Fluorene photoinitiator, preparation method thereof, photocuring composition containing fluorene photoinitiator and application of fluorene photoinitiator in field of photocuring

A photoinitiator and compound technology, applied in the field of photocuring, can solve the problems of high initiation efficiency, photoinitiator cannot maintain zero mobility, high yellowing resistance, etc., to achieve improved absorption efficiency, good photoinitiation efficiency, durability Excellent effect of yellowness

Active Publication Date: 2020-12-01
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD +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 photoinitiator, its preparation method, its photocurable composition and its application in the field of photocuring, so as to solve the problem that existing photoinitiators cannot maintain zero mobility at the same time. , high yellowing resistance and high initiation efficiency

Method used

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  • Fluorene photoinitiator, preparation method thereof, photocuring composition containing fluorene photoinitiator and application of fluorene photoinitiator in field of photocuring
  • Fluorene photoinitiator, preparation method thereof, photocuring composition containing fluorene photoinitiator and application of fluorene photoinitiator in field of photocuring
  • Fluorene photoinitiator, preparation method thereof, photocuring composition containing fluorene photoinitiator and application of fluorene photoinitiator in field of photocuring

Examples

Experimental program
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Effect test

preparation example Construction

[0025] Another aspect of the present application also provides a kind of preparation method of above-mentioned fluorene photoinitiator, and this preparation method comprises:

[0026] 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:

[0027]

[0028] Among them, X 1 is a halogen atom;

[0029] 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:

[0030]

[0031] Among them, X 2 and X' are independently selected from halogen atoms;

[0032] 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 to 12

[0049] Step (1): Preparation of 9,9-dibenzylphenyl ketone fluorene (a1)

[0050]

[0051] Add 150mL of dichloromethane, 27g of phenyl ketone fluorene, 28.05g of benzyl chloride and 0.54g of tetrabutylammonium bromide into a 250mL four-necked flask, slowly add 40g of 50% sodium hydroxide solution dropwise, and control the temperature of the system at 30 Below ℃, the addition is completed in 15 minutes, the reaction is heated in a water bath at 50 ℃, the nitrogen protection is stopped, the system is kept warm for 8 hours, and the reaction is stopped. After the temperature of the system dropped to room temperature, 60 g of water was added, the system was separated into layers, and the organic layer was separated. The organic layer was washed 3 times with 200 g of water until neutral. Pour the organic phase into a 250mL four-port screen, distill off the solvent, add 54g of methanol, stir and crystallize in an ice-water bath for 1h, filter, rinse the filter cake with a little me...

Embodiment 13-24

[0068] Referring to the synthesis methods of intermediates a1, b2, and c3 in Examples 1-12, compounds 13-24 were synthesized by different preparation methods.

[0069] Synthesis of compound 13:

[0070]

[0071] Add 50g of intermediate a3 and 200g of morpholine to a 250mL four-neck flask, heat and reflux at 100°C for 6h, track the liquid phase until the reaction is complete, then pour the reaction solution into water and stir, and a beige solid precipitates, suction filters, washes with water, and reconstitutes with methanol Crystallization gave 51 g of a white solid, namely compound 11, with a yield of 88.5% and a purity of 98.01%.

[0072] The structure of the product was confirmed by H NMR and mass spectrometry:

[0073] 1 H-NMR (CDCl 3 , 400MHz): δ8.10–7.94(m,5H),7.87–7.78(m,2H),7.70–7.62(m,2H),7.55(t,J=8.3Hz,3H),7.48-7.37(m ,3H),7.33-7.27(m,1H),6.65(d,J=8.3Hz,4H),3.61–3.43(m,12H),2.48–2.35(m,8H),1.20(s,12H). .

[0074] MS (m / z): 761 (M+1) + .

[0075] Referring...

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Abstract

The invention provides a fluorene photoinitiator, a preparation method thereof, a photocuring composition containing the fluorene photoinitiator and application of the fluorene photoinitiator in the field of photocuring. The fluorene photoinitiator has a structure shown as a formula (I), wherein R3 is selected from photoactive groups. A benzophenone alkyl substituent group is introduced to a No.9carbon atom position of a fluorene structure, and fragments formed by the initiator still have high stability and photocuring effect after initiation reaction; meanwhile, the introduction of the photoactive group R3 can improve the light absorption efficiency of the photoinitiator so that the improvement of the sensitivity of the photoinitiator is facilitated. In addition, due to the fact that thephotoinitiator is large in component 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 photoinitiator, a preparation method thereof, a photocuring composition containing the same and its application in the field of photocuring. Background technique [0002] Nowadays, people pay more and more attention to safety, especially the safety of substances that are closely related to people's lives and often come into contact with in daily life, such as food safety and living environment safety. With the gradual improvement of global environmental protection requirements, the VOC emission requirements of chemical related industries are becoming more and more stringent, and strict control has been made on the emission. 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. In 2005, four European countries detected a sensitizer ITX in the milk powder of a certain manufactur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C08F222/14G03F7/027C07C45/64C07C49/83C07C201/12C07C205/45C07D333/22C07D307/46C07D213/50C07D295/108
CPCC07C45/46C07C45/64C07C45/68C07C201/12C07C221/00C07D213/50C07D295/108C07D307/46C07D333/22C08F2/48C08F222/10C07C2601/14C07C2603/18G03F7/027C07C49/792C07C49/813C07C49/83C07C205/45C07C225/18
Inventor 钱晓春胡春青陈亮于培培
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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