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Long wavelength photoinitiator containing carbazole derivatives and preparation method thereof

A technology of carbazole derivatives and photoinitiators, applied in the field of long-wavelength photoinitiators and their preparation, can solve problems such as toxicity and application limitations, and achieve the effects of enhanced conjugation, reduced dosage, and good solubility

Active Publication Date: 2019-07-05
BEIJING UNIV OF CHEM TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cleavage-type photoinitiators can quickly initiate the polymerization of monomers, but their own structure is cleaved into smaller molecules, such as benzaldehyde, during the process of initiating polymerization, so they are toxic, so their applications are limited

Method used

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  • Long wavelength photoinitiator containing carbazole derivatives and preparation method thereof
  • Long wavelength photoinitiator containing carbazole derivatives and preparation method thereof
  • Long wavelength photoinitiator containing carbazole derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1) Weigh 2 mol of ethylcarbazole formaldehyde and 1 mol of tetrahydrothiopyrone dissolved in 20 ml of ethyl acetate, stir and mix well. Add 3-5 drops of 5% NaOH aqueous solution (0.5g NaOH, 9.5g water) to the prepared mixed solution dropwise, adjust the pH value to 13, and react under nitrogen protection at 30°C for 3h, then use an ice bath to continue the reaction 3h, pale yellow crystals were precipitated.

[0040] 2) Wash the light yellow crystal in step 1) with ethanol, dry in vacuo to remove the solvent, and obtain a pure light yellow product, the synthesized product is 2,6-(N-ethyl)-carbazoleethylene-tetrahydrothiopyrone .

[0041] 2,6-(N-Ethyl)carbazoleethylene-tetrahydrothiopyrone at a molar concentration of 1×10 -5 Soluble in chromatographic grade acetonitrile, test its ultraviolet absorption spectrum, its maximum absorption wavelength can reach 500nm, such as figure 1 shown.

[0042] Dissolve 2,6-(N-ethyl)carbazoleethylene-tetrahydrothiopyrone in monomer P...

Embodiment 2

[0044] 1) Weigh 2 mol of ethylcarbazole formaldehyde and 1 mol of tetrahydropyrone and dissolve in 20 ml of ethyl acetate, stir and mix evenly, then add dropwise 3 to 5 drops of 5% NaOH solution (0.5 g NaOH, 9.5 g of water), adjust the pH to 13, react under nitrogen protection at 30° C. for 3 h, then use an ice bath to continue the reaction for 3 h, and pale yellow crystals are precipitated.

[0045] 2) The light yellow crystal in step 1) was washed with ethanol, and the solvent was removed by vacuum drying to obtain a pure light yellow product, which was 2,6-(N-ethyl)carbazoleethylene-tetrahydropyrone.

[0046] 2,6-(N-Ethyl)carbazoleethylene-tetrahydropyrone at a molar concentration of 1×10 -5 It is dissolved in chromatographic grade acetonitrile, and its ultraviolet absorption spectrum is tested. The results show that its maximum absorption wavelength can reach 500nm.

[0047] Dissolve 2,6-(N-ethyl)carbazoleethylene-tetrahydropyrone in PEGDA and HDDA at concentrations of 1%...

Embodiment 3

[0049]1) Weigh 2 mol of ethyl carbazole formaldehyde and 1 mol of tetrahydro-N-methylpiperidone and dissolve in 20 ml of ethyl acetate, stir and mix evenly. Add 3-5 drops of NaOH solution (0.5g NaOH, 9.5g water) with a mass fraction of 5% to the prepared mixed solution dropwise, adjust the pH value to 13, and react under nitrogen protection at 30°C for 3h, then use an ice bath to continue the reaction 3h, pale yellow crystals were precipitated.

[0050] 2) Wash the light yellow crystals in step 1) with ethanol, dry in vacuo to remove the solvent, and obtain a pure light yellow product, which is 2,6-(N-ethyl)carbazoleethylene-tetrahydro(N-methyl) base) piperidone.

[0051] Add 2,6-(N-ethyl)carbazoleethylene-tetrahydro(N-methyl)piperidone to a molar concentration of 1×10 -5 Soluble in chromatographic grade acetonitrile, test its ultraviolet absorption spectrum, its maximum absorption wavelength can reach 500nm.

[0052] 2,6-(N-ethyl)carbazoleethylene-tetrahydro(N-methyl)piper...

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Abstract

The invention discloses a long wavelength photoinitiator containing carbazole derivatives, and relates to the field of photo-cured materials. The photoinitiator is synthesized by Claisen-Schmidt reactions. Aldehyde that participates in the reactions contains carbazole derivatives and does not contain alpha-H. Due to the carbazole groups, the conjugate action of the molecular structure is enhanced,and thus the maximum absorption wavelength of the synthesis product is prolonged. The provided initiator can be well dissolved in most photo-polymerized monomers; the UV absorption peaks can be matched with corresponding LED lamps; under the irradiation of LED lamps, polymerization of multiple monomers is triggered, and the curing effect is good. The invention also discloses a preparation methodof the long wavelength photoinitiator. The preparation method is simple, and the preparation conditions are mild.

Description

technical field [0001] The invention relates to the field of photocurable materials, in particular to a long-wavelength photoinitiator and a preparation method thereof. Background technique [0002] The photoinitiator is the core component of the photopolymerization reaction. In the photocuring process, the photoinitiator determines whether the oligomer and diluent of the formulation system can quickly change from liquid to solid under light irradiation. In addition, the development of photoinitiators is closely related to the development of ultraviolet light sources. Traditional light source mercury lamps are gradually banned due to mercury pollution problems and replaced by new LED light sources. The preparation technology of short-wavelength (below 365nm) LED light source is not yet mature, and the initiator with the traditional mercury lamp light source often triggers a shorter wavelength. Therefore, designing and synthesizing a new type of photoinitiator suitable for L...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07D405/14C07D401/14C08F2/48
CPCC07D401/14C07D405/14C07D409/14C08F2/48
Inventor 朱晓群钟美娟聂俊
Owner BEIJING UNIV OF CHEM TECH
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