IP Library Granted Patent US 6,998,425
Granted Patent B2
US 6,998,425 · App. 10/747,713 · Granted Feb 14, 2006

UV curable coating compositions and uses thereof

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Quick Facts
Patent No.
US 6,998,425
App. No.
10/747,713
Granted
Feb 14, 2006
Kind
B2
Abstract

The present invention is directed to curable acrylate coating compositions and coated articles resulting therefrom. The curable acrylate coating composition comprises at least two polyfunctional acrylate derivatives, at least one photoinitiator and at least one nanoscale filler.

Claims (35)

1. A curable acrylate coating composition comprising at least two polyfunctional acrylate derivatives, and at least one of said polyfunctional acrylate derivatives comprises a hexafunctional acrylate derivative;

a photoinitiator; and

a nanoscale filler.

2. The curable acrylate coating composition according to claim 1 wherein said at least two polyfunctional acrylate derivatives are selected from a group consisting of hexafunctional urethane acrylates, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol tetraacrylate, di-trimethylolpropane tetraacrylate, pentaerythritol triacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, butanediol diacrylate, tripropylene glycol diacrylate, trimethylolpropane trimethacrylate, difunctional urethane acrylates, tetraacrylate monomer, polyester acrylate oligomers, and combinations thereof.

3. The curable acrylate coating composition according to claim 1 wherein the polyfunctional acrylate derivatives are present in an amount such that the total amount of all polyfunctional acrylates present corresponds to between about 30 and about 95 percent by weight of the curable acrylate coating composition.

4. The curable acrylate coating composition according to claim 3 wherein the polyfunctional acrylate derivatives are present in an amount such that the total amount of all polyfunctional acrylates present corresponds to between about 50 and about 90 percent by weight of the curable acrylate coating composition.

5. The curable acrylate coating composition according to claim 1 wherein said hexafunctional acrylate derivative is present in an amount corresponding to between about 0.1 and about 30 percent by weight of the curable acrylate coating composition.

6. The curable acrylate coating composition according to claim 1 wherein said coating composition further comprises a solvent selected from the group consisting of aliphatic alcohols, glycol ethers, cycloaliphatic alcohols, aliphatic esters, cycloaliphatic esters, aliphatic hydrocarbons, cycloaliphatic hydrocarbons, aromatic hydrocarbons, halogenated aliphatic compounds, halogenated cycloaliphatic compounds, halogenated aromatic compounds, aliphatic ethers, cycloaliphatic ethers, amide solvents, sulfoxide solvents.

7. The curable acrylate coating composition according to claim 6 wherein said solvent is 1-methoxy-2-propanol.

8. The curable acrylate coating composition according to claim 1 wherein said photoinitiator is activated by light having a wavelength of less than about 420 nm.

9. The curable acrylate coating composition according to claim 1 wherein said photoinitiator comprises 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide; and 2-hydroxy-2-methyl-1-phenylpropan-1-one.

10. The curable acrylate coating composition according to claim 1 wherein said nanoscale filler is selected from the group consisting of silica, zirconia, titania, alumina, ceria, and mixtures thereof.

11. The curable acrylate coating composition according to claim 1 wherein said nanoscale filler has a particle size of about 10 nanometers to about 250 nanometers.

12. The curable acrylate coating composition according to claim 1 wherein said nanoscale filler has a particle size in the range of between about 15 and about 50 nanometers.

13. The curable acrylate coating composition according to claim 1 wherein said nanoscale filler comprises silica having organic functional groups.

14. The curable acrylate coating composition according to claim 13 wherein said nanoscale filler comprises an acrylate functionalized silica.

15. The curable acrylate coating composition according to claim 1 wherein said nanoscale filler is present in an amount corresponding to between about 2 and about 15 percent by weight of the coating composition.

16. The curable acrylate coating composition according to claim 1 further comprising a UV absorber selected from a group consisting of hydroxybenzophenones, benzotriazoles, cyanoacrylates, triazines, oxanilide derivatives, poly(ethylene naphthalate), hindered amine, formamidines, cinnamates, malonate derivatives and combinations thereof.

