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WO2018070360A1 - Corps de détection de substance organique volatile et son procédé de fabrication, procédé de détection de substance organique volatile et dispositif de détection de substance organique volatile - Google Patents

Corps de détection de substance organique volatile et son procédé de fabrication, procédé de détection de substance organique volatile et dispositif de détection de substance organique volatile Download PDF

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Publication number
WO2018070360A1
WO2018070360A1 PCT/JP2017/036572 JP2017036572W WO2018070360A1 WO 2018070360 A1 WO2018070360 A1 WO 2018070360A1 JP 2017036572 W JP2017036572 W JP 2017036572W WO 2018070360 A1 WO2018070360 A1 WO 2018070360A1
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Prior art keywords
volatile organic
organic substance
detector
substance detector
substance detection
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Ceased
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PCT/JP2017/036572
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English (en)
Japanese (ja)
Inventor
克行 養父
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Murata Manufacturing Co Ltd
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Murata Manufacturing Co Ltd
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Publication date
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • 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
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
    • G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators

Definitions

  • the present invention relates to a volatile organic substance detector and a method for producing the same, a volatile organic substance detection method, and a volatile organic substance detector.
  • VOC volatile organic compound
  • Patent Document 1 Although the use of an organic-inorganic hybrid membrane has also been studied to increase selectivity (Patent Document 1), the problem that the operating temperature is high and takes time to stabilize has not been solved.
  • the present invention has been made in view of such circumstances, and has a high selectivity, a low operating temperature, and a short time until stabilization, a volatile organic substance detector, a method for producing the same, and detection of volatile organic substances. It is an object to provide a method and a volatile organic substance detection device.
  • a volatile organic substance detector includes a base and a hexaarylbisimidazole represented by the following general formula (1), which is included in the base.
  • R 1 to R 30 each independently represents a hydrogen atom or a substituent.
  • the method for producing a volatile organic substance detector includes a step of impregnating the hexaarylbisimidazole represented by the general formula (1) and a step of drying the substrate.
  • the method for detecting a volatile organic substance includes a step of irradiating the above-described volatile organic substance detector with an electromagnetic wave to color the volatile organic substance detector, and detecting a decoloration of the volatile organic substance detector based on the presence of the volatile organic substance. And a step of performing.
  • the volatile organic substance detection device includes the above-described volatile organic substance detector, a coloring means for irradiating the volatile organic substance detector with electromagnetic waves and coloring, and a volatile organic substance based on the presence of the volatile organic substance.
  • a decoloring detecting means for detecting decoloring of the detection body.
  • a volatile organic substance detector a method for manufacturing the same, a volatile organic substance detection method, and a volatile organic substance detector, which have high selectivity, low operating temperature, and short time for stabilization. be able to.
  • the volatile organic substance detector according to the present embodiment includes a base and hexaarylbisimidazole (HABI) represented by the general formula (1) included in the base.
  • HABI hexaarylbisimidazole
  • R 1 to R 30 each independently represents a hydrogen atom or a substituent.
  • the substrate is an absorbent substrate capable of absorbing HABI inside.
  • the substrate is preferably a substrate containing cellulose, and more preferably a substrate such as paper mainly composed of cellulose.
  • the cellulose content in the substrate is 80% or more, preferably 90% or more.
  • Hexaarylbisimidazole is represented by the above general formula (1), and in the general formula (1), R 1 to R 30 each independently represents a hydrogen atom or a substituent.
  • FIG. 1 is a diagram for explaining the operation of the volatile organic substance detector according to the present embodiment.
  • HABI is dispersed in a substrate such as cellulose.
  • HABI shows a photochromism in which the CN bond connecting two imidazole rings is equally cleaved by irradiation with electromagnetic waves such as ultraviolet light, and a triphenylimidazolyl radical (TPIR: lophyll radical) as a color former is generated. Color develops.
  • TPIR triphenylimidazolyl radical
  • the inventor of the present application has found that a reaction (radical recombination) from TPIR to HABI occurs and discolors in an atmosphere in which a specific organic vapor exists. This is presumed that certain organic vapors accelerate TPIR motion and promote recombination. For this reason, it discovered that the base
  • the color retention period can be extended by impregnating and dispersing HABI in a substrate such as cellulose.
