Disazo dyestuffs for ink jet printing

Details Disazo dyestuffs for ink jet printing Disazo dyestuffs for ink jet printing

2002-03-26

2004-02-24

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031500, C534S797000, C534S836000, C427S466000, C428S032100, C347S100000

Reexamination Certificate

active

06695899

ABSTRACT:

This invention relates to dyes, to 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 of Formula (1) and salts thereof:
wherein:
A is a substituted phenyl group carrying a group of the formula —NR
3
R
4
and an ortho carboxy group;
n is 0 or 1;
L
1
and L
2
are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or L
1
and L
2
together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring;
R
1
and R
2
are each independently optionally substituted alkyl or optionally substituted alkoxy; and
R
3
and R
4
are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or R
3
and R
4
together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring; or
R
3
is H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl and R
4
is an acyl group.
In a first preferred embodiment n is 0; L
1
and L
2
are H; and R
3
and R
4
are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or R
3
and R
4
together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring.
In a second preferred embodiment n is 1; L
1
and L
2
are H; and R
3
and R
4
are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or R
3
and R
4
together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring.
In a third preferred embodiment n is 0; L
1
and L
2
are H; R
3
is H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl; and R
4
is an acyl group.
In a fourth preferred embodiment n is 1; L
1
and L
2
are H; R
3
is H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl; and R
4
is an acyl group.
Preferred acyl groups represented by R
4
are of the formula —COR
5
, —SOR
5
or —SO
2
R
5
wherein, R
5
is H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl. It is especially preferred that R
4
is of the formula CH
3
(CH
2
)
a
CO—wherein a has a value from 0 to 3.
Optional substituents which may be present on L
1
, L
2
R
1
, R
2
, R
3
, R
4
and R
5
are preferably selected from —NH
2
; halo, especially Cl, Br and F; ester, especially —CO
2
—C
1-4
-alkyl; —O—C
1-4
-alkyl; —CO
2
H; —SO
3
H; —OR
6
; or —SR
6
; wherein each R
6
independently is H or C
1-4
-alkyl.
Preferably at least one of R
1
and R
2
, or more preferably both R
1
and R
2
, carries an —OH group.
When L
1
, L
2
, R
1
, R
2
, R
3
, R
4
or R
5
is an optionally substituted alkyl group it is preferably an optionally substituted C
1-4
-alkyl group, more preferably a C
1-4
-alkyl group or a C
1-4
-alkyl-OH group.
When R
1
or R
2
is an optionally substituted alkoxy group it is preferably an optionally substituted C
1-4
-alkoxy group, more preferably a C
1-4
-alkoxy or C
1-4
-alkoxy-OH group.
R
1
and R
2
are preferably each independently optionally substituted C
1-4
-alkyl or optionally substituted C
1-4
-alkoxy, provided that at least one of R
1
and R
2
carries an —OH group, more preferably optionally substituted C
1-4
-alkoxy, especially C
1-4
-alkoxy-OH.
In one embodiment one of R
1
and R
2
is —OC
1-4
-alkyl-OH and the other is —OC
1-4
-alkyl or —OC
1-4
-alkyl-OH.
When L
1
, L
2
, R
3
, R
4
or R
5
is optionally substituted aryl it is preferably optionally substituted phenyl, more preferably phenyl or phenyl carrying a carboxy and/or sulpho group. When R
3
and R
4
or L
1
and L
2
together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring such ring is preferably an optionally substituted morpholino or piperidino ring.
Based on the above preferences it is preferred that R
3
and R
4
are each independently selected from optionally substituted C
1-4
-alkyl and optionally substituted phenyl, or R
3
and R
4
together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring. It is especially preferred that R
3
and R
4
are each independently selected from C
1-4
-alkyl, C
1-4
-alkyl-OH, phenyl and phenyl carrying a carboxy and/or sulpho group, or R
3
and R
4
together with the nitrogen to which they are attached form an optionally substituted morpholino or piperidino ring.
It is also preferred that when R
4
is acyl that R
3
is selected from optionally substituted C
1-4
-alkyl and optionally substituted phenyl. It is especially preferred that when R
4
is acyl, R
3
is selected from C
1-4
-alkyl, C
1-4
-alkyl-OH, phenyl and phenyl carrying a carboxy and/or sulpho group.
It is especially preferred that the group of the formula —NR
3
R
4
is in the para position with respect to the azo linkage because this gives particularly good high optical density.
The dyes of Formula (1) may be prepared by diazotising a compound of the Formula (2) to give a diazonium salt and coupling the resultant diazonium salt with a 1-hydroxy-3-sulphonaphthalene or 1-hydroxy-3,6-disulphonaphthalene, in each case carrying an NL
1
L
2
substituent at the 7-position:
wherein A, L
1
, L
2
, R
1
and R
2
are as hereinbefore defined.
The hydroxy group(s) on R
1
and/or R
2
may be protected during the diazotisation, for example using an acid labile or base labile protecting group. The acetoxy protecting group is particularly convenient and inexpensive.
The diazotisation is preferably performed at room temperature or below. Preferably the diazotisation is performed in water, preferably at a pH below 7. Dilute mineral acid, e.g. HCl or H
2
SO
4
, may be used to achieve the desired acidic conditions.
The compound of Formula (2) may be prepared by diazotising a compound of formula A—NH
2
and coupling onto an aniline compound carrying R
1
and R
2
groups at the 2- and 5- positions respectively, wherein A, R
1
and R
2
are as hereinbefore defined.
Preferred salts are alkali metal salts (especially lithium, sodium and potassium salts), ammonium and substituted ammonium salts and mixtures thereof. Especially preferred salts are sodium, potassium and lithium salts, salts with ammonia and volatile amines and mixtures thereof. The lithium salts have good solubility, forming particularly storage stable inks with low tendency to block ink jet nozzles.
The dyes may be converted into a desired salt using known techniques. For example, an alkali metal salt of a dye may be converted into the ammonium or substituted ammonia salt by dissolving an alkali metal salt of the dye in water, 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 or by use of an ion exchange resin.
Examples of amines which may be used to form such salts include methylamine, dimethylamine, trimethylamine, ethylamine, n-propylamine, iso-propylamine, n-butylamine, iso-butylamine, sec-butylamine, tert-butylamine, piperidine, pyridine, morpholine, allylamine, diethylamine, triethylamine and mixtures thereof. It is not essential that the dyes are completel

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