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Nylon is a family of
synthetic polymer Some familiar household synthetic polymers include: Nylons in textiles and fabrics, Teflon in non-stick pans, Bakelite for electrical switches, polyvinyl chloride (PVC) in pipes, etc. The common PET bottles are made of a synthetic polymer, polyet ...
s characterised by
amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...
linkages, typically connecting
aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...
or semi-aromatic groups. Nylons are generally brownish in color and can possess a soft texture, with some varieties exhibiting a
silk Silk is a natural fiber, natural protein fiber, some forms of which can be weaving, woven into textiles. The protein fiber of silk is composed mainly of fibroin and is most commonly produced by certain insect larvae to form cocoon (silk), c ...
-like appearance. As
thermoplastics A thermoplastic, or thermosoftening plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplastics have a high molecular weight. The polymer chains as ...
, nylons can be melt-processed into fibres,
films A film, also known as a movie or motion picture, is a work of Visual arts, visual art that simulates experiences and otherwise communicates ideas, stories, perceptions, emotions, or atmosphere through the use of moving images that are gen ...
, and diverse shapes. 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
diamine A diamine is an amine with two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to Primary (chemistry), primary diamines, as those are the most reactive. In terms of ...
s and
dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic.Boy Cornils, Peter Lappe "Dicarbox ...
s of carbon chain lengths X and Y, respectively. An important example is nylon-6,6 (). Another family, designated nylon-Z, is derived from aminocarboxylic acids with carbon chain length Z. An example is nylon- Nylon polymers have extensive commercial applications, including uses in
textiles Textile is an Hyponymy and hypernymy, umbrella term that includes various Fiber, fiber-based materials, including fibers, yarns, Staple (textiles)#Filament fiber, filaments, Thread (yarn), threads, and different types of #Fabric, fabric. ...
and fibres (such as apparel, flooring and rubber reinforcement), molded components for automotive and electrical equipment, and films (mostly for
food packaging Food packaging is a packaging system specifically designed for food and represents one of the most important aspects among the processes involved in the food industry, as it provides protection from chemical, biological and physical alterations ...
).


History


DuPont and the invention of nylon

Researchers at
DuPont Dupont, DuPont, Du Pont, duPont, or du Pont may refer to: People * Dupont (surname) Dupont, also spelled as DuPont, duPont, Du Pont, or du Pont is a French surname meaning "of the bridge", historically indicating that the holder of the surname re ...
began developing cellulose-based fibres, culminating in the synthetic fibre
rayon Rayon, also called viscose and commercialised in some countries as sabra silk or cactus silk, is a semi-synthetic fiber made from natural sources of regenerated cellulose fiber, cellulose, such as wood and related agricultural products. It has t ...
. DuPont's experience with rayon was an important precursor to its development and marketing of nylon. 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 The 1939 New York World's Fair (also known as the 1939–1940 New York World's Fair) was an world's fair, international exposition at Flushing Meadows–Corona Park in Queens, New York City, New York, United States. The fair included exhibitio ...
. The project grew from a new organisational structure at DuPont, suggested by
Charles Stine Charles Milton Altland Stine (18 October 1882 – 28 May 1954) was a chemist and a vice-president of DuPont who created the laboratory from which nylon and other significant inventions were made. He was also a devout Christian who authored a boo ...
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". Harvard instructor
Wallace Hume Carothers Wallace Hume Carothers (; April 27, 1896 – April 29, 1937) was an American chemist, inventor, and the leader of organic chemistry at DuPont, who was credited with the invention of nylon. Carothers was a group leader at the DuPont Experimen ...
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 Hermann Staudinger (; 23 March 1881 – 8 September 1965) was a German organic chemist who demonstrated the existence of macromolecules, which he characterized as polymers. For this work he received the 1953 Nobel Prize in Chemistry. He is also ...
. He was very successful, as research he undertook greatly improved the knowledge of polymers and contributed to the science. Nylon was the first commercially successful synthetic
thermoplastic A thermoplastic, or thermosoftening plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplastics have a high molecular weight. The polymer chains as ...
polymer. DuPont began its research project in 1927. The first nylon,
nylon 66 Nylon 66 (loosely written nylon 6-6, nylon 6/6, nylon 6,6, or nylon 6:6) is a type of polyamide or nylon. It, and nylon 6, are the two most common for textile and plastic industries. Nylon 66 is made of two monomers each containing six carbon at ...
, was synthesised on February 28, 1935, by Wallace Hume Carothers at DuPont's research facility at the
DuPont Experimental Station The DuPont Experimental Station is the largest research and development facility of DuPont, located on the banks of the Brandywine Creek (Christina River), Brandywine Creek in Wilmington, Delaware. On the morning of January 24, 2007, President ...
. In response to Carothers' work,
Paul Schlack Paul Schlack (22 December 1897 – 19 August 1987) was a German chemist. He completed his studies at the Technical University of Stuttgart in 1921 and worked as a research chemist in Copenhagen for a year, before returning to Stuttgart. He re ...
at
IG Farben I. G. Farbenindustrie AG, commonly known as IG Farben, was a German Chemical industry, chemical and Pharmaceutical industry, pharmaceutical conglomerate (company), conglomerate. It was formed on December 2, 1925 from a merger of six chemical co ...
developed nylon 6, a different molecule based on
caprolactam Caprolactam (CPL) is an organic compound with the chemical formula, formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately five million tons per year, and the vast ...
, on January 29, 1938. In the spring of 1930, Carothers and his team had already synthesised two new polymers. One was
neoprene Neoprene (also polychloroprene) is a family of synthetic rubbers that are produced by polymerization of chloroprene.Werner Obrecht, Jean-Pierre Lambert, Michael Happ, Christiane Oppenheimer-Stix, John Dunn and Ralf Krüger "Rubber, 4. Emulsion Rub ...
, a synthetic rubber greatly used during World War II. 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". It was not until the beginning of 1935 that a polymer called "polymer 6-6" was finally produced. Carothers' coworker,
Washington University Washington University in St. Louis (WashU) is a private research university in St. Louis, Missouri, United States. Founded in 1853 by a group of civic leaders and named for George Washington, the university spans 355 acres across its Danforth ...
alumnus Julian W. Hill had used a cold drawing method to produce a
polyester Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natura ...
in 1930. This cold drawing method was later used by Carothers in 1935 to fully develop nylon. The first example of nylon (nylon 6.6) was produced on February 28, 1935, at DuPont's research facility at the DuPont Experimental Station. 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, and quickly achieved a monopoly of the fibre. Carothers died 16 months before the announcement of nylon, therefore he was never able to see his success. 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. Nylon was first used commercially in a nylon-
bristle A bristle is a stiff hair or feather (natural or artificial), either on an animal, such as a pig, a plant, or on a tool such as a brush or broom. Synthetic types Synthetic materials such as nylon are also used to make bristles in items such as b ...
d
toothbrush A toothbrush is a special type of brush used to clean the Human tooth, teeth, gingiva, gums, and tongue. It consists of a head of tightly clustered bristles, atop of which toothpaste can be applied, mounted on a handle (grip), handle which facil ...
in 1938, followed more famously in women's
stocking Stockings (also known as hose, especially in a historical context) are close-fitting, variously elastic garments covering the leg from the foot up to the knee or possibly part or all of the thigh. Stockings vary in color, design, and transpar ...
s or "nylons" which were shown at the 1939 New York World's Fair and first sold commercially in 1940, 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 Plastics are a wide range of synthetic or semisynthetic materials composed primarily of polymers. Their defining characteristic, plasticity, allows them to be molded, extruded, or pressed into a diverse range of solid forms. This adaptab ...
greatly increased the market for the new materials. 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", 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 The Great Depression was a severe global economic downturn from 1929 to 1939. The period was characterized by high rates of unemployment and poverty, drastic reductions in industrial production and international trade, and widespread bank and ...
by creating jobs and revenue at DuPont. DuPont's nylon project demonstrated the importance of
chemical engineering Chemical engineering is an engineering field which deals with the study of the operation and design of chemical plants as well as methods of improving production. Chemical engineers develop economical commercial processes to convert raw materials ...
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. The ability to acquire a large number of chemists and engineers quickly was a huge contribution to the success of DuPont's nylon project. 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 The American Chemical Society (ACS) is a scientific society based in the United States that supports scientific inquiry in the field of chemistry. Founded in 1876 at New York University, the ACS currently has more than 155,000 members at all ...
.


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 Tribune''s yearly "Forum on Current Problems", on the site of the approaching New York City world's fair. 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. Nylon was introduced as part of "The world of tomorrow" at the 1939 New York World's Fair and was featured at DuPont's "Wonder World of Chemistry" at the
Golden Gate International Exposition The Golden Gate International Exposition (GGIE) was a World's Fair held at Treasure Island in San Francisco, California, U.S. The exposition operated from February 18, 1939, through October 29, 1939, and from May 25, 1940, through September 29, ...
in San Francisco in 1939. 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. 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. 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. 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. 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. 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. 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 Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor. It is present in small quantities in living organisms but is often associated with the putrefaction of Tiss ...
(pentamethylenediamine), 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. 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. Nylon was thus domesticated, 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!".


