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Benzophenone macromolecular photoinitiator and preparation method thereof

A technology of benzophenones and photoinitiators, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of intractable waste water, low migration and high cost, and achieve mild reaction conditions. , Simple operation, low cost effect

Active Publication Date: 2015-10-21
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are many companies and institutions developing and producing benzophenone macromolecular photoinitiators. The published patents are: Beijing University of Chemical Technology (CN102993339, CN103122041), Changzhou University (CN103193899, CN103755842), Beijing Yingli (CN101434543 ), Shanghai Jiaotong University (CN100372875), Wuhan University (CN100395267), etc. The synthesis methods reported in such patents mostly use 2- or 4-position phenolic hydroxyl groups to undergo chemical reactions to introduce polymer chain segments. The prepared photoinitiators generally contain The electron-donating ether bond leads to low activity of this type of photoinitiator. At the same time, the synthesis pollution of benzophenone containing phenolic hydroxyl group is relatively large, the waste water is difficult to treat, and the cost is high, which restricts the application of this type of photoinitiator.
CN104327199 discloses a self-hydrogen-supply type difunctional group benzophenone photoinitiator, first introduces a halogen on the methyl group of 4-methylbenzophenone through a halogenation reaction, and then prepares a macromolecular benzophenone through a nucleophilic substitution reaction A ketone initiator. In the preparation process, the method prepares elemental bromine by oxidizing hydrobromic acid with hydrogen peroxide and replaces it. The reaction is too violent and difficult to control, and the safety risk of hydrogen peroxide is high. It is not suitable for industrial production; US2011028091 discloses a class of macromolecular bismuth The preparation method of benzophenone photoinitiator, prepared a series of difunctional benzophenone derivatives with different intermediate chains through the ring-opening reaction of 2-carboxybenzophenone to propylene oxide, the compound has high photoinitiation efficiency and low migration

Method used

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  • Benzophenone macromolecular photoinitiator and preparation method thereof
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  • Benzophenone macromolecular photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Preparation of 2-benzoyl-benzoyloxy-acetic acid diethylene glycol diester (Ia)

[0043]In a 250ml four-necked flask equipped with mechanical stirring, add 25.0g of diethylene glycol, 100ml of dichloromethane, and 59.6g of triethylamine, cool down to 0~5°C in an ice-water bath, add dropwise 55.9g of chloroacetyl chloride, and control dropwise Acceleration, keep the temperature of the reaction solution at 0~5°C, after the dropwise addition, raise the temperature to 20~25°C and continue stirring for 3 hours, and control the monoester content in GC to 1 H NMR (CDCl 3 ) δ: 8.82 (m, 1H), 8.56 (m, 1H), 8.43 (m, 1H), 7.90 (d, 1H), 7.75 (m, 2H), 7.61 (m, 1H), 5.37 (m, 1H ), 3.76 (s, 3H), 1.62 (d, 3H).

Embodiment 2

[0044] Example 2: Preparation of 2-benzoyl-benzoyloxy-acetic acid diethylene glycol diester (Ia)

[0045] In a 250ml four-necked bottle equipped with mechanical stirring, add 25.0g of diethylene glycol, 100ml of dichloromethane, 59.6g of triethylamine, cool down to 0~5°C in an ice bath, add dropwise 55.9g of chloroacetyl chloride, and control dropwise Acceleration, keep the temperature of the reaction solution at 0~5°C, after the dropwise addition, raise the temperature to 20~25°C and continue stirring for 3 hours, and control the monoester content in GC to <1.0%. Add 40ml of water to the reaction solution, separate after stirring, wash the organic phase twice with 40ml of saturated sodium bicarbonate, once with 40ml of saturated brine, once with 40ml of water, and transfer to another machine equipped with mechanical stirring after removing the solvent. In a 1000ml four-neck flask, add 400ml N,N'-dimethylformamide, 106.5g 2-benzoylbenzoic acid, 55.0g sodium carbonate, heat to ...

Embodiment 3

[0046] Example 3: Preparation of 2-benzoyl-benzoyloxy-butylene glycol diester (Ib)

[0047] In a 250ml four-neck flask equipped with mechanical stirring, add 20.0g 1,4-butanediol, 100ml tetrahydrofuran, 71.7g diisopropylethylamine, cool down to 0~5℃ in an ice bath, and dropwise add 52.6g Chloroacetyl chloride, control the rate of addition, keep the temperature of the reaction solution at 0~5°C, raise the temperature to 20~25°C after the dropwise addition and continue stirring for 4 hours, and control the monoester content in GC to 1 H NMR (CDCl 3 ) δ: 8.82 (m, 1H), 8.56 (m, 1H), 8.43 (m, 1H), 7.90 (d, 1H), 7.75 (m, 2H), 7.61 (m, 1H), 5.37 (m, 1H ), 3.76 (s, 3H), 1.62 (d, 3H).

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Abstract

The invention relates to a preparation method of benzophenone macromolecular photoinitiator. The benzophenone macromolecular photoinitiator is a compound with the structural formula (I) shown in the specifications, wherein carboxylic ester substituent groups of benzophenone can be 2-position carboxylic ester substituent groups or 3-position carboxylic ester substituent groups or 4-position carboxylic ester substituent groups, each R1 and each R2 are independently selected from hydrogen, optionally substituted alkyl groups and optionally substituted aryl groups, n is an integer from 1 to 6, and L is residues of polyhydric alcohols. The preparation method has the advantages that reaction conditions are mild, operation is easy, the yield is high, and the cost is low; the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a benzophenone macromolecular photoinitiator and a preparation method thereof. Background technique [0002] Photoinitiators are an important part of UV light-curable materials. With the continuous improvement of people's attention to environmental pollution, the pollution problems caused by small molecule photoinitiators, especially those used in food and pharmaceutical packaging materials, are becoming more and more serious. more prominent. For the sustainable development of the environment and to meet the possible environmental legislation requirements in the future, the ideal photoinitiator should have a low Mobility and solvent extraction. [0003] Compared with small molecule photoinitiators, macromolecular or macromolecular photoinitiators have many advantages, such as: low volatility, low mobility, environmental friendliness, good compatibility with photocuring systems, and diverse functions. Therefore, in recent yea...

Claims

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Application Information

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IPC IPC(8): C08F2/48C09D175/14C09D7/12C09D11/101C07C69/78C07C67/10
Inventor 赵建新董子瑞董月国王晓蒙武瑞张齐赵国锋
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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