WO2017076883A1 - Use of a substituted zinc phthalocyanine as a sensitive material in a chemical sensor for detecting the presence of drugs in a gaseous medium - Google Patents
Use of a substituted zinc phthalocyanine as a sensitive material in a chemical sensor for detecting the presence of drugs in a gaseous medium Download PDFInfo
- Publication number
- WO2017076883A1 WO2017076883A1 PCT/EP2016/076396 EP2016076396W WO2017076883A1 WO 2017076883 A1 WO2017076883 A1 WO 2017076883A1 EP 2016076396 W EP2016076396 W EP 2016076396W WO 2017076883 A1 WO2017076883 A1 WO 2017076883A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sensor
- cathinone
- sensitive material
- vapors
- ambient air
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 18
- 239000000126 substance Substances 0.000 title claims abstract description 13
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000011701 zinc Substances 0.000 title claims abstract description 11
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 11
- 150000003751 zinc Chemical class 0.000 title claims abstract description 8
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- 229960003920 cocaine Drugs 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- PUAQLLVFLMYYJJ-ZETCQYMHSA-N cathinone Chemical compound C[C@H](N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-ZETCQYMHSA-N 0.000 claims abstract description 8
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Classifications
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- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/0004—Gaseous mixtures, e.g. polluted air
- G01N33/0009—General constructional details of gas analysers, e.g. portable test equipment
- G01N33/0027—General constructional details of gas analysers, e.g. portable test equipment concerning the detector
- G01N33/0036—General constructional details of gas analysers, e.g. portable test equipment concerning the detector specially adapted to detect a particular component
- G01N33/0047—Organic compounds
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N29/00—Investigating or analysing materials by the use of ultrasonic, sonic or infrasonic waves; Visualisation of the interior of objects by transmitting ultrasonic or sonic waves through the object
- G01N29/02—Analysing fluids
- G01N29/022—Fluid sensors based on microsensors, e.g. quartz crystal-microbalance [QCM], surface acoustic wave [SAW] devices, tuning forks, cantilevers, flexural plate wave [FPW] devices
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N29/00—Investigating or analysing materials by the use of ultrasonic, sonic or infrasonic waves; Visualisation of the interior of objects by transmitting ultrasonic or sonic waves through the object
- G01N29/22—Details, e.g. general constructional or apparatus details
- G01N29/24—Probes
- G01N29/2437—Piezoelectric probes
- G01N29/2443—Quartz crystal probes
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2291/00—Indexing codes associated with group G01N29/00
- G01N2291/02—Indexing codes associated with the analysed material
- G01N2291/021—Gases
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2291/00—Indexing codes associated with group G01N29/00
- G01N2291/02—Indexing codes associated with the analysed material
- G01N2291/025—Change of phase or condition
- G01N2291/0256—Adsorption, desorption, surface mass change, e.g. on biosensors
Definitions
- the present invention relates to the field of narcotics detection.
- a substituted zinc phthalocyanine as a sensitive material in a chemical sensor which is intended to detect the presence of narcotics, their precursors and / or their degradation products in a gaseous medium.
- the invention finds particular application in the fight against drug trafficking, also called narcotrafic.
- sniffer dogs trained and trained for this purpose.
- the use of sniffer dogs has the disadvantage of requiring a long training of dogs and their masters and being unsuited to prolonged operations because of the fact that dogs' attention span is limited.
- sniffer dogs are not able to detect narcotics to which they have not been sensitized.
- ion mobility spectrometry In the field of portable devices, there are devices that detect narcotics by ion mobility spectrometry. These devices have the advantage of allowing a rapid detection (in a few tens of seconds at most) and low costs of the presence of narcotics.
- ionic mobility spectrometry is a powerful technique for detecting the presence of narcotic drugs on surfaces, but it proves to be much less reliable when it comes to detecting narcotics in the form of vapors.
- this technique requires the presence of a radioactive source, which means that the devices can only be used under the responsibility of a person competent in radiation protection and by persons with notions of radiation protection.
- a chemical sensor for detecting the presence in gaseous medium of at least one compound selected from opiates, cocaine, cannabinoids, amphetamines, lysergic acid diethylamide, cathine, cathinone, synthetic derivatives of cathinone, ⁇ -hydroxybutyric acid, ketamine, isoamyl nitrite, n-amyl nitrite, their isomers, their salts, their esters, their ethers, their precursors and their degradation products.
- opiates opiates, cocaine, cannabinoids, amphetamines, lysergic acid diethylamide, cathine, cathinone, synthetic derivatives of cathinone, ⁇ -hydroxybutyric acid, ketamine, isoamyl nitrite, n-amyl nitrite, their isomers, their salts, their esters, their ethers, their precursors and their degradation products.
- the substituted zinc phthalocyanine shown above is commonly referred to as zinc 2,3,9,10,16,17,23,24-octakis (octyloxy) -29 / - ⁇ - / phthalocyanine. It is available from Sigma Aldrich under the reference 459720.
- narcotic means any psychotropic substance whose production, trade, transport, import, export, possession, use and consumption are unlawful or subject to regulation.
- psychotropic any chemical substance, of natural or synthetic origin, which acts on the central nervous system by inducing changes in perception, sensations, mood or consciousness.
- Opioid means any compound that acts on opiate receptors in humans and that is either naturally present in opium such as: morphine, codeine or thebaine, or is synthetically obtained as heroin, hydromorphone, hydrocodone, oxymorphone, oxycodone, methadone, tilidine, tramadol, buprenorphine, fentanyl or dihydrocodeine.
- cannabinoid is meant any compound that acts on the cannabinoid receptors in humans and is naturally present in cannabis such as: 9-tetrahydrocannabinol (or THC) or tetrahydrocannabivarin, or is synthetically obtained as -pentyl-3- (1-naphthoyl) indole (or JWH-018), 2 - [(1R, 3S) -3-hydroxycyclohexyl] -5- (2-methyloctan-2-yl) phenol (or CP 47,497) 2 - [(1R, 3S) -3-hydroxycyclohexyl] -5- (1,1-dimethylhexyl) phenol (or (C6) -CP 47,497), 2 - [(1R, 3S) -3-hydroxycyclohexyl) 1- (2-methylnonan-2-yl) phenol (or (C8) -CP 47,497), 2 - [(1R, 3
- amphetamine means any compound derived from phenylethylamine by methylation of the carbon atom located in a of the amino group of phenylethylamine, such as: amphetamine sensu stricto, 4-fluoroamphetamine, 4- methylamphetamine (or 4-MA), methamphetamine, 3,4-methylene-dioxy- / V-methylamphetamine (or MDMA, better known as ecstasy), 3,4-methylenedioxy- / V-ethylamphetamine ( or MDEA), 3,4-methylenedioxy-amphetamine (or MDA), or 2,5-dimethoxy-4-methylamphetamine (or DOM).
- cathinone means any compound derived from cathinone by substitution of one or more carbon atoms of the phenyl group of the cathinone and / or by substitution of the nitrogen atom of the amino group of the cathinone.
- cathinone such as: ephedrone (or methcathinone), methedrone (or 4-methoxymethinone), ethylcathinone, butylone, mephedrone, methylone, amphetamrone, metamfepramone, ethylcathinone (or ethylcathinone), or flhephedrone.
- the PcZn (Ooct) s is present in the sensor preferably in the form of a thin film which covers one or both sides of a suitably selected substrate depending on the physical property whose variations are intended to be measured by this sensor.
- the PcZn (Ooct) s can also be present in the sensor in the form of a massive object such as, for example, a cylinder having a certain porosity so as to make accessible to the compounds that it is desired to detect the together the molecules of this phthalocyanine.
- this film preferably has a thickness of 1 nanometer to 10 microns and more preferably 10 nanometers to 1 micrometer.
- Such a film can be obtained by any of the techniques proposed to date for making a thin film on the surface of a substrate and, in particular, by so-called "wet” deposition techniques because requiring the solution in solution of PcZn (Ooct) s in a volatile organic solvent of the chloroform type, such as spray deposition, spin coating ("spin coating” in English), deposition by drop, deposition-evaporation (or “Drop coating” in English) or soaking-withdrawal (or “dip coating” in English), or by the deposition techniques that do not require dissolution of this phthalocyanine as sublimation.
- the substrate and the measurement system of the sensor are chosen according to the physical property of the PcZn (Ooct) s whose variations induced by the presence of the compounds to be detected are intended to be measured by the sensor.
- the senor is preferably a gravimetric sensor and, more specifically, a quartz microbalance sensor or a surface acoustic wave sensor.
- a gravimetric sensor and, more specifically, a quartz microbalance sensor or a surface acoustic wave sensor.