17. An article coated with the curable acrylate coating composition according to claim 1 .

18. A curable acrylate coating composition comprising a photoinitiator, a nanoscale filler, at least one hexafunctional urethane acrylate, and at least one polyfunctional acrylate derivative.

19. The curable acrylate coating composition according to claim 18 wherein said hexafunctional urethane acrylate is a hexafunctional aliphatic urethane acrylate derivative.

20. The curable acrylate coating composition according to claim 18 wherein said at least one polyfunctional acrylate derivative is selected from a group consisting of 1,4-butanediol diacrylate, pentaerythitol triacrylate, trimethanol trimethacrylate derivatives and mixtures thereof.

21. The curable acrylate coating composition according to claim 18 wherein the at least one polyfunctional acrylate derivative is present in an amount such that the total amount of all polyfunctional acrylates present corresponds to between about 30 and about 95 percent by weight of the curable acrylate coating composition.

22. The curable acrylate coating composition according to claim 21 wherein the polyfunctional acrylate derivatives are present in an amount such that the total amount of all polyfunctional acrylates present corresponds to between about 50 and about 90 percent by weight of the curable acrylate coating composition.

23. The curable acrylate coating composition according to claim 18 wherein said hexafunctional acrylate derivative is present in an amount corresponding to between about 0.1 and about 30 percent by weight of the curable acrylate coating composition.

24. The curable acrylate coating composition according to claim 18 wherein said coating composition further comprises a solvent selected from the group consisting of aliphatic alcohols, glycol ethers, cycloaliphatic alcohols, aliphatic esters, cycloaliphatic esters, aliphatic hydrocarbons, cycloaliphatic hydrocarbons, aromatic hydrocarbons, halogenated aliphatic compounds, halogenated cycloaliphatic compounds, halogenated aromatic compounds, aliphatic ethers, cycloaliphatic ethers, amide solvents, sulfoxide solvents and mixtures thereof.

25. The curable acrylate coating composition according to claim 24 wherein said solvent is 1-methoxy-2-propanol.

26. The curable acrylate coating composition according to claim 18 wherein said photoinitiator is activated by light having a wavelength of less than about 420 nm.

27. The curable acrylate coating composition according to claim 26 wherein said photoinitiator comprises 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide; and 2-hydroxy-2-methyl-1-phenyl-propan-1-one.

28. The curable acrylate coating composition according to claim 18 wherein said nanoscale filler is selected from a group consisting of silica, zirconia, titania, alumina, and mixtures thereof.

29. The curable acrylate coating composition according to claim 28 wherein said nanoscale filler comprises silica having organic functional groups.

30. The curable acrylate coating composition according to claim 29 wherein said nanoscale filler comprises an acrylate functionalized silica.

31. The curable acrylate coating composition according to claim 18 wherein said nanoscale filler is present in an amount corresponding to between about 2 and about 15 percent by weight of the coating composition.

32. The curable acrylate coating composition according to claim 18 further comprising a UV absorber selected from a group consisting of hydroxybenzophenones, benzotriazoles, cyanoacrylates, triazines, oxanilide derivatives, poly(ethylene naphthalate), hindered amine, formamidines, cinnamates, malonate derivatives and combinations thereof.

33. A curable acrylate coating composition comprising a photoinitiator, a nanoscale filler, at least one hexafunctional urethane acrylate, and at least one additional polyfunctional acrylate derivative selected from the group consisting of 1,4-butanediol diacrylate, pentaerythitol triacrylate, and trinmethanol trimthacrylate derivatives and mixtures thereof.

Assignments (23)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
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FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
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TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
RELEASE OF SECURITY INTEREST Recorded Dec 24, 2020
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054883/0855 →
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To: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH & CO KG; MOMENTIVE PERFORMANCE MATERIALS JAPAN HOLDINGS GK
Reel/Frame 054387/0001 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
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To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
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FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
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RELEASE OF SECURITY INTEREST Recorded May 15, 2019
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RELEASE OF SECURITY INTEREST Recorded May 15, 2019
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NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
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NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
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