Chemistry

Project Report
On

POLYMERS
“Synthesis and Property Analysis”
Session: 2018-19

Under Supervision of
Submitted by
Mr. Manish
Harshdeep
(Lecturer in Chemistry) Roll No.
Class XII (Non-
Medical)
GREENFIELD PUBLIC SCHOOL,
KURUKSHETRA
CERTIFICATE

This is to certify that Harshdeep Roll No.________________ student of

XII of school Greenfield Public School. Kurukshetra has carried out of work in

project “Polymers” under the supervision & guidance as partial fulfillment of the

requirement for passing the XIIth Class examination under scheme of C.B.S.E.,

New Delhi.

Mr. Manish
Lecturer in Chemistry
 ACKNOWLEDGEMENT

I express my deep sense of gratitude to Mr. Manish, Lecturer of

Chemistry, Greenfield Public School, Kurukshetra for her inspiration,

valuable guidance and constant encouragement in the completion of this project.

Without her it would have been an impossible task for me. I have put my sincere

effort to make this project interesting. I have fully consulted all the available

books on this subject and I am thankful to esteemed authors

Manish
12th (Non-Medical)
Roll No. ……………
 CONTENTS
Acknowledgements

Aim of the Project

General Overview

Brief Theory, Synthesis and Analysis of

1. Bakelite

2. Polystyrene

3. Epoxy Resin

Result
 Aim of the Project

The aim of this project is to find out the optimum conditions for synthesis of the
following polymers,
1. Bakelite*
2. Polystyrene**
3. Epoxy Resin**
and to study their physical properties like flexibility, strength, bounciness,
color etc.
[* Synthesized using chemicals available in the school laboratory] [**
Synthesized using Industrial Reagents]
 General Overview

A polymer is a large molecule (macromolecule) composed of repeating structural

units typically connected by covalent chemical bonds. While polymer in popular
usage suggests plastic, the term actually refers to a large class of natural and
synthetic materials with a variety of properties.

Due to the extraordinary range of properties

accessible in polymeric materials, they have come
to play an essential and ubiquitous role in everyday
life - from plastics and elastomers on the one hand
to natural biopolymers such as DNA and proteins
that are essential for life on the other. A simple
example is polyethylene, whose repeating unit is
based on ethylene (IUPAC name ethene) monomer (Image 2.1). Most commonly,
as in this example, the continuously linked backbone of a polymer consists
mainly of carbon atoms. However, other structures do exist; for example,
elements such as silicon form familiar materials such as silicones, examples being
silly putty and waterproof plumbing sealant. The
backbone of DNA is in fact based on repeating units of
polysaccharides (e.g. cellulose) which are joined together by glycosidic bonds via
oxygen atoms.

Natural polymers (from the Greek poly meaning “many” and meros meaning
“parts”) are found in many forms such as horns of animals, tortoise shell, rosin
(from pine trees), and from distillation of organic materials.

One of the most useful of the natural polymers was rubber, obtained from the sap
of the hevea tree. (Rubber was named by a chemist found that a piece of
solidified latex gum was good for rubbing out pencil marks on paper. In Great
Britain, erasers are still called “rubbers”.)

Natural rubber had only limited use as it became brittle in the cold and melted
when warmed. In 1839, Charles Goodyear discovered, through a lucky accident,
that by heating the latex with sulfur, the properties were changed making the
rubber more flexible and temperature stable. That process became known as
vulcanization.

The first synthetic polymer, a phenol-

formaldehyde polymer, was introduced
under the name “Bakelite” (Image 2.2 &
2.3), by Leo Baekeland in 1909. Its original
use was to make billiard balls. Rayon, the
first synthetic fiber was developed as a
replacement for silk in 1911. Although many
polymers were made in the following years,
the technology to mass produce them was
not developed until World War II, when there was a need to develop synthetic
rubber for tires and other wartime applications and nylon for parachutes. Since
that time, the polymer industry has grown and diversified into one of the
fastest growing industries in the world. Today, polymers are commonly used in
thousands of products as plastics, elastomers, coatings, and adhesives. They make
up about 80% of the organic chemical industry with products produced at
approximately 150 kg of polymers per person annually in the United States.

Furthermore, conductive polymers are organic polymers that conduct electricity.