- the operating principle of these sensors has been described by Sanchez-Pedrono et al. in Analitica Chimica Acta 1986, 182, 285 [6] for quartz microbalance sensors, and by Hoummady et al. in Smart Materials and Structures 1997, 6, 647-657 [7] for SAW sensors.
- PcZn (Ooct) s as a sensitive material in sensors designed to measure variations of a physical property other than the mass such as, for example, optical sensors based on the measurement of variations. of fluorescence, on the measurement of absorbance variations in the UV-visible range or on the measurement of wavelength variations in the infrared range.
- PcZn (Ooct) s as a sensitive material in sensors for detecting the aforementioned narcotic drugs, their isomers, their salts, their esters, their ethers, their precursors and their degradation products has proved to be numerous. advantages.
- this phthalocyanine is very sensitive to all of these substances when present in a a gaseous medium, it reacts to the presence of these substances in an immediate or almost immediate, reproducible and reversible manner.
- the compound to be detected is, preferably, methyl benzoate, cocaine, heroin, an amphetamine or isoamyl nitrite.
- FIG. 1 represents the evolution of the oscillation frequency (F), expressed in Hz (hertz), as a function of the time (t), expressed in seconds, of a quartz microbalance sensor comprising a thin film of PcZn (Ooct) s, when this sensor is exposed successively to the ambient air and vapors of methyl benzoate which is a degradation product of cocaine in the presence of water vapor.
- F oscillation frequency
- t time
- FIG. 2 represents the variations of the oscillation frequency (AF), expressed in Hz, as a function of the time (t), expressed in seconds, of a quartz microbalance sensor comprising a thin film of PcZn (Ooct) s , when this sensor is successively exposed to the ambient air and isoamyl nitrite vapor which is one of the main component of the poppers.
- AF oscillation frequency
- t time
- Ooct PcZn
- FIG. 3 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a microwave sensor.
- quartz balance comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and to cocaine vapors.
- FIG. 4 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a quartz micro-balance sensor comprising a thin film of PcZn ( Ooct) s, when this sensor is successively exposed to ambient air and heroin vapors.
- FIG. 5 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a quartz microbalance sensor comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and amphetamine vapors.
- FIG. 6 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a SAW sensor comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and to methyl benzoate vapors.
- FIG. 7 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a SAW sensor, comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and to isoamyl nitrite vapors.
- a quartz microbalance sensor is made by covering the two faces of a cut crystal AT, with a nominal oscillation frequency of 9 M Hz, provided with two circular gold measuring electrodes (model Q.A9RA -50, Ametek Precision I nstruments), a thin film of PcZn (Ooct) s (Sigma-Aldrich, reference 459720).
- the deposition of this thin film is carried out by performing on the two faces of quartz 5 sprays of 0.1 second each of a solution of PcZn (Ooct) in chloroform, with a concentration of 15 g / l.
- the variation of the oscillation frequency of the sensor related to this deposit is 10 kHz.
- the sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
- FIG. 1 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
- the fall in the oscillation frequency of the sensor induced by the exposure to methyl benzoate vapors is very much greater than this threshold value since it is 500 Hz, which means that the PcZn (Ooct) s present in the sensor is very sensitive to methyl benzoate vapors.
- EXAMPLE 2 Detection of isoamyl nitrite vapor (constituting poppers) by a quartz microbalance sensor
- a quartz microbalance sensor identical to that used in Example 1 above is used. This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
- FIG. 2 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
- the drop in the oscillation frequency of the sensor induced by exposure to isoamyl nitrite vapor which is of the order of 600 Hz, shows a very high sensitivity of the PcZn (Ooct) s vis-à-vis the vapors of this narcotic.
- This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
- FIG. 3 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
- F frequency of oscillation
- t time
- This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
- FIG. 4 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
- This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
- amphetamine sensu stricto at a concentration of 0.4 ppt in ambient air for 5 minutes (ie 300 seconds); and ambient air for 5 minutes.
- FIG. 5 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
- a SAW sensor with a nominal oscillation frequency of 433 MHz, is made by covering the two faces of the piezoelectric substrate of this sensor with a PcZn (Ooct) s thin film (Sigma-Aldrich, reference 459720). .
- the deposition of this thin film is carried out by spraying 0.02 to 0.2 seconds of a solution of PcZn (Ooct) in chloroform, with a concentration of between 0.5 and 1 g / l.
- the sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
- FIG. 6 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
- the increase in the oscillation frequency of the sensor induced by its exposure to methyl benzoate vapors is of the order of 12 000 Hz, which means that the PcZn (Ooct) s present in this sensor is very sensitive to vapors. of this compound.
- This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
- FIG. 7 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
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Abstract
The invention relates to the use of a substituted zinc phthalocyanine of the following formula as a sensitive material in a chemical sensor for detecting, in a gaseous medium, the presence of at least one compound selected from opiates, cocaine, cannabinoids, amphetamines, lysergic acid diethylamide, cathine, cathinone, synthetic derivatives of cathinone, γ-hydroxybutyric acid, ketamine, isoamyl nitrite, n -amyl nitrite, the isomers thereof, the salts thereof, the esters thereof, the ethers thereof, the precursors thereof and the degradation products thereof. Applications of the invention: control of drug trafficking, detection of illicit consumption of drugs in public spaces or as part of security checks or judicial inquiries.
Description
UTILISATION D'UNE PHTALOCYANINE DE ZINC SUBSTITUÉE COMME MATÉRIAU SENSIBLE DANS UN CAPTEUR CHIMIQUE DESTINÉ À DÉTECTER LA PRÉSENCE DE STUPÉFIANTS DANS UN MILIEU GAZEUX USE OF A SUBSTITUTED ZINC PHTHALOCYANINE AS A SENSITIVE MATERIAL IN A CHEMICAL SENSOR FOR DETECTING THE PRESENCE OF NARCOTIC DRUGS IN A GASEOUS MEDIUM
DESCRIPTION DESCRIPTION
DOMAINE TECHNIQUE TECHNICAL AREA
La présente invention se rapporte au domaine de la détection de stupéfiants. The present invention relates to the field of narcotics detection.
Plus spécifiquement, elle se rapporte à l'utilisation d'une phtalocyanine de zinc substituée comme matériau sensible da ns un capteur chimique qui est destiné à détecter la présence de stupéfiants, de leurs précurseurs et/ou de leurs produits de dégradation dans un milieu gazeux et, en particulier, d'opiacés, de cocaïne, de cannabinoïdes, d'amphétamines, d'acide lysergique de diéthylamide (ou LSD), de cathine et de cathinone (qui sont deux alcaloïdes présents dans le khat), de dérivés synthétiques de la cathinone, d'acide γ-hydroxybutyrique (aussi appelée « drogue des violeurs »), de kétamine, de nitrite d'isoamyle et de nitrite de n-amyle (qui entrent dans la composition des poppers), ainsi que de leurs isomères, leurs sels, leurs esters et de leurs éthers. More specifically, it relates to the use of a substituted zinc phthalocyanine as a sensitive material in a chemical sensor which is intended to detect the presence of narcotics, their precursors and / or their degradation products in a gaseous medium. and, in particular, opiates, cocaine, cannabinoids, amphetamines, lysergic acid diethylamide (or LSD), cathine and cathinone (which are two alkaloids present in khat), synthetic derivatives of cathinone, γ-hydroxybutyric acid (also called "rapist drug"), ketamine, isoamyl nitrite and n-amyl nitrite (which are part of the poppers), as well as their isomers, their salts, their esters and their ethers.
L'invention trouve notamment application dans la lutte contre le trafic des stupéfiants, aussi appelé narcotrafic. The invention finds particular application in the fight against drug trafficking, also called narcotrafic.
Elle trouve également a pplication dans le dépistage de la consommation illicite de stupéfiants dans des lieux à usage collectif, qu'ils soient publics ou privés, comme les établissements scolaires (collèges, lycées, universités, etc), les installations sportives, les transports publics, les gares, les aéroports, les administrations, les entreprises, les boites de nuit, etc, ainsi que da ns le cadre de contrôles sécuritaires (contrôles routiers par exemple) ou d'enquêtes judiciaires.
ÉTAT DE LA TECHNIQUE ANTÉRIEURE It is also used in the detection of the illegal consumption of narcotics in public places, whether public or private, such as schools (colleges, high schools, universities, etc.), sports facilities, public transport. , railway stations, airports, administrations, businesses, nightclubs, etc., as well as within the framework of security controls (roadside checks for example) or judicial investigations. STATE OF THE PRIOR ART
D'après l'Organisation Mondiale de la Santé, le trafic de stupéfiants, est, en dollars, le troisième commerce en importance dans le monde, derrière ceux du pétrole et de l'alimentation mais juste avant ceux des armes et des médicaments. According to the World Health Organization, drug trafficking is the third largest dollar trade in the world, behind those of oil and food, but just ahead of arms and medicine.
