Azo dibasic alcohol in symmetrical structure and preparation method thereof

A symmetrical structure and azobis technology, which is applied in the field of azodiols with symmetrical structures and its preparation, can solve the problems of few types of azodiols, low reactivity, asymmetric hydroxyl structure, etc., and achieve raw material Easy to obtain, simple process, and long-lasting photoelectric properties

Inactive Publication Date: 2014-03-12
UNIV OF SCI & TECH OF CHINA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of azodiols with symmetrical structure and its preparation method, to solve the problems of few types of azodiols, asymmetric hydroxyl structure, low reactivity, etc. The small molecular diol used in the synthesis of polymers such as carbonate, polyether, polyether ester or polyurethane introduces azo groups by chemical keying, so that the obtained small molecular diol contains both A hydroxyl group with a symmetrical structure and the same reactivity, and an azo chromophore

Method used

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  • Azo dibasic alcohol in symmetrical structure and preparation method thereof
  • Azo dibasic alcohol in symmetrical structure and preparation method thereof
  • Azo dibasic alcohol in symmetrical structure and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add 3 grams (32 mmol) of aniline to 20 mL of water, then slowly add 9.8 grams of concentrated hydrochloric acid with a concentration of 37% by mass, keep the reaction system at 0-5°C, and add 2.22 grams (32 mmol) dropwise within 1 minute while stirring A solution prepared by sodium nitrite and 3.5mL water was kept at 0-5°C for 1 hour to obtain the diazonium salt solution of aniline;

[0032] Add 5 mL of water, 10 mL of methanol, and 6 mL of acetic acid into 5.8 g (32 mmol) of N,N-dihydroxyethylaniline, and stir until the N,N-dihydroxyethylaniline is completely dissolved. Keep the reaction system at 0-5°C, add the diazonium salt solution of aniline prepared above dropwise, and adjust the pH value of the system to 6 through the sodium hydroxide solution with a substance concentration of 1M, filter after 2 hours of reaction, and wash the precipitate with water Once, and then recrystallized with a mixture of ethanol and water at a volume ratio of 2.5:1 to obtain azodiol N,N...

Embodiment 2

[0037] Add 3mL of acetic acid to 7.5mL of water, then add 1.5g (10mmol) of 1-naphthylamine, and then slowly add 3g of concentrated hydrochloric acid with a concentration of 37% by mass. Change to an ice bath at 0-5°C, add a solution prepared by 0.72 g (10 mmol) sodium nitrite and 1.5 mL water dropwise under stirring, and keep the reaction for 2 hours to form a diazonium salt solution of 1-naphthylamine;

[0038] Add 1mL of acetic acid and 5.7mL of methanol into 1.9g (10mmol) of N,N-dihydroxyethylaniline, keep the reaction system at 0-5°C, add the diazonium salt of 1-naphthylamine prepared above dropwise, and pass Add the amount of substance concentration and adjust the pH value of 1M aqueous sodium hydroxide solution to be 6, adjust the pH value of the system after 2 hours of reaction under magnetic stirring to be 7, filter the product and wash it with water, then use ethanol and water in a volume ratio of 5: 1 After recrystallization of the prepared mixture, azodiol N,N-dihyd...

Embodiment 3

[0044] Add 15.35 grams (127 mmol) of 4-ethylaniline to 100 mL of water, then slowly add 45 grams of concentrated sulfuric acid with a concentration of 98% by mass, stir for 5 minutes, cool down to 0-5°C, and drop the solution within 1 minute. 8.75 g (127 mmol) of sodium nitrite and 15 mL of water were prepared, and the system was kept at 0-5 ° C for 1 hour to obtain the diazonium salt solution of 4-ethylaniline;

[0045] Add 25mL of water, 24mL of methanol and 5mL of acetic acid into 23.45g (129mmol) of N,N-dihydroxyethylaniline. After forming a solution, keep the reaction system at 0-5°C, and add the above-prepared 4-ethanediline dropwise under magnetic stirring. The diazonium salt solution of base aniline, and the pH value of the system is adjusted to 6 by adding a sodium hydroxide solution with a concentration of 1M, keeping the reaction at 0-5°C for 2 hours, and then filtering, and the obtained precipitate is mixed with ethanol and water according to The mixture prepared a...

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Abstract

The invention discloses an azo dibasic alcohol in a symmetrical structure and a preparation method thereof. The invention is characterized in that the azo dibasic alcohol is prepared by carrying out diazotization-coupling reaction on monoamine containing azo dibasic alcohol para-position group R. The structural general formula of the azo dibasic alcohol is disclosed in the specification, wherein the azo dibasic alcohol para-position group R is selected from benzene ring and derivative groups thereof, or naphthalene ring and derivative groups thereof. The azo group is introduced into the main raw material micromolecular dibasic alcohol used in the synthesis process of polyester, polycarbonate, polyether, polyester ether, polyurethane or other polymers in a chemical bonding mode, so that the obtained micromolecular dibasic alcohol molecules contain azo chromophores and also contain two structurally symmetrical hydroxy groups with the same reaction activity, and can partially or wholly substitute micromolecular dibasic alcohol without azo characteristic used in the synthesis, thereby solving the problems of poor migration resistance and nonuniform distribution of azo chromophores in the azo blend material prepared by a micromolecular azo compound blending process.

Description

technical field [0001] The invention belongs to the technical field of azodiols, in particular to azodiols with symmetrical structures for synthesizing azo-type polymers such as polyesters, polycarbonates, polyethers, polyether esters or polyurethanes with azo functional groups and its preparation method. Background technique [0002] Diol is often used as the main raw material to participate in the polymerization reaction to form polymers such as polyester, polycarbonate, polyether, polyether ester or polyurethane. Changing the type and content of diol can change the properties of the polymer. If the diol molecular structure contains certain functional groups, it can impart functional properties to the polymer. With the demand for polymer materials with new functional properties, endowing polymers with functionality can greatly increase the application range of polymers. [0003] "Chemical Reviews" (Chemical Reviews, 2000, Volume 100, 1817-1845) reported the linear and no...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C07C245/10C08G18/32
Inventor 张兴元李军配李发萍
Owner UNIV OF SCI & TECH OF CHINA
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