1. A New, Short Chain Fluorosurfactant Christina Marlier Northwest Coatings Fest October 9, 2014

2. Packing improves the surface tension of short chain fluorosurfactants ≤ 18 mN/m 23-25 mN/m C2F5C2F5 n Branched surfactants Perfluorooxetane Concepts to Meet Legal and Customer Requirements Branched short chain fluorosurfactant 16-25 mN/m 21-23 mN/m 30-34 mN/m Hydrophilic moiety Simply cutting the perfluoro chain worsens the performance! REDUCTION OF BIOACCUMULATION C2F5C2F5 C2F5C2F5 C2F5C2F5 2Short Chain Fluorosurfactants | C. Marlier | September 2014

3. The Concept Branched short chain fluorosurfactant Perfluorinated part Possible higher fluorine packing density of branched short chain fluorosurfactants Branched surfactant structures should have advantages regarding static and dynamic surface tension. RfRf RfRf RfRf Hydrophilic part Ionic or Nonionic chemistry 3Short Chain Fluorosurfactants | C. Marlier | September 2014

4. Toxicity Profile Short Chain Fluorosurfactants | C. Marlier | September 20144 No bioaccumulationNo skin or eye irritationNo oral toxicityNo mutagenicityNo inhalation toxicity Inhalation and Bioaccumulation key factors when comparing to other FS

5. Static Surface Tension Results in Water Branched FS (C2F5) 5Short Chain Fluorosurfactants | C. Marlier | September 2014

6. Dynamic Surface Tension Results in Water Branched FS (C2F5)Branched FS (C3F7) Gemini Hydrocarbon Linear FS (C6F13) Silicone surfactant 6Short Chain Fluorosurfactants | C. Marlier | September 2014

7. Leveling with and without C2 Branched Flow and Leveling Short Chain Fluorosurfactants | C. Marlier | September 20147

8. Foaming Tendency Aqueous Acrylic Floor Polish 0,1% branched fluorosurfactant 60 sec 0,1% C 8 F 17 -ref anionic 0 sec 0,1% C 8 F 17 -ref anionic 120 sec 0,1% C 8 F 17 -ref anionic 60 sec 0,1% branched fluorosurfactant 0 sec 0,1% branched fluorosurfactant 120 sec 8Short Chain Fluorosurfactants | C. Marlier | September 2014

9. De-wetting Resistance No surfactant ethoxylated, acetylenic diol (non- fluorinated) Branched, C2- perfluorinated Fluorosurfactant C6-based Fluorosurfactant System: White Aqueous Low VOC Alkyd Enamel Application: images of variable thickness draw downs (between 100 to 0 microns thickness) of samples inoculated with the various test additives. Aqueous Alkyd Enamel Layer thickness 9Short Chain Fluorosurfactants | C. Marlier | September 2014

10. Visual Evaluation Acid Cure Wood Coating Ranking Most Effective to Least Effective Branched C3 Fluorosurfactant Linear C4F9 – A Linear C4F9 – B Branched C2 Fluorosurfactant No Fluorosurfactant Linear C6F14 Branched C3 top in both gloss and visual C4 shows good gloss but creates pin holes 10Short Chain Fluorosurfactants | C. Marlier | September 2014

11. Improvement of Gloss – Longwave Scan Result Comparison of C4- linear C2- branched Fluorosurfactant => C2-branched structure creates smother coating Acid Cure Wood Coating 11Short Chain Fluorosurfactants | C. Marlier | September 2014

12. Block Resistance Acid Cure Branched FS Linear C4 12Short Chain Fluorosurfactants | C. Marlier | September 2014 Least force required to separate face to face Branched FS Both welding and stick slip behavior Linear C4s

13. Gloss vs. Concentration UV-Curing Enamel Silicone Linear FS, C6F13 Superwetter Branched FS, C2F5 Branched FS, C3F7 13Short Chain Fluorosurfactants | C. Marlier | September 2014

14. Visual Evaluation UV- Curing Enamel Ranking Best to Worst Branched C2 Fluorosurfactant Branched C3 Fluorosurfactant Silicone Linear C6F13 Superwetter None Branched Fluorosurfactants top in both gloss and visual 14Short Chain Fluorosurfactants | C. Marlier | September 2014

15. Branched short-chain fluorosurfactant VERY FAST acting – excellent dynamic surface tensionGood static surface tension reductionProven good surface wetting & leveling effectsNo bioaccumulation or inhalation toxicityVery small perfluorinated chains (C2F5 – components) Major advantages 15Short Chain Fluorosurfactants | C. Marlier | September 2014

16. Critical Surfaces PolymerAbbreviation Surface free energy (SFE) at 20 °C [mN/m] Polyethylene terephthalatePET42 PolymethylmethacrylatePMMA41 PolyvinylalcoholPVA37 PolystyrenePS34 PolyethylenePE30 PolypropylenePP30 Fluorinated PE/PPFEP20 PolytetrafluoroethylenePTFE19 Upcoming Molecules Short Chain Fluorosurfactants | C. Marlier | September 201416

17. Infinite Wetting Branched short-chain fluorosurfactants 17Short Chain Fluorosurfactants | C. Marlier | September 2014

18. CMC Concentration Non-ionic Surfactant 18Short Chain Fluorosurfactants | C. Marlier | September 2014

19. Branched <C4 Chain FS Platform Conclusion Results are formulation dependent. Branched fluorosurfactants can prove effective in the most challenging coatings applications Best visual and gloss Best wetting on critical surfaces Best block resistence of FSReduced Foaming Tendency Excellent Toxicity and Bioaccumulation 19Short Chain Fluorosurfactants | C. Marlier | September 2014

20. Thank you for your attention! 20Short Chain Fluorosurfactants | C. Marlier | September 2014