CN110204734B - Polyethyleneimine/salicylaldehyde modified cellulose material and preparation method and application thereof - Google Patents
Polyethyleneimine/salicylaldehyde modified cellulose material and preparation method and application thereof Download PDFInfo
- Publication number
- CN110204734B CN110204734B CN201910515693.0A CN201910515693A CN110204734B CN 110204734 B CN110204734 B CN 110204734B CN 201910515693 A CN201910515693 A CN 201910515693A CN 110204734 B CN110204734 B CN 110204734B
- Authority
- CN
- China
- Prior art keywords
- salicylaldehyde
- polyethyleneimine
- compound
- modified cellulose
- drying
- 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.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Plasma & Fusion (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention relates to a polyethyleneimine/salicylaldehyde modified cellulose material and a preparation method and application thereof, wherein an oxidant is added into a cellulose suspension, and the mixture is subjected to light-resistant reaction, separation and drying to obtain a compound A; adding the compound A into a polyethyleneimine solution, and separating and drying after reaction to obtain a compound B; and adding the compound B into a salicylaldehyde solution, and separating and drying after reaction to obtain the polyethyleneimine/salicylaldehyde modified cellulose material. The detection material cellulose is used as a raw material, oxidized cellulose is prepared by oxidizing with an oxidant, and then the oxidized cellulose is sequentially reacted with polyethyleneimine and salicylaldehyde by continuous two-step Schiff base reaction to prepare the polyethyleneimine/salicylaldehyde modified cellulose material, the synthetic method is simple, and the detection material can be used for detecting Fe in water3+Ions can achieve high selectivity and high sensitivity detection.
Description
Technical Field
The invention belongs to the field of metal ion detection, and particularly relates to a polyethyleneimine/salicylaldehyde modified cellulose material as well as a preparation method and application thereof.
Background
Iron ions are one of the most important transition ions in the physiological environment, are cofactors of many enzymatic reactions, and play a vital role in processes such as energy generation, oxygen transport, cellular metabolism and DNA synthesis of cells. Insufficient or excessive iron content can lead to a range of diseases such as anemia, angina, diabetes, cancer, alzheimer's disease and parkinson's disease. And iron in wastewater in the traditional industries of metallurgy, electrolysis, electroplating and the like is not treated and is randomly discharged, so that serious harm is brought to the growth and the healthy development of human beings, animals and plants. Therefore, it is important to detect iron in water.
At present, the conventional detection methods for iron ions in aqueous solutions mainly include: atomic absorption spectrometry, inductively coupled plasma atomic emission spectrometry, spectrophotometry, chemiluminescence techniques, and the like, but these methods require sophisticated and expensive instruments, are cumbersome and time-consuming in operation process, and are not conducive to detection of a large number of actual samples, thereby limiting wide practical applications. In 2018, Xiaohong Han, Xiaohua Guo, Dandan Wang, et al Rapid detection of ion [ J ]. Food Science and Technology,2018,43,267 of Wanjunping et al, a new complex was synthesized with copper nitrate and gallic acid as raw materials, and the detection limit of the complex on iron ions was 0.04 ppm. In Yuan Xu, Yanhua Chen, Lan Ding, one-dot Microwave-assisted Synthesis of conserved Fluorescent Carbon Dots for Fe (III) Detection [ J ]. Chemical Journal of Chinese university, 2018,39,1420, citric acid is used as Carbon source and propanetriol is used as reaction solvent, and the Detection limit of the Detection material on iron ions is 0.12 ppm. But other materials still have the problems of poor selectivity and high detection limit in the application of detecting iron at present.
Disclosure of Invention
The invention aims to overcome the problems in the prior art, and provides a polyethyleneimine/salicylaldehyde modified cellulose material, a preparation method and application thereof, which can be used for preparing a detection material for detecting iron ions in water, and has the advantages of low detection cost and high efficiency.
