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Fluorene initiator, photocurable composition containing same, and application thereof

An initiator and light-curing technology, applied in the field of light-curing, can solve the problem of not being able to have zero migration, high sensitivity to yellowing resistance at the same time, and achieve the effect of improving sensitivity, high light curing effect and excellent yellowing resistance.

Pending Publication Date: 2021-02-26
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main purpose of the present invention is to provide a fluorene-based initiator, a photocurable composition containing it and its application, so as to solve the problem that existing fluorene-based photoinitiators cannot have zero migration, yellowing resistance and high sensitivity at the same time. question

Method used

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  • Fluorene initiator, photocurable composition containing same, and application thereof
  • Fluorene initiator, photocurable composition containing same, and application thereof
  • Fluorene initiator, photocurable composition containing same, and application thereof

Examples

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preparation example Construction

[0042] Another aspect of the present application also provides a kind of preparation method of above-mentioned fluorene photoinitiator, and this preparation method comprises:

[0043] S1, in the presence of the first organic solvent, intermediate a undergoes a substitution reaction with a halogenated compound to generate intermediate b, and the synthetic route is as follows:

[0044]

[0045] Among them, X 1 is a halogen atom;

[0046] S2, in the presence of a second organic solvent, the Friedel-Crafts reaction of the intermediate b and the halogenated alkanoyl compound is carried out to obtain the intermediate c, and the synthetic route is as follows:

[0047]

[0048] Among them, X 2 and X' are independently selected from halogen atoms;

[0049] S3, hydrolyzing the intermediate c with water to obtain a fluorene-based photoinitiator, or performing a dehalogenation reaction between the intermediate c and a compound containing a non-hydroxyl photoactive group to obtain...

Embodiment 1-16

[0067] Step (1): Preparation of dibenzylfluorene (a1)

[0068]

[0069] Add 400g of dichloromethane, 50g of fluorene, 80g of benzyl chloride and 1g of tetrabutylammonium bromide into a 1L four-necked flask, stir, and under nitrogen protection, add 120g of 50% sodium hydroxide solution dropwise in a water bath at 30°C to control the system The temperature was below 35°C, and the addition was completed in 15 minutes. After the addition, the system was heated to reflux for 8 hours. Samples were taken to detect the complete reaction of the raw materials, and the reaction was stopped, and the temperature was lowered to room temperature. Add 100g of water to the reaction solution, separate the organic layer, wash the organic layer with water 3 times until neutral, evaporate the organic phase to dryness, add 200g of methanol to crystallize, stir and crystallize for 1h, filter, and dry the wet product to obtain off-white Solid 95.8g, yield 92.1%, purity 99.2%.

[0070] The structu...

Embodiment 17-26

[0088] Referring to the synthesis methods of Examples 1-16, compounds 17-26 were synthesized by different preparation methods.

[0089] Synthesis of compound 17:

[0090]

[0091] Add 50 g of toluene, 22 g of dibenzylfluorene trichloroisobutyryl chloride Friedel-Crafts, and 1.32 g of tetrabutylammonium bromide into a 250 mL four-neck flask, stir, add 75 g of 25% sodium hydroxide solution dropwise, and control the temperature of the system at Below 30°C, the addition was completed in 10 minutes, and the system was heated in a water bath at 80°C for 1 hour to stop the reaction. When the temperature of the system drops to room temperature, separate the organic layer, wash the organic layer with 300 g of water until neutral, pour the organic layer into a 250 mL four-neck flask, add 2 g of activated carbon, stir for 1 h, filter, rinse the filter cake with a little toluene, and combine the organic phases , pour the filtrate into a 250mL four-neck flask, distill off the organic s...

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Abstract

The invention provides a fluorene initiator, a photocurable composition containing the same and an application of the fluorene initiator and the photocurable composition. The fluorene photoinitiator has a structure as shown in a formula (I). According to the photoinitiator, one or more alkyl ketone substituents are introduced to a fluorene structure, and two aryl ketone substituents are introducedto a No.9 carbon atom, so that fragments formed by the initiator still have relatively high stability and photocuring effect after initiation of an initiation reaction; meanwhile, due to the introduction of a plurality of photoactive groups R3, the number of free radicals generated by the photoinitiator per unit mass can be increased, and the sensitivity of the photoinitiator can be improved. Inaddition, due to the fact that the photoinitiator is large in molecular weight and light in color, the photoinitiator further has the advantages of being not prone to migration and excellent in yellowing resistance, and therefore the photoinitiator further has the advantages of being almost free of VOC emission, low in smell and excellent in yellowing resistance.

Description

technical field [0001] The invention relates to the field of photocuring, in particular to a fluorene initiator, a photocuring composition containing it and applications thereof. Background technique [0002] People pay more and more attention to safety, especially the safety of items that are closely related to people's lives and often come into contact with in daily life, such as food safety, safe and comfortable living environment, etc. At the same time, the environmental protection requirements of various industries are becoming more and more stringent, especially the chemical industry has strict control on VOC emissions and emissions. The green technology of light-cured coatings and light-cured inks with almost no VOC emissions has been widely concerned and has been developed rapidly. Increasing the molecular weight of initiator and sensitizer molecules is an effective means to solve the mobility of photoinitiator. Due to the increase of molecular weight, the proporti...

Claims

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Application Information

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IPC IPC(8): C07D295/108C07D213/50C07D307/46C07C225/16C07C225/06C07C225/18C07C49/83C07C205/45C07D333/22C08F2/48
CPCC07D295/108C07D213/50C07D307/46C07C225/16C07C225/06C07C225/18C07C49/83C07C205/45C07D333/22C08F2/48C07C2601/14C07C2603/18
Inventor 钱晓春胡春青陈亮于培培
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS
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