Coatings for Optical Elements

• US 20080311404A1
• Filed: 12/21/2006
• Published: 12/18/2008
• Est. Priority Date: 12/21/2005
• Status: Abandoned Application

• Current Assignee: Carl Zeiss Vision Incorporated (Carl-Zeiss-Stiftung)
• Original Assignee: Carl Zeiss Vision Incorporated (Carl-Zeiss-Stiftung)
• Inventors: Diggins, David Robert
• Application Number:
  US12/158,446
• Publication Number:
  US 20080311404A1
• Time in Patent Office: Days
• US Class Current: 428/413
• CPC Class Codes: C08F 222/104 of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• 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
• CPC Class Codes: G02B 1/105 Protective coatings
• CPC Class Codes: G02B 1/14 Protective coatings, e.g. hard coatings
• CPC Class Codes: Y10T 428/31511 Of epoxy ether

Abstract

The invention provides an abrasion resistant coating composition for an optical element. The composition includes a polymerisable epoxy monomer having an average of at least two epoxy groups in the monomer molecule. The composition is capable of forming an abrasion resistant coating on an optical element after ionic polymerisation. The coating composition may also include an ionically polymerisable alkene monomer having an average of at least two polymerisable double bonds in the molecule.

Claims

1. An abrasion resistant coating composition for an optical element, the composition including a polymerisable epoxy monomer having an average of at least two epoxy groups in the monomer molecule wherein the composition is capable of forming an abrasion resistant coating on an optical element after ionic polymerisation.

2. An abrasion resistant coating composition according to claim 1, further including an ionically polymerisable alkene monomer having an average of at least two polymerisable double bonds in the molecule.

3. An abrasion resistant coating composition according to claim 2, wherein the ionically polymerisable alkene monomer is cationically polymerisable.

4. An abrasion resistant coating composition according to claim 1, wherein the epoxy monomer is selected from one or more of the group consisting of:

ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6 hexane diol diglycidyl ether, glycerine diglycidyl ether, pentaerythritol diglycidyl ether, bisphenol-A diglycidyl ether (BPADGE), bisphenol-F diglycidyl ether, and their extended chain analogs, 1,4-butanediol diglycidyl ether, diglycidyl ethers of tetrabromo-bisphenol-A, and epoxy based ethers of 4,4′

-biphenylene.

5. An abrasion resistant coating composition according to claim 1, wherein the epoxy monomer has an average of at least three epoxy groups per molecule.

6. An abrasion resistant coating composition according to claim 5, wherein the epoxy monomer is selected from one or more of the group consisting of:

trimethylol propane triglycidyl ether, pentaerythritol triglycidyl ether, glycerol triglycidyl ether, diglycerol triglycidyl ether, diglycerol tetraglycidyl ether, pentaerythritol tetraglycidyl ether, and dipentaerythritol tetraglycidyl ether.

7. An abrasion resistant coating composition according to claim 2, wherein the ionically polymerisable alkene monomer has an average of at least three polymerisable double bonds in the molecule.

8. An abrasion resistant coating composition according to claim 7, wherein the ionically polymerisable alkene monomer has an average of at least four polymerisable double bonds in the molecule.

9. An abrasion resistant coating composition according to claim 2, wherein the ionically polymerisable alkene monomer is selected from one or more of the group consisting of:

an acrylate monomer, a methacrylate monomer, a vinyl monomer, and an allyl monomer.

10. An abrasion resistant coating composition according to claim 9, wherein the ionically polymerisable alkene monomer is selected from one or more of the group consisting of:

pentaerythritol tetraacrylate, tris(2-hydroxyethyl)isocyanurate triacrylate, trimethylol propyl triacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, 2,2,4,4,6,6-hexahydro-2,2,4,4,6,6-hexakis(2-((2-methyl-1-oxo-2-propenyl)oxy)ethoxy)-1,3,5,2,4,6-triazatriphosphorine, U6HA (hexafunctional urethane (meth)acrylate), U4HA (tetrafunctional urethane (meth)acrylate), tricyclodecane dimethanol diacrylate, and tris(2-hydroxyethyl)isocyanurate diacrylate.

11. An abrasion resistant coating composition according to claim 10, wherein the ionically polymerisable alkene monomer is pentaerythritol tetraacrylate.