In order to achieve the purpose, the invention adopts the following technical scheme:
the method comprises the following steps:
(1) adding an oxidant into the cellulose suspension, reacting in a dark place, and separating and drying to obtain a compound A; wherein the mass ratio of the cellulose to the oxidant is (8-12): (10-15);
(2) adding the compound A into a polyethyleneimine solution, and separating and drying after reaction to obtain a compound B; wherein the mass ratio of the compound A to the polyethyleneimine is (10-20): (30-60);
(3) adding the compound B into a salicylaldehyde solution, and separating and drying after reaction to obtain a polyethyleneimine/salicylaldehyde modified cellulose material; wherein the mass ratio of the compound B to the salicylaldehyde is (20-40): (60-90).
Further, the cellulose suspension is obtained by adding cellulose into deionized water and uniformly stirring; the cellulose is microcrystalline cellulose; the oxidant is sodium periodate.
Furthermore, the concentration of the cellulose suspension is 8-12 g/L.
Further, the reaction temperature of the step (1) is 40-70 ℃, and the reaction time is 4-8 h.
Further, the polyethyleneimine solution in the step (2) is obtained by adding polyethyleneimine into ethanol and uniformly stirring; the concentration of the polyethyleneimine solution is 30-60 g/L.
Further, the reaction temperature of the step (2) is 50-80 ℃, and the reaction time is 12-36 h.
Further, the salicylaldehyde solution in the step (3) is obtained by adding salicylaldehyde into ethanol and uniformly stirring; the concentration of the salicylaldehyde solution is 60-90 g/L.
Further, the separation in the steps (1) to (3) adopts a suction filtration mode, and the drying is vacuum drying; the drying temperature in the step (1) is 50-80 ℃, and the drying time is 5-10 h; the drying temperature in the step (2) and the drying time in the step (3) are both 60-90 ℃, and the drying time is both 5-10 hours.
The polyethyleneimine/salicylaldehyde modified cellulose material prepared by the preparation method is used.
The use of a polyethyleneimine/salicylaldehyde modified cellulosic material as described above in the detection of iron ions in water.
Compared with the prior art, the invention has the following beneficial technical effects:
in the preparation method, firstly, an oxidant is added into the cellulose suspension, and the mixture is separated and dried after being reacted in a dark place to prepare a compound A; adding the compound A into a polyethyleneimine-containing solution, reacting, separating and drying to prepare a compound B; and adding the compound B into a salicylaldehyde solution, and separating and drying after reaction to obtain the polyethyleneimine/salicylaldehyde modified cellulose material. The detection material adopts natural green, cheap and easily-obtained degradable cellulose as a raw material, oxidized cellulose is prepared by oxidizing with an oxidant, and then the oxidized cellulose reacts with polyethyleneimine and salicylaldehyde continuously for two steps to prepare the polyethyleneimine/salicylaldehyde modified cellulose material, and the synthesis method is simple, green and environment-friendly.
After the polyethyleneimine/salicylaldehyde modified cellulose material prepared by the invention is mixed with a metal ion solution to be detected, the fluorescence intensity is obviously quenched when the ions to be detected are iron ions through a fluorescence emission spectrum test, other metal ions are not obviously quenched, the detection limit is 0.01ppm and is lower than Fe in drinking water specified by the world health organization3+Standard 0.28ppm of ion concentration, therefore the material of the invention is for Fe in water3+Ions can achieve high selectivity and high sensitivity detection. The detection material disclosed by the invention realizes high-selectivity detection on iron ions, has the advantages of low detection limit, small using amount and accurate detection result, and is a green, environment-friendly, visible to naked eyes, simple, rapid, high-selectivity and high-sensitivity detection material.
The modified cellulose material can be used for detecting samples in large scale, and can quickly judge whether the sample solution contains iron ions or not by adding a small amount of the modified cellulose material, so that the operation steps are reduced, and the cost is reduced.
Drawings
FIG. 1 is a diagram showing fluorescence spectra of different solutions of metal ions to be measured after adding polyethyleneimine/salicylaldehyde modified cellulose material;
FIG. 2 shows different Fe to be measured3+Ion concentration and ultraviolet-visible absorption spectrum value A501Is shown in linear relationship.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings.
