- 197 Views
- Uploaded on

Download Presentation
## PowerPoint Slideshow about ' Topics for Today' - tamera

**An Image/Link below is provided (as is) to download presentation**

Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author.While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server.

- - - - - - - - - - - - - - - - - - - - - - - - - - E N D - - - - - - - - - - - - - - - - - - - - - - - - - -

Presentation Transcript

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 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

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

Topics for Today

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

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

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!!!!

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 polyamide for ANY given diacid and diamine!!!!

- PP, PS, HDPE, LDPE, PVC, Teflon

1 monomer

No byproducts!

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

[

]n

H

H

R·

–CH2–CH2–

n

C = C

H

H

EXPAND!

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 polyamide for ANY given diacid and diamine!!!!

Does the orientation matter?

H

H

H

H

R·

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

Does the orientation matter?

H

H

H

H

R·

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

Glassy and brittle

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

- Can be injected with a gas to make foam!

We used to use CFCs!

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

H

H

H

H

R·

— C – C—

n

C = C

n

H

H

HEAD

TAIL

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

What orientation?

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

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

H

H

H

H

R·

— 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

Has order – packs well

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

PVCCl

Cl

Cl

Cl

Cl

Head-to-tail

Has order – packs well

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

PVCCl

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

Less order – does not pack as well

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

PVCCl

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!!!!

- Can also be shiny! polyamide for ANY given diacid and diamine!!!!

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

Why not?

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

PVCCl

Cl

Cl

Cl

Cl

Random

Less order – does not pack as well

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!

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

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)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

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

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

CH3

2-ethyl-1-hexanolH

H

H

H

H

H

HO

H

C

C

C

C

C

C

H

H

H

H

H

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

- The “squiggly” notation

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

CH3

2-ethyl-1-hexanolH

H

H

H

H

H

HO

H

C

C

C

C

C

C

H

H

H

H

H

HO

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

O

C

HO

+

OH

O

C

OH

Phthalic Acid

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

O

C

O

+

H2O

O

C

O

+

H2O

- How do plasticizers soften plastic? polyamide for ANY given diacid and diamine!!!!

“The elephant in the parade.”

- How do plasticizers soften plastic? polyamide for ANY given diacid and diamine!!!!

“The elephant in the parade.”

O

C

O

O

C

O

- How do plasticizers soften plastic? polyamide for ANY given diacid and diamine!!!!

Creates more space between the polymer branches

“The elephant in the parade.”

O

C

O

O

C

O

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?

Where do we find plasticizers? 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

Health Risks of DEHP? solutions

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!!!

Download Presentation

Connecting to Server..