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Visible light photobase generator and preparation method thereof

A base generating agent and visible light technology, applied in the chemical industry, can solve the problems of enhancing alkalinity, increasing the conjugation degree, and increasing the long-wavelength absorption range of photosensitizers, etc., to increase the conjugation degree, increase the absorption range, and synthesize easy effect

Active Publication Date: 2019-06-28
广州五行材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The initiator molecule of the present invention takes cyclic ketone as the center, forms a C=C double bond through the classic principle of aldehyde group and ketone reaction, constructs a chromophore with long conjugation, and introduces a carboxyl structure at the end, which is compatible with a variety of strong Alkali forms an ionic visible light base generator; the photobase generator prepared by the present invention not only has a wider spectral absorption range, but also has a strong absorption band in the visible light region, which solves the problem that the photosensitizer cannot be used at long wavelengths by increasing the degree of conjugation. The problem of increasing the absorption range, and the photobase generator of the present invention can produce alkaline active substances through photodecarboxylation under visible light excitation, enhance alkalinity, and react to Michael addition reaction, mercapto-epoxy resin, mercapto-isocyanate Resin and other systems have the ability of alkali-catalyzed polymerization

Method used

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  • Visible light photobase generator and preparation method thereof
  • Visible light photobase generator and preparation method thereof
  • Visible light photobase generator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]Add 30mL of ethanol to a 100mL single-necked flask, stir and add 1.04g of N-(4-formylphenyl)-N-methylglycine methyl ester, and after fully dissolving, add 0.20g of cyclopentanone and 1.02g of sodium hydroxide , the temperature was raised to 50°C for 18h. The reaction solution was slowly added dropwise with hydrochloric acid to precipitate a red-black precipitate, which was filtered and dried, and then separated by column chromatography. The eluent was a 20:1 dichloromethane-methanol mixed solvent to obtain 0.40 g of the product with a yield of 36.8%. Disperse 0.24 g of the product in 10 mL of methanol, dropwise add 0.12 g of TBD methanol solution, react in a 50 mL single-necked flask at 30° C. for 1 h, and evaporate the methanol under reduced pressure to obtain 0.34 g of a visible light base generator (yield 94.4%). The ultraviolet-visible absorption spectrum of the obtained alkali generator is as follows: figure 1 (represented by VA).

[0051] 1 H NMR(400MHz, Chlorof...

Embodiment 2

[0055] 30mL of methanol was added to a 100mL single-necked flask, 1.03g of N-(4-formylphenyl)-N-methylglycine methyl ester was added with stirring, and 0.24g of 4-methylcyclohexanone and 1.11 g of 4-methylcyclohexanone were added after being fully dissolved. g potassium hydroxide, and the temperature was raised to 40°C for 24h. The reaction solution was slowly added dropwise with sulfuric acid to precipitate a black precipitate, which was filtered and dried, and then separated by column chromatography. The eluent was a 20:1 dichloromethane-methanol mixed solvent to obtain 0.29 g of the product with a yield of 28.6%. Disperse 0.29g of the product in 10mL of methanol, dropwise add 0.14g of TBD methanol solution, react in a 50mL single-necked flask at 20°C for 12h, and evaporate the methanol under reduced pressure to obtain 0.41g of visible light alkali generator (yield 95.3%). The ultraviolet-visible absorption spectrum of the obtained alkali generator is as follows: figure 1 (...

Embodiment 3

[0060] Add 30 mL of ethanol to a 100 mL single-necked flask, stir and add 1.6 g of N-(4-formylphenyl)-N-methylglycine methyl ester, and after fully dissolving, add 0.3 g of cyclopentanone and 0.86 g of potassium hydroxide , the temperature was raised to 60°C for 4h. The reaction solution was slowly added dropwise with nitric acid to precipitate a red-black precipitate. After suction filtration and drying, column chromatography was performed. The eluent was a 20:1 dichloromethane-methanol mixed solvent to obtain 0.35 g of the product with a yield of 21.6%. Disperse 0.3 g of the product in 10 mL of N,N-dimethylformamide, add DBU methanol solution containing 0.15 g dropwise, react at 60°C for 5 h in a 50 mL single-necked flask, and evaporate the N,N-dimethylformamide under reduced pressure , to obtain 0.42 g of a visible light base generator (yield 93.3%).

[0061] 1 H NMR(400MHz, Chloroform-d)δ7.50(d,J=8.6Hz,6H),6.79(d,J=8.9Hz,4H),4.01(s,4H),3.57-3.31(m,6H) ,3.23(q,J=5.6Hz,20...

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Abstract

The invention provides a visible light photobase generator and a preparation method thereof. The chemical structural formula of the visible light pohtobase generator is shown in the description, wherein Z represents any of the chemical structural formulas in the description, and B<+> represents the formula as shown in the description. The prepared photobase generator not only has a wide spectral absorption range, but also has a strong absorption band in a visible light region and has the high quantum yield, and the problem that by means of the method of increasing the conjugated degree, the long wavelength absorption range of a photosensitizer cannot be increased is solved; in addition, the photobase generator can generate alkaline active substance through photoinduced decarboxylation under visible light excitation, the alkalinity is enhanced, and the base catalyzed polymerization capacity is achieved for a Michael addition reaction, thiol-epoxy resin, thiol-isocyanate resin and othersystems. Accordingly, the photoinitiator has the wide application prospects in a high molecular photosensitive system and in the aspects of photoresist, epoxy resin curing, paint, ink and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and particularly relates to a visible light alkali generator and a preparation method thereof. Background technique [0002] Photoinitiators play an important role in many fields, such as coatings, adhesives, dental materials, microelectronic materials, and 3D printing. Photobase generator (Photobase generator) is a new class of photoinitiators developed in recent years. It is a class of compounds that can release alkaline active substances after being excited by irradiation, and can achieve effective base-catalyzed reactions under certain conditions. . The alkali-catalyzed photopolymerization reaction system has the advantages of small polymerization shrinkage, no oxygen-free polymerization, and no corrosion to the substrate. [0003] As early as the late 1980s, Kutal et al. first proposed the first type of photobase generators—cobalamin complexes. After that, many different photobas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/18C07C227/16C07C227/18C07D487/04G03F7/004
Inventor 李治全刘仁朱俊哲郑元俭刘晓亚
Owner 广州五行材料科技有限公司
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