Abrasion-resistant optical coating composition containing pentaerythritol based polyacrylates and cellulose esters

• US 4,308,119 A
• Filed: 01/07/1980
• Issued: 12/29/1981
• Est. Priority Date: 02/21/1979
• Status: Expired due to Term

• Current Assignee: Panelgraphic Corp.
• Original Assignee: Panelgraphic Corp.
• Inventors: Russell, Raymond J.
• Primary Examiner(s): Bleutge, John C.
• Assistant Examiner(s): KOECKERT JR, ARTHUR
• Application Number:
  US06/104,351
• Time in Patent Office: 722 Days
• Field of Search: 204/159.12
• US Class Current: 522/45
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 251/02 on to cellulose or derivatives thereof

Abstract

Actinic radiation curable coating compositions are provided applicable to many substrates comprising a pentaerythritol-based polyacrylate or polymethacrylate such as pentaerythritol tetraacrylate, a cellulose ester such as cellulose acetate butyrate and a photoinitiator. The compounds are preferably applied to the substrate by spraying a solution of the composition in one or more solvents selected from the group consisting of lower alcohols and ester, ketones having from 3 to 7 carbon atoms and lower alkyl Cellosolves, and removing the solvents.

Upon curing in air the compositions form extremely abrasion resistant coatings on the substrate and are also characterized by being scratch resistant and resistant to attack by chemical and organic solvents.

Claims

1. A composition curable by actinic radiation to form an abrasion-resistant optical product consisting essentially of a pentaerythritol based polyacrylate selected from the group consisting of a pentaerythritol polyacrylate, a pentaerythritol polymethacrylate, a dipentaerythritol polyacrylate, a dipentaerythritol polymethacrylate, a tripentaerythritol polyacrylate and a tripentaerythritol polymethacrylate, a cellulose ester comprising the reaction product of cellulose with at least one organic carboxylic acid having from about 2 to 4 carbon atoms or nitric acid and a photoinitiator, wherein the weight ratio of said polyacrylate to said ester is from about 6 to 1 to about 100 to 1.

2. The composition of claim 1 wherein said pentaerythritol polyacrylate is selected from the group consisting of pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, tripentaerythritol octaacrylate and mixtures thereof.

3. The composition of claim 1 wherein said pentaerythritol polyacrylate is pentaerythritol tetraacrylate.

4. The composition of claim 1 wherein said dipentaerythritol polyacrylate is dipentaerythritol pentaacrylate.

5. The composition of claim 1 wherein said pentaerythritol polymethacrylate is selected from the group consisting of pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate, dipentaerythritol pentamethacrylate, tripentaerythritol octamethacrylate and mixtures thereof.

6. The composition of claim 1 wherein said pentaerythritol polymethacrylate is pentaerythritol tetramethacrylate.

7. The composition of claim 1 wherein said cellulose ester is cellulose acetate butyrate.

8. The composition of claim 7 wherein said cellulose acetate butyrate contains on the average from about 15% to 50% butyryl groups, from about 1% to 30% acetyl groups and from about 1% to 5% hydroxyl groups.

9. The composition of claim 8 wherein said cellulose acetate butyrate has a viscosity in Poises of from about 50 to 200 at 25°

C. in a solution comprising 20 wt. % cellulose acetate butyrate, 72 wt. % acetone and 8 wt. % ethyl alcohol.

10. The composition of claim 1 wherein said photoinitiator is alphachloroacetyldiphenyloxide.

11. The composition of claim 1 wherein said photoinitiator is benzoyl peroxide.

12. The composition of claim 1 which further comprises at least one solvent selected from the group consisting of lower alcohols, lower alkyl acetates, alkyl ketones having from 3 to 7 carbon atoms and ethylene glycol lower alkyl ethers.

