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

AI Technical Summary

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 currently few types of azo compounds (azodiols) with a double hydroxyl structure, most of which are mainly phenolic hydroxyl groups, and have low reactivity.
Chinese patents 201310572158.1 and 201310573640.7 disclose a variety of azodiols with symmetrical hydroxyl structures and methods for preparing azo-type water-based polyurethanes through these azodiols. The method uses azodiols to partially or completely replace small molecules The diol chain extender prepares side chain azo polyurethane materials, but the amount of azodiol added is affected by the ratio of raw materials (the molar ratio of isocyanate to hydroxyl in polyurethane synthesis is generally between 0.8-1.2) and small molecule diols The ratio in the system has a great influence, and the use of hydrophilic chain extenders and azodiols at the same time will also lead to increased production costs, and due to the addition of water-resistant azodiols, the water resistance will decrease after the self-emulsification process The azo component enters the interior of the electric double layer structure of the water-based polyurethane emulsion ball, and the weakly penetrating ultraviolet light or visible light is difficult to irradiate the azo group located inside the emulsion ball, which affects the cis-trans isomerization efficiency of the azo group (Under the irradiation of ultraviolet light of a specific wavelength, the percentage of trans-configuration of azobenzene converted to cis-configuration), it is difficult to reach 100%

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
Comparison scheme
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

1. Technical field [0001] The invention relates to an azo hydrophilic compound and its preparation method and application. The azo hydrophilic compound of the invention can be used as a hydrophilic chain extender for synthesizing waterborne polyurethane. 2. Background technology [0002] Hydrophilic chain extender is one of the raw materials that must be used in the synthesis and preparation of waterborne polyurethane. Its purpose is to introduce hydrophilic groups into polyurethane and endow waterborne polyurethane with hydrophilicity. Conventional hydrophilic chain extenders mainly include dimethylol propionic acid, dimethylol butyric acid and sodium ethylenediaminoethanesulfonate, etc. These chain extenders often contain carboxyl groups, sulfonic acid groups or secondary amino groups , when it is combined into the polyurethane molecule, the polyurethane side chain or the main chain has a characteristic group that can be ionized, which only provides the function of the hyd...

Claims

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Application Information

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IPC IPC(8): C07C245/08C07C309/46C07C303/22C08G18/38
Inventor 张兴元彭腾李军配周操许飞
Owner UNIV OF SCI & TECH OF CHINA
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