Mono-azo dyes and inks for ink-jet printing

Details Mono-azo dyes and inks for ink-jet printing Mono-azo dyes and inks for ink-jet printing

2000-06-05

2003-02-04

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031770, C106S496000, C534S798000, C427S466000, C428S195100

Reexamination Certificate

active

06514329

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 mono-azo compound of Formula (1) or a salt thereof:
wherein:
A is N, C—Cl, C—CN or C—NO
2
;
R
1
is H or optionally substituted alkyl;
G is H, sulpho, carboxy, optionally substituted alkyl, optionally substituted alkoxy, —CF
3
, halo or —PO
3
H
2
;
L
1
and L
2
each independently is —SR
2
, —OR
3
or —NR
4
R
5
;
R
2
, R
3
, R
4
and R
5
each independently is H, optionally substituted alkyl or optionally substituted aryl; or
R
4
and R
5
together with the nitrogen to which they are attached form an optionally substituted five or six membered ring;
provided that L
1
and L
2
are free from carboxy, sulpho and —PO
3
H
2
groups.
The term mono-azo refers to compounds of Formula (1) with one azo group (—N═N—).
Preferably A is N.
R
1
is preferably H or optionally substituted C
1-4
-alkyl, more preferably H or C
1-4
-alkyl optionally 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
is H.
G is preferably attached ortho to the azo group. Preferably G is —SO
3
H, —COOH, —CF
3
, alkyl (preferably optionally substituted C
1-4
-alkyl), alkoxy (preferably optionally substituted C
1-4
-alkoxy) or —PO
3
H
2
, more preferably —SO
3
H, —COOH or —CF
3
and especially —SO
3
H. Preferred optional substituents on G are selected from —OH, —SO
3
H, —COOH and —NH
2
.
When R
2
, R
3
, R
4
or R
5
is optionally substituted alkyl it is preferably optionally substituted C
1-30
-alkyl, The alkyl group may be straight-chain, branched-chain or cyclic (for example cyclohexyl). When it is a branched-chain alkyl, it is preferably an &agr;-branched alkyl group, for example —CH(CH
3
)CH
2
CH
2
CH
3
or —CH(CH
3
)CH
2
CH(CH
3
)
2
. In one preferred embodiment the alkyl group is optionally substituted C
1-10
-alkyl, more preferably optionally substituted C
1-6
-alkyl and especially optionally substituted C
1-4
-alkyl. In a further preferred embodiment the alkyl group is optionally substituted C
5-20
-alkyl.
Preferred optional substituents on the alkyl groups represented by any of R
2
, R
3
, R
4
or R
5
include hydroxy, cyano, halo (especially F or Cl), nitro, C
1-6
-alkoxy, C
1-6
hydroxyalkoxy, a 5 or 6 membered heterocyclic group, or a group represented by T, wherein T is an optionally substituted amino group. Especially preferred substituents are selected from hydroxy, a 5 or 6 membered heterocyclic group and a group represented by T. Preferred 5 or 6 membered heterocyclic groups are optionally substituted furanyl and tetrahydrofuranyl, more preferably furanyl or tetrahydrofuranyl and especially furan-2-yl and tetrahydrofuran-2-yl.
Preferably T is a group of the formula —NR
6
R
7
wherein R
6
and R
7
are each independently H, optionally substituted alkyl, —CO(alkyl), —CO(phenyl), or R
6
and R
7
together with the nitrogen to which they are attached form an optionally substituted morpholinyl, piperazinyl or piperidinyl ring.
When R
6
or R
7
is optionally substituted alkyl it is preferably optionally substituted C
1-20
-alkyl, more preferably optionally substituted C
1-6
alkyl, and especially C
1-4
-,alkyl, for example methyl, ethyl, n-propyl and iso-propyl. Preferred optional substituents on R
6
and R
7
are selected from —OH or —NH
2
.
When R
6
or R
7
is —CO(alkyl) it is preferably —CO(C
1-6
-alkyl), more preferably —CO(C
1-4
-alkyl). For example —COCH
2
CH
3
and —COCH
2
CH
2
CH
3
.
When R
6
and R
7