25. A product comprising the cured composition of claim 1.

26. A product comprising the cured composition of claim 3.

27. A product comprising the cured composition of claim 8.

33. An abrasion-resistant product comprising a substrate having coated thereon the cured composition of claim 1.

36. A product comprising a substrate having coated thereon the composition of claim 1.

37. A product comprising a substrate having coated thereon the composition of claim 3.

38. A product comprising a substrate having coated thereon the composition of claim 8.

13. A composition curable by actinic radiation to form an abrasion resistant optical product comprising a pentaerythritol based polyacrylate selected from the group consisting of a pentaerythritol polyacrylate, a pentaerythritol polymethacrylate, a dipentaerythritol polyacrylate, a dipentaerythritol polymethacrylate, a tripentaerythritol polyacrylate and a tripentaerythritol polymethacrylate, a cellulose acetate butyrate containing on the average from about 13% to 50% butyryl groups, from about 1% to 30% acetyl groups and from about 1% to 5% hydroxyl groups and a photoinitiator, wherein the weight ratio of said polyacrylate to said butyrate is from about 6 to 1 to about 100 to 1.

14. The composition of claim 13 wherein said cellulose acetate butyrate has a viscosity in Poises of from about 50 to 200 at 25°

C. in a solution comprising 20 wt. % cellulose acetate butyrate, 72 wt. % acetone and 8 wt. % ethyl alcohol.

15. The composition of claim 13 wherein said cellulose acetate butyrate contains on the average 37% butyryl groups, 13% acetyl groups and 2% hydroxyl groups and has a viscosity in Poises of from about 64 to 124 at 25°

C. in a solution comprising 20 wt. % cellulose ester, 72 wt. % acetone and 8 wt. % ethyl alcohol.

16. The composition of claim 13 wherein said photoinitiator is alpha chloroacetyldiphenyloxide.

17. The composition of claim 13 wherein said photoinitiator is benzoyl peroxide.

18. The composition of claim 13 which further comprises at least one solvent selected from the group consisting of lower alcohols, lower alkyl acetates, alkyl ketones having from 3 to 7 carbon atoms and ethylene glycol lower alkyl ethers.

19. The composition of claim 13 wherein said weight ratio is from about 8 to 1 to about 20 to 1.

20. The composition of claim 13 wherein said weight ratio is about 10:

1.

21. The composition of claim 13 wherein said pentaerythritol polyacrylate is pentaerythritol tetraacrylate.

22. The composition of claim 13 wherein said dipentaerythritol polyacrylate is dipentaerythritol tetraacrylate.

23. The composition of claim 13 wherein said dipentaerythritol polymethacrylate is dipentaerythritol tetramethacrylate.

28. A product comprising the cured composition of claim 13.

29. A product comprising the cured composition of claim 14.

30. A product comprising the cured composition of claim 15.

31. A product comprising the cured composition of claim 21.

34. An abrasion resistant product comprising a substrate having coated thereon the cured composition of claim 13.

39. A product comprising a substrate having coated thereon the composition of claim 13.

40. A product comprising a substrate having coated thereon the composition of claim 14.

41. A product comprising a substrate having coated thereon the composition of claim 15.

42. A product comprising a substrate having coated thereon the composition of claim 21.

24. A composition curable by actinic radiation to form an abrasion resistant optical product comprising pentaerythritol tetraacrylate, a cellulose acetate butyrate containing on the average 37% butyryl groups, 13% acetyl groups and 2% hydroxyl groups and having a viscosity in Poises of from 64 to 124 at 25°

C. in a solution comprising 20 wt. % cellulose ester, 72 wt. % acetone and 8 wt. % ethyl alcohol and a photoinitiator wherein the weight ratio of said tetraacrylate to said cellulose acetate butyrate is from about 6 to 1 to 100 to 1.

32. A product comprising the cured composition of claim 24.

35. An abrasion resistant product comprising a substrate having coated thereon the cured composition of claim 24.

43. A product comprising a substrate having coated thereon the composition of claim 24.