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Polymerizable free radical II type photoinitiators and preparation method thereof

A photoinitiator and free radical technology, applied in the field of polymerizable free radical type II photoinitiator and its preparation, can solve the problems of difficult promotion, poor storage stability, complex synthesis process, etc., and achieve strong operability and strong adaptability , The preparation process is simple and controllable

Active Publication Date: 2018-01-26
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This kind of polymerizable photoinitiator containing co-initiator effectively reduces the risk of small molecule photoinitiator and co-initiator residue and migration, and the method of use is simpler, but due to the complex synthesis process, high cost and poor storage stability and other shortcomings, making it difficult to promote in practical applications

Method used

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  • Polymerizable free radical II type photoinitiators and preparation method thereof
  • Polymerizable free radical II type photoinitiators and preparation method thereof
  • Polymerizable free radical II type photoinitiators and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: methyl thioxanthone-4-formyloxyacetate

[0051] In a 500ml four-neck flask equipped with mechanical stirring, add 50.0g thioxanthone-4-carboxylic acid, 250 ml tetrahydrofuran, 23.6g triethylamine, 25.6 g methyl chloroacetate, and 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, 53.7g of yellow flaky crystals were obtained. The yield was 84%, 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 (s, 2H), 3.55 (s, 3H).

Embodiment 2

[0052] Embodiment 2: methyl thioxanthone-4-formyloxyacetate

[0053] In a 500ml four-neck flask equipped with mechanical stirring, add 50.0g thioxanthone-4-carboxylic acid, 250 ml tetrahydrofuran, 35.9g diisopropylethylamine, 28.9g 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, 48.1g of yellow flaky crystals are obtained. The yield is 75%, and the content is ≥ 98.0%.

Embodiment 3

[0054] Embodiment 3: Methyl benzophenone-2-formyloxyacetate

[0055] Add 22.6g of benzophenone-2-carboxylic acid, 120ml of tetrahydrofuran, 15.1g of triethylamine, and 11.8g of methyl chloroacetate into a 250ml four-necked flask equipped with mechanical stirring, and heat to 50~60°C for 8 hour, suction filtration, the filtrate was cooled to 0~5°C, stirred and crystallized for 2 hours, and the crude product was obtained by suction filtration. The crude product was recrystallized with toluene, and after drying, 27.1g of white crystals were obtained. The yield was 91%, and the content was ≥95.0%. 1 H NMR (DMSO) δ: 8.30 (t, 1H), 8.12 (d, 1H), 7.88 (m, 2H), 7.73 (d,1H), 7.51~7.63 (m, 4H), 5.20 (s, 2H) , 3.58 (s, 3H).

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Abstract

The invention discloses polymerizable free radical II type photoinitiators shown as formulae I and II in the description and a preparation method of the photoinitiators. Carboxylic acid compounds containing type II photo-initiation functional groups are taken as raw materials and subjected to a substitution reaction with methyl chloroacetate under an alkaline condition, then a product is subjectedto transesterification with hydroxy compounds containing polymerizable groups, and the polymerizable photoinitiators are generated. The photoinitiators structurally contain the polymerizable groups,so that the compatibility of the photoinitiators with a photopolymerization system is improved, and surface mobility is reduced greatly in the photocuring process; the photoinitiators can also serve as monomers for synthesis of macromolecular photoinitiators, thereby having broad application prospect in the field of photocuring.

Description

technical field [0001] The invention relates to a novel polymerizable free radical type II photoinitiator and a preparation method thereof. Background technique [0002] UV curing technology is an environmentally friendly green technology in the fields of coatings, inks, adhesives, etc. Compared with traditional solvent-containing systems, UV curing technology has outstanding features such as no solvent emission, high efficiency, and energy saving. The main body of the material is generally composed of oligomers, monomers and photoinitiators, which are all cured under the action of sufficient ultraviolet light. With the application of UV light curing materials more and more widely, some unexpected problems have appeared, such as the baby milk powder in 2005 The pollution incident was caused by the migration of type II photoinitiator isopropylthioxanthone (ITX) remaining in the photocurable ink of the outer packaging. [0003] Free radical type II photoinitiators, also known...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C09D11/101C07D335/16C07C69/76C07C67/28
Inventor 赵建新武瑞董子瑞马小文张齐
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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