Production of nylon fabric

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.  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.  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. 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 Silk is a natural fiber, natural protein fiber, some forms of which can be weaving, woven into textiles. The protein fiber of silk is composed mainly of fibroin and is most commonly produced by certain insect larvae to form cocoon (silk), c ...
stockings ($4.27 per pound of nylon versus $2.79 per pound of silk). Sales of nylon stockings were strong in part due to changes in women's fashion. As Lauren Olds explains: "by 1939 emlineshad 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. However, as of February 11, 1942, nylon production was redirected from being a consumer material to one used by the military. 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 World War II or the Second World War (1 September 1939 – 2 September 1945) was a World war, global conflict between two coalitions: the Allies of World War II, Allies and the Axis powers. World War II by country, Nearly all of the wo ...
. Although nylon stockings already made before the war could be purchased, they were generally sold on the black market for as high as $20. 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. In 1946, the demand for nylon stockings could not be satisfied, which led to the
nylon riots The nylon riots were a series of disturbances at American stores created by a nylon stocking shortage. Background Nylon was patented by DuPont in 1935, and the company began manufacturing nylon stockings in 1939. The product quickly became pop ...
. In one instance, an estimated 40,000 people lined up in Pittsburgh to buy 13,000 pairs of nylons. In the meantime, women cut up nylon tents and parachutes left from the war in order to make blouses and wedding dresses. 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'. People also reported that pure nylon textiles could be uncomfortable due to nylon's lack of absorbency. Moisture stayed inside the fabric near the skin under hot or moist conditions instead of being "wicked" away. Nylon fabric could also be itchy and tended to cling and sometimes spark as a result of static electrical charge built up by friction. Also, under some conditions, nylon could degrade, perforating or shredding stockings. Scientists explained this as acid hydrolysis resulting from
air pollution Air pollution is the presence of substances in the Atmosphere of Earth, air that are harmful to humans, other living beings or the environment. Pollutants can be Gas, gases like Ground-level ozone, ozone or nitrogen oxides or small particles li ...
, attributing it to London smog in 1952, as well as poor air quality in New York and Los Angeles. The solution found to problems with pure nylon fabric was to blend nylon with other existing fibres or polymers such as
cotton Cotton (), first recorded in ancient India, is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure ...
,
polyester Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natura ...
, and
spandex Spandex, Lycra, or elastane is a synthetic fiber known for its exceptional elasticity. It is a polyether- polyurea copolymer that was invented in 1958 by chemist Joseph Shivers at DuPont. Name The name ''spandex'', which is an anagram of t ...
. 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. As of 1950, the New York Quartermaster Procurement Agency (NYQMPA), which developed and tested textiles for the
Army An army, ground force or land force is an armed force that fights primarily on land. In the broadest sense, it is the land-based military branch, service branch or armed service of a nation or country. It may also include aviation assets by ...
and
Navy A navy, naval force, military maritime fleet, war navy, or maritime force is the military branch, branch of a nation's armed forces principally designated for naval warfare, naval and amphibious warfare; namely, lake-borne, riverine, littoral z ...
, 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". Fabric blends included mixes like "Bunara" (wool-rabbit-nylon) and "Casmet" (wool-nylon-fur). 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. DuPont's Fabric Development Department cleverly targeted French fashion designers, supplying them with fabric samples. In 1955, designers such as
Coco Chanel Gabrielle Bonheur "Coco" Chanel ( , ; 19 August 1883 – 10 January 1971) was a French fashion designer and Businessperson, businesswoman. The founder and namesake of the Chanel brand, she was credited in the post-World War I era with populari ...
,
Jean Patou Jean Patou (; 27 September 1887 – 8 March 1936) was a French fashion designer, and founder of the Jean Patou brand. Early life Patou was born in Paris, France in 1880. Patou's family's business was tanning and furs. Patou worked with his u ...
, and
Christian Dior Christian Ernest Dior (; 21 January 1905 – 24 October 1957) was a French fashion designer and founder of one of the world's top fashion houses, Dior, Christian Dior SE. His fashion house is known all around the world, having gained promi ...
showed gowns created with DuPont fibres, and fashion photographer Horst P. Horst was hired to document their use of DuPont fabrics. ''American Fabrics'' credited blends with providing "creative possibilities and new ideas for fashions which had been hitherto undreamed of."


Etymology

DuPont went through an extensive process to generate names for its new product. 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 Cotton (), first recorded in ancient India, is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure ...
and
rayon Rayon, also called viscose and commercialised in some countries as sabra silk or cactus silk, is a semi-synthetic fiber made from natural sources of regenerated cellulose fiber, cellulose, such as wood and related agricultural products. It has t ...
. 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". A persistent
urban legend Urban legend (sometimes modern legend, urban myth, or simply legend) is a genre of folklore concerning stories about an unusual (usually scary) or humorous event that many people believe to be true but largely are not. These legends can be e ...
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.


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. 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. The appeal of "new" technologies wore off, and nylon fabric "was going out of style in the 1970s". 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. Synthetic fibres have not dominated the market since the 1950s and 1960s. , the worldwide production of nylon is estimated at 8.9 million tons. 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. The
Lunar Flag Assembly The Lunar Flag Assembly (LFA) was a kit containing a flag of the United States designed to be erected on the Moon during the Apollo program. Six such flag assemblies were planted on the Moon. The nylon flags were hung on telescoping staffs and h ...
, 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". One historian describes nylon as "an object of desire", comparing the invention to Coca-Cola in the eyes of 20th century consumers.


