Research proposal

On

The Study On The Properties Of Synthesis Of Nylon

610

By

Moyibon Amsalu Mosisa

Submitted in partial fulfillments of the requirements for the degree of
Bachelor (BSc) of Science in physics
In School of Applied Natural Science at Adama Science and
Technology University

Advisor: Dr.Mesfin Asfew

Adama Science and Technology University

March 2018
Contents
1. Introduction........................................................................................................................................... 1

1.1. Background ............................................................................................................................ 1

1.2. Statement of the problem ....................................................................................................... 2

1.3. Significance of the study ........................................................................................................ 2

1.4. Objective of the study ............................................................................................................ 2

1.4.1. General objective ............................................................................................................ 2

1.4.2. Specific objective ............................................................................................................ 2

2. Literature review ................................................................................................................................... 3

2.1. Origin of the name ................................................................................................................. 4

3. Materials and methods used .................................................................................................................. 7

3.1. Chemicals and solvent............................................................................................................ 7

3.2. Apparatus ............................................................................................................................... 7

3.2.1. Synthesis of nylon 610 ................................................................................................... 7

3.2.2. Methods And Methodology’s ......................................................................................... 8

3.3. Characterization methods for nylon 610 synthesis ................................................................ 8

4. Work Plan and Budget ........................................................................................................................ 10

4.1. Work plan ............................................................................................................................. 10

5. Budget Breakdown .............................................................................................................................. 11

6. References ............................................................................................................................................... 12
1. Introduction
1.1. Background
Nylon is a thermoplastic and silky polymer type of material. The chemical structure of nylon is
made of repeating units linked by amid bonds and frequently referred to as poly amide (PA). It
was the first commercially successful synthetic thermoplastic polymer.

Nylon is used in many applications including clothe fabrics, bridal veils, package papers, carpets
musical strings, pipes and rope. Solid nylon is used in hair combs. Nylon product includes
hosiery, parachutes, tents, tooth brush, bristles. There are two major types of polymer formation
reaction. Thus are addition polymerization and condensation polymerization. From the two of
them, condensation polymerization is use in the production of the nylon 610. Nylon is a
thermoplastic produced by interfacial polymerization between two monomer units, i.e. Sebacoyl
chloride and Hexamethylene diamine. Nylon 610 is a silky material used as textile materials for
cloth which is prepared from two monomer units.

Nylon 610 is produced by condensation reaction, i.e. the polymer repeat unit arises from reacting
two different functional groups in our case ketone and amide, which usually originate on
different monomers (sebacoyl chloride and Hexamethylenediamine). In addition small molecules
are often eliminated during condensation reaction in this case hydrochloric acid.

The amidation of the reactive groups in interfacial polymerization is governed by the rates at

which these two immiscible liquid phases can diffuse to the surface where the growing polymer

is deposited . [9]

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1.2. Statement of the problem
In the previous work many researchers have been investigating the synthesis of nylon 610.In
this work, we will going to study the properties and mechanisms of synthesis of nylon 610 and to
synthesis nylon 610.

1.3. Significance of the study

The use of synthesis of nylon 610 is lower brittle temperature, lower water absorption, stronger
and, retains room temperatures toughness at low temperature

1.4. Objective of the study

1.4.1. General objective
To study the tensile properties of the synthesized collapsed film and compare it to the tensile properties of
Nylon tire cord.

1.4.2. Specific objective

To synthesize supported membranes of Nylon 6,10 on hydrophilic Millipore membranes.

To synthesize unsupported membranes of Nylon 6,10 by unstirred interfacial step

polymerization of hexamethylene diamine (HMDA) and sebacoyl chloride.