  • a substrate such as cellulose.
  • the return reaction of TPIR can be effectively suppressed by using a substrate containing cellulose as the substrate. For this reason, it is suppressed that it returns to the original structure gradually in the presence of factors other than organic substances, for example, heat at room temperature or visible light, and fading.
  • the volatile organic substance detector can be returned to the initial state by heating at 50 ° C. or higher.
  • the above-mentioned volatile organic substance detector using HABI has a low operating temperature and does not have to wait for stabilization. It does not react at all with hexane, ammonia and alcohol vapors, but reacts with other organic solvent (acetone, ethyl acetate, tetrahydrofuran, etc.) vapors and immediately disappears. This has a selectivity not found in the semiconductor type sensors. Moreover, since it can return to an initial state by heating, it can be used any number of times.
  • At least one of R 1 to R 30 is a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group.
  • a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group By introducing such an electron-withdrawing substituent, the return (radical recombination) reaction from TPIR to HABI can be suppressed, and fading can be significantly suppressed.
  • a volatile organic matter detector having improved stability and repeated durability can be provided.
  • At least one of R 1 to R 5 and R 16 to R 20 is a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group.
  • the method for producing a volatile organic substance detector includes a step of impregnating a substrate with hexaarylbisimidazole (HABI) represented by the general formula (1) and a step of drying the substrate impregnated with HABI. And including.
  • HABI hexaarylbisimidazole
  • HABI hydroxyadiene styrene
  • a substrate such as a cellulose substrate is impregnated with a solution in which HABI is dissolved in an organic solvent.
  • the cellulose substrate may be immersed in a solution containing HABI, or a solution containing HABI may be applied to the cellulose substrate.
  • the cellulose substrate impregnated with HABI is dried to produce a volatile organic substance detector.
  • a method for detecting a volatile organic substance will be described. At least a part of the volatile organic substance detector impregnated with HABI is irradiated with an electromagnetic wave such as ultraviolet light. Thereby, HABI at the site irradiated with ultraviolet light is cleaved to become TPIR and colored. Then, the colored volatile organic substance detector is placed in a predetermined atmosphere. When the target volatile organic substance is contained in the atmosphere, the volatile organic substance detector is decolored, so the presence of the target volatile organic substance can be confirmed by detecting this decoloration. . By heating the volatile organic substance detector after measurement to 50 ° C. or higher, the volatile organic substance detector can be returned to the initial state. Thereby, a volatile organic matter detector can be used repeatedly.
  • FIG. 2 is a diagram illustrating a schematic configuration of the volatile organic substance detection device according to the present embodiment.
  • the volatile organic matter detection device 10 includes the volatile organic matter detector 1, the activation light source (coloring means) 2, the detection light source 3, the light receiving unit 4, the heating unit 5, and a housing that houses these. 6, a flow rate control unit 7 that controls the flow rate of the target gas 11 to the hole 6 a provided in the housing 6, a calculation unit 8, and a storage unit 9.
  • storage part 9 are equivalent to the decoloring detection means of this invention.
  • the activation light source 2 irradiates an electromagnetic wave composed of 200 to 450 nm ultraviolet light.
  • an ultraviolet fluorescent tube central emission wavelength 254 nm
  • the detection light source 3 emits detection light including visible light having a wavelength of 500 to 600 nm.
  • a green LED emission wavelength: 505 to 555 nm
  • the light receiving unit 4 is composed of a photodiode that detects the intensity of the detection light reflected from the volatile organic substance detector 1.
  • the light receiving unit 4 may detect the intensity of the detection light that has passed (transmitted) through the volatile organic substance detector 1.
  • the heating unit 5 is a heater for heating the volatile organic substance detector 1 after measurement.
  • the volatile organic substance detector 1 is returned to the initial state by heating the volatile organic substance detector 1 to 50 ° C. or higher by the heating unit 5.
  • the calculation unit 8 calculates the intensity (initial data) of the detection light from the volatile organic substance detector 1 before exposure to the target gas and the intensity (measurement) of the detection light from the volatile organic substance detector 1 after exposure to the target gas. Data) difference. If this difference is larger than a preset threshold value, it can be determined that the volatile organic substance detector 1 has been extinguished due to the presence of the organic substance, and it is determined that the target gas 11 contains a volatile organic substance.
  • the storage unit 9 records initial data and measurement data of the light intensity detected by the light receiving unit 4.
  • the detection light source 3 detects the detection light (visible light).
  • the light receiving unit 4 detects the intensity of the detection light reflected from the volatile organic substance detector 1.
