Dyes, inks and their use in ink-jet printing

Details Dyes, inks and their use in ink-jet printing Dyes, inks and their use in ink-jet printing

2002-07-24

2003-10-21

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C008S639000, C106S031480, C427S466000, C428S195100, C347S086000

Reexamination Certificate

active

06635747

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 a first aspect of the present invention there is provided a mono-azo compound of Formula (1) and salts thereof:
wherein:
D is the residue of a mono-azo chromophore;
Z is an optionally substituted nitrogen containing heterocyclic group;
R
1
is H or optionally substituted alkyl;
the dyes of Formula (1) being free from fibre reactive groups;
provided that the compound of Formula (1) is other than the compound of Formula (A):
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.
The nitrogen containing heterocyclic group represented by Z is preferably attached to the triazine ring in Formula (1) by a bond to a nitrogen atom in the heterocyclic group.
Z may contain more than one nitrogen atom. Z may also contain other heteroatoms in addition to nitrogen, for example one or more sulphur or oxygen atom(s).
Z may be a monocyclic or polycyclic nitrogen containing heterocyclic group which may be saturated, unsaturated or aromatic. It is preferred however that Z is a bicyclic or, more preferably, a monocyclic nitrogen containing heterocyclic group. It is especially preferred that Z is a 6 or more especially a 5 membered monocyclic nitrogen containing heterocyclic group.
Preferably Z is free from primary and secondary amino groups because we have found that the presence of such groups reduces the light-fastness of the compounds of Formula (1).
Preferred groups represented by Z include morpholino, pyrrolyl, imidazolyl, isoindolyl, indazolyl, pyrazolyl, pyrrolidinyl, pyrrolinyl, imadazolidinyl, imidazolinyl, pyrazolidinyl, pyrazolinyl, piperidino, piperazinyl, indolinyl, isoindolinyl, isothiazolinone, benzisothiazolinone or tetrahydroisoquinolinyl each of which is optionally substituted.
Preferred optional substituents on Z include sulpho, carboxy, halogen (preferably chloro) alkoxy (preferably C
1-6
-alkoxy) or alkyl ((preferably C
1-6
-alkyl) optionally substituted by hydroxy, carboxy or sulpho. Especially preferred optional substituents on Z are C
1-4
-alkyl, carboxy or sulpho.
It is especially preferred that Z is morpholino or pyrrolidinyl optionally substituted by C
1-4
-alkyl, carboxy or sulpho.
The mono-azo group represented by D contains one azo group (—N═N—). Preferably D is a group of the Formula (2):
wherein:
Ar is optionally substituted aryl or optionally substituted heteroaryl; and
L is optionally substituted arylene.
Preferred groups represented by Ar contain up to 20, more preferably up to 15 and especially up to 12 carbon atoms.
When Ar is optionally substituted aryl it is preferably optionally substituted phenyl, optionally substituted naphthyl or optionally substituted indanyl.
When Ar is optionally substituted heteroaryl it is preferably optionally substituted pyrazolonyl, optionally substituted pyridonyl (especially optionally substituted hydroxypyridonyl), optionally substituted thiophenyl, optionally substituted thiazolyl or optionally substituted benzisothiazolyl.
Preferably Ar is optionally substituted phenyl or optionally substituted naphthyl.
Preferred optional substituents on Ar include halogen (especially F and Cl), nitro, cyano, —CF
3
, —OR
2
, —SR
2
, —NR
3
R
4
, —C(O)R
5
, —C(O)OR
6
, —SO
2
R
7
, —SOR
8
or C
1-6
-alkyl optionally substituted by —OH, —SO
3
H, —COOH, —PO
3
H
2
, C
1-4
-alkoxy or hydroxy-C
