• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
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    • 专利摘要:
    Non-instrumental colorimetric device and method for volatile chemical species. The present invention relates to a device based on a solid substrate, more specifically paper, and to the non-instrumental colorimetric method carried out therewith which allows the qualitative and quantitative determination of different analytes by formation of volatile derivatives and colorimetric chemical reaction with a reactive substance confined to the analytical device on paper. In the invention, the reactive substance is confined in the detection zone (2) of the paper substrate by hydrophobic barriers (4), which physically separate the detection zone (2) from the injection zone (3), through from which a liquid reagent (11) can be injected which allows the generation of a volatile form of the analyte without the reactive substance present in the detection zone (2) being affected in said process. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2679643A1
    申请号:ES201700149
    申请日:2017-02-24
    公开日:2018-08-29
    发明作者:José Carlos BENDICHO HERNÁNDEZ；Francisco Javier PENA PEREIRA；Lorena VILLAR BLANCO；María Isela LAVILLA BELTRÁN
    申请人:Universidade de Vigo；
    IPC主号:
    专利说明:

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    NON-INSTRUMENTAL COLORIMETRIC DEVICE AND METHOD FOR VOLATILE CHEMICAL SPECIES
    SECTOR OF THE TECHNIQUE
    The present invention falls within the field of chemical analysis, with application in sectors such as environmental, food and pharmaceutical, among others. More specifically, the invention relates to a device based on a solid substrate, more specifically paper, which allows the qualitative and quantitative determination of different analytes by formation of a volatile species, extraction thereof and colorimetric chemical reaction.
    BACKGROUND OF THE INVENTION
    The use of solid supports of different nature (cellulose, plastic polymers, metals, etc.) has been and continues to be fundamental in different areas of analytical chemistry. Particularly, cellulose is a very attractive functional material that is used as a solid support, for example, in gout analysis (called spot tests in English), in chromatography, as well as in pH indicator paper and in portable kits for rapid analysis. .
    Currently, several commercial houses offer a wide variety of colorimetric kits that allow you to perform semi-quantitative analyzes quickly. These systems can be used by non-specialized personnel, and are characterized by their low cost and speed, being applicable in the determination of numerous individual analytical parameters. These colorimetric kits are based on the formation of a colored product by the reaction between the analyte and a chemical reagent impregnated in test strips. Subsequently, the visual comparison between the color of the generated product and the color areas of a printed card corresponding to increasing concentrations of analyte is carried out. Commonly, the test strips of these kits are immersed in the test sample, although, in some cases, the determination of analytes can be carried out by generating a volatile form thereof and subsequent colorimetric reaction with a reagent
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    chemical present in the test strip. Patent documents US3741727 (A) and US 2008/0069728 A1 describe systems based on the use of flexible sample containers into which at least one vial containing the reagents necessary for the formation of the components is introduced, together with the test sample. corresponding volatile products. The test strip is exposed to the gas phase generated on the sample through an open tongue (US3741727 A), or in the holes present in the upper part of a flexible bag (US 2008/0069728 A1). These open systems result in losses of the analyte, which significantly compromises the accuracy and precision of the method, and there is also a risk of exposure to the generated vapors. To avoid these problems, closed systems must be used that allow the generation of the volatile in situ and its reaction with the reactive substance. Likewise, the sensitivity achieved with the systems described above is very limited, so it is not possible to detect the analyte of interest when it is present at concentration levels lower or equivalent to the maximum allowed limit (above which significant risks occur for the environment and / or human health).
    In recent years, interest in the development of paper analytical devices (called paper-based analytical devices in English) as a basis for chemical and biological analysis has been greatly increased following the important contributions of the research group of Prof. Whitesides (Martínez et al., Angew. Chemie - Int. Ed. 46 (2007) 1318-1320; Martínez et al., Anal. Chem. 82 (2010) 3-10). As a solid substrate, the paper allows working with minimal amounts of reagents and is susceptible to being chemically modified to incorporate specific functional groups. The combination of analytical devices on paper with various widely implemented electronic systems, such as digital cameras, mobile phones, tablets, etc., as well as with image analysis software, allows quantitative chemical analysis to be carried out without the use of the most sophisticated instrumental analytical techniques commonly used for this purpose. This strategy has allowed the development of new analysis methodologies characterized by their low cost, simplicity and speed, which makes them especially useful for field measurements (Martínez et al. Anal. Chem. 82 (2010) 3-10; Martínez et al., Anal. Chem. 80 (2008) 3699-3707).
