CN108445155B - Test paper for detecting benzene reagent - Google Patents

Test paper for detecting benzene reagent Download PDF

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Publication number
CN108445155B
CN108445155B CN201810216107.8A CN201810216107A CN108445155B CN 108445155 B CN108445155 B CN 108445155B CN 201810216107 A CN201810216107 A CN 201810216107A CN 108445155 B CN108445155 B CN 108445155B
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benzene
test paper
calixarene
detecting
polyamide
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CN108445155A (en
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苗瑞祥
刘冬青
任顺
朱泽晛
李珂
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Tianjin Polytechnic University
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2301/08—Cellulose derivatives
    • C08J2301/10—Esters of organic acids
    • C08J2301/12—Cellulose acetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08J2327/16—Homopolymers or copolymers of vinylidene fluoride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2477/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers

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  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Analytical Chemistry (AREA)
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  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

The invention relates to test paper for detecting a benzene reagent and a preparation method thereof, belonging to the fields of macromolecular amphiphilic self-assembly and new material preparation. The invention adopts calixarene acyl chloride derivative to react with piperazine to prepare linear poly (calixarene-piperazine) amide. The main chain of the polyamide macromolecule has a calixarene block, so that benzene and derivatives thereof can be complexed. After the polyamide is complexed with benzene, the chains shrink and distort, i.e., a "stimulus-response" reaction occurs. This feature can be used to detect the presence of benzene and its derivatives. The polyamide is mixed with other high polymers to prepare a film, and the flat test paper-like detection material is prepared and used for rapidly detecting benzene and derivatives thereof in the environment. The method provides a simple, convenient and practical new scheme for detecting the benzene substances.

Description

Test paper for detecting benzene reagent
Technical Field
The invention relates to preparation of polyamide and preparation of a solution blending material thereof, which are used for detecting aromatic organic molecules, and relates to a preparation technology of a stimulus-response material.
Background
Aromatic hydrocarbons with benzene rings are harmful to the environment and the human body, and can cause harm to the nervous system, the blood system, the digestive system and the skin of the human body. Especially, the blood system is very sensitive to benzene substances, and the first-line operators can cause diseases of various organ systems after contacting the benzene substances for a long time. Therefore, the detection of benzene in environment, solution and the like is very important, and the research and development of the technology and the material for quickly and conveniently detecting the existence of benzene are prepared. The test paper capable of quickly and simply detecting the structure of aromatic hydrocarbons such as benzene is a product with market potential.
The preparation method comprises the step of polymerizing piperazine with an organic solution of monomer calixarene diacid chloride with a reactive group to prepare linear poly (calixarene-piperazine) amide. The polyamide is a polymer chain structure formed by linking aromatic rigid large-ring building blocks and small-molecular-weight heterocycles, and multiple contrast factors are alternately presented on a large molecular chain, so that the polyamide is endowed with the self-assembly characteristic and rich stimulus-response behaviors. After the polymer is contacted with a benzene reagent, the molecular chain generates violent contraction, bending torsion and other stimulus-response behaviors due to pi-pi interaction. The poly (calixarene-piperazine) amide and other polymers can be uniformly distributed in the membrane casting solution after being blended, and can be uniformly distributed in the membrane and on the surface of the membrane after being subjected to wet membrane scraping. The film was a flat paper package under dry conditions. After the benzene substances are contacted with the blending membrane, the benzene ring enters a pi-electron-rich cavity of the calixarene under the driving of pi-pi interaction, the polyamide molecular chain is induced to shrink and bend and twist, finally, the whole blending flat membrane is deformed, and the potential of directional detection of the benzene and other toxic substances is shown.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of a benzene detection reagent test paper.
The technical scheme of the invention is summarized as follows:
the test paper for detecting the benzene reagent is characterized in that a polymer III is generated by polymerizing a calixarene monomer I and piperazine. Dissolving the polymer III in an organic solvent, adding the polymer A, uniformly mixing to obtain a casting solution, and preparing a flat membrane by using deionized water as a coagulating bath through a phase inversion method to obtain the benzene substance detection test paper.
The structural formula of calixarene monomer I is as follows:
Figure GSB0000190693580000011
the polymer A is one or a mixture of two of polyvinylidene fluoride and/or cellulose acetate; the organic solvent is one and/or a mixture of N, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone and/or dimethyl sulfoxide.
Drawings
FIG. 1 is a test strip for detecting benzene reagent;
FIG. 2 is a diagram showing the test effect of test paper on toluene;
FIG. 3 is a graph showing the test effect of the test paper on aniline.
Examples
Synthesis of Polymer I
All examples
Example 1
5mL of I with a concentration of 5mg/mL1The solution was added dropwise to 10mL of a piperazine solution having a concentration of 30mg/mL, reacted for 5min, and the interfacial polymerization product was collected. Alternately washing with 20mL of n-hexane and 20mL of deionized water for 3 times, and drying to obtain white powdery polymer III12mg。
Example 2
10mL of a piperazine solution having a concentration of 30mg/mL was added dropwise to 5mL of I having a concentration of 5mg/mL1Stirring the solution at a constant speed of 100r/min for 10min to generate a solution polymerization product, and collecting the solution polymerization product. Washing with n-hexane and deionized water, and drying to obtain white flaky polymer III22.8mg。
Preparation of test paper
Example 3
Mixing polymer III1Dissolving in N, N-dimethylformamide to prepare 4mL of solution with the concentration of 0.5 mg/mL. Adding 500mg of the compound A, stirring, defoaming in vacuum, scraping a flat membrane, putting into deionized water for solidification, and drying to prepare the test paper capable of detecting the benzene reagents. (the test paper has the detection effect on the benzene reagents and is shown in the attached drawing of the specification.)
Example 4
4mL of Polymer III are prepared20.5mg/mL of dimethyl sulfoxide solution. Adding 500mg of polymer A, stirring, defoaming in vacuum, scraping a flat membrane, putting into deionized water for solidification, and drying to obtain the test paper capable of detecting the benzene reagents.

