Quaternized amido cyclic amine surfactant
View Patent ↗A quaternary surfactant comprising a cyclic diamine group, compositions comprising the quaternized amido cyclic amine surfactant, a gelled aqueous composition comprising the quaternized amido cyclic amine surfactant, use of the gelled aqueous well treatment applications and methods of preparation and intermediates used to prepare the quaternized amido cyclic amine surfactant.
1. A quaternized amido cyclic amine surfactant of formula
wherein R is selected from the group consisting of C 12 –C 30 alkenyl, C 12 –C 30 arylalkyl and C 12 –C 30 cycloalkylalkyl; R 1 and R 2 are independently selected from C 3 –C 8 cycloalkyl, aryl, C 6 –C 10 arylalkyl, C 2 –C 5 hydroxyalkyl and C 1 –C 5 alkyl; m and n are independently integers of 1 to about 4; X is absent; and one of R 1 and R 2 is substituted with carboxylate or sulfonate.
2. The quaternized amido cyclic amine surfactant of claim 1 wherein R is C 12 –C 30 alkenyl.
3. The quaternized amido cyclic amine surfactant of claim 2 wherein R is C 18 –C 30 alkenyl.
4. The quaternized amido cyclic amine surfactant of claim 3 wherein m and n are both 2.
5. The quaternized cyclic diamine of claim 4 wherein R 1 is C 1 –C 5 alkyl and R 2 is C 1 –C 5 alkyl or C 2 –C 5 hydroxyalkyl wherein the alkyl or hydroxyalkyl is substituted with carboxylate or sulfonate.
6. The quaternized cyclic diamine of claim 5 wherein R 1 is methyl and R 2 is —CH 2 CH 2 CH 2 SO 3 − .
7. An aqueous composition comprising
a) about 75 to about 90 weight percent of a quaternized cyclic diamine composition comprising about 20 to about 60 weight percent of one or more C 1 –C 4 alcohols or C 2 –C 6 diols and about 40 to about 80 weight percent of one or more quaternized cyclic diamines of formula
wherein R is selected from the group consisting of C 12 –C 30 alkyl, C 12 –C 30 alkenyl, C 12 –C 30 arylalkyl and C 12 –C 30 cycloalkylalkyl; R 1 and R 2 are independently selected from C 3 –C 8 cycloalkyl, aryl, C 6 –C 10 arylalkyl, C 2 –C 5 hydroxyalkyl and C 1 –C 5 alkyl; m and n are independently integers of 1 to about 4; and X is absent or is selected from halide and methyl sulfate, provided that when X is absent, one of R 1 and R 2 is substituted with carboxylate or sulfonate;
b) about 1 to about 15 weight percent of one or more glycols or C 1 –C 8 alcohols; and
c) about 1 to about 10 weight percent water.
8. The aqueous composition of claim 7 wherein the C 1 –C 4 alcohol is isopropanol.
9. The aqueous composition of claim 7 wherein the C 2 –C 6 diol is 1,2-propane diol.
10. A gelled aqueous composition comprising
a) about 0.5 to about 10 weight percent of the aqueous composition of claim 7 ;
b) about 0.5 to about 20 weight percent of one or more salts or one or more C 4 –C 10 alcohols; and
c) water.
11. The gelled aqueous composition of claim 10 wherein the salt is potassium chloride, ammonium chloride or sodium salicylate.
12. The gelled aqueous composition of claim 10 wherein the C 4 –C 10 alcohol is selected from the group consisting of hexanol, octanol and decanol.
13. The gelled aqueous composition of claim 10 further comprising one or more particulate proppants suspended therein.
14. A method of preparing a quaternized cyclic diamine of formula
wherein R is selected from the group consisting of C 12 –C 30 alkyl, C 12 –C 30 alkenyl, C 12 –C 30 arylalkyl and C 12 –C 30 cycloalkylalkyl; R 1 is selected from C 3 –C 8 cycloalkyl, aryl, C 6 –C 10 arylalkyl, C 2 –C 5 hydroxyalkyl and C 1 –C 5 alkyl; R 2 is selected from C 3 –C 8 cycloalkyl, aryl, C 6 –C 10 arylalkyl, C 2 –C 5 hydroxyalkyl and C 1 –C 5 alkyl wherein the cycloalkyl, aryl, arylalkyl, hydroxyalkyl or alkyl is substituted with carboxylate or sulfonate; m and n are independently integers of 1 to about 4; and X absent, comprising reacting a cyclic diamine of formula
with a C 3 –C 4 sultone, a halo-substituted C 3 –C 8 cycloalkyl-, aryl-, C 6 –C 10 arylalkyl-, C 2 –C 5 hydroxyalkyl- or C 1 –C 5 alkylsulfonate or a halo-substituted C 3 –C 8 cycloalkyl-, aryl-, C 6 –C 10 arylalkyl-, C 2 –C 5 hydroxyalkyl- or C 1 –C 5 alkylcarboxylate or carboxylic acid ester.
15. The method of claim 14 wherein the cyclic diamine is reacted with 1,3-propane sultone, sodium salt of 3-chloro-2-hydroxy-1-propanesulfonic acid or sodium chloroacetate.
16. The aqueous composition of claim 7 wherein R is selected from the group consisting of C 12 –C 30 alkyl and C 12 –C 30 alkenyl.
17. The aqueous composition of claim 16 wherein R is C 12 –C 30 alkenyl.
18. The aqueous composition of claim 16 wherein R is C 18 –C 30 alkenyl.
19. The aqueous composition of claim 18 wherein m and n are both 2.
20. The aqueous composition of claim 19 wherein R 1 is C 1 –C 2 alkyl; and R 2 is C 1 –C 2 alkyl, C 6 –C 8 arylalkyl or C 2 –C 3 hydroxyalkyl.
21. The aqueous composition of claim 20 wherein R 1 is methyl and R 2 is methyl, ethyl or hydroxyethyl.
22. The aqueous composition of claim 21 wherein R 1 and R 2 are methyl.