Outre d'être à l'origine de réels problèmes sanitaires (décès par surdose, transmission d'agents infectieux du type VIH ou VHC) et sociaux, le trafic de stupéfiants génère une criminalité spécifique et la création de réseaux de type mafieux, avec leur contingent de guerres des gangs, de règlements de compte, etc. In addition to causing real health problems (overdose deaths, transmission of infectious agents like HIV or HCV) and social problems, drug trafficking generates specific crime and the creation of mafia type networks, with their contingent of gang wars, settling of scores, etc.
La lutte contre le trafic de stupéfiants constitue donc un enjeu majeur. Toutefois, elle implique que les services en charge de cette lutte et, en particulier, les services douaniers et policiers puissent disposer de moyens leur permettant de détecter sur sites la présence de stupéfiants, notamment dans l'air environnant. The fight against drug trafficking is therefore a major issue. However, it implies that the services in charge of this fight and, in particular, the customs and police services may have means enabling them to detect on site the presence of narcotics, particularly in the surrounding air.
À l'heure actuelle, la méthode la plus couramment utilisée pour détecter sur sites des vapeurs de stupéfiants est l'emploi de chiens renifleurs, dressés et entraînés à cet effet. Toutefois, l'utilisation de chiens renifleurs présente l'inconvénient de nécessiter une longue formation des chiens et de leurs maîtres et d'être inadaptée à des opérations prolongées en raison de ce que la durée d'attention des chiens est limitée. De plus, les chiens renifleurs ne sont pas capables de détecter les stupéfiants auxquels ils n'ont pas été sensibilisés. Currently, the most commonly used method for on-site drug vapor detection is the use of sniffer dogs trained and trained for this purpose. However, the use of sniffer dogs has the disadvantage of requiring a long training of dogs and their masters and being unsuited to prolonged operations because of the fact that dogs' attention span is limited. In addition, sniffer dogs are not able to detect narcotics to which they have not been sensitized.
On cherche donc de plus en plus à remplacer les chiens renifleurs par des appareils portables. We are therefore looking more and more to replace sniffer dogs with portable devices.
En matière d'appareils portables, il existe des appareils qui détectent les stupéfiants par spectrométrie à mobilité ionique. Ces appareils présentent l'avantage de permettre une détection rapide (en quelques dizaines de secondes au plus) et à faible coûts de la présence de stupéfiants. Par contre, autant la spectrométrie à mobilité ionique est une technique performante pour détecter la présence de stupéfiants sur des surfaces, autant elle se révèle être beaucoup moins fiable lorsqu'il s'agit de détecter des stupéfiants à l'état de vapeurs. En outre, cette technique nécessite la présence d'une
source radioactive, ce qui implique que les appareils ne peuvent être utilisés que sous la responsabilité d'une personne compétente en radioprotection et par des personnes ayant des notions de radioprotection. In the field of portable devices, there are devices that detect narcotics by ion mobility spectrometry. These devices have the advantage of allowing a rapid detection (in a few tens of seconds at most) and low costs of the presence of narcotics. On the other hand, ionic mobility spectrometry is a powerful technique for detecting the presence of narcotic drugs on surfaces, but it proves to be much less reliable when it comes to detecting narcotics in the form of vapors. In addition, this technique requires the presence of a radioactive source, which means that the devices can only be used under the responsibility of a person competent in radiation protection and by persons with notions of radiation protection.
Depuis quelques années, le développement de capteurs capables de détecter en temps réel des espèces chimiques gazeuses est en plein essor. Le fonctionnement de ces capteurs est basé sur l'utilisation d'un film d'un matériau sensible, c'est-à-dire d'un matériau dont au moins une propriété physique P (masse, température, conductivité électrique, absorbance, fluorescence, etc) est modifiée au contact des molécules gazeuses recherchées, qui revêt un système apte à mesurer en temps réel toute variation de cette propriété physique et de mettre ainsi en évidence la présence des molécules gazeuses recherchées. In recent years, the development of sensors able to detect in real time gaseous chemical species is in full swing. The operation of these sensors is based on the use of a film of a sensitive material, that is to say of a material of which at least one physical property P (mass, temperature, electrical conductivity, absorbance, fluorescence , etc.) is modified in contact with the desired gas molecules, which has a system capable of measuring in real time any variation of this physical property and thus highlight the presence of the desired gas molecules.
Les avantages des capteurs chimiques sont multiples : instantanéité des résultats, possibilité de miniaturisation et, donc, portabilité, maniabilité et autonomie importante, faibles coûts de fabrication et d'exploitation, etc. Par contre, il est évident que leurs performances sont extrêmement variables selon la nature du matériau sensible utilisé. The advantages of chemical sensors are multiple: instantaneous results, possibility of miniaturization and, therefore, portability, maneuverability and significant autonomy, low manufacturing and operating costs, etc. By cons, it is obvious that their performance is extremely variable depending on the nature of the sensitive material used.
À ce jour, les matériaux sensibles qui ont été proposés pour la détection de stupéfiants sous forme de vapeurs se limitent à des polymères à empreinte moléculaire, contenant des complexes de lanthanides, et à des complexes antigènes/ anticorps faisant appel à des essais immunologiques (US 2003/0003587, [1] ; Stubbs et al., IEEE Sensors Journal 2005, 5, 335-339, [2] ; Frisk et al., Lab on a Chip 2008, 8, 1648- 1657, [3]), ce qui est très peu. To date, sensitive materials that have been proposed for the detection of narcotic vapors are limited to molecularly imprinted polymers containing lanthanide complexes, and to antigen / antibody complexes using immunoassays (US 2003/0003587, [1], Stubbs et al., IEEE Sensors Journal 2005, 5, 335-339, [2], Frisk et al., Lab on a Chip 2008, 8, 1648-1657, [3]), which is very little.
I l est, par ailleurs, connu d'utiliser des phtalocyanines métallées ou non métallées comme matériaux sensibles dans des dispositifs destinés à détecter des gaz et, notamment, des gaz halogénés, les oxydes d'azote, en particulier N02, et l'ozone (Paoletti et al., Sensors 2009, 9, 5277-5297 [4] ; Brunet et al., Thin Solid Films 2005, 490, 1, 28-35 It is, moreover, known to use metallated or non-metallated phthalocyanines as sensitive materials in devices intended to detect gases and, in particular, halogenated gases, nitrogen oxides, in particular N0 2 , and Ozone (Paoletti et al., Sensors 2009, 9, 5277-5297 [4], Brunet et al., Thin Solid Films 2005, 490, 1, 28-35
[5]). Par contre, à la connaissance des I nventeurs, l'utilisation de phtalocyanines et, en particulier, de phtalocyanines de zinc substituées comme matériaux sensibles pour détecter la présence de stupéfiants dans un milieu gazeux n'a jamais été proposée à ce jour.
Or, dans le cadre de leurs travaux sur le développement de capteurs chimiques destinés à la détection de stupéfiants, les Inventeurs ont constaté qu'une phtalocyanine de zinc substituée par des groupes octyloxy (ou octoxy) réagit avec une très grande sensibilité aux vapeurs d'un certain nombre de stupéfiants et est donc susceptible de constituer un matériau sensible de choix pour des capteurs chimiques destinés à détecter la présence de ces stupéfiants dans un milieu gazeux. [5]). On the other hand, to the knowledge of the inventors, the use of phthalocyanines and, in particular, of substituted zinc phthalocyanines as sensitive materials for detecting the presence of narcotic drugs in a gaseous medium has never been proposed to date. However, as part of their work on the development of chemical sensors for the detection of narcotics, the inventors have found that a zinc phthalocyanine substituted by octyloxy (or octoxy) groups reacts with a very high sensitivity to vapors. a number of narcotics and is therefore likely to be a sensitive material of choice for chemical sensors for detecting the presence of these narcotics in a gaseous medium.
Et c'est sur cette constatation qu'est basée la présente invention. And it is on this observation that the present invention is based.
