Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2000-02-16
2002-06-25
Green, Anthony (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S493000, C106S495000, C106S496000, C106S497000, C106S498000, C106S499000
Reexamination Certificate
active
06409816
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel pigment preparations based on diketopyrrolopyrrole pigments and basic perylene dispersants, having improved coloristic and rheological properties, and to their preparation and use for pigmenting high molecular mass materials.
2. Description of the Related Art
Pigment preparations are combinations of pigments and pigment dispersants that are structurally analogous to pigments and are substituted by groups having a specific effect. The dispersants are added to the pigments in order to facilitate their dispersion in the application media, especially in varnishes, and in order 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 reduced. This makes it possible, for example, to enhance the transparency and gloss. Such enhancement is particularly desirable in the case of metallic pigments.
JP-A-03-026 767 discloses basic sulfonamides of diketopyrrolopyrroles and their use as dispersants with various pigments.
DE-A-197 09 798 discloses pigment preparations comprising asymmetric, and U.S. Pat. No. 4,762,569 the production of pigment preparations comprising symmetric, perylene-3,4,9,10-tetracarboxylic diimides. The use of these perylene dispersants with diketopyrrolopyrrole pigments, however, has not been described.
In the case of diketopyrrolopyrrole pigments there was a need for improvement and thus the object was to provide diketopyrrolopyrrole pigment preparations which satisfy the present-day requirements of the state of the art in terms of coloristics, rheology and universal applicability.
SUMMARY OF THE INVENTION
It has been found that this object is surprisingly achieved by means of pigment preparations which in addition to the diketopyrrolopyrrole pigment comprise certain symmetric or asymmetric perylene-3,4,9,10-tetracarboxylic diimides. It was unforeseeable that a combination of a diketopyrrolopyrrole pigment with a pigment dispersant that was not a structural derivative of a diketopyrrolopyrrole would exhibit advantages over the diketopyrrolopyrrole pigment alone.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention provides pigment preparations comprising
a) at least one diketopyrrolopyrrole pigment or a mixed crystal containing a diketopyrrolopyrrole pigment, and
b) at least one pigment dispersant of the formula (I),
in which the two radicals Z are identical or different and have the definition Z
3
or Z
4
with the proviso that both radicals Z are not simultaneously Z
4
, and in which
Z
3
is a radical of the formula (Ic),
in which
R
2
and R
3
are identical or different and 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, possible substituents being hydroxyl, phenyl, cyano, chloro, bromo, C
2
-C
4
-acyl and C
1
-C
4
-alkoxy and preferably being 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 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 1 or 2 further C
5
-C
7
-cycloalkyl radicals;
Z
4
is hydrogen, hydroxyl, amino, phenyl, (C
1
-C
4
-alkyl)phenyl or C
1
-C
20
-alkyl, it being possible for the phenyl ring and the alkyl group 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—e.g., methoxy or ethoxy—and for the phenyl ring to be substituted by NR
2
R
3
, R
2
and R
3
being as defined above, or for the alkyl group to be perfluorinated or partly fluorinated.
Depending on the radicals Z selected, symmetric or asymmetric pigment dispersants of the formula (I) are obtained, asymmetric pigment dispersants of the formula (I) including those having different radicals Z
3
.
Advantageous pigment dispersants, for example, are those of the formula (I) in which X is a C
2
-C
4
-alkylene radical or cyclohexylene.
Advantageous pigment dispersants, for example, are those of the formula (I) in which
R
2
and R
3
independently of one another are a hydrogen atom, a C
1
-C
6
-alkyl group, or a C
1
-C
6
-alkyl group substituted by 1 or 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, piperidyl, morpholinyl, pipecolinyl, pyrrolyl, pyrrolidinyl, pyrazolyl or piperazinyl ring.
Particularly advantageous pigment dispersants are, for example, those of the formula (I) in which Z
3
has one of the definitions —(CH
2
)
2
—NH
2
, —(CH
2
)
3
—NH
2
,
—CH
2
—CH(CH
3
)—NH
2
, —CH
2
—C(CH
3
)
2
—CH
2
—NH
2
,
—(CH
2
)
2
—NH—CH
3
, —(CH
2
)
2
—N(CH
3
)
2
, —(CH
2
)
2
—NH—CH
2
—CH
3
, —(CH
2
)
2
—N(CH
2
—CH
3
)
2
, —(CH
2
)
3
—NH—CH
3
, —(CH
2
)
3
—N(CH
3
)
2
, —(CH
2
)
3
—NH—CH
2
—CH
3
and —(CH
2
)
3
—N(CH
2
—CH
3
)
2
.
Advantageous pigment dispersants are, for example, those of the formula (I) in which Z
4
is hydrogen, amino, phenyl, benzyl, NR
2
R
3
-substituted phenyl or benzyl, C
1
-C
6
-alkyl or a C
2
-C
6
-alkyl substituted by 1 or 2 substituents from the group consisting of hydroxyl, acetyl, methoxy and ethoxy, and with particular preference hydrogen,
methyl, ethyl, propyl, butyl, benzyl, hydroxyethyl, hydroxypropyl or methoxypropyl.
The perylene compounds of the formula (I) that are used in accordance with the invention as pigment dispersants as per b) can be prepared, for example, in accordance with DE-A-197 09 798 or in accordance with U.S. Pat. No. 4,762,569.
Component a) comprises diketopyrrolopyrrole pigments, mixtures of at least 2—e.g., 2 or 3—such pigments, or mixtures comprising at least 1—e.g., 1, 2 or 3—diketopyrrolopyrrole pigments, and also mixed crystals containing diketopyrrolopyrrole pigments, which may also be present in the form of conventional pigment preparations.
For the purposes of the present invention, suitable diketopyrrolopyrroles include or are, for example, C.I. Pigment Red 254 (C.I. No. 56 110), C.I. Pigment Red 255 (C.I. No. 56 1050), C.I. Pigment Red 264 (C.I. No. 561 300), C.I. Pigment Red 270, C.I. Pigment Red 272 (C.I. No. 56 1150), C.I. Pigment Orange 71 (C.I. No. 561 200), C.I. Pigment Orange 73 (C.I. No. 561 170). Component a) can also, for example, be a mixture of a diketopyrrolopyrrole and a quinacridone pigment.
The amount of the pigment dispersants of b) of the formula (I) in the pigment preparations of the invention can vary within wide limits provided it does not adversely affect the target pigment quality; in general, however, the amount is from 1 to 40% by weight, preferably from 2 to 30% by weight, based on the overall weight of the pigment preparation.
The pigment preparations of the invention may further include surface-active agents and other conventional additives, such as, for example, fillers, standardizers, resins, defoamers, antidust agents, extenders, shading colorants, preservatives and drying retarders.
Preferred pigment preparations for the purposes of the present invention consist essentially of
i) from 40 to 99% by weight, preferably from 70 to 98% by weight, of component a);
ii) from 1 to 40% by weight, preferably from 2 to 30% by weight, of at least one, preferably 1, 2 or 3, pigment dispersants as per b) of the formula (I);
iii) from 0 to 20% by weight, preferably from 0.1 to 15% by weight, of surface-active agents; and
iv) from 0 to 20% by weight, preferably from 0.1 to 10% by weight, of other, conventional additives,
the fractions of the respective components being based on the overall weight of the preparat
Dietz Erwin
Weber Joachim
Clariant GmbH
Green Anthony
Hanf Scott E.
Jackson Susan S.
LandOfFree
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