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Topics for Today. Back to PVC and Addition Polymers Stiff or Flexible? Plasticizers. Topics for Today. Orientation of the polymer Head-to-head? Head-to-tail? What else is in plastic?. Readings for Today. Review 9.2 The Big Six 9.3 Addition Polymers. Topics for Friday. Exam #3!.

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topics for today
Topics for Today
  • Back to PVC and Addition Polymers
    • Stiff or Flexible? Plasticizers
topics for today1
Topics for Today
  • Orientation of the polymer
    • Head-to-head? Head-to-tail?
  • What else is in plastic?
readings for today
Readings for Today
  • Review
    • 9.2 The Big Six
    • 9.3 Addition Polymers
exam 3
Exam #3!

This Friday!

Same format as always

exam 31
Exam #3!

Non-memory calculators OK.

Please, no cell phones

topics for monday
Topics for Monday
  • Lipids, Fats, and Oils!
topics for monday1
Topics for Monday
  • What is a fat? Fatty acid?
  • Saturated vs unsaturated fats
  • Animal versus plant
readings for monday
Readings For Monday
  • 11.3 Fat & Oils: Part of the lipid family
  • 11.4 Saturated and Unsaturated Fats & Oils
slide10

Figures Alive!

http://chemincontext.eppg.com/chapter11/FiguresAlive.html

topics for today2
Topics for Today
  • Back to PVC and Addition Polymers
    • Stiff or Flexible? Plasticizers
summary pet

Monomers?

Summary… PET

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

summary nylon 6 6

Monomers?

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

slide16

Be able to write the overall reaction for production of a polyamide for ANY given diacid and diamine!!!!

Same for the production of a polyester for ANY given diacid and dialcohol!!

slide18

Equation 9.7

(p. 414)

Built from amino acids!

condensation polymers1
Condensation Polymers
  • Nylon and PET (polyester)

A small molecule is released as a byproduct

Can be built from one or two monomers

addition polymers
Addition Polymers
  • PP, PS, HDPE, LDPE, PVC, Teflon

1 monomer

No byproducts!

polyethylene
Polyethylene

[

]n

H

H

–CH2–CH2–

n

C = C

H

H

EXPAND!

polyethylene1
Polyethylene

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

polypropylene
Polypropylene

Does the orientation matter?

H

H

H

H

— C – C—

n

C = C

n

H

CH3

H

CH3

Expand out…

slide24

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

Same or different?

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

slide25

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

CH3

CH3

CH3

CH3

CH3

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

CH3

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

CH3

CH3

CH3

CH3

CH3

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

polyproylene
Polyproylene

Does the orientation matter?

H

H

H

H

— C – C—

n

C = C

n

H

CH3

H

CH3

HEAD

TAIL

slide27

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

polypropylene head to tail
Polypropylene Head-to-Tail

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

Any other options?

= methyl

= H

slide29

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

These are all head-to-tail!!

CH3

CH3

CH3

CH3

CH3

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

CH3

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

CH3

CH3

CH3

CH3

CH3

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

polypropylene head to head
Polypropylene Head-to-Head

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

Any other options?

= methyl

= H

slide31

Polypropylene - Random

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

H

CH3

H

H

CH3

H

H

H

H

H

H

H

H

C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

-C

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

= methyl

= H

polystyrene
Polystyrene

Glassy and brittle

polystyrene1
Polystyrene
  • Can be injected with a gas to make foam!

We used to use CFCs!

polystyrene2
Polystyrene?

H

H

H

H

— C – C—

n

C = C

n

H

H

HEAD

TAIL

polystyrene3
Polystyrene

What orientation?

slide37

Polymerize!

