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3- or 4- carbonyl substituted coumarin connected with naphthenones and its synthesis method and use

A technology of cycloalkane ketone and coumarin ketone, which is applied in the field of visible light sensitizing dyes, can solve the problem of wide absorption band coverage and achieve the effect of wide absorption band

Inactive Publication Date: 2007-12-19
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] One of the purposes of the present invention is to solve the problem of absorbing long-wavelength lasers that ordinary coumarin ketones do not have, and the problem of wide coverage of the absorption band, and to provide a class of lasers that have both long absorption wavelengths and wide wavelength coverage. , a coumarinone dye that matches the wavelength of commonly used visible lasers

Method used

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  • 3- or 4- carbonyl substituted coumarin connected with naphthenones and its synthesis method and use
  • 3- or 4- carbonyl substituted coumarin connected with naphthenones and its synthesis method and use
  • 3- or 4- carbonyl substituted coumarin connected with naphthenones and its synthesis method and use

Examples

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Effect test

Embodiment 1

[0113] Synthesis of coumarin ketones (CP-KETOCOU) substituted with 3 or 4 carbonyl groups linked by cyclopentanone

[0114](1) Put 40 millimoles of cyclopentanone and 10 millimoles of p-dimethylaminobenzaldehyde into the flask, add 7 milliliters of absolute ethanol and 10 milliliters of water, add 0.5 milliliters of hexahydropyridine dropwise, at room temperature The reaction was conducted at 25°C for 5 hours, the orange precipitate was filtered, and column chromatography was performed with 0.2wt% ethanol / chloroform to obtain semi-p-dimethylaminobenzylidene cyclopentanone dye with a yield of 85%.

[0115] (2) (Refer to the literature "Journal of Medicinal Chemistry" 1983, volume 31, page 3014, ChemPharm Bull, 1983, 31, 3014) 10 millimoles of 4-acetyl-5-pyrrolyl coumarin, 12 millimeters Place moles of selenious acid in the flask, add 50 ml of xylene and heat to dissolve, reflux for 10 hours, hot filter to remove the gray-black selenium, let the filtrate stand and cool to precipitat...

Embodiment 2

[0118] Synthesis of coumarin ketones (CHE-KETOCOU) substituted with 3 or 4 carbonyl groups linked with cyclohexanone

[0119] (1) Put 30 millimoles of cyclohexanone and 10 millimoles of acetaldehyde into the flask, add 20 milliliters of absolute ethanol and 5 milliliters of water, drop 2 milliliters of 10wt% NaOH aqueous solution, and react at 60°C for 24 hours , Filter the orange precipitate, and perform column chromatography with 0.2wt% ethanol / chloroform to obtain half 2-ethylcyclohexanone dye with a yield of 75%.

[0120] (2) (Refer to the literature "Journal of Medicinal Chemistry" 1983, Volume 31, page 3014, ChemPharm Bull, 1983, 31, 3014) (Refer to the literature "Journal of Medicinal Chemistry", ChemPharm Bull, 1983, 31, 3014) 10 millimoles of 3-acetyl-7-methoxycoumarin, 15 milliliters Place moles of selenous acid in the flask, add 60 ml of ethanol to heat to dissolve, reflux for 15 hours, hot filter to remove the gray-black selenium, leave the filtrate to stand and cool t...

Embodiment 3

[0123] Synthesis of coumarin ketones (CHP-KETOCOU) substituted with 3 or 4 carbonyl groups linked by cycloheptanone

[0124] (1) Put 20 millimoles of cycloheptanone and 10 millimoles of benzaldehyde into the flask, add 20 milliliters of absolute ethanol and 2 milliliters of water, drop 3 milliliters of 10wt% KOH aqueous solution, and react at 65°C for 36 hours , Filter the orange precipitate, and perform column chromatography with 0.2wt% ethanol / chloroform to obtain the hemibenzylidene cycloheptanone dye with a yield of 65%.

[0125] (2) (Refer to the literature "Journal of Medicinal Chemistry" 1983, Volume 31, page 3014, ChemPharm Bull, 1983, 31, 3014) (Refer to the literature "Journal of Medicinal Chemistry", ChemPharm Bull, 1983, 31, 3014) 10 millimoles of 3-methyl-6-phenyl coumarin, 18 millimoles Place selenous acid in a flask, add 70 ml of 1,4-dioxane and heat to dissolve, reflux for 24 hours, hot filter to remove gray-black selenium, let the filtrate stand and cool to precip...

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Abstract

The invention relates to a process for synthesizing 3- or 4- carbonyl substituted coumarin connected by naphthenones and its use. The preparation process using general aldol condensation reaction comprises cyclanone and its corresponding aldehyde compounds with A1 group are added in reactor to produce semi-cyclanone with A1 group; 3- or 4- acetyl substituted coumarin with A2 group and selenious acid are added in another reactor to produce coumarin aldehyde with A2 group; said semi-cyclanone with A1 group dye reacts with coumarin aldehyde with A2 group in the presence of xylene and ethanol mixed solvent to form 3- or 4- carbonyl substituted coumarin connected by naphthenones. The product can be used for visible light polymerization of olefine monomer in photosensitized initiation system and used as photo curing materials, etc.

Description

Invention field [0001] The invention belongs to the field of visible light sensitizing dyes, and particularly relates to a method for synthesizing coumarin ketones substituted by carbonyl groups at 3 or 4 positions connected by cycloalkanones and their use. Background technique [0002] In recent years, lasers with visible wavelengths such as Ar + (488nm, 514nm), YAG (532nm), He-Ne (633nm) lasers are widely used in the fields of holographic recording, laser direct plate making, photocuring, and laser stereolithography. The efficient visible light photosensitive polymerization system has become the current photopolymerization Important areas of research. Regardless of whether it is the mechanism of direct light-sensing by the polymerization initiator or the mechanism of the dye-sensitized polymerization initiator, synthesizing efficient visible light-sensitizing dyes is an effective way to increase the initiation speed of photopolymerization and improve the properties of materials...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/06C09B57/02C08F2/50G03F7/028
Inventor 吴飞鹏王涛李妙贞王尔鉴
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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