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n, n'-m-phenylene bismaleimide and preparation method thereof
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A technology of bismaleimide and m-phenylenediamine, applied in the direction of organic chemistry, can solve the problems of unfavorable industrial production, high production cost, and increased production cost
Inactive Publication Date: 2017-01-25
LIAOCHENG UNIV
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[0003] At present, the relevant PDM synthesis methods at home and abroad are mainly as follows: one method is to use acetone, dimethylformamide, etc. as solvents, use acetic anhydride as a dehydrating agent, and use maleic anhydride and m-phenylenediamine to react synthetically. But in this method, dimethylformamide is not only expensive, but also toxic, and produces a large amount of by-product acetic acid in the cyclodehydration process of acetic anhydride, making the production cost higher (Amit M. Patel, International Journal of PolymericMaterials, 2010, 59:98-108); Another method is to use benzene and toluene as solvent, use p-toluenesulfonic acid, etc. as catalyst, and react maleic anhydride and m-phenylenediamine at reflux temperature. There are relatively complicated steps, which are not conducive to industrial production (Ludger Heiliger, United States Patent, No.5994561); in addition, m-phenylene bismaleimide was synthesized using acetic acid as a solvent, nickel acetate and acetic anhydride as catalysts. Amines (Xie Feng, Sichuan Institute of Technology (Natural Science Edition), 2007, 88-91)
For the above method, acetic anhydride, nickel acetate, etc. are used as catalysts, which inadvertently increases the production cost
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Embodiment 1
[0016] Example 1: Add 10.0 mmol of m-phenylenediamine and 20 mL of toluene to the reaction flask, and stir on a magnetic stirrer. After the temperature rises to 60° C., add 21.0 mmol of maleic anhydride and 5 ml of acetic acid dropwise Ethyl ester solution, after the dropwise addition, was heated to reflux, reacted for 5 hours, a yellow solid was formed, cooled, filtered with suction, and dried. The yield was 93%, and the purity was 97%. The obtained N,N'-m-phenylene bismaleimide has a yellow powder appearance and a melting point of 202-204°C. The structural formula is as follows:
[0017] .
[0018] The nuclear magnetic data of gained product is as follows:
[0019] 1 H NMR (400MHz, DMSO ， ppm), δ = 7.16(4H, s, Vinilic), 7.52-7.29 (m,4H, C 6 h 4 ).
[0020] Infrared analysis is as follows: IR(KBr, cm -1 ): 3446, 3287, 3102, 1715, 1636, 1557, 1488, 1404, 1306, 1218, 849, 683.
[0025] Example 2: Add 10.0 mmol of m-phenylenediamine and 20 mL of toluene to the reaction flask, and stir on a magnetic stirrer. After the temperature rises to 60° C., add 21.0 mmol of maleic anhydride and 5 ml of acetic acid dropwise Ethyl ester solution, after the dropwise addition, was heated to reflux, reacted for 4 hours, a yellow solid was formed, cooled, filtered with suction, dried, and the yield was 86%.
Embodiment 3
[0026] Example 3: Add 10.0 mmol of m-phenylenediamine and 20 mL of toluene to the reaction flask, and stir on a magnetic stirrer. After the temperature rises to 50° C., add 21.0 mmol of maleic anhydride and 5 ml of acetic acid dropwise Ethyl ester solution, after the dropwise addition, was heated to reflux, reacted for 4 hours, a yellow solid was formed, cooled, filtered with suction, dried, and the yield was 82%.
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Abstract
The invention provides a preparation method of a multifunctional rubber vulcanizer N,N'-m-phenylenedimaleimide under the condition of no acetic anhydride. M-phenylenediamine, cis butenyl maleic anhydride, toluene and ethyl acetate are used as raw materials to synthesize the N,N'-m-phenylenedimaleimide. The reaction process is simple and does not need acid anhydride or any other catalyst; and the obtained product has high purity.
Description
technical field [0001] The invention relates to a multifunctional rubber vulcanizing agent N,N'-m-phenylene bismaleimide and a preparation method thereof, belonging to the technical field of chemical auxiliary agents. Background technique [0002] N,N'-m-phenylene bismaleimide (abbreviated as PDM) is a class of multifunctional rubber additives with dual functional groups. As a multifunctional rubber additive, PDM can be used not only as a rubber vulcanizing agent in the processing of natural rubber, but also as a rubber co-vulcanizing agent in a peroxidesystem, as well as a rubber anti-scorch agent and a rubber tackifier. It is very useful. widely. In addition, PDM can be applied to both general rubber and special rubber systems. In natural rubber, when PDM and sulfur are mixed in a certain proportion, it can not only prevent the vulcanization of the rubber, improve the heat resistance of the rubber, but also increase the adhesion between the rubber and the cord and the m...
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