CN105136789A - Color-change indicator used for detecting oxygen, synthesizing method thereof, oxygen sensor and preparation method of oxygen sensor - Google Patents
Color-change indicator used for detecting oxygen, synthesizing method thereof, oxygen sensor and preparation method of oxygen sensor Download PDFInfo
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- CN105136789A CN105136789A CN201510557054.2A CN201510557054A CN105136789A CN 105136789 A CN105136789 A CN 105136789A CN 201510557054 A CN201510557054 A CN 201510557054A CN 105136789 A CN105136789 A CN 105136789A
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Abstract
The invention relates to preparation and application of oxygen indicators, and discloses a color-change indicator used for detecting oxygen, a synthesizing method thereof, an oxygen sensor and a preparation method of the oxygen sensor. The purpose is to solve the technical problems that an existing indicator for detecting the oxygen is complex in composition and preparation, response speed is low, and repeated usability is low. The indicator is an inclusion complex which is formed by subjecting N,N'-2 (alkyl carbamoyl methyl)-4,4'-bipyridyl halide and beta-cyclodextrin to self-assembling in a water solution. The preparation method includes the steps that CnBpyeaX2 and beta-cyclodextrin are dissolved in water to be heated to be clarified and then cooled to stand, and after the water is thoroughly evaporated, the indicator is obtained. The inclusion complex is supported on a matrix to be subjected to ultraviolet or natural light irradiation treatment to obtain the oxygen sensor, and the sensor is easy and convenient to prepare and operate, high in response speed, low in cost, good in light stability and capable of being repeatedly used and can be used for detecting oxygen inside air and food package.
Description
Technical field
The present invention relates to the Synthesis and applications of the synthesis of oxygen color changing reagent and test paper thereof.
Background technology
Oxygen maintains the mankind and the requisite material of animals and plants life, also closely related with industrial and agricultural production, environment measuring, food storing and scientific research.Therefore, people need to carry out detection and control to the content of oxygen.The method of conventional detection oxygen content has Winkler titrimetry, Clark electrode method, vapor-phase chromatography etc.But said method has some shortcomings to a certain extent, as instrument is complicated, testing process is consuming time, need expensive instrument, equipment volume is large, cost is high, can not adapt to the needs of in-site measurement.Use is simple, cost is low, disturb the advantages such as little to utilize the method for Luminescence based Oxygen Sensor detection oxygen to have.Application number be 201310624716.4 Chinese patent disclose a kind of oxygen indicator, its preparation method first prepares a kind of nano-titanium dioxide powder, again this nano-titanium dioxide powder is mixed with electron donor, oxidation-reduction quality dyestuff, polymkeric substance etc., disperse, with what obtain after UV-irradiation.This oxygen indicator composition more complicated, reaction velocity is slow.
Summary of the invention
The present invention will solve existing oxygen indicator composition and preparation process is complicated, response speed is slow, reusability is low technical matters, and provides a kind of color indicator for detecting oxygen and synthetic method, lambda sensor and preparation method thereof.
Color indicator for detecting oxygen of the present invention be N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide and beta-schardinger dextrin-in aqueous self assembly form inclusion complex, be expressed as C
nbpyeaX
2m β – CD; C
nbpyeaX
2inm β – CD formula: C
nfor C
4~ C
22alkyl, X is halogen, and m is that 1 ~ 6 ， β – CD represents beta-schardinger dextrin-.
The synthetic method of the above-mentioned color indicator for detecting oxygen, carry out according to the following steps:
By N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide (C
nbpyeaX
2) and beta-schardinger dextrin-take mol ratio as 1:(2 ~ 6) soluble in water, and be placed in container, be heated to clarification, then cooling leaves standstill, and treating that water volatilizees completely, obtaining the color indicator for detecting oxygen, this indicator is inclusion complex C
nbpyeaX
2m β – CD is a kind of white solid.
Lambda sensor is formed by above-mentioned color indicator and matrix composition for detecting oxygen; Color indicator for detecting oxygen is carried on matrix, and also needs after load with ultraviolet light or natural light irradiation.
