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Single-component visible light initiator and preparation method thereof

A photoinitiator and visible light technology, applied in the direction of organic chemistry, etc., can solve the problems of peculiar smell of the initiator system, low utilization rate of visible light, easy yellowing, etc., and achieves colorless film formation, easy deep curing, and wide spectral absorption range. Effect

Inactive Publication Date: 2015-07-29
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The photoinitiator of the present invention overcomes the problems of low utilization rate of visible light, peculiar smell, toxicity, and easy yellowing of the initiator system existing in existing photoinitiators, and has the advantages of simple synthesis, high utilization rate of visible light, non-toxicity and no yellowing. Variable and other advantages, has a huge application potential

Method used

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  • Single-component visible light initiator and preparation method thereof
  • Single-component visible light initiator and preparation method thereof
  • Single-component visible light initiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] refer to figure 1 In the shown synthetic route, weigh 0.27g (1mmol) of 2-thioxanthone acetic acid and 0.138g (1mmol) of sesamol in a single-necked flask, then add 8mL of anhydrous toluene, and the dehydrating agent dicyclohexylcarbodiethylene Amine 0.619g (3mmol), catalyst 4-dimethylaminopyridine 0.365g (3mmol), after reflux reaction in the dark for 10 hours, spin the solvent, add 10mL of dichloromethane and 10mL of water for extraction, and dry the organic phase over anhydrous magnesium sulfate Overnight and filtered, the filtrate was concentrated and separated by column chromatography to obtain a colorless solid (eluent: ethyl acetate / petroleum ether=5 / 1), which was obtained after vacuum drying figure 1 Shown target product (yield 61%), the product is as follows through nuclear magnetic resonance spectrum determination structure:

[0046] 1 H NMR (400MHz, CDCl 3 )δ8.68-8.60 (m, 2H), 7.74-7.49 (m, 6H), 6.79-6.53 (m, 3H), 5.99 (s, 2H), 3.99 (s, 2H).

[0047] The ult...

Embodiment 2

[0050] refer to figure 2In the synthetic route shown, weigh 0.228g (1mmol) of 2-hydroxythioxanthone and 0.186g of 5-(2-bromoethyl)-1,3-benzodioxole in a single-necked flask (1mmol), then add 8mL of anhydrous toluene, reflux reaction in the dark for 10 hours, spin to dry the solvent, add 10mL of dichloromethane and 10mL of water for extraction, the organic phase is dried overnight with anhydrous magnesium sulfate and filtered, and the filtrate is concentrated and passed through the column Chromatographic separation gave a colorless solid (eluent: ethyl acetate / petroleum ether=10 / 1), which was obtained after vacuum drying figure 2 Shown target product (yield 58%), the product is as follows through nuclear magnetic resonance spectrum determination structure:

[0051] 1 H NMR (400 MHz, DMSO) δ 10.18 (s, 1H), 8.46 (m, 1H), 7.90-7.52 (m, 5H), 7.32-7.23 (m, 1H).

[0052] The ultraviolet-visible light absorption spectrum figure of gained photoinitiator is shown in Figure 4 ,Dep...

Embodiment 3

[0054] refer to image 3 In the synthetic route shown, add 0.228g (1mmol) of 2-hydroxythioxanthone and 0.184g (1mmol) of piperonyl chloride into a single-necked flask, then add 8mL of anhydrous toluene, and then reflux the reaction in the dark for 10 hours, then spin to dry the solvent , adding dichloromethane 10mL and saturated sodium bicarbonate solution 10mL for extraction three times, the organic phase was dried overnight over anhydrous magnesium sulfate and filtered, the filtrate was concentrated and separated by column chromatography to obtain a colorless solid (eluent: ethyl acetate / petroleum ether=5 / 1), obtain photoinitiator of the present invention (productive rate 42%) after vacuum-drying, product determines structure as follows through nuclear magnetic resonance spectrum:

[0055] 1 H NMR (400MHz, CDCl 3 )δ8.64-8.60 (m, 1H), 8.42 (d, J = 2.5Hz, 1H), 7.85 (m, 1H), 7.64-7.49 (m, 6H), 6.92 (d, J = 8.2Hz, 1H ), 6.09(s,2H).

[0056] The ultraviolet-visible light abs...

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Abstract

The invention discloses a single-component visible light initiator. The light initiator is prepared by reacting an anthrone derivative with a piperonyl cyclonene derivative. The light initiator solves problems of low visible light utilization rate, smelly initiator system, toxicity, high possibility of yellowing of an existing light initiator; the light initiator has the advantages of simplicity for single-component synthesis, high visible light utilization rate, no toxicity, no yellowing and the like, thereby having huge application potential.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to a single-component visible light initiator containing an anthrone structure and a piperonyl ring and a preparation method thereof. Background technique [0002] Photocuring technology has the advantages of high efficiency, energy saving, and environmental protection, and has been widely used in the fields of ink, microelectronics and UV-curable coatings. Photoinitiator is an important part of the photopolymerization system. Due to the advantages of convenient synthesis route, low price and high initiation efficiency of anthrone compounds, a large number of high-efficiency commercial products have appeared. Isopropylthioxanthone (trade name: ITX) is an outstanding representative among them, and its absorption wavelength is in the visible region. Thioxanthone is the most common hydrogen-abstracting initiator. It does not split when it is in an excited state, but extracts a hydrogen ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/12
CPCC07D409/12
Inventor 李治全董晓庆胡鹏刘仁刘敬成刘晓亚
Owner JIANGNAN UNIV
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