Mixed fluoroalkyl-alkyl surfactants
View Patent ↗A surfactant of formula 1 (R f -A) a -Q-([B] k —R) b Formula 1 wherein a and b are each independently 1 or 2; R f is a linear or branched perfluoroalkyl radical having from 2 to about 20 carbon atoms, optionally interrupted with at least one oxygen; R is a C 1 to C 20 linear, branched or cyclic alkyl, or a C 6 to C 10 aryl; B is —(CH 2 CHR 1 O) x —, k is 0 or 1, x is 1 to about 20, A is —(CH 2 ) m [(CHR 1 CH 2 O)] s —[(CH 2 ) m (CH) t CHOH(CH 2 ) m ] e —, wherein each m is independently 0 to 3, s is 0 to about 30, t is 0 or 1, and e is 0 or 1, R 1 is H or CH 3 , Q is: —OP(O)(O − M + )(O)—, —O—, —S—(CH 2 ) m —C(O)—O—, —SO 2 —O— —CH 2 CH 2 O—C(O)CH 2 C(OH)(V)CH 2 C(O)O—; —(CH 2 CH 2 O) x CH 2 CH(OH)—(CH 2 CH 2 O) x —(CH 2 ) m —Si[OSi(R 2 ) 3 ] 2 —, —SO 2 NR 2 —, —(CH 2 CH 2 O) z C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) z — wherein z is 1 to about 15, or a bond when s is a positive integer, V is —C(O)OR 3 and R 3 is H, CH 3 or R f ; R 2 is C 1 to C 4 alkyl, and M + is a Group 1 metal or an ammonium (NH x R 2 y ) + cation wherein x+y=4, and R 2 is C 1 to C 4 alkyl, provided that when Q is —OP(O)(O − M + )(O)— or when Q is —(CH 2 CH 2 O) z —C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) z —, then at least one of s or e is a positive integer.
1. A surfactant of formula 1
(R f -A) a -Q-([B] k —R) b Formula 1
wherein
a and b are each independently 1 or 2;
R f is a linear or branched perfluoroalkyl radical having from 2 to about 20 carbon atoms, optionally interrupted with at least one oxygen;
R is a C 1 to C 20 linear, branched or cyclic alkyl, or a C 6 to C 10 aryl;
B is —(CH 2 CHR 1 O) x —,
k is 0 or 1, x is 1 to 20,
A is (CH 2 ) m [(CHR 1 CH 2 O)] s —[(CH 2 ) m (CH) t CHOH(CH 2 ) m ] e —,
wherein
each m is independently 0 to 3, s is 0 to 30, t is 0 or 1, and e is 0 or 1,
R 1 is H or CH 3 ,
Q is:
—S—(CH 2 ) m —C(O)—O—,
—SO 2 —O—
—CH 2 CH 2 O—C(O)CH 2 C(OH)(V)CH 2 C(O)O—;
(CH 2 CH 2 O) x CH 2 CH(OH)—CH 2 O—(CH 2 CH 2 O) x —(CH 2 ) m —Si[OSi(R 2 ) 3 ] 2 —,
—SO 2 NR 2 —,
—(CH 2 CH 2 O) z C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) z — wherein z is 1 to 15, or
a bond when s is a positive integer,
V is —C(O)OR 3 and R 3 is H, CH 3 or R f ;
R 2 is C 1 to C 4 alkyl, and
M + is a Group 1 metal or an ammonium (NH x R 2 y ) + cation wherein x and y are each independently 0 to 4, and x+y=4, and R 2 is C 1 to C 4 alkyl,
provided that when Q is —(CH 2 CH 2 O) z —C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) z —, then at least one of s or e is a positive integer.
2. The surfactant of claim 1 having the following formula
R f (CH 2 ) 2 S(CH 2 ) 2 C(O)O(CHR 1 CH 2 O) x R
wherein
R f , R 1 , x and R are as defined in claim 1 .
3. The surfactant of claim 1 having the following formula
R f (CH 2 ) 2 S(O 2 )O(CHR 1 CH 2 O) x R
wherein
R f , R 1 , x and R are as defined in claim 1 .
4. The surfactant of claim 1 having the following formula
R f (CH 2 ) 2 O(CHR 1 CH 2 O) x C(O)CH 2 C(OH)(C(O)OH)CH 2 C(O)O(CHR 1 CH 2 O) x R
wherein
R f , R 1 , x and R are as defined in claim 1 .
5. The surfactant of claim 1 wherein A is —(CH 2 ) m [(CHR 1 CH 2 O)] s —[(CH 2 ) m (CH) t CHOH(CH 2 ) m ] e — wherein m is 0, s is 2, e is 0, and R 1 is as defined in claim 1 ; a is 1; Q is —(CH 2 CH 2 O) x CH 2 —CH(OH)CH 2 O—(CH 2 CH 2 O) x —(CH 2 ) m Si[OSi(R 2 ) 3 ] 2 — wherein x, m, and R 2 are as defined in claim 1 ; k is 0; b is 1; and R f and R are as defined in claim 1 .
6. The surfactant of claim 1 having the following formula
R f (CH 2 ) 2 S(O 2 )N(R 2 )(CHR 1 CH 2 O) x R
wherein
R f , R 1 , R 2 , x and R are as defined in claim 1 .
7. The surfactant of claim 1 wherein Q is —(CH 2 CH 2 O) z C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) z —, wherein z is 1 to 15, and R f , A, a, B, k, R, and b are as defined in claim 1 .
8. The surfactant of claim 1 having a surface tension of less than about 25 mN/in at a concentration of 0.1% by weight in water.
9. The surfactant of claim 1 having a surface tension of less than about 20 mN/in at a concentration of 0.5% by weight in water.