Synthesis and application of p-methoxyl-containing Schiff base type visible light photosensitizer with conjugated structure

A technology of conjugated structure and p-methoxy group is used in the synthesis and application of visible light photosensitizers, which can solve the problems of poor solubility of dyes and need to improve the initiation efficiency, and achieves convenient and easy-to-obtain raw material sources and large molar extinction. Coefficients, Methods of Combining and Separating Simple Effects

Inactive Publication Date: 2009-12-16
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under the illumination of visible light, squaraine acts as a visible light photosensitizer to sensitize the ultraviolet photoinitiator iodonium salt, and generates free radicals to initiate the polymerization of ethylenic monomers through intermolecular photoelectron transfer. However, the solubility of such dyes is not very good. Good, and its triggering efficiency needs to be improved
Traditional photoinitiators include benzophenone, trichloromethyl-s-triazine, iodonium salt, benzoin ether and its derivatives, etc. These photoinitiators have high initiation efficiency, but they can only absorb 200-300nm Ultraviolet light, almost no absorption in the visible region

Method used

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  • Synthesis and application of p-methoxyl-containing Schiff base type visible light photosensitizer with conjugated structure
  • Synthesis and application of p-methoxyl-containing Schiff base type visible light photosensitizer with conjugated structure
  • Synthesis and application of p-methoxyl-containing Schiff base type visible light photosensitizer with conjugated structure

Examples

Experimental program
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Effect test

Embodiment 1

[0039] The synthesis of 4-(4-(4-methoxybenzylamino) styryl)-N,N-dimethylaniline is carried out in three steps:

[0040] (1) N,N-Dimethyl-4-(4-nitrostyryl)aniline

[0041] Put 2.733g of p-nitrophenylacetic acid and 1.500g of p-dimethylaminobenzaldehyde into a three-necked flask with a molar ratio of 1.5:1 and mix them, add a condensing device, and add 1.271g (about 1.5ml) dropwise under constant stirring. For hydropyridine, reflux at 100°C for 3 hours, then raise the temperature to 130°C and continue to reflux for 4-5 hours until no bubbles come out and stop the reaction. The solid obtained after the reaction was recrystallized twice with absolute ethanol, and dried in a vacuum oven for further use, with a yield of 95%.

[0042] (2) Synthesis of 4-(4-aminostyryl)-N,N-dimethylaniline

[0043] Add 0.750 g of the first step product N, N-dimethyl-4-(4-nitrostyryl) aniline and 1.263 g of stannous chloride dihydrate into a three-necked flask in a molar ratio of 1:2 and mix , under...

Embodiment 2

[0047] The synthesis of N, N-diethyl-4-(4-(4-methoxybenzylamino) styryl) aniline is carried out in three steps:

[0048] (1) 4-(4-nitrostyryl)-N,N-diethylaniline

[0049] Add 1.470g of p-nitrophenylacetic acid and 1.500g of p-4-(diethylamino)benzaldehyde in a three-necked flask with a molar ratio of 1.5:1 and mix them. Add a condensing device and add 1.271g (approx. 1.5ml) hexahydropyridine, reflux at 100°C for 3 hours, then raise the temperature to 130°C and continue to reflux for 4 to 5 hours until no bubbles emerge to stop the reaction. The dark red solid obtained after the reaction was recrystallized twice with absolute ethanol, and dried in a vacuum oven for further use, with a yield of 94%.

[0050] (2) 4-N, the synthesis of N-diethyl-(4-aminostyryl) aniline

[0051] Add 1.500 g of the first step product 4-(4-nitrostyryl)-N,N-diethylaniline and 2.045 g of stannous chloride dihydrate into a three-necked flask in a molar ratio of 1:2 and mix , under continuous stirring,...

Embodiment 3

[0055] Will 1×10 -5 The 4-(4-(4-methoxybenzylamino) styryl)-N,N-dimethylaniline of mol / L is dissolved in ethyl acetate, and its ultraviolet-visible absorption spectrum is measured, as figure 1 .

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Abstract

The invention relates to synthesis and application of p-methoxyl-containing Schiff base type visible light photosensitizer with a conjugated structure. A photosensitizer plays important roles of absorbing light and performing light action. The peak value of UV-visible absorption reaches over 380 nm, the half-peak width is about 100 nm, so that the visible light photosensitizer completely meets the requirement of visible light absorption and can be used for visible light polymerization. A general formula of a chemical structure of the visible light photosensitizer is shown as right, wherein compounds in the molecular structural formula (I) represent A:R1, R3:H, R2:OCH3, OCH2CH3, OCH2CH2CH3, OCH2CH2CH2CH3, N(CH3)2, N(CH2CH3)2, N(CH2CH2CH3)2, N(CH2CH2CH2CH3)2, N(Ph)2; B:(R1:H, OCH3, R2, R3:OCH3). The p-methoxyl-containing Schiff base type visible light photosensitizer with the conjugated structure is performed chemical modification to ensure that the peak value of the UV-visible absorption shifts to over 380 nm; and the p-methoxyl-containing Schiff base type visible light photosensitizer with the conjugated structure can be used as a visible light photosensitizer to form a photosensitive system used for visible light polymerization of vinyl monomers in solution with an ultraviolet initiator and other auxiliary agents, or can be used for a photocuring material.

Description

technical field [0001] The invention belongs to the field of visible photosensitizers, in particular to the synthesis and application of visible photosensitizers containing p-methoxy groups and having a conjugated Schiff base type. 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/50C07C251/24C07C249/02C08F120/14
Inventor 高放徐晓芳仲晓林李红茹张胜涛
Owner CHONGQING UNIV
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