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Polymerizable benzophenone photoinitiator and preparation method thereof

A technology of benzophenones and photoinitiators, which is applied in the field of polymerizable benzophenone photoinitiators and its preparation, can solve the problems of unfavorable application and popularization of polymerizable photoinitiators, long routes, and high costs. Achieve the effect of reducing surface migration and toxicity, simple synthesis method, and no post-processing

Pending Publication Date: 2022-07-29
江西五行材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the current methods for synthesizing polymerizable photoinitiators are relatively complicated, with long routes and high costs, which are unfavorable for the application and promotion of polymerizable photoinitiators.

Method used

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  • Polymerizable benzophenone photoinitiator and preparation method thereof
  • Polymerizable benzophenone photoinitiator and preparation method thereof
  • Polymerizable benzophenone photoinitiator and preparation method thereof

Examples

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preparation example Construction

[0045] The present invention also provides a preparation method of a polymerizable benzophenone photoinitiator, comprising the following steps:

[0046] The target products (I) and (II) are obtained by heating and stirring the benzophenone derivative A and the epoxy acrylate compound B in the presence of a catalyst and a polymerization inhibitor. The reaction formula is as follows:

[0047]

[0048] A is a benzophenone derivative, and B is an epoxy acrylate compound;

[0049] (I) is a mono-epoxy reaction product, (II) is a poly-epoxy reaction product;

[0050] Wherein, R1 represents oxygen, ethoxy of O(CH2)2O, and propoxy of O(CH2)3O.

[0051] The substitution of R1 in the present embodiment on benzophenone is mono-substituted or polysubstituted, and the position of R1 includes ortho-position, para-position and meta-position relative to the carbonyl position of benzophenone;

[0052] Described R2 represents hydrogen or methyl;

[0053] The n is greater than or equal to 1...

Embodiment 1

[0063] Take 100 mL, 0.1 mol (19.82 g) of 4-hydroxybenzophenone, 0.2 mol (28.43 g) of glycidyl methacrylate, 24 mg of p-hydroxyanisole, and 480 mg of triphenylphosphine, stir at 100 ° C for 6 h, pass The reaction was monitored by thin layer chromatography until the reaction of the starting material was complete. The resulting product was a yellow oily liquid comprising a mixture of mono- and poly-epoxy reaction products. The reaction product is processed by column chromatography to obtain a mono-epoxy reaction product. figure 1 and figure 2 They are the nuclear magnetic H spectrum and the nuclear magnetic C spectrum of the mono-epoxy reaction product prepared in this example. figure 1The chemical shifts of the peaks in the hydrogen spectrum 1H NMR (400 MHz, CDCl3) are δ7.81 (d, J = 8.8 Hz, 2H), 7.74 (d, J = 7.1 Hz, 2H), 7.56 (t, J =7.4 Hz, 1H), 7.46 (t, J = 7.5 Hz, 2H), 6.97 (d, J = 8.8 Hz, 2H), 6.15 (s, 1H), 5.62 (s, 1H), 4.43 – 4.36 (m, 2H) ), 4.32 (dt, J = 9.7, 3.9 Hz, ...

Embodiment 2

[0065] Take 100mL, 4-hydroxybenzophenone 0.1mol (19.82g), glycidyl methacrylate 0.2mol (28.43g), p-hydroxyanisole 24mg, benzyltrimethylammonium chloride 480mg, at 100 ℃ Stir for 6 h and monitor the reaction by thin layer chromatography until the reaction of the starting material is complete. The product was obtained as a yellow oily liquid.

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Abstract

The invention relates to a method for synthesizing and preparing a polymerizable benzophenone photoinitiator, which comprises the following step of: initiating an epoxy ring-opening reaction between a benzophenone derivative containing hydroxyl and an acrylate compound with an epoxy group under the action of a catalyst, so that the benzophenone compound has a polymerizable unsaturated bond. In the application of a photocuring coating, the mobility of a photoinitiator is reduced, the odor is reduced, the preparation method is simple, post-treatment and small molecule removal are avoided, and the atom utilization rate is high, so that the method has a wide application prospect in the field of photocuring.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a polymerizable benzophenone-based photoinitiator and a preparation method thereof. Background technique [0002] Photopolymer coatings are widely used in all aspects of life due to their high efficiency in industrial production. Such as wood furniture, packaging materials, dental filling materials, 3D printing materials, etc. [0003] Photopolymerization coatings are mainly composed of photoinitiators, oligomers, monomers and additives. Among them, the photoinitiator plays a crucial role in the polymerization speed and degree of polymerization. [0004] Common benzophenone photoinitiators have obvious defects and deficiencies, mainly due to the strong odor and the migration of residual photoinitiators in the material, which leads to certain toxicity. [0005] At present, many people have been conducting research in this field. Nie Jun et al. designed and synthesize...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C08F220/30C08F222/20C09D175/14C07C67/29C07C69/54
CPCC08F2/48C08F220/302C08F222/205C09D175/14C07C67/29C07C69/54
Inventor 王肖峰李天依陈奎达贾国忠
Owner 江西五行材料科技有限公司
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