# US 2017/0283631 A1 · Fast curing uv inkjet inks based on hyper-branched polyester acrylates

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- Number: US 2017/0283631 A1
- Document ID: US20170283631A1
- Status: Published application
- Kind: A1
- Application number: 14/978,027
- Filed: 2015-12-22
- Published: 2017-10-05
- Earliest claimed: 2014-12-22
- Assignees: Heidelberger Druckmaschinen AG
- Applicants: Heidelberger Druckmaschinen AG
- Inventors: Thomas Paul; Jonas Philipp Presser; Sima Payandeh; Mauela Hannelore Wolf; Silvia Worgt; Jessica Gioia
- Web page: https://patentgrep.com/patent/US20170283631A1

## 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
- C08F 2/06: Organic solvent
- C08F 2/48: by ultraviolet or visible light
- C09D 11/033: characterised by the solvent
- C09D 11/107: from unsaturated acids or derivatives thereof
- C09D 11/322: Pigment inks
- C09D 11/38: characterised by non-macromolecular additives other than solvents, pigments or 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A fast-curing UV inkjet ink is based on hyperbranched polyester acrylates. The ink contains the following components: 1 wt % to 20 wt % of at least one hyperbranched polyester acrylate having a functionality in the range from 6 to 30, 1 wt % to 30 wt % of at least one reactive diluent, 1 wt % to 20 wt % of at least one free-radical photoinitiator of the Norrish I type, 30 wt % to 70 wt % of at least one multifunctional (meth)acrylate monomer, and 0 wt % to 30 wt % of at least one monofunctional (meth)acrylate monomer. The ink is particularly suited for inkjet printing and it is used in an inkjet printing process.

## Claims

### Claim 1

A UV curable ink, comprising:
1-20 wt % of at least one hyperbranched polyester acrylate having a functionality in a range from 6 to 30;
1-30 wt % of at least one reactive diluent selected from the group consisting of ethylene glycol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, propylene glycol divinyl ether, n-butanediol divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, 1,4-cyclohexanedimethanol divinyl ether and mixtures thereof;
1-20 wt % of at least one free-radical photoinitiator of the Norrish I type;
30-70 wt % of at least one multifunctional (meth)acrylate monomer; and
0 wt % to 30 wt % of at least one monofunctional (meth)acrylate monomer.

### Claim 2 (depends on 1)

The ink according to claim 1, wherein the ink contains at least one hyper-branched polyester acrylate having a functionality in a range from 12 to 20.

### Claim 3 (depends on 1)

The ink according to claim 1, wherein the reactive diluent is selected from the group consisting of N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylformamide and vinyl ethers, such as ethyl vinyl ether, propyl vinyl ether, isopropyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether, tert-butyl vinyl ether, amyl vinyl ether, 2-ethylhexyl vinyl ether, dodecyl vinyl ether, octadecyl vinyl ether, cyclohexyl vinyl ether, ethylene glycol monovinyl ether, ethylene glycol divinyl ether, diethylene glycol monovinyl ether, triethylene glycol monovinyl ether, tetraethylene glycol monovinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, propylene glycol divinyl ether, polyethylene glycol divinyl ether, ethylene glycol butyl vinyl ether, triethylene glycol methyl vinyl ether, polyethylene glycol methyl vinyl ether, butanediol monovinyl ether, butanediol divinyl ether, hexanediol monovinyl ether, hexanediol divinyl ether, cyclohexanedimethanol monovinyl ether, cyclohexanedimethanol divinyl ether, trimethylolpropane trivinyl ether, aminopropyl vinyl ether, diethylaminoethyl vinyl ether and polytetrahydrofuran divinyl ether, vinyl esters, and vinylaromatics, 1,4-cyclohexanedimethanol divinyl ether and mixtures thereof.

### Claim 4 (depends on 3)

The ink according to claim 3, wherein the vinyl esters are selected from the group consisting of vinyl acetate, vinyl propionate, vinyl stearate and vinyl laurate, and the vinylaromatics are selected from the group consisting of vinyltoluene, styrene, 2-butylstyrene, 4-butylstyrene and 4-decylstyrene.

