Nylon 11

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Skeletal formula of a polyamide 11 repeating unit PA11 repeating unit.png
Skeletal formula of a polyamide 11 repeating unit

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. It is produced from castor beans by Arkema under the trade name Rilsan. [1]

Contents

Nylon 11 is applied in the fields of oil and gas, aerospace, automotive, textiles, electronics and sports equipment, frequently in tubing, wire sheathing, and metal coatings. [2]

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. [3] Thann & Mulhouse had already been involved in processing castor oil for 10-undecenoic-acid, which would eventually be converted into the first amount of 11-aminoundecanoic acid in 1940 with the help of coworkers Michel Genas and Marcel Kastner. In 1944, Kastner sufficiently improved the monomer process and the first patents for Nylon 11 were filed in 1947. [4] The first nylon 11 thread was created in 1950 and full industrial production began with the opening of the Marseilles production facility in 1955, which remains the sole producer of 11-aminoudecanoic acid today.

Currently Arkema polymerizes Nylon 11 in Birdsboro, PA, Changshu, and Serquigny. [5]

Chemistry

The chemical process of creating Nylon 11 begins with ricinoleic acid which makes up 85-90% of castor oil. Ricinoleic acid is first transesterified with methanol creating methyl ricinoleate, which is then cracked to create heptaldehyde and methyl undecylenate. These undergo hydrolysis to create methanol, which is re-used in the initial transesterification of ricinoleic acid, and undecylenic acid that is added on to hydrogen bromide. After hydrolysis, hydrogen bromide then undergoes nucleophilic substitution with ammonia to form 11-aminoundecanoic acid, which is polymerized into nylon 11. [5]

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 amides. 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. [2]

General properties of Nylon 11, Nylon 6
Density [6] Young's modulus [2] [7] Flexural modulus [2] Elongation

at break [6]

Water absorption

at 0.32 cm thick

and 24 h [6]

Melting point [6] Glass

transition

temperature [6]

Nylon 111.03-1.05 g/cm3335 MPa1200 MPa300-400%0.4%180-190 °C42 °C
Nylon 61.13 - 1.16 g/cm3725 - 863 MPa2400 Mpa300%1.3-1.9%210 - 220 °C48-60 °C

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, catheters, and beverage tubing. [2]

Electrical

Nylon 11 is used in cable and wire sheathing as well as electrical housings, connectors and clips. [2]

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. [8]

Textiles

Nylon 11 is used in textiles through brush bristles, lingerie, filters, as well as woven and technical fabrics. [2] [9]

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. [2]

Related Research Articles

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

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<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">Castor oil</span> Vegetable oil pressed from castor beans

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 313 °C (595 °F) and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about 90 percent of fatty acids are ricinoleates. Oleic acid and linoleic acid are the other significant components.

<span class="mw-page-title-main">Thermoplastic</span> Plastic that softens with heat and hardens on cooling

A thermoplastic, or thermosofteningplastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling.

<span class="mw-page-title-main">Aramid</span> Class of synthetic fiber

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

In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups. The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, three and four hydroxyl groups are diols, triols, and tetrols, respectively.

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 HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.

<span class="mw-page-title-main">Polyphthalamide</span> Semi-crystalline high-temperature plastic in the Nylon family

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<span class="mw-page-title-main">Zytel</span> Trademark

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

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<span class="mw-page-title-main">Polyglycerol polyricinoleate</span> Emulsion used in food production

Polyglycerol polyricinoleate (PGPR), E476, is an emulsifier made from glycerol and fatty acids. In chocolate, compound chocolate and similar coatings, PGPR is mainly used with another substance like lecithin to reduce viscosity. It is used at low levels, and works by decreasing the friction between the solid particles in molten chocolate, reducing the yield stress so that it flows more easily, approaching the behaviour of a Newtonian fluid. It can also be used as an emulsifier in spreads and in salad dressings, or to improve the texture of baked goods. It is made up of a short chain of glycerol molecules connected by ether bonds, with ricinoleic acid side chains connected by ester bonds.

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 skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.

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

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 the seeds of castor plant, the plant that produces ricin. It is also found in the sclerotium of ergot. About 90% of the fatty acid content in castor oil is the ricinolein.

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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 ; adhesives, advanced materials and coatings. A further segment covers chemical intermediates.

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<span class="mw-page-title-main">2-Octanol</span> Chemical compound

2-Octanol is an organic compound with the chemical formula CH3CH(OH)(CH2)5CH3. It is a colorless oily liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol is classified fatty alcohol. A secondary alcohol, it is chiral.

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.

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

References

  1. ↑ Herzog, Ben; Kohan, Melvin I.; Mestemacher, Steve A.; Pagilagan, Rolando U.; Redmond, Kate (2013), "Polyamides", Ullmann's Encyclopedia of Industrial Chemistry, American Cancer Society, doi:10.1002/14356007.a21_179.pub3, ISBN   9783527306732, S2CID   241272519
  2. 1 2 3 4 5 6 7 8 "Rilsan PA11 Brochure". Arkema. 2005. Retrieved 2018-11-28.
  3. ↑ Seymour, Raymond B.; Kirshenbaum, Gerald S., eds. (1987). High Performance Polymers: Their Origin and Development. doi:10.1007/978-94-011-7073-4. ISBN   978-94-011-7075-8.
  4. ↑ Arkema. "Arkema celebrates the 70th birthday of its flagship Rilsan® polyamide 11 brand". www.arkema-americas.com. Retrieved 2018-11-18.
  5. 1 2 Devaux, Jean-François. "APPLICATION OF ECO-PROFILE METHODOLOGY TO POLYAMIDE 11" (PDF). Arkema.
  6. 1 2 3 4 5 Selke, Susan E.M.; Culter, John D. (2015-12-11), "Major Plastics in Packaging", Plastics Packaging, Carl Hanser Verlag GmbH & Co. KG, pp. 101–157, doi:10.3139/9783446437197.004, ISBN   9783446407909
  7. ↑ Permeability and other film properties of plastics and elastomers. 1996-01-01.
  8. ↑ "Nylon Coating Services". www.wrightcoating.com. Retrieved 2018-12-02.
  9. ↑ Gordon., Cook, J. (1984-01-01). Handbook of textile fibres. Volume 1, Natural fibers (Fifth ed.). Cambridge, England. ISBN   9781845693152. OCLC   874158248.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: multiple names: authors list (link)
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