EXPOSÉ DE L'INVENTION STATEMENT OF THE INVENTION
L'invention a donc pour objet l'utilisation d'une phtalocyanine de zinc substituée de formule ci-après : The subject of the invention is therefore the use of a substituted zinc phthalocyanine of the following formula:
comme matériau sensible dans un capteur chimique pour détecter la présence dans milieu gazeux d'au moins un composé choisi parmi les opiacés, la cocaïne, cannabinoïdes, les amphétamines, le diéthylamide de l'acide lysergique, la cathine, cathinone, les dérivés synthétiques de la cathinone, l'acide γ-hydroxybutyrique,
kétamine, le nitrite d'isoamyle, le nitrite de n-amyle, leurs isomères, leurs sels, leurs esters, leurs éthers, leurs précurseurs et leurs produits de dégradation. as a sensitive material in a chemical sensor for detecting the presence in gaseous medium of at least one compound selected from opiates, cocaine, cannabinoids, amphetamines, lysergic acid diethylamide, cathine, cathinone, synthetic derivatives of cathinone, γ-hydroxybutyric acid, ketamine, isoamyl nitrite, n-amyl nitrite, their isomers, their salts, their esters, their ethers, their precursors and their degradation products.
La phtalocyanine de zinc substituée représentée ci-avant est communément appelée 2,3,9,10,16,17,23,24-octakis(octyloxy)-29/-/-31/-/-phtalocyanine de zinc. Elle est disponible auprès de la société Sigma Aldrich sous la référence 459720. The substituted zinc phthalocyanine shown above is commonly referred to as zinc 2,3,9,10,16,17,23,24-octakis (octyloxy) -29 / -β- / phthalocyanine. It is available from Sigma Aldrich under the reference 459720.
Elle sera dénommée plus simplement PcZn(Ooct)s dans ce qui suit. It will be called more simply PcZn (Ooct) s in what follows.
Dans ce qui précède et ce qui suit, on entend par « stupéfiant », tout psychotrope dont la production, le commerce, le transport, l'importation, l'exportation, la détention, l'emploi et la consommation sont illicites ou sujets à une réglementation. In the foregoing and the following, "narcotic" means any psychotropic substance whose production, trade, transport, import, export, possession, use and consumption are unlawful or subject to regulation.
On entend par « psychotrope », toute substance chimique, d'origine naturelle ou synthétique, qui agit sur le système nerveux central en induisant des modifications de la perception, des sensations, de l'humeur ou de la conscience. By "psychotropic" is meant any chemical substance, of natural or synthetic origin, which acts on the central nervous system by inducing changes in perception, sensations, mood or consciousness.
On entend par « opiacé », tout composé qui agit sur les récepteurs opiacés chez l'homme et qui est, soit naturellement présent dans l'opium comme : la morphine, la codéine ou la thébaïne, soit obtenu par synthèse comme l'héroïne, l'hydromorphone, l'hydrocodone, l'oxymorphone, l'oxycodone, la méthadone, la tilidine, le tramadol, la buprénorphine, le fentanyl ou la dihydrocodéine. "Opioid" means any compound that acts on opiate receptors in humans and that is either naturally present in opium such as: morphine, codeine or thebaine, or is synthetically obtained as heroin, hydromorphone, hydrocodone, oxymorphone, oxycodone, methadone, tilidine, tramadol, buprenorphine, fentanyl or dihydrocodeine.
On entend par « cannabinoïde », tout composé qui agit sur les récepteurs cannabinoïdes chez l'homme et qui est, soit naturellement présent dans le cannabis comme : le A9-tétrahydrocannabinol (ou THC) ou la tétrahydrocannabivarine, soit obtenu par synthèse comme le l-pentyl-3-(l-naphthoyl)indole (ou JWH-018), le 2-[(lR,3S)-3-hydroxycyclohexyl]-5-(2-méthyloctan-2-yl)phénol (ou CP 47,497), le 2-[(l ?,3S)-3-hydroxycyclohexyl]-5-(l,l-diméthylhexyl)phénol (ou (C6)-CP 47,497), le 2-[(lR,3S)-3-hydroxycyclohexyl]-5-(2-méthylnonan-2-yl)phénol (ou (C8)-CP 47,497), le 2-[(lR,3S)-3-hydroxycyclohexyl]-5-(2-methyldecan-2-yl)phénol (ou (C9)-CP 47,497), ou le (6a ?,10a ?)-9-(hydroxyméthyl)-6,6-diméthyl-3-(2-méthyl-octan-2-yl)-6a,7,10,10a- tétrahydrobenzo[c]-chromèn-l-ol (ou HU-210). By "cannabinoid" is meant any compound that acts on the cannabinoid receptors in humans and is naturally present in cannabis such as: 9-tetrahydrocannabinol (or THC) or tetrahydrocannabivarin, or is synthetically obtained as -pentyl-3- (1-naphthoyl) indole (or JWH-018), 2 - [(1R, 3S) -3-hydroxycyclohexyl] -5- (2-methyloctan-2-yl) phenol (or CP 47,497) 2 - [(1R, 3S) -3-hydroxycyclohexyl] -5- (1,1-dimethylhexyl) phenol (or (C6) -CP 47,497), 2 - [(1R, 3S) -3-hydroxycyclohexyl) 1- (2-methylnonan-2-yl) phenol (or (C8) -CP 47,497), 2 - [(1R, 3S) -3-hydroxycyclohexyl] -5- (2-methyldecan-2-yl) phenol (or (C9) -CP 47,497), or (6a, 10a) -9- (hydroxymethyl) -6,6-dimethyl-3- (2-methyl-octan-2-yl) -6a, 7 10,10-tetrahydrobenzo [c] -chromen-1-ol (or HU-210).
On entend par « amphétamine », tout composé dérivé de la phényléthylamine par méthylation de l'atome de carbone situé en a du groupe aminé de la phényléthylamine comme : l'amphétamine sensu stricto, la 4-fluoroamphétamine, la 4-
méthylamphétamine (ou 4-MA), la méthamphétamine, la 3,4-méthylène-dioxy-/V- méthylamphétamine (ou MDMA, plus connue sous le nom d'ecstasy), la 3,4-méthylènedioxy-/V-éthylamphétamine (ou MDEA), la 3,4-méthylènedioxy- amphétamine (ou MDA), ou la 2,5-diméthoxy-4-méthylamphétamine (ou DOM). The term "amphetamine" means any compound derived from phenylethylamine by methylation of the carbon atom located in a of the amino group of phenylethylamine, such as: amphetamine sensu stricto, 4-fluoroamphetamine, 4- methylamphetamine (or 4-MA), methamphetamine, 3,4-methylene-dioxy- / V-methylamphetamine (or MDMA, better known as ecstasy), 3,4-methylenedioxy- / V-ethylamphetamine ( or MDEA), 3,4-methylenedioxy-amphetamine (or MDA), or 2,5-dimethoxy-4-methylamphetamine (or DOM).
On entend par « dérivé synthétique de la cathinone », tout composé dérivé de la cathinone par substitution d'un ou plusieurs atomes de carbone du groupe phényle de la cathinone et/ou par substitution de l'atome d'azote du groupe aminé de la cathinone comme : l'éphédrone (ou méthcathinone), la méthédrone (ou 4-méthoxy- méthcathinone), l'éthylcathinone, la butylone, la méphédrone, la méthylone, l'amphépramone, la métamfépramone, l'éthycathinone (ou éthylcathinone), ou la fléphédrone. The term "synthetic derivative of cathinone" means any compound derived from cathinone by substitution of one or more carbon atoms of the phenyl group of the cathinone and / or by substitution of the nitrogen atom of the amino group of the cathinone. cathinone such as: ephedrone (or methcathinone), methedrone (or 4-methoxymethinone), ethylcathinone, butylone, mephedrone, methylone, amphetamrone, metamfepramone, ethylcathinone (or ethylcathinone), or flhephedrone.
Conformément à l'invention, la PcZn(Ooct)s est présente dans le capteur de préférence sous la forme d'un film mince qui recouvre l'une ou les deux faces d'un substrat convenablement choisi en fonction de la propriété physique dont les variations sont destinées à être mesurées par ce capteur. According to the invention, the PcZn (Ooct) s is present in the sensor preferably in the form of a thin film which covers one or both sides of a suitably selected substrate depending on the physical property whose variations are intended to be measured by this sensor.
En variante, la PcZn(Ooct)s peut également être présente dans le capteur sous la forme d'un objet massif comme, par exemple, un cylindre présentant une certaine porosité de sorte à rendre accessible aux composés que l'on souhaite détecter l'ensemble des molécules de cette phtalocyanine. Alternatively, the PcZn (Ooct) s can also be present in the sensor in the form of a massive object such as, for example, a cylinder having a certain porosity so as to make accessible to the compounds that it is desired to detect the together the molecules of this phthalocyanine.
