Ink jet inks having IR-absorbing dye

Patent metadata

Field	Value
Publication number	US-10767064-B2
Application number	US-201716343804-A
Country	US
Kind code	B2
Filing date	Oct 12, 2017
Priority date	Oct 28, 2016
Publication date	Sep 8, 2020
Grant date	Sep 8, 2020

Abstract

An ink jet ink includes water, a water-soluble organic solvent, a resin, and an anionic heptamethine cyanine dye including a substituted or unsubstituted five or six membered ring in the heptamethine chain, the dye having a maximum absorption between 800 and 1200 nm to increase drying speed and improve image quality when dried with NIR or CIR dryers.

First claim

The invention claimed is:

1. An ink jet ink comprising:
water;
a water-soluble organic solvent;
a resin; and
an anionic heptamethine cyanine dye including a substituted or unsubstituted five or six membered ring in a chain of the anionic heptamethine cyanine dye, the anionic heptamethine cyanine dye having a maximum absorption between 800 nm and 1200 nm and including a structural moiety according to formula I or formula II:

wherein
L 1 and L 2 independently represent a substituted or unsubstituted alkylene group;
R 1 is selected from the group consisting of a hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, a substituted or unsubstituted aryl or heteroaryl group, a halogen, a hydroxyl, an alkoxy group, a thioether, a sulfoxide, a sulfone, a sulfonic acid or salt thereof, a carboxylic acid or salt thereof, an ester, an amide, and an amine;
M represents a hydrogen or a counterion that compensates for a negative charge of the sulfonate group MO 3 S;
R 2 and R 3 are independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, and a substituted or unsubstituted aryl or heteroaryl group, and R 2 and R 3 may represent atoms necessary to form a substituted or unsubstituted five to eight membered ring; and
R 4 and R 5 are independently selected from the group consisting of a hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, a substituted or aryl or heteroaryl group, a halogen, a hydroxyl, an alkoxy group, a thioether, a sulfoxide, a sulfone, a sulfonic acid or salt thereof, a carboxylic acid or salt thereof, an ester, an amide, and an amine, and R 4 and R 5 may represent atoms necessary to form a substituted or unsubstituted five to eight membered ring.

2. The ink jet ink according to claim 1 , wherein the anionic heptamethine cyanine dye includes a compound according to formula III:

wherein
R 6 and R 7 represent atoms necessary to form a five or six membered ring;
R 8 is selected from the group consisting of a hydrogen, a halogen, a thioether, and an alkoxy group;
L 3 represents a substituted or unsubstituted alkylene group;
X is selected from the group consisting of a halogen, an amide, a carbamate, a sulphonamide, an alkoxy group, a thioether, and a sulfone; and
Me is a methyl group.

3. The ink jet ink according to claim 2 , wherein R 6 and R 7 represent an unsubstituted carbocyclic five or six membered ring, and X represents a halogen.

4. The ink jet ink according to claim 2 , further comprising a colorant.

5. The ink jet ink according to claim 4 , wherein the colorant is a pigment.

6. The ink jet ink according to claim 1 , wherein the anionic heptamethine cyanine dye includes a compound having the formula IV:

wherein
R 9 and R 10 represent atoms necessary to form a five or six membered ring;
R 11 and R 12 are independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, and a substituted or unsubstituted aryl or heteroaryl group;
R 13 is selected from the group consisting of a hydrogen, a halogen, and an alkoxygroup; and
L 4 represents a substituted or unsubstituted alkylene group.

7. The ink jet ink according to claim 6 , wherein R 9 and R 10 represent an unsubstituted carbocyclic five or six membered ring, and R 13 represents hydrogen.

8. The ink jet ink according to claim 6 , further comprising a colorant.

9. The ink jet ink according to claim 8 , wherein the colorant is a pigment.

10. The ink jet ink according to claim 8 , wherein the resin includes a polyurethane resin.

11. The ink jet ink according to claim 10 , wherein the polyurethane resin is obtained by reacting a polyester polyol, a polyether diol, a polyol including an anionic group, and a polyisocyanate; and
the polyester polyol is obtained by reacting an aromatic polycarboxylic acid and a polyol.

12. The ink jet ink according to claim 1 , further comprising a colorant.

13. The ink jet ink according to claim 12 , wherein the colorant is a pigment.

14. The ink jet ink according to claim 1 , wherein the resin includes a polyurethane resin.

15. The ink jet ink according to claim 14 , wherein the polyurethane resin is obtained by reacting a polyester polyol, a polyether diol, a polyol including an anionic group, and a polyisocyanate; and
the polyester polyol is obtained by reacting an aromatic polycarboxylic acid and a polyol.

16. The ink jet ink according to claim 12 , wherein the resin includes a polyurethane resin.

17. A method of ink jet recording comprising:
providing a substrate;
jetting on the substrate the ink jet ink according to claim 1 ; and
heating the ink jetted on the substrate with a Near Infra Red heater or a Carbon Infra Red heater.

18. The method according to claim 17 , wherein the ink jet ink includes a colorant.

19. The method according to claim 17 , wherein the resin includes a polyurethane resin.

20. The method according to claim 19 , wherein
the polyurethane resin is obtained by reacting a polyester polyol, a polyether diol, a polyol including an anionic group, and a polyisocyanate; and
the polyester polyol is obtained by reacting an aromatic polycarboxylic acid and a polyol.

Assignees

• Agfa Nv

Inventors

• Loccufier Johan
• Bertels Ellen

Classifications

• B41J11/00216

  using infrared [IR] radiation or microwaves · CPC title

• C09B67/0033

  Blends of pigments; Mixtured crystals; Solid solutions · CPC title

• C09D11/033

  characterised by the solvent · CPC title

• B41M5/0023

  Digital printing methods characterised by the inks used (inks per se C09D11/00) · CPC title

• C09D11/322

  Pigment inks · CPC title