1. Developing Practical Applications of Phosphonic Acid Skanda Amarnath, Matthew Chalkley, Rachel Chen, Reena Clements, Kevin Gu, Gawain Lau, Stephen Leh, Sarvagna Patel, Mark Vander Schaaf, Phyllis Schlafly, Smith Shah Advisor: Michael Avaltroni Assistant: Jennifer Cowell

2. Octadecylphosphonic Acid (OPA) Bonds easily to many surfaces 1 Bonds easily to many surfaces 1 Creates a durable hydrophobic layer that adheres to hydrophilic surfaces Creates a durable hydrophobic layer that adheres to hydrophilic surfaces Bonds chemically rather than physically Bonds chemically rather than physically 1 Maege I, Jaehne E, Henke A, Adler H.-JP, Bram C, Jung C, Stratmann M. 1998. Self-assembling adhesion promoters for corrosion resistant metal polymer interfaces. Progress in Organic Coatings. 34: 1-12.

3. The Structure of OPA Schreiber F. Dec 2000. Structure and growth of self-assembling monolayers. Progress in Surface Science [cited 16 July 2008] 65: 151-256..http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TJF-428DK9M- 1&_user=799667&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000038258&_version=1&_urlVersion=0&_u serid=799667&md5=274b633832f0a166f28f2213b36a4ad5 Diprotic acid Both protons are acidic Octadecyl alkyl group increases hydrophobicity

4. Oxide Surfaces O MM O M µ-oxo Group Hydroxyl Group OH M M M

5. Octadecylphosphonic Acid Bonding to an Oxide Layer Schreiber F. Dec 2000. Structure and growth of self-assembling monolayers. Progress in Surface Science [cited 16 July 2008] 65: 151-256..http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TJF-428DK9M- 1&_user=799667&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000038258&_version=1&_urlVersion=0&_userid=799667&md5=274b633832f0 a166f28f2213b36a4ad5

6. Purpose To investigate the effectiveness of OPA in: To investigate the effectiveness of OPA in: Repelling water and residue buildup 3 Repelling water and residue buildup 3 Contact Angle, Surface Adhesion Contact Angle, Surface Adhesion Irreversible attaching to a surface 4 Irreversible attaching to a surface 4 Attenuated Total Reflectance Attenuated Total Reflectance Resisting corrosion Resisting corrosion Electrochemical Cell, Salinity, Acidity 3 Freedman LD, Doak GO. 1956. The Preparation and Properties of Phosphonic Acid. University of North Carolina Press. 4 Schreiber F. Dec 2000. Structure and growth of self-assembling monolayers. Progress in Surface Science [cited 16 July 2008] 65: 151-256. Available from: http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TJF-428DK9M-1&_user=799667&_rdoc=1&_fmt=&_orig=http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TJF-428DK9M-1&_user=799667&_rdoc=1&_fmt=&_orig= search&_sort=d&view=c&_acct=C000038258&_version=1&_urlVersion=0&_userid=799667&md5=274b633832f0a166f28f2213b36a4ad5

7. Hypothesis An OPA coating will repel unwanted materials and act as a barrier to corrosion An OPA coating will repel unwanted materials and act as a barrier to corrosion

8. Methods and Materials Three materials were considered: Three materials were considered: Glass Glass Copper Copper Stainless Steel (Grade 316L) Stainless Steel (Grade 316L) They were coated using a “spray and spread” method 5 They were coated using a “spray and spread” method 5 Exposed to solutions of varying pHs, as well as material-specific situations Exposed to solutions of varying pHs, as well as material-specific situations 5 Appicella T, et al. 2007. Phosphonic Acid: A Zero-Energy Approach to Teflon Replacement. New Jersey Governor’s School of the Sciences. [cited 17 July 2008]..http://depts.drew.edu/govschl/NJGSS2007/Journal/TeamPapers/Team2.pdf

9. WD-40 ® Used for comparison Used for comparison Cleaner/lubricant/protectant Cleaner/lubricant/protectant Aerosol Aerosol Greasy Greasy Not permanent – physical bond Not permanent – physical bond

10. Contact Angle Tests A goniometer measures the hydrophobicity of a surface A goniometer measures the hydrophobicity of a surface Greater angles imply that the surface has greater hydrophobicity Greater angles imply that the surface has greater hydrophobicity θ θ

11. Average Contact angle(degrees) (Results after 7 days) Effectiveness of Stainless Steel Coatings

12. Average Contact angle (degrees)(degrees) (Results after 7 days) Effectiveness of Copper Coatings

13. Test Results for Acids Qualitative data based on appearance Qualitative data based on appearance Corrosion scaled from 0 to 5, with 0 being no corrosion and 5 being most corroded Corrosion scaled from 0 to 5, with 0 being no corrosion and 5 being most corroded ControlOPAWD-40 pH 1.5311 pH 3420 pH 3.5500 pH 4500 pH 7000

14. Salinity Test OPA-coated steel was placed in a saline solution, simulating average salt content of ocean’s surface OPA-coated steel was placed in a saline solution, simulating average salt content of ocean’s surface Simulates steel-hulled ship in ocean Simulates steel-hulled ship in ocean

15. Salinity Test Results

16. ASTM Test for Surface Adhesion “Sharpie Test” “Sharpie Test” Sharpie markers were used to simulate residue buildup Sharpie markers were used to simulate residue buildup Glass and copper samples with different coatings were marked and wiped Glass and copper samples with different coatings were marked and wiped

17. Sharpie Test Results - Glass Sharpie on slides before Sharpie on slides before wiping

18. Sharpie Test Results - Glass Sharpie on slides after wiping

19. Sharpie Test Results - Glass Sharpie on slides with ethanol treatment after wiping

20. Sharpie Test Results - Copper Sharpie on copper before wiping with dry paper towel

21. Sharpie on copper after wiping with paper towel Sharpie Test Results - Copper

22. Electrochemical Cells Cu V Zn Zn 2+, Cl - Cu 2+, SO 4 2- NH 4 + NO 3 -

23. Electrochemical potential (V) Resulting Voltages

24. Attenuated Total Reflectance (ATR) Test An ATR test analyzes the chemical composition of a surface An ATR test analyzes the chemical composition of a surface Measures amount of OPA on surface Measures amount of OPA on surface PerkinElmer, Inc. “FT-IR Spectroscopy: Attenuated Total Reflectance (ATR).” 2005. [cited 22 July 2008].. Surface

25. ATR Test Results Copper, OPA coated, pH 1.5 2917 2845

26. Conclusion OPA will be a suitable replacement for current coating OPA will be a suitable replacement for current coating

27. Conclusion - Results Corrosion Resistance Electrochemical cells Salinity Acid Durability ATR Hydrophobicity Contact Angle Adhesion Resistance Sharpie Test

28. Conclusion – Further Tests Polar/Non-Polar Wash Polar/Non-Polar Wash Confirm results in acid/contact angle Confirm results in acid/contact angle Longer Duration Tests Longer Duration Tests Simulate consumer conditions Simulate consumer conditions

29. Acknowledgements Dr. Michael Avaltroni Jennifer Cowell NJGSS 2008 Staff: Dr. David Miyamoto, Dr. Steven Surace, Dr. Paul Quinn, Myrna Papier, professors, and counselors

30. Special Thanks to… The many alumni and parents who donated, especially Laura and John Overdeck Schering-Plough Foundation Novartis The Dorr Foundation The Jennifer A. Chalsty Foundation The Edward W. & Stella C. Van Houten Memorial Fund The Jewish Communal Fund

31. Questions?