Such compounds may be true metallic conductors or semiconductors. It is
generally accepted that metals conduct electricity well and that organic
compounds are insulating, but this class of materials combines the properties of
both. The biggest advantage of conductive polymers is their processibility.
Conductive polymers are also plastics (which are organic polymers) and therefore
can combine the mechanical properties (flexibility, toughness, malleability,
elasticity, etc.) of plastics with high electrical conductivities. Their properties can
be fine-tuned using the exquisite methods of organic synthesis.
 BRIEF THEORY

1. BAKELITE

Brief Description

Bakelite is a material based on the thermosetting phenol formaldehyde resin,

developed in 1907–1909 by Belgian Dr. Leo Baekeland. Formed by the reaction
under heat and pressure of phenol (a toxic, colourless crystalline solid) and
formaldehyde (a simple organic compound), generally with a wood flour filler, it
was the first plastic made from synthetic components. It was used for its
electrically nonconductive and heat-resistant properties in radio and telephone
casings and electrical insulators, and was also used in such diverse products as
kitchenware, jewellery, pipe stems, and children's toys. In 1993 Bakelite was
designated an ACS National Historical Chemical Landmark in recognition of its
significance as the world's first synthetic plastic. The retro appeal of old Bakelite
products and labor intensive manufacturing has made them quite collectible in
recent years.
PRECAUTION

1. Wear safety goggles at all times in the laboratory.

2. Formalin is an irritant to the skin, eyes, and mucous membranes.
3. Phenol is toxic via skin contact. It is listed as a carcinogen.
4. Glacial acetic acid is an irritant and can cause burns on contact.
5. Work under a hood and wear gloves and protective clothing when working
with these materials.

MATERIAL NEEDS

Chemicals
1. 25g 40% formaldehyde
2. 20 g phenol
3. 55 mL glacial acetic acid
4. conc Hydrochloric acid
Apparatus:

1. 150-mL beaker
2. stirring rod
PROCEDURE

First make the Phenol-formaldehyde reaction mixture by mixing 25 g 36-40%

formaldehyde + 20 g phenol + 55 mL glacial acetic acid.
Under a hood, measure 25 mL of the phenol-formaldehyde reaction mixture into a
150-mL beaker.
Place the beaker on a white paper towel.
Add 10 mL of concentrated hydrochloric acid, slowly, with stirring.
Add additional hydrochloric acid, dropwise, with stirring. (You will need
approximately 2 mL of HCl.) As the polymerization point is reached, a white
precipitate will form and dissolve. At the point where polymerization begins, the
white precipitate will not dissolve.
Continue to stir as the plastic forms and becomes pink in color.
Wash the plastic well before handling.

WHAT ACTUALLY HAPPENED

I was slightly nervous to try out something absolutely new and was uncertain of
its results. I took the chemicals given to me by Baboolal sir and followed the
instructions. I took the phenol-formaldehyde reaction mixture in a beaker, placed
it over a sheet of paper. Took a test tube full of HCl, and added it to the beaker
slowly with constant stirring. And by slowly I mean I almost emptied the test tube
in about two minutes. I couldn’t figure the polymerization point as no precipitate
appeared. Thinking there’s something wrong with the procedure, I went to ask for
ma’ams advice. She asked me to indirectly heat it. Due to certain reasons, I didn’t
hear indirectly and heated the beaker over the flame for about 30 seconds.
Nothing happened. Depressed, I walked away from it wondering what to do next.
And then suddenly there was this loud noise of some kind of explosion. It was the
beaker. All the contents had poured out like foam, except solid. It was light pink
in color. It had lots of pours in it and kind of looked like pumice stone. Ma’am
said it happened because I’d supplied a lot of heat by direct heating, and it
seemed the most plausible explanation to it and so to obtain a proper polymer, I
modified the experimental setup after discussing it with ma’am.

I set up a large water filled beaker on a tripod stand with wire gauze and in a
boiling tube took the reaction mixture. I fixed this boiling tube using a clamp
stand, half dipped in the beaker so that the contents were evenly heated. I added
the same amount HCl as before, except this time, I added a few drops after every
30 seconds. This time, after 3 minutes, I could see something suddenly happen in
the boiling tube. I alerted ma’am but again it exploded. The sudden reaction broke
the boiling tube, and caused a crack in the beaker. I collected the polymer and
washed it. Its physical appearance was the same as before.

