Detection of organic chemicals

Abstract

The present application relates to the detection of organic chemicals. In particular, the present application discloses a detection device for detecting organic compounds, wherein the device comprises a sample collection container for receiving a sample, optical means for emitting a light source signal to the sample and optical means for detecting a response optical signal from the sample, and a molecularly imprinted polymer according to the solvatochromic properties of a target organic chemical in the sample to determine qualitative and / or quantitative information of the target organic chemical in the sample, and a microprocessor to display the qualitative and / or quantitative information of the target organic chemical.

Description

[0001] This application is a divisional application of Chinese invention patent application No. 201780008976.5 (PCT / IB2017 / 050431), filed on January 27, 2017, entitled "Detection of Organic Chemicals". Technical Field

[0002] This invention relates to the detection of organic chemicals, and more specifically to the detection of organic chemicals based on phthalates. Background Technology

[0003] Organic compounds are ubiquitous in the environment. Rubber, plastics, fuels, pharmaceuticals, cosmetics, detergents, paints, dyes, volatile organic compounds (VOCs), and agricultural chemicals are just some of the organic compounds present in the environment, which people are exposed to almost daily. Some organic compounds are harmful, unfriendly, or noteworthy.

[0004] Plasticizers, or dispersants, are organic compound additives that enhance the flowability or plasticity of materials. Although plasticizers are primarily used in plastics, especially polyvinyl chloride (PVC), they can also be used in other materials, including concrete, clay, and related products, to improve or alter their properties.

[0005] While plasticizers are useful, long-term exposure to some are known to pose health risks. For example, long-term exposure to DEHP can affect the liver and kidneys, as well as the reproduction and development of laboratory animals. DEHP is classified as possibly carcinogenic to humans. Compared to DEHP, DINP has lower toxicity. Chronic, high-dose DBP exposure has been found to affect the reproduction and development of laboratory animals and cause birth defects.

[0006] Currently, gas chromatography-mass spectrometry (GC-MS) is commonly used to detect plasticizers and other organic compounds. However, these mass spectrometers are bulky, expensive, and require cumbersome operating procedures.

[0007] Therefore, a simple and advantageous testing scheme and testing equipment for detecting plasticizers and other organic compounds with reasonable accuracy is needed. Summary of the Invention

[0008] An organic compound detector is disclosed. The detector comprises a solvation-chromic molecularly imprinted polymer (“SMIP”) that is affinity- or complementary to a target organic compound, and the molecularly imprinted polymer (or more specifically, its solvation-chromic functional groups, such as its solvation-chromic functional monomers) will change color when the target organic compound binds to or is captured by the SMIP.

[0009] In some embodiments, molecularly imprinted polymers are used to capture organic compounds containing one or more functional groups, as shown in Tables 1A-1H.

[0010] In some embodiments, the detector has a receptor site that has an affinity for or is complementary to the target phthalate or phthalate-based plasticizer. The target phthalate or phthalate-based plasticizer is any of the phthalates shown in Table 3.

[0011] In part, the molecularly imprinted synthetic molecule contains a solvation-chromic functional monomer, the chemical structure of which is shown in the figure below:

[0012]

[0013] Because molecularly imprinted polymers can be tailored to or bind to specific organic compounds, and more specifically to specific or characteristic functional groups of those compounds, detectors are specific to particular organic compounds, especially those with specific functional groups. Qualitative and quantitative analyses can achieve test results with little or no interference and instability because the mixing of different organic compounds in the sample can be reduced. It is the unique solvochromic property of solvochromic MIPs that allows the wavelength distribution and / or intensity of characteristic wavelengths of the composite analytes formed by the target organic compound to change with the concentration of the composite analyte. This unique solvochromic property is used in this paper to facilitate rapid and efficient solvochromic detection of organic compounds.

[0014] A method for detecting the presence and / or determining the concentration of a target organic compound in a sample is disclosed. The method includes dissolving the target sample in an organic solvent to obtain a sample solution; applying a probe device to the sample solution to form a target analyte, said probe device comprising a solvation-chromic molecularly imprinted polymer or SMIP, wherein the SMIP comprises a solvation-chromic functional group or a solvation-chromic functional monomer whose color and / or fluorescence properties change upon coupling with or encountering the target organic compound or when the target organic compound is captured by the SMIP; and detecting or determining the presence and / or concentration of the target organic compound by referring to the colorimetric, luminescent, and / or fluorescent response of the target analyte.

[0015] A detection device for detecting organic compounds is disclosed. The device includes a sample container for receiving a sample, an optical device for emitting a light source optical signal to the sample and for detecting the response optical signal from the sample, and a processor for determining qualitative and / or quantitative information of the organic compound based on the solvation colorimetric properties of the sample, such as based on the solvation colorimetric properties and / or the colorimetric, luminescence, and / or fluorescence response of a reference target analyte. The target analyte comprises a composite analyte, and each composite analyte comprises a probe device and a target organic compound or at least one characteristic functional group thereof. The probe device comprises a solvation colorimetric molecularly imprinted polymer or SMIP, and the SMIP comprises a solvation colorimetric functional group or a solvation colorimetric functional monomer. The color and / or fluorescence properties of the solvation colorimetric functional group or the solvation colorimetric functional monomer change upon encountering or coupling with the target organic compound.

[0016] This detector is lightweight, portable, and inexpensive, while providing fast, reasonably accurate, and cost-effective test results. It is particularly suitable for small purchasing offices, retailers, and manufacturing plants to help determine whether finished product materials meet concentration limits or allow the use of specific types of organic compounds, such as phthalates or plasticizers, in accordance with CPSC ASTM F963 Part 3 and 2009 / 48 / EC EN71 Part 3.

[0017] Also disclosed is a sample extraction device for rapid sample extraction to facilitate the detection of organic compounds or multiple organic compounds. The device includes a heating chamber and a sealed sample container. The sealed sample container has a bottom and a sealed top. The heating chamber is used to heat the sample at the bottom for sample collection in the sealed top.

[0018] A method for extracting organic compound samples for quantitative or concentration determination is disclosed. The method includes placing a first predetermined weight of a sample containing an organic compound in a sample container and closing the sample container to form a closed sample container, the closed sample container including a bottom, a top, and an upper portion, the upper portion including a middle wall dependent on the top; while the sample is on the bottom of the closed sample container, heating the bottom of the sample container to evaporate the organic compound to deposit it on the top and / or upper portion of the closed sample container; and dissolving the organic compound from the sample container in a second predetermined amount of polar organic solvent.

[0019] In some parts, the extraction methods for organic chemicals in the samples involve the use of ethanol as an organic solvent. In other parts, the extraction methods involve high-temperature sealing.

[0020] The extraction of organic chemicals from the sample does not require trained operators with chemical knowledge because the solvent used in the extraction process is non-toxic ethanol.

[0021] Therefore, the combination disclosed herein provides a sample extraction apparatus for detecting target organic compounds in a sample, and an organic compound detection and / or detection apparatus.

[0022] The novel rapid extraction method and instrument for organic chemicals, combined with electronic sensors and the solvated color-changing biomarker synthesized herein, facilitates rapid, highly sensitive, and accurate confirmation of the identification signal of a specific target organic chemical substance in a rapid scanning assay; for example, determining the presence of a specific target organic chemical substance at a rate of 40-100 micrograms per kilogram of solid or liquid sample. As an example, the rapid sample extraction method is four to six times faster than conventional sample extraction techniques. The SMIP receptor or probe can detect a specific target organic chemical substance one minute faster than conventional UV optical qualitative assays and three minutes faster than conventional UV optical quantitative assays. Furthermore, the function of SMIP receptors or probes can be customized to target specific organic chemicals for detection. Unlike other biochemical probes such as antibodies, which are easily affected by other non-target substances in the extract, SMIP receptors or probes do not have this capability. For example, milk, wine, or other liquid samples may contain other antigens or enzymes that react to the antibody. In addition, other detection methods such as Fourier-transform infrared spectroscopy are easily affected by unstable infrared light absorption caused by extraction methods (such as burning the sample to release enough organic chemicals in the smoke) in order to achieve stable qualitative or rough quantitative analysis.

[0023] Solvent-chromic MIP capture reagents are low-cost chemical sensors that are stable and therefore better suited for long-term storage, for example due to their inert polyacrylate materials, and can achieve higher detection sensitivity. Therefore, the use of solvent-chromic MIP capture reagents for the qualitative and / or quantitative detection of organic compounds such as phthalates and plasticizers provides a useful alternative for rapid materials testing. Attached Figure Description

[0024] The following image provides an explanation of the aforementioned disclosed documents:

[0025] Figure 1 This is a conceptual diagram illustrating the operational layout of a sample detection instrument that uses a sample-loaded chip (matrix-type solvated color-changing blot synthetic molecular acceptor / probe chip).

[0026] Figure 2 This is a conceptual diagram describing the testing instrument used in the example.

[0027] Figure 3 This is a schematic diagram illustrating an exemplary card-shaped detector.

[0028] Figure 4A-4J It is a graph showing the solvation color change emission characteristics of analytes containing different concentrations of target analytes.

