Unsymmetrical fragrant diamine containing fluorine, preparation and application in synthesizing polyimide thereof

A technology of aromatic diamine and polyimide, which is applied in the field of aromatic diamine, can solve the problems of high melting temperature and limited application of polyimide, and achieve the effect of excellent comprehensive performance and high purity

Inactive Publication Date: 2008-09-24
DONGHUA UNIV
View PDF0 Cites 25 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although polyimides have excellent comprehensive properties, due to their rigid benzene rings and imide rings, as well as the strong interaction between molecules and the close packing of molecular chains, most polyimides have Very high melting temperature, and generally insoluble in organic solvents, which limits their further applications in related fields

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Unsymmetrical fragrant diamine containing fluorine, preparation and application in synthesizing polyimide thereof
  • Unsymmetrical fragrant diamine containing fluorine, preparation and application in synthesizing polyimide thereof
  • Unsymmetrical fragrant diamine containing fluorine, preparation and application in synthesizing polyimide thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Preparation of fluorine-containing asymmetric aromatic diamine

[0044] ①At 0~5℃, add 12.2g (0.1mol) 2,6-dimethylphenol and 28.0g (0.21mol) aluminum trichloride to 250ml containing 120ml 1,2-dichloroethane respectively In the three-neck flask, after fully stirring for half an hour, add 18.6g (0.1mol) p-nitrobenzoyl chloride in batches, stir fully for one hour, then raise the temperature to 10-20°C, react for 4-6 hours, and then pour 1000ml of dilute hydrochloric acid The reaction was completed by settling in the aqueous solution. After the precipitate was steam distilled, it was repeatedly washed with methanol / water (volume ratio 1:1) and recrystallized with ethanol to obtain a light yellow solid powder (4'-hydroxyl-3',5 '-Dimethylbenzene)-(4-nitrophenyl)methanone, the yield is about 80-90%, and the melting point is 214-215°C. FT-IR(KBr)v / cm -1 : 3434(O-H), 1655(C=O), 1523, 1350(-NO 2 ). 1 H NMR (DMSO-d 6 , 400MHz) δ: 8.48 (s, 1H), 8.38 (d, 2H), 7.99 (d, ...

Embodiment 2

[0047] The preparation of embodiment 2 polyimide

[0048] Add 0.4004g (0.001mol) of asymmetric fluorine-containing aromatic diamine and 0.3102g (0.001mol) of diphenyl ether tetra-acid dianhydride monomer into a 50ml three-necked round-bottomed flask that is dry and ventilated with nitrogen, and then add 8ml of m-formazine Phenol and 0.1ml isoquinoline, heat the reaction system to 100-120°C for 2-5 hours, then raise the temperature to 190-200°C for about 15 hours, cool to 120°C, pour the reaction solution into methanol to settle to obtain white fibers The polymer sample was filtered and washed twice with boiling water, and the polymer sample was vacuum-dried at 150°C. FT-IR(film)v / cm -1 : 1781, 1728(C=O), 1371(C-N), 1237(C-O-C), 1127(C-F). 1 H NMR (DMSO-d 6 , 400MHz) δ: 8.06-8.09 (d, 2H), 7.95-7.97 (d, 3H), 7.56-7.69 (d, 9H), 6.77-6.79 (d, 1H), 2.18 (s, 6H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
tensile strengthaaaaaaaaaa
elongation at breakaaaaaaaaaa
Login to view more

Abstract

The present invention relates to fluorine-containing asymmetric aromatic diamine, a preparation method and an application thereof in the synthesis of polyimide. The compound has a constitutional formula as shown in the right. The preparation method comprises the following steps: (1) 2, 6-dimethyl phenol, paranitrobensoyl chloride and alchlor have catalytic reaction in an organic solvent to prepare (4'-hydroxy-3', 5'-dimethyl benzene)-(4-nitrophenyl) ketone; (2) the (4'-hydroxy-3', 5'-dimethyl benzene)-(4-nitrophenyl) ketone reacts with 2-chlorine-5-nitro trifluorotoluene with alkaline, to prepare (3', 5'-dimethyl-4'-(4''-nitro-2''-trifluoromethyl phenoxy) benzene)-(4-nitrophenyl) ketone; (3) the prepared product in the second step is reduced by reducing agent with organic solvents and catalysts; thus the fluorine-containing asymmetric aromatic diamine can be prepared. The fluorine-containing asymmetric aromatic diamine can be used for preparing fluorine-containing polyimide. The fluorine-containing asymmetric aromatic diamine prepared in the method has high purity and can keep stable at the room temperature; the polyimide made of the fluorine-containing asymmetric aromatic diamine has excellent solubility, film forming capability, optical transparency, mechanical properties and heat resistance.

Description

technical field [0001] The invention belongs to the field of aromatic diamines, and in particular relates to a fluorine-containing asymmetric aromatic diamine, its preparation and its application in synthesizing soluble polyimide materials. Background technique [0002] Polyimide is a class of high-performance polymer materials with excellent comprehensive properties. Since the development and industrialization of DuPont in the United States in the 1960s, it has been applied in various fields. Especially as a heat-resistant material and electronic packaging material, it is widely used in aerospace and microelectronics industries. [0003] Although polyimides have excellent comprehensive properties, due to their rigid benzene rings and imide rings, as well as the strong interaction between molecules and the close packing of molecular chains, most polyimides have High melting temperature and generally insoluble in organic solvents limit their further applications in related ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/22C07C221/00C08G73/10
Inventor 汪称意李光彭为亚杨胜林金俊弘江建明
Owner DONGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap