# US 10,864,753 B2 · Electron beam curable inkjet formulations with improved chemical resistance

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- Number: US 10,864,753 B2
- Document ID: US10864753B2
- Status: Granted
- Kind: B2
- Application number: 16/091,869
- Filed: 2017-04-10
- Published: 2019-12-05
- Granted: 2020-12-15
- Earliest claimed: 2016-04-11
- Assignees: Sun Chemical Corporation
- Applicants: Sun Chemical Corporation
- Inventors: Stephen Anthony Hall; Derek Ronald Illsley
- Web page: https://patentgrep.com/patent/US10864753B2

## CPC

- B05D 3/0209: {Multistage baking}
- B05D 3/067: {Curing or cross-linking the coating}
- B05D 3/068: {using ionising radiations (gamma, X, electrons)}
- B41M 5/0023: {Digital printing methods characterised by the inks used (inks per se C09D11/00)}
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
- C09D 11/30: Inkjet printing inks
- C09D 11/32: characterised by colouring agents
- C09D 11/36: based on non-aqueous solvents
- C09D 11/38: characterised by non-macromolecular additives other than solvents, pigments or dyes
- B05D 2502/00: Acrylic polymers
- B05D 2506/25: PVC (B05D2520/10 takes precedence)
- B05D 2508/00: Polyesters
- B05D 2518/00: Other type of polymers
- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P)
- 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

## Abstract

The present invention is directed to a method for printing energy curable ink and coating compositions comprising high amounts of monofunctional monomers that exhibit both good adhesion to plastic substrates, and good solvent resistance. The method of the present invention employs electron beam curing of the ink and coating compositions, at accelerating voltages greater than or equal to 70 keV, and electron beam doses greater than or equal to 30 kGy, and preferably greater than or equal to 40 kGy.

## Claims

### Claim 1

A method for printing an energy curable ink or coating composition comprising:
a) providing an energy curable ink or coating composition, wherein the ink or coating composition comprises:
i) greater than or equal to 20% (w/w) one or more monofunctional ethylenically unsaturated monomers or oligomers, based on the total weight of the ink or coating composition;
ii) less than or equal to 50% (w/w) one or more multifunctional ethylenically unsaturated monomers or oligomers, based on the total weight of the ink or coating composition;
iii) 0% to 5% (w/w) one or more solvents, based on the total weight of the ink or coating composition;
iv) 0% to 5% (w/w) one or more photoinitiators, based on the total weight of the ink or coating composition;
v) 0% to 7% (w/w) one or more organic pigments or dyes, based on the total weight of the ink or coating composition; and
vi) 0% to 40% (w/w), one or more inorganic pigments, based on the total weight of the ink or coating composition;
b) applying the ink or coating composition of step a) to a substrate; and
c) curing the applied ink or coating composition by exposure to electron beam radiation with an electron beam emitter, wherein:
i) the accelerating voltage of the electron beam emitter is equal to or greater than 70 keV;
ii) cure dose is equal to or greater than 50 kGy.

### Claim 2 (depends on 1)

The method of claim 1, wherein the one or more monofunctional ethylenically unsaturated monomers or oligomers are present in an amount of greater than or equal to 30% (w/w).

### Claim 3 (depends on 1)

The method of claim 1, wherein the one or more multifunctional ethylenically unsaturated monomers or oligomers are present in amount of less than or equal to 40% (w/w).

### Claim 4 (depends on 1)

The method of claim 1, wherein the one or more solvents are present in an amount of less than or equal to 3% (w/w).

### Claim 5 (depends on 1)

The method of claim 1, wherein the one or more colorants comprise 0.1% to 7% (w/w) one or more organic pigments or dyes.

### Claim 6 (depends on 1)

The method of claim 1, wherein the one or more colorants comprise 1% to 40% (w/w) one or more inorganic pigments.

### Claim 7 (depends on 1)

The method of claim 1, wherein the energy curable ink or coating composition further comprises 0.1% to 5% (w/w) one or more photoinitiators.

### Claim 8 (depends on 7)

The method of claim 7, wherein the one or more photoinitiators are each independently selected from the group consisting of thioxanthone, acylphosphine oxide, aminoketone, oxime, and ketocoumarin.

### Claim 9 (depends on 7)

The method of claim 7, wherein the energy curable ink or coating composition comprises less than 1% (w/w) of an acylphosphine oxide photoinitiator, based on the total weight of the ink or coating composition.

### Claim 10 (depends on 7)

The method of claim 7, wherein the energy curable ink or coating composition comprises the photoinitiator bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide.

### Claim 11 (depends on 1)

The method of claim 1, wherein the energy curable ink or coating composition further comprises 1% to 15% (w/w) one or more passive/inert resins.

### Claim 12 (depends on 1)

The method of claim 1, wherein the energy curable ink or coating composition further comprises 0.1% to 5% (w/w) one or more additives selected from the group consisting of de-aerators, defoamers, surface control additives, rheology modifiers, dispersants, stabilizers, inhibitors, wetting agents.

### Claim 13 (depends on 1)

The method of claim 1, wherein the accelerating voltage is greater than or equal to 80 keV.

### Claim 14 (depends on 1)

The method of claim 1, wherein the accelerating voltage of the electron beam emitter is between 70 keV and 200 keV.

### Claim 15 (depends on 1)

The method of claim 1, wherein the cure dose is between 70 kGy and 200 kGy.

### Claim 16 (depends on 1)

The method of claim 1, wherein the substrate is a plastic substrate.

### Claim 17 (depends on 1)

The method of claim 1, wherein the energy curable ink or coating composition is an inkjet ink or coating composition.

### Claim 18 (depends on 1)

A printed substrate prepared by the method of claim 1.

### Claim 19 (depends on 18)

The printed substrate of claim 18, wherein the substrate is selected from a plastic film, a plastic laminate, and a plastic-paperboard laminate.