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A kind of visible light alkali generator and preparation method thereof

An alkali generator and visible light technology, applied in the chemical industry, can solve the problems of increasing the degree of conjugation, enhancing the alkalinity, increasing the long-wavelength absorption range of the photosensitizer, etc., and achieving the increase of the degree of conjugation, strong alkalinity, and simple synthesis method. Effect

Active Publication Date: 2021-09-07
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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  • A kind of visible light alkali generator and preparation method thereof
  • A kind of visible light alkali generator and preparation method thereof
  • A kind of visible light alkali generator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0051] 1 H NMR (400MHz, Chloroform-d) δ7.51(d, J=8.6Hz, 6H), 6.76(d, J=8.9Hz, 4H), 3.97(s, 4H),...

Embodiment 2

[0055] Add 30mL of methanol into a 100mL single-necked flask, stir and add 1.03g of N-(4-formylphenyl)-N-methylglycine methyl ester, after fully dissolving, add 0.24g of 4-methylcyclohexanone and 1.11 g potassium hydroxide, heated to 40 ° C for 24 hours. The reaction solution was slowly added dropwise with sulfuric acid to precipitate a black precipitate, which was filtered and dried by column chromatography, and the eluent was a 20:1 mixed solvent of dichloromethane-methanol 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, evaporate the methanol under reduced pressure, and obtain 0.41g of visible light base generator (95.3% yield). The ultraviolet-visible light absorption spectrum of gained base generator is as figure 1 (Denoted by VB).

[0056] 1 H NMR (400MHz, Chloroform-d) δ7.74(s, 2H), 7.41(d, J=8.8Hz, 4H), 6.73(d, J...

Embodiment 3

[0060] Add 30mL of ethanol to a 100mL single-necked flask, stir and add 1.6g of N-(4-formylphenyl)-N-methylglycine methyl ester, after fully dissolved, add 0.3g of cyclopentanone and 0.86g of potassium hydroxide , warming up to 60°C for 4h. The reaction solution was slowly added dropwise with nitric acid to precipitate a red-black precipitate, which was then filtered and dried by column chromatography. The eluent was a 20:1 mixed solvent of dichloromethane-methanol to obtain 0.35 g of the product with a yield of 21.6%. Disperse 0.3g of the product in 10mL N,N-dimethylformamide, add dropwise DBU methanol solution containing 0.15g, react in a 50mL single-necked flask at 60°C for 5h, evaporate N,N-dimethylformamide under reduced pressure , to obtain 0.42g 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,20H),2.73(d,J=2.2Hz,3H),1.92-1.79(m,2H),1.45-1.72(...

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Abstract

The invention provides a visible light alkali generator and a preparation method thereof. The chemical structure of the visible light alkali generator is shown in the following formula: wherein, Z represents any one of the following chemical structural formulas: B + It means that the photobase generator prepared by the invention not only has a wide spectral absorption range, but also has a strong absorption band in the visible light region and has a high quantum yield, which solves the problem that the method of increasing the degree of conjugation cannot make the photosensitizer in the long-term. The problem of increasing the wavelength absorption range, and the photobase generator of the present invention can generate alkaline active substances through photodecarboxylation under the excitation of visible light, enhance the alkalinity, and react to Michael addition reaction, mercapto-epoxy resin, Systems such as mercapto-isocyanate resins have the ability to base-catalyze polymerization. The invention realizes that the photoinitiator has wide application prospects in the polymer photosensitive system, photoresist, epoxy resin curing, paint, ink and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a visible light base 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 is a new type of photoinitiator developed in recent years. It is a kind of compound that can release alkaline active substances after being excited by radiation, and can realize effective base-catalyzed reaction under certain conditions. . The alkali-catalyzed photopolymerization reaction system has the advantages of small polymerization shrinkage, no oxygen inhibition, and no corrosion to the substrate. [0003] As early as the late 1980s, Kutal et al. first proposed the first type of photobase generator—cobalamin complex, and many different photobase generators were developed one after another. Be...

Claims

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Application Information

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Patent Type & Authority Patents(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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