### Claim 5 (depends on 1)

The ink according to claim 1, wherein the multifunctional (meth)acrylate monomer is selected from the group consisting of pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexaacrylate, 1,2-ethylene glycol diacrylate, 1,2-ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, triethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,12-dodecanol diacrylate, 1,12-dodecanol dimethacrylate, tris(2-hydroxyethyl) isocyanurate triacrylate, polyethylene glycol diacrylates and the acrylic esters of ethoxylated or propoxylated glycols and polyols, and mixtures thereof.

### Claim 6 (depends on 5)

The ink according to claim 5, wherein the polyethylene glycol diacrylates are selected from the group consisting of tetraethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, tripropylene glycol triacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, glycerol propoxylate triacrylate, dipentaerythritol pentaacrylate, ethoxylated pentaerythritol tetraacrylate, propoxylated neopentylglycol diacrylate, neopentylglycol diacrylate, and bis(pentaerythritol) hexaacrylate, and the acrylic esters of ethoxylated or propoxylated glycols and polyols are selected from the group consisting of propoxylated neopentylglycol diacrylate, ethoxylated or propoxylated trimethylolpropane triacrylate and mixtures thereof.

### Claim 7 (depends on 1)

The ink according to claim 1, wherein the at least one monofunctional (meth)acrylate monomer is selected from the group consisting of lauryl acrylate, lauryl methacrylate, isodecyl acrylate, isodecyl methacrylate, myristyl acrylate, octadecyl acrylate, behenyl acrylate, cyclohexanedimethanol diacrylate, isobornyl acrylate, isobornyl methacrylate, caprolactone acrylate, 2-phenoxyethyl acrylate, isooctyl acrylate, isooctyl methacrylate, butyl acrylate and mixtures thereof.

### Claim 8 (depends on 1)

The ink according to claim 1, comprising the at least one hyperbranched polyester acrylate having a functionality in the range from 6 to 30 in an amount of 5 wt % to 10 wt %, the at least one reactive diluent in an amount of 5 wt % to 20 wt % and the at least one multifunctional (meth)acrylate monomer in an amount of 35 wt % to 60 wt %.

### Claim 9 (depends on 1)

The ink according to claim 1, wherein the at least one monofunctional (meth)acrylate monomer is present in an amount of 5 wt % to 15 wt %.

### Claim 10 (depends on 1)

The ink according to claim 1, wherein the photoinitiator is selected from the group consisting of 2-benzyl-2-dimethylamino-1-(4-morpholino-phenyl)butan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2-hydroxy-1-{4-[4-(2-hydroxy-2-methylpropionyl)benzyl]phenyl}-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, phenylbis-2,4,6-trimethylbenzoylphosphine oxide, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-ylphenyl)butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methylpropriophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-1-[4-(methylothio)phenyl]-2-morpholinopropan-1-one, 2,2-dimethoxy-1,2-diphenylethan-1-one, methyl benzoylformate, 2-hydroxy-4′-hydroxyethoxy-2-methylpropiophenone, 2-hydroxy-4′-methoxy-2-(4-methoxyphenyl)acetophenone, 2,2-diethoxyacetophenone and 2,4,6-ethyl trimethylbenzoylphenylphosphinate or a mixture of two or more.

### Claim 11 (depends on 1)

The ink according to claim 1, wherein the photoinitiator is present in an amount of 7 wt % to 17 wt %.

### Claim 12 (depends on 1)

The ink according to claim 1, which further comprises at least one colorant.

### Claim 13 (depends on 12)

The ink according to claim 12, wherein the colorant is present in an amount of 0.5 wt % to 15 wt %.

### Claim 14 (depends on 1)

The ink according to claim 1, wherein the ink has a viscosity at 45° C. in a range from 5 mPas to 25 mPas.

### Claim 15 (depends on 14)

The ink according to claim 14, wherein the viscosity at 45° C. lies in a range from 5 mPas to 15 mPas.

### Claim 16 (depends on 1)

The ink according to claim 1, wherein the ink has a surface tension of between 15 mN/m an 40 mN/m at 25° C.

### Claim 17 (depends on 1)

A process for inkjet printing, which comprises providing the ink according to claim 1 and printing with the ink.