Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Polyalkyl-substituted aromatic diamine monomer and preparation and application thereof

A technology of aromatic diamine and polyalkyl group, which is applied in the field of polyalkyl substituted aromatic diamine monomer and its preparation and application, can solve the problems of limited solubility, loss, and reduced high temperature resistance of polyimide, and achieve Excellent mechanical properties, low cost, and improved solubility

Inactive Publication Date: 2009-08-26
DONGHUA UNIV
View PDF0 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this kind of fluorine-containing polyimide still shows limited solubility properties, especially the polymers based on rigid pyromellitic dianhydride and biphenyltetralic dianhydride are almost insoluble in most common solvents such as N, N-di Methylacetamide (DMAc), N,N-dimethylformamide (DMF), chloroform, etc.
At the same time, due to the introduction of relatively large-density flexible structural units (ether bonds) into the main chain of the polymer molecule, the glass transition temperature of this type of fluorine-containing polyimide is generally only between 200 and 300 ° C, which is different from that of commercial products. Compared with the chemicalized polyimide, there is a greater loss, which reduces the high temperature resistance of polyimide to a certain extent.

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
  • Polyalkyl-substituted aromatic diamine monomer and preparation and application thereof
  • Polyalkyl-substituted aromatic diamine monomer and preparation and application thereof
  • Polyalkyl-substituted aromatic diamine monomer and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of α,α-(4-amino-3,5,-dimethylphenyl)-4'-isopropyltoluene:

[0036] Under the protection of nitrogen, 100 parts of 2,6-dimethylaniline was heated to 110°C under the protection of nitrogen, and then a mixed solution of 35 parts of 4-isopropylbenzaldehyde and 20 parts of hydrochloric acid was added dropwise thereto. After the dropwise addition, the reactant mixture was heated to reflux at 155°C for 12 hours. Cool to 60°C, add dropwise to neutral with 10% aqueous sodium hydroxide solution. Excessive ethanol was added to produce a large amount of precipitate; filtered, washed with methanol, dried, and further separated and purified by silica gel column chromatography to obtain a white diamine product with a yield of about 60-80% and a melting point of 157-158°C. FT-IR(KBr): 3440, 3368, 3226, 2961, 2925, 2866, 1623, 1600, 1488, 1303, 1152, 1022, 883, 843 and 653cm -1 . 1 H-NMR (400MHz, DMSO-d 6 , ppm): 7.09 (d, J = 8.0Hz, 2H), 6.96 (d, J = 8.0Hz, 2H), 6.52 (s,...

Embodiment 2

[0038] α, α-(4-amino-3,5,-dimethylphenyl)-4'-tert-butyltoluene preparation:

[0039] Under the protection of nitrogen, 100 parts of 2,6-dimethylaniline was heated to 110°C under the protection of nitrogen, and then a mixed solution of 30 parts of 4-tert-butylbenzaldehyde and 5 parts of hydrochloric acid was added dropwise thereto. After the dropwise addition, the reactant mixture was heated to reflux at 160°C for 15 hours. Cool to 60°C, add dropwise to neutral with 10% aqueous sodium hydroxide solution. Excessive ethanol was added to produce a large amount of precipitate; filtered, washed with methanol, dried, and further separated and purified by silica gel column chromatography to obtain a white diamine product with a yield of about 60-80% and a melting point of 184-185°C. FT-IR(KBr): 3446, 3366, 2966, 2904, 2865, 1623, 1489, 1306, 1150, 1022, 841, 843 and 651cm -1 . 1 H-NMR (400MHz, DMSO-d 6 , ppm): 7.24(d, J=8.2Hz, 2H), 6.98(d, J=8.2Hz, 2H), 6.54(s, 4H), 5.03(s, 1H), 4...

Embodiment 3

[0041] Add 1.5mmol of polyalkylated aromatic diamine and 1.5mmol of diphenyl ether tetraacid dianhydride to a 50ml three-neck round-bottomed flask that is dry and ventilated with nitrogen, and then add 15ml of m-cresol solvent (the solid content of the system is between 5 and 20 %), then add about 0.4g of isoquinoline as a catalyst, raise the temperature of the reaction system to 100°C for 2-3 hours, then raise the temperature to 190-200°C for about 10 hours, and pour the polymer solution into 300ml after cooling to 120°C In methanol or ethanol, the precipitate was collected by filtration, washed twice with boiling water, and vacuum-dried at 150°C to obtain a white fibrous polyimide.

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

No PUM Login to View More

Abstract

The invention relates to a polyalkyl-substituted aromatic diamine monomer, and the general formula of the structural formula is shown in the figure, wherein R is -CH(CH3)2 or -C(CH3)3; and the preparation is as follows: under nitrogen protection, 2,6-methyl toluidine is heated to the temperature of 100 to 120 DEG C, and the mixed liquid of aromatic formaldehyde and hydrochloric acid is slowly dropped in the 2,6-methyl toluidine and then the mixture is heated for carrying out reflux; after being cooled, 10% aqueous sodium hydroxide solution is dropped into the mixture till the pH value thereof is neutral, and then alcohol is added, the obtain sediment is washed with methanol; after drying of the mixture, chromatographic separation and purification is carried out on the mixture by silicagel column, thus obtaining the polyalkyl-substituted aromatic diamine monomer; the application can be used to prepare soluble, high-temperature resistant polyimide film material with high transparency and low dielectric constant. The substituted aromatic diamine monomer containing polyalkyl prepared in the invention has high purity and is table at room temperature; the preparation method has simple operation and low cost without any special requirement for equipment, thereby being applied to industrial production.

Description

technical field [0001] The invention belongs to the field of aromatic diamine compounds and their preparation and application, and in particular relates to polyalkyl-substituted aromatic diamine monomers and their preparation and application. Background technique [0002] Polyimide is a kind of heat-resistant polymer material with excellent comprehensive performance. Since the industrialization began in the 1960s and 1970s, they have been applied in various fields. Especially as a high-performance fiber, a high heat-resistant composite material matrix and an electronic packaging material, it has been widely used in aerospace, machinery, microelectronics, petrochemical and other industries. Although such high temperature resistant materials have excellent comprehensive properties, most polyimides have high Melting temperature, and insoluble in organic solvents (only soluble in concentrated sulfuric acid), brings difficulties to its molding process. This limits their furthe...

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
IPC IPC(8): C07C211/50C07C209/78C08G73/10
Inventor 汪称意李光赵晓燕杨胜林金俊弘江建明
Owner DONGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com