Polymers Chemistry Project

Polymers Synthesis and Property Analysis
Chemistry Project
Chemistry Project
Chemistry Project
Polymers
Synthesis and property Analysis
Chemistry Project
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
Acknowledgments
I am very greatful to my chemistry teacher, Mr. Nadeem Ahmad, who has been a constant source of
inspiration and guidance. He supported me with all my ideas and helped me to the maximum extend possible. She
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 she encouraged me to search for something similar, yet interesting enough for me. This project
would never have existed, if it wasn’t for her passion to teach.
I would also like to thank our lab assistant, Mr. Dinesh Kumar 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.
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
Image 2.1
polysaccharides (e.g. cellulose) which are joined together by glycosidic bonds via
oxygen atoms.
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Chemistry Project
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. Image 2.2
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,
Image 2.3 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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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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Chemistry Project
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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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.
intermediate
High AE
energy
reactant
product
reaction progress
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Chemistry Project
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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+ +
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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Chemistry Project
Precautions
2. Styrene may pose health risks if it comes in contact with the body.
3. Styrene resin is sticky, so use gloves.
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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Concentration of catalyst Time taken to cure

0.5 3 hours 14 minutes
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Chemistry Project
Property Analysis
Test Result
Flexibility Low
Strength Medium
Color Yellowish, Transparent
Texture Smooth
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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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
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.
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Chemistry Project
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)

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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at 40 *C 30
25
20
Time (min)15
10
0 0.5 1 1.5 2 2.5

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

Concentration
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Chemistry Project
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
Color Transparent
Texture Smooth
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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+ +
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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Chemistry Project
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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Polymers Synthesis and Property Analysis

Aim of the Project 1

Brief Theory, Synthesis and Analysis of

Aim of the Project

[* Synthesized using chemicals available in the school laboratory] [**

Due to the extraordinary range of properties accessible in polymeric

The first synthetic polymer, a phenol-formaldehyde polymer, was

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.

What actually happened

The structure below shows the growing molecule of BAKELITE.

3. Styrene resin is sticky, so use gloves.

What actually happened

Concentration of catalyst Time taken to cure

What actually happened

0 0.5 1 1.5 2 2.5

0 0.5 1 1.5 2 2.5

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