# US 12,180,383 B2 · Curable coating composition

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- Number: US 12,180,383 B2
- Document ID: US12180383B2
- Status: Granted
- Kind: B2
- Application number: 18/007,577
- Filed: 2021-06-03
- Published: 2023-07-13
- Granted: 2024-12-31
- Earliest claimed: 2020-06-03
- Assignees: Essilor International
- Applicants: Essilor International
- Inventors: Robert Valeri
- Web page: https://patentgrep.com/patent/US12180383B2

## CPC

- C09D 133/12: Homopolymers or copolymers of methyl methacrylate
- C08F 222/1006: {of polyhydric alcohols or polyhydric phenols}
- C09D 7/63: organic
- C09J 4/00: Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16}
- G02B 1/04: made of organic materials, e.g. plastics (G02B1/08 takes precedence)
- G02B 1/14: Protective coatings, e.g. hard coatings
- G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence)
- G03F 7/029: Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F 7/031: Organic compounds not covered by group G03F7/029
- G03F 7/0755: {Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)}
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## Abstract

The present invention relates to a curable coating composition, especially a radiation curable coating composition comprising at least one poly(meth)acrylate compound comprising at least 6 (meth)acrylate groups, at least one unsaturated silane compound, and at least one photoinitiator. Said at least one poly(meth)acrylate compound comprising at least 6 (meth)acrylate groups and said at least one unsaturated silane compound represent at least 95% of the weight of polymerizable compounds present in the composition. Upon radiation-curing, the composition provides an abrasion- and/or scratch-resistant coating.

## Claims

### Claim 1

A radiation-curable coating composition comprising:
at least one poly(meth)acrylate compound comprising at least 6 (meth)acrylate groups;
at least one unsaturated silane compound that is radiation-curable; and
at least one photoinitiator;
wherein said at least one poly(meth)acrylate compound comprising at least 6 (meth)acrylate groups and said at least one radiation-curable unsaturated silane compound represent at least 95% of the weight of polymerizable compounds present in the composition; and
the radiation-curable unsaturated silane compounds are present in an amount higher than or equal to 30% by weight, as compared to the composition total weight.

### Claim 2 (depends on 1)

The coating composition of claim 1, wherein the at least one photoinitiator is a free radical generating photoinitiator.

### Claim 3 (depends on 1)

The coating composition of claim 1, wherein the composition comprises from 0.1% to 5% photoinitiator by weight relative to the total weight of the composition.

### Claim 4 (depends on 1)

The coating composition of claim 1, wherein the photoinitiator is selected from the group consisting of benzophenone compounds, acetophenone compounds, monoacyl and bisacyl phosphine oxides and combinations thereof.

### Claim 5 (depends on 1)

The coating composition of claim 1, wherein the poly(meth)acrylate compound is a hexa (meth)acrylate compound.

### Claim 6 (depends on 5)

The coating composition of claim 5, wherein the poly(meth)acrylate compound is dipentaerythritol hexaacrylate.

### Claim 7 (depends on 1)

The coating composition of claim 1, wherein the radiation-curable unsaturated silane compound is a vinyl silane.

### Claim 8 (depends on 7)

The coating composition of claim 7, wherein the radiation-curable unsaturated silane compound is a vinyl alkoxysilane.

### Claim 9 (depends on 7)

The coating composition of claim 7, wherein the vinyl silane is a vinyl alkoxysilane selected from the group consisting of vinyl mono-, di- and tri-alkoxysilanes.

### Claim 10 (depends on 9)

The coating composition of claim 9, wherein the vinyl silane is vinyltrimethoxysilane.

### Claim 11 (depends on 1)

The coating composition of claim 1, wherein the composition further comprises from 0.05 to 1% by weight of a surfactant, as compared to the composition total weight.

### Claim 12 (depends on 1)

The coating composition of claim 1, wherein the composition does not comprise any solvent.

### Claim 13 (depends on 1)

The coating composition of claim 1, wherein the poly(meth)acrylate compounds are present in an amount higher than or equal to 33% by weight, as compared to the composition total weight.

### Claim 14 (depends on 1)

The coating composition of claim 1, wherein the radiation-curable unsaturated silane compounds are present in an amount higher than or equal to 33% by weight, as compared to the composition total weight.

### Claim 15 (depends on 1)

An optical article having a substrate coated on at least one main face with an abrasion- and/or scratch-resistant coating obtained by curing a radiation-curable coating composition of claim 1.

### Claim 16 (depends on 15)

The optical article of claim 15, wherein the coating has a thickness ranging from 1 to 10 μm.

### Claim 17 (depends on 15)

The optical article of claim 15, wherein the optical article is an ophthalmic lens.

### Claim 18 (depends on 15, 16)

A method for manufacturing the optical article of claim 15, comprising:
providing an optical article comprising a substrate having at least one main face;
depositing onto said at least one main face a layer of a radiation-curable coating composition of claim 16; and
radiation-curing said composition to form an abrasion- and/or scratch-resistant coating.

### Claim 19 (depends on 18)

The method of claim 18, wherein the optical article substrate is selected from the group consisting of thermoplastic, thermoset, and mineral substrates.
