Dye compositions

Details Dye compositions Dye compositions

1998-12-04

2001-07-31

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031500, C106S031520

Reexamination Certificate

active

06267806

ABSTRACT:

This invention relates to a composition comprising two or more dyes, to inks containing such compositions and to processes using said inks in printing and imaging technologies, especially ink jet printing.
Ink jet printing is a non-impact printing technique which involves ejecting, thermally or by action of an oscillating piezo crystal, droplets of ink continuously or on demand from a fine nozzle directly onto a substrate. The inks used in an ink jet printer are required to meet a number of criteria. For example they desirably provide sharp, non-feathered images which have good waterfastness, lighffastness and optical density. Furthermore, the inks are required to dry quickly when applied to a substrate, however, they must not dry or crust over in the ink jet head as this can result in clogging of the ink jet nozzle. The inks are also required to be storage stable for long periods of time without deterioration in the properties of the ink.
We have found that mixtures of certain dyes are valuable as colorants for ink jet printing inks.
According to a first aspect of the present invention there is provided a composition comprising a black dye and a dye of Formula (A) or salt thereof:
wherein:
R
1
is C
1-4
-alkoxy or C
1-4
-alkyl;
R
2
is H or C
1-4
-alkyl; and
R
3
and R
4
are each independently H, C
1-4
-alkyl or C
1-4
-hydroxyalkyl;
wherein the black dye is selected from dyes of Formula (1), (2), (3), (4), (5), (6), (7) or (8) and salts thereof:
wherein
R
5
is —COOH or —PO(OH)
2
;
B is 1,4-phenylene carrying two groups selected from C
1-4
-alkyl and C
1-4
-alkoxy;
m is 1 or 2; and
R
6
is vinyl sulphonyl, hydroxyethyl sulphonyl or a group which is convertible to vinyl sulphonyl when treated with aqueous alkali.
The —SO
3
H group in the left hand phenyl group in Formula (A) is preferably at the 3-position.
R
1
is preferably meta to the azo group.
The group represented by R
1
is preferably methyl, ethyl, methoxy or ethoxy, especially methoxy.
The group represented by R
2
is preferably H or methyl, especially H. The group represented by R
3
and R
4
are preferably each independently H, methyl, ethyl or —CH
2
CH
2
OH. It is preferred that one of R
3
and R
4
is H and the other is —CH
2
CH
2
OH.
An especially preferred dye of the Formula (A) is of the formula below or a salt thereof:
The above dye is available commercially as C.I.Direct Yellow 142.
The composition may contain a single dye selected from the dyes of Formulae (1) to (8), or a mixture of two or more of the dyes of Formulae (1) to (8).
The composition preferably comprises:
(a) from to 99 to 50 parts, more preferably 95 to 60 parts, especially 90 to 65 parts of one or more of the black dye(s); and
(b) from 1 to 50 parts, more preferably 5 to 40 parts, especially 10 to 35 parts of a dye of Formula (A);
wherein the parts are by weight and the sum of the parts (a) and (b)=100.
A preferred mixture of dyes of Formulae (1) to (8) comprises a mixture of two or three different dyes of Formula (1). Such mixtures are described in EP 761,771A and EP 771,860A.
A preferred black dye of Formula (1) is of the Formula (9) or a salt thereof:
wherein:
R
5
is as hereinbefore defined;
one of X and Y is C
1-4
-alkoxy and the other is C
1-4
-alkyl or C
1-4
-alkoxy; and
m is 1 or 2.
When R
6
in the dye of Formula (7) is a group which is convertible to a vinyl sulphonyl group when treated with aqueous alkali it is preferably of the formula: —SO
2
CH
2
CH
2
OSO
3
H, —SO
2
CH
2
CH
2
SSO
3
H, —SO
2
CH
2
CH
2
Cl or —SO
2
CH
2
CH
2
OCOCH
3
. It is preferred that R
6
is —SO
2
CH
2
CH
2
OH or, more preferably, —SO
2
CH
2
CH
2
OSO
3
H. R
6
is preferably attached in the para position relative to the azo group in the dye of Formula (7).
Dyes of Formula (A) may be prepared by reacting an amine of formula HNR
3
R
4
with a chlorotriazine analogue of the compound of Formula (A) in which there is a Cl atom in place of the —NR
3
R
4
