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Double trifluoromethyl substituent-containing asymmetric aromatic diamine monomer and preparation method thereof

A bistrifluoromethyl and trimethylhydroquinone technology, which is applied in the field of fluorine-containing aromatic diamine compounds and its preparation, can solve the problems of polyimide dark color and poor optical transparency, and achieve easy purification and separation , Excellent optical properties, excellent mechanical properties

Inactive Publication Date: 2012-11-28
CHANGZHOU UNIV +1
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Problems solved by technology

[0004] The technical problem to be solved by the present invention is: to overcome the problems of insoluble organic solvent, dark color and poor optical transparency of polyimide in the prior art, and provide a kind of asymmetric aromatic diamine monomer containing bistrifluoromethyl substitution and preparation method thereof, the aromatic diamine has high purity and good stability at room temperature

Method used

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  • Double trifluoromethyl substituent-containing asymmetric aromatic diamine monomer and preparation method thereof
  • Double trifluoromethyl substituent-containing asymmetric aromatic diamine monomer and preparation method thereof
  • Double trifluoromethyl substituent-containing asymmetric aromatic diamine monomer and preparation method thereof

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Embodiment 1

[0024] Preparation of 1,4-bis(4-amino-2-trifluoromethylphenoxy)-2,3,5-trimethylbenzene:

[0025] ①Under nitrogen protection, add 15.22g (0.1mol) 2,3,5-trimethylhydroquinone and 45.11g (0.2mol) 2-chloro-5-nitrobenzotrifluoride into a 500ml three-necked flask Add 28.98g (0.21mol) of potassium carbonate and 130ml of N,N-dimethylformamide respectively, react at 120°C for 12h, pour the product into 1000ml of methanol / water (1:1) and fully stir, precipitate and filter. The product was washed repeatedly with hot water, and further recrystallized with NN-dimethylformamide / methanol (3:2) mixed solvent to obtain a light yellow fluorine-containing dinitro compound: 1,4-bis(4-nitro-2- Trifluoromethylphenoxy)-2,3,5-trimethylbenzene, the yield is 85%, and the melting point is 256-257°C. 1 H NMR (DMSO-d 6 ,400MHz)δ:8.64(d,J=2.8Hz,1H),8.62(d,J=2.8Hz,1H),8.32(dd,J 1 =2.8Hz,J 2 =9.2Hz,1H),8.30(dd,J 1 =2.8Hz,J 2 =9.2Hz,1H),6.91(s,1H),6.80(d,J=9.2Hz,1H),6.62(d,J=9.2Hz,1H),2.13(s,3H),2.11(s,...

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Abstract

A double trifluoromethyl substituent-containing asymmetric aromatic diamine monomer is 1,4-bis(4-amino-2-trifluoromethylphenoxy)-2,3,5-trimethylbenzene. The synthetic route of the monomer is simple, the yield is high, the purification is easy, and the monomer is stable at room temperature and can be used for the preparation of soluble fluorine-containing polyimide polymers. The preparation method of the double trifluoromethyl substituent-containing asymmetric aromatic diamine monomer includes the following steps: reacting 2,3,5-trimethylhydroquinone with 2-chloro-5-nitrobenzotrifluoride under alkaline conditions with the protection of nitrogen, sufficiently stirring, precipitating and leaching, washing the product with hot water, further recrystallizing to get a fluorine-containing dinitrocompound which is 1,4-bis(4-nitro-2-trifluoromethylphenoxy)-2,3,5-trimethylbenzene, and reacting the fluorine-containing dinitrocompound with a catalyst and a reducing agent in the presence of an organic solvent to get 1,4-bis(4-amino-2-trifluoromethylphenoxy)-2,3,5-trimethylbenzene by reduction.

Description

technical field [0001] The invention belongs to the field of fluorine-containing aromatic diamine compounds and the preparation thereof, in particular to a bistrifluoromethyl-substituted asymmetric aromatic diamine monomer and a preparation method thereof. Background technique [0002] Polyimide is an important class of functional high-temperature-resistant polymers, which can be used in modern high-tech fields as composite material substrates, electronic packaging materials, and gas separation membranes. Although such high-temperature resistant materials have excellent thermal and mechanical properties, due to their rigid main chain structure, strong interactions between molecules and close packing of molecular chains, most commercial polyimides Both have a high melting temperature and are insoluble in organic solvents (mostly only soluble in concentrated sulfuric acid), which brings difficulties to their molding and processing. In addition, due to the high degree of aroma...

Claims

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Application Information

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IPC IPC(8): C07C217/90C07C213/02
Inventor 汪称意赵晓燕李光
Owner CHANGZHOU UNIV
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