Polymers PDF

Organic
Polymer
Chemistry
Organic Polymer Chem.
Polymer: from the Greek, poly + meros, many parts.

Any long-chain molecule synthesized by linking
together single parts called monomers
Monomer: from the Greek, mono + meros, single

part. The simplest nonredundant unit from which a
polymer is synthesized
Plastic: a polymer that can be molded when hot and

retains its shape when cooled
Copyright 2000 by John Wiley & Sons, Inc. All rights reserved.
Organic Polymer Chem
Thermoplastic: a polymer that can be melted and

molded into a shape that is retained when it is cooled
Thermoset plastic: a polymer that can be molded

when it is first prepared, but once it is cooled,
hardens irreversibly and cannot be remelted
Notation & Nomenclature
Show the structure by placing parens around the repeat

unit
n = average degree of polymerization
Notation & Nomenclature
To name a polymer, prefix poly to the name of the

monomer from which the polymer is derived
if the name of the monomer is one word, no parens are necessary
for more complex monomers or where the name of the monomer
is two words, enclose the name of the monomer is parens, as for
example
poly(vinyl chloride)
poly(ethylene terephthalate)
Chain-Growth Polymers
Addition Polymerization
Chain-growth polymerization: a polymerization in
which monomer units are joined together without
loss of atoms. For example:
nCH2 = CH2 catalyst
CH2 CH2
n
Ethyle ne Polyethylene
Polyethylenes
Monomer Polymer Name(s) and
Formula Common Uses
CH2 =CH 2 polyethylene, Polythene;
break-resistant containers
and packaging materials
CH2 =CHCH 3 polypropylene, Herculon;

textile and carpet fibers
CH2 =CHCl poly(vinyl chloride), PVC;

construction tubing
CH2 =CCl 2 poly(1,1-dichloroethylene) Saran;
food packaging
Polyethylenes
CH 2 =CHCN polyacrylonitrile, Orlon;

acrylics and acrylates
CF 2 =CF 2 polytetrafluoroethylene, Teflon;

nonstick coatings
CH 2 =CHC 6 H5 polystyrene, Styrofoam;

insulating materials
CH 2 =CHCO 2 CH 2 CH 3 poly(ethyl acrylate); latex paints

CH 2 =CCO 2 CH 3 poly(methyl methacrylate), Lucite,
Plexiglas; glass substitutes
CH 3
Polymerization
Radical: a molecule or ion containing one or more

unpaired electrons
Fishhook arrow: a curved and barbed arrow used to
show the repositioning of a single electron
To account for the polymerization of alkenes in the
presence of peroxides, chemists propose a three-step
radical chain mechanism
Radical Chain-Growth
Among the initiators used for radical chain-growth

polymerization are organic peroxides, which
decompose as shown on mild heating
O O
O O
Dibenzoyl
peroxide O
O 2 + 2 CO 2
2
A benzoyloxy A phenyl
radical radical
Polymerization
Step 1: chain initiation

In In In + In
In + CH2 = CH2 In-CH 2 CH2

An alkyl radical
Chain initiation: a step in a radical chain reaction

characterized by the formation of radicals from nonradical
compounds
Polymerization
Step 2: chain propagation

In-CH 2 CH2 + CH2 = CH2 In-CH 2 CH2 CH2 CH2
In-CH 2 CH2 + ( n- 1 ) CH2 = CH2 In-( CH2 CH2 ) n
Chain propagation: a step in a radical chain reaction

characterized by the reaction of a radical and a molecule to
give a new radical
Chain length, n: the number of times the cycle of chain
propagation steps repeats in a chain reaction
Polymerization
Step 3: chain termination

CH2 CH2 + CH2 CH2
CH2 CH2 -CH 2 CH2
Chain termination: a step in a radical chain mechanism that

involves destruction of radicals
Radical Chain-Growth
The first commercial polyethylenes produced by

radical polymerization were soft, tough polymers
known as low density polyethylene (LDPE)
LDPE chains are highly branched due to chain-transfer
reactions
because this branching prevents polyethylene chains from
packing efficiently, LDPE is largely amorphous and
transparent
approx. 65% is fabricated into films for consumer items such
as baked goods, vegetables and other produce, and trash bags
Polymerization
Propylene and other substituted ethylene monomers

can also be polymerized under a variety of
experimental conditions
radical polymerization of propylene involves 2 radical
intermediates to give polypropylene, with methyl groups
repeating on every other carbon
CH3
nCH3 CH= CH2 i nitator CHCH2
n
Propene Polypropylene
(Propylene)
Homework
Please read section 2.1

