Ink compositions containing monoazo dyes

Details Ink compositions containing monoazo dyes Ink compositions containing monoazo dyes

1999-08-27

2001-02-06

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C534S839000, C534S841000, C534S862000, C534S879000

Reexamination Certificate

active

06183549

ABSTRACT:

This invention relates to dyes, to inks, to compositions 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:
Ar
1
is substituted aryl carrying at least one —COOH group;
R
1
is H or optionally substituted alkyl;
L is substituted phenyl carrying at least one substituent at the 2-position, or optionally substituted naphthyl.
Preferably the compound of Formula (1) is a mono-azo compound (i.e. it contains only one —NO═N— group).
Preferably R
1
is H or optionally substituted C
1-6
-alkyl, more preferably H or C
1-4
-alkyl optionally substituted by —OH, —COOH, —SO
3
H or —CN. It is especially preferred that R
1
is methyl, ethyl or H, more especially H.
Ar
1
is preferably substituted naphthyl or, more preferably, substituted phenyl, wherein at least one of the substituents is —COOH. It is especially preferred that Ar
1
is a group of the Formula (2):
wherein:
each B independently is a substituent other than H;
p is 0 to 4;
n is 1 or 2; and
(n+p) is 5 or less.
Preferably each B independently is —SO
3
H, —PO
3
H
2
, —CF
3
, optionally substituted alkoxy, optionally substituted alkyl, optionally substituted amino, halo, —CN, —OH, —NO
2
or —SO
2
W; wherein
W is optionally substituted alkyl (preferably optionally substituted C
1-10
-alkyl), optionally substituted aryl (preferably optionally substituted phenyl), —NR
2
R
3
, vinyl or a group convertible to vinyl on treatment with aqueous alkali; and
R
2
and R
3
are each independently H, optionally substituted alkyl or optionally substituted aryl, or R
2
and R
3
together with the nitrogen to which they are attached form an optionally substituted piperazinyl, morpholinyl or piperidinyl ring.
Preferably R
2
and R
3
are each independently H, optionally substituted C
1-10
-alkyl or optionally substituted phenyl, more preferably H, optionally substituted C
1-6
-alkyl or optionally substituted phenyl.
When W is a group which is convertible to vinyl on treatment with aqueous alkali it is preferably of the formula —CH
2
CH
2
OSO
3
H, —CH
2
CH
2
SSO
3
H, —CH
2
CH
2
Cl or —CH
2
CH
2
OCOCH
3
. Preferably W is —NR
2
R
3
, —CH═CH
2
or —CH
2
CH
2
OSO
3
H and especially —CH═CH
2
or —NR
2
R
3
, wherein R
2
and R
3
are as hereinbefore defined. In a preferred embodiment each B independently is —SO
3
H, —PO
3
H
2
, —CF
3
, optionally substituted C
1-10
-alkoxy, optionally substituted C
1-10
-alkyl, optionally substituted amino, —F —Cl, —Br, —CN, —OH, —NO
2
or —SO
2
NR
2
R
3
, wherein R
2
and R
3
are as hereinbefore defined.
When B, R
2
or R
3
is substituted the substituent(s) is/are preferably selected from C
1-4
-alkyl, C
1-4
-hydroxyalkyl, C
1-4
-alkoxy, C
1-4
-alkylCO, —OH, —SO
3
H, —COOH, —PO
3
H
2
, halo and —NH
2
.
It is especially preferred that each B independently is —SO
3
H, —CF
3
, —NH
2
, halo, —NHCOC
1-4
-alkyl (preferably —NHCOCH
3
), C
1-6
-alkoxy, —SO
2
NHC
1-4
-alkyl, —SO
2
NHC
1-4
-hydroxyalkyl or C
1-6
-alkyl optionally substituted by —OH, —COOH, —NH
2
or —SO
3
H.
When Ar
1
is a group of the Formula (2), preferably p=0 and n=1 or 2. It is especially preferred that p=0, n=1 and that the —COOH group is attached ortho to the azo group shown in Formula (1).
When Ar
1
is substituted naphthyl it is preferably substituted by one —COOH and optionally one or more of the hereinbefore defined groups B. This —COOH group is preferably attached ortho to the azo group shown in Formula (1). An especially preferred substituted naphthyl group represented by Ar
