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Phenazine derivative-series photoinitiator as well as preparation method and application thereof

A technology of photoinitiators and derivatives, applied in the direction of organic chemistry, can solve the problems of limited application range, low light absorption efficiency, poor emission wavelength matching, etc., and achieve the improvement of light absorption efficiency, high photocuring efficiency, and reduced mobility Effect

Active Publication Date: 2021-04-27
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current commercial ultraviolet light-emitting diode (UV-LED) mainly emits invisible light with a single wavelength, and the wavelength includes 385nm, 395nm, 405nm, etc., while the ultraviolet absorption wavelength of photoinitiator 907 is concentrated at 231nm and 307nm, which is different from UV - The emission wavelength matching of LED is poor, resulting in low light absorption efficiency; and the photoinitiator 907 has the risk of migration during use, which limits its application range;
[0005] Phenazine, alias diazanthracene, is mainly used in dyestuff, medicine, organic synthesis intermediate and biochemical research; Prior art discloses a kind of benzophenazine photosensitizer, can be used for free radical and cationic polymerization, but its to The light source requirements are relatively strict, and the photocuring reaction can only be carried out under the irradiation of high-intensity xenon lamps, which limits its application

Method used

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  • Phenazine derivative-series photoinitiator as well as preparation method and application thereof
  • Phenazine derivative-series photoinitiator as well as preparation method and application thereof
  • Phenazine derivative-series photoinitiator as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0094] The molecular formula of the phenazine derivative photoinitiator in the present embodiment is shown in the following formula (II):

[0095]

[0096] The present embodiment provides the preparation method of phenazine derivative photoinitiator as shown above, described method comprises the following steps:

[0097] (1) Disperse 1 mol of 1,2-naphthoquinone and 1.4 mol of aluminum trichloride in 500 mL of dichloroethane, then add 1.2 mol of isobutyryl chloride dropwise, and perform Friedel-Crafts acylation reaction at 13°C for 2 hours, then Mixed with 800mL of 2.5wt% hydrochloric acid for hydrolysis, liquid separation, washing with water, and precipitation to obtain the compound shown in formula (III);

[0098]

[0099] (2) Mix and dissolve the compound represented by formula (III) obtained in step (1) and o-phenylenediamine in acetic acid at a molar ratio of 1:1, and react under stirring at 65°C for 1.5h to remove dissolved to obtain the compound shown in the follo...

Embodiment 2

[0112] The difference between this embodiment and Example 1 is that in the step (2), an equimolar amount of o-phenylenediamine is replaced by 4-methyl o-phenylenediamine, and the molecular formula is as follows;

[0113]

[0114] Other parameters and conditions are exactly the same as in Example 1.

[0115] Include the following two structures in the photoinitiator gained in the present embodiment;

[0116]

[0117] The HPLC content of the two is 1:1;

[0118] The mass spectrometric analysis result of photoinitiator described in the present embodiment is as follows;

[0119] MS: m / z [M+1]+=400.19 (Mw=399.48).

[0120] The H-NMR analysis result of photoinitiator in the present embodiment is as follows;

[0121] 1H-NMR (400MHz, CDCl3): δ8.18~8.10(m,1H),7.95-7.80(m,2H),7.75~7.67(m,3H),7.55(m,1H),7.30~7.20(m ,1H) 3.65(t,4H), 2.40~2.30(m,7H), 1.45(s,6H).

Embodiment 3

[0123] The difference between this example and Example 1 is that in step (2), the equimolar amount of o-phenylenediamine is replaced by 3,4-dimethyl-o-phenylenediamine, and the molecular formula is as follows;

[0124]

[0125] Other parameters and conditions are exactly the same as in Example 1.

[0126] Include the following two structures in the photoinitiator gained in the present embodiment;

[0127] The HPLC content of the two is 1:1;

[0128] The mass spectrometric analysis result of photoinitiator described in the present embodiment is as follows;

[0129] MS: m / z [M+1]+=423.21 (Mw=413.51).

[0130] The H-NMR analysis result of photoinitiator in the present embodiment is as follows; 1H-NMR (400MHz, CDCl ): δ8.08 (d, 1H), 7.85~7.67 (m, 4H), 7.36 (d, 1H) ,7.28(t,1H),3.68(t,4H),2.5~2.40(m,10H),1.45(s,6H).

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Abstract

The invention relates to a phenazine derivative-series photoinitiator as well as a preparation method and application thereof. The phenazine derivative-series photoinitiator comprises a phenonaphthazine group and a 2-methyl-2-morpholinyl-acetonyl group connected to the benzene ring of the phenonaphthazine group. Compared with a photoinitiator 907, the absorption wavelength of the phenazine derivative-series photoinitiator undergoes red shift, so the phenazine derivative-series photoinitiator has higher matching degree with the emission wavelength of a UV-LED, and light absorption efficiency is obviously improved; and the phenonaphthazine group in the phenazine derivative-series photoinitiator is an electron-rich group, and interacts with the 2-methyl-2-morpholinyl-acetonyl group to make the phenazine derivative-series photoinitiator have high curing efficiency, and a migration rate in the use process is obviously reduced, so the application range of the phenazine derivative-series photoinitiator is obviously broadened.

Description

technical field [0001] The invention belongs to the field of photoinitiators, and relates to a phenazine derivative photoinitiator, a preparation method and application thereof. Background technique [0002] 2-methyl-1-(4-methylthiophenyl)-2-morpholine-1-propanone (photoinitiator 907) is a free radical (I) type photoinitiator, mainly used for the corresponding UV polymerization curing of the resin; its molecular formula is as follows: [0003] [0004] The current commercial ultraviolet light-emitting diode (UV-LED) mainly emits invisible light with a single wavelength, and the wavelength includes 385nm, 395nm, 405nm, etc., while the ultraviolet absorption wavelength of photoinitiator 907 is concentrated at 231nm and 307nm, which is different from UV - The emission wavelength matching of LED is poor, resulting in low light absorption efficiency; and the photoinitiator 907 has the risk of migration during use, which limits its application range; [0005] Phenazine, alias...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/38C08F2/48
CPCC07D241/38C08F2/48
Inventor 赵国锋张齐毛桂红武锦鹏
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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