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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 problems of wide absorption band coverage and the like, and achieve the effect of wide absorption band

Inactive Publication Date: 2005-07-06
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 laser light that ordinary coumarin ketone dyes do not possess, and the problem of wide coverage of the absorption band, and provide a class of lasers with both long absorption wavelength and wide wavelength coverage. range, coumarinone dyes that match commonly used visible laser wavelengths

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

Experimental program
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Effect test

Embodiment 1

[0112] Synthesis of Ketocoumarin Substituted by Carbonyl at 3 or 4 Position Linked by Cyclopentanone (CP-KETOCOU)

[0113] (1) 40 millimoles of cyclopentanone and 10 millimoles of p-dimethylaminobenzaldehyde are placed in a flask, add 7 milliliters of dehydrated alcohol and 10 milliliters of water, drop 0.5 milliliters of hexahydropyridine, and After reacting at 25°C for 5 hours, the orange precipitate was filtered and separated by column chromatography with 0.2wt% ethanol / chloroform to obtain half-p-dimethylaminobenzylidene cyclopentanone dye with a yield of 85%.

[0114] (2) (synthetic method refers to literature "Journal of Medicinal Chemistry" 1983 volume 31 page 3014, ChemPharm Bull, 1983,31,3014) with 10 mmoles of 4-acetyl-5-pyrrolylcoumarin, 12 mmoles Put selenous acid in a flask, add 50 ml of xylene to heat and dissolve, reflux for 10 hours, heat filter to remove gray-black selenium, leave the filtrate to cool and precipitate red needle-like crystals, and filter to obt...

Embodiment 2

[0117] Synthesis of Ketocoumarin (CHE-KETOCOU) Substituted by 3 or 4 Carbonyl Linked by Cyclohexanone

[0118] (1) Put 30 millimoles of cyclohexanone and 10 millimoles of acetaldehyde into a flask, add 20 milliliters of absolute ethanol and 5 milliliters of water, drop 2 milliliters of 10 wt % NaOH aqueous solution, and react at 60 ° C for 24 hours , filtered the orange precipitate, and separated by column chromatography with 0.2wt% ethanol / chloroform to obtain half 2-ethylcyclohexanone dye with a yield of 75%.

[0119] (2) (for the synthesis method, refer to the literature "Acta Medicinal Chemistry" 1983, Volume 31, page 3014, ChemPharm Bull, 1983, 31, 3014) with 10 mmoles of 3-acetyl-7-methoxycoumarin, 15 mmoles Put molar selenous acid in a flask, add 60 milliliters of ethanol to heat and dissolve, reflux for 15 hours, heat filter to remove gray-black selenium, leave the filtrate to cool and precipitate yellow needle-like crystals, and filter to obtain pure 3-ketoaldehyde B...

Embodiment 3

[0122] Synthesis of Ketocoumarin (CHP-KETOCOU) Substituted by 3 or 4 Carbonyl Linked by Cycloheptanone

[0123] (1) Put 20 millimoles of cycloheptanone and 10 millimoles of benzaldehyde into a flask, add 20 milliliters of absolute ethanol and 2 milliliters of water, add dropwise 3 milliliters of 10 wt % KOH aqueous solution, and react at 65 ° C for 36 hours , filtered the orange precipitate, and separated by column chromatography with 0.2wt% ethanol / chloroform to obtain a hemibenzylidene cycloheptanone dye with a yield of 65%.

[0124] (2) (synthetic method refers to literature "Acta Medicinal Chemistry" 1983 volume 31 page 3014, ChemPharm Bull, 1983,31,3014) 10 mmoles of 3-methyl-6-phenylcoumarin, 18 mmoles Put selenous acid in a flask, add 70 ml of 1,4-dioxane and heat to dissolve, reflux for 24 hours, heat filter to remove gray-black selenium, let the filtrate stand and cool to precipitate red crystals, and filter to obtain pure product 3-ketoaldehyde-6-phenylcoumarin, yie...

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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

field of invention [0001] The invention belongs to the field of visible light-sensitizing dyes, in particular to a synthesis method and application of a class of 3- or 4-carbonyl-substituted coumarin ketones linked by cycloalkane ketones. 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. important area of ​​research. Whether it is the direct photosensitization mechanism of the polymerization initiator or the dye-sensitized polymerization initiator mechanism, the synthesis of efficient visible light-sensitized dyes is an effective way to increase the speed of photopolymerization initiation and improve the properties of materials. Coumarin dye is a very fast-response laser dye, in which 7-aminocoumarin dye, as an electron donor, can effec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/06C08F2/50C09B57/02G03F7/028
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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