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Alternate titles: nylon 6,6, polyhexamethylene adipamide
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Sep 26, 2022
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In October 1938, DuPont announced the invention of the first wholly synthetic fibre ever produced. Given the trade name Nylon (which has...
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nylon , any synthetic plastic material composed of polyamides of high molecular weight and usually, but not always, manufactured as a fibre . Nylons were developed in the 1930s by a research team headed by an American chemist, Wallace H. Carothers , working for E.I. du Pont de Nemours & Company . The successful production of a useful fibre by chemical synthesis from compounds readily available from air, water, and coal or petroleum stimulated expansion of research on polymers , leading to a rapidly proliferating family of synthetics .
Nylon can be drawn, cast, or extruded through spinnerets from a melt or solution to form fibres, filaments, bristles, or sheets to be manufactured into yarn , fabric, and cordage; and it can be formed into molded products. It has high resistance to wear, heat, and chemicals.
When cold-drawn, it is tough, elastic, and strong. Most generally known in the form of fine and coarse filaments in such articles as hosiery, parachutes, and bristles, nylon is also used in the molding trade, particularly in injection molding, where its toughness and ability to flow around complicated inserts are prime advantages.
Polyamides may be made from a dicarboxylic acid and a diamine or from an amino acid that is able to undergo self-condensation, or its lactam, characterized by the functional group ―CONH― in a ring, such as ε -caprolactam. By varying the acid and the amine , it is possible to make products that are hard and tough or soft and rubbery. Whether made as filaments or as moldings, polyamides are characterized by a high degree of crystallinity, particularly those derived from primary amines. Under tension, orientation of molecules continues until the specimen is drawn to about four times its initial length, a property of particular importance in filaments.
Two of the ingredients that are used to synthesize the most common nylon, adipic acid and hexamethylenediamine, each contain six carbon atoms, and the product has been named nylon-6,6. When caprolactam is the starting material, nylon-6 is obtained, so named because it has six carbon atoms in the basic unit.
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Using stories from science’s past to understand our world
The invention of nylon in 1938 ushered in a textile revolution for consumers and the military alike, ultimately helping the Allies win World War II.
A giant leg, 35 feet high, advertised nylons to the Los Angeles area.
When it first entered the public consciousness in 1938, nylon claimed a novelty no other product could match. Its predecessor, rayon, had been touted as “artificial silk,” a phrase that implied both economy and imitation. But nylon was billed by its manufacturer, DuPont, as a thing unto itself. As the first commercially viable synthetic fiber, nylon ushered in a fashion revolution based on comfort, ease, and disposability. Its strength, elasticity, weight, and resistance to mildew helped the Allies win World War II. Behind the scenes the invention of nylon also transformed the chemical industry by proving that the composition of polymers could be predicted and engineered like many other chemical products. Today nylon—in toothbrushes, carpet, racket and guitar strings, surgical sutures, car parts, and, of course, hosiery—is all around us.
The first venture of E. I. du Pont de Nemours and Company into artificial fibers came in 1920 when it purchased a 60% interest in Comptoir des Textiles Artificiels, a French rayon company, for $4 million. The combined firm, named the DuPont Fiber Company, eventually became the Rayon Department of the DuPont Company. Although rayon proved popular and profitable, the company expended considerable resources in improving the brittle fiber’s texture and performance—in 1934 alone the company spent $1 million on rayon research.
In December 1926 Charles M. A. Stine, the director of DuPont’s Chemical Department, circulated a memo to the company’s executive committee that suggested the committee was looking in the wrong place for innovation. Rather than investing in practical research directly related to such existing products as rayon or ammonia, Stine argued, DuPont should fund “pure science work.” This work would be centered on “the object of establishing or discovering new scientific facts” instead of research that “applied previously established scientific facts to practical problems.” Stine’s proposal was not new to industry—both General Electric and Bell Telephone operated industrial research laboratories—but his insistence that the research be “pure” or “fundamental” was a fairly radical idea for a company focused on profits. Nevertheless, the executive committee approved a slightly modified version of Stine’s proposal in March 1927. Stine was granted $25,000 a month for research and was told to hire 25 of the best chemists he could find. The committee also approved funds to build a new laboratory, soon dubbed “Purity Hall” by DuPont chemists.
[LEFT] Photograph of a nylon tulle dress “glittering with brilliants” from a 1958 Christian Dior collection, circulated by DuPont’s public relations department. [RIGHT] A 35-foot-high leg display advertising nylon in Los Angeles, California. The leg was modeled by movie star Marie Wilson, shown suspended from the crane.
Stine encountered much more difficulty in attracting chemists to DuPont than he had anticipated, largely because academic scientists doubted whether they would truly be allowed to do pure research in an industrial setting. A year later, however, he made a spectacular hire when he convinced Wallace H. Carothers, a young organic chemistry lecturer at Harvard University, to join DuPont. Carothers proposed to center his research on polymerization, the process by which individual short molecules form long-chain macromolecules. Before Carothers’s groundbreaking work most chemists based their polymers on complicated “recipes” largely determined by chance. Moreover, the nature of polymers was poorly understood, with some researchers convinced that the sticky resins represented complex colloidal systems, while others advocated the long-chain molecule theory originally advanced by Hermann Staudinger, a German chemist. Carothers hoped to offer definitive proof of Staudinger’s theory by constructing polymers from small organic molecules with known reactivity at both ends.
Carothers’s success was almost immediate. In April 1930 Julian W. Hill, a research associate in Carother’s group, produced a long polymeric ester with a molecular weight of more than 12,000 by combining a dialcohol and a diacid—this was the first “polyester.” Hill’s polyester fibers had a remarkable property: when cooled, the thin, brittle filaments could be pulled into an elastic thread four times their original length. DuPont researchers soon realized, however, that this first polyester would never succeed as a commercial fiber because its low melting point made laundering and ironing impractical.
For the next four years attempts to create commercially viable synthetic fibers were stymied by the twin problems of low melting points and high solubility in water. In 1934 Elmer Bolton, the new chemical director at DuPont, urged Carothers to return to the problem. Carothers agreed, but this time he would focus on polyamides rather than polyesters. On 24 May 1934 a member of his research team, Donald D. Coffman, successfully pulled a fiber of a polymer based on an aminoethylester. His fiber—ultimately the first nylon—retained the remarkable elastic properties of the polyesters but lacked their drawbacks. However, since the intermediate used to form the polymer, aminononanoic ester, was tremendously difficult to produce, Carothers and his associates kept looking.
Within a year Carothers’s six researchers had narrowed the field to two possibilities: polyamide 5,10, made from pentamethylene diamine and sebacic acid; and polyamide 6,6, made from hexamethylenediamine and adipic acid. (The molecules are named for the number of carbons in the starting materials.) Carothers preferred 5,10, but Bolton pushed for 6,6 because the intermediates could be more easily prepared from benzene, a readily available starting material derived from coal tar. As Carothers’s declining mental health kept him increasingly absent from the laboratory, Bolton’s choice prevailed, and all hands turned to improving fiber 6,6.
Joseph Labovsky, a chemical engineer working as a technician in the lab, later recalled that the lab workers were scaling up fiber 6,6 “from 1 ounce to 1 pound, 2 pounds, 50 pounds, 250 pounds, and eventually to 2,000 pounds.” Paul Flory, a young physical chemist who would later win the Nobel Prize in Chemistry for his work on polymers, helped the researchers stabilize the reaction by developing a mathematical model for the kinetics of the polymerization reaction. In 1938 DuPont started construction on a nylon production facility in Seaford, Delaware, that could produce up to 12 million pounds of the synthetic fiber a year. It was time to introduce nylon to the American public.
Nylon’s characteristics made for an ideal material to suit any number of uses, but DuPont decided early on that it would focus on a single market: ladies’ full-fashioned hosiery. As hemlines continued to rise throughout the 1930s, silk and rayon stockings had become an increasingly necessary part of every woman’s wardrobe. American women bought an average of eight pairs of stockings per year, earning Japanese silk producers over $70 million annually. DuPont never intended to produce the stockings directly; rather, the company would provide nylon thread to mills that would knit and sell the hosiery.
As hemlines continued to rise throughout the 1930s, silk and rayon stockings had become an increasingly necessary part of every woman’s wardrobe.
Before DuPont could take its new miracle fiber to the public, however, its leaders had to decide what to call it. In-house researchers had alternately been referring to what would become nylon as Rayon 66, Fiber 66, or “Duparon,” a creative acronym for “DuPont pulls a rabbit out [of] nitrogen/nature/nozzle/naphtha.” In 1938, through a decision-making process that remains somewhat obscure, the company settled on the word nylon . According to Ernest Gladding, manager of the Nylon Division in 1941, the name had originally been “Nuron,” which not only implied novelty but cleverly spelled “no run” backwards. Unfortunately, Nuron and other closely related words posed trademark conflicts, so the division proposed “Nilon.” Changing the i to a y removed any ambiguity surrounding pronunciation, and “nylon” was born. The company then decided not to trademark the name, hoping instead to encourage consumers to think of nylon as a generic preexisting material, like wood or glass.
Since 1931, when Carothers first reported on his polyester fibers at an American Chemical Society meeting, newspapers had been reporting rumors that DuPont had developed a new fiber as good as or better than silk. By early 1938 the press was producing a steady stream of articles that suggested that stockings made from the mystery fiber would outlast silk and never run. If DuPont executives had begun to grow nervous about unrealistic expectations, they grew truly alarmed in September 1938 when the Washington News ran a story based on the newly released patent (U.S. 2,130,948). The article claimed that nylon could be prepared from cadaverine, a substance formed during putrefaction in dead bodies. When combined with reports of Carothers’s suicide earlier that year, coverage of nylon took on an oddly morbid tone. Perhaps to counteract these rumors, for many years thereafter DuPont’s publicity department stressed that nylon was derived solely from coal, air, and water.
DuPont regained control of nylon’s publicity on 27 October 1938, when it officially introduced the stockings to a crowd of 4,000 enthusiastic middle-class women at the future site of the New York World’s Fair. But while the excitement was b
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