# US 11,028,281 B2 · Free radical polymerizable water-based inkjet compositions

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- Number: US 11,028,281 B2
- Document ID: US11028281B2
- Status: Granted
- Kind: B2
- Application number: 16/320,233
- Filed: 2017-07-25
- Published: 2019-08-29
- Granted: 2021-06-08
- Earliest claimed: 2016-07-27
- Assignees: Sun Chemical Corporation
- Applicants: Sun Chemical Corporation
- Inventors: Andrew Balch; Derek Ronald Illsley
- Web page: https://patentgrep.com/patent/US11028281B2

## CPC

- C09D 11/38: characterised by non-macromolecular additives other than solvents, pigments or dyes
- B41M 7/0045: {using protective coatings or film forming compositions cured by mechanical wave energy, e.g. ultrasonics, cured by electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams, or cured by magnetic or electric fields, e.g. electric discharge, plasma}
- B41M 7/0081: {using electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams}
- 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 11/322: Pigment inks
- C09D 11/52: Electrically conductive inks
- C09D 11/324: containing carbon black
- C09D 11/328: characterised by dyes
- 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)
- 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)

## Abstract

Described herein are free radically polymerizable aqueous inkjet compositions that include water, a water-soluble or water-dispersible component polymerizable by free radical polymeration, and one or more water-soluble organic solvents in compliance with following Formula I: Σ(Xn·Hn·Bn)≤ρ (I), where ρ is 2,000,000. The variables of the formula are defined herein. Also described are printed articles that include the inkjet compositions of the disclosure. The inkjet compositions dry rapidly while remaining fluid during printing, thereby avoiding clogging in the print head.

## Claims

### Claim 1

A free radically polymerizable water-based inkjet composition comprising:
water;
a water-soluble or water-dispersible component polymerizable by free radical polymerization; and
one or more water-soluble organic solvents in compliance with following Formula I:
Σ(Xn·Hn·Bn)≤ρ (I)
wherein each individual n represents a water-soluble organic solvent present in the composition;
n is an integer≥1;
Xn is the amount on a weight basis of each water-soluble organic solvent present in the composition expressed as 100(wn/wtotal);
wn is the weight of a water-soluble organic solvent present in the composition represented by a value of n;
wtotal is the weight of the ink jet composition;
Hn is Heat of Vaporization of each water-soluble organic solvent (J/g);
Bn=Boiling Point of each water-soluble organic solvent (° C.);
Σ=sum of the multiplication products of Xn, Hn and Bn for each water-soluble organic solvent present in the composition; and
ρ is 2,000,000;
wherein the total amount of water-soluble organic solvents in the composition is 10 wt % to 40 wt %, based on the total weight of the composition; and wherein the composition comprises less than or equal to 2.5 wt % water-soluble organic solvents having boiling points of 150° C. or greater and heats of vaporization of equal to or greater than 400 J/g.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the water-soluble or water-dispersible component comprises water-dispersible acrylated polyurethane polymerizable by free radical polymerization.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the water-dispersible acrylated polyurethane has a weight average molecular weight of 500 to 50,000 Daltons.

### Claim 4 (depends on 1)

The composition of claim 1, further comprising one or more monomers, oligomers and polymers that are polymerizable by free radical polymerization selected from acrylate, methacrylate, acrylamide, methacrylamide, ethylenic, vinyl-ether, propenyl ether, vinyl-ester, maleate, fumarate, and combinations thereof.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the boiling point of each of the one or more water-soluble organic solvents present in the composition is 150° C. or greater.

### Claim 6 (depends on 5)

The composition of claim 5, wherein the amount of the one or more water-soluble organic solvents having boiling points of 150° C. or greater is 5 wt % to 30 wt %, based on the total weight of aqueous inkjet compositions.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the total amount of the one or more water-soluble organic solvents having boiling points of 150° C. or greater and heats of vaporization of 400 J/g or greater is, based on the total weight of the composition, 0.01 wt % to 2.5 wt %.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the one or more water soluble organic solvents are selected from alkylene glycol ethers and ether acetates selected from 4-hydroxy-4-methyl-2-pentanone, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monopropyl ether, dipropylene glycol ethyl ether, dipropylene glycol methyl ether, ethylene glycol butyl ether, ethylene glycol ethyl ether, ethylene glycol isopropyl ether, ethylene glycol methyl ether, ethylene glycol propyl ether, glycerine carbonate, N-methyl 2-pyrrolidone, propylene glycol, propylene glycol ethyl ether, propylene glycol ethyl ether acetate, propylene glycol methyl ether, propylene glycol n-propyl ether, triethylene glycol butyl ether, triethylene glycol methyl ether, tripropylene glycol, tripropylene glycol methyl ether, and combinations thereof.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the water-soluble or water-dispersible component comprises water-dispersible acrylated polyurethane polymerizable by free radical polymerization, wherein the water-dispersible acrylated polyurethane is present in the composition, based on the weight of the polyurethane and the total weight of the composition, in an amount of 2.0 wt % to 20 wt %.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the water-soluble organic solvent comprises glycerol, propylene glycol, 3-methoxy-3-methyl-1-butanol, dipropylene glycol methyl ether, propylene glycol n-butyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether, 3,3,5-triemthylcyclohexanone, and combinations thereof.

