Trisazo dyes, inks comprising same and their use in ink jet printing

• US 5,423,906 A
• Filed: 08/19/1993
• Issued: 06/13/1995
• Est. Priority Date: 08/24/1992
• Status: Expired due to Term

• Current Assignee: FUJIFILM Imaging Colorants Limited (Fujifilm Holdings Corporation)
• Original Assignee: Zeneca Incorporated (Astrazeneca PLC)
• Inventors: Mistry, Prahalad M., Gregory, Peter
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US08/108,425
• Time in Patent Office: 663 Days
• Field of Search: 106/22 K, 106/20 D, 534/666, 534/680, 534/754, 534/755, 534/815, 428/537.5
• US Class Current: 106/31.48
• CPC Class Codes: C09B 35/461 D being derived from diaminobenzene
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: Y10T 428/31993 Of paper

Abstract

A compound of Formula (1) or salt thereof: ##STR1## wherein: R¹ is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H, SO₃ H or --NR³ R⁴ ;

R² is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H or SO₃ H;

R³ and R⁴ are each independently H, C_1-18 -alkyl or R³ and R⁴, together with the nitrogen atom to which they are attached, form an optionally substituted 5- or 6-membered ring;

W is --OH and X is --NH₂, or W is --NH₂ and X is --OH; and

Y and Z are each independently --OH or --NR³ R⁴.

The compound is suitable for use as a black component of ink jet printing inks.

Claims

1. A compound of Formula (1) or salt thereof:

##STR6## wherein;

R¹ is CO₂ H;

R² is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H or SO₃ H;

R³ and R⁴ are each independently H, C_1-18 -alkyl or R³ and R⁴, together with the nitrogen atom to which they are attached, form an optionally substituted 5- or 6-membered ring;

W is --OH and X is --NH₂, or W is --NH₂ and X is --OH; and

Y and Z are each independently --OH or --NR³ R⁴.

2. A compound according to claim 1 wherein X is --OH and the carboxy group on Ring A is at the 2-position.

3. A compound according to claim 1 wherein X is --NH₂ and the carboxy group on Ring A is at the 3-position.

4. A compound according to any one of the preceding claims wherein one of Y and Z is --OH and the other is --NR³ R⁴.

5. A compound according to claim 1 wherein R² is H.

6. A compound according to claim 1 wherein R³ and R⁴ are H or C_2-6 -alkyl.

7. A compound according to claim 1 in the form of an ammonium or substituted ammonium salt.

12. Paper printed with a compound according to claim 1.

8. A composition containing a first and second compound, each of which is of the Formula (1) or salt thereof:

##STR7## wherein;

R¹ is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H, SO₃ H or --NR³ R⁴ ;

R² is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H, SO₃ H;

R³ and R⁴ are each independently H, C_1-18 -alkyl or R³ and R⁴, together with the nitrogen atom to which they are attached, form an optionally substituted 5- or 6-membered ring;

W is --OH and X is --NH₂, or W is --NH₂ and X is --OH; and

Y and Z are each independently --OH or --NR³ R⁴ ; and

wherein the first and second compound are identical in every respect except that in the first compound Y is --NH₂ and Z is --OH and in the second compound Y is --OH and Z is --NH₂.

9. An ink comprising one or more compounds of Formula (1) or salt thereof:

##STR8## wherein;

R¹ is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H, SO₃ H or --NR³ R⁴ ;

R² is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H, SO₃ H;

R³ and R⁴ are each independently H, C_1-18 -alkyl or R³ and R⁴, together with the nitrogen atom to which they are attached, form an optionally substituted 5- or 6-membered ring;

W is --OH and X is --NH₂, or W is --NH₂ and X is --OH; and

Y and Z are each independently --OH or --NR³ R⁴ ; and

a liquid medium wherein the liquid medium comprises water and a water-soluble organic solvent in a weight-to-weight ratio of 95;

1 to 50;

50.

10. An ink according to claim 9 wherein the liquid medium comprises water and a water-soluble organic solvent in a weight-to-weight ratio of 90:

10 to 60;

40.

11. A process for printing a substrate with an ink using an ink jet printer, characterised in that the ink contains at least one compound of Formula (1) or salt thereof ##STR9## wherein:

R¹ is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H, SO₃ H or --NR³ R⁴ ;

R² is H, C_1-4 -alkyl, C_1-4 -alkoxy, CO₂ H, SO₃ H;

R³ and R⁴ are each independently H, C_1-18 -alkyl or R³ and R⁴, together with the nitrogen atom to which they are attached, form an optionally substituted 5- or 6-membered ring;

W is --OH and X is --NH₂, or W is --NH₂ and X is --OH; and

Y and Z are each independently --OH or --NR³ R⁴ ; and

which process comprises forming the ink into small droplets by ejection from a reservoir through a small orifice by the application of heat so that the droplets of ink are directed at the substrate.