Photochromic optical article

• US 7,189,456 B2
• Filed: 03/04/2004
• Issued: 03/13/2007
• Est. Priority Date: 03/04/2004
• Status: Active Grant

• Current Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Original Assignee: Transitions Optical, Inc. (EssilorLuxottica SA)
• Inventors: King, Eric M.
• Primary Examiner(s): WOODWARD, ANA LUCRECIA
• Application Number:
  US10/793,589
• Publication Number:
  US 20050196617A1
• Time in Patent Office: 1,104 Days
• Field of Search: 428/412, 428/411.1, 428/480, 428/447, 428/423.7, 252/582, 252/586, 351/163, 359/580, 359/586
• US Class Current: 428/412
• CPC Class Codes: B29K 2069/00 Use of PC, i.e. polycarbonates or derivatives thereof, as moulding material
• CPC Class Codes: B29K 2995/0018 having particular optical properties, e.g. fluorescent or phosphorescent
• CPC Class Codes: B32B 27/00 Layered products comprising a layer of synthetic resin fibrous or filamentary layer made of a synthetic resin B32B5/02; particulate layer made of a synthetic resin B32B5/16; foamed layer made of a synthetic resin B32B5/18
• CPC Class Codes: C03C 4/06 for phototropic or photochromic glass
• CPC Class Codes: C09D 201/005 Dendritic macromolecules
• CPC Class Codes: G02B 1/10 Optical coatings produced by application to, or surface treatment of, optical elements G02B1/08 takes precedence
• CPC Class Codes: G02B 5/23 Photochromic filters
• CPC Class Codes: G03C 1/733 with macromolecular compounds as photosensitive substances, e.g. photochromic photodegradable or photocrosslinkable compositions G03F7/004
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31507 Of polycarbonate
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31565 Next to polyester [polyethylene terephthalate, etc.]
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers

Abstract

Describes a photochromic plastic article, e.g., an ophthalmic photochromic article, such as a lens, in which the article includes (1) a rigid substrate, e.g., polymeric substrate, such as a thermoset or thermoplastic substrate, (2) a photochromic polymeric coating appended to at least one surface of the substrate, the photochromic polymeric coating containing a photochromic amount of at least one photochromic material, e.g., spirooxazine, naphthopyran and/or fulgide, and (3) a dendritic polyester acrylate film coherently appended to the photochromic coating. Describes also the aforedescribed photochromic article having an abrasion-resistant coating affixed to the dendritic polyester acrylate film, e.g., an abrasion-resistant coating comprising an organo silane; and a photochromic article having an antireflective coating affixed to the abrasion-resistant coating.

Claims

1. A photochromic article comprising:

(a) a rigid substrate,

(b) a photochromic organic polymeric coating appended to at least a portion of at least one surface of said substrate, said polymeric coating comprising a photochromic amount of at least one photochromic material, and

(c) a transparent dendritic polyester acrylate film superposed on said photochromic polymeric coating.

2. The photochromic article of claim 1 wherein the dendritic polyester acrylate film is prepared from a liquid composition prepared by acrylating a dendritic polyester macromolecule and an organic alcohol having a molecular weight of less than 2000.

3. The photochromic article of claim 1 wherein the dendritic polyester acrylate film is prepared from a composition comprising dendritic polyester acrylate and at least one other radiation or thermally curable acrylic material.

4. The photochromic article of claim 3 wherein the at least one other radiation or thermally curable acrylic material is (meth)acrylic monomeric material selected from monoacrylates and polyacrylates.

5. The photochromic article of claim 4 wherein the polyacrylate is a diacrylate, triacrylate or mixture of diacrylate(s) and triacrylate(s).

6. The photochromic article of claim 4 wherein the weight ratio of the dendritic polyester acrylate to the other radiation or thermally curable (meth)acrylic monomeric material(s) ranges from 90:

10 to 10;

90.

7. The photochromic article of claim 6 wherein the weight ratio of the dendritic polyester acrylate to the other radiation or thermally curable (meth)acrylic monomeric material(s) ranges from 70:

30 to 30;

70.

8. The photochromic article of claim 6 wherein the weight ratio of the dendritic polyester acrylate to the other radiation or thermally curable (meth)acrylic monomeric material(s) ranges from 60:

40 to 40;

60.

9. The photochromic article of claim 3 wherein at least one photoinitiator is present in photoinitiating amounts in the composition comprising the dendritic polyester acrylate and the at least one other radiation curable acrylic material.

10. The photochromic article of claim 4 wherein the dendritic polyester acrylate film is prepared from a composition further comprising at least one other radiation curable monomeric material containing polymerizable group(s), other than acrylic functional groups, said at least one other radiation curable monomeric material being present in amounts of up to 40 weight percent of said composition.

