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NYLON

Chemical Properties, Process and Applications

Author:

Date started: 13 th October 2010

Cameron Kashani

The report has been prepared for ACME Textile Company technical division

October 2010 Cameron Kashani The report has been prepared for ACME Textile Company – technical division
October 2010 Cameron Kashani The report has been prepared for ACME Textile Company – technical division
October 2010 Cameron Kashani The report has been prepared for ACME Textile Company – technical division

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CONTENTS

CONTENTS EXECUTIVE SUMMARY 2 1 Introduction 3 2 History 3 3 Chemical Properties 3 4

EXECUTIVE SUMMARY

2

1 Introduction

3

2 History

3

3 Chemical Properties

3

4 Applications

9

5 Production Process

10

6 Transportation Criteria

11

7 Laws and Regulations

11

8 Conclusion

11

Appendix A References

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Executive Summary

Aim To write an informative report on Nylon.

Objectives

- To highlight the history of nylon, its origins and its inventors.

- To describe the chemistry of Nylon, the most common version of nylon and to review the chemical structure of an example of nylon, its structure and its properties.

- To describe the uses of nylon, both in everyday life and industry.

- To state how nylon is processed and produced.

- To identify nylon's storage requirements and transportation.

- To state any laws and regulations on any of the above in the UK.

- To list the references used in compiling this report.

Writing process Firstly, various sources were found on the internet and from books. The sources were checked for validity. This was done by checking from where the source originated (eg. if the source originated from a company or university then it was valid).

Before it was written, the sections of the report were planned.

The report was then written with special attention to referencing sources when stating the relevant information.

Additional information and Conclusion Information on the transport and delivery and laws and regulations were harder to find. All the aims and objectives were fulfilled.

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1 Introduction

This is a report investigating the textile polymer called Nylon. The report will also attempt to give a brief history and informative description of what nylon is. The report will also include references and sources of information.

2 History

Nylon is a material that was first produced by a team of scientists, led by "American chemist Wallace Hume Caruthers (1896-1937)" at Du Pont in the 1930s, as described by Hegde et al (2004). According to Hegde et al (2004) it was "the first truly synthetic fiber to be commercialized (1939)."

3 Chemical Properties

Nylon is an artificially produced "thermoplastic" polymer (Hegde et al [2004]) with several useful properties. As explained by Hegde et al (2004) it is produced by reacting a diamine with a dioic acid.

The most commonly used version of nylon is 6-nylon as Aharoni (1997) explains in his book. To demonstrate the chemistry of polymers, however, 6,6-nylon will be used as an example.

6,6-nylon involves two monomers; "hexamethylenediamine (1,6-diaminohexane, H 2 N- (CH 2 ) 6 -NH 2 )" and "adipic acid (Hexane-1,6-dioic acid, HOOC-(CH 2 ) 4 -COOH)" which Cotton (2010) states in his report. The structures of 6,6-nylon's two monomers are shown in the table (page 4).

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Picture

Description

The chemical structure of hexamethylenediamine. Picture by ChemBlink (2010).

The chemical structure of hexamethylenediamine. Picture by ChemBlink (2010).

The chemical structure of adipic acid. (picture: Biological Magnetic Resonance Data Bank 2010).

The chemical structure of adipic acid. (picture: Biological Magnetic Resonance Data Bank 2010).

A table showing the mechanism of the production of 6,6-nylon. All the information is taken
A table showing the mechanism of the production of 6,6-nylon. All the information is taken from the diagrams
which are taken from the Polymer Science learning center (2010).
Step of the mechanism
What occurs in the
mechanism
Oxygen from one
adipic acid molecule,
donates a pair of
electrons to a
hydrogen atom of a
hydroxide group in
another adipic acid
molecule. This
causes the oxygen
atom to become
protonated, making
the carbon atom it is
bonded to vulnerable
to nucleophilic attack.
1
A nitrogen atom from the hexamethylenediamin e atom donates an electron pair to the slightly
A
nitrogen atom from
the
hexamethylenediamin
e
atom donates an
electron pair to the
slightly positive
carbon atom on the
protonated adipic acid
molecule.
2
The hydrogen atom
bonded to the
protonated oxygen
atom, donates an
electron pair to the
oxygen atom, which
then donates an
electron pair to the
carbon atom, which
then donates an
electron pair to the
hydroxide group. The
hydroxide group then
donates an electron
pair to a hydrogen
atom, which donates
an electron pair to the
positive nitrogen
atom. This results in a
"dimer" being
produced as well as a
molecule of water and
a
hydrogen ion.
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The final product is shown in the diagram (6,6 – nylon).
The final product is
shown in the diagram
(6,6 – nylon).

