Organic Polymer Chemistry

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 Ethyle ne catalyst n Polyethylene CH2 CH2
Polyethylenes
Monomer Formula CH2 =CH 2 Polymer Name(s) and Common Uses polyethylene, Polythene; break-resistant containers and packaging materials polypropylene, Herculon; textile and carpet fibers poly(vinyl chloride), PVC; construction tubing poly(1,1-dichloroethylene) Saran; food packaging
CH2 =CHCH 3 CH2 =CHCl CH2 =CCl 2
Polyethylenes
CH 2 =CHCN CF 2 =CF 2 CH 2 =CHC 6 H5 polyacrylonitrile, Orlon; acrylics and acrylates polytetrafluoroethylene, Teflon; nonstick coatings polystyrene, Styrofoam; insulating materials
CH 2 =CHCO 2 CH 2 CH 3 poly(ethyl acrylate); latex paints poly(methyl methacrylate), Lucite, CH 2 =CCO 2 CH 3 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 O 2 A phenyl radical + 2 CO 2 O
Dibenzoyl peroxide 2
A benzoyloxy 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 + ( n- 1 ) CH2 = CH2
In-CH 2 CH2 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 Propene (Propylene) n Polypropylene CHCH2
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 1,2-Ethane diol (Ethylene glycol) O COCH2 CH2 O + 2 nH2 O
1,4-Be nzenedicarboxylic acid (Terephthalic acid) O C
n Poly(e thylene terephthalate) (Dacron, Mylar)

Polyesters
ethylene glycol is synthesized from ethylene
CH 2 = CH 2 Ethylene
O2 catalys t Ethylene oxide
+ O H , H2 O CH 2 - CH 2 HOCH 2 CH 2 OH
Ethylene glycol
terephthalic acid is synthesized from p-xylene, which is obtained from petroleum refining
H3 C p-Xylen e
CH3
O O2 HOC COH catalyst 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 (Adipic acid) O
1,6-He xanediamine (Hexamethyle nediamine) 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 amide (an aramid) O O is a polyaromatic
nHOC
COH + nH2 N
NH2
1,4-Be nzenedicarboxylic acid (Terephthalic acid) O C
1,4-Benze nediamine (p-Phenylen ediamine) O 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 1 PET 2 HDPE 3 V Polymer poly(ethylene te rephthalate ) high-density polyethylene poly(vinyl chloride), PVC Common Us es soft drink bottle s, hous ehold che mical bottles , films, te xtile fibe rs milk an d water jugs, grocery bags, bottles shampoo bottles , pipes, shower curtains, vinyl siding, wire ins ulation, floor tiles, credit cards shrink wrap, trash and grocery bags, s andwich bags, squeeze bottles
4 LDPE
low-de nsity polyethylene
Recycling Codes
Code 5 PP 6 PS Polymer polypropylene Common Us es plastic lids , clothing fibers, bottle caps , toys, diaper linings styrofoam cups, egg carton s, disposable utens ils, pack aging materials, appliance s variou s
polystyre ne
all oth er plastics, mixe d plastics

Organic Polymer Chemistry

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Organic Polymer Chemistry

Organic Polymer Chem.

part. The simplest nonredundant unit from which a polymer is synthesized

retains its shape when cooled

Organic Polymer Chem

molded into a shape that is retained when it is cooled

Notation & Nomenclature

unit n = average degree of polymerization

Notation & Nomenclature

monomer from which the polymer is derived

CH2 =CHCH 3 CH2 =CHCl CH2 =CCl 2

polymerization are organic peroxides, which decompose as shown on mild heating

In-CH 2 CH2 An alkyl radical

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

In-CH 2 CH2 CH2 CH2 In-( CH2 CH2 ) n

CH2 CH2 CH2 CH2 -CH 2 CH2

can also be polymerized under a variety of experimental conditions

CH3 nCH3 CH= CH2 i nitator Propene (Propylene) n Polypropylene CHCH2

polyesters polyamides polycarbonates polyurethanes epoxy resins

Dacron fibers, Mylar films, and plastic beverage containers

1,4-Be nzenedicarboxylic acid (Terephthalic acid) O C

n Poly(e thylene terephthalate) (Dacron, Mylar)

ethylene glycol is synthesized from ethylene

O2 catalys t Ethylene oxide

O O2 HOC COH catalyst Terephth alic acid

Hexan edioic acid (Adipic acid) O

1,6-He xanediamine (Hexamethyle nediamine) O

1,4-Be nzenedicarboxylic acid (Terephthalic acid) O C

1,4-Benze nediamine (p-Phenylen ediamine) O CNH NH + 2 nH2 O

low-de nsity polyethylene

all oth er plastics, mixe d plastics

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