# US 8,569,393 B2 · UV-LED curable compositions and inks

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- Number: US 8,569,393 B2
- Document ID: US8569393B2
- Status: Granted
- Kind: B2
- Application number: 13/511,374
- Filed: 2010-12-06
- Published: 2012-11-08
- Granted: 2013-10-29
- Earliest claimed: 2009-12-07
- Assignees: Agfa-Gevaert
- Applicants: Johan Loccufier
- Inventors: Johan Loccufier
- Web page: https://patentgrep.com/patent/US8569393B2

## CPC

- G03F 7/028: with photosensitivity-increasing substances, e.g. photoinitiators
- G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## Abstract

A radiation curable composition for UV LED curing includes at least one co-initiator selected from the group consisting of an aliphatic tertiary amine and a dialkyl aniline derivative; and at least one specific carbazole photoinitiator. The radiation curable composition can be advantageously used to prevent unstable yellowing behavior in an image upon storage.

## Claims

### Claim 1

A free radical radiation curable composition for UV LED curing comprising:
at least one co-initiator selected from the group consisting of an aliphatic tertiary amine and a dialkyl aniline derivative; and
at least one photoinitiator according to Formula (I):
wherein,
R1 and R2 are independently selected from the group consisting of an aromatic or heteroaromatic group and a substituent according to Formula (II):
R3 is selected from the group consisting of hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an alkaryl group, and an aryl or heteroaryl group;
S1 and S2 are independently selected from the group consisting of hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an alkaryl group, an aryl group, a heteroaryl group, a halogen, OH, an alkoxy group, a thiol group, a thioalkoxy group, an ester group, an amide group, an amine group, and a carboxylic acid group;
Y represents O or NR5;
R4 and R5 are selected from the group consisting of hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an alkaryl group, and an aryl or heteroaryl group;
n and m independently represent an integer from 1 to 3; and
X and Z represent O; and
at least one of R1 and R2 is represented by a substituent according to Formula (II).

### Claim 2 (depends on 1)

The radiation curable composition according to claim 1, wherein S1 and S2 represent hydrogen.

### Claim 3 (depends on 1)

The radiation curable composition according to claim 1, wherein R3 represents an alkyl group.

### Claim 4 (depends on 2)

The radiation curable composition according to claim 2, wherein R3 represents an alkyl group.

### Claim 5 (depends on 3)

The radiation curable composition according to claim 3, wherein R3 represents a branched alkyl group.

### Claim 6 (depends on 1)

The radiation curable composition according to claim 1, wherein the at least one photoinitiator is a diffusion hindered photoinitiator selected from the group consisting of a polymerizable photoinitiator, a multifunctional photoinitiator, a polymeric photoinitiator, and an oligomeric photoinitiator.

### Claim 7 (depends on 6)

The radiation curable composition according to claim 6, wherein the at least one photoinitiator according to Formula (I) comprises at least one polymerizable ethylenically unsaturated group.

### Claim 8 (depends on 7)

The radiation curable composition according to claim 7, wherein the at least one polymerizable ethylenically unsaturated group is selected from the group consisting of an acrylate, a methacrylate, an acrylamide a methacrylamide, a styrene, a maleimide, a vinyl ester, a vinyl ether, an allyl ether, and an allyl ester.

### Claim 9 (depends on 8)

The radiation curable composition according to claim 8, wherein the at least one polymerizable ethylenically unsaturated group is an acrylate.

### Claim 10 (depends on 6)

The radiation curable composition according to claim 6, wherein at least one of R1 to R3 is substituted with the at least one polymerizable ethylenically unsaturated group.

### Claim 11 (depends on 6)

The radiation curable composition according to claim 6, wherein one of the groups selected from R1 to R3, S1, and S2 is linked to a polymer selected from the group consisting of a star polymer, a dendritic polymer, and a hyperbranched polymer.

### Claim 12 (depends on 11)

The radiation curable composition according to claim 11, wherein the hyperbranched polymer is a polyether or a polyester.

### Claim 13 (depends on 1)

A radiation curable inkjet ink comprising:
the radiation curable composition according to claim 1.

### Claim 14 (depends on 6)

A radiation curable inkjet ink comprising:
the radiation curable composition according to claim 6.

### Claim 15 (depends on 1)

A method for preparing a radiation curable composition as defined by claim 1 comprising the steps of:
a) providing a composition containing monomers; and
b) adding to the composition the at least one photoinitiator according to Formula (I) and the at least one co-initiator selected from the group consisting of an aliphatic tertiary amine and a dialkyl aniline derivative.

### Claim 16 (depends on 6)

A method for preparing a radiation curable composition as defined by claim 6 comprising the steps of:
a) providing a composition containing monomers; and
b) adding to the composition the at least one photoinitiator according to Formula (I) and the at least one co-initiator selected from the group consisting of an aliphatic tertiary amine and a dialkyl aniline derivative.