Both these experiments suggested that the reaction was extremely fast, but its
activation energy was fairly high. So no matter if its directly heated, or indirectly,
the moment it gains sufficient energy, the polymerization starts rapidly.

For determining the optimum conditions for the synthesis of Bakelite, I decided
to take a reaction mixture in a beaker, heat it to a certain temperature (indirectly),
and then add HCl to find out the optimum temperature. I chose beaker over
boiling tube, because as was apparent by the pores, greater the surface
area, safer it would be to carry out the reaction.

PROPERTY ANALYSIS

CHEMISTRY BEHIND IT

Phenol and Formaldehyde react in the following manner to make the polymer.

The structure below shows the growing molecule of BAKELITE.

2. POLYSTYRENE

Brief Description

Polystyrene (pronounced /ˌpɒliˈstaɪriːn/) (IUPAC Poly(1-phenylethane-1,2-diyl)),

sometimes abbreviated PS, is an aromatic polymer made from the aromatic
monomer styrene, a liquid hydrocarbon that is commercially manufactured from
petroleum by the chemical industry. Polystyrene is one of the most widely used
kinds of plastic.

Polystyrene is a thermoplastic substance, which is in solid (glassy) state at room

temperature, but flows if heated above its glass transition temperature (for
molding or extrusion), and becoming solid again when cooling off. Pure solid
polystyrene is a colorless, hard plastic with limited flexibility. It can be cast into
molds with fine detail. Polystyrene can be transparent or can be made to take on
various colors.

Solid polystyrene is used, for example, in disposable cutlery, plastic models, CD

and DVD cases, and smoke detector housings. Products made from foamed
polystyrene are nearly ubiquitous, for example packing materials, insulation, and
foam drink cups.
Polystyrene can be recycled, and has the number "6" as its recycling symbol.
Polystyrene does not biodegrade, and is often abundant as a form of pollution in
the outdoor environment, particularly along shores and waterways.

PRECAUTIONS

1. Wear safety goggles at all times in the laboratory.

2. Styrene may pose health risks if it comes in contact with the body.
3. Styrene resin is sticky, so use gloves.
4. Work under a hood and wear gloves and protective clothing when working
with these materials.

MATERIAL NEEDED

Chemicals:
1. Vinyl Benzene (Styrene Casting Resin)
2. Methyl ethyl ketone (Casting resin catalyst)

Apparatus:
1. Test tubes
2. Stirring rod
3. Thermostat
4. Measuring Cylinder
5. a 5 mL Syringe
6. Stop Watch
PROCEDURE

 Take 4 clean, numbered test tubes and to each add 3mL of Vinyl Benzene.
 Fill the syringe with methyl ethyl ketone.
 Start the stop watch.
 Make the volume of Vinyl Benzene in test tube one equal to 5 mL.
 Now note the time as you add 5 divisions of the syringe, i.e. 0.5 mL to test
tube one and stir it well.
 Repeat the above 2 steps with 4.5 mL of Vinyl Benzene and 1.0 mL of
methyl ethyl ketone, in the second test tube and so one.
 Place these in the thermostat with temperature set to 40 *C.

WHAT ACTUALLY HAPPENED

PROPERTY ANALYSIS

CHEMISTRY BEHIND IT

The chemical makeup of polystyrene is a long chain hydrocarbon with every

other carbon connected to a phenyl group (the name given to the aromatic ring
benzene, when bonded to complex carbon substituents). Polystyrene's chemical
formula is (C8H8)n; it contains the chemical elements carbon and hydrogen.
Because it is an aromatic hydrocarbon, it burns with an orange-yellow flame,
giving off soot, as opposed to nonaromatic hydrocarbon polymers such as
polyethylene, which burn with a light yellow flame (often with a blue tinge) and
no soot. Complete oxidation of polystyrene produces only carbon dioxide and
water vapor.

This addition polymer of styrene results when vinyl benzene styrene monomers
(which contain double bonds between carbon atoms) attach to form a polystyrene
chain (with each carbon attached with a single bond to two other carbons and a
phenyl group).
3. EPOXY RESIN

Brief Description

Epoxy or polyepoxide is a thermosetting polymer formed from reaction of an

epoxide "resin" with polyamine "hardener". Epoxy has a wide range of
applications, including fiber-reinforced plastic materials and general purpose
adhesives.

