Topics for Today

1
Topics for Today

• PET (A Polyester)!
• Linking the Chain (Finally!!)
• Nylon!

2
Readings for Today

• 9.5 Condensation Polymers
• 9.6 Nylon and Polyamides
• 10.3 Functional Groups!

3
Topics for Wednesday

• Back to PVC and Addition Polymers
• Stiff or Flexible? Plasticizers

4
Readings for Wednesday

• Review
• 9.2 The Big Six
• 9.3 Addition Polymers

5
Topics for Friday
6
Exam 3!
This Friday!
Same format as always
7
Exam 3!
Non-memory calculators OK.
Please, no cell phones
8
Topics for Today

• PET (A Polyester)!
• Linking the Chain (Finally!!)
• Nylon

9
Review
10
H
Carboxylic Acid Alcohol
Ester Water
At home Try with benzoic acid ethanol!
Methanoic Acid (Formic Acid)
Ethanol
O
H

HO
CH2
CH3
C
H
H2O
O
H
O

C
H
CH2
CH3
O
11
Making a polyester!

• PETE (A Polyester)!

12
H
Double Double
Poly
Carboxylic Acid Alcohol
Ester Water
13
Double Double
Poly
H
Carboxylic Acid Alcohol
Ester Water
14
Terephthalic Acid
O
C
OH
Double Acid!
Monomer 1!
O
C
HO
15
H
Double Double
Poly
Carboxylic Acid Alcohol
Ester Water
16
H
Double Double
Poly
Carboxylic Acid Alcohol
Ester Water
17
Ethylene Glycol Monomer 2
A double alcohol!
H
H
C
C
HO
OH
H
H
Compare to ethanol
18
H
Double Double
Poly
Carboxylic Acid Alcohol
Ester Water
Reacting terephthalic acid with ethylene glycol!
19
Double Double
Poly
H
Carboxylic Acid Alcohol
Ester Water
H
H
H
O
O

OH
C
C
O
H
C
C
HO
OH
H
H
O
O
H
H

C
C
HOH
OH
HO
O
C
C
H
H
ESTER!
20
This is with one of each monomer.
What if we add more monomers?
21
Alcohol
O
O
H
H
C
C
HO
O
H
O
C
C
H
H
H
H
C
C
O
O
H
H
H
H
O
O
C
C
HO
OH
ACID
22
Figure 9.8 (p. 412)
23
What about 1000 (or more) links??
More Esters
Figure 9.8 (p. 412)
24
Polyester terephthalate (ester)
H
H
O
O
H

n
n
C
C
O
OH
H
C
C
HO
OH
H
H
O
O
H
H
n
H2O
C
C

O
O
C
C
H
H
n
25
Summary
O
O
H
H
C
C
O
O
C
C
H
H
n
Double Acid
Double Alcohol
Double Acid
Double Alcohol
ESTER
ESTER
ESTER
ESTER
ESTER
26
Why is PET(E) called a condensation polymer?
27
Condensation Polymerization

• When a smaller molecule (such as water) is
  produced during the polymerization process

28
Monomer(s)?
Repeating Unit?
Why is PET(E) called a condensation polymer?
Polymer?
29
Properties of PET?
30

• light weight
• shatter resistant
• withstands pressure of CO2

31

• light weight
• shatter resistant
• withstands pressure of CO2
• Clear and lustrous (glistening)
• High melting point (260oC)

32
Other condensation polymers?
33
Condensation Polymers!
Polyester
Nylon
34
First produced in the 1930s.
Nylon
Synthetic Silk
35
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36
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37
Nylon Fibers

• Strong, tough
• Flexible
• Resist abrasion
• Easily washed, dried

38
Nylon

• Melts at 265 C

39
Where else do we find nylon?
40
Kitchenware
41
Ropes
42
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43
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44
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45
Flexible and Robust!

