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Substituted di(amino mercapto) benzene hydrochloride and process for preparing same

A technology of dimethylcyclohexane dihydrochloride and cyclohexane dihydrochloride, which is applied in mercaptan preparation, organic chemistry, etc., can solve the problem of reducing intermolecular attraction and chain rigidity, difficulty in film formation, and polymerization Problems such as easy fiber formation, to achieve the effect of improving solubility

Inactive Publication Date: 2005-11-23
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the monomer for preparing PBZT polymer is mainly 2,5-diamino-1,4-benzenedimercapto dihydrochloride (US Patent 4225700), and the PBZT series polymer prepared by this monomer is due to its rigid conjugated structure, It can only be dissolved in some strong protonic acids, and the polyelectrolyte formed by protonation reduces the mutual attraction and chain rigidity between molecules. However, because these protonic acids are not volatile, the polymer is easy to form fibers and difficult to form films. The processing application of the

Method used

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  • Substituted di(amino mercapto) benzene hydrochloride and process for preparing same
  • Substituted di(amino mercapto) benzene hydrochloride and process for preparing same
  • Substituted di(amino mercapto) benzene hydrochloride and process for preparing same

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Embodiment 1

[0031] (a) Add 37.3g (0.4mol) of aniline and 37mL of 35wt% HCl solution into a three-necked flask equipped with a magnetic stirrer, a nitrogen inlet and outlet, and a reflux condenser, and stir to dissolve at 60°C. After the solution was clarified, 9.8 g (0.1 mol) of cyclohexanone was added dropwise. The mixture was reacted at 120°C for 24 hours. The solution was cooled to room temperature, 10% sodium hydroxide solution was added to pH = 10, the organic layer was separated and washed with water until neutral. Dry over anhydrous magnesium sulfate, distill off excess aniline under reduced pressure, and recrystallize from toluene to obtain 22.1 g of 1,1-bis(4-aminophenyl)cyclohexane (83.1% yield).

[0032] (b) 26.6g (0.1mol) 1,1-bis((4-amino)phenyl)cyclohexane, 398mL glacial acetic acid were added to a three-necked flask equipped with mechanical stirring, nitrogen inlet and dropping funnel, After stirring to dissolve, add 48.5g (0.51mol) potassium thiocyanate. Under the condit...

Embodiment 2

[0035] (a) 15.4g (0.1mol) 4-tert-butylcyclohexanone, 51.8g (0.4mol) aniline hydrochloride and 102.3g (1.1mol) aniline were added to a three-necked flask with magnetic stirring and nitrogen inlet, and the mixture was Stir and reflux at 140° C. for 36 hours, cool the solution to room temperature, add 10 wt % potassium hydroxide solution to pH = 10, and reflux the mixture for 10 minutes. The organic layer is separated and washed with water until neutral. Dry over anhydrous magnesium sulfate, distill off excess aniline under reduced pressure, and recrystallize from benzene to obtain 20.6 g of 1,1-bis(4-aminophenyl-4-tert-butylcyclohexane (63.9% yield).

[0036] (b) Add 16.1g (0.05mol) 1,1-bis(4-aminophenyl)-4-tert-butylcyclohexane and 240mL glacial acetic acid into a three-necked flask equipped with mechanical stirring, nitrogen inlet and dropping funnel In, stirring and dissolving, add 29.1g (0.3mol) potassium thiocyanate. Under the conditions of cooling in an ice bath and mecha...

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Abstract

The invention discloses a substituted di(amino mercapto) benzene hydrochloride and process for preparation, which is prepared by using compounds containing benzeneamine and carbonyl as starting raw material through three-step reactions. It can be used for preparing novel benzopyrene polymers together with dicarboxylic acids through polycondensation, the dissolving property of these polymers can be increased, and fine properties of high thermal stability and chemical stability can be achieved.

Description

Technical field: [0001] The invention relates to a class of organic compounds and a preparation method, in particular to a class of substituted bis(aminomercapto)benzene hydrochloride and a preparation method thereof. Background technique: [0002] As early as the 1960s, the Polymer Group (MLBP) of the SRI (Stanford Research International) Materials Laboratory began to develop high-temperature-resistant polymer materials for the US Air Force. Wolfe and others at SRI launched it in 1981 on the basis of long-term exploration. The para-aromatic polymer with 2,6-benzobiheterocyclic ring on the main chain has made great progress and success in this research, and has attracted extensive attention. It is considered to be the pioneer and leader of a new generation of polymer materials represent. Polybenzothiazole polymer (PBZT) has unique and excellent characteristics in many aspects. It is a polymer material with excellent mechanical properties, thermal oxidation resistance and ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/34
Inventor 黄炜印杰
Owner SHANGHAI JIAO TONG UNIV
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