Phthalocyanine compound, process for producing the same and colored composition containing the phthalocyanine compound

A technique for coloring compositions and manufacturing methods, applied in chemical instruments and methods, organic dyes, organic chemistry, etc., capable of solving problems such as large color change, insufficient resistance to organic solvents or acids, and achieving low environmental load and safety sex high effect

Inactive Publication Date: 2008-02-06
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this method, there are the following problems: due to the mixing of two kinds of pigments with completely different chemical structures, flooding occurs; due to the difference in light resistance due to the difference in the type of pigments mixed, there are problems in exposure to sunlight. wait for the color change
However, although this compound (a) solves the above-mentioned problems such as floating color, it has the problem of insufficient resistance to organic solvents or acids.

Method used

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  • Phthalocyanine compound, process for producing the same and colored composition containing the phthalocyanine compound
  • Phthalocyanine compound, process for producing the same and colored composition containing the phthalocyanine compound
  • Phthalocyanine compound, process for producing the same and colored composition containing the phthalocyanine compound

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Embodiment

[0070] Hereinafter, the present invention will be described in more detail through examples.

Synthetic example 1

[0072] In 100 parts by mass of anhydrous acetonitrile, add 15 parts by mass of 1,2-diamino-4,5-dicyanobenzene and 19.5 parts by mass of 1,1-carbonyldiimidazole, and stir at 70°C for 3 hours to allow the reaction . Then, after cooling the obtained reaction product to room temperature, the precipitated solid was filtered, washed with water, and dried to obtain 16.9 parts by mass (yield 96.5%) of a pink solid.

[0073] For the peach-white solid obtained in Synthesis Example 1, dimethyl sulfoxide (hereinafter, referred to as "DMSO")-d6 solution was carried out 1 H-NMR analysis (using the nuclear magnetic resonance device "JNM-LA300" produced by JEOL Ltd.) and infrared spectroscopic analysis (using the Fourier transform infrared spectrophotometer "FT / IR-550" produced by JASCO Co., Ltd.), the results obtained The following analysis results. In addition, the spectrum obtained by infrared spectroscopic analysis is shown in FIG. 1 .

[0074] 1 H-NMR analysis>

[0075] 1 H-NMR anal...

Synthetic example 2

[0083] (in the foregoing general formula (5), M is a copper atom, R 1 ~R 4 Synthesis of phthalocyanine compounds with hydrogen atoms)

[0084] In 32 parts by mass of trichlorobenzene, add 10 parts by mass of 5,6-dicyanobenzimidazolone obtained in Synthesis Example 1, 1.4 parts by mass of cuprous chloride and 10 parts by mass of DBU, and stir at 180°C for 6 hours make it react. Next, after cooling the obtained reaction product to room temperature, the precipitated solid was filtered. The obtained solid was washed successively with acetone, methanol, 10% by mass of hydrochloric acid, 8% by mass of ammonia water, and water, and dried to obtain 7.3 parts by mass (67.2% yield) of a green solid.

[0085]The green solid obtained above was subjected to FAB / MS analysis (using a mass spectrometer "JMS-LX2000" produced by Japan Electronics Co., Ltd.), and infrared spectroscopic analysis (using a Fourier transform infrared spectrophotometer "FT / IR-550"), and measuring the light absor...

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Abstract

Provided is a phthalocyanine compound represented by the following general formula (1) which is halogen-free, has a green hue, and is resistant to organic solvents and acids (in the above general formula (1), M represents 2 to 4 valent A metal atom or two hydrogen atoms, rings A1, A2, A3 and A4 each independently represent a benzene ring or a structure represented by the above-mentioned general formula (2). Among them, at least one of the rings A1, A2, A3 and A4 is the above-mentioned A structure represented by general formula (2). In addition, in the above general formula (2), R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group, a tolyl group or a xylyl group).

Description

technical field [0001] The present invention relates to a phthalocyanine compound that can be used as a green pigment, a method for producing the same, and a coloring composition containing the phthalocyanine compound. Background technique [0002] Conventionally, a polyhalogenated copper phthalocyanine is mentioned as a representative substance of a known green pigment. This polyhalogenated copper phthalocyanine has excellent fastness, but since it contains a large amount of halogen atoms such as chlorine and bromine in the molecule, there are concerns about its safety and environmental load in recent years. Therefore, there is a need for a pigment that can be colored green with a compound that does not contain a halogen atom. [0003] As a method of coloring green with a compound that does not contain a halogen atom (hereinafter referred to as "halogen-free"), a method of mixing copper phthalocyanine as a cyan pigment with a yellow organic pigment and toning it green has ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B47/067C09B47/22C07D235/26
CPCC07D487/22C09B47/0676
Inventor 永田美彰
Owner DIC CORP
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