Lorsque la PcZn(Ooct)s se présente sous la forme d'un film mince, ce film présente, de préférence, une épaisseur de 1 nanomètre à 10 micromètres et, mieux encore, de 10 nanomètres à 1 micromètre. When the PcZn (Ooct) is in the form of a thin film, this film preferably has a thickness of 1 nanometer to 10 microns and more preferably 10 nanometers to 1 micrometer.
Un tel film peut être obtenu par l'une quelconque des techniques proposées à ce jour pour réaliser un film mince sur la surface d'un substrat et, notamment, par les techniques de dépôt dites « par voie humide » car nécessitant la mise en solution de la PcZn(Ooct)s dans un solvant organique volatil du type chloroforme, telles que le dépôt par pulvérisation, le dépôt à la tournette (ou « spin coating » en anglais), le dépôt à la goutte, le dépôt-évaporation (ou « drop coating » en anglais) ou le trempage-retrait (ou « dip coating » en anglais), ou bien par les techniques de dépôt ne nécessitant pas de mise en solution de cette phtalocyanine comme la sublimation.
Le substrat ainsi que le système de mesure du capteur sont choisis en fonction de la propriété physique de la PcZn(Ooct)s dont les variations induites par la présence des composés à détecter sont destinées à être mesurées par le capteur. Such a film can be obtained by any of the techniques proposed to date for making a thin film on the surface of a substrate and, in particular, by so-called "wet" deposition techniques because requiring the solution in solution of PcZn (Ooct) s in a volatile organic solvent of the chloroform type, such as spray deposition, spin coating ("spin coating" in English), deposition by drop, deposition-evaporation (or "Drop coating" in English) or soaking-withdrawal (or "dip coating" in English), or by the deposition techniques that do not require dissolution of this phthalocyanine as sublimation. The substrate and the measurement system of the sensor are chosen according to the physical property of the PcZn (Ooct) s whose variations induced by the presence of the compounds to be detected are intended to be measured by the sensor.
En l'espèce, les variations de masse de la PcZn(Ooct)s, déposée sur un substrat piézoélectrique (ou résonateur) de type microbalance à quartz ou de type à ondes acoustiques de surface (ou SAW de « Surface Acoustic Wave »), se sont révélées particulièrement intéressantes à mesurer. In the present case, the variations in mass of the PcZn (Ooct) s, deposited on a piezoelectric substrate (or resonator) of the quartz microbalance or surface acoustic wave (or Surface Acoustic Wave) type, have proved particularly interesting to measure.
Aussi, le capteur est-il, de préférence, un capteur gravimétrique et, plus spécifiquement, un capteur à microbalance à quartz ou un capteur à ondes acoustiques de surface. Le principe de fonctionnement de ces capteurs a notamment été décrit par Sanchez-Pedrono et al. dans Analitica Chimica Acta 1986, 182, 285 [6] pour les capteurs à microbalance à quartz, et par Hoummady et al. dans Smart Materials and Structures 1997, 6, 647-657 [7] pour les capteurs SAW. Also, the sensor is preferably a gravimetric sensor and, more specifically, a quartz microbalance sensor or a surface acoustic wave sensor. The operating principle of these sensors has been described by Sanchez-Pedrono et al. in Analitica Chimica Acta 1986, 182, 285 [6] for quartz microbalance sensors, and by Hoummady et al. in Smart Materials and Structures 1997, 6, 647-657 [7] for SAW sensors.
Bien entendu, il est également possible d'utiliser la PcZn(Ooct)s comme matériau sensible dans des capteurs conçus pour mesurer des variations d'une propriété physique autre que la masse comme, par exemple, des capteurs optiques basés sur la mesure de variations de fluorescence, sur la mesure de variations d'absorbance dans le domaine UV-visible ou encore sur la mesure de variations de longueur d'onde dans le domaine des infrarouges. Of course, it is also possible to use the PcZn (Ooct) s as a sensitive material in sensors designed to measure variations of a physical property other than the mass such as, for example, optical sensors based on the measurement of variations. of fluorescence, on the measurement of absorbance variations in the UV-visible range or on the measurement of wavelength variations in the infrared range.
Par ailleurs, il est également possible de réunir au sein d'un même dispositif ou « multicapteur », plusieurs capteurs élémentaires comprenant des matériaux sensibles différents les uns des autres, ou munis de substrats et de systèmes de mesure différents les uns des autres, l'essentiel étant que l'un au moins de ces capteurs comprenne la PcZn(Ooct)s en tant que matériau sensible. Furthermore, it is also possible to gather within the same device or "multisensor", several elementary sensors comprising sensitive materials different from each other, or provided with substrates and measuring systems different from each other, l It is essential that at least one of these sensors include PcZn (Ooct) s as a sensitive material.
L'utilisation de la PcZn(Ooct)s en tant que matériau sensible dans des capteurs pour détecter les stupéfiants précités, leurs isomères, leurs sels, leurs esters, leurs éthers, leurs précurseurs et leurs produits de dégradation s'est révélée présenter de nombreux avantages. The use of PcZn (Ooct) s as a sensitive material in sensors for detecting the aforementioned narcotic drugs, their isomers, their salts, their esters, their ethers, their precursors and their degradation products has proved to be numerous. advantages.
En effet, outre que cette phtalocyanine présente une très grande sensibilité vis-à-vis de l'ensemble de ces substances lorsqu'elles sont présentes dans un
milieu gazeux, elle réagit à la présence de ces substances de manière immédiate ou quasi immédiate, reproductible et réversible. Indeed, besides this phthalocyanine is very sensitive to all of these substances when present in a a gaseous medium, it reacts to the presence of these substances in an immediate or almost immediate, reproducible and reversible manner.
Elle peut de plus être aisément mise en œuvre sous la forme de films minces, soit par des techniques de dépôt dites par voie humide, soit par sublimation, et permet de ce fait d'envisager la fabrication de capteurs miniaturisés, aisément transportables et manipulables sur tout type de sites, à des coûts compatibles avec une production de capteurs à une échelle industrielle. It can also be easily implemented in the form of thin films, either by so-called wet deposition techniques, or by sublimation, and thus makes it possible to envisage the manufacture of miniaturized sensors, easily transportable and manipulable on all types of sites, at costs compatible with the production of sensors on an industrial scale.
Conformément à l'invention, le composé à détecter est, de préférence, le benzoate de méthyle, la cocaïne, l'héroïne, une amphétamine ou le nitrite d'isoamyle. According to the invention, the compound to be detected is, preferably, methyl benzoate, cocaine, heroin, an amphetamine or isoamyl nitrite.
D'autres caractéristiques et avantages de l'invention apparaîtront mieux à la lecture du complément de description qui suit, qui se rapporte à des exemples d'utilisation de la PcZn(Ooct)s comme matériau sensible dans des capteurs gravimétriques et de démonstration des propriétés de ces capteurs. Other features and advantages of the invention will appear better on reading the additional description which follows, which relates to examples of the use of PcZn (Ooct) s as a sensitive material in gravimetric sensors and property demonstration. of these sensors.
Bien entendu, ces exemples ne sont donnés qu'à titre d'illustrations de l'objet de l'invention et ne constituent en aucun cas une limitation de cet objet. Of course, these examples are given only as illustrations of the subject of the invention and do not constitute in any way a limitation of this object.
BRÈVE DESCRIPTION DES FIGURES BRIEF DESCRIPTION OF THE FIGURES
La figure 1 représente l'évolution de la fréquence d'oscillation (F), exprimée en Hz (hertz), en fonction du temps (t), exprimé en secondes, d'un capteur à microbalance à quartz comprenant un film mince de PcZn(Ooct)s, lorsque ce capteur est exposé successivement à l'air ambiant et à des vapeurs de benzoate de méthyle qui est un produit de dégradation de la cocaïne en présence de vapeur d'eau. FIG. 1 represents the evolution of the oscillation frequency (F), expressed in Hz (hertz), as a function of the time (t), expressed in seconds, of a quartz microbalance sensor comprising a thin film of PcZn (Ooct) s, when this sensor is exposed successively to the ambient air and vapors of methyl benzoate which is a degradation product of cocaine in the presence of water vapor.
La figure 2 représente les variations de la fréquence d'oscillation (AF), exprimées en Hz, en fonction du temps (t), exprimé en secondes, d'un capteur à microbalance à quartz comprenant un film mince de PcZn(Ooct)s, lorsque ce capteur est exposé successivement à l'air ambiant et à des vapeurs de nitrite d'isoamyle qui est un des principaux constituant des poppers. FIG. 2 represents the variations of the oscillation frequency (AF), expressed in Hz, as a function of the time (t), expressed in seconds, of a quartz microbalance sensor comprising a thin film of PcZn (Ooct) s , when this sensor is successively exposed to the ambient air and isoamyl nitrite vapor which is one of the main component of the poppers.
