Pigment preparations comprising two or more perylene compounds

Details Pigment preparations comprising two or more perylene compounds Pigment preparations comprising two or more perylene compounds

2000-01-25

2002-07-02

Green, Anthony (Department: 1755)

Compositions: coating or plastic

Materials or ingredients

Pigment, filler, or aggregate compositions, e.g., stone,...

C106S413000, C106S476000, C106S494000, C106S495000, C106S496000, C106S497000, C106S498000

Reexamination Certificate

active

06413309

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel pigment preparations having improved coloristic and rheological properties and to their preparation and use for pigmenting high molecular mass materials.
DESCRIPTION OF THE RELATED ART
Pigment preparations are combinations of pigments with pigment dispersants that are structurally analogous to pigments and are substituted by groups having a specific activity. They are added to the pigments in order to facilitate dispersion in the application media, especially in varnishes, and to improve the rheological and coloristic properties of the pigments. The viscosity of the highly pigmented paint concentrates (millbase) is lowered and the flocculation of the pigment particles is lessened. By this means it is possible, for example, to increase the transparency and the gloss. This is a particular requirement in the case of metallic pigments.
A large number of proposals exist for improving the rheological and coloristic properties of organic pigments by adding pigment dispersants, although not always with the desired result. EP-A-0 321 919 describes the production of pigment preparations by mixing the base pigments with pigment derivatives that contain methyleneimidazolyl groups. In the field of perylene pigments, this results in pigment preparations whose coloristic properties no longer meet current requirements.
DE-A-3 106 906 describes the preparation of pigment dispersants that contain sulfonamide groups. The pigment dispersants described therein are based on perylene compounds but have considerable coloristic and rheological deficiencies.
DE-A-1 97 09 798 discloses pigment preparations comprising asymmetric, and U.S. Pat. No. 4 762 569 the production of pigment preparations based on symmetric, perylene-3,4,9,10-tetracarboxylic diimides. These pigment preparations are in many cases suitable only for use in solventborne systems. Also, they do not meet all of the requirements made of them in terms of rheological and coloristic properties. Especially at high levels of pigment dispersant, the coloristic properties are no longer adequate, and in many cases a distinct loss of gloss and a deviation in shade can be noted. Moreover, these pigment dispersants possess inadequate solvent fastness and fastness to overcoating, thus greatly restricting their universal application. Furthermore, in many varnish systems it is possible to observe instances of incompatibility with the binder.
EP-A-0 485 441 describes the production of pigment preparations based on acidic perylene-3,4,9,10-tetracarboxylic diimides. However, these pigment preparations do not meet all of the requirements made of them in terms of rheological and coloristic properties. When acidic perylene compounds are used in aqueous coating systems, which are often of alkaline pH, there may be problems, thus restricting their universal application.
SUMMARY OF THE INVENTION
A need for improvement existed and the object was therefore to provide pigment preparations which overcome the abovementioned disadvantages of the prior art in terms of coloristics, rheology, and universal applicability.
It has been found that the object is surprisingly achieved by pigment preparations which in addition to the base pigments comprise a combination of at least two specific perylene-3,4,9,10-tetracarboxylic diimides.
The invention provides pigment preparations comprising
a) at least one organic base pigment,
b1) at least one pigment dispersant of the formula (I),
 in which the two radicals Z are identical or different and Z has the definition Z
1
, Z
2
, Z
3
or Z
4
, with the proviso that both radicals Z are not simultaneously Z
4
