EXPERIMENT 1

Condensation Polymerization

1.0 Objective:

To synthesize Nylon 6,6 via step-growth polymerization and to examine the physical
properties of the polymer.

1.1 Introduction:

Condensation or step growth polymerization involves generally involve either one or

more types of monomers. In either case, each monomer has at least two reactive
(functional) groups. In the process, usually a small molecule such as water or ammonia,
is eliminated.

In this experiment Nylon 6,6 is prepared by Interfacial Polymerizations using a diamine

(hexamethylenediamine) and a diacid chloride (sebacyl (or Sebacoyl) chloride).

H2N(CH2)6NH2 + ClCO(CH2)4COCl
hexamethylenediamine adipoyl chloride

The reaction is done in a two-phase system where the amine is dissolved in water, and
the diacid chloride in an organic solvent. The two solutions are immiscible and the
polymerizations take place at the interface where the diacid chloride and diamine meet.

Many diamines and diacids (or diacid chlorides) can be reacted to make other
condensation products that are described by the generic name "nylon." The word "nylon"
is used to represent synthetic polyamides. Nylons are one of the most common
polymers used as a fiber. The various nylons are described by a numbering system that
indicates the number of carbon atoms in the monomer chains. For example, nylons from
diamines and dicarboxylic acids are designated by two numbers, the first representing
the diamine and the second the dicarboxylic acid.
Nylon 6,6 is a long molecular chain with denser structure. It exhibits the highest melting
point (256C) of all synthetic fibers. Therefore, it is the most heat and friction resistance
and an excellent choice for making carpet, apparel, airbags, tyres, ropes, conveyor belts,
hoses, etc.

1.2 Materials:

20% NaOH
5% aqueous solution of hexamethylenediamine, H2N(CH2)6NH2
0.25 M adipolychloride in cylohexane
80% formic acid

1.3 Apparatus:

50 ml beaker
Pipet
Tweezers

1.4 Safety Precaution:

All work should be done in the hoods. Do not handle the nylon until it has been
thoroughly washed. It may caused irritation to the skin, eyes and mucous membranes.

1.5 Procedure:

a) Add 2 ml of 20% NaOH solution and 10 ml of hexamethylenediamine in a 50 ml

reaction beaker.
b) Draw 10 ml of 0.25 M of adipoly chloride solution in cylohexane into a pipet and
carefully layer this solution on top of the aqueous solution in the beaker.
c) Leave the solutions for several minutes to allow the polymerizations to take
place.
d) Slowly lift and gently wind the nylon fiber obtain at the center of the two solutions.
Tip the beaker slightly and continue to pull the fiber.
 e) Wash the nylon thread thoroughly with water and let it dry on a clean paper
towel.
f) Weigh your product of nylon 6,6.
g) Dissolve a small amount of nylon in 80% formic acid. Place a few drops of the
solution onto a microscope slide and allow the solvent to evaporate under the
hood.
h) Observe and compare the structure of the nylon thread and the nylon film under
a miscroscope

1.6 Data analysis:

a) Describe the physical properties of the nylon thread.

b) Compare the appearance of the solvent cast nylon film with that of the nylon
thread.
c) Compare the structure of the solvent cast nylon film with that of the nylon
thread using optical microscope.
d) Determine the molecular weight of your nylon thread.

1.7 Questions:

a) Give the structure of Nylon 6,6. and state the molecule that has been eliminated
in the polymerization.
b) Name the type of condensation polymerization for the preparation of Nylon 6,6.
c) Suggest the monomer(s) for the polymerization of Nylon 6,10
d) Name the type of condensation polymerization for the preparation of Nylon 6.
e) i) Draw the structure of a polymer obtained from the polymerization of
sebacoyl chloride, ClCO(CH2)8COCl and ethylene glycol, HO(CH2)2OH.
ii) What are the molecules that have been eliminated in this condensation
reactions.
iii) Classified the polymer obtained based on its interlinkage unit.
 CHM 572
EXPERIMENT 2
REPORT SHEETS

Name :

Group Members : 1.
2.
3.

Date of Experiment :
2.0 Objective:
Write the objective of the experiment:

2.1 Procedure:
Summarized your procedure in a form of flow chart.
2.2 Results and Discussions:

a) Weight of nylon 6,6 obtained = ______ g

b) Describe the physical properties of the nylon thread.

c) Compare the appearance of the solvent cast nylon film with that of the nylon
thread.

d) Compare the structure of the solvent cast nylon film with that of the nylon
thread. Paste the optical micrographs of both nylon thread and nylon film.
 e) Determine the molecular weight of your nylon thread.

2.3 Conclusions:
Conclude or give any comments on the results obtained from the experiment.

2.4 Questions:

a) Give the structure of Nylon 6,6. and state the molecule that has been eliminated
in the polymerization.

b) Name the type of condensation polymerization for the preparation of Nylon 6,6.

c) Suggest the monomer(s) for the polymerization of Nylon 6,10

d) i) Draw the structure of a polymer obtained from the polymerization of
sebacoyl chloride, ClCO(CH2)8COCl and ethylene glycol, HO(CH2)2OH.

ii) What are the molecules that have been eliminated in this condensation
reactions.

iii) Classified the polymer obtained based on its interlinkage unit.