CN110565440A - salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof - Google Patents

salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof Download PDF

Info

Publication number
CN110565440A
CN110565440A CN201910844388.6A CN201910844388A CN110565440A CN 110565440 A CN110565440 A CN 110565440A CN 201910844388 A CN201910844388 A CN 201910844388A CN 110565440 A CN110565440 A CN 110565440A
Authority
CN
China
Prior art keywords
graphene oxide
schiff base
salicylaldehyde
oxide modified
paper
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201910844388.6A
Other languages
Chinese (zh)
Inventor
张素风
范江
杜敏
贺斌
姚雪
刘亚丽
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shaanxi University of Science and Technology
Original Assignee
Shaanxi University of Science and Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shaanxi University of Science and Technology filed Critical Shaanxi University of Science and Technology
Priority to CN201910844388.6A priority Critical patent/CN110565440A/en
Publication of CN110565440A publication Critical patent/CN110565440A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/06—Alcohols; Phenols; Ethers; Aldehydes; Ketones; Acetals; Ketals
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07—Nitrogen-containing compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
    • G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N2021/6432—Quenching

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plasma & Fusion (AREA)
  • Molecular Biology (AREA)
  • Optics & Photonics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

The invention provides a salicylaldehyde Schiff base/graphene oxide modified paper base material and a preparation method and application thereof, wherein the method comprises the following steps of 1, mixing the raw materials in a mass ratio of (30-90): (10-30) carrying out reflux reaction on the salicylaldehyde and 1,2,4, 5-benzene tetramine hydrochloride, separating a product in a reaction solution, and drying to obtain salicylaldehyde Schiff base; paper is putSoaking the paper substrate in the graphene oxide dispersion liquid and then drying to obtain a graphene oxide modified paper base material; step 2, soaking the graphene oxide modified paper base material in a solution of salicylaldehyde Schiff base, and compounding the graphene oxide and the salicylaldehyde Schiff base on paper to form a compound A; and 3, taking out the compound A and drying to obtain the salicylaldehyde Schiff base/graphene oxide modified paper base material. Through hydroxyl, carboxyl and carbon-nitrogen double bond in the material and Cu2+Electrostatic interaction and coordination chelation are generated between the two to achieve the purpose of rapidly detecting Cu2+The purpose of the ions.