1
is an optionally substituted 1-carboxy-naphth-2-yl group.
Preferably L is of the Formula (3) or (4):
wherein:
X and each T independently is a substituent other than H;
m is 0 to 4; and
q is 0 to 7.
Preferably q is 0 to 3, more preferably 0 or 1 and especially 0. m is preferably 0 or 1, more preferably 0.
Preferably X and each T independently are selected from the preferred groups described above for B or COOH, more preferably a group B as hereinbefore defined.
It is especially preferred that each T independently is —SO
3
H, —CF
3
, —NH
2
, halo, —NHCOC
1-4
-alkyl (preferably —NHCOCH
3
), C
1-6
-alkoxy, —SO
2
NHC
1-4
-alkyl, —SO
2
NHC
1-4
-hydroxyalkyl or C
1-6
-alkyl optionally substituted by —OH, —COOH, —NH
2
or —SO
3
H.
It is especially preferred that X is —SO
3
H, —CF
3
, —NH
2
, halo, C
1-6
-alkoxy or C
1-6
-alkyl optionally substituted by —OH, —COOH, —NH
2
or —SO
3
H. More especially X is C
1-4
-alkyl, C
1-4
-alkoxy, —Cl, —Br or —OH, particularly methyl or —Cl.
When L is of the Formula (4), the naphthyl group is preferably attached at the 1-, or more preferably 2-position to the carbonyl group shown in Formula (1).
It is especially preferred that L is of the Formula (3), wherein m=0.
The floating sulpho group shown in Formula (1) is preferably attached meta to the —NR
1
— group.
In view of the foregoing preferences, a preferred compound according to the first aspect of the present invention is of the Formula (5) or a salt thereof:
wherein:
X
1
is —SO
3
H, —CF
3
, —NH
2
, halo, C
1-4
-alkoxy or C
1-6
-alkyl optionally substituted by —OH, —COOH, —NH
2
or —SO
3
H; and
R
4
is H or C
1-4
-alkyl optionally substituted by —OH, —COOH or —SO
3
H.
X
1
is preferably halo (especially F, Cl or Br), C
1-6
-alkyl or —SO
3
H, more preferably C
1-4
-alkyl, C
1-4
-alkoxy, —SO
3
H, —Cl or —Br, particularly C
1-4
-alkyl, —Cl or —SO
3
H and especially —Cl or—SO
3
H.
The —COOH group shown in Formula (5) is preferably attached ortho to the azo group.
Especially preferred compounds of the Formula (5) are those in which the —COOH group is attached ortho to the azo group; R
4
is H or C
1-4
-alkyl; and X
1
is —Cl, C
1-4
-alkyl (especially methyl or ethyl) or —SO
3
H.
The compounds of the invention exhibit a high solubility in aqueous media and provide prints which exhibit good light-fastness and chroma when incorporated into inks for ink jet printing. We have found that the presence of the substituent X in Formula (3) and X
1
in Formula (5) provides compounds with a particularly high light-fastness.
The compounds of the invention may be in the free acid or salt form. Preferred salts are water-soluble, for example alkali metal salts, especially lithium, sodium and potassium salts, ammonium and substituted ammonium salts. Especially preferred salts are salts with sodium, lithium, ammonia and volatile amines. The compounds may be converted into a salt using known techniques. For example, an alkali metal salt may be converted into a salt with ammonia or an amine by dissolving an alkali metal salt in water, acidifying with a mineral acid, 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, reverse osmosis or ultrafiltration.
The compounds of the invention may be prepared using conventional techniques for the preparation of azo dyes. For example a suitable method comprises coupling the diazonium salt of an amine of the formula Ar
1
NH
2
with a compound of the Formula (6), preferably under mildly alkaline reaction conditions:
wherein, L, Ar
1
and R
1
are as hereinbefore defined.
The coupling reaction is preferably performed in a liquid medium, more preferably an aqueous medium and especially water. A reaction temperature in the range of from −5° C. t

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