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D-pi-A-type aminoazobenzene dye and preparation method therefor

A technology of aminoazobenzene and azobenzene, which is applied in the direction of azo dyes, monoazo dyes, organic dyes, etc., and can solve the problem of less blue light azo dyes

Active Publication Date: 2015-10-28
LINGNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research on azo dyes for blue light storage mainly starts from the perspective of molecular design, that is, by changing the structures of A and B and introducing different substituents on A and B to adjust the solubility and light and thermal properties of azo dyes. There are fewer reported blue light azo dyes

Method used

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  • D-pi-A-type aminoazobenzene dye and preparation method therefor
  • D-pi-A-type aminoazobenzene dye and preparation method therefor
  • D-pi-A-type aminoazobenzene dye and preparation method therefor

Examples

Experimental program
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Effect test

Embodiment 1

[0042] The present embodiment is the preparation method of 3?-bromo-4-aminoazobenzene, comprising the following steps:

[0043] (1) Preparation of diazonium salt: Add 3.4408 g of 3-bromoaniline and 8 mL of 20% hydrochloric acid into a 100 mL beaker, slowly add 1.5201 g of sodium nitrite aqueous solution dropwise at 0-5 °C, add urea after 2 h to eliminate excess nitrite Nitric acid and solid sodium acetate were used to adjust the pH value to 5, and the obtained clarified solution was placed in ice water for later use.

[0044] (2) Preparation of sodium anilinomethanesulfonate: add 10 mL of water and 2.3505 g of sodium bisulfite to a 50 mL round bottom flask, add 0.7251 g of paraformaldehyde after dissolving the sodium bisulfite, react at 60°C for 35 min, then drop Add 1.8611 g of aniline that had been distilled, and stop heating after reacting for 2 h to obtain a mixed solution of sodium anilino methanesulfonate.

[0045] (3) Preparation of azobenzene compound: After...

Embodiment 2

[0048] The present embodiment is the preparation method of 3?-bromo-3-methyl-4-aminoazobenzene, comprising the following steps:

[0049] (1) Preparation of diazonium salt: Add 3.4414 g of 3-bromoaniline and 8 mL of 20% hydrochloric acid into a 100 mL beaker, slowly add 1.5216 g of sodium nitrite aqueous solution dropwise at 0-5 °C, add urea after 2 h to eliminate excess nitrite Nitric acid and solid sodium acetate were used to adjust the pH value to 5, and the obtained clarified solution was placed in ice water for later use.

[0050] (2) Preparation of sodium o-toluanilino methanesulfonate: add 10 mL of water and 2.3517 g of sodium bisulfite to a 50 mL round bottom flask, add 0.7264 g of paraformaldehyde after dissolving sodium bisulfite, and react at 60°C for 35 After 2 min, 2.1406 g of o-methylaniline was added dropwise, and the heating was stopped after 2 h of reaction to obtain a mixed solution of sodium o-toluinomethanesulfonate.

[0051] (3) Preparation of azobenzene c...

Embodiment 3

[0054] The present embodiment is the preparation method of 3?-bromo-3-methoxy-4-aminoazobenzene, comprising the following steps:

[0055] (1) Preparation of diazonium salt: Add 3.4451 g of 3-bromoaniline and 8 mL of 20% hydrochloric acid into a 100 mL beaker, slowly add 1.5211 g of sodium nitrite aqueous solution dropwise at 0-5 °C, add urea after 2 h to eliminate excess nitrite Nitric acid and solid sodium acetate were used to adjust the pH value to 5, and the obtained clarified solution was placed in ice water for later use.

[0056] (2) Preparation of sodium o-methoxyanilino methanesulfonate: add 10 mL water and 2.3528 g sodium bisulfite to a 50 mL round bottom flask, add 0.7242 g paraformaldehyde after dissolving sodium bisulfite, and react at 60 °C After 35 min, 2.4608 g of o-methoxyaniline was added dropwise, and the heating was stopped after 2 h of reaction to obtain a mixed solution of sodium o-methoxyanilino methanesulfonate.

[0057] (3) Preparation of azobenzene co...

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Abstract

The invention relates to the technical field of compound preparation and particularly discloses a D-pi-A-type aminoazobenzene dye and a preparation method therefor. A chemical structural formula of the dye is defined in the specification, wherein R1 is hydrogen, methyl or methoxy; and R2 is hydrogen or bromine substituent. The dye has maximum absorption wavelength being about 405 nm, is remarkable in photochromic property, is matched with a 405-nm blue laser, and has high potential for use as a blue-ray disc storage medium.

Description

technical field [0001] The invention relates to the technical field of compound preparation, more specifically, to a D-π-A aminoazobenzene dye and a preparation method thereof. Background technique [0002] Data storage discs are currently one of the most convenient data storage media. With the increase in the amount of information people acquire and process, the demand for high-density Blu-ray discs is becoming more and more urgent. Blu-ray discs use blue laser light with a wavelength of 405 nm to read and write data, and their single-sided capacity is 20 to 50 GB, while that of DVD is 4.7 GB. Blu-ray disc storage media can be divided into inorganic optical storage media and organic optical storage media according to their attributes. Organic optical storage media has the advantages of high storage density, good solubility, low production cost, low environmental pollution, strong antimagnetic ability, and easy wavelength adjustment. , has become a research hotspot of blue-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B29/085G02F1/361G11B7/2467
Inventor 宋秀美冯宗财
Owner LINGNAN NORMAL UNIV
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