Monoazo dyes useful in ink compositions for printing on substrates by ink-jet printing

• US 5,755,862 A
• Filed: 04/02/1997
• Issued: 05/26/1998
• Est. Priority Date: 04/25/1996
• Status: Expired due to Fees

• Current Assignee: FUJIFILM Imaging Colorants Limited (Fujifilm Holdings Corporation)
• Original Assignee: Zeneca Incorporated (Astrazeneca PLC)
• Inventors: Patel, Prakash, Gregory, Peter
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US08/831,951
• Time in Patent Office: 419 Days
• Field of Search: 106/31.48, 427/394, 8/543
• US Class Current: 106/31.48
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: G03G 9/091 Azo dyes

Abstract

An ink composition comprising

(i) a medium comprising a mixture of water and one or more water-soluble organic solvent(s), an organic solvent, or a low melting point solid; and

(ii) a dye of Formula (1) or salt thereof: ##STR1## wherein: each X¹ independently is a labile or non-labile substituent;

each T independently is --O--, --S-- or --NR¹ --;

each L¹ independently is a divalent organic linker group;

each V¹ independently is a group which is capable of undergoing an addition reaction or an elimination and addition reaction;

each R¹ independently is H or optionally substituted alkyl;

Z is the residue of a coupling component; and

m and n are each independently 0 or 1.

Also claimed is a composition comprising the ink and a nucleophilic agent; a process for ink jet printing of a substrate wherein the ink is applied to the substrate using an ink jet printer together with a nucelophilic agent and heating and/or basifying the ink and nucelophilic agent thereby causing the dye present in the ink and the nucleophilic agent to react together; and a toner resin composition comprising a toner resin and a dye of Formula (1).

Claims

1. An ink composition comprising

(i) a medium comprising a mixture of water and one or more water-soluble organic solvent(s), an organic solvent, or a low melting point solid;

and

(ii) a dye of Formula (1) or salt thereof;

##STR10## wherein each X¹ independently is a labile or non-labile substituent;

each T independently is --O--, --S-- or --NR¹ --;

each L¹ independently is a divalent organic linker group;

each V¹ independently is a group which is capable of undergoing an addition reaction or an elimination and addition reaction;

each R¹ independently is H or optionally substituted alkyl;

Z is the residue of a coupling component; and

m and n are each independently 0 or 1.

2. An ink composition according to claim 1 wherein V¹ is a vinyl sulphone group or a group which is convertible to vinyl sulphone on treatment with an aqueous alkali or a group of the formula --SO₂ NHCH₂ CH₂ --Y wherein Y is --OSO₃ H, --SSO₃ H, --Cl or --OCOCH₃.

3. An ink composition comprising a medium and a dye of the Formula (2) or a salt thereof:

##STR11## wherein;

each R⁴ independently is H or C_1-4 -alkyl;

G is H, alkyl, alkoxy, amido, ureido, halo, nitro, carboxy, amino or sulpho;

each X² independently is F, Cl, a quaternary ammonium group or a non labile group; and

each V² independently is a vinyl sulphone group or a group which is convertible to a vinyl sulphone group on treatment with aqueous alkali, a group of formula --SO₂ NHCH₃ CH₂ --Y wherein Y is --OSO₃ H, --SSO₃ H, --Cl or --OCOCH₃ or a group or formula --NHCOCR⁴ ═

CH₂ or --NHCOCBr═

CH₂ ; and

the medium is as defined in claim 1.

4. An ink composition according to claim 3 wherein X² is F, Cl or a quaternary ammonium group.

5. An ink composition according to any one of the preceding claims wherein the medium comprises water and one or more water-soluble organic solvent(s).

6. An ink composition according to any one of claims 1 to 4 comprising:

(a) 0.5 to 20 parts of the dye;

(b) 2 to 60 parts of water-soluble organic solvent(s); and

(c) 1 to 95 parts of water;

wherein all parts are by weight based upon the total weight of the ink and the parts (a)+(b)+(c)=100.

7. A process for printing a substrate with an ink composition comprising forming the ink composition into small droplets by ejection from a reservoir through a small orifice so that the droplets of ink are directed at a substrate wherein the ink composition is as defined in any one of claims 1 to 4.

8. A paper, an overhead projector slide or a textile material printed by means of the process according to claim 7.

9. A process for the coloration of a textile material with an ink composition according to any one of claims 1 to 4 which comprises the steps:

i) applying the ink composition to the textile material by ink jet printing; and

ii) heating the textile material at a temperature from 50°

C. to 250°

C. to fix the dye on the material.

10. A process for the coloration of a substrate comprising applying to the substrate:

(i) an ink compostion according to any one of claims 1 to 4 by forming the ink composition into small droplets by ejection from a reservoir through a small orifice so that the droplets of ink are directed at a substrate; and

(ii) a nucleophilic agent; and

heating and/or basifying the ink and nucleophilic agent thereby causing the dye present in the ink and the nucleophilic agent to react together.

11. A process according to claim 10 wherein the nucleophilic agent contains at least one group selected from the group consisting of thiols, thiones, aliphatic primary amino groups and aliphatic secondary amino groups.

12. A process according to claim 10 wherein the nucleophilic agent has a molecular weight below 600.

13. A process according to claim 11 wherein the nucleophilic agent has a molecular weight below 600.

14. A process according to claim 10 wherein the nucleophilic agent is applied to the substrate by an ink jet printer.

15. A composition comprising:

(i) an ink composition according to any one of claims 1 to 4; and

(ii) a nucleophilic agent having at least one group selected from the group consisting of thiols, thiones, aliphatic primary amino groups and aliphatic secondary amino groups.

16. A composition according to claim 15 wherein the nucelophilic agent has a molecular weight below 600.

17. A composition according to claim 15 comprising:

(a) 0.5 to 20 parts of the dye of Formula (1);

(b) 2 to 60 parts of water soluble organic solvent(s);

(c) 1 to 95 parts water; and

(d) 1 to 25 parts of the nucleophilic agent;

wherein all parts are parts by weight based upon the total weight of the composition and the parts (a)+(b)+(c)+(d)=100.

18. A composition according to claim 17 wherein the nucleophilic agent has a molecular weight below 600.

19. An ink composition obtained by heating or basifying or heating and basifying a composition according to claim 15.

20. A toner resin composition comprising a toner resin and a dye, wherein the dye is of Formula (1) or Formula (2) as defined in any one of claims 1 to 4.