# US 7,608,710 B2 · Cationic surfactants

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- Number: US 7,608,710 B2
- Document ID: US7608710B2
- Status: Granted
- Kind: B2
- Application number: 11/448,619
- Filed: 2006-06-07
- Published: 2006-12-28
- Granted: 2009-10-27
- Earliest claimed: 2005-06-07
- Assignees: OMNOVA Solutions Inc.
- Inventors: Charles M. Kausch; Yongsin Kim; Richard R. Thomas; David L. Hardman, Jr.
- Web page: https://patentgrep.com/patent/US7608710B2

## CPC

- C11D 1/004: {Surface-active compounds containing F}
- C09D 7/47: Levelling agents
- C09G 1/00: Polishing compositions (French polish C09F11/00; detergents C11D)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09G: POLISHING COMPOSITIONS (French polish C09F11/00); SKI WAXES

## 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

### Claim 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.

### Claim 2 (depends on 1)

The surfactant of claim 1, wherein the surfactant includes a salt including a counter anion.

### Claim 3 (depends on 1)

The surfactant of claim 1, where said polyether segment includes at least one repeat unit defined by the formula
where R1 is a monovalent organic group or a substituent defined by the formula —R2—O—R3—Rf, R2 is a divalent organic group, R3 is a divalent organic group or a bond, and Rf is a monovalent organic group with at least 25% of the hydrogen atoms being replaced by fluorine.

### Claim 4 (depends on 3)

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, R1 is a hydrogen atom or monovalent organic group, and Rf 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.

### Claim 5 (depends on 1)

The surfactant of claim 1, where said polyether segment includes from about 1 to about 20 repeat or mer units.

### Claim 6 (depends on 5)

The surfactant of claim 5, where at least 75% of the repeat or mer units of said polyether segment include the pendant alkoxyfluoroalkyl groups.

### Claim 7 (depends on 6)

The surfactant of claim 6, where said polyether segment includes repeat or mer units deriving from tetrahydrofuran.

### Claim 8 (depends on 6)

The surfactant of claim 6, where Rf is perfluorinated.

### Claim 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.

### Claim 10 (depends on 9)

The method of claim 9, where said initiator includes halogenated alcohols defined by the formula
where R4 is a bond or divalent organic group, R5 is a monovalent organic group or halogen atom, and X is a halogen atom.

### Claim 11 (depends on 10)

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.

### Claim 12 (depends on 9)

The method of claim 9, where said amine includes 1,4-diazabicyclo[2.2.2.]octane, 3-quinucidinol, and mixtures thereof.

### Claim 13 (depends on 9)

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.

### Claim 14 (depends on 13)

The method of claim 13, where said step of reacting an amine compound with the precursor compound takes place at elevated temperatures.