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9-phenylacridine photoinitiator and preparation method thereof

A technology of phenylacridine and photoinitiator, which is applied in the direction of organic chemistry, can solve the problems of poor solubility, great influence of oxygen photocuring, and low sensitivity, and achieve the effect of stable properties, excellent sensitivity and solubility

Active Publication Date: 2009-09-09
JIANGSU POLYTECHNIC UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because these traditional photoinitiators have more or less shortcomings such as low sensitivity (low polymerization rate and conversion rate), poor solubility (low transparency and many photolithographic residues), large influence of oxygen on photocuring, and poor storage stability. , so the use of them and photosensitive materials is greatly restricted, and also greatly affects the performance of photosensitive materials

Method used

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  • 9-phenylacridine photoinitiator and preparation method thereof
  • 9-phenylacridine photoinitiator and preparation method thereof
  • 9-phenylacridine photoinitiator and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment one: compound 1 synthesis process

[0026] method 1

[0027] Put 16.9g (0.1mol) of diphenylamine, 14.7g (0.12mol) of benzoic acid and 51.0g (0.375mol) of zinc chloride into a 250ml four-necked flask equipped with a water separator, heat up to 120°C, and start stirring , react at 240-250°C for 6 hours; then lower the temperature to 130-140°C, slowly add 90g of hot 33.0% sulfuric acid solution through the cooling nozzle, and stir for 30min at 100°C; when the temperature drops to about 40°C, Black sticky matter separated from the acid water appears in the bottle, pour out the acid water, add 100ml of 25% ammonia water and 120ml of toluene, stir and heat up to 60°C, after the black sticky matter is completely dissolved, separate the liquid while it is hot, and the ammonia water layer Extract with 50ml×2 toluene at 60°C, combine the toluene layers, decolorize with activated carbon, filter while hot, rotate the remaining 80ml of the toluene layer, transfer to a b...

Embodiment 2

[0032] Embodiment two: compound 2 synthesis process

[0033] Put 16.9g (0.1mol) of diphenylamine, 16.3g (0.12mol) of p-toluic acid and 51.0g (0.375mol) of zinc chloride into a 250ml four-necked flask equipped with a water separator, and heat up to 120°C , start stirring, and react for 6 hours at 240-250°C; then cool down to 130-140°C, slowly add hot 90g of 33.0% sulfuric acid solution through the condensation nozzle, and stir for 30min at 100°C; when the temperature drops to 40°C At around 10 minutes, a black sticky substance separated from the acidic water appeared in the bottle. Pour out the acidic water, add 100ml of 25% ammonia water and 120ml of toluene, stir and heat up to 60°C. The ammonia layer was extracted with 50ml×2 toluene at 60°C, the toluene layers were combined, decolorized with activated carbon, filtered while hot, and 80ml of the toluene layer was rotary evaporated, transferred to a beaker, left to stand for crystallization, filtered with a little toluene R...

Embodiment 3

[0034] Embodiment three: compound 3 synthesis process

[0035] Put 16.9g (0.1mol) of diphenylamine, 16.3g (0.12mol) of m-toluic acid and 51.0g (0.375mol) of zinc chloride into a 250ml four-necked flask equipped with a water separator, and heat up to 120°C , start stirring, and react for 6 hours at 240-250°C; then cool down to 130-140°C, slowly add hot 90g of 33.0% sulfuric acid solution through the condensation nozzle, and stir for 30min at 100°C; when the temperature drops to 40°C At around 10 minutes, a black sticky substance separated from the acidic water appeared in the bottle. Pour out the acidic water, add 100ml of 25% ammonia water and 120ml of toluene, stir and heat up to 60°C. The ammonia layer was extracted with 50ml×2 toluene at 60°C, the toluene layers were combined, decolorized with activated carbon, filtered while hot, and 80ml of the toluene layer was rotary evaporated, transferred to a beaker, left to stand for crystallization, filtered with a little toluene ...

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Abstract

The invention relates to a 9-phenylacridine photoinitiator and a preparation method thereof, wherein 9-phenylacridine (compound 1) and some 9-(substituted phenyl) acridine compounds such as 9-(4-methyl phenyl) acridine (compound 2), 9-(3-methyl phenyl) acridine (compound 3), 9-(2-methyl phenyl) acridine (compound 4) and 9-(2-chlorophenyl) acridine (compound 5) can be used as a photoinitiator and is widely used for unsaturated resin and light-cured materials formed by monomers of the unsaturated resin. The preparation method takes diphenylamine as starting materials, and the diphenylamine is directly reacted with benzoic acid or substituted benzoic acid under the catalysis of a composite catalyst formed by zinc chloride and 85 percent phosphoric acid to produce the 9-phenylacridine (compound 1) and the 9-(substituted phenyl) acridine compounds 2 to 5, thereby the yield of the compounds 1 to 5 can reach above 70 percent, all the product purities are larger than 98 percent, and the technology can satisfy the requirements of industrial production.

Description

technical field [0001] The present invention relates to 9-phenylacridine photoinitiator and preparation method thereof, wherein 9-phenylacridine (compound 1 ) and certain 9-(substituted phenyl)acridine compounds, such as 9-(4-methylphenyl)acridine (compound 2 ), 9-(3-methylphenyl) acridine (compound 3 ), 9-(2-methylphenyl) acridine (compound 4 ), 9-(2-chlorophenyl) acridine (compound 5 ), can be widely used as a photoinitiator in photocurable materials (such as: photocurable coatings, inks and photoresists) composed of unsaturated resins and their monomers. Under ultraviolet light, X-ray or laser irradiation, these light The initiator generates active groups, and then initiates the polymerization and curing reaction of the unsaturated photocurable material. Background technique [0002] Photocurable materials (photocurable coatings, inks and photoresists) mainly composed of unsaturated resins and their monomer materials must be added with photoinitiators in order to enab...

Claims

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Application Information

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IPC IPC(8): C08F2/46C08F2/48C07D219/02
Inventor 钱晓春宋国强曹引梅胡春青刘家斌郭爱花
Owner JIANGSU POLYTECHNIC UNIVERSITY
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