Printing process using specified AZO compounds

• US 20040020404A1
• Filed: 04/11/2003
• Published: 02/05/2004
• Est. Priority Date: 06/13/2002
• Status: Active Grant

• Current Assignee: FUJIFILM Imaging Colorants Limited (Fujifilm Holdings Corporation)
• Original Assignee: Avecia Limited
• Inventors: Double, Philip John, Bradbury, Roy, Paul, Thomas, Hadjisoteriou, Maria Soteri, Wight, Paul, Popat, Ajay Haridas, Thompson, Neil James, Gregory, Peter, Dickinson, Alan
• Granted Patent: US 7,056,376 B2
• Time in Patent Office: Days
• US Class Current: 106/31.5
• CPC Class Codes: C09B 33/22 Trisazo dyes of the type A->B->K<-C
• CPC Class Codes: C09B 35/40 the component K being a dihydroxy or polyhydroxy compound
• CPC Class Codes: C09B 35/52 of the type
• CPC Class Codes: C09B 35/58 of the type
• CPC Class Codes: C09B 35/60 of the type
• CPC Class Codes: C09B 35/64 Higher polyazo dyes, e.g. of the types
• CPC Class Codes: C09B 45/24 Disazo or polyazo compounds
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: C09D 11/40 Ink-sets specially adapted for multi-colour inkjet printing
• CPC Class Codes: D06P 1/18 Azo dyes
• CPC Class Codes: D06P 5/30 Ink jet printing

Abstract

A process for printing an image on a substrate comprising applying thereto a composition comprising a liquid medium and a compound of Formula (1):

T—Q—N═N—L—T  Formula (1)

wherein:

each T independently is an azo group;

Q is an optionally substituted, optionally metallised 1,8-dihydroxy-naphthyl group; and

L is a divalent organic linker group.

Also claimed are compositions and dyes

Claims

1. A process for printing an image on a substrate comprising applying thereto a composition comprising a liquid medium and a compound of Formula (1):

T—

Q—

N—

═

N—

L—

T 

 

Formula (1)

wherein;

each T independently is an azo group;

p1 Q is an optionally substituted, optionally metallised 1,8-dihydroxynaphthyl group; and

L is a divalent organic linker group.

2. A composition comprising a compound of Formula (1), as defined in claim 1, and a liquid medium.

3. A composition according to claim 2 which further comprises a pH buffer and the composition has a pH of 4 to 8.

4. A composition according to claim 3 wherein the buffer is selected from the group consisting of (tris(hydroxymethyl)aminomethane), cationic aliphatic primary amines, zwitterionic amino acids, phosphate buffers, amino-hydroxyalkylsulfonic acid zwitterions and trishydroxymethylaminomethane derivatives.

5. A composition according to claim 2 wherein the liquid medium further comprises an oxidant.

6. A process for the preparation of a compound of Formula (1), as defined in claim 1, which comprises diazotising an amine and coupling the resultant diazonium salt with a compound of formula T—

Q—

N═

N—

LH, wherein T, L and Q are each independently as defined in claim 1.

7. A process for the preparation of a compound of Formula (1), as defined in claim 1, which comprises the reaction of a compound of formula T—

X—

N═

N—

L—

T with a strong base thereby forming a compound of Formula (1), wherein each T independently and L are as defined in claim 1 and X is an optionally substituted 1-hydroxy-8-amino-naphthylene group.

12. A compound according to claims 5 wherein:

T is A—

N═

N—

each A independently is optionally substituted phenyl, naphthyl, pyridyl or pyrazolyl;

Q is of Formula (5) or (6) or a metal complex thereof;

—

L¹(—

G—

L²)_x—

 

 

Formula (7)

wherein;

L¹ is a single covalent bond or optionally substituted phenyl or naphthyl;

L² is optionally substituted phenyl or naphthyl;

G is —

O—

, —

NR²—

, —

N═

N—

, —

NR²—

CO—

, —

NR²CON (R²)—

, —

S—

, —

SO—

, —

SO₂—

, —

SO₂NR₂—

or —

CR²═

CR²—

, wherein each R² independently is H or C_1-4-alkyl; and

X is 0, 1 or 2;

with the proviso that at least one of the groups represented by T comprises a Water-solubilising group.

13. A compound according to claim 8 or 12 wherein said optional substituents which may be present on A and L (including L¹ and L²) are selected from OH, SO₃H, PO₃H₂, CO₂H, NO₂, NH₂, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amine, optionally substituted acylamine and optionally substituted azo.

14. A compound according to claim 8 or 12 wherein said optional substituents which may be present on A and L (including L¹ and L²) are selected from OH;

SO₃H;

PO₃H₂;

CO₂H;

NO₂;

NH₂;

C_1-4-alkyl optionally carrying a sulpho, carboxy, phosphato, C_1-4-alkoxy, amino or hydroxy group;

C_1-4-alkoxy optionally carrying a sulpho, carboxy, phosphato, C_1-4-alkoxy, C_1-4alkyl, amino or hydroxy group;

N carrying one or two C_1-4-alkyl groups optionally carrying a sulpho, carboxy, phosphato, C_1-4-alkoxy, amino or hydroxy group;

C_1-4-acylamino; and

;

phenylazo, naphthylazo and heteroarylazo where the phenyl, naphthyl and heteroaryl units are optionally further substituted with one or more groups selected from OH, SO₃H, PO₃H₂, CO₂H, NO₂ and NH₂, and azo groups comprising Formula (2);

17. A paper, an overhead projector slide or a textile material printed by means of a process according to claim 1.

19. An ink jet printer cartridge, optionally refillable, comprising one or more chambers and a composition, wherein the composition is present in at least one of the chambers and the composition is as defined in claim 2.

21. An ink set comprising a black ink, a magenta ink a cyan ink and a yellow ink, wherein the black ink comprises a composition according to claim 2.

8. A compound of Formula (1):

T—

Q—

N—

═

N—

L—

T 

 

Formula (1)

wherein;

each T independently is an azo group;

Q is an optionally substituted optionally metallised 1,8-dihydroxynaphthyl group; and

L is a divalent organic linker group;

with the proviso that at least one of the groups represented by T comprises a water-solubilising group.

9. A compound according to claim 8 wherein each T independently is of the formula A—

N═

N—

wherein each A independently is an optionally substituted aryl, heteroaryl, non-aromatic heterocyclic or an alkenyl group.

10. A compound according to claim 8 wherein Q is of Formula (3) or a metal complex thereof:

11. A compound according to any one of claims 8 or 9 wherein L is of Formula (7):

—

L¹(—

(—

G—

L²)_x—

 

 

Formula (7)

wherein;

L¹ is a single covalent bond or optionally substituted phenyl or naphthyl;

L² is optionally substituted phenyl or naphthyl;

G is —

O—

, —

NR²—

, —

N═

N—

, —

NR²—

CO—

, —

NR²CONR²—

, —

S—

, —

SO—

, —

SO₂—

, —

SO₂NR²—

or —

CR²═

CR²—

, wherein each R² independently is H or C_1-4-alkyl; and

X is 0, 1 or 2.

15. A compound according to claim 8 of Formula (8) or a salt thereof:

16. A compound according to claim 8 of Formula (9) or a salt thereof:

18. A paper, an overhead projector slide or a textile material printed with a compound according to claim 8.

20. An ink set comprising a black ink, a magenta ink, a cyan ink and a yellow ink, wherein the black ink comprises a compound according to claim 8 or 15.