Coupling component containing phthalimide structure, and preparation method and application of coupling component

A technology of phthalimide and coupling components, applied in the field of coupling components and their preparation, can solve the problems of poor washing fastness and the like

Pending Publication Date: 2020-06-19
乌海青石化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] By comparing the structural formulas of the coupling components in the above-mentioned patents, it can be found that the introduction of the phthalimide structure in the coupling components is connected with the nitrogen atom of the imide. A hydrolysis reaction can occur to generate phthalic acid by-products (see ...

Method used

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  • Coupling component containing phthalimide structure, and preparation method and application of coupling component
  • Coupling component containing phthalimide structure, and preparation method and application of coupling component
  • Coupling component containing phthalimide structure, and preparation method and application of coupling component

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Add 10.8g of N-methylaniline, 13.9g of epichlorohydrin, and 20mL of acetonitrile as a solvent into a 100mL three-necked reaction flask with a stirrer and a thermometer, and add another 0.3g of zinc chloride catalyst; while stirring, heat to reflux and keep warm Reaction for 5 hours; liquid phase monitoring raw material N-methylaniline reaction is complete; cooling to room temperature, slowly adding 14g of 50% potassium hydroxide solution; adding 20 mL of water, stirring at room temperature for 4 hours; liquid phase monitoring cyclization is complete; Add 30mL of water and 30mL of ethyl acetate to the reaction solution, extract and separate the layers, wash the organic layer with 30mL×3 water, and dry with anhydrous magnesium sulfate; distill off the solvent to obtain 15.1g of oily N-(2,3-epoxypropyl) -N-methylaniline, see formula (16-1), yield 92.6%, liquid chromatography purity 95%, LC-MS (ESI) positive ion mode: m / z164, [M+H] + ,m / z186,[M+Na] + ,m / z202[M+K] + .

[0065] ...

Embodiment 2

[0071] Add 22.7g 4-amino-N-butylphthalimide, 13.9g epichlorohydrin, and 50mL acetonitrile as solvent into a 150mL three-necked reaction flask with thermometer and stirring, and add 1.40g zinc chloride as a catalyst ; Under stirring, the temperature is raised to reflux, and the temperature is kept for 8 hours; the liquid phase monitors the completion of the raw material reaction; the ice-water bath is cooled to 0-5 ℃, and 27g 30% potassium hydroxide solution is slowly added; the reaction is stirred at 0-5 ℃ for 5 hours; The monitoring and environmentalization is completed;

[0072] Post-treatment: add 30mL water and 30mL dichloromethane to the reaction solution, extract and separate the layers, wash the organic layer with 30mL×3 water, and dry with anhydrous magnesium sulfate; distill off the solvent to obtain a thick substance, crystallize with ethanol to obtain 23.4g of light yellow solid Namely 4-[N-(2',3'-epoxypropyl)]amino-N-butylphthalimide, see formula (19-1), yield 85%; li...

Embodiment 3

[0076] 13.8g 4-[N-(2',3'-epoxypropyl)]-amino-N-butylphthalimide, see formula (19-1), 9.0g m-acetamido-N- Ethylaniline and 50mL acetonitrile were added to a 100mL reaction flask with a thermometer and stirring, and another 1.0g p-toluenesulfonic acid was added; the reaction was kept under reflux and stirred for 10 hours, and the reaction progress was monitored in the liquid phase. The solvent is distilled off to obtain 18.4g of thick material that is the coupling component, see formula (8-3), the yield is 81.4%, the liquid phase purity is 92%, LC-MS (ESI) positive ion mode: m / z453, [M +H] + ,m / z475,[M+Na] + ,m / z491[M+K] + .

[0077]

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Abstract

The invention discloses a coupling component containing a phthalimide structure, and a preparation method and application of the coupling component. The structural formula of the coupling component isas shown in a formula (7). The prepared coupling component containing the phthalimide structure belongs to novel coupling components containing phthalimide; the phthalimide structure is introduced through connection with a substituent group on a phthalimide benzene ring, and the nitrogen atoms of imide can be connected to different substituent groups R1, so a dye is allowed to have different application performances and excellent color fastness to washing. Meanwhile, only an alkali washing process is used after a polyester fabric is dyed, so carcinogenic aromatic amine generated by decomposing azo groups under the condition of reduction cleaning of sodium hydrosulfite is prevented from being released into sewage, the treatment burden of washing sewage is reduced, and high environmental protection performance is achieved.

Description

Technical field: [0001] The invention relates to a coupling component and a preparation method and application thereof, in particular to a coupling component containing a phthalimide structure and a preparation method and application thereof. Background technique: [0002] Disperse dyes have become one of the most actively developed dye categories in the world dye market. Due to the industrialization of ultra-fine polyester fibers, the growth of tourism polyester fibers, and the wide application of polyester-spandex stretch fabrics in sports and casual women's clothing fabrics, conventional disperse dyes have problems with low dye uptake or poor color fastness. Therefore, it is very important to develop disperse dyes with high dye depth, high washing fastness, high heat migration fastness, and high environmental performance in the dye and printing and dyeing industries. [0003] The performance of the dye is closely related to the structure of the dye. The azo-type disperse dye co...

Claims

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Application Information

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IPC IPC(8): C07D209/48C09B29/085C09B29/09C09B29/01C09B29/042C09B29/045C09B67/38C09B67/36D06P1/18D06P3/54D06P3/56
CPCC07D209/48C09B29/08C09B29/0838C09B29/0834C09B29/0007C09B29/0085C09B29/0081C09B67/008C09B67/0079D06P1/18D06P3/54D06P3/56Y02P20/55
Inventor 尹东
Owner 乌海青石化学有限公司
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