Polymerizable thioxanthones

Patent metadata

Field	Value
Publication number	US-9278949-B2
Application number	US-201314404955-A
Country	US
Kind code	B2
Filing date	Jul 1, 2013
Priority date	Jul 10, 2012
Publication date	Mar 8, 2016
Grant date	Mar 8, 2016

Abstract

A polymerizable thioxanthone according to Formula (I):

wherein A represents a thioxanthone moiety; R1 and R2 are independently selected from the group consisting of a hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and a heteroaryl group; n represents 1 or 2; and R3 represents a moiety including at least one free radical polymerizable group selected from the group consisting of an acrylate, a methacrylate, an acrylamide, a methacrylamide, a styrene group, a maleate, a fumarate, an itaconate, a vinyl ether, a vinyl ester, an allyl ether, and an allyl ester.

First claim

The invention claimed is:

1. A polymerizable thioxanthone according to Formula (I):

wherein
A represents a thioxanthone moiety;
R1 and R2 are independently selected from the group consisting of a hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and a heteroaryl group;
n represents 1 or 2; and
R3 represents a moiety including at least one free radical polymerizable group selected from the group consisting of an acrylate, a methacrylate, an acrylamide, a methacrylamide, a styrene group, a maleate, a fumarate, an itaconate, a vinyl ether, a vinyl ester, an allyl ether, and an allyl ester.

2. The polymerizable thioxanthone according to claim 1 , wherein A represents a thioxanthone moiety substituted in a 1-position by a halogen, an alkyl group, or an alkoxy group.

3. The polymerizable thioxanthone according to claim 2 , wherein Formula (I) has a structure according to Formula (II) or Formula (III):

wherein X is selected from the group consisting of a hydrogen, a halogen, an alkyl group, and an alkoxy group.

4. The polymerizable thioxanthone according to claim 3 , wherein X represents a fluorine.

5. The polymerizable thioxanthone according to claim 1 , wherein R1 and R2 are independently selected from the group consisting of hydrogen and an alkyl group having 1 to 6 carbon atoms.

6. The polymerizable thioxanthone according to claim 5 , wherein R1 and R2 are both hydrogen.

7. The polymerizable thioxanthone according to claim 1 , wherein the at least one free radical polymerizable group is selected from the group consisting of an acrylate and a methacrylate.

8. The polymerizable thioxanthone according to claim 1 , wherein the moiety R3 includes two or three free radical polymerizable groups.

9. The polymerizable thioxanthone according to claim 8 , wherein the two or three free radical polymerizable groups are independently selected from the group consisting of an acrylate and a methacrylate.

10. The polymerizable thioxanthone according to claim 1 , wherein n is equal to 1.

11. The polymerizable thioxanthone according to claim 3 , wherein n is equal to 1.

12. A radiation curable composition including the polymerizable thioxanthone according to claim 1 .

13. A radiation curable composition including the polymerizable thioxanthone according to claim 7 .

14. The radiation curable composition according to claim 12 , further comprising a monomer according to Formula (IV):

wherein
L represents a linking group;
m and n independently represent an integer having a value from 1 to 5;
X represents O, S, or NR 6 ; and
R 5 and R 6 independently represent hydrogen or a substituted or unsubstituted alkyl group;
with the proviso that when X ═NR 6 then L and R 6 may together form a ring system.

15. The radiation curable composition according to claim 12 , wherein the radiation curable composition is an inkjet ink having a viscosity smaller than 15 mPa·s at 40° C. and at a shear rate of 1,000 s −1 .

16. A substrate including a cured layer of the radiation curable composition according to claim 12 .

17. A method of inkjet printing, the method including the step of:
jetting the radiation curable composition of claim 12 onto a substrate.

Assignees

• Agfa Graphics Nv

Inventors

• Loccufier Johan

Classifications

• C08F122/1006

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title

• C08F228/06

  by a heterocyclic ring containing sulfur · CPC title

• C07D335/16 Primary

  Oxygen atoms, e.g. thioxanthones · CPC title

• C09D11/322

  Pigment inks · CPC title

• C08F220/26

  Esters containing oxygen in addition to the carboxy oxygen · CPC title