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Fluorescent compound for isocyanate substance detection, preparation method and application thereof as test paper type detection probe

A technology of fluorescent compounds and isocyanic acid, which is applied in the preparation of imino compounds, chemical instruments and methods, and analysis using chemical indicators, etc. High discrimination, improved detection effect, strong luminous effect

Active Publication Date: 2019-10-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of this molecule is complicated, and a large amount of dangerous and irritating chemical reagents such as oxalyl chloride are required in the preparation process, which is not conducive to environmental protection; at the same time, because of the long preparation process, the final yield is not high. Not conducive to mass production
The currently reported fluorescent probe compounds used to detect isocyanate substances are basically traditional aggregation-quenching fluorescent compounds, which do not have the effect of aggregation-induced fluorescence enhancement. Therefore, these fluorescent probe compounds are used as solid-state detectors (such as detection test paper ) often leads to fluorescence quenching due to aggregation, which makes the fluorescence quantum yield of solid-state detectors such as test paper low and the luminescence is weak, thus affecting the detection effect

Method used

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  • Fluorescent compound for isocyanate substance detection, preparation method and application thereof as test paper type detection probe
  • Fluorescent compound for isocyanate substance detection, preparation method and application thereof as test paper type detection probe
  • Fluorescent compound for isocyanate substance detection, preparation method and application thereof as test paper type detection probe

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Embodiment 1

[0050] A preparation method of a fluorescent compound (BTPAP) for isocyanate substance detection, comprising the following steps:

[0051] (1) Dissolve 672 mg of N,N-diphenyl-[1,1'-biphenyl]-4,4'-diamine in 20 mL of acetonitrile, and stir uniformly with ultrasonic to obtain solution 1;

[0052] (2) 150 mg of 4-hydroxyisophthalaldehyde was dissolved in 10 mL of acetonitrile, and ultrasonically stirred to obtain solution 2;

[0053] (3) dissolve the potassium carbonate of 138mg in deionized water simultaneously, stir ultrasonically, obtain the potassium carbonate aqueous solution of 1mol / L;

[0054] (4) the solution 1 described in step (1) and the solution 2 described in step (2) are mixed uniformly, and the potassium carbonate aqueous solution of 1 mol / L obtained in step (3) is added dropwise thereto, and the solution is evacuated and filled with nitrogen, Heating reaction was carried out, and the reaction temperature was controlled at 25°C. After 3 hours of reaction, the reac...

Embodiment 2

[0057] A preparation method of a fluorescent compound (BTPAP) for isocyanate substance detection, comprising the following steps:

[0058] (1) Dissolve 1008 mg of N,N-diphenyl-[1,1'-biphenyl]-4,4'-diamine in 50 mL of acetonitrile, and stir uniformly with ultrasonic to obtain solution 1;

[0059] (2) 150 mg of 4-hydroxyisophthalaldehyde was dissolved in 50 mL of acetonitrile, and ultrasonically stirred to obtain solution 2;

[0060] (3) 690 mg of potassium carbonate was dissolved in deionized water, and ultrasonically stirred to obtain a 3 mol / L potassium carbonate aqueous solution

[0061] (4) the solution 1 described in step (1) and the solution 2 described in step (2) are mixed uniformly, and the potassium carbonate aqueous solution of 3 mol / L obtained in step (3) is added dropwise thereto, and the solution is evacuated and filled with nitrogen, Heating reaction was carried out, and the reaction temperature was controlled at 70°C. After 12 hours of reaction, the reaction wa...

Embodiment 3

[0064] A preparation method of a fluorescent compound (BTPAP) for isocyanate substance detection, comprising the following steps:

[0065] (1) Dissolve 1680 mg of N,N-diphenyl-[1,1'-biphenyl]-4,4'-diamine in 500 mL of acetonitrile, and stir uniformly with ultrasonic to obtain solution 1;

[0066] (2) 150 mg of 4-hydroxyisophthalaldehyde was dissolved in 100 mL of acetonitrile, and ultrasonically stirred to obtain solution 2;

[0067] (3) the potassium carbonate of 1380mg is dissolved in deionized water, ultrasonically stirs, obtains the potassium carbonate aqueous solution of 6mol / L;

[0068] (4) The solution 1 described in step (1) and the solution 2 described in step (2) are mixed uniformly, and the 6mol / L potassium carbonate aqueous solution obtained in step (3) is added dropwise thereto, vacuumed and filled with nitrogen to carry out The reaction was heated, and the reaction temperature was controlled at 120°C. After 24 hours of reaction, the reaction was stopped. After c...

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Abstract

The invention discloses a fluorescent compound for isocyanate substance detection, a preparation method and application thereof as a test paper type detection probe. The fluorescent compound is 2,4-bis (((4'-(diphenylamino)-[1,1'-biphenyl]-4-yl) imino) methyl) phenol. The fluorescent compound is prepared by a one-step method, is simple and convenient to prepare, has high yield, can rapidly and specifically respond to isocyanate substances, and the fluorescence intensity of the fluorescent compound is enhanced with the increase of isocyanate concentration. The fluorescent compound can be made into a portable test paper probe for detecting the isocyanate substances in air and can realize visual detection of volatile isocyanate gases. The probe has an aggregation induced luminescence effect,and can have higher fluorescence quantum yield when being detected by a test paper probe. The fluorescent probe prepared by the method can be used for detecting the isocyanate substances in a solutionand gaseous isocyanate substances, and can be used for monitoring isocyanate in atmosphere, water resources and the like.

Description

technical field [0001] The invention relates to the technical field of photochemical detection and analysis, in particular to a fluorescent compound used for the detection of isocyanate substances, a preparation method and its application as a test paper-type detection probe. Background technique [0002] Isocyanates mainly include a variety of compounds with -NCO functional groups such as monoisocyanates, diisocyanates and polyisocyanates. Because of the high reactivity of functional groups, isocyanates are widely used as raw materials in the polyurethane industry for the production of various polyurethane articles. In addition, isocyanate is also an essential component of pesticides, fungicides, herbicides, etc., and is also widely used in industrial chemistry, pharmaceutical preparation, agricultural sterilization and other fields. Polyurethane products (such as polyurethane adhesives) will release residual free isocyanates or isocyanates produced by degradation during c...

Claims

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Application Information

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IPC IPC(8): C07C251/24C07C249/02C09K11/06G01N21/78
CPCC07C251/24C09K11/06G01N21/78C09K2211/1007C09K2211/1014G01N21/643C09B55/005C09B57/008G01N31/22
Inventor 吴水珠徐灵峰曾钫
Owner SOUTH CHINA UNIV OF TECH
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