Disazodyes for ink jet printing

Details Disazodyes for ink jet printing Disazodyes for ink jet printing

2000-06-26

2002-11-19

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031770, C534S797000, C008S639000, C427S466000, C428S195100

Reexamination Certificate

active

06482255

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 waterfastness, 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:
B
1
and B
2
are each independently —SO
3
H, —COOH, —CF
3
, optionally substituted alkoxy, optionally substituted alkyl or —PO
3
H
2
;
Q is an organic linking group;
R
1
and R
2
are each independently H or optionally substituted alkyl;
each A independently is N, C—Cl, C—CN or C—NO
2
;
Z
1
and Z
2
are each independently —SR
3
, —OR
4
, —NR
5
R
6
or halogen;
R
3
, R
4
, R
5
& R
6
are each independently H, optionally substituted alkyl, optionally substituted aryl or optionally substituted aralkyl; or
R
5
and R
6
together with the nitrogen to which they are attached form an optionally substituted five or six membered ring;
provided that Q is not of the formula:
B
1
and B
2
are preferably attached ortho to the azo group. It is also preferred that B
1
and B
2
are each independently —SO
3
H, —COOH, —CF
3
, optionally substituted C
1-4
-alkoxy, optionally substituted C
1-4
-alkyl or —PO
3
H
2
, more preferably —SO
3
H, —COOH or —CF
3
and especially —SO
3
H. When B
1
or B
2
is substituted, the substituent(s) is/are preferably selected from —OH, —SO
3
H, —COOH, —NH
2
, C
1-4
-hydroxyalkyl, C
1-4
-hydroxyalkoxy and C
1-4
-alkoxy.
Preferably each A is N.
Preferably R
1
and R
2
are each independently H or optionally substituted C
1-4
-alkyl, more preferably H or C
1-4
-alkyl optionally substituted by hydroxy, carboxy, sulpho or cyano. It is especially preferred that R
1
and R
2
are methyl or H, more especially H.
The organic linking group Q is preferably an optionally substituted piperazinylene group, or a group of the formula —X
1
—L—X
2
— wherein X
1
and X
2
are each independently an optionally substituted piperazinylene group, —S—, —O— or —NR
7
— wherein R
7
is H, optionally substituted alkyl or optionally substituted aryl, and L is a divalent organic linking group.
Preferably R
7
is H, C
1-4
-alkyl or —C
1-4
-hydroxyalkyl, more preferably H or methyl, especially H.
Preferred divalent organic linking groups represented by L are alkylene, preferably C
1-20
-alkylene, more preferably C
2-10
-alkylene, each of which is optionally interrupted; alkenylene, preferably C
2-6
-alkenylene; arylene, preferably arylene containing up to ten carbon atoms, more preferably phenylene or naphthylene, especially 1,3- or 1,2-phenylene; aralkylene, more preferably C
7-10
-aralkylene, especially phenylene-C
1-6
-alkylene more especially -phenylene-CH
2
—; and two arylene groups joined together either directly or through a vinyl, oxygen, nitrogen or sulphur link; each of the above divalent organic linking groups may be substituted or unsubstituted.
The optional substituent(s) on L are preferably selected from alkyl optionally substituted by hydroxy, carboxy or sulpho, preferably hydroxy-C
1-4
-alkyl, carboxy-C
1-4
-alkyl or sulpho-C
1-4
-alkyl; alkoxy, preferably C
1-4
-alkoxy and especially methoxy; phenyl optionally substituted by C
1-4
alkyl, carboxy, hydroxy, sulpho, amino or nitro; halo, preferably F or Cl; —SO
3
H; —COOH; —OH; —CN; or —NO
2
.
When L is an alkylene group it is preferably C
2
10
-alkylene optionally interrupted by —O—; —S—; optionally substituted arylene, especially optionally substituted phenylene; —NR
8
—; —C(O)—; —CO(O)—; or an optionally substituted piperazinylene group, wherein R
8
is H, C
1-4
-alkyl, or —C
1-4
-hydroxyalkyl, more preferably H. When the interrupting group is a substituted piperazinylene group it is preferably substituted by C
