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Preparation method of C.I. pigment red 188

A pigment red and pigment technology, applied in the field of preparation of C.I. Pigment Red 188, can solve the problems of large molecular weight, difficult diazotization reaction, difficult to dissolve, etc., and achieve the effect of bright color, good solvent resistance and easy dispersion

Active Publication Date: 2013-09-11
宇虹颜料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The conventional diazotization reaction is carried out by adding the diazo component to the solution of sodium nitrite in an acidic aqueous medium at low temperature, because the diazo component 2-carboxylate group-5-(2', 5'- Dichlorophenyl)-formamidoaniline contains insoluble groups such as formamido, chlorine and methyl carboxylate, and has a large molecular weight, which is difficult to dissolve in dilute acid aqueous solution, and the diazotization reaction is difficult to carry out. Even if the reaction lasts for a long time, the diazotization cannot be completed; the synthesis and pigmentation of similar structural pigments are generally carried out in a large amount of toxic and harmful organic solvents, and the production process will cause serious pollution to the environment

Method used

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  • Preparation method of C.I. pigment red 188

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation method of C.I. Pigment Red 188 is characterized in that: comprising the steps:

[0025] (1) Preparation of diazo solution:

[0026] Dissolve 10.2 grams of 2-carboxymethylcarboxylate-5-(2', 5'-dichlorophenyl)-formamidoaniline in 80 grams of N,N-dimethylacetamide, fully stir to dissolve, and then Add 13 grams of hydrochloric acid with a concentration of 30%, add ice to cool down to 3°C, add 2.2 grams of sodium nitrite to carry out diazotization reaction for 2 hours, use sulfamic acid to remove excess nitrous, and prepare a diazonium solution for later use;

[0027] (2) Dissolution of coupling components:

[0028] Dissolve 6.8 grams of sodium hydroxide and 0.2 grams of ethylenediaminetetraacetic acid in 300 grams of water, raise the temperature to 90°C, add 9 grams of 2-hydroxy-3-naphthoyl-o-methoxyaniline, stir well to dissolve completely , after dissolving and clarifying, lower the temperature to 40°C to obtain an alkaline solution of 2-hydroxy-3-naphth...

Embodiment 2

[0034] The preparation method of C.I. Pigment Red 188 is characterized in that: comprising the steps:

[0035] (1) Preparation of diazo solution:

[0036] Dissolve 10 grams of 2-carboxymethyl-5-(2',5'-dichlorophenyl)-carboxamidoaniline in 60 grams of N-methylpyrrolidone, stir well to dissolve, and then add 10 grams of 30% hydrochloric acid, 1.5 grams of glacial acetic acid with a concentration of 80%, add ice and cool to -15°C, add 2.1 grams of sodium nitrite for diazotization reaction for 2 hours, use sulfamic acid to break the excess nitrous, and prepare Obtain diazo solution for use;

[0037] (2) Dissolution of coupling components:

[0038] Dissolve 6.8 grams of sodium hydroxide and 0.2 grams of ethylenediaminetetraacetic acid in 300 grams of water, raise the temperature to 80°C, add 8.8 grams of 2-hydroxy-3-naphthoyl-o-methoxyaniline, stir well to dissolve completely , after dissolving and clarifying, lower the temperature to 30°C to obtain an alkaline solution of 2-hyd...

Embodiment 3

[0044] The preparation method of C.I. Pigment Red 188 is characterized in that: comprising the steps:

[0045] (1) Preparation of diazo solution:

[0046] Dissolve 10 grams of 2-carboxymethylcarboxylate-5-(2', 5'-dichlorophenyl)-carboxamidoaniline in 100 grams of N, N-dimethyl sulfoxide, fully stir to dissolve, and then Add 15 grams of hydrochloric acid with a concentration of 30%, add ice to cool down to 20°C, add 2.2 grams of sodium nitrite to carry out diazotization reaction for 2 hours, use sulfamic acid to remove excess nitrous, and prepare a diazonium solution for use;

[0047] (2) Dissolution of coupling components:

[0048] Dissolve 6.8 grams of sodium hydroxide and 0.2 grams of ethylenediaminetetraacetic acid in 300 grams of water, raise the temperature to 100°C, add 9.2 grams of 2-hydroxy-3-naphthoyl-o-methoxyaniline, stir well to dissolve completely , after dissolving and clarifying, lower the temperature to 45°C to obtain an alkaline solution of 2-hydroxy-3-napht...

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Abstract

The invention relates to the preparation method of an organic pigment, in particular to a preparation method of C.I. pigment red 188. The preparation method is characterized by comprising the following steps: preparing diazonium liquid, dissolving and coupling coupling components and performing pigmentation. Therefore, the beneficial effects of the invention are as follows: the problems that the diazonium component 2-methoxycarbonyl-5-(2',5'-dichlorophenyl)-formylaminoaniline is difficult to perform diazotization reaction and the synthesis of the pigment in solvent leads to higher production cost and serious environmental pollution, are effectively solved; and the pigment prepared by the method of the invention has bright color light and is easy to disperse, and the particles of the pigment are soft and have good light fastness and solvent resistance.

Description

(1) Technical field [0001] The invention relates to a preparation method of an organic pigment, in particular to a preparation method of C.I. Pigment Red 188. (2) Background technology [0002] C.I. Pigment Red 188 is a high-performance organic pigment. C.I. Pigment Red 188 gives a yellowish red tone and has good fastness characteristics. Its main application field is printing ink and paint coloring in various printing processes. The chemical structure is insoluble Naphthalene AS azo pigments have multiple polar groups in the molecular structure, such as alkoxy groups, chlorine groups, amido groups, and methyl carboxylate groups. This type of pigment is used for coloring printing inks. The standard depth ( 1 / 1SD, 1 / 25SD), the light fastness is 5-6 grades, 5 grades, and shows excellent solvent resistance, soap resistance, fat resistance, paraffin resistance, acid and alkali resistance, this pigment variety is suitable for High-grade decorative paint, the light fastness of th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B67/20
Inventor 吕东军陈都方
Owner 宇虹颜料股份有限公司
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