The preparation method of above-mentioned lambda sensor, carries out according to the following steps:
One, the color indicator being used for detecting oxygen is dissolved in solution in solvent I, obtains solution;
Two, matrix is soaked in solution prepared by step one, then takes out, solvent flashing I, obtain the matrix of load;
Three, by the matrix of load after with ultraviolet light or natural light irradiation, obtain lambda sensor.
Wherein ultraviolet light or natural light irradiation time are 1s ~ 2h.
Lambda sensor is kept in nitrogen atmosphere.In pure nitrogen, this lambda sensor is placed for a long time does not have obvious color to change, and never degenerates.
The present invention adopts a kind of new N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide (C
nbpyeaX
2), with beta-schardinger dextrin-in aqueous self assembly form inclusion complex.Beta-schardinger dextrin-serves protection Compound C
nbpyeaX
2the effect of electro transfer, and effectively prevent the generation of subsidiary reaction.Herein by one-step synthesis method inclusion complex, preparation method's technique is simple, and reaction conditions is easy to control, and inclusion complex more easily mixes with the water of high polarity and the organic solvent etc. of low polarity, easy to use.
Lambda sensor of the present invention is carried on after in matrix by color indicator, then obtain after carrying out ultraviolet light or natural lighting process, lambda sensor preparation process is simple.After lambda sensor puts into detected gas, if there is oxygen to exist, just can be observed the color change of examination bar by naked eyes, use method of the present invention to detect the existence of oxygen, by the impact of external condition, respond fast, simple to operate, easy to use, reusability is good.In atmosphere, the color of this lambda sensor has significant change in the time range of 0 ~ 30 minute.In an atmospheric purity oxygen, the color of this lambda sensor has significant change in the time range of 1 second ~ 10 minutes, and color change is fast.Lambda sensor after using is again with after ultraviolet light or natural lighting process, and reusable, reusability is good.
This oxygen sensor can be applicable to detect in air, oxygen in food pack or container etc.In a word, the inventive method be a kind of easy and simple to handle, respond lambda sensor detection method that is fast, reusable, cheap, easily system.
Accompanying drawing explanation
Fig. 1 is the C in embodiment 1
8bpyeaCl
2, β-ring sticks with paste and inclusion complex C
8bpyeaCl
22 β – CD's
1h-NMR spectrogram;
Fig. 2 is the C in embodiment 1
8bpyeaCl
2, β-ring sticks with paste and inclusion complex C
8bpyeaCl
2the XRD spectra of2 β – CD;
Fig. 3 is the optics picture that in embodiment 1, lambda sensor fades in a nitrogen environment;
Fig. 4 is the optics picture that in embodiment 1, lambda sensor fades under air ambient;
Fig. 5 is the optics picture that in embodiment 1, lambda sensor fades under oxygen atmosphere;
Embodiment
Embodiment one: present embodiment for detect the color indicator of oxygen be N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide and beta-schardinger dextrin-in aqueous self assembly form inclusion complex, be expressed as C
nbpyeaX
2m β – CD; C
nbpyeaX
2inm β – CD formula: C
nfor the alkyl of C4 ~ C22, X is halogen, and m is that 1 ~ 6 ， β – CD represents beta-schardinger dextrin-.
Embodiment two: the preparation method of the color indicator for detecting oxygen described in embodiment one, carries out: according to the following steps by N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide (C
nbpyeaX
2) and beta-schardinger dextrin-take mol ratio as 1:(2 ~ 6) soluble in water, and be placed in container, be heated to clarification, then cooling leaves standstill, and treating that water volatilizees completely, obtaining the color indicator for detecting oxygen.This indicator is inclusion complex C
nbpyeaX
2m β – CD is a kind of white solid.
Embodiment three: present embodiment and embodiment two unlike in step 2, N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide (C
nbpyeaX
2) and beta-schardinger dextrin-take mol ratio as 1:(3 ~ 5) soluble in water; Other is identical with two of embodiment.
Embodiment four: present embodiment and embodiment two or three unlike in step 2, N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide (C
nbpyeaX
2) and the quality sum of beta-schardinger dextrin-account for 0.1% ~ 10% of total solution quality.; Other is identical with two or three of embodiment.
