FACULTY OF APPLIED SCIENCE

BACHELOR OF SCIENCE (HONS.) POLYMER TECHNOLOGY

INTRODUCTION TO POLYMER INDUSTRY (FSG567)
ASSIGNMENT 1
THE PRODUCTION OF NYLON 6, 6 IN THE POLYMER INDUSTRY

NAME : NUR AFIQAH BINTI MOHD RADZI

MATRIX NO : 2019848282
GROUP : AS2433
LECTURER NAME : RADIN SITI FAZLINA NAZRAH HIRZIN (DR.)
DATE OF SUBMISSION : 17 April 2020
Introduction

Nylon-6,6 (polyhexamethylene diamine adipamide) is a polyamide made from adipic

acid and hexamethylenediamine by polycondensation. The resulting polymer is
extruded into a wide range of fiber types. The fibers are drawn, or stretched, in a
process that increases their length and reorients the material’s molecules parallel to one
another to produce a strong, elastic filament. The thermo-plasticity of nylon permits
permanent crimping or texturing of the fibers and provides bulk and stretch properties.
This fibres are mainly used in many applications, including fabrics, bridal veils, carpets,
musical strings and rope. They are also come in many types, which is for textile and
plastic industries.
The nylon developed by Carothers at Du Pont was nylon-6, 6. Because of the
importance of starting out with equal amounts of the two reactants, salts of the diamine
and of the diacid are made and then used in the commercial synthesis of nylon-6, 6.

Figure 1: Synthesis of polyamide from hexamethylene diamine and adipic acid

METHOD OF POLYMERIZATION (Step-Growth Polymerization)

1. DEHYDRATION OF AMMONIUM SALT

Hexamethylene diamine and adipic acid are form the complex salt 1:1 hexamethylene
ammonium adipate. Direct polycondensation of diamine and dicarboxylic acid which are
Commercial aliphatic polyamides are generally produced by a simple direct polycondensation of
a diacid and a diamine. Direct polycondensation of an equimolar amount of the two monomers
can produce a high molecular weight polymer based on Figure 1.

Condensed water was removed using a vacuum, and impurities and catalyst are removed by
purification. The resulting polyamide has high thermomechanical properties. Acid catalysts such
as sulfuric acid or sulfonic acid are sometimes required to promote the polycondensation, such
as in the synthesis of high molecular weight aromatic polyamides. However, the polymerization
of these simple mixtures is not always efficient due to oxidation, vaporization, or side reactions,
which change the 1:1 stoichiometric ratio of diamine and diacid that required producing a high
molecular weight polyamide. The direct polymerization can also be performed in solution. Acetic
acid was added as the molecular weight control during reaction.

Melt polymerization of salt monomers which is nylon salts is used to overcome the stoichiometry
problems of the direct methods for preparing polyamides. The salt state of the monomers
precludes their vaporization at the high temperature of the polycondensation in order to maintain
their 1:1 stoichiometry. The salt is formed as a white powder immediately after mixing equimolar
amounts of the diacid and diamine in an alcoholic solution. After filtration of the white powder,
salt monomer is obtained in very high yields of >90 wt%. If the salt monomer is dried, it can be
used directly for polymerization in a sealed reaction tube at a temperature slightly higher than
the salt’s melting point. In the melt state of the salt, water is produced as steam. This water
should be removed under vacuum to reach high degrees of polymerization. Salt-state
polymerization is generally a kind of melt polymerization; but solid-state polymerization is also
possible when the melting points of the produced polymers are higher than the reaction
temperature. Salts of hexamethylenediamine and sebacic acid or adipic acid can be melt-
polymerized to form Nylon-6, 6, respectively.

.
Step 1: An adipic acid molecules protonates the carbonyl oxygen of another adipic acid
molecules
Step 4: The dimer can react with another molecule of the diacid, as above or it can react with
another molecules of diamine.

Formation of nylon 6,6

2. Interfacial Polymerization
 Figure
2

Interfacial Polymerization is occurs by using the reaction between adipoyl chloride and
hexamethylene diamine to synthesize the polyamide nylon-6, 6. The texture, making it difficult to
properly line up the broken pieces. When mixed, the condensation reaction proceeds and a thin
film is formed at the interface of both solvents. This thin film continues to grow until stopped
when slowly pulled from the interface. The nylon-6, 6 had a pale yellow-white. The product had
a dry texture, making it difficult to properly line up the broken pieces.

Nylons form at the interface of the immiscible solutions because neither of the reagents is
soluble in the other solvent. In addition, the nylon polymer will not soluble in either solvent. The
‘rope’ pulled from the interface is actually a column of nylon filled with solvent and reagents.
After washing and drying, the strand is considerably smaller in diameter. It lacks the strength of
something like monofilament fiber because the molecules in our nylon sample have not been
oriented by stretching. In addition, the molar mass of nylon is probably considerably lower than
of a commercial sample. So, it will have low molecular weight of nylon-6, 6.

The acid chloride and amine react and are joined in a condensation process with loss of the
small molecule HCl. The product contains a newly formed amide bond (Figure 2). The resulting
product has both an acid chloride and amine functional group that can react with molecules of
hexamethylenediamine and adipoyl chloride, respectively. This process continues until all the
reagents have reacted to form Nylon 6, 6 polymers.

The solution will be layered of adipoyl chloride in cyclohexane onto an aqueous basic solution of
hexamethylenediamine. Because cyclohexane and water are immiscible, a two-layer system will
result. The polymerization will take place at the cyclohexane-water interface. Sodium hydroxide
is added to the reaction mixture to aid in the amide formation.

CONCLUSION
As a conclusion, the best method to produce nylon-6, 6 is dehydration of ammonium salt. A
high molecular weight nylon-6, 6 is only obtained if equimolecular amounts of the components
are used. An excess of components would terminate the chain by formation of an acid or amino
end group. So, stoichiometric potions of hexamethylene diamine and adipic acid must be used
(amine to acid of 1:1). This is a formation of salt from hexamethyl diamine and adipic acid which
is required to produce a high molecular weight polyamide. Direct polycondensation of an
equimolar amount of the two monomers can produce a high molecular weight polymer.

The process involve the formation of salt and the step polymerization of nylon-6, 6 involve the
heating process of salt at high temperature in vacuum. So, there have a high temperature
during this process that contributes to the high molecular weight. So, it will produce a high
molecular weight of nylon-6, 6.

Reference

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