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P-nitro diphenyl ethylene dye containing diphenyl ketone via ether bond linkage as well as synthesis and application

A technology of benzophenone and stilbene, 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, suitable yield, simple synthesis method and separation

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

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 diphenyl ethylene dye containing diphenyl ketone via ether bond linkage as well as synthesis and application
  • P-nitro diphenyl ethylene dye containing diphenyl ketone via ether bond linkage as well as synthesis and application
  • P-nitro diphenyl ethylene dye containing diphenyl ketone via ether bond linkage as well as synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of (p-nitro-p-N-methyl-N-hydroxyethylstilbene)-(4-methylbenzophenone)-ether

[0047] The synthesis proceeds in three steps:

[0048] (1) p-nitro-p-N-methyl-N-hydroxyethyl stilbene

[0049]The ratio of 1.2g N-methyl-N-hydroxyethyl-benzaldehyde and 1.01g p-nitrophenylacetic acid (molar ratio 0.8: 1) is mixed in a three-necked ground flask, add a condensing device, and then add 0.72g Hexahydropyridine (molar ratio 1:1.25), reacted under heating at 110°C for 6 hours, dissolved in ethanol for recrystallization, filtered to obtain crystals, yield 65%: standby;

[0050] (2) Synthesis of 4-bromomethylbenzophenone

[0051] 1.0g 4-methylbenzophenone is mixed with 0.91g N-bromosuccinimide (NBS) (molar ratio 1: 1) in a three-necked ground-necked flask, and a condensing device is added. 4 Reflux for 6 hours and filter. The solid was recrystallized in benzene / cyclohexane, and the crystal was obtained by filtration, with a yield of 55%: for use;

[0052] (3) (p-nitro-p-...

Embodiment 2

[0055] Synthesis of (p-nitro-p-N-ethyl-N-hydroxyethylstilbene)-(4-methylbenzophenone)-ether

[0056] The synthesis proceeds in three steps:

[0057] (1) p-nitro-p-N-ethyl-N-hydroxyethyl stilbene

[0058] The ratio of 1.2g N-ethyl-N-hydroxyethyl-benzaldehyde to 0.83g p-nitrophenylacetic acid (molar ratio 0.9: 1) is mixed in a three-necked ground flask, add a condensing device, and then add 0.67 g of hexahydropyridine (molar ratio is 1:1.25), reacted under heating at 120°C for 6 hours, dissolved in ethanol for recrystallization, and filtered to obtain crystals with a yield of 67%: for later use;

[0059] (2) Synthesis of 4-bromomethylbenzophenone

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

[0061] (3) Synthesis of (p-nitro-p-N-ethyl-N-hydroxyethyl stilbene)-(4-methylbenzophenone)-ether

[0062] 0.8g p-nitro-p-N-ethyl-N-hydroxyethyl stilbene and 0.88g 4-bromomethylbenzophenone (molar ratio 1: 1.25) Mix and add to a three-n...

Embodiment 3

[0064] Synthesis of (p-nitro-p-N,N dihydroxyethylstilbene)-(4-methylbenzophenone)-ether

[0065] The synthesis proceeds in three steps:

[0066] (1) p-nitro-p-N, N-dihydroxyethyl-stilbene

[0067] 1.6g N, the ratio of N-dihydroxyethylbenzaldehyde and 1.39g p-nitrophenylacetic acid (molar ratio 1: 1) are mixed in three-necked ground flasks, add condensing device, then add 0.81g of six Hydropyridine (molar ratio is 1:1.25), reacted under heating at 130°C for 6 hours, dissolved in ethanol for recrystallization, filtered to obtain crystals, yield 66%: standby;

[0068] (2) Synthesis of 4-bromomethylbenzophenone

[0069] The synthesis is carried out according to the second step in the implementation case 1

[0070] (3) (p-nitro-to N, N dihydroxyethyl stilbene)-(4-methylbenzophenone)-ether synthesis

[0071] 0.9g p-nitro-p-N, N-dihydroxyethyl-stilbene and 1.89g 4-bromomethylbenzophenone (molar ratio 1: 2.5) prepared by steps (1) and (2) Mix and add to a three-necked ground-neck...

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Abstract

The invention relates to p-nitro stilbene dye with benzophenone via ether bond and the method of synthesis and application, in particular to the synthesis of p-nitro stilbenes dye connected with benzophenone via ether bond and the application under photopolymerization, belonging to the technical field of organic dye. The typical chemical structure is like the right equation (I). 4-bromonethyl benzophenone and the derivatives of p nitro stilbene compound with hydroxyl react in a glass vessel and in alkaline condition. The p nitro stilbenes dye with benzophenone is produced via ether bond, and the maximum absorption is in visible region. The invention can be used as photoinitiator combined with the promoter triethanolamine to form a photosensitive system, which is used as visible light polymerization of vinyl monomer in solution or solidifying material.

Description

technical field [0001] The invention belongs to the field of visible light initiators, in particular to a class of p-nitrostilbene organic dyes linked to benzophenone through ether bonds and applications 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 photopolymerization initiator"(Sy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/14C08F2/50
Inventor 高放谢亭程志斌胡女丹杨龙刘小娇刘建李红茹
Owner CHONGQING UNIV
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