Nylon is a generic designation for a family of synthetic polymers, based on aliphatic or semi-

aromatic polyamides. Nylon is a thermoplastic silky material[1] that can be melt-processed into

fibers, films, or shapes.[2]:2 It is made of repeating units linked by amide links[3] similar to
the peptide bonds in proteins. 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).[4]
Nylon was the first commercially successful synthetic thermoplastic polymer.[5] DuPont began its
research project in 1927.[6] The first example of nylon (nylon 6,6) using diamines on February 28,
1935, by Wallace Hume Carothers at DuPont's research facility at the DuPont Experimental
Station.[7][8] In response to Carothers' work, Paul Schlack at IG Farben developed nylon 6, a
different molecule based on caprolactam, on January 29, 1938.[9]:10[10]
Nylon was first used commercially in a nylon-bristled toothbrush in 1938,[11][12] 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.[13] 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.[14]

Contents

 1History
o 1.1DuPont and the invention of Nylon
o 1.2Early marketing strategies
o 1.3Production of nylon fabric
o 1.4Introduction of nylon blends
 2Origin of the name
 3Longer-term popularity
 4Chemistry
o 4.1Nomenclature
o 4.2Types of nylon
 4.2.1Nylon 66
 4.2.2Nylon 6
 4.2.3Nylon 510
 4.2.4Nylon 1,6
o 4.3Monomers
 4.3.1Amino acids and lactams
 4.3.2Diacids
 4.3.3Diamines
o 4.4Polymers
 4.4.1Homopolymers
 4.4.2Copolymers
 4.4.3Blends
o 4.5Hydrolysis and degradation
 5Environmental impact, incineration and recycling
 6Bulk properties
o 6.1Characteristics
 6.1.1Flammability
 7Uses of nylon
o 7.1Nylon fibers
o 7.2Molds and resins
o 7.3Food packaging
 o 7.4Filaments
o 7.5Other forms
 7.5.1Extruded Profiles
 7.5.2Powder Coating
 7.5.3Instrument strings
 8See also
 9Notes
 10References
 11Further reading
 12External links

History[edit]

Wallace Carothers

DuPont and the invention of Nylon[edit]

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.[15]: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.[6] 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".[15]: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.[16] He was very successful, as
research he undertook greatly improved the knowledge of polymers and contributed to science.[17]
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.[18] 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".[15]: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.[19] This cold drawing method was later used by
Carothers in 1935 to fully develop nylon.[20] The first example of nylon (nylon 6,6) was produced
on February 28, 1935, at DuPont's research facility at the DuPont Experimental Station.[7] 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,[21] and quickly achieved a monopoly of the
fiber.[17] Carothers died 16 months before the announcement of nylon, therefore he was never
able to see his success. [6]
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”,[15] 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.[15]
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.[15] The ability to acquire a large number
of chemists and engineers quickly was a huge contribution to the success of DuPont's nylon
project.[15]: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.[22]

Early marketing strategies[edit]

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.[16][17]: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.[17]:141 Nylon was introduced as part of "The world of tomorrow" at
the 1939 New York World's Fair[23] and was featured at DuPont's "Wonder World of Chemistry" at
the Golden Gate International Exposition in San Francisco in 1939.[16][24] 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.[17]: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.[16]
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.[17]
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.[17]:145–147[13] 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.[17]
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.[17]: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),[a] 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.[17]: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.[17]:146–147 Nylon was thus domesticated,[17]: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!".[15]:2

Production of nylon fabric[edit]

Nylon stockings being inspected in Malmö, Sweden, in 1954

After nylon's nationwide release in 1940, production was increased. 1300 tons of the fabric were
produced during 1940.[15]:100 During their first year on the market, 64 million pairs of nylon
stockings were sold.[15]:101 In 1941, a second plant was opened in Martinsville, Virginia due to the
success of the fabric.[25]

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

Nylon fibers visualized using scanning electron microscopy

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).
[15]: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.[26]
However, as of February 11, 1942, nylon production was redirected from being a consumer
material to one used by the military.[16] 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.
[27]
 Although nylon stockings already made before the war could be purchased, they were
generally sold on the black market for as high as $20.[25]
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.[16] In 1946, the demand for nylon stockings could not
be satisfied, which led to the Nylon riots. In one case, an estimated 40,000 people lined up in
Pittsburgh to buy 13,000 pairs of nylons.[13] In the meantime, women cut up nylon tents and
parachutes left from the war in order to make blouses and wedding dresses.[28][29] 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.