La figure 3 représente l'évolution de la fréquence d'oscillation (F), exprimée en Hz, en fonction du temps (t), exprimé en secondes, d'un capteur à micro-
balance à quartz comprenant un film mince de PcZn(Ooct)s, lorsque ce capteur est exposé successivement à l'air ambiant et à des vapeurs de cocaïne. FIG. 3 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a microwave sensor. quartz balance comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and to cocaine vapors.
La figure 4 représente l'évolution de la fréquence d'oscillation (F), exprimée en Hz, en fonction du temps (t), exprimé en secondes, d'un capteur à micro- balance à quartz comprenant un film mince de PcZn(Ooct)s, lorsque ce capteur est exposé successivement à l'air ambiant et à des vapeurs d'héroïne. FIG. 4 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a quartz micro-balance sensor comprising a thin film of PcZn ( Ooct) s, when this sensor is successively exposed to ambient air and heroin vapors.
La figure 5 représente l'évolution de la fréquence d'oscillation (F), exprimée en Hz, en fonction du temps (t), exprimé en secondes, d'un capteur à microbalance à quartz comprenant un film mince de PcZn(Ooct)s, lorsque ce capteur est exposé successivement à l'air ambiant et à des vapeurs d'amphétamine. FIG. 5 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a quartz microbalance sensor comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and amphetamine vapors.
La figure 6 représente l'évolution de la fréquence d'oscillation (F), exprimée en Hz, en fonction du temps (t), exprimé en secondes, d'un capteur SAW comprenant un film mince de PcZn(Ooct)s, lorsque ce capteur est exposé successivement à l'air ambiant et à des vapeurs de benzoate de méthyle. FIG. 6 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a SAW sensor comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and to methyl benzoate vapors.
La figure 7 représente l'évolution de la fréquence d'oscillation (F), exprimée en Hz, en fonction du temps (t), exprimé en secondes, d'un capteur SAW, comprenant un film mince de PcZn(Ooct)s, lorsque ce capteur est exposé successivement à l'air ambiant et à des vapeurs de nitrite d'isoamyle. FIG. 7 represents the evolution of the oscillation frequency (F), expressed in Hz, as a function of the time (t), expressed in seconds, of a SAW sensor, comprising a thin film of PcZn (Ooct) s, when this sensor is successively exposed to ambient air and to isoamyl nitrite vapors.
EXPOSÉ DÉTAILLÉ DE MODES DE RÉALISATION PARTICULIERS EXEMPLE 1 : Détection de vapeurs de benzoate de méthyle (produit de dégradation de la cocaïne en présence de vapeur d'eau) par un capteur à microbalance à quartz DETAILED DESCRIPTION OF PARTICULAR EMBODIMENTS EXAMPLE 1 Detection of Methyl Benzoate Vapor (Cocaine Degradation Product in the Presence of Water Vapor) by a Quartz Microbalance Sensor
Dans cet exemple, on réalise un capteur à microbalance à quartz en recouvrant les deux faces d'un quartz de coupe AT, de fréquence d'oscillation nominale de 9 M Hz, muni de deux électrodes de mesure circulaires en or (modèle Q.A9RA-50, Ametek Précision I nstruments), d'un film mince de PcZn(Ooct)s (Sigma-AIdrich, référence 459720). In this example, a quartz microbalance sensor is made by covering the two faces of a cut crystal AT, with a nominal oscillation frequency of 9 M Hz, provided with two circular gold measuring electrodes (model Q.A9RA -50, Ametek Precision I nstruments), a thin film of PcZn (Ooct) s (Sigma-Aldrich, reference 459720).
Le dépôt de ce film mince est réalisé en effectuant sur les deux faces du quartz 5 pulvérisations de 0,1 seconde chacune d'une solution de PcZn(Ooct)s dans le chloroforme, de concentration égale à 15 g/L.
La variation de la fréquence d'oscillation du capteur liée à ce dépôt est de 10 kHz. The deposition of this thin film is carried out by performing on the two faces of quartz 5 sprays of 0.1 second each of a solution of PcZn (Ooct) in chloroform, with a concentration of 15 g / l. The variation of the oscillation frequency of the sensor related to this deposit is 10 kHz.
Le capteur est soumis à des tests de détection qui sont réalisés à 20°C et qui consistent à l'exposer successivement à : The sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
. l'air ambiant pendant 10 minutes (soit 600 secondes) ; . ambient air for 10 minutes (600 seconds);
du benzoate de méthyle à une concentration de 350 ppm dans de l'air ambiant pendant 5 minutes (soit 300 secondes) ; et à methyl benzoate at a concentration of 350 ppm in ambient air for 5 minutes (300 seconds); and
l'air ambiant pendant 5 minutes. ambient air for 5 minutes.
La figure 1 illustre l'évolution de la fréquence d'oscillation (F) du capteur, exprimée en Hz, en fonction du temps (t), exprimé en secondes, telle qu'obtenue au cours de ces tests. FIG. 1 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
Comme le montre cette figure, on observe une chute de la fréquence d'oscillation du capteur en présence de vapeurs de benzoate de méthyle, qui commence à se produire dès la mise en contact de ce capteur avec ces vapeurs. Cette chute de fréquence est réversible puisque le fait de remettre le capteur au contact de l'air ambiant entraîne immédiatement une remontée de sa fréquence d'oscillation. As shown in this figure, there is a drop in the oscillation frequency of the sensor in the presence of methyl benzoate vapors, which begins to occur as soon as the sensor is brought into contact with these vapors. This frequency drop is reversible since bringing the sensor into contact with the ambient air immediately causes a rise in its oscillation frequency.
Il convient de préciser que, dans le domaine des capteurs à microbalance à quartz, une variation de la fréquence d'oscillation d'un capteur est considérée comme significative et, donc, exploitable dès lors qu'elle est supérieure à trois fois le bruit de fond de ce capteur, soit environ 10 Hz dans le cas présent. It should be noted that, in the field of quartz microbalance sensors, a variation of the oscillation frequency of a sensor is considered significant and therefore exploitable when it is greater than three times the noise of a sensor. bottom of this sensor, about 10 Hz in this case.
Or, comme le montre la figure 1, la chute de la fréquence d'oscillation du capteur induite par l'exposition aux vapeurs de benzoate de méthyle est très largement supérieure à cette valeur seuil puisqu'elle est de 500 Hz, ce qui signifie que la PcZn(Ooct)s présente dans le capteur est très sensible aux vapeurs de benzoate de méthyle. However, as shown in FIG. 1, the fall in the oscillation frequency of the sensor induced by the exposure to methyl benzoate vapors is very much greater than this threshold value since it is 500 Hz, which means that the PcZn (Ooct) s present in the sensor is very sensitive to methyl benzoate vapors.
EXEMPLE 2 : Détection de vapeurs de nitrite d'isoamyle (constituant des poppers) par un capteur à microbalance à quartz EXAMPLE 2: Detection of isoamyl nitrite vapor (constituting poppers) by a quartz microbalance sensor
Dans cet exemple, on utilise un capteur à microbalance à quartz identique à celui utilisé dans l'exemple 1 ci-avant.
Ce capteur est soumis à des tests de détection qui sont réalisés à 20°C et qui consistent à l'exposer successivement à : In this example, a quartz microbalance sensor identical to that used in Example 1 above is used. This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
l'air ambiant pendant 10 minutes (soit 600 secondes) ; ambient air for 10 minutes (600 seconds);
du nitrite d'isoamyle à une concentration de 35 000 ppm dans de l'air ambiant pendant 5 minutes (soit 300 secondes) ; et à isoamyl nitrite at a concentration of 35,000 ppm in ambient air for 5 minutes (300 seconds); and
l'air ambiant pendant 5 minutes. ambient air for 5 minutes.
La figure 2 illustre l'évolution de la fréquence d'oscillation (F) du capteur, exprimée en Hz, en fonction du temps (t), exprimé en secondes, telle qu'obtenue au cours de ces tests. FIG. 2 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
Comme le montre cette figure, on observe une chute de la fréquence d'oscillation du capteur en présence de vapeurs de nitrite d'isoamyle, qui commence à se produire dès la mise en contact de ce capteur avec ces vapeurs et qui est réversible puisque le retour du capteur à l'air ambiant se traduit immédiatement par un retour de sa fréquence d'oscillation à sa valeur initiale ou à une valeur proche de celle-ci. As shown in this figure, there is a drop in the oscillation frequency of the sensor in the presence of isoamyl nitrite vapor, which begins to occur as soon as the sensor is brought into contact with these vapors and which is reversible since the The return of the sensor to the ambient air immediately results in a return of its oscillation frequency to its initial value or to a value close to it.
