Pigment preparations useful for ink-jet printing

Details Pigment preparations useful for ink-jet printing Pigment preparations useful for ink-jet printing

1999-08-30

2001-06-12

Klemanski, Helen (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031890, C106S499000

Reexamination Certificate

active

06245138

ABSTRACT:

The invention relates to a method for ink-jet printing with a printing ink containing a pigment preparation and pigment preparations of specific organic pigments that are useful as printing inks for ink-jet printing.
Aqueous printing inks for ink-jet printing based both on water-soluble organic dyestuffs and on organic colored pigments are known and are described in many publications. Compared with soluble dyestuffs, pigments generally produce an improved lightfastness in the resultant print-outs. However, it is also known that ink-jet prints of most pigments do not achieve the same brilliance as those of dyestuffs. Although the brilliance of the prints can be improved by use of a particularly high fine distribution of the pigment particles, this improvement is generally accompanied by a loss in lightfastness properties. Cf. Herbst, Hunger:
Industrielle Organischle Pigmente [Industrial Organic Pigments
], VCM, Verlagsgesellschaft, Weinheim (1987), pages 135-136.
According to European Patent Application 633,142, the brilliance can be improved, for example, by a suitable choice of additives for the inks or by a suitable choice of printing substrates, such as, for example, appropriately coated papers. The problem of providing both brilliant and light-fast pigments for ink-jet printing, however, has not yet been solved satisfactorily by the prior art methods. This applies particularly to the yellow color shade range.
Despite the large number of publications, the above-mentioned object has not yet been satisfactorily achieved. Moreover, only a very few publications list examples of yellow pigments that are indeed suitable in principle in their lightfastness properties for conventional ink-jet printing, but which do not satisfy the lightfastness properties required for higher quality fields of ink-jet printing use, such as photographic image reproduction (photoreproduction, for example, for use outside or for display). E.g., European Patent Application 518,225.
SUMMARY OF THE INVENTION
The present invention, therefore, relates to a method comprising ink-jet printing with a printing ink containing a pigment preparation comprising
(a) water,
(b) a dispersing agent, and
(c) at least one pigment consisting of a barbituric acid substituted by radicals containing methine or azo groups or a derivative thereof, said pigment preferably being present as a salt or a complex, a solid solution, an inclusion compound, or an intercalation compound.
In a particularly preferred embodiment, component (c) is one or more pigments having the formulas (I) to (III) or tautomeric forms thereof
wherein
B is an isoindoline group having the formula
wherein the double bonds are linked respectively through the 1- and 3-positions of the isoindoline group;
A is a cyanomethylene group having the formula
Z
1
to Z
10
are independently O or NR
10
;
R
1
, R
2
, R
3
, and R
4
are independently hydrogen, alkyl (preferably C
1
-C
6
alkyl), cycloalkyl (preferably C
5
-C
8
cycloalkyl), aryl (preferably phenyl or substituted phenyl), aralkyl (preferably (C
6
-C
10
aryl)(C
1
-C
4
alkyl) such as benzyl or phenethyl), or heteroaryl;
R
5
, R
6
, R
7
, and R
8
are independently hydrogen, halogen (preferably F, Cl, or Br), C
1
-C
6
alkyl, C
1
-C
6
alkoxy, or C
6
-C
10
aryloxy;
R
9
is an electron-withdrawing group; and
R
10
is hydrogen or cyano.
DETAILED DESCRIPTION OF THE INVENTION
Pigments of formula (I) are known, for example, from German Offenlegungsschrift 3,935,858, pigments of formula (II) are known, for example, from U.S. Pat. No. 5,177,209, and pigments of formula (II) are known, for example, from European Patent Application 74,515.
As used herein, the term “alkyl” refers to straight or branched chain aliphatic hydrocarbon groups. Examples of the preferred C
1
-C
6
alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, and the isomeric forms thereof. The term “alkoxy” refers to straight or branched chain alkyl oxy groups. Examples of the preferred C
