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Dye Derivative, Colorant, And Coloring Method

A technology of pigment derivatives and derivatives, applied in optics, instruments, organic dyes, etc., can solve the problems of aggregation, dispersion instability, color change, etc., and achieve the effect of improving dispersibility

Active Publication Date: 2014-06-25
DAINICHISEIKA COLOR & CHEM MFG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, dyes are mostly simple pigments as a molecular structure, and although the color is excellent in transparency and vividness, there are problems in fastness such as light resistance and heat resistance.
In addition, compared with dyes, pigments have lower color tone breadth and sharpness, and most of them have a crystalline form, and among them, they are unstable to organic solvents or heat, and crystal transformation or particle coarsening occur, and the color may change
Pigment liquid colorants have the following disadvantages: they are often dispersed in liquid media such as solvents or water, and tend to settle or aggregate. Even if they are improved with dispersing aids, aggregation will occur after a long period of time. problems etc.
In addition, as a greenish blue oil-soluble dye, there is a dye in which an alkyl group is introduced into the molecular structure of copper phthalocyanine using a sulfonamide group as a linking group (for example, C.I. Solvent Blue 25). Functional aspects such as property control and redispersibility are effective, but when the amount of green-emitting components as a color toner increases, there are problems in the light fastness of printed matter, etc.
[0004] In addition, as the blue pigment used in the formation of the blue pixel of the image display material of the color filter, a reddish blue ε-type copper phthalocyanine pigment (C.I. Pigment Blue 15:6) is used, but the solvent and heat a bit unstable
Therefore, in many cases, monosulfonated copper phthalocyanine is used as an additive for suppressing the crystal transformation of the pigment or suppressing the crystal growth, but there is a tendency for the hue to be green and the chroma to be reduced. In terms of hue, it is not preferred

Method used

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  • Dye Derivative, Colorant, And Coloring Method
  • Dye Derivative, Colorant, And Coloring Method
  • Dye Derivative, Colorant, And Coloring Method

Examples

Experimental program
Comparison scheme
Effect test

manufacture example 1

[0084] [Manufacturing Example 1: Synthesis of ε-type copper phthalocyanine pigment for color filter]

[0085] (1-1) (Synthesis of anionic pigment having sulfonic acid introduced into the pigment)

[0086] Drop into 120g of anhydrous sulfuric acid in the reaction device that is provided with the electric heating heater of heating device, stirrer, reagent inlet and reflux condenser, add copper phthalocyanine blue pigment (MW (molecular weight): 576) 5.76g (0.01 mol) to dissolve it. Thereafter, it was heated to 50° C., 0.60 g (0.02 mol) of paraformaldehyde (MW: 30 (monomer)) was added, stirred for 1 hour and 30 minutes, and reacted to synthesize a methylol form.

[0087] Next, the temperature was raised to 80°C, and 3.76 g (0.02 mol) of o-cresol-4-sulfonic acid (MW: 188.2, purity 86%) was added in terms of pure components, and stirred at 80°C to 85°C for 6 hours to allow reaction . After the reaction was completed, it was cooled to normal temperature and precipitated in about ...

manufacture example 2

[0095] [Production Example 2: Production of ε-type copper phthalocyanine pigment for color filters]

[0096] (2-1) (Synthesis of anionic pigment having sulfonic acid introduced into the pigment)

[0097] Except using 2.09 g (0.015 mol) of N-methyltaurine (MW: 139) instead of o-cresol-4-sulfonic acid used in Production Example 1-1, it was performed in the same manner as Production Example 1-1, N-methyl-N-(sulfoethyl)aminomethylated copper phthalocyanine is obtained. The number of substitutions was approximately 0.4. Hereinafter, this is referred to as "blue dye derivative-2". Table 1 also shows the composition.

[0098] (2-2) (Preparation of blue pigment composition)

[0099] Using the blue pigment derivative-2 obtained above instead of the blue pigment derivative-1 used in Production Example 1-3, the production process was carried out in the same manner to obtain a reddish blue color containing ε-type copper phthalocyanine as a main component. Pigment composition. Herein...

manufacture example 3

[0100] [Production Example 3: Production of ε-type copper phthalocyanine pigment for color filters]

[0101] (3-1) (Synthesis of anionic pigment having sulfonic acid introduced into the pigment)

[0102] A sulfonamidomethylated copper phthalocyanine was obtained in the same manner except that 1.46 g (0.015 mol) of sulfamic acid (MW: 97) was used instead of o-cresol-4-sulfonic acid used in Production Example 1-1. The number of substitutions was approximately 0.4. Hereinafter, this is referred to as "blue dye derivative-3". Table 1 also shows the composition.

[0103] (3-2) (Preparation of blue pigment composition)

[0104] The blue pigment derivative-3 obtained above was used instead of the blue pigment derivative-1 used in Production Example 1-3, and the production process was carried out in the same manner to obtain a reddish blue color containing ε-type copper phthalocyanine as a main component. Pigment composition. Hereinafter, this is referred to as "blue pigment comp...

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Abstract

Disclosed is a pigment derivative, characterized by being a dye derivative obtained by linking the molecule of a water-insoluble dye (A) and the residue of a compound (C) to each other through an alkylene group formed by reacting the dye (A) with an aldehyde compound (B). By appropriately selecting the compound (C) from hydrocarbon compounds (C-1) having a methane group (-CH=) with a hydrogen group which is susceptible to substitution and amino compounds (C-2) having a reactive amino group, a deeper color effect than the color of an existing dye is brought about. Further, by using a pigment derivative effective as an additive for suppressing the crystal transfer or crystal growth of a pigment and also using the dye derivative, a colorant which has the above-mentioned effect, and also achieves a decrease in the viscosity of a pigment dispersion and has improved properties such as dispersion stability and long-term storage stability is realized. By using this colorant, a useful coloring method and a colored article are provided.

Description

technical field [0001] The present invention relates to a pigment derivative, a colorant and a coloring method. More specifically, it relates to a dye derivative in which a compound having a methine group or an amino group is connected to the molecular structure of a water-insoluble dye through an alkylene group, a colorant containing the dye derivative, and a product using the dye derivative. Coloring method of article and colored article. Background technique [0002] Conventionally, dyes that are soluble in water or solvents, or pigments that are insoluble in these media and finely dispersed in the form of fine particles are generally used as pigments used for coloring articles. However, dyes are mostly simple pigments as molecular structures, and although the colors are excellent in transparency and vividness, they have problems in fastness such as light fastness and heat resistance. In addition, compared with dyes, pigments have lower breadth and sharpness of color to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B69/00C09B67/00C09B67/20C09B67/46C09D17/00G02B5/20G02B5/22
CPCC09D7/007C09B67/0008C09B67/0085G02B5/22C09D7/41C09B67/006C09B67/0084C09B69/00G02B5/20
Inventor 中村道卫福田哲男野上敦柳本宏光高鸭雅则坂井尚之大久保利江桐慎吾
Owner DAINICHISEIKA COLOR & CHEM MFG CO LTD