Embodiment five: the lambda sensor utilizing the color indicator for detecting oxygen described in embodiment one, is formed by color indicator and matrix composition for detecting oxygen; Color indicator for detecting oxygen is carried on matrix, and also needs after load with ultraviolet light or natural light irradiation.
Embodiment six: present embodiment and embodiment five are paper, wood or thin polymer film unlike matrix, and wherein thin polymer film is tygon, polypropylene, polycarbonate or polyvinyl chloride film; Other is identical with embodiment five.
Embodiment seven: the preparation method of the lambda sensor described in embodiment five, carry out according to the following steps:
One, the color indicator being used for detecting oxygen is dissolved in solution in solvent I, obtains solution; Be 1wt% for detecting the concentration of the color indicator of oxygen in this solution;
Two, matrix is soaked in solution prepared by step one, then takes out, solvent flashing I, obtain the matrix of load;
Three, by the matrix of load after with ultraviolet light or natural light irradiation, obtain lambda sensor.
The lambda sensor of present embodiment is kept in nitrogen atmosphere.In pure nitrogen, this lambda sensor is placed for a long time does not have obvious color to change, and never degenerates.
Embodiment eight: present embodiment and embodiment seven are the combination of one or more in water, ethanol, methyl alcohol, ethyl acetate, acetone and cyclohexanone unlike the solvent I described in step one.Other is identical with embodiment seven.
In present embodiment when solvent I is composition, each solvent combines in any proportion.
Embodiment nine: present embodiment and embodiment seven or eight are 1s ~ 2h unlike step 3 medium ultraviolet light or natural light irradiation time.Other is identical with embodiment seven or eight.
Embodiment ten: one of present embodiment and embodiment seven to nine are 254nm or 365nm unlike the wavelength of step 3 medium ultraviolet light.Other is identical with one of embodiment seven to nine.
With following verification experimental verification beneficial effect of the present invention:
Embodiment 1: the synthetic method for the color indicator detecting oxygen of the present embodiment is as follows:
By N, N'-bis-(octyl carbamo, lmethyl)-4,4'-dipyridine chloride (C
8bpyeaCl
2) and beta-schardinger dextrin-take mol ratio as 1:2, configuration quality concentration is the aqueous solution of 1wt%, and is placed in flask, be heated to clarification, cooling leave standstill, treat that water volatilizees completely, obtain white solid, be i.e. inclusion complex C
8bpyeaCl
22 β – CD.This inclusion complex is the color indicator for detecting oxygen.
Utilize
1h-NMR and XRD characterizes the color indicator for detecting oxygen.C
8bpyeaCl
2, β-ring sticks with paste and inclusion complex C
8bpyeaCl
22 β – CD's
1as shown in Figure 1, I is C to H-NMR spectrogram
8bpyeaCl
2's
1h-NMR composes, and II is that β-ring is stuck with paste
1h-NMR composes, and III is inclusion complex C
8bpyeaCl
22 β – CD's
1h-NMR composes, inclusion complex C
8bpyeaCl
2the chemical displacement value of2 β – CD:
1h-NMR (D
2o, 600MHz): δ 0.81 (t, J=6.9Hz, 6H), 1.23 (s, 4H), 1.27 (br, 32H), 1.53 (m, 4H), 3.24 (t, J=7.2Hz, 4H), 3.54 (t, J=9.6Hz, 6H), 3.60 (m, 6H), 3.65 (m, 6H), 3.79 (m, 12H), 5.00 (d, J=3.6Hz, 4H), 8.57 (d, J=6.6Hz, 4H), 9.03 (d, J=6.6Hz, 4H) ppm.From Fig. 1's
1h-NMR data can be found out, the H proton displacement of dipyridine group has almost no change before and after inclusion, and C
8bpyeaCl
2alkyl chain on H proton and the H proton displacement of beta-schardinger dextrin-cavity inside there occurs change, C is described
8bpyeaCl
2alkyl chain on enter the cavity inside of beta-schardinger dextrin-molecule, and there occurs mutual chemical action with beta-schardinger dextrin-, define C
8bpyeaCl
22 β – CD inclusion complex.
