CURABLE COATING COMPOSITION

• US 20140342100A1
• Filed: 01/03/2012
• Published: 11/20/2014
• Est. Priority Date: 01/03/2012
• Status: Active Grant

• Current Assignee: Essilor International SA (EssilorLuxottica SA)
• Original Assignee: Essilor International SA (EssilorLuxottica SA)
• Inventors: Valeri, Robert Alan
• Granted Patent: US 9,557,449 B2
• Time in Patent Office: Days
• US Class Current: 427/553
• CPC Class Codes: B05D 3/067 Curing or cross-linking the coating
• CPC Class Codes: C08K 5/5435 containing oxygen in a ring
• 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 1/105 Protective coatings
• CPC Class Codes: G02B 1/12 by surface treatment, e.g. by irradiation
• CPC Class Codes: G02B 1/14 Protective coatings, e.g. hard coatings

Abstract

UV curable coating composition includes a non hydrolyzed epoxy- alkoxy-silane, polyfunctional acrylate and/or epoxy compounds and a cationic and/or free-radical photo-initiator; with polyfunctional acrylate and/or epoxy compounds representing more than 40 weight % of the total dry matter and the composition being without any hydrolyzed epoxy-alkoxy-silane. This composition is coated and cured on an optical substrate.

Claims

1-14. -14. (canceled)

15. A UV curable coating composition comprising:

a) at least one non hydrolyzed epoxyalkoxysilane;

b) at least one polyfunctional acrylate monomer and/or polyfunctional epoxy compound, different from a);

c) at least one free radical photoinitiator and/or cationic photoinitiator;

wherein the total amount of said b) is more than 40 weight %, relative to the total dry matter of the composition; and

said composition does not comprise any hydrolyzed epoxyalkoxysilane.

16. The composition according to claim 15, wherein the total amount of said epoxyalkoxysilane is from 20 (inclusive) to 60 (exclusive) weight %, relative to the total dry matter of the composition.

17. The composition according to claim 15, wherein the molar ratio between the total amount of epoxy functions and the total amount of acrylate functions is from 0.1 to 3.

18. The composition according to claim 15, wherein said epoxyalkoxysilane is selected from glycidyl(C_1-3 alkyl)-(C_1-3 alkyl)-di(C_1-3 alkoxy) silanes and glycidyl(C_1-3 alkyl)-tri(C_1-3 alkoxy)silanes, and is preferably 3-glycidoxypropyl-methyldiethoxysilane and/or 3-glycidoxypropyltrimethoxysilane.

19. The composition according to claim 15, wherein said polyfunctional acrylate monomer is selected from the group consisting of 1,4-butanedioldiacrylate, 1,6-hexanedioldiacrylate, dipropyleneglycol diacrylate pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, silicone hexaacrylate, and mixtures thereof;

and said polyfunctional epoxy compound is selected from the group consisting of diglycerol tetraglycidyl ether, dipentaerythritol tetraglycidyl ether, sorbitol polyglycidyl ether, polyglycerol polyglycidyl ether, pentaerythritol polyglycidyl ether such as pentaerythritol tetraglycidyl ether, trimethylolethane triglycidyl ether, trimethylolmethane triglycidyl ether, trimethylolpropane triglycidyl ether, triphenylolmethane triglycidyl ether, trisphenol triglycidyl ether, tetraphenylol ethane triglycidyl ether, tetraglycidyl ether of tetraphenylol ethane, p-aminophenol triglycidyl ether, 1,2,6-hexanetriol triglycidyl ether, glycerol triglycidyl ether, diglycerol triglycidyl ether, glycerol ethoxylate triglycidyl ether, Castor oil triglycidyl ether, propoxylated glycerine triglycidyl ether, ethylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, cyclohexanedimethanol diglycidyl ether, dipropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, dibromoneopentyl glycol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, (3,4-Epoxycyclohexane) methyl 3,4-epoxycylohexylcarboxylate, and mixtures thereof.

20. The composition according to claim 15, wherein the total amount of cationic photoinitiator is from 1 to 15 weight %, relative to the total dry matter of the composition, and the total amount of free radical photoinitiator is from 1 to weight %, relative to the total amount of polyfunctional acrylate monomers.

21. The composition according to claim 15, wherein said cationic photoinitiator is selected from triarylsulfonium hexafluoroantimonate, triarylsulfonium hexafluorophosphate, diaryliodonium hexafluoroantimonate and diaryliodonium hexafluorophosphate salts, and mixtures thereof;

and said free radical photoinitiator is selected from haloalkylated aromatic ketones, benzoin ethers, dialkoxyacetophenones, hydroxy ketones, alpha amino ketones, alpha-amino acetophenones, monoacyl and bisacyl phosphine oxides and sulphides, triacyl phosphine oxides, and mixtures thereof.

22. The composition according to claim 15, wherein said composition comprises a solvent.

23. The composition according to claim 15, wherein said composition comprises colloidal silica particles.

24. The composition according to claim 15, wherein said composition comprises from 0.05 to 1 weight %, relative to the total dry matter of the solution, of a surfactant.

25. A method for manufacturing a UV-cured hard-coating, comprising

a) coating an organic or mineral optical substrate with a curable composition as defined in claim 15;

b) curing the resulting coating by irradiation with UV-radiation,

said method not comprising any hydrolysis step before the UV curing step.

26. The method according to claim 25, wherein the substrate is selected from the group consisting of thermoplastic and thermoset substrates.

27. The method according to claim 26, wherein the substrate is selected from the group consisting of polycarbonates, homopolymers of diethylene glycol bis(allyl carbonate), polythiourethanes and acrylics.

28. The method according to claim 25, further comprising a step of drying of the coated layer before curing.

29. The method according to claim 25, wherein the curing step (b) comprises irradiating the coated layer with a UV radiation dosage ranging from 0.150 J/cm² to 1.20 J/cm² in the UV-C range, for about 1 to 10 seconds.