IP Library Granted Patent US 8,827,417
Granted Patent B2
US 8,827,417 · App. 13/816,967 · Granted Sep 9, 2014

Inkjet ink with polyurethane additive derived from alkoxy aromatic diols inks

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,827,417
App. No.
13/816,967
Granted
Sep 9, 2014
Kind
B2
Abstract

The invention provides an ink for inkjet printing, comprising colorant and certain polyurethane ink additives which is derived from alkoxy aromatic diol derived from alkoxy aromatic diols which enhances fastness of the print towards highlighter and finger smudge without compromising jetting performance and storage stability of the ink. The inks may be jetted from both thermal and piezo ink jet systems.

Claims (76)

1. An aqueous inkjet ink composition comprising:

(a) a colorant;

(b) an aqueous vehicle; and

(c) a first polyurethane additive comprising an alkoxy aromatic diol, a diol substituted with an ionic group, and isocyanates

wherein the alkoxy aromatic diol is Z 1

wherein Ar is an aromatic group,

n, m, p, and q are integers,

n, m are the same or different and are greater than or equal to 2 to 12,

p is greater than or equal to 1 to 15,

q is greater than or equal to 0 to 15,

R 1 , R 2 are the same or different and each is independently selected from the group consisting of hydrogen, methyl, ethyl and higher alkyls of the formula of C t H 2t+1 ;

where t is an integer and is greater than or equal to 3 to 36,

Z 2 is a diol substituted with an ionic group; and

at least one Z 1 and at least one Z 2 must be present in the first polyurethane additive.

2. The aqueous inkjet ink composition of claim 1 , wherein the polyurethane additive is from 0.05 to 10%, by weight based on the weight of the total ink composition.

3. The aqueous inkjet ink composition of claim 1 , wherein the polyurethane additive is from 0.2 to 7% by weight based on the weight of the total ink composition.

4. The aqueous inkjet ink composition of claim 1 , having from 0.1 to 10 wt % colorant based on the total weight of the ink, a surface tension in the range of 20 dyne/cm to 70 dyne/cm at 25° C., and a viscosity of lower than 30 cP at 25° C.

5. The aqueous inkjet ink composition of claim 1 , wherein the polyurethane additive has an acid number (mg KOH per gram solid polymer) of at least 10 and at most 100.

6. An aqueous inkjet ink composition of claim 1 wherein for the alkoxy aromatic diol Z 1 p is selected from the group consisting of 1, 2, 3 and 4 and q is selected from the group consisting of 1, 2, 3 and 4.

7. An aqueous inkjet ink composition of claim 1 wherein the aromatic group is a hydroquinone.

8. An aqueous inkjet ink composition of claim 1 wherein the aromatic group is a bisphenol.

9. An aqueous inkjet ink composition of claim 1 , wherein the colorant is a selected from pigments and dispersed dyes.

10. An aqueous inkjet ink composition of claim 1 , wherein the colorant is a self-dispersed pigment.

11. The ink of claim 10 , wherein the anionic hydrophilic chemical groups on the self-dispersed carbon black pigment comprise carboxyl groups.

12. An aqueous inkjet ink composition of claim 10 , wherein the self-dispersed pigment comprises a pigment that has been oxidatively treated on its surface with hypochlorous acid, sulfonic acid, or ozone so as to bond at least one functional group selected from the group consisting of carbonyl, carboxyl, hydroxyl and sulfone, onto the surface of the pigment.

13. The aqueous inkjet ink composition of claim 10 wherein the self-dispersed pigment comprises a pigment that has been oxidatively treated on its surface with ozone.

14. The aqueous inkjet ink composition of claim 1 , wherein the aqueous vehicle is a mixture of water and at least one water-miscible solvent.

15. A method of inkjet printing onto a substrate is provided comprising, in any workable order, the steps of:

providing an inkjet printer that is responsive to digital data signals;

(a) loading the printer with a substrate to be printed;

(b) loading the printer with the aqueous inkjet ink composition of claim 1 ;

(c) printing onto the substrate using the aqueous inkjet ink, in response to the digital data signals to form a printed image on the substrate.

