Aqueous ink compositions

Details Aqueous ink compositions Aqueous ink compositions

1999-03-30

2001-05-22

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031500, C106S031510, C106S031460, C106S031470, C106S031490

Reexamination Certificate

active

06235096

ABSTRACT:

This invention relates 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 intensly coloured images.
We have now found that very good ink jet printing inks may be prepared having the compositions defined below.
According to the present invention there is provided an ink comprising water, a water-dissipatable polymer and a dye, wherein the dye carries a group of the Formula (1):
wherein:
R
1
is optionally substituted branched chain alkyl; and
R
2
is H, optionally substituted alkyl or optionally substituted aryl.
Preferably R
1
is &agr;-branched optionally substituted alkyl, more preferably a group of the formula —CHR
3
R
4
wherein R
3
and R
4
are each independently optionally substituted alkyl or R
3
and R
4
together with the CH group to which they are attached from an optionally substituted 5- or 6- membered ring. Preferably R
1
has from 3 to 20 carbon atoms, more preferably 3 to 10 carbon atoms. Examples of preferred groups represented by R
1
include prop-2-yl, but-2-yl, pent-2-yl, pent-3-yl, hex-2-yl, hex-3-yl, hept-2-yl, cyclopentyl and cyclohexyl.
When the group —CHR
3
R
4
forms a 5- or 6-membered ring the ring is preferably a cyclohexyl or cyclopentyl ring.
R
2
is preferably optionally substituted aryl, more preferably optionally substituted alkyl.
When R
2
is optionally substituted aryl it is preferably an optionally substituted phenyl.
When R
2
is an optionally substituted alkyl group it can be straight chain or branched chain. Preferably R
2
is C
1-20
-alkyl, more preferably C
1-10
-alkyl, especially C
1-6
-alkyl, more especially C
2
-C
6
-alkyl, each of which is optionally substituted.
The optional substituents which may be present on R
1
, R
2
, R
3
and R
4
are preferably selected from C
1-4
-alkoxy, especially methoxy; halo, especially Cl, Br or F; C
1-4
-alkyl, especially methyl; nitro; cyano; optionally substituted amino, especially —NR
a
R
b
wherein R
a
and R
b
are each independently H, C
1-4
-alkyl or C
1-4
-alkyl substituted by hydroxy, carboxy or sulpho; or an ester group, especially —OCOR
a
or —CO
2
R
a
wherein R
a
is as hereinbefore defined.
In a preferred embodiment the group of Formula (1) is attached to a phenyl group in the dye, more preferably to a phenyl group carrying an azo, imine or alkylene substituent, especially such a substituent at the 4-position relative to the group of Formula (1).
In preferred ink the group of Formula (1) is attached to a phenyl group carrying an azo substituent at the 4-postion, more preferably the dye is of the Formula:
wherein:
A is the residue of a diazotisable aromatic or heterocyclic amine;
B is an optionally substituted 1,4-phenylene group; and R
1
and R
2
are as hereinbefore defined.
A is preferably phenyl, naphthyl, thaizolyl, isothiazolyl, benzothiazolyl, benzoisothiazolyl, pyrazolyl, thiadiazolyl, triazolyl, imidazolyl, thienyl, pyridyl or pyridoisothiazolyl, each of which is optionally substituted.
When A is phenyl it is preferably of the Formula (2):
wherein:
R
5
is —H, optionally substituted alkyl, optionally substituted alkoxy, —NO
2
, —CN, —CHO, alkenyl, —CF
3
, —SCN, halogen, acyl, ester, amide, thioalkyl or thioaryl, —SO
2
NH
2
, —SO
2
F, —SO
2
Cl, —CONH
2
, —COF or —COCl; and
n is an integer from 1 to 5.
When R
5
is acyl it is preferably —CO(C
1-4
-alkyl), —SO(C
1-4
-alkyl) or —SO
2
(C