Credit for the first synthesis of bisphenol-A-based epoxy resins is shared by Dr.
Pierre Castan of Switzerland and Dr. S.O. Greenlee of the United States in 1936.

The applications for epoxy-based materials are extensive and include coatings,
adhesives and composite materials such as those using carbon fiber and fiberglass
reinforcements (although polyester, vinyl ester, and other thermosetting resins are
also used for glass-reinforced plastic). The chemistry of epoxies and the range of
commercially available variations allows cure polymers to be produced with a
very broad range of properties. In general, epoxies are known for their excellent
adhesion, chemical and heat resistance, good-to-excellent mechanical properties
and very good electrical insulating properties. Many properties of epoxies can be
modified (for example silver-filled epoxies with good electrical conductivity are
available, although epoxies are typically electrically insulating). Variations
offering high thermal insulation, or thermal conductivity combined with high
electrical resistance for electronics applications, are available.

PRECAUTIONS

1. Wear safety goggles at all times in the laboratory.

2. The hardner, Triethylenetetramine may cause allergic reactions. Wear
gloves at all times.
3. Both the chemicals are sticky so avoid contact with bare hands.
4. Work under a hood and wear gloves and protective clothing when working
with these materials.

MATERIAL NEEDED

Chemicals:
1. Epoxy Resin (formed by reaction between epichlorohydrin and bisphenol-
A)
2. Hardener (Triethylenetetramine)
Apparatus:
1. Test tubes
2. Stirring rod
3. Thermostat
4. Measuring Cylinder
5. a 5 mL Syringe
6. Stop Watch

PROCEDURE

 Take 4 clean, numbered test tubes and to each add 3mL of Resin.
 Fill the syringe with Triethylenetetramine .
 Start the stop watch.
 Make the volume of Resin in test tube one equal to 5 mL.
 Now note the time as you add 5 divisions of the syringe, i.e. 0.5 mL to test
tube one and stir it well.
 Repeat the above 2 steps with 4.5 mL of Resin and 1.0 mL of
Triethylenetetramine , in the second test tube and so one.
 Place these in the thermostat with temperature set to 40 *C.
 Repeat all the steps and keep this set at room temperature. (7 *C)

WHAT ACTUALLY HAPPENED

PROPERTY ANALYSIS

CHEMISTRY BEHIND IT

Epoxy is a copolymer; that is, it is formed from two different chemicals. These
are referred to as the "resin" and the "hardener". The resin consists of monomers
or short chain polymers with an epoxide group at either end. Most common epoxy
resins are produced from a reaction between epichlorohydrin and bisphenol-A,
though the latter may be replaced by similar chemicals. The hardener consists of
polyamine monomers, for example Triethylenetetramine (TETA). When these
compounds are mixed together, the amine groups react with the epoxide groups to
form a covalent bond. Each NH group can react with an epoxide group, so that
the resulting polymer is heavily crosslinked, and is thus rigid and strong.
The process of polymerization is called "curing", and can be controlled through
temperature and choice of resin and hardener compounds; the process can take
minutes to hours. Some formulations benefit from heating during the cure period,
whereas others simply require time, and ambient temperatures.
 RESULT

Bakelite

It’s optimum synthesis temperature range was found to be 70-80 *C. Its
synthesis requires high activation energy but the reaction is kinetically very fast.

Polystyrene

It cures faster at higher concentrations of the catalyst. The strength of the

polymer was independent of the concentration ratio of the resin and catalyst. Its
kinetics are complex as its concentration v/s curing time graph was found to be
irregular. The optimum temperature range for synthesis of this polymer was
found to be over 40 *C at the tested concentrations of the catalyst.

Epoxy Resin

It cures faster at high concentrations of its catalyst. It also cures faster at

higher temperature. The strength of the polymer was independent of the
concentration ratio of the resin and catalyst. The reaction may be following first
order kinetics as the concentration v/s curing time graph was found to be close to
linear. The optimum temperature range for synthesis of this polymer was found to
be 5-10 *C at the tested concentrations of the catalyst.