Description

salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof
Technical Field
The invention belongs to the field of metal ion detection, and particularly relates to a salicylaldehyde Schiff base/graphene oxide modified paper base material and a preparation method and application thereof.
Background
copper ions are the most basic metal ions in the construction of a variety of plants and animals and play an important role in a variety of biological processes. Although copper ion is a trace element necessary for human body, once excessive intake of copper ion will bring serious harm to the human body, such as gastrointestinal tract dysfunction, liver and kidney function metabolic disorder, hemolytic anemia and neurodegenerative diseases. With the rapid development of modern industry and economy, industrial wastewater is discharged without treatment, which brings serious harm to the growth and the health development of human beings, animals and plants, so that the detection of copper in water is very important.
At present, the methods for measuring copper ions in solution in the prior art mainly include atomic absorption spectrometry, inductively coupled plasma atomic emission spectrometry, spectrophotometry, chemiluminescence, and the like. Although each of these methods has high sensitivity and specificity, there are some common disadvantages, requiring expensive instruments, cumbersome sample preparation procedures, time consuming, long analysis time and requiring specialized operators. Therefore, it is necessary to develop a simple, cheap, reliable, fast and environmentally friendly method for detecting Cu2+The method of (1).
In the literature, "Liu Yang, Wang Liqiu, Guo Chenxiao and Hou Yajuan [ J ]. Tetrahedron Letters,2018,59,3930", a squaric acid derivative modified paper-based detection material is designed and synthesized, and the detection limit of copper ions is 1 μ M. However, the problems of poor selectivity and high detection limit of the current paper-based materials in the application of detecting copper ions still exist.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a salicylaldehyde Schiff base/graphene oxide modified paper base material, a preparation method and application thereof, the synthesis method is simple, green and environment-friendly, the detection material for detecting copper ions in water can be prepared, the detection cost is low, the efficiency is high, and the detection material is used for detecting Cu ions in water2+High ion selection, visibility by naked eyes and convenience and rapidness in detection.
The invention is realized by the following technical scheme:
A preparation method of a salicylaldehyde Schiff base/graphene oxide modified paper base material comprises the following steps,
step 1, mixing the following components in percentage by mass (30-90): (10-30) carrying out reflux reaction on the salicylaldehyde and 1,2,4, 5-benzene tetramine hydrochloride, separating a product in a reaction solution, and drying to obtain salicylaldehyde Schiff base;
soaking paper in the graphene oxide dispersion liquid and then drying to obtain a graphene oxide modified paper base material;
Step 2, soaking the graphene oxide modified paper base material in a solution of salicylaldehyde Schiff base, and compounding the graphene oxide and the salicylaldehyde Schiff base on paper to form a compound A;
and 3, taking out the compound A and drying to obtain the salicylaldehyde Schiff base/graphene oxide modified paper base material.
Preferably, the reflux reaction in the step 1 is carried out at 65-75 ℃ for 18-30 h.
preferably, the concentration of the graphene oxide dispersion liquid in the step 1 is 0.2-1.2 g/L, and the graphene oxide dispersion liquid is obtained by adding graphene oxide into deionized water and mechanically stirring the mixture uniformly.
preferably, the time for soaking the paper in the graphene oxide dispersion liquid in the step 1 is 20-36 hours.
Preferably, in the step 1, the salicylaldehyde is added into the anhydrous methanol and uniformly stirred to obtain a salicylaldehyde solution with the concentration of 30-90 g/L, and the 1,2,4, 5-benzene tetramine hydrochloride is added into the salicylaldehyde solution with the concentration to perform reflux reaction.
Preferably, the time for soaking the graphene oxide modified paper-based material in the solution of salicylaldehyde Schiff base in the step 2 is 20-36 h.
preferably, the concentration of the solution of the salicylaldehyde Schiff base in the step 2 is 0.2-1.2 g/L, and the salicylaldehyde Schiff base is obtained by adding the salicylaldehyde Schiff base into absolute ethyl alcohol and uniformly stirring.