Chemistry

In common usage, the prefix "PA" (
polyamide A polyamide is a polymer with repeating units linked by amide bonds. Polyamides occur both naturally and artificially. Examples of naturally occurring polyamides are proteins, such as wool and silk. Artificially made polyamides can be made throug ...
) 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). 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 A polymer () is a substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeating subunits derived from one or more species of monomers. Due to their broad spectrum of properties, both ...
which is ''monadic'' or based on one amino acid (minus H2O) as monomer: : PA 6 or Nylon 6: H−(CH2)5−COsub>''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): H−(CH2)6−NH−CO−(CH2)8−COsub>''n'' made from
hexamethylenediamine Hexamethylenediamine or hexane-1,6-diamine, is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish f ...
and
sebacic acid Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula . It is a white flake or powdered solid. ''Sebaceus'' is Latin for tallow candle, ''sebum'' is Latin for tallow, and refers to its use in the manufacture of candles. ...
; For copolymers the comonomers or pairs of comonomers are separated by slashes: : PA 6/66: H−(CH2)6−NH−CO−(CH2)4−COsub>''n''− H−(CH2)5−COsub>''m'' made from caprolactam, hexamethylenediamine and adipic acid; : PA 66/610: H−(CH2)6−NH−CO−(CH2)4−COsub>''n''− H−(CH2)6−NH−CO−(CH2)8−COsub>''m'' made from hexamethylenediamine, adipic acid and sebacic acid. The term
polyphthalamide Polyphthalamide (aka. PPA, High Performance Polyamide) is a subset of thermoplastic synthetic resins in the polyamide (nylon) family defined as when 55% or more moles of the carboxylic acid portion of the repeating unit in the polymer chain is co ...
(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 Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annuall ...
(TPA) and
isophthalic acid Isophthalic acid is an organic compound with the formula C6H4(CO2H)2. This colorless solid is an isomer of phthalic acid and terephthalic acid. The main industrial uses of purified isophthalic acid (PIA) are for the production of polyethylene ...
(IPA).


Types


Nylon 66 and related heteropolymers

Nylon 66 and related polyamides are
condensation polymer In polymer chemistry, condensation polymers are any kind of polymers whose process of polymerization involves a condensation reaction (i.e. a small molecule, such as water or methanol, is produced as a byproduct). Natural proteins as well as s ...
s forms from equal parts of
diamine A diamine is an amine with two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to Primary (chemistry), primary diamines, as those are the most reactive. In terms of ...
and
dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic.Boy Cornils, Peter Lappe "Dicarbox ...
s. In the first case, the "repeating unit" has the ABAB structure, as also seen in many
polyester Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natura ...
s and
polyurethane Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...
s. Since each monomer in this copolymer has the same reactive group on both ends, the direction of the
amide bond In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a p ...
reverses between each monomer, unlike natural
polyamide A polyamide is a polymer with repeating units linked by amide bonds. Polyamides occur both naturally and artificially. Examples of naturally occurring polyamides are proteins, such as wool and silk. Artificially made polyamides can be made throug ...
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...
s, which have overall directionality: C terminal → N terminal. In the second case (so called AA), the repeating unit corresponds to the single monomer. Wallace Carothers at DuPont patented nylon 66. 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
crystal A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
line, solid "nylon
salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
" can be formed at
room temperature Room temperature, colloquially, denotes the range of air temperatures most people find comfortable indoors while dressed in typical clothing. Comfortable temperatures can be extended beyond this range depending on humidity, air circulation, and ...
, using an exact 1:1
ratio In mathematics, a ratio () shows how many times one number contains another. For example, if there are eight oranges and six lemons in a bowl of fruit, then the ratio of oranges to lemons is eight to six (that is, 8:6, which is equivalent to the ...
of the
acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...
and the base to neutralise each other. The salt is crystallised to purify it and obtain the desired precise stoichiometry. Heated to , 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 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 In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
content, nylon 610 is more hydrophobic and finds applications suited for this property, such as bristles. Examples of these polymers that are or were commercially available: * PA46 DSM Stanyl * PA410 DSM Ecopaxx * PA4T DSM Four Tii * PA66 DuPont Zytel


Nylon 6 and related homopolymers

These polymers are made from a lactam or amino acid. The synthetic route using lactams (cyclic amides) was developed by
Paul Schlack Paul Schlack (22 December 1897 – 19 August 1987) was a German chemist. He completed his studies at the Technical University of Stuttgart in 1921 and worked as a research chemist in Copenhagen for a year, before returning to Stuttgart. He re ...
at
IG Farben I. G. Farbenindustrie AG, commonly known as IG Farben, was a German Chemical industry, chemical and Pharmaceutical industry, pharmaceutical conglomerate (company), conglomerate. It was formed on December 2, 1925 from a merger of six chemical co ...
, 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 melting point of nylon 6 is lower than the melting point of
nylon 66 Nylon 66 (loosely written nylon 6-6, nylon 6/6, nylon 6,6, or nylon 6:6) is a type of polyamide or nylon. It, and nylon 6, are the two most common for textile and plastic industries. Nylon 66 is made of two monomers each containing six carbon at ...
. Homopolymer nylons are derived from one monomer. Examples of these polymers that are or were commercially available: * PA6 Lanxess Durethan B * PA11 Arkema Rilsan * PA12 Evonik Vestamid L


Nylon 1,6

Nylons can also be synthesised from dinitriles using acid catalysis. For example, this method is applicable for preparation of nylon 1,6 from
adiponitrile Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.M. T. Musser, "Adipi ...
,
formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
and water. Additionally, nylons can be synthesised from
diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...
s and dinitriles using this method as well.