The invention provides a preparation method of a polyethyleneimine/salicylaldehyde modified cellulose material, which is convenient and quick to operate, good in selectivity and high in sensitivity and is used for detecting iron ions in a water body.
The invention comprises the following steps:
(1) adding 10-15 g of sodium periodate into every 1L of microcrystalline cellulose suspension, and reacting in a dark place at the reaction temperature of 40-70 ℃ for 4-8 h. And (4) carrying out suction filtration and vacuum drying to prepare the compound A. The microcrystalline cellulose suspension is obtained by adding 8-12 g of microcrystalline cellulose into every 1L of deionized water and uniformly stirring. The vacuum drying is carried out in a vacuum drying oven at the drying temperature of 50-80 ℃ for 5-10 h.
(2) Adding the compound A obtained in the step (1) into an ethanol solution containing polyethyleneimine, continuing to react at the reaction temperature of 50-80 ℃ for 12-36 h, performing suction filtration, and performing vacuum drying to prepare a compound B. The ethanol solution of the polyethyleneimine is obtained by adding 30-60 g of polyethyleneimine into 1L of ethanol and uniformly stirring. The compound A is prepared by adding 10-20 g of the compound A into 1L of an ethanol solution of polyethyleneimine. The vacuum drying is carried out in a vacuum drying oven at the drying temperature of 60-90 ℃ for 5-10 h.
(3) Adding the compound B obtained in the step (2) into an ethanol solution containing salicylaldehyde, and continuing to react at the temperature of 50-80 ℃ for 12-36 hours; and (4) carrying out suction filtration and vacuum drying to prepare the polyethyleneimine/salicylaldehyde modified cellulose material. The ethanol solution of the salicylaldehyde is obtained by adding 60-90 g of salicylaldehyde into every 1L of ethanol and uniformly stirring; the compound B is prepared by adding 20-40 g of the compound B into 1L of ethanol solution of salicylaldehyde. The vacuum drying is carried out in a vacuum drying oven at the drying temperature of 60-90 ℃ for 5-10 h.
The application of the polyethyleneimine/salicylaldehyde modified cellulose material in detecting iron ions in water specifically comprises the following steps:
10mg of polyethyleneimine/salicylaldehyde modified cellulose material is added into 3mL of a solution to be detected, such as industrial wastewater, the solution turns yellow brown, and the solution to be detected is proved to contain iron ions. Otherwise, it is proved that no iron ions exist in the solution to be measured (industrial wastewater).
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 polyethyleneimine/salicylaldehyde modified cellulose material, which specifically comprises the following steps:
step 1, adding 10g of microcrystalline cellulose into 1L of deionized water, uniformly stirring to prepare microcrystalline cellulose suspension, adding 12g of sodium periodate, keeping out of the sun, and reacting for 6 hours at 50 ℃. And (4) carrying out suction filtration and vacuum drying at 60 ℃ for 8h to prepare the compound A.
And 2, adding 50g of polyethyleneimine into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the polyethyleneimine. 15g of Compound A were then added and reacted at 78 ℃ for 24 hours. Filtering, and vacuum drying at 70 ℃ for 8h to prepare a compound B.
And 3, adding 80g of salicylaldehyde into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the salicylaldehyde. 30g of compound B were added and reacted at 78 ℃ for 24 hours. And (4) carrying out suction filtration and vacuum drying at 70 ℃ for 8h to prepare the polyethyleneimine/salicylaldehyde modified cellulose material.
The selection performance test comprises the following specific steps:
(1) respectively preparing metal ions (Fe) to be detected containing 10ppm3+、Ca2+、Co2+、Cu2+、Mg2+、Pb2+、Cd2+、Cr3 +、Ni2+) A nitrate solution of (a).