Là également, la chute de la fréquence d'oscillation du capteur induite par l'exposition aux vapeurs de nitrite d'isoamyle, qui est de l'ordre de 600 Hz, témoigne d'une très grande sensibilité de la PcZn(Ooct)s vis-à-vis des vapeurs de ce stupéfiant. Here again, the drop in the oscillation frequency of the sensor induced by exposure to isoamyl nitrite vapor, which is of the order of 600 Hz, shows a very high sensitivity of the PcZn (Ooct) s vis-à-vis the vapors of this narcotic.
EXEMPLE 3 : Détection de vapeurs de cocaïne par un capteur à microbalance à quartz EXAMPLE 3: Detection of cocaine vapors by a quartz microbalance sensor
Dans cet exemple, on utilise un capteur à microbalance à quartz identique à ceux utilisés dans les exemples 1 et 2 ci-avant. In this example, a quartz microbalance sensor identical to those used in Examples 1 and 2 above is used.
Ce capteur est soumis à des tests de détection qui sont réalisés à 20°C et qui consistent à l'exposer successivement à : This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
l'air ambiant pendant 10 minutes (soit 600 secondes) ; ambient air for 10 minutes (600 seconds);
de la cocaïne à une concentration de 0,02 ppb dans de l'air ambiant pendant 5 minutes (soit 300 secondes) ; et à cocaine at a concentration of 0.02 ppb in ambient air for 5 minutes (300 seconds); and
l'air ambiant pendant 5 minutes. ambient air for 5 minutes.
La figure 3 illustre l'évolution de la fréquence d'oscillation (F) du capteur, exprimée en Hz, en fonction du temps (t), exprimé en secondes, telle qu'obtenue au cours de ces tests.
Comme le montre cette figure, on observe une chute de la fréquence d'oscillation du capteur en présence de vapeurs de cocaïne, qui commence à se produire dès la mise en contact de ce capteur avec ces vapeurs. La diminution de la fréquence d'oscillation du capteur est de l'ordre de 60 Hz. EXEMPLE 4 : Détection de vapeurs d'héroïne par un capteur à microbalance à quartz FIG. 3 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests. As shown in this figure, there is a drop in the oscillation frequency of the sensor in the presence of cocaine vapor, which begins to occur as soon as the sensor is brought into contact with these vapors. The decrease of the frequency of oscillation of the sensor is of the order of 60 Hz. EXAMPLE 4: Detection of heroin vapors by a quartz microbalance sensor
Dans cet exemple, on utilise un capteur à microbalance à quartz identique à ceux utilisés dans les exemples 1 à 3 ci-avant. In this example, a quartz microbalance sensor identical to those used in Examples 1 to 3 above is used.
Ce capteur est soumis à des tests de détection qui sont réalisés à 20°C et qui consistent à l'exposer successivement à : This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
. l'air ambiant pendant 10 minutes (soit 600 secondes) ; . ambient air for 10 minutes (600 seconds);
de l'héroïne à une concentration de 0,4 ppt dans de l'air ambiant pendant 5 minutes (soit 300 secondes) ; et à heroin at a concentration of 0.4 ppt in ambient air for 5 minutes (300 seconds); and
l'air ambiant pendant 5 minutes. ambient air for 5 minutes.
La figure 4 illustre l'évolution de la fréquence d'oscillation (F) du capteur, exprimée en Hz, en fonction du temps (t), exprimé en secondes, telle qu'obtenue au cours de ces tests. FIG. 4 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
Comme le montre cette figure, on observe une chute de la fréquence d'oscillation du capteur en présence de vapeurs d'héroïne, qui commence à se produire dès la mise en contact de ce capteur avec ces vapeurs. La diminution de la fréquence d'oscillation du capteur est de l'ordre de 45 Hz. As shown in this figure, there is a drop in the frequency of oscillation of the sensor in the presence of heroin vapors, which begins to occur as soon as the sensor is brought into contact with these vapors. The decrease of the oscillation frequency of the sensor is of the order of 45 Hz.
EXEMPLE 5 : Détection de vapeurs d'amphétamine par un capteur à microbalance à quartz EXAMPLE 5 Detection of Amphetamine Vapors by a Quartz Microbalance Sensor
Dans cet exemple, on utilise un capteur à microbalance à quartz identique à ceux utilisés dans les exemples 1 à 4 ci-avant. In this example, a quartz microbalance sensor identical to those used in Examples 1 to 4 above is used.
Ce capteur est soumis à des tests de détection qui sont réalisés à 20°C et qui consistent à l'exposer successivement à : This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
l'air ambiant pendant 10 minutes (soit 600 secondes) ; ambient air for 10 minutes (600 seconds);
de l'amphétamine sensu stricto à une concentration de 0,4 ppt dans de l'air ambiant pendant 5 minutes (soit 300 secondes) ; et à
l'air ambiant pendant 5 minutes. amphetamine sensu stricto at a concentration of 0.4 ppt in ambient air for 5 minutes (ie 300 seconds); and ambient air for 5 minutes.
La figure 5 illustre l'évolution de la fréquence d'oscillation (F) du capteur, exprimée en Hz, en fonction du temps (t), exprimé en secondes, telle qu'obtenue au cours de ces tests. FIG. 5 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
Comme visible sur cette figure, on observe une chute de la fréquence d'oscillation du capteur en présence de vapeurs d'amphétamine, qui commence à se produire dès la mise en contact de ce capteur avec ces vapeurs. La diminution de la fréquence d'oscillation du capteur est de l'ordre de 110 Hz. As shown in this figure, there is a drop in the frequency of oscillation of the sensor in the presence of amphetamine vapors, which begins to occur as soon as the sensor is brought into contact with these vapors. The decrease of the oscillation frequency of the sensor is of the order of 110 Hz.
EXEMPLE 6 : Détection de vapeurs de benzoate de méthyle par un capteur SAW EXAMPLE 6 Detection of methyl benzoate vapors by a SAW sensor
Dans cet exemple, on réalise un capteur SAW, de fréquence d'oscillation nominale de 433 MHz, en recouvrant les deux faces du substrat piézoélectrique de ce capteur d'un film mince de PcZn(Ooct)s (Sigma-AIdrich, référence 459720). In this example, a SAW sensor, with a nominal oscillation frequency of 433 MHz, is made by covering the two faces of the piezoelectric substrate of this sensor with a PcZn (Ooct) s thin film (Sigma-Aldrich, reference 459720). .
Le dépôt de ce film mince est réalisé en effectuant 1 pulvérisation de 0,02 à 0,2 seconde d'une solution de PcZn(Ooct)s dans le chloroforme, de concentration comprise entre 0,5 et 1 g/L. The deposition of this thin film is carried out by spraying 0.02 to 0.2 seconds of a solution of PcZn (Ooct) in chloroform, with a concentration of between 0.5 and 1 g / l.
Le capteur est soumis à des tests de détection qui sont réalisés à 20°C et qui consistent à l'exposer successivement à : The sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
l'air ambiant pendant 10 minutes (soit 600 secondes) ; ambient air for 10 minutes (600 seconds);
du benzoate de méthyle à une concentration de 350 ppm dans de l'air ambiant pendant 5 minutes (soit 300 secondes) ; et à methyl benzoate at a concentration of 350 ppm in ambient air for 5 minutes (300 seconds); and
l'air ambiant pendant 5 minutes. ambient air for 5 minutes.
La figure 6 illustre l'évolution de la fréquence d'oscillation (F) du capteur, exprimée en Hz, en fonction du temps (t), exprimé en secondes, telle qu'obtenue au cours de ces tests. FIG. 6 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
Comme le montre cette figure, on observe une augmentation de la fréquence d'oscillation du capteur en présence de vapeurs de benzoate de méthyle, qui commence à se produire dès la mise en contact de ce capteur avec ces vapeurs. Cette augmentation de fréquence d'oscillation est réversible puisque le fait de remettre le
capteur au contact de l'air ambiant se traduit immédiatement par un retour de la fréquence d'oscillation à une valeur proche de sa valeur initiale. As shown in this figure, there is an increase in the oscillation frequency of the sensor in the presence of methyl benzoate vapors, which begins to occur as soon as the sensor is brought into contact with these vapors. This increase in oscillation frequency is reversible since the fact of putting the sensor in contact with the ambient air immediately results in a return of the oscillation frequency to a value close to its initial value.
L'augmentation de la fréquence d'oscillation du capteur induite par son exposition aux vapeurs de benzoate de méthyle est de l'ordre de 12 000 Hz, ce qui signifie que la PcZn(Ooct)s présente dans ce capteur est très sensible aux vapeurs de ce composé. The increase in the oscillation frequency of the sensor induced by its exposure to methyl benzoate vapors is of the order of 12 000 Hz, which means that the PcZn (Ooct) s present in this sensor is very sensitive to vapors. of this compound.
EXEMPLE 7 : Détection de vapeurs de nitrite d'isoamyle par un capteur SAW EXAMPLE 7 Detection of Isoamyl Nitrite Vapors by a SAW Sensor
Dans cet exemple, on utilise un capteur SAW identique à celui utilisé dans l'exemple 6 ci-avant. In this example, a SAW sensor identical to that used in Example 6 above is used.
Ce capteur est soumis à des tests de détection qui sont réalisés à 20°C et qui consistent à l'exposer successivement à : This sensor is subjected to detection tests which are carried out at 20 ° C and which consist of exposing it successively to:
l'air ambiant pendant 10 minutes (soit 600 secondes) ; ambient air for 10 minutes (600 seconds);
du nitrite d'isoamyle à une concentration de 35 000 ppm dans de l'air ambiant pendant 5 minutes (soit 300 secondes) ; et à isoamyl nitrite at a concentration of 35,000 ppm in ambient air for 5 minutes (300 seconds); and
l'air ambiant pendant 5 minutes. ambient air for 5 minutes.
La figure 7 illustre l'évolution de la fréquence d'oscillation (F) du capteur, exprimée en Hz, en fonction du temps (t), exprimé en secondes, telle qu'obtenue au cours de ces tests. FIG. 7 illustrates the evolution of the frequency of oscillation (F) of the sensor, expressed in Hz, as a function of time (t), expressed in seconds, as obtained during these tests.
Cette figure montre que la mise en contact du capteur avec des va peurs de nitrite d'isoamyle se traduit par une augmentation de sa fréquence d'oscillation qui est de l'ordre de 30 000 Hz et qui témoigne d'une très grande sensibilité de la PcZn(Ooct)s présente dans ce capteur aux vapeurs de nitrite d'isoamyle. This figure shows that the contacting of the sensor with isoamyl nitrite values leads to an increase in its oscillation frequency which is of the order of 30 000 Hz and which shows a very high sensitivity of PcZn (Ooct) is present in this sensor to isoamyl nitrite vapors.
Cette augmentation de fréquence d'oscillation est réversible puisque le retour du capteur à l'air ambiant se traduit immédiatement par un retour de sa fréquence d'oscillation à une valeur proche de sa valeur initiale. RÉFÉRENCES CITÉES This increase in oscillation frequency is reversible since the return of the sensor to the ambient air immediately results in a return of its oscillation frequency to a value close to its initial value. REFERENCES CITED
[1] US 2003/0003587 [1] US 2003/0003587
[2] Stubbs et al., IEEE Sensors Journal 2005, 5, 335-339 [2] Stubbs et al., IEEE Sensors Journal 2005, 5, 335-339
[3] Frisk et al., Lab on a Chip 2008, 8, 1648-1657 [3] Frisk et al., Lab on a Chip 2008, 8, 1648-1657
[4] Paoletti et al., Sensors 2009, 9, 5277-5297
[5] Brunet et al., Thin Solid Films 2005, 490, 1, 28-35 [4] Paoletti et al., Sensors 2009, 9, 5277-5297 [5] Brunet et al., Thin Solid Films 2005, 490, 1, 28-35
[6] Sanchez-Pedrono et al., Analitica Chimica Acta 1986, 182, 285 [6] Sanchez-Pedrono et al., Analitica Chimica Acta 1986, 182, 285
[7] Hoummady et al., Smart Materials and Structures 1997, 6, 647-657
[7] Hoummady et al., Smart Materials and Structures 1997, 6, 647-657
Claims
1. Utilisation d'une phtalocyanine de zinc substituée de formule ci- après : 1. Use of a substituted zinc phthalocyanine of the following formula:
comme matériau sensible dans un capteur chimique pour détecter la présence dans un milieu gazeux d'au moins un composé choisi parmi les opiacés, la cocaïne, les cannabinoïdes, les amphétamines, le diéthylamide de l'acide lysergique, la cathine, la cathinone, les dérivés synthétiques de la cathinone, l'acide γ-hydroxybutyrique, la kétamine, le nitrite d'isoamyle, le nitrite de n-amyle, leurs isomères, leurs sels, leurs esters, leurs éthers, leurs précurseurs et leurs produits de dégradation. as a sensitive material in a chemical sensor for detecting the presence in a gaseous medium of at least one compound selected from opiates, cocaine, cannabinoids, amphetamines, lysergic acid diethylamide, cathine, cathinone, synthetic derivatives of cathinone, γ-hydroxybutyric acid, ketamine, isoamyl nitrite, n-amyl nitrite, their isomers, their salts, their esters, their ethers, their precursors and their degradation products.
2. Utilisation selon la revendication 1, dans laquelle la phtalocyanine de zinc substituée est utilisée sous la forme d'un film mince recouvrant l'une ou les deux faces d'un substrat que comporte le capteur. The use of claim 1, wherein the substituted zinc phthalocyanine is used in the form of a thin film covering one or both of a substrate of the sensor.
3. Utilisation selon la revendication 2, dans laquelle le film mince mesure de 1 nanomètre à 10 micromètres d'épaisseur.
The use of claim 2, wherein the thin film is 1 nanometer to 10 microns thick.
4. Utilisation selon l'une quelconque des revendications 1 à 3, dans laquelle le capteur est un capteur gravimétrique. 4. Use according to any one of claims 1 to 3, wherein the sensor is a gravimetric sensor.
5. Utilisation selon la revendication 4, dans laquelle le capteur est un capteur à microbalance à quartz ou un capteur à ondes acoustiques de surface. Use according to claim 4, wherein the sensor is a quartz microbalance sensor or a surface acoustic wave sensor.
6. Utilisation selon l'une quelconque des revendications 1 à 5, dans laquelle le composé est le benzoate de méthyle, la cocaïne, l'héroïne, une amphétamine ou le nitrite d'isoamyle.
The use according to any one of claims 1 to 5, wherein the compound is methyl benzoate, cocaine, heroin, amphetamine or isoamyl nitrite.
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EP16790599.1A EP3371587A1 (en) | 2015-11-03 | 2016-11-02 | Use of a substituted zinc phthalocyanine as a sensitive material in a chemical sensor for detecting the presence of drugs in a gaseous medium |
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FR1560509A FR3043209B1 (en) | 2015-11-03 | 2015-11-03 | USE OF A SUBSTITUTED ZINC PHTHALOCYANINE AS A SENSITIVE MATERIAL IN A CHEMICAL SENSOR FOR DETECTING THE PRESENCE OF NARCOTIC DRUGS IN A GASEOUS MEDIUM |
FR1560509 | 2015-11-03 |
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EP3816061A1 (en) | 2019-10-29 | 2021-05-05 | Schoeller Allibert GmbH | Container with recesses for piece goods in a side wall and associated fitting method |
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EP0921392A2 (en) * | 1997-12-03 | 1999-06-09 | TRW Inc. | Semiconductor chemical sensor |
US20030003587A1 (en) | 2002-06-28 | 2003-01-02 | Murray George M | Molecularly imprinted polymer based sensors for the detection of narcotics |
-
2015
- 2015-11-03 FR FR1560509A patent/FR3043209B1/en not_active Expired - Fee Related
-
2016
- 2016-11-02 EP EP16790599.1A patent/EP3371587A1/en not_active Withdrawn
- 2016-11-02 WO PCT/EP2016/076396 patent/WO2017076883A1/en active Application Filing
Patent Citations (2)
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EP0921392A2 (en) * | 1997-12-03 | 1999-06-09 | TRW Inc. | Semiconductor chemical sensor |
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HARBECK M ET AL: "Preferential sorption of polar compounds by fluoroalkyloxy substituted phthalocyanines for the use in sorption based gas sensors", SENSORS AND ACTUATORS B: CHEMICAL: INTERNATIONAL JOURNAL DEVOTED TO RESEARCH AND DEVELOPMENT OF PHYSICAL AND CHEMICAL TRANSDUCERS, ELSEVIER BV, NL, vol. 150, no. 2, 28 October 2010 (2010-10-28), pages 616 - 624, XP027427955, ISSN: 0925-4005, [retrieved on 20100929], DOI: 10.1016/J.SNB.2010.08.031 * |
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EP3816061A1 (en) | 2019-10-29 | 2021-05-05 | Schoeller Allibert GmbH | Container with recesses for piece goods in a side wall and associated fitting method |
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