Phase change inks containing wax-soluble near-infrared dyes

Patent metadata

Field	Value
Publication number	US-9738811-B2
Application number	US-201313975933-A
Country	US
Kind code	B2
Filing date	Aug 26, 2013
Priority date	Aug 26, 2013
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

Phase change ink compositions having a phase change carrier composition containing a wax and a wax-soluble near-infrared (NIR) dye having an absorption maximum in the wavelength region from about 700 nm to about 1400 nm. Near-infrared prints prepared with such phase change ink compositions. Methods of producing a layer of such a phase change ink on the surface of a substrate.

First claim

What is claimed is:

1. A phase change ink composition comprising: a phase change carrier composition comprising:
a wax; and
a wax-soluble near-infrared (NIR) dye having an absorption maximum in the wavelength region from about 700 nm to about 1400 nm, wherein the wax-soluble NIR dye is represented by formula (II), (III), or (IV), a tautomer thereof, or a salt thereof, wherein formulas (II), (III), and (IV) are:

wherein R 3 , R 4 , R 7 , R 8 , R 9 , or R 10 is independently a cyclic group-containing residue comprising at least one cyclic group selected from the group consisting of (a) a substituted or unsubstituted heterocyclic group comprising at least one of N, S, or O, (b) a substituted or unsubstituted cycloalkyl group, (c) a substituted or unsubstituted aryl group, and (d) a substituted or unsubstituted aralkyl group;
wherein at least one of R 3 or R 4 , comprises a substituted or unsubstituted perimidine group,
wherein at least one of R 7 or R 8 comprises a substituted or unsubstituted perimidine group,
wherein at least one of R 9 or R 10 comprises a substituted or unsubstituted perimidine group,
wherein each of R 3 , R 4 , R 7 , R 8 , R 9 , and R 10 independently comprises between about 10 and about 150 carbon atoms;
wherein each of R 5 and R 6 is independently selected from the group consisting of H and alkyl groups having from 1 to 6 carbon atoms; and
wherein X is:

 and
wherein n is 1 to 5, wherein the phase change ink composition is in a solid phase at room temperature.

2. The phase change ink composition of claim 1 , wherein the wax-soluble NIR dye has an absorption maximum in the wavelength region from about 700 nm to about 900 nm.

3. The phase change ink composition of claim 1 , wherein the wax is a polyethylene wax having: a molecular weight between about 200 Da and about 5,000 Da.

4. The phase change ink composition of claim 1 , comprising about 0.1 wt. % and about 80 wt. % of the wax relative to the total weight of the phase change ink composition, wherein an ink droplet of the phase change ink composition spreads upon exposure to infrared radiation.

5. The phase change ink composition of claim 1 , comprising between about 0.01 wt. % and about 20 wt. % of the wax-soluble NIR dye relative to the total weight of the phase change ink composition.

6. The phase change ink composition of claim 1 , wherein each of R 3 , R 4 , R 7 , R 8 , R 9 , and R 10 comprises a substituted or unsubstituted perimidine group.

7. The phase change ink composition of claim 1 , wherein at least one of R 3 , R 4 , R 7 , R 8 , R 9 , R 10 comprises at least one linear alkyl group having 5 to 50 carbon atoms in addition to the cyclic group-containing residue.

8. The phase change ink composition of claim 1 , wherein:
(i) R 3 or R 4 is independently selected from the group consisting of

(ii) R 5 or R 6 is independently selected from the group consisting of H and alkyl groups having from 1 to 6 carbon atoms;
(iii) R 7 or R 8 is independently selected from the group consisting of

(iv)) R 9 or R 10 is independently selected from the group consisting of

9. The phase change ink composition of claim 1 , wherein the phase change carrier composition comprises:
(a) a urethane resin that is the reaction product of the reaction of at least one first alcohol and a first isocyanate, the alcohol being selected from the group consisting of hydroabietyl alcohol, octylphenol ethoxylate, and octadecyl alcohol; and/or
(b) a mixed urethane/urea resin that is the reaction product of at least one second alcohol, a second isocyanate, and at least one monoamine; and
(c) at least: one monoamide; and
(d) at least one polyethylene wax.

10. The phase change ink composition of claim 9 , wherein the second alcohol is selected from the group consisting of hydroabietyl alcohol, octylphenol ethoxylate and octadecyl alcohol.

11. The phase change ink composition of claim 9 , wherein the second isocyanate is selected from the group consisting of a monoisocyanate, a diisocyanate, a triisocyanate, a copolymer of a diisocyanate, and a copolymer of a triisocyanate.

12. The phase change ink composition of claim 9 , wherein the second isocyanate is isophorone diisocyanate.

13. The phase change ink composition of claim 9 , wherein the monoamine is selected from the group consisting of an aliphatic monoamine, an aromatic monoamine, an aliphatic/aromatic monoamine, a fused ring system monoamine, and a hydroxyl/amino containing compound.

14. The phase change ink composition of claim 9 , wherein the monoamine is octadecyl amine.

15. The phase change ink composition of claim 9 , wherein the monoamide is stearyl stearamide.

16. A method for producing a layer of a phase change ink on the surface of a substrate, which comprises:
(1) employing in a printing apparatus a phase change ink composition in the solid phase comprising an admixture of (a) a phase change carrier composition and (b) a wax-soluble near-infrared (NIR) dye having an absorption maximum in the wavelength region from about 700 nm to about 1400 nm;
wherein the phase change carrier composition comprises (i) a urethane resin that is the reaction product of at least one first alcohol and a first isocyanate; and/or (ii) a urethane/urea resin that is the reaction product of at least one second alcohol, a second isocyanate and at least one monoamine; and (iii) at least one monoamide; and (iv) at least one polyethylene wax; and
wherein the wax-soluble NIR dye is represented by formula (II), (III), or (IV), a tautomer thereof, or a salt thereof, wherein formulas (II), (III), and (IV) are:

wherein each of R 3 , R 4 , R 7 , R 8 , R 9 , and R 10 is independently a cyclic group-containing residue comprising at least one cyclic group selected from the group consisting of (a) a substituted or unsubstituted heterocyclic group comprising at least one of N, S, or O, (b) a substituted or unsubstituted cycloalkyl group, (c) a substituted or unsubstituted aryl group, and (d) a substituted or unsubstituted aralkyl group;
wherein at least one of R 3 or R 4 comprises a substituted or unsubstituted perimidine group,
wherein at least one of R 7 or R 8 comprises a substituted or unsubstituted perimidine group,
wherein at least one of R 9 or R 10 comprises a substituted or unsubstituted perimidine group,
wherein each of R 3 , R 4 , R 7 , R 8 , R 9 , and R 10 independently comprises between about 10 and about 150 carbon atoms;
wherein each of R 5 and R 6 is independently selected from the group consisting of H and alkyl groups having from 1 to 6 carbon atoms; and
wherein X is:

 and
wherein n is 1 to 5, and wherein the phase change ink composition is in a solid phase at room temperature;

Assignees

• Xerox Corp

Inventors

• Banning Jeffrey H
• Thomas Jr Jule W
• Wu Bo
• Drappel Stephan V

Classifications

• C08G18/4829

  Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title

• C08K5/3417

  condensed with carbocyclic rings · CPC title

• Y10T428/24802

  Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] · CPC title

• C09D11/328 Primary

  characterised by dyes · CPC title

• C09B57/007

  Squaraine dyes · CPC title