Preferably, the drying in the step 1 is vacuum drying, wherein the drying temperature of the product after the reflux reaction is 50-90 ℃ and the drying time is 6-16 h; the drying temperature of the paper soaked in the graphene oxide dispersion liquid is 50-90 ℃, and the drying time is 10-60 min;
And 3, vacuum drying is adopted as the drying in the step 3, wherein the drying temperature is 50-90 ℃, and the drying time is 10-60 min.
The salicylaldehyde Schiff base/graphene oxide modified paper base material is prepared by the preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper base material.
Salicylaldehyde Schiff base/graphene oxide modified paper-based material for detecting Cu in water2+application of ions.
compared with the prior art, the invention has the following beneficial technical effects:
The preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper base material comprises the steps of obtaining the salicylaldehyde Schiff base by utilizing a reflux reaction, then modifying the paper base material by using graphene oxide, compounding the salicylaldehyde Schiff base and the graphene oxide modified paper base material in a solution through a physical and chemical action, wherein the salicylaldehyde Schiff base/graphene oxide modified paper base material is combined with Cu through hydroxyl, carboxyl and carbon-nitrogen double bonds in the material2+electrostatic interaction and coordination chelation are generated between the two to achieve the purpose of rapidly detecting Cu2+The purpose of the ion; the paper which is natural, green, wide in source, cheap and easily available and degradable is used as the raw material, and the synthetic method is simple, green and environment-friendly.
The salicylaldehyde Schiff base/graphene oxide modified paper-based material can be used for copper ion of large-batch samplesThe detection is convenient and quick to operate, the selectivity is good, and a small amount of solution to be detected is added to quickly judge whether the sample solution contains Cu2+And the ions reduce the operation steps and the cost.
the salicylaldehyde Schiff base/graphene oxide modified paper-based material test strip prepared by the invention is light yellow in initial color, and is mixed with a metal ion solution to be tested, and when the metal ion to be tested is Cu2+When ions are generated, the color of the test strip is changed from bright yellow to black under the irradiation of an ultraviolet lamp, and then the fluorescence emission spectrum of the material after color change is tested, the fluorescence emission intensity is obviously weakened or quenched, and other metal ions are not obviously changed or are lower in weakening degree, which indicates that the material contains Cu2+Ions but no other metal ions further prove that the material can detect Cu in water2+ions.
Drawings
Fig. 1 is a color change diagram under an ultraviolet lamp after different metal ion solutions to be detected are added to the salicylaldehyde schiff base/graphene oxide modified paper-based material prepared in embodiment 1 of the present invention.
Fig. 2 is a fluorescence spectrum of the paper-based material prepared in embodiment 1 after adding different metal ion solutions to be detected to the paper-based material modified by salicylaldehyde schiff base and graphene oxide.
Detailed Description
The present invention will now be described in further detail with reference to the attached drawings, which are illustrative, but not limiting, of the present invention.
The invention discloses a preparation method of a salicylaldehyde Schiff base/graphene oxide modified paper-based material, which is characterized by comprising the following steps of,
Step 1, adding 1,2,4, 5-benzene tetramine hydrochloride into 1L of methanol solution of salicylaldehyde according to the proportion of adding 10-30 g of 1,2,4, 5-benzene tetramine hydrochloride into 1L of methanol solution of salicylaldehyde, and carrying out reflux reaction at the reaction temperature of 65-75 ℃ for 18-30 h;
filtering the reaction solution, and then drying in vacuum to prepare a compound A, namely salicylaldehyde Schiff base; the methanol solution of the salicylaldehyde is obtained by adding 30-90 g of salicylaldehyde into every 1L of anhydrous methanol and uniformly stirring;
The vacuum drying is carried out in a vacuum drying oven at the drying temperature of 50-90 ℃ for 6-16 h;
step 2, soaking 1 piece of filter paper in the graphene oxide dispersion liquid for 20-36 hours, wherein the filter paper can be A4 or book paper; the graphene oxide dispersion liquid is obtained by adding 0.2-1.2 g of graphene oxide into every 1L of deionized water and mechanically stirring at the speed of 1500-2000 r/min for 10-100 min;
The vacuum drying is carried out in a vacuum drying oven at the drying temperature of 50-90 ℃ for 10-60 min;
