Nylon

Discovery Of Nylon:
It was discovered by W.H Carothers.
The term nylon was derived from ‘no-run’, the name
originally considered by its inventors to emphasize the
durability of ladies hosiery manufactured from it.
Definition:
Nylon is a man-made synthetic polymer, polyamide
filament or staple fibre made wholly from raw materials
from the minerals(coal, air and water). It contains atoms of
C, H, O and N.
Different Nylons: These are named depending on the
number of carbon atoms present in the molecule of raw
material.
Thus Hexamethylene Diamine(C=6) and adipic
acid(C=6) give Nylon 6,6.
H2N-(CH2)6-NH2 + HOOC-(CH2)4-COOH
Condensation

H2N-(CH2)6-NH-CO-(CH2)4-COOH + H2O
Condensation Polymerisation
…-NH-(CH2)6-NH-CO-(CH2)4-CO-…
Nylon 6,6 Or Polyamide 6,6
Amino Caproic Acid(C=6) gives Nylon 6.
H2N-(CH2)5-COOH Condensation Polymerisation -NH-(CH2)5-CO-NH-(CH2)5-CO-…
(Amino Caproic Acid) (Nylon 6 or Polyamide 6.)

Similarly, Nylon 7 and Nylon 11 are obtained from amino acids containing
7 and 11 carbon atoms per molecule respectively, while Nylon 6,10 is
made by HMDA and sebasic acid (C=10).
Manufacturing of Nylon 6,6: Raw materials are
Adipic acid & Hexamethylene diamine.

Adipic Acid:
An early method, starting from phenol, extracted from coal tar,
hydrogenating it to cyclohexanol and finally oxidising with HNO3 in presence
of metal catalyst.
Hexamethylene Diamine:
(i) From adipic acid: When it is subjected to a reaction called amination(with
ammonia in presence of boron phosphate catalyst at 350°C to 400°C
temperature) followed by dehydration, adiponitrile is produced.
HOOC-(CH2)4-COOH (Adipic Acid) Amination(350°-400°C), Ammonia vapour in presence of Boron Phosphate

NH4OOC-(CH2)4-COONH4 (Diammonium Adipate) Dehydration

NH2OC-(CH2)4-CONH2 + 2H2O (Adipamide) Dehydration

NC-(CH2)4-CN + 2H2O (Adiponitrile)

This can be reduced with hydrogen under pressure (600-625 atm. Pr.) at 125°C
in presence of Ni or Co catalyst.

H2N-(CH2)6-NH2
(Hexamethylene Diamine)
Production Of Nylon 6,6 Polymer salt from air, coal and water:

When AA and HMDA react with each other after mixing the solutions of both in
methanol, Nylon salt is precipitated, which is separated and purified at this stage.
Production of Nylon 6,6 Polymer(Polymerisation)
The purified Nylon salt is heated in an autoclave under high pressure. It
looses water and form hexamethylene adipamide which polymerises with
further elimination of water to give Nylon 6,6 Polymer.
H2N-(CH2)6-NH3-OOC-(CH2)4-COOH (Nylon Salt)
H2N-(CH2)6-NH-CO-(CH2)4-COOH + H2O (Hexamethylene Adipamide)
….HN-(CH2)6-NH-CO-(CH2)4-CO….(Nylon 6,6 Polymer)

When required DP is obtained which requires 4 hours at 280°C in an inert

atmosphere, polymerisation is stopped.
The molten polymer is casted into ribbons by forcing through a slit orifice,
solidified by spraying cold water on it as it passes over a rotating drum. The
product is then transferred to a disintegrator where it is cut into chips.

The chips obtained from different lots are mixed to ensure uniformity of the
final product and transferred to the spinning section.
Production of Nylon Polymer Chips:
Melt Spinning Drawing:
Melt Spinning:
The chips of Nylon polymer are fed through a hopper ‘A’ into a spinning
vessel, ‘B’ on an electrically heated grid ‘C’(Perforated Plate). The
perforations are so small that the chips do not pass through, but when
melted, the liquid can pass. The molten nylon is collected as a pool ‘D’ at
the bottom of the vessel. N2 is introduced into the vessel.
The molten polymer is kept at 288°C temperature and sucked by a pump
‘F’ into a spinnerette ‘E’ through a filter.
The molten polymer solidifies as soon as it emerges out of the
spinnerette by passing cold air in the cooling zone ‘G’.
The filaments are passed through steam chamber ‘H’, to wet them for
dimensional stability thereafter winding them on a bobbin, ‘L’.
Drawing: Nylon filaments as obtained are not very strong because it
contains a large number of unoriented molecules and these must be
oriented so as to lie parallel to the length of the fibre to develop full
strength.
For this, they are drawn 4-7 times their original length.
Manufacturing Of Nylon 6:
Other methods to synthesize Caprolectum
Polymerisation: This is carried out in an autoclave at 240-270°C under high
pressure. A high viscosity molten polymer consisting of 89-92% of the
polymer and 8-11% of unconverted caprolactum, collects at the bottom.
Acetic acid or Adipic acid is used to stop the polymerisation at a particular
stage to obtain a desired viscosity. Relatively volatile caprolactum is removed
by evaporation under reduced pressure.
Spinning Of Nylon 6 Yarn:
Melt Spinning:
POLYESTER
 DEFINITION
• Polyester fibres are synthetic textile fibres
which are obtained by:
1. Estrification of dicarboxylic acid with glycols
or glycol derivatives (dacron)
2. By ester exchange reaction between
dicarboxylic esters & glycols(Terylene)
• Dacron: it is made by polymerization reaction
using terephthalic acid and ethylene glycol .
 n HOOC COOH +n HO- CH2-CH2-OH

OH OC COO-CH2-CH2 O H+
n
(2n-1) H2o
• Terylene: It is made by polymerization using ester
exchange reaction between dimethyl terephthalate
(DMT) and ethylene glycol.
CH2-OH
n H3COOC COOCH3 + n
CH2-OH

H3CO OC COO-CH2-CH2 O H+
n
(2n-1) CH3- OH
• Raw materials: Terephthalic acid or dimethyl
terephthalate & ethylene glycol.
1. (a) Terephthalic acid

The use of DMT is preferred as the purity of the

reactant is essential and it is easier to purify
DMT than terephthalic acid.
2. Ethylene glycol : it is made from ethylene after
converting it into either ethylene oxide or
chlorohydrin.
 Polymerization
• The Terephthalic acid or ester and ethylene glycol
are polymerized at high temperature and
atmospheric pressure . It is completed in two
stages :
1. Ester exchange : carried out at atmospheric
pressure, starting at a temperature just above the
melting point of DMT and ending at a temperature
above 200 degree centigrade. During this, mixture
of DMT and excess glycol produce low polymers.
HCl is used to speed up the reaction.
• Poly condensation : low polymer (DGT) are
heated to 270 degree Celsius for 30 minutes at
atm. Pressure and then 10 hrs. under vacuum.
The ester polymerises into high polymer . This
high polymer is a hard white substance melting
at 256 degree centigrade and has a MW of
8000-10000.