[0029] Figure 5A and 5B The graph shows the relationship between the concentration of phthalic acid esters that were captured in ethanol solvent and the relative light intensity.

[0030] Figure 6A This is a correlation curve between the concentration of the SMIP-DnOP combinatorial analytes and the intensity of scattered light.

[0031] Figure 6B This is a schematic diagram of sample calibration for the testing instrument.

[0032] Figure 7 This is a schematic diagram depicting an exemplary detector.

[0033] Figure 8 Is with Figure 7 A schematic diagram of an example optical arrangement for detectors to cooperate in performing solvation colorimetric optical measurements.

[0034] Figure 9 Is with Figure 7 detectors and Figure 8 A schematic diagram of the detection equipment with optical arrangement cooperation.

[0035] Figure 10 This is a schematic diagram depicting an exemplary detector.

[0036] Figure 11 Is with Figure 10 A schematic diagram of an example optical arrangement for detector collaboration to perform solvent synthesis color optical measurements.

[0037] Figure 12 Is with Figure 10 detectors and Figure 11 A schematic diagram of the optical arrangement and matching of the detection equipment.

[0038] Figure 13 This is a schematic diagram of an example detector and an exemplary optical arrangement, which is consistent with... Figure 10 The detectors work together to perform lyochromic optical measurements.

[0039] Figure 14 Is with Figure 13 A schematic diagram of the detection equipment that works in conjunction with the detector.

[0040] Figure 15 This is a schematic diagram of a sample collector.

[0041] Figure 15a This is a schematic diagram depicting an example operation of a sample collection device.

[0042] Figure 16a This is a schematic diagram showing a portion of the sample extraction container.

[0043] Figure 16b This is a schematic diagram showing the sample extraction container.

[0044] Figure 17a and Figure 17b These are molecular simulation diagrams of the compounds shown in Tables 1B and 1D, respectively. Detailed Implementation

[0045] like Figure 1 As shown, an example 10 of a detection arrangement includes an optical instrument 12, a sample receiver defining a sample compartment 14, an optical arrangement 16, and an evaluation circuit 18. Figure 2 As shown, the optical arrangement includes a light source 16a and an optical receiver 16b, which is connected to the lens 16c of the optical sensor. During the detection process, the light source 16a is arranged to transmit light to a sample container holding one or more samples, i.e., position 14; simultaneously, the optical sensor receiver 16b is arranged to receive and detect the optical response signal in response to the light source signal striking the sample. To facilitate the detection of the reflected light source signal, the optical receiver includes the optical lens 16c of the optical sensor and a signal processing circuit. For example, a microprocessor based on the signal processing circuit outputs the signal from the optical lens 16c of the optical sensor. The signal processing circuit may include an output for processing the signal and a data storage function for recording the output spectrum and analyzing the data.

[0046] For example, during sample inspection, the sample inspection device 14 is positioned to receive and stabilize the sample container using a suitable sample testing method. A sample container clamp is built into the sample inspection device 14, releasably holding the sample container in a predetermined inspection position within the sample device. During sample inspection, the sample container defines a sample container and is positioned and stabilized in a predetermined detection position. The light source signal emitted by the light source 16a impacts the sample or multiple samples carried on the sample inspection device, and the optical signals reflected from the sample and the sample carried on the sample inspection device are forwarded to the optical sensor 16c. During sample inspection, when the reflected optical signal from the sample is forwarded to the optical sensor 16c, the optical sensor 16c generates an output signal. Simultaneously, the signal processing circuit of the optical receiver 16b responds to the detection of the reflected light signal by generating a processed output signal to the evaluation circuit, allowing the evaluation circuit to further process and / or evaluate the signal.

[0047] The evaluation circuit may include a processor and peripheral circuitry. The processor may include a microprocessor or microcontroller, and the peripheral circuitry may include signal processing circuitry, decision circuitry, input / output circuitry, and data storage devices, such as volatile and non-volatile memory for storing instructions and data. During sample analysis operations, the processor of the evaluation circuitry evaluates the qualitative and / or quantitative characteristics of the received optical signals by executing stored instructions and referring to stored data and / or decision criteria to determine and output the qualitative and / or quantitative characteristics of the analyte or the analyte carried on the sample carrier.

[0048] After sample testing, the sample carrier is removed from the sample container so that another sample carrier can be received for another sample inspection operation. The sample clamp may include a releasable latch for releasably holding the sample carrier in a predetermined inspection position.

[0049] like Figure 1 As shown, the example detection device 100 includes a main housing 40 and a detection device 10 mounted inside the main housing 40. The main housing 40 is designed for portable applications and is shaped and sized for portability and handheld mobility. The detection device 100 may be powered by a battery inside the main housing or may obtain operating power from an external power source (e.g., DC power) or via a USB connector.

[0050] Optical device 16 and evaluation circuitry 18 are mounted on a main printed circuit board 42, which is sequentially mounted and encapsulated within a main housing 40. An example light source includes an LED mounted on the surface of the main printed circuit board (PCB) with its emitting surface facing upwards. The optical sensor includes an optical sensor head and an optical sensor module supporting the optical sensor. The output of the optical sensor module is connected to a microcontroller, such as a microprocessor within an optical receiver. Both the optical device and the sample chip are located within the main housing and are defined between the light source and the optical sensor. Peripheral circuitry includes a data output port mounted on the main printed circuit board. The main housing includes an aperture at its rear interior, allowing an external data connector to be connected to the microcontroller for data transmission. In the example embodiment, the peripheral circuitry may include a wireless data transmission device, such as a WiFi device, to transmit measurement data to external devices such as a computer, router, or smartphone with appropriate application software installed.

[0051] In an exemplary embodiment, a solvent-chromic MIP (Mixed Ink Pulse) capturing reagent for capturing a target organic compound or multiple target organic compounds is distributed on a sample chip, for example, in a matrix format. In the example application, the sample chip is a sensor chip, which is a transparent sample carrier card 60, and it has a first body surface 62a, a second body surface 62b, and a peripheral body surface 62c, and this sample carrier is connected to the first body surface 62a and the second body surface 62b. The sample carrier card 60 includes a card-shaped substrate that can be made of transparent rigid plastic. Figure 3 As shown, multiple sample sites are deposited on the first host surface 62a or the second host surface 62b, and each sample site carries a solvation-chromogenic molecularly imprinted trapping agent. The solvation-chromogenic molecularly imprinted trapping agent can target different types of individual organic substances and can be reproducible to provide repeatable test results. Furthermore, the location of each detected sample is also a sample point appearing on the sample chip, such as... Figure 3 As shown. In some embodiments, the sensor chip can be used to detect specific types of organic compounds, and the location or site of the detected sample can be deposited on the site using a single type of solvation-based chromogenic molecular imprinting trap. In some embodiments, the sample site can carry other types of chemical sensors without loss of generality.

[0052] Therefore, the card-shaped container can be securely held in the analyte inspection position for proper sample inspection. The sample container may include a sample card support fixture. The sample card support fixture may include a mounting fixture mounted on the main printed circuit board, and when the sample container is inserted into the main housing, it is securely stabilized on the sample container at the inspection position via a receiving slot or aperture within the main housing. When the sample carrying card is in the inspection position, an LED light source is positioned below the sample carrying card, projecting the LED light source signal onto the target position of the sample carrying card, where the sample contains molecules of the captured analyte, which are in the form of a solvent-chromic imprinted polymer (SMIP) correspondingly matched to the target analyte and bonded together with the target analyte to form a composite analyte.

[0053] To allow the sample-containing card to be moved from outside the detection device to the inspection position, a sample container receiving slot or aperture is provided on the front end of the main housing, corresponding to the position of the sample container and providing an inlet for the sample container to enter the optical device. The optical sensor head is located above the sample container and is used to receive the optical signal reflected from the sample on the upper surface of the sample card.

[0054] When the sample carrier card 60 is housed within the main housing 40 and held by a mounting fixture, the sample carrier card 60 extends along the longitudinal direction X and is held between the light source 16a and the optical sensor 16c, with the upper part of the sample carrier card facing the optical sensor 16c and the lower part facing the light source 16a. The light source 16a is positioned to emit a light source signal relative to a longitudinal angle α toward the lower body surface of the sample carrier card 60. The reflected optical signal will be emitted from the upper body surface of the sample carrier card, and the optical sensor 16c is arranged to collect the reflected optical signal propagating longitudinally from the target position at a second angle β. Figure 2 In the example arrangement, the reflected optical signal propagates in a direction perpendicular to the light source signal. The substrate of the sample carrier card is made of transparent or translucent plastic material, so that after the light source signal strikes the lower body surface of the sample carrier card at a first angle α, it appears at a second angle β on the top of the sample container and faces the optical sensor.

[0055] In some implementations, the sample carrier is a test tube or other transparent container, and the sample container will be shaped accordingly and adapted for reception by an optical sensor so that proper examination can be performed.

[0056] In the example implementation text, the light source 16a is configured to emit a light excitation signal of a first frequency toward the sample carried on the sample container, and when the sample is excited by the target optical excitation signal to emit light and shadow, the light receiver 16b is configured to detect the target optical response signal having the optical properties of the target analyte.

