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Oxime ester photoinitiator and preparation method thereof

A technology of photoinitiator and oxime ester, applied in the field of oxime ester photoinitiator and preparation thereof, can solve problems such as difficulty in curing colored resists, and achieve the effects of improving initiation activity, low production cost and increasing compatibility

Inactive Publication Date: 2009-09-09
EUTEC NEW MATERIALS TECH (SUZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Curing of colored resists becomes more difficult with higher pigment content

Method used

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  • Oxime ester photoinitiator and preparation method thereof
  • Oxime ester photoinitiator and preparation method thereof
  • Oxime ester photoinitiator and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] According to the photoinitiator of present embodiment, chemical name is N-ethylcarbazole-3-imidazole (2,3-diphenyl)-6-isobutylketone oxime ethyl ester, and its structural formula is as follows:

[0031]

[0032] It is prepared by following steps carried out in sequence:

[0033] (1), the synthesis of N-ethylcarbazole-3-isobutylone-6-formaldehyde

[0034]

[0035]Add 44.6g (0.2mol) of N-ethylcarbazole-3-carboxaldehyde and 250ml of anhydrous dichloroethane to a 500ml four-neck flask equipped with electric stirring, reflux condenser, dropping funnel and tail gas absorption device, and stir After dissolving (yellow), slowly add 58.1g (0.435mol) of anhydrous aluminum trichloride, the heat release is obvious, control the temperature not to exceed 40°C, keep stirring at 20-40°C for 10-15 minutes, then stir and cool to 5 ℃ or so. Slowly add the dichloroethane solution of isobutyryl chloride [composed of 23.8g isobutyryl chloride (0.223mol) and 20ml dichloroethane] dropw...

Embodiment 2

[0046] According to the photoinitiator of the present embodiment, the chemical name is N-ethylcarbazole-3-imidazole (2,3-diphenyl)-6-isobutanone oxime benzyl ester, and its structural formula is as follows:

[0047]

[0048] This photoinitiator is prepared through the following steps:

[0049] (1), synthesize N-ethylcarbazole-3-imidazole (2,3-diphenyl)-6-isobutylone oxime according to the method of embodiment 1;

[0050] (2), generate N-ethylcarbazole-3-imidazole (2,3-diphenyl)-6-isobutanone oxime and benzoyl chloride reaction by N-ethylcarbazole-3-imidazole (2, 3-Diphenyl)-6-isobutanone oxime benzyl ester.

[0051]

[0052] Add 2.5g (0.005mol) of N-ethylcarbazole-3-imidazole (2,3-diphenyl)-6-isobutylketone oxime (content 96.4%) (synthetic with example 1), THF 50g, after stirring and dissolving, be cooled to 0-5 ℃, add triethylamine 0.9g (0.009mol), keep 0-5 ℃, dropwise the THF solution of benzoyl chloride ( 1.2g of benzoyl chloride (0.0085mol), 5g of tetrahydrofuran)...

Embodiment 3

[0054] According to the photoinitiator of the present embodiment, its chemical structural formula is as follows:

[0055]

[0056] This photoinitiator can be prepared according to the method identical with embodiment 1 and 2, and its 1 H-NMR (ppm) is: 13.067, 7.692, 7.891, 7.711, 8.776, 7.053, 7.062, 7.552, 7.071, 7.063, 7.541, 7.533, 7.884, 7.653, 8.218, 7.561, 7.588, 8.235, 8.6676, 7. 3.832, 3.805, 4.534, 1.767, 1.305, 1.066.

[0057] mp 195-197°C, decomposition temperature 346°C.

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Abstract

The invention relates to an oxime ester photoinitiator and a preparation method thereof. The chemical name of the initiator is N-substituted carbazole-3-imidazole(2,3-diphenyl)-6-ketoxime ester. The preparation method comprises the following steps: N-substituted carbazole-3-formaldehyde is taken as a raw material, and N-substituted carbazole-3-substituent-6-formaldehyde is obtained after a Friedel-Crafts acylation reaction; the obtained N-substituted carbazole-3-substituent-6-formaldehyde reacts with benzil and ammonium acetate in a solvent in the presence of organic acid to obtain N-substituted carbazole-3-imidazole(2,3-diphenyl)-6-one, and the ketone further reacts with hydroxylamine hydrochloride or hydroxylamine in a polar solvent to obtain N-substituted carbazole-3-imidazole(2,3-diphenyl)-6-ketoxime; and the ketoxime further reacts with acyl chloride or anhydride in the presence of alkali to obtain the N-substituted carbazole-3-imidazole(2,3-diphenyl)-6-ketoxime ester, that is, the photoinitiator. The oxime ester photoinitiator has the advantages of good initiation activity, wide application scope and high thermal stability and storage stability.

Description

technical field [0001] The invention belongs to the field of photoinitiators, in particular to an oxime ester photoinitiator and a preparation method thereof. Background technique [0002] Photoinitiator is one of the indispensable components of UV-curable materials, and it plays a decisive role in the sensitivity of photocurable systems. Since light-curing materials have no solvent volatilization during curing, the pollution to the environment is greatly reduced. As an environmentally friendly green technology, light-curing technology has been vigorously developed in recent years. As an important part of photocurable materials, the function of photoinitiator is to generate active free radicals or cations after absorbing light energy of a certain wavelength, and initiate or catalyze the polymerization of corresponding monomers or prepolymers. As a photoinitiator, it usually needs to meet the following conditions: ① The quantum efficiency of initiation is high; ② The range o...

Claims

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Application Information

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IPC IPC(8): C08F2/48C07D403/04C07D409/14
Inventor 曾裕峰胡汉民陈华魏海涛张兴林
Owner EUTEC NEW MATERIALS TECH (SUZHOU) CO LTD
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