Compositions containing a liquid medium and an azo dye

Details Compositions containing a liquid medium and an azo dye Compositions containing a liquid medium and an azo dye

2001-03-01

2003-08-26

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C534S803000, C008S673000, C008S674000, C427S466000, C428S032100

Reexamination Certificate

active

06610132

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 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 a first aspect of the present invention there is provided a composition comprising:
(a) a liquid medium comprising (i), (ii) or (iii):
(i) a mixture of water and an organic solvent;
(ii) an organic solvent free from water; or
(iii) a low melting point solid; and
(b) a dye of the Formula (1) or salt thereof:
 wherein:
each A independently is N, C—Cl, C—CN or C—NO
2
;
each B independently is a substituent other than —COOH;
L is optionally interrupted alkylene, optionally substituted by halo or —OH, wherein the optional interruption(s) are selected from —O—, —S—, —NR
1
—, —CR
1
═CR
1
—, —C(O)— and —C(O)O—;
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;
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; and
each n independently is 0 to 4.
Preferably the dye of Formula (1) is not of the Formula (A), (B), (C) or (D):
wherein X
1
is H or Na;
Preferably the composition has a concentration of less than 100 parts per million in total of halide ions and divalent and trivalent metal ions.
Preferably the group —XLX— shown in Formula (1) is not of the Formula (E), (F), (G), (H), (I) or (J):
—HN—V—O(—G—O—)
p
W—NH—  Formula (E)
wherein: V and W each independently represents a linear or branched alkylene group having from 1 to 8 carbon atoms; G represents a linear or branched alkylene group having from 1 to 2 carbon atoms or the following formula (a):
and p represents a number of from 0 to 20;
wherein G
1
and G
2
each represents a hydrogen atom or a methyl group;
Preferably each A is N.
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 —OH, —COOH, —SO
3
H or —CN. It is especially preferred that each R
1
independently is methyl, ethyl or H, more especially H.
Each X independently is preferably —S— or —NR
1
—, more preferably —NR
1
— and especially —NH—.
Each B independently is preferably —SO
3
H, —PO
3
H
2
,—CF
3
, optionally substituted alkoxy, optionally substituted alkyl, optionally substituted amino, halo, —CN, —SO
2
—T, —OH or —NO
2
, wherein T is optionally substituted alkyl, optionally substituted aryl, vinyl, or a group convertible to vinyl on treatment with aqueous alkali. 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
. More preferably T is —CH═CH
2
or —CH
2
CH
2
OSO
3
H and especially —CH═CH
2
.
More preferably 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, —SO
2
CH═CH
2
, —F, —Cl, —CN, —OH or —NO
2
. When B is substituted the substituent(s) is/are preferably 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
.
Still more preferably each B independently is —SO
3
H, —CF
3
, amino, —NHCOC
1-4
-alkyl, C
1-6
-alkoxy 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 or —NHCOC
1-4
-alkyl, more especially methyl, ethyl or —NHCOCH
3
.
Preferably each n independently is 0, 1 or 2, more preferably 0.
When R
2
, R
3
, R
4
, R
5
or T 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 and optionally substituted amino. Preferred 5 or 6 membered heterocyclic groups are optionally substituted furanyl, tetrahydrofuranyl, piperazinyl and niorpholinyl.
When any of R
2
, R
3
, R
4
, R
5
or T 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, C
1-6
-alkyl, —SO
2
NH
2
, —SO
2
NHC
1-4
-alkyl or C
1-6
-alkyl substituted by —OH, —COOH or —SO
3
H.
When any of R
2
, R
3
, R
4
or R
5
is optionally substituted aralkyl it is preferably of the formula:
each R
5
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, more preferably 0 or 1.
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 piperazine, piperidine or morpholine ring. The substituents 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 atoms and groups which may be represented by Z include halogen atoms, for example F or Cl; sulphonic acid groups; thiocyano groups; quaternary ammonium groups, for example trialkylammonium groups and optionally substituted pyridinium groups, for example 3- and 4-carboxy pyridinium groups. An especially preferred labile atom is Cl.
It is preferred however that each Z independently is —SR
2
, —OR
3
or —NR
4
R
5
, more preferably —OH, —SR
2
or —NR
4
R
5
wherein R
2
, R
4
and R
5
are as hereinbefore defined. It is especially preferred that each Z independently is —NR
7
R
8
wherein R
7
is C
1-6
-alkyl optionally substituted by —OH, C
1-4
-alkoxy, C
1-4
-hydroxyalkoxy, —COOH or —SO
3
H; and R
8
independently is as defined for R
7
or H.
For ease of synthesis it is preferred that each Z is the same in Formula (1).
L is preferably a branched, monocyclic (for example cyclohexylene) or more preferably linear alkylene group. Preferably L is optionally interrupted C
1-20
-alkylene, wherein the optional interruptions are as hereinbefore defined. More preferably L is C
2-20
-alkylene optionally interrupted by —O—, —S—, —CH═CH— or —NR
1
— wherein R
1
is as hereinbefore defined. It is especially preferred that L is C
2-6
-alkylene, more especially ethylene (i.e. —CH
2
CH
2
—).
When L is interrupted it preferably contains a single interrupting group or two or more interrupting groups, for example an —SS— group. Preferred interrupting groups are selected from one or more of —S—, —CH═CH— and —NR
1
— wherein R
1
is as hereinbefore defined.
Examples of optionally substituted alkylene groups represented by L include: ethylene; 1,2- &

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