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Preparation method of diamine monomer based on biomass raw materials

A biomass raw material, diamine monomer technology, applied in organic chemistry and other directions, can solve the problems of poor solubility, low transparency, inability to withstand high temperature, etc., and achieve the effects of good solubility, good thermal stability and simple operation

Active Publication Date: 2018-09-28
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, due to the wide use of aromatic monomers in commercial polyimide films, the CTC (electron transfer complexation) effect within and between molecular chains in the polymer backbone often makes the film material have a darker color and lower Transparency and poor solubility, these obvious defects restrict the application of polyimide film materials in flexible display substrates and other flexible optical devices
However, traditional polyimide materials cannot withstand high temperatures above 200°C due to their low glass transition temperature. Therefore, how to improve the optical properties of polyimide films while maintaining good thermal stability has become a research topic. hotspot

Method used

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  • Preparation method of diamine monomer based on biomass raw materials
  • Preparation method of diamine monomer based on biomass raw materials
  • Preparation method of diamine monomer based on biomass raw materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0033] Embodiment 1 Diamine monomer material preparation

[0034] Preparation of compound 1:

[0035] 3g (16.7mmol) myo-inositol, 10mL (66.6mmol) 1,1'-dimethoxycyclohexane, 0.329g (1.73mmol) p-benzenesulfonic acid were reacted in 20mL DMF solution at 100°C for 12 hours, Then add 0.7mL triethylamine, dilute the reaction solution with 70mL ethyl acetate after concentration, then wash with 5% sodium bicarbonate solution, dry the organic layer with anhydrous sodium sulfate for 12h, filter the organic layer and spin dry to obtain a viscous solid , recrystallized twice in a mixed solution of ethyl acetate: n-hexane = 1:1 to obtain 0.85 g of white crystals. (yield 15%)

[0036] Preparation of compound 2:

[0037] Mix 3.4g (10mmol) white crystals of compound 1 with 3.53g (25mmol) p-fluoronitrobenzene, 0.53g (2mmol) 18-crown-6, 1.68g (30mmol) potassium hydroxide in 20mL DMF and 12mL toluene The solution was reacted at 135°C for 12 hours to obtain a golden yellow solution, and the r...

Embodiment 2

[0056] The preparation (microwave method) of embodiment 2 polymer films

[0057] The two diamine monomers M1 and M2 react with dianhydride monomers 4,4'-diphenyl ether dianhydride (ODPA) and 4,4'-(hexafluoroisopropylene) diphthalic anhydride (6FDA), respectively, A series of PI thin films were obtained. In order to describe its usual synthetic route, PI-1(M1 / ODPA) was taken as an example.

[0058] 0.2274 g of ODPA was added to 3 mL of m-cresol dissolved with 0.3867 g of compound M1 and 10 drops of isoquinoline under anaerobic conditions. An additional 2 mL of m-cresol was added to adjust the solids content of the solution to 12%. The mixture was placed in a glass tube and carried out a two-step polymerization operation through a microwave reactor, reacted at 80 °C for 30 min to obtain PAA, and then reacted at 200 °C for 1 h to obtain PI.

[0059] After the reaction, the golden viscous solution was slowly poured into absolute ethanol to settle a white PI solid. The sediment ...

Embodiment 3

[0075] Solubility test:

[0076] The solubility of the polyimide film was tested in a series of different solutions at a concentration of 10 mg / mL. The results showed that all myo-inositol-derived polyimide films showed good solubility properties in a series of polar and non-polar film solvents and even low boiling point solvents such as methylene chloride / tetrahydrofuran / acetone. The analysis is mainly due to the bulky cyclohexyl side group in the biomass diamine monomer, which makes it easier for solvent molecules to penetrate into the molecular chain and between the chains. On the other hand, the bulky side group provides more free volume, and on the other hand, it can also reduce the chain-chain force by reducing the tight packing within and between the molecular chains. Also, polymers containing trifluoromethyl group showed better solubility. The research results show that myo-inositol-derived polyimides have good solubility and preparation capabilities, making them hig...

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Abstract

The invention provides a preparation method of a diamine monomer based on biomass raw materials. The preparation method comprises the following steps: carrying out a ketalation reaction on a dimethoxy-containing saturated cycloalkane with inositol to protect hydroxy groups, then carrying out a substitution reaction on the hydroxyl-protected compound with a halogenated nitrobenzene compound, and finally reducing the nitro groups to amino groups in the presence of a reducing agent to obtain a new diamine monomer, wherein the diamine monomer can be polymerized with an existing dianhydride monomerto synthesize a series of novel polyimide materials. The preparation method provided by the invention has wide sources of raw materials and simple operation, and the synthesized material shows excellent solubility in various solvents, has good thermal stability, excellent mechanical properties and good optical transparency, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of polyimide material preparation, and more specifically relates to a method for preparing diamine monomers based on biomass raw materials. Background technique [0002] As a polymer material, polyimide has received extensive research attention and rapid development in recent decades due to its good thermal stability, mechanical properties, reliable chemical resistance and dielectric properties. However, the material also has some defects, which restrict its development and further application. For example, due to the wide use of aromatic monomers in commercial polyimide films, the CTC (electron transfer complexation) effect within and between the molecular chains in the polymer backbone often makes the film material have a darker color, low Transparency and poor solubility, these obvious defects restrict the application of polyimide film materials in flexible display substrates and other flexible optical d...

Claims

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Application Information

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IPC IPC(8): C07D493/04C08G73/10C08J5/18
CPCC07D493/04C08G73/1007C08G73/1039C08G73/1042C08G73/1071C08G73/1085C08J5/18C08J2379/08
Inventor 张睿黄华华陈永明
Owner SUN YAT SEN UNIV
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