Polymers Synthesis and Property Analysis

Chemistry Project

Utkarsh Patel
Class: XII-A

Teacher’s Signature
 CONTENTS
Acknowledgements iii

Aim of the Project 1

General Overview 1

Brief Theory, Synthesis and Analysis of

1. Bakelite * 3

2. Polystyrene 7

3. Epoxy Resin 11

Result 15

References 16

CAUTION: Some experiments require hazardous and/or potentially hazardous chemicals.

* This refers to the level of caution required for each individual experiment.
 Acknowledgments

I am very greatful to my chemistry teacher, Mr. Praveen Kr. Agnihotri, who has been a constant
source of inspiration and guidance. He supported me with all my ideas and helped me to the
maximum extent possible. He also gave me enough extra time to find all the required information
to turn my ideas into a single project. Even though what I initially wanted to make (conductive
Polymers) wasn’t possible to do with our existing lab apparatus, yet he encouraged me to search
for something similar, yet interesting enough for me. This project would never have existed if i
t wasn’t for his passion to teach.

I would also like to thank our lab assistant for all the timely help he provided. Apart from this, I
would like to thank all those people who’ve published their useful work on the internet, without
which, I perhaps wouldn’t even have enough information to make even a single polymer.

Teacher’s Sign Examiner’s Sign Principal’s Sign

Polymers Synthesis and Property Analysis

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
Image 2.1
in fact based on repeating units of polysaccharides (e.g. cellulose) which are
joined together by glycosidic bonds via oxygen atoms.

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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 Image 2.2
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
Image 2.3
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.
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Polymers Synthesis and Property Analysis

Level of Caution
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.
Image 6.1 shows the structure of bakelite.
Image 3.1

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Precautions
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.

Materials Needed

Chemicals: Apparatus:
1. 25g 40% formaldehyde 1. 150-mL beaker
2. 20 g phenol 2. stirring rod
3. 55 mL glacial acetic acid
4. Conc. Hydrochloric acid

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.

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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.

Temperature Observations
40-35 *C No observable changes
50-45 *C Turbidity started apearing
60-55 *C Roughly Polymerization started
75-60 *C Semi Solid appeared at the bottom of the beaker
30-25 *C At long standing, the color changed to dark pink

Property Analysis

Test Result
Flexibility Brittle
Strength Low
Bounciness Negligible
Color Dark Pink
Texture Slightly Porous
Inertness Stable in air at room temp.

Chemistry Behind it

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

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Polymers Synthesis and Property Analysis

+ +

The structure below shows the growing molecule of BAKELITE.

Level of Caution
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.
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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.

Materials Needed

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

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What actually happened

Concentration of catalyst Time taken to cure

0.5 3 hours 14 minutes
1.0 2 hours 18 minutes
1.5 2 hours 10 minutes
2.0 2 hours 3 minutes

3.5
3

2.5
2
Time
1.5
1

0.5
0
0 0.5 1 1.5 2 2.5

Concentration

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Property Analysis

Test Result
Flexibility Low
Strength Medium
Bounciness Negligible
Color Yellowish, Transparent
Texture Smooth
Inertness Stable in air at room temp.

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 non-
aromatic 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).

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Polymers Synthesis and Property Analysis

Level of Caution
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.

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

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

at 40 *C
Concentration of catalyst Time taken to cure Appearance
0.5 28 minutes almost clear, yellowish
1.0 20 minutes slightly frothy, yellowish
1.5 12 minutes frothy, yellowish
2.0 10 minutes very frothy, yellowish

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Polymers Synthesis and Property Analysis
at 40 *C
30

25

20

Time (min) 15

10

0
0 0.5 1 1.5 2 2.5
Concentration

at 7 *C
180
160
140
120
100
Time (min)
80
60
40
20
0
0 0.5 1 1.5 2 2.5

Concentration

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at 7 *C
Concentration of catalyst Time taken to cure Appearance
0.5 170 minutes almost clear
1.0 150 minutes almost clear, ‘starry’
1.5 130 minutes fewer bubbles, transparent
2.0 95 minutes bubbles, almost transparent

Property Analysis

Test Result
Flexibility Low
Strength High
Bounciness Negligible
Color Transparent
Texture Smooth
Inertness Stable in air at room temp.
Unreactive to Acids

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.

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Polymers Synthesis and Property Analysis

+ +

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.

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REFERENCES
http://www.google.co.in/webhp?hl=en
http://en.wikipedia.org/wiki/Polystyrene
http://en.wikipedia.org/wiki/Styrene
http://en.wikipedia.org/wiki/Epoxy
http://en.wikipedia.org/wiki/Bakelite
http://papers.ssrn.com/sol3/papers.cfm?abstract_id=1420502
http://answers.yahoo.com/question/index?qid=20090717144012AAKmCyb
http://inventors.about.com/od/pstartinventions/a/plastics.htm
http://www.barrule.com/workshop/images/info/foams/index.htm
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2430229/
http://www.pslc.ws/mactest/styrene.htm
http://www.americanchemistry.com/s_plastics/sec_pfpg.asp?CID=1421&DID=5213

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