Metallized azo dyes and inks for ink-jet printing containing...

Compositions: coating or plastic – Coating or plastic compositions – Marking

Reexamination Certificate

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C106S031480, C106S031490, C106S031500, C106S031510, C534S692000, C534S703000, C347S100000

Reexamination Certificate

active

06712890

ABSTRACT:

The present invention relates to water soluble compounds and their salts, to compositions containing such compounds and their use in ink jet printing (“IJP”), to ink jet printer cartridges and to ink jet printing processes.
IJP is a non-impact printing technique in which droplets of coloured liquids are ejected through a fine nozzle onto a substrate without bringing the nozzle into contact with the substrate.
IJP is a relatively inexpensive way of recording multicolour images, for example pictures obtained from digital sources such as electronic cameras, scanners and the Internet. The use of ink jet printers to print colour images in the home or office environment is now becoming commonplace. However IJP has a big disadvantage compared to conventional silver halide photography in that the resultant images fade in ordinary daylight. Thus, there is a need to improve the light-fastness properties of prints to prevent images fading or vanishing, or becoming discoloured over time. In addition, there are many demanding performance requirements for dyes and inks used in IJP. For example sharp, non-feathered images having good water-fastness and optical density are required. The inks are required to dry quickly when applied to a substrate to prevent smudging, but they should not form a crust over the tip of an ink jetnozzle which stops the printer from working effectively. The inks should also be stable to storage over time without decomposing by forming a precipitate which could block the fine nozzle.
The choice of a colorant in ink jet systems is critical to image quality. The colorants should also have a high degree of light-fastness after printing onto a substrate. For aqueous dye-based inks, the dyes need to be sufficiently soluble in water to prepare a solution that is capable of producing adequate density on the substrate and be stable for extended periods of storage without precipitation. It is difficult to find dyes which meet all of these requirements, particularly yellow dyes.
U.S. Pat. Nos. 4,393,132, 4,183,755 and 4,148,643 disclose the formation of metal chelating compounds in the course of a reaction during photographic development followed by diffusion into a photographic image receiving layer in which the metallised dye is formed and immobilised. These patents do not specify the use of premetallised dyes and only refer to the formation of metal complexes on diffusion of the dye into the image receiving layer.
European patent 260,561 describes the use of related compounds for dyeing leather.
German OLS 2404314 describes certain formulations of Cr and Co coordinated dyes which would not be suitable as ink jet inks.
Water immiscible yellow dyes are described in U.S. Pat. Nos. 4,407,931 and 4,418,131 and are useful in photographic applications.
According to the present invention there is provided a water soluble compound of Formula (1) or a salt thereof:
wherein:
Y is an electron withdrawing group;
Y
1
is H,alkyl or aryl, OR or NR
2
in which each R independently is H, optionally substituted alkyl or optionally substituted aryl;
or Y and Y
1
together form a 5- or 6- membered ring;
X
1
is a group or atom which co-ordinates with M;
M is hexa co-ordinate metal;
G is a group of Formula (2), (3) or (4); and
L
1
, L
2
and L
3
, each independently represent ligands required to complete hexa-coordinate geometry around metal M;
 wherein:
S is a water solubilizing group;
Ar is a benzene or naphthalene group in which X is located ortho to the azo group;
X is a group or atom which co-ordinates with M;
Z provides atoms or groups which complete an optionally substituted 5- or 6-membered aromatic heterocyclic ring;
Ring A is an optionally substituted aromatic ring;
Ring B is an optionally substituted 5- or 6-membered aromatic heterocyclic ring;
n is 0, 1, 2 or 3;