Step 3, adding 0.2-1.2 g of the compound A into 1L of absolute ethyl alcohol, performing ultrasonic agitation to obtain an ethanol solution of the compound A, taking a piece of graphene oxide modified filter paper, and soaking the filter paper in the ethanol solution of the compound A for 20-36 hours;
And vacuum drying is carried out in a vacuum drying oven at the drying temperature of 50-90 ℃ for 10-60 min to prepare the salicylaldehyde Schiff base/graphene oxide modified paper base material.
The salicylaldehyde Schiff base/graphene oxide modified paper-based material obtained by the invention is used for detecting Cu in water2+in the case of ions, the specific procedure is as follows,
Adding a salicylaldehyde Schiff base/graphene oxide modified paper-based material test strip into 1mL of solution to be detected, such as industrial wastewater, and changing the color of the test strip from bright yellow to black under the irradiation of an ultraviolet lamp to prove that the solution to be detected contains Cu2+ion, otherwise, proof of absence of Cu in the solution to be tested, i.e. industrial wastewater2+Ions are present.
The present invention will be described in further detail with reference to specific examples.
Example 1
The invention relates to a preparation method of a salicylaldehyde Schiff base/graphene oxide modified paper base material, which specifically comprises the following steps,
step 1, adding 30g of salicylaldehyde into 1L of anhydrous methanol, uniformly stirring to prepare a methanol solution of the salicylaldehyde, adding 10g of 1,2,4, 5-benzenetetramine hydrochloride, carrying out reflux reaction at 75 ℃ for 18 hours, carrying out suction filtration on a reaction solution, and carrying out vacuum drying at 50 ℃ for 16 hours to prepare a compound A;
Step 2, adding 0.2g of graphene oxide into 1L of deionized water, performing ultrasonic treatment, mechanically stirring at the speed of 2000r/min for 10min to prepare a graphene oxide dispersion solution, taking a piece of filter paper, soaking the filter paper in the graphene oxide dispersion solution for 36h, and performing vacuum drying at 50 ℃ for 60min to prepare a graphene oxide modified filter paper material;
And 3, adding 0.2g of the compound A into 1L of absolute ethyl alcohol, performing ultrasonic agitation to prepare an ethanol solution of the compound A, soaking a piece of graphene oxide modified filter paper in the ethanol solution of the compound A for 36h, and performing vacuum drying at 50 ℃ for 60min to prepare the graphene oxide/salicylaldehyde Schiff base modified filter paper material.
The paper base material selectively tested for Cu2+The ion treatment method comprises the following specific steps of,
Step 1, respectively preparing Fe containing 10ppm of metal ions to be detected3+、Ca2+、Co2+、Cu2+、Mg2+、Pb2+、Cd2+、Cr3+And Ni2+A nitrate solution of (a);
and 2, cutting the salicylaldehyde Schiff base/graphene oxide modified paper base material into test strips of 1cm multiplied by 1cm, respectively immersing the test strips into the solution containing 10ppm of metal ions to be detected, and observing the color change of the test strips.
As can be seen from FIG. 1, when Cu is added under UV irradiation2+When the nitrate solution is added, the color of the test strip is changed from bright yellow to black, and when other metal ions are added, the color of the test strip is not obviously changed, which shows that the salicylaldehyde Schiff base/graphene oxide modified paper-based material can selectively detect Cu in the water body2+Ions.
It should be noted that, this example also configures a portion of Fe containing 10ppm of metal ion to be measured3+、Ca2+、Co2+、Cu2+、Mg2+、Pb2+、Cd2+、Cr3+And Ni2+The same conclusion as in step 1 above was reached with the mixed nitrate solution of (c).
Subsequently, the fluorescence spectra thereof were measured separately, as shown in FIG. 2, from which it can be seen that when Cu was added2+When the fluorescence emission intensity is significantly reduced or quenched, Fe is added3+、Ca2+、Co2+、Mg2+、Pb2+、Cd2+、Cr3+And Ni2+When the fluorescence emission intensity is not obviously weakened or is low, the result shows that the salicylaldehyde Schiff base/graphene oxide modified paper base material can selectively identify Cu2 +。
example 2
The invention relates to a preparation method of a salicylaldehyde Schiff base/graphene oxide modified paper base material, which specifically comprises the following steps,
Step 1, adding 45g of salicylaldehyde into 1L of anhydrous methanol, uniformly stirring to prepare a methanol solution of the salicylaldehyde, adding 15g of 1,2,4, 5-benzenetetramine hydrochloride, carrying out reflux reaction at 70 ℃ for 22 hours, carrying out suction filtration on a reaction solution, and carrying out vacuum drying at 60 ℃ for 12 hours to prepare a compound A;
