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1-phenyl-1,2-dione compound LED photoinitiators and synthesis method thereof

A technology of photoinitiator and synthesis method, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of poor absorption of light energy, poor initiation performance, etc. The effect of an economical production process

Inactive Publication Date: 2018-05-29
HUAIHUA JINXIN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption wavelength of most reported or commercialized photoinitiators is poor in absorbing light energy above 365nm. Under the illumination of LED light source, the initiation performance of these photoinitiators is not very good.
It is a huge challenge to efficiently induce various types of photopolymerization reactions under the illumination of LED light sources in such a background.

Method used

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  • 1-phenyl-1,2-dione compound LED photoinitiators and synthesis method thereof
  • 1-phenyl-1,2-dione compound LED photoinitiators and synthesis method thereof
  • 1-phenyl-1,2-dione compound LED photoinitiators and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) In the reactor of 2000 liters, add 800kg ethanol and 400kg propiophenone, pass into 78kg dry hydrogen chloride gas under the cooling of ice water, keep passing into 242kg ethyl nitrite at 30-35 ℃, continue to pass through after finishing The temperature was reacted for 2 hours, the reaction was stopped, and the ethanol was distilled off under reduced pressure to obtain a crude product. 700 kg of toluene was added for recrystallization to obtain 310 kg of 1-phenyl 1,2-propanedione-2-oxime with a yield of 63.8%.

[0023] (2) In a 1000-liter reaction kettle, add 200kg of concentrated hydrochloric acid, 200kg of 30% formaldehyde solution and 200kg of ethanol, cool under ice water cooling below 15°C, and add 200kg of 1-phenyl 1,2-propanedione-2 in batches -oxime, stirred at room temperature and reacted for 8 hours after addition, extracted with 400kg of dichloromethane, then washed once with saturated sodium bicarbonate solution and water, removed dichloromethane to obta...

Embodiment 2

[0025] (1) In a 1000 ml reaction flask, add 300 g of ethanol and 148 g of isobutyrophenone, feed 40 g of dry hydrogen chloride gas under ice water cooling, and feed 120 g of ethyl nitrite at 30-35 °C. Continue to react at this temperature for 2 hours, stop the reaction, distill off ethanol under reduced pressure, add 300kg of toluene, wash with 100g of water twice, remove toluene, and obtain 1-phenyl-3-methyl-1,2-butanedione -2-oxime 139g, yield 78.5%. Go directly to the next reaction.

[0026] (2) In a 1000ml reaction flask, add 150g of concentrated hydrochloric acid, 150g of 30% formaldehyde solution and 200kg of ethanol, and add 139g of 1-phenyl-3-methyl-1,2- Butanedione-2-oxime, stirred at room temperature and reacted for 12 hours after the addition, extracted with 200g of dichloromethane, then washed once with saturated sodium bicarbonate solution and water, removed the dichloromethane to obtain the crude product, and distilled under reduced pressure to obtain Yellow li...

Embodiment 3

[0028] (1) In a 1000 ml reaction flask, add 300 g of ethanol and 160 g of phenylcyclopropylmethyl ketone, feed 40 g of dry hydrogen chloride gas under ice water cooling, and feed 120 g of ethyl nitrite at 30-35°C After passing through, continue to react at this temperature for 2 hours, stop the reaction, evaporate ethanol under reduced pressure, add 300kg toluene, wash twice with 100g water respectively, remove toluene, and obtain 1-phenyl-2-cyclopropyl-1, 148 g of 2-propanedione-2-oxime, the yield was 78.3%. Go directly to the next reaction.

[0029] (2) In a 1000ml reaction flask, add 150g of hydrochloric acid, 150g of formaldehyde solution and 150g of ethanol, cool under ice water cooling and add 148g of 1-phenyl-2-cyclopropyl-1,2-propane in batches below 15°C Diketone-2-oxime, stirred at room temperature and reacted for 2 hours after addition, extracted with 300g dichloromethane, then washed once with saturated sodium bicarbonate solution and water, removed dichloromethan...

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Abstract

The invention relates to aryl diketone photoinitiators with the absorption wavelength of 395 nm. The compounds can be used as LED photoinitiators of the photopolymerization function of unsaturated alkene compounds or mixtures containing the compounds. Compared with traditional initiators, the photoinitiators enable the unsaturated alkene compounds to have quick polymerization reactions under LED light irradiation. Aryl akyl ketone is adopted as a raw material and reacts with ethyl nitrite under the action of hydrogen chloride to produce aryl alkyl ketoxime, the aryl alkyl ketoxime is hydrolyzed in a formaldehyde aqueous solution under the acid condition, and 1-phenyl-1,2-dione compounds are obtained. The application of the 1-phenyl-1,2-dione compounds in LED curing coatings and effects ofhydrolysis reactions under the action of hydrochloric acid are researched, and a novel 1-phenyl-1,2-dione compound synthesis technology which is simple to operate and economical is provided.

Description

technical field [0001] The invention belongs to the category of LED photoinitiators and the application of 1-aryl-1,2-diketone compounds in LED photopolymerization materials. Background technique [0002] UV light curing technology is a new technology that came out in the middle of the 20th century. It uses ultraviolet light (wavelength 200-400nm) as the energy source to trigger the process of rapid transformation of chemically reactive liquid substances into solids. Compared with the traditional thermal curing technology, it has the advantages of fast curing speed, high efficiency, less pollution, excellent performance and low cost, and is a rapidly developing "green" new technology. UV light curing products are composed of three parts, namely light curing resin, diluent and photoinitiator. [0003] In recent years, with the country's strict control of VOC emissions, UV light curing technology has become more and more important, and will gradually replace traditional heat ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/51C07C49/76C07C49/792C09D7/63
CPCC07C45/516C07C249/06C07C49/76C07C49/792C07C251/40C07C251/42
Inventor 王有名
Owner HUAIHUA JINXIN NEW MATERIAL CO LTD
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