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Diamine monomers containing asymmetric non-coplanar structure and preparation method thereof

A non-coplanar, diamine monomer technology, applied in the field of aromatic diamine monomer and its preparation, can solve problems such as reducing the thermal stability of polyimide, and achieve low cost, simple operation, high yield and high purity Effect

Inactive Publication Date: 2015-02-25
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of thermal performance, compared with commercial polyimide, although the thermal stability of polyimide is reduced to a certain extent, it is sufficient to meet its use requirements in microelectronics, optoelectronics and other application fields.

Method used

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  • Diamine monomers containing asymmetric non-coplanar structure and preparation method thereof
  • Diamine monomers containing asymmetric non-coplanar structure and preparation method thereof
  • Diamine monomers containing asymmetric non-coplanar structure and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Under nitrogen protection, mix 15 grams (0.100 moles) of 2-tert-butylaniline and 6.5 grams (0.040 moles) of 4-tert-butylbenzaldehyde, and add 3.6 grams (0.024 moles) of the catalyst dropwise within 1 hour at room temperature Trifluoromethanesulfonic acid, be warming up to 160 DEG C and reflux for 20 hours after finishing dropping, cool to room temperature after finishing the reaction, then gradually add dropwise the ammonia solution that the mass percent concentration is 26% to be neutralized to neutrality, will precipitate out and filter, Dry overnight, and the obtained crude product is further purified by silica gel column chromatography (the eluent is a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:8), and finally a light yellow powdery solid is obtained. Non-coplanar diamine monomer (3,3'-di-tert-butyl-4,4'-diaminophenyl-4''-tert-butyltoluene).

[0032] The productive rate in the present embodiment is about 90%; Melting point is 87.5 ℃ (measu...

Embodiment 2

[0034] Under nitrogen protection, mix 15 grams (0.100 moles) of 2-tert-butylaniline and 6.0 grams (0.038 moles) of 4-tert-butylbenzaldehyde, and add 3.6 grams (0.024 moles) of the catalyst dropwise within 1 hour at room temperature Trifluoromethanesulfonic acid, be warming up to 160 DEG C and reflux for 20 hours after the dropwise addition, cool to room temperature after the completion of the reaction, then gradually add dropwise an ammonia solution with a mass percentage concentration of 27% to neutralize, and filter the precipitate. Dry overnight, and the obtained crude product is further purified by silica gel column chromatography (the eluent is a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:6), and finally a white powdery solid is obtained that contains asymmetric asymmetry. Coplanar diamine monomer (3,3′-di-tert-butyl-4,4′-diaminophenyl-1-naphthalene methane).

[0035] The productive rate in the present embodiment is about 88%; Melting point is 1...

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Abstract

The invention discloses diamine monomers containing asymmetric non-coplanar structure and a preparation method thereof. The structural general formula of the diamine monomers containing asymmetric non-coplanar structure is disclosed in the specification. The preparation method comprises the following steps: in a nitrogen protective atmosphere, mixing 100 parts by mole of 2-substituted aniline and 30-40 parts by mole of aromatic substituted formaldehyde, dropwisely adding 10-30 parts by mole of catalyst trifluoromethanesulfonic acid at normal temperature within 1-1.5 hours, heating to 155-165 DEG C under reflux for 15-20 hours, cooling to room temperature after the reaction finishes, adding an alkali solution to a neutral state, filtering the precipitate, drying over night, separating and purifying the obtained crude product by silica gel column chromatography, and eluting with any one or two of dichloromethane, ethyl acetate and petroleum ether to finally obtain a powdery solid which is the diamine monomers containing asymmetric non-coplanar structure.

Description

technical field [0001] The invention belongs to the technical field of aromatic diamine monomer and its preparation, and in particular relates to a diamine monomer with an asymmetric non-coplanar structure and a preparation method thereof. Background technique [0002] Polyimide materials are widely used in high-tech fields such as aerospace, machinery, electronics, and automobiles because of their excellent thermal stability, mechanical properties, dielectric properties, chemical resistance, and corrosion resistance. Due to the unique rigid main chain structure of polyimide, most polyimides have disadvantages such as high processing temperature, insolubility and poor processing performance, which further limit their wide application in related fields. In order to meet the development needs of modern high-tech fields, overcome the above-mentioned shortcomings of polyimide materials, and prepare polyimide materials with good solubility and excellent comprehensive properties, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/50C07C209/28
Inventor 黄孝华刘婵娟裴响林梅媚徐旭韦春
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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