P-nitro azobenzene dye containing diphenyl ketone through ether bond linkage, synthesis and application thereof

A technology for nitroazobenzene and benzophenone, which is applied in directions such as etherification preparation, can solve problems such as low initiation efficiency and short absorption wavelength, and achieves convenient raw material sources, suitable yields, and easy-to-obtain raw material sources. Effect

Inactive Publication Date: 2010-01-13
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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  • P-nitro azobenzene dye containing diphenyl ketone through ether bond linkage, synthesis and application thereof
  • P-nitro azobenzene dye containing diphenyl ketone through ether bond linkage, synthesis and application thereof
  • P-nitro azobenzene dye containing diphenyl ketone through ether bond linkage, synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of (p-nitro-p-N-methyl-N-hydroxyethylazobenzene)-(4-methylbenzophenone)-ether

[0049] The synthesis proceeds in four steps:

[0050] (1) Synthesis of p-nitrodiazonium salt

[0051] 0.72g NaNO 2 Add 10% HCl solution with p-nitroaniline (1.38g) in an ice-water bath, stir vigorously at 0-5°C for 1 hour, filter, wash the precipitate twice with water, the yield is 92%, and set aside;

[0052] (2) Synthesis of p-nitro-p-N-methyl-N-hydroxyethyl azobenzene

[0053] 1.86g of p-nitrodiazonium salt was dissolved in concentrated hydrochloric acid containing 1.51g of N-methyl-N-hydroxyethylaniline and stirred at 0-5°C for 1 hour. Then use saturated sodium acetate solution to adjust the pH between 6-8, a red precipitate is formed, filter, wash twice with water, and then recrystallize in ethanol, the yield is 85%, and set aside;

[0054] (3) Synthesis of 4-bromomethylbenzophenone

[0055] 1.0g 4-methylbenzophenone is mixed with 0.91g N-bromosuccinimide (NBS) (molar rat...

Embodiment 2

[0059] Synthesis of (p-nitro-p-N-ethyl-N-hydroxyethylazobenzene)-(4-methylbenzophenone)-ether

[0060] The synthesis proceeds in four steps:

[0061] (1) Synthesis of p-nitrodiazonium salt

[0062] Synthesis is by the first step in embodiment 1;

[0063] (2) Synthesis of p-nitro-p-N-methyl-N-hydroxyethyl azobenzene

[0064] 0.72g NaNO 2 Add 10% HCl solution with p-nitro-N-ethyl-N-hydroxyethyl-aniline (1.65g) in an ice-water bath, stir vigorously at 0-5°C for 1 hour, filter, and wash the precipitate twice with water , 90% yield, standby;

[0065] (3) Synthesis of 4-bromomethylbenzophenone

[0066] The synthesis is carried out by the third step in the implementation case 1;

[0067] (4) Synthesis of (p-nitro-p-N-ethyl-N-hydroxyethyl azobenzene)-(4-methylbenzophenone)-ether

[0068] 0.314g p-nitro-to-N-methyl-N-hydroxyethyl azobenzene and 0.275g 4-bromomethylbenzophenone (molar ratio 1: 1) prepared by step (2), (3) ) mixed into a three-necked grinding-mouth flask, then di...

Embodiment 3

[0070] Synthesis of (p-nitro-p-N,N dihydroxyethylazobenzene)-(4-methylbenzophenone)-ether

[0071] The synthesis proceeds in four steps:

[0072] (1) Synthesis of p-nitrodiazonium salt

[0073] Synthesis is by the first step in embodiment 1;

[0074] (2) Synthesis of p-nitro-p-N-methyl-N-hydroxyethyl azobenzene

[0075] 0.72g NaNO 2 Add p-nitro-N,N-dihydroxyethyl-aniline (1.81g) to 10% HCl solution under ice-water bath, stir vigorously at 0-5°C for 1 hour, filter, and wash the precipitate twice with water , yield 92%, standby;

[0076] (3) Synthesis of 4-bromomethylbenzophenone

[0077] The synthesis is carried out by the third step in the implementation case 1;

[0078] (4) (p-nitro-p-N, N dihydroxyethyl azobenzene)-(4-methylbenzophenone)-ether synthesis

[0079] 0.33g p-nitro-p-N, N-dihydroxyethyl azobenzene and 0.5g 4-bromomethylbenzophenone (molar ratio 1: 2) prepared by steps (2), (3) Mix and add to a three-necked ground-necked flask for mixing, then dissolve with...

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Abstract

The invention discloses a dioxybenzone containing anitro-azobenzene dye by an ether bond and a synthesizing method and application thereof, pertaining to the organic dye field, and particularly relates to an anitro-azobenzene dye that is connected with the dioxybenzone by the ether bond and application thereof in light polymerization. A typical chemical structure general formula of the compound of the anitro-azobenzene dye is showed on the right, wherein, n in the molecular structural formula (I) represents 1-6, R represents methyl, ethyl, propyl, butyl, amyl, hexyl or is completely the same as a substituting group at the other side of N. 4-bromomethyl dioxybenzone reacts with derivative of anitro-azobenzene compound that contains hydroxyl under alkaline conditions in a glass container, and the dioxybenzone containing anitro-azobenzene dye is prepared by the ether bond. The maximum absorption of the anitro-azobenzene dye is at a visible light area; therefore, the invention can be used as photoinitiator and the photoinitiator and an addition agent, triethanolamine, form a photosensitive system that is used for polymerization of visible light of vinyl monomers in solution or as photo-curing material.

Description

technical field [0001] The invention belongs to the field of visible light initiators, in particular to the synthesis and application of a class of benzophenone-containing p-nitroazobenzene dyes through ether bonds. 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 Kawamur 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 photopolymerization initiator"(...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B43/28C08F2/50
Inventor 高放程志斌谢亭胡女丹刘建罗自萍段蓉斌李红茹
Owner CHONGQING UNIV
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