Diamine monomer containing carborane and preparation method thereof

A technology of diamine monomer and carborane is applied in the field of carborane structure-containing diamine monomer and its preparation, and the preparation of polyimide materials for high temperature resistance and neutron radiation protection. Description, unfavorable large-scale synthesis, no mention of neutron protection and other issues, to achieve the effects of low generation of side reactions and impurities, low incidence of side reactions, and high practicability

Inactive Publication Date: 2016-12-14
CHENGDU SCI & TECH DEV CENT CHINA ACAD OF ENG PHYSICS +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

CN 104945627 A discloses a method for preparing ultra-high heat-resistant polyimide polymers, but does not mention other potential applications such as neutron protection; and although it mentions the synthesis route of carborane-c

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  • Diamine monomer containing carborane and preparation method thereof
  • Diamine monomer containing carborane and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0028] In a 150ml three-necked flask equipped with magnetic stirring, add 1.4668g (10mmol) m-carborane (m-C 2 B 10 H 12 ), the reaction system is maintained at -10°C, anhydrous, oxygen-free, and argon atmosphere. Add 20ml of tetrahydrofuran (THF) treated with molecular sieves, and wait until m-C 2 B 10 H 12 After being completely dissolved in THF, slowly add 6.56ml (2.5M) n-BuLi solution (n-BuLi) dropwise through a constant pressure dropping funnel, the system is a pale white suspension, react for 5h to lithiation of carborane Complete, cool down to -35°C. Weigh 4.342g (20.1mmol) of p-nitrobenzyl bromide, dissolve it in 20ml THF, add dropwise to the carborane double lithium salt solution through a dropping funnel, react at low temperature for 3 hours, then react at room temperature for 3 hours, then The temperature was raised to reflux for 10 hours to complete the reaction. Quench with 5ml 1M hydrochloric acid, extract with ethyl acetate (20ml*3 times), wash with saturated brin...

Embodiment 2

[0030] The preparation process of carborane bisnitro compound A is the same as in Example 1. Add 3g of compound A to a three-necked flask (150ml) with nitrogen gas, add 0.3g of catalyst Pd / C and 50ml of absolute ethanol, and heat to 70°C , 10ml of reducing agent ammonium formate was added dropwise to the reaction system, stirred and heated to reflux for 5h, and the reaction was complete. After the Pd / C was filtered out, the remaining solution was dried by rotary evaporation to obtain the carborane diamine monomer, namely compound B The yield of this step is 92%.

Embodiment 3

[0032] The preparation process of carborane bisnitro compound A is the same as in Example 1. Add 3g of compound A to a three-necked flask (150ml) with nitrogen gas, add 0.3g of catalyst Pd / C and 50ml of absolute ethanol, and heat to 70°C , Pass hydrogen into the reaction system, stir and heat to reflux for 5 hours, and then the reaction is complete. After the Pd / C is filtered out, the remaining solution is dried by rotary evaporation to obtain the carborane diamine monomer, namely compound B. The yield of this step Is 90%.

[0033] FT-IR(KBr,cm -1 ):2932(C-H), 2526(B-H), 1470(CH 2 ), 1017(B-B).

[0034] 1 HNMR(400MHz,DMSO-d 6 ,ppm)δ:7.40(d,4H,Ar-H), 7.10(d,4H,Ar-H), 5.58(s,4H,NH 2 ), 2.87-1.40 (m, 14H).

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Abstract

The invention discloses a synthesis method of diamine monomer containing carborane structure. The method includes: synthesis of carborane double lithium, synthesis of carborane dinitro compound and synthesis of carborane diamine monomer. The carborane double lithium reacts with 4-nitrobenzylbromide to produce the dinitro compound containing carborane, and a nitro reduction reaction is employed for generation of the diamine monomer containing carborane. The synthesis process for diamine monomer containing carborane structure is simple, has easily controllable reaction process and high yield, can be used as an important diamine for the synthesis of high temperature resistant polyimide, and has the potential application value in high temperature and neutron protection.

Description

Technical field [0001] The invention relates to a diamine monomer containing a carborane structure and a preparation method thereof, belonging to the technical field of chemical synthesis, and is specifically applied to the preparation of polyimide materials for high temperature resistance and neutron radiation protection. Background technique [0002] Polyimide refers to a type of polymer containing imide rings in the main chain, among which polymers containing phthalimide structure are the most important. Polyimide is one of the organic polymer materials with the best overall performance, with high temperature resistance above 400℃, and long-term use temperature range -200~300℃. As a special engineering material, polyimide has been widely used in aviation, aerospace, microelectronics, nanometer, liquid crystal, separation membrane, laser and other fields. [0003] In the 1960s, all countries listed the research, development and utilization of polyimide as one of the most promisi...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/02
Inventor 李晓敏梅军黄渝鸿唐昶宇袁萍陈四龙姚曾
Owner CHENGDU SCI & TECH DEV CENT CHINA ACAD OF ENG PHYSICS
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