C
8bpyeaCl
2, β-ring sticks with paste and inclusion complex C
8bpyeaCl
2the XRD spectra of2 β – CD as shown in Figure 2, wherein C
8bpyeaCl
22 θ (°): 4.5 ° of the XRD absorption peak of2 β – CD inclusion complex, 6.2 °, 7.5 °, 9.1 °, 9.4 °, 10.6 °, 11.6 ° 12.5 °, 13.0 °, 14.7 °, 15.3 °, 16.0 °, 17.0 °, 17.7 °, 18.8 °, 19.6 ° 20.8 °, 21.6 °, 22.6 °, 23.3 °, 24.3 °, 25.1 °, 25.5 °, 27.1 °, 32.1 °, 35.3 °.As can be seen from Figure 2, C
8bpyeaCl
2c before inclusion no longer can be distinguished in2 β-CD compound
8bpyeaCl
2with the diffraction peak of beta-schardinger dextrin-, but there is new characteristic peak, therefore confirmed have new compound to exist.
Utilize C
8bpyeaCl
22 β – CD prepares the preparation method of lambda sensor, carries out according to the following steps:
One, by C
8bpyeaCl
22 β – CD is dissolved in the water, and obtains solution, C in this solution
8bpyeaCl
2the concentration of2 β – CD is 1wt%;
Two, white filter paper is soaked in solution prepared by step one, then takes out, naturally dry under room temperature, obtain load C
8bpyeaCl
2the filter paper of2 β – CD;
Three, by load C
8bpyeaCl
2filter paper wavelength be 254nm uviol lamp according to 10s, the color of filter paper becomes blueness from white, obtains lambda sensor.
Be kept in nitrogen by this lambda sensor, situation is as shown in Figure 3 over time for its color.Give in Fig. 3 that lambda sensor is initial in nitrogen, color after 5min, 10min and 15min do not change.This lambda sensor is put into air, and situation is as shown in Figure 4 over time for its color.As can be seen from Figure 4 sensor test paper fades gradually.This lambda sensor is put into oxygen, its color over time situation as shown in Figure 5, sensor test paper comparatively fast fades, bluely when 15min just become white completely.
The above-mentioned sensor test paper faded that exposes in air or oxygen is shone 10s through 254nm uviol lamp again, and sensor test paper becomes blueness again.Reuse 20 times, this sensor test paper is obviously not different to the variable color response performance of oxygen.
Embodiment 2: synthesis and the application process of the color indicator for detecting oxygen of the present embodiment are as follows:
One, by N, N'-bis-(hexyl carbamo, lmethyl)-4,4'-dipyridine chloride (C
6bpyeaCl
2) and beta-schardinger dextrin-take mol ratio as 1:2, configuration quality concentration is the aqueous solution of 2wt%, and is placed in flask, be heated to clarification, cooling leave standstill, treat that water volatilizees completely, obtain white solid, be i.e. inclusion complex (C
6bpyeaCl
22 β – CD).This inclusion complex is the color indicator for detecting oxygen.
The color indicator being used for detecting oxygen that the present embodiment synthesizes is used for following oxygen variable color sensing detection.
By the C obtained
6bpyeaCl
22 β – CD pressed powder directly irradiates 10s, C under 254nm uviol lamp
6bpyeaCl
22 β – CD becomes blueness fast from white.The C after light color
6bpyeaCl
22 β – CD blue powder is placed in nitrogen, and its color does not change; Moved in air by this blue powder, sample fades gradually, and about 15min blueness takes off completely again; In purity oxygen, fading rate is faster, and about 10min blueness takes off completely.
Embodiment 3: for detect the synthesis of the color indicator of oxygen, sensor test paper methods for making and using same as follows:
One, by N, N'-bis-(hexadecylamino carbamoylmethyl)-4,4'-dipyridine chloride (C
16bpyeaCl
2) and beta-schardinger dextrin-take mol ratio as 1:4, configuration quality concentration is the aqueous solution of 1wt%, and is placed in flask, be heated to clarification, cooling leave standstill, treat that solvent volatilizees completely, obtain white solid, be i.e. inclusion complex (C
16bpyeaCl
24 β – CD).This inclusion complex is the color indicator for detecting oxygen.
