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Carbazole cyclic derived type aromatic ketone compound as well as preparation method and photo initiator thereof

A carbazole ring and compound technology, applied in the field of photoinitiators, can solve the problems of low residual odor and need to be improved, and achieve the effects of reducing residual odor, enhancing photoinitiating activity and photocrosslinking degree, and improving solubility

Inactive Publication Date: 2011-11-23
SHENZHEN UV-CHEMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the performance of the photoinitiators disclosed in the above documents still needs to be improved in terms of practical application needs, especially in terms of higher initiating activity, lower residual odor, and compatibility with different resin systems.

Method used

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  • Carbazole cyclic derived type aromatic ketone compound as well as preparation method and photo initiator thereof
  • Carbazole cyclic derived type aromatic ketone compound as well as preparation method and photo initiator thereof
  • Carbazole cyclic derived type aromatic ketone compound as well as preparation method and photo initiator thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: The preparation method of carbazole ring-derived polyfunctional aromatic ketone compound---aminoketone (compound of general formula II).

[0032]

[0033] The first step.1, the synthesis of 6-biscarbazole hexane: under nitrogen protection, get 40.3 grams of carbazole and place in 500 milliliters of dry DMF, add 10.6 grams of NaH (60% paraffin oil dispersion) in small batches powder. After stirring and reacting at room temperature for 2 hours, 29.4 g of 1,6-dibromohexane was added dropwise, and the stirring reaction was continued overnight. The reaction solution was poured into half-saturated brine, extracted 3 times with ethyl acetate, the organic phases were combined, washed 2 times with water, dried over magnesium sulfate, the solvent was spin-dried, and the residue was recrystallized in glacial acetic acid to obtain 42.2 grams of a near-white solid product, 84 % yield.

[0034] The second step. Friedel-Crafts acylation reaction of 1,6-biscarbazole hexan...

Embodiment 2

[0036] Embodiment two: the preparation method of aryl ketone

[0037]

[0038] With reference to the second step conditions of Example 1, under the protection of nitrogen, 13.8 grams of 1,6-biscarbazole hexane and 30.0 grams of 1,3,5-mesoyl chloride were placed in 500 milliliters of dichloroethane. Slowly add 24.2 g of anhydrous aluminum trichloride powder under strong stirring (note that the HCl gas emitted by the reaction is absorbed with lye), and the mixed solution is stirred and reacted at room temperature for 10 hours, and then weakly refluxed for 2 hours. The system was cooled to room temperature, diluted with 700 ml of dichloroethane and poured into a large amount of 2N dilute hydrochloric acid under rapid stirring, the solid was filtered off, the filtrate was layered, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, evaporated After the solvent, the crude product was recrystallized in ethanol to obtain 24.5 g of the aryl ke...

Embodiment 3

[0039] Embodiment three: the preparation method of aminoketone

[0040]

[0041] The first step: under the protection of nitrogen, take 13.6 grams of 1,6-biscarbazole hexane and 13.1 grams of 1,3,5-mesoluoyl chloride in 700 ml of dichloroethane, and slowly add them under vigorous stirring 10.2 grams of anhydrous aluminum trichloride powder (note the HCl gas emitted by the absorption reaction with lye), the mixed solution was stirred and reacted for 6 hours, and then 7.7 grams of isobutyryl chloride and 11.1 grams of anhydrous aluminum trichloride powder were added successively, and the reaction system After stirring overnight, it was diluted with 400 ml of dichloroethane, the mixture was poured into a large amount of 2N dilute hydrochloric acid, the solid was filtered off, the filtrate was layered, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the crude product was obtained after distilling off the solvent. Recrystallization ...

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Abstract

The invention discloses a carbazole cyclic derived type polyfunctional aromatic ketone compound as shown in general structural formulas I and II described in the specification as well as a preparation method thereof and application of the carbazole cyclic derived type polyfunctional aromatic ketone compound as an alkenyl unsaturated system free-radical photopolymerization initiator.

Description

【Technical field】 [0001] The invention relates to the technical field of photoinitiators, in particular to a class of carbazole ring-derived polyfunctional aromatic ketone compounds, a preparation method thereof and the use of the compounds as radical photopolymerization initiators containing ethylenically unsaturated systems. 【Background technique】 [0002] Photoinitiator is the key component of UV radiation curable materials. Most of the existing photoinitiator compounds are classified into aromatic ketone compounds from the chemical structure. When the color of the UV curing system is dark, the system itself and the photoinitiator Inevitably, there will be a problem of competing light absorption, thus significantly inhibiting the photoinitiating activity and causing difficult or incomplete curing. This phenomenon is especially serious in dark ink systems with thick coatings, and it is an outstanding problem that needs to be solved urgently in this technical field. challen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D209/86C08F2/48
Inventor 王智刚赵新阳王亚朋宋怀海
Owner SHENZHEN UV-CHEMTECH CO LTD
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