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AssigneeHarmon Colors Corporation
InventorsHerman Gerson, John Francis Santimauro, Lawrence Robert Lerner
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A process is described for making quinarcridone and its derivatives, useful as organic pigments, wherein a 2,5-diarylaminoterephthalic acid and an acid catalyst are heated in a two phase liquid system, comprising ethylene glycol and an organic liquid which is immiscible with water and ethylene glycol, wherein the ethylene glycol is present in an amount of about 0.25 to 4 parts by weight per part of 2,5-diarylaminoterephthalic acid and the organic liquid is present in an amount of at least about 2 parts by weight per part of ethylene glycol, at a temperature sufficient to remove by-product water from the liquid system by vaporization.
A process for making quinacridone and its derivatives which comprises heating a 2,5-diarylaminoterephthalic acid and an acid catalyst in a two phase liquid system, comprising ethylene glycol and an organic liquid which is immiscible with water and ethylene glycol, wherein the acid catalyst is selected from the group consisting of the mono-or di-sulfonic acids of benzene, toluene, xylene, paradichlorobenzene, naphthalene, nitrobenzene and chloroparaxylene, perchloric acid and methanesulfonic acid;
A process for making a quinacridone of the following formula:
A process for making unsubstituted gamma quinacridone which comprises heating 2,5-dianilioterephthalic acid and an acid catalyst in a two phase liquid system, comprising ethylene glycol and an organic liquid which is immiscible with water and ethylene glycol, wherein the acid catalyst is selected from the group consisting of the mono- or di-sulfonic acids of benzene toluene, xylene, paradichlorobenzene, naphthalene, nitrobenzene and chloroparaxylene, perchloric acid and methanesulfonic acid, the ethylene glycol is present in an amount of about 0.25 to 4 parts by weight per part of 2,5-dianilinoterephthalic acid and the organic liquid is present in an amount of at least about 2 parts by weight per part of ethylene glycol, in the presence of finely divided unsubstitued quinacridone, at a temperature sufficient to remove by-product water from the liquid system by vaporization.
A process for making substantially solid solutions of quinacridone mixtures being characterized in that the X-ray diffraction pattern thereof is different from the sum of the X-ray diffraction patterns of the component quinacridones, which comprises heating a mixture of 2,5-diarylaminoterephthalic acids and an acid catalyst in a two phase liquid system, comprising ethylene glycol and an organic liquid which is immiscible with water and ethylene glycol, wherein the acid catalyst is selected from the group consisting of the mono- or di-sulfonic acids of benzene, toluene, xylene, paradichlorobenzene, naphthalene, nitrobenzene and chloroparaxylene, perchloric acid and methanesulfonic acid;
Dependencies are inferred from the claim text.
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Quinacridones
Organic dyes or closely-related compounds for producing dyes
Term ended 20 Dec 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
1. Field of Invention
This invention relates to a process for making quinacridones which are important commercial lightfast pigments and are extensively used in automotive finishes, textile printing and in architectural paints.
2. Description of the Prior Art
The following examples illustrate the utility of the process of this invention for the synthesis of quinacridones both substituted and unsubstituted and also for quinacridone solid solutions. Such examples should not be construed to be limitations on the scope or spirit of the instant invention. Parts indicated in the examples are parts by weight.
Into a flask equipped with an agitator, returnable trap, thermometer and electric heating jacket, are charged 2400 parts perchloroethylene and 84 parts para-toluenesulfonic acid monohydrate. The contents are refluxed at 116.degree.-121.degree. C. until all water in the system is removed (about 7.8 parts), then cooled to 90.degree. C. and 132 parts ethylene glycol, 132 parts 2,5-dianilinoterephthalic acid are added and the reaction contents heated to 116.degree. C. over 2 hours. The contents are stirred and heated at 116.degree.-117.degree. C. for a total of 16 hours. During the heating cycle, the water formed in the reaction is constantly being distilled out along with ethylene glycol and perchloroethylene. The water-ethylene glycol layer is removed while the perchloroethylene portion is returned to the reaction. The reaction mixture is filtered and the resulting solid is reslurried in 2000 parts water and 120 parts 50% sodium hydroxide solution, boiled for 3 hours, filtered, and the solid washed alkali free and dried at 180.degree. F. The yield is 94.4% of theory of a red solid comprising a mixture of gamma quinacridone and a minor amount of beta quinacridone as evidenced by its X-ray diffraction pattern.
Using the equipment of Example 1, into a flask equipped with an agitator, returnable trap, thermometer and electric heating jacket, are charged 2400 parts perchloroethylene, 90 parts 2,4-dimethylbenzenesulfonic acid and 9.3 parts quinacridone aqueous pulp (dry content 29%). The contents are refluxed at 116.degree.-121.degree. C. until all water in the system is removed, and 2,5-dianilinoterephthalic acid and 132 parts ethylene glycol are charged and the mixture heated at a reflux temperature of 116.degree.-117.degree. C. for 6 hours. After 6 hours, 33 parts of ethylene glycol is added, and the reflux is continued at a temperature of 116.degree.-117.degree. C. for a total of 16 hours. During the heating cycle, the water formed in the reaction is constantly being distilled out with ethylene glycol and perchloroethylene. The water-ethylene glycol layer is removed while the perchloroethylene is returned to the reaction. The reaction mixture is cooled, filtered, and the resulting solid is reslurried and boiled in 2000 parts water containing 80 parts 50% sodium hydroxide solution. The solid is filtered, washed alkali free and dried at 180.degree. F. The yield is 95% of theory of a red solid comprising gamma-quinacridone as evidenced by its X-ray diffraction pattern.