T.C.

YILDIZ TEKNİK ÜNİVERSİTESİ

FEN-EDEBİYAT FAKÜLTESİ
KİMYA BÖLÜMÜ

POLYESTERS

DİLRUBA KUTLU
ÖZGE ÇALDIR
MUHAMMED SAİD ENGİNAR
What Is Polyesters ?
Polyester is the third most widely used commodity plastic. It is used
extensively for clothing, food packaging, and automotive components.
Polyester is characterized by excellent mechanical strength, chemical
resistance, wear resistance, and electrical insulating properties.

Polyester is a category of polymers that contain the ester functional group in

every repeat unit of their main chain. As a specific material, it most
commonly refers to a type called polyethylene terephthalate (PET). Natural
polyesters and a few synthetic ones are biodegradable, but most synthetic
polyesters are not.
Polyester fibers are sometimes spun together with natural fibers to
produce a cloth with blended properties. Cotton-polyester blends can be
strong, wrinkle- and tear-resistant, and reduce shrinking. Synthetic fibers
using polyester have high water, wind, and environmental resistance
compared to plant-derived fibers. They are less fire-resistant and can melt
when ignited.

Liquid crystalline polyesters are among the first industrially used liquid
crystal polymers. They are used for their mechanical properties and heat-
resistance. These traits are also important in their application as an
abradable seal in jet engines.
When was Polyester Invented?
Polyester was invented in the mid-1930s by W.H.
Carothers along with his team while working at
DuPont. However, this work was not further
developed until 1941 when it was expanded upon
and patented by a group of British scientists who
created the first polyester fiber. DuPont ultimately
purchased the rights to the patent and sold it
under the brand names: Dacron and, later, Mylar.
Uses of Polyester
1) Textile Industry
Polyester is one of the most widely used synthetic fibers in the
textile industry. In the clothing industry, polyester fabrics are
frequently used in a variety of clothing products such as shirts,
trousers, dresses and coats. It is popular thanks to its durable,
lightweight and wrinkle-resistant properties.
2) Packaging Industry
Polyester also has a wide range of usage in the packaging
industry. Clear polyester film is used for food packaging, while
metallized polyester film is used to produce packaging
materials with coated and glossy surfaces. These films are
preferred in the packaging industry because they are durable,
flexible and low-cost.
Uses of Polyester
3) Automotive Industry
In the automotive industry, polyester has uses in various
components. Polyester resins are widely used in vehicle body
panels, upholstery materials and interior trim.
4) Electronic Industry
Polyester films and resins are used as insulating materials in
the electronics industry. High dielectric strength and low
dielectric loss make polyester preferred in the insulation of
electronic components.
5) Medical Applications
Polyester is also used in medical applications. Polyester
materials are preferred in many areas such as medical devices,
surgical sutures, implants and medical clothing.
Synthesis of Polyester
Polycondensation
Polyesters are another form of condensation polymer. Typically, synthesis of polyester is
obtained when a dicarboxylic acid and a diol are reacted. The general reaction equation
for a diol and a diacid is:

