Arylamine compound containing multiple sulfonic groups and preparation method thereof

A polysulfonic acid group arylamine and polysulfonic acid group technology, which is applied in the field of polysulfonic acid group-containing aromatic amine compounds and its preparation, can solve the problem of difficulty in greatly increasing the number of sulfonic acid groups, pollution, and three wastes, etc. problems, to achieve the effects of reduced energy consumption, simple operation of the preparation process, and significant low-temperature storage stability

Pending Publication Date: 2022-07-05
NANJING XIAOZHUANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a kind of arylamine compound containing polysulfonic acid groups and preparation method thereof, to solve the above-mentioned background technology and propose in the present technology, be difficult to find out suitable aminoaryl sulfonic acid intermediate from existing Diazo components or tail groups can greatly improve the solubility of these dyes. At the same time, the traditional sulfonation process will produce a large amount of three wastes, causing serious pollution. The number of sulfonic acid groups is difficult to increase greatly

Method used

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  • Arylamine compound containing multiple sulfonic groups and preparation method thereof
  • Arylamine compound containing multiple sulfonic groups and preparation method thereof
  • Arylamine compound containing multiple sulfonic groups and preparation method thereof

Examples

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Effect test

Embodiment 1

[0045] A kind of aromatic amine compound containing polysulfonic acid group, its structural formula is as follows:

[0046]

[0047] The preparation method of polysulfonic acid group-containing aromatic amine compound I-1 comprises the following steps:

[0048] S1: In the reaction equipment, 18.9 g (0.1 mol) of 100% tetraethylene pentamine was dissolved in 200 mL of water, and the temperature was raised to 60° C. with stirring. Dissolve 53.6 g (0.4 mol) of 100% sodium hydroxymethanesulfonate in 300 mL of water. The sodium hydroxymethanesulfonate aqueous solution was added dropwise to the aqueous solution of tetraethylene pentamine in the reaction equipment. After the dropwise addition, the reaction was continued at pH=10 and 60°C for 6 hours. Tetraethylene pentamine reaction solution.

[0049] S2: the polysulfonic acid group-modified tetraethylene pentamine reaction solution obtained in step S1 is heated to 70-75° C., and 22.3 g (0.12 mol) of 100% p-nitrobenzoyl chloride ...

Embodiment 2

[0054] The difference from Example 1 is that:

[0055] A kind of aromatic amine compound containing polysulfonic acid group, its structural formula is as follows:

[0056]

[0057] The preparation method of polysulfonic acid group-containing aromatic amine compound I-2 comprises the following steps:

[0058] S1: Dissolve 18.9 g (0.1 mol) of 100% tetraethylene pentamine in 200 mL of water, and raise the temperature to 60° C. with stirring. Dissolve 53.6 g (0.4 mol) of 100% sodium hydroxymethanesulfonate in 300 mL of water. The sodium hydroxymethanesulfonate aqueous solution was added dropwise to the aqueous solution of tetraethylenepentamine. After the dropwise addition, the reaction was continued at pH=10 and 60°C for 6 hours. Amine reaction solution.

[0059] S2: the polysulfonic acid group-modified tetraethylene pentamine reaction solution obtained in step S1 is heated to 80-85° C., and 24.3 g (0.12 mol) of 100% 2,4-dinitrochlorobenzene is slowly added. The time is ab...

Embodiment 3

[0062] The difference from Example 1 is that:

[0063] A kind of aromatic amine compound containing polysulfonic acid group, its structural formula is as follows:

[0064]

[0065] The preparation method of polysulfonic acid group-containing aromatic amine compound I-3 comprises the following steps:

[0066] S1: Dissolve 18.9 g (0.1 mol) of 100% tetraethylene pentamine in 200 mL of water, and raise the temperature to 60° C. with stirring. Dissolve 64.0 g (0.4 mol) of 100% sodium glycidyl sulfonate in 300 mL of water. The aqueous solution of sodium glycidyl sulfonate was added dropwise to the aqueous solution of tetraethylene pentamine. After the dropwise addition, the reaction was continued at pH=10 and 60°C for 6 hours. Pentaamine reaction solution.

[0067]S2: the polysulfonic acid group-modified tetraethylene pentamine reaction solution obtained in step S1 is heated to 70-75° C., and 26.6 g (0.12 mol) of p-nitrobenzenesulfonyl chloride (100%) is slowly added, and the ...

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Abstract

The invention discloses an arylamine compound containing multiple sulfonic groups, the compound is shown as a structural general formula I, R1 is-H,-NH2 or-CF3; r2 is-NH <->,-CONH <-> or-SO2NH <->; r3 is-CH2SO3M or-CH2CH (OH) CH2SO3M, wherein M is H or an alkali metal; n is an integer of 2-9. The molecular structure of the polysulfonic acid group-containing arylamine compound provided by the invention contains a plurality of sulfonic acid groups, so that the problem that the number of sulfonic acid groups of the existing amino aromatic sulfonic acid compound structure is small is solved, the polysulfonic acid group-containing arylamine compound has extremely high solubility, and a dye prepared by taking the compound as a diazo component or a condensation component has extremely high solubility; the method is particularly suitable for small bath ratio dyeing, cold pad batch dyeing and preparation of high-concentration liquid dye, generation and energy consumption of printing and dyeing wastewater are greatly reduced, and the problem that the solubility of the dye cannot be effectively improved due to the small number of sulfonic acid groups in a diazo component or condensation component structure for existing dye is solved.

Description

technical field [0001] The invention relates to the technical field of dye intermediates, in particular to an aromatic amine compound containing a polysulfonic acid group and a preparation method thereof. Background technique [0002] Aminoaromatic sulfonic acid is a kind of important fine chemical intermediate, which has a wide range of applications in the fields of dyes, pesticides and medicine. Especially in the field of dyes, aminoaromatic sulfonic acid compounds are often used as the diazo group of water-soluble azo dyes. Minerals, coupling components or in reactive dyes can also be used as condensation components (tail groups). [0003] Dyes are substances that color fabrics. Among the existing dyes, water-soluble dyes such as acid dyes and reactive dyes are widely used in the coloring of cotton, wool, silk and blended fibers. In recent years, people pay more and more attention to energy and environmental protection issues. In order to save energy and reduce emission...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/32C07C309/14C09B62/085C09B62/665
CPCC07C303/32C07C309/14C09B62/085C09B62/665
Inventor 杨晶晶
Owner NANJING XIAOZHUANG UNIV
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