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Diphenyl ketone containing nitryl stilbene dye formed with ester linkage, synthesis and application thereof

A technology of nitrostilbene and benzophenone, applied in the direction of styrene-based dyes, etc., can solve the problems of short absorption wavelength and low initiation efficiency, and achieve the effect of wide absorption band, convenient source of raw materials, and convenient adjustment

Inactive Publication Date: 2008-07-16
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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  • Diphenyl ketone containing nitryl stilbene dye formed with ester linkage, synthesis and application thereof
  • Diphenyl ketone containing nitryl stilbene dye formed with ester linkage, synthesis and application thereof
  • Diphenyl ketone containing nitryl stilbene dye formed with ester linkage, synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of (p-nitrostilbene)-(benzophenone acid)-ester

[0046] The synthesis proceeds in three steps:

[0047] (1) Synthesis of 4-nitro-4'-hydroxy-stilbene

[0048] The ratio of 1.2g p-Hydroxybenzaldehyde and 2.26g p-nitrophenylacetic acid (molar ratio 0.8: 1) is mixed in three-necked ground flasks, add condensing device, then add 0.72g hexahydropyridine (molar ratio 1: 1.25), reacted under heating at 110°C for 6 hours, dissolved in ethanol for recrystallization, and filtered to obtain crystals with a yield of 68%, and set aside;

[0049] (2) Synthesis of 2-acyl chloride benzophenones

[0050] 1.86g of 2-carboxybenzophenone and 11.8g of SOCl 2 (molar ratio 1:10) were mixed in a three-necked ground flask, stirred for 5 hours under heating, and unreacted SOCl was removed under reduced pressure. 2 , the viscous product was obtained without further purification, the yield was 95%, and it was used for subsequent use;

[0051] (3) Synthesis of (p-nitrostilbene)-(benzoph...

Embodiment 2

[0054] The synthesis of (4-nitro-3'-methyl-4'-hydroxyl toluene)-(benzophenone acid)-ester is carried out in three steps:

[0055] (1) Synthesis of 4-nitro-3'-methyl 4'-hydroxy-stilbene

[0056] The ratio of 1.36g 3-methyl-4 p-hydroxybenzaldehyde and 2.26g p-nitrophenylacetic acid (molar ratio 0.8: 1) is mixed in a three-necked ground flask, and a condensing device is added, and then 0.72g of hexahydro Pyridine (molar ratio 1:1.25), reacted under heating at 120°C for 6 hours, dissolved in ethanol for recrystallization, filtered to obtain crystals, yield 68%, and set aside;

[0057] (2) Synthesis of 2-acyl chloride benzophenones

[0058] Synthesis is carried out by the second step in the implementation case 1;

[0059] (3) Synthesis of (4-nitro-3'-methyl-4'-hydroxystilbene)-(benzophenone acid)-ester The step (1) 2.55g 4-nitro-3'- Methyl 4'-hydroxyl-stilbene is mixed with 2.44g 2-acyl chloride benzophenone (molar ratio 1:1) prepared in (2) and added to a three-necked ground-ne...

Embodiment 3

[0061] Synthesis of (4-nitro-3',4'-dihydroxystilbene)-bis(benzophenone acid)-ester

[0062] The synthesis proceeds in three steps:

[0063] (1) Synthesis of 4-nitro-3',4'-dihydroxy-stilbene

[0064] The ratio of 1.38g 3,4-dihydroxybenzaldehyde and 2.26g p-nitrophenylacetic acid (0.8: 1 in molar ratio) is mixed in three-necked grinding flasks, add condensing device, then add 0.72g hexahydropyridine ( Molar ratio 1:1.25), reacted under heating at 130°C for 6 hours, dissolved in ethanol for recrystallization, filtered to obtain crystals, yield 68%, and set aside;

[0065] (2) Synthesis of 2-acyl chloride benzophenones

[0066] Synthesis is carried out by the second step in the implementation case 1;

[0067] (3) Synthesis of (4-nitro-3', 4'-dihydroxystilbene)-bis(benzophenone acid)-ester

[0068] Step (1) 2.57g 4-i nitro-3', 4'-dihydroxy stilbene and 6.1g 2-acyl chloride benzophenone (molar ratio 1: 2.5) obtained from (2) are mixed and added to the third port ground-necked f...

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Abstract

The invention discloses a dioxybenzone containing anitro-diphenyl-styrene by an ester bond and a synthesizing method and application thereof, pertaining to the organic dyestuff field, and more particularly relates to a stilbene dye that is connected with the dioxybenzone by the ester bond and application thereof in light polymerization. A typical chemical structure general formula of the compound of the anitro-diphenyl-styrene is showed on the right, wherein, R in the molecular structural formula (I) represents hydrogen, methyl, ethyl, propyl, butyl, amyl, hexyl or is completely the same as a substituting group at 4th site. The dioxybenzone that goes through acyl chlorination reacts with derivative of anitro-diphenyl-styrene compound that contains hydroxyl under alkaline conditions, and the dioxybenzone containing anitro-stilbene dye is prepared by the ester bond. The maximum absorption of the stilbene dye is at a visible light area, initiates vinyl monomer polymerization effectively when being irradiated by visible light.

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 stilbene organic dyes through ester 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 (S...

Claims

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Application Information

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IPC IPC(8): C09B23/14C08F2/50
Inventor 高放谢亭程志斌胡女丹刘建罗自萍李红茹
Owner CHONGQING UNIV
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