Perfluoroalkyl composition with reduced chain length

Patent metadata

Field	Value
Publication number	US-9956448-B2
Application number	US-201414776057-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	Mar 15, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Novel fluorosurfactants are provided that contain perfluoroalkyl groups no longer than perfluorohexyl (C 6 ). The surfactants are useful in the preparation of aqueous film forming foams (AFFF) and alcohol-resistant film-forming foams (AR-AFFF) for firefighting. Unexpectedly, these compounds have activity in AFFF and AR-AFFF applications that is comparable and even superior to conventional surfactants that contain perfluoroalkyl groups that are perfluorooctyl (C 8 ) and longer. Also provided are methods of making the novel surfactants, as well as foam concentrates, methods of making foam and methods of fighting fires using foam containing the novel surfactants.

First claim

The invention claimed is:

1. A fire-fighting foam, comprising a composition comprising a surfactant having the formula

wherein R f is CF 3 (CF 2 ) n or CHF 2 (CF 2 ) n , wherein n is 3-5;
A is a linker selected from the group consisting of —CH 2 CH 2 —, —CH 2 CH 2 —S—, —CH 2 CH 2 —O—, —CH 2 CH 2 —CO—NH—, —CH 2 CH 2 —NH—CO— —SO 2 NH—, —NHSO 2 —, —OC(O)—, —C(O)O—, —S(O)—, and —SO 2 —;
X is selected from the group consisting of —S—, —O—, —SO 2 —, —NR—, —CO 2 —, —CONR—, —SO 2 NR—, —OP(O)(OR)O—, S(O), —OC(O)—, —NRC(O)—, and —NRSO 2 —;
Y is selected from the group consisting of —CONHR, CO 2 H, —CO 2 R, —OC(O)R, and —C 6 H 4 SO 3 M;
R is H or C 1 -C 6 alkyl;
R′ is H or C 1 -C 6 alkyl;
M is a metal ion; and
m is 2-8 and p is 2-100,
and wherein said composition is substantially free of any surfactant containing a perfluoroalkyl group containing more than 6 carbon atoms.

2. A method of making a fire-fighting foam, comprising foaming a composition according to claim 1 with an aqueous liquid.

3. A method of fighting a fire comprising contacting a fire with a foam prepared according to the method of claim 2 .

4. The method according to claim 2 , wherein said aqueous liquid is brackish water or seawater.

5. The fire-fighting foam according to claim 1 , wherein said composition further comprises an effective amount of one or more components selected from the group consisting of: an amphoteric hydrocarbon surfactant, an anionic hydrocarbon surfactant, a nonionic hydrocarbon surfactant, a C 6 fluorochemical surfactant, a foam aid, a freeze protection composition, a composition comprising ion sequestering, buffer, and anti-corrosion components, a polymeric film forming composition, a biocides and antimicrobial composition, an electrolyte composition, and a polysaccharide gum thickener.

6. The fire-fighting foam according to claim 5 , wherein said composition comprises an amphoteric hydrocarbon surfactant in an amount up to 3% w/w.

7. The fire-fighting foam according to claim 5 , wherein said composition comprises an anionic hydrocarbon surfactant in an amount of 2-10% w/w.

8. The fire-fighting foam according to claim 5 , wherein said composition comprises a nonionic hydrocarbon surfactant in an amount up to 5% w/w.

9. The fire-fighting foam according to claim 5 , wherein said composition comprises an additional C 6 fluorochemical surfactant in an amount up to 0.4% w/w.

10. The fire-fighting foam according to claim 5 , wherein said composition comprises a foam aid in an amount up to 15% w/w.

11. The fire-fighting foam according to claim 1 , wherein said composition comprises a freeze protection composition in an amount up to 45% w/w.

12. The fire-fighting foam according to claim 1 , wherein said composition comprises ion sequestering, buffer, and anti-corrosion components in an amount up to 5% w/w.

13. The fire-fighting foam according to claim 1 , wherein said composition comprises a polymeric film forming composition in an amount up to 2%.

14. The fire-fighting foam according to claim 1 , wherein said composition comprises biocides and/or antimicrobials in an amount up to 0.1% w/w.

15. The fire-fighting foam according to claim 1 , wherein said composition comprises electrolytes in an amount up to 3% w/w.

16. The fire-fighting foam according to claim 1 , wherein said composition comprises at least one polysaccharide gum thickener in an amount up to 10% w/w.

17. The fire-fighting foam according to claim 1 , comprising magnesium sulfate.

18. The fire-fighting foam according to claim 1 , wherein R f is CF 3 (CF 2 ) 5 .

19. The fire-fighting foam according to claim 1 , wherein A is —CH 2 CH 2 —S—.

20. The fire-fighting foam according to claim 1 , wherein m is 4.

21. The fire-fighting foam according to claim 1 , wherein X is —S—.

22. The fire-fighting foam according to claim 1 , wherein the weight average molecular weight of said surfactant is 750-7500.

23. The fire-fighting foam according to claim 1 , wherein the surfactant has the formula

24. The fire-fighting foam according to claim 1 , wherein p is 4-20.

Assignees

• Tyco Fire Products Lp

Inventors

• Martin Thomas Joseph

Classifications

• A62D1/0085 Primary

  containing perfluoroalkyl-terminated surfactant · CPC title

• C07C323/22

  containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• A62D1/0042

  "Wet" water, i.e. containing surfactant · CPC title

• C08G75/02

  Polythioethers · CPC title