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

Inactive Publication Date: 2005-01-12
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is conceivable that DMF is an organic solvent that can be miscible with water, and it is very difficult to recycle after adding water, so the production cost will be very high

Method used

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  • Method for preparing organic pigment of red benzimidazolones
  • Method for preparing organic pigment of red benzimidazolones
  • Method for preparing organic pigment of red benzimidazolones

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preparation example Construction

[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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Abstract

A method for preparing red benzimidazolone organic dyestuff includes applying diazotization process to carry out diazotization for substituted aromatic amine and aminobenzenesulfonic acid separately for obtaining relevant diazoles solutions, mixing the two diazols, using mixed diazols to couple with coupling composition for obtaining coupled material in mixed crystal form and producing final dyestuff product through pigmenting.

Description

technical field [0001] The invention relates to a preparation method of a benzimidazolone organic pigment, in particular to a preparation method of a red benzimidazolone organic pigment. Background technique [0002] Benzimidazolone organic pigments are azo pigments with 2'-hydroxy-3'-naphthoyl-5-aminobenzimidazolone or its derivatives as coupling components, and its structure is shown in formula (1) : [0003] [0004] The pigments are a class of high-performance organic pigments, their color is very firm, can meet the application requirements of most industrial sectors, mainly used in high-end occasions, such as high-grade plastic products and high-grade ink products. [0005] At present, the preparation method of red benzimidazolone organic pigments is generally divided into three steps, one is the diazotization of substituted aromatic primary amine, The coupling of 5-aminobenzimidazolone or its derivatives, the third is the pigmentation treatment of the conjugate. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B29/40
Inventor 沈永嘉张妤胡莹玉王洪太王金友
Owner EAST CHINA UNIV OF SCI & TECH
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