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A kind of LED-sensitive distyryl oxime ester type photoinitiator and its preparation and application

A distyryl-based, photoinitiator technology, applied in oxime preparation, organic chemistry, etc., can solve the problems of poor water solubility and low absorption

Active Publication Date: 2022-07-08
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, I2959 has poor water solubility and low absorption in the wavelength of LED light source

Method used

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  • A kind of LED-sensitive distyryl oxime ester type photoinitiator and its preparation and application
  • A kind of LED-sensitive distyryl oxime ester type photoinitiator and its preparation and application
  • A kind of LED-sensitive distyryl oxime ester type photoinitiator and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Preparation of Exemplary Compound (I)-1

[0040]

[0041] (a) in a single-necked flask, add ethylene glycol monomethyl ether (50mmol) and triethylamine (55mmol) in 100 ml of dichloromethane, place at room temperature and stir, dropwise add p-toluenesulfonyl chloride ( 55 mmol) in dichloromethane. After 5 hours, TCL monitored the disappearance of the raw materials, 100 ml of deionized water was added to the system, extracted with dichloromethane, the organic layer was evaporated to dryness under reduced pressure, and the product was an orange liquid with a yield of 95.64%.

[0042] (b) Add 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (48mmol), p-hydroxybenzaldehyde (48mmol) and carbonic acid to a single-necked flask Potassium (58 mmol) in 80 mL of N,N-dimethylformamide (DMF) was placed in a 110°C oil bath to stir the reaction. After 3 hours, TCL monitored the disappearance of raw materials, concentrated DMF under reduced pressure, added 50 ml...

Embodiment 2

[0047] Example 2: Preparation of Initiators 2-16

[0048] The preparation methods of these initiators are similar to the initiator (I)-1 prepared in Example 1, except that 4-bromobenzophenone with different substituents is used in step d and different acid chlorides or acid anhydrides are used in step f. As in step d, (I)-11 and (I)-12 use the same 4-bromopropiophenone as (I)-1, and (I)-2, (I)-13, (I)-14 Use 4-bromobutanone, (I)-3 use 1-(4-bromophenyl)-2-phenylethan-1-one, (I)-4 use 1-(4-bromophenyl) -2-(p-Tolyl)ethane-1-one, (I)-5 used 1-(4-bromophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1- ketone, (I)-6 used 4-bromovalerophenone. In step f, (I)-2, (I)-3, (I)-4 and (I)-5 use the same acetic anhydride or acetyl chloride as (I)-1, while (I)-6 and (I)-5 use the same acetic anhydride or acetyl chloride as (I)-1. (I)-13 uses propionic anhydride or propionyl chloride, (I)-7 uses butyric anhydride or butyryl chloride, (I)-8 uses valeric anhydride or valeryl chloride, (I)-9 and (...

Embodiment 3

[0062] Example 3: Preparation of Initiators 15-20

[0063] The preparation methods of these initiators are similar to those of Initiator 1, except that oxime ester-type photoinitiators with different degrees of water solubility are prepared by using ethylene acetal monomethyl ethers of different lengths. For example, (I)-15 uses tetraethylene glycol monomethyl ether, (I)-16 uses pentaethylene glycol monomethyl ether, (I)-17 uses hexaethylene glycol monomethyl ether, (I)- 18, (I)-19 and (I)-20 used octaethylene glycol monomethyl ether.

[0064] (I)-15, 56% yield, yellow solid. HR-MS(C 28 H 35 NO 8 ): m / e: 513.2363; experimental result: 514.2345 (M+H + ).

[0065] (I)-16, 55% yield, yellow solid. HR-MS(C 30 H 39 NO 9 ): m / e: 557.2625; experimental result: 558.2635 (M+H + ).

[0066] (I)-17, 57% yield, yellow solid. HR-MS(C 32 H 43 NO 10 ): m / e: 601.2887; experimental result: 602.2875 (M+H + ).

[0067](I)-18, 60% yield, yellow solid. HR-MS(C 36 H 51 NO 12 )...

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Abstract

The invention relates to the technical field of new material organic chemicals, and relates to an LED-sensitive distyryl oxime ester type photoinitiator and its preparation and application. In particular, it relates to a class of LED-sensitive water-soluble photopolymerization initiators, which are oxime esters of ethylene acetal monomethyl ether connected to stilbene groups represented by formula I, and its chemical preparation technology, which is used as a radiation curing photoinitiator , and its application in radiation-curable formulations, especially UV-Vis-LED-excitable light-curable water-based coatings or inks, 3D printing, hydrogels, and many other occasions.

Description

【Technical field】 [0001] The invention relates to the technical field of organic chemicals for new materials, in particular to a class of LED-sensitive water-soluble photopolymerization initiators. The ethylene glycol monomethyl ether structure is introduced into the distyryl oxime ester type photoinitiator to give it a Water solubility, its chemical preparation technology, its use as a radiation curing photoinitiator, and its application in radiation curing formulations such as coatings or inks, 3D printing, especially hydrogels and many other occasions. 【Background technique】 [0002] Photoinitiator compounds are an important class of fine organic chemical materials. In the technical field of radiation curing using ultraviolet light or visible (UV) light or LED (ie, Light-Emitting Diode) as a light source, photoinitiator compounds that can generate radically active species under light irradiation conditions are the most important compounds that induce ethylenic unsaturatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F2/48C07C251/66C07C249/08C08F283/10C08F283/01C08F222/14C08F222/20C08F120/56C08F290/06C08F220/28C08F222/40C08F2/44
CPCC08F2/48C07C251/66C08F283/105C08F283/01C08F120/56C08F290/062C08F2/44C08F222/102C08F222/104C08F220/281C08F222/404
Inventor 金明王伟杰万德成
Owner TONGJI UNIV
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