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Phenyl benzothiophene ketone compound and preparation method and application thereof

A technology of thiophenemethone and phenylbenzene, which is applied in the application field of phenylbenzothiophenemethone compound and its preparation, and UV-curable coatings, and can solve the problems of odor, poisonous gas, and low content of active ingredients in the product

Inactive Publication Date: 2012-09-26
山西亮龙涂料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the small molecular weight of benzophenone itself, it is easy to volatilize and migrate, resulting in odor and poisonous gas in the product, and benzene will be released during the use of benzophenone, which limits its use.
To overcome the shortcomings of benzophenone, new photoinitiators have been developed, such as 2-hydroxy-2-methyl-1-phenylacetone (1173), 1-hydroxycyclohexylphenyl ketone (184) And some macromolecularized benzophenone compounds, although these initiators have greatly improved in terms of odor and mobility, but the UV absorption length of 1173 and 184 only red-shifted to 244,280nm, macromolecularized benzophenone Although ketone compounds have a long red shift of UV absorption to 340nm, these products have low content of active ingredients and low reactivity per unit weight, which leads to slow curing speed

Method used

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  • Phenyl benzothiophene ketone compound and preparation method and application thereof
  • Phenyl benzothiophene ketone compound and preparation method and application thereof
  • Phenyl benzothiophene ketone compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Put a magnetic stirrer in a three-necked flask equipped with a constant pressure dropping funnel and a condenser tube (with a drying tube, which is then connected to a gas absorption device), and sequentially add 5-methyl-3-phenylbenzothiophene 2.24g (10mmol), CH 2 Cl 2 (30ml), 1.74g (13mmol) of anhydrous aluminum trichloride was added to the reactor, and after stirring evenly, 1.68g (12mmol) of benzoyl chloride was slowly added dropwise under ice bath conditions. After the dropwise addition was completed, return to room temperature and react Monitor with TLC; After the reaction finishes, put the above mixture into ice water (100ml), add concentrated hydrochloric acid (10ml) dropwise to carry out acidolysis, stir, after the solid in the mixture dissolves completely, transfer to a separatory funnel, separate the organic layer; the organic layer was washed once with an equal volume of sodium hydroxide solution and water, dried, filtered, spin-dried, and separated by colu...

Embodiment 2

[0024] Put a magnetic stirrer in a three-necked flask equipped with a constant pressure dropping funnel and a condenser tube (with a drying tube, which is then connected to a gas absorption device), and sequentially add 5-methyl-3-phenylbenzothiophene 2.24g (10mmol), CH 2 Cl 2 (30ml), 1.47g (11mmol) of anhydrous aluminum trichloride was added to the reactor, and after stirring evenly, 1.68g (12mmol) of benzoyl chloride was slowly added dropwise under ice bath conditions. After the dropwise addition was completed, return to room temperature and react Monitor with TLC; After the reaction finishes, put the above mixture into ice water (100ml), add concentrated hydrochloric acid (10ml) dropwise to carry out acidolysis, stir, after the solid in the mixture dissolves completely, transfer to a separatory funnel, separate the organic layer; the organic layer was washed once with an equal volume of sodium hydroxide solution and water, dried, filtered, spin-dried, and separated by colu...

Embodiment 3

[0026] Put a magnetic stirrer in a three-necked flask equipped with a constant pressure dropping funnel and a condenser tube (with a drying tube, which is then connected to a gas absorption device), and sequentially add 5-methyl-3-phenylbenzothiophene 2.24g (10mmol), CH2Cl2 (30ml), 2.01g (15mmol) of anhydrous aluminum trichloride were added to the reactor, after stirring evenly, 1.68g (12mmol) of benzoyl chloride was slowly added dropwise under ice bath conditions, and the dropwise addition was completed Afterwards, it was returned to room temperature, and the reaction was monitored by TLC; after the reaction, the above mixture was placed in ice water (100ml), and concentrated hydrochloric acid (10ml) was added dropwise for acidolysis, stirred, and when the solid in the mixture was completely dissolved, it was transferred to A separatory funnel was used to separate the organic layer; the organic layer was washed once with an equal volume of sodium hydroxide solution and water, ...

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Abstract

The invention discloses a phenyl benzothiophene ketone compound and a preparation method thereof. According to the method, benzothiophene used as a raw material is subjected to acylation to ensure that benzoyl is introduced a thiophene ring so as to prepare the phenyl benzothiophene ketone compound; the ultraviolet absorption wavelength of the compound can be shifted to the wavelength of 319nm; and due to the presence of the thiophene ring, the range of the ultraviolet absorption wavelength can be widened. The prepared phenyl benzothiophene ketone compound serving as a photoinitiator is used for an ultraviolet light cured composite, particularly ultraviolet light cured coating, and is high in reactivity, surface curing capacity and dissolubility; a molecule has a benzothiophene structure,so that the molecule is relatively stable; and therefore, the release amount of benzene is effectively reduced.

Description

technical field [0001] The invention relates to a sulfur-containing aryl ketone, specifically a phenylbenzothiophene ketone compound and a preparation method thereof, as well as the application of the compound as a photoinitiator in ultraviolet light curing compositions, especially ultraviolet light curing coatings. Background technique [0002] Ultraviolet curing technology (UV curing technology) has the incomparable advantages of no inert solvent volatilization, short curing time, low temperature curing and other traditional curing technologies, and is called a new generation of green technology. The photocuring system is generally composed of unsaturated resin, reactive diluent, photoinitiator and auxiliary agent. Photoinitiator is an important component of UV-curable coatings. It absorbs ultraviolet light and undergoes a chemical reaction to generate active free radicals and active cations, triggering the double bond opening polymerization of the unsaturated group of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/56C08F2/48C09D175/14
Inventor 张变香常姣杨祺吴群
Owner 山西亮龙涂料有限公司
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