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Hydrogen self-supply type photoinitiator and preparation method thereof

A photoinitiator, self-supplying hydrogen technology, applied in applications, coatings, inks, etc., can solve problems such as environmental pollution

Active Publication Date: 2017-01-25
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Another object of the present invention is to provide a kind of preparation method of new thioxanthone photoinitiator, this preparation method introduces transesterification group by the direct reaction of methyl chloroacetate and thioxanthone carboxylic acid, overcomes general method Environmental pollution caused by the use of thioxanthone chloride, the synthesis process is green and environmentally friendly, and the reaction conditions are relatively mild

Method used

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  • Hydrogen self-supply type photoinitiator and preparation method thereof
  • Hydrogen self-supply type photoinitiator and preparation method thereof
  • Hydrogen self-supply type photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Embodiment 1: methyl thioxanthone-4-formyloxyacetate

[0104] In a 250ml four-neck flask equipped with mechanical stirring, add 25.6g thioxanthone-4-carboxylic acid, 250 ml tetrahydrofuran, 12.1g triethylamine, 13.1 g methyl chloroacetate, heat to 50~60°C for 8 hours , suction filtration, the filtrate was cooled to 0~5°C, stirred and crystallized for 2 hours, and then the crude product was obtained by suction filtration. The crude product was recrystallized with toluene, and after drying, 23.9g of yellow flaky crystals were obtained. The yield was 73%, and the content was ≥98.0%. 1 H NMR (DMSO) δ: 8.25 (m, 1H), 8.16 (m, 1H), 8.01 (m, 1H), 7.83 (d,1H), 7.66 (m, 2H), 7.42 (m, 1H), 5.17 (m, 2H), 3.55 (s, 3H).

Embodiment 2

[0105] Embodiment 2: methyl thioxanthone-4-formyloxyacetate

[0106]In a 250ml four-necked flask equipped with mechanical stirring, add 25.6g thioxanthone-4-carboxylic acid, 250 ml tetrahydrofuran, 18.4g diisopropylethylamine, 14.8g methyl chloroacetate, and heat to reflux for 8 hours. Cool down to 40~50°C and filter with suction, cool the filtrate to 0~5°C, stir and crystallize for 2 hours, and then filter with suction to obtain the crude product. The crude product is recrystallized with toluene, and after drying, 23.0g of yellow flaky crystals are obtained. The yield is 70%, and the content is ≥ 98.0%.

Embodiment 3

[0107] Embodiment 3: methyl thioxanthone-2-formyloxyacetate

[0108] In a 250ml four-necked flask equipped with mechanical stirring, add 25.6g thioxanthone-2-carboxylic acid, 200 ml tetrahydrofuran, 12.1g triethylamine, 13.1 g methyl chloroacetate, heat to 50~60°C for 8 hours , suction filtration, the filtrate was cooled to 0~5°C, stirred and crystallized for 2 hours, and then the crude product was obtained by suction filtration. The crude product was recrystallized with toluene, and after drying, 27.2g of light yellow flaky crystals were obtained. The yield was 83%, and the content was ≥97.5%. 1 H NMR (DMSO) δ: 8.16 (d, 1H), 8.04 (m, 1H), 7.91 (m, 1H), 7.63 (d,1H), 7.51 (m, 2H), 7.22 (m, 1H), 5.14 (m, 2H), 3.52 (s, 3H).

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Abstract

The invention relates to a hydrogen self-supply type photoinitiator and a preparation method of the hydrogen self-supply type photoinitiator. The hydrogen self-supply type photoinitiator is a compound having a structure of Formula (I) as below, wherein L represents core framework structure of n function, and is independently selected from hydroxyl-containing small molecular compound or residual base of polyether; m and n represent integers 1-6 independently, and n is not more than m; PI is photosensitive radical group, and selected from thioxathone or substituted thioxathone radial group; R is selected from H, linear chain or branch chain C1-C18 alkyl, phenyl, substituted phenyl, benzyl or substituted benzyl as the (III), (IV), (V), (VI), (VII) structures of the Formula below: FORMULA. The photoinitiator can be the hydrogen self-supply type, and can efficiently initiate light polymerization reaction under the condition of not adding initiator, and avoid the shortcomings of volatile, migration and odor of assistant initiator. The preparation method directly introduces the ester exchange radical group through the direct reaction between methyl chloroacetate and thioxathone carboxylic acid, and overcomes the environment pollution caused by using thioxathone acyl chloride in ordinary method; the synthetic process is green and environment-friendly, and the reaction condition is relatively gentle. The FORMULA (I) is as shown in the description.

Description

technical field [0001] The invention relates to a new self-supply hydrogen Norrish II photoinitiator and a preparation method thereof. Background technique [0002] Photoinitiators mainly include free radical photoinitiators and cationic photoinitiators. Free radical photoinitiators According to the different mechanism of action of photoinitiators to generate active free radicals, free radical photoinitiators can be divided into two types: cracking free radical photoinitiators and hydrogen abstraction free radical photoinitiators. Cleavage-type free radical photoinitiators mainly include benzoin and its derivatives, benzil derivatives, dialkoxyacetophenone, α-hydroxyalkylphenone, α-aminoalkylphenone, acylphosphine oxidation The mechanism of generating free radicals is as follows: [0003] [0004] The hydrogen abstraction free radical photoinitiator consists of a hydrogen abstraction photoinitiator and a co-initiator. Hydrogen-abstracting photoinitiators are generally ...

Claims

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Application Information

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IPC IPC(8): C07D335/16C08F2/48C08G65/48C09D4/02C09D4/06C09D11/101
CPCC07D335/16C08F2/48C08G65/48C09D4/06C09D11/101C08F283/008C08F283/105
Inventor 赵建新武瑞董月国董子瑞秦静张齐赵国锋
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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