step 2, adding 0.4g of graphene oxide into 1L of deionized water, performing ultrasonic treatment, mechanically stirring at the speed of 1800r/min for 40min to prepare a graphene oxide dispersion solution, taking a piece of filter paper, soaking the filter paper in the graphene oxide dispersion solution for 30h, and performing vacuum drying at 60 ℃ for 40min to prepare a graphene oxide modified filter paper material;
and 3, adding 0.4g of the compound A into 1L of absolute ethyl alcohol, performing ultrasonic treatment to prepare an ethanol solution of the compound A, soaking a piece of graphene oxide modified filter paper in the ethanol solution of the compound A for 30h, and performing vacuum drying at 60 ℃ for 40min to prepare the graphene oxide/salicylaldehyde Schiff base modified filter paper material.
example 3
The invention relates to a preparation method of a salicylaldehyde Schiff base/graphene oxide modified paper base material, which specifically comprises the following steps,
step 1, adding 60g of salicylaldehyde into 1L of anhydrous methanol, uniformly stirring to prepare a methanol solution of the salicylaldehyde, adding 20g of 1,2,4, 5-benzenetetramine hydrochloride, carrying out reflux reaction at 74 ℃ for 26 hours, carrying out suction filtration on a reaction solution, and carrying out vacuum drying at 70 ℃ for 10 hours to prepare a compound A;
Step 2, adding 0.8g of graphene oxide into 1L of deionized water, performing ultrasonic treatment, mechanically stirring at a speed of 1600r/min for 60min to prepare a graphene oxide dispersion liquid, taking a piece of filter paper, soaking the filter paper in the graphene oxide dispersion liquid for 26h, and performing vacuum drying at 70 ℃ for 30min to prepare a graphene oxide modified filter paper material;
and 3, adding 0.8g of the compound A into 1L of absolute ethyl alcohol, performing ultrasonic agitation to prepare an ethanol solution of the compound A, soaking a piece of graphene oxide modified filter paper in the ethanol solution of the compound A for 26 hours, and performing vacuum drying at 70 ℃ for 30min to prepare the graphene oxide/salicylaldehyde Schiff base modified filter paper material.
Example 4
The invention relates to a preparation method of a salicylaldehyde Schiff base/graphene oxide modified paper base material, which specifically comprises the following steps,
step 1, adding 90g of salicylaldehyde into 1L of anhydrous methanol, uniformly stirring to prepare a methanol solution of the salicylaldehyde, adding 30g of 1,2,4, 5-benzenetetramine hydrochloride, carrying out reflux reaction at 65 ℃ for 30 hours, carrying out suction filtration on a reaction solution, and carrying out vacuum drying at 90 ℃ for 6 hours to prepare a compound A;
step 2, adding 1.2g of graphene oxide into 1L of deionized water, performing ultrasonic agitation at a speed of 1500r/min for 100min to prepare a graphene oxide dispersion solution, taking a piece of filter paper, soaking the filter paper in the graphene oxide dispersion solution for 20h, and performing vacuum drying at 90 ℃ for 10min to prepare a graphene oxide modified filter paper material;
and 3, adding 1.2g of the compound A into 1L of absolute ethyl alcohol, performing ultrasonic agitation to prepare an ethanol solution of the compound A, soaking a piece of graphene oxide modified filter paper in the ethanol solution of the compound A for 20 hours, and performing vacuum drying at 90 ℃ for 10min to prepare the graphene oxide/salicylaldehyde Schiff base modified filter paper material.
The detection effect of the invention is visible to naked eyes, the salicylaldehyde Schiff base/graphene oxide modified paper-based material test strip is added into different metal ion solutions, and when Cu is added, the test strip is found2+When the ion is irradiated by ultraviolet lamp, the color of the test paper strip changes from bright yellow to black, andWhen other ions are added, the test strip has no obvious change.
As a comparison, when the graphene oxide modified filter paper test strip obtained in step 2 of each of the above examples was added to the different metal ion solutions of example 1, Cu could not be selectively detected2+Ions.
Comparative example 1
in the step 1, salicylaldehyde is not added, and the other conditions are the same as those of the example 1, so that the obtained graphene oxide/1, 2,4, 5-benzene tetramine hydrochloride modified filter paper material is added into a Cu-containing modified filter paper test strip through testing2+After the ionic solution is irradiated by an ultraviolet lamp, the color of the test strip has no obvious color change phenomenon, and the Cu can not be selectively detected2+Ions.