[0057] The combined use of solventochromatic techniques and molecular imprinting facilitates the qualitative and / or quantitative detection of the organic compounds discussed herein. Examples of chemical functional groups listed in Tables 1A-1H are suitable for corresponding solvatochromic molecularly imprinted polymers (SMIPs) for solvation-induced color capture. Although the examples show phthalates or phthalate-based plasticizers, the detection methods, techniques, and applicable instruments described herein are applicable to organic compounds with other chemical functional groups without loss of generality. Molecularly imprinted polymers (MIPs), designed as “solventochromic molecularly imprinted polymer probes” or simply “SMIP probes,” have acceptor sites for capturing target organic chemicals and solvent-chromatic functional groups that produce a change in color and / or fluorescence properties upon capture of the target organic compound.

[0058] Molecularly imprinted polymers (MIPs) are molecular polymers that have been treated and designed with an acceptor site using molecular imprinting technology, specifically targeting an organic compound with affinity or complementarity. Solvatochromism is based on the ability of solvent-chromatic molecules to change color due to changes in the medium polarity of the solvent. The design and selection of MIP probes containing effective templates and solvochromic monomers suitable for capturing target analytes with selected or preferred solvochromic properties have been discussed in US Patent No. 8338,553; the literature entitled “How to find effective functional monomers for effective molecularly imprinted polymers” has been published in Advanced Drug Delivery Review 57, 1795-808; and the optimization, evaluation, and characterization of molecularly imprinted polymers have been documented in Advanced Drug Delivery Review 57, 1779-1794. All of the above information on solvochromic molecularly imprinted polymer technology is incorporated herein by reference.

[0059] The solvatochromic molecularly imprinted polymer (SMIP) described in this paper comprises a solvatochromic functional monomer, which binds to the SMIP to form a reporter site. The solvatochromic functional monomer possesses mediating polarity, and when a target analyte compatible with the solvatochromic functional monomer enters the reporter site of the SMIP, the mediating polarity of the solvatochromic functional monomer changes. The solvatochromic functional monomer is highly sensitive to changes in the mediating polarity of the acceptor microenvironment. While organic solvent molecules normally occupy the acceptor sites of the SMIP, the presence of an analyte compatible with the solvatochromic functional monomer at the reporter site displaces the organic solvent molecules, resulting in a significant change in the fluorescence properties and / or color of the solvatochromic functional monomer. These changes can be detected visually or using spectroscopic instruments. The formation of solvation color-changing complexes does not require molecular interactions between the target analyte and the functional monomers. Even if the analyte lacks intermolecular interaction capabilities, it can still be detected by the chemical sensor method of solvation color-changing molecularly imprinted polymers (SMIP).

[0060] By designing molecularly imprinted polymers with solvation acceptor sites, incorporating solvation chromogenic functional monomers, which have affinity or complementarity for target organic compounds, and exhibiting fluorescence and / or color transitions and / or pigmentation upon capture of the organic compound, these polymers are recorded and used to facilitate qualitative and / or quantitative determination of the presence of organic compounds containing the target analyte.

[0061] Therefore, solvatotic molecularly imprinted polymers (SMIPs), which are suitable for capturing organic compounds and possess solvatotic functional monomers that change color and / or fluorescence properties when a target organic compound is captured, can serve as solvatotic probes for detecting organic compounds. For example, by preparing a molecularly imprinted polymer having one or more acceptor sites with affinity or complementarity to functional groups of the organic chemicals listed in Tables 1A-1H, and this molecularly imprinted polymer being based on a solvatotic chemosensor; when an organic compound having one or more functional groups listed in Tables 1A-1H is captured, the color and / or fluorescence properties of the solvatotic functional monomers of the molecularly imprinted polymer of this solvatotic chemosensor will change, enabling qualitative and / or quantitative testing of the organic compound.

[0062] In the example implementation text, molecularly imprinted polymers (SMIPs) are specifically designed to identify or capture target phthalates or phthalate-based plasticizers, and to determine whether, when a phthalate or phthalate-based plasticizer is captured, a molecule with at least one solvation-chromic functional group exhibits a color change and / or a change in fluorescence properties. The probes referenced herein are the solvation-chromic molecularly imprinted polymer plasticizer probes for the various plasticizers mentioned herein.

[0063] The experimental results and Scatchard analysis of specific binding constants, non-specific binding constants, and the distribution density of acceptor sites (binding sites) in various solvation-colored molecularly imprinted polymers of various related target organic compounds are shown in Table 2 below:

[0064] Table 2

[0065]

[0066] The example solvatotic functional monomer is suitable for use in forming solvatotic chromophores within the acceptor sites of solvatotic color-changing molecularly imprinted polymers, for example, applying the solvatotic color-changing molecularly imprinted polymer molecular structure of the following plasticizers to the detection of plasticizers:

[0067]

[0068] On the one hand, the detection device 10 is arranged to detect the solvent color change characteristics of the sample analyte in order to qualitatively and / or quantitatively determine the presence of one or more target analytes in the sample.

[0069] In some implementations, the processor determines the concentration of one or more target analytes in the sample based on the color change of the detection solvent exhibited by the target analyte upon exposure to a light excitation signal.

[0070] exist Figures 4A to 4J The figures depict the solvochromic properties of various exemplary composite analytes of phthalates upon exposure to excitation light. Each type of phthalate composite is a composite analyte containing an example SMIP probe specified for capturing the target phthalate. In these figures, the vertical axis or Y-axis represents the output light intensity and is expressed in intensity units. The horizontal axis or X-axis represents the output light wavelength and is expressed in wavelength units in nm; the example excitation light is at 400 nm. Figures 4A to 4J It will be obvious that the intensity of the output light, more specifically, the peak intensity of the output light, varies with the concentration of the analyte in the composition.

[0071] refer to Figure 4A The SMIP probe was designed to capture DnOP (di(n-octyl) phthalate, C6H4[COO(CH2)7CH3]2, molecular weight = 390.56, CAS no. = 117-84-0) in ethanol. The curves show that different concentrations of the composite analyte (DnOP + SMIP) exhibit varying intensities of reflected light at different optical wavelengths (nanometers). It should be noted that when stimulated by an excitation source in the ultraviolet (UV) spectral region (e.g., a wavelength of 400 nm), reflected optical signals are observed between wavelengths of 425 nm and 745 nm, with different reflected light intensities corresponding to these wavelengths.

[0072] refer to Figure 4A The highest curve point corresponds to the optical intensity characteristics of the target analyte at a concentration of 2000 ppm. The second highest curve point corresponds to the optical intensity characteristics of the target analyte at a concentration of 1500 ppm. The third highest curve point corresponds to the reflected optical intensity characteristics of the target analyte at a concentration of 1000 ppm. The fourth highest curve point corresponds to the reflected light intensity characteristics of the target analyte at a concentration of 700 ppm. The fifth highest curve point corresponds to a concentration of 500 ppm, and so on. The lowest curve point corresponds to the zero concentration of the target analyte (0.00 ppm).

[0073] from Figure 4A The curves show that the peak light scattering intensity of the example target analyte always occurs at or near 500 nm, and the peak intensity of the emitted light generally increases with increasing concentration of the target composite analyte (or decreases with decreasing concentration). The frequency of the peak value of the emitted and reflected optical signals and the spectral range of the reflected light wavelengths can be considered characteristic parameters of the solvated color-changing functional monomers of the SMIP, and can be used selectively without loss of generality when designing SMIP probes. When the composite analyte in solution is irradiated with UV light, solutions with higher concentrations of analyte will exhibit stronger fluorescence, and vice versa, and the relative concentration of the composite analyte can be determined by the intensity of the fluorescence or emitted and reflected light. This intensity of fluorescence or emitted and reflected light can be measured, for example, by a fluorescence spectrometer.

[0074] Similar solvent discoloration properties and trends have been observed in other SMIP+phthalate or SMIP+phthalate-based plasticizer composites. A similar trend or behavior of solvent discoloration properties has been observed in other phthalate and phthalate-based plasticizer target composites (e.g., DINP, DnOP-T, DMP, DEP, DEHP, BBP, DBP, or other types of phthalates) in Table 3, generally showing that the peak intensity of their reflected light increases with increasing concentration at a relative wavelength constant.

[0075] Figure 4B Showing with Figure 4A Similar intensity curves are shown for a chemical sensor containing DMP (dimethyl phthalate) dissolved in 2 mg of a SMIP probe loaded in 3 ml of ethanol. Unless the context otherwise requires, this pertains to... Figure 4A The description is incorporated herein by reference. The curves correspond to concentration points of DMP examples at 0 ppm, 5 ppm, 10 ppm, 20 ppm, 30 ppm, 50 ppm, 70 ppm, 100 ppm, 150 ppm, 200 ppm, 300 ppm, 500 ppm, 700 ppm, 1000 ppm, 1500 ppm, and 2000 ppm; when the concentration of DMP is 2000 ppm, the highest curve point corresponds to the characteristic of the strongest reflected optical signal of the target analyte.