Copolymers

It is easy to make mixtures of the monomers or sets of monomers used to make nylons to obtain copolymers. This lowers
crystallinity Crystallinity refers to the degree of structural order in a solid. In a crystal, the atoms or molecules are arranged in a regular, periodic manner. The degree of crystallinity has a large influence on hardness, density, transparency and diffusi ...
and can therefore lower the melting point. Some copolymers that have been or are commercially available are listed below: * PA6/66 DuPont Zytel * PA6/6T BASF Ultramid T (6/6T copolymer) * PA6I/6T DuPont Selar PA * PA66/6T DuPont Zytel HTN * PA12/MACMI EMS Grilamid TR


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.


Crystallinity

According to their crystallinity, polyamides can be: * semi-
crystal A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
line: ** high crystallinity: PA46 and PA66; ** low crystallinity: PAMXD6 made from m-xylylenediamine and adipic acid; *
amorphous In condensed matter physics and materials science, an amorphous solid (or non-crystalline solid) is a solid that lacks the long-range order that is a characteristic of a crystal. The terms "glass" and "glassy solid" are sometimes used synonymousl ...
: PA6I made from hexamethylenediamine and isophthalic acid. According to this classification, PA66, for example, is an aliphatic semi-crystalline homopolyamide.


Environmental impact

The general chemical reaction involving hydrolysis of an amide to form a carboxylic acid and an amine All nylons are susceptible to
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
, especially by
strong acid Acid strength is the tendency of an acid, symbolised by the chemical formula , to dissociate into a hydron (chemistry), proton, , and an anion, . The Dissociation (chemistry), dissociation or ionization of a strong acid in solution is effectivel ...
s, a reaction essentially the reverse of their synthesis. The
molecular weight A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...
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 Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
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. 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 A carbon footprint (or greenhouse gas footprint) is a calculated value or index that makes it possible to compare the total amount of greenhouse gases that an activity, product, company or country Greenhouse gas emissions, adds to the atmospher ...
as
wool Wool is the textile fiber obtained from sheep and other mammals, especially goats, rabbits, and camelids. The term may also refer to inorganic materials, such as mineral wool and glass wool, that have some properties similar to animal w ...
, but with greater durability and therefore a lower overall carbon footprint. Data published by PlasticsEurope indicates for nylon 66 a greenhouse gas footprint of 6.4 kg CO2 equivalent per kg, and an energy consumption of 138 kJ/kg. 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 Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is ...
. Incinerating nylons to recover the high energy used to create them is usually expensive, so most nylons reach the garbage dumps, decaying slowly. Discarded nylon fabric takes 30–40 years to decompose. Nylon used in discarded fishing gear such as fishing nets is a contributor to debris in the ocean. 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. 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. US clothing company
Patagonia Patagonia () is a geographical region that includes parts of Argentina and Chile at the southern end of South America. The region includes the southern section of the Andes mountain chain with lakes, fjords, temperate rainforests, and glaciers ...
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. The Italian company Aquafil also has demonstrated recycling fishing nets lost in the ocean into apparel. Vanden Recycling recycles nylon and other polyamides (PA) and has operations in the UK, Australia, Hong Kong, the UAE, Turkey and Finland. Nylon is the most popular fibre type in the residential carpet industry today. 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 Waste-to-energy (WtE) or energy-from-waste (EfW) refers to a series of processes designed to convert waste materials into usable forms of energy, typically electricity or heat. As a form of energy recovery, WtE plays a crucial role in both wa ...
facilities, and 73% was discarded in
landfill A landfill is a site for the disposal of waste materials. It is the oldest and most common form of waste disposal, although the systematic burial of waste with daily, intermediate and final covers only began in the 1940s. In the past, waste was ...
s. 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.


