Disazo dyes and inks containing them

Details Disazo dyes and inks containing them Disazo dyes and inks containing them

2002-03-18

2004-05-18

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031500, C106S031760, C106S031770, C106S031780, C347S100000, C427S466000, C428S032100, C534S797000

Reexamination Certificate

active

06736888

ABSTRACT:

This invention relates to compounds, to inks comprising these compounds, ink jet printer cartridges containing these inks and to their use in ink jet printing (“IJP”).
IJP is a non-impact printing technique in which droplets of ink 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 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.
According to the present invention there is provided a compound comprising a disazo chromophore and an optionally substituted heterocyclic group linked together through a —SO
2
NH— group.
Preferably the nitrogen atom of the —SO
2
NH— group is attached to the heterocyclic group by means of a single covalent bond. It is especially preferred that the compound is of Formula (1):
A—NH—SO
2
—B—N═—D—N═N—E  Formula (1)
wherein:
A is an optionally substituted heterocylic group;
B and D are each independently optionally substituted phenylene or naphthylene; and
E is optionally substituted naphthylene.
The optionally substituted heterocyclic group preferably comprises an optionally substituted 5- or 6-membered heterocyclic ring, optionally having a benzene ring fused thereon. Preferred heterocyclic rings comprise 2, 3, 4 or 5 carbon atoms and 1, 2 or 3 atoms selected from oxygen, nitrogen and sulphur.
Preferably the optionally substituted heterocyclic group is an optionally substituted diazine, thiazole, benzthiazole, benzdiazine, isoxazole, benzisoxazole, thiadiazole, oxadiazole, isothiazole, triazole, benzisothiazole, pyridiazine, triazine, oxazole, thiophene, benzoxazole, pyrimidine or pyridine, preferably attached to the —NH—SO
2
— group through a carbon atom adjacent to an oxygen, sulphur or nitrogen atom (e.g. at the 2-position). Particularly preferred are optionally substituted 2-thiazole, 2-benzthiazole and 2-diazine groups.
Preferably B is optionally substituted phenylene, more preferably optionally substituted 1,4-phenylene.
Preferably D is an optionally substituted 1,4-phenylene group, more preferably a group of the formula:
wherein each:
W independently is H, optionally substituted alkyl, optionally substituted alkoxy, polyalkylene oxide, nitro, cyano, sulpho, halo, ureido, SO
2
F, hydroxy, carboxy, ester, PO
4
H
2
, —NR
1
R
2
, —COR
1
, —CONR
1
R
2
or —SO
2
NR
1
R
2
;
X independently is O, NH or S;
R
1
and R
2
are each independently H or alkyl, preferably H or C
1-4
-alkyl; and
R
3
independently is H, optionally substituted alkyl or optionally substituted aryl.
Preferably each W independently is H, C
1-4
-alkyl or C
1-4
-alkoxy more preferably H, methyl, ethyl, methoxy or ethoxy, especially H. Preferably both groups represented by W are H and X is O.
Preferably each R
3
independently is optionally substituted C
1-4
-alkyl or optionally substituted phenyl more preferably C
1-4
-alkyl or C
1-4
-alkyl-OH, phenyl or phenyl carrying one or two substituents selected from carboxy and sulpho.
Preferred optional substituents which may be present on the optionally substituted heterocyclic group, B, D or E are each independently selected from alkyl, more preferably C
1-4
-alkyl; alkoxy, more preferably C
1-4
-alkoxy; polyalkylene oxide; nitro; cyano; sulpho; halo, especially bromo, chloro or fluoro; ureido; SO
2
F; hydroxy; carboxy; ester, more preferably—CO
2
(C
1-4
-alkyl); PO
4
H
2
and —NR
1
R
2
, —COR
1
, —CONR
1
R
2
and —SO
2
NR
1
R
2
wherein R
1
and R
2
are each independently H or alkyl, preferably H or C
1-4
-alkyl.
When D is also optionally substituted naphthylene it preferably carries one or more (preferably 1 to 4) substituents selected from hydroxy, amino, sulpho and carboxy.