The bonds between the chains are hydrogen bonds as explained by the Polymer Science Learning Center (2010).

These bonds determine nylon's properties, (especially "strength" [Lagasse 2008]). How the polymer chains are arranged also determines nylon's properties.

There are two types of structures in polymers, as explained by Rosato (1997). He details how polymers can be crystalline or amorphous. In nylon, the long chains can align (crystalline). Any other structure, as Rosato (1997) explains, is amorphous.

A table taken from Rosato’s book (1997). A list of nylon’s properties from the CES

A table taken from Rosato’s book

(1997).

A table taken from Rosato’s book (1997). A list of nylon’s properties from the CES Edupack

A list of nylon’s properties from the CES Edupack

(2010).

The "non-equilibrium melting point of 6,6-nylon is around 255-60°C" as Aharoni (1997) states in his book. According to Aharoni (1997), this is determined by the number of "CH 2 units in the diamine and the dicarboxylic acid components".

Nylon is also recyclable. Here is nylon's recyle mark (CES Edupack [2010]).

As the CES Edupack (2010) details, during primary production, 5.5 5.6 kg of CO 2 is released per kg of nylon produced.

(2010) details, during primary production, 5.5 – 5.6 kg of CO 2 is released per kg

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Applications

Cotton (2010) intimates that, because of its corrosion free nature, nylon was used in toothbrushes (as shown in the advertisement).

A Dr. Westsnylon toothbrush advertisement.

Picture taken from Cotton’s nylon report (2010).

Picture taken from Cotton’s nylon report (2010). Information from the list is from the CES Edupack

Information from the list is from the CES Edupack (2010)

- Light duty gears

- Bushings

- sprockets and bearings

- electrical equipment housings

- Lenses

- Containers

- Tanks

- Tubing

- furniture casters

- plumbing connections

- bicycle wheel covers

- ketchup bottles

- Chairs

- toothbrush bristles

- Handles

- Bearings

- food packaging

- Ropes

A list of nylon uses directly from the CES Edupack (2010).

Because of the "extreme toughness, strength and peculiar ability to be formed into fibres" (Adams 1939), nylon is ideal for such applications as handles and chairs, which take loads, or for ropes and toothbrush bristles, which require fibres.

5

Production Process

Nylon salt Hexamethylene diamine Raw materials 1 2 Adipic acid 3 “Linear Concentrated Nylon solution
Nylon salt
Hexamethylene diamine
Raw materials
1
2
Adipic acid
3
“Linear
Concentrated
Nylon solution
5
4
Superpolymers”
solution.
6
6,6-Nylon
A flowchart describing the production of nylon.
All the information from this flowchart is from
the narrow fabrics website (2010).
filaments.

- Description of flow chart

1. Processing of raw materials.

2. The monomers are "combined". They are mixed together (not reacted, that occurs in the

reaction vessels).

3. The nylon salt is dissolved in water. It is possible to infer that this makes the salt easier to

transport.

4. "In the spinning mill, salt is heated in evaporators to obtain a concentrated solution." This

could be to increase the reaction rate between the "two chemicals".

5. Reaction vessels use heat to combine the "two molecules of the two chemicals into large

chainlike molucules known as 'linear superpolymers'".

6. The "linear superpolymers" move around a casting wheel. A spinneret removes strands

of nylon from the molten nylon which are "air-cooled to form filaments".