  • the intensity of the detected detection light is stored in the storage unit 9.
  • a predetermined amount of the target gas 11 is introduced into the housing 6 by the flow rate control unit 7, and then the detection light source 3 irradiates the detection light to the volatile organic substance detector 1 again and uses the light receiving unit 4 to detect the detection light.
  • the intensity is detected, and the measurement data is stored in the storage unit 9.
  • the computing unit 8 determines the extinction state of the volatile organic substance detector 1 from the difference between the initial data and the measurement data, and detects whether or not the target gas 11 contains a volatile organic substance. After the measurement is completed, the volatile organic substance detector 1 can be decolored by heating the volatile organic substance detector 1 with the heating unit 5, and the volatile organic substance detector 1 can be returned to the initial state before coloring. Therefore, the volatile organic matter detector 1 can be reused.
  • Example 1 (exposure) The produced sample of Example 1 was exposed for 1 minute using a UV lamp (UVGL-25 Compact UV Lamp, manufactured by Funakoshi Co., Ltd.) to obtain a colored sample. In the same manner as the sample of Example 1, colored samples of Examples 2 to 8 were obtained.
  • a UV lamp UVGL-25 Compact UV Lamp, manufactured by Funakoshi Co., Ltd.
  • Example 1 (Comparative sample) A comparison was carried out in the same manner except that a solution a-7 containing Compound A-7 was prepared by dropping the solution into a film using a slide glass (S1214 manufactured by MATSANAMI) without using a filter paper as a support. A sample of Example 1 was prepared and subjected to the same exposure test. The results are shown in Table 2.
  • Table 2 shows that the samples of Examples 1 to 8 can detect ethyl acetate.
  • Table 3 shows that the detectable solvent and the undetectable solvent are clearly distinguished.
  • Example of volatile organic substance detection device A model device of the volatile organic substance detection device shown in FIG. 2 was produced.
  • a green LED emission wavelength 505 to 555 nm
  • an ultraviolet fluorescent tube central emission wavelength 254 nm
  • the green LED was caused to emit light, and the absorption intensity in the reflected light was measured with a photodiode (light receiving unit 4).
  • the green LED was made to emit light again, and the absorption intensity in the reflected light was measured with a photodiode, which was 0.2. It was confirmed that the absorption intensity recovered to near 1 by heating to 100 ° C. with a heater and irradiating the ultraviolet fluorescent tube again.
  • the volatile organic substance detector according to this embodiment includes a base and a hexaarylbisimidazole represented by the general formula (1) included in the base. Thereby, the selectivity of the volatile organic substance used as a detection target is high, the operating temperature is low, and the time until stabilization is short can be provided.
  • the substrate contains cellulose. Thereby, the decoloring effect can be promoted.
  • At least one of R 1 to R 30 is a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group.
  • a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group is a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group.
  • At least one of R 1 to R 5 and R 16 to R 20 is a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group.
  • a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group is a substituent selected from a fluorine atom, a fluorinated alkyl group, or a cyano group.
  • the method for producing a volatile organic substance detector according to the present embodiment includes a step of impregnating the base with the hexaarylbisimidazole represented by the general formula (1) and a step of drying the base. According to this embodiment, a volatile organic substance detector having the above-described performance can be manufactured at low cost.
  • the method for detecting a volatile organic substance includes a step of irradiating the above-described volatile organic substance detector with an electromagnetic wave and coloring, and a step of detecting decoloration of the volatile organic substance detector based on the presence of the volatile organic substance. And including. Accordingly, it is possible to provide a method for detecting a volatile organic substance that has a high selectivity of a volatile organic substance to be detected, a low operating temperature, and a short time until stabilization.
  • the volatile organic matter detector includes the above-described volatile organic matter detector, a coloring means for irradiating and coloring the volatile organic matter detector, and a volatile organic matter detector based on the presence of the volatile organic matter. And a decoloring detecting means for detecting the decoloring.
  • the decoloring detection means includes a detection light source for irradiating the volatile organic substance detector with detection light having a wavelength of 500 to 600 nm, a detection light receiving unit for detecting the intensity of the detection light that has passed through or reflected from the volatile organic substance detector, and .
  • a heating unit for heating the volatile organic substance detector is further provided. Thereby, after completion
  • SYMBOLS 1 Volatile organic substance detection body, 2 ... Activation light source (coloring means), 3 ... Light source for detection, 4 ... Light receiving part, 5 ... Heating part, 6 ... Housing