and the * signify the points of attachment of the groups of Formulae (2), (3) and (4) to the N and M atoms in the compound of Formula (1).
The compounds of Formula (1) preferably comprise at least one water solubilising group which is preferably a carboxy, amido, sulpho, sulphonamide or phosphato group which is preferably present in Y or Y
1
, or is a substituent on Ring B or on Ring A preferably in a position para with respect to the azo group.
Y is preferably selected from CN, CO
2
H, CO
2
R, CONR
2
, COR and —SO
2
NR
2
in which each R is independently defined as above.
Where Y
1
is alkyl it is preferably C
1-8
-alkyl, more preferably C
1-4
-alkyl.
Where Y
1
is aryl it is preferably phenyl.
Where R is optionally substituted alkyl it is preferably C
1-8
-alkyl, more preferably C
1-4
-alkyl.
Where R is optionally substituted aryl it is preferably phenyl or naphthyl, more preferably phenyl.
Where R is optionally substituted alkyl or aryl optional substitutents are preferably selected from water solubilising groups, particularly SO
3
H, SO
2
NR
2
, CO
2
H or PO
3
H
2
.
Where Y and Y
1
are joined together to form a 5- or 6-membered ring it is preferably pyrazolone or triazole, more preferably pyrazolone or 1, 3, 4-triazole.
X and X
1
each independently is preferably O, CO
2
R or NR in which R is defined above. Where X or X
1
is CO
2
R co-ordination to the metal occurs through an O atom and the C atom to which it is attached is included to form a 6 -membered ring.
M is preferably Zn
2+
, Cu
2+
, Co
2+
, Co
3+
, Pt
2+
, Pd
2+
, Cr
3+
or Ni
2+
.
Optional substitutents for Rings A and B are preferably selected from C
1-4
-alkyl, aryl, SO
3
H, SO
2
NR
2
, CO
2
H or PO
3
H
2
in which R is as defined above.
In a first preferred embodiment of the present invention in the compound of Formula (1) G is a group of Formula (2), this is shown below as the compound of Formula (5).
in which Y, Y
1
, X, X
1
, M, Ar, L
1
, L
2
, L
3
, S and n are as defined above.
In a second preferred embodiment of the present invention in the compound of Formula (1) G is a group of Formula (3), this is shown below in the compound of Formula (6).
in which Y, Y
1
, X
1
, M, L
1
, L
2
, L
3
, Z, S, Ring B and n are as defined above.
In a third preferred embodiment of the present invention in the compound of Formula (1) G is a group of Formula (4), this is shown below as the compound of Formula (7);
in which Y, Y
1
, X
1
, M, L
1
, L
2
, L
3
, Z and Rings A and B are as defined above.
In a further preferred embodiment of the present invention in the compound of Formula (1) is G is a group of Formula (4):
Z preferably comprises a chain of two or three carbon atoms or one or two carbon atoms and one nitrogen atom, more preferably Z is of formula —CR
2
═CR
2
—CR
2
═wherein each R
2
is independently H or a substituent, of which one may be a hydrophilic group for example a carboxy, amido, sulpho, sulphonamide or phosphate group in order to increase the water solubility of the compound; it is preferred that any non hydrophilic substituent is H. It is especially preferred that X forms part of a quinoline group;
X
1
is preferably O or NR
3
wherein R
3
is H or optionally substituted alkyl.
Y is preferably CN, CONR
4
R
5
, SO
2
NR
4
R
5
, COR
4
or CO
2
R
4
wherein R
4
and R
5
are each independently H or C
1-4
-alkyl groups which may be substituted by water-solubilising groups preferably carboxy, amido, sulpho, sulphonamide or phosphato groups;
or R
4
and R
5
together with the nitrogen atom to which they are attached form a 5- or 6-membered ring;
M is preferably Zn
2+
, Cu
2+
, Co
2+
, Co
3+
, Pt
2+
, Pd
2+
, Cr
3+
or Ni
2+
, more preferably Ni
2+
; and
L
1
, L
2
and L
3
represent three monodentate ligands, one bidentate ligand and one monodentate ligand or one tridentate ligand.
Monodentate ligands include cosolvents for the compound, for example lower alcohols (for example C
1-6
-alkylOH, preferably C
1-4
-alkylOH), tetrahydrofuran or ammonia.
The ligands L
1
, L
2
and L
3
may be 3 separate independently selected monodentate ligands, or a monodentate ligand and a bidentate ligand or preferably a tridentate ligand; preferred tridentate ligands rep

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