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Polyesters - A Review

Technical Report · March 2017

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Neethu N Amisha Kumari

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Chemistry project
POLYESTER

SUBMITTED BY,

AMISHA KUMARI SC16B006

NEETHU N SC16B034

PALAPARTHI ALEKHYA SC16B096

SHALINI SINGH SC16B110

JUREDDY CHINMAI SAI SC16B128

10th March, 2017

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ACKNOWLEDGEMENT

We would like to express our sincere gratitude to Indian

Institute of Space Science and Technology for providing us
the opportunity to carry out a study on ​POLYESTERS​. We
take this opportunity to thank the faculty and staff ,
Department of Chemistry, IIST for their constant support
and encouragement throughout the course of this project.
Special thanks are due to Dr.Nirmala Rachel James, Head
of the Department, for her able guidance and help at every
stage. We would also like to thank all our teachers,
classmates and friends for all the help they have rendered
towards the successful completion of this project.

Thank You.

Amisha Kumari

Neethu N

Palaparthi Alekhya

Shalini Singh

Jureddy Chinmai Sai

3

​CONTENTS

SL NO TOPIC PAGE NO.

1. Introduction 4

2. History 5

3. Categories 7

4. Synthesis 8

5. Types of Polyesters 10

6. Polyethylene Terephthalate 13

7. Polyethylene Naphthalate 17

8. Space Applications 19

9. Disadvantages of Polyester 20

10. Impacts on the environment 20

11. Some Biodegradable Polyesters 23

11. Bibliography 24
4

INTRODUCTION
Polyester​ ​is a category of ​polymers​ that contain the ​ester
functional group​ in their main chain.

Polyesters include naturally occurring chemicals, such as in

the ​cutin​ of ​plant cuticles​, as well as synthetics through
step-growth polymerization​ such as ​polybutyrate​.

As a specific material, it most commonly refers to a type

called​ ​polyethylene terephthalate​ (PET) ​because it is
made up of ethylene groups and terephthalate groups.
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HISTORY

In 1926, United States-based E.I. du Pont de Nemours and

Co. began research into very large molecules and synthetic
fibers. This early research, headed by W.H. Carothers,
centered on what became nylon, the first synthetic fiber.

Soon after, in the years 1939-41, British research chemists

took interest in the du Pont studies and conducted their
own research in the laboratories of Calico Printers
Association, Ltd. This work resulted in the creation of the
polyester fiber known in England as Terylene.

In 1946, du Pont purchased the right to produce this

polyester fiber in the United States. The company
conducted some further developmental work, and in 1951,
began to market the fiber under the name Dacron.
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During the ensuing years, several companies became

interested in polyester fibers and produced their own
versions of the product for different uses.
Today, there are two primary types of polyester, PET
(polyethylene terephthalate) and PCDT (poly-1,
4-cyclohexylene-dimethylene terephthalate). PET, the more
popular type, is applicable to a wider variety of uses. It is
stronger than PCDT, though PCDT is more elastic and
resilient. PCDT is suited to the heavier consumer uses,
such as draperies and furniture coverings. PET can be used
alone or blended with other fabrics to make clothing that is
wrinkle​ and stain resistant and retains its shape.
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CATEGORIES

Depending on the chemical structure, polyester can be a

thermoplastic​ ​or​ ​thermoset​. There are also p
​ olyester
resins​ ​cured by hardeners; however, the most common
polyesters are thermoplastics.Polyesters as thermoplastics
may change shape after the application of heat. While
combustible at high temperatures, polyesters tend to shrink
away from flames and self-extinguish upon ignition.

Polyester as fibers​ have high ​tenacity​ and ​E-modulus​ as

well as low water absorption and minimal ​shrinkage​ in
comparison with other industrial fibers.Polyester fibers are
sometimes spun together with natural fibers to produce a
cloth with blended properties

Polyester can also be classified as saturated and

unsaturated polyesters. ​Saturated polyesters​ refer to that
family of polyesters in which the polyester backbones are
saturated. They are thus not as reactive as unsaturated
8

polyesters. They consist of low molecular weight liquids

used as plasticizers and as reactants in forming urethane
polymers, and linear, high molecular weight thermoplastics
such as polyethylene terephthalate (Dacron and Mylar).
Usual reactants for the saturated polyesters are a glycol
and an acid or anhydride.
Unsaturated polyesters​ refer to that family of polyesters in
which the backbone consists of alkyl thermosetting resins
characterized by vinyl unsaturation. They are mostly used
in reinforced plastics. These are the most widely used and
economical family of resins.​ ​Unsaturated polyesters​ (UPR)
are thermosetting ​resins​.

