Polyamine containing triazole ring and preparation method and application thereof

A technology of polyamines and triazole rings, applied in the field of polyamines containing triazole rings and its preparation, can solve the problems of low yield, difficult synthesis, high cost, etc., and achieve excellent heat resistance and wide application prospects

Inactive Publication Date: 2010-07-14
安徽中科达美新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The introduction of aromatic, symmetrical, basic and polar pyridine rings into polyimide not only maintains the excellent thermal stability and chemical stability of polyimide, but also greatly improves the processing properties of polymers such as Solubility and film-forming properties (a.Susanta B, MukeshK M, Vijay K.Journal of Applied Polymer Science, 2004, 93, 821; b.HariharanR, Bhuvana S, Anitha Malbi M, Sarojadevi M, Journal of Applied Polymer Science, 2004, 93, 1846), but the synthesis of monomers containing pyridine rings is difficult, the yield is low, and the cost is high

Method used

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  • Polyamine containing triazole ring and preparation method and application thereof
  • Polyamine containing triazole ring and preparation method and application thereof
  • Polyamine containing triazole ring and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] (1) Synthesis of 1,4-diazidemethylbenzene

[0048] Add p-dichloromethylbenzene (0.05mol), NaN 3 (0.15mol), toluene (20mL) and N,N-dimethylformamide (20mL), heated to 70-75°C under stirring, and reacted at constant temperature for 3 hours. After the reaction, the reaction product was cooled to room temperature, poured into 200mL of deionized water was left to stand overnight under freezing conditions to precipitate white flaky crystals, filtered, the filter cake was washed with deionized water, and dried to obtain a white powdery solid with a yield of 90%. Melting point: 27~29℃; FT-IR (KBr, v, cm -1 ): 2089 (-N 3 stretching vibration); 1 H-NMR (CDCl 3 , TMS) δ: 7.33 (s, 4H, Ha), 4.35 (s, 4H, Hb), its structural formula is:

[0049]

[0050] (2) Synthesis of 1,4-bis[4-(3-aminophenyl)-1,2,3-triazole-1-methylene]benzene

[0051] Add 1,4-diazidemethylbenzene (0.01mol), m-aminophenylacetylene (0.02mol), CuSO 4 ·5H 2 O (0.005mol), sodium ascorbate (0.01mol), N,N-dim...

Embodiment 2

[0054] (1) Synthesis of 4,4-diazidomethylbiphenyl

[0055] Add p-dichloromethylbiphenyl (0.05mol), NaN 3 (0.15mol), toluene (20mL) and DMF (20mL), heated to 70-75°C under stirring, and reacted at constant temperature for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature, poured into 200mL deionized water, and stood overnight , a white solid was precipitated, filtered, the filter cake was washed with deionized water, and dried to obtain a white powdery solid with a yield of 89%. Melting point 68~71℃; FT-IR (KBr, v, cm -1 ): 2089 (-N 3 stretching vibration); 1 H-NMR (CDCl 3 , TMS) δ: 7.33 (s, 4H, Ha), 7.29 (s, 4H, Ha), 4.35 (s, 4H, Hb), its structural formula is:

[0056]

[0057] (2) Synthesis of 4,4-bis[4-(3-aminophenyl)-1,2,3-triazole-1-methylene]biphenyl

[0058] Add 1,4-diazidemethylbenzene (0.01mol), m-aminophenylacetylene (0.02mol), CuSO 4 ·5H 2 O (0.005 mol), sodium ascorbate (0.01 mol), triethylamine (0.02 mol), N,...

Embodiment 3

[0061] (1) Synthesis of ethylene glycol diazide

[0062] The synthesis reaction is carried out in two steps, first the chlorination of polyethylene glycol, and then azidation, the reaction equation is:

[0063]

[0064] In the 500mL flask equipped with stirring, add polyethylene glycol 0.08mol, SOCl 2 200mL, equipped with a spherical condenser and a gas absorption tube, heated to 65°C with an oil bath, and stirred for 72h. After the reaction was over, excess SOCl was distilled off under reduced pressure on a rotary evaporator. 2 , add NaHCO 3 The aqueous solution was adjusted to pH > 7, and filtered with suction. Filtrate with 50mL CHCl 3 Extract 3 times, then add anhydrous magnesium sulfate to dry, filter with suction, distill off the solvent to obtain the chlorinated product of polyethylene glycol.

[0065]In a 250mL single-necked round bottom flask equipped with stirring, add 0.08mol of the chlorinated product of polyethylene glycol synthesized above, NaN 3 0.4mol,...

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Abstract

The invention relates to polyamine containing a triazole ring and a preparation method and application thereof. The preparation method of the polyamine comprises the following steps of: preparing an azide by a nucleophilic substitution reaction; synthesizing the polyamine containing the triazole ring by the Huisgen cycloaddition reaction of the azide and a compound with alkynyl amine; and applying the polyamine containing the triazole ring to the preparation of polyimide. The invention has the following advantages that: polytriazole imide has superior processable property and can be dissolved in polar solvents, such as DMAc, DMF, DMSO, NMP and the like; the prepared polytriazole imide has the properties of the polyimide, such as superior heat resistance, low-temperature resistance, chemical resistance, mechanical properties, dielectric and insulation properties, fire retardance, bonding properties and the like; the polytriazole imide can be used as a functional polyimide material and is especially suitable for serving as a metal coating material and a corrosion-resistant material; and the novel polytriazole imide material has extensive application prospect in the fields of aviation, spaceflight, ships, micro-electronics and the like.

Description

【Technical field】 [0001] The invention relates to the technical field of polyamines, in particular to a polyamine containing a triazole ring and its preparation method and use. 【Background technique】 [0002] In 1908, Bogert and Renshaw synthesized aromatic polyimides in the laboratory for the first time through the melt self-condensation of 4-aminophthalic anhydride (Kurita K, Williams R L, H-eat-Resistant Polymers Containing Bipyridyl Units.II. Polyamide-imides, Journal of PolymerScience: Polymer Edition, 1973, 11: 3151-3160), because the polymer science was in its infancy at that time, and the nature and performance of polymers had not yet been fully understood, so this discovery was not accepted. due attention. The first peak of polyimide development appeared in the late 1950s to mid-1960s. In 1955, Edwards and Robison, scientists of DuPont Corporation of the United States, applied for a patent on polyimide materials for the first time in the world. Since then, in ord...

Claims

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Application Information

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IPC IPC(8): C07D249/06C08G73/10
Inventor 黄发荣杜磊鄂彦鹏万里强周小安周燕
Owner 安徽中科达美新材料科技有限公司
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