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Drafting

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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]

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

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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

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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-aminoudecanoic acid, which is polymerized into nylon 11.[5]

Properties

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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 11 1.03-1.05 g/cm3 335 MPa 1200 MPa 300-400% .4% 180-190°C 42°C
Nylon 6 1.13 - 1.16 g/cm3 725 - 863 MPa 2400 Mpa 300% 1.3-1.9% 210 - 220°C 48-60°C

Applications

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Tubing

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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

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

Coatings

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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

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

Sporting Goods

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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]

Notes for Professor Hansen

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"Have you thought about the order of your sections? Is there a reason to have properties, then history, then chemistry?"

I re-arranged the order of the sections with inspiration from the Nylon article as it is much more complete and reviewed. Looking at how the article for nylon is arranged, it makes more sense. You sort of start all the way zoomed in to the origins of nylon with the history, back out a bit for chemistry, then to properties, etc.

"Would it be useful to have a new first sentence to this section which gives a listing of the main properties that are different from Nylon 6? Then each following sentence would talk about those properties in order."

I was leaning towards using a table when I originally wrote this section, however I sort of shy'd away from the idea due to the comparisons to Nylon 6. Based on your suggestion, I made a table of some general properties for both forms and lightly touched on the differences afterwards. It definitely took some of the bulk out of the section, but it feels less awkwardly wordy.

"Any idea if for any of these applications it is the primary type of polymer used in those applications? Is it dominating the market in any of these applications?"

From what I can tell, no. Based on how the product is described it seems as though it is a higher priced "eco-friendly" alternative to other forms of nylon that are more common, but that's just a gut feeling. I wanted to include that idea but it was difficult to find any broad data that would back up my claim. At one point I did find this report of what seemed like a global scope for the use of nylon 11, but it was like 3000 dollars from what appeared to be a consulting firm or something.

Notes

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  • Avoiding modification of summary by adding additional information to avoid throwing the article out of balance. I think it would be beneficial to spread out information into similar sized sections based on the availability of information. For layout of sections, see drafting section of this sandbox.
  • Based on the information available and my understanding of the subject, general properties of nylon 11 will be introduced in the applications section of the article as a reference to why nylon 11 is applied.
  • I would like to include a visual to illustrate the chemical production process that is found in source 3 with it's included description, however I am unsure how to rephrase this into my own words and recreate the image without further knowledge of chemistry at the level being described. i am wondering whether to include the description as a quote along with the figure with sufficient citing. I know this information to be valid as the author of the source is a chemical engineer who works directly with nylon 11.
  • Possibly include an image of ski boots or other nylon 11 products to be used in the applications section
  • Chemical structure visual along with table of relevant properties similar to the nylon page.

Planning

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Nylon 11 Article

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I plan to add the following:

  • information on the discovery of nylon 11 and relevant dates
  • Relevant graphics of nylon 11 chemical structure and the chemical steps to create nylon 11
  • Include relevant manufacturing information
  • Provide a table of relevant properties of the material from knovel

Initial Article:

  • Summary well describes key characteristics of nylon 11, despite it's questionable writing
  • Summary is all that is present for the article
  • Single source provided clearly does not supply all the information that is given
  • Source is not referenced in text
  • Applications of nylon 11 feels clunky, no source used

References

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  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, retrieved 12/04/2018 {{citation}}: Check date values in: |access-date= (help)
  2. ^ a b c d e f g h "Rislan PA11 Brochure". Arkema. 2005. Retrieved 11/28/2018. {{cite web}}: Check date values in: |access-date= (help)
  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. ^ a b Devaux, Jean-François. "APPLICATION OF ECO-PROFILE METHODOLOGY TO POLYAMIDE 11" (PDF). Arkema.
  6. ^ a b c d e 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, retrieved 2018-12-04
  7. ^ "Permeability and other film properties of plastics and elastomers". Choice Reviews Online. 33 (5): 33–2765-33-2765. 1996-01-01. doi:10.5860/choice.33-2765. ISSN 0009-4978.
  8. ^ "Nylon Coating Services". www.wrightcoating.com. Retrieved 2018-12-02.
  9. ^ Gordon., Cook, J. (January 1984). 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)