NYLON

Chemical Properties, Process and Applications

Author: Cameron Kashani

Date started: 13th October 2010

The report has been prepared for ACME Textile Company – technical division

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CONTENTS

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 12

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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, H2N-

(CH2)6-NH2)" and "adipic acid (Hexane-1,6-dioic acid, HOOC-(CH2)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 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 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.

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 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 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.

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A table taken from Rosato’s book
(1997).

A list of nylon’s properties

from the CES Edupack
(2010).

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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 "CH2
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 CO2 is released per kg of nylon produced.

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4 Applications

Cotton (2010) intimates that, because of its corrosion free

nature, nylon was used in toothbrushes (as shown in the
advertisement).

A “Dr. West’s” nylon toothbrush

advertisement.

Picture taken from Cotton’s nylon

report (2010).

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

- Light duty gears

- Bushings
- sprockets and bearings
- electrical equipment housings A list of nylon uses directly from the
- Lenses
CES Edupack (2010).
- Containers
- Tanks
- Tubing
- furniture casters
- plumbing connections
- bicycle wheel covers
- ketchup bottles
- Chairs
- toothbrush bristles
- Handles
- Bearings
- food packaging
- Ropes

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.

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 5 Production Process

Hexamethylene diamine Nylon salt

Raw materials
1 2
Adipic acid

“Linear Concentrated Nylon solution

Superpolymers” 5 solution. 4

6 A flowchart describing the production of nylon.

All the information from this flowchart is from
6,6-Nylon 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).

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

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.

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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.

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