1
-C
6
alkoxy groups are methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, and the isomeric forms thereof. The term “cycloalkyl” refers to cycloaliphatic hydrocarbon groups. Examples of the preferred C
5
-C
7
cycloalkyl are cyclopentyl, cyclohexyl, and cycloheptyl. The term “aryl” refers to aromatic hydrocarbon groups, including aromatic hydrocarbon groups substituted with groups such as alkyl, alkoxy, halogen, hydroxy (including tautomeric oxo forms), alkoxycarbonyl, aryloxycarbonyl, cyano, and nitro groups. Examples of the preferred aryl groups are phenyl and substituted derivatives thereof. The term “aryloxy” refers to aromatic hydrocarbon groups attached through an oxygen atom. Examples of the preferred C
6
-C
10
aryloxy groups are phenoxy and naphthoxy and derivatives thereof in which the aryl portion is substituted as described above for “aryl” groups. The term “aralkyl” (or, “arylalkyl”) refers to alkyl groups bearing aryl group as substituents. Examples of the preferred (C
6
-C
10
aryl)(C
1
-C
4
alkyl) groups are benzyl or phenethyl. The term “heteroaryl” refers to aromatic groups, preferably five- or six-membered aromatic groups, having one or more ring heteroatoms, such as nitrogen, oxygen, and sulfur, and fused ring analogs thereof. The term “heteroaryl” also refers to heteroaryl groups further substituted with hydroxy (including tautomeric oxo forms), halogen, alkyl, alkoxy, alkoxycarbonyl, or aryloxycarbonyl.
The group R
9
preferably represents a group in which the Hammett substituent constant &sgr; (para) is greater than zero. A corresponding list of Hammett substituent constants can be found, for example, in Sykes,
Reaktionsmechanismen der organischen Chemie [Reaction Mechanisms of Organic Chemistry
], 9th edition, Weinheim VCM Verlagsgesellschaft, 1988, or can be determined by known methods. Examples of suitable electron-withdrawing groups include —CN, —COOH and esters and amides thereof, aldehyde and ketone carbonyl, —SO
3
H and esters and amides thereof, —NO
2
, —NO, —ONO, halogen, ammonium groups, aryl, and heteroaryl.
Preferred pigments of formula (I) are symmetric isoindoline pigments corresponding to formula (IV)
wherein R
11
is hydrogen, C
1
-C
6
alkyl, or phenyl. Especially preferred pigments of formula (I) correspond to formula (IV) in which R
11
is hydrogen.
Preferred pigments of formula (II) are asymmetric isoindoline pigments corresponding to formula (V)
wherein
R
9
is —CN, aminocarbonyl or aminocarbonyl substituted with C
1
-C
6
alkyl, C
5
-C
7
cycloalkyl, aralkyl (preferably (C
6
-C
10
aryl)(C
1
-C
4
alkyl)), or C
6
-C
10
-aryl) (more preferably —CONHCH
3
), C
1
-C
6
alkoxycarbonyl, C
6
-C
10
aryloxy-carbonyl, or heteroaryl such as heteroaryl groups having the formulas (VI) or (VII)
wherein
R
13
and R
14
are independently hydrogen, halogen (preferably Cl, Br, or F), C
1
-C
6
alky, C
1
-C
6
alkoxy, or C
1
-C
6
alkoxycarbonyl, or R
13
and R
14
together form a fused-on benzene ring,
G is O, S, NH, or N(C
1
-C
4
alkyl), and
R
12
is hydrogen, C
1
-C
6
alkyl, or phenyl.
Especially preferred pigments of formula (V) are those in which R
9
is —CONHCH
3
and R
12
has the above-mentioned meaning, particularly pigments in which R
9
is —CONHCH
3
and R
12
is hydrogen.
Preferred pigments are salts, complexes, inclusion compounds, solid solutions, and intercalation compounds corresponding to the pigments of formula (III). Such pigments are known, for example, from European Patent Application 74,515. Preferred salts and complexes of the compounds of the formula (III) are the salts and complexes of the corresponding mono-, di-, tri-, and tetra-anions with the metals Li, Cs, Mg, Cd, Co, Al, Cr, Sn, and Pb, and most preferably with the metals Na, K, Ca, Sr, Ba, Zn, Fe, Ni, Cu, and Mn. The nickel salts and complexes and solid solutions and intercalation and inclusion compounds thereof are of particular importance. An inclusion compound, intercalation compound, or solid solution of a salt or a complex of azobarbituric acid (particularly of the azobarbituric acid-nickel 1:1 complex) i

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