Method for preparing organic pigment of red benzimidazolones
A technology of benzimidazolone and aminobenzimidazolone, which is applied in the field of preparation of red benzimidazolone organic pigments, and can solve problems such as difficult recycling and high production costs
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[0013] The preparation method of the red benzimidazolone organic pigment of the present invention, it comprises the steps:
[0014] (1) the diazotization reaction of substituted aromatic primary amine and aminobenzenesulfonic acid:
[0015] This is an existing technology, which will not be repeated here, and its reaction formula is as follows:
[0016]
[0017] Where: X is Cl - or HSO 4 - ; Described substituted aromatic primary amine [compound (b)] is optional: o-fluoroaniline, o-chloroaniline, p-chloroaniline, m-bromoaniline, m-iodoaniline, o-toluidine, p-toluidine, o-methoxyaniline, o-Nitroaniline, m-nitroaniline, p-nitroaniline, methyl anthranilate, n-butyl anthranilate, 2,4-dimethylaniline, o-methyl-p-chloroaniline, 2-methyl -5-Chloroaniline, 2-methyl-4-nitroaniline, 2-methyl-4-amino-5-methoxy-benzenesulfonylmethylamine, 2-methoxy-4-chloroaniline, 2 -Methoxy-5-chloroaniline, 2-methoxy-4-nitroaniline, 2-nitro-4-methyl-aniline, 2-nitro-4-methoxyaniline, 2-nitro -4-...
Embodiment 1
[0039] Preparation of n-butyl phthalate phenylazo-5-(2', 3'-hydroxynaphthoamide)-aminobenzimidazolone (C.I. Pigment Red 208)
[0040] The main reaction formula is as follows:
[0041]
[0042] Preparation of diazo liquid
[0043] 1) The diazotization of sulfamic acid
[0044] Para-aminobenzenesulfonic acid (1.73g, 10mmol) was dissolved in water (25ml, containing 10mmolNaOH), stirred at room temperature for 15min, filtered, discarded insolubles, cooled to 0-5°C in an ice bath, added NOHSO 4 (1.59 g, 12.5 mmol, composed of concentrated sulfuric acid and sodium nitrite), after the addition was completed, stirring was continued for 10 min to obtain a gray suspension, which was diluted with 1N hydrochloric acid to a total volume of 50 ml, and refrigerated for later use.
[0045] 2) The diazotization of n-butyl anthranilate
[0046] n-Butyl anthranilate (35g, 0.18mol), water (800ml) and 30% hydrochloric acid (30ml) were mixed and cooled to 0-5°C with an ice bath, a small amoun...
Embodiment 2
[0055] Preparation of n-butyl phthalate phenylazo-5-(2', 3'-hydroxynaphthoamide)-aminobenzimidazolone (C.I. Pigment Red 208)
[0056] The synthesis of the crude pigment is the same as that in Example 1.
[0057] Pigmentation processing of crude pigments
[0058] According to the weight of crude pigment (g): DMF (ml)=1:20, the dry crude pigment and solvent were added to the reactor, and after the addition was completed, the temperature was raised to 80-90° C. under stirring, and the mixture was kept stirring for 0.5-1 hour. Subsequently, the temperature was lowered to 15-20°C for filtration, the DMF mother liquor was recovered and used again, the filter cake was washed with water, dried and pulverized to obtain 65g of fine pigments.
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