Fluoroalkenyl poly[1,6]glycosides
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:
a solvent; and
a first fluorosurfactant of formula (I)
where
L is (—CH 2 CH 2 O—) n , (—CH 2 CH(OH)CH 2 O—) n , or (—CH 2 —) n ;
n is 0 to 8;
x>1; and
R f is a fluorocarbon group.
2. The composition of claim 1 , wherein R f is a C 4 -C 10 fluorocarbon group; and wherein L is (—CH 2 CH 2 O—), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
3. The composition of claim 2 , wherein R f is a C 6 fluorocarbon group.
4. The composition of claim 1 , further comprising a hydrocarbon surfactant; and a second fluorosurfactant.
5. The composition of claim 1 , wherein the solvent is selected from the group consisting of water, iso-propyl alcohol, t-butyl alcohol, glycol and butyl carbitol.
6. The composition of claim 1 , wherein the first fluorosurfactant is of formula (II):
where
L is (—CH 2 CH 2 O—) n , (—CH 2 CH(OH)CH 2 O—) n , or (—CH 2 —) n ;
n is 0 to 8;
x>1; and
R f is a fluorocarbon group.
7. The composition of claim 6 , further comprising a hydrocarbon surfactant; and a second fluorosurfactant; and
wherein R f is a C 4 -C 10 fluorocarbon group; and wherein L is (—CH 2 CH 2 O—), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
8. A method of extinguishing a fire comprising applying to said fire a composition comprising a solvent and a first fluorosurfactant of formula (I):
where
L is (—CH 2 CH 2 O—) n , (—CH 2 CH(OH)CH 2 O—) n , or (—CH 2 —) n ;
n is 0 to 8;
x>1; and
R f a fluorocarbon group.
9. The method of claim 8 , wherein R f is a C 4 -C 10 fluorocarbon group; and wherein L is (—CH 2 CH 2 O—), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
10. The method of claim 8 , wherein the composition further comprises a hydrocarbon surfactant; and a second fluorosurfactant.
11. The method of claim 8 , wherein the first fluorosurfactant is of formula (II):
where
L is (—CH 2 CH 2 O—) n , (—CH 2 CH(OH)CH 2 O—) n , or (—CH 2 —) n ;
n is 0 to 8;
x>1; and
R f is a fluorocarbon group.
12. The method of claim 11 , further comprising a hydrocarbon surfactant; and a second fluorosurfactant; and
wherein R f is a C 4 -C 10 fluorocarbon group; and wherein L is (—CH 2 CH 2 O—), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
13. A compound of formula (I):
where
L is (—CH 2 CH 2 O—) n , (—CH 2 CH(OH)CH 2 O—) n , or (—CH 2 —) n ;
n is 0 to 8;
x>1; and
R f is hydrogen or a fluorocarbon group;
with the proviso that when R f is hydrogen, n is 1 to 8.
14. The compound of claim 13 , where R f is a fluorocarbon group.
15. The compound of claim 14 , wherein R f is a C 4 -C 10 fluorocarbon group; and L is (—CH 2 CH 2 O—), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
16. The compound of claim 1 , where R f is hydrogen and L is (—CH 2 CH 2 O—), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
17. The compound of claim 13 , of formula (II):
where
L is (—CH 2 CH 2 O—) n , (—CH 2 CH(OH)CH 2 O—) n , or (—CH 2 —) n ;
n is 0 to 8;
x>1; and
R f is hydrogen or a fluorocarbon group;
with the proviso that when R f is hydrogen, n is 1 to 8.
18. The compound of claim 17 , where R f is a fluorocarbon group.
19. The compound of claim 18 , where R f is a C 4 -C 10 fluorocarbon group; and L is (—CH 2 CH 2 —), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
20. The compound of claim 17 , where R f is hydrogen and L is (—CH 2 CH 2 O—), (—CH 2 CH(OH)CH 2 O—), or —CH 2 —.
21. A fire extinguishing composition comprising:
a solvent; and
a fluoroalkenyl glycoside surfactant having a non-Flory distribution of glycosides, and enriched in fluoroalkenyl poly[1,6]glycoside.
22. The composition of claim 21 , wherein the fluoroalkenyl glycoside surfactant comprises at least 90 mole % fluoroalkenyl poly[1,6]glycoside and less than about 10 mole % fluoroalkenyl monoglycoside.
23. The composition of claim 22 , wherein the fluoroalkenyl poly[1,6]glycoside is of formula (I):
where
L is (—CH 2 CH 2 O—) n , (—CH 2 CH(OH)CH 2 O—) n , or (—CH 2 —) n ;
n is 0 to 8;
x>1; and
R f is a fluorocarbon group.
24. A fluoroalkenyl poly[1,6]glycoside surfactant made by the steps of:
providing a sugar;
providing an alkenyl alcohol;
combining the sugar and the alkenyl alcohol to form an alkenyl glycoside mixture;
removing alkenyl monoglycoside from the alkenyl glycoside mixture to form an alkenyl poly[1,6]glycoside;
providing a fluoroalkylating agent;
combining the alkenyl poly[1,6]glycoside and the fluoroalkylating agent in the presence of a radical initiator to form the fluoroalkenyl poly[1,6]glycoside.