IP Library Granted Patent US 8,399,713
Granted Patent B2
US 8,399,713 · App. 12/701,802 · Granted Mar 19, 2013

Alkyl perfluoroalkene ethers

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,399,713
App. No.
12/701,802
Granted
Mar 19, 2013
Kind
B2
Abstract

Disclosed are compositions comprising a compound having the formula CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , wherein R is CH 3 or C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=1, 2 or 3. Also disclosed are unsaturated fluoroethers selected from the group consisting of CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , CF 3 (CF 2 ) x C(OR)═CFCF 2 (CF 2 ) y CF 3 , CF 3 CF═CFCF(OR)(CF 2 ) x (CF 2 ) y CF 3 , CF 3 (CF 2 ) x CF═C(OR)CF 2 (CF 2 ) y CF 3 , and mixtures thereof, wherein R can be either CH 3 , C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3. Also disclosed herein are novel methods of using a composition comprising at least one of the compounds described above as novel solvents, carrier fluids, dewatering agents, degreasing solvents or defluxing solvents.

Claims (37)

1. A composition comprising at least one unsaturated fluoroether having a formula selected from the group consisting of CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , CF 3 (CF 2 ) x C(OR)═CFCF 2 (CF 2 ) y CF 3 , CF 3 CF═CFCF(OR)(CF 2 ) x (CF 2 ) y CF 3 , and mixtures thereof, wherein R can be either CH 3 , C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=1, 2 or 3, except that said unsaturated fluoroether is not CF 3 CF 2 CF═C(OCH 3 )(CF 2 ) 2 CF 3 .

2. The composition of claim 1 , wherein the unsaturated fluoroether comprises a compound having the formula CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , wherein R is CH 3 or C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y =1, 2 or 3.

3. The composition of claim 2 , further comprising a compound having the formula CF 3 (CF 2 ) x C(OR)═CFCF 2 (CF 2 ) y CF 3 , wherein R is CH 3 or C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=1, 2 or 3.

4. The composition of claim 1 , wherein the unsaturated fluoroether comprises a compound having the formula CF 3 (CF 2 ) x C(OR)═CFCF 2 (CF 2 ) y CF 3 , wherein R is CH 3 or C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y =1, 2 or 3, except that when x=2 and R is CH 3 , y does not equal 0.

5. The composition of claim 1 , wherein the unsaturated fluoroether comprises a compound having the formula CF 3 CF═CFCF(OR)(CF 2 ) x (CF 2 ) y CF 3 , wherein R is CH 3 or C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y =1, 2 or 3.

6. The composition of claim 2 , wherein R is C 2 H 5 .

7. The composition of claim 2 wherein R is CH 3 .

8. A method for removing residue from a surface comprising:

a. contacting the surface with a composition comprising at least one unsaturated fluoroether selected from the group consisting of CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , CF 3 (CF 2 ) x C(OR)═CFCF 2 (CF 2 ) y CF 3 , CF 3 CF═CFCF(OR)(CF 2 ) x (CF 2 ) y CF 3 , CF 3 (CF 2 ) x CF═C(OR)CF 2 (CF 2 ) y CF 3 , and mixtures thereof, wherein R can be either CH 3 , C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3;

b. recovering the surface from the composition.

9. The method of claim 8 wherein said composition further comprises a propellant.

10. The method of claim 9 wherein said propellant is selected from the group consisting of air, nitrogen, carbon dioxide, difluoromethane (CF 2 H 2 , HFC-32), trifluoromethane (CF 3 H, HFC-23), difluoroethane (CHF 2 CH 3 , HFC-152a), trifluoroethane (CH 3 CF 3 , HFC-143a; or CHF 2 CH 2 F, HFC-143), tetrafluoroethane (CF 3 CH 2 F, HFC-134a; or CF 2 HCF 2 H, HFC-134), pentafluoroethane (CF 3 CF 2 H, HFC-125), 1,3,3,3-tetrafluoro-1-propene (HFO-1234ze), 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), 1,2,3,3,3-pentafluoropropene (HFO-1225ye), 1,1,3,3,3-pentafluoropropene (HFO-1225ze), hydrocarbons, and dimethyl ether.

11. The method of claim 8 wherein said composition further comprises at least one surfactant.

12. The method of claim 8 wherein said contacting is accomplished by vapor degreasing.

13. The method of claim 12 , wherein the vapor degreasing is performed by:

a. Boiling the composition; and

b. Exposing the article to vapors of the boiling cleaning composition.

14. The method of claim 8 , wherein the contacting is accomplished by immersing the article in said composition, wherein the composition is at a temperature greater than ambient or room temperature.

15. The method of claim 14 , wherein the composition is at a temperature of about the boiling point of the composition.

16. The method of claim 14 comprising, after immersing the article in the composition, the further step of immersing the article in the composition, wherein the composition is at a temperature lower than that of the first immersing step.

17. The method of claim 16 , wherein the composition in the second immersing step is at ambient or room temperature.

18. The method of claim 16 comprising, after the second immersing step, the further steps of boiling the composition and exposing the article to vapors of the boiling composition.

19. The method of claim 8 , wherein the composition is at ambient or room temperature.

20. The method of claim 8 , wherein the contacting is accomplished by wiping the article with an object soaked in the composition.

21. A method for depositing a fluorolubricant on a surface comprising:

a. combining a fluorolubricant and a solvent, said solvent comprising at least one unsaturated fluoroether selected from the group consisting of CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , CF 3 (CF 2 ) x C(OR)═CFCF 2 (CF 2 ) y CF 3 , CF 3 CF═CFCF(OR)(CF 2 ) x (CF 2 ) y CF 3 , CF 3 (CF 2 ) x CF═C(OR)CF 2 (CF 2 ) y CF 3 , and mixtures thereof, wherein R can be either CH 3 , C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3, to form a lubricant-solvent combination;

b. contacting the combination of lubricant-solvent with the surface; and

c. evaporating the solvent from the surface to form a fluorolubricant coating on the surface.

22. The method of claim 21 , wherein the surface is that of a semiconductor material, metal, metal oxide, vapor deposited carbon, or glass.

23. The method of claim 22 , wherein the surface is that of a magnetic medium.

24. The method of claim 23 , wherein the magnetic medium is a computer disk.

25. The method of claim 21 , wherein the contacting step is accomplished by dipping or immersing the surface in a bath comprising the fluorolubricant.

26. The method of claim 21 , wherein the contacting step is accomplished by spraying or spin coating the surface with the fluorolubricant.

27. The method of claim 21 , wherein the fluorolubricant concentration in the lubricant-solvent combination is from about 0.02 weight percent to about 0.5 weight percent.

28. The method of claim 21 , wherein the evaporating step is accomplished at a temperature of from about 10° C. to about 40° C.

29. The method of claim 21 , wherein the fluorolubricant comprises a perfluoropolyether.

30. The method of claim 21 , wherein the fluorolubricant is selected from the group consisting of perfluoropolyethers and mixtures thereof.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2010
From: BARTELT, JOAN ELLEN; LOUSENBERG, ROBERT D.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 024033/0377 →