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Low-toxicity flavonol sulfonate photoinitiator, visible light initiation system and application

A technology of flavonol sulfonate and photoinitiator, applied in organic chemistry and other directions, can solve the problems of low photocuring efficiency, few photoinitiators, and few photoinitiators, etc., and achieves simple molecular structure, strong light absorption ability, The effect of a long photosensitive band

Inactive Publication Date: 2022-06-24
安庆北化大科技园有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing low-toxic photoinitiators have a small amount, and the amount of use is large, the effect of photosensitivity improvement is not good, the photocuring time is long, and the photocuring efficiency is low.
At present, functional dyes with low toxicity photoinitiators have been developed, but there are few highly efficient low toxicity visible light photoinitiators

Method used

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  • Low-toxicity flavonol sulfonate photoinitiator, visible light initiation system and application
  • Low-toxicity flavonol sulfonate photoinitiator, visible light initiation system and application
  • Low-toxicity flavonol sulfonate photoinitiator, visible light initiation system and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Synthesis of Initiator 2-(4-(Diphenylamino)phenyl)-4-oxo-4H-benzofuran-3-ylbenzenesulfonate

[0054] The synthesis process is shown in the following formula:

[0055]

[0056] 38.6 mL of DMF, 37.3 mL of phosphorus oxychloride, and 24.8 g of triphenylamine were added to a 500-ml single-neck bottle, dissolved in 1,2-dichloroethane, and heated to 80°C. TLC detected the disappearance of the starting material, poured the reaction solution into 100 mL of ice water, adjusted the pH value to neutrality with sodium hydroxide, extracted with dichloromethane several times, and concentrated to obtain 4-(diphenylamino)benzaldehyde.

[0057] In a 500ml round-bottomed flask, add 12g of sodium hydroxide, dissolve in 30ml of water, reduce the temperature to room temperature, then add 20ml of ethanol, weigh 4.86g of 2-hydroxyacetophenone and 9.78g of 4-(diphenylamino)benzaldehyde and mix, Dissolve and dilute with 70ml ethanol, add half of the mixed solution dropwise to the round-bott...

Embodiment 2

[0065] A visible light initiation system for initiating free radical curing and its application:

[0066] According to 0.125wt% photoinitiator A, the visible light initiation system is prepared, and the visible light initiation system is added to the free radical polymerizable monomer TPGDA based on the weight of the radical polymerizable monomer as 100%, and the transparent and clear photocuring reaction solution is obtained by fully mixing.

[0067] Add the prepared photocuring system to a rubber ring mold with a thickness of 1.0mm and a diameter of 7.0mm, fix it with two clean glass sheets, and irradiate it with a 405nm and 460nm laser diode to ensure the distance between the sample and the excitation light source. The light source is 30W LED lights: purple LED (JH-100B14G30-Z1C, 405nm), blue LED (JH-100B14G30-Z1C, 460nm) (LEDGUHON / Juhong Optoelectronics). In order to ensure the reliability of the experimental results, three NIR tests were performed on each photocurable sys...

Embodiment 3

[0069] A visible light initiation system for initiating free radical curing and its application:

[0070] According to 0.125wt% of photoinitiator A and 3.0wt% of triethanolamine, the visible light initiation system was prepared. Based on the weight of the free radical polymerizable monomer as 100%, the visible light initiation system was added to the free radical polymerizable monomer TPGDA, and fully mixed to obtain a transparent Clear photocurable reaction solution.

[0071] Add the prepared photocuring system to a rubber ring mold with a thickness of 1.0mm and a diameter of 7.0mm, fix it with two clean glass sheets, and irradiate it with a 405nm and 460nm laser diode to ensure the distance between the sample and the excitation light source. The light source is 30W LED lights: purple LED (JH-100B14G30-Z1C, 405nm), blue LED (JH-100B14G30-Z1C, 460nm) (LEDGUHON / Juhong Optoelectronics). In order to ensure the reliability of the experimental results, three NIR tests were perform...

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Abstract

The invention discloses a low-toxicity flavonol sulfonate photoinitiator which is structurally characterized in that the photoinitiator has a natural product flavonol skeleton structure, the structural general formula of the photoinitiator is shown in the specification, R1 is selected from one of triphenylamine, carbazole, phenothiazine, naphthalene, anthracene, pyrene and quinoline, and alkyl, connected with N, on carbazole or phenothiazine is selected from C1-C20 straight-chain alkyl or C1-C20 branched-chain alkyl; r2 is selected from one of methyl, trifluoromethyl, phenyl, 4-methyl phenyl and 4-trifluoromethyl phenyl. The photoinitiator not only can independently initiate free radical polymerization, but also can form two efficient photosensitive initiation systems with an amine compound or a diaryl iodonium salt compound to initiate free radical polymerization. The two photosensitive initiation systems have strong absorption in a visible light region, the synthesis method is simple, and a final cured product shows low toxicity and has application potential in the field of biology.

Description

technical field [0001] The invention belongs to the technical field of new material organic chemicals, and particularly relates to a low-toxicity flavonol sulfonate type photoinitiator and a visible light initiation system and application. Background technique [0002] Light curing technology has been widely used in many industrial fields such as: food packaging, 3D printing, dental materials, biological tissues, 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. It is an environmentally friendly green technology due to its fast curing rate, less pollution, and excellent cured product performance. However, commercial photoinitiators have many weaknesses: ①Due to excessive addition, the photoinitiators cannot be completely consumed in photopolymerization, which may cause corresponding environmental pollution; ②The currently used commercial photoi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C08F2/50C07D311/30
CPCC08F2/48C08F2/50C07D311/30
Inventor 王涛尤健
Owner 安庆北化大科技园有限公司
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