SYNTHESIS
Synthesis of polyesters is generally achieved by a
polycondensation reaction.The general equation for the
reaction of a diol with a diacid is :
(n+1) R(OH)​2​ + n R´(COOH)​2​ → HO[RO-OCR´COO]​nR-OH
​
+ 2n H​2O
​

Azeotrope esterification
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In this classical method, an ​alcohol​ and a ​carboxylic acid

react to form a carboxylic ester. To assemble a polymer,
the water formed by the reaction must be continually
removed by A​zeotrope​ distillation.

Alcoholic transesterification

An alcohol-terminated oligomer and an ester-terminated

oligomer condense to​ form an ester linkage, with loss of an
alcohol. R and R' are the two oligomer chains, R'' is a
sacrificial unit such as a ​methyl group​ (​methanol​ is the
byproduct of the esterification reaction).

Acylation (HCl method)

The acid begins as an acid chloride, and thus the

polycondensation proceeds with emission of ​hydrochloric
acid​ (HCl) instead of water. This method can be carried out
in solution or as an ​enamel​.
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Silyl method
In this variant of the HCl method, the carboxylic acid
chloride is converted with the trimethyl silyl ether of the
alcohol component and production of trimethyl silyl
chloride is obtained.

Ring-opening polymerizatio​n

Aliphatic​ polyesters can be assembled from ​lactones​ under

very mild conditions, catalyzed ​anionically​, ​cationically​ or
metallorganically. A number of catalytic methods for the
copolymerization of epoxides with cyclic anhydrides have
also recently been shown to provide a wide array of
functionalized polyesters, both saturated and unsaturated.
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TYPES OF POLYESTERS

According to the composition of their main chain,

polyesters can be:
Main chain Type Examples of

compositi Polyesters Manufacturing methods

on

Aliphatic Homopo Polyglycolide​ or Polycondensation​ of g

​ lycolic
lymer polyglycolic acid acid
(PGA)

Polylactic acid Ring-opening polymerization

(PLA) of l​ actide

Polycaprolactone Ring-opening polymerization

(PCL) of c​ aprolactone

Polyhydroxyalkano
ate​ (PHA)

Polyhydroxybutyra
te​ (PHB)

Copolym Polyethylene
er adipate​ (PEA)

Polybutylene Polycondensation of ​succinic

succinate​ (PBS) acid​ with ​1,4-butanediol
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Poly(3-hydroxybut Copolymerization​ of
yrate-co-3-hydroxy 3-hydroxybutanoic acid​ and
valerate)​(PHBV) 3-hydroxypentanoic acid​,

butyrolactone​, and
valerolactone​ (oligomeric
aluminoxane​ as a catalyst)

Semi-ar Copolym Polyethylene Polycondensation of

omatic er terephthalate terephthalic acid​ with
(PET) ethylene glycol

Polybutylene Polycondensation of
terephthalate terephthalic acid with
(PBT) 1,4-butanediol

Polytrimethylene Polycondensation of
terephthalate terephthalic acid with
(PTT) 1,3-propanediol

Polyethylene Polycondensation of at least

naphthalate​ (PEN) one n​ aphthalene​ ​dicarboxylic
acid​ with ethylene glycol

Aromati Copolym Vectran Polycondensation of

c er 4-hydroxybenzoic acid​ and
6-hydroxynaphthalene-2-carb
oxylic acid
13

POLYETHYLENE TEREPHTHALATE

Polyethylene terephthalate commonly abbreviated PET or

PETE is the most common ​thermoplastic ​polymer resin of
the ​polyester family and is used in ​fibers for clothing,
containers for liquids and foods, ​thermoforming for
manufacturing, and in combination with glass fiber for
engineering ​resins​.It may also be referred to by the brand
name Dacron, Terylene or Lavsan.

The majority of the world's PET production is for synthetic

fibers (in excess of 60%), with bottle production accounting
for about 30% of global demand. In the context of textile
applications, PET is referred to by its common name,
polyester​, whereas the acronym PET is generally used in
14

relation to packaging. Polyester makes up about 18% of

world polymer production and is the fourth-most-produced
polymer​.

PET consists of ​polymerized units of the monomer ethylene

terephthalate, with repeating (C​10H​
​ 8O​
​ 4)​ units. PET is
commonly ​recycled​, and has the number "1" as its ​recycling
symbol​.

SYNTHESIS AND PROCESSING

The monomer ​bis(2-hydroxyethyl) terephthalate can be

synthesized by the ​esterification reaction between
terephthalic acid and ​ethylene glycol with water as a
byproduct, or by ​transesterification reaction between
ethylene glycol and ​dimethyl terephthalate with ​methanol
as a byproduct. Polymerization is through a
polycondensation reaction of the monomers (done
15

immediately after esterification/transesterification) with

water as the byproduct.

PHYSICAL PROPERTIES

PET in its natural state is a colorless, semi-crystalline resin.

Based on how it is processed, PET can be semi-rigid to
rigid, and it is very lightweight. It makes a good gas and fair
moisture barrier, as well as a good barrier to alcohol
16

(requires additional "barrier" treatment) and solvents. It is

strong and ​impact-resistant​.

