# US 2020/0399485 A1 · Electron beam curable compositions comprising polyols

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- Number: US 2020/0399485 A1
- Document ID: US20200399485A1
- Status: Published application
- Kind: A1
- Application number: 16/979,242
- Filed: 2019-07-01
- Published: 2020-12-24
- Earliest claimed: 2018-07-13
- Assignees: Sun Chemical Corporation
- Applicants: Sun Chemical Corporation
- Inventors: Derek Ronald ILLSLEY; Stephen Anthony HALL; Shaun Lawrence HERLIHY
- Web page: https://patentgrep.com/patent/US20200399485A1

## CPC

- 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
- A61L 2/087: Particle radiation, e.g. electron-beam, alpha or beta radiation
- B41J 2/2107: {characterised by the ink properties (supplying ink in a solid state B41J2/17593)}
- B41M 1/04: Flexographic printing
- B41M 5/0047: {by ink-jet printing}
- B41M 5/0064: {on plastics, horn, rubber, or other organic polymers}
- B41M 7/0081: {using electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams}
- C09D 11/033: characterised by the solvent
- C09D 11/037: characterised by the pigment
- C09D 11/107: from unsaturated acids or derivatives thereof
- C09D 11/322: Pigment inks
- C09D 11/36: based on non-aqueous solvents
- C09D 11/38: characterised by non-macromolecular additives other than solvents, pigments or dyes
- A61L 2103/23: {Containers other than laboratory or medical, e.g. bottles or mail}
- A61L 2202/18: Aseptic storing means
- 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)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- B41J: TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- 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

Electron beam curable compositions comprising polyols, and any blend of ethylenically unsaturated monomers and oligomers. The polyols of the invention are preferably essentially free of any ethylenically unsaturated groups, have greater than one hydroxy group and preferably have boiling points in excess of 170° C.

## Claims

### Claim 1

Electron Beam (EB) curable compositions comprising alcohol containing substances, which are essentially free of ethylenically unsaturated groups, wherein the alcohol is selected from the group consisting of propylene glycol, trimethylolpropane, glycerol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, poly(ethylene glycol), poly(propylene glycol), ethoxylated trimethylolpropane, propoxylated trimethylolpropane, ethoxylated pentaerythritol, propoxylated pentaerythritol, ethoxylated ditrimethylolpropane, propoxylated ditrimethylolpropane, ethoxylated dipentaerythritol, propoxylated dipentaerythritol, and combinations thereof, wherein the compositions further comprise one or more ethylenically unsaturated monomers, and wherein the concentration of monofunctional monomer is less than 20% by weight of the total composition.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the alcohol has a boiling point greater than 150° C.

### Claim 3

(canceled)

### Claim 4 (depends on 1)

The composition of any preceding claim 1, wherein the alcohol has a molecular weight of less than 2,000.

### Claim 5 (depends on 1)

The composition of any preceding claim 1, wherein the alcohol has a molecular weight of less than 1,000.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the alcohol is present in an amount from 1-30 wt % and has a molecular weight of less than 2,000.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the alcohol is selected from the group consisting of propylene glycol, trimethylolpropane, glycerol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, poly(ethylene glycol), poly(propylene glycol), and combinations thereof.

### Claim 8 (depends on 1)

The composition of claim 1 further comprising any blend of photoinitiators.

### Claim 9 (depends on 8)

The composition of claim 8, wherein the total concentration of photoinitiators is less than 5.0 wt %.

### Claim 10 (depends on 8)

The composition of claim 8, wherein the photoinitiators are able to initiate free radical polymerization in the UVA part of the UV spectrum.

### Claim 11

(canceled)

### Claim 12 (depends on 1)

The composition of claim 1 which is a pigmented inkjet ink, or a pigmented flexo ink, or a pigmented offset ink.

### Claim 13

(canceled)

### Claim 14

(canceled)

### Claim 15 (depends on 1)

A printed substrate comprising the composition of claim 1.

### Claim 16 (depends on 15)

The substrate of claim 15 which is a plastic film.

### Claim 17 (depends on 1)

A process for preparing an article with a low migration coating or an ink printed thereon comprising;
applying any number of ink and/or coating compositions according to claim 1 to a substrate and curing the composition preferably using an EB dose ≤50 kGy and an accelerating voltage ≥70 kev.

### Claim 18 (depends on 17)

The process of claim 17, satisfying the following expression:
X=A.B/C<100
where A is the electron beam dose in kGy, B is the accelerating voltage in keV and C is the press speed in m/min.

### Claim 19

(canceled)

### Claim 20 (depends on 17)

An in-line printing and sterilization method for producing aseptic food packaging prior to the filling with foodstuffs, comprising the process of claim 17.

### Claim 21

A method of promoting the EB-cure of a free-radically polymerizable composition, comprising including in the composition alcohol containing substances which are essentially free of ethylenically unsataurated groups, wherein the alcohol is selected from the group consisting of propylene glycol, trimethylolpropane, glycerol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, poly(ethylene glycol), poly(propylene glycol), ethoxylated trimethylolpropane, propoxylated trimethylolpropane, ethoxylated pentaerythritol, propoxylated pentaerythritol, ethoxylated ditrimethylolpropane, propoxylated ditrimethylolpropane, ethoxylated dipentaerythritol, propoxylated dipentaerythritol, and combinations thereof.

### Claim 22 (depends on 21)

The use method of claim 21, wherein the alcohol has a boiling point greater than 150° C.

### Claim 23

(canceled)

### Claim 24 (depends on 21)

The method of claim 21, wherein the alcohol has a molecular weight of less than 2,000.

### Claim 25

(canceled)

### Claim 26 (depends on 21)

The method of claim 21, wherein the alcohol is used in an amount from 1-30 wt % and has a molecular weight of less than 2,000.

### Claim 27 (depends on 21)

The method of claim 21, wherein the alcohol is selected from the group consisting of propylene glycol, trimethylolpropane, glycerol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, poly(ethylene glycol), poly(propylene glycol), and combinations thereof.