Claims (2)

1. A test paper for detecting benzene reagent is characterized in that a polymer III is generated by polymerizing a calixarene monomer I and piperazine; dissolving a polymer III in an organic solvent, adding a polymer A, uniformly mixing to obtain a casting solution, and preparing a flat membrane by using deionized water as a coagulating bath through a phase inversion method to obtain benzene substance detection test paper; the structural formula of the calixarene monomer I is as follows
Figure FSB0000189529940000011
2. The polymer A according to claim 1 is one or a mixture of two of polyvinylidene fluoride and/or cellulose acetate; the organic solvent is one and/or a mixture of N, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone and/or dimethyl sulfoxide.
CN201810216107.8A 2018-03-13 2018-03-13 Test paper for detecting benzene reagent Expired - Fee Related CN108445155B (en)

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Citations (4)

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CN102276481B (en) * 2011-04-29 2014-05-14 苏州大学 Calixarene derivative and metal complex thereof, and preparation method and application of calixarene derivative and metal complex thereof
CN104628939A (en) * 2013-11-14 2015-05-20 中国科学院理化技术研究所 Novel water-soluble polymer capable of selectively identifying mercury ions and preparation method and application thereof
CN107663211A (en) * 2016-07-29 2018-02-06 沈阳药科大学 Carbazole calixarenes tetracyclic and its preparation method and application

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US8034621B2 (en) * 2009-08-18 2011-10-11 Indian Institute Of Technology Chemical sensors of zinc, nickel, and copper ions
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US8034622B2 (en) * 2009-06-30 2011-10-11 Indian Institute Of Technology Bombay Selective detection of Hg2+ by calix[4]arenes
CN102276481B (en) * 2011-04-29 2014-05-14 苏州大学 Calixarene derivative and metal complex thereof, and preparation method and application of calixarene derivative and metal complex thereof
CN104628939A (en) * 2013-11-14 2015-05-20 中国科学院理化技术研究所 Novel water-soluble polymer capable of selectively identifying mercury ions and preparation method and application thereof
CN107663211A (en) * 2016-07-29 2018-02-06 沈阳药科大学 Carbazole calixarenes tetracyclic and its preparation method and application

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Host–guest sensing by calixarenes on the surfaces;Hyun Jung Kim等;《Chem. Soc. Rev.》;20121231;第41卷;第1173-1190页 *
具有离子识别功能的新型智能膜研究;唐橙橙等;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20120415(第4期);第B014-68页 *
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