Page 102 #1-3
Page 107 #4 (top) #1-4 (bottom)
Step-Growth Polymers
Step-growth polymerization: a polymerization in

which chain growth occurs in a stepwise manner
between difunctional monomers
Condensation Polymers
There are five types of step-growth or condensation
polymers
polyesters
polyamides
polycarbonates
polyurethanes
epoxy resins
Polyesters
Poly(ethylene terephthalate) (PET) is fabricated into

Dacron fibers, Mylar films, and plastic beverage
containers
O O
nHOC COH + nHOCH2 CH2 OH heat
1,4-Be nzenedicarboxylic 1,2-Ethane diol
acid (Ethylene glycol)
(Terephthalic acid)
O O
C COCH2 CH2 O + 2 nH2 O
n
Poly(e thylene terephthalate)
(Dacron, Mylar)
Polyesters
ethylene glycol is synthesized from ethylene
O +
O2 H , H2 O
CH 2 = CH 2 CH 2 - CH 2 HOCH 2 CH 2 OH
catalys t
Ethylene Ethylene oxide Ethylene glycol
terephthalic acid is synthesized from p-xylene, which is

obtained from petroleum refining
O O
O2
H3 C CH3 HOC COH
catalyst
p-Xylen e Terephth alic acid
Polyamides
Nylon 66 (from two six-carbon monomers)
O O
heat
nHOC(CH 2 ) 4 COH + nH2 N(CH 2 ) 6 NH2
Hexan edioic acid 1,6-He xanediamine
(Adipic acid) (Hexamethyle nediamine)
O O
C(CH 2 ) 4 CNH(CH 2 ) 6 NH n + 2 nH2 O
Nylon 66
during fabrication, nylon fibers are cold-drawn to about 4
times their original length, which increases crystallinity,
tensile strength, and stiffness
Polyamides
Kevlar
O is a polyaromatic
O amide (an aramid)
nHOC COH + nH2 N NH2
1,4-Be nzenedicarboxylic 1,4-Benze nediamine

acid (p-Phenylen ediamine)
(Terephthalic acid)
O O
C CNH NH + 2 nH2 O
n

Kevlar
cables of Kevlar are as strong as cables of steel, but only about
20% the weight. Kevlar fabric is used for bulletproof vests,
jackets, and raincoats
Recycling Codes
Code Polymer Common Us es

1 poly(ethylene soft drink bottle s, hous ehold
PET te rephthalate ) che mical bottles , films,
te xtile fibe rs
2 high-density milk an d water jugs,
HDPE polyethylene grocery bags, bottles
3 poly(vinyl shampoo bottles , pipes,
V chloride), PVC shower curtains, vinyl
siding, wire ins ulation,
floor tiles, credit cards
4 low-de nsity shrink wrap, trash and
LDPE polyethylene grocery bags, s andwich
bags, squeeze bottles
Recycling Codes
Code Polymer Common Us es

5 polypropylene plastic lids , clothing
PP fibers, bottle caps , toys,
diaper linings
6 polystyre ne styrofoam cups, egg
PS carton s, disposable utens ils,
pack aging materials,
appliance s
7 all oth er variou s
plastics, mixe d
plastics

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Organic

Polymer: from the Greek, poly + meros, many parts.

Monomer: from the Greek, mono + meros, single

Plastic: a polymer that can be molded when hot and

Thermoplastic: a polymer that can be melted and

Thermoset plastic: a polymer that can be molded

Show the structure by placing parens around the repeat

To name a polymer, prefix poly to the name of the

CH2 =CHCH 3 polypropylene, Herculon;

CH2 =CHCl poly(vinyl chloride), PVC;

CH 2 =CHCN polyacrylonitrile, Orlon;

CF 2 =CF 2 polytetrafluoroethylene, Teflon;

CH 2 =CHC 6 H5 polystyrene, Styrofoam;

CH 2 =CHCO 2 CH 2 CH 3 poly(ethyl acrylate); latex paints

Radical: a molecule or ion containing one or more

Among the initiators used for radical chain-growth

Step 1: chain initiation

In + CH2 = CH2 In-CH 2 CH2

Chain initiation: a step in a radical chain reaction

Step 2: chain propagation

In-CH 2 CH2 + ( n- 1 ) CH2 = CH2 In-( CH2 CH2 ) n

Chain propagation: a step in a radical chain reaction

Step 3: chain termination

CH2 CH2 -CH 2 CH2

Chain termination: a step in a radical chain mechanism that

The first commercial polyethylenes produced by

Propylene and other substituted ethylene monomers

Please read section 2.1

Step-growth polymerization: a polymerization in

Poly(ethylene terephthalate) (PET) is fabricated into

terephthalic acid is synthesized from p-xylene, which is

1,4-Be nzenedicarboxylic 1,4-Benze nediamine

Code Polymer Common Us es

Code Polymer Common Us es

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