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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

  • 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!

This Friday!

Same format as always


Exam #3!

Non-memory calculators OK.

Please, no cell phones


Topics for Monday

  • Lipids, Fats, and Oils!


Topics for Monday

  • What is a fat? Fatty acid?

  • Saturated vs unsaturated fats

  • Animal versus plant


Readings For Monday

  • 11.3 Fat & Oils: Part of the lipid family

  • 11.4 Saturated and Unsaturated Fats & Oils


Figures Alive!

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


Topics for Today

  • Back to PVC and Addition Polymers

    • Stiff or Flexible? Plasticizers


Where were we??


Condensation Polymers!

Polyester

Nylon


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


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


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!!


Preview…


Equation 9.7

(p. 414)

Built from amino acids!


Condensation Polymers

  • Nylon and PET (polyester)

A small molecule is released as a byproduct

Can be built from one or two monomers


Addition Polymers

  • PP, PS, HDPE, LDPE, PVC, Teflon

1 monomer

No byproducts!


Polyethylene

[

]n

H

H

–CH2–CH2–

n

C = C

H

H

EXPAND!


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

Does the orientation matter?

H

H

H

H

— C – C—

n

C = C

n

H

CH3

H

CH3

Expand out…


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


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

Does the orientation matter?

H

H

H

H

— C – C—

n

C = C

n

H

CH3

H

CH3

HEAD

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

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

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


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

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


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

Glassy and brittle


Polystyrene

  • Can be injected with a gas to make foam!

We used to use CFCs!


Polystyrene?

H

H

H

H

— C – C—

n

C = C

n

H

H

HEAD

TAIL


Polystyrene

What orientation?


Polyvinyl Chloride (PVC)


Polymerize!

Cl

H

C

C

H

H

vinyl chloride


Polyvinylchloride (PVC)

H

H

H

H

— C – C—

n

C = C

n

H

Cl

H

Cl


PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail


PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well


Rigid, stiff material

PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well


PVC

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head


Rigid, stiff material

PVC

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head

Has order – packs well


PVC

Cl

Cl

Cl

Cl

Cl

Random


PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


Slightly softer

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


PVC comes in many forms!


PVC

  • Can be opaque

    and rigid


PVC

  • Can be opaque and rigid


PVC

  • Can be transparent and

    softer


often shiny


  • Can also be shiny!


PVC

Why not?


PVC

PVC is usually not recyclable

Why not?


Plasticizers

  • Big molecules added to soften a plastic

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


Still not soft enough for some uses…

Slightly softer

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


Plasticizers

Phthalates are commonly used

Where have we seen phthlate-related compounds?


DEHP

  • Di(2-ethylhexyl)phthalate

A double ester of phthalic acid!


O

Terephthalic Acid

C

OH

O

C

HO


O

Phthalic Acid

C

OH

O

C

OH


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


H+

Carboxylic Acid + Alcohol

Ester + Water


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)phthalate

  • Hexyl

= 6 carbons

H

H

H

H

H

H

HO

H

C

C

C

C

C

C

H

H

H

H

H

H


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


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!!

  • The “squiggly” notation


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)phthalate

O

C

HO

+

OH

O

C

OH

Phthalic Acid


O

C

+

H

O

OH

O

C

OH


DEHP - Di(2-ethylhexyl)phthalate

O

C

O

+

H2O

O

C

OH


Let’s add another one!

O

C

O

+

H2O

O

C

OH

HO


DEHP - Di(2-ethylhexyl)phthalate

O

C

O

+

H2O

O

C

O

+

H2O


  • How do plasticizers soften plastic?

“The elephant in the parade.”


  • How do plasticizers soften plastic?

“The elephant in the parade.”

O

C

O

O

C

O


  • How do plasticizers soften plastic?

Creates more space between the polymer branches

“The elephant in the parade.”

O

C

O

O

C

O


Plasticizers

Leading to a more flexible plastic


PVC

PVC used to be used to house food items.

Why?

Has been primarily replaced with PET


Plasticizers slowly leach from the plastic and into solutions

More likely to leach into polar or nonpolar solutions?


Where do we find plasticizers?


  • 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


Health Risks of DEHP?


In lab animals…

Liver Damage

Carcinogen (Causes Cancer)


In people…

Controversial…

What to do?


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…”


2003

  • California Assembly

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


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 Monday

  • Lipids, Fats, and Oils!

Are fats polar or nonpolar?


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