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Azobenzol dye compound and preparation thereof

A dye compound and azobenzene technology, applied in the field of azobenzene dye compounds and their preparation, can solve the problem that the photochromic process of the azo chromophore is not easy to control, and achieves improved stability, controllability and broad application. Foreground effect

Inactive Publication Date: 2009-05-27
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For this reason, we have prepared an azobenzene dye compound in which the ortho positions of the azo group are hydroxyl and alkyl respectively, and the intramolecular force between the hydroxyl and the alkyl group makes the cis structure more stable, thereby To a certain extent, it will improve the disadvantages that the photochromic process of azo chromophores is not easy to control

Method used

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  • Azobenzol dye compound and preparation thereof
  • Azobenzol dye compound and preparation thereof
  • Azobenzol dye compound and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of 2-methyl-2'-hydroxyl-3'-tert-butyl-5'-methylazobenzene

[0031] 1. Preparation of diazonium salt

[0032] In a 250mL three-necked bottle equipped with a stirrer and a thermometer, add 10.6g of o-methylaniline, 25mL of 36% hydrochloric acid, 15mL of 36% acetic acid and 75mL of water, place the three-necked bottle in an ice-salt bath, and add 25mL of 30% Keep the reaction temperature below 5°C, react for 1.5 hours, remove excess sodium nitrite with urea, and obtain a purple-red diazonium salt solution.

[0033] 2. Coupling reaction

[0034] Add 1.69g of o-tert-butyl-p-cresol and 25mL of water into a 500mL three-necked flask, and simultaneously add diazonium salt solution and 1mol / L Na 2 CO 3 Aqueous solution 150mL, control pH ≈ 7.5, react for 5h, then raise the temperature to 70°C, react for 2h, acidify with dilute hydrochloric acid to pH = 2, wash with water, filter, and vacuum dry at 80°C to obtain a crude product. Recrystallization with a ...

Embodiment 2

[0043] Example 2: Preparation of 2-nonyl-2'-hydroxyl-3'-tert-butyl-5'-methylazobenzene

[0044] 1. Preparation of diazonium salt

[0045]In a 250mL three-necked flask equipped with a stirrer and a thermometer, add 21.9g of 2-nonylaniline, 15mL of 36% sulfuric acid, 15mL of 36% acetic acid and 75mL of water, place the three-necked flask in an ice-salt bath, and add 28mL of 30 % sodium nitrite aqueous solution, keep the reaction temperature not exceeding 5°C, react for 1.5h, and remove the excess sodium nitrite with urea to obtain a purple-red diazonium salt solution.

[0046] 2. Coupling reaction

[0047] Add 1.94g of o-tert-butyl-p-cresol and 25mL of water into a 500mL three-necked flask, and simultaneously add diazonium salt solution and 2mol / L Na 2 CO 3 Aqueous solution 150mL, control pH ≈ 7.5, react for 5h, then raise the temperature to 70°C, react for 2h, acidify with dilute hydrochloric acid to pH = 2, wash with water, filter, and vacuum dry at 80°C to obtain a crude p...

Embodiment 3

[0050] Example 3: Preparation of 2-methyl-2'-hydroxyl-3'-methyl-5'-methylazobenzene

[0051] 1. Preparation of diazonium salt

[0052] In a 250mL three-necked bottle equipped with a stirrer and a thermometer, add 10.6g of o-methylaniline, 30mL of 36% hydrochloric acid, 15mL of 36% acetic acid and 75mL of water, place the three-necked bottle in an ice-salt bath, and add 23mL of 30% Keep the reaction temperature below 5°C, react for 1.5 hours, remove excess sodium nitrite with urea, and obtain a purple-red diazonium salt solution.

[0053] 2. Coupling reaction

[0054] Add 1.28g of o-methyl-p-cresol and 25mL of water into a 500mL three-necked flask, and simultaneously add diazonium salt solution and 2mol / L Na 2 CO 3 Aqueous solution 150mL, control pH ≈ 7.5, react for 7 hours, acidify with dilute hydrochloric acid to pH = 2, wash with water, filter, and vacuum dry at 80°C to obtain a crude product. Recrystallization with a mixed solvent of ethanol and water at a volume ratio ...

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Abstract

The invention provides an azobenzene dyestuff compound and a preparation method thereof, which belong to the field of optical switch and optical storage. The structure of the azobenzene dyestuff compound is shown as a formula (I), wherein n is an integer of between 0 and 8, and m is an integer of between 0 and 3. The azobenzene dyestuff compound has obvious phototropy under ultraviolet irradiation, and can improve the controllability of an azobenzene chromophore in the process of phototropy. The invention also provides the preparation method of the compound. The azobenzene dyestuff compound and the preparation method thereof have excellent development prospect in the field of optical switch and optical storage. In the formula (I), n is the integer of between 0 and 8, and m is the integer of between 0 and 3.

Description

technical field [0001] The invention relates to the preparation and application of an azobenzene dye compound, especially having broad application prospects in the fields of optical switches and optical storage. Background technique [0002] As a dye compound, azobenzene derivatives will undergo reversible photo-induced cis-trans isomerization changes under the irradiation of ultraviolet light or visible light, that is, photochromic phenomenon. The research of azo dye compounds in the fields of information storage and optical recording materials has been favored by people, and they have been applied in the fields of optical information materials, molecular wires, and molecular switches. Azo dyes are not only the first choice for the upcoming DVD-R (digital versatile disc recordable) disc storage medium with a capacity of 4.7GB, but also may become the third-generation recordable disc HD-DV-R (high density DVD-R) storage medium. In addition, the unique photochromic properti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B29/12C09K9/02
Inventor 何勇赵宇飞聂俊
Owner BEIJING UNIV OF CHEM TECH