Afzal Ahmad

SYNTHESIS
OF()
NYLON
6,10

Abstract

Nylon 6,10 has made with Diamine and Diacid Chloride with Stirred
Interfacial Polymerization technique. After the formation Nylon 6,10
Polymer Science by Prof. Jinmei Du
has placed in a patri dish for drying and further testing.

Unstirred Interfacial Polymerization

School Of Textile and

Apparel
Jiangnan University

Author: 1
Synthesis of nylon 6,10

Table of Contents
Table of Contents.............................................................................................................................1
Abstract:...........................................................................................................................................2
1. Introduction..............................................................................................................................3
1.1.

2.
3.
4.
5.
6.
7.
8.

Theory............................................................................................................ 3

1.1.1

Step Growth Polymerization Polyamides (Nylons).................................3

1.1.2

Interfacial Polymerization:.......................................................................4

1.1.3

Unstirred interfacial polymerization of Nylon 6,10...................................4

1.1.4

Safety, Handling, and Disposal................................................................5

Equipment and Materials..........................................................................................................6

Methods and Procedures..........................................................................................................6

3.1

Preparation of sample:...................................................................................6

Procedure:.................................................................................................................................6
Results......................................................................................................................................7
Advantages...............................................................................................................................7
Disadvantages...........................................................................................................................7
Reference..................................................................................................................................7

Polymer Science Experiment

Author: 2
Synthesis of nylon 6,10

Abstract:
Nylon 6,10 has made with Diamine and Diacid Chloride with Unstirred
Interfacial Polymerization technique. After the formation Nylon 6,10 has
placed in a patri dish for drying and further testing.

Polymer Science Experiment

Author: 3
Synthesis of nylon 6,10

1. Introduction
1.1. Theory
Polymers are large molecules made up by joining together many small
molecules. The small molecules that go into making a polymer are called
monomers. When just two monomers join together the product is called a
dimer.
Polymers make up a large bulk of the commercially important organic
chemicals. When a polymer is made up entirely of one monomer, it is called
a homopolymer.
A condensation reaction is a reaction where two (or more) molecules join
together to form one larger molecule and a small molecule typically water
being produced as a side product.

1.1.1

Step Growth Polymerization Polyamides (Nylons):

Polyamides are polymers where the monomer units are connected together
by amide groups (-C(=O)-NH-). Two generic schemes for polyamide
synthesis include condensation of diacid and diamine monomers in the bulk
state or at high concentrations.
The above reaction creates H2O as a byproduct, producing (n-1) moles of
water for n moles of repeat units. It turns out that the reaction above is at or
near equilibrium at low to moderate temperatures. To drive toward the
product, high temperature and very effective water byproduct removal must
be achieved for high polymer conversion.
A second approach is to use the much more reactive acid chloride group in
place of the acid. The reaction of diamines with diacid chlorides have
equilibrium constants that are about two orders of magnitude higher than
those of diamines with diacids. The reaction greatly favors the production of
amide product, and the reaction kinetics is extremely fast:
Here (n-1) moles of HCl is created as a byproduct. HCl can be neutralized by
the presence of weak base in the reaction solvent.
This second reaction is extremely rapid, and rather difficult to control in
moderate to high monomer concentrations. It is possible to accomplish a
polymerization of diamine and diacid chloride in a good solvent for both
monomers. On the other hand, the reaction is very fast, irreversible, and
Polymer Science Experiment

Author: 4
Synthesis of nylon 6,10

highly exothermic. The concentrations must be kept low, and the

temperature must also be controlled, often below room temperature, to
prevent overheating and side reactions. The solvent must be a good one not
only for the monomers, but for the resulting polymer, to achieve high
molecular weight.

1.1.2

Interfacial Polymerization:

A rapid, but more controlled approach is to take advantage of the fast

kinetics of the polymerization of diamines and diacid chlorides at the
interface between two immiscible phases. Interfacial polymerization involves
the reaction of monomer A dissolved in an organic phase with a monomer B
dissolved in an inorganic phase at the interface between the two nonmiscible phases. 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 one
where one phase is dispersed as tiny droplets in the other (continuous)
phase by using high speed stirring. This is called stirred interfacial
polymerization. Stirred interfacial polymerization is used to produce tiny
microcapsules (hollow inside) and microspheres (not hollow) for various
applications like controlled release of drugs and pesticides.

