CN114018879B - Method for sensitively detecting lead in PVC basketball material - Google Patents
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- CN114018879B CN114018879B CN202111190406.7A CN202111190406A CN114018879B CN 114018879 B CN114018879 B CN 114018879B CN 202111190406 A CN202111190406 A CN 202111190406A CN 114018879 B CN114018879 B CN 114018879B
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- 229910021645 metal ion Inorganic materials 0.000 abstract description 19
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 7
- 238000010521 absorption reaction Methods 0.000 abstract description 6
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- 239000004800 polyvinyl chloride Substances 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000003287 optical effect Effects 0.000 description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001917 fluorescence detection Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000000879 imine group Chemical group 0.000 description 2
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- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- 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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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Abstract
The invention provides a method for sensitively detecting lead in a PVC basketball material, and relates to the technical field of functional material detection; the detection material disclosed by the invention is prepared by taking salicylaldehyde and aminofluorene as reaction raw materials through one-step polymerization reaction. Because the detection material contains two metal ion action sites of imine and adjacent hydroxyl, the detection material has the double-channel signal detection performance of ultraviolet absorption and fluorescence emission on lead ions in the basketball PVC material, is accurate and rapid, and has remarkable application value; the preparation method has the advantages of high yield, simple preparation process, easy implementation and the like, is suitable for industrial popularization, and creates favorable conditions for popularization and application of the detection material.
Description
Technical Field
The invention relates to the technical field of functional material detection, in particular to an optical detection method for lead ions in a PVC basketball material.
Background
The high efficiency and fast pace of modern society limit people to communicate and know each other, but basketball courts provide opportunities for people. Basketball exercise is a collective project, and can cultivate good quality of reunion and struggling and effort collaboration; basketball activity is an creative activity, tactics have specifications and personal characteristics, no fixed mode exists, and participants are required to timely, dropoff and rapidly cope with various problems in the field according to conditions, and the ability of finding, analyzing and solving the problems is exercised and cultivated. The basketball activity form can be different from person to person, and the amount of exercise can be adjusted at will, so the basketball player is suitable for the wide participation of various crowds. Various participants can find the self-showing mode on the playground, thereby meeting the requirements of different levels. Thus, basketball sports have a very broad market. Basketball materials comprise polyvinyl chloride materials (PVC), polyurethane materials (PU) and the like; although the hand feeling and the low temperature resistance of the PVC basketball are slightly inferior to those of PU synthetic leather, the PVC basketball is waterproof, wear-resistant, mildew-resistant, and salt and alkali resistant, has the advantages of price, is economical and practical, is a good skin material for popular indoor and outdoor basketball, and has a wide consumer market. The content of heavy metal ions in the PVC basketball material is also a very important index. Once the metal ion content exceeds the standard, the service life of the basketball is reduced, and the metal ion easily enters the human body along with food due to the touch of people in the basketball movement process; in particular, children and teenagers, basketball exercise is one of the main exercise forms during the growth process, and sometimes people begin to eat after the exercise without washing hands, so that metal ions can possibly enter the body, and a series of diseases are caused. If the content of lead ions in human body is too high, the effects of reducing memory, anemia, nerve paralysis, renal function deterioration, etc. can be achieved, so that children have short stature, low immunity, hyperactivity, inattention, etc. Therefore, the method for rapidly and sensitively detecting the lead ions in the PVC basketball material has very important significance.
Conventional methods for detecting metal ions in PVC basketball materials mainly comprise chromatographic and mass spectrometry technologies, but the methods are troublesome to operate and require expensive instruments, thus limiting the wide application of the methods. The fluorescence detection method has the characteristics of high sensitivity, low cost, easy operation and the like, and has become one of the hot spots of people research. The fluorescence detection method realizes in-situ and real-time detection on single molecule level, and the analysis result is flexibleSensitive and accurate. Based on different detection requirements, a plurality of fluorescent detection materials for detecting metal ions are prepared, and the fluorescent detection materials are widely applied to the fields of chemical production, environmental monitoring, life science and the like. The fluorene group has a rigid conjugated structure and has higher light stability; the imine group has stronger metal coordination capability, and the introduction of the imine group into optical detection can increase the complexation and selectivity between the molecular material and metal ions and induce sensitive optical signal change. After combining the two, a series of fluorescence detection materials [ D.Yang, X.Liu, Y.Zhou, L.Luo, J.Zhang, A.Huang, Q.Mao, X.Chen, L.Tang ] with different recognition properties were developed.Anal. Methods, 2017,9, 1976-1990; X. Meng,D. Cao,Z. Hu,X. Han,Z. Li, W. Ma.RSC Adv., 2018, 8, 33947-33951]. However, the current fluorescence detection method is used for analysis and report of lead ions in basketball PVC materials.
Disclosure of Invention
The technical aim of the invention is to provide a molecular material with an accurate detection function on lead in a PVC basketball material.
