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Thioxanthone photoinitiator containing sulfydryl and initiator aid amine and preparation method of thioxanthone

A technology of thioxanthone light and photoinitiator, which is applied in organic chemistry and other fields, and can solve problems such as hindering and unfavorable macromolecular photoinitiators

Inactive Publication Date: 2014-12-10
HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This photoinitiator does not need to add additional co-initiators when it is used, but when it undergoes polycondensation reaction with monomers or polymers containing isocyanate groups and epoxy groups to form macromolecular photoinitiators, the Photoactive groups are easily hindered by macromolecular chain segments, which is not conducive to exerting the advantages of macromolecular photoinitiators (Allen N S. Photoinitiators for UV and visible curing of coatings: mechanisms and properties[J]. Journal of Photochemistry and Photobiology A: Chemistry, 1996, 100: 101-107)

Method used

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  • Thioxanthone photoinitiator containing sulfydryl and initiator aid amine and preparation method of thioxanthone
  • Thioxanthone photoinitiator containing sulfydryl and initiator aid amine and preparation method of thioxanthone
  • Thioxanthone photoinitiator containing sulfydryl and initiator aid amine and preparation method of thioxanthone

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Experimental program
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Embodiment 1

[0025] (1) Dissolve 1 mole of thioxanthone glycidyl ether in 0.2 L of THF solvent to form a solution, add 0.005 moles of catalyst lithium chloride and 1.2 moles of carbon disulfide to the solution, and react at -20°C for 1 hour , then react at 20°C, monitor the reaction process by infrared, when the characteristic peaks of epoxy groups at 823cm-1 and 910cm-1 disappear, the reaction is complete, pour the reaction solution into excess water, and extract with ethyl acetate , The solvent was removed under reduced pressure to obtain an intermediate product, which was detected by FTIR (KBr): 1191cm-1 (C=S), 1048cm-1 (C-O) and 643cm-1 (C-S);

[0026] (2) Add 1 mole of benzylamine dropwise to all the intermediate products obtained in step (1), and the dropwise addition is completed in 2 hours, and react at 30° C. for 3 hours. After the reaction is completed, thioxanthene containing mercapto and amine is obtained. Ketone photoinitiator, the product is detected: FTIR (KBr): 2600cm-1 (S-...

Embodiment 2

[0028] (1) Dissolve 1 mole of thioxanthone glycidyl ether in 0.6 L of NVP solvent to form a solution, add 0.05 moles of catalyst lithium bromide and 1.2 moles of carbon disulfide to the solution, react at 10°C for 4 hours, and then React at 40°C, monitor the reaction process by infrared, when the characteristic peaks of epoxy groups at 823cm-1 and 910cm-1 disappear, the reaction is complete, pour the reaction solution into excess water, extract with ethyl acetate, and decompress The solvent was removed to obtain an intermediate product, which was detected by FTIR (KBr: 1190 cm-1 (C=S), 1050 cm-1 (C-O) and 652 cm-1 (C-S).

[0029] (2) To all the intermediate products obtained in step (1), add 1 mole of methylbenzylamine dropwise, and the addition is completed in 2.5 hours, and react at 80° C. for 12 hours. Xanthone photoinitiator, the product is detected: FTIR (KBr): 2552cm-1 (S-H), 1168cm-1 (C=S), 1055cm-1 (C-O) and 3400cm-1 (N-H).

Embodiment 3

[0031] (1) 1 mole of thioxanthone glycidyl ether was dissolved in 0.3L of DMF solvent to form a solution, and 0.01 mole of catalyst lithium iodide and 1.2 mole of carbon disulfide were added to the solution, and reacted at 0° C. for 3.5 hours, Then react at 28°C, monitor the reaction process by infrared, when the characteristic peaks of the epoxy groups at 823cm-1 and 910cm-1 disappear, the reaction is complete, the reaction solution is poured into excess water, extracted with ethyl acetate, The solvent was removed under reduced pressure to obtain an intermediate product, which was detected by FTIR (KBr): 1195 cm-1 (C=S), 1051 cm-1 (C-O) and 644 cm-1 (C-S).

[0032] (2) To all the intermediate products obtained in step (1), add 1 mole of phenethylamine dropwise, dropwise in 3 hours, react at 60° C. for 5 hours, and complete the reaction to obtain thiol-containing and amine-containing thia Anthrone photoinitiator, the product is detected: FTIR (KBr): 2554cm-1 (S-H), 1163cm-1 (C...

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Abstract

The invention relates to a thioxanthone photoinitiator containing sulfydryl and initiator aid amine and a preparation method of the thioxanthone. The preparation method comprises the following steps: by using a thioxanthone derivative containing an epoxy group as a raw material, firstly, converting the epoxy group into a circular thiocarbonate group by adding carbon disulfide which is reacted with the thioxanthone derivative containing the epoxy group; and then, carrying out a ring-opening reaction with amine containing a benzene ring to obtain the thioxanthone photoinitiator containing sulfydryl and initiator aid amine, wherein the obtained compound is of a good photo-initiating effect; R1, R2 and R3 are independently selected from hydrogen, halogen, hydroxyl, and C1-C22 alkyl; R4 is selected from H, C1-C2 alkane groups or benzyl; and R5 is selected from aromatic alkyls such as benzyl, phenethyl, phenylpropyl, and phenylbutyl containing benzene rings.

Description

technical field [0001] The invention belongs to an organic compound and a preparation method thereof, in particular to a thioxanthone photoinitiator containing a mercapto group and a co-initiator amine and a preparation method thereof, which can be used as a photoinitiator in the field of photocuring. Background technique [0002] Photocuring (also known as photopolymerization) technology is an environmentally friendly technology, which has been widely used in chemical industry, machinery, electronics, light industry, communication and other fields. It has many advantages such as fast curing speed, low cost, and less pollution. Photoinitiator is an important part of the photocuring system, which generates active free radicals by absorbing light energy, thereby initiating photopolymerization. Commercially a large amount of thioxanthone (isopropylthioxanthone, US Patent6025408), which is used as a high-efficiency photoinitiator, not only has poor compatibility with the photocu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07D335/16
Inventor 聂俊鲁玉辉马贵平
Owner HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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