12. An abrasion resistant coating composition according to claim 1, further including a cationic photoinitiator.

13. An abrasion resistant coating composition according to claim 1, further including a hardness enhancer.

14. An abrasion resistant coating composition according to claim 13, wherein the hardness enhancer is a colloidal metal oxide.

15. An abrasion resistant coating composition according to claim 14, wherein the colloidal metal oxide is functionalised with a polymerisable group.

16. An abrasion resistant coating composition according to claim 13, wherein the hardness enhancer is (meth)acrylated colloidal silica or epoxylated colloidal silica.

17. An abrasion resistant coating composition according to claim 1, further including a solvent.

18. An abrasion resistant coating composition according to claim 17, wherein the solvent is a mixture of:

(a) one or more of solvents selected from the group consisting of;

a ketone solvent, an ester solvent, and an ether solvent; and

(b) a lower alcohol.

19. An optical element having an abrasion resistant coating on a surface thereof, the abrasion resistant coating having been formed by ionically polymerising an abrasion resistant coating composition according to claim 1.

20. An optical element according to claim 19, wherein the optical element is formed from a thermoset polymer.

21. An optical element according to claim 20, wherein the thermoset polymer is selected from one or more of the group consisting of:

a polymer of diethylene glycol bis(allyl carbonate), an acrylate polymer, a thiolene polymer, a urethane polymer, a thiourethane polymer, and a thioepoxide polymer.

22. An optical element according to claim 19, wherein the optical element is formed from a thermoplastic polymer.

23. An optical element according to claim 22, wherein the thermoplastic polymer is selected from one or more of the group consisting of:

a polycarbonate polymer of bisphenol A, and a polyamide.

24. An optical element according to claim 19, wherein the abrasion resistant coating has a Bayer abrasion resistance of two stars or greater.

25. An optical element according to claim 19, wherein the abrasion resistant coating has a steel wool abrasion resistance of three stars or greater.

26. An optical element according to claim 19, wherein the optical element is an ophthalmic lens.

27. An optical element according to claim 19, wherein the abrasion resistant coating is formed directly on the surface of the optical element.

28. A method of forming an abrasion resistant coating on a surface of an optical element, the method including:

providing an optical element having a surface to be coated;

coating a surface of the optical element with a coating composition according to claim 1; and

ionically polymerising the coating composition to form the abrasion resistant coating on the surface of the optical element.

29. A method of forming an abrasion resistant coating according to claim 28, wherein the optical element is formed from a thermoset polymer.

30. A method of forming an abrasion resistant coating according to claim 29, wherein the thermoset polymer is selected from one or more of the group consisting of:

a polymer of diethylene glycol bis(allyl carbonate), an acrylate polymer, a thiolene polymer, a urethane polymer, and a thiourethane polymer.

31. A method of forming an abrasion resistant coating according to claim 28, wherein the optical element is formed from a thermoplastic polymer.

32. A method of forming an abrasion resistant coating according to claim 31, wherein the thermoplastic polymer is selected from one or more of the group consisting of:

a polycarbonate polymer of bisphenol A, and a polyamide.

33. A method of forming an abrasion resistant coating according to claim 28, wherein the step of coating the optical element includes applying the coating composition directly on the surface of the optical element.

34. A method of forming an abrasion resistant coating according to claim 28, wherein the step of ionically polymerising the coating composition includes a step of irradiating the coating composition with UV light.

35. A method of forming an abrasion resistant coating according to claim 34, wherein the coating composition is irradiated with UV light for a period of 5 to 60 seconds at a dose greater than about 5 Jcm⁻

2 with a maximum intensity greater than about 0.5 Wcm<sup>−

2</sup>.

36. A method of forming an abrasion resistant coating according to claim 28, wherein the optical element is an ophthalmic lens.

37. A method of forming an abrasion resistant coating on a surface of an optical element, the method including:

coating a surface of a section of a mould used to manufacture the optical element with a coating composition according to claim 1;

at least partially ionically polymerising the coating composition;

assembling a mould containing the mould section;

filling the mould with a cross-linkable polymeric casting composition; and

polymerising the casting composition so as to form the optical element with the abrasion resistant coating on a surface.

38. (canceled)

39. (canceled)

40. (canceled)