Dye composition

Details Dye composition Dye composition

2002-09-04

2004-07-27

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C008S673000, C008S681000, C008S688000, C347S100000, C428S195100, C427S466000

Reexamination Certificate

active

06767394

ABSTRACT:

This invention relates to dye compositions and to their use in ink jet printing (“IJP”). 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.
There are many demanding performance requirements for dyes and inks used in IJP. For example they desirably provide sharp, non-feathered images having good water-fastness, light-fastness, chroma, and optical density. The inks are often 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 jet nozzle because this will stop the printer from working. The inks should also be stable to storage over time without decomposing or forming a precipitate which could block the fine nozzle. Thermal and piezoelectric ink jet printers are widely used, thus there is a need for inks, suitable for use in both types of printers, having high colour strength and giving images having good light fastness when printed on a typical substrate, especially plain paper.
Inks containing dyes are known for example from U.S. Pat. No. 5,622,550 which discloses a yellow ink composition comprising a mixture of a triazine linked carboxylated azo benzenoid dye with a triazine linked sulphonated azo benzenoid dye or a pyrazolone linked sulphonated dye.
EP 763 576 discloses the use of yellow dye mixtures comprising dyes containing carboxy groups with dyes containing a SO
3
H group.
We have found that a combination of a triazine linked azo benzenoid dyes with a pyridone dye provides an improved balance of lightfastness, chroma and dye solubility.
According to a first aspect of the present invention there is provided a composition comprising a dye of Formula (I) and a dye of Formula (II) or salts thereof:
wherein
Ar
1
, Ar
2
, Ar
3
, Ar
4
and Ar
5
are each independently optionally substituted aryl;
R
1
is alkyl, alkenyl, alkynyl, pyridinium or aryl, each of which is substituted or unsubstituted, or H;
R
2
is alkyl, alkenyl, alkynyl, pyridinium or aryl, each of which is substituted or unsubstituted, H, C(O)OH, CN, NR
5
R
6
or C(O)NR
5
R
6
; and
R
3
, R
4
, R
5
and R
6
each independently are alkyl, alkenyl, alkynyl or aryl, each of which is substituted or unsubstituted, or H;
L is H or L and R
4
together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring.
Preferably the dye of Formula (I) is of the formula:
wherein:
R
7
is alkyl, alkoxy, alkenyl, alkynyl or aryl, each of which is substituted or unsubstituted, H, SO
3
H, C(O)OH, PO
3
H, NR
5
R
6
or C(O)NR
5
R
6
;
p is 0, 1, 2or 3; and
R
1
, R
2
, R
3
, R
5
and R
6
are as defined above.
Preferably the dye of Formula (II) is of the formula:
wherein
each R
8
independently is alkyl, alkenyl, alkynyl or aryl, each of which is substituted or unsubstituted, H, NHC(O)R
5
or NHC(O)NR
5
R
6
;
each R
9
independently is alkyl, alkenyl, alkynyl, or aryl, each of which is substituted or unsubstituted, H, SO
3
H, PO
3
H or NH
3
+
;
each m independently is 0, 1, 2 or 3; and
L, R
4
, R
5
, R
6
, Ar
3
and Ar
5
are as defined above.
Preferably L is H.
Preferably R
1
is C
1
-C
25
alkyl, C
2
-C
25
alkenyl, C
2-25
alkynyl, pyridinium or aryl, each of which is substituted or unsubstituted, or H; more preferably R
1
is H or optionally substituted C
1
-C
15
alkyl; most preferably R
1
is C
1
-C
10
alkyl or —SO
3
H substituted C
1
-C
10
alkyl;
Preferably R
2
is C
1
-C
25
alkyl, C
2
-C
25
alkenyl, C
2
-C
25
alkynyl, pyridinium or aryl, each of which is substituted or unsubstituted, H, C(O)OH, CN, NR
5
R
6
or C(O)NR
5
R
6
; more preferably R
2
is pyridinium or C
1
-C
15
alkyl each of which is substituted or unsubstituted, H, C(O)OH, CN, NR
5
R
6
or C(O)NR
5
R
6
; most preferably R
2
is pyridinium or C
1
-C
10
alkyl, each of which is substituted or unsubstituted H, C(O)OH, CN, NR
5
R
6
or C(O)NR
5
R
6
.
Preferably R
3
, R
4
, R
5
and R
6
each independently are C
1
-C
25
alkyl, C
2
