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Non-conjugated p-nitro diphenyl ethylene dye containing benzophenone via ether linkage as well as synthesis and uses thereof

A technology of nitrostilbene and benzophenone, which is applied in the direction of styrene-based dyes, nitro/nitroso dyes, organic dyes, etc., can solve the problems of low initiation efficiency and short absorption wavelength, and achieve raw material The effect of convenient source, wide absorption band, and easy source of raw materials

Inactive Publication Date: 2010-05-26
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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  • Non-conjugated p-nitro diphenyl ethylene dye containing benzophenone via ether linkage as well as synthesis and uses thereof
  • Non-conjugated p-nitro diphenyl ethylene dye containing benzophenone via ether linkage as well as synthesis and uses thereof
  • Non-conjugated p-nitro diphenyl ethylene dye containing benzophenone via ether linkage as well as synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of (p-nitro-stilbene)-(4-methylbenzophenone)-ether

[0045] The synthesis proceeds in three steps:

[0046] (1) 4-nitro-4'hydroxy-stilbene

[0047] 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 1.06g of 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 66%, and set aside;

[0048] (2) Synthesis of 4-bromomethylbenzophenone

[0049] 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, filter, recrystallize the solid in benzene / cycloethane, filter to obtain crystals, the yield is 55%, and set aside;

[0050] (3) (p-nitrostilbene)-(4-methylbenzophenone)-ether

[0051] With step (1), the...

Embodiment 2

[0053] Synthesis of (4-nitro-3'-methylstilbene)-(4-methylbenzophenone)-ether

[0054] The synthesis proceeds in three steps:

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

[0056] The ratio of 1.36g 3-methyl-4-hydroxybenzaldehyde and 2.4g p-nitrophenylacetic acid (molar ratio 0.8: 1) is mixed in a three-necked ground flask, add a condensing device, and then add 1.06g of hexahydro Pyridine (molar ratio is 1:1.25), reacted under heating at 120°C for 6 hours, dissolved in ethanol for recrystallization, filtered to obtain crystals, yield 67%, and set aside;

[0057] (2) Synthesis of 4-bromomethylbenzophenone

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

[0059] (3) Synthesis of (4-nitro-3'-methylstilbene)-(4-methylbenzophenone)-ether

[0060] 2.55g of 4-nitro-3'-methylstilbene and 3.3g of 4-bromomethylbenzophenone (molar ratio 1:1.2) prepared in steps (1) and (2) were mixed and added to the third port Mix in a ground-n...

Embodiment 3

[0062] Synthesis of (p-nitrostilbene)-[3,4-bis(methylbenzophenone)]-ether

[0063] The synthesis proceeds in three steps:

[0064] (1) p-Nitro-3',4'-dihydroxystilbene

[0065] The ratio of 1.38g 3,4-dihydroxybenzaldehyde and 2.4g p-nitrophenylacetic acid (0.8: 1 in molar ratio) is mixed in three-necked ground flasks, add condensing device, then add 1.06g of hexahydropyridine ( The 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%, which was set aside;

[0066] (2) Synthesis of 4-bromomethylbenzophenone

[0067] Synthesis is carried out by the second step in the implementation case 1;

[0068] (3) Synthesis of (p-nitrostilbene)-[3,4-bis(methylbenzophenone)]-ether

[0069] 2.57g 4-nitro-3', 4'-dihydroxy stilbene and 5.5g 4-bromomethylbenzophenone (molar ratio 1: 2) were mixed with step (1), (2) prepared Add it into a three-necked ground-necked flask and mix it, ...

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Abstract

The invention relates to a non-conjugate dye with benzophenone p-nitro stilbene and the preparation and application, in particular to the preparation of non-conjugate dye with benzophenone p-nitro stilbene 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) the n represents 0 to 6, and R represents hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, or is completely the same with the substituent in the forth degree. The non-conjugate dye with benzophenone p-nitro stilbene is prepared by ether bond via 4-benzophenone diethyl phosphonate and the derivative of p-nitro stilbene compound with hydroxyl reacting in a glass vessel and in alkaline condition, themaximum 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 the synthesis and application of a class of non-conjugated benzophenone-containing p-nitrostilbene dyes. 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"(Synthe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/14C09B51/00C08F2/50
Inventor 高放谢亭程志斌胡女丹刘建李红茹
Owner CHONGQING UNIV
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