Siloxane dye comprising benzothiazole heterocycle and its synthesis method

A technology for the synthesis of benzothiazoles, which is applied in the direction of azo dyes, organic dyes, monoazo dyes, etc., can solve the problems of few and difficult preparation of azo molecules, and achieve high yield, convenient purification and excellent reaction conditions mild effect

Inactive Publication Date: 2006-11-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the weak basicity of heterocyclic arylamines, it is difficult to prepare azo molecules. At present, there are not many reports on heterocyclic aryl azo chromophore molecules, and there are no reports on siloxane dyes containing benzothiazole heterocycles.

Method used

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  • Siloxane dye comprising benzothiazole heterocycle and its synthesis method
  • Siloxane dye comprising benzothiazole heterocycle and its synthesis method
  • Siloxane dye comprising benzothiazole heterocycle and its synthesis method

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Experimental program
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Effect test

Embodiment 1

[0019] R in Structural Formula 1 is a methyl group. The synthetic route of the siloxane dye containing benzothiazole heterocycle is as follows:

[0020]

[0021] The synthesis method is:

[0022] Slowly add 3.3g (48mmol) of sodium nitrite in batches to 40ml of 98% concentrated sulfuric acid, control the temperature below 20°C, stir to dissolve it completely, then cool to 0-5°C to obtain nitrosyl sulfuric acid. Then add 50ml of glacial acetic acid to 7.8g (40mmol) of 2-amino-6-nitrobenzothiazole, stir to form a paste and cool to below 5°C, and then quickly inward under the condition that the reaction temperature is lower than 20°C Add dropwise nitrosyl sulfuric acid, react for 10 minutes after adding, then add 6.1g (40mmol) N-methyl-N-hydroxyethylaniline and 100ml volume ratio of methanol and water mixed solution of 2 / 1, use hydrogen The sodium oxide solution adjusted the pH value to 5-6 and continued the reaction for 0.5 hour. Suction filtration, the filter cake was wash...

Embodiment 2

[0025] R in Structural Formula 1 is ethyl. The synthetic route of the siloxane dye containing benzothiazole heterocycle is as follows:

[0026]

[0027] The synthesis method is:

[0028] Slowly add 2.8g (40mmol) of sodium nitrite in batches to 40ml of 98% concentrated sulfuric acid, control the temperature below 20°C, stir to dissolve it completely, then cool to 0-5°C to obtain nitrosylsulfuric acid. Add 24ml of glacial acetic acid, 16ml of concentrated phosphoric acid, 8ml of propionic acid and 8ml of formic acid to 7.8g (40mmol) of 2-amino-6-nitrobenzothiazole, stir to form a paste and cool to below 5°C, then ensure the reaction Under the condition that the temperature is lower than 20°C, nitrosyl sulfuric acid is quickly added dropwise inwardly, and reacted for 1 hour after the addition is completed, then add 7.4g (45mmol) N-ethyl-N-hydroxyethylaniline and 120ml volume ratio of 2 / 1 mixed solution of methanol and water, adjust the pH value to 5-6 with ammonia water and...

Embodiment 3

[0040] R in the general structural formula 1 is a benzene ring. The synthetic route of the siloxane dye containing benzothiazole heterocycle is as follows:

[0041]

[0042] The synthesis method is:

[0043] Slowly add 2.8g (40mmol) of sodium nitrite in batches to 40ml of 98% concentrated sulfuric acid, control the temperature below 20°C, stir to dissolve it completely, then cool to 0-5°C to obtain nitrosylsulfuric acid. Then add 30ml of concentrated sulfuric acid to 7.8g of 2-amino-6-nitrobenzothiazole, stir to form a paste and cool to below 5°C, then quickly dropwise add disulfide under the condition that the reaction temperature is lower than 20°C. Nitrosulfuric acid, after adding, reacted for 5 hours, then added 16.0g (80mmol) N-ethyl-N-hydroxyethylaniline and 200ml volume ratio of methanol and water mixed solution of 2 / 1, adjusted with sodium carbonate solution The reaction was continued for 5 hours when the pH value reached 5-6. Suction filtration, the filter cake ...

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Abstract

The invention discloses a siloxane dye with benzo thiazole heterocycle as structure formula 1 (R is methyl, ethyl group or benzene ring), which is characterized by the following: reacting 2-amino-6-nitrobenzothiazolyl and arylamine to produce the chromogen molecule with benzo thiazole heterocycle through diazo coupling reaction; reacting the chromogen molecule with isocyanate propyl triethoxy silane to proceed addition reaction to produce the product. The invention displays simple synthesizing technology, which can be used in the electrooptical modulation, optical switch and non-linear optics domains.

Description

technical field [0001] The invention relates to a class of siloxane dyes containing a benzothiazole heterocycle and a synthesis method thereof. Background technique [0002] With the advent of the information age, the fields of high-speed optical communication, optical information processing and optical storage have achieved rapid development, and the application prospects of nonlinear optical materials in the above fields have also received more and more attention. The original nonlinear optical materials were based on inorganic materials (lithium niobate and other crystals), and then it was found that some organic substances also have nonlinear optical effects (such as benzopyrene, etc.). Since the mid-1980s, the research on the development of polymer nonlinear optical materials and their deviceization has developed rapidly. This is due to the incomparable advantages of organic and polymer nonlinear optical materials compared with inorganic materials, such as: polymers ha...

Claims

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Application Information

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IPC IPC(8): C09B29/045
Inventor 钱国栋崔元靖陈鹭剑王智宇邱建荣樊先平洪樟连王民权
Owner ZHEJIANG UNIV
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