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A new type of water-soluble reactive ultraviolet absorber and preparation method thereof

A UV absorber and water-soluble technology, applied in chemical instruments and methods, other chemical processes, organic chemistry, etc., can solve problems such as poor reactivity and no active groups, and achieve simple methods, good water solubility, and wide application prospects Effect

Active Publication Date: 2019-05-10
伟格仕纺织助剂(江门)有限公司
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  • 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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  • A new type of water-soluble reactive ultraviolet absorber and preparation method thereof
  • A new type of water-soluble reactive ultraviolet absorber and preparation method thereof
  • A new type of water-soluble reactive ultraviolet absorber 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-oxy)-1,2,5,6-bisisopropylidene-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, and then slowly add an acetone-water mixed solution composed of diacetone glucose and NaOH dropwise to the solution. The mixed solution consisted of 2.60 g (10 mmol) of diacetone glucose dissolved in 20 mL of acetone, and a solution of water (10 mL) dissolved with 0.68 g (17 mmol) of NaOH was 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 (the eluent was 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-bisisopropylidene-α-D-glucose (DTDT). Yield: 73%.

[0039] The effects of alkali dosage, reaction t...

Embodiment 2

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

[0048] Dissolve 2.04g (5mmol) DTDT in 30mL acetone, mix 0.96g (4.5mmol) UV-0-dissolved acetone (20mL) and dissolve 0.20g (5mmol) NaOH aqueous solution (10mL), then slowly add dropwise into the DTDT solution. The whole system was reacted at 30°C for 2h. The solvent was removed by rotary evaporation, the remaining yellow solid was repeatedly washed with ethanol, and purified by column chromatography (the eluent was 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-bisisopropylidene-α-D-glucose (UV-DT). Yield: 74%.

[0049] The substitution of the second chlorine of cyanuric chloride is usually carried out at about room temperature, and the reaction with the hydroxyl group requires the addition of alkali as a catalyst. Therefore, the reaction tem...

Embodiment 3

[0054] Example 3: 3-(2-(2-Hydroxyphenylbenzophenone-4-oxy)-4-chloro-1,3,5-triazine-6-oxy)-1,2-isopropyl Synthesis and Properties of Fork-α-D-glucose (UV-DTM)

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

[0056] Propylene ketone protecting group can be deprotected under acidic conditions, but other ether bonds in the structure can also be disconnected when heated under acidic conditions, so adopt the method of TLC detection at room temperature, investigate different acids (acetic acid, hydrochloric acid, The effect of trifluoroacetic acid) catalysis on the hy...

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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 new type of water-soluble reactive ultraviolet absorber and a preparation method thereof. The ultraviolet absorber has excellent hydrophilicity and ultraviolet absorption properties and is biodegradable. The durable anti-ultraviolet finishing applied to cotton textiles belongs to the technical field of light chemical engineering; the utility model is applied to cosmetics and belongs to the technical field of daily chemical industry. 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, the ozone layer has been destroyed, and more ultraviolet rays can penetrate the atmosphere and irradiate the ground, which seriously threatens human health. Cotton fabrics have excellent hygroscopicity, air permeability, comfort and antistatic properties, and are ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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