Cl

H

C

C

H

H

vinyl chloride

polyvinylchloride pvc
Polyvinylchloride (PVC)

H

H

H

H

— C – C—

n

C = C

n

H

Cl

H

Cl

slide39
PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

slide40
PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well

slide41

Rigid, stiff material

PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well

slide42
PVC

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head

slide43

Rigid, stiff material

PVC

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head

Has order – packs well

slide44
PVC

Cl

Cl

Cl

Cl

Cl

Random

slide45
PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well

slide46

Slightly softer

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well

slide48
PVC
  • Can be opaque

and rigid

slide49
PVC
  • Can be opaque and rigid
slide50
PVC
  • Can be transparent and

softer

slide57
PVC

Why not?

slide58
PVC

PVC is usually not recyclable

Why not?

plasticizers
Plasticizers
  • Big molecules added to soften a plastic

Can often make-up about 30% of a plastic’s weight!

slide60

Still not soft enough for some uses…

Slightly softer

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well

plasticizers1
Plasticizers

Phthalates are commonly used

Where have we seen phthlate-related compounds?

slide65
DEHP
  • Di(2-ethylhexyl)phthalate

A double ester of phthalic acid!

dehp di 2 ethylhexyl phthalate
DEHP - Di(2-ethylhexyl)phthalate

A double ester of phthalic acid!

O

C

OH

O

C

OH

How do we make an ester?

Phthalic Acid

slide69

H+

Carboxylic Acid + Alcohol

Ester + Water

dehp di 2 ethylhexyl phthalate1
DEHP - Di(2-ethylhexyl)phthalate

Which one?

O

C

React with an alcohol!

OH

O

C

OH

How do we make an ester?

Phthalic Acid

dehp di 2 ethylhexyl phthalate2
DEHP - Di(2-ethylhexyl)phthalate
  • Hexyl

= 6 carbons

H

H

H

H

H

H

HO

H

C

C

C

C

C

C

H

H

H

H

H

H

dehp di 2 ethylhexyl phthalate3

CH2

CH3

DEHP - Di(2-ethylhexyl)phthalate
  • 2-ethyl

Ethyl group on the 2nd carbon!

H

H

H

H

H

H

HO

H

C

C

C

C

C

C

1

2

3

4

5

6

H

H

H

H

H

H

H+

Carboxylic Acid + Alcohol

Ester + Water

2 ethyl 1 hexanol

CH2

CH3

2-ethyl-1-hexanol

H

H

H

H

H

H

HO

H

C

C

C

C

C

C

H

H

H

H

H

new notation
New Notation!!
  • The “squiggly” notation
2 ethyl 1 hexanol1

CH2

CH3

2-ethyl-1-hexanol

H

H

H

H

H

H

HO

H

C

C

C

C

C

C

H

H

H

H

H

HO

dehp di 2 ethylhexyl phthalate4
DEHP - Di(2-ethylhexyl)phthalate

O

C

HO

+

OH

O

C

OH

Phthalic Acid

slide77

O

C

+

H

O

OH

O

C

OH

slide82
How do plasticizers soften plastic?

“The elephant in the parade.”

slide83
How do plasticizers soften plastic?

“The elephant in the parade.”

O

C

O

O

C

O

slide84
How do plasticizers soften plastic?

Creates more space between the polymer branches

“The elephant in the parade.”

O

C

O

O

C

O

plasticizers2
Plasticizers

Leading to a more flexible plastic

slide86
PVC

PVC used to be used to house food items.

Why?

Has been primarily replaced with PET

slide87

Plasticizers slowly leach from the plastic and into solutions

More likely to leach into polar or nonpolar solutions?

slide89

intravenous (IV) bags and tubing

  • umbilical artery catheters
  • blood bags and infusion tubing
  • enteral nutrition feeding bags
  • nasogastric tubes
  • peritoneal dialysis bags and tubing
  • tubing used in cardiopulmonary bypass (CPB) procedures
  • tubing used during hemodialysis

Over 1 billion lbs of DEHP used worldwide

in lab animals
In lab animals…

Liver Damage

Carcinogen (Causes Cancer)

in people
In people…

Controversial…

What to do?

european union
European Union
  • “…the exposure of the general population is well below (at least 280 times) levels at which their health might be put at risk.”
  • “no risk reduction measures are needed…”
slide94
2003
  • California Assembly
  • Bill to ban DEHP in medical devices (except where no alternative)
slide95

Exposure to DEHP increased with increased “use.”

DEHP leaches out extremely slowly in polar solutions

This is NOT a reason to discontinue medical treatment!!!

topics for monday2
Topics for Monday
  • Lipids, Fats, and Oils!

Are fats polar or nonpolar?

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