Nylon 11 or Polyamide 11 (PA 11) is a

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 ...

bioplastic Bioplastics are plastic materials produced from renewable biomass sources. Timeline of plastic development, Historically, bioplastics made from natural materials like shellac or Celluloid, cellulose had been the first plastics. Since the end of ...

and a member of the

nylon Nylon is a family of synthetic polymers characterised by amide linkages, typically connecting aliphatic or Polyamide#Classification, semi-aromatic groups. Nylons are generally brownish in color and can possess a soft texture, with some varieti ...

family of polymers produced by the polymerization of

11-aminoundecanoic acid 11-Aminoundecanoic acid is an organic compound with the formula H2N(CH2)10CO2H. This white solid is classified as an amine and a fatty acid. 11-Aminoundecanoic acid is a precursor to Nylon-11. Production As practiced by Arkema, 11-aminoundec ...

. It is produced from castor beans by

Arkema Arkema S.A. is a Public company, publicly listed, multi-national manufacturer of specialty materials, headquartered in La Défense, near Paris, France. It has three specialty materials segments (or divisions); Adhesive, adhesives, advanced mater ...

under the trade name Rilsan. Nylon 11 is applied in the fields of

oil and gas A fossil fuel is a flammable carbon compound- or hydrocarbon-containing material formed naturally in the Earth's crust from the buried remains of prehistoric organisms (animals, plants or microplanktons), a process that occurs within geologi ...

aerospace Aerospace is a term used to collectively refer to the atmosphere and outer space. Aerospace activity is very diverse, with a multitude of commercial, industrial, and military applications. Aerospace engineering consists of aeronautics and astron ...

, automotive,

textile 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. ...

electronics Electronics is a scientific and engineering discipline that studies and applies the principles of physics to design, create, and operate devices that manipulate electrons and other Electric charge, electrically charged particles. It is a subfield ...

and

sports equipment Sports equipment, also called sporting goods, are the tools, materials, apparel, and gear, which varies in shapes, size, and usage in a particular sport. It includes balls, nets, rackets, protective gears like helmets, goggles, etc. Since th ...

, frequently in tubing, wire sheathing, and metal coatings.

History

In 1938, a research director for Thann & Mulhouse, Joseph Zeltner, first conceived the idea of Nylon 11, which was suggested in the works of

Wallace 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 ...

. Thann & Mulhouse had already been involved in processing

castor oil Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...

for 10-undecenoic-acid, which would eventually be converted into the first amount of

in 1940 with the help of coworkers Michel Genas and Marcel Kastner. In 1944, Kastner sufficiently improved the

monomer A monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or two- or three-dimensional network in a process called polymerization. Classification Chemis ...

process and the first patents for Nylon 11 were filed in 1947. The first nylon 11 thread was created in 1950 and full industrial production began with the opening of the

Marseille Marseille (; ; see #Name, below) is a city in southern France, the Prefectures in France, prefecture of the Departments of France, department of Bouches-du-Rhône and of the Provence-Alpes-Côte d'Azur Regions of France, region. Situated in the ...

s production facility in 1955, which remains the sole producer of 11-aminoudecanoic acid today. Currently Arkema

polymerizes In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many form ...

Nylon 11 in Birdsboro, PA,

Changshu Changshu (; Suzhounese: /d͡ʐan¹³ ʐoʔ²³/) is a county-level city under the jurisdiction of Suzhou, Jiangsu province, and is part of the Yangtze River Delta. It borders the prefecture-level city of Nantong to the northeast across the Yangt ...

, and

Serquigny Serquigny () is a commune in France, commune of the Eure Departments of France, department in Normandy (administrative region), Normandy in northern France. It lies on the rail line from Cherbourg to Paris. In the village there is a privately ow ...

Chemistry

The chemical process of creating Nylon 11 begins with

ricinoleic acid Ricinoleic acid, formally called 12-hydroxy-9-''cis''-octadecenoic acid, is a fatty acid. It is an Unsaturated fatty acid, unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of casto ...

which makes up 85-90% of castor oil. Ricinoleic acid is first transesterified with

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

creating

methyl ricinoleate Methyl ricinoleate is a clear, viscous fluid that is used as a surfactant, cutting fluid additive, lubricant, and plasticizer. It is a plasticizer for cellulosic resins, polyvinyl acetate, and polystyrene. It is a type of fatty acid methyl ester ...

, which is then cracked to create heptaldehyde and methyl undecylenate. These undergo

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 ...

to create methanol, which is re-used in the initial transesterification of ricinoleic acid, and

undecylenic acid Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the s ...

that is added on to

hydrogen bromide Hydrogen bromide is the inorganic compound with the formula . It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temper ...

. After hydrolysis, hydrogen bromide then undergoes

nucleophilic substitution In chemistry, a nucleophilic substitution (SN) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile) ...

with

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

to form 11-aminoundecanoic acid, which is polymerized into nylon 11.

Properties

As seen in the table below, Nylon 11 has lower values of density, flexural and Young's modulus, water absorption, as well as melting and glass transition temperatures. Nylon 11 is seen to have increased dimensional stability in the presence of moisture due to its low concentration of

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 ...

s. Nylon 11 experiences 0.2-0.5% length variation and 1.9% weight variation after 25 weeks of submersion in water in comparison to 2.2-2.7% elongation variation and 9.5% weight variation for Nylon 6. When specially orientated into the δ' phase, Nylon 11 11 can exhibit

piezoelectric Piezoelectricity (, ) is the electric charge that accumulates in certain solid materials—such as crystals, certain ceramics, and biological matter such as bone, DNA, and various proteins—in response to applied stress (mechanics), mechanical s ...

properties.

Applications

Tubing

Due to its low water absorption, increased dimensional stability when exposed to moisture, heat and chemical resistance, flexibility, and burst strength, nylon 11 is used in various applications for tubing. In the fields of automotive, aerospace, pneumatics, medical, and oil and gas, nylon 11 is used in

fuel line A fuel line is a hose or pipe used to transfer fuel from one point in a vehicle to another. The United States Environmental Protection Agency defines a fuel line as "all hoses or tubing designed to contain liquid fuel or fuel vapor. This incl ...

s, hydraulic hoses, air lines, umbilical hoses,

catheter In medicine, a catheter ( ) is a thin tubing (material), tube made from medical grade materials serving a broad range of functions. Catheters are medical devices that can be inserted in the body to treat diseases or perform a surgical procedure. ...

s, and beverage tubing.

Electrical

Nylon 11 is used in cable and wire sheathing as well as electrical housings, connectors and clips.

Coatings

Nylon 11 is used in metal coatings for noise reduction and protection against UV exposure as well as resistance to chemicals, abrasion, and corrosion.

Textiles

Nylon 11 is used in textiles through brush bristles,

lingerie Lingerie (, , ) is a category of primarily women's clothing including undergarments (mainly brassieres), sleepwear, and lightweight robes. The choice of the word is often motivated by an intention to imply that the garments are alluring, fashio ...

, filters, as well as woven and

technical fabrics 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 ...

.{{Cite book, title=Handbook of textile fibres. Volume 1, Natural fibers, last=Gordon., first=Cook, J., isbn=9781845693152, edition= Fifth, location=Cambridge, England, oclc=874158248, date = 1984-01-01

Sports Equipment

Nylon 11 is used in the soles and other mechanical parts of footwear. It is also seen in racket sports for racket strings, eyelets, and badminton shuttlecocks. Nylon 11 is used for the top layering of skis.

References

Biotechnology products Bioplastics Polyamides