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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


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



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


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… polyamide for ANY given diacid and diamine!!!!


Equation 9.7 polyamide for ANY given diacid and diamine!!!!

(p. 414)

Built from amino acids!


Condensation polymers1
Condensation Polymers polyamide for ANY given diacid and diamine!!!!

  • Nylon and PET (polyester)

A small molecule is released as a byproduct

Can be built from one or two monomers


Addition polymers
Addition Polymers polyamide for ANY given diacid and diamine!!!!

  • PP, PS, HDPE, LDPE, PVC, Teflon

1 monomer

No byproducts!


Polyethylene
Polyethylene polyamide for ANY given diacid and diamine!!!!

[

]n

H

H

–CH2–CH2–

n

C = C

H

H

EXPAND!


Polyethylene1
Polyethylene polyamide for ANY given diacid and diamine!!!!

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 polyamide for ANY given diacid and diamine!!!!

Does the orientation matter?

H

H

H

H

— C – C—

n

C = C

n

H

CH3

H

CH3

Expand out…


CH polyamide for ANY given diacid and diamine!!!!3

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


CH polyamide for ANY given diacid and diamine!!!!3

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 polyamide for ANY given diacid and diamine!!!!

Does the orientation matter?

H

H

H

H

— C – C—

n

C = C

n

H

CH3

H

CH3

HEAD

TAIL


CH polyamide for ANY given diacid and diamine!!!!3

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 polyamide for ANY given diacid and diamine!!!!

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


CH polyamide for ANY given diacid and diamine!!!!3

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 polyamide for ANY given diacid and diamine!!!!

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 polyamide for ANY given diacid and diamine!!!!

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 polyamide for ANY given diacid and diamine!!!!

Glassy and brittle


Polystyrene1
Polystyrene polyamide for ANY given diacid and diamine!!!!

  • Can be injected with a gas to make foam!

We used to use CFCs!


Polystyrene2
Polystyrene? polyamide for ANY given diacid and diamine!!!!

H

H

H

H

— C – C—

n

C = C

n

H

H

HEAD

TAIL


Polystyrene3
Polystyrene polyamide for ANY given diacid and diamine!!!!

What orientation?


Polyvinyl chloride pvc
Polyvinyl Chloride (PVC) polyamide for ANY given diacid and diamine!!!!


Polymerize! polyamide for ANY given diacid and diamine!!!!

Cl

H

C

C

H

H

vinyl chloride


Polyvinylchloride pvc
Polyvinylchloride (PVC) polyamide for ANY given diacid and diamine!!!!

H

H

H

H

— C – C—

n

C = C

n

H

Cl

H

Cl


PVC polyamide for ANY given diacid and diamine!!!!

Cl

Cl

Cl

Cl

Cl

Head-to-tail


PVC polyamide for ANY given diacid and diamine!!!!

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well


Rigid, stiff material polyamide for ANY given diacid and diamine!!!!

PVC

Cl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well


PVC polyamide for ANY given diacid and diamine!!!!

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head


Rigid, stiff material polyamide for ANY given diacid and diamine!!!!

PVC

Cl

Cl

Cl

Cl

Cl

Cl

Head-to-head

Has order – packs well


PVC polyamide for ANY given diacid and diamine!!!!

Cl

Cl

Cl

Cl

Cl

Random


PVC polyamide for ANY given diacid and diamine!!!!

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


Slightly softer polyamide for ANY given diacid and diamine!!!!

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


PVC comes in many forms! polyamide for ANY given diacid and diamine!!!!


PVC polyamide for ANY given diacid and diamine!!!!

  • Can be opaque

    and rigid


PVC polyamide for ANY given diacid and diamine!!!!

  • Can be opaque and rigid


PVC polyamide for ANY given diacid and diamine!!!!

  • Can be transparent and

    softer


often shiny polyamide for ANY given diacid and diamine!!!!



PVC polyamide for ANY given diacid and diamine!!!!

Why not?


PVC polyamide for ANY given diacid and diamine!!!!

PVC is usually not recyclable

Why not?


Plasticizers
Plasticizers polyamide for ANY given diacid and diamine!!!!

  • 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… polyamide for ANY given diacid and diamine!!!!

Slightly softer

PVC

Cl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well


Plasticizers1
Plasticizers polyamide for ANY given diacid and diamine!!!!

Phthalates are commonly used

Where have we seen phthlate-related compounds?


DEHP polyamide for ANY given diacid and diamine!!!!

  • Di(2-ethylhexyl)phthalate

A double ester of phthalic acid!


Terephthalic acid

O polyamide for ANY given diacid and diamine!!!!

Terephthalic Acid

C

OH

O

C

HO


Phthalic acid

O polyamide for ANY given diacid and diamine!!!!

Phthalic Acid

C

OH

O

C

OH


Dehp di 2 ethylhexyl phthalate
DEHP - Di(2-ethylhexyl)phthalate polyamide for ANY given diacid and diamine!!!!

A double ester of phthalic acid!

O

C

OH

O

C

OH

How do we make an ester?

Phthalic Acid


H polyamide for ANY given diacid and diamine!!!!+

Carboxylic Acid + Alcohol

Ester + Water


Dehp di 2 ethylhexyl phthalate1
DEHP - Di(2-ethylhexyl)phthalate polyamide for ANY given diacid and diamine!!!!

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 polyamide for ANY given diacid and diamine!!!!

  • 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

CH polyamide for ANY given diacid and diamine!!!!2

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

CH polyamide for ANY given diacid and diamine!!!!2

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!! polyamide for ANY given diacid and diamine!!!!

  • The “squiggly” notation


2 ethyl 1 hexanol1

CH polyamide for ANY given diacid and diamine!!!!2

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 polyamide for ANY given diacid and diamine!!!!

O

C

HO

+

OH

O

C

OH

Phthalic Acid


O polyamide for ANY given diacid and diamine!!!!

C

+

H

O

OH

O

C

OH


DEHP - Di(2-ethylhexyl)phthalate polyamide for ANY given diacid and diamine!!!!

O

C

O

+

H2O

O

C

OH


Let’s add another one! polyamide for ANY given diacid and diamine!!!!

O

C

O

+

H2O

O

C

OH

HO


DEHP - Di(2-ethylhexyl)phthalate polyamide for ANY given diacid and diamine!!!!

O

C

O

+

H2O

O

C

O

+

H2O


“The elephant in the parade.”


“The elephant in the parade.”

O

C

O

O

C

O


Creates more space between the polymer branches

“The elephant in the parade.”

O

C

O

O

C

O


Plasticizers2
Plasticizers polyamide for ANY given diacid and diamine!!!!

Leading to a more flexible plastic


PVC polyamide for ANY given diacid and diamine!!!!

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?



  • intravenous (IV) bags solutions 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… solutions

Liver Damage

Carcinogen (Causes Cancer)


In people
In people… solutions

Controversial…

What to do?


European union
European Union solutions

  • “…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 solutions

  • California Assembly

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


Exposure to DEHP increased with increased “use.” solutions

DEHP leaches out extremely slowly in polar solutions

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


Topics for monday2
Topics for Monday solutions

  • Lipids, Fats, and Oils!

Are fats polar or nonpolar?


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