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Bisphenol fluorene oxime ester photoinitiator as well as preparation method and application thereof

A technology of bisphenol fluorene oxime and photoinitiator is applied in the field of photocurable polymer materials, which can solve the problems of easy migration, small molecular weight, easy migration, etc., and achieve the effects of good surface curing effect, increased molecular weight and high initiation efficiency.

Pending Publication Date: 2022-03-15
FUYANG XINYIHUA MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN 109957046 A Utilizes a method similar to the above to synthesize fluorine-containing fluorine oxime ester, and adds fluorine-containing groups to the basis of fluorene oxime ester, so as to solve the problems of poor surface dryness and easy migration of existing fluorene oxime ester photoinitiators
[0004] Although there have been many reports reviewing the synthesis methods of fluorene oxime esters, the fluorene oxime ester photoinitiators synthesized by the above method usually have a relatively small molecular weight, and are prone to migration in the photocuring system, which affects the photocuring efficiency and affects the material quality. application performance

Method used

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  • Bisphenol fluorene oxime ester photoinitiator as well as preparation method and application thereof
  • Bisphenol fluorene oxime ester photoinitiator as well as preparation method and application thereof
  • Bisphenol fluorene oxime ester photoinitiator as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The structural formula of compound 1

[0052]

[0053] Its synthetic method comprises the following steps:

[0054]

[0055] (1) Add a magnetic stirring bar into a 1000 mL flask after vacuum drying, and add 70.0 g of bisphenol fluorene, 33.4 g of aluminum trichloride and 100 mL of anhydrous carbon disulfide into the flask. The system was cooled to 5°C in an ice-water bath, and a solution of 20.0 g of acetyl chloride in 100.0 mL of anhydrous carbon disulfide was added dropwise to the mixture at 5°C. The resulting mixture was allowed to warm to room temperature and stirred for 5 hours. The mixture was then heated to reflux for 3 hours. After cooling to room temperature, the resulting mixture was poured into ice water and extracted with dichloromethane 3x200 mL. Then wash the dichloromethane layer with water, dry the dichloromethane layer with 150g of anhydrous magnesium sulfate, spin distill the dichloromethane product solution after filtration, recrystallize wit...

Embodiment 2

[0061] The structural formula of compound 2

[0062]

[0063] Its synthetic method comprises the following steps:

[0064]

[0065] (1) Add a magnetic stirring bar into a 1000 mL flask after vacuum drying, and add 70.0 g of bisphenol fluorene, 33.4 g of aluminum trichloride, and 100.0 mL of anhydrous carbon disulfide into the flask. The system was cooled to 5°C in an ice-water bath, and a solution of 23.3 g of propionyl chloride in 100.0 mL of anhydrous carbon disulfide was added dropwise to the mixture at 5°C. The resulting mixture was allowed to warm to room temperature and stirred for 5 hours. The mixture was then heated to reflux for 3 hours. After cooling to room temperature, the resulting mixture was poured into ice water and extracted with dichloromethane 3x200 mL. Then wash the dichloromethane layer with water, dry the dichloromethane layer with 150g of anhydrous magnesium sulfate, spin distill the dichloromethane product solution after filtration, recrystalli...

Embodiment 3

[0071] The structural formula of compound 3

[0072]

[0073] Its synthetic method comprises the following steps:

[0074]

[0075] (1) Add a magnetic stirring bar into a 1000 mL flask after vacuum drying, and add 70.0 g of bisphenol fluorene, 33.4 g of aluminum trichloride, and 100.0 mL of anhydrous carbon disulfide into the flask. The system was cooled to 5°C in an ice-water bath, and a solution of 20.0 g of acetyl chloride in 100.0 mL of anhydrous carbon disulfide was added dropwise to the mixture at 5°C. The resulting mixture was allowed to warm to room temperature and stirred for 5 hours. The mixture was then heated to reflux for 3 hours. After cooling to room temperature, the resulting mixture was poured into ice water and extracted with dichloromethane 3x200 mL. Then wash the dichloromethane layer with water, dry the dichloromethane layer with 150g of anhydrous magnesium sulfate, spin distill the dichloromethane product solution after filtration, recrystallize ...

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Abstract

According to the bisphenol fluorene oxime ester photoinitiator and the preparation method and application thereof, the bisphenol fluorene oxime ester photoinitiator has two phenol groups on fluorene oxime ester, the molecular weight of a traditional fluorene oxime ester photoinitiator can be increased, and the bisphenol fluorene oxime ester photoinitiator is not prone to migration, high in initiation efficiency and good in surface curing effect. The preparation raw materials are low in cost, high-boiling-point solvents are not involved, and the method is suitable for industrial production and can be applied to the important technical fields of coatings, printing ink, dental materials, photoresists and the like.

Description

technical field [0001] The invention belongs to the field of photocurable polymer materials, and relates to a bisphenol fluorene oxime ester photoinitiator and a preparation method and application thereof. Background technique [0002] Photocuring technology refers to the process in which liquid oligomers and polymerizable monomers rapidly become solid through polymerization under light irradiation. In the past 30 years, photocuring technology has been widely used in coatings, inks, adhesives, photoresists, 3D printing and other fields. Photoinitiator, as one of the essential components in the photocuring system, not only determines the curing rate of the entire system but also affects the degree of curing and the performance of the end product. Oxime ester compounds have been widely used as photoinitiators. Due to the presence of unstable N-O bonds in oxime ester compounds, under the irradiation of ultraviolet light, the N-O bonds are easily broken to generate imine radica...

Claims

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Application Information

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IPC IPC(8): C07C251/66C07C249/12C08F2/48C09D4/06C09D4/02C09D11/101
CPCC07C251/66C08F2/48C09D4/06C09D11/101C07C2603/18
Inventor 龙文号
Owner FUYANG XINYIHUA MATERIAL TECH
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