Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-04-19
2002-11-19
Pryor, Alton N (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S186000
Reexamination Certificate
active
06482817
ABSTRACT:
The present invention relates to the preparation of hybrid pigments consisting of benzimidazolone triphenodioxazines and diketopyrrolo [3,4-c] pyrrole, thiazine-indigo, quinacridone or copper phthalocyanine pigments, to a process for their preparation and to the use of the hybrid pigments for the mass pigmentation of substrates, as colorants in electrophotographic toners and developers, in powders and powder coating materials, in ink-jet inks and cosmetics.
BACKGROUND OF THE INVENTION
Benzimidazolone triphenodioxazine compounds belong to an important series of pigments. A general overview and preparation processes are described in the patents GB 2284427, DE 4442291.1 and DE 19727079 A1. These compounds are particularly useful as pigments for coloring plastics mass including both solvent-free and solvent-containing masses of plastics or plastics resins. These include oil-based or aqueous paint systems and lacquers of various kinds. These compounds are also suitable for spin coloring of viscose or cellulose acetate, for pigmenting of polyethylene, polystyrene, polyvinylchloride, rubber or artificial leather. They can also be used for printing graphic fabrics, for coloring paper masses, for coating of textiles or for any other pigment printing process. The resulting pigmentations have excellent fastness to heat, light and weathering and chemicals. The pigments retain good strength of color and have good application properties. In particular, they have good fastness to migration, blooming, overcoating and solvents.
SUMMARY OF THE INVENTION
It is known that, under certain conditions, hybrid pigments which are either solid solutions or mixed crystals or crystal mixtures having improved properties can be obtained with two or more pigments. The process of the invention describes the preparation of such hybrid pigments consisting of benzimidazolone triphenodioxazine and other pigments which can be formed in high yield and which exhibit new pigmentary properties. More specifically, the invention relates to a method for preparing mixed crystals or solid solutions or crystal mixtures by synthesizing and/or finishing of the pre-cited pigments in the presence of another pigment of the class comprising diketopyrrolo-pyrrole, thiazine-indigo, quinacridone and copper phthalocyanine. The solid solutions and/or the mixtures of a benzimidazolone triphenodioxazine pigment and another pigment can be prepared by dissolving both of them in concentrated sulfuric acid or polyphosphoric acid, at temperatures from 0° C. to 200° C., and to precipitate the pigment particles by adding ice or water or a mixture of water and an alcohol, or by pouring the acidic medium in ice or water or a mixture of water and an alcohol.
One can also use additives known in the state-of-the-art to control the particle size of the pigment.
An obvious condition for the performance of this process is the possibility to dissolve the starting materials in concentrated sulfuric or polyphosphoric acid.
With the hybrid pigments so obtained, it is possible to generate highly advantageous shifts in shades, which are of great interest. Moreover, the hybrid pigments of the present invention possess excellent dispersability, high color strength, high weather and light fastness, high saturation and outstanding heat stability in engineering plastics.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention, therefore, provides hybrid pigments containing:
(a) at least one benzimidazolone triphenodioxazine compound of the formula (I)
wherein
both X represent hydrogen or a halogen atom;
R
1
and R
2
are, independently of each other, hydrogen, C
1-18
alkyl, unsubstituted phenyl or phenyl which is mono- or polysubstituted with halogen or nitro groups, C
1-8
alkyl, trifluoromethyl or C
1-2
alkoxy; and
(b) at least one pyrrolo[3,4-c]pyrrole compound of the formula (II)
in which A and B are, independently of each other, a group of the formulae
in which R
3
and R
4
are, independently of each other, hydrogen, halogen, C
1-5
alkyl, C
1-5
alkoxy, CN or a group of the following formulae
with the same meanings of R
3
and R
4
as above; or
(c) at least one thiazine-indigo compound of the formula (III)
wherein
R
5
and R
6
are, independently of each other, residues which consist of the atoms necessary to complete a benzene ring which is optionally substituted with, for example halogen, alkyl, trifluoromethyl, nitro, cyano, alkyl, alkoxy, amino, alkylamino, thioalkyl, phenoxy, phenylamino, phenylthio, acyl, acyloxy or acylamino; or
(d) at least one quinacridone compound of the formula (IV)
in which
R
7
, R
8
, R
9
and R
10
are, independently of each other, hydrogen, halogen, C
1-5
alkyl or C
1-5
alkoxy; or
(e) at least one copper phthalocyanine compound of the formula (V)
in which n=0-16 (randomly distributed).
These hybrid pigments which are either solid solutions or mixed crystals or crystal mixtures are highly suitable for use as pigments for coloring high molecular weight organic material.
The term “halogen” includes fluorine and especially chlorine and bromine. The term “alkyl” or “alkoxy” includes said functionality having from 1 to 4 carbon atoms. The terms “alkylamino” and “phenylamino” include N,N-dialkylamino and N,N-diphenylamino as well as N-monoalkylamino and N-monophenylamino. The aforementioned alkyl, alkoxy, phenyl and phenoxy substituents may themselves contain one or more substituents selected from the substituents above described.
Depending on the nature of the components which are present in the hybrid pigments of the invention, the products are either solid solutions or mixed crystals or crystal mixtures and the structure of these products can be determined by x-ray powder diffraction. In general, mixtures of similar structures will result in solid solutions or mixed crystals whereas mixtures of quite different structures will result in crystal mixtures.
This invention relates in particular to the preparation of mixed crystals or solid solutions or crystal mixtures of benzimidazolone triphenodioxazine with other pigments. The benzimidazolone triphenodioxazine pigment is obtained via a cyclisation step in concentrated sulfuric acid using manganese dioxide as oxidant. One method consists in adding to this, the diketopyrrolo [3,4-c] pyrrole or thiazine-indigo or quinacridone or copper phthalocyanine pigment at the end of the reaction. The mixture is stirred for a few hours and then discharged into water or a mixture of water and alcohol and the precipitate obtained is isolated by filtration. Mixed crystals or solid solutions or crystal mixtures of benzimidazolone triphenodioxazine and diketopyrrolo [3,4-c] pyrrole or thiazine-indigo or quinacridone or copper phthalocyanine pigments are formed thereby.
Another method is to mix already isolated benzimidazolone triphenodioxazine pigment with, for example, a diketopyrrolo [3,4-c] pyrrole pigment in concentrated sulfuric acid at a temperature in the order of 10 to 100° C., preferably from 20 to 50° C. The mixture is stirred, preferably at or below 50° C., until it is homogeneous. If necessary, the solution can be heated to a temperature in the order of 60 to 200° C., preferably from 80 to 130° C.
The hybrid pigments are then precipitated from the solution by precipitation methods known in the art. For example, suitable precipitation methods include drowning into water or an alcohol, or by adding an alcohol and/or water to the pigment solution. The water and/or alcohol can be used in any desired mixing ratio between 5 and 20 parts by weight per 1 part of the pigment formed. One can also use additives known in the state-of-the-art to control the particle size of the pigment composition. It's also possible to control the particle size of the pigment composition by heating under pressure the final pigment suspension at the end of the precipitation or the pigment suspension during the mixing step.
When the ripening of the pigment crystals is complete, the conditioned pigment is isolated by filtration, with th
Born Roland
Kaul Bansi Lal
Piastra Bruno
Plug Carsten
Steffanut Pascal
Bisulca Anthony A.
Clariant Finance (BVI) Limited
Pryor Alton N
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