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Water-soluble photopolymerization initiator containing diphenyl sulfide ketone formate and preparation method of water-soluble photopolymerization initiator

A diphenyl sulfide ketoformic acid and photoinitiator technology, which is applied in the field of diphenyl sulfide ketoformate photoinitiators, can solve the problems of limited use, achieve good water solubility, convenient purification, and simple synthesis method Effect

Inactive Publication Date: 2021-03-05
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, such high-efficiency photoinitiators are insoluble in water, which also limits their use in such environmentally friendly solvents

Method used

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  • Water-soluble photopolymerization initiator containing diphenyl sulfide ketone formate and preparation method of water-soluble photopolymerization initiator
  • Water-soluble photopolymerization initiator containing diphenyl sulfide ketone formate and preparation method of water-soluble photopolymerization initiator
  • Water-soluble photopolymerization initiator containing diphenyl sulfide ketone formate and preparation method of water-soluble photopolymerization initiator

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of (A)-1 to (A)-18

[0026] The preparation process of compound (A)-1

[0027]

[0028] (a) Dissolve bromobenzene (0.1mol) in 100 ml of anhydrous dichloromethane, add anhydrous aluminum chloride (0.2mol) in batches, add monomethyl oxalyl chloride (0.1mol) dropwise at 0-10°C , the dropwise addition is completed in half an hour, the reaction is stirred at room temperature for 2-6 hours, the reaction is completed by pointing the plate, slowly added to ice water equal to the volume of the solvent, the organic layer is washed with deionized water, dried with anhydrous sodium sulfate, and can be prepared by distillation under reduced pressure Methyl 4-bromophenyl ketone formate was directly used in the next reaction.

[0029] (b) Methyl 4-bromophenyl ketone formate (0.05mol) and thiophenol (0.05mol) were dissolved in N, N-dimethylformamide (DMF) (100 ml), potassium carbonate (0.06 mol) and CuI (0.006mol), stirred and reacted at 140°C for 4 hou...

Embodiment 2

[0051] Embodiment 2: Synthesis of (A)-19 to (A)-24

[0052] The structural formula of compound (A)-19

[0053]

[0054] Add dimethyl sulfoxide (100 ml) and sodium 2-hydroxyethanesulfonate (0.05 mol) to (A)-1c (0.05 mol) obtained by the same operation as above, and stir the reaction at 90°C for 24 hours, and monitor the reaction by spot plate After the reaction was completed, 200 ml of saturated saline was added to the reaction solution, extracted three times with 200 ml of acetonitrile, dried over magnesium sulfate, concentrated under reduced pressure to obtain a light yellow solid, which was recrystallized with isopropanol to obtain (A)-19 , 90% yield.

[0055] (A)-20 was synthesize|combined by the same reaction except having changed sodium 2-hydroxyethanesulfonate into potassium 2-hydroxyethanesulfonate.

[0056] (A)-21 and (A)-22 were synthesized by the same reaction as (A)-20 and (A)-21, respectively, except that monoethyl oxalyl chloride was replaced with monomethyl ...

Embodiment 3

[0057] Embodiment 3: the synthesis of (A)-23

[0058]

[0059] (a) methyl 4-bromophenyl ketone formate (0.05mol) and 2,4,6-trimethylthiophenol (0.05mol) were dissolved in 100 ml of DMF, anhydrous potassium carbonate (0.06mol) was added and CuI (0.006mol), under the protection of nitrogen, stirred at 100°C for 4 h, spotted the plate to monitor the reaction, recovered DMF under reduced pressure, added the residue to 100 ml of water, and extracted the two parts with 100 ml of 1,2-dichloroethane. After drying with anhydrous sodium sulfate, concentrate and recrystallize with ethanol, the product is light yellow powder (A)-7b with a yield of 85%.

[0060] (b) (A)-7b (0.04mol) was added to 50 ml of anhydrous dichloromethane, anhydrous aluminum chloride (0.12mol) was added in portions, and chloroacetyl chloride was added dropwise at 0-10°C ( 0.04mo) of dichloromethane solution, and stirred at room temperature for 10 hours, point plate monitoring after the end of the reaction. The...

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Abstract

The invention relates to the technical field of new material organic chemicals, in particular to a water-soluble photopolymerization initiator containing diphenyl sulfide ketone formate and a preparation method of the water-soluble photopolymerization initiator. The invention particularly relates to a new compound which is shown as a formula (A) and takes diphenyl sulfide ketone formate as a corestructure. Hydrophilic groups such as quaternary ammonium salt, sulfonate radicals and the like are introduced into a core structure, so that the water solubility is realized. The synthesis steps aresimple, the preparation cost is low, the water solubility of the product is good, and the product can be directly used as a photolysis type photoinitiator and has a wide application prospect in the field of ultraviolet and visible light curing.

Description

【Technical field】 [0001] The invention relates to the technical field of new material organic chemicals, in particular to a class of diphenyl sulfide-based ketoformate photoinitiators whose water solubility is achieved by introducing hydrophilic groups such as quaternary ammonium salts and sulfonate groups into the core structure. . It has broad application prospects in the field of ultraviolet-visible light curing. 【Background technique】 [0002] Photoinitiator compounds are an important class of fine organic chemical materials. The photoinitiator compound that generates free radical active species under the irradiation conditions of ultraviolet light or visible light is the key species to induce the high-efficiency photopolymerization reaction of the system containing ethylenic unsaturation, so it is one of the important radiation curing formulation components. Among the many photoinitiator products that have been commercially applied, diphenyl sulfide compounds occupy a...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C319/20C07C323/62C07C67/343C07C69/738C08F2/48
CPCC07C67/343C07C319/14C07C319/20C07C323/62C08F2/48C07C69/738
Inventor 金明万德成
Owner TONGJI UNIV
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