Quaternary cationic polymers
A cationic polymer salt composition is provided that includes a reaction product derived from reaction of a polyamine or a polyalkyleneimine and a substituted alkyl trialkyl quaternary ammonium salt. Also provided are surfactant compositions. The compositions may also include carriers, such as water, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, monoethyleneglycol, an ethyleneglycol monobutyl ether, and hexylene glycol.
1. A cationic polymer salt comprising a reaction product derived from a reaction of a polyamine or a polyalkyleneimine and a substituted alkyl trialkyl quaternary ammonium salt of formula (I):
wherein
each X − is independently an anion;
R 1 is C 1 -C 6 alkylene substituted with a hydroxyl or —OR 5 and an X − end group;
R 2 , R 3 , and R 4 are each independently C 1 -C 22 alkyl or C 7 -C 22 arylalkyl; and
R 5 is C 1 -C 6 alkyl;
wherein any one of the following:
(A) the cationic polymer salt has no substitutions within its main chain, no alkyl-quaternized ammonium within its main chain, and comprises at least 4 quaternary ammonium groups; or
(B) the cationic polymer salt has one or more terminal tertiary amine groups having the formula (IV):
wherein R 11 is R 1 without the X − end group, and either: the polymer salt has no substitutions within its main chain or at least 1 of R 2 , R 3 , and R 4 is a C 9 -C 22 alkyl group; or
(C) R 2 and R 3 are C 6 -C 22 alkyl or C 7 -C 22 arylalkyl and R 4 is methyl.
2. The polymer salt of claim 1 , wherein X − is selected from the group consisting of chloride, bromide, fluoride, iodide, acetate, aluminate, cyanate, cyanide, dihydrogen phosphate, dihydrogen phosphite, formate, hydrogen carbonate, hydrogen oxalate, hydrogen sulfate, hydroxide, metaniobate, metavanadate, nitrate, nitrite, thiocyanate, and any combination thereof.
3. The polymer salt of claim 2 , wherein X − is chloride or bromide.
4. The polymer salt of claim 1 , wherein R 1 is C 2 -C 3 alkylene substituted with hydroxyl.
5. The polymer salt of claim 1 , wherein R 2 , R 3 , and R 4 are independently C 1 -C 22 alkyl.
6. The polymer salt of claim 1 , wherein R 2 is C 6 -C 22 alkyl or C 7 -C 22 arylalkyl and R 3 and R 4 are methyl.
7. The polymer salt of claim 1 , wherein R 2 and R 3 are C 6 -C 22 alkyl or C 7 -C 22 arylalkyl and R 4 is methyl.
8. The polymer salt of claim 5 , wherein R 2 , R 3 , and R 4 are methyl.
9. The polymer salt of claim 1 , wherein the substituted alkyl trialkyl quaternary ammonium salt comprises 3-chloro-2-hydroxypropyl-trimethylammonium chloride, 3-chloro-2-hydroxypropyl-dodecyl-dimethylammonium chloride, 3-chloro-2-hydroxypropyl-stearyl-dimethylammonium chloride, or any combination thereof.
10. The polymer salt of claim 1 , wherein the polyamine has the formula (II):
wherein
n is an integer from 0 to 100;
each R 6 is independently C 2 -C 6 alkylene; and
each R 7 is independently hydrogen or —R 6 —NH 2 , —R 6 —NH—R 6 —NH 2 , or —R 6 —N—(R 6 —NH 2 ) 2 .
11. The polymer salt of claim 10 , wherein n is selected from the group consisting of 1 to 50, 1 to 10, 1 to 5, 0 to 50, 0 to 10, and 0 to 5.
12. The polymer salt of claim 10 , wherein R 6 is a C 2 -C 3 alkyl.
13. The polymer salt of claim 12 , wherein R 6 is ethyl.
14. The polymer salt of claim 1 , wherein (A) the cationic polymer salt has no substitutions within its main chain, no alkyl-quaternized ammonium within its main chain, and comprises at least 4 quaternary ammonium groups.
15. The polymer salt of claim 1 , wherein (B) the cationic polymer salt has one or more terminal tertiary amine groups having the formula (IV):
wherein R 11 is R 1 without the X − end group, and either: the polymer salt has no substitutions within its main chain or at least 1 of R 2 , R 3 , and R 4 is a C 9 -C 22 alkyl group.
16. The polymer salt of claim 1 , wherein (C) R 2 and R 3 are C 6 -C 22 alkyl or C 7 -C 22 arylalkyl and R 4 is methyl.
17. The polymer salt of claim 1 , wherein the polyamine comprises an alkyleneamine, the alkyleneamine comprising ethylenediamine, diethylenetriamine, triethylenetetraamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexaethyleneheptamine, or a combination thereof.
18. The polymer salt of claim 1 , wherein the polyalkyleneimine comprises ethyleneimine; propyleneimine; butyleneimine; pentyleneimine; hexyleneimine; heptyleneimine; branched, linear, or dendrimer polyethyleneimine; or any combination thereof.
19. The polymer salt of claim 1 , wherein the molar ratio of the polyamine or polyalkyleneimine to the substituted alkyl trialkyl quaternary ammonium salt ranges from 1:1 to 1:100, 1:1 to 1:50, 1:1 to 1:25, 1:1 to 1:10, 1:1 to 1:5, or 1:1 to 1:2.
20. A cationic polymer salt having the formula (III):
wherein
each R 6 is independently C 2 -C 6 alkylene;
each R 7 is independently —R 8 , —R 6 —N(R 8 ) 2 , —R 6 —N(R 8 )—R 6 —N(R 8 ) 2 , or —R 6 —N—(R 6 —N(R 8 ) 2 ) 2 ;
each R 8 is
each R 9 is independently C 2 -C 6 alkylene substituted with hydroxyl or —OR 13 ;
R 10 , R 11 , and R 12 are each independently C 1 -C 22 alkyl or C 7 -C 22 arylalkyl;
R 13 is C 1 -C 6 alkyl;
n is an integer from 1 to 100; and
each X − is independently an anion.
21. The polymer salt of claim 20 , wherein n is from 1 to 50 or 1 to 25.
22. The polymer salt of claim 20 , wherein each R 6 and R 9 is independently C 2 -C 3 alkylene.
23. The polymer salt of claim 22 , wherein each R 6 is ethylene.
24. The polymer salt of claim 20 , wherein each R 9 is hydroxypropylene; R 10 and R 11 are methyl; and each R 12 is independently methyl or C 8 -C 22 alkyl.
25. The polymer salt of claim 24 , wherein at least one R 12 is C 8 -C 22 alkyl.
26. The polymer salt of claim 20 , wherein the polymer salt is any one of Compounds 1 through 13: