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PPP Pooo olll lyyy ymmm meee errr r SSS Sccc ciii ieee ennn nccc ceee e aaa

aa annn nddd d EEE Ennn nggg giii innn neee eeee errr riii innn nggg g
"I am inclined to think that the
development of polymerization
is perhaps the biggest thing that
chemistry has done, where it has
had the biggest effect on
everyday life
Lord Todd,1980
Ethylene Polyethylene
CH
2
= CH
2
[-CH
2
- CH
2
-]
n
Magic ?
USE NATURAL SYNTHETIC
Fibers Wool, Silk,
Cellulose
Nylon, PET,
Lycra

Elastomers Natural Rubber,


Elastin
SBR, Silicones,
Polybutadiene
Plastics Gutta Percha,
DNA,
Polypeptides
Polyethylene,
Polypropylene,
Polystyrene
Composites Wood,
Bone,
Teeth
Polyester/Glass,
Carbon Fiber/Epoxy
Formica
Adhesives Barnacles! Elmers Glue-All
Super-Glue
Paints Shellac Acrylics
AAA A UUU Usss seee efff fuuu ulll l CCC Clll laaa asss ssss siii ifff fiii iccc caaa attt tiii iooo onnn n
HHH Hiii isss sttt tooo orrr riii iccc caaa alll l BBB Baaa accc ckkk kggg grrr rooo ouuu unnn nddd d
NATURAL POLYMERS - used throughout recorded
history
SYNTHETIC POLYMERS - initially chemically modified
natural polymers
RUBBERS OR ELASTOMERS - unique materials, both
natural and synthetic
HH
H H
ii
i i
ss
s s
tt
t t
oo
o o
rr
r r
ii
i i
cc
c c
aa
a a
ll
l l
BB
B B
aa
a a
cc
c c
kk
k k
gg
g g
rr
r r
oo
o o
uu
u u
nn
n n
dd
d d
SCHOENBEIM - nitration reactions
MENARD - collodion films ;nitrated
cellulose
PARKES - "Parkesine" ; added
camphor (and other stuff)
- plasticizers
HYATT - billiard balls !!
CHARDONNET - extrusion

CROSS, BEVAN, - regenerated cellulose
& BEADLE rayon,cellophane
BAEKELAND - Bakelite, the first thermoset
STAUDINGER - the macromolecular hypothesis
NEW THERMOPLASTICS - (more on these later)
1845
1848
1862
1870s
1884
1890s
1905
1920
> 1920
NN
N N
aa
a a
tt
t t
uu
u u
rr
r r
aa
a a
ll
l l
PP
P P
oo
o o
ll
l l
yy
y y
mm
m m
ee
e e
rr
r r
ss
s s
A natural fiber
on the hoof
Silk
NATURAL POLYMERS - - used throughout recorded history
Better hope your garden never looks like this
CC
C C
oo
o o
tt
t t
tt
t t
oo
o o
nn
n n
O
OH
CH
2
OH
O
HO
n
Cellulose
NN
N N
ii
i i
tt
t t
rr
r r
aa
a a
tt
t t
ee
e e
dd
d d
CC
C C
ee
e e
ll
l l
ll
l l
uu
u u
ll
l l
oo
o o
ss
s s
ee
e e
Schoenbeim
Glycerol
CH
2
OHCHOHCH
2
OH
Nitroglycerin
C
C
C
C
C
C
O
O
O
O
O
O
O O
O
O O
O
N
N
N
EE
E E
xx
x x
pp
p p
ll
l l
oo
o o
ss
s s
ii
i i
vv
v v
ee
e e
SS
S S
tt
t t
uu
u u
ff
f f
ff
f f
!!
! !
SSS Sooo ommm meee e BBB Baaa asss siii iccc c CCC Chhh heee emmm miii isss sttt trrr ryyy y::: :
AAA Attt tooo ommm msss s aaa annn nddd d BBB Booo onnn nddd diii innn nggg g
H H
H H
Na
Cl
Na
Cl
Covalent Ionic
Metallic

+
Molecule
Does not form NaCl molecule!
C
SSS Sooo ommm meee e BBB Baaa asss siii iccc c CCC Chhh heee emmm miii isss sttt trrr ryyy y::: :
SSS Siii innn nggg glll leee e aaa annn nddd d DDD Dooo ouuu ubbb blll leee e BBB Booo onnn nddd dsss s
C C C

