# US 11,441,048 B2 · One component UV curable compositions and methods for making same

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- Number: US 11,441,048 B2
- Document ID: US11441048B2
- Status: Granted
- Kind: B2
- Application number: 17/062,115
- Filed: 2020-10-02
- Published: 2021-01-21
- Granted: 2022-09-13
- Earliest claimed: 2018-09-26
- Assignees: Dvorchak Enterprises LLC
- Applicants: Dvorchak Enterprises LLC
- Inventors: Michael J. Dvorchak; Michael E. Zupancic
- Web page: https://patentgrep.com/patent/US11441048B2

## CPC

- C09D 133/06: of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D 133/08: Homopolymers or copolymers of acrylic acid esters
- B05D 3/06: by exposure to radiation (B05D3/02 takes precedence {; plasma treatment B05D3/141})
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D 175/14: Polyurethanes having carbon-to-carbon unsaturated bonds
- 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)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)

## Abstract

A composition is provided and includes an unsaturated (meth)acrylate polymer or oligomer, an allophanate unsaturated urethane (meth)acrylate, a lactone-containing (meth)acrylate, a first reactive diluent, an adhesion promoter, a second reactive diluent, a light stabilizer, and a photoinitiator.

## Claims

### Claim 1

A composition comprising:
an unsaturated (meth)acrylate polymer or oligomer in an amount of about 25 to about 45 percent by weight, the unsaturated (meth)acrylate polymer or oligomer is a reaction product of a first composition having:
an organic polyisocyanate;
a polyol having a number average molecular weight of about 600 to about 4000 g/mol; and
at least one of: (1) a hydroxyl-functional (meth)acrylate and (2) an unsaturated (meth)acrylate polyol based on a polyester, a polyether, a polythioether, a polyacetal, a polycarbonate, a dimer fatty alcohol and/or an esteramide, in each case with a number average molecular weight of 400 to 8000 g/mol, at an isocyanate to hydroxyl equivalent ratio of from 0.5:1 to 1:0.5;
an allophanate unsaturated urethane (meth)acrylate in an amount of about 5 to about 25 percent by weight;
a lactone-containing (meth)acrylate in an amount of about 2 to about 12 percent by weight;
a first reactive diluent in an amount of about 15 to about 50 percent by weight, the first reactive diluent having a monomer;
a surfactant in an amount up to about 0.3 percent by weight;
an adhesion promoter in an amount of about 1 to about 5 percent by weight;
a second reactive diluent in an amount of about 1 to about 5 percent by weight, the reactive diluent having a phosphoric acid ester;
a light stabilizer in an amount of about 0.5 to about 2 percent by weight; and
a photoinitiator in an amount of about 0.5 to about 15 percent by weight.

### Claim 2 (depends on 1)

The composition of claim 1, further comprising a first additive of a fluorinated urethane acrylate oligomer, a fluorinated acrylate oligomer, a fluorinated polyether, or a fluorinated oxetane oligomer.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the first additive is present in an amount of about 0.5 to about 10 percent by weight.

### Claim 4 (depends on 3)

The composition of claim 3, wherein the reaction product includes an unsaturated aliphatic urethane acrylate.

### Claim 5 (depends on 4)

The composition of claim 4, wherein the allophanate unsaturated urethane (meth)acrylate includes an unsaturated aliphatic allophanate urethane acrylate.

### Claim 6 (depends on 5)

The composition of claim 5, wherein the lactone-containing (meth)acrylate includes an unsaturated aliphatic urethane acrylate based on a hydroxyl functional lactone ester (meth) acrylate.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the first reactive diluent includes an isobornyl acrylate or 4-tert-butyl cyclohexyl acrylate.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the surfactant includes a wetting and dispersing copolymer with an acidic group.

### Claim 9 (depends on 8)

The composition of claim 8, wherein the adhesion promoter includes a phosphoric acid ester having a photopolymerizable unsaturated bond.

### Claim 10 (depends on 9)

The composition of claim 9, wherein the second reactive diluent includes Trimethylolpropane ethoxy triacrylate.

### Claim 11 (depends on 10)

The composition of claim 10, wherein the light stabilizer includes an acidic liquid hinder amine light stabilizer, liquid non-basic hindered amine light stabilizer (HALS), or liquid hydroxyphenyl-triazine (HPT) UV absorber.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the photo initiator includes Bis Acyl Phosphine (BAPO) and fluorinated diaryl-bis-cyclopentadienyl titanium complex.