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Abstract

L'invention concerne un corps de détection de substance organique volatile et son procédé de fabrication, un procédé de détection de substance organique volatile, ainsi qu'un dispositif de détection de substance organique volatile présentant une sélectivité élevée, une température de fonctionnement basse et un temps de stabilisation court. Selon un aspect de la présente invention, un corps de détection de substance organique volatile comprend un substrat et un hexaarylbisimidazole exprimé par la formule générale (1) et compris dans le substrat. (Dans la formule générale (1), R1 à R30 représentent chacun indépendamment un atome d'hydrogène ou un groupe substituant.)
PCT/JP2017/036572 2016-10-11 2017-10-10 Corps de détection de substance organique volatile et son procédé de fabrication, procédé de détection de substance organique volatile et dispositif de détection de substance organique volatile Ceased WO2018070360A1 (fr)

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JP2016-200386 2016-10-11
JP2016200386 2016-10-11

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WO2018070360A1 true WO2018070360A1 (fr) 2018-04-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113466221A (zh) * 2021-06-23 2021-10-01 重庆大学 一种高分子材料热真空稳定性测试装置及测试方法

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US5501945A (en) * 1994-08-30 1996-03-26 The University Of Akron Method of using multichromic polymers in packaging
JPH11125901A (ja) * 1997-08-19 1999-05-11 Dainippon Printing Co Ltd 感光性樹脂フイルム、該フイルムを用いる蛍光体パターンの形成方法、該フイルムを用いるプラズマディスプレイパネル用背面板の製造方法、該製造方法により得られたプラズマディスプレイパネル用背面板及びプラズマディスプレイパネル
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US5501945A (en) * 1994-08-30 1996-03-26 The University Of Akron Method of using multichromic polymers in packaging
JPH11125901A (ja) * 1997-08-19 1999-05-11 Dainippon Printing Co Ltd 感光性樹脂フイルム、該フイルムを用いる蛍光体パターンの形成方法、該フイルムを用いるプラズマディスプレイパネル用背面板の製造方法、該製造方法により得られたプラズマディスプレイパネル用背面板及びプラズマディスプレイパネル
JP2010501655A (ja) * 2006-08-24 2010-01-21 チバ ホールディング インコーポレーテッド Ｕｖ線量インジケータ
JP2010209047A (ja) * 2009-03-12 2010-09-24 Tokyo Institute Of Technology フェニルテルピリジン化合物、錯化合物または複合体及びそれらの製造方法並びにそれらを含む発光体及び有機化合物の検出材
CN101709998A (zh) * 2009-10-13 2010-05-19 刘灿 节能、便携式紫外指数测量仪

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SCHROEDNER M: "Oscillations of the lophyl radical concentration during the photo-decomposition of o-Cl-hexaarylimidazole", J PHOTOCHEM PHOTOBIOL A CHEM, vol. 233, 1 April 2012 (2012-04-01), pages 60 - 64, XP028478456, DOI: doi:10.1016/j.jphotochem.2012.02.013 *
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WANG BAO-HU ET AL.: "High Efficient Photoinitiator of Hexaphenylbisimidazole Derivatives with Substituents in the 2-Phenyl Ring", JOURNAL OF PHOTOPOLYMER SCIENCE AND TECHNOLOGY, vol. 24, no. 6, 2011, pages 611 - 615, XP055604330, DOI: 10.2494/photopolymer.24.611 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113466221A (zh) * 2021-06-23 2021-10-01 重庆大学 一种高分子材料热真空稳定性测试装置及测试方法

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