Synthesis method of azoic coupling component AS-D series pigment for aqueous application system and product obtained by synthesis method

A synthesis method and chromophenol technology, applied in the application, chemical instruments and methods, azo dyes and other directions, can solve the problems that do not involve the influence of product crystals, environmental pollution, process complexity, etc., and achieve bright colors, easy dispersion, simple craftsmanship

Active Publication Date: 2011-06-15
杭州百合辉柏赫颜料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method is effective for the surface treatment of pigments, but the organic matter used must be recovered, which complicates the process, and will pollute...

Method used

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  • Synthesis method of azoic coupling component AS-D series pigment for aqueous application system and product obtained by synthesis method
  • Synthesis method of azoic coupling component AS-D series pigment for aqueous application system and product obtained by synthesis method
  • Synthesis method of azoic coupling component AS-D series pigment for aqueous application system and product obtained by synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Synthesis of C.I. Pigment Red 112 Using Sulfonated Succinic Acid Surfactant IIB

[0034] The structure of sulfosuccinic acid surfactant IIB is as follows:

[0035]

[0036] Preparation of 2,4,5-trichloroaniline diazonium salt solution: Add 49.0g 2,4,5-trichloroaniline (0.25mol) and 150ml of water into a large beaker, stir for 40 minutes to fully moisten the trichloroaniline wet. Add 150 g of 30% hydrochloric acid again, and continue stirring for 8 hours. Add crushed ice to cool it down to -5 to 0°C, quickly add 53.0g (35%, 0.27mol) of sodium nitrite solution under liquid, and stir for 60 minutes. If necessary, add additional sodium nitrite or sulfamic acid to ensure a slight excess of sodium nitrite. Filter and adjust the volume of the solution to 800ml, and ensure that the temperature of the diazo solution is between 0 and 5°C by adding ice.

[0037] Preparation of naphthol AS-D coupling component suspension: Add 70.0g of 30% liquid caustic soda and...

Embodiment 2

[0042] Example 2 Synthesis of C.I. Pigment Red 112 Using Sulfonated Succinic Acid Surfactant IID

[0043] The structure of sulfonated succinic acid surfactant IID is as follows:

[0044]

[0045] According to the process synthesis conditions of Example 1, C.I. Pigment Red 112 was synthesized as the sample of Example 2 with sulfosuccinic acid surfactant IID instead of sulfosuccinic acid surfactant IIB.

[0046] The sample of Example 2 was pressed into tablets with KBr, and the infrared absorption spectrum was measured and compared with the infrared spectrum of permanent red FGR. Strong absorption (1673, 1592, 1552 and 1484 cm -1 ) and absorption in the fingerprint region (1250, 1203, 1159, 1011, 750, 516 cm -1 ) is completely consistent with the spectrum of Everlasting Red FGR. By color measurement, the coloring power of the sample of Example 2 in polyacrylic resin is 12% higher than that of permanent red FGR.

Embodiment 3

[0047] Example 3 Sulfonated succinic acid surfactant IIB dosage experiment

[0048] According to the synthesis conditions of Example 1, 11.3g (42%, 0.01mol) of sulfosuccinic acid surfactant IIB was used to synthesize C.I. Pigment Red 112 as the sample of Example 3-1. Through color measurement, the coloring power in polyacrylic resin is 4% higher than that of permanent red FGR.

[0049] According to the synthesis conditions of Example 1, 70.5g (42%, 0.062mol) of sulfosuccinic acid surfactant IIB was used to synthesize C.I. Pigment Red 112 as the sample of Example 3-2. The sample can be instant dissolved in polyacrylic resin after milling. Although the tinting strength is lower than that of permanent red FGR when diluting the color measurement due to the high content of surfactant, the natural color concentration is equivalent to that of permanent red FGR. The advantage is that it can be used as an instant pigment in water-based concentrated color systems without pre-dispersi...

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Abstract

The invention belongs to the field of pigment synthesis and provides a synthesis method of azoic coupling component AS-D series pigment for an aqueous application system and a product obtained by the synthesis method. The synthesis method comprises the steps of coupling azoic coupling component AS-D as a coupling component with substituted aromatic amine diazonium salt to obtain the azoic coupling component AS-D series pigment with a structure satisfying a general formula (I), wherein sulfonated succinic acid surfactant activated agent with the structure satisfying a formula (II) is used, andthe formulas (I) and (II) are as shown in the specification, in the formulas, R1 is selected from CH3, NO2, OCH3 or Cl, R2 is selected from NO2, H, Cl, CH3 or SO2NHCH3, R3 is selected from H, Cl, NO2or CONH2, and R is selected from C4H9, C5H11,C6H13, C8H17, C10H21, C12H25, C13H27 or C18H37. The invention also provides the product obtained by the synthesis method. By using the synthesis method, the problems that in the existing pigment synthesis, chemical oxygen demand (COD) in waste water is over high, environment is polluted, and the like are solved. The pigment product prepared by the synthesis method is easy to disperse in aqueous solution and has bright color and high tinting power.

Description

[0001] technical field [0002] The invention belongs to the field of pigment synthesis, specifically relates to a water-based pigment synthesis method, and more specifically provides a synthesis method of naphthol AS-D series pigments used in water-based application systems. Background technique [0003] Naphthalene AS pigments are azo pigments prepared by coupling 2-hydroxy-3-naphthylamide derivatives with substituted arylamine diazonium salts as coupling components, mainly giving red spectrum (W.Herbst, K.Hunger, Industrial Organic Pigments, Third Edition, Pages 280-286. WILEY-VCH Verlag GmbH & Co. KGaA). In this paper, the naphthol AS pigment whose coupling component is naphthol AS-D (2-hydroxy-3-naphthoyl-o-toluidine, CAS number: 135-61-5) is called naphthol AS-D series pigments . Since naphthol AS-D is synthesized from o-methylaniline, which is a cheap isomer in the production process of p-toluidine, this makes this kind of pigment relatively inferior to other naphth...

Claims

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Application Information

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IPC IPC(8): C09B29/20C09B67/36C09B67/02C09D11/10C09D7/12
Inventor 马引民胡海涛王寒
Owner 杭州百合辉柏赫颜料有限公司
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