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A kind of macromolecular photoinitiator and its preparation method and application

A technology of photoinitiators and oxime esters, which is applied in the field of oxime ester macromolecular photoinitiators and its preparation, can solve the problems of affecting material performance, high mobility, poor resin compatibility, etc., and achieves simple preparation methods and high product quality. The effect of high purity

Active Publication Date: 2014-10-29
CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Macromolecular photoinitiators are designed and developed on the basis of traditional small molecule photoinitiators, such as: CN03813893X, CN101333278A, CN102020726A, this improvement solves the problem of poor compatibility between small molecule photoinitiators and resins, large VOC emissions, Migration and other issues, but the problem of low sensitivity of small molecule photoinitiators not only cannot be solved, but will become lower due to macromolecularization, resulting in incomplete curing of photocurable materials in use, or the need to add a large amount of light initiators, which greatly affect the properties of the material
[0004] The purpose of the present invention is to provide a macromolecular photoinitiator of oxime esters, which can solve the problem of generally low sensitivity of macromolecular photoinitiators at present, and can greatly overcome the deficiencies caused by small molecular photoinitiators, such as Poor resin compatibility, large VOC emissions, high mobility, etc.

Method used

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  • A kind of macromolecular photoinitiator and its preparation method and application
  • A kind of macromolecular photoinitiator and its preparation method and application
  • A kind of macromolecular photoinitiator and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of macromolecular photoinitiator TR-01 with the following structure

[0038]

[0039] Step (1): Preparation of 1-[4-(4-o-benzoylphenylthio)phenyl]-ethanone

[0040]

[0041] Drop into 22.3g diphenyl sulfide, 20.5g AlCl in the 500ml four-necked flask 3 (Grind finely), 100mL dichloromethane, stir, pass through argon protection, and cool in an ice bath. When the temperature drops to 0°C, start adding 11.3g of acetyl chloride dropwise, keep the temperature below 10°C, and finish adding in about 1.5h , continue to stir for 2h, then add 43gAlCl to the flask 3 (Grind finely), add dropwise a mixture of 19.5g phthalic anhydride and 20mL dichloromethane, control the temperature below 10°C, drop it in about 1.5h, then raise the temperature to 15°C, continue stirring for 2h, and discharge.

[0042] Post-processing:

[0043] Under stirring, slowly pour the material into 400g of ice water, use a separatory funnel to separate the lower layer of feed liquid, extrac...

Embodiment 2

[0063] Preparation of macromolecular photoinitiator TR-02 with the following structure

[0064]

[0065] Step (1): Preparation of an intermediate with the following structure

[0066]

[0067] In a 250ml four-necked flask, drop 1-[4-(4-o-formylphenylsulfanyl)phenyl]-ethanone-1-oxime [see Example 1 step (2) for the preparation method] 10g, bis Phenol A epoxy resin 4.4g, tetrabutylammonium chloride 0.1g, toluene 50mL, reflux reaction for 5h. Then add hot water and stir to separate the layers, remove the lower layer of water, wash with hot water once, then dehydrate the upper organic phase with molecular sieves, evaporate the solvent, and bake at 70°C for 5 hours to obtain 13.8 g of white solid dry product.

[0068] The product is tested by infrared spectroscopy (IR), and there is no ethylene oxide The band indicates that the reaction is complete.

[0069] Step (2): Preparation of TR-02

[0070] 11.6 g of the product of step (1), 11 g of acetic anhydride, and 50 mL of ...

Embodiment 3

[0074] Preparation of macromolecular photoinitiator TR-03 with the following structure

[0075]

[0076] For the specific preparation method and characterization method, please refer to Example 1.

[0077] Tested by gel permeation chromatography (GPC), the molecular weight Mw=1247.

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Abstract

The invention discloses an oxime ester photoinitiator. The photoinitiator has a chemical structure which is shown in a formula (I), (II), (III) or (IV), is high in application performance, high in light sensitivity, and can completely or partially overcome the problems of a micromolecular photoinitiator in use, such as low light sensing activity, poor compatibility of the micromolecular photoinitiator and resins, large emission of volatile organic components (VOC), more residues after photo-etching in a photoresist and high migration property. The invention also relates to a preparation method of the photoinitiator and application of the photoinitiator in a photocuring composition.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to an oxime ester macromolecular photoinitiator and its preparation method and application. Background technique [0002] As one of the key components of the photocurable composition, the photoinitiator is the most important factor affecting the photosensitivity of the photocurable composition. A large part of traditional photoinitiators are small molecular compounds, and there are many shortcomings in application, such as low photoactivity, poor compatibility with resins, large VOC emissions, and many residues after photolithography in photoresists. These shortcomings not only affect Material performance, but also pollute the environment. More importantly, the small molecule photoinitiator has mobility, and it is easy to ooze out from the cured film after UV curing, so it cannot meet the requirements of food packaging, pharmaceuticals and other industries. [0003] Macromolecules o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/06C07C323/62C07C319/20C08F2/48
Inventor 钱晓春胡春青王兵
Owner CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS