Para nitro toluylene visible light photosencitizer, synthesis and uses thereof

A technology of nitrostilbene and visible light, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of no absorption and low initiation efficiency, and achieve suitable yield, convenient source of raw materials, and The effect of readily available sources

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

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
Traditional photoinitiators mainly include benzophenone, benzoin ether and its derivatives, etc. These photoinitiators have high initiation efficiency, but they can only absorb 200-300nm ultraviolet light, and there is almost no absorption in the visible light region.

Method used

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  • Para nitro toluylene visible light photosencitizer, synthesis and uses thereof
  • Para nitro toluylene visible light photosencitizer, synthesis and uses thereof
  • Para nitro toluylene visible light photosencitizer, synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of (p-nitrostilbene)-(toluene)-ether

[0035] The synthesis proceeds in two steps:

[0036] (1) Synthesis of 4-hydroxyl-p-nitrostilbene

[0037] Add compound p-nitrophenylacetic acid (5.0g), 4-hydroxybenzaldehyde (5.1g) and hexahydropyridine (3.5g or 4.1ml) in a three-necked flask (p-nitrophenylacetic acid: 4-hydroxybenzaldehyde: six Hydropyridine (1:1.5:1.5) mixed, heated to 100 ℃ reflux reaction for 3-4 hours, until no bubbles are 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 (4.8 g) with a yield of 72%.

[0038] (2) Synthesis of (p-nitrostilbene)-(toluene)-ether

[0039] Add compound 4-hydroxyl-p-nitrostilbene (2.0g), benzyl bromide (2.1g or 1.5ml), potassium carbonate (2.3g) into a three-necked flask (4-hydroxyl-p-nitrostilbene: benzyl Bromine: Potassium carbonate (1:1.5:2) was mixed, then dissolved in 150m...

Embodiment 2

[0041] Synthesis of (p-nitrostilbene)-(xylene)-ether

[0042] The synthesis proceeds in two steps

[0043] (1) Synthesis of 3,4-dihydroxy-p-nitrostilbene

[0044] 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%.

[0045] (2) Synthesis of (p-nitrostilbene)-(xylene)-ether

[0046]Add compound 3,4-dihydroxy-p-nitrodiphenylethylene (2.0g), benzyl bromide (4.0g or 2.8ml), potassium carbonate (4.5g) (4-hydroxyl-p-nitrodiphenyl Ethylene: benzyl bromide: potassium carbonate (1:3:4) were mixed, then dissolved in 150ml ...

Embodiment 3

[0048] Will 1×10 -5 The (p-nitrostilbene)-(toluene)-ether of mol / L is dissolved in methylene chloride, and its ultraviolet-visible absorption spectrum is measured, and its maximum absorption is at 381nm, 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 p-nitro-stilbene type photosencitizer containing ester bond and an application thereof. The peak value of the ultraviolet visible absorption band can reach at least 380nm and the peak half-width is about 100nm, which fully satisfies the requirement of visible light absorption and can be used for visible light polymerization. The typical general formula of the chemical structure is shown as the above. In the molecular structural formula (I), the R group represents the aromatic substituent of benzene, naphthaline, anthracene and the like. In the molecular structural formula (II), the R group represents alkyls, such as methyl, ethyl, propyl, butyl and the like and the aromatic substituent of benzene, naphthaline, anthracene and the like, wherein, the two R groups are the same. The invention makes the peak value of the ultraviolet visible absorption shift to at least 380nm 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 visible light polymerization of vinyl monomers in the solution or be used as curable material.

Description

technical field [0001] The invention belongs to the field of visible light photosensitizers, in particular to p-nitrostilbene visible light photosensitizers and their synthesis methods and applications. Background technique [0002] Efficient visible light photoinitiator system is an important field in photopolymerization research. With the advancement of laser imaging and photocuring technology, photosensitive polymer materials such as photoresists, photocurable inks, coatings and photosensitive printing plates have been developed rapidly. A key technology of these photofunctional materials is how to extend the spectral response range to long wavelengths and obtain high sensitivity. For this reason, the development of a new type of photopolymerization initiation system with high sensitivity and low energy, which is sensitive to long-wavelength visible laser light, has become a hot research topic today. One way to shift the spectral absorption of the initiator to the long-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/50C07C205/35C07C201/12
Inventor 高放杨刘峰杨龙刘小娇王建超彭华勇谢亭李红茹张胜涛
Owner CHONGQING UNIV
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