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Double-donor aromatic amine photosensitizer and application thereof in LED visible light curing

An aromatic amine, electron donating technology, applied in the field of photofunctional organic molecules, can solve the problems of poor sensitivity improvement effect, long photocuring time, low photocuring efficiency, etc. strong effect

Active Publication Date: 2016-06-15
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, when the existing photosensitizers are used, they have poor solubility, poor sensitivity enhancement effect, long photocuring time, low photocuring efficiency, matching light source wavelength is shorter, and are more biased towards ultraviolet light sources. Therefore, The synthesis of photosensitizers with long-wavelength absorption and better photosensitivity has become a research and development hotspot in this field

Method used

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  • Double-donor aromatic amine photosensitizer and application thereof in LED visible light curing
  • Double-donor aromatic amine photosensitizer and application thereof in LED visible light curing
  • Double-donor aromatic amine photosensitizer and application thereof in LED visible light curing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of Sensitizer TPN

[0041] The synthesis process is shown in the following formula:

[0042]

[0043] Add N-ethyl-6-bromophenothiazine-3-aldehyde (0.2409g, 0.8mmol), Pd(PPh 3 ) 2 Cl 2 (8.5mg, 0.012mmol), CuI (7.6mg, 0.04mmol), triphenylphosphine (10.5mg, 0.04mmol), TEA10ml and DMF40ml, under the protection of nitrogen, dissolve triphenylamine acetylene (0.2574g, 0.96mmol) Add DMF20ml dropwise to the system, 85C 。Heat the oil bath until the reaction of N-ethyl-6-bromophenothiazine-3-aldehyde is complete. After the reaction system is cooled, it is poured into water, filtered, and dried in the air. Purified by column chromatography (PE:DCM=4:1) to obtain an orange-yellow solid. Under nitrogen protection, orange solid (0.2611g, 0.5mmol), cyanoacetic acid (0.2102g, 2.5mmol), 0.5ml of piperidine and 20ml of chloroform were sequentially added to a 100ml one-necked bottle. Reflux until the reaction of the raw material is complete, configure hydrochloric acid ...

Embodiment 2

[0046] Synthesis of Sensitizer CPN

[0047] The synthesis process is shown in the following formula:

[0048]

[0049] Add N-ethyl-6-bromophenothiazine-3-aldehyde (0.2409g, 0.8mmol), Pd(PPh 3 ) 2 Cl 2 (8.5mg, 0.012mmol), CuI (7.6mg, 0.04mmol), triphenylphosphine (10.5mg, 0.04mmol), TEA10ml and DMF40ml, under the protection of nitrogen, dissolve N-ethylcarbazolyne (0.2103g, 0.96mmol) DMF20ml dropwise into the system, 85C 。 Heat the oil bath until the reaction of N-ethyl-6-bromophenothiazine-3-aldehyde is complete. After the reaction system is cooled, it is poured into water, filtered, and dried in the air. Purified by column chromatography (PE:DCM=4:1) to obtain an orange-yellow solid. Under the protection of nitrogen, orange solid (0.2361g, 0.5mmol), cyanoacetic acid (0.2102g, 2.5mmol), 0.5ml of piperidine and 20ml of chloroform were sequentially added to a 100ml one-necked bottle. Reflux until the reaction of the raw material is complete, prepare the hydrochloric aci...

Embodiment 3

[0052] The proportion of each component of a visible light initiating system that initiates free radical curing:

[0053] Photosensitizer TPN: 0.2wt%;

[0054] Free radical photoinitiator: 2wt%;

[0055] Additives: 0.2wt%.

[0056] Prepare the visible light triggering system according to the above-mentioned ratio, and add the visible light triggering system to the free radical polymerizing monomer: TPGDA based on the weight of the free radical polymerizing monomer as 100%, and mix thoroughly to obtain a transparent and clear photocuring reaction solution. Add the prepared light-curing system into a rubber ring mold with a thickness of 1.8mm and a diameter of 1.5mm, fix it with two clean glass pieces, and irradiate it with 455nm and 532nm laser diodes respectively to ensure that the sample and the excitation light source are consistent. The distance is 15cm. In order to ensure the credibility of the experimental results, three NIR tests were performed on each photocuring sys...

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Abstract

The invention discloses a double-donor aromatic amine photosensitizer, structurally characterized by having an aromatic amine double-donor conjugated group and a structurally general formula shown as I. Compared with commonly reported visible light initiating systems, this photosensitizer has high absorbability in a visible light area, is simple to synthesize, is applicable to visible LED light source free radicals and cationic curing systems and has application potential.

Description

technical field [0001] The invention belongs to the technical field of photofunctional organic molecules, and in particular relates to a class of double electron-donating aromatic amine photosensitizer and its application in photocuring of visible LED light sources. Background technique [0002] UV curing technology has been widely used in many industrial fields such as: printing, ink, coating, adhesives, optical devices, electronic circuits, etc. In recent years, it has also been involved in emerging digital storage, three-dimensional precision machining and other fields. Compared with thermal polymerization or thermal curing, it has the characteristics of fast curing rate, simple equipment, small footprint, room temperature operation, less pollution, and excellent performance of cured products. It is an environmentally friendly green technology. However, there are many weaknesses in UV curing: ① UV radiation is harmful to the human body, poor in environmental protection a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/22C07D417/06C08F2/50C08F122/14C08G59/68
CPCC07D279/22C07D417/06C08F2/50C08F122/1006C08G59/68
Inventor 王涛周腾飞
Owner BEIJING UNIV OF CHEM TECH
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