### Claim 13 (depends on 1)

The composition of claim 1, further comprising a pigment.

### Claim 14 (depends on 13)

The composition of claim 13, wherein the pigment includes iron oxide, rutile TiO2, or carbon black.

### Claim 15 (depends on 1)

The composition of claim 1, further comprising a dispersant.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the dispersant includes a copolymer with acidic groups.

### Claim 17 (depends on 1)

The composition of claim 1, wherein:
the reaction product is in an amount of about 32 to about 38 percent by weight;
the allophanate unsaturated urethane (meth)acrylate is in an amount of about 13 to about 15 percent by weight;
the lactone-containing (meth)acrylate is in an amount of about 6 to about 8 percent by weight;
the first reactive diluent is in an amount of about 26 to about 31 percent by weight;
the adhesion promoter is in an amount of about 1 to about 4 percent by weight;
the second reactive diluent is in an amount of about 1 to about 4 percent by weight; and
the photoinitiator is in an amount of about 0.5 to about 5 percent by weight.

### Claim 18

A method of making a one component UV curable coating, comprising:
applying a composition to a substrate at a thickness of at least 0.1 mils, the composition having:
an unsaturated (meth)acrylate polymer or oligomer in an amount of about 25 to about 45 percent by weight, the unsaturated (meth)acrylate polymer or oligomer is a reaction product of a first composition having:
an organic polyisocyanate;
a polyol having a number average molecular weight of about 600 to about 4000 g/mol; and
at least one of: (1) a hydroxyl-functional (meth)acrylate and (2) an unsaturated (meth)acrylate polyol based on a polyester, a polyether, a polythioether, a polyacetal, a polycarbonate, a dimer fatty alcohol and/or an esteramide, in each case with a number average molecular weight of 400 to 8000 g/mol, at an isocyanate to hydroxyl equivalent ratio of from 0.5:1 to 1:0.5;
an allophanate unsaturated urethane (meth)acrylate in an amount of about 5 to about 25 percent by weight;
a lactone-containing (meth)acrylate in an amount of about 2 to about 12 percent by weight;
a first reactive diluent in an amount of about 15 to about 50 percent by weight, the first reactive diluent having a monomer;
a surfactant in an amount up to about 0.3 percent by weight;
an adhesion promoter in an amount of about 1 to about 5 percent by weight;
a second reactive diluent in an amount of about 1 to about 5 percent by weight, the reactive diluent having a phosphoric acid ester;
a light stabilizer in an amount of about 0.5 to about 2 percent by weight; and
a photoinitiator in an amount of about 0.5 to about 15 percent by weight; and
exposing the composition to actinic radiation without using any oxygen inhibition mitigation techniques to produce a cured film.

### Claim 19 (depends on 18)

The method of claim 18, wherein:
the allophanate unsaturated urethane (meth)acrylate includes an unsaturated aliphatic allophanate urethane acrylate;
the lactone-containing (meth)acrylate includes an unsaturated aliphatic urethane acrylate based on a hydroxyl functional lactone ester (meth) acrylate;
the first reactive diluent includes an isobornyl acrylate or 4-tert-butyl cyclohexyl acrylate;
the surfactant includes a wetting and dispersing copolymer with an acidic group;
the adhesion promoter includes a phosphoric acid ester having a photopolymerizable unsaturated bond;
the second reactive diluent includes Trimethylolpropane ethoxy triacrylate;
the light stabilizer includes an acidic liquid hinder amine light stabilizer, liquid non-basic hindered amine light stabilizer (HALS), or liquid hydroxyphenyl-triazine (HPT) UV absorber; and
the photo initiator includes Bis Acyl Phosphine (BAPO) and fluorinated diaryl-bis-cyclopentadienyl titanium complex.

### Claim 20 (depends on 18)

The method of claim 18, wherein:
the reaction product is in an amount of about 32 to about 38 percent by weight;
the allophanate unsaturated urethane (meth)acrylate is in an amount of about 13 to about 15 percent by weight;
the lactone-containing (meth)acrylate is in an amount of about 6 to about 8 percent by weight;
the first reactive diluent is in an amount of about 26 to about 31 percent by weight;
the adhesion promoter is in an amount of about 1 to about 4 percent by weight;
the second reactive diluent is in an amount of about 1 to about 4 percent by weight; and
the photoinitiator is in an amount of about 0.5 to about 5 percent by weight.