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Coumarin-carbazole type oxime ester compound as well as preparation method and application thereof

An ester compound, coumarin technology, applied in the field of photocurable coatings or inks, coumarin-based oxime ester-type compounds, can solve problems such as the inability to meet the research needs of visible light initiators

Active Publication Date: 2017-09-15
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption spectrum of coumarin itself is in the ultraviolet region (λ=310nm; ε=5170L mol - 1 cm -1 ), which cannot meet the research needs of visible photoinitiators

Method used

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  • Coumarin-carbazole type oxime ester compound as well as preparation method and application thereof
  • Coumarin-carbazole type oxime ester compound as well as preparation method and application thereof
  • Coumarin-carbazole type oxime ester compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 1. Preparation and characterization of compound (1)

[0045]

[0046] The initial substance is 4-hydroxycarbazole, and the product is obtained through acylation, esterification, etc. and reaction. The used synthetic route of this preparation method is expressed as follows:

[0047]

[0048] The specific process is as follows:

[0049] Step 1, the synthesis of compound (A). in N 2 Under protection, 6.96g (0.038mol) 4-hydroxycarbazole, 9.6mL (0.076mol) ethyl acetoacetate, 1.19g (0.0038mol) BiCl were added to a 100mL round bottom flask 3 After reacting in an oil bath at 100°C for 72 h under vigorous stirring, 500 mL of absolute ethanol was added to the reaction mixture, ultrasonically dispersed, filtered, and the filter cake was washed several times with ethanol to obtain an off-white solid, which was vacuum-dried at room temperature to obtain the product ( 1) 5.84g Yield: 61.7%. The product can be directly used in the next reaction.

[0050] Step 2, the synthe...

Embodiment 2

[0067] Embodiment two: preparation and characterization of compound (2)

[0068]

[0069] Compound (2) was prepared by the same preparation method as in the above-mentioned Example 1, the only difference being that p-isovaleryl chloride was used instead of n-butyryl chloride as the raw material. The yield of the target molecule in this example was 66.3%.

[0070] The structure of the product was confirmed by nuclear magnetic resonance spectroscopy, and the specific characterization results are as follows:

[0071] 1 H NMR (400MHz, CDCl 3 )δ8.83(s, 1H), 7.95(t, J=8.0Hz, 1H), 7.52(dd, J=8.6, 2.7Hz, 1H), 7.28(d, J=8.7Hz, 1H), 7.16( s,1H),6.07(s,1H),4.05(t,J=7.4Hz,2H),2.38(s,3H),1.92–1.79(m,3H),1.34–1.11(m,15H),0.79 (dt,J=13.5,7.0Hz,7H). 13 C NMR (101MHz, CDCl 3 )δ188.82,159.34,152.29,149.02,143.13,142.86,142.73,127.37,126.63,125.57,124.25,121.82,119.98,111.50,110.62,109.23,108.29,105.25,46.84,38.46,35.88,29.83,27.66,23.24,22.51 , 21.91, 18.26, 16.11, 12.94, 9.79.

Embodiment 3

[0072] Embodiment three: preparation and characterization of compound (3)

[0073]

[0074] Compound (3) was prepared by the same preparation method as in the above-mentioned Example 1, the only difference being that benzoic anhydride was used instead of acetic anhydride as the raw material. The productive rate of present embodiment target molecule is 80.2%,

[0075] The structure of the product was confirmed by mass spectrometry, and the specific characterization results are as follows:

[0076] HRMS (M+H) for C32H25F3NO3S4: 656.0624 (calculated), 656.0619 (experimental); (M+Na) for C32H24NaF3NO3S4: 678.0443 (calculated), 678.0449 (experimental).

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Abstract

The invention relates to the technical field of novel material organic chemicals, relates to a coumarin-carbazole type oxime ester compound as well as a preparation method and application thereof, and in particular relates to a novel compound of a structure of formula (I) or (II) as shown in the specification, a chemical preparation process technique of the novel compound, application of the novel compound as a radiation curing light-sensitive initiator, a radiation curing formula product of the novel compound, and particularly application of the novel compound in multiple places such as UV-Vis-LED excited light cured coatings or ink.

Description

【Technical field】 [0001] The present invention relates to the technical field of new material organic chemicals, in particular to a new class of coumarin-based oxime ester-type compounds, their chemical preparation technology, their use as radiation-curing photoinitiators, and their use in radiation-curing formulations. Products, especially in UV-Vis-LED excitable light-curable coatings or inks, and many other applications. 【Background technique】 [0002] Photoinitiator compounds are an important class of fine organic chemical materials. In the field of radiation curing technology using ultraviolet light or visible (UV) light or LED (i.e. Light-Emitting Diode) as light source, the photoinitiator compound that can generate free radical active species under light irradiation conditions is to induce ethylenically unsaturated It is a key species for efficient photopolymerization in the system, so it is one of the important components of radiation curing formulations. Photocuri...

Claims

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Application Information

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IPC IPC(8): C08F2/48C07D491/052G03F7/004G03F7/027
CPCC07D491/052C08F2/48G03F7/004G03F7/027
Inventor 金明孙新万德成潘海燕
Owner TONGJI UNIV
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