UV resistant naphthalate polyester articles

• US 7,153,588 B2
• Filed: 05/30/2003
• Issued: 12/26/2006
• Est. Priority Date: 05/30/2003
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Goenner, Emily S., Nelson, Eric W., Jones, Clinton L., Johnson, Stephen A., McMan, Steven J.
• Primary Examiner(s): Chen, Vivian
• Application Number:
  US10/448,894
• Publication Number:
  US 20040241469A1
• Time in Patent Office: 1,306 Days
• Field of Search: None
• US Class Current: 428/483
• CPC Class Codes: C08J 2367/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds; C08J2367/06 takes precedence
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/043 Improving the adhesiveness of the coatings per se, e.g. forming primers adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: Y10T 428/25 Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31797 Next to addition polymer from unsaturated monomers

Abstract

Naphthalate polyester articles can be coated with polymerizable compositions containing a vinyl-functional crosslinkable film former, a large amount of benzotriazole and a copolymerizable monomer that solubilizes the benzotriazole. The cured compositions help protect the naphthalate polyester from UV exposure and other weathering effects.

Claims

1. An article comprising a support comprising a naphthalate polyester overcoated with all resistant coating comprising the polymerized reaction product of a homogenous mixture comprising:

a) at least one vinyl-functional crosslinkable film former;

b) more than 10 weight percent benzotriazole UV absorber; and

c) at least one copolymerizable monomer that solubilizes a sufficient amount of the benzotriazole so that the mixture is homogenous.

2. An article according to claim 1 wherein the support comprises polyethylene naphthalate.

3. An article according to claim 1 wherein the support comprises a multilayer optical film.

4. An article according to claim 1 wherein the benzotriazole comprises 2-(2-hydroxy-3,5-di-tert-amyl-phenyl)-2H-benzotriazole, 2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole or 5-trifluoromethyl-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole.

5. An article according to claim 1 wherein the monomer comprises isooctyl acrylate, 2-ethylhexyl acrylate, t-butyl acrylate, glycidyl methacrylate, benzyl methacrylate, isobornyl acrylate, isobornyl methacrylate, t-butylcyclohexyl acrylate, cyclohexyl acrylate, n-octyldecyl acrylate, butanediol diacrylate, 1-adamantyl acrylate, dicyclopentenyl acrylate or n-vinyl caprolactam.

6. An article according to claim 1 wherein the monomer comprises isobornyl acrylate or t-butylcyclohexyl acrylate.

7. An article according to claim 1 wherein the film former and monomer are chemically distinct species.

8. An article according to claim 1 wherein the film former and monomer are the same species.

9. An article according to claim 1 wherein the mixture comprises about 11 to about 35 weight percent benzotriazole and the coating does not exhibit blooming.

10. An article according to claim 1 wherein the mixture further comprises submicron inorganic particles.

11. An article according to claim 1 wherein the coating has a T_vis of at least about 60%.

12. An article according to claim 1 wherein the coating can withstand an exposure of at least 18,700 kJ/m² at 340 nm before the b* value obtained using the CIE L*a*b color space increases by 4 or more, or before the onset of significant cracking, peeling, delamination or haze, when evaluated using the weathering cycle described in ASTM G155 and a D65 light source operated in the reflected mode.

13. An article according to claim 1 comprising a light tube, lamp reflector, bulb cavity reflector, solar concentrator or solar collector.

14. An article according to claim 1 comprising a mirror or imitation chrome.

15. An article according to claim 1 comprising vehicular glazing, architectural glazing or a greenhouse panel.

16. An article according to claim 1 comprising a sensor, solar cell, sign, graphic arts film, point of purchase display, decorative film, cell-phone body, apparel or home appliance.

17. An article according to claim 1 wherein the homogenous mixture comprises about 16 to about 35 weight percent benzotriazole.

18. An article according to claim 1 wherein the homogenous mixture comprises about 21 to about 35 weight percent benzotriazole.

19. An article comprising a support comprising a naphthalate polyester overcoated with a UV resistant coating comprising the polymerized reaction product of a homogenous mixture comprising:

a) at least one vinyl-fbnctional crosslinkable film former;

b) more than 5 weight percent benzotriazole UV absorber or absorbers comprising 2-(2-hydroxy-3-alpha-cumyl-5-t-octylphenyl)-5-trifluoromethylbenzotriazole; and

c) at least one copolymerizable monomer that solubilizes the benzotriazole.

20. An article according to claim 19 wherein the support comprises polyethylene naphthalate.

21. An article according to claim 19 wherein the support comprises a multilayer optical film.

22. An article according to claim 19 wherein the monomer comprises isooctyl acrylate, 2-ethylhexyl acrylate, t-butyl acrylate, glycidyl methacrylate, benzyl methacrylate, isobornyl acrylate, isobornyl methacrylate, t-butylcyclohexyl acrylate, cyclohexyl acrylate, n-octyldecyl acrylate, butanediol diacrylate, 1-adamantyl acrylate, dicyclopentenyl acrylate or n-vinyl caprolactam.

