# US 11,299,649 B2 · Polyurethane-polyacrylate hybrid systems for packaging inks and coatings

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- Number: US 11,299,649 B2
- Document ID: US11299649B2
- Status: Granted
- Kind: B2
- Application number: 16/084,150
- Filed: 2017-04-04
- Published: 2020-09-17
- Granted: 2022-04-12
- Earliest claimed: 2016-04-05
- Assignees: Sun Chemical Corporation
- Applicants: Sun Chemical Corporation
- Inventors: David Klein; Michael J. Jurek; Juanita Parris
- Web page: https://patentgrep.com/patent/US11299649B2

## CPC

- C09D 175/14: Polyurethanes having carbon-to-carbon unsaturated bonds
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 27/06: as the main or only constituent of a layer, {which is} next to another layer of {the same or of} a {different material (next to a layer of a particular substance B32B9/045; next to a bituminous or tarry layer B32B11/046; next to a water setting substance layer B32B13/12; next to a metal layer B32B15/08; next to a glass layer B32B17/10; next to a layer formed of natural mineral fibres or particles B32B19/045; next to a wood layer B32B21/08; next to a cellulosic plastic layer B32B23/08; next to a natural or synthetic rubber layer B32B25/08)}
- B32B 27/16: specially treated, e.g. irradiated
- B32B 27/32: comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)}
- B32B 27/36: comprising polyesters
- C08F 283/00: Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F 283/006: {on to polymers provided for in C08G18/00 (C08F283/004 takes precedence)}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/3206: {aliphatic}
- C08G 18/348: {Hydroxycarboxylic acids}
- C08G 18/4854: {Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group}
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C09D 11/10: based on artificial resins
- C09D 175/04: Polyurethanes
- B32B 2255/10: on synthetic resin layer or on natural or synthetic rubber layer
- B32B 2255/26: Polymeric coating
- B32B 2439/70: Food packaging
- 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)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- 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

## Abstract

Described herein are compositions suitable for use as binder components for inclusion in printing inks and coatings, such as those used in the gravure and flexographic printing process and which are printed on substrates such as polyolefin (e.g., polyethylene, polypropylene) and poly(ethylene terephthalate) (PET). The compositions are non-aqueous dispersions in which an one or more ethylenically unsaturated acrylates or (meth)acrylates is polymerized with a polyurethane, polyurethane-urea or polyurea in a non-aqueous polymerization medium, such as esters, ketones, and mixtures thereof, forming polymeric hybrid resins in the polymerization medium, which are solvent-dispersible hybrid resins of polyurethane-polyacrylate, polyurethane-urea-polyacrylate, and polyurea-polyacrylate. Films of hybrid resins are also disclosed. These materials exhibit improved film adhesion and are suitable for flexographic and gravure printing inks, especially for printing applications where adhesive lamination bond strengths are required, especially plastic films packaging applications.

## Claims

### Claim 1

A non-aqueous dispersion comprising dispersed polymeric hybrid resins in a non-aqueous medium, wherein the non-aqueous medium consists of one or more solvents selected from the group consisting of alcohols, esters and ketones, the dispersed polymeric hybrid resins selected from polyurethane-polyacrylate, polyurethane-urea-polyacrylate, and polyurea-polyacrylate, which hybrid resins are produced in the non-aqueous medium in a polymerization reaction between one or more ethylenically unsaturated acrylates and one or more of a polyurethane, a polyurethane-urea, and a polyurea polymer soluble in the medium, wherein the non-aqueous dispersion contains no aromatic hydrocarbon solvents.

### Claim 2 (depends on 1)

The non-aqueous dispersion of claim 1, wherein the non-aqueous medium is selected from the group consisting of one or more of esters and ketones wherein the ethylenically unsaturated acrylate monomers are soluble in the medium.

### Claim 3 (depends on 1)

The non-aqueous dispersion of claim 1, wherein the one or more ethylenically unsaturated acrylates are selected from monofunctional ethylenically unsaturated acrylate monomers, multifunctional ethylenically unsaturated acrylate monomers, and mixtures thereof.

### Claim 4 (depends on 1)

The non-aqueous dispersion of claim 1, wherein the ratio of the polyurethane, polyurethane-urea, or polyurea to polyacrylate in the hybrid resins is, on a molar basis, 10/90 to 90/10.

### Claim 5 (depends on 1)

The non-aqueous dispersion of claim 1, wherein the hybrid resins in the dispersion have a number average molecular weight of about 1,000 Daltons to about 200,000 Daltons.

### Claim 6 (depends on 1)

A non-aqueous dispersion comprising the polymeric hybrid resins of the non-aqueous dispersion of claim 1, transferred to a second non-aqueous medium consisting of solvents selected from the group consisting of alcohols, esters, ketones and ethers that is different from the non-aqueous medium of claim 1, wherein the non-aqueous dispersion formed by transfer to a second non-aqueous medium contains no aromatic hydrocarbon solvents.

### Claim 7 (depends on 1)

The non-aqueous dispersion of claim 1, wherein the hybrid resins are at least partially insoluble in the non-aqueous medium.

### Claim 8 (depends on 1)

An ink-, coating-, primer-, or overprint varnish-composition, comprising the non-aqueous dispersion of claim 1.

### Claim 9 (depends on 8)

The composition of claim 8, further comprising a colorant.

### Claim 10 (depends on 8)

The composition of claim 8 wherein the composition comprises, by weight, about 15 wt % to about 50 wt % of the hybrid resin; about 6 wt % to about 30 wt % of a colorant; and about 10 wt % to about 60 wt % of the organic solvent.

### Claim 11 (depends on 8)

A process of coating a substrate, comprising applying the composition of claim 8 to a substrate.

### Claim 12 (depends on 11)

The process of claim 11, wherein the composition is applied by a deposition method selected from of flexo, gravure, digital, rod, curtain, cascade, roll, slot, or spray processes or a combination thereof.