1. Bonding with Color Chemistry and Outreach Opportunities of Tie Dye Anne E. Moody Truman State University amoody@truman.edu

2. AEMoody: Truman State U Truman Freshmen 2007

3. AEMoody: Truman State U Color is Everywhere!

4. AEMoody: Truman State U Color Results from Interaction of Light and Matter

5. AEMoody: Truman State U Must BOND Dyes to Clothes

6. AEMoody: Truman State U Natural Dyes Tyrian Purple From Shellfish Kermesic Acid From Insects

7. AEMoody: Truman State U Molecular Structure Determines Color of Matter Note extended conjugated pi systems in these synthetic dyes:

8. AEMoody: Truman State U Fiber Structure Determines Interactions with Dyes Wool has many reactive sites in its structure:

9. AEMoody: Truman State U Cheaper Fabric Structures In Cotton, R = H In Acetate Rayon, R= C(O)CH 3

10. AEMoody: Truman State U Vat Dyes depend on Mechanical Retention and Redox Chemistry

11. AEMoody: Truman State U Fiber Reactive Dyes In General: W-D-Q-RG-X Where: W = water solubilizing groups D = Chromophore of Dye Q = Bridging Group RG = Reactive Group X = Leaving Group

12. AEMoody: Truman State U Procion Synthetic Dye Example Fiber Reactive Dye Covalently Bonds to Fabric

13. AEMoody: Truman State U “Stylized” Procion Dye Reaction with Cotton

14. AEMoody: Truman State U Closer Look at Dye-Fabric Bond Formation

15. AEMoody: Truman State U Hydrolysis of C-Cl of Dye

16. AEMoody: Truman State U Acid-Base Chemistry Inactivates Dyes

17. AEMoody: Truman State U Today’s Experiment Your T-shirt starts out very clean and dry! It goes into our bucket of base solution and now it is very wet and basic. We’ll wring it out when we give it to you!

18. AEMoody: Truman State U Your Task for Today Twist and fold the damp, basic shirt in particular patterns; secure it with rubber bands. Apply the dyes using squirt bottles…. Place wet, dyed shirt in zip-lock bag and let reactions proceed.

19. AEMoody: Truman State U Patience with the Experiment! Wait 24 hours! Wash in hot water with dish soap; dry in hot dryer. Enjoy cool shirt! ;-)

20. AEMoody: Truman State U Tie Dye and Chemistry are FUN! Fun and creative outlet Excellent outreach activity Excellent fund-raising activity Chemistry at many levels ;-)