Properties

Above their melting temperatures, ''T''m,
thermoplastic A thermoplastic, or thermosoftening plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplastics have a high molecular weight. The polymer chains as ...
s like nylon are
amorphous solid In condensed matter physics and materials science, an amorphous solid (or non-crystalline solid) is a solid that lacks the long-range order that is a characteristic of a crystal. The terms "glass" and "glassy solid" are sometimes used synonymousl ...
s or viscous
fluid In physics, a fluid is a liquid, gas, or other material that may continuously motion, move and Deformation (physics), deform (''flow'') under an applied shear stress, or external force. They have zero shear modulus, or, in simpler terms, are M ...
s in which the chains approximate
random coil In polymer chemistry, a random coil is a conformation of polymers where the monomer subunits are oriented randomly while still being bonded to adjacent units. It is not one specific shape, but a statistical distribution of shapes for all the cha ...
s. Below ''T''m, amorphous regions alternate with regions which are
lamellar A lamella (: lamellae) is a small plate or flake, from the Latin, and may also refer to collections of fine sheets of material held adjacent to one another in a gill-shaped structure, often with fluid in between though sometimes simply a set of ...
crystal A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
s. The amorphous regions contribute elasticity, and the crystalline regions contribute strength and rigidity. The planar amide (-CO-NH-) groups are very
polar Polar may refer to: Geography * Geographical pole, either of the two points on Earth where its axis of rotation intersects its surface ** Polar climate, the climate common in polar regions ** Polar regions of Earth, locations within the polar circ ...
, so nylon forms multiple
hydrogen bond In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...
s 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. 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 In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...
oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...
s and amide
hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...
s 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 The beta sheet (β-sheet, also β-pleated sheet) is a common motif of the regular protein secondary structure. Beta sheets consist of beta strands (β-strands) connected laterally by at least two or three backbone hydrogen bonds, forming a gene ...
, a strong and tough supermolecular structure similar to that found in natural silk fibroin and the β-keratins in
feather Feathers are epidermal growths that form a distinctive outer covering, or plumage, on both avian (bird) and some non-avian dinosaurs and other archosaurs. They are the most complex integumentary structures found in vertebrates and an exa ...
s. (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 In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...
hydrocarbon chain In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...
depends on
rotation Rotation or rotational/rotary motion is the circular movement of an object around a central line, known as an ''axis of rotation''. A plane figure can rotate in either a clockwise or counterclockwise sense around a perpendicular axis intersect ...
s about the 109.47°
tetrahedral In geometry, a tetrahedron (: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular Face (geometry), faces, six straight Edge (geometry), edges, and four vertex (geometry), vertices. The tet ...
bonds of singly bonded carbon atoms. When
extruded Extrusion is a process used to create objects of a fixed cross-sectional profile by pushing material through a die of the desired cross-section. Its two main advantages over other manufacturing processes are its ability to create very complex ...
into fibres through pores in an industry
spinneret A spinneret is a silk-spinning organ of a spider or the larva of an insect. Some adult insects also have spinnerets, such as those borne on the forelegs of Embioptera. Spinnerets are usually on the underside of a spider's opisthosoma, and ar ...
, the individual polymer chains tend to align because of
viscous Viscosity is a measure of a fluid's rate-dependent resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for example, syrup h ...
flow. If subjected to cold drawing afterwards, the fibres align further, increasing their crystallinity, and the material acquires additional
tensile strength Ultimate tensile strength (also called UTS, tensile strength, TS, ultimate strength or F_\text in notation) is the maximum stress that a material can withstand while being stretched or pulled before breaking. In brittle materials, the ultimate ...
. In practice, nylon fibres are most often drawn using heated rolls at high speeds. Block nylon tends to be less crystalline, except near the surfaces due to
shearing Sheep shearing is the process by which the woollen fleece of a sheep is cut off. The person who removes the sheep's wool is called a '' shearer''. Typically each adult sheep is shorn once each year (depending upon dialect, a sheep may be sai ...
stresses during formation. Nylon is clear and colourless, or milky, but is easily
dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...
d. 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 A flame () is the visible, gaseous part of a fire. It is caused by a highly exothermic chemical reaction made in a thin zone. When flames are hot enough to have ionized gaseous components of sufficient density, they are then considered plasm ...
or
electrode An electrode is an electrical conductor used to make contact with a nonmetallic part of a circuit (e.g. a semiconductor, an electrolyte, a vacuum or a gas). In electrochemical cells, electrodes are essential parts that can consist of a varie ...
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 The glass–liquid transition, or glass transition, is the gradual and reversible transition in amorphous materials (or in amorphous regions within semicrystalline materials) from a hard and relatively brittle "glassy" state into a viscous or rub ...
(''T''g), and consequently the elastic modulus at temperatures below the ''T''g When dry, polyamide is a good electrical insulator. However, polyamide is
hygroscopic Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption (chemistry), absorption or adsorption from the surrounding Natural environment, environment, which is usually at normal or room temperature. If water mol ...
. The absorption of water will change some of the material's properties such as its
electrical resistance The electrical resistance of an object is a measure of its opposition to the flow of electric current. Its reciprocal quantity is , measuring the ease with which an electric current passes. Electrical resistance shares some conceptual paral ...
. 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 () * 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 The specific strength is a material's (or muscle's) strength (force per unit area at failure) divided by its density. It is also known as the strength-to-weight ratio or strength/weight ratio or strength-to-mass ratio. In fiber or textile applic ...
* Transparent to infrared light (−12 dB) Nylon clothing tends to be less flammable than cotton and rayon, but nylon fibres may melt and stick to skin.


Uses

Nylon was first used commercially in a nylon-
bristle A bristle is a stiff hair or feather (natural or artificial), either on an animal, such as a pig, a plant, or on a tool such as a brush or broom. Synthetic types Synthetic materials such as nylon are also used to make bristles in items such as b ...
d
toothbrush A toothbrush is a special type of brush used to clean the Human tooth, teeth, gingiva, gums, and tongue. It consists of a head of tightly clustered bristles, atop of which toothpaste can be applied, mounted on a handle (grip), handle which facil ...
in 1938, followed more famously in women's
stocking Stockings (also known as hose, especially in a historical context) are close-fitting, variously elastic garments covering the leg from the foot up to the knee or possibly part or all of the thigh. Stockings vary in color, design, and transpar ...
s or " nylons" which were shown at the
1939 New York World's Fair The 1939 New York World's Fair (also known as the 1939–1940 New York World's Fair) was an world's fair, international exposition at Flushing Meadows–Corona Park in Queens, New York City, New York, United States. The fair included exhibitio ...
and first sold commercially in 1940. Its use increased dramatically during World War II, when the need for fabrics increased dramatically.


