Novel hydroxy-ketone photoinitiator and preparation and application thereof

A technology of photoinitiator and hydroxyketone, which is applied in the field of new hydroxyketone compounds, and can solve problems such as not easy to prepare

Active Publication Date: 2017-02-01
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Hydroxyketone macromolecular photoinitiators, such as the meta-substituted difunctional α-hydroxyketone photoinitiator 4, because the meta-substituted Darocur 1173 has better solubility than the para-position, it is generally liquid, easy to use, and relatively Good application prospects, but due to the positioning effect of the substituent on the aromatic ring, which affects the product of the Friedel-Crafts reaction, the meta-substituted α-hydroxy ketones are not easy to prepare

Method used

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  • Novel hydroxy-ketone photoinitiator and preparation and application thereof
  • Novel hydroxy-ketone photoinitiator and preparation and application thereof
  • Novel hydroxy-ketone photoinitiator and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Compound 1 preparation of

[0047] 1) Dissolve triphenylmethane (48.9g, 0.2mol) in 300ml chlorobenzene, control the reaction temperature at 0-10°C, add aluminum trichloride (82.7g, 0.62mol) and stir well, then add isobutyl dropwise Acyl chloride (66.1, 0.62mol), stirring for 2 hours after dropping, stop the reaction, pour the reaction solution into dilute hydrochloric acid made of 800g and 130ml concentrated hydrochloric acid, stir for 0.5h, let stand to separate the organic phase, and extract the water with dichloromethane phase, combined the organic phases, and washed with 200ml saturated sodium bicarbonate solution until the pH value of the organic phase became neutral, dried, and the solvent was recovered by precipitation to obtain a light yellow oil with a purity of 97%. It is also possible not to recover the solvent, and the organic phase is used Dry over anhydrous magnesium sulfate and proceed directly to the next reaction.

[0048] 2) Add chlorine ...

Embodiment 2

[0051] Example 2: Compound 2 preparation of

[0052] 1) Dissolve triphenylphosphine (52.5g, 0.2mol) in 300ml chlorobenzene, control the reaction temperature at 0-10°C, add aluminum trichloride (82.7g, 0.62mol) and stir well, then add isobutyl dropwise Acyl chloride (66.1, 0.62mol), after dropping, stir and react for 2 hours, stop the reaction, pour the reaction solution into dilute hydrochloric acid made of 800g and 130ml concentrated hydrochloric acid, stir for 0.5h, let stand to separate the organic phase, and extract with dichloromethane Water phase, combined organic phase, and washed with 200ml saturated sodium bicarbonate solution until the pH value of the organic phase became neutral, dried, and the solvent was recovered by precipitating to obtain a light yellow oil with a purity of 95%. It is also possible not to recover the solvent, and the organic phase After drying with anhydrous magnesium sulfate, proceed directly to the next reaction.

[0053] 2) Add chlorine ga...

Embodiment 3

[0057] Example 3: Compound 3 preparation of

[0058] 1) Dissolve triphenylphosphine (52.5g, 0.2mol) in 300ml chlorobenzene, control the reaction temperature at 0-10°C, add aluminum trichloride (82.7g, 0.62mol) and stir well, then add isobutyl dropwise Acyl chloride (66.1, 0.62mol), after dropping, stir and react for 2 hours, stop the reaction, pour the reaction solution into dilute hydrochloric acid made of 800g and 130ml concentrated hydrochloric acid, stir for 0.5h, let stand to separate the organic phase, and extract with dichloromethane Water phase, combined organic phase, and washed with 200ml saturated sodium bicarbonate solution until the pH value of the organic phase became neutral, dried, and the solvent was recovered by precipitating to obtain a light yellow oil with a purity of 96%. It is also possible not to recover the solvent, and the organic phase After drying with anhydrous magnesium sulfate, proceed directly to the next reaction.

[0059] 2) Add chlorine ga...

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PUM

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Abstract

The invention discloses a novel hydroxy-ketone photoinitiator and preparation and application thereof. The novel hydroxy-ketone photoinitiator is shown in the general formula I. The photoinitiator has excellent performance on the aspects of high activity, low smells, low migration, yellowing resistance and the like. The novel alpha-hydroxy-ketone photoinitiator has the general formula I shown in the specification.

Description

technical field [0001] The present invention relates to a kind of new hydroxy ketone compound, their preparation method, and this kind of compound is used as photopolymerization initiator of ethylenically unsaturated compound system. Background technique [0002] Darocur 1173 and Irgacure 184 are the most commonly used α-hydroxy ketone photoinitiators at present. Darocur 1173 and Irgacure 184 are the main initiators in various photocurable varnishes. They have excellent thermal stability, easy to use, high activity, and Good yellowing, low price and other advantages, but the disadvantage is that a series of volatile harmful organic compounds including benzaldehyde, acetone and cyclohexanone will be produced during the photolysis process, which has bad smell. The tendency to volatilize and migrate easily, and the resulting environmental and health pollution has become a growing concern in this field. [0003] [0004] There have been quite a few patent documents reporting...

Claims

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Application Information

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IPC IPC(8): C07C49/83C07C45/64C07F9/50C07F9/53C07C221/00C07C225/22C08F2/48C09D163/10C09D175/14C09D11/101C09D11/102
CPCC07C45/64C07C49/83C07C221/00C07C225/22C07F9/5022C07F9/5325C08F2/48C09D11/101C09D11/102C09D163/10C08L75/14
Inventor 武瑞董月国孙乡鹏张志鹏秦静张齐
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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