USES

Because PET is an excellent water and moisture barrier

material, plastic bottles made from PET are widely used for
soft drinks​.

Biaxially oriented PET film (often known by one of its trade

names, "Mylar") can be aluminized by ​evaporating a ​thin
film of metal onto it to reduce its permeability, and to make
it reflective and opaque (​MPET​). These properties are
useful in many applications, including flexible food
packaging​ and ​thermal insulation​.

Because of its high mechanical strength, PET film is often

used in tape applications, such as the carrier for ​magnetic
tape​ or backing for ​pressure-sensitive adhesive tapes​.

Non-oriented PET sheet can be ​thermoformed to make

packaging trays and ​blister packs​. If crystallizable PET is
17

used, the trays can be used for ​frozen dinners​, since they
withstand both freezing and oven baking temperatures.

PET is also used as a substrate in thin film solar cells.

Terylene is also spliced into bell rope tops to help prevent

wear on the ropes as they pass through the ceiling.

POLYETHYLENE NAPHTHALATE

Polyethylene naphthalate (poly(ethylene 2,6-naphthalate

or PEN) is a ​polyester with good barrier properties (even
better than ​Polyethylene terephthalate​). Because it
provides a very good oxygen barrier, it is particularly
well-suited for bottling beverages that are susceptible to
oxidation, such as ​beer​. It is also used in making high
performance ​sailcloth​. It also has been found to show
18

supreme scintillation properties and is expected to replace

classic plastic ​scintillators​.

PRODUCTION
PEN is a polyester polymer of ​naphthalene-2,6-dicarboxylic
acid​ and ​ethylene glycol​.

There are two major manufacturing routes for PEN, i.e. an

ester or an acid process, named according to whether the
starting monomer is a diester or a diacid ​derivative of
naphthalene​, respectively. In both cases for PEN, the glycol
monomer is ethylene glycol.

BENEFITS WHEN COMPARED TO PET

The two condensed aromatic rings of PEN confer on it
improvements in strength and modulus, chemical and
hydrolytic resistance, gaseous barrier, thermal and
thermo-oxidative resistance and ultraviolet (UV) light barrier
resistance compared to ​polyethylene terephthalate (PET).
19

PEN is intended as a PET replacement, especially when

used as a substrate for flexible integrated circuits.

PET has a low glass transition temperature which makes it

unsuitable for high-temperature applications. PET bottles

will melt if filled with hot water. PEN, on the other hand with

a higher glass transition temperature can withstand this

heat. So a ​ copolymer of PET and PEN ​is now used for

such applications. This is economic and effective.

SPACE APPLICATIONS

With the space industry moving to composite materials

and more advanced technology that can withstand long
space missions and extremely harsh environments,
polyester finds use as a significant component of important
composites. It is the most commonly used matrix.
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DISADVANTAGES OF POLYESTERS
● The main problem with the synthetic fabrics like the
polyester is that they don’t breathe. So, we experience
humidity.
● The synthetic fabrics don’t give you the same sense of
luxury , comfort and happiness as the natural fabrics
like the cotton , the wool .
● Some polyesters are non biodegradable too so we
can’t use them extensively.

IMPACTS ON THE ENVIRONMENT

Stage Positive Impacts on Negative Impacts on

Environment Environment
21

Extraction Mining for non renewable resources

that create polyester, (coal and
petroleum) destroy natural habitats
during the process.

Transportati Fuel released by vehicles used to

on transport the raw materials before
and after manufacturing pollutes the
atmosphere.

Manufacturi The process of Industries are multiplying and

ng creating polyester manufacturing polyester at a very fast
reduces energy rate, which produces pollution.
consumption.Polyest
er itself does not
leave behind many
by products during
production, therefore
produces a low
toxicity level.

Packaging PET bottles are To keep the product new and

recyclable which undamaged of whatever polyester
don’t require as may be used for, packaging is always
much packaging as excessive, and mostly ends up at a
other polyester landfill.
products.
22

Disposal Recycled PET Sometimes polyester is blended with

polyester from soda other materials such as nylon, taking
bottles is remade by 30-40 years to decompose.
re-melting and
extruding the fiber.

Polyester reduces
the amount of solid
waste sent to
landfills.
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SOME BIODEGRADABLE POLYMERS

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BIBLIOGRAPHY

http://en.wikipedia.org/wiki/Polyester
http://www.whatispolyester.com/
http://www.madehow.com/Volume-2/Polyester.html
http://www.pslc.ws/macrog/pet.htm
http://scienceperspectives.blogspot.in/p/impacts-on-enviro
nment.html
http://aerospaceengineeringblog.com/composite-materials/
https://en.wikipedia.org/wiki/Polyethylene_naphthalate
https://en.wikipedia.org/wiki/Polyethylene_terephthalate
http://www.hitachi.com/businesses/infrastructure/product_s
ite/ip/process/pet.html