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A photopolymerizable thioxanthone photoinitiator containing co-initiator amine and preparation method thereof

A technology of thioxanthone light and thioxanthone, which is applied in the field of substituted derivatives of thioxanthone, can solve the problems of large synthesis pollution, complicated process route, difficult promotion, etc., and achieve good matching effect

Active Publication Date: 2020-02-14
开普瑞环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent CN 102212150 A discloses a polymerizable thioxanthone containing a co-initiator, whose synthetic raw material uses highly toxic and flammable liquid halopropene, and the process route is relatively complicated
The above-mentioned preparation routes all have the problem of large synthesis pollution, which is difficult to promote in practical applications

Method used

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  • A photopolymerizable thioxanthone photoinitiator containing co-initiator amine and preparation method thereof
  • A photopolymerizable thioxanthone photoinitiator containing co-initiator amine and preparation method thereof
  • A photopolymerizable thioxanthone photoinitiator containing co-initiator amine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1. Mix 4.7g (0.015mol) 2,2′-dithiosalicylic acid and 28mL (0.50mol) concentrated sulfuric acid evenly, control the reaction temperature in an ice-salt bath at 0-5°C, add 6.1g (0.04mol) Phenoxyacetic acid, stirred for 8 hours, quenched with ice water, filtered with suction, and dried. The crude product was recrystallized with a mixed solvent of ethanol and water (volume ratio 4:1) to obtain the product O-(thioxanthone-[2]-yl)-oxyacetic acid with a yield of 78%.

[0029] 2. Put the above 2.89g (0.01mol) of O-(thioxanthone-[2]-yl)-oxyacetic acid, 0.75g (0.01mol) of propanolamine and 30mL of acetone solvent into a three-necked flask, and then add 0.62g of dicyclohexylcarbodiimide dehydrating agent and 0.24g of 4-dimethylaminopyridine catalyst, react at room temperature for 4h, filter with thin-layer activated carbon after cooling, remove acetone by evaporation, dissolve with dilute hydrochloric acid, wash with toluene, and use ammonia water Adjust the pH value to 8-9, extr...

Embodiment 2

[0034] 1. Mix 4.7g (0.015mol) 2,2′-dithiosalicylic acid and 28mL (0.50mol) concentrated sulfuric acid evenly, control the reaction temperature in an ice-salt bath at 0-5°C, add 6.7g (0.04mol) 2-phenoxypropionic acid, stirred for 8 hours, quenched with ice water, filtered with suction, and dried. The crude product was recrystallized with a mixed solvent of ethanol and water (volume ratio 4:1) to obtain the product O-(thioxanthone-[2]-yl)-oxypropionic acid with a yield of 72%.

[0035] 2. Put the above 3.03g (0.01mol) O-(thioxanthone-[2]-yl)-oxypropionic acid, 1g (0.01mol) of 2-(propylamino)ethanol and 30mL of acetone solvent into the three ports Add 0.45g of dicyclohexylcarbodiimide dehydrating agent and 0.18g of 4-dimethylaminopyridine catalyst to the flask, react at room temperature for 5h, filter with thin-layer activated carbon after cooling, remove acetone by evaporation, dissolve with dilute hydrochloric acid, and dissolve with toluene Wash, adjust the pH value to 8-9 wi...

Embodiment 3

[0040] 1. Mix 4.7g (0.015mol) 2,2′-dithiosalicylic acid and 28mL (0.50mol) concentrated sulfuric acid evenly, control the reaction temperature in an ice-salt bath at 0-5°C, add 6.1g (0.04mol) Phenoxyacetic acid, stirred for 8 hours, quenched with ice water, filtered with suction, and dried. The crude product was recrystallized with a mixed solvent of ethanol and water (volume ratio 4:1) to obtain the product O-(thioxanthone-[2]-yl)-oxyacetic acid with a yield of 78%.

[0041] 2. Put the above 2.89g (0.01mol) O-(thioxanthone-[2]-yl)-oxyacetic acid, 0.76g (0.01mol) of N-methyl monoethanolamine and 30mL of acetone solvent into a three-necked flask , then add 0.62g of dicyclohexylcarbodiimide dehydrating agent and 0.24g of 4-dimethylaminopyridine catalyst, react at room temperature for 4h, filter with thin-layer activated carbon after cooling, remove acetone by evaporation, dissolve with dilute hydrochloric acid, and wash with toluene , adjust the pH value to 8-9 with ammonia wat...

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PUM

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Abstract

The invention discloses a photopolymerizable thioxanthone photoinitiator containing an auxiliary initiator amine and a preparation method. The structural general formula of the photopolymerizable thioxanthone photoinitiator containing the auxiliary initiator amine is as follows: as shown in the specification. As the molecular structure of the thioxanthone photoinitiator disclosed by the inventioncontains a photoinitiator, the auxiliary initiator amine and an end group of an acryloyl oxygen bond, the photopolymerizable thioxanthone photoinitiator is high in initiation activity, can participatein photopolymerization without migration, and also can be used as a monomer for synthesizing a macromolecular photoinitiator. The product raw materials are easy to obtain; the reaction process is mild; toxic substances such as a halogen compound and a high-boiling-point solvent are not involved, so that the photoinitiator is environmentally friendly and suitable for industrial production. The photopolymerizable thioxanthone photoinitiator is well matched with a UV-LED light source and can be applied to photocuring molding in the field of coatings, micro-electronics, packaging and the like.

Description

technical field [0001] The invention relates to substituted derivatives of thioxanthone, which can be used as photoinitiators and photosensitizers for free radical curing, specifically a photopolymerizable thioxanthone photoinitiator containing co-initiator amines and Preparation. Background technique [0002] Photopolymerization (light curing) technology is the process of using ultraviolet light or visible light to trigger the rapid transformation of chemically reactive liquid substances into solid substances. Compared with traditional thermal polymerization, it has the advantages of energy saving, environmental protection, and high efficiency. It is used in coatings, inks , microelectronics, photoresist, dental materials and other fields have a wide range of applications. The photoinitiator is a key component in the photopolymerization system. Thioxanthone derivatives are a class of valuable photoinitiators, which have the advantages of strong ultraviolet absorption, wide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F2/48C09D4/02C09D4/06C07D335/16
CPCC07D335/16C08F2/48C09D4/06
Inventor 汪瑾相可创肖亚辉
Owner 开普瑞环保科技有限公司