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Preparation method of bromofluorescein type cosmetic dyestuff

A technology of fluorescein and cosmetics, applied in chemical instruments and methods, organic dyes, azo dyes, etc., can solve the problems of non-compliance with green chemistry and low utilization rate of bromine atoms, and achieve low price, easy acquisition, and high utilization rate Effect

Inactive Publication Date: 2018-04-20
上海染料研究所有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] All the above-mentioned documents have a common defect. From the perspective of the feeding ratio, the utilization rate of bromine atoms is lower than 50% (also there is no expression for the recovery of the remaining bromine elements in the later stage), which is not in line with the design at the source. The concept of green chemistry, and bromine is a consumable resource, with the market price of bromine rising all the way in the past ten years, this shortcoming has become more prominent

Method used

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  • Preparation method of bromofluorescein type cosmetic dyestuff
  • Preparation method of bromofluorescein type cosmetic dyestuff

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 (preparation of 4', 5'-dibromofluorescein)

[0042] In a 250mL four-neck flask, add 30.5g of sodium hypochlorite solution (10%, 43mmol), place an ice-water bath outside, start stirring, add about 18g of water, 12.2g of 32% liquid caustic soda, and slowly drop Add 7.0 g of bromine (99%, 43 mmol), and control the reaction temperature below 15°C. Measure the content (available bromine is about 20%) and set it aside.

[0043] Add 100 g of 95% ethanol into a 500 mL four-neck flask, start stirring, add 14.3 g of fluorescein (97.5%, 42 mmol), heat up to 40-50° C., and dissolve. Add 13.6g of phosphoric acid (85%, 118mmol), cool down to 20-25°C, slowly add 67g of the above-mentioned sodium hypobromite solution (84mmol) dropwise within 1.5 hours, during which the reaction temperature is controlled at 20-25°C. Keep warm and stir for another 1 hour.

[0044] The temperature of the reaction solution was raised to 60° C., and about 80 g of ethanol was evaporated under va...

Embodiment 2

[0046] Example 2 (2', 4', 5', 7'-tetrabromofluorescein preparation)

[0047]Add in a 250mL four-neck flask, add 61.0g of sodium hypochlorite solution (10%, 86mmol), place an external ice-water bath, start stirring, add about 36g of water, 24.3g of 32% liquid caustic soda, after the temperature of the material reaches 0-5°C, slowly 13.9 g bromine (99%, 86 mmol) was added dropwise, and the reaction temperature was controlled below 15°C. Measure the content (available bromine is about 20%) and set it aside.

[0048] Add 250g of acetic acid into a 500mL four-neck flask, start stirring, add 13.6g of fluorescein (97.5%, 40mmol), heat up to 50-60°C, and stir rapidly (300-400rpm) for 30min. The temperature was lowered to 25-30°C, and 134.0 g of the above-mentioned sodium hypobromite solution (20%, 168 mmol) was slowly added dropwise within 3-4 hours, during which the reaction temperature was controlled at 25-30°C. Insulated and stirred for another 2 hours, a sample was taken to dete...

Embodiment 3

[0050] Example 3 (2', 4', 5', 7'-tetrabromofluorescein preparation)

[0051] Replace "13.6g fluorescein (97.5%, 40mmol)" with "12.9g fluorescein (97.5%, 38mmol)", and the rest are the same as in Example 2 to obtain 24.0g light pink target product (HPLC purity 97.6%, content 97.5%, 36mmol), yield 95%.

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Abstract

The invention discloses a preparation method of a bromofluorescein type cosmetic dyestuff. Specifically, the dyestuff disclosed by the invention is prepared from 4',5'-dibromofluorescein (C.I.45370: 1) , 2',4',5',7'-tetrabromofluorescein (C.I.45380: 2), 2',4',5',7'-tetrabromo-4,7-dichlorofluorescein (C.I.45405: 1) and 2',4',5',7'-tetrabromo-4,5,6,7-tetrabromofluorescein (C.I.45410: 1). The preparation method comprises the following steps: (I) putting bromine into liquid alkali and a water solution of sodium hypochlorite at low temperature to prepare a sodium hypobromite solution; (II) dissolving fluorescein or corresponding chlorofluorescein or partially dissolving the fluorescein or the corresponding chlorofluorescein into an acid-containing solvent; dropwise adding the sodium hypobromitesolution at room temperature and carrying out bromination; (III) after reaching a bromination finishing point, adding a proper amount of a reducing agent to eliminate hypobromous acid if residual hypobromous acid exists; after removing a solvent, washing an obtained crude product with diluted hydrochloric acid and desalting; drying to obtain a target product.

Description

technical field [0001] The invention relates to a preparation method of cosmetic dyes, in particular to a preparation method of bromofluorescein cosmetic dyes. Background technique [0002] According to the 2015 edition of "Safety and Technical Specifications for Cosmetics", the varieties of bromofluorescein cosmetic dyes include 4',5'-dibromofluorescein, 2',4',5',7'-tetrabromofluorescein, 2',4',5',7'-tetrabromo-4,7-dichlorofluorescein, 2',4',5',7'-tetrabromo-4,5,6,7-tetrachlorofluorescein white. These four dyes and their respective disodium salt dyes or lakes are allowed for the coloring of cosmetics. [0003] There is a common unit reaction in the synthesis process of the above four dyes, that is bromination, and the bromination methods are basically the same. According to the literature, the bromination method can be divided into two categories, one is the electrolytic bromination method, and the other is the chemical reagent bromination method. [0004] The represent...

Claims

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Application Information

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IPC IPC(8): C09B57/00
CPCC09B57/00
Inventor 丁秋龙乐一鸣刘晓梅汪海麟
Owner 上海染料研究所有限公司
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