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2,5-di(methoxyanilino) terephthalic acid polymorphs and quinacridones realized therefrom

a technology of terephthalic acid and dimethoxyanilino, which is applied in the field of new crystal types of 2, 5di (pmethoxyanilino) terephthalic acid, can solve the problems of lack of evidence in the literature that the 2,5-dianilinoterephthalic quinacridone and the precursor of quinacridones exhibit polymorphism

Inactive Publication Date: 2009-07-23
SUN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0006]In accordance with the present invention, two distinctly different crystal forms of 2,5-di(p-methoxyanilino)terephthalic acid, crystal type I and crystal type II, are produced by controlling the pH recovery conditions to which the oxidized dicondensed product of dimethylsuccinyl succinate and 4-methoxyaniline is subjected. Crystal type I is characterized by being brown (powder or wet cake) and has the distinctive X-ray pattern shown in FIG. 1 with the strongest peak at about d=6.3 angstroms (2θ=13.9 via CuKα). It can be produced by first adjusting the pH during product recovery to about neutral and thereafter further reducing the pH to about 4.5 to about 6.5. Crystal type II is characterized by being violet (powder or wet cake) and has the distinctive X-ray pattern shown in FIG. 2 with the strongest peak at about d=16.1 angstroms (2θ=5.5 via CuKα). It can be produced by adding a 2,5-di(p-methoxyanilino)terephthalic acid solution to a strong acid such that the final pH is below about 5.0. Alternatively, type I can be converted into type II.
[0007]Further in accordance with the present invention, the 2,5-di(p-methoxyanilino)-terephthalic acid is converted into a 2,9-dimethoxyquinacridone or a solid solution thereof whose final properties are changed and / or improved relative to the prior art. The quinacridone intermediate's crystal form during quinacridone production, e.g., ring closure, is employed to manipulate the quinacridone's properties. The quinacridone can be used as a colorant in inks, coating compositions and masses of materials such as plastics.

Problems solved by technology

However, there is no evidence in the literature that the 2,5-dianilinoterephthalic quinacridone precursors exhibit polymorphism.

Method used

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  • 2,5-di(methoxyanilino) terephthalic acid polymorphs and quinacridones realized therefrom
  • 2,5-di(methoxyanilino) terephthalic acid polymorphs and quinacridones realized therefrom
  • 2,5-di(methoxyanilino) terephthalic acid polymorphs and quinacridones realized therefrom

Examples

Experimental program
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Effect test

example 1 (

CRYSTAL TYPE I)

[0028]To a pressure reactor were charged 489.8 g of methanol. With agitation, 50 g of dimethylsuccinyl succinate were charged and stirred for ˜10 minutes. To the stirring slurry were added 56.7 g of p-anisidine. After stirring for ˜15 minutes, 0.8 g of 96% H2SO4 were added dropwise. The reactor was sealed, heated to 95-100° C. and held at this temperature for approximately 5 hours. After cooling to 40-50° C., the reactor was opened and with agitation, 55.6 g of m-nitrobenzenesulfonic acid, sodium salt, were added. After stirring for ˜5 minutes, 127.8 g of 45% KOH were charged over a 15 minute period. The reactor was sealed, heated to 90-95° C. and held at this temperature for approximately 4 hours. Upon cooling to 40-50° C., the reaction slurry was transferred to a container containing 800 g of H2O. Once the transfer was complete, an additional 275 g of H2O were added and with stirring, the solution was heated to 30-40° C. The pH was then adjusted from 13 to 7.5-7.0 w...

example 2 (

CRYSTAL TYPE II)

[0030]To a pressure reactor were charged 489.8 g of methanol. With agitation, 50 g of dimethylsuccinyl succinate were charged and stirred for ˜10 minutes. To the stirring slurry were added 56.7 g of p-anisidine. After stirring for ˜15 minutes, 0.8 g of 96% H2SO4 were added dropwise. The reactor was sealed, heated to 95-100° C. and held at this temperature for approximately 5 hours. After cooling to 40-50° C., the reactor was opened and with agitation, 55.6 g of m-nitrobenzenesulfonic acid, sodium salt, were added. After stirring for ˜5 minutes, 127.8 g of 45% KOH were charged over a 15 minute period. The reactor was sealed, heated at 90-95° C. and held at this temperature for approximately 4 hours. Upon cooling to 55-65° C., the reaction slurry was transferred to a container using water to a total volume of 1200 mL. The solution was held 15 minutes at 55-65° C., then transferred over 45-60 minutes, via a pump, to a vessel containing 1344 g of a 3.6% HCl solution. The...

example 3

[0033]A portion of the brown product of Example 1 (50 g) was dissolved in water having a basic pH (955 g water and 75.2 g 45% KOH). The resulting solution was stirred for 55-65° C. for 60 minutes and then allowed to cool to 35-40° C. The pH was then adjusted from 12.8 to 5.3 with 31.7 g 96% H2SO4. The resulting violet slurry was stirred for 60 minutes at 35-40° C., at which time it was filtered and the resulting presscake washed with water until conductivity free (<120% of incoming wash water). The washed presscake was then dried in an oven to obtain 43 g of violet powder. When evaluated by HPLC, the purity profile was 93.3% 2,5-di(p-methoxyanilino)terephthalic acid. Evaluation by LC-MS confirmed that the major component was indeed 2,5-di(p-methoxyanilino)terephthalic acid. The mass spectra (FIGS. 5A to 5C) and X-ray diffraction pattern (FIG. 6) confirms that the violet type intermediate was obtained.

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Abstract

2,5-di(p-methoxyanilino)terephthalic acid crystal types I and II are made by controlling the pH during the recovery of the oxidized product of the condensation of dimethylsuccinyl succinate with p-methoxyaniline. The resulting 2,5-di(p-methoxyanilino)-terephthalic acid can be converted into 2,9-dimethoxyquinacridone or a solid solution thereof having controlled characteristics.

Description

FIELD OF THE INVENTION[0001]This invention relates to new crystal types of 2,5-di(p-methoxyanilino)terephthalic acid and their use in the production of 2,9-dimethoxyquinacridone and solid solutions thereof.BACKGROUND OF INVENTION[0002]A conventional method for the production of pigments which are 2,9-dimethoxyquinacridone or its solid solutions involves the conversion of 2,5-di(p-methoxyanilino)terephthalic acid to the desired quinacridone. Color manipulation of the final pigment can then be achieved by modifying selected post-synthetic quinacridone manufacture treatments so as to cause changes in the particle size, particle shape, particle size distribution and / or crystal form of the final pigment. These steps can entail milling procedures (wet, dry, with and without milling aids) and heat treatments (with and without particle growth inhibitors or dispersing aids). It is also known that the use of fully-formed quinacridone derivatives and / or their quinacridone intermediate precurso...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09D11/02C07C229/52C07D471/04C09D9/00B32B3/00
CPCC07C229/62C07D471/04C09B48/00Y10T428/24802C09D7/007C09D11/037C09B67/0027C09D7/41
Inventor THOMPSON, BRIANRICE, DAPHNETIBBS, TRACIEWU, WENGANBRITANAK, JOHNSUNG, EDWARD H.
Owner SUN CHEM CORP
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