### Claim 11 (depends on 1)

The composition of claim 1, further comprising one or more photoinitiators.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the one or more photoinitiators are water-soluble or dispersible in an aqueous phase.

### Claim 13 (depends on 11)

The composition of claim 11, wherein the amount of migration of photoinitiator from the printed substrate to another material is less than 50 ppb.

### Claim 14 (depends on 1)

A method for printing an article comprising:
printing, by inkjet printing, the composition of claim 1 on a substrate;
removing at least a portion of the water and organic solvent from the composition; and
energy curing the composition.

### Claim 15 (depends on 14)

The method of claim 14, wherein energy curing comprises exposing the article to UV light or electron beam radiation.

### Claim 16 (depends on 14)

The method of claim 14, wherein the printed article is food packaging.

### Claim 17 (depends on 1)

A printed article comprising
a substrate; and
at least one printed layer comprising the composition of claim 1.

### Claim 18 (depends on 17)

The printed article of claim 17, wherein the film thickness of a single printed layer, before the energy curing step, is less than 3.0 μm.

### Claim 19 (depends on 17)

The printed article of claim 17, wherein the substrate is comprised of a material selected from vinyl, acrylic, polystyrene, polycarbonate, polyester, polyethylene terephthalate, glycol modified polyethylene terephthalate, poly(olefin), nylon, polypropylene, polyethylene, cellulose acetates, poly(lactic acid), aluminum, aluminum oxide, silicon oxide, poly(vinylidene dichloride), and nitrocellulose.

### Claim 20

A method for printing an article, consisting essentially of:
a) providing a substrate;
b) providing a free-radically polymerizable water-based inkjet composition, wherein the free-radically polyerizable water-based inkjet composition comprises:
i. water;
ii. a water-soluble or water-dispersible component polymerizable by free radical polymeration; and
iii. one or more water-soluble organic solvents in compliance with following Formula I:
Σ(Xn·Hn·Bn)≤ρ (I)
wherein each individual n represents a water-soluble organic solvent present in the composition;
n is an integer≥1;
Xn is the amount on a weight basis of each water-soluble organic solvent present in the composition expressed as 100(wn/wtotal);
wn is the weight of a water-soluble organic solvent present in the composition represented by a value of n;
wtotal is the weight of the ink jet composition;
Hn is Heat of Vaporization of each water-soluble organic solvent (J/g);
Bn=Boiling Point of each water-soluble organic solvent (° C.);
Σ=sum of the multiplication products of Xn, Hn and Bn for each water-soluble organic solvent present in the composition; and
ρ is 2,000,000;
c) applying the composition of step (b) to the substrate of step (a);
d) removing at least a portion of the water and organic solvent from the composition applied on the substrate; and
e) energy curing the composition on the substrate;
wherein:
i. the total amount of water-soluble organic solvents in the composition is 10 wt % to 40 wt %, based on the total weight of the composition; and wherein the composition comprises less than or equal to 2.5 wt % water-soluble organic solvents having boiling points of 150° C. or greater and heats of vaporization of equal to or greater than 400 J/g;
ii. the substrate is selected from the group consisting of vinyl, acrylic, polystyrene, polycarbonate, polyester, polyethylene terephthalate, glycol modified polyethylene terephthalate, poly(olefin), nylon, polypropylene, polyethylene, cellulose acetates, poly(lactic acid), aluminum, aluminum oxide, silicon oxide, poly(vinylidene dichloride), and nitrocellulose; and
iii. the article is a food packaging article.

### Claim 21 (depends on 20)

A food packaging article prepared by the method of claim 20.