JPH05171054A - Synthesis of organic coloring agent - Google Patents

Abstract

PURPOSE:To synthesize a coloring agent soluble in an organic solvent and having excellent water resistance and coloring properties from an organic dye as a raw material. CONSTITUTION:An organic dye is reacted with a surfactant, and the reaction liquid (e.g. water phase) is brought into contact with an organic solvent to shift the equilibrium of the reaction to the product side. Thus, an organic coloring agent soluble in an organic solvent is synthesized at a high concentration.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a method of synthesizing an organic colorant suitable for coloring mortar, plastic, paper or cloth.

[0002]

2. Description of the Related Art Conventionally, organic dyes used for coloring mortar, plastics, paper, cloth, etc. have a wide variety of colors and are easily soluble in water. It cannot be used in an environment where it comes into contact with or in a humid place, and its application is limited. On the other hand, organic pigments are not easily dissolved in water or organic solvents, so there is no limit to their use, but it is difficult to find a suitable solvent and it is necessary to disperse them. Need. Therefore, there is also a problem that the coloring process is troublesome. For example, in the case of coloring cement with a pigment, a method of dispersing the pigment in water, stirring and mixing with the cement, or coating the surface of the material in a spray state is used.

[0003] In order to solve these problems, it is considered to add surface activity to the organic dye.
A synthetic procedure such as the r method is required, which involves handling difficult substances such as sulfuric acid and other dangerous substances and refining. Also, color mixing is difficult.

[0004]

Therefore, there is a demand for a colorant which is excellent in color developability and water resistance using an organic dye having a wide variety of colors and easy to handle, and an object of the present invention is to provide a colorant of this type. To provide a simple synthetic method of.

[0005]

[MEANS FOR SOLVING THE PROBLEMS] An organic dye and a surfactant are reacted with each other, and the reaction solution is brought into contact with an organic solvent to easily synthesize a high-concentration colorant soluble in the organic solvent.

[0006]

[Function] When the reaction solution of the organic dye and the surfactant is brought into contact with the organic solvent, the reaction equilibrium is shifted to the product side.
00% reaction proceeds.

[0007]

EXAMPLES Examples of the present invention will be described below.

Prior to the description of the examples, the basic concept of the colorant synthesis method according to the present invention will be described.

In the synthesis method according to the present invention, an organic dye and a surfactant are reacted with each other, and the reaction liquid (for example, water) is brought into contact with an organic solvent to shift the equilibrium of the reaction to the product side, so that the organic solvent can be used. It synthesizes soluble, high-concentration organic dyes. Next, an example of a method for synthesizing a colorant according to the present invention will be described. (1) About 0.4 mmol (0.238 g) of distearyldimethylammonium chloride as a surfactant
Is dissolved in 100 ml of water at room temperature. (2) After dissolving the surfactant, about 0.1 mmol (0.088 g) of nickel phthalocyanine sulfonic acid, which is a dye, is added.
Add and heat up to about 40 ° C if necessary. (3) Add chloroform to the 500-mL separatory funnel beforehand.
Put 00 ml in it and pour the mixed solution prepared in (2) gently. (4) Let stand at room temperature until the water phase becomes transparent. (5) The chloroform phase is collected and colored. (6) Methanol cleaning is performed as necessary to reduce the mixed surfactant.

With respect to the above synthetic method, the present inventor has tried the following various surfactants. (1) Quaternary ammonium chloride containing a long alkyl chain R: R: C ₁₂ H ₂₅ ... Lauryl trimethyl ammonium chloride R: C ₁₆ H ₃₃ ... Cetyl trimethyl ammonium chloride R: C ₁₈ H ₃₇ ... Stearyl trimethyl ammonium chloride (2) Quaternary ammonium bromide containing two long chain alkyl chains R: R: C ₁₂ H ₂₅ ... Dilauryl dimethyl ammonium bromide (3) 4 containing four long chain alkyl chains R grade ammonium iodide: R: C ₈ H ₁₇ ··· tetra -n- octyl ammonium iodide (4) two quaternary ammonium chloride comprises a long alkyl chain _{R: R: C 18 H 37} ··· di Stearyl dimethyl ammonium chloride As a result, any of the surfactants to Although pressure can be water-soluble, chloroform solubility, in terms of conversion rate that the best results are obtained it has been found.

