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Benzotriazol derivatives containing o-nitro-diphenyl ethylene fragments

A technology of o-nitrostilbene and nitrostilbene, which is applied in the field of near-ultraviolet photosensitizers, can solve the problems of low initiation efficiency, inability to realize near-ultraviolet photopolymerization, etc. High absorption and polymerization efficiency

Inactive Publication Date: 2013-04-17
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional photoinitiators mainly include benzophenone, benzoin ether and its derivatives, etc. These photoinitiators have low initiation efficiency and have been widely used in actual production, but they can only absorb 200~300nm ultraviolet light , unable to achieve near-ultraviolet photopolymerization

Method used

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  • Benzotriazol derivatives containing o-nitro-diphenyl ethylene fragments
  • Benzotriazol derivatives containing o-nitro-diphenyl ethylene fragments
  • Benzotriazol derivatives containing o-nitro-diphenyl ethylene fragments

Examples

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Embodiment 1

[0040] When the benzotriazole derivative is 2-(2-hydroxyl-5-(2-nitro)styryl)-2H-benzotriazole, its synthesis steps are as follows:

[0041] 2-(2-Hydroxy-5-(2-nitro)styryl)-2H-benzotriazole

[0042] Add o-nitrophenylacetic acid (4mmol, 0.724g) and 2-(2-hydroxy-5-formaldehyde)-2H-benzotriazole (1mmol, 0.239g) into a three-necked flask, and drop them under constant stirring Add a small amount of hexahydropyridine, raise the temperature to 100°C under the protection of argon, reflux for 3 hours, then raise the temperature to 130°C and continue to reflux for 4 hours, separate with a silica gel column, use dichloromethane and cyclohexane with a volume ratio of 1:1 as Developing agent, obtains the 2-(2-hydroxyl-5-(2-nitro) styryl)-2H-benzotriazole of claim 1. Melting point 216°C, yield 40%. Its NMR H spectrum is as figure 1 as shown, 1 H-NMR(500MHz,DMSO-d6)δ(ppm):10.826(s,1H,Ar-OH),8.080-8.049(m,3H,Ar-H),7.979-7.951(t,2H,J=7Hz ,Ar-H),7.751-7.712(m,2H,Ar-CH=CH),7.558-7.502(m,3H,A...

Embodiment 2

[0044]When the benzotriazole derivative is 2-(2-methoxy-5-(2-nitro)styryl)-2H-benzotriazole, its synthesis steps are as follows:

[0045] 2-(2-Methoxy-5-(2-nitro)styryl)-2H-benzotriazole

[0046] Add 2-(2-hydroxy-5-(2-nitro)styryl)-2H-benzotriazole (2.5mmol, 0.895g) and potassium carbonate (5mmol, 0.69g) into a two-necked flask, After mixing evenly, add 60ml of dry acetone, add a small amount of phase transfer catalyst 18-C-6, add dropwise methyl iodide (10mmol, 0.4ml), stir at room temperature under argon protection for 24 hours, and the reaction is completed; remove the solid by filtration, remove the solvent under reduced pressure, Separation with a silica gel chromatographic column, with a volume ratio of 5:3 dichloromethane and cyclohexane as a developing agent, to obtain the 2-(2-methoxyl group-5-(2-nitro)styrene group of claim 1 )-2H-benzotriazole. The melting point is 148°C, and the yield is 95%. Its NMR H spectrum is as figure 2 as shown, 1 H-NMR (500MHz, DMSO-d...

Embodiment 3

[0048] Prepare 2-(2-hydroxy-5-(2-nitro)styryl)-2H-benzotriazole in N,N-dimethylformamide to make 1×10 -5 mol / L solution, measure its ultraviolet absorption spectrum, such as image 3 shown.

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Abstract

The invention relates to a benzotriazol derivative containing o-nitro-diphenyl ethylene fragments. The chemical structural general formula of the benzotriazol derivatives is shown in the specification; when a functional group R of the benzotriazol derivatives containing the o-nitro-diphenyl ethylene fragments is hydroxyl, the chemical structural formula of the benzotriazol derivatives is shown in the specification; and when the functional group R of the benzotriazol derivatives containing the o-nitro-diphenyl ethylene fragments is methoxyl, the chemical structural formula of the benzotriazol derivative is shown in the specification. When the diameter of the benzotriazol derivatives is between 300 and 400 nm, the benzotriazol derivatives have an obvious function of absorbing near ultraviolet, the benzotriazol derivatives and an assistant initiator triethanolamine are mixed together to form a photoinitiator system, and the benzotriazol derivatives can be used for performing near ultraviolet polymerization on acrylic acid type monomers in a solution.

Description

technical field [0001] The invention belongs to the field of near-ultraviolet photosensitizers, in particular to benzotriazole derivatives containing o-nitrostilbene fragments. Background technique [0002] UV-curable coatings refer to the photochemical reactions that occur after being irradiated by ultraviolet light, so that the coatings are quickly polymerized, cross-linked and cured. After entering the 1990s, with the continuous development of post and telecommunications, computer, printing and electronic industries and the continuous improvement of people's living standards, there has been a great demand for UV-curable coatings. Jianwen Xu et al. in the article "Progress in radiation curing-marketing and technology" (published in "Journal of Coatings Technology", "Journal of Coatings Technology", 2002,74(928):67-72) It is expected that UV curable materials will continue to grow at an average annual growth rate of 25%. The most important component in the free radical re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/20C08F2/50C08F120/14
Inventor 曹红霞院兴龚玉龙李红茹高放
Owner CHONGQING UNIV