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Single-component flavonol sulfonate visible light initiator as well as preparation method and application thereof

A technology of flavonol sulfonate and initiator, which is applied in the direction of organic chemistry, can solve the problems of incomplete curing, poor solubility, low photocuring efficiency, etc., to reduce the cost of photocuring, reduce cytotoxicity, and improve the molecular structure simple effect

Pending 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

This photoinitiator can only be cured by UV light and cannot be used in the visible light region
[0004] However, UV curing has the following disadvantages: ① UV radiation and easy to generate ozone, pollute the environment, harmful to the human body, poor environmental safety; Strong absorption of ultraviolet light, resulting in serious attenuation of light intensity, incomplete curing, and poor performance of light-cured films
However, the existing photosensitizers have disadvantages such as poor solubility, strong fluorescence, short triplet life, poor sensitivity enhancement effect, long photocuring time, and low photocuring efficiency.
At present, the use of natural product framework structure as a low-toxicity photosensitizer has made progress, but the use of natural product framework structure as a one-component high-efficiency initiator is still blank in photopolymerization technology

Method used

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  • Single-component flavonol sulfonate visible light initiator as well as preparation method and application thereof
  • Single-component flavonol sulfonate visible light initiator as well as preparation method and application thereof
  • Single-component flavonol sulfonate visible light initiator as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of Initiator 2-(4-(Diphenylamino)phenyl)-4-oxo-4H-benzofuran-3-ylbenzenesulfonate

[0051] The synthesis process is shown in the following formula:

[0052]

[0053]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.

[0054] 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 70 ml of ethanol, add half of the mixed solution dropwise to the round-b...

Embodiment 2

[0060] Synthesis of Initiator 2-(10-ethyl-10H-phenothiazin-3-yl)-4-oxo-4H-chromium-3-ylbenzenesulfonate

[0061] The synthesis process is shown in the following formula:

[0062]

[0063] 38.6 mL of DMF, 37.3 mL of phosphorus oxychloride, and 23.0 g of 10-ethyl-10H-phenothiazine 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 several times with dichloromethane, and concentrated to obtain 10-ethyl-10H-phenothiazine-3- formaldehyde.

[0064] Add 12g of sodium hydroxide to a 500ml round-bottomed flask, dissolve in 30ml of water, reduce the temperature to room temperature, then add 20ml of ethanol, weigh 4.86g of 2-hydroxyacetophenone and 9.13g of 10-ethyl-10H-phenothiazine- 3-formaldehyde was mixed, dissolved and diluted with 70 ml of ethanol, half o...

Embodiment 3

[0070] Synthesis of Initiator 2-(9-hexyl-9H-carbazol-3-yl)-4-oxo-4H-benzofuran-3-yl 4-(trifluoromethyl)benzenesulfonate

[0071] The synthesis process is shown in the following formula:

[0072]

[0073] 38.6 mL of DMF, 37.3 mL of phosphorus oxychloride, and 25.4 g of 9-hexyl-9H-carbazole 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 raw material point, poured the reaction solution into 100 mL of ice water, adjusted the pH value to neutrality with sodium hydroxide, extracted several times with dichloromethane, and concentrated to obtain 9-hexyl-9H-carbazole-3-carbaldehyde.

[0074] Add 12g of sodium hydroxide to a 500ml round-bottomed flask, dissolve in 30ml of water, reduce the temperature to room temperature, then add 20ml of ethanol, weigh 4.86g of 2-hydroxyacetophenone and 9.99g of 9-hexyl-9H-carbazole-3- Formaldehyde was mixed, dissolved and diluted with 70 ml of ethanol, half of t...

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Abstract

The invention discloses a single-component flavonol sulfonate visible light initiator, which has a natural product flavonol skeleton structure, and the structural general formula is shown in the specification, in the formula, R1 is selected from one of triphenylamine, carbazole, phenothiazine, naphthalene, anthracene, pyrene and quinoline; 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. An ester bond of the photoinitiator has low bond energy, so that active species are generated under mild visible light irradiation to initiate free radical polymerization, and the photoinitiator has a high molar extinction coefficient in a visible light region and is sufficient to initiate TPGDA polymerization at low concentration; meanwhile, compared with a common visible light initiation system, the visible light initiation system has the advantages of longer photosensitive wave band, stronger light absorption capability, simple molecular structure, easiness in preparation, low cost and industrial application potential.

Description

technical field [0001] The invention belongs to the technical field of new material organic chemicals, in particular to a single-component flavonol sulfonate visible light initiator and a preparation method and application thereof. Background technique [0002] Light curing technology is an environmentally friendly green technology due to its fast curing rate, less pollution, and excellent cured product performance. It has been widely used in many industrial fields such as: printing, ink, coating, adhesive, optical devices, electronic circuits, etc. Although the amount of photoinitiator in the light curing formulation is very small, its function is the most critical and important. [0003] The Chinese patent application with publication number CN102120783A discloses a preparation method of a thioxanthone photoinitiator containing aliphatic tertiary amine groups. The method first passes thiosalicylic acid and a benzene ring-containing aliphatic primary amine salt through Co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/62C07D417/04C07D405/04C08F2/50C08F122/20
CPCC07D311/62C07D417/04C07D405/04C08F2/50C08F122/1006
Inventor 王涛尤健
Owner 安庆北化大科技园有限公司
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