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 th ...

bioplastic Bioplastics are plastic materials produced from renewable biomass sources, such as vegetable fats and oils, corn starch, straw, woodchips, sawdust, recycled food waste, etc. Some bioplastics are obtained by processing directly from natural bi ...

and a member of the

nylon Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic. Nylon is a silk-like thermoplastic, generally made from pet ...

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-aminound ...

. It is produced from

castor bean ''Ricinus communis'', the castor bean or castor oil plant, is a species of perennial flowering plant in the spurge family, Euphorbiaceae. It is the sole species in the monotypic genus, ''Ricinus'', and subtribe, Ricininae. The evolution of ...

s by

Arkema Arkema S.A. is a publicly listed, multi-national manufacturer of specialty materials, headquartered in Colombes, near Paris, France. It has three specialty materials segments (or divisions); adhesives, advanced materials and coatings. A furt ...

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

oil and gas A fossil fuel is a hydrocarbon-containing material formed naturally in the Earth's crust from the remains of dead plants and animals that is extracted and burned as a fuel. The main fossil fuels are coal, oil, and natural gas. Fossil fuels ...

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 ast ...

, 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, different #Fabric, fabric types, etc. At f ...

electronics The field of electronics is a branch of physics and electrical engineering that deals with the emission, behaviour and effects of electrons using electronic devices. Electronics uses active devices to control electron flow by amplification ...

and

sports equipment Sports equipment, sporting equipment, also called sporting goods, are the tools, materials, apparel, and gear used to compete in a sport and varies depending on the sport. The equipment ranges from balls, nets, and protective gear like helmets. ...

, 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. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about ...

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

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 ( , , ; also spelled in English as Marseilles; oc, Marselha ) is the prefecture of the French department of Bouches-du-Rhône and capital of the Provence-Alpes-Côte d'Azur region. Situated in the camargue region of southern Fra ...

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 for ...

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 Yan ...

, and

Serquigny Serquigny () is a commune of the Eure department in Normandy in northern France. It lies on the rail line from Cherbourg to Paris. In the village there is a privately owned manor house called Chateau de Maubuisson. Population Démographie ...

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 omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from mature castor plant (''Ricinus communis'' ...

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 and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...

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, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...

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 tem ...

. After hydrolysis, hydrogen bromide then undergoes

nucleophilic substitution In chemistry, a nucleophilic substitution 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). The ...

with

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous ...

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 compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...

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.

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 lines, hydraulic hoses, air lines, umbilical hoses,

catheter In medicine, a catheter (/ˈkæθətər/) 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 surgi ...

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, fash ...

, filters, as well as woven and technical fabrics.{{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