PERFLUOROALKYL SUBSTITUTED QUATERNARY AMMONIUM SALTS

• US 3,723,512 A
• Filed: 06/09/1970
• Issued: 03/27/1973
• Est. Priority Date: 06/11/1969
• Status: Expired due to Term

• Current Assignee: Hans Niederprum, Peter Voss, Volker Beyl
• Original Assignee: Hans Niederprum, Peter Voss, Volker Beyl
• Inventors: Niederprum, Hans, Voss, Peter, Beyl, Volker
• Primary Examiner(s): Mars, Howard T.
• Assistant Examiner(s): Schwartz, Gerald A.
• Application Number:
  US05/044,871
• Time in Patent Office: 1,022 Days
• Field of Search: 260/501.15,448.2E,247.1,294.8F,309,326.82 23/205
• US Class Current: 562/113
• CPC Class Codes: A62D 1/0085 containing perfluoroalkyl-terminated surfactant
• CPC Class Codes: C07C 309/00 Sulfonic acids; Halides, esters, or anhydrides thereof
• CPC Class Codes: C07D 213/20 Quaternary compounds thereof
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 233/56 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 249/08 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: Y10S 260/20 Antistatic agent contains pentavalent nitrogen
• CPC Class Codes: Y10S 516/07 Organic amine, amide, or n-base containing

Abstract

Quaternary ammonium salts of perfluorinated alkylsulfonic acids and their production from a tertiary amine, a perfluorinated alkylsulfonyl fluoride and an alkoxy- or aryloxy-silane which contributes its alkyl or aryl radical to make up the fourth substituent of the resulting quaternary ammonium nitrogen atom.

Claims

2. A process according to claim 1, wherein three of R1, R2, R3 and R4 are lower alkyl.

3. A process according to claim 2, wherein the fourth of R1, R2, R3, and R4 is higher alkyl or benzyl.

4. A process according to claim 1, wherein RF is a perfluorinated alkyl radical containing up to about eight carbon atoms.

5. A process according to claim 4, wherein R5 is a lower alkyl radical and n is 1.

6. A process according to claim 1, wherein the reaction is carried out in an inert solvent at a temperature of from -50* to +100*C.

7. A compound of the general formula:

)R1R2R3R4N) (RFSO3) in which RF represents a straight chain or branched perfluorinated aliphatic hydrocarbon radical having from one to 12 C atoms and R1, R2, R3 and R4, which may be the same or different, are alkyl, alkenyl, cycloalkyl or aralkyl radicals having up to 20 C atoms or two or three of R1, R2 and R3 form a heterocyclic ring together with the nitrogen selected from the group consisting of pyridine, imidazole, pyrrolidine and morpholine rings.

8. A compound according to claim 7, wherein R1, R2 and R3 are methyl or ethyl.

9. A compound according to claim 8, wherein R4 is higher alkyl having up to 20 C atoms or benzyl.

10. A compound according to claim 2, wherein RF is a perfluorinated alkyl radical containing up to eight carbon atoms.