Fibres

Bill Pittendreigh,
DuPont Dupont, DuPont, Du Pont, duPont, or du Pont may refer to: People * Dupont (surname) Dupont, also spelled as DuPont, duPont, Du Pont, or du Pont is a French surname meaning "of the bridge", historically indicating that the holder of the surname re ...
, and other individuals and corporations worked diligently during the first few months of World War II to find a way to replace Asian
silk Silk is a natural fiber, natural protein fiber, some forms of which can be weaving, woven into textiles. The protein fiber of silk is composed mainly of fibroin and is most commonly produced by certain insect larvae to form cocoon (silk), c ...
and
hemp Hemp, or industrial hemp, is a plant in the botanical class of ''Cannabis sativa'' cultivars grown specifically for industrial and consumable use. It can be used to make a wide range of products. Along with bamboo, hemp is among the fastest ...
with nylon in parachutes. It was also used to make
tire A tire (North American English) or tyre (Commonwealth English) is a ring-shaped component that surrounds a Rim (wheel), wheel's rim to transfer a vehicle's load from the axle through the wheel to the ground and to provide Traction (engineeri ...
s,
tent A tent is a shelter consisting of sheets of fabric or other material draped over or attached to a frame of poles or a supporting rope. While smaller tents may be free-standing or attached to the ground, large tents are usually anchored using g ...
s,
rope A rope is a group of yarns, Plying, plies, fibres, or strands that are plying, twisted or braided together into a larger and stronger form. Ropes have high tensile strength and can be used for dragging and lifting. Rope is thicker and stronger ...
s,
poncho A poncho (; ; ; "blanket", "woolen fabric") is a kind of plainly formed, loose outer garment originating in the Americas, traditionally and still usually made of fabric, and designed to keep the body warm. Ponchos have been used by the Indige ...
s, and other
military A military, also known collectively as armed forces, is a heavily armed, highly organized force primarily intended for warfare. Militaries are typically authorized and maintained by a sovereign state, with their members identifiable by a d ...
supplies. It was even used in the production of a high-grade paper for U.S.
currency A currency is a standardization of money in any form, in use or circulation as a medium of exchange, for example banknotes and coins. A more general definition is that a currency is a ''system of money'' in common use within a specific envi ...
. At the outset of the war,
cotton Cotton (), first recorded in ancient India, is a soft, fluffy staple fiber that grows in a boll, or protective case, around the seeds of the cotton plants of the genus '' Gossypium'' in the mallow family Malvaceae. The fiber is almost pure ...
accounted for more than 80% of all fibres used and manufactured, and
wool Wool is the textile fiber obtained from sheep and other mammals, especially goats, rabbits, and camelids. The term may also refer to inorganic materials, such as mineral wool and glass wool, that have some properties similar to animal w ...
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. Nylon 6 and 66 fibres are used in
carpet A carpet is a textile floor covering typically consisting of an upper layer of Pile (textile), pile attached to a backing. The pile was traditionally made from wool, but since the 20th century synthetic fiber, synthetic fibres such as polyprop ...
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. Molded nylon is used in hair combs and
mechanical Mechanical may refer to: Machine * Machine (mechanical), a system of mechanisms that shape the actuator input to achieve a specific application of output forces and movement * Mechanical calculator, a device used to perform the basic operations o ...
parts such as
machine screw A screw is an externally helical threaded fastener capable of being tightened or released by a twisting force (torque) to the head. The most common uses of screws are to hold objects together and there are many forms for a variety of materi ...
s,
gear A gear or gearwheel is a rotating machine part typically used to transmit rotational motion and/or torque by means of a series of teeth that engage with compatible teeth of another gear or other part. The teeth can be integral saliences or ...
s, gaskets, and other low- to medium-stress components previously cast in metal. Engineering-grade nylon is processed by
extrusion Extrusion is a process used to create objects of a fixed cross section (geometry), cross-sectional profile by pushing material through a Die (manufacturing), die of the desired cross-section. Its two main advantages over other manufacturing pro ...
,
casting Casting is a manufacturing process in which a liquid material is usually poured into a mold, which contains a hollow cavity of the desired shape, and then allowed to solidify. The solidified part is also known as a casting, which is ejected or ...
, and
injection molding Injection moulding (U.S. spelling: injection molding) is a manufacturing process for producing parts by injecting molten material into a mould, or mold. Injection moulding can be performed with a host of materials mainly including metals (for ...
. 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. For use in tools such as
spudger A spudger (also known as a spludger, non-marring nylon black stick tool) is a tool that has a wide flat-head screwdriver-like end that extends as a wedge, used to separate pressure-fit plastic components without causing damage during separation. ...
s, nylon is available in glass-filled variants which increase structural and impact strength and rigidity, and
molybdenum disulfide Molybdenum disulfide (or moly) is an inorganic chemistry, inorganic compound composed of molybdenum and sulfur. Its chemical formula is . The compound is classified as a transition metal dichalcogenide. It is a silvery black solid that occurs as ...
-filled variants which increase
lubricity Lubricity is the measure of the reduction in friction and/or wear by a lubricant. The study of lubrication and wear mechanisms is called tribology. Measurement of lubricity The lubricity of a substance is not a material property, and cannot be m ...
. Nylon can be used as the matrix material in
composite material A composite or composite material (also composition material) is a material which is produced from two or more constituent materials. These constituent materials have notably dissimilar chemical or physical properties and are merged to create a ...
s, with reinforcing fibres like glass or carbon fibre; such a composite has a higher
density Density (volumetric mass density or specific mass) is the ratio of a substance's mass to its volume. The symbol most often used for density is ''ρ'' (the lower case Greek letter rho), although the Latin letter ''D'' (or ''d'') can also be u ...
than pure nylon. 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. Nylon was used to make the stock of the Remington Nylon 66 rifle. The frame of the modern
Glock Glock (; stylized as GLOCK) is a brand of polymer- framed, short-recoil-operated, striker-fired, locked-breech semi-automatic pistols designed and produced by Austrian manufacturer Glock Ges.m.b.H. The firearm entered Austrian military an ...
pistol is made of a nylon composite.


