Method of preparing alpha, alpha'-di(substituted benzylidene)cyclohexanone ultraviolet radiation absorbent

An ultraviolet and absorber technology, applied in the field of ultraviolet absorbers, can solve the problem that the sunscreen effect is not very high, and achieve the effect of stable chemical properties

Inactive Publication Date: 2009-05-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

They are not very effective at absorbing UV rays

Method used

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  • Method of preparing alpha, alpha'-di(substituted benzylidene)cyclohexanone ultraviolet radiation absorbent
  • Method of preparing alpha, alpha'-di(substituted benzylidene)cyclohexanone ultraviolet radiation absorbent

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add 0.5ml of concentrated sulfuric acid, 7ml of acetic acid and 0.25ml of 30% hydrogen peroxide into a 100ml three-necked bottle (the volume ratio of concentrated sulfuric acid: acetic acid: 30% hydrogen peroxide is 2:28:1), when concentrated sulfuric acid, acetic acid, 30% hydrogen peroxide mixture After cooling to room temperature (20-25°C), slowly add the mixture of cyclohexanone and benzaldehyde, the molar ratio of ketone and aromatic aldehyde in the mixture is 1:2, after stirring at room temperature for about 7 hours, there is a large amount of Precipitation was formed, after adding 40-60ml of water, the solid was filtered out with suction, washed with distilled water, and then rinsed with aqueous methanol (the volume ratio of methanol:water was 1:1). The obtained solid was recrystallized from dichloromethane and ethanol respectively. The corresponding product α,α'-dibenzylidene cyclohexanone was obtained. The solid was weighed after drying, and the yield calculat...

Embodiment 2

[0026] Add 4ml concentrated sulfuric acid, 20ml acetic acid and 2ml hydrogen peroxide (the volume ratio of concentrated sulfuric acid: acetic acid: 30% hydrogen peroxide is 4:20:2) in a 100ml three-necked bottle, control the reaction temperature to 35°C, slowly add cyclohexanone dropwise Mixed solution with m-nitrobenzaldehyde, the molar ratio of ketone and m-nitrobenzaldehyde in the mixed solution is 1:2, after stirring at 35°C for about 20 hours, add 50% sodium hydroxide solution to neutralize the reaction solution to medium After allowing the reaction solution to stand for 3 to 4 hours, a large amount of precipitate formed, and the solid was filtered out with suction and washed with 5 to 10 ml of ethyl acetate. The resulting solid was recrystallized from dichloromethane and ethanol, respectively. The corresponding product α,α'-bis(m-nitrobenzylidene)cyclohexanone is obtained. The solid was weighed after drying, and the yield calculation and structure identification were ca...

Embodiment 3

[0028] Add 2ml of concentrated sulfuric acid, 14ml of acetic acid and 1ml of hydrogen peroxide into a 100ml three-necked bottle (the volume ratio of concentrated sulfuric acid: acetic acid: 30% hydrogen peroxide is 2:14:1), control the reaction temperature to 35°C, and slowly add cyclohexanone dropwise Mixed solution with p-chlorobenzaldehyde, the molar ratio of ketone and aromatic aldehyde in the mixed solution is 1:1.6, after stirring at 45°C for about 10 hours, add 50% sodium hydroxide solution to neutralize the reaction solution to neutral, let the reaction After the solution was left to stand for 3 to 4 hours, a large amount of precipitate formed, and the solid was filtered out with suction and washed with 5 to 10 ml of ethyl acetate. The resulting solid was recrystallized from dichloromethane and ethanol, respectively. The corresponding product α,α'-bis(p-chlorobenzylidene)cyclohexanone is obtained. The solid was weighed after drying, and the yield calculation and structu...

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Abstract

The present invention relates to a method for preparing ultraviolet absorber of alpha, alpha'-di(substituted benzilidene)cyclohexanones type which generated by using cyclohexanone reacting with balminess aldehyde in solution of mixing concentrated sulfuric acid, acetic acid and 30% hydrogen peroxide, in which volume ratio of concentrated sulfuric acid : acetic acid : 30% hydrogen peroxide is 2~4 : 20~28 : 1~2 in above mixed solution, and the molar ratio of cyclohexanone to aromatic aldehyde is 1 : 1.5~3, and the reaction temperature is 10~50 DEG C. The prepared ultraviolet absorber of alpha, alpha'-di(substituted benzilidene)cyclohexanones type has stable chemical property, can intensely absorbing ultraviolet in which its absorption range is 230-400n, and it can be used as wide spectrum ultraviolet absorbent.

Description

technical field [0001] The present invention relates to properties and preparation methods of α, α'-bis(substituted benzylidene) cyclic ketones used as ultraviolet absorbers. More specifically, it refers to the property and preparation method of α,α'-bis(substituted benzylidene)cyclohexanone as an ultraviolet absorber. Background technique [0002] Ultraviolet light refers to the part of the wavelength range of light in the range of 200nm to 400nm. Ultraviolet rays can be divided into short-wave ultraviolet rays (UVC) from 190nm to 280nm, medium-wave ultraviolet rays (UVB) from 280nm to 320nm, and long-wave ultraviolet rays (UVA) from 320nm to 400nm. Long-term exposure to UV radiation can cause sunburn, premature aging of the skin, and damage to the immune cells in the skin. Cause systemic immune function suppression, ultraviolet radiation can also lead to skin cancer in severe cases. Ultraviolet absorbers can effectively absorb ultraviolet rays UVB and UVA, convert light...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/683C07C49/753C07C45/68C07C205/45C08K5/07C09D7/12
Inventor 徐伟亮吴坚
Owner ZHEJIANG UNIV
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