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Amphiphilic hyper-branched thioxanthone photoinitiator and preparation method thereof

An amphiphilic hyperbranched, xanthone light technology, applied in the field of photochemistry, can solve the problems of odor, toxicity, migration, and volatility, and achieve the effects of reducing toxicity, improving photo-initiating performance, and improving solubility.

Inactive Publication Date: 2010-03-10
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor compatibility of traditional small molecules with photocuring systems, they are easy to volatilize and migrate after curing, and even more serious will produce odor and toxicity

Method used

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  • Amphiphilic hyper-branched thioxanthone photoinitiator and preparation method thereof
  • Amphiphilic hyper-branched thioxanthone photoinitiator and preparation method thereof
  • Amphiphilic hyper-branched thioxanthone photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1. Slowly add 1.54g (0.01mol) of thiosalicylic acid into 15ml of concentrated sulfuric acid at room temperature, slowly add 5.0g (0.055mol) of phenol under the condition of full stirring, and the addition time is 30 minutes, then Stir at room temperature for 1 hour, raise the temperature to 80° C. for 2 hours, then cool down to room temperature and let stand for 12 hours. The reaction mixture was slowly poured into 150ml of boiling water, then further boiled for 10 minutes, filtered after cooling, washed three times with water, and then reconstituted in a mixed solvent with a volume ratio of 1,4-dioxane:water=4:1 Crystallization gives 2-hydroxythioxanthone. Add 2.3g (0.01mol) of 2-hydroxythioxanthone, 15ml of epichlorohydrin, 5g (0.036mol) of anhydrous potassium carbonate, 15ml of toluene and 0.5ml of polyethylene glycol (molecular weight 400) into a three-necked flask , stirred at 80°C for 2 hours, then refluxed in an oil bath at 135°C for 1 hour, poured out the organ...

Embodiment 2

[0035] Steps 1 and 2 are the same as in Example 1.

[0036] 3. Mix 0.284g (1mmol) 2ETX, 0.108g (0.2mmol) polyethyleneimine (M n =600) and 10ml ethanol were added in the there-necked flask, after dissolving completely, the solution was reacted at 80°C for 24 hours under nitrogen protection, then added 0.081g (0.2mmol) polyethylene glycol monomethyl ether containing epoxy groups, Continue to react at 80°C for 24 hours under the protection of nitrogen, then precipitate into anhydrous ether 10 times the volume of the reaction solution, pour out the solvent, and dry in vacuum to obtain the target product amphiphilic hyperbranched thioxanthone photoinitiator . 1 H NMR (CDCl 3 ): δ=8.58-7.21 (aromatic), 4.10-3.80 (-OCH 2 , -OCH), 3.72-3.40 (-OCH 2 CH2 ), 3.35 (-OCH 3 ), 2.8-2.4 (-NCH 2 CH 2 ).FTIR(KBr): 3326(-OH), 2880(-CH), 1630(C=O).

Embodiment 3

[0038] 1. Slowly add 1.54g (0.01mol) of thiosalicylic acid into 15ml of concentrated sulfuric acid at room temperature, slowly add 5.4g (0.05mol) of m-cresol under the condition of sufficient stirring, and the addition time is 30 minutes , then stirred at room temperature for 1 hour, heated to 80° C. for 2 hours, and then stood overnight at room temperature. The reaction mixture was slowly poured into 150ml of boiling water, then further boiled for 10 minutes, filtered after cooling, washed three times with water, and then reconstituted in a mixed solvent with a volume ratio of 1,4-dioxane:water=4:1 Crystallization affords 4-methyl-2-hydroxythioxanthone. Then 2.3g (0.01mol) of 4-methyl-2-hydroxythioxanthone, 15ml epichlorohydrin, 5g (0.036mol) of anhydrous potassium carbonate, 15ml toluene and 0.5ml polyethylene glycol (molecular weight 400) into a three-necked flask, stirred at 80°C for 2 hours, then refluxed in an oil bath at 135°C for 1 hour, poured out the organic layer a...

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Abstract

The invention discloses an amphiphilic hyper-branched thioxanthone photoinitiator and a preparation method thereof. The small molecule photoinitiator thioxanthone and water-soluble methoxy polyethylene glycol containing epoxy group are introduced on a hyper-branched polymeric coinitiator polyethyleneimine by a method of ring-opening addition, thus preparing a novel amphiphilic hyper-branched polymeric photoinitiator thioxanthone. The polymeric photoinitiator thioxanthone can be used under a condition without a coinitiator, improves the photoinitiation efficiency of the thioxanthone, has excellent compatibility with many solvents and has excellent application prospect in the fields such as coating, micro-electron, food packaging and the like.

Description

technical field [0001] The invention relates to an organic functional polymer material and a preparation method thereof, in particular to an amphiphilic hyperbranched thioxanthone photoinitiator and a preparation method thereof. It belongs to the field of photochemical technology. Background technique [0002] UV curing technology has a wide range of applications in industrial fields such as coatings, inks, photoresists, electronic packaging materials, adhesives, and paper glazing. In the UV curing system, the photoinitiator system is an important component, and its research and development occupy a very important position in the UV curing system. Among them, thioxanthone is an important photoinitiator with good initiation performance. Industrialized thioxanthone photoinitiators (2-chlorothioxanthone and isopropyl thioxanthone, US Patent 6025408) not only have poor compatibility with light-curing systems, but also must be activated under the action of co-initiator amines. ...

Claims

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Application Information

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IPC IPC(8): C08G81/02C08F26/02C08F8/34C08F2/48C07D409/12
Inventor 温延娜姜学松印杰
Owner SHANGHAI JIAO TONG UNIV
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