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Aromatic ring-containing benzophenone derivatives, and preparation method and application thereof

A technology of benzophenone and methoxybenzophenone, which is applied in the field of benzophenone derivatives and its preparation, can solve the problems of narrow absorption range, unsatisfactory activity, and weak absorption strength, etc., and achieves easy preparation , Reduce the release of benzene, good compatibility effect

Active Publication Date: 2020-05-12
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the weak UV absorption intensity and narrow absorption range of benzophenone, the photoinitiation activity is not ideal.

Method used

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  • Aromatic ring-containing benzophenone derivatives, and preparation method and application thereof
  • Aromatic ring-containing benzophenone derivatives, and preparation method and application thereof
  • Aromatic ring-containing benzophenone derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 0.228g (1mmol) of 2-hydroxy-4-methoxybenzophenone and 0.150g (1.5mmol) of triethylamine into the container, dissolve it with 3ml of dichloromethane, and slowly add 4 -Toluyl chloride 0.185g (1.2mmol), stirred for 3 hours. After the reaction, add water to the reaction solution and extract with ethyl acetate, collect the organic phase, wash with water, dry over anhydrous sodium sulfate, and remove the organic solvent by rotary evaporation; and use petroleum ether / ethyl acetate (volume ratio 12:1) as The eluent was subjected to column chromatography to obtain derivative 1.

[0035] Derivative 1: colorless transparent liquid, yield: 94%, 1 H NMR (600MHz, CDCl 3 )δ7.78–7.72 (m, 4H), 7.60 (t, J = 8.0Hz, 1H), 7.45 (dt, J = 8.6, 4.1Hz, 1H), 7.37 (dd, J = 16.1, 8.3Hz, 2H ),7.16(t,J=8.7Hz,2H),6.93–6.86(m,2H),3.96–3.86(m,3H),2.43–2.36(m,3H). 13 C NMR (151MHz, CDCl 3 )δ194.30, 164.74, 163.05, 151.03, 144.35, 138.51, 132.59, 132.40, 130.10, 129.62, 129.03, 128.21, 126.12, 1...

Embodiment 2

[0037] Add 0.228g (1mmol) of 2-hydroxy-4-methoxybenzophenone and 0.150g (1.5mmol) of triethylamine into the container, dissolve it with 3ml of dichloromethane, and slowly add 2 - Thienoyl chloride 0.175g (1.2mmol), stirred for 3 hours. After the reaction, add water to the reaction solution and extract with ethyl acetate, collect the organic phase, wash with water, dry over anhydrous sodium sulfate, and remove the organic solvent by rotary evaporation; and use petroleum ether / ethyl acetate (volume ratio 12:1) as The eluent was subjected to column chromatography to obtain derivative 2.

[0038] Derivative 2: white solid, yield: 96%, m.p.86-88°C. 1 H NMR (600MHz, CDCl 3 )δ7.75(t, J=7.9Hz, 2H), 7.69–7.65(m, 1H), 7.60(dd, J=10.4, 5.5Hz, 1H), 7.58–7.55(m, 1H), 7.47(dd ,J=14.3,7.0Hz,1H),7.41–7.35(m,2H),7.04(dd,J=11.1,6.4Hz,1H),6.93–6.86(m,2H),3.94–3.88(m,3H ). 13 C NMR (151MHz, CDCl 3 )δ 194.18, 163.01, 160.00, 150.48, 138.43, 134.79, 133.67, 132.67, 132.42, 132.11, 129.61, 128...

Embodiment 3

[0040] Add 0.228g (1mmol) of 2-hydroxy-4-methoxybenzophenone and 0.150g (1.5mmol) of triethylamine into the container, dissolve it with 3ml of dichloromethane, and slowly add 2 - 0.156 g (1.2 mmol) of furoyl chloride, stirred and reacted for 3 hours. After the reaction, add water to the reaction solution and extract with ethyl acetate, collect the organic phase, wash with water, dry over anhydrous sodium sulfate, and remove the organic solvent by rotary evaporation; and use petroleum ether / ethyl acetate (volume ratio 12:1) as The eluent was subjected to column chromatography to obtain derivative 3.

[0041] Derivative 3: white solid, yield: 91%, m.p.105-108°C. 1 H NMR (600MHz, CDCl 3 )δ7.74(d, J=7.7Hz, 2H), 7.63–7.55(m, 2H), 7.47(q, J=7.3Hz, 1H), 7.39(t, J=7.6Hz, 2H), 7.05– 6.99(m,1H),6.94–6.86(m,2H),6.46(dd,J=3.3,1.5Hz,1H),3.94–3.87(m,3H). 13 C NMR (151MHz, CDCl 3 )δ194.09, 163.05, 156.27, 150.18, 147.23, 143.37, 138.41, 132.78, 132.40, 129.61, 128.20, 123.93, 119.57, 11...

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Abstract

The invention provides aromatic ring-containing benzophenone derivatives, and a preparation method and an application thereof. 2-hydroxy-4-methoxybenzophenone used as a raw material reacts with aromatic acyl chloride so as to synthesize three benzophenone derivatives containing aromatic rings. The preparation method has the advantages of simplicity in operation, mild reaction conditions, high yield and the like. The derivatives have high ultraviolet light absorption performance and can effectively absorb ultraviolet light of 250-310 nm, and the utilization rate of a light source is increased;the derivatives have the characteristics of good compatibility with resin or monomers, no odor and the like, and a cured film has good hardness and adhesive force. The three aromatic ring-containing benzophenone derivatives synthesized in the invention can be respectively applied to the fields of photocuring compositions such as coatings, printing ink, adhesives and the like as ultraviolet light initiators.

Description

technical field [0001] The invention relates to a benzophenone derivative, in particular to a benzophenone derivative containing an aromatic ring, a preparation method and application thereof. Background technique [0002] Photocuring technology has many advantages such as energy saving, environmental protection, high efficiency and fast speed, and has been widely used in traditional fields such as coatings, inks, and adhesives, as well as high-tech products such as 3D printing. The photoinitiator is the key component in the photocuring system, and it plays a decisive role in the photocuring speed. The development of cured products depends on the development of the photoinitiator to a certain extent. Benzophenone is a common photoinitiator with low price, simple synthesis and easy storage, and is widely used in UV-curable coatings. However, due to the weak ultraviolet absorption intensity of benzophenone and narrow absorption range, the photoinitiating activity is not ideal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/76C07C67/14C07D307/68C07D333/38C08F2/50C09D4/02C09J4/02C09D11/101
CPCC07C67/14C07C69/76C07D307/68C07D333/38C08F2/50C09D4/00C09D11/101C09J4/00
Inventor 张变香赵子任
Owner SHANXI UNIV
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