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Asymmetric compound taking triphenylamine as nucleus and containing benzophenone fragment and synthesis and application thereof

A technology of benzophenone and triphenylamine, which is applied in the field of visible light initiators, can solve the problems of short absorption wavelength and low initiation efficiency, and achieve the effects of wide absorption band, convenient raw material source, and easy-to-obtain raw material source

Inactive Publication Date: 2009-11-04
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under visible light irradiation, trichloro-s-triazine and visible light cyanine dye undergo photo-induced electron transfer to generate free radicals to initiate the polymerization of vinyl monomers. However, the synthesis of this type of compound requires many steps, and its initiation efficiency is not high. Trichloro S-triazine light often produces harmful gases such as chlorine, so it will be subject to many restrictions in practical applications
Benzophenone is a commercialized UV photoinitiator, but its absorption wavelength is very short, between 250-300nm, and there is almost no absorption in the visible region

Method used

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  • Asymmetric compound taking triphenylamine as nucleus and containing benzophenone fragment and synthesis and application thereof
  • Asymmetric compound taking triphenylamine as nucleus and containing benzophenone fragment and synthesis and application thereof
  • Asymmetric compound taking triphenylamine as nucleus and containing benzophenone fragment and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The synthesis of 4-(4-benzophenone)-4'-(styrene)-triphenylamine is carried out in six steps:

[0054] (1) Bis-(4-formylphenyl)-aniline

[0055] Add 25ml of N,N-dimethylformamide into a 250ml three-necked flask under an ice-water bath, and slowly add 20ml of phosphorus oxychloride dropwise under the protection of Ar gas. After the dropwise addition, 3 g of triphenylamine was added, and the reaction was refluxed at 95° C. for 4 h. After the reaction is completed, cool to room temperature, add 200ml of distilled ice water, and adjust the pH to 7-8. Pour into 200ml of dichloromethane for extraction, then extract with distilled water 3 times, and dry over anhydrous sodium sulfate. Dichloromethane was evaporated to dryness, and the product was separated by a chromatographic column, concentrated, and recrystallized (ethyl acetate:cyclohexane=1:1) to obtain a yellow solid with a yield of 43.81%, which was set aside;

[0056] (2) Synthesis of diethyl phenylphosphonate

[005...

Embodiment 2

[0067] Synthesis of 4-(4-benzophenone)yl-4'-(4-methylstyrene)yl-triphenylamine

[0068] (1) Bis-(4-formylphenyl)-aniline

[0069] Synthesis is carried out by the first step of embodiment 1;

[0070] (2) Synthesis of 4-methylphenylphosphonic acid diethyl ester

[0071] Mix 0.57g of 4-methylbenzyl bromide and 3.02g of triethyl phosphite in a three-necked ground flask with a molar ratio of 1:10, add a condensing device, and react at 130°C-160°C for 6 hours. Excessive triethyl phosphite was distilled under pressure to obtain diethyl 4-methylphenylphosphonate with a yield of 80%;

[0072] (3) Synthesis of N-phenyl-N-(4-methylstilbene)-4-benzaldehyde

[0073] Add 1.50g of bis-(4-formylphenyl)-aniline and 0.82g of 4-methylphenyl phosphate diethyl ester (molar ratio 3:1) synthesized in step (1) into the three-necked flask, and use Dissolve 100-500 times the volume ratio of tetrahydrofuran solvent, add 0.34g potassium tert-butoxide, react for 12 hours under the protection of Ar gas...

Embodiment 3

[0081] Synthesis of 4-(4-benzophenone)yl-4'-(3,4,5-trimethoxystyrene)yl-triphenylamine

[0082] The synthesis proceeds in six steps:

[0083] (1) Synthesis of two-(4-formylphenyl)-aniline

[0084] Synthesis is carried out by the first step of embodiment 1;

[0085] (2) Synthesis of 3,4,5-trimethoxyphenyl phosphonic acid diethyl ester

[0086] Mix 1.02g of 3,4,5-trimethoxyphenyl bromide and 4.47g of triethyl phosphite into a three-necked flask at a molar ratio of 1:10, add a condensing device, and react at 130°C-160°C for 6 Hours, the excess triethyl phosphite was distilled under reduced pressure to obtain 3,4,5-trimethoxyphenyl phosphonic acid diethyl ester with a yield of 70%, which was set aside;

[0087] (5) Synthesis of N-phenyl-N-(3,4,5-trimethoxystilbene)-4-benzaldehyde

[0088] Add 0.60g of 3,4,5-trimethoxyphenyl phosphonic acid diethyl ester and 0.23g of basic catalyst sodium methoxide (molar ratio 1:2.5) into the three-necked flask, stir under ice-water bath for hal...

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Abstract

An asymmetric compound taking triphenylamine as nucleus and containing benzophenone fragment and a synthesis and an application thereof, belonging to the field of organic dye, in particular relating to the application of the asymmetric compound taking triphenylamine as nucleus and containing benzophenone fragment in photopolymerization. The general formula of the typical chemical structure is shown in formula (I), wherein compound in molecular structural formula (I) represents A: R1, R2: H, R3: CH3, OCH3, OCH2CH3, OCH2CH2CH3, OCH2CH2CH2CH3, N(CH3)2, N(CH2CH3)2, N(CH2CH2CH3)2, N(CH2CH2CH2CH3)2, CN, F, NO2; B: (R1, R2,:, R3: OCH3). 4-diethyl benzophenone phosphonate and derivative containing 4-aldehydegroup-triphenylamine compound react in a glass vessel under the alkaline condition to prepare the asymmetric non-conjugated compound taking triphenylamine as nucleus and containing benzophenone fragment, the absorption maximum thereof is at visible region, the organic dye can be used as light trigger to form a photosensitive system together with auxiliary agent trolamine to be used for visible light polymerization of alkene monomer in solution or to be used as photocuring material.

Description

technical field [0001] The invention belongs to the field of visible light initiators, in particular to the application of asymmetric organic dyes containing benzophenone fragments with triphenylamine as the core and a synthesis method thereof. Background technique [0002] In recent years, long-wavelength lasers such as Ar+ (488nm, 514nm), YAG (532nm), and He-Ne (633nm) have been widely used in computer-to-plate, photocuring, two-photon photopolymerization, and high-density digital optical storage. Efficient visible light photoinitiators have become an important field of optical information research. One approach is to attach a UV photoinitiator to a visible light dye through a chemical bond. Koichi Kawamura found that the ultraviolet photoinitiator trichloro-s-triazine attached to the visible light cyanine dye can increase the absorption light to 500-600nm. The title is: "Synthesis and evaluation of a new dye-linked bis(trichloromethyl )-1,3,5-triazine as visible light p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/14C08F2/50
Inventor 高放刘建李红茹张胜涛杨龙王坤
Owner CHONGQING UNIV
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