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Intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-aminoketone as well as preparation method and application of intramolecular sensitized macromolecular photoinitiator

A technology of photoinitiator and pyrazoline, applied in the field of intramolecular sensitized macromolecular photoinitiator and its preparation, can solve problems such as toxicity and limitation, and achieve the effects of low volatility, reduced odor and low mobility

Pending Publication Date: 2022-06-07
内蒙古扬帆新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] (1) Photoinitiator 907 has certain toxicity and is not suitable for packaging and printing fields such as food, medicine, and hygiene products; Physically entrapped in the acrylate cross-linked network, it becomes a residual photoinitiator. When it comes into contact with hot water, solvents, oils and other substances, molecular migration, penetration or extraction occurs, so it is restricted in use
[0009] (2) The absorption spectrum of photoinitiator 907 is mainly in the UVB region, and it can be cured very well under the mercury lamp, but it is greatly restricted in the growing UV-LED field
However, ITX faces the same toxicity problem as 907, and its use is restricted in many fields

Method used

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  • Intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-aminoketone as well as preparation method and application of intramolecular sensitized macromolecular photoinitiator
  • Intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-aminoketone as well as preparation method and application of intramolecular sensitized macromolecular photoinitiator
  • Intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-aminoketone as well as preparation method and application of intramolecular sensitized macromolecular photoinitiator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Preparation of α-aminoketone-based small molecule photoinitiator PI-2 containing double bonds

[0073]

[0074] 30.9 g of 2-morpholino-4'-(2-hydroxyethylthio)-2-methylpropiophenone (0.1 mol) and 300 ml of n-heptane were added to the double-layer reaction flask, and then 2-morpholine was added. In the mixed solution of base-4'-(2-hydroxyethylthio)-2-methylpropiophenone and n-heptane; add 12 grams of 50% aqueous sodium hydroxide solution dropwise to the double-layer reaction flask and 0.3 g of tetrabutyl ammonium bromide, turn on the condensed water, control the reaction temperature at room temperature 25 ° C, under the protection of nitrogen atmosphere, dropwise add the n-heptane solution of 50 ml of allyl bromide, the allyl bromide is 0.12mol After the dropwise addition, the temperature of the reaction system will rise immediately, control the dropwise temperature to be below 30°C, and finish dropping in about 30 minutes, and then stir the reaction at room...

Embodiment 2

[0076] Example 2: Preparation of α-aminoketone-based small molecule photoinitiator PI-1 containing double bonds

[0077]

[0078] 30.9 g of 2-morpholinyl-4'-(2-hydroxyethylthio)-2-methylpropiophenone (0.1 mol) and 300 ml of anhydrous dichloromethane were added to the double-layer reaction flask, followed by 12.2 g of Triethylamine (0.12mol), turn on the low temperature cycle, lower the temperature in the double-layer reaction flask to 0°C, and under the protection of nitrogen atmosphere, add methanesulfonyl chloride (0.105mol) or p-toluene dropwise to the double-layer reaction flask 50 ml of dichloromethane solution of sulfonyl chloride (0.105mol), the temperature of the reaction system will rise immediately, control the dropwise temperature to be below 5 ℃, and the dropwise addition is completed in about 30 minutes, then stir at low temperature for 30 minutes, and then rise to room temperature and react for 2 hours , monitor the reaction by spot plate to the end of the rea...

Embodiment 3

[0085] Embodiment 3: Utilize thiol-ene click reaction to prepare target product photoinitiator 1

[0086]

[0087] Add 6.98 g (20 mmol) of photoinitiator PI-2 and 3.54 g (10 mmol) of pyrazoline derivative A containing double bonds to the three-necked flask of 100 ml, then add 3.98 g (10 mmol) of trithiol and azobis 0.180 g of isobutyronitrile, evacuated, filled with nitrogen for three cycles, placed the three-necked flask in an oil bath at 50 °C, stirred for 30 minutes, heated to 70 °C, reacted for 2 hours, and then reacted at 90 °C for 1 hour; Spectral monitoring found 2570cm -1 The peak of thiol disappears, and the reaction ends after thin-plate chromatography is free of raw materials; α-aminoketone small molecule photoinitiator PI containing double bond, pyrazoline derivative A containing double bond and polythiol compounds B was prepared by the thiol-alkene click reaction to prepare the target product photoinitiator 1.

[0088] After the reaction is completed, it is not...

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Abstract

The invention discloses an intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-aminoketone as well as a preparation method and application of the intramolecular sensitized macromolecular photoinitiator, and belongs to the technical field of new material organic chemicals. The invention relates to an intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-aminoketone. The intramolecular sensitized macromolecular photoinitiator containing pyrazoline and alpha-aminoketone is a macromolecular photoinitiator I which is formed by jointly grafting an alpha-aminoketone micromolecular photoinitiator PI containing double bonds, a pyrazoline derivative A containing double bonds and a polythiol compound B through a thiol-olefin click reaction. The modified initiator can effectively reduce the odor of a photoinitiator curing product, and meanwhile, the modified initiator can utilize a current hottest LED light source as an excitation light source when a curing system is initiated for curing.

Description

technical field [0001] The invention relates to the technical field of new material organic chemicals, more particularly, to an intramolecular sensitized macromolecular photoinitiator containing pyrazoline and α-aminoketone, and a preparation method and application thereof. Background technique [0002] Light-curing technology is a process in which liquid photosensitive resin is polymerized into a solid under light induction. It has the characteristics of high efficiency, rapidity, economical energy saving, and environmental protection. , biomedicine and other fields. The photoinitiator is a key factor controlling the entire photopolymerization process, and its activity directly affects the photocuring rate, curing degree, and end product properties. In particular, food and drug packaging, children's toys, etc. that are in direct contact with the human body have higher requirements for the migration and smell of the residual photoinitiator. Therefore, photoinitiators with ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06C07D403/12C07D487/04C08F2/48
CPCC07D231/06C07D403/12C07D487/04C08F2/48Y02P20/10
Inventor 金明廖文郭峰李敬东杨成双林立东
Owner 内蒙古扬帆新材料有限公司
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