together with the nitrogen to which they are attached form a substituted morpholinyl, piperidinyl or piperazinyl ring it is preferably substituted by C
1-4
-alkyl, C
1-4
-hydroxyalkyl, —CO(C
1-4
-alkyl) or a group of the formula —M—NR
8
R
9
wherein M is an alkylene linking group and R
8
and R
9
each independently is H or C
1-6
-alkyl optionally substituted by hydroxy or C
1-6
-alkoxy. M is preferably C
1-6
-alkylene, more preferably C
2-6
-alkylene and especially —(CH2)
g
—, wherein g is from 2 to 6.
Further preferred groups represented by T include —NH
2
; —NH(C
1-30
(-alkyl), for example ethylamino, —NHCH(CH)
3
CH
2
CH
3
and —NHC
16
H
33
; —N(C
1-6
-alkyl)
2
, for example di-ethylamino; —NHCO(C
1-4
-alkyl), for example —NHCOCH
3
and —NHCOCH
2
CH
3
; —NH(Phenyl); morpholinyl; piperazinyl; and substituted piperazinyl groups of the Formula (2):
wherein:
Y is C
1-4
-alkyl, C
1-4
-hydroxyalkyl, —CO(C
1-4
-alkyl) or a group of the formula —M—NR
8
R
9
; and
M, R
8
and R
9
are as hereinbefore defined.
Preferred groups of the Formula (2) include for example:
A preferred alkyl group substituted by T which may be represented by any of R
2
, R
3
, R
4
and R
5
is of the formula —(C
d
H
2d
)—T wherein d is 1 to 6, more preferably 2 to 6 and T is as hereinbefore defined.
A further preferred optionally substituted alkyl group represented by any of R
2
, R
3
, R
4
and R
5
is of the Formula (3):
—(C
a
H
2a
O)
t
(C
b
H
2b
O)
q
R
10
  Formula (3)
wherein:
R
10
is H or alkyl optionally substituted by —NH
2
;
a and b are different and from 1 to 6;
t is from 1 to 4; and
q is from 0 to 3.
Preferably R
10
is H or C
1-4
-alkyl, more preferably H.
Preferably a and b are each independently 2 to 6, more preferably 2 or 3, t is 1 or 2 and q is 0.
Preferred groups of Formula (3) include —(C
2-6
-alkylene)O(C
2-6
-alkylene)OC
1-4
alkyl, for example —C
2
H
4
OC
2
H
4
OCH
3
, and —(C
2-6
-alkylene)O(C
2-6
-alkylene)OH, for example —C
2
H
4
OC
2
H
4
OH, —CH
2
CH(CH
3
)CH
2
OC
2
H
4
OH and —C
3
H
6
OC
2
H
4
OH.
When R
2
, R
3
, R
4
or R
5
is optionally substituted aryl it is preferably optionally substituted phenyl or optionally substituted naphthyl, more preferably a group of the Formula (4) or (5):
wherein:
each R
11
independently is C
1-6
-alkoxy, C
1-6
-hydroxyalkoxy, hydroxy, halo (preferably F or Cl), nitro, amino, —COC
1-6
-alkyl, —NHCOC
1-6
-alkyl or —NHC
1-6
-hydroxyalkyl;
each Q independently is optionally substituted C
1-30
-alkyl or a group of the Formula —Z—Q
1
;
each Z independently is a divalent linking group;
each Q
1
independently is optionally substituted C
1-30
-alkyl;
n and m each independently is 0 to 5; and
(n+m)=0 to 5.
m is preferably 0, 1 or 2, more preferably 1 or 2.
n is preferably 0 or 1.
(n+m) is preferably 1 to 3 more preferably 1 or 2.
Each Z is preferably independently selected from —O—, —S—, —NR
a
—, —SO
2
— and —SO
2
NR
a
—, wherein R
a
is H or C
30
-alkyl optionally substituted by a group other than —COOH, —SO
3
H or —PO
3
H
2
. Preferably R
a
is H or C
1-20
-alkyl, more preferably H or C
1-6
-alkyl and especially H.
Q and Q
1
may be a straight chain or branched chain alkyl group. When any of Q or Q
1
is a branched chain alkyl group it is preferably branched at the &agr;-carbon. In a preferred embodiment Q and Q
1
are each independently C
1-4
-alkyl. In a further preferred embodiment Q and Q
1
are each independently optionally substituted C
5-20
-alkyl.
When any of Q or Q
1
is substituted, the substituents are preferably selected from hydroxy, cyano, halo (especially F or Cl), nitro, C
1-6
-alkoxy, C
1-6
-hydroxyalkoxy, a 5 or 6 membered heterocyclic group, or a group represented by T, wherein T is as hereinbefore defined. It is preferred, howev

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