Ink composition

Details Ink composition Ink composition

2000-04-06

2002-04-30

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031520, C534S701000, C534S724000, C427S466000, C428S195100

Reexamination Certificate

active

06379442

ABSTRACT:

This invention relates to a composition comprising two or more dyes, to inks containing such compositions and to processes using said inks in printing and imaging technologies, especially ink jet printing.
Ink jet printing is a non-impact printing technique which involves ejecting, thermally or by action of an oscillating piezo crystal, droplets of ink continuously or on demand from a fine nozzle directly onto a substrate such as paper, plastics, textile, metal or glass. The inks used in an ink jet printer are required to meet a number of criteria. For example, they must provide sharp, non-feathered images which have good water-fastness, light-fastness and optical density. Furthermore, the inks must dry quickly when applied to a substrate, however, they must not dry or crust over in the ink jet head as this can result in clogging of the ink jet nozzle. The inks must also be stable to storage over long periods of time without deterioration in the properties of the ink.
We have surprisingly found that mixtures comprising a magenta dye and certain copper complex azo dyes are valuable as colorants for ink jet printing inks. In particular inks containing the mixture of dyes give enhanced operability in ink jet printers, and provide prints with a surprising increase in light-fastness and an improved print quality compared with inks containing the magenta dye alone. Many of the prints also exhibit a higher reflected optical density with little or no loss of chroma compared with prints obtained using the magenta dye alone.
According to a first aspect of the present invention, there is provided a composition comprising:
(a) a water-soluble magenta dye; and
(b) a dye of the Formula (1) or a salt thereof:
wherein:
R
1
is H, halo, vinyl sulphonyl or a group which is convertible to vinyl sulphonyl on treatment with aqueous alkali;
R
2
is H or optionally substituted alkyl;
R
3
is acetyl, optionally substituted benzoyl or a group of the Formula (2):
X is a labile or a non labile atom or group;
Y is halo, —NR
4
R
5
, —SR
5
or —OR
5
;
R
4
and R
5
each independently is H, optionally substituted alkyl, optionally substituted phenyl, or R
4
and R
5
together with the nitrogen to which they are attached form a 5 or 6 membered ring; and
n is 0 or 1.
When R
1
is halo it is preferably F or Cl, more preferably Cl. It is especially preferred that when R
1
is halo it is attached ortho to the oxygen.
When R
1
is a group which is convertible to vinyl sulphonyl on treatment with aqueous alkali it is preferably of the formula —SO
2
CH
2
CH
2
OSO
3
H, —SO
2
CH
2
CH
2
SSO
3
H, —SO
2
CH
2
CH
2
Cl or —SO
2
CH
2
CH
2
OCOCH
3
.
R
2
is preferably H or optionally substituted C
1-4
alkyl, more preferably H or C
1-4
-hydroxyalkyl. It is especially preferred that R
2
is H.
When R
3
is optionally substituted benzoyl the optional substituent(s) is/are preferably selected from C
1-4
alkyl, C
1-4
alkoxy, C
1-4
-hydroxyalkyl, C
1-4
alkylamino, hydroxy-C
1-4
-alkylamino, halo (especially F or Cl), hydroxy, carboxy, sulpho, nitro, amino and cyano. More preferably the benzoyl group is unsubstituted.
R
3
is preferably acetly, benzoyl or a group of the Formula (2).
When X represents a labile atom or group, it is preferably an atom or group which is bound by a covalent bond to the triazine nucleus, which atom or group is displaceable by a hydroxyl group of cellulose under mildly alkaline aqueous conditions to form a covalent bond between the triazine nucleus and cellulose. As examples of such atoms or groups represented by X there may be mentioned halo, for example F and 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.
More preferably when X is a labile atom or group it is a quaternary ammonium group or halo, especially 3- or 4-carboxypyridinium, F or Cl, and more especially Cl.
When X is a non-labile group it is preferably —OR
6
, —SR
6
or —NR
7
R
8
wherein R
6
, R
7
and R
8