[0076] Figure 4C Showing with Figure 4A and 4B Similar intensity curves were generated, but the chemical sensor containing DEP (diethyl phthalate) and 2 mg of the SMIP probe was placed in 3 ml of ethanol. Unless the context otherwise requires, this article refers to... Figure 4A and 4B The description has been modified as necessary for reference. The Te curve corresponds to example concentrations of phthalates between 0 ppm and 1000 ppm, with the corresponding concentrations shown on one side of the curve. When the concentration of DEP is 1000 ppm, the highest curve corresponds to the light intensity characteristics of the target analyte.

[0077] Figure 4D Showing with Figure 4A and 4B Similar intensities, but concerning DNOP (dibutyl phthalate) and 2 mg SMIP chemiluminescence (CMS) loaded in 3 ml ethanol. Unless the context otherwise requires, [the following is a separate section, likely related to DNOP and SMIP]. Figure 4A and 4BThe relevant descriptions are provided here with necessary modifications for reference. The curves correspond to example concentrations of phthalates between 0 ppm and 1,000 ppm, with the corresponding concentrations shown on one side of the curve. The highest concentration of the target analyte, corresponding to a DBP concentration of 1,000 ppm, is also shown. Figure 4E Showing Figure 4A and 4B Similar intensity curves were obtained, but for DNOP (dioctyl phthalate) and 2 mg of SMIP chemiluminescence with a sensor loaded in 3 ml of ethanol. Unless the context otherwise requires, this is introduced with... Figure 4A and 4B The relevant descriptions are for reference only. The curves correspond to example concentrations of phthalates between 0 ppm and 2000 ppm, with the corresponding concentrations shown on one side of the curve. The highest curve corresponds to the light intensity characteristics of the target analyte when the concentration of DNOP is 2000 ppm.

[0078] Figure 4F Showing with Figure 4A and 4B Similar intensity curves were obtained, but for DIDP (Diisodecylphthalate) and a 2 mg SMIP chemiluminescence sensor loaded in 3 ml of ethanol. Unless the context otherwise requires, this article refers to... Figure 4A and 4B The description has been modified as necessary for reference. The curves correspond to example concentrations of phthalates between 0 ppm and 1000 ppm, with the corresponding concentrations shown on one side of the curve. When the concentration of DIDP is 2000 ppm, the highest curve corresponds to the highest light intensity characteristic of the target analyte.

[0079] Figure 4G Showing with Figure 4A and 4B Similar intensity curves were obtained, but for DEHP(Di(2-ethylhexyl(phthalate)) and 2 mg of SMIP chemiluminescence sensor loaded in 3 ml of ethanol. Unless the context otherwise requires, this article refers to... Figure 4A and 4B The description has been modified as necessary for reference. The curves correspond to example concentrations of phthalates between 0 ppm and 2 mM, with the corresponding concentrations shown on one side of the curve. When the concentration of DEHP is 2 mM, the highest curve corresponds to the highest light intensity characteristic of the target analyte.

[0080] Figure 4H Showing with Figure 4A and 4BSimilar intensity curves were obtained, but for DNHP (Di-n-hexylphthalate) and 2 mg of SMIP chemiluminescence sensor loaded in 3 ml of ethanol. Unless the context otherwise requires, this article refers to... Figure 4A and 4B The description has been modified as necessary for reference. The curves correspond to example concentrations of phthalates between 0 ppm and 2000 ppm, with the corresponding concentrations shown on one side of the curve. When the concentration of DNHP is 2000 ppm, the highest curve corresponds to the highest light intensity characteristic of the target analyte.

[0081] Figure 4I Showing with Figure 4A and 4B Similar intensity curves were obtained, but for DINP (Diisononylphthalate) and 2 mg SMIP chemiluminescence loaded in 3 ml ethanol. Unless the context otherwise requires, this article refers to... Figure 4A and 4B The description has been modified as necessary for reference. The curves correspond to example concentrations of phthalates between 0 ppm and 2000 ppm, with the corresponding concentrations shown on one side of the curve. When the concentration of DINP is 2000 ppm, the highest curve corresponds to the highest light intensity characteristic of the target analyte.

[0082] Figure 4J Showing with Figure 4A and 4B Similar intensity curves were generated, but for BBP (Butyl benzylphthalate) and 2 mg of the SMIP chemiluminescence sensor loaded in 3 ml of ethanol. Unless the context otherwise requires, this article refers to... Figure 4A and 4B The description has been modified as necessary for reference. The curves correspond to example concentrations of phthalates between 0 ppm and 2000 ppm, with the corresponding concentrations shown on one side of the curve. When the concentration of BBP is 2000 ppm, the highest curve corresponds to the highest light intensity characteristic of the target analyte.

[0083] Figure 5A and 5B The relationship between the luminescence intensity and the concentration of the target composite analyte for different types of SMIP+phthalate or SMIP+phthalate-based plasticizer complexes is shown.

[0084] Reference Figure 5A and 5BThe target analyte (DnOP+SMIP complex) in ethanol was excited by 400 nm UV light, and the intensity of the 500 nm fluorescence response was measured and plotted on the Y-axis. Simultaneously, the concentration of the target analyte (in ppm) was plotted on the X-axis. The intensity values ​​on the Y-axis are relative, with the emission intensity at zero concentration as the unit reference. Figure 5A and 5B As shown, it is noted that the intensity of the response increases with increasing concentration of the target complex analyte in ethanol. For example, the intensity of light is measured by measuring the photocurrent output of the optical sensor. Figure 5A and 5B The data were obtained by loading 2 mg of MIP powder into 3 ml of ethanol and then measuring the response luminescence 16 hours after the target composite analyte was loaded into the solvent ethanol.

[0085] In addition to emitting fluorescence in response to excitation light, the frequency of the fluorescence response light was also observed to change slightly with variations in the concentration of the target composite analyte. For example... Figure 4A As shown, with increasing concentration, the peak of emitted light shifts slightly towards the larger or highest wavelength.

[0086] In addition, a visible change in fluorescence color can be observed with the naked eye as the concentration of the target complex analyte increases from zero. For example, the SMIP-DEHP probe in ethanol causes the reagent to change from purplish-blue to yellow, and the fluorescence response changes from purple to cyan as the concentration of the target complex analyte (i.e., SMIP_DEHP) increases from zero.

[0087] When using ethanol as a solvent, it should be understood that other organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), methanol, ethanol, isopropanol, tetrahydrofuran (THF), acetone, acetonitrile, dichloromethane, chloroform, ethyl acetate, water, etc. are also suitable solvents for carrying SMIP-plasticizer probes.

[0088] The relationship or correlation between the response luminescence intensity of the target composite analyte and its concentration was studied, and a plasticizer detection scheme and device were designed.

[0089] For example, Figure 6A Showing Figure 5A The SMIP-DnOP target composite analyte concentration range is shown to exhibit partial solvent colorimetric properties between 0 and 1200 ppm. (Reference) Figure 6AFive data points corresponding to concentrations of 200, 400, 600, 800, and 1000 ppm were plotted. These five data points are basically linearly distributed according to the equation Y = 0.0004X + 0.9284 (Equation 1), where Y is the intensity ratio (Ix / Io), X is the concentration in ppm, Ix is the emission intensity at concentration X, and Io is the emission intensity at zero concentration. It is noteworthy that the R² (squared R) value of the data points is 0.9883, where R is the Pearson correlation coefficient, indicating that the data points fit the linear equation very well. The corresponding experimental results are listed in Table 4 below:

[0090] Table 4

[0091]

[0092] This disclosure describes example applications of the correlation between detection and / or optical properties, such as fluorescence emission intensity, and the concentration of target composite analytes for determining and / or detecting the presence and / or concentration of phthalates and phthalate-based plasticizers.

[0093] For example, refer to Figure 3 Multiple SMIP probes are placed on a transparent plastic card to form a card-shaped SMIP probe carrier or SMIP detector. The SMIP probes are distributed at selected probe positions on a 10-row, 10-column matrix. The probe positions are selected such that adjacent probes are separated by at least one empty interval of the matrix to improve visibility. Each SMIP probe is targeted at a specific target analyte. For example, interval 3,3 is a SMIP probe for capturing BBP (SMIP_BBP probe), interval 3,7 is a SMIP probe for capturing DBP (SMIP_DBP probe), interval 5,4 is a SMIP probe for capturing DEHP (SMIP_DEHP probe), interval 5,8 is a SMIP probe for capturing DnOP (SMIP_DnOP probe), interval 7,2 is a SMIP probe for capturing DIDP (SMIP_DIDP probe), and interval 7,6 is a SMIP probe for capturing DINP (SMIP_DINP probe). Using such a multi-probe carrier, the presence and concentration of multiple different target analytes and their specific types can be conveniently determined using detection device 100.

[0094] Each of the six selected probe sites stores a predetermined amount of a specific SMIP probe (or reagent) to facilitate quantitative and / or qualitative measurements. In this example, each target probe site is square with an area of ​​1 mm × 1 mm, and the overall target site is a probe region 64 depicted within a circular area with a diameter of 10 mm × 10 mm.

[0095] To calibrate the detection device 100, a calibration sample carrier card with a selected and known target complex analyte concentration is placed inside the sample container. Optical measurements are performed, and calibration readings are obtained and stored. The processor then uses these calibration readings to determine the actual sample concentration of the target complex analyte subsequently inserted into the sample carrier card. For example, with Figure 6A Similar calibration data consistently fall within a linear correlation region. A linear relationship similar to Equation 1 can be used to determine the concentration of the target analyte complex, even if this concentration is not one of the calibration data points. When calibration data is not in a linear region, the best-fit curve can be used to determine the target analyte complex when the concentration is not one of the calibration data points. Calibration can be performed by measuring the output current of the optical sensor at selected calibration data points, and the accuracy of calibration can be improved by increasing the number of calibration data points. Additionally, calibration data points can be selected to be at, approximately, and / or above selected concentration limits to provide qualitative information about whether critical limits have been reached, not reached, or exceeded. After obtaining and storing calibration data on light intensity versus target analyte concentration, the process of executing pre-stored instructions will determine whether the concentration of the target analyte complex, or multiple target analytes, is at a specific concentration, below a critical limit, or above a critical limit, without loss of generality. To facilitate quantitative analysis and calibration, each target probe is completely reacted with a predetermined amount or volume of target analyte. For example, a predetermined weight of target analyte complex is dissolved in a predetermined weight of solvent to form a calibration sample of a predetermined concentration. For example, calibration samples of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 40, 60, 80, 100, 200, 400, 600, 800, and 100 ppm were originally used.

[0096] For example, calibration can be performed using a calibration sample in a solution with a predetermined concentration (e.g., 3 ml).

[0097] In evaluation applications, a predetermined weight of sample in a predetermined volume of solution will react fully with a specific probe, and the processor will determine the concentration of the target analyte or multiple target analytes based on pre-stored and inferred correlations between the intensity and concentration of the solvation color change light.

[0098] During the calibration operation, the calibration sample on the sample carrier card is received into the sample container. When the instrument is set to operate in calibration mode, the processor turns on the light source, emitting source light (e.g., at 400 nm) onto the calibration sample on the sample carrier, and measures the intensity of the response light (e.g., 500 nm), which is emitted by the calibration sample in response to the excitation of the source light. By recording the intensity of the received response light for various calibration samples, such as as represented by the output current of the optical sensors, calibration data points are obtained and stored in a storage device such as the on-device's non-volatile memory. The processor then executes the stored instructions to identify the best-fit line or best-fit curve based on the calibration data points, and then establishes the correlation between the received response light intensity and the concentration of the target composite analyte. The correlation is then stored for use during application evaluation. To provide specific calibration to a specific target location, multiple corresponding optical sensors are positioned to receive light from multiple specific target locations without loss of generality.

[0099] The calibration process establishes a relationship between the concentration of the target organic compound and the light intensity at a selected single wavelength, several wavelengths, and / or a range of wavelengths for subsequent detection and quantitative analysis. During the calibration process, the processor correlates the measured light intensity, the concentration of the target organic compound in the target analyte solution, and the concentration of the target organic compound in the target material to form and store calibration data or curves for subsequent detection. In this example, the measured light intensity is the intensity of light emitted by the target analyte solution in response to excitation source light in the UV spectrum, and more specifically, at selected UV wavelengths, for example, from 270 nm to 420 nm, including the UV at 280 nm, 315 nm, 350 nm, 385 nm, or 400 nm, or any range or range between the aforementioned wavelengths. In some embodiments or combinations, the intensity measurement may be a transmittance and / or reflectance measurement without loss of generality.

[0100] In detection mode, a sample-carrying card containing multiple field samples is received within a sample container. The device is configured to operate in detection mode, and the processor operates a light source to emit source light toward the field samples on the sample carrier, measuring the intensity of the response light generated by the field samples excited by the light source. By correlating the measured intensity with the intensity-to-concentration relationship obtained during calibration, the concentration of the target organic compound in the target material can be determined.

[0101] To prepare a field sample, a predetermined weight of the target analyte (e.g., DEHP) is dissolved in a predetermined weight or volume (e.g., 3 ml) of a predetermined solvent (e.g., ethanol). The solution containing the target analyte is then applied to a SMIP detector, allowing the target analyte to react well with the SMIP probe or multiple probes on the SMIP detector (e.g., for 30 minutes). After sufficient reaction, the SMIP detector is placed in the sample container of the detection device to determine the concentration of the target analyte (e.g., DEHP) using a target composite analyte (e.g., SMIP_DEHP).

[0102] like Figure 6B The example calibration curve is shown. The emission intensity is plotted against a predetermined concentration of DEHP. An empirical relationship between DEHP emission intensity and concentration is obtained through linear regression analysis. The calibration curve provides a simple and reliable method for calculating the uncertain concentration of DEHP from measured emission intensity.

[0103] The exemplary detector 70 has a microfluidic capillary device or multiple such devices. Figure 7 The sample carrier of the microfluidic capillary device is shown. The sample carrier is cartridge-type and includes a transparent, UV-transmissive carrier shell having a base 72 extending longitudinally, a first sidewall 74a extending upward from a first side of the base, and a second sidewall 74b extending upward from a second side of the base. A fluid inlet 76a and a fluid outlet 76b are defined at opposite longitudinal ends of the carrier shell. Multiple microfluidic capillary devices, each carrying a specific SMIP probe, are disposed on the shell between the fluid inlet 76a and the fluid outlet 76b.

[0104] exist Figure 7In this example, a total of six microfluidic capillary devices (each carrying a specific SMIP probe) are arranged laterally on the carrier housing, such that the capillary components of the microfluidic capillary devices are substantially parallel to the longitudinal direction of the liquid in the carrier housing, allowing the analyte to flow through the microfluidic capillary devices in a direction substantially parallel to the longitudinal direction of the carrier housing. The microfluidic capillary devices are arranged such that the SMIP_DEHP probe is adjacent to the second sidewall, the SMIP_DnOP probe is close to and adjacent to the SMIP_DEHP probe, the SMIP_DNIP probe is close to and adjacent to the SMIP_DnOP probe, further adjacent to and adjacent to the SMIP_BBP probe and the SMIP_DNIP probe, and close to and adjacent to the SMIP_DBP probe, and finally has the SMIP_DIDP probe in the middle adjacent to the first sidewall 74a and the SMIP_DBP probe. When the required number of probes is insufficient, probes with a larger width or probes of the same width plus filler can be used to fill the lateral space without loss of generality. The microfluidic capillary device comprises nanoscale SMIP nests made of polydimethylsiloxane (PDMS).

[0105] In this example, each SMIP probe is 1mm wide, 1mm high, and 2mm long, with a specified cubic volume of 2mm for each probe. The entire sample holder is 6mm wide, 10mm long, and 1mm high.

[0106] In practical applications, the liquid analyte will enter the detector’s microfluidic capillary device at fluid inlet 76a at a rate of 0.0005 cubic millimeters per second and remain in the microfluidic capillary device at a rate of 0.002 cubic millimeters per second.

[0107] Using the exemplary detector 70, the optical device will, as Figure 8 Arranged as shown. Figure 8 As shown, excitation light sources 86a1 and 86a2 are disposed on two sides of the carrier housing, such that the excitation light is projected in a direction perpendicular to the longitudinal direction and in the transverse direction toward the microfluidic capillary device. An optical sensor 16C is disposed above the microfluidic capillary device to collect response light orthogonal to the irradiation direction of the source light 86a1 and 86a2.

[0108] The detection device used in conjunction with detector 70 will include a liquid delivery device, such as... Figure 9As shown. The liquid delivery device includes a first pump and a second pump. The first pump delivers the liquid analyte to the detector inlet, and the second pump removes residual liquid from the delivery outlet. Except for the specific modified arrangement described above, the above operation and other descriptions are applicable, and the relevant descriptions are incorporated herein by reference. During operation, an electromagnetic field is applied to attract superparamagnetic iron oxide (SPIO) nanoparticles attached to the target composite analyte, and the resulting fluorescence intensity is measured at wavelengths from 480 nm to 510 nm to determine the concentration.

[0109] Exemplary detector 80 includes a PDMS microfluidic capillary electrophoresis device, such as Figure 10 As shown. The operation and properties of the detector 80 are described in... Figure 11 As shown, the detection device that mates with detector 80 will include a liquid delivery device, such as... Figure 12 As shown. Apart from the specific improved apparatus described above, the above operation and other descriptions are applicable, and the relevant descriptions are incorporated herein.

[0110] An exemplary detector 90 includes a transparent tube for receiving liquid analytes, such as Figure 13 As shown. The corresponding optical arrangement and detection device are in Figure 13 and 14 As shown in the diagram. Apart from the specific modifications described above, the above operations and other descriptions are applicable and are incorporated herein by reference.

[0111] An exemplary on-site sample extraction device, including a heating station and a sample collection unit, is available in [location missing]. Figure 15 As shown in Figure 15a, the heating station includes a hot block and a heating assembly for heating the hot block. The hot block is made of metal, with one or more sample containers formed inside the metal block. During operation, a sample collector containing the sample, such as a field-collected sample, is received and placed inside the sample container, and the heating assembly heats the collected sample to a predetermined temperature for a predetermined time set by the operator. Field-collected samples can be heated at high temperatures under sealed conditions for faster and more efficient extraction. For example, the collected sample can be heated, for example, between 180°C and 200°C for, for example, 15-30 minutes. In some embodiments, the heating assembly can be controlled by a processor for better operational control and accuracy.

[0112] In one example of a sample extraction procedure, a known or predetermined weight (e.g., 100 mg) of random sample is taken and placed in a sample collection container (e.g., a glass tube) containing a predetermined weight (e.g., 5 mg) of solvent (e.g., ethanol). Heating is required to extract the target analyte. The extracted analyte solution can then be used for analysis.

[0113] In an exemplary extraction operation, a random sample of known or predetermined weight (e.g., 100 mg) is taken and placed inside a sample collector. The sample collector includes a lower container (in this case, a glass tube, such as a cuvette tube) with a tightly fitting fluid connector at its upper end, such as… Figure 16a As shown, the sample collector is sealed with a cap, forming a "pressure-assisted solvent extraction tube." The sample collector containing the sample is then transferred to the sample extraction device for heated analyte extraction, while the device is sealed, causing the pressure inside the container to increase due to heating. When the sample-containing plasticizer is under sealed and pressurized conditions, i.e., using "pressure-assisted solvent extraction," the extraction rate is increased. When the analyte begins to evaporate, the cap is removed, and the upper container (in this example, a glass test tube, such as a cuvette) is connected to the upper and lower containers via a fluid connector with an open end facing downwards, as shown in the figure. Figure 16b As shown. With continued heating, the target analyte will be completely vaporized and move upward through the channel defined in the connector, and deposited on the upper closed end or the peripheral wall adjacent to the upper closed end of the upper container. The connector is tightly fitted to both the lower and lower containers, and a channel is formed in the connector such that the lower and upper containers are in fluid communication only through the holes on the connector defining the channel.

[0114] After a predetermined time (which will be a time (e.g., 1 minute) allowing all the target plasticizer analytes to be fully vaporized and deposited into the upper container), the upper container will detach from the lower container, with the connector and upper container containing a predetermined amount of solvent, such as 3 ml of ethanol. The extracted sample is then ready for qualitative and / or quantitative analysis as described herein.

[0115] In applications where the sample has not fully entered the upper container, the upper and / or lower containers will be reweighted after the process is completed to determine the actual amount of target material that has been moved into the upper container in preparation for quantitative analysis.

[0116] Using current sample extraction equipment, samples can be extracted quickly with virtually no problems.

[0117] In another example, the extraction method for preparing qualitative and quantitative analysis is as follows:

[0118] Mix 5 ml of ethanol with 100 mg of sample in the following container or container;

[0119] Insert the lower container into the thermal control chamber defined by the hot block of the sample extraction device.

[0120] Assemble the connector to the upper free end of the lower container, and then assemble the free end of the upper container to the connector.

[0121] Turn on the sample extraction device and heat the sample in the lower container to 140°C for 30 minutes. After heating for 30 minutes, remove the upper container, invert it so that the free end is facing up, and fill the upper container with 3 ml of ethanol.

[0122] When the target analyte is evaluated in a liquid state, a predetermined weight of the SMIP probe (e.g., 20 mg) is applied to a solution containing ethanol and the target analyte. The resulting mixture is then subjected to qualitative and / or quantitative analysis in accordance with this disclosure.

[0123] When evaluating a target analyte using a solid detector such as detectors 60 and 70 described herein, a solution containing a predetermined weight of ethanol and the target analyte is applied to the solid detector.

[0124] Alternatively, the target sample can be extracted by direct heating with a high-energy laser or by microwave heating (e.g., for 15 minutes).

[0125] Although this disclosure has been described with reference to examples and exemplary embodiments, it should be understood that the examples and exemplary embodiments are for the purpose of aiding understanding and are not intended to be limiting. For example, although plasticizers such as DINP, DnOP-T, DMP, DEP, DEHP, BBP, and DBP are mentioned herein, the invention will be applicable to other phthalate or phthalate-based plasticizers listed in Table 3, without loss of generality.

[0126] Table 3. Phthalate or Phthalate-based Plasticizers

[0127]

[0128]

[0129]

[0130] Other examples of organic compounds that can be detected according to this disclosure may include, for example, organic functional groups such as phthalates, AZO, phenol, DOTE (PVC stabilizer), amides, nitrobenzene cosmetic fragrances, phosphates, and other organic compounds, as shown herein and in the figures below, without loss of generality.

[0131]

[0132] Table 1A: Functional Groups of Organic Compounds

[0133]

[0134] Table 1B: Functional Groups of Organic Chemicals

[0135]

[0136] Table 1C: Functional Groups of Organic Chemicals

[0137]

[0138] Table 1D: Functional Groups of Organic Chemicals

[0139]

[0140] Table 1E: Functional Groups of Organic Chemicals

[0141] Table 1F: Functional Groups of Organic Chemicals

[0142] Table 1G: Functional Groups of Organic Chemicals

[0143]

[0144] Table 1H: Functional Groups of Organic Chemicals

[0145] Specifically, this application relates in particular to the following implementation methods:

[0146] 1. A method for detecting the presence and / or determining the concentration of a target organic compound in a sample, the method comprising:

[0147] The target sample is dissolved in an organic solvent to obtain a sample solution.

[0148] A probe device is applied to a sample solution to form a target analyte. The probe device comprises a solvatotic molecularly imprinted polymer or SMIP. Upon coupling with or encountering a target organic compound, or when the target organic compound is captured by the solvatotic molecularly imprinted polymer or SMIP, the SMIP containing solvatotic functional groups or solvatotic functional monomers undergoes a color and / or fluorescence property change.

[0149] The presence and / or concentration of a target organic compound are detected or determined by referring to the colorimetric, luminescent, and / or fluorescent responses of the target analyte.

[0150] 2. The method according to embodiment 1, characterized in that the presence and / or concentration of the target organic compound is determined by applying an excitation optical signal to the target analyte and measuring the intensity of a response light signal emitted by the target analyte in response, and / or wherein the intensity of the response light signal is measured at the intensity of a selected wavelength or a plurality of selected wavelengths, wherein the selected single wavelength is different from the wavelength of the excitation light signal, and the selected plurality of wavelengths also include wavelengths different from the wavelength of the excitation light signal.

[0151] 3. A detection device for detecting a target organic compound in a sample, wherein the device comprises a sample container for receiving a target analyte, an optical sensor for emitting an excitation light signal to the target analyte and for detecting a response light signal generated by the target analyte in response to the received excitation optical signal, and an optical arrangement for a processor to determine qualitative and / or quantitative information of the target organic compound in the sample based on solvation colorimetric properties and / or colorimetric, autoluminescence, and / or fluorescence responses of the target analyte; wherein the target analyte comprises an analyte complex, and each analyte complex comprises a probe device and a target organic compound or at least one characteristic functional group thereof; wherein the probe device comprises a solvation colorimetric molecularly imprinted polymer or SMIP, and the SMIP comprises a solvation colorimetric functional group or a solvation colorimetric functional monomer whose color and / or fluorescence properties change upon contact with or coupling with the target organic compound.

[0152] 4. The detection device according to embodiment 3, wherein the processor determines the intensity of the response light signal with reference to the selected single wavelength or multiple wavelengths.

[0153] The concentration of the target organic compound, the selected wavelength being different from the wavelength of the excitation light signal, and the selected multiple wavelengths including those wavelengths being different from the wavelength of the excitation light signal.

[0154] 5. The detection device according to embodiment 3, wherein the optical device includes an optical chamber and a sample container placed inside the optical device, and wherein the light source emits ultraviolet excitation light to the sample container during operation.

[0155] 6. A sample extraction apparatus for detecting organic compounds, the apparatus comprising a heating chamber and a closed sample container having a bottom and a closed upper portion, wherein the heating chamber is used to heat a sample placed at the bottom, and the closed upper portion of the heating chamber is used for sample collection.

[0156] 7. An extraction method for organic compound samples, used for quantitative or concentration determination, the method comprising:

[0157] A sample containing a first predetermined weight of the target organic compound is placed in a sample container and the sample container is closed to form a sealed sample container, the sealed sample container comprising a bottom device, a top device and an upper device, the upper device comprising an intermediate wall which depends on the top device;

[0158] Heating the bottom of the sample container, while the sample is at the bottom of the sealed sample container, vaporizes organic compounds deposited on the top and / or upper part of the sealed sample container; and

[0159] The organic compound from the sample container is dissolved in a second predetermined amount of polar organic solvent.

[0160] 8. The method for extracting organic compound samples according to Embodiment 7, wherein the polar organic solvent is ethanol; and / or high-temperature heating is performed under sealed conditions.

[0161] 9. The detection apparatus, sample extraction apparatus, organic compound sample extraction method or detection method according to the foregoing embodiments, wherein the target organic compound is a phthalate or a phthalate-based plasticizer, and / or contains one or more functional groups listed in List 1A-1H, and / or has Figure 4A-4I The solvation color change concentration property; and / or the target phthalate or the phthalate-based plasticizer is any of the phthalates identified in Table 3.