Introduction of nylon blends[edit]

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'.[15]:101 People also reported that pure nylon textiles could be uncomfortable due to nylon's
lack of absorbency.[30] Moisture stayed inside the fabric near the skin under hot or moist
conditions instead of being "wicked" away.[31] Nylon fabric could also be itchy, and tended to cling
and sometimes spark as a result of static electrical charge built up by friction.[32][33] Also, under
some conditions stockings could decompose[17] 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.[34][35][36]
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.[27]: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".[37] Fabric blends included
mixes like "Bunara" (wool-rabbit-nylon) and "Casmet" (wool-nylon-fur).[38] 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.[39]
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.[13] American Fabrics credited blends with providing
"creative possibilities and new ideas for fashions which had been hitherto undreamed of."[38]

Origin of the name[edit]

DuPont went through an extensive process to generate names for its new product.[17]: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."[13][40]

Longer-term popularity[edit]
In spite of oil shortages in the 1970s, consumption of nylon textiles continued to grow by 7.5 per
cent per annum between the 1960s and 1980s.[41] 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.[41] The appeal of "new" technologies wore off, and nylon fabric "was
going out of style in the 1970s".[15] 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.[41] Synthetic fibers have not dominated the market since the 1950s
and 1960s. As of 2007, nylon continued to represent about 12% (8 million pounds) of the world's
production of synthetic fibers.[13] 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%.[42]
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.[13] 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".[43][44] One historian describes nylon as "an object of desire", comparing the invention to
Coca-Cola in the eyes of 20th century consumers.[15]

Chemistry[edit]
External video

 "Making Nylon", Bob Burk, CHEM

1000, Carleton University, Ottawa,

Canada

 "Making Nylon 6,6"

 "Nylon production", Royal Society

of Chemistry

 "Nylon and Rayon Manufacture

1949", Encyclopedia Britannica Films

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).[45] 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.[9]:45–50[46]

Nomenclature[edit]
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).[47][48] Subsequent use of cyclic and aromatic
monomers required the use of letters or sets of letters. One number after "PA" or "Nylon"
indicates a homopolymer which is monadic or based on one amino acid (minus H2O) as
monomer:
PA 6 or Nylon 6: [NH−(CH2)5−CO]n made from ε-Caprolactam.
Two numbers or sets of letters indicate a dyadic homopolymer formed from two monomers:
one diamine and one dicarboxylic acid. The first number indicates the number of carbons in
the diamine. The two numbers should be separated by a comma for clarity, but the comma is
often omitted.
PA or Nylon 6,10 (or 610) : [NH−(CH2)6−NH−CO−(CH2)8−CO]n made
from hexamethylenediamine and sebacic acid;
For copolymers the comonomers or pairs of comonomers are separated by slashes:
PA 6/66 : [NH-(CH2)6−NH−CO−(CH2)4−CO]n−[NH−(CH2)5−CO]m made from caprolactam,
hexamethylenediamine and adipic acid ;
PA 66/610 : [NH−(CH2)6−NH−CO−(CH2)4−CO]n−[NH−(CH2)6−NH−CO−(CH2)8−CO]m made
from hexamethylenediamine, adipic acid and sebacic acid.
The term polyphthalamide (abbreviated to PPA) is used when 60% or more
moles of the carboxylic acid portion of the repeating unit in the polymer chain is
composed of a combination of terephthalic acid (TPA) and isophthalic
acid (IPA).

Types of nylon[edit]
Nylon 66[edit]
Main article: Nylon 66
Wallace Carothers at DuPont patented nylon 66 using amides.[21][49][50] 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.
Nylon 6