# US 10,308,834 B2 · UV curable coating compositions containing aliphatic urethane acrylate resins

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- Number: US 10,308,834 B2
- Document ID: US10308834B2
- Status: Granted
- Kind: B2
- Application number: 15/997,658
- Filed: 2018-06-04
- Published: 2018-11-29
- Granted: 2019-06-04
- Earliest claimed: 2008-05-30
- Assignees: Red Spot Paint & Varnish Co., Inc.
- Applicants: Eileen M. Weber
- Inventors: Eileen M. Weber
- Web page: https://patentgrep.com/patent/US10308834B2

## CPC

- C09D 175/16: having terminal carbon-to-carbon unsaturated bonds
- C08F 290/06: Polymers provided for in subclass C08G
- C08F 290/061: {Polyesters; Polycarbonates}
- C08F 290/067: {Polyurethanes; Polyureas}
- C08G 18/7887: {having two nitrogen atoms in the ring}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08K 5/17: Amines; Quaternary ammonium compounds
- C08K 5/3465: condensed with carbocyclic rings
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L 2205/02: containing two or more polymers of the same C08L -group
- 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
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Described in preferred embodiments are UV curable coating compositions including a unique blend of aliphatic urethane acrylate resins. Also described are coated articles and methods for their production involving the use of the coating compositions.

## Claims

### Claim 1

A UV curable coating composition, comprising:
(1) an inert solvent;
(2) a first aliphatic urethane acrylate resin, which is a reaction product of a polyisocyanate component represented by formula I below with an alcohol component containing at least one monobasic, hydroxy-functional, linear or branched C1-C12 alkyl ester of (meth)acrylic acid:
wherein R1, R2, and R3 of formula I are the same or different, and each comprise linear or branched, C4-C20 (cyclo)alkyl groups, wherein X is the same or different and comprises isocyanate groups and wherein R1, R2, and R3 of formula I are attached to a nitrogen atom;
(3) a second aliphatic urethane acrylate resin comprising the structure of formula II:
wherein A1, A2, and A3 are each a group comprising the structure of formula III:
wherein R1, R2, and R3 of formula III are the same or different, and each comprise a linear aliphatic group having from 2 to 12 carbon atoms, or a cycloaliphatic group having from 4 to 12 carbon atoms, wherein the second urethane acrylate has an average molecular weight of 500 to 2,000, wherein the second urethane acrylate resin contains 6 polymerizable acrylate groups per molecule, and wherein the first aliphatic urethane acrylate resin and the second aliphatic urethane acrylate resin comprise a weight ratio of 1:3 to 3:1;
(4) a first multifunctional acrylate, wherein the first multifunctional acrylate has an average molecular weight of 170 to 1,000, and wherein the first multifunctional acrylate comprises two polymerizable unsaturated groups per molecule;
(5) a second multifunctional acrylate, wherein the second multifunctional acrylate is selected from at least one of pentaerythritol triacrylate and trimethylolpropane triacrylate;
(6) a first photoinitiator and a second photoinitiator, wherein the first and second photoinitiators are selected from the group consisting of diphenylphosiphine oxides, pheylglyoxylates, α-hydoxyketones, difunctional α-hydoxyketones and combinations thereof;
(7) a hindered amine light stabilizer;
(8) a UV absorber comprising at least one of a benzotriazole and a benzotriazine;
(9) an acrylated organic-inorganic hybrid material;
(10) a phenolic based antioxidant; and
(11) a flow additive.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein, exclusive of the solvent, the composition comprises 10% to 40% by weight of the first aliphatic urethane acrylate resin and 20% to 50% by weight of the second aliphatic urethane acrylate resin.

### Claim 3

A UV curable coating composition, comprising:
(1) a solvent;
(2) a first aliphatic urethane acrylate resin, which is a reaction product of a polyisocyanate component represented by formula I below with an alcohol component containing at least one monobasic, hydroxy-functional, linear or branched C1-C12 alkyl ester of (meth)acrylic acid:
wherein R1, R2, and R3 of formula I are the same or different, and each comprise linear or branched, C4-C20 (cyclo)alkyl groups, wherein X is the same or different and comprises isocyanate groups and wherein R1, R2, and R3 of formula I are attached to a nitrogen atom;
(3) a second aliphatic urethane acrylate resin comprising the structure of formula II:
wherein A1, A2, and A3 are each a group comprising the structure of formula III:
wherein R1, R2, and R3 of formula III are the same or different, and each comprise a linear aliphatic group having from 2 to 12 carbon atoms, or a cycloaliphatic group having from 4 to 12 carbon atoms, wherein the second urethane acrylate has an average molecular weight of 500 to 2,000, wherein the second urethane acrylate resin contains 6 polymerizable acrylate groups per molecule, and wherein the first aliphatic urethane acrylate resin and the second aliphatic urethane acrylate resin comprise a weight ratio of 1:3 to 3:1;
(4) a first multifunctional acrylate, wherein the first multifunctional acrylate has an average molecular weight of 170 to 1,000, and wherein the first multifunctional acrylate comprises two polymerizable unsaturated groups per molecule;
(5) a second multifunctional acrylate, wherein the second multifunctional acrylate is selected from at least one of pentaerythritol triacrylate and trimethylolpropane triacrylate;
(6) a photoinitiator;
(7) a hindered amine light stabilizer; and
(8) a UV absorber.

### Claim 4 (depends on 3)

The composition according to claim 3, wherein, exclusive of the solvent, the composition comprises 10% to 40% by weight of the first aliphatic urethane acrylate resin and 20% to 50% by weight of the second aliphatic urethane acrylate resin.