1-4
-alkylene-oxy;
wherein:
R
2
is H, C
1-6
-alkyl optionally substituted by —OH, —SO
3
H or —COOH, or phenyl optionally substituted by C
1-4
-alkyl, —OH, —SO
3
H, —COOH, —NH
2
or —NO
2
;
R
3
and R
4
are each independently H, —CO(C
1-6
-alkyl), —CONH
2
, C
1-6
-alkyl optionally substituted by —OH, —SO
3
H or —COOH, or phenyl optionally substituted by C
1-4
-alkyl, —OH, —SO
3
H, —COOH, —NH
2
or —NO
2
; or
R
3
and R
4
together with the nitrogen to which they are attached form a 5- or 6-membered ring (preferably morpholine or piperazine); and
R
6
, R
7
, R
8
and R
9
are each independently C
1-6
-alkyl or phenyl.
Especially preferred optional substituents on Ar include one or more of C
1-4
-alkyl, C
1-4
-alkoxy, —OH, —COOH, —PO
3
H
2
, —SO
3
H, nitro, —Cl, —F,—CF
3
, amino and —COOC
1-4
-alkyl.
Preferred examples of groups represented by Ar include 2-carboxyphenyl, 3,5-dicarboxyphenyl, 2-sulphophenyl, 3-sulphophenyl, 2-carboxy-4-sulphophenyl, 3,4-dimethyl-6-sulphophenyl, 4-amino-2-hydroxyphenyl, 4-carboxy-2-hydroxyphenyl, 1,5-disulphonaphth-2-yl, 1-sulphonaphth-2-yl, 3,6,8-trisulphonapth-2-yl, 8-hydroxy-2,4-disulphonaphth-1-yl, 1-amino-8-hydroxy-3,6-disulphonaphth-2-yl, 2-amino-8-hydroxy-6-sulphonaphth-1-yl, 2-amino-8-hydroxy-6-sulphonaphth-7-yl, 2-amino-8-hydroxy-3,6-sulphonaphth-1-yl or 6-sulpho-indan-5-yl.
Preferably L is optionally substituted phenylene or optionally substituted naphthylene. Preferred optional substituents on L are the preferred optional substituents as hereinbefore described in relation to Ar.
When L is optionally substituted phenylene it is preferably a group of the Formula (3):
wherein:
G is sulpho, carboxy, optionally substituted alkyl, optionally substituted alkoxy, —CF
3
or —PO
3
H
2
; and
n is 0 to 4.
Preferably G is —SO
3
H, —COOH, —CF
3
, optionally substituted C
1-4
-alkyl, 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
, more preferably —OH.
n is preferably 0, 1 or 2, more preferably 1 or 2 and especially 1.
It is especially preferred that when L is of the Formula (3) it is a 1,4-phenylene group optionally carrying a substituent represented by G at the ortho position relative to the azo group in Formula (2).
When L is optionally substituted naphthylene it is preferably of the Formula (4):
wherein:
G is as hereinbefore defined; and
q is 0 to 4.
Preferably q is 1 to 4. Preferably the group of Formula (4) carries at least one, more preferably two sulpho group(s). It is especially preferred that the compound of Formula (4) is of the Formula (5):
wherein:
t is 0 or 1.
When t is 1 in Formula (5) the sulpho group is preferably attached at the 4- or more preferably the 3-position in the naphthylene ring. Preferably the azo group is attached at the 7-position of the naphthylene ring in Formula (5).
In a preferred embodiment L is a naphthylene group, preferably a group of the Formula (5) as hereinbefore described.
It is especially preferred that the compound of Formula (1) is magenta in colour.
In view of the foregoing preferences the compound of Formula (1) is preferably a compound of the Formula (6) or a salt thereof:
wherein:
Ar
1
is optionally substituted phenyl or optionally substituted naphthyl;
Z
1
is an optionally substituted nitrogen containing heterocyclic group which is attached to the triazine ring by a bond to a nitrogen atom in the heterocyclic group;
R
2
is H or C
1-4
-alkyl optionally substituted by —OH, —COOH or —SO
3
H; and
t is 0 or 1.
Preferably Z
1
is as hereinbefore defined for Z except the heterocyclic group is attached to the triazine ring in Formula (6) by a bond to a nitrogen ato

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