The invention further aims to provide a method for detecting lead ions in the PVC basketball material, which has the advantages of rapidness, sensitivity, easiness in operation, easiness in popularization and the like.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a functional material capable of sensitively detecting lead ions in basketball PVC material has a molecular structure as follows:
a functional material capable of sensitively detecting lead ions in PVC basketball materials is prepared by the following steps:
putting alpha mmol salicylaldehyde and beta mmol aminofluorene into a round-bottomed flask containing gamma mL absolute ethyl alcohol, and heating to reflux for reaction for 3-5 hours; filtering the mixture obtained by the reaction, washing with absolute ethyl alcohol and drying to obtain a tan salicyl-aminofluorene material; alpha, beta and gamma are 1:1:15.
The preparation reaction formula of the material with the sensitive detection function on lead ions in basketball PVC materials is as follows:
the invention has the following technical effects: the functional material for detecting the lead ions in the basketball PVC material contains two ion action sites of imine and o-hydroxyl, and the synergistic effect of the two ion action sites has stronger complexing ability on the lead ions; along with the continuous increase of the concentration of lead ions in the solution, the fluorescence emission of the detection material at the position 370 and nm is obviously enhanced, meanwhile, the maximum absorption peak 355 and nm is disappeared, the wide absorption without structural features appears in the range 260-500 and nm, a sensitive double-channel detection signal is presented, and the detection material is accurate and rapid and has higher application value; the preparation process of the material with sensitive detection function on lead ions in the basketball PVC material has the advantages of simple preparation process, mild reaction condition, high yield and the like, is suitable for industrial implementation, and creates favorable conditions for popularization and application of the detection material.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the test material obtained in example 1-2.
FIG. 2 shows the optical detection performance of the material with sensitivity to lead ions in basketball PVC material by adding different metal ions into 70% acetonitrile aqueous solution.
FIG. 3 shows the fluorescence detection performance of the material with sensitivity to lead ions in basketball PVC material by adding different metal ions into 70% methanol aqueous solution.
FIG. 4 shows the competitive performance of the functional material sensitive to lead ions in basketball PVC material in 70% acetonitrile water solution with other metal ions.
Detailed Description
The invention discloses a functional material capable of sensitively detecting lead ions in basketball PVC materials, which has the molecular structure as follows:
；
the preparation method can be prepared by adopting salicylaldehyde and aminofluorene as raw materials through one-step polymerization, and the preparation reaction formula is as follows:
。
example 1
1 mmol of salicylaldehyde and 1 mmol of aminofluorene are put into a round-bottom flask containing 15 mL absolute ethyl alcohol, and then the temperature is raised to reflux for reaction for 3 hours; the resulting mixture was filtered, washed with absolute ethanol and dried to give a tan material a,171 mg in 60% yield.
Example 2
1 mmol of salicylaldehyde and 1 mmol of aminofluorene are put into a round-bottom flask containing 15 mL absolute ethyl alcohol, and then the temperature is raised to reflux for reaction for 5 hours; the reaction mixture was filtered, washed with absolute ethanol and dried to give a tan material B,173.9 mg in 61% yield.
Materials a and B obtained in examples 1-2 were analyzed and determined to be identical in nuclear magnetic hydrogen spectra, and the data were as follows: at the position of 1 H NMR (CCl 3 D, 400 MHz), comprising 1 OH proton signal peak: 13.74 (s, 2H); proton signal peak on 1 c=n-carbon: 10.30 (s, 2H); 11 aromatic ring proton signal peaks: 8.95 (s, 1H), 7.99 (m, 2H), 7.65 (d, 2H), 7.50 (d, 1H), 7.45 (t, 2H), 7.37 (t, 1H), 6.44 (d, 1H), 6.34 (s, 1H); CH on 2 fluorene groups 2 Proton signal peak: 4.0 (s, 2H) which is substantially in accordance with the theory of salicyl-aminofluorene. From this, it was confirmed that the molecular structure of the material A, B was:
namely the salicyl-aminofluorene detection material.
Example 3
Optical detection of different metal ions by using salicyl-aminofluorene detection material in 70% acetonitrile aqueous solutionPerformance: in 70% acetonitrile aqueous solution, the concentration is 4×10 -5 The mol/L salicyl-aminofluorene detection material has a weak fluorescence emission peak near the 370 nm position; adding 10 times of equivalent Pb 2+ After that, the maximum fluorescence emission intensity of the detection material at the 370 nm position is increased by 13.4 times, the maximum absorption peak at the 355 nm position is disappeared, and meanwhile, the broad absorption without structural characteristics appears in the range of 260-500 nm; other metal ions such as Li + 、Na + 、K + 、Ba 2+ 、Ca 2+ 、Mg 2+ 、Co 2+ 、Zn 2+ 、Mn 2+ 、Ni 2+ 、Cd 2+ 、Hg 2+ The spectrum of the detection material is hardly changed after the addition of the plasma. This indicates that the salicyl-aminofluorene detection material is specific to Pb 2+ The ions have accurate dual optical detection properties.