H
H
H H
C
C

H
H
H C

H
H
H
C C C

H
H
C

H
H

CH
4
C
2
H
6
C
2
H
4
SSS Sooo ommm meee e BBB Baaa asss siii iccc c CCC Chhh heee emmm miii isss sttt trrr ryyy y::: :
FFF Fuuu unnn nccc cttt tiii iooo onnn naaa alll l GGG Grrr rooo ouuu uppp psss s
Functional Groups are small groups of atoms held together in a specific
arrangement by covalent bonds. They are responsible for the principle chemical
properties of the molecule in which they are found.
CH
2
=CH
2
ROH RCOH
=
O
RCOR
=
O
RNH
2
RCOH
=
O
RCNHR
=
O
+
+
Alcohol Carboxylic Acid Ester
Carboxylic Acid Amine Amide
Ethylene
CC
C C
oo
o o
nn
n n
dd
d d
ee
e e
nn
n n
ss
s s
aa
a a
tt
t t
ii
i i
oo
o o
nn
n n
RR
R R
ee
e e
aa
a a
cc
c c
tt
t t
ii
i i
oo
o o
nn
n n
ss
s s
Acetic Acid Ethyl Alcohol
or Ethanol
Reversible
Reaction!
Ethyl Acetate
If you dont
know what this
is you should
be castigated
unmercifully
Ester linkage
CH
3
- C - OH + CH
3
- CH
2
- OH CH
3
- C - O - CH
2
- CH
3
+ H
2
O
O O
WW
W W
hh
h h
yy
y y
dd
d d
oo
o o
MM
M M
oo
o o
ll
l l
ee
e e
cc
c c
uu
u u
ll
l l
ee
e e
ss
s s
RR
R R
ee
e e
aa
a a
cc
c c
tt
t t
??
? ?
CH
3
- C - OH
O
HO - CH
2
- CH
3

Acetic Acid
kersplat!
Ethyl Alcohol
or Ethanol
WW
W W
hh
h h
yy
y y
dd
d d
oo
o o
MM
M M
oo
o o
ll
l l
ee
e e
cc
c c
uu
u u
ll
l l
ee
e e
ss
s s
RR
R R
ee
e e
aa
a a
cc
c c
tt
t t
??
? ?
H:O - CH
2
- CH
3

CH
3
- C:OH
O
HO
.
+
.
H HO:H ~ H
2
O
CH
3
- C
.
+
.
O - CH
2
- CH
3
CH
3
- C:O - CH
2
- CH
3

OO O
This isnt what really happens, but shows you
how the valency electrons get rearranged
MM
M M
aa
a a
kk
k k
ii
i i
nn
n n
gg
g g
aa
a a
PP
P P
oo
o o
ll
l l
yy
y y
mm
m m
ee
e e
rr
r r
Acetic Acid Ethyl Alcohol
or Ethanol
Reversible
Reaction!
Ethyl Acetate
Ester linkage
CH
3
- C - OH + CH
3
- CH
2
- OH CH
3
- C - O - CH
2
- CH
3
+ H
2
O
O O
If we heat acetic acid and ethanol up to just over 100
0
C,
to get the reaction going and drive off water, why dont
we form polymer?
Glycerol
CH
2
OHCHOHCH
2
OH
Nitroglycerin
C
C
C
C
C
C
O
O
O
O
O
O
O O
O
O O
O
N
N
N
EE
E E
xx
x x
pp
p p
ll
l l
oo
o o
ss
s s
ii
i i
vv
v v
ee
e e
SS
S S
tt
t t
uu
u u
ff
f f
ff
f f
!!
! !
GG
G G
uu
u u
nn
n n
cc
c c
oo
o o
tt
t t
tt
t t
oo
o o
nn
n n

