Polymerizable type thioxanthone visible light initiator containing acrylate or methacrylate and preparation method

A technology of methacrylate and thioxanthone is applied in the field of visible light initiator of thioxanthone and preparation thereof, and can solve the problems of unfavorable macromolecular photoinitiator, hindered photoactive group, complicated synthesis method, etc. Wide application prospects, high initiation efficiency, and strong penetrating energy

Active Publication Date: 2016-06-22
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The traditional ultraviolet photoinitiator thioxanthone (isopropylthioxanthone, US Patent6025408) widely used commercially has poor compatibility with the photocuring system and requires the joint action of additives, which is easy to produce odor, toxicity, and migration. , yellowing and other issues
Chinese patent CN1546488A discloses a preparation method of thioxanthone containing co-initiator amino groups, but the photoactive group on the main chain is easily hindered by macromolecular chain segments, which is not conducive to exerting the advantages of macromolecular photoinitiators ; Chinese patent CN1594399A discloses a method for preparing copolymerized thioxanthone photoinitiator, but its synthetic method is complicated
Chinese patent CN102120783 discloses a preparation method of thioxanthone photoinitiators containing aliphatic tertiary amino groups, but these small molecule photoinitiators cannot be used in the visible light region

Method used

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  • Polymerizable type thioxanthone visible light initiator containing acrylate or methacrylate and preparation method
  • Polymerizable type thioxanthone visible light initiator containing acrylate or methacrylate and preparation method
  • Polymerizable type thioxanthone visible light initiator containing acrylate or methacrylate and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Preparation of thioxanthone containing phenolic hydroxyl

[0035] In a 100mL round bottom flask, add 2.41g (10mmol) of 2-methylaminothioxanthone, 2.46g (10mmol) of 4-benzoyloxybenzyl chloride, 2.76g (20mmol) of anhydrous potassium carbonate, potassium iodide 0.1g, 50mL of N,N-dimethylformamide, stirred at room temperature for 10h, a yellow solid precipitated, filtered, the filter cake was introduced into a 100mL round bottom flask, heated to reflux with methanol for 2h, hot filtered, the filter cake was dissolved in tetrahydrofuran, The filtrate was poured into petroleum ether for reprecipitation to obtain 2.74 g of 2-(N-methyl-N-p-hydroxybenzyl)aminothioxanthone with a yield of 79%.

[0036] (2) Preparation of thioxanthone containing acrylate

[0037] Add 0.69 g (2 mmol) of 2-(N-methyl-N-p-hydroxybenzyl) aminothioxanthone into a 100 mL single-necked flask equipped with a stirring bar, seal it with a saline plug, and inject dry Dichloromethane 20mL, anhydrous trie...

Embodiment 2

[0044] (1) Preparation of thioxanthone containing phenolic hydroxyl

[0045] In a 100mL round bottom flask, add 2.83g (10mmol) of 3-methyl-2-isopropylaminothioxanthone, 2.70g (11mmol) of 4-benzoyloxybenzyl chloride, and 2.12g of anhydrous sodium carbonate (20mmol), potassium iodide 0.1g, N,N-dimethylformamide 50mL, stirred at room temperature for 16h, a yellow solid precipitated, filtered, the filter cake was introduced into a 100mL round-bottomed flask, methanol was heated to reflux for 3h, hot filtered, filtered The cake was dissolved in tetrahydrofuran, and the filtrate was poured into petroleum ether for reprecipitation to obtain 2.96 g of 3-methyl-2-[N-isopropyl-N-(4-hydroxybenzyl)]aminothioxanthone with a yield of 76%. .

[0046] (2) Preparation of thioxanthone containing alcoholic hydroxyl

[0047] Add 1.17 g (3 mmol) of 3-methyl-2-[N-isopropyl-N-(4-hydroxybenzyl)]aminothioxanthone to a 100 mL single-necked flask equipped with a stirring bar, 3-chloro 0.31g (3.3mmol)...

Embodiment 3

[0056] (1) Preparation of thioxanthone containing phenolic hydroxyl

[0057] In a 100mL round bottom flask, add 3.39g (10mmol) of 3-ethyl-2-hexylaminothioxanthone, 3.20g (13mmol) of 4-benzoyloxybenzyl chloride, and 2.76g of anhydrous potassium carbonate (20mmol), potassium iodide 0.1g, N,N-dimethylformamide 50mL, stirred at room temperature for 24h, a yellow solid precipitated, filtered, the filter cake was introduced into a 100mL round-bottomed flask, methanol was heated to reflux for 5h, hot filtered, filtered The cake was dissolved in tetrahydrofuran, and the filtrate was poured into petroleum ether for reprecipitation to obtain 3.85 g of 3-ethyl-2-[N-hexyl-N-(4-hydroxybenzyl)]aminothioxanthone with a yield of 87%.

[0058] (2) Preparation of thioxanthone containing alcoholic hydroxyl

[0059] Add 1.33 g (3 mmol) of 3-ethyl-2-[N-hexyl-N-(4-hydroxybenzyl)]aminothioxanthone to a 100 mL single-necked flask equipped with a stirring bar, 6-bromo-n-hexane Alcohol 0.65g (3.6mmol...

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Abstract

The invention discloses a polymerizable type thioxanthone visible light initiator containing acrylate or methacrylate and a preparation method of the polymerizable type thioxanthone visible light initiator. Thioxanthone containing an aromatic amino group can be directly reacted with various types of halogenated alcohol to generate thioxanthone containing an aliphatic hydroxyl group; the thioxanthone containing the aromatic amino group can also be reacted with 4-benzoyloxy benzyl chloride, and then is subjected to alcoholysis to generate thioxanthone containing a phenolic hydroxyl group; the thioxanthone containing the phenolic hydroxyl group can be reacted with the various types of halogenated alcohol to generate thioxanthone containing the aliphatic hydroxyl group; then the thioxanthone containing the phenolic hydroxyl group or the thioxanthone containing the aliphatic hydroxyl group is reacted with acryloyl chloride or methacryloyl chloride to form the polymerizable type thioxanthone visible light initiator containing an acrylate structure or a methacrylate structure. The compound disclosed by the invention has very good compatibility with a light curing system; in an application process, any additive does not need to be added, and any auxiliary agent does not need to be added; the polymerizable type thioxanthone visible light initiator is high in initiation efficiency, green and environment-friendly and low in energy consumption, meets the requirements of green chemistry, and has a wide application prospect in the field of visible light curing.

Description

technical field [0001] The invention relates to the field of photoinitiators, in particular to a polymerizable thioxanthone visible photoinitiator containing acrylate or methacrylate and a preparation method thereof. Background technique [0002] Photopolymerization is a very important technology that is widely used in many fields, such as photocurable coatings, adhesives, inks, microelectronics, photoresists, etc. In these applications, the key process of controlling photopolymerization is photoinitiation. The photoinitiator absorbs light energy under the irradiation of light, and generates active species by itself or interacts with co-initiators. play a decisive role. The absorption wavelength of the traditional photoinitiating system is generally less than 400nm, and it is mainly used in UV curing systems. The photoinitiating system developed in the early stage, such as organic peroxide, can modify its molecular structure by introducing various color-aiding groups, such...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C07D335/12C08F122/14C08F120/14C08F112/08C08F116/12
CPCC07D335/12C08F2/48C08F112/08C08F116/12C08F120/14C08F122/14
Inventor 唐红定熊英武青青
Owner WUHAN UNIV
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