(2) 10mg of polyethyleneimine/salicylaldehyde modified cellulose material and 3mL of the metal ion solution to be detected are mixed in a cuvette, shaken up and sufficiently shaken for 20min at room temperature. Subsequently, the fluorescence emission spectrum of the mixed solution was measured at room temperature. The fluorescence emission spectrum is as follows:
as seen from FIG. 1, Co was added separately2+,Cu2+,Cr3+When the fluorescence intensity is reduced, Fe is added3+The fluorescence intensity is obviously quenched, which shows that the polyethyleneimine/salicylaldehyde modified cellulose material can selectively detect Fe in the water body3+Ions.
The sensitivity performance test comprises the following specific steps:
(1) respectively preparing the mixture to be treated with 1-100ppmMeasuring Fe3+Ionic nitrate solutions.
(2) 10mg of polyethyleneimine/salicylaldehyde-modified cellulose material and 3mL of Fe to be tested3+The ionic solution was mixed in a cuvette, shaken well and shaken well for 20min at room temperature. Subsequently, the mixed solution was tested for the UV-VIS absorption spectrum value A at 501nm at room temperature501。
As seen from FIG. 2, Fe3+When the ion concentration is in the range of 4-20ppm, the ion concentration and the ultraviolet-visible absorption value form a good linear relation, the linear regression equation is that y is 0.0425x +0.1529, and the correlation coefficient R20.9986, detection limit of 0.01ppm, lower than that of drinking water Fe regulated by world health organization3+Standard 0.28ppm of ion concentration. Illustrating the polyethyleneimine/salicylaldehyde modified cellulose material to Fe in water3+The ions have higher detection sensitivity.
Example 2
The invention relates to a preparation method of a polyethyleneimine/salicylaldehyde modified cellulose material, which specifically comprises the following steps:
step 1, adding 8g of microcrystalline cellulose into 1L of deionized water, uniformly stirring to prepare microcrystalline cellulose suspension, adding 15g of sodium periodate, keeping out of the sun, and reacting for 5 hours at 40 ℃. Filtering, and vacuum drying at 70 ℃ for 6h to prepare the compound A.
And 2, adding 40g of polyethyleneimine into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the polyethyleneimine. 12g of Compound A was added and reacted at 80 ℃ for 12 hours. And (4) carrying out suction filtration and vacuum drying at 80 ℃ for 6h to prepare a compound B.
And 3, adding 90g of salicylaldehyde into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the salicylaldehyde. 40g of compound B was added and reacted at 80 ℃ for 12 hours. And (4) carrying out suction filtration and vacuum drying at 80 ℃ for 6h to prepare the polyethyleneimine/salicylaldehyde modified cellulose material.
Example 3
The invention relates to a preparation method of a polyethyleneimine/salicylaldehyde modified cellulose material, which specifically comprises the following steps:
step 1, adding 12g of microcrystalline cellulose into 1L of deionized water, uniformly stirring to prepare microcrystalline cellulose suspension, adding 14g of sodium periodate, keeping out of the sun, and reacting for 4 hours at 70 ℃. Filtering, and vacuum drying at 80 ℃ for 5h to prepare the compound A.
And 2, adding 30g of polyethyleneimine into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the polyethyleneimine. 10g of Compound A was added and reacted at 60 ℃ for 36 hours. And (4) carrying out suction filtration and vacuum drying at 90 ℃ for 5h to prepare a compound B.
And 3, adding 70g of salicylaldehyde into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the salicylaldehyde. Then 25g of compound B was added and reacted at 60 ℃ for 36 hours. And (4) carrying out suction filtration and vacuum drying at 90 ℃ for 5h to prepare the polyethyleneimine/salicylaldehyde modified cellulose material.
Example 4
The invention relates to a preparation method of a polyethyleneimine/salicylaldehyde modified cellulose material, which specifically comprises the following steps:
step 1, adding 11g of microcrystalline cellulose into 1L of deionized water, uniformly stirring to prepare microcrystalline cellulose suspension, adding 10g of sodium periodate, keeping out of the sun, and reacting for 8 hours at 60 ℃. Filtering, and vacuum drying at 50 ℃ for 10h to prepare the compound A.