aa
a a
nn
n n
dd
d d

CC
C C
oo
o o
ll
l l
ll
l l
oo
o o
dd
d d
ii
i i
oo
o o
nn
n n
GG
G G
uu
u u
nn
n n
cc
c c
oo
o o
tt
t t
tt
t t
oo
o o
nn
n n
aa
a a
nn
n n
dd
d d
CC
C C
oo
o o
ll
l l
ll
l l
oo
o o
dd
d d
ii
i i
oo
o o
nn
n n
PP
P P
aa
a a
rr
r r
kk
k k
ee
e e
ss
s s
aa
a a
nn
n n
dd
d d
PP
P P
aa
a a
rr
r r
kk
k k
ee
e e
ss
s s
ii
i i
nn
n n
ee
e e
He wasnt this
miserable.
TT
T T
hh
h h
ee
e e
CC
C C
rr
r r
yy
y y
ss
s s
tt
t t
aa
a a
ll
l l
PP
P P
aa
a a
ll
l l
aa
a a
cc
c c
ee
e e
HH
H H
yy
y y
aa
a a
tt
t t
tt
t t
aa
a a
nn
n n
dd
d d
tt
t t
hh
h h
ee
e e
EE
E E
ll
l l
ee
e e
pp
p p
hh
h h
aa
a a
nn
n n
tt
t t
ss
s s
CCC Ceee elll llll luuu ulll looo oiii iddd d
What a sales pitch
CCC Chhh haaa arrr rddd dooo onnn nnnn neee ettt t aaa annn nddd d MMM Mooo ottt thhh heee errr r--- -iii innn n--- -LLL Laaa awww w SSS Siii illl lkkk k

O
HO
OH
O
CH
2
OH
CH
2
ONa
O
HO
OH
O
O
HO
OH
O
CH
2
OCSNa
S
CH
2
OH
O
HO
OH
O
NaOH
CS
2
H
+
RR
R R
ee
e e
gg
g g
ee
e e
nn
n n
ee
e e
rr
r r
aa
a a
tt
t t
ee
e e
dd
d d
CC
C C
ee
e e
ll
l l
ll
l l
uu
u u
ll
l l
oo
o o
ss
s s
ee
e e
CCC Ceee elll llll looo oppp phhh haaa annn neee e aaa annn nddd d RRR Raaa ayyy yooo onnn n
MMM Mooo orrr reee e
CCC Ceee elll llll looo oppp phhh haaa annn neee e
RRR Raaa ayyy yooo onnn n
BBB Baaa aeee ekkk keee elll laaa annn nddd d aaa annn nddd d BBB Baaa akkk keee elll liii ittt teee e
The first true synthetic plastic
A Bakelite telephone
A Bakelite microphone A Bakelite camera
Clear Bakelite items
A Bakelite radio
Clock made of a phenolic resin
and celluloid
BBB Baaa akkk keee elll liii ittt teee e --- - MMM Maaa attt teee errr riii iaaa alll l ooo offf f aaa a TTT Thhh hooo ouuu usss saaa annn nddd d UUU Usss seee esss s
NN
N N
ee
e e
tt
t t
ww
w w
oo
o o
rr
r r
kk
k k
FF
F F
oo
o o
rr
r r
mm
m m
aa
a a
tt
t t
ii
i i
oo
o o
nn
n n

OH
CH
2
OH
OH
CH
2
OH
CH
2
CH
2
OH
CH
2
OH
OH OH
CH
2
CH
2

OH
+ CH
2
O
*
*
* *
The hydrogens in the ortho and para positions to
the OH group, which by convention are not
usually shown but here are indicated by a , can
react with fomaldehyde to form (initially)
oligomers.
OH
H
H
H
H H
OH
H
H
H
H H
H
H
O
H H
O
OH
H
H
H
H H
AA
A A
CC
C C
oo
o o
nn
n n
dd
d d
ee
e e
nn
n n
ss
s s
aa
a a
tt
t t
ii
i i
oo
o o
nn
n n
RR
R R
ee
e e
aa
a a
cc
c c
tt
t t
ii
i i
oo
o o
nn
n n
!!
! !

OH
CH
2
O
H
2
C
CH
2
HO
OH
CH
2
CH
2
OH
CH
2
HO
CH
2
OH
CH
2
CH
2
O
OH
CH
2
CH
2
OH
O
CH
2
HO
CH
2
CH
2
OH
CH
2
CH
2
OH
HO
CH
2
HO
CH
2 CH
2
H
2
C
HO
NN
N N
ee
e e
tt
t t
ww
w w
oo
o o
rr
r r
kk
k k
FF
F F
oo
o o
rr
r r
mm
m m
aa
a a
tt
t t
ii
i i
oo
o o
nn
n n
Continued reaction
builds up a densely
cross-linked network.
This is Bakelite, a
thermosetting
polymer. Once the
reaction is complete,
the material cannot
be reheated and
reformed. So, what do
you think the
definition of a
thermoplastic is?
NNN NEEE EXXX XTTT T;;; ;
SSS Sttt taaa auuu uddd diii innn nggg geee errr r aaa annn nddd d ttt thhh heee e
MMM Maaa accc crrr rooo ommm mooo olll leee eccc cuuu ulll laaa arrr r
HHH Hyyy yppp pooo ottt thhh heee esss siii isss s