Application of curcumin derivatives in the field of visible light-curing

A technology of curcumin derivatives and curcuminoids, which is applied in the field of organic photofunctional molecule synthesis and visible light photopolymerization, can solve the problems of insensitization of iodonium salt photopolymerization, etc., and achieve good photobleaching properties and ultraviolet-visible absorption wavelength range and light-absorbing ability to improve, the effect of easy synthesis

Inactive Publication Date: 2018-08-24
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although curcumin can sensitize the photopolymerization of iodonium salt photoinitiators in the visible light region, its relatively simple structure makes its absorption spectrum mainly concentrated in the blue-violet light region, and cannot sensitize iodonium salts to light sources with longer wavelengths. under photopolymerization

Method used

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  • Application of curcumin derivatives in the field of visible light-curing
  • Application of curcumin derivatives in the field of visible light-curing
  • Application of curcumin derivatives in the field of visible light-curing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of curcumin derivative CMD1:

[0044]

[0045] Add 0.35g (5mmol) diboron trioxide and 0.5g (5mmol) acetylacetone to 10mL of DMF and stir magnetically in an oil bath at 80°C for 30 minutes. Then 9.6 g (20 mmol) of tributyl borate were added and stirring was continued for 30 minutes. Dissolve N-hexylcarbazole aldehyde in 10 mL of DMF and add it into the reaction system, followed by slowly adding 5 mL of a DMF solution containing 2 mmol of n-butylamine dropwise. After the completion of the reaction was monitored by thin-layer chromatography, 1N hydrochloric acid solution was added to adjust the pH value of the system to 5, and the stirring was continued for 1 hour. The resulting product was extracted with ethyl acetate. The obtained organic phase was washed with water, dried and rotary evaporated to remove ethyl acetate, and purified by column chromatography to obtain the product. Red crystals, yield 65%. The hydrogen spectrum is as follows: 1 H NMR (400 ...

Embodiment 2

[0047] Synthesis of curcumin derivative CMD2:

[0048]

[0049] Add 0.35g (5mmol) diboron trioxide and 0.5g (5mmol) acetylacetone to 10mL of DMF and stir magnetically in an oil bath at 80°C for 30 minutes. Then 9.6 g (20 mmol) of tributyl borate were added and stirring was continued for 30 minutes. Dissolve N-ethylphenothiazinaldehyde in 10 mL of DMF and add it into the reaction system, followed by slowly adding 5 mL of a DMF solution containing 2 mmol of n-butylamine dropwise. After the completion of the reaction was monitored by thin-layer chromatography, 1N hydrochloric acid solution was added to adjust the pH value of the system to 5, and the stirring was continued for 1 hour. The resulting product was extracted with ethyl acetate. The obtained organic phase was washed with water, dried and rotary evaporated to remove ethyl acetate, and purified by column chromatography to obtain the product. Dark red crystals, yield 62%. The hydrogen spectrum is as follows: 1 H NM...

Embodiment 3

[0051] The proportion of each component of a visible light initiating system that initiates free radical curing:

[0052] Curcumin derivative CMD1: 0.2 wt%;

[0053] Photoinitiator: 2 wt%;

[0054] Additives: 0.2 wt%.

[0055] Prepare the visible light-initiating system according to the above-mentioned ratio. Based on the weight of the radical-type polymerizable monomer as 100%, add the visible-light-initiating system to the free-radical photopolymerizable monomer: TPGDA, 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 0.6 mm and a diameter of 1.5 mm, fix it with two clean glass pieces, and irradiate it with blue light (460nm) and green light (520nm) LEDs respectively. Ensure that the distance between the sample and the radiation source is 5cm. In order to ensure the credibility of the experimental results, three NIR tests were performed on each photocuring s...

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Abstract

The invention relates to applications of a series of curcumin derivatives in the field of visible light-curing, wherein the curcumin derivatives are produced from a curcumin structural framework as abasis with modification of aromatic groups connected to two ends of acetylacetone. The curcumin derivatives have strong absorption in blue and green light zones and can serve as a photosensitizer which has effective electron transfer photosensitization effect on iodonium salt. A photo-initiation system composed of the curcumin derivatives and the iodonium salt photo-initiator can effectively induce photo-polymerization of cations and free radicals under a long-wavelength LED light source. Besides, the curcumin derivatives have excellent photo-beaching property and can be applied to the field of deep free radical photo-curing.

Description

technical field [0001] The invention belongs to the field of synthesis of organic photofunctional molecules and visible light photopolymerization, and relates to the application of a class of curcumin derivatives in the field of visible light curing. Background technique [0002] Light curing has many advantages: no organic solvent volatilization, low energy consumption, fast and complete curing at room temperature, and high curing performance. Therefore, photocuring technology has developed rapidly, and it has been widely used in coatings, photoresists, 3D printing materials, electronic packaging materials, adhesives and other fields. At present, the traditional UV curing technology tends to be mature, and photoinitiators with absorption in the ultraviolet region are very common. [0003] However, ultraviolet radiation is harmful to the human body and has poor environmental safety. In addition, the relatively short wavelength of ultraviolet light also limits its applica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48
CPCC08F2/48
Inventor 王涛韩卫祥
Owner BEIJING UNIV OF CHEM TECH
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