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Monosubstituted and polysubstituted functional group aromatic ketone compounds, and preparation method and photopolymerization initiator thereof

A multi-functional group and photoinitiator technology, applied in the field of photopolymerization initiators and aromatic ketones, can solve the problems of reduced photopolymerization activity and high cost, and achieve the effect of reducing overall cost and improving photoinitiation efficiency

Pending Publication Date: 2021-12-31
湖南勤润新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example: while the KIP150 product overcomes the problem of VOCs, it also has new problems of greatly reduced photopolymerization activity (the photopolymerization activity is only 1 / 4 of that of Darocure1173) and a substantial increase in cost

Method used

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  • Monosubstituted and polysubstituted functional group aromatic ketone compounds, and preparation method and photopolymerization initiator thereof
  • Monosubstituted and polysubstituted functional group aromatic ketone compounds, and preparation method and photopolymerization initiator thereof
  • Monosubstituted and polysubstituted functional group aromatic ketone compounds, and preparation method and photopolymerization initiator thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1 Preparation Example 1

[0047]

[0048] The specific operation steps are:

[0049] Under the protection of nitrogen, put 300 liters of anhydrous chlorobenzene into the reactor, start stirring and lower the temperature, put 130 kg of aluminum trichloride into the reactor, keep stirring and cooling for 1 hour, and then add isophthalic acid dropwise into the reactor. 100 kg of butyryl chloride was added dropwise for 2 hours and the temperature of the kettle was kept lower than 5° C. After the dropwise addition was completed, stirring was continued for 6 hours to obtain a Friedel-crafts acylation intermediate. Then, the positive and secondary chlorination tanks are alternately set up in two stages in series. First, the positive and secondary chlorination tanks are respectively put into 400 kg of Friedel-crafts acylation intermediates, and chlorine gas is introduced into the positive tank. After the chlorine gas is absorbed by the positive tank, the exhaust gas ...

Embodiment 2

[0051] Embodiment 2 Preparation Example 2

[0052]

[0053] Under the protection of nitrogen, put 300 liters of anhydrous chlorobenzene into the reactor, start stirring and lower the temperature, put 130 kg of aluminum trichloride into the reactor, keep stirring and cooling for 1 hour, and then add cyclic 135 kg of hexanoyl chloride, the time for the dropwise addition was 2 hours and the temperature of the kettle was kept lower than 5° C. After the dropwise addition, the stirring was continued for 6 hours to obtain the Friedel-crafts acylation intermediate. Then, the positive and secondary chlorination tanks are alternately set up in two stages in series. First, the positive and secondary chlorination tanks are respectively put into 400 kg of Friedel-crafts acylation intermediates, and chlorine gas is introduced into the positive tank. After the chlorine gas is absorbed by the positive tank, the exhaust gas containing chlorine Pass it into the auxiliary kettle for environme...

Embodiment 3

[0055] Example 3 Preparation Example 3

[0056]

[0057] Mix concentrated nitric acid and concentrated sulfuric acid to prepare a mixed solution, add trichloromethylbenzene into the reaction kettle, stir and add the mixed solution dropwise at a temperature of 50-55°C, and the dropping time is 50 -60min, after the dropwise addition, continue to stir for 15-20h to obtain the intermediate trichloro compound, dissolve 100 kg of the purified trichloro compound in dry tetrahydrofuran, and add dropwise to 10.5 Suspension of kilograms of magnesium chips and dry tetrahydrofuran, slowly add 27 kilograms of dry acetone dropwise after the reaction is completed, stir for 2 hours, add water and continue stirring for 30 minutes, collect the organic phase and obtain nitro-substituted aromatic ketones through vacuum distillation Product, yield 78%.

[0058] 1 H NMR (300 MHz, CDCl3), δ: 1.36 (6H, s), 8.34 (2H, dd), 8.42 (2H, dd).

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Abstract

The invention belongs to the field of radiation curing new materials, and relates to an aromatic ketone compound, in particular to a monosubstituted or polysubstituted polyfunctional group aromatic ketone compound, a preparation method thereof and a photopolymerization composition containing an ethylenically unsaturated compound system, which takes the compound as an effective component. The invention provides monosubstituted and polysubstituted polyfunctional group aromatic ketone compounds. The polyfunctional group aromatic ketone compounds have a general formula structure as shown in (I). The invention also discloses a preparation method and an application of the polyfunctional aromatic ketone compound. According to the invention, industrial-grade raw materials which are low in cost and easy to obtain are used as a starting point to prepare the monosubstituted or polysubstituted functionalized aromatic ketone compound in a breakthrough way, and the compound is applied to a photoinitiator in radiation curing, so that the problems of toxicity and VOCs pollution of the photoinitiator are solved, and the economic competitiveness of the photoinitiator is strived; the overall cost is reduced, and the photo-initiation efficiency is improved.

Description

technical field [0001] The invention belongs to the field of radiation curing new materials and relates to an aromatic ketone compound. In particular, it relates to a class of single-substituted or multi-substituted polyfunctional aromatic ketone compounds, a preparation method thereof, and a photopolymerization initiator for an ethylenically unsaturated compound system containing such compounds as active ingredients. Background technique [0002] In ultraviolet (UV) radiation curable materials, some hydroxy ketones, bisaryl ketones and macromolecular hydroxy ketones are known to be used as radical photopolymerization initiators for systems containing ethylenically unsaturated compounds, listed below Darocur 1173, Irgacure184, Irgacure 907 and bisaryl ketones BP are all successful models of industrialization. [0003] [0004] However, these photoinitiators generally produce a series of volatile harmful organic compounds (Volatile Organic Compounds, referred to as VOCs) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/82C07C45/63C07C225/22C07C221/00C07C255/56C07C253/30C07C323/22C07C319/20C08F2/48
CPCC07C49/82C07C225/22C07C255/56C07C323/22C08F2/48C07C2601/14
Inventor 梁建军刘国龙侯占峰
Owner 湖南勤润新材料有限公司
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