Azo hydrophilic compound as well as preparation method and application thereof

A hydrophilic compound and azo technology, applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problems that affect the cis-trans isomerization efficiency of azo groups, poor migration resistance of colored materials, and difficulty in reaching 100%. Achieve the effects of long-lasting maintenance of azo functional properties, not easy migration, and simplified production process

Active Publication Date: 2015-09-30
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Most commonly used hydrophilic chain extenders are complicated to produce and cost high, such as commonly used dimethylolpropionic acid, a common preparation method is to synthesize dimethylolpropionaldehyde from formaldehyde and propionaldehyde, and then oxidize it into dihydroxymethylpropionaldehyde with hydrogen peroxide. Methpropionic acid
[0003] At present, the research on new hydrophilic chain extenders has attracted more and more people's attention, such as Chinese patents 2012102156119, 201210045962X, 201310632545X and other new hydrophilic chain extenders such as sulfonic acid type, sulfonic acid/carboxylic acid type, sulfonic acid/tertiary amine Water chain extender, the hydrophilic chain extender is only to simply increase the hydrophilicity of the resin, without other functional properties, the synthesis process is complicated, the molecular weight is large, and the industrial prospect is not ideal
[0004] The application of azo dyes in water-based polyurethane is mainly to prepare water-based polymer dyes, water-based colored coatings, water-based colored paints and water-based polyurethane coatings with photoelectric properties. At present, oil-soluble azo dyes are mostly used to disperse through dispersants, and then blended into In water-based polyurethane, the production process is complicated, and the obtained colored material has poor migration resistance
Although azo polymers with good migration resistance can be obtained through reactive azo compounds, there are curr

Method used

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  • Azo hydrophilic compound as well as preparation method and application thereof
  • Azo hydrophilic compound as well as preparation method and application thereof
  • Azo hydrophilic compound as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] 1. Take 15 grams of aniline-2,4-disulfonic acid and add it to a 250 ml three-necked bottle, add 60 ml of water at room temperature to fully dissolve it, slowly add 17.8 grams of concentrated hydrochloric acid (mass concentration 36.5%, the concentration used below The same as hydrochloric acid) and put it in an ice-water bath, keep the reaction system at 0-5°C, add dropwise 4.1 grams of sodium nitrite with a concentration of 50% aqueous solution, keep the ice-water bath for 1 hour to obtain aniline-2,4-disulfonic acid Diazonium salt solution;

[0032] 2. Dissolve 11.2 g of N,N-dihydroxyethylaniline in 35 ml of methanol and 0.5 g of acetic acid to form a N,N-dihydroxyethylaniline solution, add it to a 1000 mL three-necked flask, and place the three-necked flask in an ice-water bath , keep the reaction system at 0-5°C, drop the diazonium salt solution of aniline-2,4-disulfonic acid prepared in step 1 into the N,N-dihydroxyethylaniline solution, and drop it within 0.5h. K...

Embodiment 2

[0035] 1. Take 5 grams of 2-aminoterephthalic acid and add it to a 150 ml three-necked bottle, add 50 ml of water at room temperature to fully dissolve it, slowly add 9 grams of concentrated hydrochloric acid and place it in an ice-water bath to keep the reaction system 0- 5°C, dropwise add 1.89 grams of sodium nitrite in an aqueous solution with a concentration of 50% by mass, and keep the reaction in an ice-water bath for 1 hour to obtain a diazonium salt solution of 2-aminoterephthalic acid;

[0036] 2. Dissolve 5.11 grams of N,N-dihydroxyethylaniline in 10 ml of methanol and 0.5 grams of acetic acid to form a N,N-dihydroxyethylaniline solution, add it to a 500ml three-necked flask, and place the three-necked flask in an ice-water bath , keep the reaction system at 0-5°C, drop the diazonium salt solution of aniline-2,4-disulfonic acid prepared in step 1 into the N,N-dihydroxyethylaniline solution, and drop it within 0.5h. Keep the pH of the reaction system at 6 with 1 mol / L...

Embodiment 3

[0039] 1. Take 300 grams of aniline-2,4-disulfonic acid and add it to the reaction kettle, add 1 liter of water at room temperature to fully dissolve it, slowly add 356 grams of concentrated hydrochloric acid and place it in an ice-water bath to keep the reaction system 0-5 ℃, quickly drop 82 grams of sodium nitrite in an aqueous solution with a concentration of 50% by mass, and keep the reaction in an ice-water bath for 1 hour to obtain a diazonium salt solution of aniline-2,4-disulfonic acid;

[0040] 2. Dissolve 222 grams of N,N-dihydroxyethylaniline in 600 ml of methanol and 10 grams of acetic acid to form a N,N-dihydroxyethylaniline solution, add it to the reaction kettle, and place the three-necked bottle in an ice-water bath , keep the reaction system at 0-5°C, drop the diazonium salt solution of aniline-2,4-disulfonic acid prepared in step 1 into the N,N-dihydroxyethylaniline solution, drop it within 0.5h, pass 1mol / L sodium hydroxide aqueous solution to keep the pH o...

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Abstract

The invention discloses an azo hydrophilic compound as well as a preparation method and application thereof. The azo hydrophilic compound comprises a carboxylic acid type azo hydrophilic compound or a sulfonic acid type azo hydrophilic compound. During the self-emulsifying process that the azo hydrophilic compound provided by the invention is used as a chain extender to form a polyurethane emulsion, the azo hydrophilic chain extender with good hydrophilic property is distributed on the surfaces of emulsified ball particles to form a stable double-electrode-layer structure, and the cis-trans isomerization efficiency can reach 100%; the variation of the particle diameter of the polyurethane emulsion under the ultraviolet irradiation shows that the functional material can be used as an ultraviolet responsive nano-carrier, and has potential application prospect in the aspect of forming azo water-soluble polyester and other color-changing polymer materials.

Description

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Claims

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Application Information

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Owner UNIV OF SCI & TECH OF CHINA
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