16. An inkjet ink set wherein at least one of the inks in the inkjet ink set is an aqueous inkjet ink composition comprising

(a) a colorant;

(b) an aqueous vehicle; and

(c) a polyurethane first additive comprising an alkoxy aromatic diol, a diol substituted with an ionic group, and isocyanates

wherein the alkoxy aromatic diol is Z 1

wherein Ar is an aromatic group,

n, m, p, and q are integers,

n, m are the same or different and are greater than or equal to 2 to 12,

p is greater than or equal to 1 to 15,

q is greater than or equal to 0 to 15,

R 1 , R 2 are the same or different and each is independently selected from the group consisting of hydrogen, methyl, ethyl and higher alkyls of the formula of C t H 2t+1 ;

where t is an integer and is greater than or equal to 3 to 36,

Z 2 is a diol substituted with an ionic group; and

at least one Z 1 and at least one Z 2 must be present in the first polyurethane additive.

17. A method of inkjet printing onto a substrate is provided comprising, in any workable order, the steps of:

a. providing an inkjet printer that is responsive to digital data signals;

b. loading the printer with a substrate to be printed;

c. loading the printer with the aqueous inkjet ink set of claim 16 ;

d. printing onto the substrate using the aqueous inkjet ink set, in response to the digital data signals to form a printed image on the substrate.

18. An aqueous inkjet ink composition comprising

(a) a colorant;

(b) an aqueous vehicle; and

(c) a second polyurethane additive comprising an alkoxy aromatic diol, a diol substituted with an ionic group, and isocyanates

wherein the alkoxy aromatic diol is Z 1

wherein Ar is an aromatic group,

n, m, p, and q are integers,

n, m are the same or different and are greater than or equal to 2 to 12,

p is greater than or equal to 1 to 15,

q is greater than or equal to 0 to 15,

R 1 , R 2 are the same or different and each is independently selected from the group consisting of hydrogen, methyl, ethyl and higher alkyls of the formula of C t H 2t+1 ;

where t is an integer and is greater than or equal to 3 to 36;

and wherein the second polyurethane additive has the structure II,

R 3 is alkyl, substituted alkyl, substituted alkyl/aryl from diisocyanate,

R 4 is Z 1 or Z 2 ,

R 5 is hydrogen; alkyl; branched alkyl or substituted alkyl from the amine terminating group,

R 6 is alkyl, branched alkyl or substituted alkyl from the amine terminating group,

s is an integer greater than or equal to 2 to 30;

Z 1 or Z 2 are defined above as the alkoxy aromatic diol and Z 2 as the diol substituted with an ionic group.

19. The aqueous inkjet ink composition of claim 18 , having from 0.05 to 10 wt % second polyurethane additive based on the total weight of the ink, having from 0.1 to 10 wt % colorant based on the total weight of the ink, a surface tension in the range of 20 dyne/cm to 70 dyne/cm at 25° C., and a viscosity of lower than 30 cP at 25° C.

20. An aqueous inkjet ink composition of claim 18 wherein for the alkoxy aromatic diol Z 1 p is selected from the group consisting of 1, 2, 3 and 4 and q is selected from the group consisting of 1, 2, 3 and 4.

21. An aqueous inkjet ink composition of claim 18 , wherein the colorant is a selected from pigments and dispersed dyes.

22. An aqueous inkjet ink composition of claim 18 , wherein the colorant is a self-dispersed pigment.

23. The ink of claim 22 , wherein the anionic hydrophilic chemical groups on the self-dispersed carbon black pigment comprise carboxyl groups.

24. An aqueous inkjet ink composition of claim 22 , wherein the self-dispersed pigment comprises a pigment that has been oxidatively treated on its surface with hypochlorous acid, sulfonic acid, or ozone so as to bond at least one functional group selected from the group consisting of carbonyl, carboxyl, hydroxyl and sulfone, onto the surface of the pigment.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2026
From: DUPONT ELECTRONICS, INC.
To: SP HOLDING II ET, INC.
Reel/Frame 075315/0340 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: DUPONT ELECTRONICS, INC.
Reel/Frame 049583/0269 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 14, 2014
From: ANTON, WAIFONG LIEW
To: E. I. DUPONT DE NEMOURS AND COMPANY
Reel/Frame 032888/0576 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2013
From: ROBERTS, C. CHAD; MCINTYRE, PATRICK F.
To: E.I. DUPONT DE NEMOURS AND COMPANY
Reel/Frame 029993/0187 →