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Application of a Class of Dianilino-Biphenyl Carbonyl Compounds in Photocuring Formula System

A compound and light-curing technology, which is applied in the field of diphenylamino biphenyl carbonyl compounds and radiation-cured formula products, can solve the problems of high energy consumption and short life, mercury vapor does not conform to new strategic trends, etc., and achieve great development significance. The effect of high monomer conversion

Active Publication Date: 2020-12-08
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The current light-curing light sources usually use mercury lamps with high energy consumption and short life, and the mercury vapor produced does not conform to the new strategic trend of the world's energy-saving and environmental protection industries. Therefore, in recent years, low-energy, environmentally friendly and energy-saving LED light sources have gained increasing popularity. Emphasis on and rapid development, and the application of LED light curing technology has greatly reduced energy consumption and ozone generation, and the industry continues to grow strongly

Method used

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  • Application of a Class of Dianilino-Biphenyl Carbonyl Compounds in Photocuring Formula System
  • Application of a Class of Dianilino-Biphenyl Carbonyl Compounds in Photocuring Formula System
  • Application of a Class of Dianilino-Biphenyl Carbonyl Compounds in Photocuring Formula System

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: DPA-BPHO is synthesized according to the following route

[0021]

[0022] (a): caproyl chloride, aluminum trichloride, anhydrous dichloromethane;

[0023] (b): Potassium carbonate, tetrakis(triphenylphosphine) palladium, toluene / ethanol / water, 90°C, 12h;

[0024] 1. Synthesis of p-1-p-bromophenylhexanone

[0025] Quickly put aluminum trichloride (5.32g, 0.04mol) in a dried 250mL three-neck flask, vacuumize and fill with nitrogen several times, then weigh bromobenzene (3.14g, 0.02mol) and inject it, cool to 0°C, Add hexanoyl chloride (4.03g, 0.03mol) slowly, and after the dropwise addition is complete, remove the ice bath, stir at room temperature for 5h, and monitor the reaction by TLC until the end. The system was then poured into ice water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to obtain 3.0 g of a white flaky solid.

[0026] 1 H NMR (400MHz, CDCl 3 )δ7.82(d, J=8.6Hz, 2H), 7.59(d, J=8.6Hz, 2H), 2.93(dd,...

Embodiment 2

[0030] Embodiment two: the photochemical physical property of molecule

[0031] Molecular DPA-BPHO in embodiment one has carried out ultraviolet-visible light spectral analysis, as figure 1 It is the ultraviolet spectrogram of the photoinitiator molecule at different concentrations. According to the Lambert-Beer law and the linear fitting of the relationship between the absorbance and the concentration in the figure, the molar extinction coefficient of the target product at different wavelengths can be calculated, as shown in the following table :

[0032]

Embodiment 3

[0033] Example three: photodegradation properties of molecules

[0034] The molecule in Example 1 is illuminated, and the real-time spectrum change is determined by ultraviolet analysis, and the acetonitrile solution of a certain concentration of DPA-BPHO placed in a 3ml ultraviolet cuvette is irradiated with a 385nm LED light source, and then the length of illumination is compared to the spectrum. influence, such as figure 2 shown. It is found that the target molecule does not undergo photolysis basically under light irradiation, so adding 2 equivalents of iodonium salt solution, repeating the above experiment, it is found that the molecule undergoes obvious photodegradation, such as image 3 As shown, it is speculated that DPA-BPHO can act as a sensitizer of diphenyliodonium salt to initiate cationic polymerization.

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Abstract

The invention relates to the technical field of novel material organic chemicals, in particular to a diphenylamino biphenyl carbonyl compound shown as a formula (I), a purpose of the compound as a radiation curing photoinitiator, and application purposes of the compound in various occasions such as radiation curing recipe products, particularly photocuring paint or ink and the like. The formula (I) is shown in the description.

Description

【Technical field】 [0001] The present invention relates to the technical field of new material organic chemicals, in particular to a class of dianilino biphenyl carbonyl compounds, their use as radiation curing photoinitiators, and their use in radiation curing formula products, especially in UV-Vis- LED light-curing coatings or inks, and many other applications involving light-curing occasions. 【Background technique】 [0002] Photoinitiator compounds are an important class of fine organic chemical materials, and are one of the important components in the photocuring technology system of high efficiency, energy saving and environmental protection. In the field of radiation curing technology with ultraviolet light or visible (UV) light or LED (i.e. Light-Emitting Diode) as light source, the photoinitiator compound that can generate free radical active species under light irradiation conditions is the one that induces ethylenically unsaturated systems. Key species for efficien...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/22C07C221/00C07C45/46C07C49/807C09D11/101C09D7/63
CPCC07C45/46C07C221/00C09D11/101C07C49/807C07C225/22
Inventor 金明周茹春潘海燕万德成
Owner TONGJI UNIV
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