Perylene compounds and pigment preparations

Details Perylene compounds and pigment preparations Perylene compounds and pigment preparations

1999-02-22

2001-04-24

Green, Anthony (Department: 1755)

Compositions: coating or plastic

Materials or ingredients

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

C106S493000, C106S494000, C106S495000, C106S496000, C106S497000, C106S413000, C546S037000

Reexamination Certificate

active

06221150

ABSTRACT:

CROSS-REFERENCES TO RELATED APPLICATIONS
The present invention is described in the German priority applications Nos. 198 07 422.0, filed Feb. 21, 1998 and 198 35 757.5, filed Aug. 6, 1998, which are hereby incorporated by reference as is fully disclosed herein.
BACKGROUND OF THE INVENTION
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, which is desirable especially 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-B-0 321 919 describes the preparation 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.
U.S. Pat. No. 4,762,569 describes the preparation of pigment preparations on the basis of symmetrical perylene-3,4,9,10-tetracarboxylic diimides. These pigment preparations are suitable only for use in solventborne systems. They do not meet all of the requirements in terms of rheological and coloristic properties that are made of pigment preparations. At high pigment dispersant contents in particular the coloristic properties are no longer adequate and in many cases a distinct loss of gloss and marked shade deviation can be noted. Furthermore, these pigment dispersants possess inadequate solvent fastness and fastness to overcoating, thus greatly restricting their universal application. Moreover, in many varnish systems it is possible to observe instances of incompatibility with the binder, which is prohibitive for their use.
SUMMARY OF THE INVENTION
The present invention relates to novel pigment dispersants and pigment preparations having improved coloristic and rheological properties and to their preparation and use for pigmenting high molecular mass materials. 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 one or more particular perylene-3,4,9,10-tetracarboxylic diimides.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention provides perylene compounds of the formula (I)
in which
Z
1
is a radical of the 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 from 1 to 4 C
1
-C
4
-alkyl radicals, hydroxyl radicals, hydroxyalkyl radicals having 1 to 4 carbon atoms, and/or by from 1 to 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, but are not simultaneously zero, and s is different from zero, if Y
1
is —O—; and
Z is defined as Z
1
, Z
2
or Z
3
, where Z
2
is a radical of the 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 Z
3
is hydrogen, hydroxyl, amino or C
1
-C
8
-alkyl where the alkyl group can be substituted by from 1 to 4 substituents from the group consisting of Cl, Br, CN, OH, C
6
H
5
, carbamoyl, C
1
-C
4
-acyl, C
1
-C
4
-alkoxy and NR
2
R
3
, or is perfluorinated or partly fluorinated, and where
R
2
and R
3
independently of one another are a hydrogen atom, a substituted or unsubstituted or partly fluorinated or perfluorinated alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted or partly fluorinated or perfluorinated alkenyl group of 2 to 20 carbon atoms, where the substituents can be hydroxyl, phenyl, cyano, chloro, bromo, C
2
-C
4
-acyl or C
1
-C
4
-alkoxy, or R
2
and R
3
, together with the nitrogen atom, form a saturated, unsaturated or aromatic heterocyclic ring which if desired contains a further nitrogen, oxygen or sulfur atom in the ring.
Depending on the selection of the radicals Z and Z
1
symmetrical or asymmetrical pigment dispersants of the formula (I) are obtained. Asymmetrical pigment dispersants of the formula (I) include those having different radicals Z
1
.
Preference is given to perylene compounds of the formula (I) in which X, X
1
and X
2
are a C
2
-C
4
-alkylene radical or cyclohexylene.
Of particular interest, for example, are perylene compounds of the formula (I) in which Z
1
has one of the definitions —(CH
2
)
3
—NH—(CH
2
)
3
—NH
2
, —(CH
2
)
2
—NH—(CH
2
)
2
—NH
2
, —(CH
2
)
3
—NH—(CH
2
)
2
—NH—(CH
2
)
3
—NH
2
,
—(CH
2
)
3
—O—(CH
2
)
2
—O—(CH
2
)
3
—NH
2
, —(CH
2
)
3
—O—(CH
2
)
3
—O—(CH
2
)
3
—NH
2
, —(CH
2
)
2
—NH—(CH
2
)
3
—NH
2
, —(CH
2
)
3
—NH—(CH
2
)
2
—NH
2
, —(CH
2
)
2
—NH—(CH
2
)
2
—NH—(CH
2
)
2
—NH
2
, —(CH
2
—CH
2
—NH)
4
—H, —(CH
2
—CH
2
—NH)
5
—H or —(CH
2
)
3
—O—(CH
2
)
4
—O—(CH
2
)
3
—NH
2
.
Examples of perylene compounds of interest are those of the formula (I) in which Z
2
has one of the definitions —CH(CH
2
OH)
2
or —(CH
2
)
2
—O—(CH
2
)
2
OH.
Also of interest, for example, are perylene compounds of the formula (I) in which Z
3
is hydrogen, benzyl, C
1
-C
6
-alkyl or a C
2
-C
6
-alkyl which is substituted by from 1 to 2 substituents from the group consisting of hydroxyl, acetyl, methoxy and ethoxy, and with particular preference is hydrogen, methyl, ethyl, propyl, butyl, benzyl, hydroxyethyl, hydroxypropyl or methoxypropyl.
Of further interest are perylene compounds of the formula (I) in which Z
3
is a radical of the group —(CH
2
)
n
—NR
2
R
3
in which n is a number from 1 to 6, preferably from 2 to 4, and
R
2
and R
3
independently of one another are a hydrogen atom, a C
1
-C
6
-alkyl group, a C
1
-C
6
-alkyl group which is substituted by from 1 to 2 substituents from the group consisting of hydroxyl, acetyl, methoxy, ethoxy, chloro and bromo, or R
2
and R
3
, together with the adjacent nitrogen atom, form an imidazolyl, piperidinyl, morpholinyl, pipecolinyl, pyrrolyl, pyrrolidinyl, pyrazolyl or piperazinyl ring.
Of particular interest in this context are perylene compounds in which
n is the number 2 or 3, and
R
2
and R
3
are each a methyl or ethyl group or R
2
and R
3
, together with the adjacent nitrogen atom, form an imidazolyl, piperazinyl or morpholinyl radical.
The present invention also provides a process for preparing the perylene compounds of the formula (I) by reacting perylene-3,4,9,10-tetracarboxylic monoanhydride monoimides of the formula (IIa)
with one or more, preferably 1 or 2, amines of the formula (IIIa) or (IIIb)
Z—NH
2
  (IIIa)
Z
1
—NH
2
  (IIIb);
or by reacting perylene-3,4,9,10-tetracarboxylic monoanhydride monoimides of the formula (IIb)
with one or more, preferably 1 or 2, amines of the formula (IIIb); or by reacting perylene-3,4,9,10-tetracarboxylic dianhydride of the formula (IIc)
with one or more, preferably 1 or 2, amines of the formula (IIIb).
The anhydride groups in the formulae (IIa), (IIb) and (IIc) ca

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