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Novel bifunctional benzoyl formic acid hydroxy ketone ester compounds and photoinitiators containing the compounds

A kind of technology of hydroxy ketone group benzoylformate, compound, applied in the field of photoinitiator, can solve the problems such as unreported

Active Publication Date: 2014-04-09
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] We found that if the benzoylformate compound and the α-hydroxy ketone compound are combined to form a composite structure, and the original functional groups of the benzoyl formate and the α-hydroxy ketone compound are retained in the molecule, the obtained compound has Good photocuring performance, and this type of compound has not been reported

Method used

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  • Novel bifunctional benzoyl formic acid hydroxy ketone ester compounds and photoinitiators containing the compounds
  • Novel bifunctional benzoyl formic acid hydroxy ketone ester compounds and photoinitiators containing the compounds
  • Novel bifunctional benzoyl formic acid hydroxy ketone ester compounds and photoinitiators containing the compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Preparation of 4-(2-hydroxy-2-methylpropionyl)phenylbenzoylformate (Compound 1)

[0046]

[0047] 2-Hydroxy-2-methyl-1-(4-hydroxyphenyl)-1-propanone (22.5g, 0.125mol) was dissolved in 50ml of dichloromethane, triethylamine (19.0g, 0.188mol) was added, Under the condition of stirring, heat to 60 ℃, add dropwise methyl benzoylformate (20.5g, 0.125mol), keep warm after dropping, monitor the reaction with thin layer chromatography or liquid phase, after the reaction is complete, cool down to room temperature, use Wash with an equal volume of water, dry, and desolventize. The obtained residue is dissolved in dichloromethane, and purified on a silica gel column with petroleum ether / ethyl acetate as eluent to obtain a light yellow product.

[0048] Elemental analysis: Molecular formula C 18 h 16 o 5

[0049] Theoretical content: carbon element content 69.22%; hydrogen element content 5.16%

[0050] Measured content: carbon element content 69.11%; hydrogen elem...

Embodiment 2

[0051] Example 2: Preparation of 4-(2-hydroxy-2-methylpropionyl)phenylbenzoylformate (Compound 1)

[0052]

[0053] 1) Preparation of benzoyl chloride

[0054] Add benzoylformic acid (30.0g, 0.2mol) and 50ml of thionyl chloride into the reaction vessel, stir and reflux the reaction, recover the excess thionyl chloride after 2 hours, and the remaining raffinate can be extracted by vacuum distillation or The next reaction was carried out directly without purification.

[0055] 2) Preparation of phenyl benzoylformate

[0056] Dissolve the unpurified benzoyl chloride prepared above in 120ml of dichloromethane, add phenol (20.6g, 0.22mol) and 30ml of triethylamine and stir the reaction at room temperature. Phase monitoring reaction, after the reaction is complete, add an equal volume of water to wash, separate the organic phase, dry with anhydrous sodium sulfate, remove the solvent, distill under reduced pressure (3mmHg), collect the fraction at 145 ° C to obtain 40.7g of benz...

Embodiment 3

[0064] Example 3: Preparation of 2-(4-(2-hydroxy-2-methylpropionyl)phenoxy)ethylbenzoylformate (Compound 2)

[0065]

[0066] Dissolve methyl benzoylformate (16.4g, 0.1mol) in 50ml of toluene, add pyridine (15.8g, 0.2mol), heat to 70°C under stirring conditions, add Irgacure2959 (22.4g, 0.1mol), After dripping and keeping warm for about 20 hours, monitor the reaction with thin-layer chromatography or liquid phase. After the reaction is complete, cool down to room temperature, wash with an equal volume of water, dry, and remove the solvent. After the residue is dissolved in dichloromethane, use it on a silica gel column. Petroleum ether / ethyl acetate was used as the eluent to obtain a light yellow product.

[0067] Elemental analysis: Molecular formula C 20 h 20 o 6

[0068] Theoretical content: carbon element content 67.41%; hydrogen element content 5.66%

[0069] Measured content: carbon element content 67.23%; hydrogen element content 5.60%

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Abstract

The invention relates to a class of novel bifunctional benzoyl formic acid hydroxy ketone ester compounds and photoinitiators containing the compounds. The general formula I and II of the compounds are shown in the specification, wherein n is 0-90, R1 and R2 are selected from hydrogen, alkane or aryl groups with C1-C12 straight chains or branched chains and cyclic structures containing C5-C12 carbocycles, Ar is selected from phenyl rings or substituted phenyl rings wherein the substituent is one or more R, OR and halogen atom, and R is selected from alkyl, phenyl ring or benzyl with C1-C12 straight chains or branched chains. The compounds are suitable as photoinitiators of olefinic unsaturated compounds or mixtures containing the compounds for photopolymerization. The compounds can also be used with combination of another photoinitiator and / or other additives.

Description

technical field [0001] The invention describes a series of novel difunctional benzoylformic acid hydroxy ketone ester aromatic ketone compounds, a preparation method of the compounds and a photoinitiator containing the compounds used in the photopolymerization reaction of the ethylenically unsaturated compound system. Background technique [0002] Benzoylformyl esters and α-hydroxy ketones are two known highly efficient non-yellowing free radical photoinitiators, and some compounds have been commercialized: methyl benzoylformate (Darocur MBF ), 2-(2-oxy-2-phenyl-acetoxy-ethoxy)-ethyl hydroxyphenylacetate and 2-(2-oxy-2-ethoxy)hydroxyphenylacetate -Ethyl ester mixture (Irgacure754), 2-hydroxy-2-methyl-1-phenylacetone (Darocur1173), 1-hydroxycyclohexyl phenyl ketone (Irgacure184), 2-hydroxy-4'-(2-hydroxy Ethoxy)-2-methylpropiophenone (Irgacure 2959). [0003] [0004] Irgacure754 is a photoinitiator with better performance introduced by Ciba Company on the basis of the st...

Claims

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Application Information

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IPC IPC(8): C07C69/738C07C67/29C08F2/46C08G65/48
CPCC07C67/29C08F2/48C08G65/00C08G2650/04C07C69/738
Inventor 李钰武瑞张齐马小文石智铭毛桂红杨文杰赵国锋
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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