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CHM 585 / 490. Chapter 6 Condensation polymers. Chapter 6 Condensation Polymers. PBT PEN PC Nylon Polyimides. 1,4-Butanediol. Polybutyleneterephthalate PBT. Polyethylene naphthalate PEN. Phosgene. Phosgene. 4 billion pounds per year Poisonous gas - PowerPoint PPT Presentation
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CHM 585 / 490
Chapter 6Condensation polymers
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Chapter 6 Condensation Polymers
• PBT• PEN• PC• Nylon• Polyimides
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1,4-Butanediol
+H H
O2 CH2OHHOH2C
CH2OHHOH2C OHHOH2
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PolybutyleneterephthalatePBT
CO2CH3
CO2CH3
+ OHHOCO2CH2CH2CH2CH2O
O(
)n
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Polyethylene naphthalatePEN
CO2H
HO2C+
OHHO
CO2CH2CH2O
O(
)n
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Phosgene
Cl2 + COCl
O
Cl
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Phosgene
• 4 billion pounds per year• Poisonous gas• Mostly captive: GE, BASF, Dow, PPG• Van deMark at 20 million pounds is the
only merchant supplier (purchased by SNPE)
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Polycarbonate
OHHO
+ 2 NaOH +
Cl
O
Cl OOO
( )n
+ 2 NaCl
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Polycarbonate
OHHO OOO
( )n
+ OO
O
OH
+ 2
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Diphenylcarbonate
OH
OO
OH3CO
O
OCH3+ + 2 CH3OH2
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Nylons
RCO2H + R'NH2 R
O
NHR'
Amide
+ H2O
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Nylons
• Diamine and Dicarboxylic acid to form a polyamide
• Nylon 4,6 is from diaminobutane and adipic acid
R' NH2H2N + R CO2HHO2C R'HN
HN
OR
O( )n
O
OH
O
HO
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Nomenclature
• Nylon 6,6 is from 1,6-hexanediamine and adipic acid
• Nylon 6,12 is from a 6 carbon diamine and a 12 carbon dicarboxylic acid
• What is nylon 6 ????
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Nylon 6
• From the polymerization of caprolactam
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16
17
18
19
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21
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U.S. Nylon Consumption
Nylon 6,6 55%
Nylon 6 38%
Nylons 4,6; 6,9; 6,10; 6,12; 11, 12 and various others
7%
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High Heat Nylons
• Kevlar: all para
• Nomex: meta
HN
OHN
O( )
n
HN(
HN
O
O)
n
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Polyimides
O
O
O
RNH2 + NR
O
O
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Kapton
H2N O NH2 OO
O
O
O
O
+
N
O
O
O
O
O N( )n
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