Cationic surfactants
View Patent ↗A surfactant comprising a polyether segment including at least one pendant alkoxyfluoroalkyl group, and a cationic substituent defined by one of the formulae: or the substituted derivatives thereof.
1. A surfactant comprising:
a polyether segment including at least one pendant alkoxyfluoroalkyl group; and
a cationic substituent defined by one of the formulae:
or the substituted derivatives thereof.
2. The surfactant of claim 1 , wherein the surfactant includes a salt including a counter anion.
3. The surfactant of claim 1 , where said polyether segment includes at least one repeat unit defined by the formula
where R 1 is a monovalent organic group or a substituent defined by the formula —R 2 —O—R 3 —R f , R 2 is a divalent organic group, R 3 is a divalent organic group or a bond, and R f is a monovalent organic group with at least 25% of the hydrogen atoms being replaced by fluorine.
4. The surfactant of claim 3 , where said polyether segment is defined by one or more of the formulae
where m is an integer from 1 to about 3, n is an integer from about 0 to 3, R 1 is a hydrogen atom or monovalent organic group, and R f is a linear or branched alkyl group including 1 to about 20 carbon atoms with at least 25% of the hydrogen atoms being replaced by fluorine.
5. The surfactant of claim 1 , where said polyether segment includes from about 1 to about 20 repeat or mer units.
6. The surfactant of claim 5 , where at least 75% of the repeat or mer units of said polyether segment include the pendant alkoxyfluoroalkyl groups.
7. The surfactant of claim 6 , where said polyether segment includes repeat or mer units deriving from tetrahydrofuran.
8. The surfactant of claim 6 , where R f is perfluorinated.
9. A method of preparing a cationic surfactant, the method comprising:
(i) providing an initiator compound including at least one hydroxyl group and at least one halogen atom;
(ii) initiating the polymerization of cyclic ether monomers with the initiator compound, where the monomers include one or more monomer having a pendant alkoxyfluoroalkyl group to provide a polyether precursor compound;
(iii) reacting the precursor compound and an amine compound defined by one of the formulae
as well as the substituted derivatives thereof.
10. The method of claim 9 , where said initiator includes halogenated alcohols defined by the formula
where R 4 is a bond or divalent organic group, R 5 is a monovalent organic group or halogen atom, and X is a halogen atom.
11. The method of claim 10 , wherein said halogenated alcohol is selected from the group consisting of 3-chloro-1-propanol, 3-iodo-1-propanol, 3-bromo-1-propanol, and mixtures thereof.
12. The method of claim 9 , where said amine includes 1,4-diazabicyclo[2.2.2.]octane, 3-quinucidinol, and mixtures thereof.
13. The method of claim 9 , where said step of reacting an amine compound with the precursor compound takes place in a solvent selected from the group consisting of isopropanol, diethyleneglycolmonobutylether, and mixture thereof.
14. The method of claim 13 , where said step of reacting an amine compound with the precursor compound takes place at elevated temperatures.