Nylon 6

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Nylon 6
Polycaprolactam.svg
Names
IUPAC name
Poly(azepan-2-one); poly(hexano-6-lactam)
Systematic IUPAC name
Poly[azanediyl(1-oxohexane-1,6-diyl)]
Other names
Polycaprolactam, polyamide 6, PA6, poly-ε-caproamide, Perlon, Dederon, Capron, Ultramid, Akulon, Nylatron, Kapron, Alphalon, Tarnamid, Akromid, Frianyl, Schulamid, Durethan, Technyl, Nyorbits ,Winmark Polymers
Identifiers
ChemSpider
  • None
ECHA InfoCard 100.124.824 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
Properties
(C6H11NO)n
Density 1.084 g/mL [ citation needed ]
Melting point 218.3 °C (493 K)
Hazards
434 °C; 813 °F; 707 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Caprolactam molecule used to synthesize Nylon 6 by ring opening polymerization Caprolactam-2D-skeletal.png
Caprolactam molecule used to synthesize Nylon 6 by ring opening polymerization

Nylon 6 or polycaprolactam is a polymer, in particular semicrystalline polyamide. Unlike most other nylons, nylon 6 is not a condensation polymer, but instead is formed by ring-opening polymerization; this makes it a special case in the comparison between condensation and addition polymers. Its competition with nylon 6,6 and the example it set have also shaped the economics of the synthetic fibre industry. It is sold under numerous trade names including Perlon (Germany), Dederon (former East Germany), [1] Nylatron, Capron, Ultramid, Akulon, Kapron (former Soviet Union and satellite states), Rugopa (Turkey) and Durethan.

Contents

History

Polycaprolactam was developed by Paul Schlack at IG Farben in late 1930s (first synthesized in 1938) to reproduce the properties of Nylon 66 without violating the patent on its production. (Around the same time, Kohei Hoshino at Toray also succeeded in synthesizing nylon 6.) It was marketed as Perlon, and industrial production with a capacity of 3,500 tons per year was established in Nazi Germany in 1943, using phenol as a feedstock. At first, the polymer was used to produce coarse fiber for artificial bristle, then the fiber quality was improved, and Germans started making parachutes, cord for aircraft tires and towing cables for gliders.

The Soviet Union began its development of an analog in the 1940s, while negotiating with Hitler on building an IG Farben plant in Ukraine, basic scientific work was ongoing in 1942. The production only started in 1948 in Klin, after USSR got its hands on the 2000 volumes of IG Farben, and 10,000 volumes of AEG technical documentation [2] , as a result of victory in the World War II.

Synthesis

Nylon 6 can be modified using comonomers or stabilizers during polymerization to introduce new chain end or functional groups, which changes the reactivity and chemical properties. It is often done to change its dyeability or flame retardance. [3] Nylon 6 is synthesized by ring-opening polymerization of caprolactam. Caprolactam has 6 carbons, hence Nylon 6. When caprolactam is heated at about 533  K in an inert atmosphere of nitrogen for about 4–5 hours, the ring breaks and undergoes polymerization. Then the molten mass is passed through spinnerets to form fibres of nylon 6.

Polymerization of caprolactam to Nylon 6. Caprolactam polymerization.png
Polymerization of caprolactam to Nylon 6.

During polymerization, the amide bond within each caprolactam molecule is broken, with the active groups on each side re-forming two new bonds as the monomer becomes part of the polymer backbone. Unlike nylon 6,6, in which the direction of the amide bond reverses at each bond, all nylon 6 amide bonds lie in the same direction (see figure: note the N to C orientation of each amide bond).

Nylon 6 (above) has a structure similar to Nylon 6,6 (below). Nylon 6 and Nylon 6-6.svg
Nylon 6 (above) has a structure similar to Nylon 6,6 (below).

Properties

Nylon 6 fibres are tough, possessing high tensile strength, elasticity and lustre. They are wrinkleproof and highly resistant to abrasion and chemicals such as acids and alkalis. The fibres can absorb up to 2.4% of water, although this lowers tensile strength. The glass transition temperature of Nylon 6 is 47 °C.

As a synthetic fibre, Nylon 6 is generally white but can be dyed in a solution bath prior to production for different color results. Its tenacity is 6–8.5  gf/D with a density of 1.14 g/cm3. Its melting point is at 215 °C and can protect heat up to 150 °C on average. [4]

Biodegradation

Flavobacterium sp. [85] and Pseudomonas sp. (NK87) degrade oligomers of Nylon 6, but not polymers. Certain white rot fungal strains can also degrade Nylon 6 through oxidation. Compared to aliphatic polyesters, Nylon 6 has been said to have poor biodegradability. Strong interchain interactions from hydrogen bonds between molecular nylon chains is said to be the cause by some sources. [5] However, in 2023 a catalyst that rapidly breaks Nylon 6 down was reported. [6]

Production in Europe

At present, polyamide 6 is a significant construction material used in many industries, for instance in the automotive industry, aircraft industry, electronic and electrotechnical industry, clothing industry and medicine. Annual demand for polyamides in Europe amounts to a million tonnes. They are produced by all leading chemical companies.

The largest producers of polyamide 6 in Europe: [7]


  1. Fibrant, 260,000 tonnes per year
  2. BASF, 240,000 tonnes per year
  3. Lanxess, 170,000 tonnes per year
  4. Radici, 125,000 tonnes per year
  5. DOMO, 100,000 tonnes per year
  6. Grupa Azoty, 100,000 tonnes per year [8] [9]

Related Research Articles

<span class="mw-page-title-main">Nylon</span> Early synthetic polymer developed as a textile fiber

Nylon is a family of synthetic polymers with amide backbones, usually linking aliphatic or semi-aromatic groups.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Fiber</span> Natural or synthetic substance made of long, thin filaments

Fiber or fibre is a natural or artificial substance that is significantly longer than it is wide. Fibers are often used in the manufacture of other materials. The strongest engineering materials often incorporate fibers, for example carbon fiber and ultra-high-molecular-weight polyethylene.

<span class="mw-page-title-main">BASF</span> German chemicals company

BASF SE, an initialism of its original name Badische Anilin- und Sodafabrik, is a European multinational company and the largest chemical producer in the world. Its headquarters are located in Ludwigshafen, Germany.

Synthetic fibers or synthetic fibres are fibers made by humans through chemical synthesis, as opposed to natural fibers that are directly derived from living organisms, such as plants or fur from animals. They are the result of extensive research by scientists to replicate naturally occurring animal and plant fibers. In general, synthetic fibers are created by extruding fiber-forming materials through spinnerets, forming a fiber. These are called synthetic or artificial fibers. The word polymer comes from a Greek prefix "poly" which means "many" and suffix "mer" which means "single units"..

Aramid fibers, short for aromatic polyamide, are a class of heat-resistant and strong synthetic fibers. They are used in aerospace and military applications, for ballistic-rated body armor fabric and ballistic composites, in marine cordage, marine hull reinforcement, as an asbestos substitute, and in various lightweight consumer items ranging from phone cases to tennis rackets.

A polyamide is a polymer with repeating units linked by amide bonds.

Twaron is a para-aramid. It is a heat-resistant and strong synthetic fibre developed in the early 1970s by the Dutch company Akzo Nobel's division Enka BV, later Akzo Industrial Fibers. The research name of the para-aramid fibre was originally Fiber X, but it was soon called Arenka. Although the Dutch para-aramid fiber was developed only a little later than DuPont's Kevlar, the introduction of Twaron as a commercial product came much later than Kevlar due to financial problems at the Akzo company in the 1970s.

Polymer chemistry is a sub-discipline of chemistry that focuses on the structures of chemicals, chemical synthesis, and chemical and physical properties of polymers and macromolecules. The principles and methods used within polymer chemistry are also applicable through a wide range of other chemistry sub-disciplines like organic chemistry, analytical chemistry, and physical chemistry. Many materials have polymeric structures, from fully inorganic metals and ceramics to DNA and other biological molecules. However, polymer chemistry is typically related to synthetic and organic compositions. Synthetic polymers are ubiquitous in commercial materials and products in everyday use, such as plastics, and rubbers, and are major components of composite materials. Polymer chemistry can also be included in the broader fields of polymer science or even nanotechnology, both of which can be described as encompassing polymer physics and polymer engineering.

Nylon is a generic term for a class of polymers.

<span class="mw-page-title-main">Caprolactam</span> Chemical compound

Caprolactam (CPL) is an organic compound with the 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 majority is used to make Nylon 6 filament, fiber, and plastics.

<span class="mw-page-title-main">Polyester</span> Category of polymers, in which the monomers are joined together by ester links

Polyester is a category of polymers that contain the ester functional group 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 naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.