23. An article according to claim 19 wherein the monomer comprises isobornyl acrylate or t-butylcyclohexyl acrylate.

24. An article according to claim 19 wherein the film former and monomer are chemically distinct species.

25. An article according to claim 19 wherein the film former and monomer are the same species.

26. An article according to claim 19 wherein the mixture comprises about 6 to about 35 weight percent benzotriazole and the coating does not exhibit blooming.

27. An article according to claim 19 wherein the mixture further comprises submicron inorganic particles.

28. An article according to claim 19 wherein the coating can withstand an exposure of at least 18,700 kJ/m² at 340 nm before the b* value obtained using the CIE L*a*b* color space increases by 4 or more, or before the onset of significant cracking, peeling, delamination or haze, when evaluated using the weathering cycle described in ASTM G155 and a D65 light source operated in the reflected mode.

29. A process for applying a UV resistant coating to a naphthalate polyester article comprising:

a) providing a support comprising a napthalate polyester;

b) coating at least a portion of the support with a homogenous mixture comprising (i) at least one vinyl-functional crosslinkable film former;

(ii) more than 10 weight percent benzotriazole UV absorber; and

(iii) at least one copolymerizable monomer that solubilizes the benzotriazole; and

c) polymerizing the coating.

30. A process according to claim 29 wherein the support comprises polyethylene naphthalate.

31. A process according to claim 29 wherein the support comprises a multilayer optical film.

32. A process according to claim 29 wherein the film former comprises a di-, tri- or higher functional acrylate or methacrylate.

33. A process according to claim 29 wherein the film former comprises butanediol diacrylate, hexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate or trimethylolpropane triacrylate.

34. A process according to claim 29 wherein the benzotriazole comprises 2-(2-hydroxy-3,5-di-tert-amyl-phenyl)-2H-benzotriazole, 2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotrizole or 5-trifluoromethyl-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole.

35. A process according to claim 29 wherein the monomer comprises isooctyl acrylate, 2-ethylhexyl acrylate, t-butyl acrylate, glycidyl methacrylate, benzyl methacrylate, isobornyl acrylate, isobornyl methacrylate, t-butylcyclohexyl acrylate, cyclohexyl acrylate, n-octyldecyl acrylate, butanediol diacrylate, 1-adamantyl acrylate, dicyclopentenyl acrylate or n-vinyl caprolactam.

36. A process according to claim 29 wherein the monomer comprises isobornyl acrylate or t-butylcyclohexyl acrylate.

37. A process according to claim 29 wherein the film former and monomer are chemically distinct species.

38. A process according to claim 29 wherein the film former and monomer are the same species.

39. A process according to claim 29 wherein the mixture comprises a photoinitiator and is photopolymerizable.

40. A process according to claim 29 wherein the mixture comprises about 11 to about 35 weight percent benzotriazole and the polymerized coating does not exhibit blooming.

41. A process according to claim 29 wherein the mixture further comprises submicron inorganic particles.

42. A process according to claim 29 wherein the homogenous mixture comprises about 16 to about 35 weight percent benzotriazole.

43. A process according to claim 29 wherein the homogenous mixture comprises about 21 to about 35 weight percent benzotriazole.

44. A process for applying a UV resistant coating to a naphthalate polyester article comprising:

a) providing a support comprising a naphthalate polyester;

b) coating at least a portion of the support wit a homogenous mixture comprising (i) at least one vinyl-functional crosslinkable film former;

(ii) more than 5 weight percent benzotriazole UV absorber or absorbers comprising 2-(2-hydroxy-3-alpha-cumyl-5-octylphenyl)-5-trifluromethylbenzotriazole;

(iii) at least one copolymerizable monomer that solubilizes the benzotriazole; and

c) polymerizing the coating.

45. A process according to claim 44 wherein the support comprises polyethylene naphthalate.

46. A process according to claim 44 wherein the support comprises a multilayer optical film.

47. A process according to claim 44 wherein the film former comprises a di-, tri- or higher functional acrylate or methacrylate.

48. A process according to claim 44 wherein the film former comprises butanediol diacrylate, hexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate or trimethylolpropane triacrylate.

49. A process according to claim 44 wherein the monomer comprises isooctyl acrylate, 2-ethylhexyl acrylate, t-butyl acrylate, glycidyl methacrylate, benzyl methacrylate, isobornyl acrylate, isobornyl methacrylate, t-butylcyclohexyl acrylate, cyclohexyl acrylate, n-octyldecyl acrylate, butanediol diacrylate, 1-adamantyl acrylate, dicyclopentenyl acrylate or n-vinyl caprolactam.

50. A process according to claim 44 wherein the monomer comprises isobornyl acrylate or t-butylcyclohexyl acrylate.

51. A process according to claim 44 wherein the film former and monomer are chemically distinct species.

52. A process according to claim 44 wherein the film former and monomer are the same species.

53. A process according to claim 44 wherein the mixture comprises a photoinitiator and is photopolymerizable.

54. A process according to claim 44 wherein the mixture comprises about 6 to about 35 weight percent benzotriazole and the polymerized coating does not exhibit blooming.

55. A process according to claim 44 wherein the mixture further comprises submicron inorganic particles.