[0162] 10. An organic compound detector, wherein the detector comprises a solvation-chromic molecularly imprinted polymer (SMIP), the SMIP comprising a solvation-chromic functional group or a solvation-chromic functional monomer, the color and / or fluorescence properties of which change when it is coupled to or encounters a target organic compound.

[0163] 11. The detector according to embodiment 10, wherein the molecularly imprinted polymer contains acceptor sites for selectively capturing or selectively attaching to target organic chemicals and / or wherein the acceptor sites are configured to interact non-covalently with the target organic compound to perform the selective capture.

[0164] 12. The detector according to embodiment 10 or 11, wherein the molecularly imprinted polymer or SMIP is held on a solid substrate or in a polar organic solvent; and / or wherein a plurality of N molecularly imprinted polymers are deposited on a solid substrate at corresponding plurality of target sites, where N is an integer greater than 1; and the N molecularly imprinted polymers are used to detect corresponding plurality of N target organic compounds; and / or wherein the target sites are arranged in an array or a matrix comprising a plurality of arrays; and / or wherein the solid substrate is transparent or translucent; and / or wherein the solid substrate is in the form of a card or cartridge; and / or wherein the detector is in the form of a cartridge.

[0165] 13. A detector according to any one of embodiments 10 to 12, wherein after the molecularly imprinted polymer or SMIP captures the target organic compound, the molecularly imprinted polymer or SMIP emits fluorescence at a second frequency when excited by a light source of a first frequency different from the second frequency; and / or wherein the light source is ultraviolet light; and / or wherein the intensity of the fluorescence is correlated with the concentration of the target organic compound.

[0166] 14. The detector according to any one of embodiments 10-13, wherein the molecularly imprinted polymer or SMIP is used to capture organic compounds containing one or more functional groups as shown in Tables 1A-1H; and / or wherein the molecularly imprinted polymer has an affinity or complementarity with the target phthalate or a phthalate-based plasticizer.

[0167] 15. The detector according to embodiment 14, wherein the target phthalate or the phthalate-based plasticizer comprises functional groups:

[0168]

[0169] And / or the target phthalate or the phthalate-based plasticizer is any of the phthalates identified in Table 3.

[0170] 16. The detector according to any one of embodiments 10-15, wherein the molecularly imprinted polymer comprises a solvated color-changing functional monomer having the following structure:

[0171]

Claims

1. A method of detecting the presence of and / or determining the concentration of a target organic compound in a sample, the method comprising: dissolving a target sample in an organic solvent to obtain a sample solution, applying a probe device to the sample solution to form a target analyte, the probe device comprising a solvatochromic molecularly imprinted polymer, SMIP, which comprises a solvatochromic functional group or a solvatochromic functional monomer that undergoes a change in color and / or fluorescence properties upon coupling or encountering the target organic compound or when the target organic compound is captured by the solvatochromic molecularly imprinted polymer, SMIP, wherein the probe device comprising the SMIP is disposed in one or more microfluidic capillary devices through which the sample solution is caused to flow during the detection process; and, detecting or determining the presence and / or concentration of the target organic compound by reference to the colorimetric, luminescent and / or fluorescent response of the target analyte.

2. The method of claim 1, wherein, The presence and / or concentration of the target organic compound is determined by applying an excitation light signal to the target analyte and by measuring the intensity of a response light signal emitted in response to the target analyte, and / or wherein the intensity of the response light signal is measured at a selected wavelength or a plurality of selected wavelengths, the selected wavelength or wavelengths being different from the wavelength of the excitation light signal and the plurality of selected wavelengths also being different wavelengths from the wavelength of the excitation light signal.

3. The method of claim 2, wherein, The excitation light signal is in the UV spectral region.

4. The method of claim 1, wherein, The target analyte comprises a target complex analyte, and each target complex analyte comprises a probe device and a target organic compound or at least one characteristic functional group thereof.

5. The method according to any one of claims 1 to 4, characterized in that, The method further comprises a calibration process establishing a relationship between the concentration of the target organic compound and the intensity of the light at the selected wavelength or wavelengths, the plurality of selected wavelengths, and / or a range of wavelengths, for subsequent use in qualitative and quantitative analysis of the detection.

6. The method of claim 5, wherein, During the calibration process, the measured light intensity is correlated with the concentration of the target organic compound in the target material analyte solution to form and store calibration data or curves for subsequent use in the detection.

7. The method of claim 5, wherein, For calibration of the detection device, a calibration sample holder card having a selected and known concentration of target complex analyte is placed in the sample container, an optical measurement is made and a calibration reading is obtained and stored, and the calibration reading is then used to determine the actual sample concentration of the target complex analyte carried on the sample holder card subsequently inserted.

8. The method according to any one of claims 1 to 4, characterized in that, The target organic compound is a phthalate ester or phthalate ester-based plasticizer, and / or contains one or more of the following functional groups: phthalate ester chemical structure functional group, azo chemical structure functional group, phenol chemical structure functional group, amide chemical structure functional group, nitrobenzene chemical structure functional group, phosphate chemical structure functional group, thione chemical structure functional group, ether chemical structure functional group, 1-bromopropane chemical structure functional group, 1,2-dichloroethane chemical structure functional group, 1,2,3-trichloropropane (TCP) chemical structure functional group, trichloroethylene chemical structure functional group, alkane chemical structure functional group, polycyclic aromatic hydrocarbon chemical structure functional group, amine chemical structure functional group, anhydride chemical structure functional group, 1,3,5-tris(oxirane-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione chemical structure functional group, Michler's ketone chemical structure functional group; or has solvatochromic concentration properties of phthalate di(n-octyl) (DnOP); and / or has solvatochromic concentration properties of dimethyl phthalate (DMP); and / or has solvatochromic concentration properties of diethyl phthalate (DEP); and / or has solvatochromic concentration properties of di-n-butyl phthalate (DBP); and / or has solvatochromic concentration properties of dioctyl phthalate (DNOP); and / or has solvatochromic concentration properties of diisodecyl phthalate (DIDP); and / or has solvatochromic concentration properties of di(2-ethylhexyl) phthalate (DEHP); and / or has solvatochromic concentration properties of di-n-hexyl phthalate (DNHP); and / or has solvatochromic concentration properties of diisononyl phthalate (DINP); and / or has solvatochromic concentration properties of butyl benzyl phthalate (BBP); or wherein the target phthalate or phthalate-based plasticizer is any one of the following phthalates identified: dimethyl phthalate (DMP), diethyl phthalate (DEP), diallyl phthalate (DAP), di-n-propyl phthalate (DPP), di-n-butyl phthalate (DBP), diisobutyl phthalate (DIBP), butyl cyclohexyl phthalate (BCP), di-n-pentyl phthalate (DPENP / DNPP), dicyclohexyl phthalate (DCP / DCHP), butyl benzyl phthalate (BBP), di-n-hexyl phthalate (DHEXP / DNHP), diisohexyl phthalate (di(4-methyl-2-pentyl) phthalate) (DIHxP), diisohexyl phthalate (DIHpP), butyl decyl phthalate (BDP), di(2-ethylhexyl) phthalate (DEHP, DOP), di(n-octyl) phthalate (DNOP), diisooctyl phthalate (DIOP), n-octyl n-decyl phthalate (ODP), diisononyl phthalate (DINP), di(2-propylheptyl) phthalate (DPHP), diisodecyl phthalate (DIDP), diundecyl phthalate (DUP), diisoundecyl phthalate (DIUP), ditridecyl phthalate (DTDP), diisotridecyl phthalate.

9. The method of claim 4, wherein, During operation, an electromagnetic field is applied to attract superparamagnetic iron oxide SPIO nanoparticle material attached to a target complex analyte, wherein the target complex analyte comprises the SMIP and a target organic compound or at least one characteristic functional group thereof.

10. A detection device for detecting a target organic compound in a sample, wherein the device comprises: a sample container for receiving a target analyte, an optical device for emitting an excitation light signal to the target analyte and for detecting a response light signal generated from the target analyte in response to receiving the excitation light signal, and a processor for determining qualitative and / or quantitative information of the target organic compound in the sample based on the solvatochromic property and / or a colorimetric, spontaneous light and / or fluorescence response of the target analyte; wherein the target analyte comprises a target complex analyte, and each target complex analyte comprises a probe device and a target organic compound or at least one characteristic functional group thereof; wherein the probe device comprises a solvatochromic molecularly imprinted polymer or SMIP, and the SMIP comprises a solvatochromic functional group or solvatochromic functional monomer that changes in color and / or fluorescence properties upon encountering or coupling with a target organic compound; wherein the probe device comprising the SMIP is disposed in one or more microfluidic capillary devices disposed on a housing intermediate a fluid inlet and a fluid outlet; and the detection device further comprises a liquid delivery device comprising a first pump and a second pump, the first pump delivering a liquid analyte to the fluid inlet and the second pump removing liquid analyte residue from the fluid outlet, such that the liquid analyte flows through the microfluidic capillary device.

11. The detection device of claim 10, wherein, The processor determines the concentration of the target organic compound by reference to the intensity of a response light signal at a selected single wavelength or a plurality of wavelengths, the selected single wavelength being different from the wavelength of the excitation light signal and the selected plurality of wavelengths being different from the wavelength of the excitation light signal.

