Chapter 3 Polyester:
Polyester:
The word “ester” is the name given to salts formed from the reaction between an alcohol and
acid. “Polyester” means many organic salts. Polyester is a man made, synthetic polymer,
polyester filament or staple fibre.
Polyester fibre are chemically composed of at least 85% by wt. of an ester of a substituted
aromatic carboxylic acid, including but not restricted to substituted Terephthalate units and
Para substituted hydroxybenzoate units.
Polyethylene Terephthalate, the repeating unit of the polyester polymer with a degree of
polymerisation of 115-140 units (i.e. n= 115-140).
COO C
H2
O C
Manufacturing process:
1. Continuous process of PET:
Raw mtls:
The main raw mtls required for the manufacture of polyester fibre are P-xylene, ethylene glycol
and methanol.
1) Terephthalic acid or D.M.T:
Terephthalic acid is made by oxidizing P- xylene with air and nitric acid.
CH3 CH3 COOH
Air
HNO3
CH3 COOH COOH
Terephthalic acid is esterified with methyl alcohol to form Dimethyl terephthalate (DMT).
COOH COOCH3
CH3OH
COOH COOCH3
2) Ethylene glycol:
Ethylene glycol is made by catalytic oxidation of ethylene.
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CH2 H2C CH2
[O] H2O H2C OH
CH2 O H2C OH
Ethylene oxide Ethylene glycol
Polymerization:
PET is produced by condensing ethylene glycol with Terephthalic acid or Dimethyl
terephthalate.
Condensation of Ethylene Glycol with DMT is an ester interchange reaction, methyl alcohol
eliminated as the reaction takes place.
In either case, the condensation is carried out by heating the ethylene glycol and Terephthalic
acid and removing the water or methyl alcohol in Vacuum. When the desired degree of
polymerisation has been reached, colorless polyester is extruded through a slot on to a casting
wheel. The polymer solidifies into an endless ribbon which is fed to cutter and cut into chips.
The chips are dispatched to the spgn room via a suction pipe.
Spinning:
PET melts at about 2600C, and the molten polymer is stable. In
spinning, the chips of polymer are dried to remove moisture and then passed to storage hoppers.
From the hoppers the chips are fed as required to the spinning m/cs. In spinning, the molten
polymer from hopper is pumped through holes in a spinneret. Then filaments emerge and
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solidify and are wound into packages of undrawn yarn. The undrawn yarn is stretched to about 5
times its original length on draw-twist m/cs then the drawn filament is wound.
In case of staple fibre production, the filaments from spinning head are passed through draw
rollers, and the crimped mechanically and the crimp is set in the fibre by heat treatment. The tow
is then cut into staple of the desired length.
Reaction in polymerization of PET polyester:
COOH
H2C OH Polymerisation
n +n HO OC COO-(CH2)2-O H + (2n-1) H2O
H2C OH
n
COOH
PET
Terephthalic acid Dacron (USA)
COOCH3
CH2OH
Polyn
n + n CH3O co COO(CH2)2O H
CH20H n
PET
COOCH3
+ (2n-1)CH3OH
Terelene ( UK)
2. Batch process:
The raw mtls required for the manufacturing of polyester fibres are Dimethyl Terephthalate and
Ethylene glycol.
1. Terephthalic acid is esterified with methyl alcohol to form DMT.
COOH COOCH3
+ CH3OH + H2O
COOH COOCH3
2. Ethylene glycol is made by catalytic oxidation of ethylene
CH2 [O] H2C CH2 H2O H2C OH
CH2 H2C OH
O
This process is performed in two stages:
1) Ester interchange
2) Polycondensation
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1) Ester interchange reaction is occurred by mixing DMT with excess EG with catalyst (0-
1.4%) by heating of temp of 130-250oC and removing CH3OH.
COOCH3
H2 H2
H2C OH
+H C HO C C OOC COO C C OH + CH OH
3
OH H2 H2
2
COOCH3
2) Polycondensation reaction,
Polyn O
HO (CH2)2 OOC COO (CH2)2 HO CH3O C COO (CH2)2O H
By collecting polymer of chips with pressure 0.1 mm Hg. Polymer are kept spinneret for
spinning.
