Acetophenone type photoinitiators using fluorene as conjugated structure as well as preparation method and application of acetophenone type photoinitiators

A technology of photoinitiator and conjugated structure, which is applied in the field of preparation of substituted acetophenone-based photoinitiators, can solve the problems of small molar extinction coefficient, weak absorption, and restrictions on the wide application of photoinitiators, and achieve easy dissolution, fast High initiation rate and high yield

Inactive Publication Date: 2015-12-16
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption wavelength of acetophenone itself is in the far ultraviolet region (absorption wavelength <300nm), and its molar extinction coefficient is very small, so the absorption of light is very weak
These properties limit the wide application of this class of photoinitiators

Method used

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  • Acetophenone type photoinitiators using fluorene as conjugated structure as well as preparation method and application of acetophenone type photoinitiators
  • Acetophenone type photoinitiators using fluorene as conjugated structure as well as preparation method and application of acetophenone type photoinitiators
  • Acetophenone type photoinitiators using fluorene as conjugated structure as well as preparation method and application of acetophenone type photoinitiators

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) Synthesis of 4,4-(N,N diphenylamino) 4-bromo-9,9-dimethylfluorene

[0045] Diphenylamine (33.6g, 0.2mol), 2,7-dibromo-9,9-dimethylfluorene (91.0g, 0.255mol), copper powder (6.4g, 0.1mol), potassium carbonate (56g, 0.4mol), potassium iodide (6.0g, 0.036mol), 18-crown-6 (6.0g, 0.025mol), ortho-dichlorobenzene (200g, 1.36mol) were added to a 500mL flask, vacuum-gas three times System placed at 200 o Heat and reflux in a C oil bath for 96 hours in the dark. After the reaction, o-dichlorobenzene was distilled off under reduced pressure, washed with petroleum ether, and by-products were removed by suction filtration. After the petroleum ether was removed by rotary evaporation, it was extracted three times with dichloromethane, and the organic phase was dried with anhydrous sodium sulfate. v:v), a white powder was obtained after rotary evaporation. Drying in a vacuum oven for 24 hours, the product was 32.0g of 4,4-(N,N diphenylamino)4-bromo-9,9-dimethylfluorene, The yi...

Embodiment 2

[0051] The preparation method is the same as in Example 1, except that in the process of preparing the photoinitiator, 4-bromoacetophenone is used to replace 4-bromo-2,2,2 trifluoroacetophenone to prepare a photoinitiator molecule containing a methyl structure , the molecular structure is the target molecule 2.

Embodiment 3

[0052] Embodiment 3 photoinitiated polymerization process is as follows:

[0053] (1) Free radical polymerization, first prepare the photoinitiation system, monomer (trimethylolpropanetriacrylate, TMPTA): photoinitiator 1: auxiliary agent (N-vinylcarbazole, NVK) = 100: 1.5: 4.5 / 0 (m: m: m) Stir again to fully dissolve. At 4~48mW / cm 2 Under the irradiation of 365nm light sources with different light intensities, the polymerization kinetics and the final monomer conversion rate were speculated by the change of the characteristic peak of the monomer by the method of online infrared spectrum monitoring.

[0054] (2) Cationic polymerization, first prepare photoinitiation system, monomer epoxy cyclohexane: photoinitiator: iodonium salt = 100: 1.5: 4.5 / 0 (m: m: m) and then stir to fully dissolve. Under the irradiation of 365nm light source with different light intensity from 4 to 48mw, the conversion rate of polymerization was estimated by the change of characteristic peak of monom...

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Abstract

The invention relates to acetophenone type photoinitiators using fluorene as a conjugated structure as well as a preparation method and an application of the acetophenone type photoinitiators. According to the photoinitiators, substituted acetophenone with high electron-attracting capability is taken as an electron-attracting group, and fluorene molecules with different lengths are taken as the conjugated structure and form a D-pi-A type molecule system with electron-donating triphenylamine groups. Two types of Type II photoinitiators are provided according to different conjugated structures and different acetophenone substituted positions. The synthesis steps of the photoinitiators are simple, purification is easy, the yield is high, the light absorption property is good, the photoinitiators are easy to dissolve in a monomer, the absorption peak of the photoinitiators ranges from 365 nm to 405 nm, and the photoinitiators can initiate free radical and cationic polymerization under the initiation of ultraviolet and visible light and has a faster initiation speed and very high polymerization conversion rate. Two types of photoinitiators have wide application in the field of UV photocuring.

Description

technical field [0001] The invention relates to a class of ultraviolet-visible light-sensitive substituted acetophenone photoinitiators with fluorene as the main conjugated structure, specifically the preparation of substituted acetophenone photoinitiators with different lengths of fluorene molecules as the conjugated system And its application in the field of photocuring. Background technique [0002] UV curing technology is an environmentally friendly technology in the fields of coatings, inks, adhesives, etc. The main body of the material is generally composed of acrylicphthalein-based resins, polyol acrylates and photoinitiators. Under the action of sufficiently strong ultraviolet light, All cured. Compared with the traditional solvent-containing system, it has outstanding characteristics such as no solvent emission, high efficiency, and energy saving, so it is used in many fields, such as sheet metal processing, composite materials, etc. [0003] Photoinitiator (Photo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07C221/00C07C225/22
Inventor 金明于嫚贾瀚万德成
Owner TONGJI UNIV
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