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Para nitro toluylene near ultraviolet photosencitizer, synthesis and uses thereof

A technology of nitrostilbene and near-ultraviolet light, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as inability to realize near-ultraviolet photopolymerization, and achieve convenient and easy source of raw materials The effect of obtaining and yield is suitable

Inactive Publication Date: 2009-02-18
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 high initiation efficiency and have been widely used in actual production, but they can only absorb 200-300nm ultraviolet light. Unable to achieve near-ultraviolet light polymerization

Method used

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  • Para nitro toluylene near ultraviolet photosencitizer, synthesis and uses thereof
  • Para nitro toluylene near ultraviolet photosencitizer, synthesis and uses thereof
  • Para nitro toluylene near ultraviolet photosencitizer, synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (Diacetic acid)-(p-nitrostilbene)-ester is synthesized in two steps:

[0034] (1) Synthesis of 3,4-dihydroxy-p-nitrostilbene

[0035] Add compound p-nitrophenylacetic acid (5.0g), 3,4-dihydroxybenzaldehyde (5.7g) and hexahydropyridine (4.1ml) in a three-necked flask (p-nitrophenylacetic acid: 3,4-dihydroxybenzene Formaldehyde: Hexahydropyridine (1:1.5:1.5) mixed, heated to 100°C and refluxed for 3-4 hours, until no bubbles were generated. Then the temperature was raised to 130° C., and the reaction was continued for 2 hours. The reactant was recrystallized twice from hot absolute ethanol to obtain the target compound (5.0 g) with a yield of 70%.

[0036] (2) Synthesis of (diacetic acid)-(p-nitrostilbene)-ester

[0037] Add 3,4-dihydroxy-p-nitrostilbene (1.5g), acetic anhydride (3.3ml), triethylamine (5.8ml) into the three-necked flask (3,4-dihydroxy-p-nitrostilbene : acetic anhydride: triethylamine = 1:6:8) mixed, add a condensing device, then dissolve with 150ml of...

Embodiment 2

[0039] Synthesis of (dibenzoic acid)-(p-nitrostilbene)-ester

[0040] The synthesis proceeds in two steps

[0041] (1) Synthesis of 3,4-dihydroxy-p-nitrostilbene

[0042] Synthesis is carried out by step (1) in the implementation case 1.

[0043] (2) Synthesis of (dibenzoic acid)-(p-nitrostilbene)-ester

[0044] In the three-necked flask, add 3,4-dihydroxy-p-nitrostilbene (1.5g), benzoyl chloride (4.1ml), triethylamine (5.8ml) (3,4-dihydroxy-p-nitrostilbene Ethylene: benzoyl chloride: triethylamine = 1:6:8) mixed, add a condensing device, then dissolve with 150ml of dry tetrahydrofuran, reflux for 24 hours. After the reaction was completed, the precipitate was filtered off, and the crude product was obtained by passing through the column with dichloromethane, and recrystallized from benzene to obtain the target compound (1.1 g) as a yellow crystal, with a yield of 40%.

Embodiment 3

[0046] Will 1×10 -5 The (diacetic acid)-(p-nitrostilbene)-ester of mol / L is dissolved in methylene chloride, and its ultraviolet-visible absorption spectrum is measured, and its maximum absorption is at 337nm, such as figure 1 .

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Abstract

A photosencitizer has important functions of absorbing lights and causing light reaction. The invention discloses synthesis of the paranitrostilbene type photosencitizer containing ester bond and an application thereof. The peak value of the ultraviolet absorption band is about 340nm and the peak half-width is about 50nm, which fully satisfies the requirement of near ultraviolet absorption and can be used for near ultraviolet polymerization. The typical general formula of the chemical structure is shown as the right, wherein, the R in the molecular structural formula (I) and (II) represents methyl, ethyl, propyl, butyl or the aromatic substituent of benzene, naphthaline, anthracene and the like. In the compound (II), the two R groups are the same. The invention makes the peak value of the ultraviolet visible absorption blue shift to about 340nm through chemically modifying the paranitrostilbene type photosencitizer. The photosencitizer of the invention can be used as a photoinitiator to form a photosensitive system with the other accessory ingredient for the near ultraviolet polymerization of vinyl monomers in the solution or be used as curable material.

Description

technical field [0001] The invention belongs to the field of near-ultraviolet photosensitizers, in particular to p-nitrostilbene-based near-ultraviolet photosensitizers and their synthesis methods and applications. Background technique [0002] Ultraviolet curing coating (UVCC) is an environmentally friendly and energy-saving coating developed by Bayer in Germany in the late 1960s. The coating undergoes a photochemical reaction after being irradiated by ultraviolet light, so that the coating is rapidly polymerized, cross-linked and cured. In the early 1970s, my country began to research and develop UVCC, but the development was slow due to the limitations of raw materials and curing equipment. 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 (UVCC), and the introduction of for...

Claims

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Application Information

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IPC IPC(8): C08F2/46C07C205/42C07C201/12
Inventor 高放杨刘峰刘小娇杨龙王建超谢亭李红茹张胜涛
Owner CHONGQING UNIV
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