Fluoroalkenyl sulfate surfactants
Fire extinguishing compositions and methods of extinguishing a fire comprising compounds of formula (I) where R f is a fluorocarbon group. The compounds and compositions described herein are useful as intermediates in the preparation of or as additives to AFFF (aqueous film forming foam) formulations used for the extinguishment of fuel and solvent fires.
1. A fire extinguishing composition comprising:
at least one solvent; and
a first fluorosurfactant of formula (I)
where
L is absent, C 1 -C 10 alkylene-O—, (—CH 2 CH 2 O—) n , (—CH 2 CH(CH 3 )O—) n , or (—CH 2 CH(OH)CH 2 O—) n ;
n is an integer from 1 to 10;
R f is a C 4 -C 10 alkyl group substituted with 2m or (2m+1) fluoro atoms where m is the number of carbons in the alkyl backbone;
M is an alkali metal cation, an alkaline earth metal cation, ammonium cation, a C 1 -C 4 mono-substituted ammonium cation, a C 1 -C 4 di-substituted ammonium cation, a C 1 -C 4 tri-substituted ammonium cation, or a C 1 -C 4 tetra-substituted ammonium cation; and
x is an integer selected from 1 or 2, and corresponds to the valency of M.
2. The composition of claim 1 , further comprising a hydrocarbon surfactant; and a second fluorosurfactant.
3. The composition of claim 1 , wherein said solvent is selected from the group consisting of water, iso-propyl alcohol, t-butyl alcohol, glycol, butyl carbitol, and hexylene glycol.
4. A method of extinguishing a fire comprising:
applying to said fire a composition comprising:
at least one solvent; and
a compound of formula I
where
L is absent, C 1 -C 10 alkylene-O—, (—CH 2 CH 2 O—) n , (—CH 2 CH(CH 3 )O—) n , or (—CH 2 CH(OH)CH 2 O—) n ;
n is an integer from 1 to 10;
R f is a C 4 -C 10 alkyl group substituted with 2m or (2m+1) fluoro atoms where m is the number of carbons in the alkyl backbone;
M is an alkali metal cation, an alkaline earth metal cation, ammonium cation, a C 1 -C 4 mono-substituted ammonium cation, a C 1 -C 4 di-substituted ammonium cation, a C 1 -C 4 tri-substituted ammonium cation, or a C 1 -C 4 tetra-substituted ammonium cation; and
x is an integer selected from 1 or 2, and corresponds to the valency of M.
5. The method of claim 4 , wherein the composition further comprises a hydrocarbon surfactant; and a second fluorosurfactant.
6. The method of claim 4 , wherein R f is C 4 F 9 , C 6 F 13 , or C 8 F 17 .
7. The method of claim 4 , wherein said solvent is selected from the group consisting of water, iso-propyl alcohol, t-butyl alcohol, glycol, butyl carbitol, and hexylene glycol.
8. A compound of formula (I):
where
L is absent, C 1 -C 10 alkylene-O—, (—CH 2 CH 2 O—) n , (—CH 2 CH(CH 3 )O—) n , or (—CH 2 CH(OH)CH 2 O—) n ;
n is an integer from 1 to 10;
R f is a C 4 -C 10 alkyl group substituted with 2m or (2m+1) fluoro atoms where m is the number of carbons in the alkyl backbone;
M is an alkali metal cation, an alkaline earth metal cation, ammonium cation, a C 1 -C 4 mono-substituted ammonium cation, a C 1 -C 4 di-substituted ammonium cation, a C 1 -C 4 tri-substituted ammonium cation, or a C 1 -C 4 tetra-substituted ammonium cation; and
x is an integer selected from 1 or 2, and corresponds to the valency of M.
9. The compound of claim 8 , wherein M is an alkali metal cation selected from the group consisting of a potassium, lithium, and sodium cation, and x is 1.
10. The compound of claim 8 , wherein M is a magnesium cation, and x is 2.
11. The compound of claim 8 , wherein M is an ammonium cation, a C 1 -C 4 mono-substituted ammonium cation, a C 1 -C 4 di-substituted ammonium cation, a C 1 -C 4 tri-substituted ammonium cation, or a C 1 -C 4 tetra-substituted ammonium cation and x is 1.
12. The compound of claim 9 , wherein R f is a C 4 -C 10 alkyl containing (2m+1) fluoro atoms where m is the number of carbons in the alkyl backbone.
13. The compound of claim 12 , wherein R f is C 4 F 9 , C 6 F 13 , or C 8 F 17 .
14. The compound of claim 13 , wherein L is (—CH 2 CH 2 O—) n .
15. The compound of claim 14 , wherein n is 0, 1 or 2.
16. The compound of claim 8 , wherein said compound is selected from the group consisting of:
2-(4,4,5,5,6,6,7,7,7-nonafluorohept-2-enyloxy)ethyl hydrogen sulfate;
4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoronon-2-enyl hydrogen sulfate;
2-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoronon-2-enyloxy)ethyl hydrogen sulfate;
2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundec-2-enyloxy)ethyl hydrogen sulfate; and
34,34,35,35,36,36,37,37,38,38,39,39,39-tridecafluoro-3,6,9,12,15,18,21,24,27,30-decaoxatetracont-32-enyl hydrogen sulfate.