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Mono-component polysiloxane photoinitiator capable of overcoming oxygen polymerization inhibition and preparation method therefor

A technology of photoinitiator and polysiloxane, applied in the field of photoinitiator, can solve problems such as poor compatibility and influence effect, and achieve the effects of high initiation efficiency, convenient cost control and convenient adjustment

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

AI Technical Summary

Problems solved by technology

There is a problem of poor compatibility between low-polarity hydrogen-containing polysiloxane and active monomers, which makes the physically added hydrogen-containing polysiloxane easy to phase-separate from the photopolymerization system and affect its effect

Method used

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  • Mono-component polysiloxane photoinitiator capable of overcoming oxygen polymerization inhibition and preparation method therefor
  • Mono-component polysiloxane photoinitiator capable of overcoming oxygen polymerization inhibition and preparation method therefor
  • Mono-component polysiloxane photoinitiator capable of overcoming oxygen polymerization inhibition and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]

[0042] Preparation method: Weigh 0.14g (0.5mmol) 2-(N-methyl-N-allyl)thioxanthone and 0.7g 0.30wt% hydrogen-containing polysiloxane (x=0.75 , y+z=0.25, n=28), under an argon atmosphere, add 30 mL of anhydrous tetrahydrofuran and a system of 500 ppm [Pt] Karstedt catalyst, stir the reaction at 25 ° C, and wait for 2-(N-methyl-N-ene After the reaction of propyl)thioxanthone was complete, the tetrahydrofuran was removed under reduced pressure to obtain a single-component polysiloxane photoinitiator capable of overcoming oxygen inhibition, which weighed 0.84 g after drying.

[0043] Proton NMR spectrum:

[0044] 1 H NMR (CDCl3 ,300MHz)δppm: -0.25~0.30(br,40H,Si-CH 3 ),0.35~0.60(br,2H,SiCH 2 ),1.16~1.36(br,2H,SiCH 2 CH 2 ),2.89~3.12(br,3H,NCH 3 ),3.18~3.49(br,2H,NCH 2 ), 4.68(s, 0.67H, Si-H), 6.90~7.15(br, 1H, Ar-H), 7.31~7.48(br, 2H, Ar-H), 7.49~7.66(br, 2H, Ar- H), 7.70-7.90 (br, 1H, Ar-H), 8.56-8.72 (br, 1H, Ar-H). FT-IR (film, cm -1 ):ν=2154(Si-H), 1594(C=...

Embodiment 2

[0048]

[0049] Preparation method: weigh 0.32g (1.0mmol) 4-(N-methyl-N-allyl)-N-(2-methoxyethyl) naphthalene diimide and 0.28g 0.70wt% hydrogen-containing polysiloxane (x=0, y+z=1, n=2), under an argon atmosphere, add 20mL of anhydrous dioxane and a system of 100ppm [Pt] Sperier's catalyst, control The reaction temperature was 40°C. After the reaction of 4-(N-methyl-N-allyl)-N-(2-methoxyethyl)naphthalene diimide was completed, it was cooled to room temperature under an argon atmosphere. The dioxane was removed under reduced pressure to obtain a one-component polysiloxane photoinitiator capable of overcoming oxygen inhibition, which weighed 0.60 g after drying.

[0050] Proton NMR spectrum:

[0051] 1 H NMR (CDCl 3 ,300MHz) δppm: -0.01~0.210(Si-CH 3 ),0.84~0.93(SiCH 2 ), 1.17~1.24 (SiCH 2 CH 2 ), 3.04 (NCH 3 ), 3.37 (OCH 3 ),3.67~3.78(NCH 2 ,CH 3 NCH 2 ),4.41~4.46(OCH 2 ), 4.67(Si-H), 7.12~7.16(Ar-H), 7.61~7.67(Ar-H), 8.40~8.43(Ar-H), 8.47~8.49(Ar-H), 8.56~8.58...

Embodiment 3

[0055]

[0056] Preparation method: Weigh 0.13g (0.5mmol) 2-(allyloxy)thioxanthone and 0.89g0.14wt% hydrogen-containing polysiloxane (x=0.9, y+z=0.1 , n=200), under argon atmosphere, add 20mL of anhydrous tetrahydrofuran and the Sperier's catalyst of system 500ppm [Pt], control the reaction temperature to tetrahydrofuran reflux, after the reaction of 2-(allyloxy)thioxanthone is complete , cooled to room temperature under argon atmosphere. The tetrahydrofuran was removed under reduced pressure to obtain a one-component polysiloxane photoinitiator capable of overcoming oxygen inhibition, which weighed 1.00 g after drying.

[0057] Proton NMR spectrum:

[0058] 1 H NMR (CDCl 3 ,300MHz) δppm: -0.01~0.21(Si-CH 3 ), 0.72 (SiCH 2 ), 1.62 (SiCH 2 CH 2 ), 3.90 (O-CH 2 ), 6.94(Ar-H), 7.09(Ar-H), 7.26(Ar-H), 7.35(Ar-H), 7.42(Ar-H), 7.51(Ar-H), 7.58(Ar-H) .

[0059] UV maximum absorption peak: λ max = 402nm.

[0060] It can be seen from the spectrum data that 0.72(SiCH 2 )...

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Abstract

The invention discloses a mono-component polysiloxane photoinitiator capable of overcoming oxygen polymerization inhibition. The mono-component polysiloxane photoinitiator has a specific structure represented by a formula shown in the description, wherein R is a photoinitiator. According to the initiator, a photoinitiator is introduced to a hydrogen-containing polyoxosilane lateral chain, a certain quantity of silicon-hydrogen bonds are reserved, and the action of overcoming oxygen polymerization inhibition is achieved by using the silicon-hydrogen bonds as a hydrogen donor. Simultaneously, the invention discloses a preparation method for the mono-component polysiloxane photoinitiator capable of overcoming oxygen polymerization inhibition. The method comprises the steps of mixing a terminal alkene containing photoinitiator with hydrogen-contained polysiloxane in an argon gas atmosphere, then, dissolving the mixture in a solvent, adding a proper amount of silicon hydrogenation catalyst,carrying out a reaction at a certain temperature, carrying out depressurizing to remove the solvent after the reaction is completed, thereby obtaining the mono-component polysiloxane photoinitiator.The photoinitiator has good compatibility with a light-curing system, a co-initiator is not required to be added additionally during light-curing, the efficiency of initiation is high, polymerizationcan be completed under aerobic conditions, and thus, the photoinitiator is environmentally friendly and energy-saving, meets the requirements of green chemistry and has a broad application prospect inthe field of light-curing.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to a single-component polysiloxane initiator capable of overcoming oxygen inhibition. Background technique [0002] Photopolymerization technology is widely used in many fields such as photocurable coatings, adhesives, inks, microelectronics, and photoresists. However, in the process of use, some inherent difficulties or shortcomings also affect its use, such as the oxygen inhibition effect in the free radical photocuring system. [0003] In the free radical photocuring system, the ground state of the general substance is a singlet state, and the O 2 The stable state of , however, is a triplet state, with two unpaired electrons with the same spin direction. Therefore, it competes with free radical polymerization and consumes free radicals. Oxygen inhibition is mainly manifested in the air curing process, which often leads to the curing of the bottom layer of the coating, and the su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F283/12C08F226/02C08F226/06C08F216/14C08F220/30C08F122/14C08F2/48C08G18/16
Inventor 唐红定杨建静武青青熊英
Owner WUHAN UNIV
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