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Acrylate-substituted pyrazoline derivative, photocurable composition and preparation method

A technology of acrylate and pyrazoline, applied in the field of preparation of pyrazoline derivatives, can solve the problems of poor sensitization efficiency and slow curing rate of formula

Inactive Publication Date: 2021-04-27
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the smaller the photosensitizer content and the lower the concentration, the worse the sensitization efficiency and the slower the curing rate of the formulation

Method used

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  • Acrylate-substituted pyrazoline derivative, photocurable composition and preparation method
  • Acrylate-substituted pyrazoline derivative, photocurable composition and preparation method
  • Acrylate-substituted pyrazoline derivative, photocurable composition and preparation method

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preparation example Construction

[0092] [Preparation method of acrylate-substituted pyrazoline derivatives]

[0093] The preparation method of the acrylate-substituted pyrazoline derivative of the present invention comprises the following steps (c):

[0094]

[0095] In the step (c), the compound shown in formula (I)-b or formula (I)-b' and R 4 The substituted acryloyl chloride reaction obtains the acrylate substituted pyrazoline derivative shown in formula (I),

[0096] The R 1 , R 2 , R 3 , R 4 The definitions of z and z are the same as those defined in the aforementioned acrylate-substituted pyrazoline derivatives represented by the formula (I).

[0097] As an example of the aforementioned step (c), for example, combining the compound shown in formula (I)-b with R 4 Substitute acryloyl chloride in the system formed by triethylamine and dichloromethane to generate acrylate-substituted pyrazoline. After extraction, separation and recrystallization, the target product can be obtained.

[0098] Prefe...

Embodiment 1

[0116] Embodiment 1: The target molecule (I)-1 is synthesized according to the following route

[0117]

[0118] (a) Sodium hydroxide, absolute ethanol, normal temperature, 2h;

[0119] (b) Sodium hydroxide, absolute ethanol, 80°C, 2h;

[0120] (c) Triethylamine, dichloromethane, 0°C, 30min; room temperature, 10h.

[0121] 1. Synthesis of 1-phenyl-3-(4-hydroxymethyl)phenyl-2-en-1-one

[0122] Acetophenone (12.00 g, 0.10 mol), 4-hydroxymethylbenzaldehyde (13.62 g, 0.10 mol) and absolute ethanol (25 mL) were added to a 100 mL three-necked flask containing a magnetic rotor, and stirred at room temperature. An aqueous solution of sodium hydroxide (8.00 g, 0.20 mol, 10 mL) was added dropwise to the reaction system through a constant pressure dropping funnel. After the addition was completed, the reaction was carried out for 2 h, monitored by TLC. After the reaction, the solid obtained by filtration was washed once with water and twice with absolute ethanol, then dried and re...

Embodiment 2

[0127] Embodiment two: Synthesize the target molecule (I)-3 according to the following route

[0128]

[0129] (a) sodium hydroxide, absolute ethanol, room temperature, 2h; hydrochloric acid, pH=7;

[0130] (b) Acetic acid, 135°C, 2h;

[0131] (c) Potassium tert-butoxide, dichloromethane, 0°C, 30min; room temperature, 10h.

[0132] 1. Synthesis of 1-phenyl-3-(4-hydroxyphenyl)-2-en-1-one

[0133] Add acetophenone (12.00 g, 0.10 mol), 4-hydroxybenzaldehyde (12.21 g, 0.10 mol) and absolute ethanol (25 mL) into a 100 mL three-necked flask containing a magnetic rotor, and stir at room temperature. Then an aqueous solution of sodium hydroxide (12.00 g, 0.30 mol, 12 mL) was prepared and added dropwise to the reaction system through a constant pressure dropping funnel. After the addition was completed, the reaction was carried out for 2 hours, and the reaction process was monitored by a silica gel chromatography plate. After the reaction was finished, brine was added to make th...

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Abstract

The present application relates to an acrylate-substituted pyrazoline derivative represented by formula (I), a photocurable composition, and a preparation method and application of the acrylate-substituted pyrazoline derivative represented by formula (I). The acrylate-substituted pyrazoline derivative shown in the formula (I) has good absorption at the wavelength of 350 nm or above, compared with a common sensitizer, the synthesis steps of the molecule are simpler and more convenient, and the molecule can react with polymerizable components in the radiation curing process and can be connected with a polymer system through chemical bonds, so that the low mobility of small molecule components in the formula is reduced.

Description

technical field [0001] The invention belongs to the field of organic chemistry of new materials, and in particular relates to the preparation of an acrylate-substituted pyrazoline derivative and its application as a sensitizer in a photocuring system. Background technique [0002] Photocuring technology is the process of using ultraviolet-visible light to trigger a chemically reactive liquid substance to rapidly transform it into a solid substance. This technology has the characteristics of high efficiency, economy, energy saving, wide adaptability and environmental friendliness, and is widely used in the fields of printing plate making, ink, coating, stereolithography, adhesives, food packaging and medical biomaterials. [0003] In the photocuring process, free radical polymerization is currently the most commonly used curing method. After the photoinitiator absorbs photon energy, it breaks or hydrogen abstracts to generate free radicals, which then initiates the polymeriz...

Claims

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Application Information

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IPC IPC(8): C07D231/06C07D405/04C07D409/04C07D403/04C08F2/50C09D175/14
CPCC07D231/06C07D405/04C07D409/04C07D403/04C08F2/50C09D175/14
Inventor 金明陈世雄万德成
Owner TONGJI UNIV
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