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Preparation of cation light initiator ferrocene arene salt and application thereof

A cationic and aromatic hydrocarbon technology, applied in the field of cationic photopolymerization initiators, can solve the problems of weak absorption, low photosensitizing activity, and cannot be a photosensitizer, etc., and achieves the effects of strong absorption and simple and convenient preparation.

Inactive Publication Date: 2008-06-04
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The absorption of a substituted aryl ferrocene salt in the long-wave ultraviolet and visible light regions is enhanced, so its photosensitive activity is enhanced, but compared with free radical photoinitiators, its photosensitive activity is still low. Weak absorption, molar extinction coefficient less than 1000M -1 cm -1 , so cannot be an effective photosensitizer using visible light as the light source

Method used

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  • Preparation of cation light initiator ferrocene arene salt and application thereof
  • Preparation of cation light initiator ferrocene arene salt and application thereof
  • Preparation of cation light initiator ferrocene arene salt and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 prepares [two (cyclopentadiene-iron)-diphenyl ether] hexafluorophosphate

[0035] Put 0.15mol ferrocene, 7.83ml diphenyl ether, 0.3mol anhydrous AlCl into the three-necked flask 3 , 0.15 mol of Al powder and 200 ml of cyclohexane to stir and dissolve, then slowly raise the temperature to 80° C., and maintain the reflux state for 24 hours.

[0036] After the reaction solution is cooled, pour 5% 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 In the aqueous solution, a khaki precipitate precipitated out. The solid was dried and purified by column chromatography to obtain the product [bis(cyclopentadiene-iron)-diphenyl ether] hexafluorophosphate with a yield of 38.58%.

Embodiment 2

[0037] Embodiment 2 prepares [two (cyclopentadiene-iron)-carbazole] hexafluorophosphate

[0038] Put 0.135mol ferrocene, 0.045mol carbazole, 0.27mol anhydrous AlCl into the three-necked flask 3 , 0.135 mol of Al powder and 250 ml of cyclohexane to stir and dissolve, then slowly raise the temperature to 84° C., and maintain the reflux state for 18 hours.

[0039] 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 [bis(cyclopentadiene-iron)-carbazole] hexafluorophosphate with a yield of 66.7%.

Embodiment 3

[0040] Embodiment 3 prepares [two (cyclopentadiene-iron)-biphenyl] hexafluorophosphate

[0041] Put 0.1125mol ferrocene, 0.0375mol biphenyl, 0.225mol anhydrous AlCl into the three-necked flask 3 , 0.1125mol of Al powder and 210ml of decahydronaphthalene were stirred and dissolved, and then the temperature was slowly raised to 160° C., and the reflux state was maintained for 24 hours.

[0042] After the reaction liquid is cooled, pour 12% 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 6A pale yellow precipitate appeared in the aqueous solution. The solid was dried and purified by column chromatography to obtain the product [bis(cyclopentadiene-iron)-biphenyl]hexafluorophosphate with a yield of 49.12%.

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Abstract

The invention relates to the preparation of biferrocene aromatic salt which is used as novel cationic photo initiator and the application thereof, pertaining to the technical field of organic synthesis and cationic photo polymerization. The invention provides a biferrocene aromatic salt that is collectively named (2(cyclopentadienyl-Fe) aromatic) salt, which is used as a photo initiator in the cationic photo polymerization. In the preparation of the compound, the ferrocene and polycyclic aromatic hydrocarbon are used as the raw materials and Lewis acid is adopted as an activator, providing simple and convenient preparation. The compound still has relatively high absorbency over 300nm and can match with a long-wave ultraviolet source, thus efficiently activating the photopolymerization of epoxy compounds and vinyl ether compounds.

Description

technical field [0001] The invention relates to a novel cationic photopolymerization initiator, which synthesizes a series of [bis(cyclopentadiene-iron) arene] salts and belongs to the technical field 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 photo-initiated cationic monomers and prepolymers; ② Not subject to oxygen inhibition; ③ Cationic photopolymerization is a living aggregate. [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 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C08G59/40C08J3/28C08K5/56
Inventor 任晓玲王涛张影李治权马丽景
Owner BEIJING UNIV OF CHEM TECH
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