Paul Schlack 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 received his PhD in 1924. Around this time he developed a keen interest in amide chemistry. He synthesized Nylon 6, widely known by its tradename Perlon, on 29 January 1938 whilst working for IG Farben.

Nylon 66 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 6 carbon atoms, hexamethylenediamine and adipic acid, which give nylon 66 its name. Aside from its superior physical characteristics, nylon 66 is attractive because its precursors are inexpensive.

<span class="mw-page-title-main">Polyaspartic acid</span> Chemical compound

Polyaspartic acid (PASA) is a biodegradable, water-soluble condensation polymer based on the amino acid aspartic acid. It is a biodegradable replacement for water softeners and related applications. PASA can be chemically crosslinked with a wide variety of methods to yield PASA hydrogels. The resulting hydrogels are pH-sensitive such that under acidic conditions, they shrink, while the swelling capacity increases under alkaline conditions.

<span class="mw-page-title-main">Polybutylene succinate</span> Biodegradable polymer

Polybutylene succinate (PBS) is a thermoplastic polymer resin of the polyester family. PBS is a biodegradable aliphatic polyester with properties that are comparable to polypropylene.

<span class="mw-page-title-main">Grupa Azoty ATT Polymers GmbH</span>

Grupa Azoty ATT Polymers GmbH - one of the leading polyamide 6 (PA6) manufacturing companies in Western Europe. The company is based in Guben (Germany). Grupa Azoty ATT Polymers GmbH is part of Grupa Azoty, a leader in the production of fertilisers, engineering plastics, caprolactam and other highly processed chemicals such as OXO, plasticisers and titanium white. The Group is also the largest supplier of ammonia and phosphoric acid in Poland. The effect of the company's acquisition by Grupa Azoty S.A. is the integration of caprolactam production, giving both companies the opportunity to effectively apply mutual synergies to increase customer and partner satisfaction.

Gérard Berchet was a French-American chemist who played a pivotal role in the invention of both nylon and neoprene. Berchet worked under the direction of Wallace Carothers at DuPont Experimental Station and first synthesized nylon 6 on February 28, 1935, from equal parts hexamethylenediamine and adipic acid. Berchet was the first to synthesize neoprene. However, Arthur Collins is credited with its discovery on April 17, 1930, after he accidentally reacted hydrochloric acid with vinylacetylene. Berchet's leaving of his sample unexamined on a laboratory bench until after Collin's discovery prevented him from being credited with its discovery.

Polyesteramides are a class of synthetic polymers connected by ester and amide bonds.

References

  1. Rubin, E. (2014), Synthetic Socialism: Plastics and Dictatorship in the German Democratic Republic. The University of North Carolina Press. ISBN   978-1469615103
  2. Zaharov, V.V. (2007). Советская военная администрация в Германии 1945-1949: Деятельность Управления СВАГ по изучению достижений немецкой науки и техники в Советской зоне оккупации Германии[Soviet military administration in Germany 1945-1949: Activities of the SMAG Directorate for studying the achievements of German science and technology in the Soviet zone of occupation of Germany] (in Russian). Moscow: ROSSPEN, Russian State Archive. p. 65. ISBN   978-5-8243-0882-2.
  3. "Synthesis of Modified Polyamides (Nylon 6)", NPTEL (National Programme On Technology Enhanced Learning), retrieved May 9, 2016
  4. Polyamide Fiber Physical and Chemical Properties of Nylon 6”, textilefashionstudy.com, retrieved May 9, 2016.
  5. Tokiwa, Y.; Calabia, B. P.; Ugwu, C. U.; Aiba, S. (2009). "Biodegradability of Plastics". International Journal of Molecular Sciences. 10 (9): 3722–42. doi: 10.3390/ijms10093722 . PMC   2769161 . PMID   19865515.
  6. https://scitechdaily.com/new-catalyst-completely-breaks-down-durable-plastic-pollution-in-minutes/
  7. "Segment Tworzywa 2015" (PDF) (in Polish). static.grupaazoty.com. Retrieved 2016-04-12.
  8. "Alphalon™ (PA6)" (in Polish). att.grupaazoty.com. Archived from the original on 2016-04-26. Retrieved 2016-04-12.
  9. "Grupa Azoty: Nowa wytwórnia pozwoli zająć pozycję 2. producenta poliamidu w UE" (in Polish). wyborcza.biz. Retrieved 2016-04-12.