Monoazo dyestuffs, a composition and an ink for ink jet...

Details Monoazo dyestuffs, a composition and an ink for ink jet... Monoazo dyestuffs, a composition and an ink for ink jet...

2000-08-28

2002-12-03

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C534S772000

Reexamination Certificate

active

06488752

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 and tautomers thereof:
wherein:
R
1
and R
2
each independently is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted arylalkyl;
each W and each X independently is —COOH, —SO
3
H, —PO
3
H
2
or alkyl substituted by one or more groups selected from —COOH, —SO
3
H and —PO
3
H
2
;
each Y and each Z independently is a substituent other than those defined for W and X;
a and d each independently is 1 to 5;
b and c each independently is 0 to 4;
(a+b) has a value of 5 or less; and
(c+d) has a value of 5 or less.
b and c are preferably each independently 0, 1 or 2, more preferably 0 or 1.
a and d are preferably each independently 1, 2, or 3, more preferably 1 or 2.
Preferably (a+b) has a value of 1, 2 or 3, more preferably 1 or 2. Preferably (c+d) has a value of 1, 2 or 3, more preferably 2 or 3.
The compounds of Formula (1) are preferably mono azo compounds (i.e. they contain only one azo (—N═N—) group).
Preferably each W and each X independently is —COOH, —SO
3
H, —PO
3
H
2
or C
1-10
alkyl (more preferably C
1-6
-alkyl) substituted by one, two or three (more preferably one) groups selected from —COOH, —SO
3
H, and —PO
3
H
2
.
More preferably each W and each X independently is —COOH, —SO
3
H or C
1-6
-alkyl substituted by —COOH or —SO
3
H. It is especially preferred that each X is —COOH. It is especially preferred that each W independently is —COOH or —SO
3
H.
Preferably at least one W is ortho to the azo group (—N═N—).
Preferably Y and Z are each independently optionally substituted aryl, optionally substituted arylalkyl, halogen (especially F and Cl), nitro, cyano, —CF
3
, —OR
3
, —NR
4
R
5
, —SR
6
, —C(O)R
7
, —C(O)OR
8
, —SO
2
R
9
, —SOR
10
or alkyl optionally substituted by a group other than —SO
3
H, —COOH or —PO
3
H
2
; or
Z together with the carbon atom to which it is attached and a second carbon atom in the phenyl group form a 5- or 6-membered ring;
 wherein:
R
3
is H, optionally substituted alkyl or optionally substituted aryl;
R
6
is H, optionally substituted alkyl, optionally substituted aryl or a group of the Formula (2);
R
7
, R
8
, R
9
and R
10
are each independently optionally substituted alkyl or optionally substituted aryl;
R
4
and R
5
are each independently H, optionally substituted alkyl, optionally substituted aryl, —CO(C
1-6
-alkyl), —CONH
2
, a group of the Formula (2) or R
4
and R
5
together with the nitrogen to which they are attached form a 5- or 6- membered ring:
L
1
and L
2
each independently is —OR
11
, —SR
12
or —NR
13
R
14
;
R
11
and R
12
each independently is H, optionally substituted aryl or optionally substituted alkyl; and
R
13
and R
14
each independently is H, optionally substituted aryl, optionally substituted alkyl, —CO(C
1-6
-alkyl) or —CONH
2
or R
13
and R
14
together with the nitrogen to which they are attached form an optionally substituted morpholine or piperazine ring.
In a preferred embodiment Y and Z are each independently optionally substituted aryl, optionally substituted arylalkyl, halogen (especially F and Cl), nitro, cyano, —CF
3
, —OR
3
, —NR
4
R
5
, —SR
6
, —C(O)R
7
, —C(O)OR
8
, —SO
2
R
9
, —SOR
10
or alkyl optionally substituted a group other than —SO
3
H, —COOH or —PO
3
H
2
; wherein R
3
, R
4
, R
5
, R
7
, R
8
, R
9
and R
10
are as hereinbefore defined and R
6
is H, optionally substituted alkyl or optionally substituted aryl.
Preferably R
7
, R
8
, R
9
and R