Two, the color indicator being used for detecting oxygen of synthesis is dissolved in ethanol, obtains solution (C
16bpyeaCl
2c in4 β – CD ethanolic solution
16bpyeaCl
2the concentration of4 β – CD is 1wt%).Filter paper is immersed in 2min in this solution, takes out, naturally volatilize under room temperature, then through 254nm ultraviolet lighting 10s, obtain the sensor test paper for detecting oxygen.
The sensor test paper prepared by the present embodiment 3 is used for following test.
Placed in nitrogen by sensor test paper, sensor test paper color does not change; This sensor test paper is put into air, fades gradually, about 15min blueness takes off completely.Sensor test paper after this light color is put into purity oxygen, and fading rate is very fast, and about 10min blueness takes off completely.
Embodiment 4: the synthetic method for the color indicator detecting oxygen of the present embodiment is as follows:
One, by N, N'-bis-(decyl carbamo, lmethyl)-4,4'-dipyridine chloride (C
10bpyeaCl
2) and beta-schardinger dextrin-take mol ratio as 1:2, configuration quality concentration is the aqueous solution of 1wt%, and is placed in flask, be heated to clarification, cooling leave standstill, treat that solvent volatilizees completely, obtain white solid, be i.e. inclusion complex (C
10bpyeaCl
22 β – CD).This inclusion complex is the color indicator for detecting oxygen.
Placed in nitrogen by sensor test paper, sensor test paper color does not change; This sensor test paper is put into air, fades gradually, about 20min, blueness takes off completely; Sensor test paper after this light color is put into purity oxygen, and fading rate is very fast, and about 15min, blueness takes off completely.
Embodiment 5: the methods for making and using same of the sensor of the variable color for detecting oxygen of the present embodiment is as follows:
The volume ratio that the color indicator 20mg that embodiment 1 is synthesized being used for detecting oxygen is dissolved in 5mL is, in the ethyl acetate of 1:1 and cyclohexanone mixed liquor, obtain indicator solution.Polyvinyl chloride film is soaked 30s wherein, then polyvinyl chloride film is taken out, natural solvent flashing under room temperature, then through 254nm uviol lamp according to 25s, colorimetric sensor films becomes blueness from white, obtains the colorimetric sensor films for detecting oxygen.
Colorimetric sensor films for detecting oxygen is placed in nitrogen, and its color does not change.The colorimetric sensor films being used for detecting oxygen is put into air, and sensor test paper fades gradually, and about 50min blueness takes off completely.The colorimetric sensor films being used for detecting oxygen is put into oxygen, and sensor test paper comparatively fast fades, and about 25min blueness takes off completely.
Embodiment 6: the synthetic method for the color indicator detecting oxygen of the present embodiment is as follows:
One, by N, N'-bis-(decyl carbamo, lmethyl)-4,4'-bipyridinium bromide (C
10bpyeaBr
2) and beta-schardinger dextrin-take mol ratio as 1:2, configuration quality concentration is the aqueous solution of 1wt%, and is placed in volumetric flask, be heated to clarification, cooling leave standstill, treat that solvent volatilizees completely, obtain white solid, be i.e. inclusion complex (C
10bpyeaBr
22 β – CD).This inclusion complex is the color indicator for detecting oxygen.
The preparation method of oxygen sensor implements according to the preparation method of the lambda sensor in embodiment 1 and step.
Placed in nitrogen by sensor test paper, sensor test paper color does not change; This sensor test paper is put into air, fades gradually, about 25min, blueness takes off completely; Sensor test paper after this light color is put into purity oxygen, and fading rate is very fast, and about 15min, blueness takes off completely.
Claims (10)
1., for detecting a color indicator for oxygen, it is characterized in that this indicator is N, N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide and beta-schardinger dextrin-self assembly formation inclusion complex in aqueous, being expressed as C
nbpyeaX
2m β – CD, in formula: C
nfor the alkyl of C4 ~ C22, X is halogen, and m is 1 ~ 6 ， β – CD is beta-schardinger dextrin-.
