Monoazo dyes and inks containing them

Details Monoazo dyes and inks containing them Monoazo dyes and inks containing them

1999-12-30

2002-02-05

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C534S803000, C427S466000, C428S195100

Reexamination Certificate

active

06344076

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 a first aspect of the present invention there is provided a compound of Formula (1):
wherein:
A is N, C—Cl, C—CN or C—NO
2
;
L
1
is —OR
3
;
Z is —O—, —S— or —NR
2
—;
R
1
and R
2
are each independently H or optionally substituted alkyl;
R
3
is H or alkyl;
each W independently is —CO
2
Q or —SO
3
Q;
each X independently is an optionally substituted amino group or a group which is substituted by an optionally substituted amino group;
each Y independently is a substituent other than those defined for W and X;
each Q independently is ammonium or substituted ammonium;
m, n and p each independently have a value of from 0 to 3; and
(m+n+p) has a value of from 0 to 5.
Preferably A is N.
Preferably m, n and p each independently have a value of 0 or 1.
Preferably n is 1 when m is 0
Preferably (m+n+p) has a value of 1, 2 or 3, more preferably 1 or 2.
Z is preferably —NR
2
—, more preferably —NH—.
Preferably each Y independently is halo, more preferably F or Cl; hydroxy; nitro; cyano; optionally substituted alkyl, preferably optionally substituted C
1-10
-alkyl, especially C
1-4
-alkyl; optionally substituted alkoxy, preferably optionally substituted C
1-10
-alkoxy, more preferably C
1-4
-alkoxy; optionally substituted aryl, preferably optionally substituted phenyl or optionally substituted naphthyl; optionally substituted aralkyl, preferably optionally substituted C
7-12
-aralkyl, more preferably phenyl-(C
1-6
-alkylene)-, especially phenyl-—CH
2
—; —SR
a
; —COR
a
; —COOR
a
; SO
3
R
a
; —SO
2
R
a
; or —SOR
a
; wherein R
a
is optionally substituted C
1-4
-alkyl; wherein the optional substituents are selected from carboxy, sulpho, hydroxy, nitro, cyano and halo.
R
1
and R
2
are preferably each independently H or optionally substituted C
1-4
-alkyl, more preferably H, C
1-4
-alkyl or C
2-4
-alkyl substituted by hydroxy, carboxy, sulpho or cyano. Examples include methyl, ethyl, n-propyl, iso-propyl, hydroxyethyl, cyanoethyl, sulphopropyl and carboxyethyl. It is especially preferred that R
1
and R
2
are H.
Preferably the compounds of Formula (1) are monoazo compounds (i.e. they contain only one azo (—N═N—) group).
R
3
is preferably H or C
1-10
-alkyl, more preferably H or C
1-6
alkyl, especially H or C
1-4
-alkyl, more especially H.
When X is, or is substituted by, an optionally substituted amino group, the optionally substituted amino group preferably has a pK
a
of from 12 to 4, more preferably of from 10 to 6.
The optionally substituted amino groups referred to in the definition of X are preferably of the formula —NR
4
R
5
wherein R
4
and R
5
are each independently H or optionally substituted alkyl; or R
4
and R
5
together with the nitrogen atom to which they are attached form a 5- or 6-membered ring.
When R
4
or R
5
is optionally substituted alkyl it is preferably optionally substituted C
1-6
-alkyl, more preferably optionally substituted C
1-4
-alkyl. Preferred substituents are selected from carboxy, sulpho, hydroxy, amino and C
1-4
-alkoxy.
When R
4
and R
5
together with the nitrogen to which they are attached form an optionally substituted 5- or 6-membered ring they preferably form optionally substituted morpholine, more preferably optionally substituted piperazine. The substituents are preferably selected from hydroxy, carboxy, sulpho, C
1-6
-alkoxy, C
1-6
-alkyl and C
1-6
-alkyl substituted by hydroxy, carboxy, sulpho or an optionally substituted amino group.
