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Macromolecule difunctional group alpha-hydroxy-ketone photoinitiator and preparation method thereof

A bifunctional, photoinitiator technology, applied in the field of macromolecular bifunctional α-hydroxyketone photoinitiator and its preparation, can solve the problems of restricted application, easy migration and volatilization of fragments, poor polymer compatibility, etc. The effect of high product yield, good compatibility and easy availability of raw materials

Inactive Publication Date: 2011-04-20
CHANGSHANG NEWSUN CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As small molecule photoinitiators, these two products inevitably have disadvantages such as poor compatibility with polymers, easy migration and volatilization of fragments after photolysis, which seriously restrict their application in the food and pharmaceutical industries. application

Method used

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  • Macromolecule difunctional group alpha-hydroxy-ketone photoinitiator and preparation method thereof
  • Macromolecule difunctional group alpha-hydroxy-ketone photoinitiator and preparation method thereof
  • Macromolecule difunctional group alpha-hydroxy-ketone photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 64g (0.5mol) of cyclohexanecarboxylic acid into a 500mL three-necked flask equipped with stirring, start stirring, and slowly add 30.3g (0.22mol) of phosphorus trichloride dropwise at a controlled temperature of 40°C-50°C, and drop it over in 2 hours , after the dropwise addition was completed, the reaction was continued for 4 hours, left to stand for stratification, and the residue in the lower layer was separated to obtain 70.9 g of cyclohexanoyl chloride, with a yield of 96.8%.

[0032] Take 72g (0.54mol) of anhydrous aluminum trichloride and place it in a reaction flask, add 139.4g (1.45mol) of fluorobenzene, stir, cool to 10°C and slowly add 70.9g (0.48mol) of cyclohexanecarbonyl chloride dropwise, add After completion, raise the temperature to 35°C-40°C and stir for 2 hours. After the reaction, slowly pour the reaction liquid into 10% hydrochloric acid solution, stir vigorously, separate the organic phase, wash, and recover the fluorobenzene by distillation, th...

Embodiment 2

[0037] Catechol was used instead of hydroquinone in Example 1 to obtain 46.5 g of intermediate 1,2-bis[4-cyclohexylmethanone)phenoxy]benzene with a yield of 44.2%.

Embodiment 3

[0039] Resorcinol was used instead of hydroquinone in Example 1 to obtain 60.2 g of intermediate m-1,3-bis[(4-cyclohexylketone)phenoxy]benzene with a yield of 57.1%.

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Abstract

The invention discloses a macromolecule difunctional group alpha-hydroxy-ketone photoinitiator shown in the following formula and a preparation method thereof. The preparation method comprises: firstly, preparing acyl chloride by hexahydrobenzoic acid; carrying out Friedel-Crafts acylations reaction on the acyl chloride and halogeno benzene in the presence of catalysis by lewis acid; then, in the presence of the catalysis, synthetizing a diketone midbody by ketone and bisphenol; and carrying out alpha-site halogenating and hydrolyzing on the diketone midbody to obtain a target product by. The macromolecule difunctional group alpha-hydroxy-ketone photoinitiator has good compatibility with resin, the volatility of the difunctional group alpha-hydroxy-ketone photoinitiator is greatly improved if compared with corresponding micromolecule photoinitiato, but the photo-initiation activity is not obviously reduced. Most importantly, because of the influence by conjugation, the photoinitiator disclosed by the invention has obvious red shift of absorption wavelength, has higher light absorption efficiency and has good application prospect in the material industries of paint, ink and the like.

Description

Technical field: [0001] The invention relates to the field of photoinitiators, in particular to a class of macromolecular bifunctional α-hydroxy ketone photoinitiators and a preparation method thereof. Background technique: [0002] As a "new technology for green industry in the 21st century", light curing technology has many advantages such as solvent-free, pollution-free, energy-saving, and resource-saving. It has been well applied and has increasingly shown good development prospects. More than 80% of all photocuring technology products are ultraviolet (UV) curing technology, and photoinitiators are an important component of UV curing systems, which determine the curing of the system. One of the main factors of speed and degree of cure. Hydroxyketone compounds are a class of highly efficient and widely used photoinitiators, and their representative products are DAROCUR 1173 and IRGACURE 184, and their structures are as follows: [0003] [0004] As small-molecule pho...

Claims

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Application Information

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IPC IPC(8): C08F2/48C07C49/84C07C45/64
Inventor 叶正培周谭陈健林海兰
Owner CHANGSHANG NEWSUN CHEM IND
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