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Novel water-soluble reaction type ultraviolet absorbent and preparation method thereof

A UV absorber, water-soluble technology, applied in chemical instruments and methods, other chemical processes, sugar derivatives, etc., can solve the problems of no active group, poor reactivity, etc., to achieve simple method, good water solubility, high yield high effect

Active Publication Date: 2017-01-11
伟格仕纺织助剂(江门)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few studies on this type of UV absorber, and carboxymethyl chitosan-based water-soluble UV absorbers and polymers produced by polymerization of polymerizable UV absorber monomers and carbohydrate monomers have been reported. UV absorbers, such UV absorbers have good water solubility and biological safety, but have no active groups and poor reactivity

Method used

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  • Novel water-soluble reaction type ultraviolet absorbent and preparation method thereof
  • Novel water-soluble reaction type ultraviolet absorbent and preparation method thereof
  • Novel water-soluble reaction type ultraviolet absorbent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: 3-(4,6-dichloro-1,3,5-triazine-2-oxyl)-1,2,5,6-diisopropylidene-α-D-glucose (DTDT) Synthesis

[0038]Dissolve 1.46g (8mmol) of cyanuric chloride (TCT) in 20mL of acetone, stir and swell at 0°C for 10min, then slowly add diacetone-glucose and NaOH to the solution dropwise in an acetone-water mixed solution. The mixed solution is composed of 2.60 g (10 mmol) of diacetone glucose dissolved in 20 mL of acetone, and the water (10 mL) solution in which 0.68 g (17 mmol) of NaOH is dissolved is added dropwise with stirring at zero temperature. The reaction was followed by TLC. After the reaction was completed, the solvent was removed by rotary evaporation to obtain a light yellow oily product, which was purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:6) to obtain a white solid 3-(4,6-dichloro-1,3 ,5-triazine-2-oxy)-1,2,5,6-diisopropylidene-α-D-glucose (DTDT). Yield: 73%.

[0039] Using the method of parallel experiment, the effects of t...

Embodiment 2

[0047] Example 2: 3-(2-(2-Hydroxyphenylbenzophenone-4-oxyl)-4-chloro-1,3,5-triazine-6-oxyl)-1,2,5, Synthesis of 6-diisopropylidene-α-D-glucose (UV-DT)

[0048] Dissolve 2.04g (5mmol) DTDT in 30mL of acetone, mix acetone (20mL) with 0.96g (4.5mmol) of UV-0 dissolved in it and an aqueous solution (10mL) with 0.20g (5mmol) of NaOH, and slowly add it dropwise into the DTDT solution. The whole system was reacted at 30°C for 2h. The solvent was removed by rotary evaporation, and the remaining yellow solid was washed repeatedly with ethanol, and purified by column chromatography (eluent: acetone:n-hexane=1:1) to obtain a white powder 3-(2-(2-hydroxyphenylbenzophenone-4 -oxy)-4-chloro-1,3,5-triazine-6-oxy)-1,2,5,6-diisopropylidene-α-D-glucose (UV-DT). Yield: 74%.

[0049] The substitution of the second chlorine of cyanuric chloride is often reacted at room temperature, and the reaction with the hydroxyl group needs to add alkali as a catalyst. Therefore, the ratio of the reaction ...

Embodiment 3

[0054] Example 3: 3-(2-(2-hydroxyphenylbenzophenone-4-oxyl)-4-chloro-1,3,5-triazine-6-oxyl)-1,2-isopropyl Synthesis and properties of fork-α-D-glucose (UV-DTM)

[0055] Dissolve 0.59g (1mmol) of UV-DT in 10mL of tetrahydrofuran, add 0.50mL of hydrochloric acid (36%) solution, stir at room temperature for 5 hours, and remove the solvent by rotary evaporation. The crude product is subjected to column chromatography (eluent is ethyl acetate : Petroleum ether = 1: 1) to obtain the hydrolyzed product 3-(2-(2-hydroxyphenylbenzophenone-4-oxyl group)-4-chloro-1,3,5-triazine-6-oxyl group )-1,2-Isopropylidene-α-D-glucose (UV-DTM). Yield: 74%.

[0056] The protection group of propylidene ketone will be deprotected under acidic conditions, but other ether bonds in the structure will also be broken when heated under acidic conditions. Trifluoroacetic acid) catalyzes the impact on the hydrolysis reaction, wherein almost no product is generated when acetic acid is used, and the point of U...

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Abstract

The invention discloses a water-soluble ultraviolet absorbent with reactive groups and a synthesis method of the absorbent, and belongs to the technical field of functional agent and chemical engineering. With ultrasonic absorbent such as cyanuric chloride and UV-0 and carbohydrate such as diacetone-D-glucose as the raw materials, the water-soluble ultraviolet absorbent with the reactive groups is synthesized through three-step reaction. The three-step synthesis process includes the steps of firstly, n cyanuric chloride, n diacetone-D-glucose and n NaOH react for 8 h in mixed liquid of acetone and water at 0 DEG C according to the ratio of n cyanuric chloride to n diacetone-D-glucose to n NaOH being 0.9:1:1.7; secondly, n intermediate, n UV-0 and n NaOH react for 2 h in mixed liquid of acetone and water at 30 DEG C according to the ratio of n intermediate to n UV-0 to n NaOH being 1:1.1:1; thirdly, the product (1 mmol) obtained in the second step and 0.5 mL of hydrochloric acid react for 5 h at 25 DEG C in THF. The synthesis method is easy and convenient to operate and easy to implement. The ultrasonic absorbent is excellent in ultrasonic absorption performance and good in water solubility and can be applied to ultrasonic resistant modification of cotton, wool and other textile materials. Organic solvent can be prevented from being used in application, and the application prospects are wide.

Description

technical field [0001] The invention relates to a novel water-soluble reactive ultraviolet absorber and a preparation method thereof. The ultraviolet absorber has excellent hydrophilicity and ultraviolet absorption performance and is biodegradable. The durable anti-ultraviolet finish applied to cotton textiles belongs to the technical field of light chemical engineering; the method is applied to cosmetics and belongs to the technical field of daily chemical engineering. The preparation method belongs to the technical field of chemical industry. Background technique [0002] Due to industrial development and scientific and technological progress, environmental pollution has become more and more serious, and the ozone layer has been destroyed. More ultraviolet rays can penetrate the atmosphere and shine on the ground, seriously threatening human health. Cotton fabrics have excellent hygroscopicity, air permeability, comfort and antistatic properties, and are the first choice ...

Claims

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Application Information

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IPC IPC(8): C07H17/02C09K3/00
CPCC07H17/02C09K3/00
Inventor 黄丹丁阳杨秀刘欢任学宏
Owner 伟格仕纺织助剂(江门)有限公司
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