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Two-component cationic visible-light initiator and application of two-component cationic visible-light initiator in photocuring technology

A cationic, two-component technology, applied in the field of photopolymerization, can solve the problems of increased cost and environmental hazards, poor environmental safety, high equipment requirements, etc., and achieve the effects of shortening the induction period, fast initiation speed and low synthesis cost

Active Publication Date: 2018-11-30
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Initiator is an important part of the photocuring system. Common commercial cationic photoinitiators are mostly ultraviolet photoinitiators, which can match ultraviolet light sources. However, traditional ultraviolet light sources have high energy consumption, large radiation, and high requirements for equipment. , poor environmental protection and safety, in the light curing molding technology, the cost and environmental hazards are increased, which greatly limits its application

Method used

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  • Two-component cationic visible-light initiator and application of two-component cationic visible-light initiator in photocuring technology
  • Two-component cationic visible-light initiator and application of two-component cationic visible-light initiator in photocuring technology
  • Two-component cationic visible-light initiator and application of two-component cationic visible-light initiator in photocuring technology

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1 Preparation of organic dye 1 based on benzothiadiazole structural unit

[0057] Prepare the dyestuff preparation process shown in formula (III):

[0058]

[0059]Intermediate 1: Take a 500mL two-necked bottle, add benzothiadiazole (10g, 73.4mmol) and hydrobromic acid (100mL, 48%), and then dropwise add HBr (100mL, 48%) containing Br2 (220.3mmol) . After refluxing for 6h, a large amount of orange solid was produced, the reaction was stopped and cooled, and then neutralized with NaHCO3 saturated solution. Suction filtration, washing with a lot of water, the yield is 95%. Intermediate 2: Take a 100mL single-necked round-bottom flask, add p-fluorobromobenzene (10mmol), KOH 20mmol and DMSO solution 20mL in sequence, and stir at room temperature. After 10 minutes, 10 mmol of p-fluoroaniline was added to the reaction system, protected from light, and the reaction was completed at room temperature for 2 hours. Tap water ethyl acetate (40mL / 20mL) extraction, ...

Embodiment 2

[0061] Embodiment 2 Preparation of organic dye 2 based on benzothiadiazole structural unit

[0062] Prepare the dyestuff preparation process shown in formula (Ⅳ):

[0063]

[0064] Intermediate 1 was synthesized as described in Example 1.

[0065] Intermediate 3: Prepared according to a method similar to that described in Intermediate 2, the only difference is that p-fluorobromobenzene needs to be replaced by p-methoxybromobenzene (10 mmol).

[0066] Dye 2: Prepared according to a method similar to that described in Dye 1, the only difference is that intermediate 2 (3.0 mmol) needs to be replaced by intermediate 3 (3.0 mmol).

[0067] 1H NMR (400MHz, DMSO) δ7.09–7.01 (m, 10H), 6.93–6.86 (m, 8H), 3.73 (s, 6H).

Embodiment 3

[0068] Embodiment 3 contains the preparation of dyestuff 1 curing sample

[0069] Weigh 0.2000g (0.469mmol) of diphenyliodonium hexafluorophosphate, add 0.0500g (0.092mmol) of the dye 1 prepared in Example 1 and place it in a brown bottle, then add 2mL of epichlorohydrin, stir fully to make The initiator was completely dissolved, and then 10 g of bisphenol A epoxy prepolymer E51 was added, and stirred evenly to obtain a cured sample, which was stored away from light.

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Abstract

The invention discloses a two-component cationic visible-light initiator and application of the two-component cationic visible-light initiator in the photocuring technology. The two-component cationicvisible light initiator comprises diphenyl iodonium hexafluorophosphate and benzothiadiazole structural unit-based organic dye at a weight ratio of 1:(0.02-1), wherein diphenyl iodonium hexafluorophosphate with a CAS No. Of 58109-40-3) is a commercial ultraviolet photoinitiator, and the benzothiadiazole structural unit-based organic dye is adopted as a sensitizer of diphenyl iodonium hexafluorophosphate. The two-component cationic visible-light initiator has a wide absorption spectrum, curing molding of epoxide can be initiated under irradiation of a visible light source, and rapid curing canbe performed under low illumination of less than 30 mW / cm<2>, so that adoption of a traditional UV source with high energy consumption and large radiation is avoided; in addition, the benzothiadiazole structural unit-based organic dye has small synthesis difficulty, few steps and low-cost raw materials.

Description

technical field [0001] The invention belongs to the technical field of photopolymerization, and in particular relates to a two-component cationic visible light initiator and its application in the photocuring field. Background technique [0002] Cationic photocuring can avoid the phenomenon of oxygen inhibition in free radical photocuring, such as epoxy monomers or prepolymers with strong shrinkage resistance. Compared with free radical photocuring, the curing speed of cationic photocuring process is slow, and there is an induction period. Initiator is an important part of the photocuring system. Common commercial cationic photoinitiators are mostly ultraviolet photoinitiators, which can match ultraviolet light sources. However, traditional ultraviolet light sources have high energy consumption, large radiation, and high requirements for equipment. , Poor environmental protection and safety. In the light curing molding technology, the cost and environmental hazards are incr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/68
CPCC08G59/687C08G59/688
Inventor 陈瑜姜珊安静雯李鹤
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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