1-4
-alkyl); when R
5
is an ester it is preferably —OCO(C
1-4
-alkyl), —COO(C
1-4
-alkyl) or —SO
3
(C
1-4
-alkyl); when R
5
is amide it is preferably a carbonamido or sulphonamido group, more preferably—CONH(C
4
-alkyl), —NHCO(C
1-3
-alkyl), —CON(C
1-4
-alkyl)
2
, —SO
2
NH(C
1-4
-alkyl), —NHSO
2
(C
1-4
-alkyl) or —SO
2
N (C
1-4
-alkyl)
2
; when R
5
is thioalkyl or thioaryl it is preferably —S(C
1-4
-alkyl) or —S(phenyl).
When A is naphthyl it is preferably of the Formula (3):
wherein:
R
5
is as hereinbefore defined; and
n
1
is an integer from 1 to 4.
When A is thiazolyl it is preferably of the Formula (4):
wherein:
R
6
is —H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, halogen or —Salkyl; and
R
7
is —H, optionally substituted alkyl, alkenyl, —CN, —NO
2
, —SO
2
alkyl, —COOalkyl, halogen or —CHO.
When A is isothiazolyl it is preferably of the Formula (5):
wherein:
R
8
is —H, optionally substituted alkyl, optionally substituted aryl, optionally substituted pyridyl, —SO
2
alkyl, —Salkyl, —Saryl or halogen; and
R
9
is —H, —CN, —NO
2
, —SCN or —COOalkyl.
When A is benzothiazolyl it is preferably of the Formula (6):
wherein:
R
10
is —H, —SCN, —NO
2
, —CN, halogen, optionally substituted alkyl, optionally substituted alkoxy, —COOalkyl, —OCOalkyl or —SO
2
alkyl; and
n
2
is from 1 to 4.
When A is benzoisothiazolyl it is preferably of the Formula (7):
wherein:
R
10
as hereinbefore defined; and
n
3
is from 1 to 4.
When A is pyrazolyl it is preferably of the Formula (8):
wherein:
each R
7
independently is as hereinbefore defined; and
R
11
is —H, optionally substituted alkyl or optionally substituted aryl,
When A is thiadiazolyl or triazolyl it is preferably of Formula (9) or (10):
wherein:
R
12
is —Salkyl, —Saryl, —SO
2
alkyl, halogen or optionally substituted C
1-4
-alkyl; and
W is S or N.
When A is imidazolyl it is preferably of the Formula (11):
wherein:
R
13
is —CN, —CHO, —CH═C(CN)
2
or —CH═C(CN)(COOalkyl);
R
14
is —CN or —Cl; and
R
15
is —H or optionally substituted alkyl.
When A is thienyl it is preferably of the Formula (12):
wherein:
R
16
is —NO
2
, —CN, alkylcarbonylamino or alkoxycarbonyl;
R
17
is —H, halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl or —Salkyl; and
R
18
is —H, optionally substituted alkyl, —CN, —NO
2
, —SO
2
alkyl, —COOalkyl, halogen, —CH═C(CN)
2
or —CH═C(CN)(COOalkyl).
When A is pyridyl it is preferably of the Formula (13):
wherein:
R
5
is as hereinbefore; and
n
4
is from 1 to 4.
When A is pyridoisothaizolyl it is preferably of the Formula (14):
wherein:
R
19
is —CN or —NO
2
; and
R
20
is optionally substituted alkyl.
When any of R
2
to R
20
is optionally substituted alkyl, optionally substituted alkoxy or optionally substituted aryl the optional substituents are preferably selected from —CN, —SCN, —NO
2
, halogen, especially —F, —Cl and —Br, —SC
1-4
-alkyl, —Sphenyl, C
1-4
-alkoxy and —COOC
1-4
-alkyl.
When any of R
3
to R
20
is or contains an alkyl or alkoxy group it is preferably C
1-6
-alkyl or C
1-6
-alkoxy, more preferably C
1-4
-alkyl, or C
1-4
-alkoxy.
The halogen group represented by R
5
, R
6
, R
7
, R
8
, R
10
, R
12
or R
18
is preferably —F, —Cl or —Br.
Especially preferred groups represented by R
5
are selected from —NO
2
, —CN, —COOC
1-4
-alkyl and C
1-4
-alkyl.
In phenyl groups of Formula (2) n is preferably from 1 to 3, more preferably 1 or 2. When the phenyl group of Formula (2) carries 3 substituents these are preferably in the 2-, 4- and 6-positions. When the phenyl group of Formula (3) carries 1 or 2 substituents these are p

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