UV curable coating compositions for improved abrasion resistance

• US 10,459,248 B2
• Filed: 12/30/2014
• Issued: 10/29/2019
• Est. Priority Date: 12/30/2014
• Status: Active Grant

• Current Assignee: Essilor International SA
• Original Assignee: Essilor International SA
• Inventors: Valeri, Robert
• Primary Examiner(s): Schwartz, Jordan M
• Application Number:
  US15/540,197
• Publication Number:
  US 20180003861A1
• Time in Patent Office: 1,764 Days
• Field of Search: 35115957, 351 44, 35115949, 35115959, 35115962, 3511596, 35115973, 35115975, 427166, 428411, 428412, 10628711
• 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: C09D 183/04 Polysiloxanes
• CPC Class Codes: G02B 1/11 Anti-reflection coatings
• CPC Class Codes: G02B 1/14 Protective coatings, e.g. hard coatings
• CPC Class Codes: G02C 2202/16 Laminated or compound lenses
• CPC Class Codes: G02C 7/02 Lenses; Lens systems ; Methods of designing lenses
• CPC Class Codes: G02C 7/022 Ophthalmic lenses having special refractive features achieved by special materials or material structures G02C7/049 takes precedence
• CPC Class Codes: G02C 7/024 Methods of designing ophthalmic lenses

Abstract

An ophthalmic article and methods of manufacturing the ophthalmic article are described herein. The ophthalmic article can include a first coating and a second coating. The first coating can include an abrasion resistant coating that includes flexible materials. The abrasion resistant coating can be radiation cured. The second coating can include a sputter-applied anti-reflective (AR) coating. Such an ophthalmic article can have a Bayer value of at or between 1.25 and 2.6, between 1.25 and 2.0 or 1.25 and 1.75; and a hand steel wool value of 3 or less.

Claims

1. An ophthalmic article comprising:

a first coating comprising an abrasion resistant coating comprising at least one flexible material having a glass transition temperature ranging from −

150°

C. to 25°

C., wherein the abrasion resistant coating is radiation-cured; and

a second coating comprising a sputter-applied anti-reflective (AR) coating,

wherein the ophthalmic article has a Bayer value of at or between 1.25 and 2.6 and a hand steel wool value of 3 or less.

2. The ophthalmic article of claim 1, wherein the second coating is adhered directly to the first coating.

3. The ophthalmic article of claim 1, wherein the at least one flexible material comprises at least one of an aliphatic epoxy, a difunctional acrylate, a vinyl silane, a vinyl ether, a urethane, or a polyester.

4. The ophthalmic article of claim 1, wherein the first coating further comprises at least one rigid material, wherein the rigid material comprises at least one of an epoxy alkoxysilane, a mono-organoalkoxysilane, a tetraorganoxysilane, or a polyorganoxysiloxane.

6. The ophthalmic article of claim 1, wherein the first coating further comprises highly cross-linkable materials, wherein the highly cross-linkable materials comprise at least one of SiO₂, pentaerythritol tri- and tetra acrylate, pentaerythritol triacrylate, ethoxylated pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, or dipentaerthritolhexaacrylate.

7. The ophthalmic article of claim 1, wherein the first coating is a single layer.

8. The ophthalmic article of claim 1, wherein the anti-reflective coating comprises at least four layers.

16. The ophthalmic article of claim 1, wherein the first coating further comprises at least one rigid material.

17. The ophthalmic article of claim 1, wherein the first coating further comprises at least one rigid material having a glass transition temperature ranging from 25°

C. to 250°

C.

5. The ophthalmic article of 4, wherein the first coating comprises flexible material in a greater weight amount than a weight amount of rigid material.

9. A method of manufacturing an ophthalmic article comprising:

applying a first coating to an ophthalmic article, wherein the first coating comprises a radiation-curable abrasion resistant coating comprising at least one flexible material having a glass transition temperature ranging from −

150°

C. to 25°

C.;

radiation-curing the first coating; and

sputter-applying a second coating onto the first coating, the second coating comprising an anti-reflective coating;

wherein the article, after application of the second coating, has a Bayer value of at or between 1.25 and 2.6 and a hand steel wool value of 3 or less.

10. The method of claim 9, wherein the second coating is adhered directly to the first coating.

11. The method of claim 9, wherein the at least one flexible material comprises at least one of an aliphatic epoxy, a difunctional acrylate, a vinyl silane, a vinyl ether, a urethane, a polyester, or any combination thereof.

12. The method of claim 9, wherein the first coating further comprises at least one rigid material, wherein the rigid material comprises at least one of an epoxy alkoxysilane, a mono-organoalkoxysilane, a tetraorganoxysilane, or a polyorganoxysiloxane, and wherein a weight amount of flexible material is greater than a weight amount of rigid material.

13. The method of claim 9, wherein the first coating is a single layer.

14. The method of claim 9, wherein the anti-reflective coating comprises at least four layers.

15. An ophthalmic article manufactured by the method of claim 9.

18. The method of claim 9, wherein the first coating further comprises at least one rigid material.

19. The method of claim 9, wherein the first coating further comprises at least one rigid material having a glass transition temperature ranging from 25°

C. to 250°

C.