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A class of double electron-donating aromatic amine photosensitizer and its application in visible LED light curing

An electron-donating and aromatic amine technology, applied in the field of photofunctional organic molecules, can solve the problems of poor sensitivity enhancement, low photocuring efficiency, and long photocuring time, and achieve long photosensitive wavelength band, strong light absorption ability, and low cost. cheap effect

Active Publication Date: 2018-01-19
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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  • A class of double electron-donating aromatic amine photosensitizer and its application in visible LED light curing
  • A class of double electron-donating aromatic amine photosensitizer and its application in visible LED light curing
  • A class of double electron-donating aromatic amine photosensitizer and its application in visible LED light curing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of Sensitizer TPN

[0036] The synthesis process is shown in the following formula:

[0037]

[0038] 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), TEA 10ml and DMF 40ml, under the protection of nitrogen, will dissolve triphenylamine acetylene (0.2574g, 0.96mmol ) DMF 20ml was added dropwise to the system, and heated in an oil bath at 85°C until N-ethyl-6-bromophenothiazine-3-aldehyde was completely reacted. After the reaction system was cooled, it was poured into water, filtered, and dried in the air. Purified by column chromatography (PE:DCM=4:1), an orange-yellow solid was obtained. 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, co...

Embodiment 2

[0041] Synthesis of Sensitizer CPN

[0042] The synthesis process is shown in the following formula:

[0043]

[0044] 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), TEA 10ml and DMF 40ml, under the protection of nitrogen, will dissolve N-ethylcarbazole alkyne (0.2103 g, 0.96mmol) of DMF 20ml was added dropwise to the system, heated in an oil bath at 85°C until the reaction of N-ethyl-6-bromophenothiazine-3-aldehyde was complete, the reaction system was cooled, poured into water, filtered, and dried in the air . Purified by column chromatography (PE:DCM=4:1), an orange-yellow solid was obtained. 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, pr...

Embodiment 3

[0047] The proportion of each component of a visible light initiating system that initiates free radical curing:

[0048] Photosensitizer TPN: 0.2wt%;

[0049] Free radical photoinitiator: 2wt%;

[0050] Additives: 0.2 wt%.

[0051] 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 sy...

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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 Patents(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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