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Ferrocenium salt photoinitiators containing N-alkyl substituted carbazole ligand and preparation method thereof

A carbazole and alkyl technology, applied in the field of cationic photopolymerization initiators, can solve problems such as inability to match light sources and limit the application of cationic photopolymerization

Inactive Publication Date: 2010-01-13
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many kinds of free radical photoinitiators, and the development has been relatively mature, while there are fewer types of cationic photoinitiators. The commonly used ones are diaryl iodonium salts and triaryl sulfonium salts, but most iodonium salts and sulfur Onium salts have little or no absorption above 300nm, which cannot match some commonly used light sources, which severely limits the application of cationic photopolymerization

Method used

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  • Ferrocenium salt photoinitiators containing N-alkyl substituted carbazole ligand and preparation method thereof
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  • Ferrocenium salt photoinitiators containing N-alkyl substituted carbazole ligand and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1 prepares cyclopentadiene-iron-carbazole hexafluorophosphate

[0022] Put 0.025mol ferrocene, 0.0375mol carbazole, 0.075mol anhydrous AlCl into the four-necked flask 3 , 0.025mol Al powder and 50ml cyclohexane to make it stir and dissolve, and pass into N 2 , and then slowly raised the temperature to 84°C and maintained the reflux state for 10h.

[0023] After the reaction liquid is cooled, pour 10% methanol solution into it, stir and hydrolyze, filter, separate liquids, wash the organic phase with water, combine with the water phase, wash repeatedly with cyclohexane, and then add excess KPF 6 The aqueous solution has a yellow precipitate. The solid was dried and purified by column chromatography to obtain the product cyclopentadiene-iron-carbazole hexafluorophosphate.

Embodiment 2

[0024] Embodiment 2 prepares cyclopentadiene-iron-N-ethylcarbazole hexafluorophosphate

[0025] Put 0.025mol ferrocene, 0.0375mol N-ethylcarbazole, 0.075mol anhydrous AlCl into the three-necked flask 3 , 0.025mol Al powder and 50ml cyclohexane to make it dissolve by stirring, pass N 2 Then slowly raise the temperature to 84°C and maintain the reflux state for 10h.

[0026] After the reaction liquid is cooled, pour 10% methanol solution into it, stir and hydrolyze, filter, separate liquids, wash the organic phase with water, combine with the water phase, wash repeatedly with cyclohexane, and then add excess KPF 6 The aqueous solution has a yellow precipitate. The solid was dried and purified by column chromatography to obtain the product cyclopentadiene-iron-N-ethylcarbazole hexafluorophosphate.

Embodiment 3

[0027] Embodiment 3 prepares cyclopentadiene-iron-N-butylcarbazole hexafluorophosphate

[0028] Take 0.0375mol N-butylcarbazole, 0.025mol ferrocene, 0.075mol anhydrous AlCl 3 , 0.025mol Al powder and 50ml cyclohexane were put into a three-necked flask, stirred and dissolved, and passed N 2 Then slowly raise the temperature to 84°C and maintain the reflux state for 10h.

[0029] After the reaction liquid is cooled, pour 10% methanol solution into it, stir and hydrolyze, filter, separate liquids, wash the organic phase with water, combine with the water phase, wash repeatedly with cyclohexane, and then add excess KPF 6 An orange-yellow precipitate appeared in the aqueous solution. The solid was dried and purified by column chromatography to obtain the product cyclopentadiene-iron-N-butylcarbazole hexafluorophosphate.

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Abstract

The invention discloses ferrocenium salt compounds containing N-alkyl substituted carbazole ligand used as photoinitiators in cationic photopolymerization, and belongs to the technical fields of organic synthesis and cationic photopolymerization. The compounds are prepared from raw materials, namely ferrocene and N-alkyl substituted carbazole through ligand exchange reaction under the catalysis of Lewis acid. The preparation method for the compounds is simple and convenient, and has easy acquisition of the raw materials. As the cationic photoinitiators, the compounds have good ultraviolet absorptivity and photo initiating activity, and can initiate polymerization of epoxy compounds and vinyl ethers compounds. The solubility of the compounds in nonpolar resin is obviously strengthened due to the introduction of alkyl, and the compounds have wide study potential and application prospect in the field of photocuring application.

Description

technical field [0001] The invention relates to the preparation and application of a cationic photopolymerization initiator containing carbazole and an alkyl-substituted carbazole group with carbon chains of different lengths on nitrogen atoms, and belongs to the technical fields of organic synthesis and cationic photopolymerization. Background technique [0002] Ultraviolet (UV) curing has the characteristics of fast curing speed, energy saving, no environmental pollution, excellent coating performance, and high economic benefits. The earliest researched UV curing system is the free radical photocuring system. Compared with it, the cationic photocuring system has the following outstanding features: ① There are many types of monomers and prepolymers that can be photo-initiated cationic polymerization; ② Not subject to oxygen inhibition; ③ Cationic photopolymerization Photopolymerization is living polymerization. [0003] There are many kinds of free radical photoinitiators,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C08F2/50C08G59/70
Inventor 王涛张影汉森
Owner BEIJING UNIV OF CHEM TECH
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