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Fluorine-bearing diketopyrrolopyrrole quaternary ammonium salt compound and preparation method and application thereof

A technology for diketopyrrolopyrrole and quaternary ammonium salts is applied in the field of fluorine-containing diketopyrrolopyrrole quaternary ammonium salt compounds and their preparation, which can solve the problems of increasing the brittleness and stress of a coating, and achieve excellent solvent resistance, The effect of suppressing the deposition of copper ions and stabilizing the structure

Active Publication Date: 2019-06-18
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Dye additives can greatly improve the brightness and flatness of copper deposits, but such additives will increase the brittleness and stress of the coating, and at the same time will bring greater pressure to subsequent waste treatment, especially water treatment

Method used

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  • Fluorine-bearing diketopyrrolopyrrole quaternary ammonium salt compound and preparation method and application thereof
  • Fluorine-bearing diketopyrrolopyrrole quaternary ammonium salt compound and preparation method and application thereof
  • Fluorine-bearing diketopyrrolopyrrole quaternary ammonium salt compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The preparation method of compound I-1 is as follows:

[0057]

[0058] (1) Preparation of intermediate 3-1

[0059] Add 100ml of tert-amyl alcohol into a 250ml three-neck flask, then cut 4g of sodium into sodium particles and add it, and then add ferric chloride with a catalytic amount of 20-40mg as a catalyst. Heat to 100~105°C, react for 2~3h. Cool down to 50-60°C, add 68.6mmol of compound 2-1, then heat to 100-105°C, add 8ml of diisopropyl succinate compound 1 and 40ml of tert-amyl alcohol into the three-necked flask with a constant pressure dropping funnel , 3 ~ 5s / d, 2-3h drop. Finally, react for another 4 hours, stop the reaction, pour the reaction product into a beaker, add 100ml of methanol to dilute, then add acetic acid to adjust the pH to 7, filter with suction, wash the filter cake with methanol, take the filter cake, heat and dry it, and then use N, N-dimethylformamide was dissolved in heat, cooled and suction filtered, the filter cake was washed wit...

Embodiment 2

[0069] Compound I-2

[0070]

[0071] (1) Preparation of Intermediate 3-2

[0072] Add 100ml of tert-amyl alcohol into a 250ml three-neck flask, then cut 4g of sodium into sodium pellets and add in it, and then add a catalytic amount of 20-40mg of ferric chloride as a catalyst. Heat to 100~105°C, react for 2~3h. Cool down to 50-60°C, add 68.6mmol of compound 2-2, and then heat to 100-105°C. Add 8ml of diisopropyl succinate compound 1 and 40ml of tert-amyl alcohol mixture into a three-necked flask with a constant pressure dropping funnel, drop it in 3-5s / d, and drop it in 2-3h. Finally, react for another 4 hours, stop the reaction, pour the reaction product into a beaker, add 100ml of methanol to dilute, then add acetic acid to adjust the pH to 7, filter with suction, wash the filter cake with methanol, take the filter cake, heat and dry it, and then use N, N-dimethylformamide was dissolved in heat, cooled and suction filtered, the filter cake was washed with water and me...

Embodiment 3

[0082] Preparation of Compound I-3

[0083]

[0084] (1) Preparation of intermediate 3-3

[0085] Add 100ml of tert-amyl alcohol into a 250ml three-necked flask, then cut 4g of sodium into sodium particles and add it, and then add a catalytic amount of 20-40mg of ferric chloride as a catalyst. Heat to 100~105°C, react for 2~3h. Cool down to 50-60°C, add 68.6mmol of compound 2-3, and then heat to 100-105°C. Add 8ml of diisopropyl succinate compound 1 and 40ml of tert-amyl alcohol mixture into a three-necked flask with a constant pressure dropping funnel, drop it in 3-5s / d, 2-3h. Finally, react for another 4 hours, stop the reaction, pour the reaction product into a beaker, add 100ml of methanol to dilute, then add acetic acid to adjust the pH to 7, filter with suction, wash the filter cake with methanol, take the filter cake, heat and dry it, and then use N, N-dimethylformamide was dissolved in heat, cooled and suction filtered, the filter cake was washed with water and met...

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Abstract

The invention discloses a fluorine-bearing diketopyrrolopyrrole quaternary ammonium salt compound, having a structure shown as the formula (I) which is shown in the description, wherein R1 is one of F, CH2F, CHF2, CF3, OCH2F, OCHF2, OCF3, SCH2F, SCHF2, SCF3, CF2(CF2)nCF3, n is an integer of 0-10, and X is F, Cl, Br or I. The fluorine-bearing diketopyrrolopyrrole quaternary ammonium salt compound is prepared from diisopropyl succinate and benzonitrile of different substituents and can act as a plating leveling agent.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a fluorine-containing diketopyrrolopyrrole quaternary ammonium salt compound and a preparation method and application thereof. Background technique [0002] Electroplating is the process of plating a thin layer of other metals or alloys on the surface of certain metals using the principle of electrolysis. It is a process of using electrolysis to attach a layer of metal film to the surface of metal or other material parts to prevent metal oxidation ( Such as rust), improve wear resistance, electrical conductivity, reflective properties, corrosion resistance (copper sulfate, etc.) and enhance the appearance. Electroplating technology is widely used. There are electroplating products around our lives, such as: necklaces, rings, clocks, belt buckles and other accessories, pens, staplers, pencil cases, scissors and other stationery, air conditioners, refrigerato...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C25D3/38
Inventor 王利民李俊徐杰王峰王桂峰魏小川王康何玉龙吕进阁杨青颖张盈宁徐萌田禾陈立荣
Owner EAST CHINA UNIV OF SCI & TECH
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