And 2, adding 60g of polyethyleneimine into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the polyethyleneimine. Then 20g of compound A was added and reacted at 50 ℃ for 30 hours. And (4) carrying out suction filtration and vacuum drying at 60 ℃ for 10h to prepare a compound B.
And 3, adding 60g of salicylaldehyde into 1L of ethanol, and uniformly stirring to prepare an ethanol solution of the salicylaldehyde. Then 20g of compound B was added and reacted at 50 ℃ for 30 hours. And (4) carrying out suction filtration and vacuum drying at 60 ℃ for 10h to prepare the polyethyleneimine/salicylaldehyde modified cellulose material.
The detection effect of the invention is visible to naked eyes: the polyethyleneimine/salicylaldehyde modified cellulose material was added to a solution of different metal ions and it was found that when iron ions were added, the solution changed from colorless to tan, while when other ions were added, the solution did not change significantly.
Comparative example 1
Sodium periodate is replaced by other oxidants such as potassium permanganate, potassium dichromate, concentrated sulfuric acid, concentrated nitric acid and the like, and corresponding materials cannot be generated.
Comparative example 2
The other conditions were the same as in example 1, except that salicylaldehyde was not added, and a polyethyleneimine-modified cellulose material was obtained. The modified cellulose material is added into the solution containing iron ions through testing, and the solution has no color change phenomenon.
Detection of Fe by using polyethyleneimine/salicylaldehyde modified cellulose material prepared by using method3+The advantages of ionic methods over other materials are mainly reflected in: the material has simple synthesis method, is green and environment-friendly, and realizes the aim of Fe3+High selectivity and high sensitivity of ion detection. The invention relates to a polyethyleneimine/salicylaldehyde modified cellulose material and a preparation method thereof, which comprises the steps of adding sodium periodate into microcrystalline cellulose suspension, carrying out light-resistant reaction, carrying out suction filtration, and carrying out vacuum drying to prepare a compound A; adding the compound A into an ethanol solution containing polyethyleneimine, heating for reaction, performing suction filtration, and performing vacuum drying to prepare a compound B; and adding the compound B into an ethanol solution containing salicylaldehyde, heating for reaction, performing suction filtration, and performing vacuum drying to obtain the polyethyleneimine/salicylaldehyde modified cellulose material. The polyethyleneimine/salicylaldehyde modified cellulose material is used for treating Fe in water3+Ions can achieve high selectivity and high sensitivity detection.
Claims (8)
1. A preparation method of polyethyleneimine/salicylaldehyde modified cellulose material is characterized by comprising the following steps: the method comprises the following steps:
(1) adding an oxidant into the cellulose suspension, reacting in a dark place, and separating and drying to obtain a compound A; wherein the mass ratio of the cellulose to the oxidant is (8-12): (10-15); the drying temperature is 50-80 ℃, and the drying time is 5-10 h;
(2) adding the compound A into a polyethyleneimine solution, and separating and drying after reaction to obtain a compound B; wherein the mass ratio of the compound A to the polyethyleneimine is (10-20): (30-60); the reaction temperature of the step (2) is 50-80 ℃, and the reaction time is 12-36 h;
(3) adding the compound B into a salicylaldehyde solution, and separating and drying after reaction to obtain a polyethyleneimine/salicylaldehyde modified cellulose material; wherein the mass ratio of the compound B to the salicylaldehyde is (20-40): (60-90);
wherein, the separation in the steps (1) to (3) adopts a suction filtration mode, and the drying is vacuum drying; the drying temperature in the step (2) and the drying time in the step (3) are both 60-90 ℃, and the drying time is both 5-10 hours.
2. The method of claim 1, wherein the polyethyleneimine/salicylaldehyde modified cellulose material is prepared by: the cellulose suspension is obtained by adding cellulose into deionized water and uniformly stirring; the cellulose is microcrystalline cellulose; the oxidant is sodium periodate.
