UV curable coatings having improved weatherability

• US 5,559,163 A
• Filed: 08/31/1994
• Issued: 09/24/1996
• Est. Priority Date: 01/28/1991
• Status: Expired due to Term

• Current Assignee: Sherwin-Williams Company
• Original Assignee: Sherwin-Williams Company
• Inventors: Gupta, Goutam, Dawson, William R.
• Primary Examiner(s): Hoke, Veronica P.
• Application Number:
  US08/298,730
• Time in Patent Office: 755 Days
• Field of Search: 522/22, 522/183, 522/75, 522/40, 522/43
• US Class Current: 522/75
• CPC Class Codes: C08F 220/00 Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

Abstract

UV curable coatings comprising at least one photoinitiator and at least one photopolymerizable UV absorber, wherein the photoinitiator has the ability to absorb a significant portion of the total energy needed to cure the coating from wavelengths in which the UV absorber does not appreciably absorb.

Claims

1. A UV curable coating composition comprising:

a) at least one photoinitiator selected from the group consisting of acylphosphine oxides, Michler'"'"'s ketone, benzil, 2-chlorothioxanthone, and mixtures thereof;

b) at least one photopolymerizable UV absorber having ethylenic unsaturation;

c) at least one UV curable acrylic monomer; and

d) silica;

wherein said photoinitiator has the ability to absorb a significant portion of the total energy needed to cure said coating from wavelengths in which said UV absorber does not appreciably absorb.

3. The UV curable coating composition of claim 1 wherein said photoinitiator comprises an acylphosphine oxide.

4. The UV curable coating composition of claim 1 wherein said photoinitiator comprises 2,4,6-trimethylbenzoyl diphenyl phosphine oxide.

5. The UV curable coating composition of claim 1 wherein said UV absorber comprises 2-hydroxy-4-acryloyloxyethoxy benzophenone.

6. The UV curable coating composition of claim 3 wherein said UV absorber comprises 2-hydroxy-4-acryloyloxyethoxy benzophenone.

7. The UV curable coating composition of claim 1 wherein the UV absorber is a photopolymerizable benzotriazole.

8. The UV curable coating composition of claim 7 wherein the UV absorber is selected from the group consisting of ##STR4##

9. The UV curable coating composition of claim 1 comprising a mixture of at least two photoinitiators.

10. The UV curable coating composition of claim 9 wherein said photoinitiator mixture comprises at least about 10% by weight of acylphosphine oxide based on the total weight of photoinitiator.

11. The UV curable coating composition of claim 9 wherein said photoinitiator mixture further comprises a photoinitiator selected from 2-hydroxy-2-methyl-1-phenyl-propan-1-one, and hydroxycyclohexyl phenyl ketone.

12. The UV curable composition of claim 1 wherein the total amount of photoinitiator in the composition comprises between about 0.5% and about 7.0% by weight of the total composition.

13. The UV curable composition of claim 9 wherein tile total amount of photoinitiator in the composition comprises between about 0.5% and about 7.0% by weight of the total composition.

14. The UV curable composition of claim 1 wherein said UV absorber is present in an amount of between about 5 % and about 20% by weight of the total composition.

15. The UV curable composition of claim 5 wherein said UV absorber is present in an amount of between about 5% and about 20% by weight of the total composition.

16. The UV curable composition of claim 1 wherein said UV absorber is present in an amount of between about 6% and about 15 % by weight of the total composition.

17. The UV curable composition of claim 5 wherein said UV absorber is present in an amount of between about 6% and about 15% by weight of the total composition.

18. The UV curable composition of claim 1 wherein the silica has been surface treated according to a process comprising:

a) admixing water and a catalytic amount of acid with a silica organosol comprising silica dispersed in a water-miscible organic solvent;

b) gradually adding a trialkoxysilane to the admixture under reactive conditions; and

c) removing substantially all of the water;

wherein the trialkoxysilane is present at a level up to about 30% by weight based upon the weight of the silica and the water is added at an amount up to about 15 % by weight based upon the weight of the water-miscible organic solvent.

19. The UV curable coating composition of claim 18 wherein said trialkoxysilane is polymerizable.

20. The UV curable coating composition of claim 1 further comprising a hindered amine light stabilizer.

21. The UV curable coating composition of claim 20 wherein said hindered amine light stabilizer is selected from the group consisting of bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperdinyl) sebacate, ##STR5##

22. The UV curable coating composition of claim 20 wherein said hindered amine light stabilizer comprises bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperdinyl) sebacate.

2. The UV curable coating composition of claim I wherein said UV absorber comprises a photopolymerizable benzophenone.

23. A UV curable coating composition comprising:

a) a photoinitiator having the ability to absorb energy from wavelengths above 380 nm;

b) a photopolymerizable UV absorber having the ability to absorb energy from the range of wavelengths of less than about 340-360 nm and does not appreciably absorb energy above about 380 nm;

c) at least one UV curable acrylic monomer; and

d) silica.

24. The UV curable coating composition of claim 23 wherein said photoinitiator is selected from the group consisting of acylphosphine oxides, Michler'"'"'s ketone, benzil, 2-chlorothioxanthone, and mixtures thereof.

25. The UV curable coating composition of claim 23 wherein said photoinitiator comprises an acylphosphine oxide.

26. The UV curable coating composition of claim 23 wherein said photoinitiator comprises 2,4,6-trimethylbenzoyl diphenyl phosphine oxide.

27. The UV curable coating composition of claim 23 wherein said photopolymerizable UV absorber comprises an ethylenically unsaturated benzophenone.

28. The UV curable coating composition of claim 23 wherein said UV absorber comprises 2-hydroxy-4-acryloyloxyethoxy benzophenone.

29. The UV curable coating composition of claim 23 wherein said UV absorber comprises a photopolymerizable benzotriazole.

30. The UV curable coating of claim 23 wherein said UV absorber is selected from the group comprising ##STR6##

31. The UV curable coating composition of claim 23 wherein the silica has been surface treated according to a process comprising:

a) admixing water and a catalytic amount of acid with a silica organosol comprising silica dispersed in a water-miscible organic solvent;

b) gradually adding a trialkoxysilane to the admixture under reactive conditions; and

c) removing substantially all of the water;

wherein the trialkoxysilane is present at a level up to about 30 % by weight based upon the weight of the silica and the water is added at an amount up to about 15% by weight based upon the weight of the water-miscible organic solvent.

32. The UV curable coating composition of claim 23 further comprising a hindered amine light stabilizer.