are each independently H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aralkyl, optionally substituted aryl or R
7
and R
8
together with the nitrogen atom to which they are attached form a 5 or 6 membered ring.
Preferably R
6
, R
7
and R
8
are each independently selected from H; optionally substituted C
1-10
-alkyl, more preferably optionally substituted C
1-4
-alkyl; optionally substituted phenyl; and optionally substituted —(CH
2
)
1-4
-phenyl, especially optionally substituted benzyl.
The preferred optional substituents on R
6
, R
7
or R
8
are selected from C
1-4
-alkyl, C
1-4
-alkoxy, C
1-4
-alkylamino, C
2-4
-hydroxyalkyl, di-(C
1-4
-alkyl)amino, C
2-4
-hydroxyalkylamino di-(C
2-4
-hydroxyalkyl)amino, —OH, —CN, —COOH, PO
3
H
2
and NH
2
. More preferably the substituents are selected from —OH, —CH
3
, —OCH
3
, —SO
3
H and —CO
2
H.
When R
6
and R
7
together with the nitrogen atom to which they are attached form a 5- or 6-membered ring it is preferably morpholine, piperidine or piperazine optionally substituted by C
1-4
-alkyl or hydroxy-C
2-4
-alkyl, more preferably it is piperazine optionally substituted at the 4-position by C
1-4
-alkyl or hydroxy-C
2-4
-alkyl.
Preferred groups of the formula —OR
6
, —SR
6
or —NR
6
R
7
include OH; SH; C
1-4
-alkoxy, for example methoxy or ethoxy; mono- or di-(C
2-4
-hydroxyalkyl)amino, for example mono or di-(2-hydroxyethyl)amino; morpholinyl; piperidinyl; piperazinyl; 4-(hydroxy-C
2-4
-alkyl)-piperazin-1-yl, for example 4-hydroxyethylpiperazin-1-yl; 4-(C
1-4
-alkyl)piperazin-1-yl, for example 4-methylpiperazin-1-yl; C
1-6
-alkylamino, for example dimethylamino, n-butylamino or n-hexylamino; carboxy-C
1-4
-alkylamino, for example 2-carboxymethylamino; arylamino, for example phenylamino, mono-3- or di-3,5-carboxyanilino; or aralkylamino, for example benzylamino, mono-3- or di-3,5-carboxyphenylmethylamino.
It is especially preferred that X is selected from Cl, —OH and —NHR
9
wherein R
9
is H, C
1-4
-alkyl or C
2-4
-hydroxyalkyl.
Y is preferably —NR
4
R
5
or —OR
5
.
Preferably R
4
and R
5
are each independently selected from H; optionally substituted C
1-10
-alkyl, especially optionally substituted C
1-4
-alkyl; and optionally substituted phenyl. Preferred optional substituents on R
4
and R
5
are selected from —OH, C
1-4
-alkyl, C
1-4
-alkoxy, C
1-4
-alkoxycarbonyl-, C
1-4
-alkylcarbonyl, —PO
3
H
2
, —COOH, —SO
3
H, —NO
2
, —CN, —NH
2
, C
1-4
-alkylamino-, hydroxy C
2-4
-alkylamino- and hydroxy C
2-4
-alkyl.
It is especially preferred that R
4
and R
5
are each independently selected from H, C
1-4
-alkyl, hydroxyC
2-4
-alkyl-, or phenyl optionally substituted by —SO
3
H, —PO
3
H
2
, —COOH or —OH, more especially R
4
is H and R
5
is selected from H, C
1-4
-alkyl, or phenyl optionally substituted by —COOH, —SO
3
H, —PO
3
H
2
or —OH.
When R
4
and R
5
together with the nitrogen to which they are attached form a 5 or 6 membered ring it is preferably a piperazine or morpholine ring.
Preferred groups represented by Y include, for example, —OH, phenoxy, —NH
2
, sulphophenylamino (especially 3-sulphophenylamino) and phosphonophenylamino (especially 3-phosphonophenylamino).
In a first preferred embodiment component (b) of the composition is a dye of the Formula (1) wherein X is selected from Cl, —OH and —NHR
9
wherein R
9
is as hereinbefore defined; Y is —OH, phenoxy, —NH
2
, sulphophenylamino or phosphonophenylamino; n is 0 or 1; and R
1
is Cl or vinylsulphone.
In view of the foregoing preferences, component (b) is a dye of the Formula (3), (4), (5) or (6) or a salt thereof:
wherein:
each X
1
independently is Cl, OH or —NH
2
;
R
10
is —NH
2
or phenoxy; and
R
11
is —COCH
3
or —COC6H
5
.
It is especially preferred that component (b) is a compound of the Formula (3) wherein X
1
is Cl or —OH, and especially Cl.
The dye of Formula (1) may be prepared using known processes for the preparation of other similar azo compounds. For example, a suitable method com

Affiliated with

Also associated with

Rating

Ink composition does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Ink composition, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Ink composition will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2828285