2. preparing the method for a kind of color indicator for detecting oxygen as claimed in claim 1, it is characterized in that the method is carried out according to the following steps:
By N; N'-bis-(alkyl-carbamoyl methyl)-4; 4'-dipyridine halogenide and beta-schardinger dextrin-take mol ratio as 1:(2 ~ 6) preparation mass concentration be the aqueous solution of 0.1% ~ 10%; and be placed in flask; be heated to clarification; cooling leaves standstill, and treating that water volatilizees completely, obtaining the color indicator for detecting oxygen.
3. the preparation method of a kind of color indicator for detecting oxygen according to claim 2; it is characterized in that in step one; N; the quality sum of N'-bis-(alkyl-carbamoyl methyl)-4,4'-dipyridine halogenide and beta-schardinger dextrin-accounts for 0.1% ~ 10% of solution gross mass.
4., for detecting the lambda sensor of oxygen, it is characterized in that this lambda sensor forms for the color indicator and matrix composition detecting oxygen by described in claim 1; Color indicator for detecting oxygen is carried on matrix, and also needs after load with ultraviolet light or natural light irradiation.
5. the lambda sensor for detecting oxygen according to claim 4, is characterized in that described matrix is paper or polyvinyl chloride film.
6., for the preparation of the method for the lambda sensor of detection oxygen, it is characterized in that the method is carried out according to the following steps:
One, the color indicator being used for detecting oxygen is dissolved in solution in solvent I, obtains solution;
Two, matrix is soaked in solution prepared by step one, then takes out, solvent flashing I, obtain the matrix of load;
Three, by the matrix of load after with ultraviolet light or natural light irradiation, obtain lambda sensor.
7. the preparation method of the lambda sensor for detecting oxygen according to claim 6, is characterized in that in step 2, solvent I is the combination of one or more in water, ethanol, methyl alcohol, ethyl acetate, acetone and cyclohexanone.
8. the preparation method of the lambda sensor for detecting oxygen according to claim 6 or 7, is characterized in that step 3 medium ultraviolet light or natural light irradiation time are 1s ~ 2h.
9. the preparation method of the lambda sensor for detecting oxygen according to claim 6 or 7, is characterized in that the wavelength of step 3 medium ultraviolet light is 254nm or 365nm.
10. the matrix according to claim 6 or 7 is paper, wood or thin polymer film; Wherein thin polymer film is tygon, polypropylene, polycarbonate or polyvinyl chloride film.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109060789A (en) * | 2018-09-04 | 2018-12-21 | 山东大学 | A kind of visualization oxygen indicator and preparation method thereof |
| CN109187527A (en) * | 2018-10-12 | 2019-01-11 | 晋江拓普旺防霉材料有限公司 | A kind of oxygen indicator and the method using oxygen indicator production oxygen instruction product |
| CN113310630A (en) * | 2021-05-28 | 2021-08-27 | 山东大学 | Method for rapidly judging damage condition of food package |
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| JP2007003259A (en) * | 2005-06-22 | 2007-01-11 | Mitsubishi Gas Chem Co Inc | Oxygen sensing agent composition |
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| JP2007003259A (en) * | 2005-06-22 | 2007-01-11 | Mitsubishi Gas Chem Co Inc | Oxygen sensing agent composition |
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| JIALU TONG 等: "A novel viologen-based visible and reversible paper sensor for oxygen", 《MATERIALS LETTERS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109060789A (en) * | 2018-09-04 | 2018-12-21 | 山东大学 | A kind of visualization oxygen indicator and preparation method thereof |
| CN109060789B (en) * | 2018-09-04 | 2021-08-13 | 山东大学 | Visual oxygen indicator and preparation method thereof |
| CN109187527A (en) * | 2018-10-12 | 2019-01-11 | 晋江拓普旺防霉材料有限公司 | A kind of oxygen indicator and the method using oxygen indicator production oxygen instruction product |
| CN113310630A (en) * | 2021-05-28 | 2021-08-27 | 山东大学 | Method for rapidly judging damage condition of food package |
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Application publication date: 20151209 |