Food packaging

Nylon resins are used as a component of food packaging films where an oxygen barrier is needed. Some of the terpolymers based upon nylon are used every day in packaging. Nylon has been used for
meat Meat is animal Tissue (biology), tissue, often muscle, that is eaten as food. Humans have hunted and farmed other animals for meat since prehistory. The Neolithic Revolution allowed the domestication of vertebrates, including chickens, sheep, ...
wrappings and
sausage A sausage is a type of meat product usually made from ground meat—often pork, beef, or poultry—along with salt, spices and other flavourings. Other ingredients, such as grains or breadcrumbs, may be included as fillers or extenders. ...
sheaths. The high temperature resistance of nylon makes it useful for oven bags.


Filaments

Nylon filaments are primarily used in brushes especially toothbrushes and
string trimmer A string trimmer, also known by the portmanteau strimmer and the trademarks Weedwacker, Weed Eater and Whipper Snipper, is a garden power tool for cutting grass, small weeds, and groundcover. It uses a whirling monofilament line instead of a b ...
s. They are also used as monofilaments in
fishing line A fishing line is any flexible, high-tensile cord used in angling to tether and pull in fish, in conjunction with at least one hook. Fishing lines are usually pulled by and stored in a reel, but can also be retrieved by hand, with a fixed att ...
. 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 3D printing, or additive manufacturing, is the construction of a three-dimensional object from a CAD model or a digital 3D model. It can be done in a variety of processes in which material is deposited, joined or solidified under computer ...
; specifically, as a filament in consumer and professional grade
fused deposition modeling Fused filament fabrication (FFF), also known as fused deposition modeling (with the trademarked acronym FDM), or ''filament freeform fabrication'', is a 3D printing process that uses a continuous filament of a thermoplastic material. Filament is ...
3D printers.


Other forms

Nylon resins can be extruded into rods, tubes, and sheets. Nylon powders are used to powder coat metals.
Nylon 11 Nylon 11 or Polyamide 11 (PA 11) is a polyamide, bioplastic and a member of the nylon family of polymers produced by the polymerization of 11-Aminoundecanoic acid, 11-aminoundecanoic acid. It is produced from castor beans by Arkema under the trad ...
and nylon 12 are the most widely used. In the mid-1940s, classical guitarist
Andrés Segovia Andrés Segovia Torres, 1st Marquis of Salobreña (21 February 1893 – 2 June 1987), was a Spanish virtuoso classical guitarist. Many professional classical guitarists were either students of Segovia or students of Segovia's students. Segovia ...
mentioned the shortage of good guitar strings in the United States, particularly his favorite Pirastro
catgut Catgut (also known as gut) is a type of cord that is prepared from the natural fiber found in the walls of animal intestines. Catgut makers usually use sheep or goat intestines, but occasionally use the intestines of cattle, hogs, horses, mules, ...
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 In music, timbre (), also known as tone color or tone quality (from psychoacoustics), is the perceived sound of a musical note, sound or tone. Timbre distinguishes sounds according to their source, such as choir voices and musical instrument ...
which he hoped could be eliminated. Nylon strings were first tried on stage by Olga Coelho in New York in January 1944. 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. 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.


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Polyamide Nylon Plastic

Joseph X. Labovsky Collection of Nylon Photographs and Ephemera
Science History Institute The Science History Institute is an institution that preserves and promotes understanding of the history of science. Located in Philadelphia, Pennsylvania, it includes a library, museum, archive, research center and conference center. It was ...
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). {{Authority control Products introduced in 1935 American inventions Commodity chemicals Dielectrics DuPont products Plastics Polyamides Synthetic fibers de:Polyamide#Nylon