IP Library Granted Patent US 12,054,635
Granted Patent B2
US 12,054,635 · App. 16/142,408 · Granted Aug 6, 2024

Curable composition for coatings having an anti-adhesive property

Inventors: Tim-Frederic Sloot (Haltern am See, DE); Michael Fiedel (Essen, DE); Katrin Roland (Essen, DE); Frauke Henning (Essen, DE); Stefan Busch (Bochum, DE); Sabine Krusenbaum (Essen, DE); Stefanie Redeker (Essen, DE)
Assignee: Evonik Operations GmbH
C09D183/04C09D5/1675C09D5/1687C09D7/63C09D183/06C09D183/08C08G77/14C08G77/26
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Quick Facts
Patent No.
US 12,054,635
App. No.
16/142,408
Granted
Aug 6, 2024
Kind
B2
Abstract

Curable composition for producing coating systems having an anti-adhesive property containing at least one film-forming polymer and at least one organo-modified, branched siloxane of formula (I) or mixtures thereof.

Claims (71)

1. A curable composition, comprising: a film-forming polymer and an organo-modified, branched siloxane of formula (I) or mixtures thereof:

M a M′ a1 D b T c Q d   Formula (I)

where:

M=(R 1 3 SiO 1/2 )

M′=(R 2 R 1 2 SiO 1/2 )

D=(R 1 2 SIO 2/2 )

T=(R 3 SiO 3/2 )

Q=(SiO 4/2 )

a=from 0 to 30,

a1=from 0 to 30, wherein a+a1>2,

b=from 10-1000,

c=from 0 to 30,

d=from 0 to 15, wherein c+d>=1,

R 1 =independently of one another hydrocarbon radicals having 1 to 30 carbon atoms,

R 2 is selected from the group consisting of organic polyether, hydroxyl, amine, carboxyl, alkoxy, epoxy, alkylalkoxysilylalkyl and alkoxysilylalkyl radicals,

R 3 =R 1 or R 2 ,

wherein the average degree of branching K of the siloxanes according to formula (I) is greater than 1,

wherein the siloxanes of formula (I) have an average number of directly successive D units F1=D/(1+T*2+Q*3)=of at least 5,

wherein the siloxane has a number-average molecular weight of 5,000-50,000,

wherein the siloxane comprises at least one R 2 group,

wherein the siloxanes of formula (I) are organo-modified siloxanes singly or multiply branched in the siloxane part, and

wherein the film-forming polymer is an epoxy-functional silane or siloxane, aromatic or aliphatic glycidyl ethers or condensates thereof or mixtures thereof reactive with an amine-containing curing agent, or wherein the film-forming polymer is a film-forming alkoxysilyl-containing polymer which cures by the mechanism of hydrolysis condensation, optionally in combination with at least one catalyst,

wherein the siloxanes of formula (I) have terminal and/or lateral organic radicals selected from OH-bearing organic radicals, carboxylate groups, alkoxysilylalkyl groups, dodecyl groups or aminoalkyl groups, and

wherein the OH-bearing organic radicals are present and comprise hydroxyethylpropyl groups.

2. The curable composition according to claim 1 , wherein the average degree of branching K of the siloxanes according to formula (I) is greater than 1.25.

3. The curable composition according to claim 1 , wherein the siloxanes of formula (I) have an average number of directly successive D units F1=D/(1+T*2+Q*3)=of at least 10.

4. The curable composition according to claim 1 , wherein the siloxanes of formula (I) have a viscosity measured according to DIN 53015 of from 50-2000 mPa s (25° C.).

5. The curable composition according to claim 1 , wherein the film-forming polymer is selected from the group of epoxy-functional siloxane, aromatic or aliphatic glycidyl ethers or condensates thereof or mixtures thereof reactive with an amine-containing curing agent.

6. The curable composition according to claim 1 , wherein the film-forming polymer is a film-forming alkoxysilyl-containing polymer which cures by the mechanism of hydrolysis condensation, optionally in combination with at least one catalyst.

7. The curable composition according to claim 1 , wherein the siloxanes of formula (I) are employed in concentrations of from 0.1% by weight to 40% by weight based on the curable composition.

8. The curable composition according to claim 1 , wherein the siloxanes of formula (I) are employed in concentrations of from 2% by weight to 20% by weight based on the curable composition.

9. The curable composition according to claim 5 , wherein the siloxane is present in the curable film-forming composition in an amount from 2% by weight to 20% by weight.

10. A coating having anti-adhesive properties, containing the composition as defined in claim 1 .

11. A coating having anti-soiling properties, containing the composition as defined in claim 1 .

12. A coating having anti-graffiti properties, containing the composition as defined in claim 1 .

13. A coating having anti-icing properties, containing the composition as defined in claim 1 .

14. A coating having anti-fouling properties, containing the composition as defined in claim 1 .

15. A universal anti-adhesive additive containing the composition as defined in claim 1 .

16. An anti-fouling additive, containing the composition as defined in claim 1 .

17. An anti-soiling additive, containing the composition as defined in claim 1 .

18. An anti-icing additive, containing the composition as defined in claim 1 .

19. An anti-graffiti additive, containing the composition as defined in claim 1 .

20. The curable composition according to claim 1 , wherein variable a is not zero.

21. The curable composition according to claim 1 , wherein variable d is not zero.

22. The curable composition according to claim 1 , comprising a mixture of the organo-modified, branched siloxanes of formula (I).

23. The curable composition according to claim 1 , wherein R 1 is phenyl dodecyl, or hexadecyl.

24. The curable composition according to claim 1 , wherein variable a1 is not zero.

25. The curable composition according to claim 1 , wherein variable c is not zero.

26. The curable composition according to claim 1 ,

wherein formula (I) is an organo-modified siloxane singly branched in the siloxane part.

27. The curable composition according to claim 26 ,

wherein formula (I) has a viscosity measured according to DIN 53015 of from 100-1500 mPa s (25° C.), and wherein the film-forming polymer is a film-forming alkoxysilylcontaining polymer which cures by the mechanism of hydrolysis condensation, in combination with at least one catalyst.

28. The curable composition according to claim 1 ,

wherein the film-forming polymer is selected from the group consisting of epoxy-functional silane or siloxane, aromatic or aliphatic glycidyl ethers or condensates thereof and mixtures thereof reactive with an amine-containing curing agent.

29. The curable composition according to claim 1 ,

wherein the film-forming polymer is a film-forming alkoxysilyl-containing polymer which cures by the mechanism of hydrolysis condensation, in combination with at least one catalyst.

30. A coating comprising the curable composition

according to claim 1 wherein the coating has anti-adhesive properties, anti-soiling properties, anti-graffiti properties, anti-icing properties or anti-fouling properties.

31. An additive comprising the curable composition of claim 1 , wherein the additive is a universal anti-adhesive additive, an anti-fouling additive, anti-soiling additive, anti-icing additive or anti-graffiti additive.

32. A process for forming an anti-adhesive coating on a substrate comprising applying a curable film-forming composition according to claim 1 atop a substrate.

33. The process according to claim 32 , wherein the siloxane (b) has a number-average molecular weight of 7000-35 000 g/mol.

34. The process according to claim 32 , wherein the siloxane (b) is present in the curable film-forming composition in an amount from 0.1% by weight to 40% by weight.

35. The process according to claim 32 , wherein the curable film-forming composition is cured at ambient temperature.

36. The process according to claim 32 , wherein the substrate contains metal, concrete, wood, plastic and/or glass fiber and/or carbon fiber composite.

37. The process according to claim 36 , wherein the substrate comprises a ship's hull, underwater structures and/or oil drilling platforms.

38. The process according to claim 32 , wherein an undercoat and/or film-forming top coat composition is applied atop the substrate before application of the curable film-forming composition.

39. The curable composition according to claim 1 , wherein a is 0 to 12.

40. The curable composition according to claim 1 , wherein a1 is more than 0 and less than or equal to 12.

41. The curable composition according to claim 1 , wherein R 1 is methyl, ethyl, phenyl, dodecyl or hexadecyl.

42. The curable composition according to claim 1 , wherein R 3 is methyl, phenyl or alkoxy radicals.

43. The curable composition according to claim 1 , wherein the siloxanes of formula (I) are or multiply branched in the siloxane part.

Assignments (2)
CHANGE OF NAME Recorded Dec 27, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051428/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2018
From: SLOOT, TIM-FREDERIC; FIEDEL, MICHAEL; ROLAND, KATRIN; HENNING, FRAUKE; BUSCH, STEFAN; KRUSENBAUM, SABINE; REDEKER, STEFANIE
To: EVONIK DEGUSSA GMBH
Reel/Frame 047886/0771 →
Priority Claims (1)
EP 17196290 · Oct 13, 2017 · regional
Continuity (1)
Related Publication 20190112502A1 · Apr 18, 2019