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A kind of benzophenone and Schiff base ultraviolet absorber and preparation method thereof

A technology of benzophenone and Schiff bases, which is applied in the field of benzophenone and Schiff base ultraviolet absorbers and their preparation, and can solve the problems of poor product compatibility and stability, high cost, and difficulty in formulating processes, etc. problem, to achieve the effect of strong market potential, low preparation cost, and easy industrial production

Active Publication Date: 2022-03-29
HUBEI MEIKAI CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] It can be seen from Table 1 that the chemical absorption type UV absorbers sold on the market mainly focus on protecting the UVB band, while there are relatively few products protecting the UVA band; in addition, there are fewer single products that can cover the UVA and UVB bands
[0011] At present, the general practice of commercialization is to reasonably compound and use ultraviolet absorbers that protect UVA and UVB, but the compounding has disadvantages such as poor product compatibility and stability, difficult formulation process, and high cost.

Method used

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  • A kind of benzophenone and Schiff base ultraviolet absorber and preparation method thereof
  • A kind of benzophenone and Schiff base ultraviolet absorber and preparation method thereof
  • A kind of benzophenone and Schiff base ultraviolet absorber and preparation method thereof

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preparation example Construction

[0036] The present invention also provides the preparation method of the benzophenone-Schiff base ultraviolet absorber described in the above scheme, comprising the following steps:

[0037] Condensing 2,4-dihydroxy-5-formyl benzophenone and aromatic amine compounds to obtain a benzophenone and Schiff base ultraviolet absorber with a structure shown in formula I;

[0038] In the present invention, the aromatic amine compounds include aniline, p-chloroaniline, 1-naphthylamine, 2,3-dimethylaniline, p-methoxyaniline, p-hydroxyaniline, o-hydroxyaniline or p-methylaniline .

[0039]In the present invention, the molar ratio of the 2,4-dihydroxy-5-formylbenzophenone to the aromatic amine compound is preferably 1:1~2, more preferably 1:1.5; the condensation reaction The temperature is preferably 50-100°C, more preferably 60-90°C, and the condensation reaction time is preferably 2-6h, more preferably 3-5h; The response is complete.

[0040] In the present invention, the solvent of t...

Embodiment 1

[0046] Add 1.21g (5.0mmol) of 2,4-dihydroxy-5-formylbenzophenone in ethanol (20mL) solution to a 100mL round bottom flask, add dropwise 0.74g (6.0mmol) of p-methoxyaniline Ethanol (10mL) solution, at this time the molar ratio of 2,4-dihydroxy-5-formylbenzophenone to p-methoxyaniline is 1:1.2. Control the reaction temperature to 75°C and react for 4h. After the complete reaction of the raw materials was monitored by TLC, 20 mL of ethanol solvent was distilled off under reduced pressure, filtered by suction, and dried to obtain 1.51 g of a yellow solid, which was the corresponding product (E)-2,4-dihydroxy-5-((4-methoxy phenylimino)methyl)benzophenone. Yield 87.0%, m.p.129-131°C, TLC (PE:EA=5:1, R f =0.24), FT-IR (KBr) (cm -1 ):3416m, 3058m, 2990m, 2834m, 1750m, 1624s, 1560s, 1504s, 1448s, 1030s, 876m, 826s, 780m, 704m. 1 H NMR (CDCl 3 ,400MHz),δ:14.75(s,1H),12.77(s,1H),8.42(s,1H),7.69-7.49(m,6H),7.25-7.19(m,2H),6.93-6.88(m ,2H),6.56(s,1H),2.74(s,3H).

Embodiment 2

[0048] Add 1.21g (5.0mmol) of 2,4-dihydroxy-5-formylbenzophenone in ethanol (20mL) to a 100mL round bottom flask, and add 0.79g (6.5mmol) of 2,3-dimethyl An ethanol (10 mL) solution of phenylaniline, at this time, the molar ratio of 2,4-dihydroxy-5-formylbenzophenone to 2,3-dimethylaniline is 1:1.3. Control the reaction temperature to 85°C, and react for 3.5 hours. After the complete reaction of the raw materials was monitored by TLC, 20 mL of ethanol solvent was distilled off under reduced pressure, filtered by suction, and dried to obtain 1.46 g of a yellow solid, which was the corresponding product (E)-2,4-dihydroxy-5-(((2,3 -dimethylphenyl)imino)methyl)benzophenone. Yield 84.7%, m.p.126-127°C, TLC (PE:EA=5:1, R f =0.73), FTIR (KBr) (cm -1 ):3428m, 3054m, 2966m, 2918m, 2860m, ​​1622s, 1588s, 1562s, 1474s, 1354s, 1310s, 850m, 776m, 704m. 1 H NMR (CDCl 3 ,400MHz),δ:14.84(s,1H),12.78(s,1H),8.36(s,1H),7.68-7.49(m,6H),7.14-7.07(m,2H),6.91-6.88(m ,1H),6.58(s,1H),2.33(s,3H),...

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Abstract

The invention relates to the technical field of ultraviolet absorbers, and provides a benzophenone-Schiff base ultraviolet absorber and a preparation method thereof. The UV absorber structure provided by the present invention includes unsaturated carbon-nitrogen double bonds, oxygen-hydrogen-oxygen-hydrogen bonds, nitrogen-hydrogen-oxygen-hydrogen bonds and conjugated structures of different substituted phenyl groups (R groups), which mainly absorb ultraviolet light in the range of 250-400nm, is a new type of broad-spectrum ultraviolet absorber, compared with the existing ultraviolet absorber, the ultraviolet absorber provided by the present invention has better absorption capacity and stronger market potential. The preparation method provided by the invention can obtain the product only through one-step condensation reaction, the steps are simple, the preparation cost is low, and industrial production is easy.

Description

technical field [0001] The invention relates to the technical field of ultraviolet absorbers, in particular to a benzophenone-Schiff base ultraviolet absorber and a preparation method thereof. Background technique [0002] In recent years, with the continuous destruction of the atmospheric ozone layer, the amount of ultraviolet radiation has become one of the most concerned global environmental issues today. Ultraviolet rays in solar radiation pose obvious hazards to human health, causing skin dark spots, keratin growth, aging, relaxation, etc., and even skin cancer and suppression of the body's immune system. Ultraviolet rays are divided into UVA (wavelength 320-400nm, long wave), UVB (wavelength 280-320nm, medium wave) and UVC (wavelength 100-280nm, short wave). UVC can be absorbed by the ozone layer and cannot reach the surface of the earth; UVB can reach the epidermis of the skin and cause intense light damage, and the skin will appear erythema, inflammation, aging and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/24C07C249/02
CPCC07C251/24
Inventor 王治国杨春来
Owner HUBEI MEIKAI CHEM