1. Thiadiazole Technology: -Motor Oil Antiwear -Grease Extreme Pressure Tom Karol, Ph.D. Research Director

2. 1,3,4-Thiadiazole Chemistry –Physical /Performance Properties Liquid Wear/EP performance equivalent to or better than heavy metal technology Environmentally friendly wear/EP agent Ashless Biodegradable preferred Cost effective – Commercially viable process

3. Theory of Thiadiazoles as EP additives Theory of simple thiadiazole coordination Theory of dimer thiadiazole complexation Theory of poly thiadiazole coordination

4. Simple Thiadiazole Coordination

5. SEQUENCE VD WEAR RESULTS conducted in the same prototype motor oil base formulation ____Wear____ Max. Avg. 0.08P ZnDTP fail fail 0.09P ZnDTP pass pass 0.1% thiadiazole technology plus 0.08P ZnDTP 0.0040 0.0029 Sequence VD limits 0.0080 0.0040

6. Dimer Thiadiazole Complexation Bidentate Coordination

7. Theory of Poly-Thiadiazole Coordination Polydentate association

8. Introduction of VANLUBE 972 -Achieves polydentate propertiesthrough poly- thiadiazole coordination -Useful as a Grease Extreme Pressure additive

9. 2,5-Dimercapto-1,3,4- Thiadiazole Disulfide Dimer

10. VANLUBE 972 Metal Coordination Polydentate association

11. IR ABSORPTION Major shifts in peaks are further evidence for the complex formation: Compound Absorption Peaks (cm -1 ) DMTD disulfide bis-dimer 1487, 1435, 1406, 1262, 1212 Triethylene glycol monobutyl ether 1460, 1351, 1297, 1248 Complex, 40% monosulfide bis-dimer 1510, 1433, 1350, 1244

12. SATURATION POINT SOLVENT % DIMER THF 16.6 Acetone 2.4 Acetonitrile <0.04 Triethylene Glycol Monobutyl Ether 48 Triethylene Glycol Dimethyl Ether 56 Polyethylene Glycol (MW 400) 45

13. Modified ASTM D 4048 Cu Corrosion 24h @ 100°C VANLUBE 972 mass percent 1235 Li-12 OH Grease 99989795 Heptane and towel rub Wt Change, mg +5.8+8.4+14.8+22.1 DMK Towel Rubbing, Wt Change, mg +1.9+0.1+1.6+5.8 Rating2e DMK = dimethylketone (acetone)

14. Effect of VANLUBE 972 VANLUBE 972 1% Molybdenum Dithiophosphate, mass 1% Li-12OH Stearate Grease, mass 99%98% Copper Strip Weight Before, g25.417527.0688 Weight Change, mg -2.1+4.0 Heptane & Paper Towel, Weight Change, mg -2.8+4.2 Acetone & Paper Towel, Weight Change, mg -3.1+3.2 Rating, ASTM D 4048 4a2e

15. Modified ASTM D 4048 Copper Corrosion Test mass percent

16. VANLUBE 972 and Fe Corrosion Inhibitors Grease VL 972 Mass % Timken, lb 4- Ball Weld,kgf 4-Ball Wear, mm Aluminum Complex #2 0.00 - - 1.00 40 - 0.50, 0.49, 0.43 1.25 Failed 50 - - 1.50 Failed 50 - - 1.75 60 315 0.96, 0.71, 0.73 2.00 80 - - Aluminum Complex #2 With 0.5% OD-9316 1.00 Failed 50 315 0.60, 0.67 1.75 60 - 0.60, 0.67 Aluminum Complex #2 With 1.0% OD-9316 1.00 50 250 0.63, 0.67

17. Biodegradation Study of VANLUBE 972:

18. MaterialMass (mg) % Degradation VANLUBE 972 18.278.0 23.146.5 Sodium Benzoate 36.078.4 Canola Oil 30.138.5