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Polymerizable thioxanthone carbazole visible light initiator containing co-initiator amine and preparation method thereof

A technology based on thioxanthone carbazoles and visible light, applied in organic chemistry and other fields, can solve problems such as poor compatibility, easy migration of fragments, and low initiation efficiency

Active Publication Date: 2016-08-24
JINYU HENAN PACKAGING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor compatibility with the photopolymerization system and low initiation efficiency of the traditional visible light initiation, the fragments of the photoinitiator are easy to migrate after polymerization, and even more serious will produce odor and toxicity

Method used

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  • Polymerizable thioxanthone carbazole visible light initiator containing co-initiator amine and preparation method thereof
  • Polymerizable thioxanthone carbazole visible light initiator containing co-initiator amine and preparation method thereof
  • Polymerizable thioxanthone carbazole visible light initiator containing co-initiator amine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The product of the present invention 3-(diethylamino)-2-(13-oxothiochromeno[2,3-B]carbazol-7-(13H)-yl)propyl methacrylate, which The structural formula is:

[0051]

[0052] Preparation of product 3-(diethylamino)-2-(13-oxothiochromeno[2,3-B]carbazol-7-(13H)-yl)propyl methacrylate of the present invention method, the detailed steps are as follows:

[0053] a. Put 29.24g (0.4mol) of diethylamine into a 100ml reaction flask, start stirring, heat to 56°C, slowly add 28.40g (0.2mol) of glycidyl methacrylate (GMA) into the reaction flask, and react 2h; warming up to 80°C, reacting for 3h; after the reaction, the resulting reactant was distilled to remove residual diethylamine to obtain 42.80g 3-(diethylamino)-2-hydroxypropyl methacrylate ( GMA-DEA) (see the attached infrared spectrum figure 1 );

[0054] b. Add 4.30g (0.02mol) of GMA-DEA and 0.79g (0.01mol) of pyridine into a 100ml reaction flask containing 30ml (44.50g) of chloroform at 1 to 3°C, and then dropwise ad...

Embodiment 2

[0058] Embodiment 2: basically the same as Embodiment 1, the difference is:

[0059] Preparation of product 3-(diethylamino)-2-(13-oxothiochromeno[2,3-B]carbazol-7-(13H)-yl)propyl methacrylate of the present invention method, the detailed steps are as follows:

[0060] a. Put 29.24g (0.4mol) of diethylamine into a 100ml reaction bottle, start stirring, heat to 40°C, slowly add 28.40g (0.2mol) of GMA into the reaction bottle, react for 1h; raise the temperature to 70°C for 4h ; After the reaction finished, the gained reactant was distilled to remove remaining diethylamine to obtain 42.08g GMA-DEA;

[0061] b. Add 4.30g (0.02mol) GMA-DEA into a 100ml reaction flask containing 40ml (59.20g) chloroform at 1-3°C, then add 5.40g (0.02mol) PBr dropwise 3 and a mixed solution of 10ml (14.80g) chloroform, reacted at 1-3°C for 1h; raised the temperature to 70°C for 4h;

[0062]After the reaction finished, the gained reactant was cooled to 20°C, added in 15ml of distilled water, then ...

Embodiment 3

[0065] Embodiment 3: basically the same as Embodiment 1, the difference is:

[0066] Preparation of product 3-(diethylamino)-2-(13-oxothiochromeno[2,3-B]carbazol-7-(13H)-yl)propyl methacrylate of the present invention method, the detailed steps are as follows:

[0067] a. Put 14.63g (0.2mol) of diethylamine into a 100ml reaction flask, start stirring, and heat to 60°C; slowly add 28.40g (0.2mol) of GMA into the reaction flask at this temperature, and react for 4 hours; heat up to Reaction at 70°C for 3 hours; after the reaction, the obtained reactant was distilled to remove residual diethylamine to obtain 38.95 g of GMA-DEA;

[0068] b. Add 4.30g (0.02mol) GMA-DEA and 1.58g (0.02mol) pyridine into a 100ml reaction flask containing 50ml (74.00g) chloroform at 1-3°C, then add 16.20g (0.06 mol)PBr 3 and a mixed solution of 15ml (22.20g) of chloroform, reacted at 1-3°C for 2h; raised the temperature to 40°C for 5h;

[0069] After the reaction was finished, the gained reactant ...

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Abstract

The invention discloses an assisted initiator amine-containing polymerizable thioxanthone carbazole visible light photoinitiator and a preparation method thereof. The preparation method comprises that a compound containing polymerizable and epoxy groups is added into an amine compound, the mixture undergoes a reaction, the amine is removed so that alcohol containing polymerizable and assisted initiator amine groups is obtained, the alcohol or the alcohol and pyridine are added into chloroform, a mixture of PBr3 and chloroform is dropwisely added into the mixture, the mixture undergoes a reaction, the reaction product is treated to form a bromo-compound containing polymerizable and assisted initiator amine groups, thioxanthone carbazole and alkali are added into N, N-dimethyl formamide (DMF), the mixture is stirred to form a uniform mixture, the bromo-compound, cupferron and the N, N-dimethyl formamide mixture are dropwisely added into the reaction system, the reaction system undergoes a reaction, and the reaction product is treated to form a product. The visible light photoinitiator avoids yellowing and toxicity caused by the micromolecule assisted initiator, reduces oxygen inhibition influences and improves a curing rate and cured film stability.

Description

1. Technical field: [0001] The invention relates to a photoinitiator and a preparation method thereof, in particular to a polymerizable thioxanthone carbazole visible photoinitiator containing co-initiator amine and a preparation method thereof. 2. Background technology: [0002] Compared with thermal polymerization technology, photopolymerization technology has the characteristics of low energy consumption, low pollution, rapid and complete polymerization at room temperature, etc., making photopolymerization technology widely used in photocuring coatings, inks, adhesives, photoresists, dental restorations , microelectronics and biomaterials have been widely used in many fields. However, the ultraviolet light source is usually provided by a harmful and expensive high-pressure mercury lamp, which has a great impact on the human body and the environment, and the penetration of ultraviolet light is weak, the curing depth is limited, and there is photoaging effect on some substr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F2/48C07D495/04
Inventor 许敬王经武李中灵郑世军李飞王毛力徐慎刚
Owner JINYU HENAN PACKAGING
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