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Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2
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Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Jan 01, 2016

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Page 1: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings

Group T2

Page 2: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

History of TeflonPolytetrafluoroethylen

eDiscovered: 19381944: Manhattan

project 1960: cookware,

insulation

Page 3: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Characteristics of TeflonNon-stick Hydrophobic, oleophobic Low coefficient of friction Low heat dissipation factorProblems?

◦Flakes off◦Possible carcinogen

Page 4: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Goals Find a hydrophobic surface

coating (an alternative for Teflon)

Compare octadecylphosphonic acid (OPA) with perfluoroctylphosphonic acid (P-FOPA)

Improve speed of reactionExplore further applications for

OPA

Page 5: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

OOOH

Page 6: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

OOOH

OO OOO

H H

+

H+

H+

Page 7: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

OOO

P

OH

O 16

OOO

P-O

O 16

OOH+O

P-O

O 16

OOO

P

O 16

H+

OH

Page 8: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Experimental o Use of Primers to facilitate bonding

o Comparison of Phosphonic acids and simulation of real world conditions

oUse of SEM to visualize coating coverage

Page 9: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Comparing and Testing PrimersPrimers used

◦ Diethyl Phthalate◦ PDMS-PFDD

(Polydimethylsiloxane-co-dimer acid, bis(perfluorododecyl) terminated)

◦ PDMS-OH (Polydimethylsiloxane hydroxyl terminated)

◦ Tantalum(V) 2-Ethylhexoxide◦ Tantalum (V) Ethoxide◦ Tantalum (V) Chloride

Durability tests Conducted

Page 10: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Ramé-hart Goniometer

Page 11: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.
Page 12: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

About PrimersApplication is faster more

efficient Primers as linkers What makes a good primer?Industrial v. Medical Criteria

◦Tantalum as replacement for chromium.

◦Toxicity and cost

Page 13: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

OHOH

Ta

EtO

OEt

EtO O

OEt

CH2

CH3O-OH H+

Ta

EtO

OEt

EtO

OEt

OOH

EtO OEt

EtO OEt

OO

Ta

EtO

OEt

OEt

Metal OxideSurface

Primer Coating

Phosphonic Acid Coating

OO

Ta

EtO

O

OEt

PO

16

OH

Page 14: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Three Testing MethodsBake on primer, bake on acid

Bake on primer, Iron on acid

Iron on primer, Iron on acid

Page 15: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

After Primer Tests

Unprimed DE Phthalate

T 2-Eox-ide

PDMS- PFDD

PDMS- OH T Ethox-ide

T Chloride Uncoated40.0

50.0

60.0

70.0

80.0

90.0

100.0

58.4

78.5

76.5

94.6

90.3

81.0

89.5

44.6

89.2

83.8

93.7

96.1

91.7

95.2

89.2

Bake and Bake Contact Angles

Unwashed

Washed

Primer

Con

tact

An

gle

(D

eg

rees)

N=3

Page 16: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

After Primer Tests

Unprimed DE Phthalate

T 2-Eox-ide

PDMS- PFDD

PDMS- OH T Ethox-ide

T Chloride Uncoated40.0

50.0

60.0

70.0

80.0

90.0

100.0

110.0

120.010

1.7

101.

8

100.

9

107.

2

115.

5

110.

5

107.

7

44.6

95.9

104.

5

96.0

106.

6

104.

4

103.

8

100.

8

Iron and Iron Contact Angles

Unwashed

Washed

Primers

Con

tact

An

gle

(D

eg

rees)

Page 17: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

After Primer Tests

Unprimed DE Phthalate

T 2-Eox-ide

PDMS- PFDD

PDMS- OH T Ethox-ide

T Chloride Uncoated40.0

50.0

60.0

70.0

80.0

90.0

100.0

110.0

120.0

130.011

2.9

113.

3

109.

8

113.

6

109.

1

111.

3

107.

2

44.6

104.

1

118.

0

111.

8

106.

7

113.

1

107.

4

108.

1

97.3

104.

2

104.

0

105.

7

104.

3

102.

0

102.

4

Bake and Iron Contact Angles

Unwashed

Washed once with Ethanol

Washed with Ethanol, and then Soap and Wa-ter

Primers

Con

tact

An

gle

(D

eg

rees)

N=3

Page 18: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Durability Tests

Page 19: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Durability Test Applications OPA dissolved in ethanol solventP-FOPA dissolved in

chloroform/ethanol solution ◦Able to wet and coat surface!

Page 20: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Durability Test ApplicationsMaterials: aluminum, steel, glass

◦Clean with ethanol and hot waterBake in oven, heat gun, infrared

Page 21: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Durability TestsSteel wool – 10 seconds Heat test – ½ hour @ 250C

◦Hot ethanol bath for 5 minutes Washed with hand soap and

sponge

Page 22: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

After Durability Tests

Heat Gun Infrared0.0

20.0

40.0

60.0

80.0

100.0

120.0

140.0125.2

119.5

97.589.786.8

94.2

117.1

133.1

102.8

91.5

P-FOPA Contact Angles--Stainless Steel

InitialAfter steel woolAfter heatAfter ethanolAfter soap/water

Application Method

Con

tact

An

gle

Page 23: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

A

B

C

Aluminum A: UncoatedB: OPA C: P-FOPA

Page 24: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Mixing Primers & P-FOPA

Page 25: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

After Durability Tests

DE Phthalate T Ethoxide Uncoated0.0

20.0

40.0

60.0

80.0

100.0

120.0

140.0127.4

116.7

59.6

108.6103.0

118.6

95.6

113.8

100.8

Primer Contact Angles--P-FOPA on Stainless Steel

InitialAfter washingAfter steel woolAfter heat

Coating

Con

tact

An

gle

n =1

Page 26: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Sources of ErrorQuick washes Lack of replication

◦3 samples Human Error

◦Application method◦Possible multi-layers: lower angles

for unwashed samples

Page 27: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

ConclusionBest primers

◦ Diethyl phthalate◦ PDMS-PFDD (polydimethylsiloxane-co-dimer

acid, bis(perfluorododecyl) terminated) ◦ Tantalum(V) ethoxide ◦ Neither worked well with P-FOPA except when

applied to stainless steel

OPA, P-FOPA◦Heat gun – least time consuming◦316L stainless steel discs

SEM: view coatings

Page 28: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Acknowledgements

Thanks to: ◦Dr. Avaltroni ◦Darius Rackus◦Aculon, Inc. ◦Sponsors of the NJGSS 2009 Program

Page 29: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Picture Creditshttp://www.wired.com/images/articl

e/full/2009/04/teflon (2)

http://greatgreengadgets.com/gadgets/2007/08/22/green-alternative-to-teflon-cookware/ (2)

http://www.healthbase.com/resources/orthopedics/total-hip-replacement-surgery-implants/zimmer-hip-replacement-implant-cemented-cementless-press-fit-india-affordable-medical-tourism.html (2)

http://www.ramehart.com/goniometers/index.htm (10)

http://www.ramehart.com/goniometers/contactangle.htm (11)

Page 30: Transforming Teflon A Systematic Investigation of Hydrophobic Material Coatings Group T 2.

Works Cited Shannon, Fintan J.; Cottrell, Jocelyn M., Deng, Xiang-Hua, Doty, Steven B.; Warren, Russell F.; Wright, Timothy M.;

Crowder, Katherine, N.; Avaltroni, Michael J.; Schwartz, Jeffrey; “A Novel Surface Treatment for Porous Metal Implants That Improves The Rate of Bony Ingrowth”  J Biomed Mater Res A. 2008; 86(4):857-64.

Danahy, M. P.; Avaltroni, M. J.; Midwood, K. S.; Schwarzbauer, J. E., Schwartz, J. “Self Assembled Monolayers of a,w-Diphosphonic Acids on Ti Enable Complete of Spatially Controlled Surface Derivitization.” Langmuir, 2004, 20, 5333 – 5337

Schwartz, J.; Avaltroni, M. J.; Danahy, M. P.; Silverman, B. M.; Hanson, E. L. ; Schwarzbauer, J. E.; Midwood, K.; Gawalt, E. S. “Cell Attachment and Spreading on Metal Implant Materials.” Materials Science and Engineering C, 2003, 23, 395-400

Gawalt, E. S.; Avaltroni, M. J.; Danahy, M. P.; Silverman, B. M.; Hanson, E. L.; Midwood, K. S.; Schwarzbauer, J. E.; Schwartz, J. “Bonding Organics to Ti Alloys: Facilitating Human Osteoblast Attachment and Spreading on Surgical Implant Materials.”  Langmuir, 2003, 19, 200-204

Gawalt, E. S.; Avaltroni, M. J.; Koch, N.; Schwartz, J. “Self Assembly and Bonding of Alkanephosphonic Acids on the Native Oxide Surface of Titanium.” Langmuir, 2001, 17, 5736-5740

Schwartz; Jeffrey (Princeton, NJ), Avaltroni; Michael J. (Staten Island, NY), Danahy; Michael P. (Princeton, NJ), Silverman; Brett M. (Princeton, NJ), Carrier Applied Coating Layers. U.S. Patent 7396594, July 8, 2008

Schwartz; Jeffrey; (Princeton, NJ) ; Danahy; Michael; (Lewiston, ME) ; Avaltroni; Michael; (Staten Island, NY) ; Guo; Jing; (Sunnyvale, CA), Enhanced Bonding Layers on Native Oxide Surfaces, U.S. Provisional Patent Award 20080166470, July 10, 2008

Schwartz, J.; Gawalt, E.; Avaltroni, M. “Enhanced bonding of phosphoric and phosphonic acids to oxidized subtrates”; United States Patent #6,645,644 

Avaltroni, Michael J.; Bruner, Eric L. Hanson, Eric L.; “Organophosphate Adhesion Promoters“ U.S. Patent, Submitted 2006

Avaltroni, M.J.; Bruner, E.L.; Hanson, E.; „“Thin Films“, 2006, United States Patent Pending Schwartz, J; Avaltroni, M.J.; “Devices With Multiple Surface Functionality“; 2006, United States Patent Pending Schwartz, J; Avaltroni, M.J.; “Devices With Multiple Surface Functionality“; 2005, United States Patent

60/737,397 Schwartz, J; Avaltroni, M.J.; Danahy, Michael P.; Silverman, Brett M.; “Carrier Applied Coating Layers”; 2005,

United States Patent 10/876,294 Schwartz, J.; Avaltroni, M.; Carolus, M.; Hanson, E.; Schwarzbauer, J.; Midwood, K.; Danahy, M.   “Enhanced

bonding layers on native oxide surfaces”; 2004, United States Patent 10/405,557. Schwartz, J.; Danahy, M.; Avaltroni, M.; Midwood, K.; Scwarzbauer, J.; Carolus, M.; Gawalt, E.  “ Enhanced bonding

layers on titanium materials”; 2004, United States Patent 10/179,743