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Hydroxyl-containing benzimidazole diamines and preparation method thereof

A kind of technology of hydroxybenzimidazole diamine and triaminobenzene, which is applied in the field of synthesis of organic compounds

Active Publication Date: 2016-02-24
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The above method can prepare 5-amino-2-(4-aminobenzene)benzimidazole, but there is still room for further improvement in the mechanical properties such as strength and modulus of the polyimide synthesized from this raw material.

Method used

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  • Hydroxyl-containing benzimidazole diamines and preparation method thereof
  • Hydroxyl-containing benzimidazole diamines and preparation method thereof
  • Hydroxyl-containing benzimidazole diamines and preparation method thereof

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preparation example Construction

[0045] The present invention also provides a kind of preparation method of hydroxy-containing benzimidazole diamine, comprising the following steps:

[0046] A1) Reaction of 1,2,4-triaminobenzene hydrochloride with a salicylic acid derivative having a structure shown in formula (IV) to obtain a hydroxy-containing benzimidazole diamine having a structure shown in formula (I) ;

[0047]

[0048] or

[0049] A2) Reaction of 1,2,4-triaminobenzene hydrochloride with a salicylic acid derivative having a structure shown in formula (V) to obtain a hydroxy-containing benzimidazole diamine having a structure shown in formula (II) ;

[0050]

[0051] or

[0052] A3) Reaction of 3,3',4,4'-tetraaminobiphenyl with a salicylic acid derivative having a structure shown in formula (IV) to obtain a hydroxy-containing benzimidazole having a structure shown in formula (III) Diamine;

[0053]

[0054] In the present invention, the step A1) preferably specifically includes the following ...

Embodiment 1

[0126] (1) Under the condition of nitrogen protection, 58.82g (0.3mol) of 1,2,4-triaminobenzene hydrochloride, 600gP 2 o 5 Content is 80% polyphosphoric acid, 1.35g (0.006mol) SnCl 2 · 2 h 2 O, stirred at 80°C for 8h to obtain the first mixed solution of 1,2,4-triaminobenzene;

[0127] (2) Add 60g (0.42mol) P to the above first mixed solution 2 o 5 , 46.84g (0.33mol) 4-aminosalicylic acid, reacted at 210°C for 8h to obtain a reaction mixture;

[0128] (3) Cool the above reaction mixture to 120°C, then pour it into ice water and stir for 2 hours, then filter and wash with distilled water, then take out the filter cake, add a small amount of water, wash with saturated NaHCO 3 The pH value of the solution was adjusted to 8, then filtered, washed with distilled water, and finally vacuum-dried at 120°C for 24 hours to obtain a crude product of hydroxybenzimidazole-containing diamine;

[0129] (4) Using dimethyl sulfoxide as a solvent, recrystallize the crude diamine containi...

Embodiment 2

[0135] (1) Under the condition of nitrogen protection, 58.82g (0.3mol) of 1,2,4-triaminobenzene hydrochloride, 650gP 2 o 5 Polyphosphoric acid with a content of 80%, 0.36g (0.003mol) tin powder, stirred at 100°C for 6h to obtain the first mixed solution of 1,2,4-triaminobenzene;

[0136] (2) Add 42.57g (0.3mol) P 2 o 5 , 45.34g (0.3mol) of 5-aminosalicylic acid, reacted at 200°C for 6h to obtain a reaction mixture;

[0137] (3) Cool the above reaction mixture to 120°C, then pour it into ice water and stir for 2 hours, then filter and wash with distilled water, then take out the filter cake, add a small amount of water, wash with saturated NaHCO 3 The pH value of the solution was adjusted to 8, then filtered, washed with distilled water, and finally vacuum-dried at 120°C for 24 hours to obtain a crude product of hydroxybenzimidazole-containing diamine;

[0138] (4) The crude product of hydroxy-containing benzimidazole diamine was sublimed at 330° C. to obtain hydroxy-contai...

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Abstract

The invention provides hydroxyl-containing benzimidazole diamines and a preparation method thereof. The hydroxyl-containing benzimidazole diamines possess the structures shown as a formula (I), a formula (II) or a formula (III). The preparation method comprises the following steps: A1) reacting 1,2,4-benzenetriamine dihydrochloride with a salicylic acid derivative with the structure shown as a formula (IV), so as to obtain a hydroxyl-containing benzimidazole diamine with the structure shown as a formula (I); or A2) reacting 1,2,4-benzenetriamine dihydrochloride with a salicylic acid derivative with the structure shown as a formula (V), so as to obtain a hydroxyl-containing benzimidazole diamine with the structure shown as a formula (II); or A3) reacting 3,3'-diaminobenzidine with a salicylic acid derivative with the structure shown as a formula (IV), so as to obtain a hydroxyl-containing benzimidazole diamine with the structure shown as a formula (III). Compared with the prior art, polyimides prepared from the provided hydroxyl-containing benzimidazole diamines are high in strength and large in modulus.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic compounds, in particular to a hydroxy-containing benzimidazole diamine and a preparation method thereof. Background technique [0002] Polyimide is one of the organic polymer materials with the best comprehensive performance. It can withstand high temperature above 400°C and has a long-term service temperature range of -200°C to 300°C. The loss is only 0.004~0.007, which belongs to F to H class insulating materials. At present, polyimide containing benzimidazole structure is replacing traditional polyimide materials due to its excellent performance, and is widely used in the field of microelectronics manufacturing and aerospace. For example, the flexible printed circuit substrate prepared by gluing polyimide film containing benzimidazole structure and copper foil has the characteristics of light weight, high reliability and easy assembly, which has accelerated the development of the ...

Claims

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Application Information

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IPC IPC(8): C07D235/18C08G73/10D01F6/74
CPCC07D235/18C08G73/1067D01F6/74
Inventor 邱雪鹏代学民董志鑫矫龙
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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