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A new aminoketone photoinitiator and its application in uv‑led light curing system

A photoinitiator, aminoketone technology, applied in organic chemistry, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of limited absorption, single radiation wave peak of UV-LED light source, unable to provide initiating activity, etc. Simple, strong intramolecular electron transfer performance, and the effect of excellent optoelectronic properties

Active Publication Date: 2017-04-26
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the single peak of UV-LED light source radiation, the energy is concentrated in a narrow ultraviolet spectrum segment, and most of the peaks of UV-LED light sources on the market are concentrated at 365-395nm, which is the best point for curing
Among the existing photoinitiators, only two types of photoinitiators, thioxanthone and acylphosphine oxide, have certain absorption in the range of 365-395nm, which can barely be used with LED light sources, but the absorption in the range of 365-395nm is still very low. It is limited and cannot provide sufficient initiation activity, so it is still very urgent to develop a photoinitiator with stronger light absorption ability and higher initiation activity that matches the 365-395nm UV-LED light source

Method used

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  • A new aminoketone photoinitiator and its application in uv‑led light curing system
  • A new aminoketone photoinitiator and its application in uv‑led light curing system
  • A new aminoketone photoinitiator and its application in uv‑led light curing system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: Preparation of intermediate 1-p-fluorophenyl-2-dimethylamino-2-benzyl-1-butanone

[0062] 1) Preparation of 1-p-fluorophenyl-1-butanone

[0063] Add 58.1g (0.44mol) of anhydrous aluminum trichloride, 34.9g (0.36mol) of fluorobenzene and 90mL of To 1,2-dichloroethane, slowly add 46.5g (0.44mol) of n-butyryl chloride below 10°C, and stir for 4-6h at 35-45°C. After the reaction solution is cooled to room temperature, pour it into hydrochloric acid-ice water, stir for 30 minutes, let it stand for layers, separate the organic phase, and wash the organic phase with sodium hydroxide solution (to remove n-butyric acid in the system), and then wash the organic phase once with water , solvent removal, and solvent recovery to obtain 1-p-fluorophenyl-1-butanone.

[0064] 2) Preparation of 1-p-fluorophenyl-2 bromo-1-butanone

[0065] Add 80mL of 1,2-dichloroethane, 36.9g of concentrated sulfuric acid and the prepared 1-p-fluorophenyl-1-butanone into a 500mL vessel e...

Embodiment 2

[0070] Example 2: Preparation of 1-p-chlorophenyl-2-dimethylamino-2-benzyl-1-butanone

[0071] 1) Preparation of 1-p-chlorophenyl-1-butanone

[0072] Add 46.1g (0.35mol) of anhydrous aluminum trichloride, 31.5g (0.28mol) of chlorobenzene and 70mL of To 1,2-dichloroethane, slowly add 36.8g (0.35mol) of n-butyryl chloride below 10°C, and stir for 4-6 hours at 35-45°C. After the reaction solution is cooled to room temperature, pour it into hydrochloric acid-ice water, stir for 30 minutes, let it stand for layers, separate the organic phase, and wash the organic phase with sodium hydroxide solution (to remove n-butyric acid in the system), and then wash the organic phase once with water , solvent removal, and solvent recovery to obtain 1-p-chlorophenyl-1-butanone.

[0073] 2) Preparation of 1-p-chlorophenyl-2 bromo-1-butanone

[0074] Add 65mL of 1,2-dichloroethane, 28.8g of concentrated sulfuric acid and the prepared 1-p-chlorophenyl-1-butanone into a 500mL vessel equipped wit...

Embodiment 3

[0079] Example 3: Preparation of 1-[4-(4-isopropylphenylthio)phenyl]-2-dimethylamino-2-benzyl-1-butanone

[0080] 1) Using 1-p-fluorophenyl-2-dimethylamino-2-benzyl-1-butanone as raw material

[0081] In a 250mL four-neck flask equipped with a mechanical stirrer, a thermometer, a constant pressure dropping funnel, and a spherical reflux condenser, add 80mL of N,N-dimethylformamide solution dissolved in 2.8g (0.050mol) of potassium hydroxide , Slowly add 7.6g (0.050mol) p-isopropylthiophenol dropwise under stirring, and stir at room temperature for 1h. Add 10.0g (0.033mol) of 1-p-fluorophenyl-2-dimethylamino-2-benzyl-1-butanone, stir and raise the temperature to 100~120℃, and react for 10~15h. Cool the reaction solution, slowly add it dropwise to a large amount of ice water, then extract it several times with a small amount of ethyl acetate, separate the organic phase, wash the organic phase with saturated sodium chloride solution several times, dry over anhydrous sodium sulfa...

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Abstract

The invention provides a novel aminoketones photoinitiator suitable for UV-LED light source curing. The novel aminoketones photoinitiator can be higher in adsorption in a long-wavelength region (365-395nm), is suitable for UV-LED light source curing, and overcomes the defects of high energy consumption and heavy pollution in traditional curing. The novel aminoketones photoinitiator is good in eectron delocalizability, has high intramolecular electron transfer performance and excellent photoelectric property, is higher in adsorption in the range of 365nm to 395nm in the long-wavelength region, is suitable for a high-power UV-LED ultraviolet photocuring system, and has considerable advantages compared with the photoinitiator in the prior art.

Description

technical field [0001] The invention relates to a new aminoketone photoinitiator and its application in UV-LED light curing system. Background technique [0002] The photocuring system is generally composed of oligomers, reactive diluents, additives and photoinitiators. The mass fraction of photoinitiators is generally 3% to 5%. Although it is small, it plays an irreplaceable role. , is one of the important factors affecting the speed of photocuring. [0003] A photoinitiator refers to a compound that can absorb energy of a certain wavelength in the ultraviolet region (250~420nm) or visible region (400~800nm) and generate free radicals, cations, etc., thereby initiating monomer polymerization, crosslinking and curing. [0004] With the continuous development of light curing technology, a new UV-LED technology based on LED light source has emerged. This technology is more energy-saving, environmentally friendly, does not contain mercury, can work under low temperature condi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/16C07C221/00C07C319/14C07C323/32C07C323/20C07D295/096C08L63/10
Inventor 吴吉王俊权武瑞董月国王涛罗想张齐赵国锋
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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