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Coumarin oxime ester photoinitiator and preparation method thereof

A technology of photoinitiator and coumarin oxime, which is applied in the field of photoinitiator containing coumarin structural unit and oxime ester group and its preparation, can solve the problem of hindering the development of oxime ester initiators, inability to match LED light sources, Curing material surface damage and other problems, to achieve the effect of easy implementation, mature preparation method and fast curing speed

Active Publication Date: 2015-08-05
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the excitation wavelength of most initiators is in the ultraviolet region, which cannot match the increasingly common LED light source, and the ultraviolet light will cause damage to the surface of the cured material, which is harmful to the human body. These deficiencies hinder the development of oxime ester initiators. development of

Method used

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  • Coumarin oxime ester photoinitiator and preparation method thereof
  • Coumarin oxime ester photoinitiator and preparation method thereof
  • Coumarin oxime ester photoinitiator and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044]

[0045] The preparation of photoinitiator A1-1, concrete preparation steps are as follows:

[0046] (1) In a 250mL three-necked flask with a condenser tube, 4.62g of 4-methyl-7-diethylaminocoumarin and 3.3g of selenium dioxide were dissolved in 120mL of xylene, and the whole system was N 2 Under protection, stirred and reacted at 130°C for 12h; filtered off the solid residue in the mixture while it was hot, and spin-dried the solvent to obtain a crude product; the crude product was separated by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) Purification afforded red solid B-1. Yield: 74%.

[0047] NMR: 1 H NMR (400MHz, CDCl 3 )δ10.06(s, 1H), 8.33(d, J=9.2Hz, 1H), 6.66(dd, J=9.2, 2.6Hz, 1H), 6.55(d, J=2.6Hz, 1H), 6.48( s, 1H), 3.46 (q, J = 7.1 Hz, 4H), 1.25 (t, J = 7.1 Hz, 6H).

[0048] (2) In a 25mL three-necked flask with a condenser tube, 0.163g of B-1 and 0.072g of NH 2 OH·HCl was dissolved in 10mL of absolute ethanol, under N 2 Stir...

Embodiment 2

[0053]

[0054] The preparation of photoinitiator A2-1, concrete preparation steps are as follows:

[0055] (1) In a 100mL three-neck flask with a condenser tube, dissolve 1.93g of 4-diethylamino salicylaldehyde, 3.2g of diethyl malonate and 1mL of piperidine in 30mL of absolute ethanol, and N 2 Under protection, stir, and react at 75°C for 6 hours; spin dry ethanol to obtain the intermediate product, add it to a 100mL three-neck flask with a condenser tube, add 20mL concentrated hydrochloric acid and 20mL glacial acetic acid to the bottle, N 2 Under protection, heat up to 100°C and stir for 6h; then cool the mixture to room temperature, pour it into 100mL of ice water, adjust its pH value to about 5 with 40% sodium hydroxide solution, a light yellow solid precipitates, continue to stir for 30min The solid crude product was obtained by filtration, washed several times with water, rinsed several times with absolute ethanol, and dried to obtain pure product C, yield: 86%.

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Abstract

The invention discloses a coumarin oxime ester photoinitiator and a preparation method thereof. The coumarin oxime ester photoinitiator is obtained by performing an oximation reaction on a coumarin compound containing a formyl group and NH2OH.HCl to obtain an oxime compound, and finally performing an esterification reaction on the oxime compound and acyl chloride. The photoinitiator is capable of initiating a polymerization reaction under visible light enough in intensity, and has the characteristics of high initiation activity and high curing speed.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to a photoinitiator containing a coumarin structural unit and an oxime ester group and a preparation method thereof. Background technique [0002] Environmental and energy issues in today's society are becoming more and more prominent. Photocurable materials are widely accepted and paid attention to as a green, environmentally friendly, and low-energy-consumption environment-friendly material because there is no or only a small amount of solvent volatilization during the curing process. [0003] Photoinitiator is an essential part of photocuring technology, it plays a key role in the photocuring process, determines the speed of photocuring, and even affects the performance of photocuring materials. As an important part of photocuring, the photoinitiator undergoes a photolysis reaction under the excitation of the light source to generate reactive free radicals or ions, and then initiat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07D311/16
Inventor 李治全朱桂刚刘仁刘敬成刘晓亚
Owner JIANGNAN UNIV
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