2
2. Literature review
Du Pont founded by Éleuthère Irénée du Pont, first produced gunpowder and later cellulose-
based paints. Following WWI, DuPont produced synthetic ammonia and other chemicals.
DuPont began experimenting with the development of cellulose based fibres, eventually
producing the synthetic fibre rayon. DuPont's experience with rayon was an important precursor
to its development and marketing of nylon. [12] DuPont’s invention of nylon spanned a nine-year
period, ranging from the start of the project in 1930 to its exhibition at the World Fair in New
York in 1939.[12] The project grew from a new structure at DuPont, suggested by Charles
Stine in 1927, in which the chemical department would be composed of several small research
teams that would focus on “pioneering research” in chemistry and would “lead to practical
applications”. [12] Harvard instructor Wallace Hume Carothers was hired to direct the polymer
research group. Initially he was allowed to focus on pure research, building on and testing the
theories of German chemist Hermann Staudinger.
[10]He was very successful as research he undertook greatly improved the knowledge of polymers
and contributed to science.[11]

In the spring of 1930, Carothers and his team had already synthesized two new polymers. One
was neoprene, a synthetic rubber greatly used during the war. The other was a white elastic but
strong paste that would later become nylon. After these discoveries Carother’s team was made to
shift its research from a more pure research approach investigating general polymerization to a
more practically-focused goal of finding “one chemical combination that would lend itself to
industrial applications”.[12]

It wasn’t until the beginning of 1935 that a polymer called "polymer 6-6" was finally produced.
The first example of nylon (nylon 6,6) was produced by Wallace Carothers on February 28,
1935, at DuPont's research facility at the DuPont Experimental Station.[2] It had all the desired
properties of elasticity and strength. However, it also required a complex manufacturing process
that would become the basis of industrial production in the future.

DuPont obtained a patent for the polymer in September 1938,[13] and quickly achieved a
monopoly of the fibre.[11]

3
The production of nylon required interdepartmental collaboration between three departments at
DuPont: the Department of Chemical Research, the Ammonia Department, and the Department
of Rayon. Some of the key ingredients of nylon had to be produced using high pressure
chemistry, the main area of expertise of the Ammonia Department. Nylon was considered a
“godsend to the Ammonia Department”, [12]which had been in financial difficulties. The reactants
of nylon soon constituted half of the Ammonia department’s sales and helped them come out of
the period of the Great Depression by creating jobs and revenue at DuPont.[12] DuPont's nylon
project demonstrated the importance of chemical engineering in industry, helped create jobs, and
furthered the advancement of chemical engineering techniques. In fact, it developed a chemical
plant that provided 1800 jobs and used the latest technologies of the time, which are still used as
a model for chemical plants today.[12] “The success of the nylon project thus had to do with its
ability to achieve the rapid mobilization of a large number of DuPont’s chemists and engineers”.
[12]The first nylon plant was located at Seaford, Delaware, beginning commercial production on
December 15, 1939. On October 26, 1995, the Seaford plant was designated a National Historic
Chemical Landmark by the American Chemical Society.[12]

2.1. Origin of the name

DuPont went through an extensive process to generate names for its new product[11] In 1940,
John W. Eckelberry of DuPont stated that the letters "nyl" were arbitrary and the "on" was
copied from the suffixes of other fibers such as cotton and Rayon.

A later publication by DuPont (Context, vol. 7, no. 2, 1978) explained that the name was
originally intended to be "No-Run" ("run" meaning "unravel"), but was modified to avoid
making such an unjustified claim.

4
Since the products were not really run-proof, the vowels were swapped to produce "nuron",
which was changed to "nilon" "to make it sound less like a nerve tonic". For clarity in
pronunciation, the "i" was changed to "y".[17]

An important part of nylon’s popularity stems from DuPont’s marketing strategy. The fibre was
promoted to increase demand before the product was available to the general market. Nylon’s
commercial announcement occurred on October 27, 1938, at the final session of the Herald
Tribune's yearly "Forum on Current Problems", on the site of the approaching New York City
world's fair.[10] The “first man-made organic textile fiber” which was derived from “coal, water
and air” and promised to be “as strong as steel, as fine as the spider’s web” was received
enthusiastically by the audience, many of them middle-class women, and made the headlines of
most newspapers.[11] Nylon was introduced as part of "The world of tomorrow" at the 1939 New
York World's Fair[4]and was featured at DuPont's "Wonder World of Chemistry" at the Golden
Gate International Exposition in San Francisco in 1939[10].Actual nylon stockings were not
shipped to selected stores in the national market until May 15, 1940. However, a limited number
were released for sale in Delaware before that.[11] The first public sale of nylon stockings
occurred on October 24, 1939, in Wilmington, Delaware. 4,000 pairs of stockings were
available, all of which were sold within three hours.[10]

Another added bonus to the campaign was that it meant reducing silk imports from Japan, an
argument that won over many wary customers. Nylon was even mentioned by President’s
cabinet, which addressed its “vast and interesting economic possibilities” five days after the
material was formally announced.[11] However, the early excitement over nylon also caused
problems. It fueled unreasonable expectations that nylon would be better than silk, a miracle
fabric as strong as steel that would last forever and never run.