(n+1) R(OH)2 + n R´(COOH)2 → HO[ROOCR´COO]nROH + 2n H2O

The ester product has a free (unreacted) carboxyl group at one end and a free alcohol
group at the other after the first reaction. Subsequent esterification utilizing step-growth
polymerization results in the formation of polyester. Polyethylene terephthalate (PET),
the most significant polyester, is produced from the reaction of 1,4-
benzenedicarboxylic (terephthalic acid) and 1,2-ethanediol (ethylene glycol) monomers.
Synthesis of Polyester
Azeotrope Esterification
The esterification of azeotropes is a traditional condensation technique. By azeotropic distillation,
the water produced by the reaction of alcohol and a carboxylic acid is continuously eliminated.
When the melting temperatures of the monomers are low enough, a polyester can be generated
by direct esterification while vacuuming away the reaction water.
Alcoholic Transesterification
Transesterification is the process by which an alcohol-terminated oligomer and an ester-
terminated oligomer condense to create an ester bond, with the loss of an alcohol. R and R’ are
the oligomer chains, whereas R” is a sacrifice unit such as a methyl group.
Synthesis of Polyester
Acylation
In acylation, the acid begins as an acyl chloride, therefore the polycondensation occurs
with hydrochloric acid (HCl) emission rather than water. The reaction between diacyl
chlorides and alcohols or phenolic compounds has been extensively utilized to the
production of polyester.
The reaction of a diacyl chloride with a dialcohol at high temperatures (100 to > 300 °C)
produces polyester and hydrogen chloride. Without a catalyst, the reaction proceeds
quickly at these relatively high temperatures:
Synthesis of Polyester
Poly(lactic)acid (PLA)
PLA, or poly(lactic acid), is another kind of polyester. Nevertheless, PLA is produced with
only a single monomer, lactic acid. Each molecule of the monomer comprises carboxylic
acid and alcohol groups. As a biodegradable alternative to petroleum-based plastics,
polyester PLA, whose source material is plant starch such as maize, is now in use. When
items containing polyester are disposed of in landfills, the ester bonds within the
polymer can be broken down due to acidic conditions, causing the polymer chains to
degrade. Alcohol and carboxylic acids are the byproducts of polyesters’ acid hydrolysis.
 CONSIDERATIONS
FOR SYNTHESIS
OF POLYESTERS
The process of producing polyester via the chemical
synthesis route requires a high temperature (above 180 °C)
which may lead to excessive oxidation or even significantly
damage the stability of product performance. Such high
reaction temperatures would produce undesirable side
reactions when using monomers with low thermal or
chemical stability.
Conventional methods for synthesizing aliphatic polyesters
usually use alkoxy aluminum, zinc-like, and tin-like metal-
containing oxides or organic compounds as catalysts. This
toxic metal catalyst normally might negatively affect the
biosafety and biocompatibility of the end product if it
cannot be removed after the process of making the
polymer.
 Additionally, a significant quantity of organic
solvents in the production process may cause
CONSIDERATIONS environmental pollution (solution
polymerization) if the management of the
FOR SYNTHESIS organic solvent is inappropriate. Generally, the
OF POLYESTERS hydrocarbon solvent is used to manufacture
polyester, such as xylene or benzene, to avoid
the viscosity buildup during the polymerization
and to remove water produced from the
esterification process via azeotropic distillation.
 AN ALTERNATIVE:
ENZYME-CATALYZED SYNTHESIS
Polyesters can also be synthesized by enzyme catalysis. The Nobel Prize
Winner Sumner proved in 1947 that enzymes are proteins with
catalytic properties. There are many studies have been previously
conducted to produce polyester using an enzymatic process due to
several advantages;
• Enzymes are derivable from renewable resources
• Mild reaction conditions where thermal degradation of the raw
materials or product can be avoided
• No metal catalyst residue which makes the product achieve better
biocompatibility
• Stereoselective, regioselective, and chemoselective, usually only a
single substrate or a class of structurally similar substrates can
participate in the reaction, retaining the active function of other
groups of the monomer, avoiding unwanted side reactions
• Biodegradable polyester can be synthesized using enzymes as a
catalyst.
 DISADVANTAGES OF ENZYME-
CATALYZED SYNTHESIS
As a comparison with chemical methods, enzyme-catalyzed polymerization of
polyesters is a green process, which may be considered an alternative route for
polyester synthesis. However, enzyme-catalyzed synthesis may have
disadvantages;
• High cost,
• Large enzyme consumption,
• And a lesser number of high molecular weight polymers that can be
produced.
With the development of the enzyme-catalyzed synthesis of polyesters, the
challenges are believed to be addressed when more attempts are conducted.
 PHYSICAL PROPERTIES
OF POLYESTERS
Tenacity
Polyester filaments and staple fibre are strong due to
their crystalline nature. The crystalline nature permits
for the formation of highly effective Vander wall’s
forces as well as since hydrogen bonds which provided
the fibre its good tenacity. The tenacity remains
unchanged when wet since the fibre resists the entry
of water molecules to a significant extent.
Elastic Plastic Nature
The very crystallinity of the fibre prevents wrinkling
and creasing. Repeated stretching and straining
causes, distortion of the polymer system as the Vander
wall’s forces cannot withstand much stretching.
 PHYSICAL PROPERTIES OF
POLYESTERS
Hygroscopic Nature
Filaments and staple fibers are hydrophobic. The lack of polarity and
the very crystalline structure resists the entry of water molecules into
the polymer system. The hydrophobic nature of the polymer system
attracts fats, greases, oils, acid or any other greasy soils. It is believed
to be oleophilic. The oleophilic nature makes it not easy to remove
grease by soap but by dry-cleaning with organic solvents.
Thermal Properties
It is a poor heat conductor and it has low resistance to heat. It melts
on heating. Polyester textile materials can be permanently heat-set. It
is a thermoplastic fiber meaning that it is capable of being shaped or
turned when heated. Thermoplastic fibers heated under strictly
controlled temperatures soften and can then be made to similar to a
flat, creased or pleated configuration. When cooled thermoplastic
fibers retain the new configuration.
 CHEMICAL PROPERTIES
OF POLYESTER
Effect of Acids
These polymers are resistant to acids.
Effect of Alkalis
Alkaline conditions as seen in laundering hydrolyze
the ester groups in polyester polymers. The
crystalline nature prohibits hydrolysis to a greater
extent and it is the surface of filament which gets
hydrolyzed. Continued laundering results in
hydrolysis and materials get fewer as the surface
film of the fiber gets lost.
 CHEMICAL PROPERTIES
OF POLYESTER
Effect of Bleaches
It does not require bleaching. It retains its whiteness and
requires only chlorine bleaches to be used when essential.
Sunlight
It withstands the sun’s ultra-violate radiations and is resistant to
acidic pollutants in atmosphere.
Color Fastness
It is not easy for dye molecule to penetrate the fibre when
dyed, it retains its color after regular wash.
Micro-Organisms
It is resistant to bacteria and other micro-organisms.
Application of
Polyesters

