrics.[14] American Fabrics credited blends with providing "creative possibilities and new ideas for fashions which had been hitherto undreamed of."[39]
DuPont went through an extensive process to generate names for its new product.[18]:138–139 In 1940, John W. Eckelberry of DuPont stated that the letters "nyl" were arbitrary, and the "on" was copied from the suffixes of other fibers 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".[14][41]
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.[42]
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.[43] Overall production of synthetic fibers, however, dropped from 63% of the worlds textile production in 1965, to 45% of the world's textile production in early 1970s.[43] The appeal of "new" technologies wore off, and nylon fabric "was going out of style in the 1970s".[16] 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 fiber, and eventual waste disposal of materials that were not biodegradable.[43] Synthetic fibers have not dominated the market since the 1950s and 1960s. As of 2020, the worldwide production of nylon is estimated at 8.9 million tons.[44] As one of the largest engineering polymer families, the global demand of nylon resins and compounds was valued at roughly US$20.5 billion in 2013. The market is expected to reach US$30 billion by 2020 by following an average annual growth of 5.5%.[45]
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.[14] 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".[46][47] One historian describes nylon as "an object of desire", comparing the invention to Coca-Cola in the eyes of 20th century consumers.[16]
 "Making Nylon", Bob Burk, CHEM 1000, Carleton University, Ottawa, Canada
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.g. PA66) or a lactam or amino acid with itself (e.g. PA6).[48] In the first case, the "repeating unit" consists of one of each monomer, so that they alternate in the chain, similar to the so-called ABAB structure of 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.[11]:45–50[49]
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).[50][51] 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:
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.
For copolymers the comonomers or pairs of comonomers are separated by slashes:
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).
Wallace Carothers at DuPont patented nylon 66 using amides.[22][52][53] 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 (u). 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 neutralize each other. The salt is crystallized to purify it and obtain the desired precise stoichiometry. Heated to 285 °C (545 °F), the salt reacts to form nylon polymer with the production of water.
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 polymerization. The peptide b
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