5
[11] Realizing the danger of claims such as “New Hosiery Held Strong as Steel” and “No More
Runs”, Du Pont scaled back the terms of the original announcement, especially those stating that
nylon would possess the strength of steel.[11] Also, DuPont executives marketing nylon as a
revolutionary man-made material did not at first realize that some consumers experienced a
sense of unease and distrust, even fear, towards synthetic fabrics.[11]A particularly damaging
news story, drawing on DuPont's 1938 patent for the new polymer, suggested that one method of
producing nylon might be to use cadaverine, a chemical extracted from corpses. Although
scientists asserted that cadaverine was also extracted by heating coal, the public often refused to
listen, as in the case of a woman who confronted one of the lead scientists at DuPont and refused
to accept that the rumour was not true.[11] DuPont changed its campaign strategy, emphasizing
that nylon was made from “coal, air and water”, and started focusing on the personal and
aesthetic aspects of nylon, rather than its intrinsic qualities.[11] Nylon was thus domesticated,[11]

and attention shifted to the material and consumer aspect of the fiber with slogans like “If it’s
nylon, it’s prettier, and oh! How fast it dries!”[12]

6
3. Materials and methods used
3.1. Chemicals and solvent.
The following chemicals and solvents will used in this work.
Dichloromethane,Sebacoyl chloride, Hexamethylenediamine, Sodium hydroxide

3.2. Apparatus
The laboratory apparatus used for this work are the following.

Stirrer, Stirrer bar, Reactor, Balance

3.2.1. Synthesis of nylon 610

First, I will make two solutions separately, to make the first solution. Then I will dissolve 0.8mL of
Sebacoyl chloride in 10mL of dichloromethane. Secondly, I will dissolve 0.46g of Hexamethylene
diamine and 0.08g of NaOH in 10mL of water. After I made these two separate solutions I will add the
second solution to the first solution slowly by pouring down the side of the beaker. In this step I will not
stir it. As a result a film (Nylon 6-10 will be formed at the interface of the two solutions.
Finally I will hook carefully the film with a glass rod and will pull the film from the beaker in a long
strand.

7
3.2.2. Methods And Methodology’s

3.3. Characterization methods for nylon 610 synthesis

This nylon is synthesis by the process of interfacial polymerization. Interfacial polymerization is
the reaction of monomers to form a very large molecule at the contact between two immiscible
liquid layers. The monomers are dissolved in different layers, and only come into contact at into
Different layers, and only come into contact at the interface.
The main functional group present in nylon molecules is the amide functional group. Interfacial
polymerization can be of two types. In one case, there are two separate macroscopic layers in
contact with each other. This is called unstirred interfacial polymerization. This is what we are
going to study in this experiment. Unstirred interfacial polymerization is used to produce
membranes and to create polymer by continuous removal in a single rope.
The other case is stirred interfacial polymerization.
H O O
H

N CH
CH
2 CH
2 CH
2 CH
2 CH
2 2N + C CH
CH
2 CH
2 CH
2 CH
2 CH
2 CH
2 CH
2 2C

H H Cl Cl

Hexamethylene diamine O Sebacoyl

O chloride
H H H H
N CH
CH
2 CH
2 CH
2 CH
2 CH
2 2 N C CH
CH
2 CH
2 CH
2 CH
2 CH
2 CH
2 CH
2 2 C N CH
CH
2 CH
2 CH
2 CH
2 CH
2 2 N + HCl

O O

H H
N
ylo
n6,1
0= N )6N
(CH
2 C (CH
)8C
2
n n

 In order to make a polyamide, such as Nylon 610, the amine molecule must have

a –NH2 group at each end, and the acid chloride must have a –COCl group at

each end.

