Pyridonazo dyes and inks containing them

Details Pyridonazo dyes and inks containing them Pyridonazo dyes and inks containing them

1999-12-21

2001-10-16

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C523S161000, C106S031450, C106S031480

Reexamination Certificate

active

06303763

ABSTRACT:

This invention relates to dyes, to inks and to their use in ink jet printing.
Ink jet printing methods involve printing an image onto a substrate using ink droplets emitted from a small nozzle without bringing the nozzle into contact with the substrate. Over recent years ink jet printers have become popular because they are quieter and more versatile than impact printers, for example conventional basket typewriters are noisy and the images they can print are restricted to the shapes moulded onto the end of each mechanical lever. The most popular ink jet printers are the thermal and piezoelectric.
The requirements for inks used in ink jet printers include:
i) they should not clog the small nozzle from which they are emitted, or form a blocking crust over the end,
ii) the resultant image should have good water-fastness so that it does not smudge excessively on contact with sweat or water,
iii) the image should also have a good light-fastness so that it does not fade quickly on exposure to daylight,
iv) they should dry quickly on paper and give discrete, sharp images,
v) they should have good storage stability, and
vi) they should have a high colour strength to give intensely coloured images.
WO91/06608 describes aqueous inks containing a polyester, water, a pigment and a wax. Whilst these inks are useful in printing presses, the pigments they contain require intensive and expensive milling to make them fine enough to pass through ink jet printer heads and the pigments have a tendency to settle out from the ink on standing for long periods. Furthermore, images formed from inks containing insoluble pigments are generally opaque and dull, limiting their usefulness on overhead projector slides.
There is a need for dyes and inks which have good storage stability, a high colour strength and produce images having a high light-fastness and water-fastness when printed on a substrate.
According to the present invention there is provided a dye of the Formula (1) and tautomers thereof:
wherein:
A is optionally substituted phenyl;
R
1
is H, optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkynyl;
R
2
is H, CN, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or a carbonamido group; and
R
3
is an optionally substituted 5- or 6- membered ring;
provided that R
1
is not methyl.
In a first preferred embodiment A is phenyl or mono substituted phenyl, more preferably mono substituted phenyl.
In a second preferred embodiment A is di-, tri-, tetra- or penta- substituted phenyl.
The optionally substituted alkyl, alkenyl or alkynyl group represented by R
1
is preferably optionally substituted C
2-12
-alkyl, C
2-12
-alkenyl or C
2-12
-alkynyl, more preferably optionally substituted C
2-12
-alkyl, especially C
2-4
-alkyl, more especially ethyl, n-propyl or iso-propyl.
When R
2
is optionally substituted alkyl, alkenyl or alkynyl it is preferably optionally substituted C
1-12
-alkyl, C,
1-12
-alkenyl or C
1-12
-alkynyl, more preferably optionally substituted C
1-12
-alkyl, especially C
1-4
-alkyl, more especially methyl.
When R
2
is optionally substituted aryl it is preferably optionally substituted phenyl.
R
2
is preferably CN or a carbonamido group. A preferred carbonamido group is of the formula CONHR
4
wherein R
4
is H or optionally substituted alkyl or aryl.
R
4
is preferably optionally substituted C
1-6
-alkyl or optionally substituted phenyl, more preferably C
1-4
-alkyl.
R
3
is preferably an optionally substituted 5- or 6-membered ring comprising carbon atoms and optionally one or two atoms selected from O, N and S, more preferably one O or S atom and four or five carbon atoms. R
3
is more preferably optionally substituted phenyl, cyclohexyl, cyclopentyl, furanyl, tetrahydrofuranyl, pyranyl, dihydropyranyl or tetrahydropyranyl. Still more preferably R
3
