Bix-azo naphthylene compounds and their use in compositions...

Details Bix-azo naphthylene compounds and their use in compositions... Bix-azo naphthylene compounds and their use in compositions...

2000-07-10

2003-01-14

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031770, C534S803000, C008S639000, C427S466000, C428S195100

Reexamination Certificate

active

06506241

ABSTRACT:

This invention relates to compositions, to inks and to dyes 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 in 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 first aspect of the present invention there is provided a compound of the Formula (1) and salts thereof:
wherein:
each A independently is N, C—Cl, C—CN or C—NO
2
,
each Ar independently is a substituted aryl group carrying a —COOH group ortho to the azo (—N═N—) group;
L is an aliphatic group carrying a —COOH, —SO
3
H or —PO
3
H
2
group;
each Z independently is —SR
2
, —OR
3
, —NR
4
R
5
or a labile atom or group;
each X independently is —S—, —O— or —NR
1
—;
each R
1
independently is H or optionally substituted alkyl; and
R
2
, R
3
, R
4
and R
5
are each independently H, optionally substituted alkyl, optionally substituted aryl or optionally substituted aralkyl; or
R
4
and R
5
together with the nitrogen to which they are attached form an optionally substituted five or six membered ring.
Preferably each A is N.
Preferably the aryl groups represented by Ar contain up to 12 carbon atoms, more preferably up to 10 carbon atoms and optionally contain one or more hetero atoms selected from O, S and N. The aryl groups optionally carry one or more substituents in addition to the —COOH group ortho to the azo group in Formula (1).
Suitable aryl groups containing one or more hetero atoms include pyridyl, pyrazolyl, thienyl or indanyl. It is preferred however that the aryl groups are free from hetero atoms, for example phenyl or naphthyl.
More preferably each Ar independently is optionally substituted 1-carboxy-naphth-2-yl or optionally substituted 2-carboxy phenyl. It is especially preferred that each Ar independently is of the Formula (2) or (3):
wherein:
each B independently is —OH, —SO
3
H, —PO
3
H
2
, —COOH, —CF
3
, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amino, halo, —NO
2
, —CN or —SO
2
T;
T is optionally substituted alkyl (preferably optionally substituted C
1-10
-alkyl) optionally substituted aryl (preferably optionally substituted phenyl), —NR
6
R
7
, vinyl or a group convertible to vinyl on treatment with aqueous alkali;
R
6
and R
7
are each, independently, H, optionally substituted alkyl or optionally substituted aryl, or R
6
and R
7
together with the nitrogen to which they are attached form an optionally substituted piperazinyl, morpholinyl or piperidinyl ring;
n is 0 to 6; and
p is0 to 4.
Preferably R
6
and R
7
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 T 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 T is —NR
6
R
7
, —CH═CH
2
or —CH
2
CH
2
OSO
3
H and especially —CH═CH
2
or —NR
6
R
7
, wherein R
6
and R
7
are as hereinbefore defined.
Preferably each B independently is —COOH, —SO
3
H, —PO
3
H
2
, —CF
3
, optionally substituted C
1-10
-alkoxy, optionally substituted C
1-10
-alkyl, optionally substituted amino —SO
2
CH═CH
2
, —Cl, —Br, —I, —CN, —OH, —NO
2
or —SO
2
NR
6
R
7
, wherein R
6
and R
7
are as hereinbefore defined.
Preferred optional substituents on B are selected from C
1-6
-alkyl, C
1-6
-hydroxyalkyl, C
1-6
-alkoxy, C
1-4
-alkylCO, —OH, —SO
3
H, —COOH, —CN, —PO
3
H
2
, halo and —NH
2
.
In a preferred embodiment each B independently is —COOH, —SO
3
H, —OH, —CF
3
, Cl, —NH
2
, —NHCOC
1-4
-alkyl, —NHC
1-4
-alkyl, —NHC
1-4
-hydroxyalkyl, 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 each B independently is C
1-4
-alkyl, —COOH, —OH, —SO
3
H or —NHCOC
1-4
-alkyl, more especially methyl, ethyl, —NHCOCH
3
or —COOH.
Preferably any substituents represented by B in Formulae (2) and (3) are located in a position other than the ortho position relative to the azo group in Formula (1).
Preferably each n independently is 0, 1 or 2, more preferably 0.
Preferably each p independently is 0, 1 or 2, more preferably 0.
In a preferred embodiment each Ar is, independently, of the Formula (3) wherein each p is 0, 1 or 2 (preferably 0) and each B is as hereinbefore defined, more preferably —COOH, —OH, —SO
3
H or —Cl. It is especially preferred that each Ar is 2-carboxyphenyl. For ease of synthesis it is preferred that each Ar is the same.
Preferably each R
1
independently is H or optionally substituted C
1-6
-alkyl, more preferably H or C
1-4
-alkyl optionally substituted by —COOH, —SO
3
H, —CN or more preferably —OH. It is especially preferred that each R
1
independently is H, methyl, ethyl or hydroxyethyl. It is most preferred that each R
1
is H.
Preferably each X independently is —S— or —NR
1
—, more preferably —NR
1
— and especially —NH—.
When R
2
, R
3
, R
4
or R
5
is optionally substituted alkyl it is preferably optionally substituted C
1-20
-alkyl, more preferably optionally substituted C
1-10
-alkyl and especially optionally substituted C
1-6
-alkyl. Preferred optional substituents include C
1-6
-alkoxy, C
1-6
-hydroxyalkoxy, —OH, —COOH, —SO
3
H, —PO
3
H
2
, —CN, a 5- or 6-membered heterocyclic group or optionally substituted amino. Preferred 5- or 6-membered heterocyclic groups are furanyl, tetrahydrofuranyl, piperazinyl and morpholinyl each of which is optionally substituted by —OH, —COOH, —SO
3
H or C
1-4
-alkyl.
When any of R
2
, R
3
, R
4
or R
5
is optionally substituted aryl it is preferably optionally substituted phenyl or naphthyl, more preferably optionally substituted phenyl. Preferred optional substituents are C
1-6
-alkoxy, halo (preferably F or Cl), —OH, —CN, —COOH, —SO
3
H, —PO
3
H
2
, —NO
2
, —NH
2
, —COC
1-4
-alkyl, —NHCOC
1-4
-alkyl-(C
1-6
-alkylene)O(C
1-6
-alkylene)OC
1-4
-alkyl,-(C
2-6
-alkylene)O(C
2-6
-alkylene)OH, —SO
2
NH
2
, —SO
2
NHC
1-4
-alkyl, C
1-6
-alkyl or C
1-6
-alkyl substituted by —OH, —COOH or —SO
3
H.
Examples of aryl groups which may be represented by any of R
2
, R
3
, R
4
or R
5
include 2-sulphophenyl, 2-carboxyphenyl, 4-sulphophenyl, 4-carboxyphenyl, 2-carboxy-4-suiphophenyl, 3-carboxy-2-methyl-phenyl, 4-methyl-3-sulpho-phenyl or 2,6-dimethylphenyl.
When any of R
2
, R
3
, R
4
or R
5
is optionally substituted aralkyl it is preferably of the formula:
wherein
each R
8
independently is C
1-4
-alkyl, C
1-4
-alkoxy, halo, —OH, —NH
2
, —COOH, —SO
3
H or —PO
3
H
2
; and
a is 0 to 5.
a is preferably 0, 1 or 2.
Especially preferred aralkyl groups which may be represented by R
2
, R
3
, R
4
or R
5
are benzyl or 2-phenylethyl, each of which is optionally substituted by —COOH, —OH or —SO
3
H.
When R
4
and R
5
together with the nitrogen to which they are attached form an optionally substituted 5 or 6 membered ring it is preferably an optionally substituted piperazinyl, piperidinyl or morpholinyl ring. The optional substituents on the ring are preferably selected from —OH, —COOH, —SO
3
H, C
1-6
-alkoxy, C
1-6
-alkyl and C
1-6
-alkyl substituted by —OH, —COOH or —SO
3
H.
When Z is a labile atom or group, it is preferably an atom or group which is displaceable by a hydroxyl group of cellulose under mildly alkaline aqueous conditions to form a covalent bond between the dye of Formula (1) and cellulose.
Preferred labile a

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