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Process for making perylene pigment compositions.

A kind of perylene pigment and perylene technology are applied in the field of manufacturing perylene pigment compositions, and can solve the problems such as the preparation of perylene diimide is not described

Inactive Publication Date: 2007-10-31
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 small particle size co-precipitated mixture of perylene diimide and perylene dicarbamidine imide with a uniform particle size distribution

Method used

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  • Process for making perylene pigment compositions.
  • Process for making perylene pigment compositions.
  • Process for making perylene pigment compositions.

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-5

[0075] Examples 1 and 2 describe the preparation of perylene dicarbamidine imide compositions. Comparative Example 3 describes the preparation of N,N'-dimethylperylene tetracarboxylic diimide (Pigment Red 179) without the perylene dicarbamidine imide of the present invention. Examples 4 and 5 describe the preparation of N,N'-dimethylperylene tetracarboxylic diimide in the presence of perylene dicarbamidine imide.

[0076] Particle Size Test Method

[0077] The particle size of the compositions prepared in the examples below was determined by QLS laser light scattering, DCP discs and X-ray powder diffraction. For laser light scattering and disc centrifugation, each pigment composition sample was diluted with water, dispersed with an ultrasonic signal (600W for two minutes), and further diluted. For X-ray determination, powder samples are used.

[0078] Using a Brookhaven Instruments Laser Scattering Particle Size Analyzer equipped with a BI-9000 correlator detector, a photom...

Embodiment 1

[0082] To 500 ml of deionized water in an autoclave were added 7 g of perylene monoimide / monoanhydride and 2.6 g of 2,2-dimethyl-1,3-propanediamine. The autoclave was sealed and heated and stirred at 140°C for 14 hours. The autoclave was cooled, and the contents were collected by vacuum filtration, and washed with deionized water until none flowed out. The filter cake was reslurried in 300 ml of deionized water and the pH of the suspension was adjusted to 12 with 12% aqueous potassium hydroxide. The suspension was heated at 80°C for 2 hours, cooled to 60°C and filtered. The filter cake was washed with deionized water until no flow-through occurred. A total of 20.5 g of filter cake was obtained, corresponding to 4.79 g of (VIII).

[0083]

Embodiment 2

[0085] To 500 ml of deionized water in an autoclave was added 10 g of perylene monoimide / monoanhydride and 6.91 g of 1,3-diamino-2-hydroxypropane. A solution of 4.91 g of 96% sulfur in 50 ml of deionized water was added with stirring. The autoclave was sealed and heated and stirred at 140°C for 14 hours. The autoclave was cooled, and the precipitate was collected by vacuum filtration and washed with deionized water until nothing flowed out. A filter cake of about 81 g was obtained, corresponding to about 10.1 g (IX).

[0086]

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PUM

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Abstract

This invention relates to a process of preparing a 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) wherein R is hydrogen, C1-C6 alkyl, C5-C8 cycloalkyl, C7-C16 aralkyl, or C6-C10 aryl, A is C1-C6 alkyl, C1-C6 alkoxy, a sulfonyl group, amino, ammonium, hydroxy, nitro, or halogen, and m 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) wherein W is optionally substituted or modified C2-C3 alkylene.

Description

Background of the invention [0001] The present invention relates to a process for the manufacture of perylene pigment compositions which, in addition to the perylene pigment component, contain certain asymmetrical compounds which act as crystal growth inhibitors during the preparation of said pigment compositions. perylene dicarboxamidine (dicarboxamidine) imide. [0002] Perylenes, including imides of perylene-3-,4,9,10-10-tetracarboxylic acid, can be prepared by methods well known in the art. For example, W.Herbst and K.Hunger, Industrial Organic Pigments Organic Pigments , 2nd ed. (New York: VCH Publishers, INC, INC., 1997), pages 9 and 476-479; H. Zollinger, Color Chemistry (VCHVERLAGSGESSELLSCHAFT, 1991), pages 227-228 and 297-298; and M.A. Perkins, "Pyridines and Pyridones" in The Chemistry of Synthetic Dyes Synthetic Dyes and Pigments , ed. H.A. Lubs (Malabar, Florida: Robert E. Krieger Publishing Company Publishing Company, 1955) pages 481-482. However, the i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B67/22C09B57/12C09B5/62C09B67/20
CPCC09B57/12C09B5/62C09B67/0034
Inventor 格雷戈里·舒尔茨
Owner SUN CHEM CORP
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