Photosensitive quaternary ammonium salt and its preparation method and use

A technology of quaternary ammonium salt and quaternary ammonium salt compound is applied in the field of double-effect photosensitive quaternary ammonium salt, which can solve the problems of low photoamine production efficiency, unattempted dual-curing performance, and difficulty in obtaining raw materials, and achieves the effect of adjusting comprehensive performance.

Inactive Publication Date: 2006-10-25
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Early ketoxime ester photoamine generators generally have low photoamine efficiency. The quaternary ammonium salt photobase generator developed by Neckers and Kadooka Masahiro is based on aromatic ketone structures such as benzophenone and α-quaternary ammonium acetylation structures. , the efficiency of photobase generation is not high, the raw materials used for synthesis are not easy to obtain, and it is difficult to be practical
And they are only used in epoxy resin systems, and their dual-curing properties have not been tried

Method used

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  • Photosensitive quaternary ammonium salt and its preparation method and use
  • Photosensitive quaternary ammonium salt and its preparation method and use
  • Photosensitive quaternary ammonium salt and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of photosensitive quaternary ammonium salt: add 0.04mol 2-benzyl-2-dimethylamino-1-( Phenylphenyl)-butanone-1 (Irgacure 369, Ciba Company) and 50ml of dry treated ethyl acetate, heated to the substrate dissolved, slowly added dropwise with dry redistilled neutral dimethyl sulfate 6.51g (0.05mol, pH=6), reflux and stir for 6 hours. After the reaction, the solvent was removed by a rotary evaporator to obtain a viscous crude product N-(2-(N', N'-dimethylamino)-2-benzyl-n-butyryl)phenyl-N-methyl Morpholine sulfate monomethyl ester quaternary ammonium salt, the product is soluble in water. The reaction equation is shown in formula (3).

[0032]

[0033] Formula (3)

Embodiment 2

[0035] Anion exchange: Add 2.58g of the synthesized quaternary ammonium salt intermediate and 50ml of deionized water in a single-necked flask equipped with a stirrer and a constant pressure dropping funnel, and add dropwise 3.8% tetraphenyl at a concentration of 3.8% under stirring Sodium borate aqueous solution 60ml, about 0.007mol sodium tetraphenylborate in total. A white precipitate gradually formed during the dropwise addition. After the dropwise addition, 50ml of deionized water was added, stirred thoroughly, filtered with suction, and rinsed with a small amount of mixed solvent of acetone and water (V / V 1:1). Dry to obtain a light yellow powder, which is determined to be N-(2-(N',N'-dimethylamino)-2-benzyl-n-butyryl)phenyl-N-methylmorpholine tetraphenylboron Quaternary ammonium salt, easily soluble in acetone, acetonitrile, insoluble in water, ethanol and ether. The melting point is 245-146°C, and the melting point of the substrate Irgacure 369 is 117-119°C. The reac...

Embodiment 3

[0039] Add 0.04mol 2-benzyl-2-dimethylamino-1-(morpholinephenyl)-butanone to a three-necked flask equipped with a magnetic stirrer, reflux condenser (with drying tube), thermometer and dropping funnel -1 (Irgacure 369, Ciba Company) and 50ml of dry treated ethyl acetate, heated to the dissolution of the substrate, and slowly added dropwise with dry redistilled neutral diethyl sulfate 7.7g (0.05mol, pH=6 ), reflux stirred and reacted for 6 hours. After the reaction, the solvent was removed by a rotary evaporator to obtain a viscous crude product N-(2-(N', N'-dimethylamino)-2-benzyl-n-butyryl)phenyl-N-ethyl Morpholine sulfate monoethyl ester quaternary ammonium salt, the product is soluble in water. The reaction equation is shown in formula (5).

[0040]

[0041] Formula (5)

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Abstract

The present invention relates to a class of double-effect photosensitive quaternary ammonium salts that are not only photoamine generators but also free radical photoinitiators and their preparation methods, and their uses as photoinitiators and photobase generators, especially as photocurable coatings, Photoinitiator in photocurable ink, photocurable adhesive and photoresist, etc. The photosensitive quaternary ammonium salt of the present invention can be prepared by taking dialkylamino aryl ketone as a starting material, reacting with alkylating reagents such as haloalkane and sulfuric acid ester under mild conditions, and undergoing nucleophilic substitution reaction. The structure of the photosensitive quaternary ammonium salt of the present invention is shown in formula (1), and they have the dual functions of a free radical photoinitiator (including a water-soluble photoinitiator) and a photobase generator. The definition of formula (1) is as described in the description. ∴

Description

technical field [0001] The present invention relates to a class of double-effect photosensitive quaternary ammonium salts that are both photoamine generators and free radical photoinitiators and their preparation methods, and their use as photoinitiators and photobase generators, especially as photocurable coatings, Photoinitiator in photocurable ink, photocurable adhesive and photoresist, etc. Background technique [0002] With the increasing awareness of environmental protection, the governments of various countries have become increasingly strict on the solvent evaporation control of chemical products such as coatings and inks. Therefore, vigorously researching and developing low-solvent volatilization and low-pollution coatings and inks has become an inevitable trend in the development of the industry. Internationally, powder coatings, light-curing coatings and water-based coatings are environmentally friendly because of their low solvent volatilization, so they are cal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/64C07C209/00C07C225/22C07C221/00G03F7/029C08F2/50
Inventor 杨建文曾兆华许文杰陈用烈
Owner SUN YAT SEN UNIV
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