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Diamine monomer containing carborane structure, dianhydride monomer containing carborane structure and preparation method and application of diamine monomer and dianhydride monomer containing carborane structure

A diamine monomer and carborane-containing technology, which is applied in the field of polyimide monomers containing carborane structure and its preparation, can solve the problem that the preparation technology of dianhydride monomers and diamine monomers is immature and unable to To meet the requirements of mass production and other problems, to achieve the effect of high yield, convenient raw materials, and easy availability of raw materials

Pending Publication Date: 2021-07-20
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation technology of domestic carborane-containing dianhydride monomers and diamine monomers is still immature and cannot meet the requirements of mass production

Method used

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  • Diamine monomer containing carborane structure, dianhydride monomer containing carborane structure and preparation method and application of diamine monomer and dianhydride monomer containing carborane structure
  • Diamine monomer containing carborane structure, dianhydride monomer containing carborane structure and preparation method and application of diamine monomer and dianhydride monomer containing carborane structure
  • Diamine monomer containing carborane structure, dianhydride monomer containing carborane structure and preparation method and application of diamine monomer and dianhydride monomer containing carborane structure

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preparation example Construction

[0076] Another aspect of the embodiments of the present invention also provides a method for preparing a diamine monomer containing a carborane structure, which includes:

[0077] (1) Adding the first uniformly mixed reaction system comprising decaborane, acetonitrile and the first solvent at 80-120° C. for 3-6 hours to prepare a complex of decaborane and acetonitrile;

[0078] (2) The second homogeneously mixed reaction system comprising the complex of decaborane and acetonitrile, the alkynyl compound, silver nitrate and the second solvent is reacted at 80-120°C for 3-8 hours, and then obtained by post-treatment Compounds containing carborane structures;

[0079] (3) The third homogeneously mixed reaction system comprising the compound containing the carborane structure, concentrated nitric acid and concentrated sulfuric acid is subjected to nitration reaction at 0-60°C for 4-10 hours to obtain a nitro compound containing the carborane structure ;

[0080] (4) The fourth un...

Embodiment 1

[0144] Step 1: Add decaborane (122.3g) and acetonitrile (82.1g) into 1L of toluene and mix, heat to reflux at 80°C for 4h, after the reaction is completed, distill under reduced pressure and wash (washed twice with cyclohexane) , the white solid (0.99mol, productive rate 99%) obtained after drying is the complex compound of decaborane and acetonitrile;

[0145] Step 2: Add toluene (160.4g), the complex of decaborane and acetonitrile (0.99mol) obtained in Step 1, and silver nitrate (0.45mol) into 1.5L of toluene and mix, and heat to reflux at 100°C 8h, after the reaction was completed, the white solid (219.1g, 0.73mol, yield 81%) obtained after vacuum distillation, washing (sequentially with methanol 2 times, hydrochloric acid 2 times, and water 3 times) and drying was carbon-containing boron Compounds with alkane structure (NMR spectrum see figure 1 );

[0146] Step 3: Add the carborane-containing compound (0.5 mol) obtained in Step 2 into a mixture of concentrated nitric ac...

Embodiment 2

[0150] Step 1: Add decaborane (122.3g) and acetonitrile (82.1g) into 1L of toluene and mix, then heat and reflux at 120°C for 4h, after the reaction is completed, distill under reduced pressure, wash (washed twice with cyclohexane), The white solid obtained after drying (0.99mol, yield rate 99%) is the complex of decaborane and acetonitrile;

[0151] Step 2: In an ice-water bath, slowly add di-tert-butyl dicarbonate (523.8g) dropwise to a dichloromethane solution containing an alkynyl-containing diamine compound (222.3g), and stir the reaction at room temperature after the dropwise addition is complete After 10 h, the white solid (0.99 mol, yield 99%) obtained by distillation and washing is the Boc-protected alkyne-containing diamine compound;

[0152] Step 3: Add the Boc-protected alkynyl-containing diamine compound (380.3g) obtained in Step 3, the complex (199.8g) of decaborane and acetonitrile obtained in Step 1, and silver nitrate (15.3g) to 1.5L of toluene , heated to re...

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Abstract

The invention discloses a diamine monomer containing a carborane structure, a dianhydride monomer containing a carborane structure and a preparation method and application of the diamine monomer and the dianhydride monomer. The invention also discloses high-temperature-resistant polyimide containing the carborane structure. The polyimide is prepared by condensation polymerization of the diamine monomer containing the carborane structure and a dianhydride monomer containing the carborane structure. The preparation method comprises the following steps: taking decaborane and alkyne as initial raw materials, preparing a carborane structural unit through addition reaction of the decaborane and the alkyne, and then preparing the diamine monomer containing the carborane structure through nitration reaction and reduction reaction, or preparing the dianhydride monomer containing the carborane structure through oxidation and dehydrating reaction of methyl. The method for preparing the diamine monomer or dianhydride monomer containing the carborane structure has the advantages of simple operation, wide universality, convenient and easily available raw materials, high yield and the like, and is convenient for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a polyimide monomer containing a carborane structure and a preparation method and application thereof. Background technique [0002] Polyimide resin-based composite materials are widely used in the aerospace field because of their excellent heat resistance, low temperature resistance, solvent resistance and flame retardancy, as well as excellent dielectric properties and mechanical properties. . With the continuous and in-depth development of the aerospace industry, the requirements for the temperature resistance level of composite materials are getting higher and higher. At present, most of the polyimide composite materials with all-organic molecules used in the aerospace field have a heat resistance limit below 450°C, which cannot meet the development needs of the aerospace field in the future. [0003] In order to solve the above problems, in recent ye...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/05C08G73/10
CPCC07F5/05C08G73/1057
Inventor 王献伟孟祥胜蔡牧航阎敬灵王震
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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