10
are each independently optionally substituted alkyl.
When any of Y and Z is optionally substituted alkyl it is preferably optionally substituted C
1-10
-alkyl, more preferably C
1-6
alkyl optionally substituted by —OH, nitro, cyano, halogen (especially F or Cl), amino, —NH(C
1-4
-hydroxyalkyl) or —NH(C
1-4
-alkyl).
When any of R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
and R
14
is optionally an substituted alkyl it is preferably optionally substituted C, ,
0
-alkyl, more preferably optionally substituted C
1-6
-alkyl. Preferred optional substituents are —OH, —COOH, —SO
3
H, —PO
3
H
2
, nitro, amino and halogen (preferably F or Cl), more especially Cl, —OH, —COOH and —SO
3
H.
When any of R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
and R
14
is optionally substituted aryl it is preferably optionally substituted phenyl or optionally substituted naphthyl, especially optionally substituted phenyl. Preferred optional substituents are C
1-4
-alkoxy, (C
1-4
-hydroxyalkoxy)-C
1-4
-alkoxy-, —OH, —COOH, —SO
3
H, —CF
3
, amino, —NH(C
1-4
-alkyl), —NH(C
1-4
-hydroxyalkyl), —NH(—CO(C
1-4
-alkyl)), halogen (especially F or Cl), nitro, —CO(C
1-4
-alkyl), —SO
2
(C
1-4
alkyl) and C
1-4
-alkyl optionally substituted by —OH, —COOH and —SO
3
H.
When any of R
1
, R
2
, Y or Z is arylalkyl it is preferably optionally substituted phenyl-(alkylene)- or optionally substituted naphthyl-(alkylene)- more preferably optionally substituted phenyl-(C
1-6
-alkylene)- or optionally substituted naphthyl-(C
1-6
-alkylene)- and especially optionally substituted benzyl. Preferred optional substituents on the arylalkyl groups are those listed above for the aryl groups, more preferably C
1-4
-alkyl, C
1-4
-alkoxy, —SO
3
H, —COOH, amino, nitro, F or Cl.
When Z together with the carbon atom to which it is attached and a second carbon atom in the phenyl group form a 5- or 6-membered ring, the group attached to the azo group of Formula (1) is preferably a substituted indanyl group, more preferably a group of the Formula (A):
wherein:
k is 0, 1 or 2;
W and d are as hereinbefore defined; and
each T independently is as hereinbefore defined for Z.
Preferably each T independently is C
1-6
-alkyl or C
1-6
-alkoxy each of which is optionally substituted by —OH.
In Formula (A) k is preferably 0. Preferably d is 1 or 2. It is especially preferred in Formula (A) that k is 0, d is 1 or 2 and at least one W is ortho to the azo group in Formula (1).
When R
4
and R
5
together with the nitrogen to which they are attached form a 5 or 6 membered ring it is preferably optionally substituted morpholine or optionally substituted piperazine.
Preferred optional substituents on the rings which may be formed by R
4
and R
5
, and R
13
and R
14
, together with the nitrogen to which they are attached are selected from —OH, —COOH, —SO
3
H, C
1-4
-alkoxy and C
1-4
-alkyl optionally substituted by —OH, —COOH or —SO
3
H.
R
7
, R
8
, R
9
and R
10
are preferably each independently C
1-4
-alkyl, more preferably methyl or ethyl.
When R
4
or R
5
is a group of the Formula (2), the other group attached to the nitrogen (R
5
and R
4
respectively) is preferably H or C
1-4
-alkyl.
Preferably each Z and each Y is free from —COOH, —SO
3
H and —PO
3
H
2
groups.
Preferably R
1
is H, optionally substituted C
1-10
-alkyl, optionally substituted phenyl or optionally substituted phenyl-(C
1-6
-alkylene), more preferably H, phenyl, benzyl or C
1-6
-alkyl optionally substituted by —OH, —SO
3
H or —COOH, especially H or C
1-4
-alkyl, more especially H.
Preferably R
2
is optionally substituted C
1-10
-alkyl, optionally substituted phenyl or optionally substituted benzyl, more preferably phenyl, benz

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