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A kind of benzophenone derivative photoinitiator containing hexamethylsilylamine structure and preparation method thereof

A technology of hexamethylsilamine and benzophenone is applied in the field of preparation of benzophenone derivative photoinitiator photoinitiator, which can solve the problem of weak light intensity, low power conversion efficiency, influence on irradiation efficiency, etc. problem, to achieve the effect of high reaction rate, strong application value, and high photo-initiated activity

Active Publication Date: 2021-01-05
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The power conversion efficiency of traditional mercury lamps as irradiation light sources is not high, and there is still a lot of room for exploration in terms of energy saving, and the ultraviolet light produced by them is in a continuous band, and the intensity of the strongest absorbed ultraviolet light is weak, which affects the irradiation. efficiency

Method used

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  • A kind of benzophenone derivative photoinitiator containing hexamethylsilylamine structure and preparation method thereof
  • A kind of benzophenone derivative photoinitiator containing hexamethylsilylamine structure and preparation method thereof
  • A kind of benzophenone derivative photoinitiator containing hexamethylsilylamine structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Using 80ml tetrahydrofuran solvent as the medium, add 3.0g (0.015mol) of 4-fluorobenzophenone and 2.75g (0.015mol) sodium bis(trimethylsilyl)amide, heat the reaction system to 80°C, and reflux for 4h; After the reaction was complete, the solid was filtered off, the solvent was spin-dried, heated and dissolved with 200ml of absolute ethanol, and cooled to crystallize to obtain 1.7g of a slightly yellow powder with a yield of 33.3% (theoretical yield 5.11g). The product 4-hexamethylsilylamine- The structure of benzophenone is shown in II, and the NMR data is: 1 H NMR (400MHz, DMSO): δ7.84(t, J=7.8Hz, 4H), 7.62(t, J=7.4Hz, 1H), 7.58–7.48(m, 4H), 0.04(s, 18H). The relative molecular mass in the mass spectrum ESI-MS normal spectrum is 341.1, confirming that the target product was synthesized.

[0029]

Embodiment 2

[0031] In 150ml of N,N-dimethylformamide (DMF) as a medium, add 6.5g (0.03mol) of 4,4-difluorobenzophenone and 5.68g (0.031mol) of bis(trimethylsilyl) Sodium amide, the reaction system was heated to 130°C, and refluxed for 6h; after the reaction was completed, the solid was filtered off, the solvent was spin-dried, heated and dissolved with 200ml of absolute ethanol, and 2.9g of slightly yellow powder was obtained by cooling and crystallization, with a yield of 27% (theoretical yield 10.77g), the structure of the product 4-hexamethylsilylamine-9-fluoro-benzophenone is shown in IV, and the NMR data are: 1 H NMR (400MHz, DMSO): 7.83–7.76(m,2H), 7.76–7.68(m,2H), 7.54(t,J=7.4Hz,2H), 7.13–7.06(m,2H), 0.02(s , 18H). Product M=359.15, Me 3 Si=73.05, mass spectrum ESI-MS (+) showed the following molecular ion peaks: 359.0 (65%), 287.0 (42%), confirming that the target product was synthesized.

[0032]

Embodiment 3

[0034]With 150ml of N,N-dimethylformamide (DMF) as the medium, add 6.5g (0.03mol) of 4,4-difluorobenzophenone and 12.81g (0.07mol) of bis(trimethylsilyl) Sodium amide, the reaction system was heated to 150°C, and refluxed for 6h; after the reaction was completed, the solid was filtered off, the solvent was spin-dried, heated and dissolved with 200ml of absolute ethanol, and cooled to crystallize to obtain 6.3g of slightly yellow powder with a yield of 42% (theoretical yield 15g), the structure of product 4,9-bis(hexamethylsilylamine)-benzophenone is as shown in (Ⅲ), and the NMR data are: 1 H NMR (400MHz, DMSO): 7.83–7.74(m,2H), 7.73–7.61(m,2H), 7.56(t,J=7.3Hz,2H), 7.11–7.03(m,2H), 0.05(s ,36H). Product M=500.5, Me 3 Si=73.05, mass spectrum ESI-MS (+) appeared the following molecular ion peaks: 500.5 (5%), 429.4 (15%), 428.3 (32%), 356.3 (100%), confirming that the target product was synthesized.

[0035]

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Abstract

The invention provides a benzophenone derivative photoinitiator comprising a hexamethylsilylamine structure and a preparation method of the photoinitiator. The photoinitiator comprises the hexamethylsilylamine structure. Bi-hexamethylsilylamine is directly connected with a benzophenone aromatic ring; a chemical general formula of the photoinitiator is shown as formula (I) as shown in the specification; and the photoinitiator can be used for a photocuring system and has the characteristics of high initiation activity and applicability to UV (ultraviolet) LED (light-emitting diode) light sourcecuring. A group X is H, F, (Me3Si)2N or dialkyl amino R1R2N; R1 and R2 of dialkyl amino R1R2N are at least two carbon atom alkyl groups; or R1 and R2 are merged into alkylene with 2-5 carbon atoms; orR1 and R2 are merged into -CH2CH2OCH2CH2-.

Description

technical field [0001] The invention relates to the field of photosensitive materials and light curing, in particular to a benzophenone derivative photoinitiator photoinitiator containing a hexamethylsilamine structure, and also to a benzophenone derivative photoinitiator containing a hexamethylsilamine structure The preparation method of the ketone derivative photoinitiator photoinitiator. Background technique [0002] In recent years, with the introduction of the concept of green environmental protection and sustainable development, photocuring (photopolymerization) technology has been favored by many industries because of its energy saving, high efficiency, and pollution-free, and its application prospects are broader. Photoinitiator (Photoinitiator, PI) is a key component of the photocuring system, which is related to whether the oligomer and reactive diluent can be quickly cross-linked and cured when the formulation system is exposed to light radiation. Therefore, deve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F2/50G03F7/004C07F7/10
CPCC07F7/10C08F2/50G03F7/004
Inventor 廖焕妍杨建文曾兆华
Owner SUN YAT SEN UNIV
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