is optionally substituted furanyl or tetrahydrofuranyl, especially optionally substituted tetrahydrofuranyl.
Examples of groups represented by R
3
include furan-2-yl, tetrahydrofuran-2-yl, furan-3-yl, tetrahydrofuran-3-yl, pyran-2-yl, pyran-3-yl, pyran4-yl, dihydropyran-2-yl, dihydropyran-3-yl, dihydropyran-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl and tetrahydropyran-4-yl.
In one preferred embodiment at least one of the substituents on A is a hypsochromic substituent. A hypsochromic substituent is a substituent which causes a shift in the absorption maximum of the dye to a shorter wavelength relative to a dye which is identical in every respect except that in place of the substituent there is a hydrogen atom, as measured in CH
2
Cl
2
at 20° C.
Preferred substituents, most of which are hypsochromic, on A are of the formula CO
2
R
5
, OCOR
5
, COR
5
, COCOR
5
, SO
2
R
5
, SO
2
NH
2
, SO
2
NR
5
R
6
, SOR
5
, SO
2
OR
5
, CN, CONR
5
R
6
, CONH
2
and CF
3
; wherein each R
5
independently is optionally substituted phenyl or optionally substituted alkyl which is optionally interrupted by one or more oxygen, sulphur or nitrogen atoms; and each R
6
independently is H or a substituent as defined for R
5
; or R
5
and R
6
together with the nitrogen to which they are attached form a 5 or 6 membered ring.
Especially preferred hypsochromic substituents are of the formula CO
2
R
7
and CONHR
7
wherein each R
7
independently is [(CH
2
)
m
O]
n
R
8
, m is 2 or 3, n is 1, 2, 3 or 4 and R
8
is H or C
1-4
-alkyl.
The optional substituents present on A may also be selected from NHCOR
5
, wherein R
5
is as hereinbefore defined; alkoxy, preferably C
1-4
-alkoxy; alkyl, preferably C
1-4
-alkyl; halo, preferably Cl or F; nitro; hydroxy; and optionally substituted amino, preferably —NR
a
R
b
wherein R
a
and R
b
each independently H, C
1-4
-alkyl or C
1-4
-alkyl substituted by hydroxy, carboxy or sulpho.
When R
5
and R
6
together with the nitrogen to which they are attached form a 5 or 6 membered ring it is preferably optionally substituted morpholine, piperazine, piperidine, piperidone or piperidone monohydrate, more preferably 4-piperidone or 4-piperidone monohydrate.
Preferably R
5
is optionally substituted phenyl, optionally substituted C
1-4
-alkyl or R
7
wherein R
7
is as hereinbefore defined.
Preferably R
6
is H or optionally substituted C
1-4
-alkyl, more preferably H.
The optional substituents which may be present on R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are preferably selected from C
1-4
-alkoxy, especially methoxy; halo, especially Cl, Br or F; C
1-4
-alkyl, especially methyl; nitro; cyano; CF
3
hydroxy; optionally substituted amino, especially —NR
a
R
b
wherein R
a
and R
b
are as hereinbefore defined; amido, especially —CONR
a
R
b
wherein R
a
and R
b
are as hereinbefore defined; or ester, especially —CO
2
R
a
wherein R
a
is as hereinbefore defined other than H.
Preferably in the dyes according to the first preferred embodiment of the invention A is phenyl carrying one group of the formula CO
2
R
7
wherein R
7
is as hereinbefore defined.
Preferably in the dyes according to the second preferred embodiment of the invention A carries a total of 2, 3, 4 or 5 substituents, more preferably 2 or 3 substituents, especially 2 substituents.
More preferably in the dyes of the second preferred embodiment A is phenyl carrying two, more preferably one hypsochromic substituent, and two, more preferably one of the alternative substituents mentioned above.
In view of the foregoing preferences a preferred dye of Formula (1) is of the Formula (2) and tautomers thereof:
wherein:
each hyp independently is a group of the formula CO
2
R
5
, OCOR
5
, COR
5
, COCOR
5
, SO
2
R
5
, SO
2
NHR
5
, SO
2
NH
2
, SO
2
NR
5
R
5
, SOR
5
, SO
2
OR
5
, CN, CONHR
5
, CR
3
, CONHR
7
or CO
2
R
7
;
each R
9
independently is C
1-4
-alkoxy, halo, C
1-4
-alkyl, nitro, hydroxy or optionally substituted amino;
r is 0, 1 or 2;
q is 0, 1, or 2;
(r+q) is 1 ,2, 3 or 4; and
R
1
, R
2
, R
3
, R
7
and each R
5
independently are as hereinbefore defined.
Preferably R
1
in Formula (2) is optionally substituted C
2-12
-alkyl, more preferab

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