UV-CURABLE COMPOSITION FOR COATING OR PRINTING OF A SUBSTRATE AND/OR A SUBSTRATE SURFACE

• US 20190309179A1
• Filed: 04/04/2019
• Published: 10/10/2019
• Est. Priority Date: 04/06/2018
• Status: Active Grant

• Current Assignee: Marabu Gmbh & Co. Kg
• Original Assignee: Marabu Gmbh & Co. Kg
• Inventors: Bohringer, Oliver, Rupp, Jochen
• Granted Patent: US 10,851,250 B2
• Time in Patent Office: Days
• CPC Class Codes: C08F 20/18 with acrylic or methacrylic acids
• CPC Class Codes: C08F 20/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08K 5/07 Aldehydes; Ketones
• CPC Class Codes: C08K 5/357 Six-membered rings
• CPC Class Codes: C08K 5/5397 Phosphine oxides
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: 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
• CPC Class Codes: C09D 11/107 from unsaturated acids or derivatives thereof
• CPC Class Codes: C09D 133/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C09D 133/10 Homopolymers or copolymers of methacrylic acid esters

Abstract

A UV-curable composition for coating or printing, in particular digital printing, of a substrate and/or a substrate surface, includes a monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted monocycloaliphatic hydrocarbon radical, at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical, at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical and at least one photoinitiator; and a method for coating and/or printing, in particular digital printing, of a substrate and/or a substrate surface, a kit and a substrate coated or printed, in particular digitally printed, with the UV-curable composition.

Claims

1. UV-curable composition for coating or printing, in particular digital printing, of a substrate and/or a substrate surface, comprising

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted monocycloaliphatic hydrocarbon radical,

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical,

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical and

at least one photoinitiator.

2. UV-curable composition according to claim 1, characterized in that the monocycloaliphatic hydrocarbon radical is a monocycloalkyl radical, in particular with 3 ring-forming carbon atoms to 8 ring-forming carbon atoms.

3. UV-curable composition according to claim 1, characterized in that the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted monocycloaliphatic hydrocarbon radical is selected from the group composed of 3,3,5-trimethylcyclohexyl acrylate, 2-(1,1-dimethylethyl)cyclohexyl acrylate, 3-(1,1-dimethylethyl)cyclohexyl acrylate, 4-(1,1-dimethylethyl)cyclohexyl acrylate, 4-tert-butylcyclohexyl acrylate, 4-tert-butylcyclohexyl methacrylate, cyclohexyl methacrylate, 3,3,5-trimethylcyclohexyl methacrylate and mixtures of at least two of said monofunctional acrylate monomers/methacrylate monomers.

4. UV-curable composition according to claim 1, characterized in that the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted monocycloaliphatic hydrocarbon radical is contained in an amount of 5% by weight to 30% by weight, in particular 10% by weight to 25% by weight, and preferably 15% by weight to 25% by weight, based on the total weight of the composition.

5. UV-curable composition according to claim 1, characterized in that the UV-curable composition is free of a monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted linear aliphatic hydrocarbon radical.

6. UV-curable composition according to claim 1, characterized in that the heterocyclic, non-aromatic organic radical is a heterocycloalkyl radical, in particular with 3 ring-forming atoms to 8 ring-forming atoms.

7. UV-curable composition according to claim 1, characterized in that the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical is selected from the group composed of N-acryloylmorpholine, cyclic trimethylolpropane formal acrylate, tetrahydrofurfuryl acrylate and mixtures of at least two of said monofunctional acrylate monomers/methacrylate monomers.

8. UV-curable composition according to claim 1, characterized in that the at least one monofunctional acrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical is contained in an amount of 20% by weight to 40% by weight, in particular 25% by weight to 40% by weight, and preferably 30% by weight to 40% by weight, based on the total weight of the composition.

9. UV-curable composition according to claim 1, characterized in that the bicyclic, non-aromatic hydrocarbon radical is a bridged hydrocarbon radical.

10. UV-curable composition according to claim 1, characterized in that the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical is selected from the group composed of isobornyl acrylate, isobornyl methacrylate, dihydrocyclopentadienyl acrylate, ethoxylated dihydrocyclopentadienyl acrylate and mixtures of at least two of said monofunctional acrylate monomers/methacrylate monomers.

11. UV-curable composition according to claim 1, characterized in that the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical is contained in an amount of 5% by weight to 30% by weight, in particular 10% by weight to 25% by weight, and preferably 15% by weight to 25% by weight, based on the total weight of the composition.

12. UV-curable composition according to claim 1, characterized in that the molar mass ratio of the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical to the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical is >

1.

13. UV-curable composition according to claim 1, characterized in that the molar ratio of the sum of the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical and the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical to the at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted monocycloaliphatic hydrocarbon radical is in the range of 1 to 8, preferably 1 to 5, more preferably 2 to 4, and in particular 3 to 4.

14. UV-curable composition according to claim 1, characterized in that the at least one photoinitiator is of Norrish type I, in particular selected from the group composed of 2-hydroxy-1-(4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl)-2-methyl-propan-1-one, 1-hydroxycyclohexyl-phenyl-ketone, phenylbis-(2,4,6-trimethylbenzoyl-)phosphine oxide, 2-benzyl-2-dimethylamino-1-(4-morpholino-phenyl)-butanone-1, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-hydroxy-2-methylpropriophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-1[4-(methylthio)phenyl]-2-morpholinopropan-1-one and mixtures of at least two of said photoinitiators.

15. UV-curable composition according to claim 1, characterized in that the at least one photoinitiator is contained in an amount of <

15% by weight, in particular 1% by weight to 14% by weight, based on the total weight of the composition.

16. UV-curable composition according to claim 1, characterized in that it further comprises at least one colouring agent, preferably at least one pigment, in particular selected from the group composed of pigments based on quinacridones, pigments based on isoindolines, pigments based on isoindolinones, pigments based on phthalocyanines, pigments based on benzimidazolones and mixtures of at least two of said pigments.

17. UV-curable composition according to one of claim 1, characterized in that it is free of colouring agents and/or pigments.

18. Method for coating or printing, in particular digital printing, of a substrate and/or a substrate surface, comprising the following steps:

coating or printing, in particular digital printing, of a substrate surface with a UV-curable composition according to claim 1 and

UV curing of the composition.

19. Kit for coating or printing, in particular digital printing, of a substrate and/or a substrate surface, comprising, spatially separated from one another,

at least two UV-curable compositions according to claim 1 that are distinguishable from one another

and/or

at least one UV-curable composition for coating or printing, in particular digital printing, of a substrate and/or a substrate surface, comprising

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted monocycloaliphatic hydrocarbon radical,

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical,

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical and

at least one photoinitiator and a non-UV-curable composition

and/or

at least one UV-curable composition for coating or printing, in particular digital printing, of a substrate and/or a substrate surface, comprising

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted monocycloaliphatic hydrocarbon radical,

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted heterocyclic, non-aromatic organic radical,

at least one monofunctional acrylate monomer/methacrylate monomer with a substituted or unsubstituted bicyclic, non-aromatic hydrocarbon radical and

at least one photoinitiator and at least one further component selected from the group composed of a UV lamp, an LED emitter, an LED UV dryer, a digital print head, a digital printing system, pigment dispersions and combinations of at least two of said components.

20. Substrate, coated or printed with a composition according to claim 1.