Since all of the typical commercially available organic dyes are sulfonates (--SO ₃ Na), all dyes can be selected in the present invention, but the surfactant used for synthesis has the following structure. If so, all reactions proceed. Incidentally.
It is preferable that the mixing ratio of the surfactant be in an excess condition with respect to the -sulfonic acid group.

X: Cl, I, F, Br R: C _{1 to} C ₂₀ Hydrocarbons The present inventor has confirmed by experiments that the following organic dyes can be used in the synthesis method of the present invention.

Blue: Blue 86 Torquoise Blue G1 Blue 15 Direct Sky Blue 5B Yellow: Yellow 12 Chryso Phenine G Yellow 44 Direct Fast Yellow GC Red: Red 2 Benezopurpurine 4B Red 81 Sirius Red 4B The colorant synthesized by the present invention is paper. It was confirmed that many materials such as cloth, cement, and plastic can be colored, but especially in the case of coloring cement, a small amount of color is developed.
As an example, FIG. 1 and FIG. 2 are used to compare the color development of a copper phthalocyanine surface active dye synthesized according to the present invention with a commercially available blue inorganic dye to color white Portland cement with a spectrometer. The reflectance is measured by the method, and a considerable difference is observed in the coloring intensity depending on the density. Here, the horizontal axis represents the concentration (% by weight) of the dye, and the vertical axis represents (100-reflectance (about 500 mm))%, which indicates the strength of color development. To increase the color intensity to 40%,
A commercially available product requires a concentration of 5% by weight, but the surface-active dye according to the present invention can achieve the same level of color development intensity in an amount of about 1/10. This indicates that the addition of the dye can suppress the strength decrease of the base material. When it was immersed in water for 1 month, it had sufficient water resistance because the color development did not change.

[0014]

As described above, according to the present invention, an organic dye soluble in a high concentration is synthesized by reacting an organic dye with a surfactant and bringing the reaction solution into contact with an organic solvent. As a result, it is possible to obtain a thick colorant having a wide variety of colors and excellent in water resistance, dispersibility and color development. The colorant synthesized according to the present invention can obtain sufficient color development even when the amount of the surfactant added is small, so that it is possible to prevent the strength of the base material from being lowered by the addition of the dye.
In addition, since the synthetic procedure is extremely simple, it is possible to perform coloring on site. It can also be used in environments where water resistance is required.

[Brief description of drawings]

FIG. 1 is a diagram showing the coloring strength of white Portland cement with a conventional pigment (inorganic, blue).

FIG. 2 is a diagram showing the coloring strength of white Portland cement with an organic colorant synthesized according to the present invention.

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[Procedure amendment]

[Submission date] February 14, 1992

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be corrected] Brief description of the drawing

[Correction method] Change

[Correction content]

[Brief description of drawings]

FIG. 1 is a diagram showing the coloring strength of white Portland cement with an organic colorant synthesized according to the present invention.

FIG. 2 is a diagram showing the coloring strength of white Portland cement with a conventional pigment (inorganic, blue).

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Claims (4)

[Claims] 1. A method for synthesizing an organic colorant, which comprises reacting an organic dye with a surfactant and bringing the reaction solution into contact with an organic solvent. 2. The method for synthesizing an organic colorant according to claim 1, wherein the surfactant is a quaternary ammonium halide containing 1 to 4 long alkyl chains. 3. The organic dye is a sulfonate (--SO ₃ X).
The method for synthesizing an organic colorant according to claim 1, wherein 4. The method for synthesizing an organic colorant according to claim 1, wherein the organic solvent is a solvent immiscible with water such as chloroform.