• Toothbrush bristles

46
Nylon
Nylon is a generic term.
A polyamide!
Chemically, what is nylon?
47
Natural Polyamides
Spider Webs and Silk
48
Natural Polyamides
Proteins!
49
Nylon is a polyamide!
Whats an amide?
50
Functional Groups
Making an amide
Ester R C O R

O
Carboxylic R C O H Acid

O
..
Amide R C N R

O
H
51
Review - Ester
H
Carboxylic Acid Alcohol
Ester Water
52
NEW!! (Amide)
H
Carboxylic Acid Amine
Amide Water
Polyamide?
53
NEW!! (Polyamide)
Double Double
Poly
H
Acid Amine
Amide Water
Hydrocarbon groups with nitrogen
?
54
Where have we seen nitrogen-containing compounds
before?
55
Nitrogen, N2
A colorless, odorless, tasteless gas
56
Nitrogen Compounds

• N2

57
NO NO2 nasty odor
nasty odor highly reactive reactive
poisonous poisonous colorless
red-brown
58
Nitrogen Compounds

• N2
• NO and NO2

59
NH3 H2O ? NH4OH
60
Nitrogen Compounds

• N2
• NO and NO2
• NH3 and NH4

Other compounds?
61
Ester R C O R

O
Carboxylic R C O H Acid

O
..
Amide R C N R

O
H
..
Amine
N
R
R
R
62
Nitrogen Compounds
Drawing Amines!

• N2
• NO and NO2
• NH3 and NH4
• Amines and Amides

63
Amines
..
N
R
R
R
64
Amines
Based off of ammonia!
..
N
H
H
H
65
Methylamine
Draw ethylamine!
..
N
CH3
H
H
66
Ethylamine
One more
..
N
CH2CH3
H
H
67
Dimethylamine
Name?
..
N
CH3
H3C
H
68
Nitrogen Compounds
Where do we find amines?

• N2
• NO and NO2
• NH3 and NH4
• Amines and Amides

69
Drugs
Where do we find amines?
70
Celebrex
Figure 10.9 (p. 444)
71
Oxy-contin
Figure 10.35 (p. 476)
72
Methamphetamine
Figure 10.33 (p. 475)
73
Morphine
74
Quinine

• Anti-malarial drug

75
Caffeine!
76
Nicotine
77
In us!
Where do we find amines in nature?
78
Amino Acids
Histidine
79
Serotonin

• A neurochemical

80
Putrescine Cadaverine
Products from the breakdown of amino acids
81
Nitrogen Compounds

• N2
• NO and NO2
• NH3 and NH4
• Amines and Amides

82
NEW!! (Amide)
H
Carboxylic Acid Amine
Amide Water
83
NEW!! (Amide)
H
Carboxylic Acid Amine
Amide Water
..
O
H
N

C
H
CH3
H
H
O
H
O
..

H2O
CH3
C
H
N
H
Amide
84
NEW!! (Polyamide)
Double Double
Poly
H
Acid Amine
Amide Water
85
Adipic acid (Monomer 1)
A diacid!
Equation 9.8 (p. 414)
86
NEW!! (Polyamide)
Double Double
Poly
H
Acid Amine
Amide Water
87
Hexamethylenediamine (Monomer 2)
Equation 9.8 (p. 414)
88
NEW!! (Polyamide)
Double Double
Poly
H
Acid Amine
Amide Water
One of each monomer
89
Equation 9.8 (p. 414)
90
Amide!
Equation 9.8 (p. 414)
91
What happens when you add 100s more monomers?
Equation 9.8 (p. 414)
92
Summary Nylon 6,6
O
H
H
O
N
C
N
(CH2)6
C
(CH2)4
n
Double Acid
Double Amine
Double Acid
Double Amine
AMIDE
AMIDE
AMIDE
AMIDE
AMIDE
93
Monomers?
Repeating Unit?
Be able to write the overall reaction for the
production of a polyamide for ANY given diacid
and diamine!!!!