Preferably E is optionally substituted naphthylene, more preferably carrying one or more (preferably from 1 to 4) groups selected from hydroxy, amino, sulpho and carboxy. More preferably E is naphthylene carrying one hydroxy group, one amino group and 0, 1 or 2 sulpho groups. It is especially preferred that E is a 1-hydroxy-3-sulphonaphth-2-ylene group carrying an optionally substituted amino group at the 7-position; or a 1-hydroxy-5-sulphonaphth-2-ylene group carrying an optionally substituted amino group at the 8-position; or a 1-hydroxy-3,6-disulphonaphth-2-ylene group carrying an optionally substituted amino group at the 8-position or a 1-hydroxy-3,6-disulphonaphth-2-ylene group carrying an optionally substituted amino group at the 7-position.
Preferred optionally substituted amino groups are of the formula —NR
4
R
5
where R
4
and R
5
are independently selected from H, optionally substituted alkyl and optionally substituted phenyl. Preferably R
4
and R
5
are both H.
The compounds described hereinbefore are preferably soluble in water. To achieve this solubility, the compounds preferably have 1, 2 or 3 water-dispersing substituents. Preferred water-dispersing substituents are polyalkylene oxides and more preferably sulpho and carboxy.
Preferred polyalkylene oxide groups which may be present on A, B, D and/or E are poly(C
2-3
-alkylene oxide) groups, more preferably polyethylene glycol or polypropylene glycol, preferably having from 1 to 20 glycol units and terminated with a hydroxy or C
1-4
-alkoxy group.
Preferably A, B, D and E are selected from the definitions given above such that the pKa of the linking —NH— group is from 8 to 3, more preferably 7.5 to 4, especially 7 to 4.5. These preferences arise from the finding that compounds having such an —NH— group have a particularly good combination of water-fastness and optical density when printed on paper.
Any acid or basic groups on the compound, particularly carboxylic acid and sulphonic acid groups, are preferably in the form of a salt. Thus the Formulae shown herein include the compounds in free acid and in salt form.
The compounds of the invention may be prepared by condensing a diazo chromophore and an optionally substituted heterocyclic compound, where one has a sulphonyl halide substituent and the other has an amino substituent. This condensation is preferably performed in the present of base to absorb hydrogen halide as it is generated during the condensation.
The compound of Formula A—NH—SO
2
—B—N═N—D—N═N—E may be prepared by diazotising an amine of the formula A—NH—SO
2
—B—N═N—D—NH
2
and coupling the resultant diazonium salt with a compound of the formula H—E.
The compound of Formula A—NH—SO
2
—B—N═N—D—NH
2
may be prepared by diazotising an amine of the formula A—NH—SO
2
—B—NH
2
and coupling the resultant diazonium salt with an amine of the formula H—D—NH
2
. In some cases it may be necessary for the amino group to carry a protecting group which should be removed on completion of the reaction.
Many compounds of the formula A—NH—SO
2
—B—NH
2
are commercially available.
Preferably they may be prepared by condensing an amine of formula B—(NH
2
)
2
, in which one of the amino groups is protected, with a compound of formula Cl—SO
2
—NH—A followed by removal of the protecting group.
More preferably they may be prepared by condensing an amine of formula A—NH
2
with a compound of formula Cl—SO
2
—B—NH
2
carrying a protecting group on the amino group. of the Cl—SO
2
—B—NH
2
compound, followed by removal of the protecting group.
Diazotisation is preferably performed at a temperature below 6° C., more preferably at a temperature in the range −10° C. to 5° C. Preferably diazotsation is performed in water. The coupling reactions are performed at a pH below 7 for the monoazo intermediate and above pH 7 to form compounds of Formula (1). Dilute mineral acid, e.g. HCl or H
2
SO
4
, may be used to achieve the desi

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