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Preparation method of macromolecular low-migration phosphine oxide UV-LED photoinitiators

A UV-LED and photoinitiator technology, which is applied in chemical instruments and methods, photomechanical equipment, photoplate-making process of patterned surface, etc., can solve the problem of non-drying on the surface of light-curing products and high migration of low-molecular-weight initiators And other issues

Active Publication Date: 2019-06-18
TIANJIN MOSEN TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The problem to be solved in the present invention is to provide a preparation method of a class of macromolecular low-mobility phosphine oxide UV-LED photoinitiators, which effectively solves the problem of high mobility of low-molecular weight initiators, and at the same time the absorption peak fully migrates to 365nm-405nm, Solved the problem of curing in the UV-LED band, and introduced the structure of benzophenone and α-hydroxyketone in the structure, so that the problem of non-drying of the surface of the light-cured product was solved

Method used

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  • Preparation method of macromolecular low-migration phosphine oxide UV-LED photoinitiators
  • Preparation method of macromolecular low-migration phosphine oxide UV-LED photoinitiators
  • Preparation method of macromolecular low-migration phosphine oxide UV-LED photoinitiators

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preparation example Construction

[0032] A kind of preparation method of macromolecule low migration phosphine oxide UV-LED photoinitiator, is characterized in that: comprise the following steps:

[0033] Step (1): Using 1,3,5-trimethylbenzene as a raw material, carry out Friedel-Crafts reaction with trichloroacetyl chloride or benzoyl chloride under the catalysis of Lewis acid or solid superacid to obtain intermediate a:

[0034]

[0035] Wherein R4 is trichloromethyl, 2-chloroisopropyl, 2-bromoisopropyl, 1-chlorocyclohexyl, 1-bromocyclohexylbenzene ring or substituted benzene ring; R5, R6, R7 are the following Any one of the structures or hydrogen;

[0036]

[0037] Step (2): Intermediate a is hydrolyzed under acidic or alkaline conditions to obtain 2,4,6-trimethylbenzene substituted by mono-, di-, and tri-carboxylates:

[0038]

[0039] Wherein R8, R9, R10 are any one of the following structures or hydrogen respectively;

[0040]

[0041] Step (3): the product in the step (2) generates an acyl...

Embodiment 1

[0064] Example 1 Preparation of ethyl 3-benzoyl-2,4,6-trimethylbenzoylphosphonate

[0065]Put 500g of 1,3,5-trimethylbenzene and 150g of anhydrous aluminum trichloride into a 2000mL four-neck flask under nitrogen protection, start stirring and cool down to 0-5°C, slowly add 140g of benzoyl chloride dropwise, and react After 2 hours, add 100g of aluminum trichloride, then slowly add 180g of trichloroacetyl chloride dropwise and keep the temperature below 10°C. After the dropwise addition, continue to react for 2 hours, add the reaction solution to 2000ml of dilute hydrochloric acid in ice water for hydrolysis , stand to separate the organic layer, distill off the unreacted 1,3,5-trimethylbenzene for recycling to obtain 3-benzoyl-2,4,6-trimethylbenzoic acid, dissolve it In 500ml of dichloromethane, 150g of thionyl chloride was added dropwise, and after 1 hour of reaction, the unreacted raw materials and solvent were removed under reduced pressure to obtain 3-benzoyl-2,4,6-trimet...

Embodiment 2

[0066] Example 2 Preparation of 6-benzoyl-2,4-di(ethyl benzoylphosphonate)-1,3,5-trimethylbenzene

[0067] Put 500g of 1,3,5-trimethylbenzene and 150g of anhydrous aluminum trichloride into a 2000mL four-neck flask under nitrogen protection, start stirring and cool down to 0-5°C, slowly add 140g of benzoyl chloride dropwise, and react After 2 hours, add 250g of aluminum trichloride, then slowly add 360g of trichloroacetyl chloride dropwise and keep the temperature below 10°C. After the dropwise addition, continue to react for 2 hours, add the reaction solution to 2000ml of dilute hydrochloric acid in ice water for hydrolysis , let stand to separate the organic layer. Unreacted 1,3,5-trimethylbenzene was distilled off under reduced pressure for recycling to obtain 3-benzoyl-2,4,6-trimethyl-1,5-dibenzoic acid, which was dissolved in 500ml In dichloromethane, 300g of thionyl chloride was added dropwise, and after 1 hour of reaction, the unreacted raw materials and solvent were r...

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Abstract

The invention provides a preparation method of macromolecular low-migration phosphine oxide UV-LED photoinitiators. The preparation method comprises the steps of using 1,3,5-trimethylbenzene as a rawmaterial, enabling the raw material to be subjected to a Friedel-Craft reaction with trichloro-acetic chloride or benzoyl chloride under the catalytic action of Lewis acid or solid superacid, hydrolyzing the obtained product under acidic or basic conditions to obtain a mono-, di-, or tricarboxy-substituted 2,4,6-trimethylbenzene, enabling the mono-, di-, or tricarboxy-substituted 2,4,6-trimethylbenzene to interact with phosphorus trichloride, thionyl chloride or phosgene to form acyl chloride, enabling the acyl chloride and ethoxyphenylphosphine or diethoxyphenylphosphine to be subjected to phosphine oxide reaction to obtain macromolecular low-migration phosphine oxide UV-LED photoinitiators; the invention claims a new structure of new type of macromolecular phosphine oxide initiators, andobtains a polyacyl chloride substituent by an innovative method, thereby obtaining a polyfunctional macromolecule phosphine oxide initiator.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, in particular to a preparation method of a class of macromolecular low migration phosphine oxide UV-LED photoinitiators. Background technique [0002] UV is also used as the abbreviation of radiation curing. UV is also UV ultraviolet light curing. It is cured by using medium and short waves (300-800 nanometers) in UV ultraviolet light. Stimulus changes to free radicals or cations, thereby initiating the process of polymerizing polymer materials (resins) containing active functional groups into insoluble / non-melting solid coating films. Phosphine oxide initiators such as TPO / 819 / TPO-L are widely used in UV-cured inks, coatings and other industries. However, with the safety requirements of food packaging, there are high requirements for the low migration of the initiators used. Energy saving and environmental protection and emerging UV-LED curing require initiators to have strong absorpt...

Claims

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Application Information

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IPC IPC(8): C07F9/53C07F9/32G03F7/004G03F7/027
Inventor 孙建郑康健
Owner TIANJIN MOSEN TECH CO LTD
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