1-6
-alkyl optionally substituted by hydroxy, carboxy or sulpho.
An especially preferred interrupted alkylene group is of the formula:
wherein:
R
9
and R
10
each independently is H or C
1-4
-alkyl optionally substituted by hydroxy, sulpho or carboxy.
Preferably R
9
and R
10
are H.
Examples of optionally substituted alkylene and alkenylene groups represented by L include: ethylene; 1,2- & 1,3-propylene; 2-hydroxy-1,3-propylene; 1-, & 2-phenyl-1,3-propylene; 1,4-, 2,3- and 2,4-butylene; 2-methyl-1,3-propylene; 2-(4′-sulphophenyl)-1,3-propylene; 2-methyl-2,4-pentylene; 2,2-dimethyl-1,3-propylene; 1-chloro-2,3-propylene; 1,6- & 1,5-hexylene; 1-carboxy-ethylene 1-carboxy-1,5-pentylene; 2,7-heptylene; 3-methyl-1,6-hexylene; —CH
2
CH═CHCH
2
— and 1-(methoxycarbonyl)-1,5-pentylene.
Examples of optionally interrupted alkylene groups represented by L include —CH
2
NHCH
2
—; —CH
2
CH
2
OCH
2
CH
2
—; —(CH
2
)
3
O(CH
2
)
2
O(CH
2
)OCH
2
OCH
2
—; —CH
2
CH
2
SCH
2
CH
2
—; o-, m- and p-xylylene and
A preferred aralkyl group represented by L is of the Formula (2):
wherein:
each R
11
independently is H, C
1-4
-alkoxy, F, Cl, —SO
3
H, —COOH, —OH, —CN, —NO
2
or C
1-4
-alkyl optionally substituted by —OH, —COOH or —SO
3
H; and
y is 1 to 4.
Preferably y is 1, 2 or 3, more preferably 1.
We have found that compounds wherein L is of the Formula (2) exhibit a high solubility in aqueous media and when incorporated into an ink, the ink exhibits very good operability in ink jet printers.
Examples of preferred arylene and aralkylene groups include —C
6
H
4
—CH
2
—, —C
6
H
4
—CH
2
CH
2
—, 1,2-, 1,3- and 1,4-phenylene and 1,4-naphthylene.
When L is two arylene groups joined together directly it is preferably an optionally substituted biphenylene group, more preferably optionally substituted 4,4′-biphenylene.
When L is a two arylene groups joined by a divalent linking group it is preferably two of the hereinbefore defined arylene groups (especially optionally substituted phenylene) joined together by a linking group selected from —O—, —S—, —NR
8
—, —CH═CH— and C
2-6
-alkylene optionally interrupted by —O—, —S— or —NR
8
—, wherein R
8
is as hereinbefore defined. Examples of two arylene groups joined by a divalent linking group include diphen-4,4′-ylene-methane, —C
6
H
4
—CH
2
CH
2
—C
6
H
4
—, —C
6
H
4
—CH═CH—C
6
H
4
—, —C
6
H
4
—O—C
6
H
4
—, —C
6
H
4
—S—C
6
H
4
— and —C
6
H
4
—NHCH
2
—C
6
H
4
—.
When Q, X
1
or X
2
is an optionally substituted piperazinylene group it is preferably of the Formula (3):
wherein R
9
and R
10
are each independently as hereinbefore defined.
Where one or both of X
1
and X
2
is an optionally substituted piperazinylene group, Q (i. e. the group X
1
LX
2
—) is preferably one of the following formulae:
wherein R
7
is as hereinbefore defined.
In a preferred embodiment Q is an optionally substituted piperazinylene group or Q is a group of the formula —X
1
—L—X
2
— wherein X
1
and X
2
are each independently selected from optionally substituted piperazinylene, —S— or —NR
7
— wherein R
7
is as hereinbefore defined; and L is a group of Formula (2), 1,3-phenylene, or C
2-6
-alkylene optionally interrupted by —O—, —S—, phenylene, —NR
8
—, —C(O)—, —CO(O)— or an optionally substituted piperazinylene group, wherein R
8
is as hereinbefore defined. In this embodiment preferred optionally substituted piperazinylene groups are of Formula (3).
When R
3
, R
4
, R
5
, R
6
or R
7
is optionally substituted alkyl it is preferably optionally substituted C
1-20
-alkyl, more preferably optionally substituted C
1-4
-alkyl and especially optionally substituted C
1-6
-alkyl. Preferred optional substituents include hydroxy, carboxy, sulpho, —PO
3
H
2
, cyano, a 5 or 6 membered hetero

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