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Conjugated benzophenone-containing triphenylamine dyes as well as synthesis and uses thereof

A technology of benzophenone triphenylamine and diethyl benzophenone phosphonate, which is applied in the directions of diaryl/triarylmethane dyes, diaryl/triarylmethane dyes, organic dyes, etc., can solve the problem of absorption Short wavelength, low initiation efficiency, etc., to achieve the effect of simple synthesis method and separation, convenient source of raw materials, and improved visible light initiation efficiency

Inactive Publication Date: 2008-07-23
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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  • Conjugated benzophenone-containing triphenylamine dyes as well as synthesis and uses thereof
  • Conjugated benzophenone-containing triphenylamine dyes as well as synthesis and uses thereof
  • Conjugated benzophenone-containing triphenylamine dyes as well as synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of (triphenylamine)-(benzophenone)-stilbene

[0048] The synthesis is carried out in three steps:

[0049] (1) Synthesis of 4-bromomethyl benzophenone

[0050] 1.0g 4-methylbenzophenone and 0.91g N-bromosuccinimide (NBS) (molar ratio 1:1) are mixed in a three-necked ground-necked flask, and a condenser is added to the CCl 4 Reflux for 6 hours, filter, recrystallize the solid in benzene / cycloethane, filter to obtain crystals, with a yield of 55%, ready for use;

[0051] (2) Synthesis of diethyl 4-benzophenone phosphonate

[0052] The ratio of 2.75g 4-bromomethylbenzophenone synthesized in the second step to 16.6g triethyl phosphonite (molar ratio 1:10)

[0053] (2) Synthesis of diethyl 4-benzophenone phosphonate

[0054] 2.75g of 4-bromomethylbenzophenone synthesized in the second step and 16.6g of triethyl phosphonite (molar ratio 1:10) were reacted at 145°C for some time, cooled, and the excess sulfonate was removed under reduced pressure. Triethyl phosphonate to...

Embodiment 2

[0058] Synthesis of (triphenylamine)-bis(benzophenone)-bis(stilbene)

[0059] (1) Synthesis of 4-bromomethyl benzophenone

[0060] The synthesis is carried out according to the first step in the implementation case 1;

[0061] (2) Synthesis of diethyl 4-benzophenone phosphonate

[0062] The synthesis is carried out according to the second step in the implementation case 1.

[0063] (3) Synthesis of (triphenylamine)-bis(benzophenone)-bis(stilbene)

[0064] Mix 6.64 g of 4-benzophenone phosphonic acid diethyl ester prepared in step (2) with 3.01 g of dialdehyde-based triphenylamine (molar ratio 2:1) and add them to a three-necked ground flask. Put it on the condenser, then dissolve it with 350ml of tetrahydrofuran solvent, add 1.5g of sodium ethoxide, stir for 20 hours at room temperature, filter the precipitate after cooling, evaporate the solvent in the filtrate, and separate with a silica gel column to obtain the compound of claim 1, yield 53%.

Embodiment 3

[0066] Synthesis of (triphenylamine)-tris(benzophenone)-tris(stilbene)

[0067] (1) Synthesis of 4-bromomethyl benzophenone

[0068] The synthesis is carried out according to the first step in the implementation case 1;

[0069] (2) Synthesis of diethyl 4-benzophenone phosphonate

[0070] The synthesis is carried out according to the second step in the implementation case 1.

[0071] (3) Synthesis of (triphenylamine)-tris(benzophenone)-tris(stilbene)

[0072] Mix 11.62g of diethyl 4-benzophenone phosphonate prepared in step (2) with 3.29 trialdehyde-based triphenylamine (molar ratio 3.5:1) and add them to a three-necked ground-necked flask. Condensing device, then dissolve with 500ml tetrahydrofuran solvent, add 2.38g of sodium ethoxide, stir at room temperature for 24 hours, after cooling, filter the precipitate, evaporate the solvent in the filtrate, and separate with silica gel column to obtain the compound of claim 1 with a yield of 50 %.

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Abstract

The invention relates to a conjugate dye with benzophenone triphenylamine and the preparation and application, in particular to the preparation of conjugate dye with benzophenone triphenylamine and the application in polymerization, belonging to the field of organic dye, the typical chemical formula of which is the right formula; wherein, in the molecular structural formula (I) R represents hydrogen, methyl, or is completely the same with the substituent in the other side of triphenylamine. The conjugate dye with benzophenone triphenylamine is prepared via 4-benzophenone diethyl phosphonate and the derivative of formaldehyde triphenylamine reacting in a glass vessel and alkaline condition, the maximum absorption of which is in visible light region, and can be used as photoinitiator forming a photosensitive system together with promoter triethanolamine to be the visible photopolymerization of vinyl monomer in solution, or be light cured material.

Description

Technical field [0001] The invention belongs to the field of visible light initiators, in particular to conjugated benzophenone triphenylamine-containing dyes and applications of their synthesis methods. Background technique [0002] In recent years, long-wavelength lasers such as Ar+ (488nm, 514nm), YAG (532nm), 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 of the methods is to link the ultraviolet photoinitiator to the visible light dye through a chemical bond. Koichi Kawamura discovered that the UV photoinitiator trichloro-s-triazine attached to visible light cyanine dyes can increase the absorption to 500-600nm. The title is: "Synthesis and Evaluation of a New Dye-Linked Bis(Trichloromethyl) )-1,3,5-triazine as a visible light polymerization initiator" (Synthesis and evalu...

Claims

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Application Information

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IPC IPC(8): C09B11/16C08F2/50
Inventor 高放胡女丹程志斌谢亭刘建李红茹
Owner CHONGQING UNIV
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