11. The photochromic article of claim 4 wherein at least one photoinitiator is present in photoinitiating amounts in the composition comprising the dendritic polyester acrylate.

12. The photochromic article of claim 11 wherein the at least one photoinitiator is present in an amount of from 0.1 to 10 weight percent.

13. The photochromic article of claim 11 wherein the at least one photoinitiator is present in an amount of from 0.5 to 6 weight percent.

14. The photochromic article of claim 1 further comprising an abrasion-resistant coating superposed on the surface of the dendritic polyester acrylate film.

15. The photochromic article of claim 14 wherein the abrasion-resistant coating comprises an organo silane-based coating.

16. The photochromic article of claim 14 further comprising an antireflective coating affixed to the surface of the abrasion-resistant film.

17. The photochromic article of claim 1 wherein the thickness of the dendritic polyester acrylate film ranges from 2 to 20 microns.

18. The photochromic article of claim 1 wherein the dendritic polyester acrylate film is compatible with abrasion-resistant organo silane-containing coatings.

19. The photochromic article of claim 18 wherein the photochromic organic polymeric coating is softer than the dendritic polyester acrylate film.

20. The photochromic article of claim 1 wherein the rigid substrate is an organic polymeric substrate chosen from thermoset or thermoplastic materials having a refractive index of from 1.48 to 1.74.

21. The photochromic article of claim 20 wherein the polymeric substrate is a substrate chosen from thermoset substrates prepared from polymerizable compositions comprising allyl diglycol carbonate monomer(s), substrates prepared from thermoplastic polycarbonates, substrates prepared from polyurea urethanes or substrates prepared from compositions comprising the reaction product of polyfunctional isocyanate(s) and/or isothiocyanate(s) with polythiol or polyepisulfide monomer(s).

22. The photochromic article of claim 21 wherein the allyl diglycol carbonate is diethylene glycol bis(allyl carbonate).

23. The photochromic article of claim 1 wherein the photochromic organic polymeric coating is chosen from photochromic polyurethane-based coatings, photochromic polyurea urethane-based coatings, photochromic poly(meth)acrylic-based coatings, photochromic aminoplast resin-based coatings, or photochromic epoxy resin-based coatings.

24. The photochromic article of claim 1 wherein the photochromic material is an organic photochromic material chosen from photochromic spirooxazines, benzopyrans, naphthopyrans, fulgides, metal dithizonates, diarylethenes or mixtures of such photochromic materials.

25. The photochromic article of claim 24 wherein the photochromic naphthopyran is chosen from naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spiro-9-fluoreno[1,2-b]pyrans, phenanthropyrans, quinopyrans or indeno-fused naphthopyrans, and the spirooxazine is chosen from naphthoxazines or spiro (indoline)pyridobenzoxazines.

26. A photochromic:

article comprising;

(a) a transparent rigid organic polymeric substrate,

(b) a photochromic organic polymeric coating appended to at least a portion of at least one surface of said polymeric substrate, said polymeric coating comprising a photochromic amount of at least one organic photochromic material, and

(c) a transparent dendritic polyester acrylate film coherently appended to said photochromic polymeric coating.

27. The photochromic article of claim 26 wherein the polymeric substrate is chosen from thermoset or thermoplastic materials having a refractive index of from 1.48 to 1.74.

28. The photochromic article of claim 26 wherein the polymeric substrate is a substrate chosen from thermoset substrates prepared from polymerizable compositions comprising allyl diglycol carbonate monomer(s), substrates prepared from thermoplastic polycarbonates, substrates prepared from polyurea urethanes or substrates prepared from compositions comprising the reaction product of polyfunctional isocyanate(s) and/or isothiocyanate(s) with polythiol or polyepisulfide monomer(s).

29. The photochromic article of claim 28 wherein the dendritic polyester acrylate film is prepared from a liquid composition prepared by acrylating a dendritic polyester macromolecule and an organic alcohol having a molecular weight of less than 2000.

30. The photochromic article of claim 28 wherein the dendritic polyester acrylate film is prepared from a composition comprising dendritic polyester acrylate and at least one other radiation curable acrylic material, and said at least one other radiation curable acrylic material is (meth)acrylic monomeric material chosen from monoacrylates, polyacrylates and mixtures of such acrylic materials.

31. The photochromic article of claim 30 wherein the dendritic polyester acrylate film is prepared from a composition comprising dendritic polyester acrylate and neopentylglycol-2-propoxylate diacrylate.

32. The photochromic article of claim 30 wherein at least one photoinitiator is present in photoinitiating amounts in the composition comprising the dendritic polyester acrylate.

