Black azo dyes

• US 20020049309A1
• Filed: 06/18/2001
• Published: 04/25/2002
• Est. Priority Date: 08/18/2000
• Status: Active Grant

• Current Assignee: Funai Electric Co., Ltd. (Funai Electric Holdings Company Limited)
• Original Assignee: Lexmark International Incorporated (Ninestar Corporation)
• Inventors: Holloway, Ann P., Beach, Bradley Leonard, Feeman, James F.
• Granted Patent: US 6,451,989 B1
• Time in Patent Office: Days
• US Class Current: 534/827
• CPC Class Codes: C09B 31/08 from a coupling component "C" containing directive hydroxyl and amino groups
• CPC Class Codes: C09D 11/328 characterised by dyes

Abstract

Provided are novel black azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness.

Claims

1. A compound of Formula (I):

2. A compound of Formula (II):

3. The compound of claim 2, which is a compound of Formula (III):

4. The compound of claim 3, wherein R₂ is —

H.

5. The compound of claim 3, wherein R₅ is —

NH₂.

6. The compound of claim 4, wherein R₅ is —

NH₂.

7. The compound of claim 4 which has the formula:

8. The compound of claim 4 which has the formula:

9. The compound of claim 4 which has the formula:

10. The compound of claim 4 which has the formula:

11. The compound of claim 10, wherein M is selected from the group consisting of —

NH₄, —

N(CH₃)₄, —

N(CH₂CH₃)₄, and —

NH(CH₂CH₂OH)₃;

12. The compound of claim 4 having the formula:

14. The ink composition of claim 13, wherein the compound of Formula (I) is a compound of Formula (II):

15. The ink composition of claim 13, wherein the compound of Formula (I) is a compound of Formula (III):

16. The ink composition of claim 15, wherein R₂ is H and R₄ is methoxy.

17. The ink composition of claim 13, wherein the compound of Formula (I) is selected from

18. A substrate or medium coated with the ink composition of claim 13.

19. The medium of claim 13, wherein said medium is selected from paper, projector slides and textile materials.

13. An ink composition comprising:

(a) at least 0.1% by weight of a compound of Formula I;

 

wherein;

R₁ is —

O—

(CH₂)_m—

CO₂M, —

(CH₂)_n—

CO₂M, —

CO₂M, or —

SO₃M;

R₂ is —

H, —

CO₂M, -lower alkyl, -lower alkoxy, nitro;

—

CF₃, halogen, —

NHCO-lower alkyl, —

O—

(CH₂)_m—

CO₂M, or —

(CH₂)_n—

CO₂M;

R₃ is -lower-alkyl, —

O—

(CH₂)_m—

CO₂M, —

(CH₂)_n—

CO₂M, —

NHCO-lower-alkyl;

—

NHC(O)O-lower-alkyl;

or —

NH—

CO—

CO₂M;

R₄ is -lower-alkyl, -lower alkoxy, —

O—

(CH₂)_m—

CO₂M, —

(CH₂)_n—

CO₂M, —

NHCO-lower-alkyl;

—

NHC(O)O-lower-alkyl;

or NH₂CO₂M;

R₅ is —

N—

(R₆)(R₇), or a group of the formula

R₆ is —

H, -lower-alkyl, —

(CH₂)_n—

CO₂M, -lower-hydroxyalkyl, or lower-cyanoalkyl;

R₇ is —

H, -lower-alkyl, —

(CH₂)_n—

CO₂M, lower-hydroxyalkyl;

or -lower-cyanoalkyl;

R₈ is —

H, lower-alkyl, -lower-hydroxyalkyl, —

(CH₂)_nCO₂M;

R₉ is —

H, -lower-alkyl, -lower-hydroxyalkyl, —

(CH₂)_nCO₂M;

R₁₀ is —

H, -lower-alkyl, -lower alkoxy, -lower-hydroxyalkyl, —

(CH₂)_n—

CO₂M, -halogen, —

NR₈R₉, —

(CH₂)_nSO₃M, or —

O—

(CH₂)_mCO₂M;

m is 1, 2, or 3;

n is 1, 2, or 3;

M is —

H, —

Li, Na, —

K, or —

N—

(R₁₁)₄;

R₁₁ is —

H, -lower alkyl, or —

(CH₂—

CH(R₁₂)—

O)_p—

H;

p is 1 to 4;

x is 1 or 2;

R₁₂ is —

H, —

CH₃, —

CH₂—

CH₃, or —

CH₂—

OH; and

R₁₃ is —

H, lower alkyl, lower alkoxy, halogen, —

CO₂M, or —

SO₃M;

(b) water, and

(c) at least one cosolvent.