IP Library Granted Patent US 10,792,633
Granted Patent B2
US 10,792,633 · App. 16/078,721 · Granted Oct 6, 2020

Composition comprising a fluorine-containing surfactant

Inventors: Michael Hummel (Innsbruck, AT); Benjamin Naier (Innsbruck, AT); Herwig Schottenberger (Patsch, AT); Hubert Huppertz (Innsbruck, AT); Gabriel Partl (Fliess, AT); Michael Noisternig (Nassereith, AT)
Assignee: HWK-KRONBICHLER GMBH
B01F17/0057B01F17/0035B01F17/0042C07C49/167C07C309/12C07C309/15C07D233/84C07F9/17
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Quick Facts
Patent No.
US 10,792,633
App. No.
16/078,721
Granted
Oct 6, 2020
Kind
B2
Abstract

The invention relates to a composition comprising a fluorine-containing surfactant having a cationic group, a divalent sulfur-containing group and a fluorinated group, further comprising an anion that corresponds to the cationic group of the fluorine-containing surfactant, the cationic group being an N-alkylated heterocyclic group.

Claims (28)

1. A composition comprising:

1) a surfactant having:

a cationic group,

a bivalent or polyvalent sulfurous group, and

a fluorinated group;

2) an anion corresponding to the cationic group of the surfactant;

wherein the cationic group is an N-substituted heterocyclic group selected from the group consisting of an N,N-disubstituted imidazolium group, an N,N-disubstituted imidazolinium group, and an N,N-disubstituted benzimidazolium group.

2. The composition in accordance with claim 1 , wherein the cationic group is an N,N-disubstituted imidazolium group.

3. The composition in accordance with claim 1 , wherein the fluorinated group is a fully fluorinated hydrocarbon group of the type C n F 2n+1 , where n is 5, 6, or 7.

4. The composition in accordance with claim 1 , wherein the sulfurous group is a thioether.

5. The composition in accordance with claim 1 , wherein the anion is selected form the group consisting of a fluoride, a chloride, a bromide, an iodide, an aryl sulfonate, an alkyl sulfonate, an alkyl sulfate, a sulfate, an aryl phosphonate, an alkyl phosphonate, a monoalkyl phosphate, a dialkyl phosphate, a (di)hydrogen phosphate, a phosphate, a hexafluorophosphate, a hydrogen carbonate, a carbonate, a carbamate, an alkyl carbonate, a trifluoromethanesulfonate, a bis(trifluoromethane sulfonyl)imide, a nonaflate, and a carboxylate.

6. The composition in accordance with claim 1 , wherein the anion is covalently bonded to the surfactant.

7. The composition in accordance with claim 6 , wherein the anion is covalently bonded to a nitrogen atom of the cationic group via an interposed spacer.

8. The composition in accordance with claim 7 , wherein the spacer is a linear or branched C1-C10 alkylene group.

9. The composition in accordance with claim 7 , wherein characterized in that the spacer is a linear or branched C1-C5 alkylene group.

10. The composition in accordance with claim 7 , wherein the spacer is an ethylene group.

11. The composition in accordance with claim 6 , wherein the anion is covalently bonded to the sulfurous group of the surfactant, either directly or via an interposed spacer.

12. The composition in accordance with claim 1 , wherein the fluorinated group is bonded to a nitrogen atom of the cationic group, either directly or via an interposed spacer.

13. The composition in accordance with claim 1 , wherein the surfactant has one of the following structures:

where one of the residues R 1 , R 2 or R 3 represents a (CH 2 ) 1-5 (CF 2 ) 3-10 CF 3 group and the two further ones of the residues represent, independently of one another, hydrogen or a linear or branched C1-C10 alkyl group that has a crosslinkable group or is covalently bonded to the anion.

14. The composition in accordance with claim 1 , wherein the fluorinated group is covalently bonded to the sulfurous group, either directly or via an interposed spacer.

15. The composition in accordance with claim 1 , wherein the fluorinated group is a fully fluorinated and linear group of the type C n F 2n+1 , wherein n is from 3 to 10.

16. The composition in accordance with claim 1 , wherein the fluorinated group is a fully fluorinated and linear group of the type C n F 2n+1 , wherein n is 5, 6, or 7.

17. A method for altering a property of a solution comprising adding the composition of claim 1 to the solution, wherein said property is surface tension, foaming, an optical property, oxygen solubility or oxygen permeability.

18. A method of preparing a composition in accordance with claim 1 , wherein

said method comprises the step of a conversion of an uncharged compound having an N-alkylated heterocyclic group, a divalent sulfurous group, and a fluorinated group with an acid.

19. A method of preparing a composition in accordance with claim 1 , wherein

the method comprises a metathesis for exchanging the anion corresponding to the cationic group of the surfactant containing fluorine.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2024
From: HWK KRONBICHLER GMBH
To: GSCHNALLER, JOCHEN ALFRED
Reel/Frame 066564/0913 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2024
From: GSCHNALLER, JOCHEN ALFRED
To: AIRPLUS GMBH
Reel/Frame 066564/0916 →
CHANGE OF NAME Recorded Feb 10, 2020
From: UNIVERSITÄT INNSBRUCK
To: HWK-KRONBICHLER GMBH
Reel/Frame 051767/0525 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 16, 2018
From: HUMMEL, MICHAEL; NAIER, BENJAMIN; SCHOTTENBERGER, HERWIG; HUPPERTZ, HUBERT; PARTL, GABRIEL; NOISTERNIG, MICHAEL
To: UNIVERSITÄT INNSBRUCK
Reel/Frame 047182/0861 →
Priority Claims (1)
EP 16157380 · Feb 25, 2016 · regional
Continuity (1)
Related Publication 20190060858A1 · Feb 28, 2019