    Paper analytical devices have been used to determine analytes of a very diverse nature (Cate et al., Anal. Chem. 87 (2015) 19-41). However, despite the potential of such systems, the development of colorimetric methods
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    Based on analytical devices on paper by formation of volatile analyte derivatives is still very limited. These are based on the design of relatively complex three-dimensional systems {Jayawardane et al., Anal. Chem. 87 (2015) 4621-4626; Phansi et al., Anal. Chem. 88 (2016) 8749-8756). In addition, paper-based analytical devices have a lower sensitivity than that achieved using analogous analysis methods in solution. This aspect significantly limits its application when it comes to determining compounds present at trace or ultratrace concentration levels in samples of interest. Such is the case of those contaminants regulated by the corresponding legislation whose maximum permissible concentration is lower than the detection limit obtained with paper analytical devices. To mitigate this limitation, different strategies have recently been proposed in order to pre-concentrate analytes in combination with paper analytical devices. Thus, Wong et al. Have proposed evaporation by applying a high temperature (220 ° C) on the end of a paper device (Wong et al., Anal. Chem. 86 (2014) 11981-11985). The successive sampling and evaporation produced in a localized way makes it possible to pre-concentrate significantly the analytes present in the sample. Satarpai et al. Employ circular discs prepared from modified filter paper with an adsorbent for solid phase extraction of lead in aqueous samples (Satarpai et al., Talanta 154 (2016) 504-510). After the pre-concentration stage, the circular disk is introduced into the central area of the paper analysis device and the analyte retained therein is directed towards the detection zone with the consequent formation of a colored product that allows its determination. Although both systems allow substantially increasing the sensitivity of the analysis, the preconcentration time is high and the corresponding procedures are complex. More recently, it has been shown that the implementation of paper analytical devices in pre-concentration systems such as thin-layer microextraction in head space (called headspace-thin film microextraction in English) (Jiang and Pawliszyn, TrAC - Trends Anal Chem. 39 (2012) 245-253) allows high sensitivity (and selectivity) to be achieved in combination with non-instrumental fluorescence detection. This strategy has been used for the determination of selenium in urine by generating a volatile form of the analyte (hydrogen selenide) and its thin layer microextraction in the head space (Huang et al., Anal. Chem. 88 (2016) 789 -795). For this, fluorescent semiconductor nanocrystals immobilized in paper substrate are used. The decrease in fluorescence intensity produced by the interaction of hydrogen selenide with immobilized semiconductor nanocrystals allows the determination of selenium at
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    low levels of concentration The configuration of the device used, however, presents a problem that significantly limits its application. Said device is prepared by immersing the paper substrate in a solution of reactive substance, so that it is present on the entire surface of the paper substrate. Thus, the injection of the derivatizing agent through the device can affect and even prevent the quantitative determination of the analytes of interest as a result of the possible reaction with the reactive substance present in the paper substrate. Therefore, the applicability of the system depends on the compatibility of the reactive substance present in the paper analytical device and the reagent used to generate the volatile form of the analyte, since the reactive substance is not physically separated from the injection zone.
    In view of the above, there is a need to use a new device that allows the injection zone to be separated from the detection zone so that the application of this type of paper analytical systems can be generalized. The use of the device described in the present invention solves this problem.
    EXPLANATION OF THE INVENTION
    The present invention relates to a device and the non-instrumental colorimetric method carried out therewith which allows the determination of analytes by formation of volatile derivatives and that solves the limitations of the methods described in the prior art.
    In the present invention, "reactive substance" is understood as a substance that reacts selectively with the volatile form of the analyte, producing a colorimetric reaction with said substance on the paper substrate, thus allowing the determination of the analyte present in the sample.
    "Colorimetric reaction" means that reaction in which a product whose color differs from that of the reactive substance present in the paper substrate is generated, as well as the increase or decrease in the color intensity of the product generated with respect to the of the reactive substance.
    By "derivatizing agent" is understood that substance that allows to form, by
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    chemical reaction with the analyte, a product that has more appropriate physical-chemical properties to carry out the chemical analysis.
    One aspect of the present invention relates to a device for the determination of volatile derivatives of non-volatile analytes comprising a paper substrate, preferably filter paper or chromatographic paper, which in turn comprises a detection zone in which it is immobilized the reactive substance, physically separated from an injection zone by a hydrophobic barrier, said paper substrate is inserted into a screw cap with a flexible septum, such that the detection zone of the modified paper substrate can be exposed inside the vial.
    The device of the invention makes it possible to carry out the separation and pre-concentration of the analyte by generating a volatile form thereof capable of giving rise to a colorimetric reaction in the detection zone of the paper substrate. It should be noted that the physical separation obtained through the formation of hydrophobic barriers makes it possible to carry out the generation reaction of the volatile form of the analyte independently by external injection through the injection zone without the reactive substance present in the area of detection may be affected in the process.
    Another aspect of the present invention relates to a method for the determination of volatile analyte species by using the device described above, which comprises the following steps:
    a) Preparation of the paper substrate and immobilization of the reactive substance in the detection zone;
    b) Introduction of the sample containing the analyte to be determined in the vial for later analysis;
    c) Generation of the volatile form of the analyte by introducing the needle of a syringe containing the reagent required for the generation of the volatile derivative of the analyte through the injection zone of the modified paper substrate and injection of the syringe contents inside the vial;
    d) Simultaneously to step c) the transfer of the volatile species of the analyte to the headspace occurs and, subsequently, to the detection area of the paper analytical device, in which the corresponding colorimetric reaction occurs;
    e) Digitization of the detection area of the analytical device on paper;
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    f) Processing and analysis of the image obtained.
    A preferred embodiment of the method is characterized in that the reactive substance used can be immobilized in the detection zone chemically (by chemical reaction with the paper substrate) or physically (by deposition of the solution of the reactive substance on the corresponding area of the substrate of paper).
    A preferred embodiment in step d) of transferring the volatile analytes into the headspace can be favored by the use of thermostated systems, as well as by vortex agitation systems, ultrasound systems or, preferably, by magnetic stirring. In the latter case it is necessary to introduce a magnetic stirrer inside the vial together with the sample before carrying out the step of generating the volatile form of the analyte.
    Another preferred embodiment, the scanning of the detection area of the analytical device on paper, is performed by using digital capture devices, such as a digital camera, a mobile phone or a scanner.
    Another preferred embodiment, the step of processing and analyzing the image obtained, is carried out by using an image analysis software.
    Another aspect of the present invention relates to the use of a non-instrumental colorimetric analysis method by using the system described above for the determination of analytes such as arsenic, ammonium, antimony, bromide, bromate, cyanide, hypochlorite, mercury, methylmercury, nitrate, nitrite, sulfite, sulfide, trimethylammonium, iodide, iodate, etc., by forming their corresponding volatile derivatives and selective reaction thereof with the reactive substance present in the detection zone of the paper analytical device.
    BRIEF DESCRIPTION OF THE DRAWINGS
    To complement the description that is being made and in order to help a better understanding of the characteristics of the invention, according to a preferred example of practical realization thereof, a set of figures in the accompanying part is accompanied as an integral part of said description. where, by way of illustration and not limitation,
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    The following has been represented:
    Figure 1 shows the components of the device according to a preferred embodiment of the invention.
    Figure 2 shows the device used for preconcentration of volatile forms of nonvolatile analytes by derivatization according to a preferred embodiment of the invention (a) and a schematic view showing the device (b).
    Figure 3 shows the effect of the different experimental variables on the analytical signal corresponding to arsenic (As): a) color modes (RGB); b) mass of silver nitrate (AgN03) present in the detection zone; c) concentration of reducing agent (sodium borohydride, NaBFU) used for the generation of arsine or arsenic hydride (ASH3); d) concentration of HCI used to generate AsH3 from two species of inorganic As (l (l)) and As (V)); e) concentration of citric acid used for the generation of AsH3 from two species of inorganic As (l (l)) and As (V)); f) extraction time.
    Figure 4 shows how the analytical signal varies with the concentration for the determination of As (lll) and total inorganic As: a) relationship between the analytical signal and the concentration of As (lll); b) relationship between the analytical signal and the total inorganic As concentration.
    Figure 5 shows how K / (Omax / lmedia) ~ l) varies with the concentration for the determination of As (lll) and total inorganic As: a) relationship between K / ((max / Imedia) - l) and the As concentration (lll); b) relationship between K / ((lmax // media ') - l) and total inorganic As concentration.
    PREFERRED EMBODIMENT OF THE INVENTION
    In any case, in all possible embodiments of the invention, part of the device of the invention, represented in Figure 1 and Figure 2, which comprises a paper substrate (1), commonly filter paper or chromatographic paper, is provided. in turn it comprises a detection zone (2) in which the reactive substance is physically immobilized (physically or chemically) separated from the injection zone (3) by
    hydrophobic barriers (4). The modified paper substrate is insertable inside a screw cap (5) with flexible septum (6), such that the detection zone (2) of the paper substrate! modified is exposed inside a vial (7). The sample to be analyzed (8) is inside the vial (7) attachable to the screw cap (5), so that the closed system comprises a head space (9). The device of the invention allows the generation of a volatile form of the analyte present in the sample to be analyzed (8) by external injection of a solution of the corresponding reagent (11) through the injection zone (3) of the paper substrate ( one). The volatiles generated are transferred to the head space (9), and react with the reactive substance present in the detection zone of the paper substrate (2), so that a colorimetric reaction occurs therein.
    A possible embodiment of the invention for the analysis of As speciation in aqueous matrices is described below, which includes: the preparation of a paper analytical device for the detection of arsine, the evaluation of different experimental parameters that affect the determination Non-instrumental colorimetric of As, the obtaining of the analytical characteristics, the evaluation of possible interferences and the application of the invention to the determination of As (lll) and total inorganic As in water samples for human consumption. The applicability of the present invention should not be considered in any way restricted to that described in the illustrative example set forth.
    Example
    Preparation of a paper analytical device for detection of arsine 25 Initially a paper substrate (1) is prepared with a shape and dimensions equivalent to those of the septum (6) included inside the screw cap (5) compatible with the vial ( 7). The dimensions of the detection zone (2) are set according to the diameter of the upper hole of! screw cap (5) compatible with the vial (7). In the example, the paper substrate (1) houses, in its central area, a 0.64 cm2 square profiled with a permanent marker that delimits the detection zone (2). Permanent markers are a simple and economical option to prepare the paper analytical device in situ (Nie et al. Anal. Chem. 84 (2012) 6331-6335). When the ink penetrates the pores of the paper, the solvent evaporates and the resin remains in the substrate forming the hydrophobic barriers that physically delimit the different areas of the paper. Other methods of manufacturing analytical devices on paper, including wax printing, are also applicable (Cate et al., Anal. Chem. 87 (2015) 19-41; Carrilho et al., Anal. Chem. 81 (2009) 7091-7095;
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    Jiang and Fan, Annu. Anal Rev. Chem. 9 (2016) 203-222). The hydrophobic barriers (4) thus obtained allow the reactive substance to be confined in the detection zone (2) and, therefore, physically separate the detection zone (2) from the injection zone (3).
    The detection zone (2) is modified by adding 5-10 pL of AgNC solution> 3 thereon, and allowed to dry for later use. Thus, the reactive substance (AgNCb) is confined in the detection zone (2), physically separated from the unmodified area of the paper substrate corresponding to the injection zone (3), through which it is possible inject a reagent in solution (NaBFL) that allows the generation of a volatile form of the analyte (in this case AsFh) without the reactive substance present in the detection zone (2) being affected in said process (by reduction of ions Ag * present in the detection zone).
    Evaluation of experimental parameters that affect the non-instrumental colorimetric determination of arsenic
    An evaluation was made of the different experimental variables that affect the non-instrumental selective determination of As through the use of! paper analytical device whose preparation is illustrated in the previous section. The method is based on the in situ generation of Ashh and subsequent reaction of the volatile with the Ag + ions present in the detection zone (2) of the paper substrate (1), which results in the formation of a colored product (due to the generation of Ag ° and AS2O3). To obtain the corresponding analytical signal (color intensity), the paper substrate is digitized with a scanner and the color intensity corresponding to the most appropriate color channel (RGB) of the detection zone (2) is determined. The image obtained.
    First, the influence of the different color channels (RGB) on the analytical signal of patterns and targets was evaluated (Figure 3a). Different channels allow you to obtain similar color intensity values, although the red (R) channel provides the lowest color intensity values for white, which means a higher signal / noise ratio.
    The effect of the reactive substance mass (in the example, AgNÜ3 mass) present in the detection zone (2) of the paper analytical device (1) was evaluated. The mass selection in the range 0.5-1.0 mg allows to obtain a high sensitivity with a low reagent consumption (Figure 3b).
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    The effect of reducer concentration (NaBH4) for As (lll) was evaluated. As seen graphically in Figure 3c, a concentration of NaBH4 between 1 and 1.5% (m / v) is required to obtain maximum sensitivity.
    The effect of the concentration and type of acid on the analytical signal with As (lll) and As (V) was also evaluated. A concentration of 1-2 M HCI is adequate to obtain an equivalent analytical signal for both species of As (Figure 3d). The use of citric acid up to 1% (m / v) allows AsFb to be generated selectively from As (lll) in the presence of As (V) (Figure 3e). This makes it possible to determine As (lll) using citric acid or total inorganic As [As (lll) + As (V)] by using HCI.
    The evaluation of the extraction time (Figure 3f) shows that the analytical signal increases significantly with this variable, reaching maximum sensitivity with extraction times of at least 3 minutes.
    Analytical characteristics
    Under optimal conditions, the response curves that relate the concentration of As with the analytical signal obtained were obtained, both for the quantification of As (lll) (Figure 4a), and for that of total inorganic As (Figure 4b). As can be seen in Figure 4, when representing the sign! Analytical versus analyte concentration a hyperbolic rectangular relationship is obtained, as described in the literature (Chaplan et al., Anal. Methods 6 (2014) 1296-1300; Pena-Pereira et al., Talanta 147 (2016 ) 390-396). The hyperbolic rectangular relationship relates the
    color intensity (I) with concentration (C) according to the equation:
    i __ maxC
    K + C ^ '
    Where lmax is the maximum color intensity value at which the curve tends and K is the
    concentration that corresponds to half of the lmax. Equation (1) can be expressed as a function of concentration as follows:
    C ~ (i »» * - 1) (2)
    Ideally, the representation of K / (Umax / 1media) - l) vs C fits a line in which the ideal parameters for the slope and ordered in the origin are 1 and 0,
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    respectively.
    Figure 5 shows the representation of K / (Umax / 1 measured) -l) versus the concentration of As (lll) (Figure 5a) and total inorganic As (Figure 5b) according to equation (2). In both cases a linear response is obtained in the concentration range of 5 to 400 ng / mL. The detection limit reached was 1 ng / mL. Consequently, the sensitivity achieved is, unlike different commercial colorimetric kits whose detection limits are in the range 20100 ng / mL (Pande et al., Environ. Monit. Assess. 68 (2001) 1-18), sufficient for the determination of As in samples of water for human consumption, whose maximum concentration allowed is 10 ng / mL according to Royal Decree 140/2003, of February 7 (Ministry of the Presidency, Royal Decree 140/2003, of February 7, which establishes the sanitary criteria of the quality of water for human consumption., Bol. Of. Del Estado. (2003) 7228-7245).
    Evaluation of possible interference
    The tolerance of the described method was evaluated for the presence of different compounds that can produce a significant effect (positive or negative) on the analytical signal of As. This study included different salts, transition metals, hydride generating elements and humic acid . The high tolerance levels obtained indicate that the method is applicable to the analysis of water samples for human consumption, since the concentration levels of the different compounds evaluated are typically lower in said samples.
    Application of the invention to the determination of As (lll) and total inorganic As in water samples for human consumption
    The utility of the described invention is demonstrated, by way of example, by applying it to the determination of As (lll) and total inorganic As in water samples for human consumption. Three aqueous samples (bottled mineral water, source water and river water) were analyzed, obtaining in all cases concentrations of As (lll) and total inorganic As below the detection limit. For the evaluation of the accuracy of the method, recovery studies were carried out using different levels of concentration of As (lll) and As (V). The results obtained (Table 1) show recovery values close to the theoretical value of 100% for both As (lll) and total inorganic As. It can be confirmed, therefore, that the sample matrix evaluated does not produce a significant effect and the proposed method is applicable to the analysis of As speciation in aqueous matrices.
    Tabial: Recovery studies.
     Sample  Concentration added (ng / mL) Recovery (%)
     As (lll)  As (V) As (lll) * Total inorganic ace *
     Mineral water  10 - 96 ± 18 102 ± 11
     bottled up  10 10 107 ± 3 105 ± 5
     Source water  10 - 111 ± 1 101 ± 12
     10 10 94 ± 7 101 ± 14
     River water  10 - 102 ± 6 93 ± 6
     10 10 101 ± 5 106 ± 5
    * Mean value ± standard deviation
    权利要求:
    Claims (9)
    [1]
    1. Device for the non-instrumental colorimetric determination of volatile derivatives of non-volatile analytes comprising a vial (7) where the sample to be analyzed (8) is located, to which a screw cap (5) with hole is attached
    upper, so that in the closed system a head space (9) is created, characterized in that a paper substrate (1) is inserted inside the screw cap (5) which in turn comprises a detection zone (2) in which the reactive substance, physically separated from the injection zone (3) is immobilized by a hydrophobic barrier (4), said paper substrate (1)
    it is inserted inside the screw cap (5) with a flexible septum (6), so that the detection zone (2) of the modified paper substrate can be exposed inside the vial (7).
    Device according to claim 1, characterized in that in the area of
    detection (2) a reactive substance physically or chemically capable of producing a colorimetric reaction with volatile derivatives of the analyte is immobilized.
    Device according to claims 1 to 2, characterized in that the
    dimensions of the detection zone (2) will depend on the diameter of the top hole of the screw cap (5) compatible with the vial (7).
    25
    [4]
    Device according to claims 1 to 2, characterized in that the shape and dimensions of the paper substrate (1) are equivalent to those of the flexible septum (6).
    [5]
    5. Device according to claims 1 to 3, characterized in that the paper substrate (1) can be filter paper or chromatographic paper.
    30
    [6]
    Device according to claims 1 to 3, characterized in that the preparation of the hydrophobic barrier (3) can be carried out by printing with wax, or preferably manually with permanent markers.
    35 7. Non-instrumental colorimetric analysis method for chemical species
    volatile according to previous claims comprising:
    a) Preparation of the paper substrate (1) and immobilization of the reactive substance in the detection zone (2);
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    b) Introduction of the sample (8) in the vial (7) for further analysis;
    c) Generation of the volatile form of the analyte by inserting the needle of a syringe (10) containing the derivatizing reagent (11) required for the generation of the volatile derivative of the analyte through the injection zone (3) of the paper substrate Modified and injection of the contents of the syringe (10) inside the vial (7):
    d) Simultaneously to step c) the transfer of the volatile species of the analyte to the headspace (9) occurs and, subsequently, to the detection zone (2) of the paper analytical device, in which the reaction occurs corresponding colorimetric;
    e) Digitalization of the detection zone (2) of the paper analytical device (1);
    f) Processing and analysis of the image obtained.
    [8]
    Method according to claim 7, characterized in that the reactive substance can be immobilized in the detection zone (2) either chemically by chemical reaction with the paper substrate (1) or physically by depositing the solution of reactive substance on the corresponding area of the paper substrate (1).
    [9]
    9. Method according to claims 7 to 8, characterized in that step d) of transferring the volatile form of the analyte to the headspace (9) is carried out by using thermostated systems, magnetic stirring, vortex stirring, or ultrasonic systems
    [10]
    10. Colorimetric analysis method according to claim 7, characterized in that the step of scanning the detection zone (2) is carried out by using digital capture devices, such as a digital camera, a mobile phone or a scanner .
    [11]
    11. Colorimetric analysis method according to claim 7, characterized in that the analytical information is obtained by using an image analysis software.
    [12]
    12. Use of a non-instrumental colorimetric analysis method according to previous claims, characterized in that it can be applied for the determination of analytes such as arsenic, ammonium, antimony, bromide,
    bromate, cyanide, hypochlorite, mercury, methylmercury, nitrate, nitrite, sulphite, sulphide, trimethylammonium, iodide, iodate, as well as other analytes that allow the formation of their corresponding volatile derivatives and selective reaction thereof with the reactive substance present in the detection zone (2) of the analytical device on paper (1).
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    同族专利:
    公开号 | 公开日
    ES2679643B1|2019-03-21|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US6397658B1|1997-11-15|2002-06-04|Brechbuhler Ag|Method and equipment for measuring global volatile substances|
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