Ketocoumarins as photoinitiators and photosensitizers in printing inks and coatings

Patent metadata

Field	Value
Publication number	US-9382433-B2
Application number	US-201314417299-A
Country	US
Kind code	B2
Filing date	Jul 26, 2013
Priority date	Jul 27, 2012
Publication date	Jul 5, 2016
Grant date	Jul 5, 2016

Abstract

A series of novel ketocoumarin photoinitiators are disclosed for use in radiation curing.

First claim

What is claimed is:

1. A compound of formula (I):

where:
R is an alkyl or alkoxy substituents;
A=—CH 2 —R 1 —(CH 2 ) n —[O(CHR 2 CHR 3 ) a ] y —, where
n=0 or 1
a=1 to 2
R 1 =—C═O or —CH(OH)—
y=0 to 10,
one of R 2 and R 3 represents a hydrogen atom and the other represents a hydrogen atom, methyl group or ethyl group;

Q is a residue selected from the group consisting of: monohydroxy compounds having from 1 to 6 hydroxy groups, polyhydroxy compounds having from 1 to 6 hydroxy groups, and C 2 -C 12 polyalkylene glycols in which the alkylene part has from 2 to 12 carbon atoms; and
x is an integer from 1 to 6.

2. The compound of claim 1 , where Q is a residue of polyhydroxy compounds selected from the group consisting of: ethylene glycol, propylene glycol, butylene glycol, glycerol, 2,2-propanediol, polyethylene glycol, polypropylene glycol, polybutylene glycol, trimethylolpropane, di-trimethylolpropane, pentaerythritol and di-pentaerythritol.

3. The compound of claim 1 , where Q is a residue of monohydroxy compounds selected from the group consisting of: a compound of formula R 4 —OH where R 4 is a C 1 to C 12 alkyl group, and a group of formula —[O(CHR 2 CHR 3 ) a ] y —OCH 3 where a is a number from 1-2, y is a number from 0 to 10, and R 2 and R 3 are the same or different and each represents a hydrogen atom or a C 1 -C 4 alkyl group.

4. The compound of claim 1 , where Q is a residue of polyalkylene glycols selected from the group consisting of: butane-1,4-diol, hexane-1,6-diol, octane-1,8-diol, decane-1,10-diol and dodecane-1,12-diol.

5. The compound according to claim 1 , wherein x=1.

6. The compound of claim 1 having the structure:

7. The compound of claim 1 having the structure:

8. The compound of claim 1 having the structure:

Where x+y+z=3.

9. The compound of claim 1 having the structure:

10. A radiation curable composition comprising the compound of claim 1 .

11. The radiation curable composition of claim 10 , wherein the composition is selected from the group consisting of radiation curable coatings, printing inks, varnishes and adhesives.

12. The radiation curable composition of claim 11 further comprising one or more materials selected from the group consisting of polymerizable monomers, prepolymers, oligomers, other photoinitiators, an amine synergist and sensitizers.

13. The radiation curable composition of claim 12 further comprising one or more materials selected from the group consisting of waxes, flow aids, stabilizers, colorants, defoamers, dispersants, silicones, rheological modifiers and plasticizers.

14. A method of preparing a cured polymeric composition comprising exposing a radiation curable coating composition containing the compound of claim 1 to actinic radiation.

15. A method according to claim 14 , in which the actinic radiation is ultraviolet radiation.

16. A method of preparing a radiation curable composition comprising combining the compound of claim 1 with one or more materials selected from the group consisting of polymerizable monomers, prepolymers, oligomers, other photoinitiators, amine synergists and sensitizers.

17. The method of claim 16 , wherein the radiation curable composition is selected from the group consisting of inks, coatings, varnishes and adhesives.

18. The method of claim 16 , wherein the radiation curable composition is suitable for food packaging.

19. The radiation curable composition of claim 10 , wherein the compound of claim 1 has the structure:

Where x+y+z=3.

20. The method of claim 16 , wherein the compound of claim 1 has the structure:

Where x+y+z=3.

Assignees

• Sun Chemical Corp

Inventors

• Rowatt Brian
• Herlihy Shaun
• Davidson Robert

Classifications

• C07D311/08 Primary

  not hydrogenated in the hetero ring · CPC title

• C09D11/101 Primary

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• C07D311/16 Primary

  substituted in position 7 · CPC title

• C09D133/06

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title