Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2003-04-24
2004-11-23
Green, Anthony J. (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S402000, C106S413000, C106S476000, C106S493000, C106S494000, C106S495000, C106S496000, C106S497000, C106S499000, C106S031780, C430S106100, C524S081000, C524S086000, C524S087000, C524S088000, C524S089000, C524S090000, C524S104000
Reexamination Certificate
active
06821335
ABSTRACT:
The present invention is situated in the field of aqueous pigment preparations.
In the production of preparations and dispersions of colorants, for example, disperse dyes or organic and inorganic pigments, for applications in aqueous or organic media, a large number of nonionic, anionic, and cationic surfactants is presently in use. The incorporation of pigments or their preparations into coating systems, printing inks, plastics, and other applications is sometimes accompanied by difficulties, since the fine and flocculation-stable dispersion of numerous pigments in the respective application medium is very unsatisfactory and involves a high level of dispersing effort. Consequently, the performance properties are very often inadequate. For instance, during the dispersing operation and thereafter as well, flocculation phenomena and formation of sediment may occur, which lead to changes in the viscosity of the application medium, to changes in shade and to losses in color strength, opacity, gloss, homogeneity, and brightness and also to shades which are difficult to reproduce and to an excessive tendency for paints to run in the case of the materials colored.
For improving the pigment properties a variety of derivatives of pigment molecules are known which are said to enhance the dispersibility. For example, for quinacridone pigments, additives are described which are based on the chemical bonding of isoindole-1,3-diones to this pigment class. One example of this class of compound is the 2-(phthalimido-methyl)quinacridone U.S. Pat. No. 4,478,968 describes for enhancing the dispersing properties of the quinacridone pigment.
EP-A-0 636 666 describes imide and bisimide derivatives which derive from perylene-3,4,9,10-tetracarboxylic anhydride and are made available by reaction with amines. These imides are suitable for producing pigment preparations.
None of the products described in the cited documents above, however, is capable of decisively enhancing the fluidity and the flocculation stability of pigment dispersions without having a deleterious influence on other parameters, such as color strength, gloss, shade, and dispersibility. One of the disadvantages of the products described in the abovementioned documents is that the soluble pigment derivatives, which are themselves intensely colored, can lead undesirably to bleeding in binder systems or in plastics and so to the staining of adjacent materials. Moreover, owing to the low solubility of the parent pigments, the preparation of pigment-derived compounds of this kind involves difficult conditions and a high cost. A further disadvantage is the limited application scope, which because of their intrinsic color remains restricted to pigments of the same or similar color.
The present invention was based on the object of providing pigment preparations which are suitable for producing highly fluid, flocculation-resistant, and storage-stable colorant dispersions for exterior and interior coating and are largely free from the disadvantages specified above.
The object stated is surprisingly achieved by adding below-specified nonpigmentary cyclic imides having aliphatic or olefinic carbon chains, which are virtually colorless or only very slightly colored, to organic or inorganic pigments.
The present invention provides pigment preparations comprising
a) at least one organic or inorganic pigment;
b) at least one cyclic imide of the general formula (1)
where
R
1
[lacuna] for a straight-chain, branched or cyclic aliphatic radical having 10 to 30, preferably 12 to 25, carbon atoms; for an alkenyl radical having 10 to 30, preferably 12 to 25, carbon atoms, it being possible for the radicals stated to be substituted by one or more, e.g., 2, 3, 4 or 5, substituents from the group consisting of C
1
-C
6
alkyl, C
1
-C
6
alkoxy, C
6
-C
10
aryl, hydroxyl, carboxyl, and sulfo;
R
2
, R
3
, R
4
and R
5
are identical or different and denote hydrogen, C
1
-C
10
alkyl, C
1
-C
10
alkoxy, halogen, —OR
6
, —NR
6
R
7
, —COOR
6
, —CONR
6
R
7
, —NR
6
—COR
7
, SO
2
NR
6
R
7
, —SO
3
M, —NO
2
, —CN or CF
3
, R
6
and R
7
standing for H or an alkyl radical having 1 to 10 carbon atoms and M standing for one equivalent of a 1 to 3 valent cation, e.g. hydrogen or alkali metal; and
c) if desired, further customary additives.