Claims (10)

1. A preparation method of a salicylaldehyde Schiff base/graphene oxide modified paper base material is characterized by comprising the following steps of,
step 1, mixing the following components in percentage by mass (30-90): (10-30) carrying out reflux reaction on the salicylaldehyde and 1,2,4, 5-benzene tetramine hydrochloride, separating a product in a reaction solution, and drying to obtain salicylaldehyde Schiff base;
Soaking paper in the graphene oxide dispersion liquid and then drying to obtain a graphene oxide modified paper base material;
Step 2, soaking the graphene oxide modified paper base material in a solution of salicylaldehyde Schiff base, and compounding the graphene oxide and the salicylaldehyde Schiff base on paper to form a compound A;
and 3, taking out the compound A and drying to obtain the salicylaldehyde Schiff base/graphene oxide modified paper base material.
2. The preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper-based material according to claim 1, wherein the reflux reaction in the step 1 is carried out at 65-75 ℃ for 18-30 h.
3. the preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper-based material according to claim 1, wherein the concentration of the graphene oxide dispersion liquid in the step 1 is 0.2-1.2 g/L, and the preparation method is obtained by adding graphene oxide into deionized water and mechanically stirring the mixture uniformly.
4. The preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper-based material according to claim 1, wherein the time for soaking the paper in the graphene oxide dispersion liquid in the step 1 is 20-36 h.
5. The preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper base material according to claim 1, wherein in the step 1, salicylaldehyde is added into absolute methanol and uniformly stirred to obtain a salicylaldehyde solution with the concentration of 30-90 g/L, and 1,2,4, 5-benzenetetramine hydrochloride is added into the salicylaldehyde solution with the concentration to perform reflux reaction.
6. The preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper-based material according to claim 1, wherein the time for soaking the graphene oxide modified paper-based material in the solution of the salicylaldehyde Schiff base in the step 2 is 20-36 h.
7. The preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper-based material according to claim 1, wherein the concentration of the salicylaldehyde Schiff base solution in the step 2 is 0.2-1.2 g/L, and the salicylaldehyde Schiff base solution is obtained by adding the salicylaldehyde Schiff base into absolute ethyl alcohol and uniformly stirring.
8. The preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper-based material according to claim 1, wherein the drying in the step 1 is vacuum drying, wherein the drying temperature of the product after the reflux reaction is 50-90 ℃ for 6-16 h; the drying temperature of the paper soaked in the graphene oxide dispersion liquid is 50-90 ℃, and the drying time is 10-60 min;
And 3, vacuum drying is adopted as the drying in the step 3, wherein the drying temperature is 50-90 ℃, and the drying time is 10-60 min.
9. A salicylaldehyde Schiff base/graphene oxide modified paper-based material obtained by the preparation method of the salicylaldehyde Schiff base/graphene oxide modified paper-based material according to any one of claims 1 to 8.
10. The salicylaldehyde schiff base/graphene oxide modified paper-based material of claim 9, for detecting Cu in water2+Application of ions.
CN201910844388.6A 2019-09-06 2019-09-06 salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof Pending CN110565440A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910844388.6A CN110565440A (en) 2019-09-06 2019-09-06 salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910844388.6A CN110565440A (en) 2019-09-06 2019-09-06 salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof

Publications (1)

Publication Number Publication Date
CN110565440A true CN110565440A (en) 2019-12-13

Family

ID=68778498

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910844388.6A Pending CN110565440A (en) 2019-09-06 2019-09-06 salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN110565440A (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102584700A (en) * 2011-12-26 2012-07-18 上海师范大学 Salicylaldehyde Schiff base as well as preparation method and application thereof
CN104961647A (en) * 2015-06-26 2015-10-07 西北师范大学 Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof
CN105842209A (en) * 2016-03-18 2016-08-10 中国科学院合肥物质科学研究院 Paper sensor for rapid on-site detection of fluorine ions in water and preparation method thereof
CN106198518A (en) * 2016-07-05 2016-12-07 河南城建学院 A kind of copper ion quick detection test paper and preparation method thereof
US20170276607A1 (en) * 2016-03-28 2017-09-28 King Fahd University Of Petroleum And Minerals Fluorescent schiff base conjugate cu(ii) chemosensors and methods thereof
CN108195830A (en) * 2017-12-19 2018-06-22 浙江理工大学 A kind of visible detection method for trace copper ion

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102584700A (en) * 2011-12-26 2012-07-18 上海师范大学 Salicylaldehyde Schiff base as well as preparation method and application thereof
CN104961647A (en) * 2015-06-26 2015-10-07 西北师范大学 Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof
CN105842209A (en) * 2016-03-18 2016-08-10 中国科学院合肥物质科学研究院 Paper sensor for rapid on-site detection of fluorine ions in water and preparation method thereof
US20170276607A1 (en) * 2016-03-28 2017-09-28 King Fahd University Of Petroleum And Minerals Fluorescent schiff base conjugate cu(ii) chemosensors and methods thereof
CN106198518A (en) * 2016-07-05 2016-12-07 河南城建学院 A kind of copper ion quick detection test paper and preparation method thereof
CN108195830A (en) * 2017-12-19 2018-06-22 浙江理工大学 A kind of visible detection method for trace copper ion

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
KELLY CHICHAK等: "The Construction of (Salophen)ruthenium(II) Assemblies Using Axial Coordination", 《EUROPEAN JOURNAL OF INORGANIC CHEMISTRY》 *
方碧云: "基于新型荧光材料生物传感器的构建及其应用", 《中国博士学位论文数据库工程科技I辑》 *
段久芳（编著）: "《天然高分子材料》", 30 September 2016, 华中科技大学出版社 *
谢昆等（著）: "《纳米技术在水污染控制中的应用》", 30 June 2014, 武汉大学出版社 *

Similar Documents

Publication Publication Date Title
Oguz et al. Low-cost and environmentally sensitive fluorescent cellulose paper for naked-eye detection of Fe (III) in aqueous media
CN113621081B (en) Dialdehyde cellulose-based Schiff base fluorescent probe for detecting Al3+, and preparation method and application thereof
Cheng et al. A simple chemosensor for the dual-channel detection of cyanide in water with high selectivity and sensitivity
CN107064131A (en) A kind of detection carrier and its detection method for detecting various heavy
Li et al. Chitosan based macromolecular probes for the selective detection and removal of Fe3+ ion
Kim et al. An imidazole-appended p-phenylene-Cu (II) ensemble as a chemoprobe for histidine in biological samples
CN113234068A (en) Near-infrared cyanine analog color fluorescent probe and preparation method and application thereof
CN110483746B (en) Synthesis of novel covalent organic framework material and application of novel covalent organic framework material in metal ion recognition and dye adsorption
Saçmacı et al. A new chelating reagent: its synthesis/characterization and application for the determination of Cd (II) and Ni (II) in various food and make-up product samples by FAAS using simultaneous microextraction sampling
CN110565440A (en) salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof
CN113087651A (en) Compound containing indole group and preparation method and application thereof
CN106749240B (en) It is a kind of can high selectivity detect and remove fluorescent optical sensor molecule and its synthesis and the application of mercury ion
CN110204734B (en) Polyethyleneimine/salicylaldehyde modified cellulose material and preparation method and application thereof
CN106076295B (en) It is a kind of can trivalent chromium and the preparation method of magnetic nanometer adsorbent for quickly removing it in fluorescence detection water body
CN108051415B (en) Method for detecting hexavalent chromium ions by fluorescence ratio
CN107831165B (en) Double-channel copper ion detection test paper and preparation method thereof
CN114032096A (en) N-doped carbon dot and preparation method thereof and Cu-doped carbon dot2+Applications in assays
CN107314979A (en) A kind of copper ion sensor based on rhodamine 6G, preparation and application
Yang et al. Tetraphenylethene functionalized rhodamine dye for fluorescence detection of HCl vapor in the solid state
CN109232526B (en) Iron ion detection probe based on luminescence enhancement and preparation method and application thereof
CN110578270A (en) Salicylaldehyde-polyethyleneimine modified rhodamine/graphene oxide paper base material and preparation method and application thereof
CN117447992B (en) Nano gold-manganese dioxide nano fluorescent probe and preparation method and application thereof
CN113398902B (en) Preparation method and application of biomass cellulose-based detection material
CN113264898B (en) Benzoxazole colorimetric fluorescent probe ZY15 for detecting mercury ions and preparation method and application thereof
CN110031439B (en) Method for detecting divalent copper ions

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication

Application publication date: 20191213

RJ01 Rejection of invention patent application after publication