All information from the description above is from the narrow fabrics website (2010).

A more complex and in depth flow chart is shown below.

A more complex and in depth flow chart is shown below. A flow chart from the

A flow chart from the Pall corporation (accessed 2010).

6 Transportation Criteria

Inchem (2010) states that "crystalline AH salt" (which it says is "produced in closed systems by mixing adipic acid and 1,6-hexanediamine in water at approx. 90 °C") is transported at 90 °C "on tank trucks, ships or tank wagons" in "stainless steel tanks". It also states how the tanks are insulated as to ensure the AH salt remains a liquid.

7 Laws and regulations

Direct Plastics (2004) states that there is "no warning necessary" under "EU guidelines". Under "potential risks", the website explains that nylon is not harmful.

Direct Plastics (2004) also states that 6,6-nylon can be recycled and "if no use is possible, product waste can, in accordance with official local regulations, be mixed with household waste or incinerated in an appropriate place".

The "conditions to avoid" are also stated; apparently temperatures above 300°C results in thermal decomposition which can produce toxic gases (e.g. carbon monoxide and nitric oxide).

8 Conclusion

The chemistry, properties and production of nylon are far easier to find than the laws and transportation of nylon. However, I feel I have succeeded in fulfilling my aims and objectives for this report.

Appendix A References

"n-Nylons: Their Synthesis, Structure and Properties"; pages 63, 170 Shaul M. Aharoni

(1997)

"The Columbia Encyclopedia Sixth Edition"; Paul Lagasse (2008)

" http://www.narrow-fabrics-manufacturers.com/articles/nylon6-6.html"; Online B2B Marketplace narrow fabrics (consulted 13/10/2010 at 17:21)

"http://www.engr.utk.edu/mse/Textiles/Nylon%20fibers.htm"; Raghavendra R. Hegde, Atul Dahiya, M. G. Kamath (Monika Kannadaguli and Ramaiah Kotra) University of Tennessee Knoxville (consulted 14/10/2010 at 11:48, last updated April 2004)

"http://www.chm.bris.ac.uk/motm/nylon/nylonv.htm"; Simon Cotton, Uppingham School, Rutland, UK from the University of Bristol school of chemistry (consulted 14/10/2010 at 12:29, last updated 01/06/2010)

" http://www.chemblink.com/products/124-09-4.htm"; ChemBlink (consulted 14/10/2010 at

13:20)

"http://www.bmrb.wisc.edu/metabolomics/mol_summary/?molName=Adipic_acid"; Biological Magnetic Resonance Data Bank (consulted 15/10/2010 at 12:24)

"http://pslc.ws/macrogcss/nysyn.html"; Polymer science learning center (consulted 23/10/2010 at 16:46)

"http://pslc.ws/macrog/lab/lab01.htm"; Polymer science learning center (consulted 24/10/2010 at 21:22)

"www.nap.edu/html/biomems/wcarothers.pdf"; National academies press; National Academy of Sciences: biographical memoir of Wallace Hume Carothers by Roger Adams (presented at an annual meeting 1939) (consulted 24/10/2010 at 21:29)

"Plastics Processing Data Handbook (2nd Edition)" pages 59, 60 accessed through Knovel.com (consulted 27/10/2010 at 19:54); Author: Dominick Rosato (1997)

CES Edupack 2010; MaterialUniverse: Polyamides (Nylons, PA) (accessed 29/10/2010 at

22:57)

"http://www.pall.com/pdf/PPG3a.pdf"; Pall corporation; Nylon 66 Fiber Production (accessed 30/10/2010 a 14:00)

"http://www.inchem.org/documents/sids/sids/3323533.pdf"; INCHEM Chemical Safety Information from Intergovernmental Organizations (accessed 30/10/2010 at 15:44)

"http://www.directplasticsonline.co.uk/pdf/HSE_Nylon_66.pdf"; Direct Plastics (written 15/04/2004) (accessed 30/10/2010 at 16:37)

Word count: Around 1090 words excluding references, subtitles, tables, the title page, flowcharts and this sentence.