 The diamine and the diacid chloride bond together, end-on-end, to form very long

chains.

8
  Nylon 610 is made from hexamethylene diamine (the diamine) and sebacoyl
chloride (the diacid chloride).
Condensation polymerization is a form of step- growth polymerization, is the process by
which two molecules join together, resulting loss of small molecules which is often
water. The type of the end product depends on the number of functional end groups of the
monomer which can react the monomers that are involved are not the same as those in
addition polymerization. The name is coined due to water is condenses out in the
process.
The meaning of the number 610 in the IUPAC name of the nylon is one type of naming
the nylon synthetic polymer based on the nomenclature of the chemical structure of the
nylon forming monomers. That means the diamines (hexamethylendiamine) made from
6 carbon and the diacid chloride(sebacoyl chloride ) made from 10 carbon.

The chemical structure of nylon 610 is drawn as this.

Chemical structure of nylon 610.

The NaOH is used as a catalyst and neutralizing agent since hydrochloric acid is formed
during experiment.
The nylon silk produced is not uniform in thickness due to non-uniform speed of hooking
and error in pouring down the side of the beaker, i.e. Hexamethylenediamin in water
sinks in one side down in Sebacoyl Chloride in dichloromethane.

9
4. Work Plan and Budget
4.1. Work plan
Table 1: Time Schedule

No Activities Periods
March April May June
1 Proposal development 
2 Gathering reviewing literature 
3 First draft proposal 
Submission
4 Second draft proposal 
submission
5 Final draft proposal 
6 Proposal defense 
7 Organizing UG research 
8 UG research writing 
9 Submission of first draft of UG 
research
10 Submission of second draft 
UG research
11 Submission of final draft UG 
research
12 UG research defense 

10
5. Budget Breakdown
Table 2. Budget Breakdown

No Activities Unit Quantity Unit Price Total

(Birr)
Price
(Birr)
1 Printing paper Number 3 150.00 450.00
2 Duplicating and binding Number 90 0.50 45.00
3 Flash Disk Number 1 300.00 300.00
4 CD Number 5 100.00 400.00
5 Stationaries Number 100 5.00 500.00
6 Memory Card Number 2 200.00 400.00
7 Software training
8 Telephone 500.00
9 Materials(chemicals,apparatus,solvents) 10,000.00
10 Internet service 5,000.00

TOTAL = 17595

11
6. References
[1] Algeo, John (2009).
[2] American Chemical Society National Historic Chemical Landmarks,2015
[3] American Chemical Society. Retrieved 26 June 2017
[4] Blakinger, Keri (April 30, 2016).
[5] Herman L. Wagner. The Mark-Houwink-Sakurada Equation for the Viscosity of Atactic
Polystyrene. J. Phys. Chem. Ref. Data (1985) 14, 1101-1106.
[6] Islam, M.; Hornedo, N.; Ciotti. S.; Ackermann. C. Rheological Characterization of Topical
Carbomer Gels Neutralized to Different pH. Pharma. Res. (2004) 21, 1192-1199.
[7] J. Huang, P. F. Miller, J. C. De Mello, A. J. De Mello, D. D. C. Bradley, Synthetic Metals,
(2003), 139, 569-572
[8] Kabanov av,Okano , T: Challenges in polymer therapeutics: state of the art and prospects of
polymer drugs. Adv. Exp Med. Biol. (2003) 519:1-27.
[9] Kang, M.; Myung S. J.; Jin. H. Nylon 610 and Carbon Nanotube Composite by in situ
Interfacial Polymerization. Polymer (2006) 47, 3961-3966.
[10] Kativa, Hillary (2016)
[11] Meikle, Jeffrey L. (1995)

[12] Ndiaye, Pap A.; Forster, Elborg (2007)

[13] Patents. Retrieved19 June 2017.

[14] Sundberg, Richard J. (2017
[15] Taolei Sun and Guangyan Qing: Biomimetic Smart Interface Materials for Biological
Applications, Adv. Mater. 2011, 23, H57-H77.
[16] WWW.Wikipedia.

[17] Wolfe, Audra J. (2008).

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