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Application of a kind of polymerizable azo dye compound in preparation of artificial lens

A technology for azo dyes and intraocular lenses, applied in azo dyes, monoazo dyes, intraocular crystals, etc., can solve the problems of high protection requirements, complex structure, and high toxicity of reaction raw materials.

Active Publication Date: 2016-04-06
SHANGHAI ANOKY GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem solved by the present invention is to provide a polymerizable azo dye compound and Its preparation method and use

Method used

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  • Application of a kind of polymerizable azo dye compound in preparation of artificial lens
  • Application of a kind of polymerizable azo dye compound in preparation of artificial lens
  • Application of a kind of polymerizable azo dye compound in preparation of artificial lens

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～8

[0051] Compound 4-1 (R 1 for nitro, R 2 is bromine, R 3 is methyl, R 4 is ethyl, R 5 for the preparation of ethylene)

[0052] Accurately weigh 10g of 98% sulfuric acid and 13.34g of 40% nitrosylsulfuric acid into a 100ml dry three-neck flask, stir evenly, cool down in an ice-water bath to below 15°C, control the temperature of the system not higher than 15°C, and slowly add about 10.48g of 2,4- Add dinitro-6-bromoaniline for about 1-1.5 hours, then slowly raise the temperature to 20-23°C, and keep warm at this temperature for 4 hours. Then add 7.53g of N-ethyl-N-hydroxyethyl-m-toluidine dropwise within 1h for coupling reaction. During the reaction, add ice to control the reaction temperature at 0-5°C, and keep it at 0-5°C for 2h to complete the reaction The coupling reaction was naturally stirred to room temperature, filtered, washed with water, and dried to obtain compound 4-1 (R 1 for nitro, R 2 is bromine, R 3 is methyl, R 4 is ethyl, R 5 ethylene) disperse dye f...

Embodiment 9～16

[0057] Compound 1-1 (R 1 for nitro, R 2 is bromine, R 3 is methyl, R 4 is ethyl, R 5 is ethylene, R 6 for the preparation of methyl)

[0058] Accurately weigh 13.57g of compound 4-1 dry product into a 100ml three-neck flask, then add about 30ml of anhydrous acetone, stir well at room temperature, then slowly raise the temperature to 30-35°C, add 3ml of triethylamine, methacrylic acid in batches Anhydride 3ml, keep warm at this temperature, monitor the reaction by TLC or HPLC, until the reaction of compound 4-1 is complete. After the reaction, distill off most of the acetone, then add 30ml of anhydrous methanol, stir evenly and cool down to room temperature, filter, wash with a small amount of methanol, and then wash with water until the filtrate is basically colorless. The compound 1-1 filter cake was obtained. Dry at 30°C, the yield is 75.72%, the HPLC purity is 94.3%, and the result of compound 1-1 determined by LC-MS is [M+H] + 521.4, [M+Na] + 543.3.

[0059] Comp...

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Abstract

The invention discloses an application of a polymerizable azo dye compound in preparing artificial lens. The polymerizable azo dye compound is shown as formula I. A preparation method of the polymerizable azo dye compound comprises the following step of subjecting a compound 4 and a compound 5 to an esterification reaction in a non-alcohol organic solvent and under the effect of an organic alkali. The invention also discloses an application of the polymerizable azo dye compound 1 in preparing the artificial lens. The azo dye compound provided by the invention has a simple structure; and the preparation method is mild in reaction conditions and easily available in raw materials. Due to the polymerizable reaction characteristic, the polymer has good durable effect. The formula I is shown in the description.

Description

technical field [0001] The invention relates to the field of azo dyes, in particular to the application of a polymerizable azo dye compound suitable for medical use in the preparation of artificial crystals. Background technique [0002] Eyes are the windows to the soul, but with bad eye habits and the influence of environmental factors, there are various health problems in the eyes. Therefore, people have to choose to improve or adjust by means of ophthalmic medical equipment such as glasses, contact lenses, intraocular lenses, artificial corneas, and goggles. But along with the raising of living standard, people just not only require to solve eye problem, but also require attractive in appearance, fashion. [0003] In order to meet people's needs, U.S. Patents US5662707, US5470932, US5528322, US5543502 and Japanese Patent JP8503997 have introduced the structures and synthesis methods of various yellow azo dyes, which are then used to copolymerize with acrylic acid monomer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B69/10C09B29/08C08F220/18C08F220/36A61F2/16G02B1/04
Inventor 韩伟鹏赵敏周洁
Owner SHANGHAI ANOKY GRP