Example 4
Optical detection performance of the salicyl-aminofluorene detection material on different metal ions in 70% methanol aqueous solution: in 70% aqueous methanol solution, the concentration is 4×10 -5 The mol/L salicyl-aminofluorene detection material has a weak fluorescence emission peak near the 368 nm position; adding 10 times of equivalent Pb 2+ After that, its maximum fluorescence emission intensity at 368 nm increased 3.9-fold; other metal ions such as Li + 、Na + 、K + 、Ba 2+ 、Ca 2+ 、Mg 2+ 、Co 2+ 、Zn 2+ 、Mn 2+ 、Ni 2+ 、Cd 2+ 、Hg 2+ After plasma addition, the fluorescence emission spectrum of the detection material is hardly changed. This indicates that the salicyl-aminofluorene detection material is used for detecting Pb in methanol solvent 2+ The ions have sensitive fluorescence detection performance.
Example 5
The selective competition performance of the salicyl-aminofluorene detection material in 70% acetonitrile water solution between lead ions and other metal ions: at a concentration of 4X 10 -5 mol/L of salicyl-aminofluorene detection material 70% acetonitrile aqueous solution is added with 10 times equivalent Pb at the same time 2+ And other different metal ions. Spectral studies have shown that: adding 10 times equivalent Pb into the salicyl-aminofluorene detection material 2+ After that, itThe weak fluorescence emission is obviously enhanced at the position 370 and nm; when Pb is contained 2+ With Li + 、Na + 、K + 、Ba 2+ 、Ca 2+ 、Mg 2+ 、Co 2+ 、Zn 2+ 、Mn 2+ 、Ni 2+ 、Cd 2+ 、Hg 2+ After the metal ions are added with the salicyl-aminofluorene detection material at the same time, the mixed system fluorescence emission spectrum and the salicyl-aminofluorene detection material are added with Pb only 2+ Similarly. Correspondingly, the salicyl-aminofluorene detection material is added with Pb at the same time 2+ With Li + 、Na + 、K + 、Ba 2+ 、Ca 2+ 、Mg 2+ 、Co 2+ 、Zn 2+ 、Mn 2+ 、Ni 2+ 、Cd 2+ 、Hg 2+ After the metal ions are removed, only Pb is added into the salicyl-aminofluorene detection material after ultraviolet spectrum change 2+ Near, a broad absorption without structural features occurs in the range of 260-500 nm. This indicates that even Pb 2+ In the coexistence with other metal ions, the salicyl-aminofluorene detection material is still specific to Pb only 2+ Shows good selective detection performance.
Example 6
Pb in PVC basketball material by using salicyl-aminofluorene detection material 2+ Actual detection performance of ions: weighing a certain amount of PVC basketball raw materials, regulating pH to be neutral through microwave digestion, acid removal and alkaline solution, and determining that the PVC basketball raw materials have no Pb based on an inductively coupled plasma (ICP-MS) 2+ The method comprises the steps of carrying out a first treatment on the surface of the Weighing a certain amount of basketball PVC raw material, adding a certain amount of Pb 2+ Through digestion, acid expelling, pH regulation to neutrality and distilled water volume setting, pb containing different concentration is prepared 2+ Is used for detecting Pb through the salicyl-aminofluorene material 2+ Reproduction rate. The results are shown in the following table, and the detection material pair Pb of salicyl-aminofluorene 2+ The reproduction rate of the system is 100.5% -102%, and the system is within an allowable error range. This shows that the salicyl-aminofluorene detection material is used for detecting Pb in PVC basketball raw material 2+ The analysis and detection have higher accuracy and wide application prospect.
TABLE 1 detection of Pb in PVC basketball Material by salicyl-aminofluorene 2+ Actual detection performance of ions
| Pb addition 2+ (M ) | Pb detection 2+ (M ) | Reproduction ratio (%) | R.S.D. a (%) | |
| Basketball PVC material | -- | -- | ||
| Synthesis solution 1 b | 4.0 × 10 -6 | (4.04 ± 0.02) × 10 -6 | 101 | 1 |
| Synthesis solution 2 b | 4.0 × 10 -5 | (4.02 ± 0.03) × 10 -5 | 100.5 | 0.5 |
| Synthesis solution 3 b | 4.0 × 10 -4 | (4.08 ± 0.02) × 10 -4 | 102 | 2 |
a n = 3; b Adding Mg 2+ 、Ca 2+ 、Li + 、Na + K is as follows + (10.00 mu M) basketball PVC material, and testing conditions are that 40 mu M salicyl-aminofluorene detection material is mixed with acetonitrile-water (7:3).
Claims (1)
1. The application of the salicyl-aminofluorene detection material in detecting lead ions in PVC basketball materials is characterized in that the detection material has the following structure:
the molecular material contains two ion action sites of imine and o-hydroxyl, has stronger complexing ability to lead ions, and has sensitive ultraviolet and fluorescent double-channel detection function to lead ions in the PVC basketball material.
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| NL2030282A NL2030282B1 (en) | 2021-10-13 | 2021-12-23 | Method for sensitive detection of lead in polyvinyl chloride (pvc)-based basketball material |
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- 2021-10-13 CN CN202111190406.7A patent/CN114018879B/en active Active
- 2021-12-23 NL NL2030282A patent/NL2030282B1/en active
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