• Clothing : Polyester fabric has

properties that make it ideal for use
as clothing as it is both breathable
and stain-resistant.
• Home Furnishings : Polyester’s stain
resistance makes it an excellent
material for furniture coverings.
• Tires : Polyester is used as a
reinforcing material, placed in
strategic positions throughout the
tire.
• Conveyor Belts : Polyester is used in reinforcing carcasses throughout
the conveyor belt due to its durability and tensile strength.

• Safety Belts :Polyester has excellent tensile strength, especially when

woven into a dense textile.

• Bottles : Polyester is used for disposable plastic bottles due to its

resistance to microorganisms and does not degrade biologically.
Padding Upholstery, Sports Gear, Sprays : Polyester
Cushioning, and Insulating Sportswear, is used in a
Gloves & Mitts : Polyester is Upholstery, Covers, number of spray
used as a batting material for and Table coating
cushions and upholstery as it Cloths : Polyester is applications due
tends to retain its volume used in manufacturing to its good
and shape even after being products often utilized performance and
compressed multiple times. outdoors due to its lower cost
durability and stain compared to
resistance. epoxy coatings.
 How Is
Polyester
Fabric
Made?
 Polyester
Manufacturi
ng Scheme
Polyest
er
Recycli
ng
There are two ways of
polyester recycling. They
are mechanical recycling
and chemical recycling.
Mechanical Poly
ester Recycling

• Mechanical
recycling, plastic is melted
to make new yarn. This
process can only be done
a few times before the
fiber loses its quality.
Chemical
Polyester
Recycling
• Chemical
recycling involves
breaking down the plastic
molecules and reforming
them into yarn. This
process maintains the
quality of the original fiber
and allows the material to
be recycled infinitely, but
it is more expensive.
Environmental Facts About Polyester
Production

Energy requirements for fiber production are high. Energy inputs and
greenhouse gas emissions in polyester production are high (125 MJ/kg fiber
versus 100 MJ/kg of viscose fiber)

Most commonly, the chemicals used in production are not released to the
environment

However factories without end-of-pipe wastewater treatment systems, release

antimony along with a host of other potentially dangerous substances like
cobalt, manganese salts, sodium bromide, and titanium dioxide.
Recycled • Saves petroleum and dependency on oil.
Polyester is • Requires 70 percent less energy than virgin fiber.
a Better • Keeps bottles out of landfills
Environment • However it costs about 15 to 20 percent more than
virgin fiber.
al Choice • The output of rPET is also of lesser grade quality
and Gaining than virgin polyester.
In Popularity
 • https://textileapex.com/physical-and-chemical-properties-of-polyester/
REFERENCES • https://www.mdpi.com/2073-4360/14/23/5059
• https://www.xometry.com/resources/materials/polyester/

• https://en.wikipedia.org/wiki/Polyester

• https://www.xometry.com/resources/materials/uses-of-polyester/

• https://en.wikipedia.org/wiki/Polyester#Uses_and_applications

• https://www.essentialchemicalindustry.org/polymers/polyesters.html

• https://scienceinfo.com/synthesis-of-polyester/

• https://www.xometry.com/resources/materials/uses-of-polyester/

• https://www.jcfa.gr.jp/english/seni/list/06.html

• https://www.nrdc.org/sites/default/files/CBD_FiberFacts_Polyester.pdf