, and in which
Z
1
is a radical of formula (Ia),
—[X—Y]
q
—[X
1
—Y
1
]
r
—[X
2
—NH]
s
H  (Ia)
 in which
X, X
1
and X
2
are identical or different and are a branched or unbranched C
2
-C
6
-alkylene radical or a C
5
-C
7
-cycloalkylene radical which can be substituted by 1 to 4 C
1
-C
4
-alkyl radicals, hydroxyl radicals, hydroxyalkyl radicals having 1 to 4 carbon atoms, and/or by 1 or 2 further C
5
-C
7
-cycloalkyl radicals;
Y and Y
1
are identical or different and are an NH, —O or N(C
1
-C
6
-alkyl) group, preferably —NCH
3
, or
q is a number from 1 to 6, preferably 1, 2, 3 or 4;
r and s independently of one another are a number from 0 to 6, preferably 0, 1 or 2, r and s not simultaneously being zero; and in which
Z
2
is a radical of formula (Ib),
—[X—O]
q1
—[X
1
—O]
q
H  (Ib)
 in which
q
1
is a number from 0 to 6, preferably 0, 1, 2, 3 or 4;
and in which
Z
3
is a radical of formula (Ic),
 in which
R
2
and R
3
independently of one another are a hydrogen atom, a substituted or unsubstituted or partly fluorinated or perfluorinated alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted or partly fluorinated or perfluorinated alkenyl group having 2 to 20 carbon atoms, the substituents being able to be hydroxyl, phenyl, cyano, chloro, bromo, C
2
-C
4
-acyl or C
1
-C
4
-alkoxy and preferably from 1 to 4 in number, or
R
2
and R
3
together with the nitrogen atom, form a saturated, unsaturated or aromatic heterocyclic ring with or without a further nitrogen, oxygen or sulfur atom in the ring; and
X is as defined above;
Z
4
is hydrogen, hydroxyl, amino, phenyl or C
1
-C
20
-alkyl, the phenyl ring and the alkyl group being able to be substituted by one or more, e.g. 1, 2, 3 or 4, substituents from the group consisting of Cl, Br, CN, OH, C
6
H
5
, carbamoyl, C
2
-C
4
-acyl and C
1
-C
4
-alkoxy, such as methoxy or ethoxy, and the phenyl ring also being able to be substituted by NR
2
R
3
, where R
2
and R
3
are as defined above, or the alkyl group is perfluorinated or partly fluorinated;
b2) at least one pigment dispersant of the formula (II),
 in which
V is a bivalent radical —O—, >NR
4
, or >N—R
5
—Y
−
X
+
, and
W is the bivalent radical >N—R
5
—Y
−
X
+
,
D is a chlorine or bromine atom and, if o >1, may be a combination thereof, and
o is a number from 0 to 4;
R
4
is a hydrogen atom or a C
1
-C
20
-alkyl group, especially C
1
-C
4
-alkyl, or is a phenyl group which can be unsubstituted or substituted one or more times, e.g., 1, 2 or 3 times, by halo such as chloro or bromo, C
1
-C
4
-alkyl such as methyl or ethyl, C
1
-C
4
-alkoxy such as methoxy or ethoxy, or phenylazo,
R
5
is a C
1
-C
18
-alkylene group which can be interrupted one or more times within the C—C-chain by a bridge member from the series consisting of —O—, —NR
6
, —S—phenylene, —CO—, —SO
2
—, or —CR
7
R
8
or a chemically logical combination thereof, in which R
6
, R
7
and R
8
independently of one another are each a hydrogen atom or a C
1
-C
4
-alkyl group which can be unsubstituted or substituted by a heterocyclic radical, preferably imidazole or piperazine,
but in particular is a straight-chain or branched C
1
-C
6
-alkylene group such as ethylene or propylene; or is a phenylene group which can be unsubstituted or substituted one or more times, e.g., 1, 2 or 3 times, by C
1
-C
4
-alkyl such as methyl or ethyl, or C
1
-C
4
-alkoxy such as methoxy or ethoxy,
Y
−
is one of the anionic radicals —SO
3
−
or COO
−
, and
X
+
is H
+
or the equivalent
 of a metal cation M
m+
from main groups 1 to 5 or from transition groups 1 or 2 or 4 to 8 of the Periodic Table of the Chemical Elements, m being one of the numbers 1, 2 and 3, and M
m+
defining, for example, Li
1+
, Na
1+
, K
1+
, Mg
2+
, Ca
2+
, Sr
2+
, Ba
2+
, Mn
2+
, Cu
2+
, Ni
2+
, Co
2+
, Zn
2+
, Fe
2+
, Al
3+
, Cr
3+
or Fe
3+
;
or an ammonium ion N
+
R
9
R
10
R
11
R
12
, in which the substituents R
9
, R
10
, R
11
and R
12
independently of one another are each a hydrogen atom, C
1
-C
30
-alkyl, C
1
-C
30
-alkenyl, C
5
-C
30
-cycloalkyl, unsubstituted or C
1
-C
8
-alkyl-substituted phenyl, (C
1
-C
4
)-alkylene-phenyl, preferably benzyl, or are a (poly)alkyleneoxy

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