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Star-like visible light initiator having conjugated structure and containing benzophenone fragments as well as synthesis and application of visible light initiator

A benzophenone and conjugated structure technology is applied in the field of star-shaped visible light initiators, which can solve the problems of short absorption wavelength and low initiation efficiency, and achieve the effects of simple synthesis method, convenient source of raw materials and easy-to-obtain raw material sources.

Inactive Publication Date: 2014-08-13
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under visible light irradiation, trichloro-s-triazine and visible light cyanine dye undergo photo-induced electron transfer to generate free radicals to initiate the polymerization of acrylic monomers. However, the synthesis of such compounds requires many steps, and the initiation efficiency is not high. Trichloro-s-triazine light irradiation Harmful gases such as chlorine gas are often produced, so there are many restrictions in practical applications
Benzophenone is a commercialized ultraviolet photoinitiator, but its absorption wavelength is short, roughly between 250-300nm, and there is basically no absorption in the visible region

Method used

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  • Star-like visible light initiator having conjugated structure and containing benzophenone fragments as well as synthesis and application of visible light initiator
  • Star-like visible light initiator having conjugated structure and containing benzophenone fragments as well as synthesis and application of visible light initiator
  • Star-like visible light initiator having conjugated structure and containing benzophenone fragments as well as synthesis and application of visible light initiator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of 4-benzoyl-styryl-4',4''-di(phenyl)triphenylamine

[0040] The synthesis proceeds in two steps:

[0041] (1) Synthesis of 4-benzoyl-styryl-4’,4’’-dibromotriphenylamine

[0042]4-benzoyl-benzyl-diethyl phosphate (7.54mmol, 2.51g) and 4-formyl-4',4''-dibromotriphenylamine (5.8mmol, 2.5g) were dissolved in 50ml of dry tetrahydrofuran In , sodium methoxide (17.4mmol, 0.94g) was used as a basic catalyst and reacted at room temperature for 24 hours. After tetrahydrofuran was removed under reduced pressure, it was extracted with dichloromethane, and the organic layer was collected and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. After column separation, 4-benzoyl-styryl-4',4''-dibromotriphenylamine was obtained, and recrystallized in benzene to obtain a yellow solid with a yield of 60%.

[0043] (2) Synthesis of 4-benzoyl-styryl-4’,4’’-di(phenyl)triphenylamine

[0044] 4-benzoyl-styryl-4',4''-dibromotriphenylamine (3....

Embodiment 2

[0048] Synthesis of 4-benzoyl-styryl-4',4''-di(methyl-phenyl)triphenylamine

[0049] 4-Benzoyl-styryl-4',4''-dibromotriphenylamine (3.77mmol, 2.3g) and p-tolylboronic acid (4.524mmol, 0.615g) were dissolved in 100ml of dry tetrahydrofuran, carbonic acid Potassium (18.85mmol, 2.6g) was used as a basic catalyst, and was refluxed for 24 hours under the protection of argon. After tetrahydrofuran was removed under reduced pressure, it was extracted with dichloromethane, and the organic layer was collected and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. After column separation, 4-benzoyl-styryl-4',4''-di(methyl-phenyl)triphenylamine was obtained, and recrystallized in benzene to obtain an orange solid with a yield of 73%.

[0050] The prepared 4-benzoyl-styryl-4',4''-bis(methyl-phenyl)triphenylamine was formulated into 1×10 in dichloromethane -5 mol / L solution, measure its ultraviolet absorption spectrum. Such as image 3 As shown, th...

Embodiment 3

[0053] Synthesis of 4-benzoyl-styryl-4',4''-bis(methoxy-phenyl)triphenylamine

[0054] 4-benzoyl-styryl-4',4''-dibromotriphenylamine (3.77mmol, 2.3g) and p-methoxyphenylboronic acid (4.524mmol, 0.688g) were dissolved in 100ml of dry tetrahydrofuran, Potassium carbonate (18.85mmol, 2.6g) was used as a basic catalyst, and was refluxed for 24 hours under the protection of argon. After tetrahydrofuran was removed under reduced pressure, it was extracted with dichloromethane, and the organic layer was collected and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. After column separation, 4-benzoyl-styryl-4',4''-di(methoxy-phenyl)triphenylamine was obtained, which was recrystallized in benzene to obtain an orange solid with a yield of 75%.

[0055] The prepared 4-benzoyl-styryl-4',4''-bis(methoxy-phenyl)triphenylamine was prepared in dichloromethane to 1×10 -5 mol / L solution, measure its ultraviolet absorption spectrum. Such as Figure 5 A...

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Abstract

The invention discloses a star-like visible light initiator having a conjugated structure and containing benzophenone fragments as well as synthesis and application of the visible light initiator, belonging to the field of visible light initiators. The star-like visible light initiator has a chemical structural general formula shown in a formula (I), wherein the compound in a molecular structure (I) refers to R: H, CH3, OCH3, OCH2CH3, N(CH3)2, N(CH2CH3)2. The synthesis method comprises the following steps: reacting 4-benzoyl-styryl-4',4''-dibromotriphenylamine and a phenylboronic acid compound in a glass container under an alkaline condition, and preparing the star-like visible light initiator having the conjugated structure and containing benzophenone fragments. The maximum absorption is in a visible light area, and the star-like visible light initiator serving as a visible light initiator and co-initiator triethanolamine form a light-sensitive system to be used for visible-light photopolymerization of acrylic monomers in the solution or to serve as a photo-curing material.

Description

technical field [0001] The invention belongs to the field of visible light initiators, in particular to a star-shaped visible light initiator with a conjugated structure containing a benzophenone segment and its synthesis and application. Background technique [0002] Efficient visible photoinitiators are currently an important area of ​​photopolymerization research. With the advancement of laser imaging and photocuring technology, photoresist, photocurable ink, photocurable coating and photosensitive printing plate have been developed rapidly. A key technology of these photofunctional materials is how to extend their spectral response range to long wavelengths. Therefore, the development of new high-sensitivity, low-energy photopolymerization systems that are sensitive to long-wavelength visible light has become a hot research topic today. In recent years, long-wavelength lasers such as Ar + (488nm, 514nm), YAG (532nm), and He-Ne (633nm) are widely used in the fields of c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07C225/22C07C221/00C08F120/14
Inventor 朱凯凯彭光跃李红茹高放
Owner CHONGQING UNIV
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