33. The photochromic article of claim 26 further comprising an abrasion-resistant coating affixed to the surface of the dendritic polyester acrylate film.

34. The photochromic article of claim 33 wherein the abrasion-resistant coating comprises an organo silane-based coating.

35. The photochromic article of claim 33 further comprising an antireflective coating affixed to the surface of the abrasion-resistant film.

36. A photochromic article comprising:

(a) a transparent organic polymeric substrate chosen from thermoset substrates prepared from polymerizable compositions comprising allyl diglycol carbonate monomer(s), substrates prepared from thermoplastic polycarbonates, substrates prepared from polyurea urethanes or substrates prepared from compositions comprising the reaction product of polyfunctional isocyanate(s) and/or isothiocyanates with polythiols or polyepisulfide monomer(s), said substrate having a refractive index of from 1.48 to 1.74,

(b) a transparent photochromic organic polymeric coating appended to at least one surface of said polymeric substrate, said polymeric coating comprising a photochromic amount of at least one organic photochromic material chosen from spirooxazines, benzopyrans, naphthopyrans, fulgides, metal dithizonates, diarylethenes, or mixtures of such photochromic materials, said photochromic polymeric coating having a thickness of from 5 to 200 microns, and

(c) radiation-cured, transparent dendritic polyester acrylate film coherently appended to said photochromic polymeric coating.

37. The photochromic article of claim 36 wherein the photochromic coating is chosen from photochromic polyurethane-based coatings, photochromic polyurea urethane-based coatings, photochromic poly(meth)acrylic-based coatings, photochromic aminoplast resin-based coatings, or photochromic epoxy resin-based coatings, and has a thickness of from 10 to 50 microns.

38. The photochromic article of claim 36 further comprising an abrasion-resistant coating affixed to the surface of the dendritic polyester acrylate film.

39. The photochromic article of claim 38 wherein the abrasion-resistant coating comprises an organo silane-based coating.

40. The photochromic article of claim 38 further comprising an antireflective coating affixed to the surface of the abrasion-resistant coating.

41. The photochromic article of claim 36 wherein the polymeric substrate is a substrate comprising a thermoplastic polycarbonate.

42. The photochromic article of claim 41 wherein the dendritic polyester acrylate film is prepared from a composition comprising dendritic polyester acrylate and at least one other radiation curable acrylic material.

43. The photochromic article of claim 42 wherein the at least one other radiation curable acrylic material is (meth)acrylate monomeric material(s) chosen from monoacrylates or polyacrylates.

44. The photochromic article of claim 43 wherein the polyacrylate material(s) is a diacrylate, triacrylate or mixture of diacrylate(s) and triacrylate(s).

45. The photochromic article of claim 43 wherein the weight ratio of the dendritic polyester acrylate to the other radiation curable (meth)acrylate acrylic material(s) ranges from 70:

30 to 30;

70.

46. The photochromic article of claim 36 wherein the dendritic polyester acrylate film is prepared from a liquid composition prepared by acrylating a dendritic polyester macromolecule and an aliphatic alcohol having a molecular weight of from 60 to 1000.

47. The photochromic article of claim 41 wherein the photochromic coating is chosen from photochromic polyurethane-based coatings, photochromic polyurea urethane-based coatings, photochromic poly(meth)acrylic-based coatings, photochromic aminoplast resin-based coatings, or photochromic epoxy resin-based coatings, and has a thickness of from 10 to 50 microns, and the dendritic polyester acrylate film is prepared from a composition comprising dendritic polyester acrylate and at least one other radiation curable (meth)acrylic material.

48. The photochromic article of claim 47 wherein at least one photoinitiator is present in amounts of from 0.1 to 10 weight percent in the composition comprising the dendritic polyester acrylate and the at least one other radiation curable (meth) acrylic material.

49. The photochromic article of claim 48 wherein the article is an ophthalmic article.

50. The photochromic article of claim 49 wherein the ophthalmic article is a lens.

51. The photochromic article of claim 50 further comprising an abrasion-resistant coating affixed to the surface of the dendritic polyester acrylate film.

52. The photochromic article of claim 51 further comprising an antireflective coating affixed to the surface of the abrasion-resistant coating.

53. The photochromic article of claim 42 wherein at least one photoinitiator is present in photoinitiating amounts in the composition comprising the dendritic polyester acrylate and the at least one other radiation curable acrylic material.

54. The photochromic article of claim 53 wherein the at least one photoinitiator is present in amounts of from 0.5 to 6 weight percent.

55. The photochromic article of claim 36, wherein the article is an ophthalmic article.

56. The photochromic article of claim 55 wherein the ophthalmic article is a lens.