-C
25
alkyenyl, C
2
-C
25
alkynyl or aryl, each of which is substituted or unsubstituted, or H; more preferably R
3
, R
4
, R
5
and R
6
each independently are C
1
-C
20
alkyl, C
2
-C
20
alkyenyl, C
2
-C
20
alkynyl or aryl, each of which is substituted or unsubstituted, or H; most preferably R
3
, R
4
, R
5
and R
6
each independently are H or optionally substituted C
1
-C
10
alkyl.
Preferably R
7
is C
1
-C
25
alkyl, C
1
-C
25
alkoxy, C
2
-C
25
alkenyl, C
2
-C
25
alkynyl or aryl, each of which is substituted or unsubstituted, H, SO
3
H, C(O)OH, PO
3
H, NR
5
R
6
or C(O)NR
5
R
6
; more preferably R
7
is C
1
-C
15
alkyl or aryl, each of which is substituted or unsubstituted, H, SO
3
H, C(O)OH, PO
3
H, NR
5
R
6
or C(O)NR
5
R
6
; most preferably R
7
is C
1
-C
10
alkyl or aryl, each of which is substituted or unsubstituted, H, SO
3
H, C(O)OH, PO
3
H, NR
5
R
6
or C(O)NR
5
R
6
.
Preferably each R
8
independently is C
1
-C
25
alkyl, C
2
-C
25
alkyenyl, C
2
-C
25
alkynyl or aryl, each of which is substituted or unsubstituted, H, NHC(O)R
5
or NHC(O)NR
5
R
6
; more preferably each R
8
independently is optionally substituted C
1
-C
10
alkyl, H, NHC(O)R
5
or NHC(O)NR
5
R
6
; most preferably each R
8
independently is H, optionally substituted C
1
-C
5
alkyl, NHC(O)R
5
or NHC(O)R
5
R
6
.
Preferably each R
9
independently is C
1
-C
25
alkyl, C
2
-C
25
alkyenyl, C
2
-C
25
alkynyl or aryl, each of which is substituted or unsubstituted, H, SO
3
H, PO
3
H or NH
3
+
; more preferably each R
9
independently is optionally substituted C
1
-C
10
alkyl, H, SO
3
H, PO
3
H, or NH
3
+
; most preferably each R
9
independently is H or SO
3
H.
Preferably Ar
1
, Ar
2
, Ar
3
, Ar
4
and Ar
5
each independently are phenyl or napthyl; more preferably Ar
1
, Ar
2
and Ar
4
each independently are phenyl; and more preferably Ar
3
and Ar
5
each independently are napthyl.
Preferably each m independently is 1, 2 or 3.
In a particularly preferred embodiment of the present invention R
1
is C
1
-C
10
alkyl or —SO
3
H substituted C
1
-C
10
alkyl; R
2
is CN, optionally substituted pyridinium or optionally substituted C
1
-C
10
alkyl; R
3
, R
4
, R
5
and R
6
each independently are H or optionally substituted C
1
-C
10
alkyl; R
7
is SO
3
H, C(O)OH or optionally substituted C
1
-C
10
alkyl; each R
8
is independently H, C
1
-C
5
alkyl, NHC(O)R
5
, NHC(O)NR
5
R
6
; each R
9
independently is SO
3
H; Ar
1
, Ar
2
and Ar
4
are phenyl; Ar
3
and Ar
5
are napthyl; and each m independently is 1 or 2.
When R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
or the 5- or 6-membered ring formed by L and R
4
together with the N atom to which they are attached are optionally substituted the optional substituents include but are not limited to —S—; —O—; hydroxy; cyano; carboxyl; sulpho; nitro; ureido; C
1
-C
4
alkyl, for example methyl, ethyl propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl or iso-butyl; halogen, for example fluorine, chlorine or bromine; C
1
-C
4
alkoxy, for example methoxy, ethoxy, propoxy or butoxy; C
1
to C
4
alkoxycarbonyl, for example methoxy carbonyl or ethoxy carbonyl; —NHC(O)R
10
, —NR
10
R
11
, —C(O)NR
10
R
11
, —CHR
10
R
11
where R
10
and R
11
each independently are H or C
1
-C
6
alkyl or where R
10
and R
11
together with the atom to which they are attached form an optionally substituted 5- or 6-membered ring, preferably an optionally substituted pyrrolidino, morpholino, piperidino or tetrahydrofuran ring.
When L and R
4
together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring, the ring preferably comprises 3, 4 or 5 carbon atoms and optionally sulphur, oxygen and/or nitrogen atom(s). In a preferred embodiment L and R
4
form an optionally substituted pyrrolidino, morpholino, piperidino or tetrahydrofuran ring, most preferably a morpholino ring.
Preferably the weight ratio of the dye of Formula (I) to the dye of Formula (II) is from 1:10 to 10:1, more preferably 1:5 to 5:1, especially 1:3 to 3:1, more especially 1:2 to 1:2, particularl

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