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Heterocyclic azo metal chelate compound, their preparation and use

A metal chelate, heterocyclic azo technology, which is applied in the recording/reproducing, instrument, recording information storage and other directions by optical methods, can solve the problems of difficult coupling reaction control, reduce the purity of azo compounds, etc., and achieve good optical performance. Effects of recording properties

Inactive Publication Date: 2004-03-31
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the diazotization reaction of thiazole, imidazole, pyrazole, pyridine or pyrimidine rings containing amino groups needs to be carried out in a relatively strong acidic environment due to the low basicity of amino groups, such as diazonium in nitrosyl sulfuric acid system In the subsequent coupling reaction, a strongly acidic nitrosylsulfuric acid system needs to be added dropwise to the coupling component containing water. On the one hand, it is difficult to control the coupling reaction at low temperature due to the strong exotherm. On the other hand, On the one hand, it causes the decomposition of diazonium salts and reduces the purity of azo compounds

Method used

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  • Heterocyclic azo metal chelate compound, their preparation and use
  • Heterocyclic azo metal chelate compound, their preparation and use
  • Heterocyclic azo metal chelate compound, their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 150mg (1.5mmol) of 2-aminothiazole was dissolved in 4ml of 85% phosphoric acid, cooled to 0-5°C with an ice-salt bath, and 109mg of solid sodium nitrite was added at this temperature, kept for 2 hours, and then a small amount of urea was added to Destroy excess nitrous acid.

[0027] Dissolve 477mg of the coupling component 3-(p-toluenesulfonamido)-N,N-diethylaniline (1.5mmol) in a mixture of 3mL water and 3mL acetic acid, and add 2g sodium acetate to form a buffer. The solution was cooled to 0-5° C. with an ice-salt bath, and the above diazonium salt solution was slowly added dropwise and kept for 2 hours. After filtering and drying, the crude dye was 365mg, and the yield was 85.1%. The dye was purified by column chromatography on neutral alumina (eluent was dichloromethane). Azo dye MS(C 20 h 23 N 5 S 2 o 2 ):M + =429. Elemental analysis (C 20 h 23 N 5 S 2 o 2 ): Calculated: C, 55.92; H, 5.40; N, 16.30; S, 14.93%; Found: C, 55.49; H, 5.51; N, 16.40; S, 1...

Embodiment 2

[0033]1.3g (5mmol) of 2-amino-5-bromothiazole hydrogen bromide was dissolved in 10ml of 85% phosphoric acid, cooled to 0-5°C with an ice-salt bath, and 360mg of solid sodium nitrite was added at this temperature, and kept for 2 hours, and then add a small amount of urea to destroy excess nitrous acid.

[0034] Dissolve 825 mg of coupling component 3-diethylaminophenol (5 mmol) in 15 ml of 95% ethanol, and cool the reaction system to 0-5° C. with an ice-salt bath. The above diazonium salt solution was slowly added dropwise, and the reaction was stirred at this temperature for 3 hours. Then 20 ml of water was added, and the reaction was stirred for 3 hours. The reaction mixture was left overnight, at which time the temperature of the system was allowed to rise to room temperature. Filter, wash with water, and dry to obtain 1.53 g of crude dye, with a yield of 86.2%. The dye was separated and purified by neutral alumina column chromatography (the eluent was chloroform). Dye M...

Embodiment 3

[0040] 200mg (2.0mmol) of 2-aminothiazole was dissolved in 4ml of 85% phosphoric acid, cooled to 0-5°C with an ice-salt bath, and 145mg of solid sodium nitrite was added at this temperature, kept for 2 hours, and then a small amount of urea was added to Destroy excess nitrous acid.

[0041] Dissolve 518mg of coupling component 3-(N,N-diethyl)amino-4-methoxybenzenesulfonic acid (2.0mmol) in 4mL of water and 4mL of acetic acid mixture, add 3g of sodium acetate to make a buffer . The solution was cooled to 0-5° C. with an ice-salt bath, and the above diazonium salt solution was slowly added dropwise and kept for 2 hours. After filtering and drying, the crude dye was 575mg, and the yield was 77.7%. The dye was purified by column chromatography on neutral alumina (eluent was dichloromethane). Its structural formula is

[0042]

[0043] 120mg (0.32mmol) of azo dye was dissolved in 10ml of ethanol solvent, and nickel acetate (0.64mmol) dissolved in 2ml of water was added to th...

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Abstract

A heterocyclic sulphonazo metal chelate compound and its preparation method. In a phosphoric acid system, getting a diazonium salt of a nitrogen heterocyclic aromatic amine by a mild diazotization method, the diazonium salt coupling with different components, and getting a series of heterocyclic sulphonazo compounds; the heterocyclic sulphonazo compound chelating with different bivalent metal to get a series of heterocyclic sulphonazo metal chelate compounds. The heterocyclic sulphonazo metal chelate compound could produce an excellent film by spin coating, and be used for the optical storagemedium for DVD-R. The compound has a low thermal decomposition temperature ( no more than 350degree C), which is advantageous for improving sensitivity of DVD-R dyes.

Description

technical field [0001] The invention relates to a heterocyclic azo metal chelate. [0002] The present invention also relates to a preparation method of the above-mentioned heterocyclic azo metal chelate. [0003] The present invention also relates to the application of the heterocyclic azo metal chelate in optical storage media. Background technique [0004] Optical disc storage technology is an information storage technology developed in the 1970s. After more than 30 years of development, a large-capacity high-density digital versatile disc (Digital Versatile Disc, DVD) has appeared. With the DVD technology With the wide application and popularization of products, recordable DVD discs (DVD-R) are bound to become the leading products of the new generation of optical recording media. [0005] Similar to the recordable disc (CD-R), the core layer of the DVD-R disc is a layer of photofunctional dyes sensitive to 635nm laser, because the writing process of the optical recordi...

Claims

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Application Information

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IPC IPC(8): C07D231/38C07D277/50G11B7/2467
Inventor 王双青许慧君杨国强
Owner INST OF CHEM CHINESE ACAD OF SCI
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