Impurities of polyester: 2 impurities present in polyester fibre.
I) A small part of ethylene glycol used in the synthesis is converted to diethyl
glycol.
H2
H2C OH H2C O CH2 C OH
2
H2C OH H2C OH
DEG
and from this there occur in the polyester a few (1-3%) groups such as:
OCH2CH2OCH2CH2OO CO
which contain an ether linkage.
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II) The other impurity present to the extent of 1.5% in the polymer is cyclic trimer
(R= -COOC2H4OOC-)
R R
This can be washed out during fabric dyeing.
Commercial or Trade name:
Trade name Country
Dacron USA
Terylene UK
Fortrel USA
Tetoron Japan
Trivera Japan
Pentron Japan
Lambda USA
Modification process of polyester:
Polyester fibre has some properties which are not available in natural fibre, such as they have
low MR%, so less use as apparel and dyeing of these fibre are difficult due to higher
crystallinity. To remove this problems different radical are added chemically to it and new
polyester with new properties.
I) By organic acid: (gives an affinity for Acid dye)
Modification is carried out by using a dibasic organic acid,
H2C OH
HOOC COOH + HOOC (CH2)6 COOH +
H2C OH
Sebasic acid
O
C OOC (CH2)2 COO (CH2)6 OOC (CH2)2 O
Modified polyester
II) By sulpho isophthalic acid:(gives an affinity for basic dye)
For modification, sulpho isophthalic acid is used as following,
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HOOC COOH
H2C OH
HOOC COOH + +
H2C OH
HO3S
O
C OOC (CH2)2 COO OOC (CH2)2 O
HO3S
Types of polyester:
Polyesters are subdivided into the following types, based upon their chemical structures and
abbreviations shown are used in referring to the fibres:
1) Polyethylene Terephthalate fibre (PET polyester)
2) Poly- 1,4- cyclo hexylene Dimethylene Terephthalate fibres (PCDT polyester fibres)
3) Other types of polyester fibres.
1. PET polyester:
PET is made by the condensation of Terephthalic acid or a derivative such as dimethyl
terephthalate with ethylene glycol.
COOH COOCH3
+ CH3OH + H2O
COOH COOCH3
COOCH3
H2
H2C OH
COO C C OH
+H C 2 OH
HO (CH2)2 OOC
H2
Diethylene Glycol Terephthalate
COOCH3
O(CH2)2OOC COO(CH2)2OOC COO(CH2)2O
PET
2. PCDT:
PCDT polyester fibres are spun from poly -1,4- cyclo hexylene dimethylene terephthalate made
by condensing Terephthalic acid with 1,4- cyclo hexane dimethanol,
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H2 H2
C C
HOOC COOH + HOH2C CH
CH CH2OH
CH2 C
H2
1,4-Cyclo hexane dimethanol
H2 H2
C C
O CH2 CH
CH C COO CO
H2 n
C C
H2 H2
PCDT
3. Special type of polyester fibre:
Dacron:
The fibres are made by the polymerisation of Terephthalic acid and ethylene glycol.
n COOH COOH + n HO-(CH2)2OH
OH OC COO(CH 2)2O H + (2n-1)H2O
n
Dacron
Terylene: Terylene is made by polymerizing the dimethyl terephthalate and ethylene glycol.
COOCH3
H2C OH
+ n
H2C OH
COOCH3
H2
H3CO C
O
COO C C
H2
O H
+ (2n-1)CH3OH
n
Terelene
Kodel: It is polymerization of 1,4- cyclo hexane dimethanol and terephthalic acid.
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H2 H2
C C
HOOC COOH + HOH2C CH
CH CH2OH
CH2 C
H2 H2
H2
C C
H2
H O CH2 CH
CH C COO CO OH
C C
H2 H2
Kodel
n
+ 2nH2O
Difference between Dacron & Terylene:
Dacron Terylene
1. It is the Trade name of USA 1. It is the trade name of US.
2. Monomer is TPA and EG 2. Monomer is DMT and EG
3. H2O is eliminated. 3. Methanol eliminated.
4. Chemical reaction. 4. Chemical reaction.
Feature of polyester fibre:
Diameter: 12 µm to 25 µm.
Appearance: Smooth with round cross-section.
Moisture regain: 0-0.4% (Hydrophobic for extreme crystallinity).
Shrink away from flame.
Disperse, Acid,Basic,azoic, some pigments are used for dyeing fibre.
Polymer system:
The polyester polymer is linear and is usually based on Polyethylene Terephthalate. The degree
of polymerisation range from about 115 to 140 resulting in a polymer length of about 120 nm to
150 nm with a thickness of about of 0.6 nm.
The important chemical groups in the polyester polymer are the methylene groups (-CH2-), the
slightly polar carbonyl groups (-CO-), and the ester groups (-OCO-).The polymer system is
estimated to be about 65-85% crystalline and about 35-15% amorphous. This is supported by the
hydrophobic nature, poor dye ability, but good overall chemical resistance of polyester filaments
or staple fibres.
O O O O O
C C O (CH2)2 O C C O (CH2)2 O C C O
O n
ester group ethylene glycol terephthalate unit
Fig: A section of polyester polymer.
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Monomer of polyester:
Monomer Polymer
1. The monomer of most common polyester are Polyethylene terephthalate
ethylene glycol O
H2C OH O C COO (CH2)2
n
H2C OH
and Terephthalic acid
COOH
COOH
1,4 cyclo hexane dimethanol
2. 1,4 cyclo hexane dimethanol Poly-1,4- cyclohexylene-Di
methylene
H2 H2
C C Terephthalate (PCDT polyester)
HOH2C CH H2 H2
CH CH2OH
C C
CH2 C COO CO
H2 O CH2 CH
CH C
and Terephthalic acid C C
H2
COOH
H2 H2 n
COOH
Physical properties:
1. Tenacity:
Polyester filaments and staple fibres are strong to very strong because of their extremely
crystalline polymer system. The tenacity of polyester filaments or staple fibres remains unaltered
when wet because of the completely hydrophobic and extremely crystalline polymer system.
High tenacity filament 7-8 gm/den.
Normal tenacity filament 4.5-5.0”
2.Hygroscopic nature:
Polyester filaments and staple fibre are hydrophobic. The lack of polarity and the extremely
crystalline structure of polyester polymers resist the entry of water molecules into the polymer
system. MR% - 0-0.4%.
Chemical properties:
1. Effect of acid:
The ester groups of the polyester polymers are resistant to acid hydrolysis. This resistance is
further enhanced by the extreme crystallinity of the polyester polymer system which prevents the
entry of any acid and water molecules into the filament of staple fibre.
2. Effect of alkali:
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Sensitive to alkali.
3. Effect of bleaches:
Normally polyester textile mtls do not need to be bleached. If bleaching is required this is
achieved by using hypo chloride bleaching.
4. Sunlight:
The acid resistance of polyesters helps protect polyester textile mtls from the slightly acidic
conditions that occur in polluted atmospheres. The benzene rings of the polyester polymer
provide stability to the whole polymer, enabling the polymers to withstand the detrimental effect
of the sun’s ultra violet radiation.
5. Dye ability:
It is very difficult for dye molecules to penetrate the extremely crystalline polymer system of
polyester fibres.
6. Biological agents:
Resistance to moths, mildews, fungus.
7. Flammability: Burn slowly.
End use of polyester:
The polyester fibres are wrinkle free appearance and ease of care in use. Fabrics resist
wrinkling. It requires little or no ironing are easy to launder and quick to dry.
I) Apparel use:
Men’s, women’s, children’s wear, tropical suiting, blending with cotton, wool, acrylic, nylon
etc. for dress goods and other purposes.
II) Domestic use:
floor covering, carpet etc.
III) Industrial use:
High tenacity PET for tire cords, v-belt, ropes, fire hoses, sail cloth, conveyor belts, paper
making.
Use of polyester higher than any other synthetic fibre:
The use of polyester is higher than any other synthetic fibre due to low cost, more durable, no
fading, easy care, no ironing.
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