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Oxime ester photoinitiators containing five-membered heteroaromatic ring structure, and preparation and use thereof

A technology of aromatic heterocycle and oxime ester, applied in the direction of organic chemistry, etc., can solve the problems of general stability, poor stability, difficult practical application, etc.

Active Publication Date: 2019-12-10
HUBEI GURUN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In addition, although the oxime ester photoinitiator OXE-02 currently on the market has high photoinitiation activity, its stability is general, especially in photopolymerizable monomers. Photosensitive compositions are not suitable for long-term storage and transportation, which brings certain difficulties to practical applications

Method used

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  • Oxime ester photoinitiators containing five-membered heteroaromatic ring structure, and preparation and use thereof
  • Oxime ester photoinitiators containing five-membered heteroaromatic ring structure, and preparation and use thereof
  • Oxime ester photoinitiators containing five-membered heteroaromatic ring structure, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0136] Preparation Example 1: Preparation of Compound 1

[0137]

[0138] The synthetic route of compound 1 is as follows:

[0139]

[0140] Synthesis of intermediate compound 1a

[0141] 2,2'-dithiophene (0.08mol, 13.6g) was dissolved in 50ml of dichloroethane, then trifluoroacetic anhydride (0.7mol, 145g) and Mg(ClO 4 ) 2 (0.08mol, 17.87g), and the resulting mixture was heated to 80°C for 4h. Then stop the reaction, add 200g of ice, stir until the ice dissolves, add saturated aqueous sodium bicarbonate solution to neutralize the reaction solution until neutral. The organic phase was then extracted with dichloromethane and dried over anhydrous magnesium sulfate. After drying, it was filtered, and the organic phase was distilled off under reduced pressure to obtain a crude product, which was recrystallized from petroleum ether to obtain 17 g of the final product with a yield of 80%, which was identified as intermediate compound 1a. 1HNMR (400MHz, CDCl 3 , ppm) δ7.1...

preparation Embodiment 2-3

[0148] The method of Preparation Example 1 was repeated, and the reaction raw materials were appropriately changed to obtain compounds 2-3 and their NMR data in the following table respectively. Preparation Example 4: Preparation of Compound 4 Synthesis of Intermediate Compound 4a

preparation Embodiment 4

[0148] The method of Preparation Example 1 was repeated, and the reaction raw materials were appropriately changed to obtain compounds 2-3 and their NMR data in the following table respectively. Preparation Example 4: Preparation of Compound 4 Synthesis of Intermediate Compound 4a

[0149] 2,2'-dithiophene (0.027mol, 4.4g) was dissolved in 44ml of dichloroethane, then N,N-dimethylformamide (0.053mol, 3.9g) was added, and the POCl was added dropwise to the resulting mixture 3 (0.042mol, 6.3g), then stirred at room temperature for 5h. Then the reaction was stopped, and saturated aqueous sodium bicarbonate solution was added to neutralize the reaction solution to neutrality. The organic phase was then extracted with dichloromethane and dried over anhydrous magnesium sulfate. After drying, filter and remove the organic phase under reduced pressure to obtain a crude product, which is recrystallized with petroleum ether to obtain 3.9 g of the final product with a yield of 75%, wh...

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Abstract

The invention relates to oxime ester compounds containing a five-membered heteroaromatic ring structure and represented by the formula (I) and (II), wherein m, n, n', A1, A2, R1, R2, R3, R4, R5, R6, R6'R7 and R7' are defined in the specification. The compounds represented by the formula (I) and (II) have excellent light absorption at 350-450 nm, can initiate the polymerization of acrylate monomersat low concentration, and have excellent thermal stability in the acrylate monomers, are oxime ester photoinitiators good in stability and suitable for a UV-Vis LED light source. The invention also relates to preparation of the compounds represented by the formula (I) and (II) and a use of the compounds represented by the formula (I) and (II) as photoinitiators or photosensitizers.

Description

technical field [0001] The invention relates to an oxime ester compound containing a five-membered aromatic heterocyclic structure. The invention also relates to the preparation of the oxime ester compound and its use as a photoinitiator in a photopolymerization composition. Background technique [0002] Photoinitiators, also known as photosensitizers or photocuring agents, are a type of energy that can absorb certain wavelengths in the ultraviolet region (250-400nm) or visible region (400-600nm), and generate free radicals, cations, etc., thereby initiating monomer polymerization. Cross-linked cured compounds. In the photocuring system, the photoinitiator generally accounts for 3-5%. Although the content is low, it is the key component and plays a decisive role in the photocuring speed. It is related to whether the oligomer and diluent can be quickly cross-linked and solidified when the formulation system is irradiated with light, thereby changing from liquid to solid. A...

Claims

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Application Information

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IPC IPC(8): C07D333/22C07D409/06C07D307/52C07D207/323C07D409/04C08F2/48C08F122/20
CPCC07D207/323C07D307/52C07D333/22C07D409/04C07D409/06C08F2/48C08F122/20
Inventor 庞玉莲邹应全樊书珩
Owner HUBEI GURUN TECH CO LTD
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