Curable coating composition

Patent metadata

Field	Value
Publication number	US-9557449-B2
Application number	US-201214370298-A
Country	US
Kind code	B2
Filing date	Jan 3, 2012
Priority date	Jan 3, 2012
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

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.

First claim

The invention claimed is:

1. 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 said at least one non hydrolyzed epoxyalkoxysilane;
c) at least one free radical photoinitiator and/or cationic photoinitiator;
wherein the total amount of said at least one polyfunctional acrylate monomer and/or polyfunctional epoxy compound is more than 40 weight %, relative to the total dry matter of the composition; the total amount of said at least one non hydrolyzed epoxyalkoxysilane is from 20 to less than 60 weight % relative to the total dry matter of the composition; and
said composition does not comprise any hydrolyzed epoxyalkoxysilane.

2. The composition according to claim 1 , wherein the molar ratio between the total amount of epoxy functions and the total amount of acrylate functions is from 0.1 to 3.

3. The composition according to claim 1 , wherein said epoxyalkoxysilane is selected from the group consisting of 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, 3-glycidoxypropyl-methyldiethoxysilane and 3-glycidoxypropyltrimethoxysilane.

4. The composition according to claim 1 , 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.

5. The composition according to claim 1 , 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 15 weight %, relative to the total amount of polyfunctional acrylate monomers.

6. The composition according to claim 1 , wherein said cationic photoinitiator is selected from the group consisting of triarylsulfonium hexafluoroantimonate, triarylsulfonium hexafluorophosphate, diaryliodonium hexafluoroantimonate and diaryliodonium hexafluorophosphate salts, and mixtures thereof; and said free radical photoinitiator is selected from the group consisting of 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.

7. The composition according to claim 1 , wherein said composition comprises a solvent.

8. The composition according to claim 1 , wherein said composition comprises colloidal silica particles.

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

10. The composition according to claim 1 , wherein the total amount of said at least one polyfunctional acrylate monomer and polyfunctional epoxy compound is more than 40 weight %, relative to the total dry matter of the composition.

11. 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 1 ;
b) curing the resulting coating by irradiation with UV-radiation,
said method not comprising any hydrolysis step before the UV curing step.

12. The method according to claim 11 , wherein the substrate is selected from the group consisting of thermoplastic and thermoset substrates.

13. The method according to claim 11 , wherein the substrate is selected from the group consisting of polycarbonates, homopolymers of diethylene glycol bis(allyl carbonate), polythiourethanes and acrylics.

14. The method according to claim 11 , further comprising a step of drying of the coated layer before curing.

15. The method according to claim 11 , wherein the curing step (b) comprises irradiating the coated layer with a UV radiation dosage ranging from 0.150 J/cm 2 to 1.20 J/cm 2 in the UV-C range, for about 1 to 10 seconds.

Assignees

• Valeri Robert Alan
• Essilor Int

Inventors

• Valeri Robert Alan

Classifications

• G02B1/14 Primary

  Protective coatings, e.g. hard coatings · CPC title

• C08K5/5435

  containing oxygen in a ring · CPC title

• B05D3/067

  Curing or cross-linking the coating · CPC title

• G02B1/10

  Optical coatings produced by application to, or surface treatment of, optical elements (G02B1/08 takes precedence) · CPC title

• G02B1/12

  by surface treatment, e.g. by irradiation · CPC title