Synthesis of a Triamine Containing a Symmetrical Triarylpyridine Structure and Its Hyperbranched Polyimide

A technology of triarylpyridine and polyimide, which is applied in the field of hyperbranched polyimide polymers, can solve the problems that the product structure is difficult to control, rarely used, and prone to gel.

Inactive Publication Date: 2011-12-07
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In addition, among the many synthetic methods of hyperbranched polyimide, by AB x The product structure obtained by (x≥2) type monomer is not easy to control, so it is rarely used; A 2 +B 3 Although the method is widely accepted, gels are prone to occur during the reaction, so a B with a slightly different functional group a

Method used

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  • Synthesis of a Triamine Containing a Symmetrical Triarylpyridine Structure and Its Hyperbranched Polyimide
  • Synthesis of a Triamine Containing a Symmetrical Triarylpyridine Structure and Its Hyperbranched Polyimide
  • Synthesis of a Triamine Containing a Symmetrical Triarylpyridine Structure and Its Hyperbranched Polyimide

Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Add 12.2g (0.1mol) of p-hydroxybenzaldehyde, 27.2g (0.2mol) of p-hydroxyacetophenone, 75g of ammonium acetate and 250mL of glacial acetic acid into a three-necked flask, heat it to reflux for 2 hours after passing nitrogen, and discharge In deionized water, the filtered filter residue was recrystallized by ethanol to obtain a yellow trihydroxypyridine compound 2,4,6-tris(4-hydroxyphenyl)pyridine.

[0032] Yield: 33wt%; FT IR (cm -1 , KBr): 3295 (-OH), 1607, 1548 and 1445 (C=N and C=C on pyridine ring and benzene ring); 1 H NMR (ppm, DMSO-d 6): 9.76 (s, 1H), 9.68 (s, 2H), 8.09-8.08 (d, 4H), 7.83 (s, 2H), 7.80-7.79 (d, 2H), 6.88-6.85 (d, 6H).

[0033] (2) Under nitrogen protection, 8.0g (0.023mol) of the trihydroxypyridine compound obtained by (1), 12.6g (0.080mol) of p-chloronitrobenzene, 11.1g (0.080mol) of potassium carbonate, and N, N- Add 100mL of dimethylacetamide into a three-necked flask, then add 40mL of toluene and raise the temperature to reflux for 15h....

Embodiment 2

[0038] (1) Add 61.1g (0.5mol) of p-hydroxybenzaldehyde, 136.2g (1.0mol) of p-hydroxyacetophenone, 375g of ammonium acetate and 1250mL of glacial acetic acid into a three-necked flask, and heat to reflux for 3 hours after passing through nitrogen, and discharge In deionized water, the filtered filter residue was recrystallized by ethanol to obtain a yellow trihydroxypyridine compound 2,4,6-tris(4-hydroxyphenyl)pyridine.

[0039] Yield: 35wt%; FT IR (cm -1 , KBr): 3297 (-OH), 1605, 1541 and 1439 (C=N and C=C on pyridine ring and benzene ring); 1 H NMR (ppm, DMSO-d 6 ): 9.76 (s, 1H), 9.68 (s, 2H), 8.09-8.07 (d, 4H), 7.83 (s, 2H), 7.79-7.78 (d, 2H), 6.88-6.86 (d, 6H).

[0040] (2) Under nitrogen protection, 40.0g (0.113mol) of the trihydroxypyridine compound obtained by (1), 53.6g (0.340mol) of p-chloronitrobenzene, 47.0g (0.340mol) of potassium carbonate and N, N- Add 500 mL of dimethylacetamide into a three-necked flask, then add 100 mL of toluene and heat up to reflux for 18...

Embodiment 3-8

[0044] The following Examples 3-8 use 2,4,6-tris[4-(4-aminophenoxy)-phenyl]pyridine as a raw material to prepare amino-terminated hyperbranched polyimide polymers.

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Abstract

The invention relates to synthesis of a triamine containing a symmetrical triaryl pyridine structure and hyperbranched polyimide thereof. The triamine monomer is BB'2-type aromatic triamine, namely 2,4,6-tris[4-(4-aminophenoxy)-phenyl] pyridine the structure of which is shown in the specification. The triamine is prepared by the following three steps: firstly reacting p-hydroxybenzaldehyde with p-hydroxyacetophenone in acetic acid to obtain 2,4,6-tris(4-hydroxyphenyl) pyridine, then reacting 2,4,6-tris(4-hydroxyphenyl) pyridine with p-chloronitrobenzene to obtain 2,4,6-tris[4-(4-nitrophenoxy)-phenyl] pyridine, and finally reducing the trinitro compound by use of hydrazine hydrate in the presence of a carbon-supported palladium catalyst to synthesize 2,4,6-tris[4-(4-aminophenoxy)-phenyl] pyridine. The hyperbranched polyimide of the triamine is an amino-terminated or anhydride-terminated hyperbranched polyimide polymer obtained by polymerization of the triamine monomer and a commercial dianhydride monomer. The prepared hyperbranched polyimide has excellent high-temperature resistance, solubility and optical properties; and the hyperbranched polyimide polymer material has great application value and prospects in the fields of photosensitive, optical waveguide and gas permeation separation membranes and other materials.

Description

technical field [0001] The invention belongs to the field of macromolecular materials, and specifically relates to 2,4,6-tris[4-(4-aminophenoxy)-phenyl]pyridine monomer, which contains BB' of symmetrical triarylpyridine structure 2 The synthetic method of type triamine monomer and the hyperbranched polyimide polymer synthesized from this triamine monomer. Background technique [0002] In recent years, hyperbranched polyimide has a series of excellent comprehensive properties due to the advantages of both polyimide and hyperbranched polymer, such as high temperature resistance, high strength, high dielectric, low or no crystallinity Crystallization, low solution viscosity, and good solubility have attracted the attention and research of many scientific researchers. Its products have been developed and applied to membrane materials such as gas separation membranes and permeable membranes, as well as other high-tech materials such as photosensitive, optical waveguides, liquid ...

Claims

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Application Information

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IPC IPC(8): C07D213/30C08G73/10
Inventor 徐祖顺易昌凤陈文求严微
Owner HUBEI UNIV
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