A preferred substituted morpholine or piperazine ring carries a group of the formula —M—NR
6
R
7
wherein M is an alkylene linking group and R
6
and R
7
are each independently H, C
1-6
-alkyl or C
1-6
-alkyl substituted by hydroxy, carboxy, sulpho, amino or C
1-4
-alkoxy.
M is preferably C
1-6
-alkylene, more preferably C
2-6
-alkylene and especially —(CH
2
)
g
—, where g is from 2 to 6.
An especially preferred substituted piperazinyl group is of the Formula (2):
wherein M, R
6
and R
7
are as hereinbefore defined.
Preferred groups of the Formula (2) include
Examples of optionally substituted amino groups include: —NH
2
, —NHCH
2
CH
3
, —N(CH
2
CH
3
)
2
, —NHCH
2
CH
2
OH:
—NH(CH
2
)
2
N(CH
3
)
2
, —NH(CH
2
)
2
N(CH
3
)
2
,
When X is a group which is substituted by an optionally substituted amino group it preferably comprises optionally interrupted alkylene carrying a —NR
4
R
5
group wherein R
4
and R
5
are as hereinbefore defined.
Preferably the optionally interrupted alkylene group comprise one, two or three C
2-10
-alkylene chains and 0, 1, 2, 3 or 4 interrupting groups selected from O, CO, CO
2
, S, SO, SO
2
, NH, optionally substituted phenylene, CONH and SO
2
NH. The interrupting groups may link each of the C
2-10
-alkylene chains and/or be at a terminal position in the interrupted alkylene chain.
Preferred interrupted alkylene groups having one C
2-10
-alkylene chain and one interrupting group are of the formula —SO
2
NH—(C
2-10
-alkylene)-; —NHSO
2
(C
2-10
-alkylene)—; —CONH—(C
2-10
-alkylene)—; —NHCO—(C
2-10
-alkylene)—; —[(O, S or NH)—C
2-10
-alkylene]—; —SO—(C
2-10
-alkylene)—; and SO
2
—(C
2-10
-alkylene)—.
Preferred interrupted alkylene groups having two C
2-10
-alkylene chains and two interrupting groups are any two of the groups described in the previous paragraph attached together, especially —SO
2
—(C
2-10
-alkylene)—NH—(C
2-10
-alkylene)—.
Q is preferably of the formula
+
NT
4
wherein each T independently is H or optionally substituted alkyl, or two groups represented by T are H or optionally substituted alkyl and the remaining two groups represented by T, together with the N atom to which they are attached, form a 5- or 6-membered ring (preferably a morpholine, pyridine or piperidine ring).
Preferably each T independently is H or C
1-4
-alkyl, more preferably H, CH
3
or CH
3
CH
2
, especially H. Thus Q is preferably ammonium (i.e.
+
NH
4
).
Examples of groups represented by Q include
+
NH
4
, morpholinium, piperidinium, pyridinium, (CH
3
)
3
N
+
H, (CH
3
)
2
N
+
H
2
, H
2
N
+
(CH
3
)(CH
2
CH
3
),CH
3
N
+
H
3
, CH
3
CH
2
N
+
H
3
, H
2
N
+
(CH
2
CH
3
)
2
, CH
3
CH
2
CH
2
N
+
H3, CH
3
CH
2
CH
2
N
+
H
3
, (CH
3
)
2
CHN
+
H
3
, N
+
(CH
3
)
4
, N
+
(CH
2
CH
3
)
4
, N-methyl pyridinium, N,N-dimethyl piperidinium and N,N-dimethyl morpholinium.
A first preferred embodiment of the present invention comprises a compound of the Formula (1) and salts thereof wherein:
A is N;
m is 0, 1 or 2;
n is 0 or 1;
p is 0 or 1;
X is of the formula —NR
4
R
5
or a group which is substituted by —NR
4
R
5
;
Y is halo, hydroxy, cyano, C
1-4
-alkyl, C
1-4
-alkoxy, —SR
a
, —COR
a
, —COOR
a
, —SO
3
R
a
, —SO
2
R
a
or SOR
a
; and
R
1
, R
2
, R
3
, R
4
, R
5
, R
a
, Q and W are as hereinbefore defined.
In the first preferred embodiment it is especially preferred that Y is C
1-4
-alkyl.
A second preferred embodiment comprises a monoazo compound of the Formula (3):
wherein:
Z is —O—, —S— or —NR
8
—;
R
8
is H or C
1-4
-alkyl optionally substituted by hydroxy, carboxy, sulpho or cyano;
L
2
is —OR
9
;
R
9
is H or C
1-4
-alkyl;
each W independently is —CO
2
Q or —SO
3
Q;
each X
1
is —NR
4
R
5
, —SO
2
—NR
4
R
5
, —SO
2
(C
1-10
-alkylene)—NR
4
R
5
or C
1-6
-alkyl substituted by —NR
4
R
5
;
each Y
1
indep

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