IP Library Granted Patent US 7,608,710
Granted Patent B2
US 7,608,710 · App. 11/448,619 · Granted Oct 27, 2009

Cationic surfactants

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Quick Facts
Patent No.
US 7,608,710
App. No.
11/448,619
Granted
Oct 27, 2009
Kind
B2
Abstract

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.

Claims (24)

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.

Assignments (4)
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL Recorded Apr 1, 2020
From: JPMORGAN CHASE BANK, N.A.
To: OMNOVA SOLUTIONS INC.
Reel/Frame 052286/0971 →
GRANT OF SECURITY INTEREST IN CERTAIN PATENTS AND TRADEMARKS Recorded Jul 24, 2007
From: OMNOVA SOLUTIONS INC.
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 019597/0227 →
SECURITY AGREEMENT Recorded May 30, 2007
From: OMNOVA SOLUTIONS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 019353/0566 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 5, 2006
From: KAUSCH, CHARLES M.; KIM, YONGSIN; THOMAS, RICHARD R.; HARDMAN, DAVID L., JR.
To: OMNOVA SOLUTIONS INC.
Reel/Frame 018272/0330 →