Pendant naphthalene group-containing benzene ligand ferrocenium salt cationic photoinitiators and preparation method thereof

A technology of naphthyloxy pendant group and ferrocene salt, which is applied in the fields of organic synthesis and cationic photopolymerization, and can solve the problems of inability to match the light source

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

AI Technical Summary

Problems solved by technology

The absorption peaks of these two types of compounds in the UV-Vis absorption spectrum are located below 300nm, and there is almost no absorption above 300nm, so they cannot match some commonly used light sources such as high-pressure mercury lamps

Method used

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  • Pendant naphthalene group-containing benzene ligand ferrocenium salt cationic photoinitiators and preparation method thereof
  • Pendant naphthalene group-containing benzene ligand ferrocenium salt cationic photoinitiators and preparation method thereof
  • Pendant naphthalene group-containing benzene ligand ferrocenium salt cationic photoinitiators and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1 prepares cyclopentadiene-iron-chlorobenzene hexafluorophosphate

[0035] N 2 Add 0.05mol ferrocene, 0.15mol anhydrous AlCl to a 250ml three-neck flask under protection 3 , 0.15mol of aluminum powder and 10ml of chlorobenzene, with 50ml of cyclohexane as a solvent, stirred, and maintained heating and reflux for 10 hours.

[0036] After the reaction solution is cooled, slowly add 10% methanol to the reaction solution, then pour the reaction mixture into a beaker filled with ice water, fully stir, filter, separate liquids, wash the organic phase with water, and combine with the water phase, Repeated washing with cyclohexane, and then adding excess KPF6 aqueous solution that is a yellow precipitate. After the solid was dried, it was purified by column chromatography to obtain cyclopentadiene-iron-chlorobenzene hexafluorophosphate with a yield of 40%.

Embodiment 2

[0037] Example 2 Preparation of benzene ligand ferrocene hexafluorophosphate of α-naphthyloxy side group

[0038] N 2 Under protection, in a 100ml round bottom flask, 0.01mol cyclopentadiene-iron-chlorobenzene hexafluorophosphate and 0.02mol α-naphthol were dissolved in 10ml N, N-dimethylformamide, catalyzed by 0.02mol potassium carbonate After the reaction was completed, add 15% hydrochloric acid to adjust to acidity, filter with suction, add saturated KPF 6 aqueous solution, a yellow crude product was obtained. Drying, column chromatography purification to obtain the benzene ligand ferrocene hexafluorophosphate of α-naphthyloxy side group, the yield is 85%.

Embodiment 3

[0039] Example 3 Preparation of benzene ligand ferrocene hexafluorophosphate of β-naphthyloxy side group

[0040] N 2 Under protection, in a 100ml round bottom flask, 0.01mol cyclopentadiene-iron-chlorobenzene hexafluorophosphate and 0.02mol β-naphthol were dissolved in 10ml N, N-dimethylformamide, catalyzed by 0.02mol potassium carbonate Reaction at lower temperature for 7 hours, add 15% hydrochloric acid to adjust to acidity, filter with suction, add saturated KPF 6 aqueous solution, a yellow crude product was obtained. Drying, column chromatography purification to obtain the benzene ligand ferrocene hexafluorophosphate of the product β-naphthyloxy side group, the yield is 88%.

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Abstract

The invention discloses pendant naphthalene group-containing cyclopentadienyl-iron-benzyl ferrocenium salt compounds used as photoinitiators for cationic photopolymerization, and belongs to the technical fields of organic synthesis and cationic photopolymerization. The preparation method of the compounds comprises two steps: 1, taking ferrocene and chlorobenzene as raw materials, and generating ligand exchange reaction to obtain cyclopentadienyl-iron-chlorobenzene salts under the catalysis of Lewis acid; and 2, generating nucleophilicsubstitutionreaction with corresponding naphthol compounds under alkaline environment, and introducing the pendant naphthalene group onto the benzene ligand. The compounds have good ultraviolet absorptivity and photo initiating activity, can initiate polymerization of epoxy compounds and vinyl ethers compounds, and have wide study potential and application prospect in the field of photocuring application.

Description

technical field [0001] The invention relates to a benzene ligand ferrocene hexafluorophosphate cationic photoinitiator containing a naphthyloxy side group and a preparation method thereof, belonging to the technical fields of organic synthesis and cationic photopolymerization. Background technique [0002] Since Crivello et al. successfully studied the cationic photopolymerization initiating activity of diaryl iodonium salt and triaryl sulfonium salt in the 1970s, the research and application of cationic photopolymerization have made great progress. Compared with the radical photocuring system, the cationic photocuring system has the advantages of photoinitiated cationic monomers and prepolymers, and is not free from oxygen inhibition and active polymerization. Compared with the many types of free radical photoinitiators used in free radical photopolymerization systems that have been developed more maturely, there are fewer types of initiators for cationic photopolymerizatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 王涛李治全
Owner BEIJING UNIV OF CHEM TECH
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