12. The detection device of claim 10, wherein the optical device comprises an optical compartment and a sample container disposed within the optical device, and wherein the light source emits ultraviolet excitation light to the sample container during operation.

13. The detection device of claim 10, wherein, The excitation light signal is in the UV spectral region.

14. The detection device according to any one of claims 10 to 13, characterized in that The processor is configured to perform a calibration process establishing a relationship between the concentration of the target organic compound and the intensity of the light at the selected single wavelength, the selected plurality of wavelengths, and / or a range of wavelengths for subsequent use in qualitative and quantitative analysis of the detection.

15. The detection device of claim 14, wherein, The processor is operative to correlate the measured intensity of the light with the concentration of the target organic compound in the target material analyte solution to form and store calibration data or curves for subsequent use in the detection.

16. The detection device of claim 14, wherein, To calibrate the detection device, a calibration sample holder card having a selected and known concentration of the target complex analyte is placed in the sample container, an optical measurement is made and a calibration reading is obtained and stored, and the calibration reading is then used to determine the actual sample concentration of the target complex analyte carried on a subsequent sample holder card inserted in the sample container.

17. The detection device according to any one of claims 10 to 13, characterized in that The target organic compound is a phthalate or phthalate-based plasticizer, and / or comprises one or more of the following functional groups: a phthalate chemical structure functional group, an azo chemical structure functional group, a phenol chemical structure functional group, an amide chemical structure functional group, a nitrobenzene chemical structure functional group, a phosphate chemical structure functional group, a thione chemical structure functional group, an ether chemical structure functional group, a 1-bromopropane chemical structure functional group, a 1,2-dichloroethane chemical structure functional group, a 1,2,3-trichloropropane (TCP) chemical structure functional group, a trichloroethylene chemical structure functional group, an alkane chemical structure functional group, a polycyclic aromatic hydrocarbon chemical structure functional group, an amine chemical structure functional group, an anhydride chemical structure functional group, a 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione chemical structure functional group, a Michler's ketone chemical structure functional group; or have solvatochromic concentration properties with phthalate di(n-octyl) (DnOP); and / or have solvatochromic concentration properties with dimethyl phthalate (DMP); and / or have solvatochromic concentration properties with diethyl phthalate (DEP); and / or have solvatochromic concentration properties with di-n-butyl phthalate (DBP); and / or have solvatochromic concentration properties with dioctyl phthalate (DNOP); and / or have solvatochromic concentration properties with diisodecyl phthalate (DIDP); and / or have solvatochromic concentration properties with di(2-ethylhexyl) phthalate (DEHP); and / or have solvatochromic concentration with di-n-hexyl phthalate (DNHP); and / or have solvatochromic concentration with diisononyl phthalate (DINP); and / or have solvatochromic concentration with butyl benzyl phthalate (BBP); or wherein the target phthalate or phthalate-based plasticizer is any one of the following phthalates identified: dimethyl phthalate (DMP), diethyl phthalate (DEP), diallyl phthalate (DAP), di-n-propyl phthalate (DPP), di-n-butyl phthalate (DBP), diisobutyl phthalate (DIBP), butyl cyclohexyl phthalate (BCP), di-n-pentyl phthalate (DPENP / DNPP), dicyclohexyl phthalate (DCP / DCHP), butyl benzyl phthalate (BBP), di-n-hexyl phthalate (DHEXP / DNHP), diisohexyl phthalate (di(4-methyl-2-pentyl) phthalate) (DIHxP), diisohexyl phthalate (DIHpP), butyl decyl phthalate (BDP), di(2-ethylhexyl) phthalate (DEHP, DOP), di(n-octyl) phthalate (DNOP), diisooctyl phthalate (DIOP), n-octyl n-decyl phthalate (ODP), diisononyl phthalate (DINP), di(2-propylheptyl) phthalate (DPHP), diisodecyl phthalate (DIDP), diundecyl phthalate (DUP), diisoundecyl phthalate (DIUP), ditridecyl phthalate (DTDP), diisotridecyl phthalate.

18. The detection device according to any one of claims 10 to 13, characterized in that Also included are: a device for applying an electromagnetic field to attract superparamagnetic iron oxide SPIO nanoparticle material attached to a target complex analyte during operation.

19. An organic compound detector for use in a method of detecting the presence of and / or determining the concentration of a target organic compound in a sample as claimed in claim 1, wherein the detector comprises a solvatochromic molecularly imprinted polymer, SMIP, the SMIP comprising a solvatochromic functional group or a solvatochromic functional monomer which undergoes a change in its color and / or fluorescence properties when it is coupled to or encounters the target organic compound, wherein the detector has a sample carrier comprising one or more microfluidic capillary devices, the sample carrier being of a cartridge type and comprising a transparent and UV-transparent carrier housing having a base (72) extending in a longitudinal direction, a first side wall (74a) extending upwardly from a first side of the base (72) and a second side wall (74b) extending upwardly from a second side of the base (72), a fluid inlet (76a) and a fluid outlet (76b) being defined on opposite longitudinal ends of the carrier housing, each microfluidic capillary device carrying a specific SMIP probe being disposed on the housing intermediate the fluid inlet (76a) and the fluid outlet (76b).

20. The detector of claim 19, wherein the molecularly imprinted polymer comprises receptor sites for selectively capturing or binding the target organic chemical and / or wherein the receptor sites are for producing non-covalent bonding interactions with the target organic compound for the selective capture.

21. The detector of claim 19 or 20, wherein the molecularly imprinted polymer or SMIP, after capturing the target organic compound, emits fluorescence at a second frequency when excited by a light source at a first frequency different from the second frequency; and / or wherein the light source is ultraviolet light; and / or wherein the intensity of the fluorescence is correlated to the concentration of the target organic compound.

22. The detector of claim 19 or 20, wherein the molecularly imprinted polymer is affinity or complementary to the target phthalate or phthalate-based plasticizer.

23. The detector of claim 22, wherein the target phthalate or phthalate-based plasticizer comprises a functional group: 。 24. The detector of claim 19 or 20, wherein the molecularly imprinted polymer comprises a solvatochromic functional monomer having the following structure: 。 25. The detector of claim 19 or 20, wherein the target organic compound is a phthalate or phthalate-based plasticizer, and / or comprises one or more of the following functional groups: a phthalate chemical structure functional group, an azo chemical structure functional group, a phenol chemical structure functional group, an amide chemical structure functional group, a nitrobenzene chemical structure functional group, a phosphate chemical structure functional group, a thione chemical structure functional group, an ether chemical structure functional group, a 1-bromopropane chemical structure functional group, a 1,2-dichloroethane chemical structure functional group, a 1,2,3-trichloropropane (TCP) chemical structure functional group, a trichloroethylene chemical structure functional group, an alkane chemical structure functional group, a polycyclic aromatic hydrocarbon chemical structure functional group, an amine chemical structure functional group, an anhydride chemical structure functional group, a 1,3,5-tris(oxirane-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione chemical structure functional group, a Michler's ketone chemical structure functional group; or has solvatochromic concentration properties of phthalate di(n-octyl) (DnOP); and / or has solvatochromic concentration properties of dimethyl phthalate (DMP); and / or has solvatochromic concentration properties of diethyl phthalate (DEP); and / or has solvatochromic concentration properties of di-n-butyl phthalate (DBP); and / or has solvatochromic concentration properties of dioctyl phthalate (DNOP); and / or has solvatochromic concentration properties of diisodecyl phthalate (DIDP); and / or has solvatochromic concentration properties of di(2-ethylhexyl) phthalate (DEHP); and / or has solvatochromic concentration properties of di-n-hexyl phthalate (DNHP); and / or has solvatochromic concentration properties of diisononyl phthalate (DINP); and / or has solvatochromic concentration properties of butyl benzyl phthalate (BBP); or wherein the target phthalate or phthalate-based plasticizer is any one of the following phthalates as identified: dimethyl phthalate (DMP), diethyl phthalate (DEP), diallyl phthalate (DAP), di-n-propyl phthalate (DPP), di-n-butyl phthalate (DBP), diisobutyl phthalate (DIBP), butyl cyclohexyl phthalate (BCP), di-n-pentyl phthalate (DPENP / DNPP), dicyclohexyl phthalate (DCP / DCHP), butyl benzyl phthalate (BBP), di-n-hexyl phthalate (DHEXP / DNHP), diisohexyl phthalate (di(4-methyl-2-pentyl) phthalate) (DIHxP), diisohexyl phthalate (DIHpP), butyl decyl phthalate (BDP), di(2-ethylhexyl) phthalate (DEHP, DOP), di(n-octyl) phthalate (DNOP), diisooctyl phthalate (DIOP), n-octyl n-decyl phthalate (ODP), diisononyl phthalate (DINP), di(2-propylheptyl) phthalate (DPHP), diisodecyl phthalate (DIDP), diundecyl phthalate (DUP), diisoundecyl phthalate (DIUP), ditridecyl phthalate (DTDP), diisotridecyl phthalate.

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