Perfluoroaminoethers

• US 4,788,339 A
• Filed: 08/14/1986
• Issued: 11/29/1988
• Est. Priority Date: 09/06/1985
• Status: Expired due to Fees

• Current Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Original Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Inventors: Moore, George G. I., Hansen, John C.
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US06/894,311
• Time in Patent Office: 838 Days
• Field of Search: 564/453, 564/457, 564/461, 564/504, 564/505, 564/508
• US Class Current: 564/457
• CPC Class Codes: C07D 207/10 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 211/38 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 265/30 not condensed with other rings
• CPC Class Codes: C09K 5/00 Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
• CPC Class Codes: C25B 3/28 Fluorination

Abstract

Perfluoroaminoethers are provided. The perfluoroaminoethers have two or more tertiary amino nitrogen atoms each of which is connected to the other(s) adjacent thereto by (1) a catenary, ether oxygen-containing, perfluoroalkylene linking group the catenary carbon atoms of which are in the form of segments of vicinal carbon atoms that are 2 to 4 in number, said segments having up to 5 carbon atoms, a catenary ether oxygen-containing perfluorocyclohexylene linking group, or (3) a catenary ether oxygen-containing linking group having perfluoroalkylene and perfluorocyclohexylene moieties, the sum of the catenary ether oxygen atoms being 1 to 6.

Claims

1. Perfluorinated aminoether compositions comprising perfluoroaminoethers having two or more tertiary amino nitrogen atoms each of which is connected to the other(s) adjacent thereto by (1) a catenary, ether oxygen-containing perfluoroalkylene linking group, the catenary carbon atoms of which are in the form of perfluoroalkylene segments of carbon atoms that are 2 to 4 in number, said segments having up to 5 carbon atoms, (2) a catenary ether oxygen-containing perfluorocyclohexylene linking group, or (3) a catenary ether oxygen-containing linking group having said perfluoroalkylene segments and perfluorocyclohexylene moieties, the sum of the catenary ether oxygen atoms in said linking groups being 1 to 3 and each of the terminal amino nitrogen atoms having bonded thereto two perfluoroalkyl radicals.

2. Perfluorinated aminoether compositions comprising perfluoroaminoethers having the general formula ##STR42## where each R¹ and R² is independently selected from perfluoroalkyl radicals, each R³ is independently selected from acyclic perfluoroalkylene groups having 2 to 5 carbon atoms at least 2 of which are vicinal, catenary atoms, perfluorocyclohexylene, and groups having said perfluoroalkylene group and said perfluorocyclohexylene, and n is 1 to 3.

3. Compositions of claim 2 wherein each R³ is independently selected from --CF₂ CF₂ --, --CF₂ CF₂ CF₂ --, --CF₂ CF₂ CF₂ CF₂ --, --CF₂ CF(CF₃)--, --CF(CF₃)CF₂ --, --CF₂ CF(C₂ F₅)--, --CF(C₂ F₅)CF₂ --, --CF₂ C(CF₃)₂ CF₂ --, ##STR43##

4. Compositions of claim 2 wherein each R³ is independently selected from --CF₂ CF₂ -- --CF₂ CF(CF₃)-- and --CF(CF₃)CF₂ --.

5. Compositions of claim 2 wherein each ##STR44## is independently selected from --N(CF₂ CF₃)₂, --N(CF₂ CF₂ CF₃)₂, --N(C₄ F₉)₂, --N(C₅ F₁₁)₂ and --N(C₆ F₁₃)₂.

6. Compositions of claim 2 wherein each ##STR45## is independently selected from --N(CF₂ CF₂ CF₃)₂ and --N(C₄ F₉)₂.

12. A composition of claim 2 wherein said perfluoroaminoether has the formula

13. A composition of claim 2 wherein said perfluoroaminoether has the formula ##STR50##

14. A composition of claim 2 wherein said perfluoroaminoethers has the formula

15. A composition of claim 2 wherein said perfluoroaminoethers comprise a mixture of ##STR51##

16. A composition of claim 2 wherein said perfluoroaminoether has the formula

17. A composition of claim 2 wherein said perfluoroaminoether has the formula

18. A composition of claim 2 wherein said perfluoroaminoether has the formula

19. A composition of claim 2 wherein said perfluoroaminoether has the formula

20. A composition of claim 2 wherein said perfluoroaminoether has the formula

21. A composition of claim 2 wherein said perfluoroaminoether has the formula

7. Perfluorinated aminoether compositions comprising perfluoroaminoethers having the general formula ##STR46## where each R¹ and R² are independently selected from perfluoroalkyl radicals, each R³ is independently selected from acyclic perfluoroalkylene groups having 2 to 5 carbon atoms at least 2 of which are vicinal, catenary atoms, perfluorocyclohexylene groups, and groups having said perfluoroalkylene group and said perfluorocyclohexylene, R⁴ is a perfluoroalkyl radical having one to six carbon atoms, or perfluorocyclohexyl, and n is 1 to 3 and p is 0 or 1.

8. Compositions of claim 7 wherein each R³ is independently selected from --CF₂ CF₂ --, --CF₂ CF₂ CF₂ --, --CF₂ CF₂ CF₂ CF₂ --, --CF₂ CF(CF₃)--, --CF(CF₃)CF₂ --, --CF₂ CF(C₂ F₅)--, --CF(C₂ F₅)CF₂ --, --CF₂ C(CF₃)₂ CF₂ --, ##STR47##

9. Compositions of claim 7 wherein each R³ is independently selected from --CF₂ CF₂ --, --CF₂ CF(CF₃)--, and --CF(CF₃)CF₂ --.

10. Compositions of claim 7 wherein each ##STR48## is independently selected from --N(CF₂ CF₃)₂, --N(CF₂ CF₂ CF₃)₂, --N(C₄ F₉)₂, --N(C₅ F₁₁)₂, and --N(C₆ F₁₃)₂.

11. Compositions of claim 7 wherein each ##STR49## is --N(CF₂ CF₂ CF₃)₂.