IP Library Granted Patent US 10,894,885
Granted Patent B2
US 10,894,885 · App. 16/078,726 · Granted Jan 19, 2021

Crosslinkable composition and method for producing a coated article

Inventors: Benjamin Naier (Innsbruck, AT); Herwig Schottenberger (Patsch, AT); Anna Daxenbichler (Innsbruck, AT); Thomas Bechtold (Dornbirn, AT); Gabriel Parti (Innsbruck, AT); Maximilian Andre (Achenkirch, AT); Simon Kronbichler (Ebbs, AT); Reinhard Kronbichler (Ebbs, AT)
Assignee: HWK—KRONBICHLER GMBH
C09D4/00C08F26/06C09D5/00C09G3/00D06M13/144D06M13/272D06M13/348C08F226/06D06M2200/11D06M2200/12
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Quick Facts
Patent No.
US 10,894,885
App. No.
16/078,726
Granted
Jan 19, 2021
Kind
B2
Abstract

The invention relates to a crosslinkable composition comprising functionalized monomers comprising a crosslinkable group, a cationic group and a fluorinated group, wherein the composition comprises anions corresponding to the cationic groups of the functionalized monomers, wherein the cationic group is an N-substituted cyclic and in particular heteroaromatic group comprising a 5-membered ring and/or at least two heteroatoms and wherein a spacer which is an uncharged and unfluorinated organyl group and preferably an alkylene group is arranged between the cationic group and the fluorinated group.

Claims (18)

1. A method of manufacturing a coated article,

said method comprising wetting a surface of an article with a crosslinkable composition and wherein the crosslinkable composition is subsequently crosslinked to form a coating on the article, and said crosslinkable composition comprising functionalized monomers that have a crosslinkable group, a cationic group, and a fluorinated group, and anions corresponding to the cationic group of the functionalized monomers, and wherein the cross-linkable group comprises a crosslinkable ethylenic functionality and the cationic group is an N-substituted cyclic group that comprises a 5-membered ring and/or at least two heteroatoms; and in that a spacer is arranged between the cationic group and the fluorinated group, said spacer being an uncharged and unfluorinated organyl group.

2. The method of claim 1 , wherein the cationic group is an N,N-disubstituted imidazolium group.

3. The method of claim 1 , wherein the spacer is a linear alkylene group having 1 to 10 carbon atoms.

4. The method of claim 1 , wherein the fluorinated group is a completely fluorinated hydrocarbon group.

5. The method of claim 1 , wherein the functionalized monomer further comprises a thioether.

6. The method of claim 5 , wherein the sulfur-bonded organyl residue of the thioether carries the crosslinkable group or a further crosslinkable group, with the further crosslinkable group being able to be a crosslinkable ethylenic functionality or a non-ethylenic crosslinkable group.

7. The method of claim 5 , wherein the functionalized monomer has a further group that is substituted at the organyl residue of the organyl sulfide group or that represents the sulfur-bonded organyl residue of the thioether.

8. The method of claim 5 , wherein the sulfur-bonded organyl residue of the thioether carries the anion corresponding to the cationic group, with the anion being a sulfate group, a sulfonate group, a phosphonate group, a phosphate group, a carbonate group, a carbamate group, a triflate group, or a carboxylate group substituted at the organyl residue.

9. The method of claim 1 , wherein at least some of the anions are not covalently bonded to the copolymer, with provision being made that the free anion is chloride, iodide, bromide, aryl sulfonate, alkyl sulfonate, alkyl sulfate, sulfate, aryl phosphonate, alkyl phosphonate, monoalkyl phosphate, dialkyl phosphate, hydrogen phosphate, phosphate, hexafluorophosphate, hydrogen carbonate, carbonate, carbamate, alkyl carbonate, trifluoromethanesulfonate, bis(trifluoromethane)sulfonamide, nonaflate, or carboxylate.

10. The method of claim 1 , wherein at least some of the anions are covalently bonded to the functionalized monomer, with it being an organyl-bonded sulfate group, sulfonate group, phosphonate group, phosphate group, carbonate group, carbamate group, triflate group, or carboxylate group.

11. The method of claim 1 , wherein at least some of the anions are a halogenide.

12. The method of claim 11 , wherein the composition further comprises a halogenoalkane.

13. The method of claim 1 , wherein the composition comprises additional monomers that have at least one crosslinkable group, but do not further have either a cationic group or a fluorinated group.

14. The method of claim 1 , wherein the composition further comprises an initiator; and/or the composition further has an ionic additive.

15. The method of claim 1 , wherein said spacer is an alkylene group.

16. The method of claim 1 , wherein said crosslinkable group comprises a substituted or unsubstituted vinyl group.

17. The method of claim 1 , wherein the fluorinated group has the formula C n F 2n+1 , where n is 3 to 10.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2024
From: GSCHNALLER, JOCHEN ALFRED
To: AIRPLUS GMBH
Reel/Frame 066564/0907 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2024
From: HWK KRONBICHLER GMBH
To: GSCHNALLER, JOCHEN ALFRED
Reel/Frame 066564/0910 →
CHANGE OF NAME Recorded Feb 10, 2020
From: UNIVERSITÄT INNSBRUCK
To: HWK-KRONBICHLER GMBH
Reel/Frame 051767/0525 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2018
From: NAIER, BENJAMIN; SCHOTTENBERGER, HERWIG; DAXENBICHLER, ANNA; BECHTOLD, THOMAS; PARTL, GABRIEL; ANDRE, MAXIMILIAN; KRONBICHLER, SIMON; KRONBICHLER, REINHARD
To: UNIVERSITÄT INNSBRUCK; HWK KRONBICHLER GMBH
Reel/Frame 047476/0316 →
Priority Claims (1)
EP 16157388 · Feb 25, 2016 · regional
Continuity (1)
Related Publication 20190048203A1 · Feb 14, 2019