Higher pentafluorosulfanyl-fluoroaliphatic carbonyl and sulfonyl fluorides, and derivatives

• US 5,159,105 A
• Filed: 02/28/1990
• Issued: 10/27/1992
• Est. Priority Date: 02/28/1990
• Status: Expired due to Fees

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Savu, Patricia M., Hansen, John C.
• Primary Examiner(s): Killos, Paul J.
• Application Number:
  US07/486,115
• Time in Patent Office: 972 Days
• Field of Search: 560/125, 560/223, 560/147, 562/605, 562/825, 562/849, 568/842
• US Class Current: 560/125
• CPC Class Codes: B61F 17/36 with other, e.g. mixed, lubricating agents
• CPC Class Codes: C07C 381/00 Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
• CPC Class Codes: C08F 8/18 Introducing halogen atoms or halogen-containing groups
• CPC Class Codes: C25B 3/28 Fluorination
• CPC Class Codes: D06M 11/55 with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
• CPC Class Codes: D06M 13/256 Sulfonated compounds esters thereof, e.g. sultones

Abstract

Pentafluorosulfanyl fluoroaliphatic carbonyl and sulfonyl fluorides, derivatives of the acid fluorides and the preparation and use of the acid fluorides and derivatives. The fluoroaliphatic moiety of said acid fluorides comprise at least three fully-fluorinated carbon atoms. The derivatives of the acid fluorides are useful as surface-active agents and surface-treating agents.

Claims

1. Fluorochemical composition comprising one or a mixture of pentafluorosulfanyl, saturated fluoroaliphatic carbonyl or sulfonyl fluorides, wherein the fluoroaliphatic moiety in said acid fluorides comprises at least three fully-fluorinated carbon atoms.

2. The fluorochemical composition of claim 1 wherein said fluorides have the general formula F₅ S--R_f --X where X is COF or SO₂ F, and R_f is a saturated fluoroaliphatic radical having a chain of at least three fully-fluorinated carbon atoms, one of which is bonded to the sulfur atom of the depicted F₅ S moiety in said formula.

3. The fluorochemical composition of claim 2 wherein said F_f is --C_n F_2n -- where n is at least 3.

4. The fluorochemical composition of claim 2 wherein said R_f is a saturated perfluorocycloaliphatic moiety.

5. The fluorochemical composition of claim 2 wherein said R_f is cyclohexylene.

6. The fluorochemical composition of claim 2 wherein F₅ S--R_f --X is F₅ S--C₃ F₆ --COF.

7. The fluorochemical composition of claim 2 wherein F₅ S--R_f --X is F₅ S--C₄ F₈ --COF.

8. The fluorochemical composition of claim 2 wherein F₅ S--R_f --X is F₅ S--C₅ F₁₀ --COF.

9. The fluorochemical composition of claim 2 wherein F₅ S--R_f --X is ##STR12##

10. Fluorochemical composition comprising a derivative of a pentafluorosulfanyl, saturated fluoroaliphatic carbonyl or sulfonyl fluoride, said derivative having a fluoroaliphatic moiety comprising at least three fully-fluorinated carbon atoms.

14. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₃ F₆ --COOH.

15. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₄ F₆ --COOH.

16. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₅ F₆ --COOH.

17. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₄ F₈ --COOLi.

18. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₄ F₈ --COONH₄.

19. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₄ F₈ --COOCH₃.

20. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₄ F₈ --CH₂ OH.

21. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₄ F₈ --CH₂ OCOCH═

CH₂.

22. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₃ F₆ --COOCH₃.

23. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₃ F₆ --CH₂ OH.

24. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₃ F₆ --COOCH₂ C₃ F₆ CH₂₀ CO--C₃ F₆ --SF₅.

25. The fluorochemical composition of claim 10 wherein said derivative is F₅ S--C₅ F₁₀ --COONH₄.

26. The fluorochemical composition of claim 10 wherein said derivative is ##STR13##

27. The fluorochemical composition of claim 10 wherein said F₅ S--R₄ --S is F₅ S--C₄ F₈ --SO₂ F.

11. Fluorochemical composition comprising a compound of the formula F₅ S--R_f --Z where R_f is a saturated fluoroaliphatic radical having a chain of at least three fully-fluorinated carbon atoms, one of which is bonded to the sulfur atom of the F₅ S moiety depicted in said formula, and Z is an organic moiety or an oxygen-containing inorganic moiety, wherein Z is a functional group capable of undergoing electrophilic, nucleophilic, or free radical reactions.

12. The fluorochemical composition of claim 11 wherein Z is --COOH or --SO₃ H, or the ammonium, amine, or metal salt of either acid.

13. The fluorochemical composition of claim 11 herein Z contains a polymerizable group.