group. The chlorotriazine analogue may be prepared by condensing 2 moles of a compound of Formula (B) with one mole of cyanuric chloride:
The compounds of Formula (B) may be prepared by diazotising a sulphoaniline and coupling onto benzene carrying an R
1
and NR
2
H group.
Certain dyes of Formula (A) are commercially available, for example C.I. Direct Yellow 142.
The dyes of Formula (1) may be prepared using methods known in the art for the preparation of azo compounds. For example, suitable methods for the preparation of the dyes of Formula (1) are described in European patent applications No. EP 761,771A, EP 771,860A and EP 356 080A. The dyes of Formula (1) may be converted into the free acid form or into a salt with a counter ion other than sodium by using well known techniques. For example, the alkali metal salts of the dye of Formula (1) may be converted into a salt with ammonia or an amine by dissolving the dye in the form of a salt with an alkali metal, acidifying with a mineral acid and adjusting the pH of the solution to pH 9 to 9.5 with ammonia or the amine and removing the alkali metal cations by dialysis. An example of a suitable process for converting the sodium salt of the dye of Formula (1) to the ammonium salt is analogous to that described in Example 21 of EP 356, 080A.
The dye of Formula (2) is Food Black 2 and is commercially available from Bayer.
The dye of Formula (3) is commercially available from various manufacturers as C.I.Direct Black 19. The dye of Formula (3) may be prepared using conventional techniques for the preparation of azo dyes. For example a suitable method comprises:
(1) diazotising 1,4-phenylenediamine using, for example, sodium nitrite in a mineral acid at 0 to 5° C.;
(2) coupling 8-amino-1-naphthol-3,6-disulphonic acid with an approximately equimolar quantity of the diazotised 1,4-phenylene diamine from stage (1) under slightly acidic conditions;
(3) adjusting the pH of the solution resulting from stage (2) so that it is alkaline, preferably in the range pH 8 to 9, and adding a further equimolar quantity of diazotised 1,4-phenylenediamine from stage (1); and
(4) coupling the diazotised disazo dye formed in stage (3) with approximately 2 molar equivalents of 1,3-phenylenediamine to give the dye of Formula (3).
The dyes of Formulae (4) to (6) may be prepared using methods analogous to those used for the preparation of similar azo dyes. A suitable method comprises:
(1) diazotising 4,4′-diamino-stilbene-2,2′-disulphonic acid using, for example, sodium nitrite in a mineral acid at 0 to 5° C.; and
(2) coupling the diazonium salt from stage (1) with approximately 2 molar equivalents of a compound XH, preferably under mildly alkaline conditions. For the dye of formula (4) the compound XH is 2-amino-8-naphthol-6-sulphonic acid. For the dye of formula (5) the compound XH is 8-amino-1-naphthol-3,6-disulphonic acid. For the dye of Formula (6) the compound XH is an approximately equimolar mixture of 8-amino-1-naphthol-3,6-disulphonic acid and 2-amino-8-naphthol-6-sulphonic acid.
The dye of Formula (7) wherein R
6
is —SO
2
CH
2
CH
2
OSO
3
H, is commercially available from various manufacturers as C.I.Reactive Black 31. The dye of Formula (7) may be prepared using conventional methods for the preparation of azo dyes. For example, a suitable method comprises:
(1) diazotising 2-amino-8-naphthol-6-sulphonic acid and coupling the resultant diazonium salt with the pyrazolone compound of the formula:
(2) diazotising the compound of the formula:
wherein R
6
is as hereinbefore defined;
(3) coupling the diazonium salt from stage (2) with the product of stage (1), preferably under alkaline conditions; and
(4) heating the azo dye formed in stage (3) in the presence of cuprammonium sulphate and a suitable alkanolamine, such as dihydroxyethylamine, to give the dye of Formula (7).
When R
6
is hydroxyethylsulphonyl, it is preferred that the dye is prepared by hydrolysing a dye of the Formula (7) wherein R
6
is —SO
2
CH
2
CH
2
OSO
3
H.
The dye of Formula (8) is commercially available as C.I.Direct Black 168.
Dyes of the Formula (9) are described in EP 356 080A.
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