1.1.3

Unstirred interfacial polymerization of Nylon 6,10:

We shall study the reaction of 1,6 diamino hexane (HMDA) with diacid
chloride (sebacoyl dichloride-SC) to form Nylon 6,10. The polymer will form
at the interface between a layer of diamino hexane dissolved in water
(aqueous phase) and a layer of diacid chloride dissolved in dichloromethaneDCM (organic phase).

Polymer Science Experiment

Author: 5
Synthesis of nylon 6,10

The aqueous phase also contains sodium bicarbonate as a getter for HCl.

2HCl + Na2CO3 > 2NaCl + H2O+CO2

The denser organic phase forms the lower phase (chlorinated solvents are
used, which are denser than water) while the aqueous phase will be carefully
poured on top of the organic phase. Interfacial polymerization occurs
instantly forming a thin film of solid nylon 6,10 at the interface. The film at
the interface stops further reaction by preventing the monomers from
meeting each other (actually some monomers do reach other by diffusion
through the film but this is so slow that the film appears to have stopped
growing). The hydrochloric acid is rapidly neutralized by the carbonate in the
aqueous phase. If the nylon film is pulled up, out of the interface, new film is
formed continuously.
In contrast to reaction in the bulk, there is no need to control of the
stoichiometric ratio in this experiment. The stoichiometry at the interface is
controlled perfectly by the mass transfer controlled rate of diffusion and
consumption of each monomer species. In other words, in this diffusion
controlled situation, the monomer a to b ratio is essentially one to one.

Polymer Science Experiment

Author: 6
Synthesis of nylon 6,10

1.1.4

Safety, Handling, and Disposal

Wear your safety goggles, gloves, and lab coat while working in lab.
Hexamethylenediamine (1,6-diaminohexane) is irritating to the skin,
eyes, and respiratory system.
Sodium hydroxide is extremely caustic and can cause severe burns.
Contact with the skin and eyes must be avoided.
Sebacoyl chloride is corrosive and irritating to the skin, eyes, and
respiratory system.
Hexane and acetone are flammable. Both hexane and acetone vapors
can irritate the respiratory tract.
Should skin contact occur with any of these reagents, wash
contaminated area immediately.
Any unused polymerization mixture should not be poured into the sink
but should be stirred until no further polymer is formed. Any remaining
solvent/material will be disposed into a provided lab waste container.
The polymer should be washed extensively with alcohol and water to
get rid of HCl.

2. Equipment and Materials

2 Glass Beaker
Stirrer
Weighing Scale
Hexamethylenediamine
Sebacoyldichloride
Water
n-Hexane
Patri Dish

3. Methods and Procedures

3.1 Preparation of sample:
i)

1g Hexamethylenediamine weigh in a glass beaker with a

weighing scale and add 25ml of water in it.

Polymer Science Experiment

Author: 7
Synthesis of nylon 6,10

ii)

1g Sebacoyldichloride weigh on scale in separate beaker and add

25ml n-Hexane in it.

4. Procedure:
1. Stirrer both solutions until a homogeneous solution formed.
2. Pour the hexamethylenediamine into the sebacoyldichloride solution.
3. Pour it in such a way that by tilting the beaker and pouring slowly
along the walls of the beaker.
4. Pour half solution of hexamethylenediamine and wait for 5 min.
5. After 5 min again pour the remaining solution
6. Stay the beaker on a shelf for some time so that the reaction
completes.
7. After some time a third layer start forming between the two layers of
monomers.
8. Then put the stirre into the third layer and pull out it by wrapping on
the stirrer.
9. Continuously wrap the fiber of Nylon on stirrer and stay some time for
drying.
10.
Get out the both liquid layers from the beaker and stirrer the
nylon 6,10 layer and collect it in a patri dish.
11.

Carefully washed all the apparatus and put back on proper place

5. Results
I get the filament of the Nylon 6,10 on the stirrer in the form of rope.

6. Advantages

This process is at room temperature.

This is the fast process.
Very small amount of ingredients used in it.

Polymer Science Experiment

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Synthesis of nylon 6,10

7. Disadvantages

Large amount of solvent used

n-Hexane is very costly
n-Hexane is volatile and toxic

8. Reference

Class Lectures

Polymer Science Experiment