3. The method of claim 1, wherein the polyethyleneimine/salicylaldehyde modified cellulose material is prepared by: the concentration of the cellulose suspension is (8-12) g/L.
4. The method of claim 1, wherein the polyethyleneimine/salicylaldehyde modified cellulose material is prepared by: the reaction temperature of the step (1) is 40-70 ℃, and the reaction time is 4-8 h.
5. The method of claim 1, wherein the polyethyleneimine/salicylaldehyde modified cellulose material is prepared by: the polyethyleneimine solution in the step (2) is obtained by adding polyethyleneimine into ethanol and uniformly stirring; the concentration of the polyethyleneimine solution is (30-60) g/L.
6. The method of claim 1, wherein the polyethyleneimine/salicylaldehyde modified cellulose material is prepared by: the salicylaldehyde solution in the step (3) is obtained by adding salicylaldehyde into ethanol and uniformly stirring; the concentration of the salicylaldehyde solution is (60-90) g/L.
7. A polyethyleneimine/salicylaldehyde-modified cellulose material produced by the production method according to claim 1.
8. Use of the polyethyleneimine/salicylaldehyde modified cellulose material according to claim 7 in detection of iron ions in water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910515693.0A CN110204734B (en) | 2019-06-14 | 2019-06-14 | Polyethyleneimine/salicylaldehyde modified cellulose material and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910515693.0A CN110204734B (en) | 2019-06-14 | 2019-06-14 | Polyethyleneimine/salicylaldehyde modified cellulose material and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110204734A CN110204734A (en) | 2019-09-06 |
| CN110204734B true CN110204734B (en) | 2021-10-01 |
Family
ID=67792852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910515693.0A Active CN110204734B (en) | 2019-06-14 | 2019-06-14 | Polyethyleneimine/salicylaldehyde modified cellulose material and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110204734B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115322262B (en) * | 2022-08-26 | 2023-04-25 | 南京林业大学 | Be used for detecting Fe 3+ Dialdehyde cellulose coumarin fluorescent probe and preparation method and application thereof |
| CN116904108A (en) * | 2023-05-15 | 2023-10-20 | 浙江工业大学 | Construction method of host and guest of photodynamic antibacterial polyethylenimine/aldehyde Schiff base coating |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011085067A1 (en) * | 2010-01-07 | 2011-07-14 | Isp Investment Inc. | Aqueous-miscible or aqueous-dispersible, voc-free biocidal compositions for the enhanced inhibition of gram-negative bacterial strains, and method of preparing the same |
| CN102229674A (en) * | 2011-04-12 | 2011-11-02 | 淮海工学院 | Multifunctional chelating cellulose and application thereof |
| CN103394334A (en) * | 2013-07-11 | 2013-11-20 | 东华大学 | Preparation method of aminated nanofiber membrane with high specific surface area |
| CN105758829A (en) * | 2015-11-20 | 2016-07-13 | 河南理工大学 | Preparation method of nano composite for quickly detecting fluorine ions in water phase |
| CN108195830A (en) * | 2017-12-19 | 2018-06-22 | 浙江理工大学 | A kind of visible detection method for trace copper ion |
| CN108219009A (en) * | 2018-01-05 | 2018-06-29 | 中海石油(中国)有限公司 | A kind of modified nanometer cellulose and preparation method and application |
| CN109401726A (en) * | 2018-08-27 | 2019-03-01 | 北京林业大学 | Composite modified gluing agent of PEI-g-HBA prepolymer vegetable protein and the preparation method and application thereof |
-
2019
- 2019-06-14 CN CN201910515693.0A patent/CN110204734B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011085067A1 (en) * | 2010-01-07 | 2011-07-14 | Isp Investment Inc. | Aqueous-miscible or aqueous-dispersible, voc-free biocidal compositions for the enhanced inhibition of gram-negative bacterial strains, and method of preparing the same |
| CN102229674A (en) * | 2011-04-12 | 2011-11-02 | 淮海工学院 | Multifunctional chelating cellulose and application thereof |
