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Single-component long-wavelength photoinitiators and preparation method thereof

A photoinitiator, one-component technology, applied in the direction of organic chemistry, can solve the problems of short wavelength, mercury pollution, etc., and achieve the effects of reduced dosage, high molar extinction coefficient, and good solubility

Active Publication Date: 2019-07-02
BEIJING UNIV OF CHEM TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Mercury lamps will cause mercury pollution problems during use, so they are gradually replaced by LED light sources, but the preparation technology for short-wavelength LED light sources is not yet mature, and the wavelengths of initiators suitable for mercury lamp light sources are relatively short. A class of long-wavelength photoinitiators suitable for LED light sources is an urgent need for the development of photopolymerization technology

Method used

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  • Single-component long-wavelength photoinitiators and preparation method thereof
  • Single-component long-wavelength photoinitiators and preparation method thereof
  • Single-component long-wavelength photoinitiators and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] 1) Weigh 1 mol of ethyl carbazole formaldehyde and 1 mol of acetylfuran, dissolve them in 20 ml of ethanol, and mix them evenly under stirring.

[0037] 2) Add 3-5 drops of ammonia solution with a mass fraction of 5% to the mixed solution prepared in step 1), adjust the pH value to 13, react at 30° C. for 3 hours, feed nitrogen gas, and continue the reaction for 3 hours in an ice bath. Pale yellow crystals precipitated.

[0038] 3) The light yellow crystal in step 2) is washed with ethanol, and the solvent is removed by vacuum drying to obtain a pure light yellow product, which is N-ethylcarbazoleethylene-furanone.

[0039] Dissolve N-ethylcarbazoleethylene-furanone in chromatography-grade acetonitrile at a concentration of 1 × 10 -5 mol / L, test its UV absorption, get its UV absorption spectrum as figure 2 As shown, the maximum absorption wavelength can reach 425nm.

[0040] Add N-ethylcarbazoleethylene-furalone to PEGDA and HDDA at a mass concentration of 1%, 0.1%,...

Embodiment 2

[0042] 1) Weigh 1mol of ethylcarbazole formaldehyde and 1mol of acetylbenzene and dissolve in 20ml of ethanol, and mix evenly under stirring.

[0043] 2) Add 3-5 drops of ammonia solution with a mass fraction of 5% to the mixed solution prepared in step 1), adjust the pH to 13, react at 30°C for 3 hours, feed nitrogen gas, continue the reaction for 3 hours in an ice bath, and precipitate Pale yellow crystals.

[0044] 3) Washing the light yellow crystal in step 2) with ethanol, drying in vacuo to remove the solvent to obtain a pure light yellow product, the synthesized product is N-ethylcarbazoleethylene-benzophenone.

[0045] Dissolve N-ethylcarbazoleethylene-benzophenone in chromatography-grade acetonitrile at a concentration of 1 x 10 -5 mol / L, test its UV absorption. The results show that its ultraviolet absorption wavelength range is 250nm-420nm.

[0046] Add N-ethylcarbazoleethylene-benzophenone to PEGDA and HDDA monomers at a mass concentration of 1%, 0.1%, 0.01%, an...

Embodiment 3

[0048] 1) Weigh 1 mol of ethylcarbazole formaldehyde and 1 mol of acetylthiophene, dissolve them in 20 ml of ethanol, and mix them evenly under stirring.

[0049] 2) Add 3-5 drops of ammonia solution with a mass fraction of 5% to the mixed solution prepared in step 1), adjust the pH value to 13, react at 30° C. for 12 hours, feed nitrogen gas, and continue the reaction for 3 hours in an ice bath. Pale yellow crystals precipitated.

[0050] 3) Washing the light yellow crystal in step 2) with ethanol, drying in vacuo to remove the solvent to obtain a pure light yellow product, the synthesized product is N-ethylcarbazoleethylene-thienyl ketone.

[0051] Dissolve N-ethylcarbazoleethylene-thiophenemethanone in chromatography-grade acetonitrile at a concentration of 1 × 10 -5 mol / L, test its UV absorption. Its ultraviolet absorption wavelength range is 250nm-420nm.

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Abstract

The invention discloses single-component long-wavelength photoinitiators, and relates to the field of photocurable materials. Photoinitiators are synthesized by a Claisen-Schmidt reaction, alpha-H-free aldehyde participating in the reaction comprises a carbazole derivative, and the carbazolyl group enhances the conjugation of the molecular structure of the photoinitiators to lengthen the maximum absorption wavelength of the synthesized products. The initiators have a good solubility in most photopolymerizable monomers, have an ultraviolet absorption peak matched with a corresponding LED lightsource, and can initiate polymerization of various monomers and achieve a good curing effect under the illumination of the LED light source. The invention also discloses a preparation method of the single-component long-wavelength photoinitiators. The preparation method has the advantages of simple conditions and mild conditions.

Description

technical field [0001] The invention relates to the field of photocurable materials, in particular to a single-component long-wavelength photoinitiator and a preparation method thereof. Background technique [0002] Photoinitiator is a key component of photocurable materials, which plays a decisive role in the photocuring speed of photocurable materials. A photoinitiator is a substance that can absorb radiation energy, undergo photochemical changes after being excited, and produce active intermediates (free radicals or cations) with the ability to initiate polymerization. [0003] Photoinitiators can be divided into ultraviolet photoinitiators (absorbing ultraviolet light region 250-420nm) and visible light initiators (absorbing visible light region 400-700nm) due to the difference in absorbing radiation energy. Photoinitiators can be divided into two categories: free radical photoinitiators and cationic photoinitiators due to the different active intermediates produced. F...

Claims

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Application Information

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IPC IPC(8): C07D405/06C07D209/86C07D409/06C08F2/48
CPCC07D209/86C07D405/06C07D409/06C08F2/48
Inventor 朱晓群钟美娟聂俊
Owner BEIJING UNIV OF CHEM TECH
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