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Synthesis and application of o-hydroxy-containing Schiff base type visible light photosensitizer with conjugated structure

A technology of conjugated structure and Schiff base type, which is applied in the synthesis and application of visible light photosensitizers, can solve the problems that the initiation efficiency needs to be improved, the dye solubility is not very good, etc., and the source of raw materials is convenient and easy to obtain, and the large molar extinction Coefficients, methods of synthesis, and effects of separating simplicity

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, biimidazole, etc. These photoinitiators have high initiation efficiency, but they can only absorb 200-300nm ultraviolet light, almost no absorption in the visible light region

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of 2-(4-(4-(dimethylamino)styryl)phenylimino)methyl)phenol

[0042] The synthesis proceeds in three steps:

[0043] (1) N,N-Dimethyl-4-(4-nitrostyryl)aniline

[0044] Put 1.8222g of p-nitrophenylacetic acid and 1.000g 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 0.847g (about 1ml) of hexahydrogen dropwise under constant stirring For pyridine, 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%.

[0045] (2) Synthesis of 4-(4-aminostyryl)-N,N-dimethylaniline

[0046] Add 0.500 g of the first step product N, N-dimethyl-4-(4-nitrostyryl) aniline and 0.842 g of stannous chloride dihydrate into a three-necked flask in a molar ratio ...

Embodiment 2

[0050] Synthesis of 2-(4-(4-(diphenylamino)styryl)phenylimino)methyl)phenol

[0051] The synthesis proceeds in three steps:

[0052] (1) 4-(4-nitrostyryl)-N,N-diphenylaniline

[0053] 0.980g of p-nitrophenylacetic acid and 1.000g of p-4-(diphenylamino)benzaldehyde were mixed in a three-necked flask with a molar ratio of 1.5:1, and a condensing device was added, and 0.847g ( About 1ml) 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 come out 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. The yield was 98%.

[0054] (2) 4-N, the synthesis of N-diphenyl-(4-aminostyryl) aniline

[0055] Add 0.500 g of the first step product 4-(4-nitrostyryl)-N,N-diphenylaniline and 0.812 g of stannous chloride dihydrate into a three-neck flask in a molar ratio of 1:2 and mix , under continu...

Embodiment 3

[0059] Synthesis of 2-(4-(4-(3,4,5-trimethoxystyryl)phenylimino)methyl)phenol

[0060] The synthesis proceeds in three steps:

[0061] (1) Synthesis of 1,2,3-trimethoxy-5-(4-nitrostyryl)aniline

[0062] Add 1.385g of p-nitrophenylacetic acid and 1.000g of 3,4,5-trimethoxybenzaldehyde in a molar ratio of 1.5:1 and mix them in a three-necked flask, 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 yellow solid obtained after the reaction was recrystallized twice with absolute ethanol, and dried in a vacuum oven for future use. The yield was 98%.

[0063] (2) Synthesis of 5-(4-aminostyryl)-1,2,3-trimethoxyaniline

[0064] Add 0.500 g of the first step product 1,2,3-trimethoxy-5-(4-nitrostyryl) aniline and 0.789 g of stannous chloride dihydrate into the three-necked flask in a molar ratio of 1:2 Mix ...

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Abstract

The invention relates to synthesis and application of o-hydroxy-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 390 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) representA: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 o-hydroxy-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 390 nm; and the o-hydroxy-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 light sensitizers, in particular to the synthesis and application of a visible light photosensitizer with a conjugated Schiff base type containing adjacent hydroxyl groups. 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 a...

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 高放仲晓林王琪李红茹张胜涛
Owner CHONGQING UNIV
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