Polymers 1

Polymerisation
Addition Polymerisation
Condensation Polymerisation
Uses of polymers
 A carbon – carbon double bond is needed in
the monomer
 A monomer is the small molecule that makes
up the polymer
H H
H H high pressure/trace O2
n C C C C
catalyst
H H H H n
ethene
poly(ethene)
 The polymer is the only product
 Involves the opening out of a double bond
 The conditions of the reaction can alter the
properties of the polymer
 Reaction proceeds by a free radical
mechanism
 Oxygen often used as the initiator
Addition polymerisation
 The board specifies that you know this addition
polymerisation reaction
H
H H H H H
C C C C C C
H
H H
Addition polymerisation
 Conditions are high pressure and an
oxygen initiator (to provide the initial free
radical).
 Monomer = phenylethene
 Polymer = poly(phenylethene)
 You are expected to be able to do the
following things with addition polymers:
 Predict the repeating unit of the polymer
given the monomer
 Predict the monomer from the polymer –
displayed formula and even empirical
formula.
 Know about stereochemistry of addition
polymers.
Prediction the repeating unit
 This is easy, basically open out the
double bond.
H Cl H H H H
C C C C C C
H H H Cl H Cl
chloroethene poly(chloroethene) aka
polyvinylchloride (pvc)
Predicting the monomer from the
polymer
 This is kind of the opposite to what you
have just done.
 They may ask you to draw different
formulae.
 You need to make sure you can convert
repeating units into monomers, and draw a
ring around the repeating unit
Stereoisomerism in Addition
polymers.
 Ziegla and Natta in the 1950s cam up with
a way of controlling the repeating unit.
 They won a Joint Nobel prize for their work
 The polymerisation process can be
controlled used a tin/aluminium catalyst at
50°C and 1.5atm
polymers.
 Previous to this only one type of
poly(ethene) could be made, called LDPE
or low density poly(ethane).
 The chains formed a tangled mass.
 HDPE could now be produced.
 This has a much stiffer structure due to
areas of crytallinity where the polymer
chains are much more ordered.
polymers.
 HDPE has a much higher boiling point due
to these more ordered regions.
 Generally used to make plastic bottles.
 Ziegler and Natta also discovered that
they could make stereo regular polymers.
Isotactic, syndiotactic and atactic.
Poly(propene) and stereoisomerism
 Isotactic. This is a very regular type of
polymer chain. All the methyl groups are
on the same side.
H CHH CHH CHH CHH CHH CHH CHH CH

3 3 3 3 3 3 3 3
 Syndiotactic. A slightly less regular but still very
ordered polymer.
 The methyl groups alternate the side of chain
they are on.
H H H H H H H
 Atactic.
 This is a completely random allocation of
methyl groups along the carbon skeleton.
H H H H H H H
 This varying degree of randomness will
affect the strength and melting point of the
polymer.
 The less random, the stronger the polymer
and the higher the melting point
 This is because in a more ordered polymer
they chains can get closer together and
hence the van der Waal’s forces will be
greater.
Condensation Polymers
 Involves 2 monomers that have different
functional groups.
 They also involve the elimination of water or
another small molecule.
 Hence the term condensation polymer.
 Monomer A + Monomer B  Polymer + small
molecule (normally water).
 Common condensation polymers include
polyesters (the ester linkage) and polyamides
(the amide linkage as in proteins).
Polyesters
 The OCR example here is terylene, a polymer of
benzene-1,4-dicarboxylic acid and ethane-1,2-
diol.
 The ester linkage is formed between the
monomers
O
C
O
the ester linkage
Polyesters
 You need to be able to reproduce the formation
of terylene, and possibly predict the structures of
other polyesters
O O
n HO C C OH + n HO CH2 CH2 OH
heat with
an acid
catalyst
O O
C C O CH2 CH2 O
poly(ethan-1,2-diyl benzene-1,4-dicarboxylate)
Polyamides
 These involve the linkage of two monomers

through the amide linkage as in proteins (e.g.
silk)
O
C N
H
the amide linkage
Nylon 6,6 a polyamide
H H O O
N (CH2)6 N C (CH2)4 C
H H HO OH
1,6-diaminohexane hexanedioic acid
O O
N (CH2)6 N C (CH2)4 C
H H
part of a nylon polymer chain
Kevlar a polyamide
O O
H2N NH2 C (CH2)4 C
HO OH
O O
N N C (CH2)4 C
H H
part of the kevlar polymer chain

Uses of polyamides
 The main use of polyesters and polyamides is as
fibres in clothing.
 Most clothing now has a degree of
manufactured fibres woven into the natural
material (such as cotton).
 This gives the material more desirable
characteristics, such as stretchiness, and better
washability.
 Don’t forget that proteins are also polyamides,
you must know how the linkage works with
natural polymers such as proteins.

Polymers 1

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Polymerisation

H CHH CHH CHH CHH CHH CHH CHH CH

 These involve the linkage of two monomers

part of the kevlar polymer chain

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