Typical Condensation Polymers Polymerization Reaction in .NET

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TABLE 1-1 Typical Condensation Polymers Polymerization Reaction
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Type
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Characteristic Linkage
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Polyamide
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NH CO
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H2N R NH2 + HO2C R CO2H H2N R NH2 + ClCO R COCl
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H NH R NHCO R CO OH + H2O H NH R NHCO R CO Cl + HCl
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H2N R CO2H
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Protein, wool, silk
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NH CO
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H NH R CO OH + H2O n Naturally occurring polypeptide polymers; degradable to mixtures of different amino acids. H NH R CONH R CO OH + H2O
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H2N R CO2H + H2N R CO2H H O R OCO H O R OCO R CO OH + H2O
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Polyester
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CO O
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HO R OH + HO2C R CO2H HO R OH + R O2C R CO2R HO R CO2H
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R CO OH + R OH
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H O R CO OH + H2O O R OCO NH R NH CO H O SiR2 OH + H2O
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n H2O n
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Polyurethane
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O NH CO
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HO R OH + OCN R NCO Cl SiR2
HCl
Polysiloxane
Si O
Cl OH
HO SiR2 OH
OH + CH2O
Phenol formaldehyde
Ar 2 CH
+ H2O
Urea formaldehyde
NH 2 CH
H2N CO NH2 + CH2O H2N C N C NH2 Cl R Cl + Na2Sm N N C NH2 + CH2O
HN CO NH CH2 HN C N N C
+ H2O C NH CH2 N NH2 Sm R
Melamine formaldehyde
NH 2 CH
+ H2O
Polysul de
Sm
+ NaCl O R OCHR
Polyacetal
O CH O
R CHO + HO R OH
+ H2O
INTRODUCTION
sense cellulose is considered a condensation polymer, since its hydrolysis yields glucose, which contains the repeating unit of cellulose plus the elements of water
CH2OH H CH O CH CH OH O CH CH OH
CH2OH OH + (n 1)H2O CH nHO CH CH OH O CH OH CH OH
1-4
Cellulose
Glucose
Addition polymers were classi ed by Carothers as those formed from nonomers without the loss of a small molecule. Unlike condensation polymers, the repeating unit of an addition polymer has the same composition as the monomer. The major addition polymers are those formed by polymerization of monomers containing the carbon carbon double bond. Such monomers will be referred to as vinyl monomers throughout this text. (The term vinyl, strictly speaking, refers to a CH2 CH group attached to some substituent. Our use of the term vinyl monomer is broader it applies to all monomers containing a carbon carbon double bond, including monomers such as methyl methacrylate, vinylidene chloride, and 2-butene as well as vinyl chloride and styrene. The term substituted ethylenes will also be used interchangeably with the term vinyl monomers.) Vinyl monomers can be made to react with themselves to form polymers by conversion of their double bonds into saturated linkages, for example
1-5
nCH2
CH2 CHY
where Y can be any substituent group such as hydrogen, alkyl, aryl, nitrile, ester, acid, ketone, ether, and halogen. Table 1-2 shows many of the common addition polymers and the monomers from which they are produced. The development of polymer science with the study of new polymerization processes and polymers showed that the original classi cation by Carothers was not entirely adequate and left much to be desired. Thus, for example, consider the polyurethanes, which are formed by the reaction of diols with diisocyanates without the elimination of any small molecule:
nHO R OH + nOCN R NCO HO R OCONH R NHCO O
(n 1)
R OCONH
R NCO
1-6
Using Carothers original classi cation, one would classify the polyurethanes as addition polymers, since the polymer has the same elemental composition as the sum of the monomers. However, the polyurethanes are structurally much more similar to the condensation polymers than to the addition polymers. The urethane linkage ( CO ) has much NH O in common with the ester ( O and amide ( CO linkages. CO ) NH ) To avoid the obviously incorrect classi cation of polyurethanes as well as of some other polymers as addition polymers, polymers have also been classi ed from a consideration of the chemical structure of the groups present in the polymer chains. Condensation polymers have been de ned as those polymers whose repeating units are joined together by functional
TYPES OF POLYMERS AND POLYMERIZATIONS
TABLE 1-2 Typical Addition Polymers Polymer Polyethylene Monomer Repeating Unit
CH2 CH3
CH2 CH3
Polyisobutylene
C CH3
C CH3
Polyacrylonitrile
CH CN
CH CN
Poly(vinyl chloride)
CH Cl
CH Cl
Polystyrene
CH CH3
CH CH3
Poly(methyl methacrylate)
C CO2CH3
C CO2CH3
Poly(vinyl acetate)
CH OCOCH3 Cl
CH OCOCH3 Cl
Poly(vinylidene chloride)
C Cl
C Cl
Polytetra uoroethylene
F F C CH CH2 CH3
F F CH2 C CH
C C F
Polyisoprene (natural rubber)
CH2 CH3
units of one kind or another such as the ester, amide, urethane, sul de, and ether linkages. Thus the structure of condensation polymers has been de ned by
R Z R Z R Z R Z R Z I
where R is an aliphatic or aromatic grouping and Z is a functional unit such as OCO , NHCO , , S OCONH , , O OCOO and 2 Addition polymers, on the , SO . other hand, do not contain such functional groups as part of the polymer chain. Such groups may, however, be present in addition polymers as pendant substituents hanging off the polymer chain. According to this classi cation, the polyurethanes are readily and more correctly classi ed as condensation polymers.
INTRODUCTION
It should not be taken for granted that all polymers that are de ned as condensation polymers by Carothers classi cation will also be so de ned by a consideration of the polymer chain structure. Some condensation polymers do not contain functional groups such as ester or amide in the polymer chain. An example is the phenol formaldehyde polymers produced by the reaction of phenol (or substituted phenols) with formaldehyde