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Coumarin oxime ester photoinitiator

A photoinitiator, coumarin oxime technology, applied in the field of a class of photoinitiator containing coumarin unit and oxime ester unit and its preparation, can solve the problems of poor activity, slow printing speed, small absorption cross section, etc.

Active Publication Date: 2019-07-05
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To a certain extent, it makes up for the shortcomings of traditional DLP 3D printing, but two-photon printing is to achieve curing at the focal point, and the printing speed is relatively slow, so it is very important to develop high-performance two-photon photoinitiators
So far, free radical two-photon polymerization is mainly based on the intermolecular electron transfer mechanism, such as the dye / amine system, that is, under two-photon excitation, the dye absorbs energy, and then transfers electrons to the amine molecule to generate an active amine, followed by Initiate polymerization, but the system will have reverse electron transfer and low initiation efficiency; another mechanism is light-induced direct cleavage to generate active species. Commercial photoinitiators such as Irgacure369 and TPO are also used in two-photon polymerization. Due to its small two-photon absorption cross-section, the activity under two-photon laser is not good, but its absorption cross-section is small
At present, LED photoinitiators are developing toward visible light. For example, CN109305951A discloses a kind of coumarin compound and its preparation and application, which is used as a visible light LED initiator, but this type of structure cannot realize multifunctional (such as two-photon initiation activity ), efficient use of

Method used

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  • Coumarin oxime ester photoinitiator
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  • Coumarin oxime ester photoinitiator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069]

[0070] The preparation of coumarin oxime ester photoinitiator H1, concrete preparation steps are as follows:

[0071] (1) Synthesis of A1

[0072] In a 50ml single-necked round bottom flask, add 3.37g (30.9mmol) 3-aminophenol, 1.25g yttrium nitrate hexahydrate (Y(NO 3 ) 3 ·6H 2O) (3.3mmol) and 4.82g (37.1mmol) ethyl acetoacetate, reacted at 90 ° C for 2 hours, then cooled to room temperature, dissolved the reactant with 50ml ethanol, then poured it into a large amount of water, and filtered it to obtain yellow The solid was dried in a vacuum oven at 40° C. to obtain 2.58 g of the final product, with a yield of 50%.

[0073]

[0074] A1 NMR characterization: 1 H NMR (400MHz, Chloroform-d) δ7.39(dd, J=2.3,1.2Hz,1H),6.61(d,J=2.3Hz,1H),6.59(d,J=1.2Hz,1H),6.05 (q, J=1.2Hz, 1H), 4.17(s, 2H), 2.38(d, J=1.2Hz, 3H).

[0075] (2) Synthesis of B1

[0076] Disperse 3.25g (18.6mmol) of A1 in 90ml of water, add 7ml of concentrated sulfuric acid dropwise, and then add 1...

Embodiment 2

[0096]

[0097] The synthesis of H2, the specific steps are as follows:

[0098] (1) Synthesis of C1

[0099] In a 100ml reaction flask, 1.5g (6.8mmol) of 3-iodophenol and 2g (21.1mmol) of anhydrous magnesium chloride were dissolved in 50ml of anhydrous acetonitrile and 6ml (43.2mmol) of triethylamine solution, and then 2g (66.7 mmol) paraformaldehyde, reacted at 85°C for 24 hours; the reaction was cooled to room temperature, then neutralized with 1N HCl solution, extracted three times with dichloromethane, anhydrous Na 2 SO 4 Drying and rotary evaporation gave a crude product, which was finally separated and purified by silica gel column chromatography to obtain 0.69 g of the product, with a yield of 40%.

[0100]

[0101] C1 NMR characterization: 1 H NMR (400MHz, Chloroform-d) δ11.05(s, 1H), 9.87(s, 1H), 7.46(s, 1H), 7.42(dd, J=8.1, 1.5Hz, 1H), 7.26(d, J = 8.1 Hz, 1H).

[0102] (2) Preparation of D1

[0103] In a 50ml single-necked round bottom flask, dissolve 0....

Embodiment 3

[0119] Compound H1 and compound H2 prepared in Example 1 and Example 2 are respectively subjected to performance measurement, and its absorption band is 360-450nm as measured by an ultraviolet-visible spectrophotometer, and its ultraviolet-visible absorption spectrum is shown in figure 1 , it can be found that its maximum absorption wavelength is around 405nm, which matches the wavelength of the longest used 405nm LED lamp.

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Abstract

The invention provides a coumarin oxime ester photoinitiator and a preparation method thereof. The molecular structure general formula is shown in the formula (I). The photoinitiator triggers photocuring under the radiation wavelength of 360-450 nm, and is applied to the fields such as single-photon 3D printing, double-photon 3D printing, printing ink and photoresist. The photoinitiator can serveas an LED photoinitiator and a double-photon photoinitiator, good triggering activity is achieved, one photoinitiator has two purposes, and the manufacturing cost is reduced to a certain degree.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to a class of photoinitiators containing coumarin units and oxime ester units and a preparation method thereof. Background technique [0002] With the increasingly prominent social environment and energy problems, light-curable materials have attracted widespread attention because of the advantages of no or only a small amount of solvent volatilization during the curing process. [0003] Photoinitiator is an essential component in photocuring technology, plays a vital role in the photocuring process, plays a decisive role in the speed of photocuring, and even affects the performance of photocuring materials. The photoinitiator is a photolysis reaction under the excitation of the light source, which generates reactive free radicals or ions, and then initiates the polymerization reaction of the monomer, thereby forming a cross-linked polymer network structure, which is used in coatings,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C08F222/20C08F222/14C08F2/48G03F7/004G03F7/027C09D11/101
CPCC07D311/16C08F2/48G03F7/004G03F7/027C08F222/10C09D11/101C08F222/103
Inventor 李治全邱婉婉李梦琦刘仁
Owner JIANGNAN UNIV
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