Compounds of the formula (1) per se are known. These compounds are described in, for example, U.S. Pat. No. 4,992,204, but are not used together with organic pigments.
U.S. Pat. No. 6,039,769 describes the use of nonpigmentary cyclic imides having short alkyl radicals for perylene pigment preparations.
Preferred imides of the formula (1) are those wherein
R
1
denotes decyl, dodecyl, tetradecyl, octadecyl, isotridecyl, lauryl, oleyl or stearyl.
Preferred imides of the formula (1) are also those wherein R
2
, R
3
, R
4
, and R
5
are identical or different and denote hydrogen, methyl, ethyl, propyl, butyl, methoxy, ethoxy, amino, methylamino, dimethylamino, ethylamino, diethylamino, carboxyl, COOCH
3
, carboxamide, CON(CH
3
)
2
, sulfonamide, SO
2
N(CH
3
)
2
, sulfo, nitro, cyano or CF
3
.
The compounds of the formula (1) used in the pigment preparations of the invention can be prepared by known methods from the aromatic parent structures, preferably the cyclic anhydrides, by reaction with the corresponding fatty amines. The cyclic anhydrides are either commercially available or can be prepared easily by known methods from the corresponding dicarboxylic acids: for example, by heating and by treatment with strong acids or dehydrogenating reagents. Of the numerous fatty amines and the natural fatty amine mixtures, only the most important will be mentioned here, such as, for example, dodecylamine, tetradecylamine, octadecylamine, isotridecylamine, coconut fatty amine, laurylamine, oleylamine, rapeseed oil fatty amine, stearylamine or tallow fatty amine. In addition to the fatty amines, mention may also be made of resin amines, and the derivatives preparable therefrom. The water formed during the reaction may be removed distillatively with the addition where appropriate of an azeotrope former: for example, a hydrocarbon or chlorohydrocarbon.
Preferably, however, the amide formation is carried out without solvent simply by distillative removal of the water of reaction formed. Owing to the quantitative yields of amide there is no need for further purification or treatment of the product.
Examples of organic pigments in the sense of the invention are monoazo pigments, disazo pigments, disazo condensation pigments, laked azo pigments, triphenylmethane pigments, thioindigo pigments, thiazine indigo pigments, perylene pigments, perinone pigments, anthanthrone pigments, diketopyrrolopyrrole pigments, dioxazine pigments, quinacridone pigments, phthalocyanine pigments, isoindolinone pigments, isoindoline pigments, benzimidazolone pigments, naphthol pigments and quinophthalone pigments, preference being given to anthanthrone pigments, dioxazine pigments, and phthalocyanine pigments, and also acid to alkaline carbon blacks from the group of the furnace blacks or gas blacks.
Examples of suitable inorganic pigments are titanium dioxides, zinc sulfides, iron oxides, chromium oxides, ultramarine, nickel and chromium antimony titanium oxides, cobalt oxides, and bismuth vanadates.
Preferred pigment preparations contain
a) 5 to 60% by weight, especially 10 to 50% by weight, of pigment;
b) 0.1 to 15% by weight, especially 0.5 to 10% by weight, of the imide of the formula (1);
c) 0 to 50% by weight, especially 1 to 30% by weight, of further additives; and
d) 10 to 80% by weight of water, based on the total weight of the pigment preparation.
Examples of further additives are anionic, cationic or nonionic surfactants, foam-reducing agents, agents which prevent the preparation drying out, and preservatives.
Suitable surfactants include all known anionic, cationic, and nonionic surface-active compounds. Surfactants which possess one or more medium- or long-chain hydrocarbon chains have proven themselves particularly. Of the multiplicity of compounds only
Harz Andreas
Metz Hans Joachim
Winter Martin Alexander
Biscula Anthony A.
Clariant GmbH
Green Anthony J.
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