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Modified azobenzene derivative for fabric dyeing and finishing and preparation method thereof

A technology of azobenzene derivatives and cross-linking modification, which is applied in dyeing, textile and papermaking, organic chemistry, etc., and can solve problems such as inconvenient storage and transportation, limited photoresponse characteristics, and less research on photosensitive surfactants. , to achieve strong surfactant effect and foaming, good surface active effect and foaming, improved photoresponsiveness and dyeing effect

Active Publication Date: 2018-09-04
常州大邦化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] (1) Poor photostability: Since azobenzene derivatives are photosensitive substances, they have poor stability under light, and have "fatigue" of light attenuation for a long time, especially when there is photodegradation under strong light And other shortcomings, bring inconvenience to storage and transportation
[0017] (2) Poor water solubility: In addition to being easily degraded by light, the azobenzene dye auxiliaries in the prior art often have poor water solubility as organic compounds, which affects the use in aqueous solution environments;
[0018] (3) Limited photoresponse characteristics: the existing azobenzene compounds have good photoresponse characteristics in organic solvents, but the response characteristics are greatly reduced in large volumes of aqueous dye solutions;
[0019] (4) The effect is single: the improvement of dyeing properties such as dyeability, fastness, and weight gain cannot be simultaneously provided
However, photosensitive surfactants based on modified azobenzene are still less studied, especially azobenzene derivatives with excellent photostability (photodegradation and light attenuation), high water solubility, high surface activity and improved dyeability Dyeing auxiliaries, still seriously lacking

Method used

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  • Modified azobenzene derivative for fabric dyeing and finishing and preparation method thereof
  • Modified azobenzene derivative for fabric dyeing and finishing and preparation method thereof
  • Modified azobenzene derivative for fabric dyeing and finishing and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Preparation of polymer (n dimethylaminoethyl acrylate: n 4-(N,N,N-trilauryl ammonium methyl bromide)-4’-methacrylamidocarbonylazobenzene=5:1)

[0057] S1, acid chloride reaction

[0058] Add 24g (100mmol) of 4-methyl-4'-carboxyazobenzene into 100mL of thionyl chloride, stir overnight at 65°C, spin evaporate the unreacted thionyl chloride to obtain 23.5g of a colorless oily crude product, That is, the compound 4-methyl-4'acyl chloride azobenzene.

[0059] S2, amidation reaction

[0060] In a 50mL three-neck flask equipped with magnetic stirring, a constant pressure dropping funnel, a condenser tube and a thermometer, add 2.25g of 4-methyl-4'-acyl chloride azobenzene and 10mL of dichloromethane as the reaction mixture 1. Add 10mL of dichloromethane, 1.2mL of triethylamine and 1.56g of methacrylamide into the pressure dropping funnel as the reaction mixture 2, heat the reaction solution 1 to 30-40°C under stirring, then open the constant pressure dropping funnel Drop th...

Embodiment 2

[0070] Preparation of (n dimethylaminoethyl methacrylate: n 4-(N,N,N-tri(hexadecyl)ammonium methyl bromide)-4'-methacrylamidocarbonylazobenzene=4: 1) polymer

[0071] S1, S2 steps are the same as embodiment 1:

[0072]S1, acid chloride reaction

[0073] Add 24g (100mmol) of 4-methyl-4'-carboxyazobenzene into 100mL of thionyl chloride, stir overnight at 65°C, spin evaporate the unreacted thionyl chloride to obtain 23.5g of a colorless oily crude product, That is, the compound 4-methyl-4'-acyl chloride azobenzene.

[0074] S2, amidation reaction

[0075] In a 50mL three-neck flask equipped with magnetic stirring, a constant pressure dropping funnel, a condenser tube and a thermometer, add 2.25g of 4-methyl-4'-acyl chloride azobenzene and 10mL of dichloromethane as the reaction mixture 1. Add 10mL of dichloromethane, 1.2mL of triethylamine and 1.56g of methacrylamide into the pressure dropping funnel as the reaction mixture 2, heat the reaction solution 1 to 30-40°C under sti...

Embodiment 3

[0083] Photostability Test

[0084] Prepare 1 x 10 with deionized water -5 The cross-linked polymerization product suspension (ultrasonic 10min in deionized water) prepared by the embodiment 1 of mol / L, detects its absorption peak with UV-Vis in the quartz absorption cell, uses 410nm monochromatic light and 450nm monochromatic light Take turns to irradiate, and regularly detect the changes in the ultraviolet absorption spectrum of the 410nm absorption peak.

[0085] The results showed that under the alternating irradiation of 410 and 450nm light, the absorbance at 410nm had almost no attenuation after 20 cycles of illumination; after 50 cycles of illumination, the absorbance at 410nm only attenuated by 2.6%. It shows that the cross-linked modified azobenzene polymer prepared by the present invention is relatively stable under light, basically does not undergo photodegradation and light attenuation, and can be used as a light-stimuli-responsive material.

[0086] Compared wit...

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Abstract

The invention provides an azobenzene derivative containing long-chain alkyl hyamine groups and a preparation method of the azobenzene derivative. The azobenzene derivative is obtained by taking 4-methyl-4'-carboxylazobenzene as a raw material, performing acylating chlorination, amidation, hyamine salinization, cross-linking reaction and the like. The obtained derivative has high water solubility,light stability and chromaticity, can substitute chemical reagents, such as foaming agents and defoaming agents, used during existing dyeing and finishing process, and can improve dyeing properties such as dyeability and color fastness.

Description

technical field [0001] The invention relates to a water-soluble modified azobenzene dye auxiliary and a preparation method thereof, belonging to the fields of textile dyes and organic synthesis. Background technique [0002] Stimuli-responsive materials can rapidly change their performance parameters when they feel stimuli from the external environment (such as light, pH value, temperature, etc.), thereby producing responsive changes to the stimuli, thereby realizing some specific functions. Among them, photostimuli-responsive materials have become one of the hotspots in recent years due to their advantages of cleanliness, safety, easy operation and control, and high efficiency. They are widely used in liquid crystals, catalysis, ion self-assembly, biomedical carriers, and molecular switches. For example, light-sensing liposomes use light-sensing materials and phospholipids to form liposomes to encapsulate drugs, and use external light sources to induce structural changes in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C08F220/34C08F220/60D06P1/52D06P1/00
CPCC07C245/08C08F220/34D06P1/0016D06P1/525C08F220/603
Inventor 杨仲辉张伟彬
Owner 常州大邦化工有限公司