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Perylene pigment compositions

A technology of perylene pigments and compositions, which is applied in the fields of anthracene dyes, organic dyes, organic chemistry, etc., and can solve the problems of not describing perylene diimides, etc.

Inactive Publication Date: 2004-09-08
SUN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

None of these patents describe the preparation of a co-precipitated mixture of perylene diimide and perylene dicarbonyl imide hydrazine amidine having small particles with a balanced particle size distribution

Method used

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  • Perylene pigment compositions
  • Perylene pigment compositions
  • Perylene pigment compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-5

[0089] Examples 1-5 describe the preparation of perylene pigment compositions and the analysis of the particle size characteristics of the compositions.

Embodiment 1

[0096] Embodiment 1 (comparison)

[0097] A suspension of 120 g (0.31 mol) of perylenedicarbonyltetracarboxylic dianhydride ("PTCA) in 1600 g of water was heated with stirring to 90°C and maintained at 90°C for 4 hours. The suspension was then cooled to 23°C, Then 120 g (1.55 mol) of 40% monomethylamine in water were added dropwise over a period of 15 minutes. Once the addition was complete, the reaction mixture was stirred at 25° C. for another 45 minutes, heated to 80° C., and maintained at 80° C. for 4 hours. After reaching room temperature, the pigment was collected by vacuum filtration, washed free of amine, and dried to obtain approximately 120 g of product.

[0098]The test results are shown in Table 1.

Embodiment 2

[0100] A mixture of 450 g (1.15 mol) of PTCA, 6000 g of water and 6 g (58.7 mmol) of 2,2 dimethyl-1,3-diaminopropane was stirred at 25° C. for 1 hour, heated to 90° C., and heated at 90° C. °C for 4 hours. The suspension was then cooled to 25° C., followed by the dropwise addition of 450 g (5.81 mol) of a 40% aqueous solution of monomethylamine over 15 minutes. Once the addition was complete, the reaction mixture was stirred at room temperature for an additional 45 minutes, heated to 80°C, and heated at 80°C for 4 hours. After cooling to room temperature, the pigment was collected by vacuum filtration, washed to be free of amine, and dried to obtain about 450 g of product containing about 5 mol% of an unsymmetrical perylenedicarbonylguanimide having the following general formula:

[0101]

[0102] The test results are shown in Table 1.

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Abstract

This invention relates to perylene pigment compositions containing a reactive co-precipitated blend of(1) about 75 to about 99.9 mol %, relative to the pigment composition, of a compound having the formula (I) whereinR is hydrogen, C1-C6 alkyl, C5-C8 cycloalkyl, C7-C6 aralkyl, or C6-C10 aryl,A is C1-C6 alkyl, C1-C6 alkoxy, a sulfonyl group, amino, ammonium, hydroxy, nitro, or halogen, andm is zero or a number from 1 to 8; and(2) about 0.1 to about 25 mol %, relative to the pigment composition, of a perylene dicarboxamidine imide having the formula (II) whereinW is optionally substituted or modified C2-C3 alkylene, andR, A, and m are defined as above.

Description

Background of the invention [0001] The present invention relates to perylene pigment compositions which, in addition to the perylene pigment component, contain certain asymmetric perylene dicarbonyl amidine imides, said perylene dicarbonyl amidine Amines (perylene dicarboxamidine imide) are used as crystal growth inhibitors during the preparation of pigment compositions. [0002] Perylenes, including perylene-3,4,9,10-tetracarboxylic diimides, can be prepared by methods known in the art. For example, W. Herbst and K. Hugner, Industrial Organic Pigments, Second Edition (New York: VCH Publishers, Inc., 1997), pp. 9 and pp. 476-479; H. Zollinger, Color Chemistry (VCHVerlagsgessellschaft, 1991), pp. 227-228 and 297-298; and M.A. Perkins, in The Chemistry of Synthetic Dyes and Pigments, ed. H.A. Lubs (Malabar, Florida: Robert E. Krieger Publishing Company, 1955), "Pyridines and Pyridones", pp. 481-482. However, perylene as initially isolated, commonly referred to as crude peryle...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B67/20C07D471/16C09B5/62C09B67/22
CPCC07D471/16C09B67/0034
Inventor 格雷戈里·R·舒尔茨
Owner SUN CHEM CORP
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