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Sulfo group-containing spirooxazine type photochromic compound as well as preparation method and application thereof

A technology containing sulfonic spirooxazine and photochromism, which is applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of unsatisfactory light fastness and achieve the effect of simple synthesis process

Active Publication Date: 2015-09-09
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, BE1006104, involving spirooxazine photochromic compounds containing sulfonic acid groups and their preparation methods, and many of the compounds involved in the patent have been commercialized due to their excellent application performance, but their light fastness is not very satisfactory.

Method used

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  • Sulfo group-containing spirooxazine type photochromic compound as well as preparation method and application thereof
  • Sulfo group-containing spirooxazine type photochromic compound as well as preparation method and application thereof
  • Sulfo group-containing spirooxazine type photochromic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The preparation of embodiment 1 compound 1

[0052] The reaction formula is as follows:

[0053]

[0054] Dissolve 3.2g (20.2mmol) of 1,3,3-trimethyl-2-methylene indoline in 10ml of 98% concentrated sulfuric acid, and add 6.5g of 30 % oleum, after adding the oleum dropwise, keep warm for 5 hours at 0-5°C. After the reaction, add the reaction liquid dropwise to 200ml of water to dilute, a large amount of solids precipitate out, filter, wash with water, and dry to obtain 4.96g of 5-sulfonic acid-1,3,3-trimethyl-2-methylene Indoline, the yield is 97%, and the melting point is 265°C.

[0055] Under the protection of nitrogen, add 2.5g (14.4mmol) 1-nitroso-2-naphthol, 3.6g (50.5mmol) tetrahydropyrrole to the flask, then add absolute ethanol until completely dissolved, stir under microwave pressure 25 volts, electric current 200 milliampere heating reaction for 20 minutes, stop the reaction, cool, remove excess tetrahydropyrrole by distillation under reduced pressure to...

Embodiment 2

[0059] The preparation of embodiment 2 compound 2

[0060] The reaction formula is as follows:

[0061]

[0062] Dissolve 6.0g (30mmol) of 1-isopropyl-3,3-dimethyl-2-methyleneindoline in 15ml of 98% concentrated sulfuric acid, drop it into the reaction solution at 0-5°C Add 14.4g of 20% fuming sulfuric acid, after the addition of fuming sulfuric acid is completed dropwise, keep the reaction at 0-5°C for 6 hours. After the reaction, add the reaction feed solution dropwise to 150ml of water to dilute, a large amount of solids precipitate out, filter, wash with water, and dry to obtain 8.26g of 5-sulfonic acid-1-isopropyl-3,3-dimethyl- 2-Methyleneindoline, the yield is 98%.

[0063] Under the protection of nitrogen, add 2.5g (14.4mmol) 1-nitroso-2-naphthol, 6.9g (57.6mmol) indoline to the flask, then add absolute ethanol until completely dissolved, stir under microwave pressure 30 volts, electric current 220 milliamperes heating reaction 25 minutes, stop reaction, cooling, ...

Embodiment 3

[0067] The preparation of embodiment 3 compound 3

[0068] The reaction formula is as follows:

[0069]

[0070] Dissolve 4.3g (20mmol) of 1-isobutyl-3,3-dimethyl-2-methylene indoline in 20ml of 98% concentrated sulfuric acid, drop it into the reaction solution at 0-5°C Add 6.9g of 30% fuming sulfuric acid, after the addition of fuming sulfuric acid is completed dropwise, keep warm for 5 hours at 0-5°C. After the reaction, add the reaction feed solution dropwise to 100ml of water for dilution, a large amount of solids precipitate out, filter, wash with water, and dry to obtain 5.7g of 5-sulfonic acid-1-isobutyl-3,3-dimethyl- 2-Methyleneindoline, the yield is 96.6%.

[0071] Under the protection of nitrogen, add 2.5g (14.4mmol) 1-nitroso-2-naphthol, 5.0g (57.6mmol) morpholine to the flask, then add absolute ethanol until completely dissolved, stir under microwave pressure 40 Volt, electric current 240 milliampere heating reaction 15 minutes, stop reaction, cooling, underp...

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PUM

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Abstract

The invention relates to an organic photochromic material, and in particular relates to a sulfo group-containing spirooxazine type photochromic compound as well as a preparation method and application thereof. The compound is shown by a general formula I, wherein R1 is SO3H, SO3Na or SO3K; R2 is C1-C18 alkyl, an aromatic ring or a heterocyclic ring substituted C1-C6 chain alkyl; and R3 is shown in the specification. The compound is applied to photochromic spectacles, light filters, optical instruments, optical devices of observers, glass partition walls, decorative items, display elements or optical information storage materials. The sulfo group-containing spirooxazine type photochromic compound provided by the invention has the advantages that the synthetic process is simple; the obtained compound has relatively good solubility in common solvents such as methylbenzene, acetone and tetrahydrofuran; the related compound contains sulfonic acid groups and can be dispersed in a waterborne adhesive more easily; and a photochromic material prepared from the compound shows excellent sun-proof performance after a light fastness test.

Description

technical field [0001] The invention relates to an organic photochromic material, in particular to a sulfonic acid group-containing spirooxazine photochromic compound and its preparation method and application. Background technique [0002] Spirooxazine is a class of compounds with good photochromic properties developed on the basis of spiropyran in the 1970s. Because it also has high fatigue resistance and photostability, it is used in photochromic eyes, Optical filters, optical devices for optical instruments or observers, glass partitions, decorative items, display elements, and optical information storage materials. [0003] Substituted spirooxazine photochromic compounds are a class of photochromic compounds with excellent photochemical properties. Patent BE1006104 once reported spirooxazine photochromic compounds containing sulfonic acid groups and introduced the preparation and application performance of photochromic materials. The general formula of the compound in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10C09K9/02
CPCC07D498/10C09K9/02C09K2211/1033
Inventor 郭林邢颖王瑛张宇鄂彦鹏马狄贾晓雷
Owner 中国中化股份有限公司