| CN103394334A (en) * | 2013-07-11 | 2013-11-20 | 东华大学 | Preparation method of aminated nanofiber membrane with high specific surface area |
| CN105758829A (en) * | 2015-11-20 | 2016-07-13 | 河南理工大学 | Preparation method of nano composite for quickly detecting fluorine ions in water phase |
| CN108195830A (en) * | 2017-12-19 | 2018-06-22 | 浙江理工大学 | A kind of visible detection method for trace copper ion |
| CN108219009A (en) * | 2018-01-05 | 2018-06-29 | 中海石油(中国)有限公司 | A kind of modified nanometer cellulose and preparation method and application |
| CN109401726A (en) * | 2018-08-27 | 2019-03-01 | 北京林业大学 | Composite modified gluing agent of PEI-g-HBA prepolymer vegetable protein and the preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 基于对羟基苯甲醛的水溶性Fe3+离子探针的研究;程如梅，等;《化学试剂》;20080415;第30卷(第4期);第241-243、254页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110204734A (en) | 2019-09-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101470363B1 (en) | Method for elemental analysis by isotope dilution inductively-coupled plasma mass spectrometry coupled with combustion sample preparation | |
| CN110204734B (en) | Polyethyleneimine/salicylaldehyde modified cellulose material and preparation method and application thereof | |
| CN109777405B (en) | Red-blue dual-emission fluorescent carbon dot and method for simultaneously detecting Al3+And Cu2+Method for fluorescence analysis of ions | |
| CN112525873B (en) | Fluorescent chemical sensor for detecting microcystin-LR and preparation method thereof | |
| CN107558208B (en) | Preparation and application of color-changing fiber APF-PAR | |
| CN110975807A (en) | Preparation method and application of magnetic biomass charcoal material | |
| CN110018146B (en) | Method for detecting palladium ions based on fluorescent carbon quantum dots | |
| CN110646496A (en) | Method for identifying hairy crab producing area by strontium isotope | |
| CN110938215A (en) | Eu3+-MOF material preparation method and application thereof | |
| CN108392853B (en) | Solid phase extraction column and preparation method and application thereof | |
| CN104788344A (en) | Bifunctional fluorescent probe adopting anthracene as matrix, as well as preparation method and application | |
| Wu et al. | An ultra-fast UV-electrochemical sensor based on Cu-MOF for highly sensitive and selective detection of ferric ions | |
| CN111363161B (en) | Thorium ion fluorescent probe based on terbium-organic framework material and preparation method thereof | |
| CN113307982A (en) | Preparation method and application of Cd/Zr-UIO-66 bimetallic organic framework material | |
| Xia et al. | Microplasma-assisted synthesis of a mixed-valence Ce-MOF with enhanced oxidase-like activity for colorimetric sensing of dopamine | |
| CN109053711B (en) | Probe compound for mercury ion detection and preparation method and application thereof | |
| CN110878100A (en) | Cyanide ion probe capable of being recognized by naked eyes, preparation method thereof and application of cyanide ion probe in detection of cyanide ions in water-containing system | |
| CN113861962B (en) | Ratiometric fluorescent probe, preparation method thereof and application thereof in detecting hydrogen peroxide | |
| CN115287055B (en) | Reagent for high-selectivity rapid detection of zinc ions and detection method | |
| CN116333005A (en) | Ferrocenyl ketene semicarbazide Schiff base detection Al 3+ 、Cu 2+ And Fe (Fe) 3+ | |
| CN102350297B (en) | Adsorbent, preparation method and application thereof | |
| CN110655919B (en) | Copper ion fluorescent probe and preparation method and application thereof | |
| CN109321237B (en) | Nitrogen-sulfur double-doped carbon dots and preparation method and application thereof | |
| CN110044884A (en) | A kind of Test paper of divalent manganesetion and the preparation method and application thereof | |
| CN113049718A (en) | Preparation of carbon-supported metal oxide composite microspheres and extraction of malachite green and crystal violet from aquatic products by using same |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |