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Long-wavelength methyl benzoylformate photoinitiator and preparation method thereof

A technology of benzoylformic acid and photoinitiator, which is applied in the field of long-wavelength methyl benzoylformate photoinitiator and its preparation, and can solve the problem that LED light sources cannot continuously and stably emit short-wavelength ultraviolet light and convert double bonds Low production rate and other problems, to achieve the effect of strong market potential, low preparation cost and simple method

Pending Publication Date: 2020-08-21
HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to packaging technology and other reasons, LED light sources cannot continuously and stably emit short-wavelength ultraviolet light, and its main emission wavelengths are concentrated at 365nm-400nm, while the main absorption wavelengths of traditional photoinitiators MBF are 255nm and 325nm
If the LED light source is used to provide the energy of the photopolymerization reaction, and MBF is used as the photoinitiator of the photopolymerization reaction, the double bond conversion rate of the polymerized monomer in the photopolymerization reaction will be relatively small

Method used

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  • Long-wavelength methyl benzoylformate photoinitiator and preparation method thereof
  • Long-wavelength methyl benzoylformate photoinitiator and preparation method thereof
  • Long-wavelength methyl benzoylformate photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] (1) Preparation examples of 2-(4-formylphenyl)-2-oxoacetic acid methyl ester:

[0047] Dissolve 2 mol of 4-methylacetophenone and 4 mol of selenium dioxide in 1000 mL of pyridine, and react for 18 hours at 120 ° C under a nitrogen atmosphere. After the reaction is completed, filter the reaction liquid and evaporate the organic solvent to obtain the remaining reaction liquid. Add 200ml of 2mol / L sodium hydroxide solution to the remaining reaction solution, then add 200ml of ethyl acetate, then dropwise add 100ml of concentrated hydrochloric acid with a mass concentration of 65%, and directly separate the liquid and rotary evaporate the organic phase to obtain light yellow oily 2-oxo -2-(p-tolyl)acetic acid;

[0048] (2) Dissolve 0.5mol of 2-oxo-2-(p-tolyl)acetic acid and 1.7mol of potassium carbonate in 200mL of DMSO, add 57ml of dimethyl sulfate dropwise, and stir the reaction mixture for 0.5h at room temperature Mix with 200ml of ether, separate the layers, collect th...

Embodiment 2

[0055] Add 0.19 mol of 2-(4-formylphenyl)-2-oxoacetic acid methyl ester and 0.1 mol of 3-pentanone into 60 mL of ethanol to dissolve, use 1.5 wt% NaOH aqueous solution as catalyst, adjust pH=9 , after reacting at 70°C for 4 hours, stop heating, cool at room temperature, and find that there is solid precipitation, filter the solid, wash with a small amount of methanol, recrystallize, and dry in vacuo to finally obtain a long-wavelength methyl benzoylformate photoinitiator. The equation is as follows:

[0056]

[0057] The structure of the novel methyl benzoylformate photoinitiator prepared by 1 H-NMR and MS confirmed, 1 H-NMR (d-DMSO, 400MHz): δ (ppm) 2.34 (s, 6H), 3.61 (s, 6H), 7.37 (s, 2H), 7.53 (m, 4H), 7.80 (m, 4H); MS(m / z):434(M+1) + ;

[0058] The maximum absorption wavelength of the prepared long-wavelength methyl benzoylformate photoinitiator is 365nm (see specification attached). image 3 ), under the irradiation of an LED point light source with a wavelength o...

Embodiment 3

[0060] Add 0.135 mol of 2-(4-formylphenyl)-2-oxoacetic acid methyl ester and 0.075 mol 4,4-cyclohexanone into 45 mL of ethanol to dissolve, and use 1 wt% KOH aqueous solution as a catalyst to adjust the pH =10, after reacting for 3 hours at 60°C, cool down and slowly precipitate solids, filter, wash with a small amount of ethanol, and vacuum-dry to finally obtain a long-wavelength methyl benzoylformate photoinitiator. The reaction equation is as follows:

[0061]

[0062] The structure of the novel methyl benzoylformate photoinitiator prepared by 1 H-NMR and MS confirmed, 1 H-NMR (d-DMSO, 400MHz): δ (ppm) 1.00 (s, 6H), 1.82 (s, 4H), 3.61 (s, 6H), 7.37 (s, 2H), 7.53 (m, 4H), 7.80(m,4H); MS(m / z):474(M+1) + ;

[0063] The maximum absorption wavelength of the prepared long-wavelength methyl benzoylformate photoinitiator is 360nm (see specification attached). Figure 4 ), under the irradiation of an LED point light source with a wavelength of 365nm, the concentration of the ...

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Abstract

The invention relates to the technical field of organic synthesis, and especially relates to a long-wavelength methyl benzoylformate photoinitiator and a preparation method thereof. The emission wavelength range of LED light sources used in the market at present is 365 nm or above. The maximum absorption wavelength of a traditional photoinitiator MBF is 255 nm, the wavelength is not matched with the emission wavelength of the LED light source, so in order to enable the maximum absorption wavelength of the MBF photoinitiator to be matched with the main emission wavelength range of the LED lightsource, the invention provides the long-wavelength methyl benzoylformate type photoinitiator and the preparation method thereof. The long-wavelength methyl benzoylformate photoinitiator is obtained by a condensation reaction of an aldehyde group and / or R1 functionalized methyl benzoylformate derivative and a ketone compound containing alpha H atoms, the maximum absorption wavelength of the long-wavelength methyl benzoylformate photoinitiator can reach 365 nm or above, and the long-wavelength methyl benzoylformate photoinitiator is matched with the LED light source used in the market and has good commercial application prospects.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a long-wavelength methyl benzoylformate photoinitiator and a preparation method thereof. Background technique [0002] Photoinitiator MBF, also known as methyl benzoylformate. Methyl benzoylformate is a colorless or light yellow liquid, soluble in organic solvents such as toluene, ethanol, ether, etc. High temperature, good thermal stability, low odor and many other advantages, it plays an important role in the photopolymerization system. [0003] With China signing the Minamata Convention, mercury lamps will be banned. LED light source is a new type of low-power light source. Compared with mercury lamps, it has many advantages, such as high efficiency, no ozone generation, no mercury pollution, and long life. It has been popularized in the field of photopolymerization in recent years. . However, due to packaging technology and other reasons, LED light sources canno...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/738C07D207/333C07D207/337C07D207/267C07D207/38C07C67/343C08F2/48
CPCC07C69/738C07D207/333C07D207/337C07D207/267C07D207/38C08F2/48C07C2601/14
Inventor 朱晓群李阳聂俊
Owner HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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