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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


Topics for friday

Topics for Friday


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


Topics for today

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


Topics for today

Where were we??


Condensation polymers

Condensation Polymers!

Polyester

Nylon


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


Topics for today

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!!


Topics for today

Preview…


Topics for today

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…


Topics for today

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


Topics for today

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


Topics for today

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


Topics for today

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


Topics for today

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?


Polyvinyl chloride pvc

Polyvinyl Chloride (PVC)


Topics for today

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


Topics for today

PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail


Topics for today

PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well


Topics for today

Rigid, stiff material

PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well


Topics for today

PVC

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head


Topics for today

Rigid, stiff material

PVC

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head

Has order – packs well


Topics for today

PVC

Cl

Cl

Cl

Cl

Cl

Random


Topics for today

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


Topics for today

Slightly softer

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


Topics for today

PVC comes in many forms!


Topics for today

PVC

  • Can be opaque

    and rigid


Topics for today

PVC

  • Can be opaque and rigid


Topics for today

PVC

  • Can be transparent and

    softer


Topics for today

often shiny


Topics for today

  • Can also be shiny!


Topics for today

PVC

Why not?


Topics for today

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!


Topics for today

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?


Topics for today

DEHP

  • Di(2-ethylhexyl)phthalate

A double ester of phthalic acid!


Terephthalic acid

O

Terephthalic Acid

C

OH

O

C

HO


Phthalic acid

O

Phthalic Acid

C

OH

O

C

OH


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


Topics for today

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


Topics for today

O

C

+

H

O

OH

O

C

OH


Topics for today

DEHP - Di(2-ethylhexyl)phthalate

O

C

O

+

H2O

O

C

OH


Topics for today

Let’s add another one!

O

C

O

+

H2O

O

C

OH

HO


Topics for today

DEHP - Di(2-ethylhexyl)phthalate

O

C

O

+

H2O

O

C

O

+

H2O


Topics for today

  • How do plasticizers soften plastic?

“The elephant in the parade.”


Topics for today

  • How do plasticizers soften plastic?

“The elephant in the parade.”

O

C

O

O

C

O


Topics for today

  • 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


Topics for today

PVC

PVC used to be used to house food items.

Why?

Has been primarily replaced with PET


Topics for today

Plasticizers slowly leach from the plastic and into solutions

More likely to leach into polar or nonpolar solutions?


Topics for today

Where do we find plasticizers?


Topics for today

  • 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


Topics for today

Health Risks of DEHP?


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…”


Topics for today

2003

  • California Assembly

  • Bill to ban DEHP in medical devices (except where no alternative)


Topics for today

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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